Learned something new about my step sisters friends M/FFFF
Posted: Sun Jul 20, 2025 4:34 pm
Finally got around to working on a follow up to my previous story: viewtopic.php?t=22525
It will likely be a bit till the next update but hope you enjoy.
It had been two weeks since I (21M) had a crazy night with my two step sisters Jen (19, blonde 5ft 5inch, tan, athletic-fit build, B sized breasts) and Katie (19,burnette, 5ft 4inch, little more curves then Jen, C sized breasts) and my friends with benefits girl Mandy (21, 5ft, slim build, tan, B sized breasts). What had started with a simple car ride had led to me eventually tying up all three, using sex toys on Jen, sucking whip cream off Katie’s toes and banging the hell out of Mandy. It was quite a night, but now two weeks later and my dad and step mom headed out for another weekend away, my step sisters had some more fun in mind.
“Oh my god I can’t believe the night we are going to have,” Jen squealed. Jen was wearing black bootie shorts and a white tank top. Our friends have been so jealous hearing about all the fun we had with you Jakey.”
“I’m pretty sure they don’t believe us still,” Katie added. She was wearing black bootie shorts and blue t shirt. “I can’t wait for them to experience some of the fun we had.”
“What exactly do you all have planned?” I asked, “and who is to say I agreed to anything, maybe I’ll just head out for the night.”
“No Jake please you have to stay and play,” Jen begged.
“Yea Jake, Jen’s been bragging to Mary, Jess and Trish since our night of fun.” Katie said, “If you bail now it will make us look so bad. Plus our night really gave me a boost and I want our friends to get that same experience.”
“Fine,” I relented “I’ll stay and play.”
Jen and Katie let out yell of joy and started skipping around the living room.
“So who all is coming to this and what exactly do you all have planned?”
“Well,” Jen started, “our friends Trish, Jess and Mary I’m pretty sure you’ve met them before, they all remember you. I played field hockey with Jess in High School and Trish was in the band with Katie. There both like five foot one with black hair. Jess has pretty athletic build but she has a bigger butt that me. Trish has a bit more curves then Katie or me but also has the biggest tits of our group. Mary well…”
“Mary is Jen’s frenemy,” giggled Katie.
“She’s still bitter I beat her for Prom Queen in high school,” Jen explained, “but she’ll probably try to fuck you just because you’re my step brother.”
‘If you don’t like her why did you invite her?” I asked.
“Of our friends she is the biggest none this happened slash you two are liars trash talker” Jen explained. “I want to show her what fun we had even if that means you show her your little solider.”
“Oh so your saying I could hook up with one of your friends tonight?” I asked intrigued.
“Probably more than one,” Jen replied. “They are all horny little things. Mary definitely, Jess thinks your cute, Trish has a crush on you. I mean I’m surprised you didn’t notice we had to practically pick Trish’s jaw off the floor the last time she was over. You had just finished mowing the lawn and came in the house without your shirt on. I’m pretty sure her tongue was on the floor while you grabbed a drink. Besides our friends, you know I’m always willing,” Jen paused and came towards me and brushed her hand across my crotch. “In fact the only one who probably isn’t horny is little miss Katie thanks her date last weekend.”
“I must not have noticed,” I replied.
“Jen its not nice to spill Trish’s secret,” Katie added.
“Its not a secret and Jake would have figured it out it two seconds tonight anyways.” Jen replied.
“You had a date,” I replied excited for Katie and trying to change the subject.
“It was a bust,” Katie responded defeated. “He said feet were gross,” Katie added looking down at her bare feet with her red painted toe nails. “Even though I got a pedicure and wore Jen’s cute sandals.”
“You stole my sandals,” Jen replied.
“I borrowed them,” Katie replied, “besides you have so many you didn’t even notice.”
“I’m sorry he wasn’t what you looking for Katie,” I said. “But hey way to put yourself out there and go after something.”
“Thanks,” Katie replied sheepishly, “Thanks to our little fun I have some boxes to check now,” Katie said laughing.
“I’m sorry he didn’t like your feet Katie,” Jen said with a smile, “Come over here and I’ll give your feet some attention.”
Jen moved towards her sister and Katie realizing what Jen was planning took off towards the other side of the kitchen table.
“Jen I’m sorry I didn’t ask to borrow your sandals,” Katie said trying to keep away from her sister.
“Too late,” Jen replied.
Katie took off, with a barefooted Jen close on her tail. Jen was faster that Katie, her teal painted toes quickly caught Katie and tackled her onto the sectional. Jen they grabbed Katie’s ankles and began raking her figure nails across Katie’s bare soles. Katie struggled, kicked and slapped at her sister trying to get free. Jen showed no mercy, keeping a tight grip on Katie’s ankles, Jen continued to move her fingers up and down Katie’s exposed soles. Katie was completely helpless and Jen’s constant tickling was sucking whatever fight she had left in her. Despite Katie’s constant screams to stop and let go, Jen continued to work on Katie’s feet. Running her fingers across the top of Katie’s feet and even mockingly playing this little piggy with Katie’s red painted toes. Eventually Jen relented and Katie collapsed face first into the sectional.
“Now that your done torturing Katie can you tell me what exactly you have planned for this evening?” I asked Jen.
“We need to wait for the rest of the girls to come,” Jen explained. “All you need to know is, you are playing a creep who breaks into the house while 5 sexy girls are having a sleep over. I’ll explain the rest when the girls join us.”
“I don’t know,” I responded “Five girls seem like a lot to handle on my own, sure I can’t have some help. I’m sure Steve would be free to help me out.”
“Uhhh no,” Jen replied disgusted, “Give a guy one BJ and he blows up your socials and won’t leave you alone. Besides Mary would eat him alive, while Jess and Trish think he’s creepy. It wouldn’t work if he was a part of this. It has to be just you, you’re the right mix of safe and sexy the girls want.”
“Alright,” I relented.
“Good,” Jen replied, “the queen has spoken, so its been said so its been done.”
“Queen of what?” Katie yelled to her sister, “Queen of Steve’s spank bank.” Katie tossed a pillow at her sister, still annoyed about her tickling attack. “But getting back to the topic at hand Jake, I won’t resist if you decide to place your hands on me tonight,” she added with a giggle.
“Really,” I replied with the grin as I made my way over to wards Katie. “Maybe we can test that right now. I quickly made my way towards Katie who was still sitting on the sectional.”
“Wait Jake what are doing no don’t,” Katie yelled but it was too late. I pounced on her and used my right hand to put her wrists together and pull her arms above her head. With my left hand I pulled her shirt up a bit to expose her stomach.
“No resisting Katie,” I said laughing as a I ran my fingers up and down her exposed stomach. Katie once again howled in a mixture of pain and pleasure begging me to stop. She struggled a little but as strong as I was there was little she could do.
“Oh look at this, time for round two,” Jen said as she came back to her sister and started tickling her feet again.
“Stop please, you are going to make me pee,” Katie begged as I continued to tickle her stomach and Jen tickled her feet. After a minute Jen stopped.
“I have an idea,” Jen said. “Jake, don’t let her go I’ll be right back.” Jen spirted up the steps towards her bedroom.
“Please let me go,” Katie begged, “I’m sorry I can’t take anymore.”
“Let’s see where Jen is going with this,” I replied.
Jen quickly returned bouncing down the steps. Hiding something behind her back.
“I was going to save this for tonight,” Jen said, “But I think Katie can help us test it out first.”
Jen revealed she was holding an electric toothbrush and it was pretty obvious what was coming. Katie made one last plea to be released but it fell on deaf ears.
“Shut her up Jakey, we don’t want to wake the neighbors,” Jen said as she turned on her weapon of torture. I placed my free hand over Katie’s mouth and she began mmmfffing like crazy into my hand. Jen placed the now running electric toothbrush on Katie’s bare soles. After attacking the bottoms of poor helpless Katie’s feet, Jen next moved the toothbrush to the tops of Katie’s feet. Katie continued to try and wiggle free and screamed loudly into my hand but my hand gag did a pretty good job keeping her quiet. Jen decided one last area needed attention and began under and in between poor Katie’s toes. As Jen moved the toothbrush across all ten of Katie’s toes, the noise Katie began making under my gag switched from pain to pleasure. With her face starting to turn redder, Katie closed her eyes and began thrusting her hips while continuing a very now sensual moan under the gag. Jen’s work with the toothbrush suddenly caused Katie’s body to tense up before Katie let out an “Oh Fuck,” stopping her resistance against me and collapsed back into the sectional. I pulled my hand from her mouth and let go of her wrists as Katie took recovery breaths and melted deeper into the sectional.
“Fuck, I’m wet you assholes,” Katie let out.
“Piss or pleasure’” Jen replied laughing at her sister.
“Screw you,” Katie replied before getting to her feet. “Now I have to shower before the girls get here.”
Katie headed up the steps too embarrassed to look back at us.
“So now can you tell what all is in store for tonight?” I asked Jen.
“Keep your shirt on boy,” Jen replied we need all the girls here so I only have to explain this once.
“ok,” I responded annoyed. I turned the tv on and relaxed on the sectional while Jen went upstairs to organize the “toys” for tonight. Katie finished her shower and came down stairs in sweats and a t shirt. Just as Katie sat down the door bell rang.
“They’re here,” Katie yelled upstairs to Jen and went to answer the door.
Katie skipped over to the door and opened it. Their friends Jess and Trish walked in. Jess was short about 5ft 1inches with dirty blonde hair. She had an athletic build similar to Jen but with a bit of a bigger ass. Her face wasn’t as pretty as Jen’s but she was cute. She was wearing tan kapri pants with a blue crop top and hey dude shoes which she quickly slipped off showing her tiny feet with pink painted toe nails. She opened her mouth to say hi but was loudly interrupted by Trish who screamed, “Oh fuck he’s really here,” while trying to hide behind her friend.
Trish was also short, maybe five feet tall with dark brown hair. She was dressed in PJ pants, oversized T-shirt and black flip flops.. She had a lot more curves than my step sisters and Jess, and even with the baggy t-shirt I could see she had a very big DD pair of breast underneath.
“Trish, what are you doing, get off of me.” Jess yelled at her friend.
“Jen said dress causal and it was just going to be girl fun, why did no one tell me he’d be here too. I look like crap.” Trish said before running upstairs, losing her flip flops in the process.
“Trish wait up,” Jess said chasing after her friend. Jen passed them coming down the stairs.
“You should have told Trish that Jake was part of the fun,” Katie said towards her sister.
“Please,” Jen huffed, “She would have bailed if I said Jake would be here. She’ll get over her little crush and be fine in a bit.”
“I guess your right,” Katie replied, “Still a little mean.”
Just as Katie was about to close the door their stunning friend Mary walked in. She truly was like a real life Stacy Keibler. She was a tall blonde, probably 5ft 10inches tall but she was wearing what looked like 3 inch black heels that made her almost as tall as me. She was dressed like a sexy secretary, in a short black skirt, tan pantyhose that really made her long legs pop and tight white blouse that seemed to be struggling to contain her perky size C breasts.
“Hey sexy, I’m Mary, nice to meet your,” Mary said giving me a wink.
“I’m Jake uhh, Katie and Jen’s step brother,” I managed to stammer out.
“Of course you are,” Mary said with a laugh, “I’m looking forward to spending some time together tonight and maybe you can show me that sweet package I’ve heard so much about.”
I stood their trying to respond while also keeping my jaw from hitting the floor, lucky Jen was there to break the tension.
“Mary, what the fuck I said dress casual,” Jen hissed.
“I brought a bag,” Mary replied, “My dad needed help at the dealership today and made me dress all professional.”
The break allowed me time to mutter that I need to go pick up food and stammered out the door. I made It to my car and took a deep breathe to compose myself before starting my car and heading to the pizza shop. After seeing Mary I didn’t care what my step sisters had planned I was in. I didn’t care if Mary was only flirting with me to piss off Jen, I was ok being used. As I pulled in to the pizza shop I got a text from Mandy asking what my plans were and if I wanted to hang out tonight. I texted her back letting her know I was helping my step sisters and friends at my parents and wouldn’t be free. I picked up the pizza, salad and drinks and headed back home.
I walked back into the house loudly announced to the girls that food was here and expected them to coming running and to give me more attention. Instead I was met with silence, confused I yelled food again and walked into the house. All the girls minus Jen were sitting at the dining room table either writing on or looking at an index card.
“umm, what gives?,” I asked Jen in the kitchen while putting the food on the counter.
“Ok so the scenario tonight is us girls are having a sleep over and you’re the creep next door that breaks in and takes advantage of us so to speak,” Jen started explaining. “You got me to thinking about trying to handle the needs-wants of five different girls plus your and everyone’s comfort level with all the different options that the girls may want to experience. That’s a lot to process, let alone communicate if the girls have gags in their mouth. So I’m having the girls write down their limits-wishing on these cards I made.”
“Oh so I’ll have a little consent cheat sheet for each girl,” I replied.
“A bit more than that,” Jen explained. “So on each card will have the minimum amount of clothes that must be on at all times, toys they are open to using, a body part they want you to focus on and one must fantasy they want to experience with you.”
“The girls realize I have my own limits right,” I asked.
“I told them they can put things down but you have to be ok too, consent goes two ways,” Jen responded. “But I mean if you can handle sucking sugar off Katie’s toes you should be able to handle whatever these girls want.”
“You sure,” I said sneaking a peak at Mary who had by now had ditched her heels and was sitting the dining room table with just pantyhose covering her feet.
“You’ll be fine,” Jen responded, “Girls come grab some food.”
The girls all came to the kitchen to grab dinner while I stood away from the food letting them all have first dibs. Trish saw me and started to blush but was at least able to be in the same room as me. Jen, Katie and Jess all grabbed food and each gave me a smile then headed back to sit in the dining room. As they exited the kitchen, Mary came into the room in all her sexy glory.
“Hi Jake,” Mary said politely, “Glad you made it back, I’m looking forward to getting close to you tonight.” Before I could respond she brushed her hand against my junk then spun herself around her ass was pressed very firmly against my crotch. I took a breath to try keep from getting hard.
“I’m looking forward to getting close to you as well,” I managed to respond. “What kind of pizza do you like, I got a few different kinds.”
“Sausage,” She replied. Mary kept her ass pressed against my crotch but turned her neck so I could see her face. “I love getting a good sausage in my mouth, the bigger the better.”
Thankfully she went over and grabbed a slice before feeling how hard she had just made my dick. She headed back to the table and got myself some food and sat down with the girls for dinner. I sat down next to Katie with Mary sitting across from me. I tried to focus on my food while the girls chatted about work, boys, college, honestly I wasn’t really paying attention. Every so often I would glace over at Jess and Trish who smile and blush at me, while anytime I looked in Mary’s direction she would wink at me and lick her lips. As everyone was finishing up Jen took the floor and snapped me back into focus.
“Ok girls,” Jen announced loudly. “Here is the plan for tonight. The five of us beautiful ladies are having a fun little sleep over, but the creep next door played by Jake, breaks in and takes us captive. Then depending on what you ladies put on your cards and what all Jake is comfortable with, he’ll have some fun with you. Oh and one other thing, write down your favorite breakfast cereal on the back of the card then cover it with a piece of tape.”
The rest of the girls and myself were a bit confused?
“What does cereal have to do with this?,” Jess asked.
“That ladies is the code word that Jakey here will need to get out you either via pain or pleasure. We all put in $20 bucks in and whoever can keep the word safe gets to split the pot. But no giving him a fake cereal, do that you are disqualified.”
“How will you get the word out of us Jake,” Trish asked me.
“Umm I don’t know I mean I probably could just tickle it out of you all or something,” I responded.
“Well I’m toast,” Jess laughed, “My feet are really ticklish.”
“I can think of some better to do with feet then tickle them,” Mary said while locking eyes with me. While continuing her conversation Mary stretched her leg under the table so her pantyhose covered foot landed right on my crotch.
“I’m more of fan of foot rubs,” Mary added with a smile. “Just having something going up and down on a sensitive area, just feels so good.”
“Yep,” I responded trying to keep my cool and avoid drawing attention to what Mary was doing under the table.
“Girls, girls,” Jen yelled, thankfully taking the focus of the group. “enough about feet jeez, the quicker we finishing eating the quicker we can get to the fun.”
Mary pulled her foot off my crotch and gave me a wink, she could tell that little move had gotten me hard. I took a big gulp from my drink trying to keep my cool. I hoped none of the girls looked under the table to see me sporting wood like a kid in middle school. The girls changed topics talking about some Bravo reality or something I wasn’t paying attention and tried to keep my cool. Eventually I calmed down enough that I could get up from the table and offered to help clean up. The girls handed Jen their cards while I was in the kitchen and then passed me on their way upstairs. Jess and Trish just smiled and giggled when they passed me but Mary made sure to drop something near me in the kitchen. She bent over right in front of me to pick it up, sticking her ass in the air. God her ass looked so good if we were alone I probably would have jumped her right there in the kitchen but with other eyes around I kept my focus on washing plates and glasses instead. Mary and Katie headed upstairs while Jen brought over the last of the dishes for me to wash.
“You leave the cards on the table for me,” I asked.
“Is Jakey a little horny from our dinner conversation,” Jen laughed. “You have to wait no peaking just yet.”
Jen headed up with the rest of the girls to get ready, while I finished cleaning. The girls took their time getting ready so I sat down in the living room waiting for them to return. I debated what order I should try and capture the girls. Should I be selfish and grab Mary first, though the rest of the girls may get bored waiting. I could grab Jen and Katie first since I would likely know what they want and could move through it quickly. Hopefully Trish wants me to play we her big tits. Eventually after some debate I decide I would grab Jen first. I could stash her in her room and use her phone to lure the rest of the girls to different parts of the house and capture them.
“Oh Jakey,” Jen called from upstairs, “your victims are ready.
The girls started to make their way down one by one. Trish came down first, she was still wearing the long pj pants but had put on a tighter t shirt that made her big tits pop. She also had done her hair and make up as well. Katie came down next wearing tight blue bicycle shorts and tight blue tank top. She had put her hair in a nice pony tail and had added some teal eye liner making her pretty eyes pop. Jess followed Katie, donning red pair of boy shorts and black sports bra. She curled her hair a bit and added make up to her face as well. The girls were cute but I was waiting the stars of the night Jen and Mary to come down.
Mary sauntered slowly down the steps. She had taken her pantyhose off and put a touch of glitter on her sexy legs. She was wearing much less than the other girls with only a tiny black thong covering her lower half and just a leopard printed strapless bra covering her breasts. It took all my strength to keep my jaw from hitting the floor as she did a little twirl to show me her mostly bare backside.
Jen sensing the hold Mary had on my eyes quicker followed. She was wearing a sexy pink lingerie top and tiny white thong. She gave Mary a passive aggressive hip check to move her out of the way. Jen was also carrying a book bag for some reason but eyes mostly focus on the five pretty barefooted girls in front of me.
“like what you see there,” Katie giggled breaking the silence.
“Very much so,” I managed to spill out, “You all look gorgeous.”
“Thank you,” Trish responded blushing a bit “Its hard to look sexy next to girls only wearing dental floss.
“You could pull off dental floss too if you weren’t so shy,” Mary responded.
“No thanks,” Trish replied, “I like having pockets,” as she pulled her phone out of her PJ pants pocket.
“Do I want to know where the rest of you are hiding your phones,” I said laughing but also trying to confirm the girls had them on their person as I would need them later to help capture them.
Katie and Jess giggled and pulled their phones from their bras while Jen gave me an eye roll.
“I’m not sure what you’ve been focusing on Jakey but it clearly wasn’t Mary and my hands,” Jen said mockingly. Both girls were clearly still holding their phones in their hands.
“Ugh can I get your all cards now,” I said trying to hide the fact that I was being a bit of a perv.
“One second,” Jen replied. “I need to explain a few more things for everyone. In this bag is every toy the girls have requested you use, along with rope, tape and gags, but if you have other restraints in mind feel free to add them to the bag. Also to make it easier you have three tools to help you capture us.”
Jen unzipped on of the pockets in the bookbag and pulled out two wash cloths and a toy gun.
“Umm a toy gun and some dish rags,” I asked confused.
“God Jake have you zero imagination,” Jen complained. “The toy gun is your scary weapon to threaten us with to make us do what you want and the wash cloths are dossed in chloroform so you can knock us out if you need to.”
“You know chloroform is just a fake thing from the movies right,” I ask confused.
“God dumbass,” Jen yelled, “We are playing a game like it’s a movie. I don’t want you to really knock any of us out with a blow to the head. Just cover our mouths with the wash cloth and say one, two, three go to sleep. Whoever you have will pass out and become dead weight.”
“You girls are all ok with me over powering you like that?” I asked.
“I think everyone is looking forward to being held in your strong arms,” Katie said drawing a blush of red to appear on Trish’s face.
I grabbed the gun and wash cloths and stuck it in my pockets. While Jen pulled out an envelope with the girls cards on it.
“There you go Jakey,” Jen said with a smile, “Happy hunting tonight.
“Uh anything else I should know or you want to tell me before I go hide?” I asked.
“Don’t be scared to be a little rough with us,” Jess said trying to hide the redness in her face. “Just cause the kidnapper is cute doesn’t mean I’m not gunna fight back.”
“Not me,” giggled Trish, “I won’t be fighting anyone, in fact,” Trish ran grabbed one of the wash cloths from my pocket and pulled it to her mouth.
“Oh no chloroform,” Trish yelled, “I’ll be knocked out and be at the kidnappers mercy.” Trish covered her mouth with the wash cloth and mmmffff into before dramatically falling to the ground. “Oh no I’m out cold and my friends can’t save me from the sexy kidnapper, in fact they are all running out of the house to leave me alone with him.”
The ladies began laughing at Trish’s bold play. I walked over to Trish picked the rag back up before heading outside to my car. I figured if the girls really wanted me to be a creep that would break in and kidnap a bunch of girls, that kind of guy would sit in his car and stare at them from outside. The girls weren’t letting the fact that I had left ruin their fun as they were busy dancing and filming each other. I watched for a few then got out of the car and made my move.
My parents house had a basement entrance to the house, that fortunately also had a set of stairs that went up the backside of the house to the main level and upstairs. It would be a big help allowing me to sneak around the house and grab the girls when they weren’t expecting it. I snuck upstairs and hid in my room and pulled out the cards to see what all the girls were willing to let me do to them.
Trish’s was pretty tame, she wanted me to throw her over my shoulder, fondle her tits (big smile from me seeing that down) and make out with her. Jess wanted me to pull her hair and spank her butt (thus her don’t be scared to be rough with her comment), Katie of course wanted me to play with her feet. Mary and Jen well I’ll just keep those wishes to myself a bit longer. I grabbed what I needed to use on Jen and snuck into her and Katie’s room. From there I sent her a text, “Come to your room, I need your help to get the other girls out of the way so we can have our fun.” I stroked Jen’s ego just enough that she wouldn’t suspect the ambush I had waiting for her.
I hid behind her door and waited with my rag to “put her to sleep.” Despite the floors being carpet and Jen being barefoot I could easily hear her dashing up the stairs. She opened the door and came in.
“ok Jake whats the mmmffff,” Jen got only a few words out before I pounced. Covering her mouth with the dish rag while pinning her arms to her side with my other arm.
“Your step brother can no longer keep us apart beautiful,” I tried say with in the creepiest voice I could think of,” “Now just take in the rag and count with me, 1, 2, 3 go to sleep.”
Jen let out a muffled motherfucker before dropping her phone and going limp. I easily scooped her up and placed her on the bed. She looked damn good dressed in her skimpy little outfit but I kept my cool. I grabbed Jen’s limp arms and a pair of fuzzy hand cuffs and cuffed her wrists to her headboard. I gently spread Jen’s legs and began tying each leg with rope and tied them off to her footboard, leaving her tied up and looking like an upside down Y.
Now that she was fully bound, I got close to her and gently caressed her face with my hand before telling to wake up. “Rise and shine my little princess it is time for our fun,” I said to her.
Jen opened her eyes and immediately shot daggers at me. “Pause,” Jen let out in a very annoyed tone.
“Pause?” I asked confused.
“Pause, as in Jen and Jake need to have a convo and pause this role play for a minute,” Jen responded.
“Um ok,” I replied.
“What the Fuck,” Jen started to yell, “Why the hell did you grab me first I swear I will kick your mmmfff,” I quickly covered Jen’s mouth with my hand as I didn’t want her to alert the remaining girls.
“Hold on there, you need to calm down,” I ordered Jen, still holding a tight grip on her mouth, “or I’ll gag you and leave you here without any toys while I play with your friends. You want to try this pause again?”
Jen shook her head yes and I took my hand off her mouth.
“Why did you grab me first?,” Jen moaned while pulling against her handcuffs. “You were supposed to save the best for last.”
“Sorry,” I replied, “I needed this to help grab your friends,” I said holding up Jen’s phone. “I thought you would be honored, getting picked first is usually a good.”
“This isn’t a popularity contest,” Jen said as she tugged against the ropes binding her legs. “I saw you at dinner and I know what Mary put on her card. Your just going to do the bare minimum to the rest of us so you can rush to bang her.”
“I haven’t looked at anyone’s card yet,” I replied “I grabbed you first so I can use your phone to trick the other girls to split themselves up so I can stay in control. You and Katie were handful last time, adding three other girls it’s a lot of pressure.”
“Sorry,” Jen responded, “Guess if wanted things to go a certain way I should have been more clear and I guess I didn’t think you would do this for me and Katie unless I included new play things. I didn’t think we may be a lot for you.”
“It’s ok,” I replied, “want to go over your card together and unpause this game.”
“its not like I’m going anywhere,” Jen giggled as she knocked her cuffed hands against her head board.”
I pulled out Jen’s card and started to read through it. She had wanted me to tie her to her bed, well one thing down, tease her with her vibrator for “Jesus Christ Jen,” I yelled, “I’m not going to fuck you, you’re my step sister.”
“uhh we are role playing tonight jackass, Jen replied annoyed. “Your some creep that broke into my house tied me up and now free to have their way with me. No connections tonight, just a random guy his sexy damsel. Come on you’ve never fantasied about what it would be like? I mean you could untie me and I could go get myself stuck in our dryer if that would help.”
“It just feels unnatural,” I tried replying. “I mean I’m supposed to look out for you not bang you.”
“uhhh Jake your impossible,” Jen replied growing more annoyed. You have a hot barely dressed girl tied up in front of you, begging for sex and your stopping cause our parents are already banging. You are going to end up fucking Mary tonight and she’s just going to hold it over me for the rest of my damn life, it will be her trump card forever.”
Jen was clearly dealing with some stuff and was actually starting to tear up. I grabbed a tissue off her night stand and went over to her to dry her tears.
“umm Jen,” I said trying to be comforting, “I don’t actually have to have sex with Mary tonight if its going to hurt you. I just don’t understand you set this all in motion to happen if you didn’t want it to?”
“She had been bragging how she could get anyone she wanted at college, she dated Kent Stevens QB, Prom king in high school, she’s just beaten me so often at so many things, I just wanted a win in my corner,” Jen lamented. “I’m tired of coming in second to her. First thing out of her mouth will be, you lived with him for how long and he wouldn’t fuck you, but hours after meeting me we screwed like rabbits.”
“Sounds like some of the convos I’ve had when Katie is venting about you,” I said trying to change Jen’s perspective.
“God if this is how I make Katie feel, I’m the worst sister ever,” Jen cried.
“You are not the worst sister ever,” I interrupted, “but you have to be your own person and stop comparing and competing so much. I mean there is always going to be someone hotter, smarter, stronger whatever. You just got to be happy with yourself.”
“I’d be a lot happier with myself if you were inside me right now,” Jen giggled. “Let’s make a deal her Jakey, if you can make me cum before I can make you hard I’ll drop the sex request forever. If I can make you hard I get to suck that damn fine dick of yours.”
“So I keep my cool while making you pop and you drop the sexual harassment for good,” I asked.
“Pinky promise,” Jen replied with a smile and holding out her pinky despite her wrists being cuffed above her head.
“Ok deal,” I responded. “I’m going need to change things up, so no resisting or do I need to put you to sleep again.”
“I’ll behave,” Jen replied.
I quickly untied each of Jen’s legs then freed her left hand from the handcuffs so Jen was now free from her bed. I ordered Jen to lay down on her stomach, put her hands behind her back and cross her ankles.
“Oh I see trying to hide my boobs to keep yourself from getting a stiffy,” Jen said mockingly as I re-cuffed her wrists and bound her ankles with rope. I stayed quiet and tried to stay focused on Jen’s ankles. Flipping her onto her stomach had now left her tone and barely covered ass out for me to see instead. I tried to remember some of the things Steve had done to her a few weeks back that got her all worked up. At the time that was happening I was busy trying to block it all out so other than remembering Jen enjoyed being treated like trash it wasn’t a big help.
I finished binding Jen’s ankles and was contemplating my next move when Jen chimed in. “Hey Jakey time to drop those shorts, I don’t want to hear its just a banana in your pocket when make you stand at attention.”
“Hell no,” I replied
“Come on” Jen pouted, “How you going to turn me on without showing me that package of yours.”
“I’ll just call you a bunch a names,” I shot back.
Jen giggled, “you alert the other girls if you start yelling at me, come on show me little Jakey. You know you want to see what I’m hiding underneath as well.”
“Boxers, final offer,” I bluntly responded.
“I’ll take it,” Jen said with a smile.
I dropped my shorts and went over to Jen’s dresser. I felt a little weird grabbing dirty underwear so I grabbed a clean pair and moved back towards Jen.
“You didn’t have to tie me up just to get into my panties,” Jen giggled, “I’ve been willing to let you mmmmfff.”
“Whores don’t talk,” I said after shoving Jen’s panties in her mouth. “whores never spit and always swallow.” I added squeezing her cheek.
Jen’s face became a little flush from the shock and despite her mouth being filled by a pair of her own panties she let out a slight smile of happiness.
“You filthily slut,” I trying say with force but not too much volume, “how dare you dress like this. I did not give you permission and now you must be punished.”
I gave Jen a hard smack on her thong covered ass. The noise was a bit louder than I wanted but the force seemed right. Jen groaned with a mix of pain and pleasure and strained against her bonds.
“Remember to keep those panties in your mouth,” I said before smacking her ass again. “That whore mouth of yours has had too many things in it lately.”
Jen moaned out of pleasure reacting to another spanking from me.
“I’m going to give you a good licking,” I said trying to keep a straight face. I pulled out one of Jen’s whips from the bag and produced to strike Jen repeatedly on her ass and legs. With each strike Jen’s moans seemed to be getting louder so I rather rudely grabbed the back of her head and shoved it into her pillow.
“You are making too much noise slut,” I said still shoving Jen’s face into her pillow in an attempt to quiet her down. I could tell Jen was enjoying herself based on the sounds she was making along with the tugs and pulls she made against her bonds. The problem was I was also enjoying myself and I wasn’t sure how much longer I could keep my solider down. I decided I may have to try and speed Jen along or she would win the bet. I went over to the back pack and dug out a finger vibrator thinking it would do the trick. Stupidly in deciding on the best way to control Jen so she couldn’t move away. I put her in the little spoon position and pushed her ass into my crotch so I could grope her breasts, keep her from moving and hold the finger vibrator in place. What I didn’t plan on was in though Jen was bound and gagged unable to move much of her body, her ass cheeks were not restrained.
As soon as I put the finger vibrator on her pussy her whole body began to pulsate. Some how she used the muscles in her ass cheeks to move those cheeks up and down against my crotch. Stubbornly I let happen, convinced I could get her off before I got hard. I was wrong. Jen’s thong covered ass rubbing and bouncing against my dick was too much and was rock hard and poking Jen’s ass. Jen screamed and giggle into her gag and she knew she had won. I shoved her bound body off me, stood up and stared in disbelief at my bulging boxers. Jen rolled herself over and mmfffed into her pantie gag attempting to tell me to take the gag out of her mouth, which I did.
“I knew I could get you hard,” Jen said triumphantly. “now drop them boxers, I’m hungry for sausage.”
“Don’t you want me to untie you first,” I said trying to delay.
“Nope,’ Jen, “I like the challenge.
I dropped my boxers and laid down, still feeling a little dirty and nervous I begged Jen that her mom and my dad could not find out about this.
“Please,” Jen laughed, “they both think we’ve already banged, they wouldn’t have left us all alone if it bothered them.”
“I’d still prefer they not find out,” I responded.
“Shut up and enjoy the blow job,” Jen replied getting herself in position. “I’m been waiting forever to get a taste, best night ever.”
Jen quickly shoved my whole dick in her mouth and started going to town. Still weirded out that my step sister was doing this I closed my eyes and tried to imagine it was some other girl. Jen was slower and more methodical than Mandy but was defiantly more excited. Jen came up for air a lot and since I wasn’t doing any dirty talk took care of that herself. Calling herself a dirty whore and slut while my dick wasn’t in her mouth. Honestly had her hands not been bound she probably would have been playing with herself while she played with me. Jen repeatedly warned me not to shove her off me and that she wanted me to blow my load down her throat. After all she said to herself, “whores never spit.” Eventually that time came and shot my load and Jen sucked it all down. She continued to suck until I’m pretty sure every last drop of sperm was out of me and I literally had to pull her off of me.
“Jezz Jen enough,” I said prying her mouth off my dick.
“Sorry,” Jen giggle, its just I mean that’s the only time I’m going to do this, I didn’t want it to end. Plus maybe you won’t have anything left for Mary and the other girls.”
I grabbed a towel and gave Jen’s face a quick wipe before drying myself off. I cut Jen loose and gave her a minute to stretch a bit. I cleaned myself up a bit and put my clothes back on.
“So how do you want to be tied now?” I asked Jen.
“Typical guy,” Jen responded, “I give you oral and soon as you finish you take off on me.”
“I still have your sister and three of your friends to capture,” I responded.
“and bang.” Jen added.
“Let’s not get a head of ourselves, lets tie you up so I can get moving.” I said.
“Spread eagle on my bed please.” Jen offered, “and give me the ball bag, I want to pretend I’m still sucking on your dick.”
“Whatever floats your boat,” I replied.
Jen got comfy on her bed and stretched her arms and legs out. I quickly grabbed 4 pieces of rope from the bag and tied each appendage to a part of the bed frame. I then grabbed one of the vibrators that had a remote so Jen could control it herself while I was busy with Katie and her friends. I put the vibrator in a spot she requested they did my best to tape it into place. Jen was once again trusted up pretty tight,
“Wait,” I spoke up before using the ball bag. “What’s your cereal?”
“I’m not telling you till you fuck me,” Jen snarkly replied.
“Jen, I don’t have time for this,” I complained, “Just tell me.”
“Nope,” Jen giggled before clamping her lips shut.
She was trying to delay me from Mary and it was starting to annoy me. Rather than play anymore I covered her mouth with one hand and pinched her nose close with the other. Jen started to struggle as I impacted her air supply but the ropes kept her from stopping me. I eventually let go and after she caught her breath she mumbled “rice crispies.”
“Any last requests,” I asked putting the ball gag close to her mouth.
“Please don’t bang Marmmfff,” I cut Jen off and strapped the ball in place and placed a towel on her chest incase the ball gag caused her to drool. I turned her TV on and put the remote in her other hand. I packed my supply bag back up, stuck Jen’s phone my pocket and prepared to use the back staircase to sneak down to the basement where I would trap Trish and Jess.
I hid near the basement steps and waited for Trish and Jess to make there way down. I had texted them both pretending to be Jen and told them to meet me in the basement so they could plan how to capture Mary and keep me from getting to play with her. I felt a little bad lying but with four girls still on the loose I needed to get them separated so I could catch them without making too much noise. Trish came down first with Jess not far behind. Fortunately they closed the basement door behind them and struggled to find the light which with made it very easier for me to grab them from behind.
I grabbed a rag and quickly pounced on Jess. I used the rag to cover her mouth and whispered into her ear 1,2,3 go to sleep. Jess was stunned but did as she was told and turned into dead weight without alerting Trish that I was down here. I quietly lowered her to the floor and left her there and went after Trish. I snuck up behind her and covered her mouth with my hand and stuck the toy gun into her back.
“Not a sound sweetie,” I announced to the surprised Trish. “Your little friend is already out cold so don’t do anything stupid or she will suffer.”
Trish nodded her head and let me guide her over to where I left Jess.
“On your knees and put your hands on your head,” I ordered Trish. She complied and sat on her bare feet and put her hands on her head. I flipped on the light so I could see the girls better. As I put the toy gun in my pocket Trish started blabbing.
“My cereal is golden grahams and Jess’s in fruity pebbles,” Trish spat out.
“Trish what the hell?” Jess said annoyed.
“Your supposed be unconscious,” I told Jess trying not to laugh.
“Sorry,” Jess replied.
“I don’t want to be tortured,” Trish whined, “wait where’s Jen she told us to meet us down here?”
“I’m afraid your little friend is a bit tied up at the moment,” I cracked, “but don’t worry I’ll check on her after I have fun with you little cuties.”
“Please don’t hurt us, just take what you want,” Trish cried out, playing the damsel in distress well.
“You girls are what I want,” I said laughing. “Now be a good girl and tie up your little friend. Don’t want her to interrupt while we play.”
“I’m not good with knots,” Trish replied making excuses.
“Luckily duct tape doesn’t requiring a merit badge,” I told Trish as I tossed a roll of duct tape at her. “Go on, get to taping.”
Trish picked up the duct tape and crawled over towards Jess, still barefoot, clad in her boy shorts and sports bra. Trish gently pulled Jess’s hands behind her back and wrapped the tape around her wrists. Trish then crossed Jess’s ankles and wrapped the duct tape multiple times around them before ripping the roll loose.
“Good girl,” I told Trish, “Now lay down, put your hands behind your back and cross your ankles.”
Trish laid down as instructed and I quickly bound her with duct tape. I wanted her off her stomach in short order so I could get a look and start playing with her big tits, compared to Jess she wasn’t showing much skin with her baggy pj pants hiding her legs and leaving only the soles of her bare feet exposed.
“You’ve tied us up, please just leave us alone,” Trish began pleading. “What do you want from us.”
“We are just going to play some games together,” I said smiling back at her. “Now lets get you off this dirty floor and put you some place more comfortable.”
Trish meekly attempted to try and crawl away from me, but with her hands and feet bound with duct tape she didn’t have much success. I got behind her and then pulled her to her feet. Despite her verbal protests I could tell she was quite enjoying my physical touch as her face once again began to turn varying shades of red. I then went to pick her up and throw her over my shoulder. It was a bit tricky as she is a good foot shorter than me. Eventually I got her over my shoulder and started walking around the basement debating the best place to put her down. Trish had put down on her card that she wanted to be carried around by me. I’m guessing being a bigger girl it had been while since someone had carried and tossed her around like this. It also gave me an excuse to have my hands on her big ass and give her cheeks a few good squeezes. Trish did offer some token resistance trying to get loose from my grasp but was probably worried I was going to drop her. So instead she just continued to talk and demand to be put down, which I eventually did by tossing her onto one of the couches.
“Let me go” Trish demanded, “I don’t have any money just leave before the cops come and arrest you.”
“You know sweetie I think I’ve had enough of you mouth,” I told Trish. “Time to shut you up and play with your little friend.”
I grabbed the roll of duct tape and pulled a pair of socks I stole from Jen from my pocket.
“Open up and say ahh,” I said trying not to laugh.”
Trish kept her lips seal and refused to open her mouth up.
“I don’t understand why your being so difficult,” I told Trish as I grabbed her nose and squeezed it closed. Eventually Trish had to open her mouth and I quickly shoved Jen’s sock in there and slapping two pieces of tape over her mouth for good measure.
“Now you be a good girl while I play with your friend for a bit,” I told Trish while giving her left breast a good squeeze. “Don’t feel left out sweetie I’ll be back to play you soon,” making sure to Trish’s other breast a good squeeze as well. Trish let out a moan of pleasure which let me know she was enjoying herself.
I went over to Jess and double checked her card. Jess didn’t want me using and toys or doing anything real dirty. Instead she wanted me to get a little physical, hair pulling, spanking among some other things. To make sure I didn’t cross any lines I got down on the floor next to the bound and still pretending to be sleeping jess and whispered in her ear, “if I get too rough for you say cherry or snap your fingers twice and I’ll stop.”
“I don’t think you’ll be too rough,” Jess whispered back, “but thank you.”
She closed her eyes and went back to pretending she was out cold.
Well here goes nothing I thought, I grabbed Jess by her hair and pulled her face off the carpet. “Wake up my dear,” I said trying to sound menacing, “Its time for you to join the fun I’m going to have with your friend.
Surprisingly Jess didn’t cry out in any pain when I pulled her hair, the only noise was the muffled cries of the bound and gagged Trish still laying on the couch watching me.
“you know there are easier ways to get a girls attention,” Jess responded, “can’t get a girl to touch you so you to resort to tying them up huh.”
Jess was having fun pushing back but I needed to remind her who was boss.
“You know dear it was an attitude like that caused your friend over there to lose her speaking privileges,” I told Jess while pulling tighter on her hair and turn her to face Trish who was mmfffing into her tape gag.
“Oh so Mr. big strong man can’t handle a little lip,” Jess quipped, “untie me and fight me like a real man or you too big a mmmfff. I decided I had enough of Jess’s comments and stuck the toy gun in her mouth.
“Now dear that’s enough,” I said keeping the gun in her mouth, “Looks like I need to beat that fight out of you and turn you into a good little submissive. Not another word or you’ll be sucking on some lead. Understand sweetie?”
Jess nodded her head yes and I pulled Jen’s other sock from my pocked and jammed it in Jess’s mouth. I added two pieces of duct tape to shut her up for good.
“Now ladies,” I said pulling Jess to her still bound feet, “we are going to play a fun little game together.”
I guided Jess over to the couch where Trish had managed to maneuver herself into a normal sitting position. I grabbed the paddle that Jess had requested be used on her then stood there for a bit to try and figure how to position myself and the girls so I would be able to smack Jess’s ass and grab Trish’s breasts from the same spot. I decided I would sit with Trish on my left and lay Jess down on her stomach with her face and mid section on the couch, her butt in my lap and her bound legs on Trish. After a a little maneuvering I got both girls where I wanted, Jess’s butt right in front of me and Trish’s nice big tits to my left.
“Ok ladies time to play our game,” I told my bound and gagged victims. “I’m going to give you a good smack on the ass, if you make any noise I’m going to help myself to a nice feel of your friends breasts.”
The girls both mmmffed in protest under their gags.
“Now now I didn’t even have to smack you to and you are chatting up a storm.” I laughed. “Sorry your friend must want you to get felt up sweetie.”
I grabbed a good hold of one of Trish’s boobs and she let out of soft moan of pleasure and her face started to turn red. I followed this up by smacking Jess’s ass with the paddle. Jess let out an “oh fuck” under her gag and I could tell she enjoyed it. I took turns smacking Jess and groping Trish. Both girls continued to moan with pleasure with each smack and squeeze and despite Jen seemingly sucking my dick dry I was getting turned on again. After spending a few minutes giving both girls attention I decided it was time to just focus on one of them at a time.
I pulled Jess back to her feet and ordered her to start hopping over to the other couch. Despite her ankles being bound Jess was able to keep her balance and get herself close to the couch. Jess had requested I be a little rough with her so rather than gently place her on the other couch, I smacked her in the ass and grabbed a hold of her hair and pulled her down so she landed on her back. I then got on top of her and loosely put my left hand on her throat and put my face inches away from hers.
“It’s time for you and I to have a little one on one fun,” I said to her very sternly. “If you resists me it will end badly for you and your friend over there. Do you understand.”
Jess nodded her head yes and I responded with a “good girl.” I then licked the side of her face to up the creep factor. While Jess had listed no toys, removing clothes or penetration on her card she didn’t have any no touch zones. I was getting turned from spanking her ass and even though they were smaller than Trishs tits, it was time to play with Jess’s chest. I continued to pull on Jess’s hair with one hand and began squeezing her boobs with the other. Jess moaned with pleasure into her gag as I continued to grope her chests, the harder I pushed and pulled on her chest the louder her moans got. I was getting more and more turned on and moved my hand down her inner thigh and squeeze my one hand up and down her legs while the other hand continued to play with her tits.
As Jess continued to moan and twitch with pleasure I continued to get bolder with my hand placement. I moved my hand onto her crotch and despite the layer of clothing I could feel that her panties under neath were starting to get wet. I continued to keep one hand working her tits and the other her crotch. Jess’s breathing into her gag was becoming more rapid and I could tell she was getting close. I got off the couch quickly flipped her onto her stomach and gave her one last hard smack on the ass. Jess let out an “oh fuck yes” under gag then arched her back before collapsing onto the couch. Hearing Jess moan and getting to feel her up had made me rock hard again. If I was going to be showing these girls my dick, displaying it when it was rock hard would give them the best show. I dropped my shorts and let my dick come out. I walked over to Jess and stuck my rock hard dick right in her face. Jess let out a soft moan as she got an up close view. I stroked her hair a bit and said, “You did quite well turning me on, lets see if your friend can finish the job.” I gave Jess’s bare feet a little tickle and walked back over towards a very excited Trish.
I couldn’t quite make out what Trish was trying to say behind her gag but it likely was, “me next, me next.” I walked over to her in my boxers with my erect dick still out and at attention. Despite being bound and gagged Trish was no longer playing a stubborn and scared damsel. Her eyes were locked on my dick and her duct tape gag was likely keeping her tongue from hanging out of her mouth. It was funny up until a few weeks ago before the show I put on for Jen, Katie and Mandy the only time I dared to pull out my dick for someone to was to get a blow job or have sex but now that shyness had gone away and I was getting a thrill out of the attention.
“Like what you see sweetie,” I said as I as shoved my dick in Trish’s face. I brought it so close to her face I could have bopped her on the nose with it. Trish’s face had now turned bright red but she didn’t care, and not like she could really go anywhere. I really wanted to keep playing with her big tits so I shoved her down on the couch and straddled her while laying my dick right on her chest. I grabbed both of her breasts and pushed them against my dick and for all intents and purposes began to fuck and grope her breasts. Trish’s face continued to look red and flush and pleasure from me using her tits caused her to move her head enough that my dick would occasionally clock her in the chin and face. After a bit of that I got bored with the position and decided to try something else.
I pulled Trish to her feet and let her know I wanted her to play with herself while I played with her tits. I told her I would cut her hands free but she was only to touch herself and not anything else. Trish smiled and moaned in agreement. I cut the duct tape from her wrists and she immediately stuck one of her hands down her pj pants and went to work on herself. I pulled her down so she was sitting in my lap. She bounced her big ass up and down rubbing it against my dick while I wrapped my arms around her waist and continued to play with her tits. Trish definitely had experience playing with herself and very quickly was causing her body to shake and her moans of pleasure became louder and louder under her gag. After a few minutes of working on herself she let out an “oh yes” from under her gag and collapsed back on me. I pushed her back onto the couch and rebound her hands with duct tape. I put my shorts back on and walked back over to Jess to tickle her feet again for a bit. Jess wasn’t lying about her feet being sensitive as she thrashed around and laughed into her gag, with what energy she had left. I turned the basement tv on for the girls and told them that I hoped they had fun, but now I needed to go play with their friends but I would be back later to untie them. Both girls moaned into their gags but it was time for me to get ready to play with Mary.
End part 1
It will likely be a bit till the next update but hope you enjoy.
It had been two weeks since I (21M) had a crazy night with my two step sisters Jen (19, blonde 5ft 5inch, tan, athletic-fit build, B sized breasts) and Katie (19,burnette, 5ft 4inch, little more curves then Jen, C sized breasts) and my friends with benefits girl Mandy (21, 5ft, slim build, tan, B sized breasts). What had started with a simple car ride had led to me eventually tying up all three, using sex toys on Jen, sucking whip cream off Katie’s toes and banging the hell out of Mandy. It was quite a night, but now two weeks later and my dad and step mom headed out for another weekend away, my step sisters had some more fun in mind.
“Oh my god I can’t believe the night we are going to have,” Jen squealed. Jen was wearing black bootie shorts and a white tank top. Our friends have been so jealous hearing about all the fun we had with you Jakey.”
“I’m pretty sure they don’t believe us still,” Katie added. She was wearing black bootie shorts and blue t shirt. “I can’t wait for them to experience some of the fun we had.”
“What exactly do you all have planned?” I asked, “and who is to say I agreed to anything, maybe I’ll just head out for the night.”
“No Jake please you have to stay and play,” Jen begged.
“Yea Jake, Jen’s been bragging to Mary, Jess and Trish since our night of fun.” Katie said, “If you bail now it will make us look so bad. Plus our night really gave me a boost and I want our friends to get that same experience.”
“Fine,” I relented “I’ll stay and play.”
Jen and Katie let out yell of joy and started skipping around the living room.
“So who all is coming to this and what exactly do you all have planned?”
“Well,” Jen started, “our friends Trish, Jess and Mary I’m pretty sure you’ve met them before, they all remember you. I played field hockey with Jess in High School and Trish was in the band with Katie. There both like five foot one with black hair. Jess has pretty athletic build but she has a bigger butt that me. Trish has a bit more curves then Katie or me but also has the biggest tits of our group. Mary well…”
“Mary is Jen’s frenemy,” giggled Katie.
“She’s still bitter I beat her for Prom Queen in high school,” Jen explained, “but she’ll probably try to fuck you just because you’re my step brother.”
‘If you don’t like her why did you invite her?” I asked.
“Of our friends she is the biggest none this happened slash you two are liars trash talker” Jen explained. “I want to show her what fun we had even if that means you show her your little solider.”
“Oh so your saying I could hook up with one of your friends tonight?” I asked intrigued.
“Probably more than one,” Jen replied. “They are all horny little things. Mary definitely, Jess thinks your cute, Trish has a crush on you. I mean I’m surprised you didn’t notice we had to practically pick Trish’s jaw off the floor the last time she was over. You had just finished mowing the lawn and came in the house without your shirt on. I’m pretty sure her tongue was on the floor while you grabbed a drink. Besides our friends, you know I’m always willing,” Jen paused and came towards me and brushed her hand across my crotch. “In fact the only one who probably isn’t horny is little miss Katie thanks her date last weekend.”
“I must not have noticed,” I replied.
“Jen its not nice to spill Trish’s secret,” Katie added.
“Its not a secret and Jake would have figured it out it two seconds tonight anyways.” Jen replied.
“You had a date,” I replied excited for Katie and trying to change the subject.
“It was a bust,” Katie responded defeated. “He said feet were gross,” Katie added looking down at her bare feet with her red painted toe nails. “Even though I got a pedicure and wore Jen’s cute sandals.”
“You stole my sandals,” Jen replied.
“I borrowed them,” Katie replied, “besides you have so many you didn’t even notice.”
“I’m sorry he wasn’t what you looking for Katie,” I said. “But hey way to put yourself out there and go after something.”
“Thanks,” Katie replied sheepishly, “Thanks to our little fun I have some boxes to check now,” Katie said laughing.
“I’m sorry he didn’t like your feet Katie,” Jen said with a smile, “Come over here and I’ll give your feet some attention.”
Jen moved towards her sister and Katie realizing what Jen was planning took off towards the other side of the kitchen table.
“Jen I’m sorry I didn’t ask to borrow your sandals,” Katie said trying to keep away from her sister.
“Too late,” Jen replied.
Katie took off, with a barefooted Jen close on her tail. Jen was faster that Katie, her teal painted toes quickly caught Katie and tackled her onto the sectional. Jen they grabbed Katie’s ankles and began raking her figure nails across Katie’s bare soles. Katie struggled, kicked and slapped at her sister trying to get free. Jen showed no mercy, keeping a tight grip on Katie’s ankles, Jen continued to move her fingers up and down Katie’s exposed soles. Katie was completely helpless and Jen’s constant tickling was sucking whatever fight she had left in her. Despite Katie’s constant screams to stop and let go, Jen continued to work on Katie’s feet. Running her fingers across the top of Katie’s feet and even mockingly playing this little piggy with Katie’s red painted toes. Eventually Jen relented and Katie collapsed face first into the sectional.
“Now that your done torturing Katie can you tell me what exactly you have planned for this evening?” I asked Jen.
“We need to wait for the rest of the girls to come,” Jen explained. “All you need to know is, you are playing a creep who breaks into the house while 5 sexy girls are having a sleep over. I’ll explain the rest when the girls join us.”
“I don’t know,” I responded “Five girls seem like a lot to handle on my own, sure I can’t have some help. I’m sure Steve would be free to help me out.”
“Uhhh no,” Jen replied disgusted, “Give a guy one BJ and he blows up your socials and won’t leave you alone. Besides Mary would eat him alive, while Jess and Trish think he’s creepy. It wouldn’t work if he was a part of this. It has to be just you, you’re the right mix of safe and sexy the girls want.”
“Alright,” I relented.
“Good,” Jen replied, “the queen has spoken, so its been said so its been done.”
“Queen of what?” Katie yelled to her sister, “Queen of Steve’s spank bank.” Katie tossed a pillow at her sister, still annoyed about her tickling attack. “But getting back to the topic at hand Jake, I won’t resist if you decide to place your hands on me tonight,” she added with a giggle.
“Really,” I replied with the grin as I made my way over to wards Katie. “Maybe we can test that right now. I quickly made my way towards Katie who was still sitting on the sectional.”
“Wait Jake what are doing no don’t,” Katie yelled but it was too late. I pounced on her and used my right hand to put her wrists together and pull her arms above her head. With my left hand I pulled her shirt up a bit to expose her stomach.
“No resisting Katie,” I said laughing as a I ran my fingers up and down her exposed stomach. Katie once again howled in a mixture of pain and pleasure begging me to stop. She struggled a little but as strong as I was there was little she could do.
“Oh look at this, time for round two,” Jen said as she came back to her sister and started tickling her feet again.
“Stop please, you are going to make me pee,” Katie begged as I continued to tickle her stomach and Jen tickled her feet. After a minute Jen stopped.
“I have an idea,” Jen said. “Jake, don’t let her go I’ll be right back.” Jen spirted up the steps towards her bedroom.
“Please let me go,” Katie begged, “I’m sorry I can’t take anymore.”
“Let’s see where Jen is going with this,” I replied.
Jen quickly returned bouncing down the steps. Hiding something behind her back.
“I was going to save this for tonight,” Jen said, “But I think Katie can help us test it out first.”
Jen revealed she was holding an electric toothbrush and it was pretty obvious what was coming. Katie made one last plea to be released but it fell on deaf ears.
“Shut her up Jakey, we don’t want to wake the neighbors,” Jen said as she turned on her weapon of torture. I placed my free hand over Katie’s mouth and she began mmmfffing like crazy into my hand. Jen placed the now running electric toothbrush on Katie’s bare soles. After attacking the bottoms of poor helpless Katie’s feet, Jen next moved the toothbrush to the tops of Katie’s feet. Katie continued to try and wiggle free and screamed loudly into my hand but my hand gag did a pretty good job keeping her quiet. Jen decided one last area needed attention and began under and in between poor Katie’s toes. As Jen moved the toothbrush across all ten of Katie’s toes, the noise Katie began making under my gag switched from pain to pleasure. With her face starting to turn redder, Katie closed her eyes and began thrusting her hips while continuing a very now sensual moan under the gag. Jen’s work with the toothbrush suddenly caused Katie’s body to tense up before Katie let out an “Oh Fuck,” stopping her resistance against me and collapsed back into the sectional. I pulled my hand from her mouth and let go of her wrists as Katie took recovery breaths and melted deeper into the sectional.
“Fuck, I’m wet you assholes,” Katie let out.
“Piss or pleasure’” Jen replied laughing at her sister.
“Screw you,” Katie replied before getting to her feet. “Now I have to shower before the girls get here.”
Katie headed up the steps too embarrassed to look back at us.
“So now can you tell what all is in store for tonight?” I asked Jen.
“Keep your shirt on boy,” Jen replied we need all the girls here so I only have to explain this once.
“ok,” I responded annoyed. I turned the tv on and relaxed on the sectional while Jen went upstairs to organize the “toys” for tonight. Katie finished her shower and came down stairs in sweats and a t shirt. Just as Katie sat down the door bell rang.
“They’re here,” Katie yelled upstairs to Jen and went to answer the door.
Katie skipped over to the door and opened it. Their friends Jess and Trish walked in. Jess was short about 5ft 1inches with dirty blonde hair. She had an athletic build similar to Jen but with a bit of a bigger ass. Her face wasn’t as pretty as Jen’s but she was cute. She was wearing tan kapri pants with a blue crop top and hey dude shoes which she quickly slipped off showing her tiny feet with pink painted toe nails. She opened her mouth to say hi but was loudly interrupted by Trish who screamed, “Oh fuck he’s really here,” while trying to hide behind her friend.
Trish was also short, maybe five feet tall with dark brown hair. She was dressed in PJ pants, oversized T-shirt and black flip flops.. She had a lot more curves than my step sisters and Jess, and even with the baggy t-shirt I could see she had a very big DD pair of breast underneath.
“Trish, what are you doing, get off of me.” Jess yelled at her friend.
“Jen said dress causal and it was just going to be girl fun, why did no one tell me he’d be here too. I look like crap.” Trish said before running upstairs, losing her flip flops in the process.
“Trish wait up,” Jess said chasing after her friend. Jen passed them coming down the stairs.
“You should have told Trish that Jake was part of the fun,” Katie said towards her sister.
“Please,” Jen huffed, “She would have bailed if I said Jake would be here. She’ll get over her little crush and be fine in a bit.”
“I guess your right,” Katie replied, “Still a little mean.”
Just as Katie was about to close the door their stunning friend Mary walked in. She truly was like a real life Stacy Keibler. She was a tall blonde, probably 5ft 10inches tall but she was wearing what looked like 3 inch black heels that made her almost as tall as me. She was dressed like a sexy secretary, in a short black skirt, tan pantyhose that really made her long legs pop and tight white blouse that seemed to be struggling to contain her perky size C breasts.
“Hey sexy, I’m Mary, nice to meet your,” Mary said giving me a wink.
“I’m Jake uhh, Katie and Jen’s step brother,” I managed to stammer out.
“Of course you are,” Mary said with a laugh, “I’m looking forward to spending some time together tonight and maybe you can show me that sweet package I’ve heard so much about.”
I stood their trying to respond while also keeping my jaw from hitting the floor, lucky Jen was there to break the tension.
“Mary, what the fuck I said dress casual,” Jen hissed.
“I brought a bag,” Mary replied, “My dad needed help at the dealership today and made me dress all professional.”
The break allowed me time to mutter that I need to go pick up food and stammered out the door. I made It to my car and took a deep breathe to compose myself before starting my car and heading to the pizza shop. After seeing Mary I didn’t care what my step sisters had planned I was in. I didn’t care if Mary was only flirting with me to piss off Jen, I was ok being used. As I pulled in to the pizza shop I got a text from Mandy asking what my plans were and if I wanted to hang out tonight. I texted her back letting her know I was helping my step sisters and friends at my parents and wouldn’t be free. I picked up the pizza, salad and drinks and headed back home.
I walked back into the house loudly announced to the girls that food was here and expected them to coming running and to give me more attention. Instead I was met with silence, confused I yelled food again and walked into the house. All the girls minus Jen were sitting at the dining room table either writing on or looking at an index card.
“umm, what gives?,” I asked Jen in the kitchen while putting the food on the counter.
“Ok so the scenario tonight is us girls are having a sleep over and you’re the creep next door that breaks in and takes advantage of us so to speak,” Jen started explaining. “You got me to thinking about trying to handle the needs-wants of five different girls plus your and everyone’s comfort level with all the different options that the girls may want to experience. That’s a lot to process, let alone communicate if the girls have gags in their mouth. So I’m having the girls write down their limits-wishing on these cards I made.”
“Oh so I’ll have a little consent cheat sheet for each girl,” I replied.
“A bit more than that,” Jen explained. “So on each card will have the minimum amount of clothes that must be on at all times, toys they are open to using, a body part they want you to focus on and one must fantasy they want to experience with you.”
“The girls realize I have my own limits right,” I asked.
“I told them they can put things down but you have to be ok too, consent goes two ways,” Jen responded. “But I mean if you can handle sucking sugar off Katie’s toes you should be able to handle whatever these girls want.”
“You sure,” I said sneaking a peak at Mary who had by now had ditched her heels and was sitting the dining room table with just pantyhose covering her feet.
“You’ll be fine,” Jen responded, “Girls come grab some food.”
The girls all came to the kitchen to grab dinner while I stood away from the food letting them all have first dibs. Trish saw me and started to blush but was at least able to be in the same room as me. Jen, Katie and Jess all grabbed food and each gave me a smile then headed back to sit in the dining room. As they exited the kitchen, Mary came into the room in all her sexy glory.
“Hi Jake,” Mary said politely, “Glad you made it back, I’m looking forward to getting close to you tonight.” Before I could respond she brushed her hand against my junk then spun herself around her ass was pressed very firmly against my crotch. I took a breath to try keep from getting hard.
“I’m looking forward to getting close to you as well,” I managed to respond. “What kind of pizza do you like, I got a few different kinds.”
“Sausage,” She replied. Mary kept her ass pressed against my crotch but turned her neck so I could see her face. “I love getting a good sausage in my mouth, the bigger the better.”
Thankfully she went over and grabbed a slice before feeling how hard she had just made my dick. She headed back to the table and got myself some food and sat down with the girls for dinner. I sat down next to Katie with Mary sitting across from me. I tried to focus on my food while the girls chatted about work, boys, college, honestly I wasn’t really paying attention. Every so often I would glace over at Jess and Trish who smile and blush at me, while anytime I looked in Mary’s direction she would wink at me and lick her lips. As everyone was finishing up Jen took the floor and snapped me back into focus.
“Ok girls,” Jen announced loudly. “Here is the plan for tonight. The five of us beautiful ladies are having a fun little sleep over, but the creep next door played by Jake, breaks in and takes us captive. Then depending on what you ladies put on your cards and what all Jake is comfortable with, he’ll have some fun with you. Oh and one other thing, write down your favorite breakfast cereal on the back of the card then cover it with a piece of tape.”
The rest of the girls and myself were a bit confused?
“What does cereal have to do with this?,” Jess asked.
“That ladies is the code word that Jakey here will need to get out you either via pain or pleasure. We all put in $20 bucks in and whoever can keep the word safe gets to split the pot. But no giving him a fake cereal, do that you are disqualified.”
“How will you get the word out of us Jake,” Trish asked me.
“Umm I don’t know I mean I probably could just tickle it out of you all or something,” I responded.
“Well I’m toast,” Jess laughed, “My feet are really ticklish.”
“I can think of some better to do with feet then tickle them,” Mary said while locking eyes with me. While continuing her conversation Mary stretched her leg under the table so her pantyhose covered foot landed right on my crotch.
“I’m more of fan of foot rubs,” Mary added with a smile. “Just having something going up and down on a sensitive area, just feels so good.”
“Yep,” I responded trying to keep my cool and avoid drawing attention to what Mary was doing under the table.
“Girls, girls,” Jen yelled, thankfully taking the focus of the group. “enough about feet jeez, the quicker we finishing eating the quicker we can get to the fun.”
Mary pulled her foot off my crotch and gave me a wink, she could tell that little move had gotten me hard. I took a big gulp from my drink trying to keep my cool. I hoped none of the girls looked under the table to see me sporting wood like a kid in middle school. The girls changed topics talking about some Bravo reality or something I wasn’t paying attention and tried to keep my cool. Eventually I calmed down enough that I could get up from the table and offered to help clean up. The girls handed Jen their cards while I was in the kitchen and then passed me on their way upstairs. Jess and Trish just smiled and giggled when they passed me but Mary made sure to drop something near me in the kitchen. She bent over right in front of me to pick it up, sticking her ass in the air. God her ass looked so good if we were alone I probably would have jumped her right there in the kitchen but with other eyes around I kept my focus on washing plates and glasses instead. Mary and Katie headed upstairs while Jen brought over the last of the dishes for me to wash.
“You leave the cards on the table for me,” I asked.
“Is Jakey a little horny from our dinner conversation,” Jen laughed. “You have to wait no peaking just yet.”
Jen headed up with the rest of the girls to get ready, while I finished cleaning. The girls took their time getting ready so I sat down in the living room waiting for them to return. I debated what order I should try and capture the girls. Should I be selfish and grab Mary first, though the rest of the girls may get bored waiting. I could grab Jen and Katie first since I would likely know what they want and could move through it quickly. Hopefully Trish wants me to play we her big tits. Eventually after some debate I decide I would grab Jen first. I could stash her in her room and use her phone to lure the rest of the girls to different parts of the house and capture them.
“Oh Jakey,” Jen called from upstairs, “your victims are ready.
The girls started to make their way down one by one. Trish came down first, she was still wearing the long pj pants but had put on a tighter t shirt that made her big tits pop. She also had done her hair and make up as well. Katie came down next wearing tight blue bicycle shorts and tight blue tank top. She had put her hair in a nice pony tail and had added some teal eye liner making her pretty eyes pop. Jess followed Katie, donning red pair of boy shorts and black sports bra. She curled her hair a bit and added make up to her face as well. The girls were cute but I was waiting the stars of the night Jen and Mary to come down.
Mary sauntered slowly down the steps. She had taken her pantyhose off and put a touch of glitter on her sexy legs. She was wearing much less than the other girls with only a tiny black thong covering her lower half and just a leopard printed strapless bra covering her breasts. It took all my strength to keep my jaw from hitting the floor as she did a little twirl to show me her mostly bare backside.
Jen sensing the hold Mary had on my eyes quicker followed. She was wearing a sexy pink lingerie top and tiny white thong. She gave Mary a passive aggressive hip check to move her out of the way. Jen was also carrying a book bag for some reason but eyes mostly focus on the five pretty barefooted girls in front of me.
“like what you see there,” Katie giggled breaking the silence.
“Very much so,” I managed to spill out, “You all look gorgeous.”
“Thank you,” Trish responded blushing a bit “Its hard to look sexy next to girls only wearing dental floss.
“You could pull off dental floss too if you weren’t so shy,” Mary responded.
“No thanks,” Trish replied, “I like having pockets,” as she pulled her phone out of her PJ pants pocket.
“Do I want to know where the rest of you are hiding your phones,” I said laughing but also trying to confirm the girls had them on their person as I would need them later to help capture them.
Katie and Jess giggled and pulled their phones from their bras while Jen gave me an eye roll.
“I’m not sure what you’ve been focusing on Jakey but it clearly wasn’t Mary and my hands,” Jen said mockingly. Both girls were clearly still holding their phones in their hands.
“Ugh can I get your all cards now,” I said trying to hide the fact that I was being a bit of a perv.
“One second,” Jen replied. “I need to explain a few more things for everyone. In this bag is every toy the girls have requested you use, along with rope, tape and gags, but if you have other restraints in mind feel free to add them to the bag. Also to make it easier you have three tools to help you capture us.”
Jen unzipped on of the pockets in the bookbag and pulled out two wash cloths and a toy gun.
“Umm a toy gun and some dish rags,” I asked confused.
“God Jake have you zero imagination,” Jen complained. “The toy gun is your scary weapon to threaten us with to make us do what you want and the wash cloths are dossed in chloroform so you can knock us out if you need to.”
“You know chloroform is just a fake thing from the movies right,” I ask confused.
“God dumbass,” Jen yelled, “We are playing a game like it’s a movie. I don’t want you to really knock any of us out with a blow to the head. Just cover our mouths with the wash cloth and say one, two, three go to sleep. Whoever you have will pass out and become dead weight.”
“You girls are all ok with me over powering you like that?” I asked.
“I think everyone is looking forward to being held in your strong arms,” Katie said drawing a blush of red to appear on Trish’s face.
I grabbed the gun and wash cloths and stuck it in my pockets. While Jen pulled out an envelope with the girls cards on it.
“There you go Jakey,” Jen said with a smile, “Happy hunting tonight.
“Uh anything else I should know or you want to tell me before I go hide?” I asked.
“Don’t be scared to be a little rough with us,” Jess said trying to hide the redness in her face. “Just cause the kidnapper is cute doesn’t mean I’m not gunna fight back.”
“Not me,” giggled Trish, “I won’t be fighting anyone, in fact,” Trish ran grabbed one of the wash cloths from my pocket and pulled it to her mouth.
“Oh no chloroform,” Trish yelled, “I’ll be knocked out and be at the kidnappers mercy.” Trish covered her mouth with the wash cloth and mmmffff into before dramatically falling to the ground. “Oh no I’m out cold and my friends can’t save me from the sexy kidnapper, in fact they are all running out of the house to leave me alone with him.”
The ladies began laughing at Trish’s bold play. I walked over to Trish picked the rag back up before heading outside to my car. I figured if the girls really wanted me to be a creep that would break in and kidnap a bunch of girls, that kind of guy would sit in his car and stare at them from outside. The girls weren’t letting the fact that I had left ruin their fun as they were busy dancing and filming each other. I watched for a few then got out of the car and made my move.
My parents house had a basement entrance to the house, that fortunately also had a set of stairs that went up the backside of the house to the main level and upstairs. It would be a big help allowing me to sneak around the house and grab the girls when they weren’t expecting it. I snuck upstairs and hid in my room and pulled out the cards to see what all the girls were willing to let me do to them.
Trish’s was pretty tame, she wanted me to throw her over my shoulder, fondle her tits (big smile from me seeing that down) and make out with her. Jess wanted me to pull her hair and spank her butt (thus her don’t be scared to be rough with her comment), Katie of course wanted me to play with her feet. Mary and Jen well I’ll just keep those wishes to myself a bit longer. I grabbed what I needed to use on Jen and snuck into her and Katie’s room. From there I sent her a text, “Come to your room, I need your help to get the other girls out of the way so we can have our fun.” I stroked Jen’s ego just enough that she wouldn’t suspect the ambush I had waiting for her.
I hid behind her door and waited with my rag to “put her to sleep.” Despite the floors being carpet and Jen being barefoot I could easily hear her dashing up the stairs. She opened the door and came in.
“ok Jake whats the mmmffff,” Jen got only a few words out before I pounced. Covering her mouth with the dish rag while pinning her arms to her side with my other arm.
“Your step brother can no longer keep us apart beautiful,” I tried say with in the creepiest voice I could think of,” “Now just take in the rag and count with me, 1, 2, 3 go to sleep.”
Jen let out a muffled motherfucker before dropping her phone and going limp. I easily scooped her up and placed her on the bed. She looked damn good dressed in her skimpy little outfit but I kept my cool. I grabbed Jen’s limp arms and a pair of fuzzy hand cuffs and cuffed her wrists to her headboard. I gently spread Jen’s legs and began tying each leg with rope and tied them off to her footboard, leaving her tied up and looking like an upside down Y.
Now that she was fully bound, I got close to her and gently caressed her face with my hand before telling to wake up. “Rise and shine my little princess it is time for our fun,” I said to her.
Jen opened her eyes and immediately shot daggers at me. “Pause,” Jen let out in a very annoyed tone.
“Pause?” I asked confused.
“Pause, as in Jen and Jake need to have a convo and pause this role play for a minute,” Jen responded.
“Um ok,” I replied.
“What the Fuck,” Jen started to yell, “Why the hell did you grab me first I swear I will kick your mmmfff,” I quickly covered Jen’s mouth with my hand as I didn’t want her to alert the remaining girls.
“Hold on there, you need to calm down,” I ordered Jen, still holding a tight grip on her mouth, “or I’ll gag you and leave you here without any toys while I play with your friends. You want to try this pause again?”
Jen shook her head yes and I took my hand off her mouth.
“Why did you grab me first?,” Jen moaned while pulling against her handcuffs. “You were supposed to save the best for last.”
“Sorry,” I replied, “I needed this to help grab your friends,” I said holding up Jen’s phone. “I thought you would be honored, getting picked first is usually a good.”
“This isn’t a popularity contest,” Jen said as she tugged against the ropes binding her legs. “I saw you at dinner and I know what Mary put on her card. Your just going to do the bare minimum to the rest of us so you can rush to bang her.”
“I haven’t looked at anyone’s card yet,” I replied “I grabbed you first so I can use your phone to trick the other girls to split themselves up so I can stay in control. You and Katie were handful last time, adding three other girls it’s a lot of pressure.”
“Sorry,” Jen responded, “Guess if wanted things to go a certain way I should have been more clear and I guess I didn’t think you would do this for me and Katie unless I included new play things. I didn’t think we may be a lot for you.”
“It’s ok,” I replied, “want to go over your card together and unpause this game.”
“its not like I’m going anywhere,” Jen giggled as she knocked her cuffed hands against her head board.”
I pulled out Jen’s card and started to read through it. She had wanted me to tie her to her bed, well one thing down, tease her with her vibrator for “Jesus Christ Jen,” I yelled, “I’m not going to fuck you, you’re my step sister.”
“uhh we are role playing tonight jackass, Jen replied annoyed. “Your some creep that broke into my house tied me up and now free to have their way with me. No connections tonight, just a random guy his sexy damsel. Come on you’ve never fantasied about what it would be like? I mean you could untie me and I could go get myself stuck in our dryer if that would help.”
“It just feels unnatural,” I tried replying. “I mean I’m supposed to look out for you not bang you.”
“uhhh Jake your impossible,” Jen replied growing more annoyed. You have a hot barely dressed girl tied up in front of you, begging for sex and your stopping cause our parents are already banging. You are going to end up fucking Mary tonight and she’s just going to hold it over me for the rest of my damn life, it will be her trump card forever.”
Jen was clearly dealing with some stuff and was actually starting to tear up. I grabbed a tissue off her night stand and went over to her to dry her tears.
“umm Jen,” I said trying to be comforting, “I don’t actually have to have sex with Mary tonight if its going to hurt you. I just don’t understand you set this all in motion to happen if you didn’t want it to?”
“She had been bragging how she could get anyone she wanted at college, she dated Kent Stevens QB, Prom king in high school, she’s just beaten me so often at so many things, I just wanted a win in my corner,” Jen lamented. “I’m tired of coming in second to her. First thing out of her mouth will be, you lived with him for how long and he wouldn’t fuck you, but hours after meeting me we screwed like rabbits.”
“Sounds like some of the convos I’ve had when Katie is venting about you,” I said trying to change Jen’s perspective.
“God if this is how I make Katie feel, I’m the worst sister ever,” Jen cried.
“You are not the worst sister ever,” I interrupted, “but you have to be your own person and stop comparing and competing so much. I mean there is always going to be someone hotter, smarter, stronger whatever. You just got to be happy with yourself.”
“I’d be a lot happier with myself if you were inside me right now,” Jen giggled. “Let’s make a deal her Jakey, if you can make me cum before I can make you hard I’ll drop the sex request forever. If I can make you hard I get to suck that damn fine dick of yours.”
“So I keep my cool while making you pop and you drop the sexual harassment for good,” I asked.
“Pinky promise,” Jen replied with a smile and holding out her pinky despite her wrists being cuffed above her head.
“Ok deal,” I responded. “I’m going need to change things up, so no resisting or do I need to put you to sleep again.”
“I’ll behave,” Jen replied.
I quickly untied each of Jen’s legs then freed her left hand from the handcuffs so Jen was now free from her bed. I ordered Jen to lay down on her stomach, put her hands behind her back and cross her ankles.
“Oh I see trying to hide my boobs to keep yourself from getting a stiffy,” Jen said mockingly as I re-cuffed her wrists and bound her ankles with rope. I stayed quiet and tried to stay focused on Jen’s ankles. Flipping her onto her stomach had now left her tone and barely covered ass out for me to see instead. I tried to remember some of the things Steve had done to her a few weeks back that got her all worked up. At the time that was happening I was busy trying to block it all out so other than remembering Jen enjoyed being treated like trash it wasn’t a big help.
I finished binding Jen’s ankles and was contemplating my next move when Jen chimed in. “Hey Jakey time to drop those shorts, I don’t want to hear its just a banana in your pocket when make you stand at attention.”
“Hell no,” I replied
“Come on” Jen pouted, “How you going to turn me on without showing me that package of yours.”
“I’ll just call you a bunch a names,” I shot back.
Jen giggled, “you alert the other girls if you start yelling at me, come on show me little Jakey. You know you want to see what I’m hiding underneath as well.”
“Boxers, final offer,” I bluntly responded.
“I’ll take it,” Jen said with a smile.
I dropped my shorts and went over to Jen’s dresser. I felt a little weird grabbing dirty underwear so I grabbed a clean pair and moved back towards Jen.
“You didn’t have to tie me up just to get into my panties,” Jen giggled, “I’ve been willing to let you mmmmfff.”
“Whores don’t talk,” I said after shoving Jen’s panties in her mouth. “whores never spit and always swallow.” I added squeezing her cheek.
Jen’s face became a little flush from the shock and despite her mouth being filled by a pair of her own panties she let out a slight smile of happiness.
“You filthily slut,” I trying say with force but not too much volume, “how dare you dress like this. I did not give you permission and now you must be punished.”
I gave Jen a hard smack on her thong covered ass. The noise was a bit louder than I wanted but the force seemed right. Jen groaned with a mix of pain and pleasure and strained against her bonds.
“Remember to keep those panties in your mouth,” I said before smacking her ass again. “That whore mouth of yours has had too many things in it lately.”
Jen moaned out of pleasure reacting to another spanking from me.
“I’m going to give you a good licking,” I said trying to keep a straight face. I pulled out one of Jen’s whips from the bag and produced to strike Jen repeatedly on her ass and legs. With each strike Jen’s moans seemed to be getting louder so I rather rudely grabbed the back of her head and shoved it into her pillow.
“You are making too much noise slut,” I said still shoving Jen’s face into her pillow in an attempt to quiet her down. I could tell Jen was enjoying herself based on the sounds she was making along with the tugs and pulls she made against her bonds. The problem was I was also enjoying myself and I wasn’t sure how much longer I could keep my solider down. I decided I may have to try and speed Jen along or she would win the bet. I went over to the back pack and dug out a finger vibrator thinking it would do the trick. Stupidly in deciding on the best way to control Jen so she couldn’t move away. I put her in the little spoon position and pushed her ass into my crotch so I could grope her breasts, keep her from moving and hold the finger vibrator in place. What I didn’t plan on was in though Jen was bound and gagged unable to move much of her body, her ass cheeks were not restrained.
As soon as I put the finger vibrator on her pussy her whole body began to pulsate. Some how she used the muscles in her ass cheeks to move those cheeks up and down against my crotch. Stubbornly I let happen, convinced I could get her off before I got hard. I was wrong. Jen’s thong covered ass rubbing and bouncing against my dick was too much and was rock hard and poking Jen’s ass. Jen screamed and giggle into her gag and she knew she had won. I shoved her bound body off me, stood up and stared in disbelief at my bulging boxers. Jen rolled herself over and mmfffed into her pantie gag attempting to tell me to take the gag out of her mouth, which I did.
“I knew I could get you hard,” Jen said triumphantly. “now drop them boxers, I’m hungry for sausage.”
“Don’t you want me to untie you first,” I said trying to delay.
“Nope,’ Jen, “I like the challenge.
I dropped my boxers and laid down, still feeling a little dirty and nervous I begged Jen that her mom and my dad could not find out about this.
“Please,” Jen laughed, “they both think we’ve already banged, they wouldn’t have left us all alone if it bothered them.”
“I’d still prefer they not find out,” I responded.
“Shut up and enjoy the blow job,” Jen replied getting herself in position. “I’m been waiting forever to get a taste, best night ever.”
Jen quickly shoved my whole dick in her mouth and started going to town. Still weirded out that my step sister was doing this I closed my eyes and tried to imagine it was some other girl. Jen was slower and more methodical than Mandy but was defiantly more excited. Jen came up for air a lot and since I wasn’t doing any dirty talk took care of that herself. Calling herself a dirty whore and slut while my dick wasn’t in her mouth. Honestly had her hands not been bound she probably would have been playing with herself while she played with me. Jen repeatedly warned me not to shove her off me and that she wanted me to blow my load down her throat. After all she said to herself, “whores never spit.” Eventually that time came and shot my load and Jen sucked it all down. She continued to suck until I’m pretty sure every last drop of sperm was out of me and I literally had to pull her off of me.
“Jezz Jen enough,” I said prying her mouth off my dick.
“Sorry,” Jen giggle, its just I mean that’s the only time I’m going to do this, I didn’t want it to end. Plus maybe you won’t have anything left for Mary and the other girls.”
I grabbed a towel and gave Jen’s face a quick wipe before drying myself off. I cut Jen loose and gave her a minute to stretch a bit. I cleaned myself up a bit and put my clothes back on.
“So how do you want to be tied now?” I asked Jen.
“Typical guy,” Jen responded, “I give you oral and soon as you finish you take off on me.”
“I still have your sister and three of your friends to capture,” I responded.
“and bang.” Jen added.
“Let’s not get a head of ourselves, lets tie you up so I can get moving.” I said.
“Spread eagle on my bed please.” Jen offered, “and give me the ball bag, I want to pretend I’m still sucking on your dick.”
“Whatever floats your boat,” I replied.
Jen got comfy on her bed and stretched her arms and legs out. I quickly grabbed 4 pieces of rope from the bag and tied each appendage to a part of the bed frame. I then grabbed one of the vibrators that had a remote so Jen could control it herself while I was busy with Katie and her friends. I put the vibrator in a spot she requested they did my best to tape it into place. Jen was once again trusted up pretty tight,
“Wait,” I spoke up before using the ball bag. “What’s your cereal?”
“I’m not telling you till you fuck me,” Jen snarkly replied.
“Jen, I don’t have time for this,” I complained, “Just tell me.”
“Nope,” Jen giggled before clamping her lips shut.
She was trying to delay me from Mary and it was starting to annoy me. Rather than play anymore I covered her mouth with one hand and pinched her nose close with the other. Jen started to struggle as I impacted her air supply but the ropes kept her from stopping me. I eventually let go and after she caught her breath she mumbled “rice crispies.”
“Any last requests,” I asked putting the ball gag close to her mouth.
“Please don’t bang Marmmfff,” I cut Jen off and strapped the ball in place and placed a towel on her chest incase the ball gag caused her to drool. I turned her TV on and put the remote in her other hand. I packed my supply bag back up, stuck Jen’s phone my pocket and prepared to use the back staircase to sneak down to the basement where I would trap Trish and Jess.
I hid near the basement steps and waited for Trish and Jess to make there way down. I had texted them both pretending to be Jen and told them to meet me in the basement so they could plan how to capture Mary and keep me from getting to play with her. I felt a little bad lying but with four girls still on the loose I needed to get them separated so I could catch them without making too much noise. Trish came down first with Jess not far behind. Fortunately they closed the basement door behind them and struggled to find the light which with made it very easier for me to grab them from behind.
I grabbed a rag and quickly pounced on Jess. I used the rag to cover her mouth and whispered into her ear 1,2,3 go to sleep. Jess was stunned but did as she was told and turned into dead weight without alerting Trish that I was down here. I quietly lowered her to the floor and left her there and went after Trish. I snuck up behind her and covered her mouth with my hand and stuck the toy gun into her back.
“Not a sound sweetie,” I announced to the surprised Trish. “Your little friend is already out cold so don’t do anything stupid or she will suffer.”
Trish nodded her head and let me guide her over to where I left Jess.
“On your knees and put your hands on your head,” I ordered Trish. She complied and sat on her bare feet and put her hands on her head. I flipped on the light so I could see the girls better. As I put the toy gun in my pocket Trish started blabbing.
“My cereal is golden grahams and Jess’s in fruity pebbles,” Trish spat out.
“Trish what the hell?” Jess said annoyed.
“Your supposed be unconscious,” I told Jess trying not to laugh.
“Sorry,” Jess replied.
“I don’t want to be tortured,” Trish whined, “wait where’s Jen she told us to meet us down here?”
“I’m afraid your little friend is a bit tied up at the moment,” I cracked, “but don’t worry I’ll check on her after I have fun with you little cuties.”
“Please don’t hurt us, just take what you want,” Trish cried out, playing the damsel in distress well.
“You girls are what I want,” I said laughing. “Now be a good girl and tie up your little friend. Don’t want her to interrupt while we play.”
“I’m not good with knots,” Trish replied making excuses.
“Luckily duct tape doesn’t requiring a merit badge,” I told Trish as I tossed a roll of duct tape at her. “Go on, get to taping.”
Trish picked up the duct tape and crawled over towards Jess, still barefoot, clad in her boy shorts and sports bra. Trish gently pulled Jess’s hands behind her back and wrapped the tape around her wrists. Trish then crossed Jess’s ankles and wrapped the duct tape multiple times around them before ripping the roll loose.
“Good girl,” I told Trish, “Now lay down, put your hands behind your back and cross your ankles.”
Trish laid down as instructed and I quickly bound her with duct tape. I wanted her off her stomach in short order so I could get a look and start playing with her big tits, compared to Jess she wasn’t showing much skin with her baggy pj pants hiding her legs and leaving only the soles of her bare feet exposed.
“You’ve tied us up, please just leave us alone,” Trish began pleading. “What do you want from us.”
“We are just going to play some games together,” I said smiling back at her. “Now lets get you off this dirty floor and put you some place more comfortable.”
Trish meekly attempted to try and crawl away from me, but with her hands and feet bound with duct tape she didn’t have much success. I got behind her and then pulled her to her feet. Despite her verbal protests I could tell she was quite enjoying my physical touch as her face once again began to turn varying shades of red. I then went to pick her up and throw her over my shoulder. It was a bit tricky as she is a good foot shorter than me. Eventually I got her over my shoulder and started walking around the basement debating the best place to put her down. Trish had put down on her card that she wanted to be carried around by me. I’m guessing being a bigger girl it had been while since someone had carried and tossed her around like this. It also gave me an excuse to have my hands on her big ass and give her cheeks a few good squeezes. Trish did offer some token resistance trying to get loose from my grasp but was probably worried I was going to drop her. So instead she just continued to talk and demand to be put down, which I eventually did by tossing her onto one of the couches.
“Let me go” Trish demanded, “I don’t have any money just leave before the cops come and arrest you.”
“You know sweetie I think I’ve had enough of you mouth,” I told Trish. “Time to shut you up and play with your little friend.”
I grabbed the roll of duct tape and pulled a pair of socks I stole from Jen from my pocket.
“Open up and say ahh,” I said trying not to laugh.”
Trish kept her lips seal and refused to open her mouth up.
“I don’t understand why your being so difficult,” I told Trish as I grabbed her nose and squeezed it closed. Eventually Trish had to open her mouth and I quickly shoved Jen’s sock in there and slapping two pieces of tape over her mouth for good measure.
“Now you be a good girl while I play with your friend for a bit,” I told Trish while giving her left breast a good squeeze. “Don’t feel left out sweetie I’ll be back to play you soon,” making sure to Trish’s other breast a good squeeze as well. Trish let out a moan of pleasure which let me know she was enjoying herself.
I went over to Jess and double checked her card. Jess didn’t want me using and toys or doing anything real dirty. Instead she wanted me to get a little physical, hair pulling, spanking among some other things. To make sure I didn’t cross any lines I got down on the floor next to the bound and still pretending to be sleeping jess and whispered in her ear, “if I get too rough for you say cherry or snap your fingers twice and I’ll stop.”
“I don’t think you’ll be too rough,” Jess whispered back, “but thank you.”
She closed her eyes and went back to pretending she was out cold.
Well here goes nothing I thought, I grabbed Jess by her hair and pulled her face off the carpet. “Wake up my dear,” I said trying to sound menacing, “Its time for you to join the fun I’m going to have with your friend.
Surprisingly Jess didn’t cry out in any pain when I pulled her hair, the only noise was the muffled cries of the bound and gagged Trish still laying on the couch watching me.
“you know there are easier ways to get a girls attention,” Jess responded, “can’t get a girl to touch you so you to resort to tying them up huh.”
Jess was having fun pushing back but I needed to remind her who was boss.
“You know dear it was an attitude like that caused your friend over there to lose her speaking privileges,” I told Jess while pulling tighter on her hair and turn her to face Trish who was mmfffing into her tape gag.
“Oh so Mr. big strong man can’t handle a little lip,” Jess quipped, “untie me and fight me like a real man or you too big a mmmfff. I decided I had enough of Jess’s comments and stuck the toy gun in her mouth.
“Now dear that’s enough,” I said keeping the gun in her mouth, “Looks like I need to beat that fight out of you and turn you into a good little submissive. Not another word or you’ll be sucking on some lead. Understand sweetie?”
Jess nodded her head yes and I pulled Jen’s other sock from my pocked and jammed it in Jess’s mouth. I added two pieces of duct tape to shut her up for good.
“Now ladies,” I said pulling Jess to her still bound feet, “we are going to play a fun little game together.”
I guided Jess over to the couch where Trish had managed to maneuver herself into a normal sitting position. I grabbed the paddle that Jess had requested be used on her then stood there for a bit to try and figure how to position myself and the girls so I would be able to smack Jess’s ass and grab Trish’s breasts from the same spot. I decided I would sit with Trish on my left and lay Jess down on her stomach with her face and mid section on the couch, her butt in my lap and her bound legs on Trish. After a a little maneuvering I got both girls where I wanted, Jess’s butt right in front of me and Trish’s nice big tits to my left.
“Ok ladies time to play our game,” I told my bound and gagged victims. “I’m going to give you a good smack on the ass, if you make any noise I’m going to help myself to a nice feel of your friends breasts.”
The girls both mmmffed in protest under their gags.
“Now now I didn’t even have to smack you to and you are chatting up a storm.” I laughed. “Sorry your friend must want you to get felt up sweetie.”
I grabbed a good hold of one of Trish’s boobs and she let out of soft moan of pleasure and her face started to turn red. I followed this up by smacking Jess’s ass with the paddle. Jess let out an “oh fuck” under her gag and I could tell she enjoyed it. I took turns smacking Jess and groping Trish. Both girls continued to moan with pleasure with each smack and squeeze and despite Jen seemingly sucking my dick dry I was getting turned on again. After spending a few minutes giving both girls attention I decided it was time to just focus on one of them at a time.
I pulled Jess back to her feet and ordered her to start hopping over to the other couch. Despite her ankles being bound Jess was able to keep her balance and get herself close to the couch. Jess had requested I be a little rough with her so rather than gently place her on the other couch, I smacked her in the ass and grabbed a hold of her hair and pulled her down so she landed on her back. I then got on top of her and loosely put my left hand on her throat and put my face inches away from hers.
“It’s time for you and I to have a little one on one fun,” I said to her very sternly. “If you resists me it will end badly for you and your friend over there. Do you understand.”
Jess nodded her head yes and I responded with a “good girl.” I then licked the side of her face to up the creep factor. While Jess had listed no toys, removing clothes or penetration on her card she didn’t have any no touch zones. I was getting turned from spanking her ass and even though they were smaller than Trishs tits, it was time to play with Jess’s chest. I continued to pull on Jess’s hair with one hand and began squeezing her boobs with the other. Jess moaned with pleasure into her gag as I continued to grope her chests, the harder I pushed and pulled on her chest the louder her moans got. I was getting more and more turned on and moved my hand down her inner thigh and squeeze my one hand up and down her legs while the other hand continued to play with her tits.
As Jess continued to moan and twitch with pleasure I continued to get bolder with my hand placement. I moved my hand onto her crotch and despite the layer of clothing I could feel that her panties under neath were starting to get wet. I continued to keep one hand working her tits and the other her crotch. Jess’s breathing into her gag was becoming more rapid and I could tell she was getting close. I got off the couch quickly flipped her onto her stomach and gave her one last hard smack on the ass. Jess let out an “oh fuck yes” under gag then arched her back before collapsing onto the couch. Hearing Jess moan and getting to feel her up had made me rock hard again. If I was going to be showing these girls my dick, displaying it when it was rock hard would give them the best show. I dropped my shorts and let my dick come out. I walked over to Jess and stuck my rock hard dick right in her face. Jess let out a soft moan as she got an up close view. I stroked her hair a bit and said, “You did quite well turning me on, lets see if your friend can finish the job.” I gave Jess’s bare feet a little tickle and walked back over towards a very excited Trish.
I couldn’t quite make out what Trish was trying to say behind her gag but it likely was, “me next, me next.” I walked over to her in my boxers with my erect dick still out and at attention. Despite being bound and gagged Trish was no longer playing a stubborn and scared damsel. Her eyes were locked on my dick and her duct tape gag was likely keeping her tongue from hanging out of her mouth. It was funny up until a few weeks ago before the show I put on for Jen, Katie and Mandy the only time I dared to pull out my dick for someone to was to get a blow job or have sex but now that shyness had gone away and I was getting a thrill out of the attention.
“Like what you see sweetie,” I said as I as shoved my dick in Trish’s face. I brought it so close to her face I could have bopped her on the nose with it. Trish’s face had now turned bright red but she didn’t care, and not like she could really go anywhere. I really wanted to keep playing with her big tits so I shoved her down on the couch and straddled her while laying my dick right on her chest. I grabbed both of her breasts and pushed them against my dick and for all intents and purposes began to fuck and grope her breasts. Trish’s face continued to look red and flush and pleasure from me using her tits caused her to move her head enough that my dick would occasionally clock her in the chin and face. After a bit of that I got bored with the position and decided to try something else.
I pulled Trish to her feet and let her know I wanted her to play with herself while I played with her tits. I told her I would cut her hands free but she was only to touch herself and not anything else. Trish smiled and moaned in agreement. I cut the duct tape from her wrists and she immediately stuck one of her hands down her pj pants and went to work on herself. I pulled her down so she was sitting in my lap. She bounced her big ass up and down rubbing it against my dick while I wrapped my arms around her waist and continued to play with her tits. Trish definitely had experience playing with herself and very quickly was causing her body to shake and her moans of pleasure became louder and louder under her gag. After a few minutes of working on herself she let out an “oh yes” from under her gag and collapsed back on me. I pushed her back onto the couch and rebound her hands with duct tape. I put my shorts back on and walked back over to Jess to tickle her feet again for a bit. Jess wasn’t lying about her feet being sensitive as she thrashed around and laughed into her gag, with what energy she had left. I turned the basement tv on for the girls and told them that I hoped they had fun, but now I needed to go play with their friends but I would be back later to untie them. Both girls moaned into their gags but it was time for me to get ready to play with Mary.
End part 1