This happened to me 4 years ago with a girl I had been dating and her younger sister. I was 23 at the time and so was my girlfriend Samantha. Her younger sister Jess was home for the summer from college and what started out as the same type of weekend we'd all shared in the past turned into one of the coolest nights of my life to that point. I guess I should explain what led up to that night first.
Sam was a tall, beautiful girl and we'd met sophomore year in college and had been dating for over three years. It was serious but at that time neither of us was even remotely thinking of marriage. As I said, Sam was tall (5'8", 120lbs) with a nice 34B chest and a great ass to go along with her long dark brown hair and pretty brown eyes. She turned heads and I always felt lucky that she was my girl.
Jess was her younger sister (21 then) and went to college out of state. I liked Jess a lot because she was a real party girl who knew how to have fun. Sam wasn't uptight but compared to her younger sister she was very responsible because when their parents died she was only 15 and helped her grandmother raise Jess and their younger brother. Besides being fun and funny I had a burning desire to see Jess' breasts, they were awesome. She was 5'5" and very athletic. She worked out at the gym so she had a very tight body. To me just made those tits look more awesome. Of course Sam knew nothing of my desires for her little sister. I jerked off more then a few times wondering what she looked like naked. I was also guilty of peeking thru her hamper when she was home from school to see her panties and to read the tag on her lacey bras. Hell, I was 23 and horny.
I guess I should tell you what I look like to. I'm 6'2" and at he time weighed about 180. I have black hair, a goatee and was in excellent shape from playing various sports year round. I'm also blessed with an 8" cock. It's not a super cock by any means but rather it's built like me, long and lean. Girls made a big deal of it when I was in high school and had just started having sex, but I had only been with Sam during college so I missed that reaction when girls first saw it. I liked being above average and playing two sports in college and sharing showers I knew I was above average (but definitely not the biggest fish in the sea).
So, now you have a picture of the three of us. This particular night had followed a day at the beach with Sam and Jess. It was July and it was hot and Sam had talked to Jess the night before and was worried because Jess had broken up with her boyfriend in April and was still down in the dumps over it. We were going to a small, private beach that we went to frequently because it was never too crowded and she suggested we pick Jess up and take her with us. I had never been to the beach with Jess and figured maybe I would get to see her in a bikini so I was all for it.
It took about 15 minutes after we got there for me to start having to fight off an erection. Sam always wore a sexy bikini so I knew what to expect when she took off her shorts and t-shirt. I was delighted though when Jess stripped down to a purple thong and an equally small top. She looked so amazing that within minutes I wanted to run off somewhere and beat my meat like it owed me money. When she adjusted the strip in front of her thong and cursed because she said she did a shitty job shaving, I saw what she meant. A few stray pubic hairs were visible. With no shame she tucked them in right in front of Sam and I.
My aroused state worsened when she started to talk about sex. Now this part wasn't uncommon. We often joked (the three of us) about sexual things. One night in a bar when Sam and I had just started dating Jess blurted out; "Sam says she really know how to use your tongue" and her sister nearly fainted from embarrassment and while I was embarrassed, I also felt a rush of pride as the group we were with responded to her statement. I remember being surprised that Sam had discussed intimate details about our relationship with her sister.
So the three of us were lying on our towels. I was trying not to stare at Jess' perfect ass. It was rounded but so tight it looked like you could bounce a quarter off it. She was asking me (for the male perspective, I guess) why guys wanted girls to shave their muffs (her word for it) and that if they wanted that so bad they should go ahead and shave their hairy nuts. I looked at Sam and we both laughed despite trying to fight it because I shaved not only my balls but also nearly all my pubic hair. I had gone out with a girl just before Sam and I started dating that shaved completely and talked me into trying it. I loved it and have kept myself smooth ever since. Jess wanted to know what we were laughing about and asked her sister if she shaved? Sam just nodded "no". Then she looked at me and raised her eyebrows and we all laughed together. Sam for the record has a full bush that she keeps trimmed but doesn't shave (only her bikini line).
The conversation stayed on that track for the next 45 minutes. Jess was talking about how lame the guys were at college and she was saying maybe next semester she'd join in on all the girl/girl experimentation that was going on. I had to lie on my stomach at this point because my cock was so hard. It was throbbing and I'm serious when I say I was tempted to go and find somewhere to jerk off to relieve the pressure. Thankfully it was quiet for a while as the three of us just enjoyed the sun.
When we drove Jess home their grandmother insisted Sam and I stay for dinner. That was fine with me because it was nearly 100 degrees out and my basement apartment had no air conditioning and Sam lived with two other girls and I hated spending the night there. So a few more hours in the cool apartment was a good idea. Besides, a home cooked meal was so rare these days.
We went and rented a movie and I brought back a couple of six packs and when grandma went to bed at 9 o'clock we all crashed on the living room couch and opened up the beers and put the movie in. We laughed and drank the beers and by the time the movie ended we were all a little buzzed. Sam got buzzed on two beers but Jess could hold her liquor a little better, as could I but we were all feeling it. I said it was time to get going but Sam said she would rather I didn't drive and asked Jess if we could stay. Jess was all for it and we went upstairs and got ready for bed.
The apartment they lived in was a duplex with two bedrooms and several times in the past Sam and I had spent the night. Jess had a king size bed and the three of us easily fit on it. We had a routine. The bed was pressed against the wall and I would sleep closest to the wall with Sam in the middle and Jess on the other end. Sam joked that I always got a hard-on in the middle of the night and she didn't want me to accidentally gorge her sister with it.
I wore my shorts to bed and the t-shirt I had been wearing since I showered that afternoon. Sam stayed in the bedroom with me and just borrowed a nightshirt and wore that on top of her panties. Jess went to the bathroom and came back in wearing a long nightshirt that went past her knees. It was pulled tight across her chest and I could see that she was also wearing a sports bra under it. I couldn't tell if she wore shorts above her panties or just panties or maybe nothing (I was fantasizing again) under that shirt.
We had the air condition cranked on hi and we were all under the blanket and Jess put the television on. Sam was sleeping within minutes, which disappointed me because I was spooning behind her with my hard cock pressed against her ass and she just wasn't interested. Jess and I stayed awake and watched something on cable, one of those soft-core movies and we both giggles quietly, careful not to wake Sam.
I'm not sure when I fell asleep but when I woke up it was 1 AM and I had to piss. I carefully climbed from my place against the wall over the two sleeping sisters and went to the john. I still had half a hard-on and I was tempted to jerk off before I went back to bed but I could hear stirring in the hallway so I flushed and left my frustrated cock as is. I went back into bed and Jess was sitting up on the edge. "Feel better?" she whispered and I nodded yes and she stood and walked out of the bedroom. I heard the bathroom door close. Sam, in my absence had rolled over and was now facing the wall. I tapped her to move over but she wouldn't budge so I lay in what was now the middle of the bed. I faced Sam's back just to be safe.
When Jess came back in I watched her and of course my eyes went to her chest. I could've sworn she had taken off her bra because for the first time I could see the outline of her obviously hard nipples. I was looking over my shoulder and as she crawled under the covers she told me to turn my nosey face back to the wall. She was joking but I knew she had busted me checking out her tits. "Don't roll over and poke your pecker into me while your sleeping. I'm not Sam, remember?" she again laughed at her own wit and I did too albeit a bit nervously.
I couldn't get to sleep. I was just so damn horny and my cock was pounding in my shorts and underwear and I was aching to give it some room. I decided to try and take my mind off my erection. I rolled over and took the remote from on top of the covers and switched the muted television to a replay of the days Yankees game. Jess was lying on her back and breathing deeply so I assumed she had fallen asleep. She had the covers pulled to her neck so she was completely covered. I lay with my head on my left hand and watched TV for a little while until I was finally feeling myself fall back to sleep.
I can't give you a time the next event occurred because besides opening my eyes in initial shock and seeing that the ball game was over, I was frozen. Jess had her sweet ass pressed up against my cock and as soon as I realized that I started to get hard. I was scared shitless and tried to stay perfectly still. Then I felt Jess pushing her ass back against my cock very gently, than she wiggled it slightly. I looked behind me to make sure Sam was still asleep and she was a foot or so away and still facing the wall. This little grinding continued in silence for a few more minutes. At that point I was still thinking clearly enough to know this was very wrong. A part of me hoped Jess was just dreaming and it would stop soon. Her eyes were closed.
Finally it did stop. Then I felt a hand take my hand. Jess pulled my right arm over her body and rested it right on her breast. I didn't move it at first but my resolve weakened and I gave it a squeeze. I had never touched a tit that big and I felt how hard the nipple was under my palm. Then her ass started to move again and her hand disappeared under the covers. She rose up slightly and I could feel her pulling her shirt up. She pulled it just above her waist and I took the opportunity to slip my hand under it and have a feel of her naked tit flesh. She shuddered quietly as my hand wrapped around her tit and I started playing with her nipple. I wasn't sure but I thought she was naked underneath. Her ass was still pressed against my clothing covered cock. For the next few minutes, that's how it went with the exception that she had slipped her hand between her legs and was obviously rubbing herself. "Take it out," she said in a breathy whisper but I wasn't sure I was hearing her right. The Whole situation was so surreal. I didn't respond right away. She looked over her shoulder at me; "Take out your fucking cock:" and her words jolted me to reach down and pull my hard cock out of the leg of my shorts. I nearly came when I felt her hand touch my cock.
She adjusted her position so that my cock was between her legs and her pubic hairs tickled me. Then I felt her wetness. Her pussy was absolutely soaked. Sam's pussy got wet but usually after some tongue work and 20 minutes of hard fucking. Jess was wetter then I ever remembered her sister getting.
Jess used her hand to keep my cock pressed against her. It seemed to slide between her swollen lips and over her clit and I could feel my entire shaft getting wet. I was playing with her tits a little more aggressively now and she seemed to really like when I pinched her fat nipples. We were trying to move without moving. By that I mean we were doing what we were doing knowing Sam was on the same bed with us and we had to be so careful. I wondered if the thought of how wrong this one was crossing Jess' mind, as it was mine. Then she buried her face in the pillow and she was cumming. I actually felt her getting wetter as she rubbed her clit frantically and came for a good minute or so. I was shocked that she came that way but more then that, I was ready to burst my balls.
She reached down and her hand was touching my cock and her wetness. She brought her hand to my face and she held it under my nose. I inhaled her sweet pussy before I put her fingers in my mouth and tasted her. She tasted so amazing. She did it again only this time she licked her shiny fingers clean. She did it again for me this time.
Without a word she raised one leg slightly and held my cock before guiding the head between her lips. This time though I slipped inside of her. Again, it took every ounce of strength not to blow my load right then. Sam couldn't take birth control pills so we always used condoms. It had been years since my cock was in a pussy bareback. But the thought of getting Jess pregnant was the furthest thing from my mind. All I could think about was how her pussy felt like satin. She was so wet and she was really tight. The head and maybe another inch or two slid in before I met resistance. It wasn't her cherry it was just that she was that tight. I had her pulled so tight to me now that I was able to lean in over her shoulder and when she turned her head we kissed. Our tongues were desperately seeking the others. "Go slow. I've never had anything that big in me" she whispered between kisses and that almost made me cum again.
Eventually I was able to slide my entire 8" into her and she lowered her leg again so we were spooning like before only this time my cock was in her velvety cunt. I forgot where I was for a minute (actually, I forgot who was asleep beside me) and started to pump my cock into her faster. She put her hand on my hip and signaled me to slow down. I did. I needed to cum but I also didn't want to be a minute- man so I was glad to slow the pace to a crawl. Besides, her pussy felt so good without even moving. So almost perfect, right?
Thankfully we heard her grandmother a few seconds before the bedroom door opened. We froze, lying there completely motionless. Thru half closed eyes I could see their grandmother in the doorway looking into the room. There was no way she could have heard us and Sam didn't. She seemed to evaluate the situation and looked perplexed at me spooning with Jess and not Sam. Then she slowly made her way across the room to the air conditioner and lowered it. That's when Jess decided to be bold and started squeezing my cock with her pussy muscles. I have never felt anything like that. I mean, I've had my cock squeezed by a pussy but Jess' muscles were so strong it was as if she were milking my cock. So with Sam a foot behind me and Grandma walking back towards the TV she was milking my cock. Grandma shut the TV and left, closing the door behind her. I heard a quiet giggle from Jess and then felt her hand at our joined crotches. She fingered her clit and gently played with my balls and I moved my hips ever so slightly causing my cock to slide in and out of her gripping cunt. That's about the time I lost it. I broke off our kiss to tell her I was going to cum and she whispered I could cum inside her.
My cock exploded with a force I never even imagined. I could feel it, rope after rope of my thick cum shooting deep in Jess' pussy. Jess must have felt it too because she exploded with her second orgasm. Her contracting cunt muscles made me feel like she was going to rip my cock off inside of her. When it finally stopped I felt like my heart would burst from my chest. Now we lay there motionless, my cock still inside her and our juices dripping out around it. I knew we had to be making a mess. Finally I rolled onto my back and stared at the ceiling and weighed what had just happened.
Sam rolled over onto her back and that nearly gave me a heart attack until I was sure she was still in a deep sleep. Jess was on her other side now and facing me. My eyes had adjusted to the total darkness enough for me to see that she was smiling. I had to smile too. I tried to fall asleep because I was so totally drained but before long I felt Jess' hand on my chest. She slowly ran her fingers down my belly to my crotch. My cock had softened but it was still hanging out of the leg of my shorts as well as my balls. She nuzzled closer to me so that her lips were touching my ears. "He feels so soft and smooth," then I felt her tongue touch my earlobe. "And so sticky. I bet he tastes like candy" I suppressed a giggle at her little joke but then she told me to keep an eye on Sam and make sure she stayed asleep. I looked at my girlfriend sleeping beside me, a peaceful look on her face. I felt so guilty at that moment.
Guilt faded and fear rushed into me as Jess slipped under the covers. I felt her breath on my cock and despite the fear I was feeling I could also feel my cock stirring again. Then I felt her tongue licking around the head. For a long time that's all Jess did. She licked my cock and balls like she was licking an ice cream cone. Whatever, the result was another throbbing erection.
I wanted nothing more then to close my eyes and enjoy the new mouth on my cock but I couldn't turn away from Sam's sleeping face. I have to say, Jess had the most amazing pussy I have ever felt but it was obvious she hadn't sucked a lot of cocks. Sam gave amazing head, the best blow- jobs I ever got. Jess by no means was terrible (if there's such a thing as a terrible blow- job) but she lacked the technique of her older sister. Still, it felt pretty fucking fantastic.
I tried to pull her away when I felt myself ready to cum. Sam didn't like to swallow. She said she hated the taste. Jess didn't go away though. She put her mouth over just the head and sucked on it while she gently stroked the shaft and I exploded. It was not the same load that I had just shot in her pussy, but it was definitely a big one. She kept at it, milking my cum only this time with her mouth and hand until I was totally empty.
She slid out from under the covers and we kissed. I had never really tasted my own cum before but as she opened her mouth I tasted not only my own cum but her own sweet taste. We kissed like that and I must admit I was devouring her mouth. I liked it.
So we didn't get caught… that night. It wasn't until after Jess returned to college that fall. We e-mailed each other and although we both admitted the sex was out of control, we were both feeling some guilt. She would also complain that I spoiled her because she had fucked this guy and he had a "little cock" and couldn't get her off. I had to admit that sex with Sam seemed lacking as well after that night. I would often imagine it was Jess sucking my cock while Sam gave me head. I would cum so fast that way.
I didn't see Jess again until the Thanksgiving holidays. Sam and I were supposed to pick her up at the airport but Sam called last minute and said she was going to be running late and couldn't get out. She asked me if I minded getting Jess myself. What could I tell her? No, I can't because I'm afraid I may fuck your little sister again? So I went.
As soon as we saw each other we were on fire. I didn't take her straight to grandma's. Instead we detoured to my tiny apartment and she begged me to eat her pussy. She was dripping wet and I ate her to two orgasms before I flipped her onto her hands and knees and buried my face in her crotch. I ate her little puckered asshole and fingered her dripping cunt until she came again. Then I slammed my cock into her from behind. I was fucking her hard and fast and she was moaning so loud I was sure my landlord upstairs could hear. That's when we got caught. Sam had a key to my apartment. She was on her way to her grandmother's when grandma called to say we weren't home yet. She stopped by my apartment. She literally caught me with my cock in her sister.