Where it happened: Friend's House
Langauge: English
Sex: Male
Rating: 8
Category: Straight
Backstory:
My friend and I had been best friends for about 8 years. We each had sisters that were about 3 years older than us and were best friends too. Many times I would stay the night at his house or his sister would stay the night at my house with my sister. Usually when I was at my friend’s house we would be up all night so there was no time for me to make a move on her. However, when she came to stay the night I was usually able to sleep in the same room with my sister and her. There were more than a few times that I would stay up until they were both asleep and then very lightly kiss my friends sister. It was so light that she usually didn’t notice or if she did it wasn’t enough for her to wake up. Then one time I decided to kiss a little harder and slide my tongue through her lips just enough to touch her teeth. I was able to do just that without her waking up and then she started to stir awake so I quickly rolled over and pretended to be asleep. I don’t know if she knows what I was doing, but it seems like she had to have known I was doing something.
The story:
So not too long after that night I was staying at my friend’s house and so was my sister. We were all hanging out together. Throughout the night my friend’s sister and I were joking around with each other about a blanket. I took it from her and ran then she chased after me and the tug of war ensued. Once when we were tugging away at it we began a war of saying “Mine” “No mine” back-and-forth. Each time we took turns speaking our faces got closer. Finally we were close enough to kiss, I felt her breath on my face. Then I let go of the blanket and she went back to hang out with my sister.
Later we were all sleeping in the same room, my friend and I on the floor and our older sisters on the bed. I was laying right next to the bed and my friend’s sister was above me on the bed. We were all laying in bed watching a movie. Then I felt my friend’s sister’s hand fall off the bed and rest on my pillow behind me. I rolled onto my stomach and reached my hand up to hers. We clenched each others hands and I knew she wasn’t just asleep. We remained holding hands the rest of the movie and occasionally I would kiss the back of hers. Eventually she took her hand away to fall asleep. I laid in bed shaking from the nervousness and excitement. (I had masturbated countless times while fantasizing about a sexual experience with her, but never let it be known that I liked her. It was a complete one-way relationship.) Soon everyone else was asleep except me and I was still shaking. I laid there for a while considering what to do. I really wanted her. I figured I could kiss her while she was sleeping like I had done many times before. Slowly I sat up and watched out for movement from anyone. Then I spun onto my knees and just stared at her shaking violently. Then before I knew it I was leaning over her, but instead of kissing her I was nudging her shoulders to wake her up. She stirred awake and looked at me for a second. Our eyes locked for a moment and then without any words we began making out. After we finished making out I laid my head against hers and wrapped my arm over her. We cuddled for a while and then I kissed her once more and she turned over to go back to sleep. I left the room shortly after and masturbated in my friend’s bathroom. I was 15 years old and she was 18. My fantasy of sharing a romantic event with her when she was conscious and willing had actually played out. But masturbating didn’t quench my 15 sexual drive and I went back to bed with a hard on. I laid in bed for about 20 minutes shaking still, wanting more and not knowing what to do. I got up again, woke her up again and we started making out again. Then she pulled away and whispered, “What are we doing?” I told her I didn’t know and then we both went back to bed. I was devastated. I thought I had just blown it.
About 2 months later I was staying at my friends house again (without my sister this time). My friend fell asleep so I snuck into his sister’s room. She was awake watching TV. She looked up at me and I leaned in and kissed me. She pushed me away and said we couldn’t do it. I kept trying to kiss her and she finally took me out to the living room and tried to tell me all the reasons that we couldn’t do it. All the while I kept trying to make out with her. One time she let our lips remain touching for about a minute before pushing away, but I couldn’t get her to open up to me (both metaphorically and literally). I went to bed that night more deflated than the first time.
It wasn’t until winter vacation (about 6 months since the first incident) that my parents were out of town and my friend and his sister were staying with me and my sister. We were sitting on the couch together and had a pillow between us. I kept trying to tickle her feet and she kept grabbing my arm and pushing it away. While doing this each time she held onto my arm a little longer and slowly slid her hand closer to mine. Finally we ended up holding hands when both our siblings were in a different room. After a while my friend decided to go home and stay there instead. That was fine with me, that meant I just had to make sure my sister would stay put, which wasn’t that hard since she was on the interenet flirting with guys. Eventually I was able to get my friend’s sister to follow me into my parents room. I sat on the bed and patted beside me. She sat down and we looked at each other for a second then leaned into each other and kissed. Slowly I slid my tongue into her mouth and we fell slowly onto the bed, laying next to each other making out. After a few minutes we went back out to my sister to not raise any suspicion then I got her to follow me back to my parents room again. More of the same making out on the bed. I was getting so hard. Then she got up and told me to scoot back on the bed and lay back. I scooted back ,but kept my knees bent so that she wouldn’t notice the bulge in my pants. She got up and I saw her through my legs and for a second thought I was about to receive my first oral sex experience. But she walked around the bed and got up on her knees behind me. She leaned over me and with our faces upside down from each others she began to make out with me. Our tongues swirling around each others was like a dream. Then she got up and said “okay that’s good.” and left to go back to my sister. The only thing we did the rest of the night was giving each other glances, laying next to each other and me kissing her on the shoulder, and slyly spanking each others butts (hers was amazing).
The next experience came when I was staying at my friend’s house. We had another friend over as well. Again I waited until they were both asleep and then snuck into her room. She was awake and when she saw me said, “Hi, what are you doing here.” I shook violently and couldn’t think of what to say. She watched me shake and then scooted over and opened the covers saying, “Come here. Why are you shaking so much?” I never really answered, but we did start kissing. Eventually we added our tongues to the equation. The main difference about this time than any other time was that I was laying on top of her. I don’t remember who started it, but soon our hips were rocking up and down in rhythm with each others. I loved the way her hips rolled up and down against me. The other difference about this time was how our hands acted. I slid my hands anywhere over her body that they could reach: her ass, her legs, her stomach, her back, her shoulders, her neck, the back of her head, and eventually her breast. I started off massaging her right breast outside of her clothes. Then I slid my hand in her shirt and massaged it inside her bra. I made a go to slide my hand inside her bra, but she pushed me away. A few minutes later I tried again and she allowed it. It was my first time touching a boob and it felt very foreign to me. It was squishier and smoother than I thought it would be. After a while I lifted her shirt up and rolled her bra up then began to suck on that right breast. It wasn’t what I expected. It was hard for me to get my mouth around a single spot and suck from there. To remedy this I kept it on the nipple and focused my efforts there. I assume she enjoyed it because she let me continue for a while. Afterwards she said, “Somebodies got a fetish.” I just giggled nervously. We continues making out and gyrating our hips for a while. Then I said, “I bet you didn’t expect to be in this position tonight.” She replied, “I didn’t expect YOU to be here tonight.” Eventually I sat up to leave and she remained laying. I asked her to give me her hand and she did then I tried to guide it to my raging hard on. About three inches away from getting her hand there she pulled back without saying anything. I took that as my notice to leave. I left and went to bed ecstatic and hard.
That night was so amazing that it usually casts a shadow over the other times that we did come together for our secret get encounters.
Some of the other more memorable times are:
She was hanging out with my sister at our house. It was the middle of the day and we had been spanking each other behind my sister’s back. I wrote a note that said “tell her you have to go to the bathroom.” I wasn’t sure whether or not she was going to do it, but she actually ended up doing that fairly quickly after getting the note. We met in the bathroom and began making out. I rubbed my hands all over her and then laid down on the ground. She laughed, but laid on top of me and we made out there. Then she went back to my sister and that was that. It was short, but memorable for some reason.
She was staying the night with my sister at my house. We were all watching a movie and my sister went to bed. She then went to bed, but as she left I told her to come out to where I was sleeping (the back room of the house) when my sister fell asleep. Again I left not knowing whether or not she would. [Remember this was a fantasy that I had usually only been able to imagine in my head with my hand pleasuring me…this wasn’t supposed to be real so I was half expecting it to end any time] However, it wasn’t long before I turned around and saw her creeping through the doorway. As she walked over to the makeshift bed I had created with just laying blankets on the ground I instantly got hard at the sight over her body. She was slim and had an amazing ass and really nice boobs. She came and laid next to me and we started making out. Soon I rolled her onto her back and got on top. We made out groping each other’s bodies. Then she left and I thought it was over so I masturbated into a sock. However, not too long after that I see her crawling back through the doorway. This was one of the greatest surprises of my life. She laid back next to me and we started making out again, but I wasn’t as into it as before because I had just spent myself masturbating. So for a while we just laid next to each other watching TV. Then I started to regain my energy and I slid my hand into her pants and let it cover her bare butt. She looked back at my hand then at me and we kissed. We started to make out after that. I got back on top and started reaching for her panties. She stopped me there and went to bed. I came in the other sock I had and went to sleep the happiest 15 year old in the world.
Another night much like the one before found us watching a movie at my house with my sister. Again my sister went to bed and left the two of us there alone. I wasn’t willing to wait this time So I walked over to her couch and sat beside her. Immediately we started making out and touching each other. I pulled her onto the carpeted floor and got on top. I was moving my hips into her rougher than I ever had. Then she stopped me and we got back up onto the couch. We continued making out and my dick was harder than I can ever remember it being. I stood up while she remained seated. [At this time I hard turned 16 while she was still 18.] I reached inside my pants and grabbed at my cock. She immediately said, “What are you doing?” I stammered nonsensically and she said, “No, I can’t.” I released my cock and stood not knowing what to do. She got up, kissed me, and left.
We were all staying at the beach (my whole family, two of my friends, and her). One day, when my parents were out on the beach and my friends and my sister were playing downstairs I went up to my parents room where she was waking up my nephew from his nap. I pretended like I was just there for something in my parents room, but after I pretended to not find was I was looking for I stood at the end of the bed nervously shaking. She watched me and smiled. I walked over to her and wrapped my arms around her and kissed her. We pulled away and she picked up my nephew and said, “Wait here.” She took my nephew to my sister and then came back to me. Sat on the end of the bed making out then laid back. Then she stood up and I scooted back on the bed so my feet were off the floor. She got on the bed and crawled until she was directly over me on all fours. She leaned in and kissed me then we made out. Eventually she laid her body on mine (the first time she was on top) and our hips began rocking. After a while I began to notice that she seemed more into it than usual. Her tongue moved in my mouth more violently and she was humping me rougher than I think even I had ever when I was on her. I grabbed her ass and helped her gyrate even stronger. My cock grew and hardened. There were moments during this that I thought, more than just a blowjob, that I was going to lose my virginity. I thought (was afraid and excited) that she was enjoying it so much that she would actually give into my teenage urges. But we heard my sister coming up the stairs. My friend’s sister rolled off of me and onto the floor behind the bed. I laid back and got in a position that made it look like I was just taking a nap. My sister quickly came through the door and saw me. Her demeanor softened and she softly said, “Have you seen [my friend’s sister]?” I said no groggily trying to impersonate a napping person and my sister left. My friend’s sister got back up and walked over to the door. She said she should go so I walked over to her and kissed her then as she turned to leave I grabbed a big handful of her ass.
Later that day everyone else was outside except her and I. I walked up behind her and wrapped my arms around her. She was on the phone, but she motioned for me to follow her to her room. We sat on the bed and I put my arm around her. Then while she was talking on the phone I reached around and began massaging her in her crotch. I had never done anything like it before, but I guess I was rubbing her the right way because she let me continue for a while. Then she finished her call and kissed me and said to come back to her room later that night.
So later that night I snuck over to her room when everyone else was asleep. I stood over her and nudged her awake. She opened the covers for me to get in, but I thought that it would have been dangerous if I needed to get away quickly. I had forgotten the feeling I had earlier that I might have lost my virginity. I don’t know that even if I had gotten under the covers with her that it would have gotten that far, but it certainly would have increased the odds. Even without being in the covers with her she still seemed to be more into it than usual. Her mouth and tongue moved more passionately and her hips gyrated more than mine even though she was under me. We made out for a while and heard footsteps over head so we paused for a second. It was just someone going to the bathroom upstairs. Once we realized we resumed what we were doing. With the thrill of doing this with more people (that could catch us) in the same house coupled with how intense she was I began to feel better than ever before while we were going at it. I knew the feeling before from masturbating, but had never done it in the presence of another person. We kept going, tongues dancing and hips rubbing together impersonating what would have been an intense sexual session had we both been naked. Soon I was moaning softly, but trying my hardest to keep it in so as not to wake up my sister in the next room over. Our breathing grew heavier and heavier and we were humping so hard that we had to keep ourselves at bay because the bed had started creaking. Then it came on suddenly without warning. I came in my pants while on top of her. I collapsed on top of her, our breaths warming each other’s necks and our chests expanding against one another’s. I lifted my head and kissed her. We made out very roughly for a second or two and then I got up. I don’t know if she saw the wet mark in my jeans…I somewhat tried to show her by facing forward and keeping it in front of her for a while, but I think it was too dark in the room for her to notice. I don’t know why I wanted to show her. I think it was sort of my way of showing her that I was more adult than she thought and that if she let me I could pleasure her the adult way. Anyway after that I changed my clothes and went to bed.
One other instance I remember is not really special in terms of what we did (it was fairly normal: I snuck into her room and we made out while rubbing our bodies together). What made it special was that her mom got up while I was still in her bed. Her mom’s room was right across the hall and the door to my friend’s sister’s room was wide open. Immediately she threw the covers over my head and tried to lay on me in a way that would make it look like she was cuddling with pillows. Her mom went to the kitchen and then to the bathroom. I could see from a crack in the covers when she passed by the doorway to go back into her room. All she would have needed to do was look inside the room and she probably would have been able to tell it was me. That was a pretty scary, but extremely exciting time.
Another time we were at home with my sister and mom watching TV. My mom took my sister to school and went to work. I had the day off and my friend’s sister (who was in college now) didn’t have class. So my mom and sister left and I immediately went to my room and stripped down to my boxers. I walked back out to the living room and crawled up to the couch she was on. She was startled at how quickly I had prepared for it, but she went with it. We made out on the couch for a second and then went into my room. We stood next to the bed making out and I tried to take off her sweater. She stopped me. I didn’t want to ruin anything so I let it rest. I laid her on the bed and got on top. We made out and I began to get hard. She didn’t seem as into it this time. Her lips seemed a little limp and she was just kind of laying there tolerating it. I picked up on this and pulled off of her. I noticed that the entire time my dick was rubbing up against her outside of my boxers. When it got hard it slipped through the hole in the front. I was nervous about this, but also excited. It was the first time she had seen it because whenever I tried to take it out she stopped me. This time it was an accident so she couldn’t stop me. I was nervous that she would be upset with it being out, but also excited that maybe if now that she finally saw it she might want to suck on it. She got up and went back out to watch TV. I sat in my room very confused and disappointed. We had been going at it for over a year and she had still never even touched my dick let alone sucked on it. I tried to tell myself that it was just because she didn’t want to go too far in case we got caught. She might have gone to jail if it ever got out that she sucked my dick. Although I wasn’t sure if what we did do would have been punishable by prison as well. Anyway I told myself that so that I wouldn’t think it was because she didn’t like me enough to do it. I went out to where she was and as I walked by her I said, “I think we should stop doing this?” She did not reply. Needless to say this was the last time we ever did anything like this. There were a few times afterwards that I tried. Once when she was giving me a ride to school I put my hand on her leg and slid it up until I was rubbing her private area. She responded to this by saying, “I thought you wanted to stop.” I told her I made a mistake…we didn’t start back up again.
I learned a lot from her about myself, my body, and how to pleasure a woman. I learned about restraint and patience. I learned about being gentle and polite. Most of all, though, I learned about listening to girls, not just what they say, but how they act; when she said no I stopped, when she hinted to me with her body that she wanted more I gave her more, and when she showed me that she didn’t want me anymore I ended it…even if I did try to reignite it again. When it’s all said and done I am grateful for what we had together and grateful that it ended. I got to live out a teenage fantasy, which not many teenage guys do, but still not become attached to it. I was able to move on and get back to reality and develop adult fantasies of finding a girl I could marry and not just sneak around and make out with. A girl I could show off to the world.
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