My first time was at my friend, Ken’s cabin (not his real name). Occasionally we (him, me, and our other friends) would spend a night over there, sometimes the whole weekend. We’d been doing so since we were small, but once we got into high school we started inviting girls along too. This time wasn’t too different at first. We all came up to the cabin and claimed our rooms (we all bunked in the basement bedrooms) and had great time outdoors. Mostly we went swimming in the lake, which was when I noticed how hot one of the girls was.
Dawn (not her real name) was friends with me, but we didn’t hang out as often as I did with the guys. She was always very pretty to me, but when she came out in a bikini, she was smoking hot! She had a flawless olive complexion, small frame, black wavy hair, and brown eyes. Her hourglass tummy and flat belly button were framed by her round tits above and wide hips and great ass below. I kept sneaking looks at her body, enough that I think she noticed. Fortunately, I was able to keep from getting hard, especially with trunks on. Instead, I kind of showed off, doing dives off the dock and racing the other guys swimming across the lake. Swim team had given me a swimmer’s body, with wide shoulders, a lean torso (even a bit of a six-pack), and strong limbs.
When it started getting dark we went inside and played video games and pool. Both were great, since Ken’s folks had an expensive pool table. Better yet, there was a whole home theater downstairs with a projector screen and two rows of reclining black leather sofas. I wasn’t very great a video games, but Dawn sat next to me, which made the whole thing better. She cheered me on when I played and criticized me playfully when I lost. Eventually we were called up for dinner, and some of us (mostly the girls) changed into pajamas afterward.
My jaw dropped when Dawn came in; she was wearing a tight T-shirt that emphasized the curve of her enormous rack and a pair of wool pajama pants that did the same with her butt. It wasn’t technically risque, but I had a hard time keeping my eyes away from it. We played video games for a couple hours; I lost every match, and without Dawn next to me anymore, it was getting boring. The girls started going to bed, but Dawn decided to stay for a nap right there. I didn’t want to miss any time with her, even if she was asleep, so I stayed as the guys started going to their rooms. Dawn woke up a while later, it was only me and two other guys playing against each other.
They finally finished and said good night; Dawn seemed rested from her nap, and I was still wakeful from the caffeine I’d had from all the sodas I’d drank. I decided to start a single player game when she came over to where I was sitting. She said her shoulders were sore and was wondering if I could massage them. I was good at that, so I offered her the controller and kneeled behind her while she played. I was careful at first, but I started really kneading her neck and shoulders after a while. I heard her let out little groans of pleasure, and it was actually turning me on.
After at least twenty minutes of this I couldn’t stand it anymore. I grabbed her shoulders, turned her around, and kissed her. She kissed me back, enveloping my whole mouth with her lips, and tossed away the controlled without a second thought. She pulled away for a second, moved her legs around to straddle me, and we made out. I’d kissed other girls before, but she was better than any of them. She wrapped her arms and legs around me and I did the same; she was practically sucking my lips into her mouth, but not in a gross way. She even slipped in her tough a little. It felt like we did it for an hour, I’m not sure how long it really was. Either way, it was making me very horny and I wanted to take it further.
I felt for the seam of her shirt and slipped my hands up her back, it was broad and strong. I moved up to undo her bra when she lifted her shirt right off and threw it down. Fantastic surprise, she wasn’t wearing a bra. I stared for a full ten-seconds at her breasts; they were big, round, and firm, with incredible cleavage. She smiled and whipped my shirt off and pulled back toward me. I kissed my way down her neck to her chest and started sucking on her nipples, which were already erect. Dawn moaned as I sucked and kissed, and my hands worked her shoulders and neck. I started moving down to her pants and got my thumbs under the waistband. Second fantastic surprise, she wasn’t wearing underwear. I slipped my hands in and massaged her butt, edging her pants down bit by bit.
Suddenly she pulled back, forcing my hands out, much to my dismay. Reaching into her pocket, she pulled out a condom and handed it to me. You’ve really thought this through, haven’t you? I said. Well, duh, she said. I undid my pants and took them off with my boxers, allowing my boner to come to full attention. As I put the rubber on, Dawn stood up and slowly pulled down her pants. Her pussy was covered in a small brush of short pubic hair, flanked by her wide hips that tapered down into her long, luscious legs. When it was on, Dawn brought over a blanket, straddled me again, and wrapped us up together. She was breathing heavily and she had a sheen of sweat that made her naked body even nicer to look at. I let her have control, she positioned her hips and eased the head of my cock into her slit. Even with all her juices flowing she was really tight, but as I slid into her, I noticed I didn’t pop her cherry. I asked her if she was a virgin and she looked up with a sheepish grin. She said she was but that she’d played with herself beforehand so there wouldn’t be any pain for her first time. I reassured her that I was glad we’d both be enjoying this, and we kissed.
I reclined our section of the couch and let her grind around on my tool, placing her legs and arms on either side of me for support. I’d heard this was the best way for her to climax since she got to control the movement and it really hit her G-spot. It turned out it was also the best way for me, too. I had to concentrate to hold back from orgasm so I could stay hard for her. I didn’t really care how pleasurable this would be for me, I just wanted to give her the best time I could. From my reclined position, I had a great view of Dawns face (and from her expression, she was enjoying herself) and her boobs bouncing as she moved in and out. After several minutes, she stopped and looked at me, both of us so wanting to make this the best first time. I was very close to orgasm, but when she stopped it subsided a little. Then she started again, going at it for a few minutes then pausing. She did this more times than I could remember, but every time I felt more and more built up cum. This kept going for what felt like forever, and it was killing me to hold it back.
Then, finally, after she paused and stared straight at me with an almost serious face. You ready? She asked me, all I could say was yeah. She started again, same as before, gradually speeding up, getting more vigorous. I grabbed her plump buttocks and held on as they bounced and jiggled. The tension in my groin was incredible and my tool was rock hard. Then she stopped for just an instant, we made eye contact; I could feel a deep tingle in my balls, and I knew I was going cum no matter what. Dawn moved with slow, drawn out pumps, dragging against my cock, staying eye to eye the whole time. Three . . . two . . . one . . . zero. She pushed herself all the way down to the base of my shaft and held it there. I saw her close her eyes and gasp, and her tight pussy squeezed my tool even more as she climaxed. The tingle in my balls rushed up my groin and I shot my massive load into her, surging in waves for a full ten seconds as I moaned with pleasure and squeezed her ass. I’ll confess I’d jacked off a couple times, but nothing compared to how I came in her.
Dawn fell back on top of me, my dick still entirely enveloped by her. We were hot and sweaty from sex, but it just made me feel more intimate with her. We made out again, big wet French kissing that she was so good at. After a while she got up and slipped off my rod, which was started to get limp. I’ll be right back, I said and grabbed my clothes to head for the bathroom. I took one last look of Dawn’s nude body standing there, nothing but the projector screen illuminating her curvy shape. Once I’d tiptoed to the bathroom, I took off the condom, wrapped it in toilet paper and buried it in the trash. Then I took a piss, got dressed, and headed back to the theater room.
I found her curled up on the couch in the blanket, seemingly asleep. For a moment I stood awkwardly, not sure whether to join her or go to my room. She opened her eyes, saw me, and told me to get over here. I undressed down to my shirt and boxers, crawled under the covers, and laid down on my side behind her, back to front. Our legs tangled together and I pulled myself up right against her. I wrapped my arm around her and she took my hand and laced finders. She turned head to me and said thanks, and so did I. Her long black hair was splayed in curling strands and it smelled sweet, like vanilla. I buried my face in her hair and inhaled the scent until I fell asleep.
Of course, in the morning all our friends found us and we woke up to them parading pictures on their phones they’d posted of us asleep together. The worst part was I had morning glory right against her ass. She was kind enough to not say anything, and I was able to hide it from the others. It was a little tense, though, we didn’t have much room to talk to each other with the others joking about us all they could. Instead, we all got dressed and went upstairs for breakfast after Dawn and I made the others swear not to tell Ken’s parents about it. That didn’t stop them from giggling about it and making all sorts of inside jokes. In fact, with all the whispering, Ken’s parents probably figured it out anyway.
After breakfast, Dawn and I claimed the two bathrooms to take showers understandably; meanwhile, the others went to play video games in the few hours until our folks came for each of us. I finished showering first and Dawn came shortly afterward and sat next to me. We turned down the game controllers and just held each other quietly. Finally I whispered to her, That was really great, thank you. She murmured back to me, I’m so glad it was with you. We kept talking to each other, mostly about how we loved each other and about doing this again. All our parents eventually came to pick us up and we went to get our packs from the rooms. Once I’d gotten my stuff I sneaked over to her room and slipped in. She seemed like she’d been waiting for me; I rushed up to her and kissed her. She kissed back, not the big sensual kissing that turned me on, just a fierce, short kiss, to say goodbye.
Turns out, it wasn’t goodbye. We started dating afterward and had many more wonderful sleepovers, not all of them at the cabin. However, I will add that cabin sleepovers became how many of my friends, including Ken, lost their virginity. Dawn and I are still together, and we’ve completely fallen for each other. And it all started with our first time.
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Cabin Sleepover
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