Where it happened: In the woods
Langauge: English
Sex: Male
Rating: 5
Category: Straight
We had been dating a while; I think about 4 months. She was older by over two years, and, unlike me, wasn’t a virgin. I had always looked older than I was though, so initially when she met me she thought I was her age. You have to understand, at the time I was really into her, but she had slept with 2 different guys before me; albeit only once with each.
The point is: at that age I didn’t want to have sex before I was married. I probably wasn’t ready, but we did a LOT of other stuff prior to this day…
One day I was at my girls house and we were in her room watching a movie. She had this cool sort of homemade wooden bunk bed thing that was like a little cocoon when you were in it, and I remember it was a beautiful day, so the sun was shining through the window and I could hear birds in the trees outside.
Anyway, I was spooning her and, as usual, I pretty soon developed a huge boner. I’m not super well endowed, just shy of 7 inches, but when that was pressing up against her butt, she knew about it. In these situations she would often grind up against me, wiggling her ass aginst my crotch without saying a word or even acknowledging she was doing it with a look. I would drive me crazy.
By this time she had already given me blowjobs on many occasions (although I have never, to this day, with any girl, come from a BJ) and I had fingered her plenty of times too, not to mention the oral play with her beautiful soft, milky white DD-cups (she was on the thick side, but hot)but this time we were lying down and her big, round ass was just right there…
I reached over and puched my thumb past the waistband of her jeans and pulled them right down over her ass, so now the head of my cock was just tickling the top of her crack. She reached round and pushed my dick between her big, juicy cheeks. It felt awesome! I could feel the pressure of her ass cheeks just pressing aound me. she started pushing her ass back towards me as she rubbed my head up and down along her cleft, right over her (clean) asshole and back again. A few times she even stopped over her ass and pushed back against me as if she was going to take my cock in her butt, but she would just stop and start the stroking again.
After a few minutes of this (it could have been an hour, I have no idea) I had my hand up her shirt, massaging her breasts the way I knew she loved, rolling her nipples between my finger tips. We were making out as well, our tongues exploring eachother and driving both of us wild. by this stage I had pulled her jeans down past her knees to allow her to spread her legs apart slightly, but it wasn’t enough. I turned her over onto her back and slid her jeans right off, and she opened her legs straight away to allow me between them.
It was the first time I had actually seen her pussy “straight on” so to speak and, truth be told, I was a little surprised. It was deep pink, almost red along her inner lips and her pubes (which were nicely trimmed) were much darker than the naturally blonde hair on her head. Either way, I didn’t spend long looking and quickly I was lying on top of her; we were making out like crazy.
I could feel the wetness and heat of her on the head of my cock and wanted nothing more than to just press inside her, but I was in completely new territory and had no idea how to do it. She obviously sensed this, because she reached down and started stroking my dick RIGHT along her opening, which drove me WILD. It was at this point that I looked her in the eye and sheepishly asked, “Do you have any…?”
She just looked at me blankly and asked, “Any what?”
She honestly had no idea. “Condoms,” I said, for some reason mortified at using the word. I knew she had some because I had seen them in her room before.
“Wait a sec,” she replied and jumped up, pulling her jeans back on. She rooted around for a bit where I had thought the condoms were, but to no avail, so she went to ask her sister if she had seen them (they obviously had quite an open and frank relationship)
Turned out her sister had actually taken the condoms and used them with her boyfriend a few days before! Needless to say, we were both pretty frustrated and I ended up going home with the worst case of blue balls I have ever had, even up to now.
ANYWAY, one false start down…
It was the following weekend and we were in town. It was another beautiful day, and as we were walking around a lake my girlfriend told me she had something to show me, and proceeded to pull a packet of six ‘extra-safes’ out of her bag. By this stage, I had gotten past the super horniness of the week before and again figured I wanted to wait and not have sex, but seeing those condoms just put it in my mind: ‘it’s right there, you can do it any time…’
Anyway, we went to the movies that afternoon to see some stupid bullshit film. There was one other couple in that screening with us sitting way down in front of us, and we were right at the back. Well, that day, I got my first (and last) cinema blowjob. I fingered her too and actually ended up soaking her right through her white lace panties: point being, we were SUPER fucking horny by the time we left that cinema.
Without saying much at all, we walked for about ten minutes to a little forest just outside the town. The tress were dense enough to provide cover but sparse enough to allow sunlight through, so there was grass on the ground. I laid down my jacket and we lay down and started making out. Before long we were both completely naked. In hindsiht that was stupid because, although this forest/wood was good cover from outside of it, people walked through occasionally, so we could have been seen…
Either way, we didn’t give a shit. My cock was pressed up against her pubic bone and her little pot belly was pressing against be own stomach. Her legs were around me, her ankles hooked just under my ass, pulling me closer. I was massaging one of her breasts with my hand and sucking the nipple of the other and I could hear her letting out soft moans of pleasure. She must not have been able to take it because she pushed my back off of her and reached over to her bag, proceeding to liberate one of the condoms from its wrapper.
She looked me in the eye, silently asking my consent. I nodded. She reached for my cock and rolled the condom on, right to the base of my shaft. Things were slowing down now that the reality of the situation was hitting me. I slowly lowered myself to her and kissed her long, but softly, still leaving space between our bodies. She reached down and took my cock in her hand, guiding me towards her glistening opening.
I could feel the heat of her again, and a slight sensation like a gentle, lingering kiss on the head of my dick. One last time, we looked each other in the eye. She gave the slightest of tugs on my cock and I took it as the signal to push into her…
Wow! It was like nothing I had ever felt before. The heat and the slipperiness of it was incredible, even through the condom. I hate using them these days, and never do (don’t worry, I’m married) but at the time it felt AMAZING. I could feel her squeezing my shaft, and it was almost as if there was a slight suction on my head. It felt like I was in about half way now, and she pulled me closer with her heels so that I was fully inside her, making her gasp a little. “Are you ok?” I said, concerned that I was hurting her.
“Of course,” she replied, “it’s just you’re quite big.” To this day I don’t know if she meant that sinceely or if she was trying to stroke my ego. In any case, she continued, “You feel great inside me. Keep going.” I didn’t need to be told twice.
I started stroking in and out of her. Being completely inexperienced, I had poor technique and needed to use my hips more, but despite my slightly awkward method, she seemed to approve, pulling me closer to rest my chin on her shoulder. I started to speed up, and now I could hear her wetness as our bodies collided again and again, making me lose all sense of time. She was digging her nails into my back slightly at this stage urging me to come. I could feel my balls slapping against her ass and smell the fresh sweat and sweet scent of her pussy mixed. I wasn’t sure where I was going with this, but I knew it felt good, and was feeling better with each stroke…
I was in top gear now, I could hear her moans in my ear, feel her breathing speeding up. She had her hands on my ass now, slippery with sweat. I was stroking in and out of her, our pubic bones rubbing. Her breasts, moving up and down beneath me, pressing against me.
Something was welling up, a pressure behind my balls, pushing, tingling. I drew out of her one last time before plunging in all the way, coming in a way I had never felt before. I collapsed onto her, and she held me, our breathing matched as we both gradually returned to a normal rate.
I pushed myself up on my elbows looking into her eyes and we kissed.
–
Later on we were bot quiet as we walked around town. I couldn’t inagine how I was going to continue a normal life after this experience.
To be honest, my orgasm, even at the time hadn’t felt spectacular (I had had better alone) but the very act of sex had totally taken me out of my normal frame of mind for hours. I knew it hadn’t been spectacular for my girlfriend, but she assured me she’d enjoyed it, and it wasn’t long before we were pros, with both of us coming almost every time and HARD.
We dated for a few more years until various things led us to grow apart and we broke up. In many ways I still wish I had waited to have sex for the first time with my wife (who I have AMAZING sex with), and I think I probably wasn’t quite ready, but I don’t regret having the experience as such; I feel like as far as first times go, it was planned and actually fairly good, plus it was with someone I cared for at the time.
Me and my first don’t talk any more, we’ve become very different people, but I’ll always remember those times if not always with fondness, then at least wistfully.
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