Where it happened: college dorm room
Langauge: English
Sex: Male
Rating: 5
Category: Straight
I was in college when I first had a girlfriend. She was a year younger than me, a very cute brown-haired, brown-eyed girl who for some reason fell in love with me. Although I wasn’t her first lover, I was the first to give her a full orgasm, and I take some pride in that to this day. My first sexual experiences were with her. We started out as just friends, but realized how much we cared for each other over the summer break when we were states apart. We managed to visit each other twice. When she came to see me, we shared our first kiss. When I went to see her, I saw my first naked woman in the flesh, and also went down on her and gave her her first orgasm.
It wasn’t until school started again and she returned the favor by jerking me off. The thought of my semen running down her hand onto me as she pressed herself against me, our lips locked, still gets me hard. This was how our sexual relationship went: we’d make out, get horny, I’d go down on her, she’d masturbate me. Pretty simple, but we were happy with it for a while. Things changed on Halloween.
For Halloween, she borrowed a cheerleader outfit from a friend. Just seeing her in that short skirt turned me on so very much. I was at her apartment and we were getting ready to go to a party at my dorm, along with her roommates. I asked if we could stay at her place instead and practice some “extra-curricular activities” but she really wanted to go to the party, so we did.
We went and had a good time. As things were winding down, she was ready to get a ride home with a friend, and I near begged her to stay the night with me. I couldn’t get the image of her wearing that short skirt and nothing else out of my head, but she was tired and I could tell that she didn’t want to have to walk home in that outfit the next day. So instead, I begged her to come over and bring the outfit with her tomorrow. She didn’t get it until I told her how hot she looked in the cheerleader costume, and she agreed to do it. I kissed her goodnight with a quick stroke of my hand between her legs. That move had changed her mind about leaving in the past, but not that night. When she left, I got an idea and ran to 7-11.
The next day she showed up around noon and I let her in and asked her to change, and not worry about a bra. She grinned at me changed. I didn’t want to see her naked yet, so I left the room until she opened the door again. Once again, seeing her in that little skirt made me instantly hard, and I went in and locked the door.
I took her in my arms and pulled her hard against me, kissing her fiercely. She could feel my hard-on against her stomach, and she reached around and cupped my ass. Our tongues explored each other’s mouths as we kissed, our hands roaming over each other’s bodies. I thrilled at running a hand down her body and feeling her bare arms, then bare legs, where I was so used to sleeves and pant legs. I led her to the bed and laid her down on it, laying down next to her. We continued to make out and caress each other, me climbing on top of her, until we were both really horny.
With our usual way of doing things, I’d take off her top, kiss her all over from face to waist, then take off her pants, repeat the kissing, but continue down past her panties and kiss and lick her thighs instead. Then I’d plant a kiss on her pussy, remove her panties, give her another deep long kiss on her lips, then kiss my way down to her pussy and give her oral. This time, however, her clothes were part of the attraction, so I didn’t want to take them off. However, I got her horny enough without needing to, so when I got to the point of wanting to go down on her, I kissed my way down one of her arms to her hand. I sucked one finger into my mouth, flicking my tongue over the tip like I would do to her clit.
I sat up and removed her socks, then kissed my way up her legs and under her skirt. In addition to panties, she had that undergarment cheerleaders wear that covers their panties. We had been making out for so long, I could see a slight wet spot through them. I hooked my fingers over the top of them, and kissed her slit, bottom to top, then pulled them down her legs and off. The way she’d arch her back to let me slide her panties over her ass is still one of the most erotic images in my mind, and this time was no exception.
I got a little harder, and I think I even could feel some pre-cum leaking out of my cock as I saw my love laying on the bed, fully dressed, but still so very sexually accessible. I laid on top of her again and kissed her hard, letting her know how much I loved her, and hearing back how much she loved me. I then kissed my way down her other arm to the bottom of her skirt. Back and forth, I kissed up her thighs, lifting the hem of the skirt up with my hands. I had to stop and stare for a moment. Seeing her very wet, very horny pussy under the skirt…damn…I had never been hornier.
I finally kissed her bare slit, bottom to top again, and then went to town on her clit. My tongue flicked over it slowly, getting faster and faster over time. I wrapped my arms around her legs and hips, hugging her to my face so that she wouldn’t slide out from under me when she started moving. It wasn’t long until she was bucking her hips up against my face, trying to eke every ounce of stimulation and pleasure from my mouth. I still remember the sounds of her panting breathing, the slick squishing sound of my tongue over her clit, her pussy rubbing my chin, the look on her face as her eyes clenched shut and her mouth opened in pleasure. And the smell and taste of her! She always smelled and tasted so good, and it was only years later that I truly came to appreciate that. It only took a couple of minutes of my tongue flicking at her clit, then she sucked in a deep breath and held it as her hips lifted off the bed, pushing hard against my face. A few seconds passed then she started panting and bucking very fast, then paused again. She did this five or six times before collapsing to the bed, every muscle relaxing at once.
I stopped licking her clit and moved my tongue down and massaged her lips, as the clit was way to sensitive right now as I had learned from past experience. I did this, waiting for her to come to her senses. Finally her hands came to my head and gently pulled me up to her. I wiped my mouth, removing her juices from it as she hated them, then I was fully atop her and she kissed me. Only our lips would touch, because she didn’t want to taste herself on my tongue either. We kissed for a little bit, then she said she wanted to give to me. I had a little more in mind.
I got up and went to my closet where I had a cup of mouthwash and rinsed my mouth out. She looked at me strangely for a minute until I told her that I wanted to really kiss her today, and couldn’t do that unless my mouth was clean after going down on her. She seemed pleased and maybe a little charmed by the thought that I liked her kisses that much. I got back on the bed and she took off my shirt, then laid me down and straddled my stomach. I could feel her wetness still dripping out of her and soaking my stomach. She leaned down and kissed me deeply, moaning her approval of the mouthwash. Moving down further, she took off my socks, then my jeans, and then my underwear. My cock shot straight up into the air as it was freed from confinement, probably harder than it had ever been before.
She crawled up to lay next to me, but I stopped her. She looked at me in confusion. I told her I had a present for her and asked her to close her eyes. She did, and I put something in her hand. Looking at it, her eyes went wide, and she looked at me again. I had put a condom in her hand, and seeing me nod, she got a huge smile on her face. We had talked about having sex, but I had told her I didn’t feel ready. I did now. She ripped the package open and rolled it down my hard cock, giving it a couple of strokes for the hell of it. I sat up and kissed her as she did, and now she knew the real reason I wanted to be able to kiss her for real this time. I unzipped the back of her cheerleader top, and helped her take it off, freeing her large breasts. Her nipples, which usually only got hard with constant stimulation, were pretty pointy at the moment, and I sucked one between my lips, rolling my tongue around it.
She asked me how I wanted to do this, and since she had told me before that being on top was her favorite, I suggested that. She gave me another smile and kiss, then pushed me down and straddled my hips. She started to unhook the skirt, but I stopped her, telling her how much of a turn on it was for me. She gave me a mischievous smile, and left it on. My hands were going up and down her legs, and reaching up to cup and caress her breasts, and hers rubbed my chest and arms. I could feel my cock pressing between her legs for the first time, even through the condom, and I started trying to slip it in her, not realizing that I really had no chance to do it without her help.
Finally taking pity on me, she took me in hand and guided me inside her. She had always joked that I was going to hurt her someday, after she had jerked me off and would look at how long and hard my dick was. Maybe she was taking that thought into account, because she moved down my shaft so very slowly. I couldn’t see because of the skirt, but could feel that I was most of the way in when she breathed “Oh God.” Then she let out a small whimper of pain when she fully engulfed me. She asked me to give her a minute to get used to it, and I let her, wrapped up in the feeling of my cock being fully surrounded for the first time ever. Every few seconds I felt her squeeze me as she clenched, and it felt so GOOD! I caressed her breasts with my hands, rolling the nipples gently between my fingers and reveled in the pleasure she was giving me.
Soon she started rocking her body back and forth, and the pleasure increased. She commented on how deep inside her I was, that it almost hurt it was so deep, but that it felt good at the same time. I pushed upwards a little bit and she gasped, and like a marionette with cut strings, her body collapsed down on top of me. I held her and asked if she was alright, and she kissed me and replied she was okay, it was just a little too much right then. We kept kissing, holding each other, and she started moving her hips. I could feel myself moving in and out of her, and I began to move with her, since I wasn’t so deep inside of her at this angle.
This was feeling pretty good, but we both wanted more and she sat up again. Using her hands on my chest, she started to push herself up and letting herself fall, moving up and down on my cock. I still couldn’t see it because of the skirt, but I was still so turned on. I pushed up again as she lowered herself, and she stiffened up, but didn’t collapse this time. She started rocking again, and I reached out to lift up the skirt. For the first time, I saw how her pussy swallowed my cock, just a tiny bit of the base still visible. I watched for a moment as more of me would appear and then disappear inside of her again as she moved. I looked up at her and I could tell she was amused by my actions. She changed to the up and down motions again, letting me see how she slid up until only the tip was still inside of her, then down, engulfing me fully.
Something about that sight set me off and I stiffened and moaned slightly as I came. She went back to rocking atop me, very quickly, which felt really good, almost too good during my orgasm. All too soon, I was done, and she slowed then stopped. She leaned over and kissed me, our tongues taking turns in each other’s mouths, then she carefully slid off my cock and laid beside me.
We held each other for a while, making out and whispering to each other. The whole time, I was still hard. I ended up rolling the condom off me while standing over the trash, to catch any escaping semen. I cleaned myself up and rinsed off a bit with some water I had kept nearby in anticipation of all this.
Normally, we’d be done after we had both cum once, but today was special. Today was our first time having sex with each other and while somewhat spent, we wanted more. I put on another condom, remembering how she had put it on me, and this time I had her lie on her back and laid down between her legs. Again she guided be into her, the skirt pulled up to make things easier, and I just lay there for a moment, enjoying the feel of her. I started to move in and out, my hips making a natural motion that is probably implanted in every man’s DNA. Having cum already, I knew that I’d last much longer this time, so I just slowly pumped in and out of her. We kissed deeply, our tongues twirling, our hands running up and down each other’s bodies as we moved together. It was heaven, pure and simple.
I knew she didn’t cum during our first time, but I was determined that she do so this time. As much as I enjoyed the kissing and touching, I knew what would guarantee her an orgasm, so I sat up on my knees. Reaching down, I started rubbing her clit with my thumb, still thrusting in and out. She let out a moan as soon as I started this, so I knew I was doing the right thing. She normally made no sounds during our lovemaking other than soft panting, so a moan was a really good sign. It took about ten minutes or so but she did her usual orgasm routine, but with some obviously muffled cries. Knowing that I was the one to make her feel so good, the first person to truly make her cum during sex, set me off and I erupted inside her once again. I couldn’t make myself keep thrusting as I came, I just felt too sensitive, so I pushed as deep as I could inside of her, all the way in, and she let out another short cry.
I laid down on her again, feeling the warmth of her skin against mine, kissing her and noticing how she didn’t kiss me back. I looked and saw her eyes were totally unfocused. It took her almost a full minute before she started responding to my kisses and touches. We just held each other close, both basking in the glow of aftersex, and it was wonderful. We only stopped because we were afraid the condom might leak, but again I didn’t get soft. Typically, as long as my mind stays aroused after orgasm, my dick does too. She was really pleased to learn of this, and in fact was the original reason she said that I was going to hurt her someday. Of course, she also said that she was going to enjoy it, and I’m glad we finally made that part true.
It had been a couple of hours since she had arrived, and we were pretty tired out. I let her finally take off the skirt, and after cleaning up, we fell asleep in each other’s arms. I’m not sure how long we slept, but I woke up first. She was on her side, facing away from me, but her legs were pulled up so I reached down and felt between her legs. She was still WET! Then again, I was still kind of hard, so who am I to complain. I slid a finger inside her slowly, gently, not wanting to wake her. Yet, anyway. I slid it in and out for probably six or seven minutes, getting harder each second, before she turned to look at me, and sleepiness vanished from her eyes as I watched.
She spread her legs and let me go down on her again, this time I fucked her with my finger as I did. She grabbed the last condom and gave it to me. I stopped for a minute to put it on, but then kept going down on her. It took a few moments more until she came. When that happened, I quickly sat up, moving my finger to rub her clit rapidly, and managed to slide my cock inside of her, making her let out a breathless gasp. This time I wasn’t gentle. I pounded in and out of her hard, and it seemed her orgasm never really stopped. She started moving with me, her arms and legs wrapping around me and pulling me into her with each thrust.
I’m not sure how long we fucked like that, but I started getting tired and stopped. She was completely out of it again, but recovered quickly. Realizing I hadn’t cum, she had me roll on my back and straddled me, taking over the hard work. She moved slower that I had been going, but that let her last longer and maybe ten minutes or so later I finally came.
Being out of condoms, we didn’t have any more sex that day, and we probably couldn’t have managed to do it again anyway, we were so worn out. But it was my first time, and still one of the best ever! Next time, I bought the biggest box of condoms I could get. She started wearing skirts more often, none that short of course, and a couple of times we had fun fucking while she was fully clothed except for her panties. We used a lot of the condoms, but unfortunately broke up before finishing the box. She’s still one of the sexiest people in the world to my mind, and she probably still knows that if she wants a really good fucking, all she needs to do is wear a skirt!
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