Where it happened: My Apartment
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My first time did not occur until I was in college and 21 years old. This story will not be like most and merely talk about the sex, since to be honest it wasn’t particularly mind blowing, and will instead focus more on the story leading up to it. I lost my virginity to my best friend at the time, whom I will call Emily. Emily and I met our freshman year, but we did not start to become close friends until partway into our sophomore year. At the time, we both liked different people and shared this knowledge and related concerns with one another. We started to hang out more often as we became closer friends, and eventually we ended up hooking up (everything but intercourse) at the end of the year. We were worried that this would endanger our friendship, but instead it only made us closer (this was also the first time either of us had legitimately hooked up with someone). After agreeing that the reason for the hookup was just to relieve stress regarding our respective romantic endeavors, we continued on as even better friends.
Emily and I spent the summer together at college doing research jobs and lived just one block from each other, so our friendship expanded even more during that time. Although we did not hookup with each other that summer (in fact, both of us hooked up with a few other people), we did end up making out at a few random parties. Nothing too serious occurred until the fall semester rolled around. The first semester of our junior year we spent an immense amount of time together, doing everything from getting dinner nearly every other night to studying in each others’ rooms. Not a single day went by where we did not text, and we never went more than two days without seeing each other. We also had a number of incredibly fun nights of drinking that still rank as some of the best memories of college (and did not involve us hooking up). Nearly all of our friends assumed or questioned whether or not we were dating, and considering all the time we spent together I cannot blame them.
During this time, I slowly began to fall for Emily. I trusted her more than anyone else and we both considered each other as best friends (even going so far already as to say that we were perhaps the most important people we met in college). Then, at the end of that semester we hooked up again, but this time was much more romantic and satisfying than before. We discussed before and after break about the possibility of dating, mainly being hung up on the issue of what would actually change since we were basically psuedo-dating until that point anyway (though we did not admit that until much later). Yet a week into the new semester we finally began to date.
By this point, I realized that Emily was one of the most incredible girls I had ever met. She was intelligent, driven, funny, kind, and absolutely beautiful. I had always believed, and still do, that starting out as friends also makes for the best relationships. Thus, dating Emily was a dream come true. However, after just four days of officially dating, she called it off. She said she was uncomfortable with the change in our friendship and just wasn’t sure she actually liked me (unfortunately another trait of hers was perpetual indecisiveness). Though I will never truly understand her reasoning given the actions leading up to it, we broke up and I was naturally devastated.
In order to reconcile and recover our friendship, we tried many a time to cut back on contacting one another, but that never lasted long as we were in the same project group for a major class and found that we hated not being able to talk to one another. Since we never truly spent time apart and tried to go on as if things were alright, I never had the opportunity to actually get over her. We continued to share things we couldn’t talk to anyone else about, including for her some romantic involvement with another guy she was indecisive about. Obviously, this killed me on the inside but, being too weak to make any changes to our dynamics, I could do nothing.
Then, the unthinkable happened when we hooked up again at the end of that semester. This hookup was the most intense one we had so far, and I even got her to orgasm three times (she never got off before so I gave her one for every time, but then again I never came during any of our hookups thus far either). We had made the mistake of being too close and allowed this to happen, but as she was going off to California for an internship that summer there was no time to really deal with emotions. There were a few weeks into the summer where I was doing research at college again for and before she left, so during this time we decided to hookup one more time.
The night it occurred, I was content with just a regular hookup, but Emily proposed having sex. She said that she trusted me more than anyone else and had done the most amount of sexual things with me to that point, so it only seemed natural. Although I was hesitant at first, after a few drinks earlier in the night my penis was doing all of my thinking for me. Moreover, I was still infatuated with her, so I could not refuse.
(Here I will finally get into some sex details, since I guess that is part of describing your first time as well). So after getting back to my apartment that night, we stripped off each others’ clothes and hopped into my bed. We made out for a long while before I moved down to sucking on her breasts and rather large nipples. As I played with one while sucking the other, she began to moan slightly. I knew from our past hookups, however, that she got off better when I teased her for a while, so afterward I began to caress and kiss her entire body while avoiding her groin. After working my way across her chest, arms, and legs, I slowly inched closer to her pussy as I spread her legs apart. With barely any tongue I began to slowly lick the entire length of her opening, gradually adding more and more tongue. As her moans increased and my tongue got tired, I put in one then two finger which worked on the walls of her pussy as I continued to lick her clit. As I became more rough, her hips arched toward my face and hands, which at this point changed to a much faster stroke along her clit and vaginal opening. To this day, one of the sexiest things I have ever heard was her saying,’Oh god, oh god’ as I continued to eat her out. I’m not sure if she actually came that night from me eating her out, but she definitely enjoyed it so I asked if she could return the favor.
We traded places and she began to suck on my cock while stroking the shaft. I told her to try a few new things that night including spitting on it to get it as wet as possible and moving her tongue in circles around the head. While her blowjob was fantastic and definitely the best was giving me so far, what really felt amazing was when she came up to suck on my nipples as she stroked my cock. As she did this it felt immensely pleasurable, and I was glad she finally stopped to ask me to put it in or I would have came right then and there. I put a condom on and we traded places to start with the missionary position, and I asked one final time if she actually wanted to do this. Upon receiving a clearly scared yes, I put the tip of my dick in her pussy and slowly pushed forward. She was obviously experiencing some pain as I pushed further and further, but eventually I was all the way in. After holding right there to make out for a bit and get her used to the feeling, I slowly moved my hips back and forth. The pleasure of finally having my penis inside a vagina, and the vagina of the girl I cared for most no less, was unimaginably satisfactory. As I began to pick up the pace she felt more discomfort that slowly passed, and as we interlocked one hand with the other around each others’ bodies, it was pure bliss. We switched to her on top for a while, but this was honestly a little uncomfortable for me as my dick bends upward slightly when erect instead of going fully straight. She also couldn’t handle me thrusting upward with her on top at this point, so we changed back into missionary. We continued to rock with each other for a while, and the sight of my cock going all the way in and out of her pussy was amazing. It became even better when she wrapped he legs around me and dug her hands into my back, which turned me on even more. Yet, for as good as it felt, I never came close to cumming. After we eventually stopped, I masturbated while holding her in my other arm and came so much that the last few spurts of semen weren’t even cloudy. She definitely did not get off during the actual intercourse and neither did I, but as we lay there next to each other making out for a bit we agreed that losing our virginity to each other was the right idea.
Emily left for California the next week after a perfect goodbye in which we simply held each other for a long while and tenderly kissed each other farewell. We continued to talk nearly every day even with her on the other side of the country, and we would video chat with each other every two weeks for three to four hours at a time. Each time we did, she would say that I should come visit, and I could never tell if this was because we were such good friends or because she was opening up to the idea of us dating again. After all, her indecision before was very abrupt and she was happy that she lost her virginity to her best and most trustworthy friend (as she put it). I finally had the time now to deal with my emotions and realized without a doubt that I loved her.
So I decided to visit her in California, profess my love for her, and lay it all on the line for one last chance. Honestly, I thought I had a pretty good shot at success and all of my friends who knew her and the majority of the situation agreed. Yet when I finally spoke to her about dating again, she said no. Her time in California had apparently cleared her head as she realized she did not want a relationship with anyone at the time. I was devastated once again, and we decided not talk again for a long while. I still have yet to talk to Emily after this occurred, and I am not sure when I ever will be ready to after she broke my heart. I imagine one day we will likely be able to converse amiably at the very least, but I do believe that I have probably forever lost her as a best friend and lover.
For all of you out there, know that just because someone you lose virginity to someone does not mean that they want to be romantically involved with you. After all, love is a two-way street.
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