Me losing my virginity is one of those stories that really defines me and my life to a tee. No one else would get laid for the first time quite like I would, especially under the circumstances, so I figured I'd make a blog about it. Hopefully I can make it sound as interesting as it really was.
So I have been friends with a young woman who, for the purposes of this blog, I will call F. F and I met through a mutual friend of ours, and we just clicked. We have similar views about life and people, and we're both rather nerdy. We both like sitting around, talking about movies and feelings and girls. She's defiantly bisexual, a product of her intense feminism. F had a boyfriend from back home, and for her first year at college, they almost broke up. It wasn't just the distance; she was moving on with her life at a university while he was stuck in community college with no prospects or grades. Last fall, they broke up for realz. It was kinda sad, but I had to be there for her. She cried for three days straight. She was on her period at the time, too, so it all kinda went to hell.
F emerged a sexually-independent, forceful, non-submissive woman. She became very flirtatious with everyone, and I found it fun. She and I started to cuddle and have emotional conversations regularly. Through this, we established a deep, personal bond. We sort of became dependent on each other. She felt like she wanted to explore affection from multiple people; I felt like I needed acceptance from women (something I've rarely even had). She opened up her feelings of insecurity with men, and I opened up about how basically all women in my life have been scornful, arrogant, spiteful bitches who have no apparent purpose on this earth but to reject me and make me feel worthless.
F saw this. She sympathized. She wanted me to feel good about myself. I have an abysmal self-esteem caused by women as a gender, and F single-handedly wanted to fix that. We would cuddle furiously and...
Me losing my virginity is one of those stories that really defines me and my life to a tee. No one else would get laid for the first time quite like I would, especially under the circumstances, so I figured I'd make a blog about it. Hopefully I can make it sound as interesting as it really was.
So I have been friends with a young woman who, for the purposes of this blog, I will call F. F and I met through a mutual friend of ours, and we just clicked. We have similar views about life and people, and we're both rather nerdy. We both like sitting around, talking about movies and feelings and girls. She's defiantly bisexual, a product of her intense feminism. F had a boyfriend from back home, and for her first year at college, they almost broke up. It wasn't just the distance; she was moving on with her life at a university while he was stuck in community college with no prospects or grades. Last fall, they broke up for realz. It was kinda sad, but I had to be there for her. She cried for three days straight. She was on her period at the time, too, so it all kinda went to hell.
F emerged a sexually-independent, forceful, non-submissive woman. She became very flirtatious with everyone, and I found it fun. She and I started to cuddle and have emotional conversations regularly. Through this, we established a deep, personal bond. We sort of became dependent on each other. She felt like she wanted to explore affection from multiple people; I felt like I needed acceptance from women (something I've rarely even had). She opened up her feelings of insecurity with men, and I opened up about how basically all women in my life have been scornful, arrogant, spiteful bitches who have no apparent purpose on this earth but to reject me and make me feel worthless.
F saw this. She sympathized. She wanted me to feel good about myself. I have an abysmal self-esteem caused by women as a gender, and F single-handedly wanted to fix that. We would cuddle furiously and flirt and tell our deepest, most secret secrets. One time we kissed out of nowhere. And it was great! She just came up to my face and her lips felt like a timeless, other-worldly palpation of heaven. It was the best kiss I've ever had, and even now as I write this on the very spot where it happened I can recall the imprint of her lips on mine. It was divine.
In mid-November, F and I were cuddling again. I mentioned ever-so casually to her that, now that she was single and had so much prurient sexual energy to share, we should have sex, which would cure my self-esteem issue (by being accepted in the most intimate way by a woman) and also let her open up herself to other people (having been in a 3 year monogamous relationship). A pause ensued. Then....
"Piyoz," she said into the empty room, "I'll have sex with you."
I honestly thought she was joking. Wouldn't you? But she insisted that she would in fact have sex with me. I couldn't believe it! Why would a woman have sex with me? That doesn't happen! F was busy with sorority business that night, so it was a no-go then, but the next day, she was almost entirely free. So it was set. On Friday, the eleventh of November, in the year of Our Lord 2011, F and Piyoz would engage in casual sexual intercourse.
It was about 6:30 at night when I arrived at her room. She was running a little late with her whole day, so she was in the shower when I was about to leave. We went into her room, where none of her room mates were present, and for some reason F got dressed again, despite the fact that we'd be taking our clothes off in a matter of minutes. We sat down on her bed, and started talking. Not about sex or anything, but regular friend-to-friend chat. Then we remembered that we were going to screw, so she turned the lights off and closed the blinds.
Now this was my first time, not hers. She knew what she was doing, so she had fun teaching me the ropes of pleasing a woman. We laid down on her bed and started kissing innocently. Smooching with her was unusual in a good and a bad way: It was good because kissing an attractive woman is a great thing for any guy to do, but it's bad/weird in that we had no real, serious sexual attraction. Yet here we are. Smacking lips and holding each other. I had never formally made out before, so this was also a new, exciting experience. I was sitting upright with my legs off the bed, and F sat on my lap, legs open, and faced me as the making out ensued.
After some time, she pulled back and told me to take off her shirt. I obeyed, and gleefully so. To take off a woman's shirt is an important moment in a man's life, and to see her partial nudity is a sort of landmark. She took off mine, too, and more making out happened, half-naked. Her skin was soft, definitely, and the way that she stroked my arms and shoulders was stimulating. I tried the same on her and I guess she had the same reaction. Before long, she got up and took off her pants. I did the same on her bed. She remounted me and then we did some more kissing mixed with touching each other all over. It was the most frightening and exhilarating experience I had ever had since seeing the Watchmen movie for the first time.
Her pink, thick bra rubbed against my chest, and I could feel the warmth and pressure of her thighs around my waist. We were both really turned on in a slow and steady sort of way, not how people are in most pornos. Real sex. I moved her hair back and started kissing her neck clumsily, like a virgin, and she giggled. She called me cute. I tried to defend myself, but that only got her more aroused. We stopped for a quick second. We knew where we were going next.
F got up off the bed and took off all her underwear. Without being told to, I did the same. A nude, gorgeous, and tempting F walked back to the skinny, afraid, naked Piyoz, and laid down next to him. She pulled the covers up on the bed, and we both got underneath. She laid down on her back and let me lie next to her, and the kissing/caressing continued, but this time, with no borders. As we kissed each other necks, panting and sighing, our hands moved around nervously. I stroked her whole body, breasts and stomach and legs. She grabbed and held on to my whole torso and clung tightly. This exposure to the entirety of her body was unbelievable, and it was probably a thrill to her, too. Her legs were clearly shaved recently, along with her bush. Her breasts, out of their normal D-cups were a pleasure to touch and feel. Breasts are incredibly soft and fun to play with. She reached down and grabbed my thing and stroked it slightly. Oh god what a feeling.
She remarked about the size of it. I was surprised; I never thought it was bigger that a normal size. She said that it was wider than her ex's, but of average length. I have big hands, so I guess I just never noticed. Her hand on my penis made me unable to concentrate on anything else. We had been going for about an hour at this point, in the dark, on her dorm room bed. We decided to go for it. Coitus. Penetration. Sex.
She leaned over to her night stand, and grabbed a condom that she had from her ex's last visit. She unwrapped it and pulled out the latex piece. I presented my penis and she did her best to place it on. Again, my tool was wider than she was used to, so these normal-sized condoms didn't quite fit. Pleased with myself, we both had to try to get it on securely. We were successful after a minute. It's latex; it will stretch. Then she made a reference to a bad movie that we had seen, and all the sexual tension dissolved into the dark. After a minute or two of movie quotes, we got back to business, but she just had to jerk me off a little until I was stiff enough again.
Then came the big moment. F re-adjusted herself on her bed, and got comfortable. She opened her legs, and directed me to lay on top of her in between them. I did so, keeping my resolve and my intelligence intact. I stroked her left boob a little and she touched my penis a little more. We decided to start it up. F grabbed my rubber-encased sex organ, and moved it to a space between her thighs. She had to fiddle for a second. Finally, she had it in place, and she told me to thrust. I guess I did it wrong, and I didn't make it in. She sighed and repositioned it again. This time, I thrust into her, and all 6 inches of my little finger slowly slipped in to this new, mysterious world of her vagina. She flinched a little, and let out a small sigh after catching her breath. I stopped briefly just to make sure I did it properly. She said yes, and to start pulling in and out.
I started to do just that. I almost pulled back too far, but after a few thrusts inward and some cleverly-timed retreats, I got a pace going. All those years of playing F-Zero finally payed off, as attention to tiny detail and precision were key. F wrapped her legs around me, and I pressed my body up against hers. We wrapped our arms around each other as I continued to thrust and pull over and over. To me, this felt crazy and wonderful and odd and amazing. I never thought a vagina would be so warm and welcoming. From my experience with women, I expected it to be address me like "What the hell are you doing here? Fine. Be quick. I'll have to urinate soon. And don't be too rough. Do this do that." But instead, F's vagina was like "Oh, hi! Welcome! Come on in! I have some tea on the stove for you and dinner is almost ready. Why don't you take your shoes off? Relax! You came at a good time; we just finished menstruating less than a week ago."
Her sighs of pleasure turned me on even more. We were finally able to keep up the sexual tension without our friendship getting in the way. The awesomeness that I was feeling was something so familiar to masturbation, but so much more intense and personal. Her pleasure was something that I craved. I've always had this desire to please women, probably stemming from my mother's constant dissatisfaction with me as a son. But now, with F, inside her body, I was good enough to make a woman happy. Her small spasms and panting, her stroking of my back and turning her head side to side all told me this. She told me, while I was penetrating her, that I was doing good for a first-timer, and that she preferred a girthy, normal-length penis to her ex's very long, thin penis that often poked at her insides and hurt. She got more stimulation and less pain from me. That's something I liked to hear.
She told me to speed up a little. So I did my best and started thrusting and pulling back quicker without losing momentum or force. It felt better for me and I could tell she appreciated the extra, lubricated friction. She panted more heavily and so did I. I don't know why I never came inside her. For F, I thought I was in a position that would be stimulating her clitoris, but she didn't have an orgasm, either. It was still sweet, though. Our sexual passion was building up more and more. She held on tighter to me as my movements inside of her got faster and harder. It was all going really well until...
Her alarm clock sounded. I stopped. She looked over, cursed, and we both saw that the time was 8:30. We had been at this for an hour and a half, but now she had a sorority function to attend. I pulled out and she got out of bed. She answered her phone. Her friend was waiting for her outside. So F got dressed while I took off the condom and got my clothes off the floor. I had never seen a woman getting re-dressed before. I found it arousing somehow. She was beautiful. I got my skinny jeans back on and she got into her semi-formal dress and brushed her hair. I came up behind her and pet her and kissed her neck, knowing that I just nailed this thing of beauty. We got our things together and left for the front hall.
There, F saw her sisters outside. She put on her coat. She turned to me, and kissed me on the lips again. She said that it was really good for a first time, and even though we are friends who are not dating, we had no regrets. It was fun. It was sexy. We did it for the lulz, but we're not going to make a habit out of this. Later on, F would start dating again, with not very good success. We both told a decent number of people about our activities, despite how we wanted to keep this secret at first. Later on, F and I would always make jokes and references to what we did, usually to piss of other people who are still virgins. Even now we still laugh about it. I'm proud to have lost my V-card to F. She's a beautiful woman and I can think of fewer people better to let me have this experience.
After that, my self-esteem rocketed. The world became much more manageable. I wasn't as afraid of women. I felt more important and capable. I felt loved, appreciated. I felt like I was good enough. As for F, this was just an experience to let her move on from her ex. This was important for her to move on in general from her old high school life. We both benefited from this. It could have gone better in some ways: I would really liked to have fingered her a little since I have big fingers, and I would really have liked to do some doggie-style for a few thrusts, but all things considered, it was a great trial run. Losing my virginity rocked.
Never forget 11-11-11.
So I have been friends with a young woman who, for the purposes of this blog, I will call F. F and I met through a mutual friend of ours, and we just clicked. We have similar views about life and people, and we're both rather nerdy. We both like sitting around, talking about movies and feelings and girls. She's defiantly bisexual, a product of her intense feminism. F had a boyfriend from back home, and for her first year at college, they almost broke up. It wasn't just the distance; she was moving on with her life at a university while he was stuck in community college with no prospects or grades. Last fall, they broke up for realz. It was kinda sad, but I had to be there for her. She cried for three days straight. She was on her period at the time, too, so it all kinda went to hell.
F emerged a sexually-independent, forceful, non-submissive woman. She became very flirtatious with everyone, and I found it fun. She and I started to cuddle and have emotional conversations regularly. Through this, we established a deep, personal bond. We sort of became dependent on each other. She felt like she wanted to explore affection from multiple people; I felt like I needed acceptance from women (something I've rarely even had). She opened up her feelings of insecurity with men, and I opened up about how basically all women in my life have been scornful, arrogant, spiteful bitches who have no apparent purpose on this earth but to reject me and make me feel worthless.
F saw this. She sympathized. She wanted me to feel good about myself. I have an abysmal self-esteem caused by women as a gender, and F single-handedly wanted to fix that. We would cuddle furiously and...