Where it happened: Her bedroom at her grandparent's house
Langauge: English
Sex: Male
Rating: 5
Category: Straight
I’ve been reading this website for awhile about others’ first experiences, and at the time when I first started reading this, I was a virgin.
I’m a 22-year-old guy, and I’ve known this girl for a couple of years and dated a few others. I considered myself as someone that girls really wouldn’t go for, as I’m a bit of a computer nerd, but these past few years I’ve really been putting a lot of effort into the dating scene to try to get a girlfriend and actually experience cuddling, kissing, having a relationship, and sex.
With the 3 girls I’ve had as girlfriends, this one girl has lasted the longest and known me the longest, and I like her a lot more compared to the other ones.
Since it was so hard for me to try to get a girl out like anyone else would, I’ve relied heavily on online dating through sites like Date Hookup, POF, and OKcupid. I met one girl on each site. I met this girl on POF. She’s very attractive in my opinion, the other girls I met from the internet weren’t really attractive to me.
She originally wanted to meet as friends, and that’s what we did. I was her best friend for a long time, and we’ve gone through a lot of ups and downs throughout our friendship, to points where we would stop talking to each other for a few months, getting back together on good terms, and that.
She asked me out last November to be her boyfriend. I was shocked at this because we tried being boyfriend/girlfriend the other year and it didn’t last very long.
I had a little bit of experience with kissing, cuddling, and things like that, but never had sex. I felt very down on myself because I felt left out compared to everyone else I known who had done it. It was just something that I couldn’t stop thinking about for awhile at times, and just tear me apart. I felt so alone.
She and I, over these past few months, have cuddled, kissed, made out, felt each other up, but this last night (technically this morning), she surprised me by asking me to go down on her and then after that, having sex with her.
She was always telling me that she wanted to wait till marriage to have sex again (she’s had 2 other sex partners in the past, she last done it in September 2007 if I remember right), so I must have really meant something to her to finally want sex now. It is Easter Sunday 2012. That’s when I lost my virginity to her, and I don’t regret it.
I met up with her last night around 9PM Saturday. She wanted to watch “The Breakfast Club” with me, because we were playing karaoke the other day, and the song “Don’t You Forget About Me” from that movie was on the game.
After the movie, we were cuddling each other, kissing for awhile. She took off her bra and pajama top, and I kissed her all over on her back, stomach, and sucking on her boobs and nipples. She did the same thing for me in return by kissing me and smothering me with love. I really enjoy it when she does it to me, it makes me feel so loved.
For awhile, these past few times I would be with her in her bed, I wanted to slide my hand over her pussy on top of her clothes to see what her reaction would be.
I fingered her only once before, maybe a month or so prior. She had told me that she wanted to wait until our 1-year anniversary before doing it again. She surprised me because she asked me to finger her again. I did for awhile.
Later, she asked me to go down on her and eat her out. I hadn’t done that before. It took me a little while to figure out what was the best way to do it, and I really enjoyed hearing her moan, squeal, say “Oh god”, the various cute little sound effects from the good sensation she was feeling. She finally reached orgasm, and she said it was fantastic, probably compared to how fingering and herself masturbating had felt.
She then hit me with another surprise – she told me that she would have sex with me if I wanted. I never thought I’d ever hear her say that, with how she told me things before about waiting until marriage and how reserved she’s been with me in the past about getting physical. The reason why I think she said that was because she was horny and that was a way for her to give me pleasure for me giving her pleasure with her orgasm.
I told her that I would, but I would need to get a condom out of the car (I had a package of them just for such occasion). I ran out to the car and got it, came in, and started.
I’ve come to realize with her that I’m a bit hard to get up, and reach orgasm with. I think it’s because of how much I’ve masturbated over these past few years and maybe because of my familiarity with her with us cuddling, kissing, all that – which I think I’ve built up a tolerance with. The thing that I like a lot in girls is their breasts (smaller ones more, like what she has, but nothing really too big), kissing, hearing her voice, cuddling, all that. I thought it was a lot of fun when she and I would pin each other against the wall and make out, feel each other up.
I know many people say that they don’t last very long their first time – but I lasted quite a long time. And I didn’t even reach orgasm. We just stopped because I was getting a bit tired.
It took me awhile to get hard and fit the condom on, and since she hadn’t had much sex before (and it was so long since she last done it), we both really didn’t know what we were doing.
It took me some time to realize how to put it in (where the spot was to fit it in), and an actual good position for both of us to be in. With this, I felt a little embarrassed. It really felt like nothing, probably because I had a condom on, but I did feel the up and down feeling that guys simulate when masturbating.
We only found like 2 possible positions that were working for us, which was her lying down on the bottom, and the other way with her on the top of me riding me in the cowgirl position.
I remember looking at the clock from 2:30AM to 2:50AM when we stopped, I don’t know how long we were doing it before when I first looked at the clock. And like I said, I didn’t even reach orgasm.
She said that it’s the most passionate sex she’s ever had, with kissing while doing it, which she’s never had before.
She doesn’t want to give me a blowjob, she says she would rather have sex with me than to give me a blowjob, which I thought as a little strange, as I think a lot of girls would say the opposite thing.
We talked about it and I said that I would go down on her anytime, because of how good of an orgasm she had.
I would like to have sex with her again, we talked about that we may get better at it if we did it more often.
For awhile, after doing it, I was worrying about she might getting pregnant. She’s not on the pill, but I did wear a condom, and I checked the condom throughout us doing it, and after we finished. I went to the bathroom and put water in it to see if anything leaked out, and nothing did. I’m just hoping that nothing happens with that, as I really want to wait to have kids until my later 20’s / early 30’s, after I’m settled down with my own place to live as I still live at my parent’s house.
Bottom line is that I don’t regret it. It’s something I wanted to experience for a long time, and I didn’t want to be looked down by people having not done it, as that’s what this society seems to be about here in the US. For awhile, I was having problems with hearing some songs on the radio (like that song S&M by Rihanna) because it’s emphasizing sex when I was a virgin.
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