1.) I'm 24 years old, male, and a virgin. I'm not exactly ashamed of this fact, yet I sometimes worry how people will react. And at the same time, I have so many hangups about sex in general, it's just absurd.
2.) My first kiss came when I was around 6-7 years old. I was at a friend's house, and his older sister was there with her friend. My friend was around 9, and his sister was around 13 or so. She tended to be domineering and almost abusive at times, or at least that's how I remember it. Me and my friend were sitting on the floor in the room he shared with his sister, while his sister and her friend were jumping on the beds and singing along to the New Kids On The Block cover of "We Will Rock You," by Queen, playing on the stereo. His sister suddenly leapt off the bed, landed on her feet in front of me, kneeled down and kissed me rather deeply. I think she even used tongue. After perhaps 3 seconds of this kiss, she pulled away, leapt over me and went back to jumping on the beds. I remember not knowing what exactly she had just done, until years later when I thought back on it and realized she'd kissed me. My friend told me a few years back that she had a big crush on me, despite our age difference, but there was no way I would've noticed.
3.) My first actual sexual experience came when I was about 8 years old, with my 6 year old female cousin. My memories are a bit foggy, but I remember us playing Truth Or Dare, and either she or I dared the other to show them their 'equipment.' It mostly progressed from there. The second or third time we played after this, I think I dared her to rub my... parts... with hers. She did so, and I remember it felt so good that my eyes rolled back in my head.
4.) We continued messing around like this for what feels like ages in my mind, but which was probably just a few months. First rubbing one another with our hands, to actually touching our genitals together more and rubbing that way. I thought we were actually having sex at the time, and put a stop to it after hearing of AIDS for the first time, completely ignorant not only of the fact that we weren't actually doing it, but that there was no risk of HIV or any other STDs involved. I actually believed just having sex at all could get you infected with HIV, and was terrified.
5.) I guess I learned the truth eventually, and stopped fearing catching HIV from innocent experimentation. My cousin moved, and perhaps a year later, my next experience was with a male friend of mine, who was my best friend at the time. My memory is a tad foggy, but I think it mostly consisted of the same activities I engaged in with my cousin. I remember he didn't seem too weirded out by what we did, or really to even take much notice of it at all. I also remember one incident of him being at my house, the two of us being alone together, and me trying to get him to come to my room so we could mess around, but he was too interested in some show that was on TV. I remember being irritated by this.
6.) I only had a few dating experiences in school. My first came when I was 10 years old or so, and we had our first dance. A girl I was acquaintances with apparently had been dropping hints for a month that she wanted me to ask her, but I was still a little boy playing with Power Rangers and such, so I didn't notice. She eventually asked me out herself, and I accepted. Shortly after this, a rather bitchy female classmate and her group of friends went around asking everyone if they were going to the dance, and who they were going with. They badgered me until I told them who had asked me out. They went to ask her, she denied it, and the bitchy girl and her friends proceeded to follow me around the playground, verbally abusing me, with the bitchy girl ending it by stepping forward and calling me a pathetic loser for lying, and declaring that I would die alone. The girl who asked me out came to talk to me after this, and said I shouldn't tell people we were going out or anything. The next day she dumped me and went to the dance with another boy instead.
7.) The first time I masturbated came when I was around 11 years old. I can't quite remember how I discovered it, I just remember noticing how good it felt to rub myself against a pillow. After a few tries of this, achieving only stimulation and not orgasm, I discovered the usual method of masturbation on my own, and had my first orgasm. I remember not knowing what the hell I just did, but at least I didn't feel ashamed or afraid of it. I masturbated for years, but didn't ejaculate until I was 13 or so. By this point, I knew enough to know what it was.
8.) My next sexual experience or experimentation came when I was around 12-13 years old. This time it was more experimenting, again, with a male friend. It was a lot of the same as above, except this time we experimented with oral. I feel kind of bad in that he went down on me and it felt unbelievable (I didn't quite come, though)... yet I absolutely could not bring myself to reciprocate. Because of this, we eventually slowed down on messing around, until we stopped completely. Unlike my previous experience with a male friend, we wouldn't talk about the times we'd mess around, and both of us felt fairly ashamed afterward.
9.) In one of the final times we messed around, he came up with the idea that we could try it at the same time, so neither of us could chicken out. This didn't work out so well, since we would mess around in a camper with two bed... cushion thingies. The cushion/bed things were small for ONE person, so when we tried, we ended up just... kind of diddling each other for a few seconds before realizing it wasn't going to work. I think that was the last time we did anything, though we stayed friends and hung out until high school, when we drifted apart.
10.) The second out of my 3 attempts at any form of dating came when I was 15 or so. There was a girl who was 2-3 years older than me that I'd known since I was 11 or so, and who I learned later had a crush on me. The details are murky in my mind, but I made an off-hand comment to a friend about she and I dating, and she confronted me about it, asking if I actually did want to go out with her. I agreed, and so it was. The problem then came with another male friend mocking me endlessly about it, to the point that within the remaining 2 hours left before school let out, I panicked. I talked to her before heading home and said I had to break things off, I didn't think I was ready for a relationship or anything. She seemed okay with it.
11.) My third and final attempt at anything resembling dating came when I met a girl online who lived in Tennessee. I was 16 years old, she was about 22 or 23. We seemed to take to each other right away, and progressed quickly to talking on the phone and sending birthday and Christmas gifts to each other in the mail. The plan was for me to go meet her when I turned 18. Things were honestly okay for about a year or so of this, and then she just started messing with me. Playing little mind games, forcing me to admit embarrassing things (some of which I've related here), and then being almost mocking to me about it, before finally, when I was 4-5 months from turning 18, she told me suddenly that she'd met a guy she likes where she lives, that she was breaking up with me, and then ceased all contact with me whatsoever. Though we never met in person, the havoc she wreaked on my emotions and mental state is still with me to this day. This, coupled with my treatment at the hands of the bitchy girls the first time I tried dating is likely why I am as repressed as I am.
12.) Ever since the above experience, I have a tendency to be afraid of girls I develop feelings for, rather than wanting to be around them. I can't quite explain it, but I find myself illogically nervous and even panicky at the prospect of being near them. I had a female friend I grew rather fond of in my senior year, and we took to talking to each other on the phone for a while during the last few months of school. And I found that when it got to be the time she'd call, I'd throw myself into a near panic and once or twice I pretended not to be home, because I was too scared to talk to her. I don't know why.
13.) As for the girl above... I've had feelings for a handful of girls in my life, but I've only felt actual DESIRE just once. And that was with her. Though I was afraid to be near her, and her calls alone made me nervous, I longed to kiss her, to caress her breasts, to feel our naked bodies pressed together, to fall asleep in each other's arms. And I even entertained thoughts of us losing our virginity to each other, even if I could never in a million years admit this to her. We fell out of contact for a while after senior year, and I learned from a friend that shortly after the year ended, she got serious with a mutual male friend of ours, and lost her virginity to him. The absolute, searing agony I felt in my heart at this news is indescribable. I hope like hell I never feel it again. We got back in contact for a few months after this, but fell out of contact once more eventually. She had managed to figure out my feelings for her at this point, but I never truly got up the guts to ask her out. After learning she'd given herself to another guy(who then proceeded to cheat on her with the school whore), I felt like I couldn't approach her with the feelings I had. Like she'd look at me like some silly boy. I didn't say it was logical. To this day, I've never felt that level of desire and yearning for another girl, and I doubt I ever will.
14.) The closest I came to the above again was from another female friend who apparently had a thing for me since junior high. There's only been a small handful of girls in my life who have had crushes on me, and I'm not sure why they did. In the case of this friend, we got to know each other better in the years after high school, and during an instant messenger conversation, she claimed she'd always fantasized about losing her virginity to me. At the time she was still 17, and I'd just turned 19. I wasn't sure how to react to this information, and she proposed we get together over the weekend, and deflower each other. I don't know what possessed me to agree to this, as I see so clearly now what a bad idea this was, but I agreed. Long story short, she got cold feet, stood me up, lied to me about even asking me in the first place(she claimed a friend was signed in as her and said it as a joke), and went out with another guy the next day. Not too long after this, she lost her virginity to another guy, got married to him, and they have kids now. It was around this time that, consciously or not, I withdrew and gave up on trying to get close to girls at all.
15.) The above encompasses the entirety of my sexual and relationship experience in my life thus far. As horny and experimental as I was when I was younger, I'm completely timid and terrified of sex now. It doesn't have to do with the mechanics of it, so much as the closeness. Once I was old enough to see it as potentially more than just two people having fun, it began to terrify me. I may never understand why, but as far as I can tell, it's the concept of letting someone get that close to me. Of them seeing me naked, knowing what gets me off, knowing fantasies I have, etc. I tend to be fairly solitary, and it just weirds me out to think about.
16.) Though two of the three people I've experimented with in my life were boys, I don't identify as gay, and am not the least bit attracted to men... yet sometimes I still masturbate when I think back on my gay experimentations when I was 12 or 13.
17.) Despite participating in it when I was younger, I'm completely put off by oral sex. Either giving or receiving. When it comes to receiving, I feel like I'd be imposing on the woman somehow, making her do some nasty thing just to get me off. In terms of giving it... I remember the "WHAT THE HELL DID I JUST *DO*?!" feeling I got after my male friend went down on me, and thinking of going down on a girl feels similar. I also feel like she'd look down on me afterwards, because she got me to do something that I find so disturbing, even if I know the girl would never think of me like that. I fully realize this kind of hang-up is usually something girls feel about giving oral to guys when they haven't tried it before, and not a lot of girls would look down on a guy like that. It's just another way that I'm weird.
18.) There are a few things I know there's no way I'd try, even if I were to open up and be more sexual. One of them is the whole money-shot-to-the-face thing. I don't see the appeal at all, and if it happens in porn I'm watching, it's a complete turnoff.
19.) Ass-to-mouth is another complete turn-off for me, and something you absolutely could not pay me to try, giving or receiving. Pretty much everything involving the anus is completely off-limits for me... yet I will admit to experimenting a few times when I was younger, trying to achieve the powerful orgasm that's supposed to result from stimulation of the prostate. I was never successful and always felt a bit like a freak for trying.
20.) I sometimes find I enjoy hentai and such more than porn with real actors. I'm not entirely sure why, but I think somehow knowing that the girls in hentai aren't real is sometimes more appealing to me. There's this illogical feeling I get, that the girls in porn with real people are looking at me and thinking "NAUGHTY BOY, I SEE YOU." Again, I'm a damned weirdo.
21.) While I sometimes enjoy hentai more than normal porn, there are limits. Too often, hentai seems to have a lot of jizz-drenched scenes, and that's a complete turn-off for me. As a rule, I pretty much don't want to see jizz, ever. Be it on a girl's face, splattered all over the place, or even the puddles of it that are left behind in a lot of hentai scenes. It just squicks me out.
22.) Of hentai, I enjoy 'straight shota' the most. As in, younger male with older female. A lot of people look down on anyone who enjoys shota, thinking they're getting off on the drawn image of the naked little boy or something. In my case, as with a lot of others, we're imagining we ARE the boy. This plays into one of my recurring fantasies, of being a boy of around 12-14, who is seduced by an older woman; from an older classmate all the way up to a middle-aged teacher.
23.) I sometimes realize I have a rather large number of fantasies or scenarios I use when I do masturbate or just let my mind wander, yet I'm absolutely terrified at the prospect of voicing any of them to anyone I know, and I'd probably have a heart attack if any attractive girl ever offered to act any of them out with me.
24.) Though I am still a virgin, I have enough knowledge about anatomy and sexuality that I sometimes surprise people that know me. People expect virgins to be completely clueless, but I know just about everything there is to know, stopping just short of the actual act itself. In high school, I even knew more about female anatomy and the mechanics of sex than my friends who had already started doing it.
25.) Most people would claim to be 'too old' to date when middle-aged or older, but... my feeling now is that indeed I am too old to start seriously trying to date. My self-esteem has never been high, and in terms of body image, I find myself repulsive, and couldn't fathom any woman being attracted to me. Besides this, I also feel that no woman my age would feel like wasting time on a virgin. Maybe I'm wrong, I don't know. But that's pretty much how I feel.