1. I’m a mostly-straight 31-year-old Caucasian guy. I started masturbating when I was 11 or 12. I had already found much of the erotic material in the house, including a copy of Anais Nin’s Little Birds and multiple boxes of my father’s naked-girls magazines, including old copies of Playboy and Oui from the early '70s through the early '80s. Throughout my teens, I raided these stores often, secreting individual magazines away in my room in various hiding places for later use and masturbating wherever they were. I tried to leave the boxes the way I found them, but I was probably about as subtle as a tornado. Probably for that reason, the boxes kept moving: first from Dad’s closet to the attic, then to the basement, etc.
2. I masturbated constantly throughout my teens, but my method changed over time. At first, I gently rubbed the inside of my right wrist against the ‘front’ of my cock, just below the head. This depended on both cock and wrist being as dry as possible; otherwise they produced unpleasant friction. As I got older, I started using my fist instead, in the more traditional/stereotypical way, usually in the shower (as I lacked lube). I also came up with another seemingly less common method that I still use when I don’t want to use lube (often when I masturbate while watching something on my computer): I place the pointer and middle fingers of my right hand at the spot just below the head of my cock – by far the best-feeling single part of my whole body – the thumb on the other side, and then rub rather hard in a tight clockwise circle until I come. Lube isn’t necessary because the skin of my fingers is in constant contact with the same patch of skin on my cock. I find the superficial visual similarity between this method of mine and the stereotypical female masturbation technique pretty interesting.
3. When I first started having orgasms, the sensation of climax was not accompanied by ejaculation. That came later (no pun intended), and when it did I was worried I’d broken myself. At around the same time, due to the weird hormonal tomfoolery that is puberty, one of my nipples (I can’t remember which one!) changed from the flat, massless thing it had been to having some sort of useless spongy tissue behind it. But it was just the one nipple, not the other. I mentioned it to my parents after awhile, and they were sufficiently concerned to bring me to a (female) doctor, who poked me and prodded me, including giving my testicles a brief, clinical fondle, and asked if there was anything else that had changed. I felt like I should say something about how now, when I masturbate, gooey fluid comes out of my cock, but I was too embarrassed. Her diagnosis probably wouldn’t have changed: you’re in the throes of puberty, and everything will be fucked up for awhile. After a few months, my other nipple underwent the same process.
4. When I was a kid, I had a largish stuffed bear. During the day, he was a stuffed animal (and had, when I was younger, been either an ally or an enemy in endless mock battles of various sorts), but at night he transformed into a girl. I made up elaborate romantic/sexual stories with a fair amount of kissing involved, the culmination of which was ‘sex,’ which involved lying on my back with her/him/it lying above me, placing my penis between her/his/its legs and masturbating the normal way until I came on her/his/its hindquarters. Needless to say, the fur on that particular patch of fabric wore off and discolored in a rather telling way. I can’t express how happy I was to hear, later in life, that many women start masturbating with the help of a particular stuffed animal. I retain no sexual interest in stuffed animals, thankfully.
5. I’ve had sex, which I define as "any of the participants have an orgasm and/or there’s penetration," with 9 people: three guys and six girls. Despite this first-glance near-parity, as I said above, I consider myself mostly straight. I’ve kissed or made out with many more girls than the above. Something like eleven. I’ve had three long term relationships, all with women. K. and I were together starting when I was 17 and split up when I was 21. The relationship with E started when I was 22 and ended when I was 25. L and I got together when I was 25, and we’re still together. I married K when I was 19, which was (of course) a bad, bad idea. We divorced when I was 22. E is a wonderful person, and we had very good sex together, though we ended up not working as a couple in other ways.
6. The other girls I’ve had sex with were as follows. The first was a high-school thing that lasted less than a year. We made out, and fumbled around under blankets, and each of us came a few times. It was all manual. The second was a sexual friendship when I was 26, when my then-and-current girlfriend, L, was away for some time in France (she knew about all of this, and did similar things during that same period – see below). We never had intercourse, but went down on each other and such. We stopped when L came back to the US, mostly at her insistence. We’re still good friends, and I’d be interested in restarting the physical aspect of our relationship, but she fairly clearly isn’t. The third was a graduate school friend of my girlfriend’s, let’s call her J.
7. The guys: A cousin, a year younger than me. We lived in neighboring states, and fooled around for a period of years during our early teens every time our families got together, which was often. It was mostly mutual masturbation or trading hand jobs, though we went down on each other a couple of times. We rarely if ever kissed or made out. The second was my best friend in high school –more on him below. The third was J’s ex-boyfriend, and again you can read more about him below.
8. I’ve been mostly-sorta-raped, by my best guy friend in high school. I spent the night at his house (okay, in his garage). We smoked pot and I got higher than I would’ve preferred, and I promptly fell asleep. I woke up with my cock in his mouth and his in mine, right before I came. I then felt obliged to finish him off, though mostly I wanted to get the fuck out of there. He came in my mouth and I swallowed most of it – some got on the collar of my shirt. I went into the house afterwards to get away, and remember not recognizing myself in the mirror. I mustered up the courage to tell my then-girlfriend, and she dumped me. His girlfriend laughed it off. That probably pissed me off more than anything.
9. I’ve had both a three-way and a four-way, both involving my current girlfriend and J. The four-way included us three and J’s ex-boyfriend. Both were nice, if somewhat confusing. The high point of the three-way was when the two girls came within seconds of each other, my girlfriend fucking me and touching her clit while the other girl straddled my face. The high points of the four-way were watching my girlfriend suck J’s ex’s cock while I fucked her from behind, and watching him fuck her. He’s the last boy I listed above, because at the end of what I may as well call the orgy, after the girls had both come at least once, I sucked him off while my girlfriend made me come with her hand. The hottest thing about making him come that way was how much the girls seemed to enjoy it.
10. My sexual fantasies have shifted considerably over time. When I was younger, my most common fantasies were of a girl masturbating, cunnilingus, or girls having sex with each other. I never fantasized about anyone going down on me, or any other man, or about any penetrative sex. Once I got the chance to go down on a girl on a regular basis, with K, that fantasy faded. But she only masturbated once when I could see her, so that fantasy kept going strong. At about that time, I also started to get off on the idea of the woman I love having sex with someone else. I still fantasize about that regularly. More recently, because I’m fortunate enough to be with a woman who lets me watch her pleasure herself, the woman-masturbating fantasy has faded somewhat. I have for the first time in my life begun fantasizing about sex involving men and women: women sucking men off, men and women fucking, men coming on various parts of women’s bodies (breasts, faces, cunts). These fantasies always involve a woman, and the most arousing part is her desire – she always desperately wants what’s happening.
11. I love, love, love going down on a girl. I knew long before I was sexually active that one of the things I most wanted to do was make a girl come with my tongue. There’s something so exquisitely sensual about it, and quims are simply the most beautiful, sexiest things in the world (unfortunately, none of the available nouns do them justice). I desperately desired to go down on the high-school girl, but she lived in the same room as another girl – and yes, this means that all of that making out and sometimes-orgasmic fondling occurred with other people around, usually doing the same things – so we had to keep up a certain ‘plausible deniability.’ The first girl I ever ate out was K, the one I later married. We were both instantly hooked. Over the four or so years we spent together, virtually all of her orgasms (at least hundreds, if not more than a thousand) were from cunnilingus. E also loved getting head, and definitely had the majority of her orgasms that way. My current girlfriend not so much. I only get to get her off with my mouth maybe once a month – but none of her other sexual partners have ever made her come that way. I’m told that I’m exceptionally good at giving head, but I’m not sure I quite understand why it would be difficult. It seems like skill is less important that sensitivity, empathy, and paying attention.
12. I’m much less partial to having someone go down on me. I prefer hand jobs to blow jobs, generally. K never went down on me. My second did, and it was sort of a revelation at the time. My current girlfriend is the first woman who has swallowed my come. I come in her mouth fairly often, but usually someone’s hand is involved.
13. I’ve had anal sex, both on the giving and receiving ends. E liked anal quite a bit – her asshole was almost like a magic ‘orgasm now’ button, especially when I used a finger there in conjunction with my tongue on her clit. I’ve been fucked in the ass with a dildo by E and my current girlfriend. We invested in a strap-on for her, which she seems to love. I don’t give it up very often, though, because I have to be in a very particular mood. The orgasms I have with something in my ass are incredibly powerful; I’m usually very quiet during sex, but orgasms involving anal make me make noise. My girlfriend is only just coming to enjoy her bum. On rare occasions she likes just a finger or a very small vibrating dildo there, usually while either my cock or fingers are inside her cunt. We’ve tried my cock in her ass twice, starting earlier this year, but it’s quite a lot for her to handle, and will likely always be a rarity.
14. I’ve always felt ‘queer’ in a gender sense, despite not being particularly ‘gay.’ Part of this is that I would’ve preferred to be female for a large chunk of my life. Girls just seem cooler, more respectable, even still. Most of the despicable bullshit in the world – war, environmental destruction, etc – comes from men or masculine thinking and action. Add to that the fact that I’ve felt weird about my cock until fairly recently. I think that’s partly because it repulsed my wife – she never wanted to do much with it other than fuck it. I’m getting over this, mostly due to the fact that my current girlfriend simply adores cock, especially mine. It’s hard to feel bad about something that someone you love is pouring adulation upon. Still, my girlfriend and I like playing around with gender roles more than I ever have before. She likes dressing me in dresses, and often when she’s fucking me she fantasizes about being a boy and coming all over me (sometimes in her fantasies I’m still a boy, sometimes I’m a girl). Sometimes it’s just incredibly arousing to be fucked as a girl.
15. I think I have a physical type: shortish, dark, with short dark hair, small breasts. So, of course, my current girlfriend – the girl with whom I’ve been happier than I’ve ever been with anyone – is a completely different physical type: tall, with blonde hair and large, luscious breasts. It’s fascinating. She is by far the best lover I have ever had. She enjoys sex quite a lot, and we have quite a lot of it. She’s a somewhat shy person, but is very outspoken and demanding sexually, which I love. She comes most often from fucking me while either rubbing her clit or using a vibrator on it, which is incredibly sexy to watch and be part of. She’s perfect for me.
16. Every long term relationship I’ve ever been in has been an open relationship. This dates back to my first long term relationship, with K. Very soon after we met, when I was 17 and she was 18, she went to South America for nine months. We carried on a long distance relationship, complete with letters and “I love yous” and every schmaltzy thing you can think of. She tearfully confessed to me a few months after she returned that she’d made out with 37 guys while down there, writing such sappy love letters to me. I realized a few things. I wasn’t particularly upset – what was the big deal? I didn’t believe that anyone would ever not at least want to do sexual things with someone other than me while in a relationship with me (and, of course, I wanted things with other people too). I would much rather find out about it at the time than be lied to and have things hidden from me. And I couldn’t deny that I found it hot. So we talked about it, and I came up with a set of rules I’ve had in every long term relationship since: fuck anyone you want, as long as you a) tell me about it first, b) be safe, c) continue to put me first in your heart and life, and d) describe it for me afterwards. Every woman I’ve been with has taken advantage of this opportunity. K let guys finger her in bars. E had sex with a guy in Fargo and, on one drunken evening when I was out of town, a mutual friend, his girlfriend, and her brother (not, thankfully, all at once). And L is racking up a truly impressive tally: since we’ve been together, she’s fucked her ex boyfriend, an Argentinian in France, two different guys in D.C., a medical student, a puppeteer, her female graduate school friend (in the three-way and one other time just the two of them), that friend’s boyfriend (in the four-way), and jerked off and been jerked off by a guy friend in a tent on a road trip. She continues to fuck her ex on a regular basis, including once within the last two weeks. I’ve taken much less advantage of these situations, mostly because it just seems to be easier for a woman in a relationship to find no-strings-attached sex than for a guy to find the same (or maybe I’m just not trying very hard).
17. Despite looking at nudie magazines as a kid, for years I really didn’t have much interest in mainstream porn. My dad’s Playboys and Ouis were so tame, just naked girls. I don’t find nudity particularly erotic – seriously, it’s just people not wearing clothes. But the porn available in the late 80s and early 90s was so bad: fake breasts, fake hair, fake nails, fake orgasms, shaved cunts, makeup, bad music, etc. Not hot. So for much of my 20s I avoided photographic or video porn, and got into literary erotica – I have a whole bookshelf filled with dirty books. I kept looking, though (I am a guy), and finally two different dynamics created visual porn that I find watchable. The first dynamic is woman-centric, real orgasm centered websites like Beautiful Agony and I Feel Myself. The second is the rise of user-generated, real-people sex tapes. I feel a little funny about these sometimes, because it’s likely that at least one of the participants has some second thoughts about having their sexuality on the internet for the rest of time, but they're undeniably hot.
18. I write erotica. Much of it is from a female perspective, though not exclusively. Having read quite a bit of the genre, I believe that my work is as good or better than most of what sells. I’d like to sell some, but I can’t figure out how. I hate the business aspect of any creative endeavor. It’s an ongoing frustration.
19. I would say that on average, since I was about eleven, I have averaged at least one orgasm a day. Very rarely does a day go by in which I don’t come somehow, at least once. It’s something as reliable at this point as eating, sleeping, etc. I find that somewhat comforting.
20. I like to do sexual things in unusual places. I’ve eaten out a girlfriend and been subsequently jerked off in a tree in the middle of a public park. I’ve masturbated at work, at school, on trains, buses, planes, in public restrooms, in the back seats of cars. I’ve had sex at friends’ houses, in my garage, in tents, in the woods, in canoes, in lakes with people swimming all around. For a while, E lived in the same room as a mutual friend, and we often had all various sorts of sex – intercourse, anal, oral, you name it – while he was in there sleeping (or pretending to sleep). I’d like to do more of this sort of thing.
21. I find phone sex and sex over the internet pretty interesting. I’ve had phone sex and ‘cybersex’ (I hate that term, it makes people sound like cyborgs) with my past two girlfriends, usually while we were physically separate for a period of weeks or months. I’m generally much more interested in hearing what my partner is actually doing than inventing some sort of grandiose fantasy in which we’re doing something together. When I was in my early 20s, back when my longing to be female was much stronger, I would often pretend to be a girl and masturbate online with strangers. More recently, I’ve only engaged in online sex with people with whom I’m already sexual. One of the most interesting things about online sex, especially via gmail, is that a record of the conversation is kept. While we’ve been together, my girlfriend has come online a couple of times with her ex-boyfriend (once in a student lounge at school!), and she’s shared the transcripts with me. They're quite hot.
22. I’m basically a big voyeur. My desire to watch and listen is much greater than my desire to be watched. I love hearing another couple get it on, even when I’m not attracted to either of them. I’m a homeowner now, but this was definitely one of the nicest things about renting apartments in duplexes and larger buildings. In one place, I shared a common wall with a couple that must have just gotten together, their lovemaking was so constant and so drawn out. I’ve heard roommates getting busy through heating vents, strangers in motels and bed and breakfasts, etc, and liked it every time. One especially interesting period was after E and I had broken up and I’d started going out with L. I’d been living with E and another friend, but moved out for a couple of months to give her some space. Then I moved back in, and lived on the front porch for awhile. During that time, she took up with another guy. We’d stayed close (to the extent that, before she started this new relationship, we masturbated together on several occasions, which had been somewhat emotionally trying but also quite lovely), and she seemed to take a certain malicious pleasure in telling me how great the sex was, that his cock was larger than mine or any other she’d ever had, etc. (She was clear that I was still the best head she’d ever had, though.) And she wasn’t shy about letting/making me hear them fuck. I got myself off a number of times while listening to them, sometimes from my 'room' on the porch, and sometimes from closer to the room we’d shared until recently. I then discovered that the light from her bedroom window reflected just so off of the windows of the neighboring house (which was only a few feet away) that I could see them. So I watched them, whenever I had the chance, and enjoyed it profusely and orgasmically. The voyeuristic thrill I’ve had more recently is that my girlfriend and her ex have, on a couple of occasions, taken pictures of themselves while they fool around. I’ve been able to see most of these pictures, and I’d very much like to see them all.
23. Recently, over the past six months or so, L and I have gotten into something new: me coming on her face. It’s something I never would have expected to find hot – it can be or seem so misogynistic, so much about hating and defiling a woman. But it’s hot, and I can’t deny it. Much (if not all) of the newfound sexiness of coming on her face is that she really, really likes it. One of our favorite new activities is for her to masturbate while I come on her face. Another helpful thing is that she also enjoys fantasizing about coming on my face, sometimes as a girl (though she never has in reality, I would love it if she did) and sometimes as a boy. And sometimes we pretend that my cock is hers, and sort of dangle my upper body off the edge of the bed so that she can, in effect, come on my face. All of these things are recent, all are an increasingly common part of our sex life, and all are exquisite.
24. I adore women’s body hair. Not just pubic hair, though that’s one of my favorites, but leg and especially armpit hair as well. This may be, in part, a preference for countercultural aesthetics more generally, but it’s also much simpler. A hairy girl is just much prettier, to me.
25. I love talking about sex. Since I was a teenager, I’ve liked having female friends that I can talk to about sex. In high school, my female friends and I talked about our sex lives almost incessantly – masturbation, oral sex, intercourse, whatever. Sex continues to be one of the most fascinating topics of conversation for me, bar none. I love this site, for that reason – it’s great to see how varied people’s sex lives are, how infinitely unique.