My first taste of sex was when I was fifteen, and I had my first girlfriend. She was short, blonde, intelligent, cute, and delightfully horny, but distressingly Christian, so "proper sex" was Right Out. However, she loved talking about all the things she'd love to do one day, and would happily get naked and let me put my hands and mouth wherever I wanted, which was good fun. I wish I hadn't been nervous about the thought of masturbating in front of her, because I bet I could have gotten away with doing it with one hand while groping her with the other, which would probably have been awesome.
That came to an end half a year later, thanks to all that Christianity and a few other issues, and I was sadly single for many years, despite a couple of near-seductions that got as far as a kiss, and one brief relationship with a girl who let me touch her breasts, or put my hands between her (clothed, alas) legs, before I met a girl at University. I can't really call her a girlfriend... she pretty much just decided we could have sex, so I finally got my cock sucked and to fuck her in a viariety of positions. I didn't come, really because I was too awed by the novelty of it all and "letting go" has never come easily to me, but that was fine - it meant I stayed hard and at it until we both got tired, which kept her coming back for more, and meant I got to leisurely experiment with different positions. It didn't last much more than a week, mainly because I wanted a girlfriend more than a fuckbuddy, so we went our seperate ways.
I had a couple of one-night stands with American friends of friends who were visiting the UK on holiday. I'm not sure where this pattern began, but it was a bit unsettling at first, as I was really after a girlfriend more than casual sex, and these first two tended to come home with me for a night of passion, then over the next few days made it clear that that was that. I still hadn't had an orgasm in the presence of a girl yet. Things improved later, though (on both fronts!)
I had a girlfriend for about a month, and we groped each other extensively, but didn't have sex as she was nervous about the pregnancy aspect. She was really lovely and I was sad it didn't last between us. We still keep in touch, a little.
I then started chatting online with a female friend of a friend of a friend (I forget how it began), and we got along well; she was quite attractive but not my type, so I could talk openly with her without the stress of wondering how I'd seduce her. Our discussions led to her telling me about her frustrated virginity (she was the kind of girl who wanted to have a lot of sex), and I commiserated with tales of my early sexual history, and when she asked if I could help with her sexual frustration, I was happy to. Although this was casual sex, the way it occurred between friends after having talked and both knowing what we were getting into removed the whole seedy aspect. She came to visit me, and we chatted, then retreated to the bedroom, nervously. I was aware that this was a scary time for a girl, so I gently broke the ice with a tickle fight that led to kissing then to groping. I remember rubbing her cunt through her tights and knickers, and her reaching down and pulling them off, spreading her legs, and looking at me hungrily. She's dressed mildly sluttily, and that "Come on... fuck me" really turned me on; I've had a taste for sluttiness ever since.
Anyway, I went down on her and fingered her and tried to get her as horny as I possible could; she hungrily sucked my cock while I used every trick I knew on her cunt and clit, then after asking if she was ready, I carefully knelt between her legs and slid my condom-sheathed cock in. I laid there for a while holding her and kissing her until she said she was relaxed about having me inside her, then, slowly at first, fucked her. I still wasn't orgasming, so we kept at it all night, trying different positions to see what she liked; then she asked me to masturbate so she could see me ejaculate, which I did and enjoyed greatly.
I got a girlfriend a while later, and we lasted for several months. Repeated sex with the same woman was leading me to relaxing into it a bit, and then one evening, she jacked me off until I came. It was the most intense orgasm I'd ever had, and semen ended up on the pillow beside my head. The next time we met up, she lay on her front and I fucked her from behind, and the memory of coming in her hand combined with the feel of her wet cunt and her shapely buttocks (I've always liked buttocks) pushed me over the edge; I filled my condom. I had soon lost count of the number of times I'd come inside her, but despite many attempts I never quite managed to do it in her mouth.
I met up with my frustrated (ex-)virgin friend again (she lived quite far away so meeting up involved train journeys and extensive planning), who I'd been fairly regularly having phone sex with for a bit. We had a lovely weekend, strolling around her town together, stopping to snog here and there, alternated with fucking her brains out back at her place. She'd gotten quite keen on the thought of anal sex, and had even tried to do herself with her vibrator to no avail, so I brought her a present of some KY jelly. Using this we had no trouble in getting the (condom-covered) vibrator surprisingly far up her arse, but I became nervous when she asked me to replace it with my cock (What if I hurt her? What if it was icky?), so we didn't get that far. I still didn't come inside her that weekend, as she wanted me to come on her face and breasts, which I did a few times, and she jacked me off in the shower while I fingered her cunt and arse and we talked dirty to each other.
I got another girlfriend in due course, under amusing circumstances: I was on a training course, so was surrounded by New People (which was a golden opportunity to try and find a new candidate girlfriend, as my life has always been depressingly male-dominated; I've had a lot of girlfriends, but the relationships have generalled failed quickly, due to the fact that I've just not had many women to choose from, and generally only had a single meeting with them to try and seduce them in, so I've had little opportunity to screen for personality compatibility...). I was sidling up to this cute blonde to try and engage her in conversation, when I spotted that this other girl standing nearby had a 1960s "golden era" sci-fi short story collection in her pocket, which we started chatting about, and found we had many common intellectual interests. It later turned out we also shared an interest in the cute blonde, but she was thankfully bisexual (although primarily gay), so after a few slightly strange dates, she invited me home with her for some satisfying sex; I found that, once she removed all the rugged black combat clothing, she had a hot body underneath. I came in her cunt, with her lying on her back on her bed on the first try. We sat around in her room, naked, looking through books and chatting, then I became turned on by her crawling around on hands and knees to pull stuff out from lower shelves, so I came up behind her while she was crouching, and we did it on all fours for a second orgasm of that night.
Our sex was pretty good, but often faintly weird. I think she really preferred women, as she was always trying to get me to wear dresses for sex; I tried this a few times and it did nothing for me, but seemed to excite her. She was a bit aggressive about everything; she was small but muscular and quick-moving, and a keen martial artist. She wanted to put things in my arse, which I was interested in experimenting with, but I felt that I didn't quite trust her to restrain her aggressiveness enough, so I declined! She was the first woman whose mouth I came in, which was gorgeous - I'd had my cock sucked lots before, which was alright, but actually filling her mouth with my come was surprisingly intense. We tended to start off with foreplay, then I'd fuck her until I got tired, then I'd go down on her, then I'd fuck her some more in a different position, and I'd either come in her cunt, or if we got tired, I'd stop and she'd suck my cock until I came. This was pretty good.
She had many lesbian friends, of course, and often tried to arrange threesomes. Or so she claimed, anyway; the only time I directly witnessed this was when we were visiting some friend of hers and it (predictably) became too late to go home so we had to stay over. She started initiating mild foreplay with me on this girl's bed, then beckoned the friend over to join in, but her friend only laughed. "Men aren't my thing," she said, "But you're welcome to screw him on my bed." We didn't, as it turned out, although I wouldn't have minded experimenting with doing it while she watched. There are few specific things that particularly turn me on, but trying new things is one of them. I like variety!
After many months together, she suggested unprotected sex. She claimed that she had 100% certainty in the rhythm method, but I was rather nervous about the risk of making her pregnant. She was quite pushy about it, though, suggesting that I didn't trust her and so on, so we did it a few times. Again, actually feeling her wet cunt directly on my cock was pretty hot, and it significantly increased the intensity of the orgasm, and I felt good about the fact that I was leaving her full of my come. But I still felt uncertain about it from a pregnancy angle, which was combining with increasing controllingness (backed up by threats of "Don't you trust me?"), so things came to an end.
I had a three-night stand with another visiting American tourist, but this one was great. She made it clear what was on offer, and we went for it. She was a lovely person, and a sexy woman, wrapped up in one. We fucked like crazy, vaginally and orally, then I took her to the airport and we snogged until she had to go through passport control. We've kept in touch.
Over the previous couple of years, I'd developed a sort of friendship with two women. They were friends of my flatmate, really, but they visited a lot. I'd had my close female friend who I chatted to online and had met up with twice for sex (although we'd drifted apart by then), but had never really had proper female friends before, so much as friends-of-friends-who-new-my-name. But anyway, I had a bit of a crush on one of these two, so I hesitantly asked her out. We had a meal, then we snogged, then she went home. A few days later she came over and stayed the night, during which she revealed she was a virgin, but a much shyer one than my previous deflowering; I gently tempted her nervousness away then shagged her until I came, which she seemed to enjoy, but she didn't throw herself into it for a night of adventorous sexual exploration. We had a few more sex sessions, and I was nearly getting her to consider the idea of, say, going on top, or touching my cock with her hands, but things fell apart for unrelated reasons.
Then I met my future wife. We went out for a meal and a long walk together, then snogged on a bench overlooking the river. We had to go to separate homes for logistical reasons, but then we met up at the weekend, at her place. We sat on the bed and snogged, then we lay down, then we slowly proceeded to shed clothes, up to a point, when she started to resist, so I stopped. She revealed her virginity, and that she was somewhat struggling with some social conditioning to not have sex on second dates, but her resolve faltered and she gave me permission to continue, so I treated her to lots of foreplay, before getting the condom on. She became nervous and dried up a little, so it took lots of attempts and further foreplay before I got inside, whereupon I executed yet another gentle deflowering, then shagged her until I came. She was a bit sore so there wasn't much afterplay, and she even bled a little. But having opened the floodgates, all of her pent-up desire for sexual experimentation came out; within a couple of weeks I'd bought her some bondage gear, and I fondly remember the first time I came in her mouth, because she was blindfolded and handcuffed. A few of my exes had been into mild bondage, of the "tying hands together with a scarf" variety; it had never done much for me, but clearly aroused them significantly. However, she was quite into it, so I got to experiment a lot more, and started to enjoy the relative freedom of tying a girl up and "doing whatever I wanted to her" (we agreed a safeword, but it's never been used to date), rather than my usual restrained gentlemanly habit of negotiating to do something we both wanted!
We got along really well, turning out to be very compatible in terms of personality and sex. After many months we moved in together, and sharing a bed every night led to sex becoming a regular event rather than something I looked forward to meeting her a few times a week for; however, it became apparent that her appetite for it was greater than mine, which had not been an issue at all when we only met a few times a week! She wants it several times a day - I prefer to stick to about five times a week!
She turned out to be interested in anal, the second woman I'd been with who'd expressed that. So we got some KY jelly, and experimented with putting the dildo in each other's arses (I trusted her more than I had my previous ex who wanted to do that!) - having a dildo in my arse was OK, sometimes producing nice sensations, but mainly enhancing my orgasm. However, she was really into it, so after a few sessions with the dildo, we tried my cock.
She got down on all fours, and I started off with the dildo to get her loosened up and ready for it; then I put on a condom, smeared my cock in KY, grabbed it in my latex-gloved hand, and pushed it in. Getting the tip in was tricky, not because she was tensed up or anything; just because I was inexperienced and it was hard to find the right angle. But I managed it, and then slowly worked my cock in by pulling back a little then pushing a little further each time. It was a very intense stimulating experience - her arse was wickedly tight, and it felt different to her cunt. The novelty of putting my cock between the buttocks of a bent-over woman and sliding it deep into her, yet feeling very different sensations, was quite exciting, and once I'd reached a good level of penetration and started gently thrusting the full length of my cock into her arse, speeding up as she got comfortable, I came pretty soon (which was probably a good thing, as I didn't want to overdo the friction on her first time).
We've done anal sex perhaps once every month or two; she has to be in the mood, and as it takes a bit more preparation and cleaning up afterwards, we only do it when we're not too tired and we get to bed early. But we're both really turned on by it (she frequently asks me for it; it's not something I have to beg her for!).
We've had sex in vehicles a few times, too. The first time was when we were staying at her parents', and sex wasn't a logistical possibility. So we drove off in the car, bought some condoms, and after MUCH searching found a dark, secluded, dead end. I was incredibly horny, having had to do without for so long. Sitting in the passenger seat, she pulled her t-shirt up so I could play with her breasts, then lost her trousers and knickers. I clambered into the passenger footwell and gave her the most vigorous pounding of our lives, making the car rock and steaming the windows up, before exploding hard inside her; that condom ended up with a record quantity of my semen in it.
She's quite kinky; I'm not particularly, but I'm happy to indulge her fantasies. Sometimes I'm not in the mood, and she used to get very disappointed when I refused sometimes, but things are better now: she's not so demanding, and as a consequence, I'm not so tired of it, so am much more likely to be up for it. Generally, she likes to role play situations with me being an older man in some position of power, and she a slutty young woman. I get some kicks out of her acting slutty, especially if she dresses for the occasion. Spanking her turns me on somewhat, too, mainly because she's bent over (and I love fucking her on all fours) and I get to feel her buttocks. Spankings often get us both in the mood for my cock going up her arse.
Trying for our children has been fun. She can't take the pill due to medical issues, so it's always been condoms; but when we're trying for a child or she's pregnant, we have lots and lots of unprotected sex. I like feeling her cunt with my naked cock, and I like the idea of filling her with my semen when I cum. We've always had a condom for the anal sex, and I have mixed feelings about trying it without; I'm sure it will be an intense sensation, but it might also be a bit icky. So we have an as-yet unrealised plan to do it in the shower, so we can clean up easily. Thing is, our shower is a lukewarm dribble, so we'll save this for if we're ever in a hotel with a decent shower together!
We'd both really like to try group sex. She's bisexual, and I like the idea of watching her being fucked (even more so if I can fuck her too at the same time), so a threesome with either gender would be nice. We'd quite like to get another guy and spit-roast her on all fours, or have her straddle him and ride his cock while I kneel behind and take her in the arse; she'd like to guide my cock into another woman and play with both our bodies while we fuck; to kneel between another woman's legs and lick her cunt while being fucked from behind by me, or to fuck a woman while I watch, then for me to fuck her afterwards.