- 33 thoughts
- Log in to add a thought
#69: She was a friend-of-a-friend and a roommate for most of a year. I kept things platonic and didn't even flirt for a few months before eventually mentioning like I liked her. Turns out she had felt the same way the whole time. We had sex pretty much right away, and had sex fourteen times in total. She was light, so it was easier to pick her up and throw her around, and she stayed up late like me, so we had many fun nights fucking until five in the morning. It felt perfect. I would ejaculate inside of her, then we would just hang out and cuddle naked for awhile, until I would say something that would make her laugh hard enough to shoot my cum back out of her. She would say "god damn it" in the same way every time and run off to the bathroom to clean up. I really liked her, but she stopped being friendly and seemed to lose interest in me fairly abruptly. On her drunken insistence one night, I had anal sex with her, which was the first and only time I've ever done that with anyone. It seemed to work great for her, but I couldn't manage to get comfortable with it.
#70: Alright, this is a weird one. The gist is that a guy offered to pay me to put on live sex shows for small audiences if I could find a partner who was into it. A friend introduced me to a girl who he said was interested, and after meeting her, we "rehearsed" in a hotel room with her boyfriend watching from across the room. Not what I thought I was going to be doing that day, not how I would have preferred it, but it ended up being fairly pleasant regardless, although quite awkward. She held my penis at one point and asked me, "Do you mind if I... uh... oral?" which amused the hell out of me. At the time of this writing, we've only had sex once.
S-E-X...Sex....it's that simple. Like most, I place far too much significance on it than need be. Basic mechanics, in/out/in/out, nothing more. If/when we invoke our emotions into it is where issues can breed. Love,lust,like,hurt,pain....th
#60: I met her at a sex club and we had sex once. Oddly, I didn't really feel up for sex that night, and I was a little offended that this girl was cozying up to our table to hit on a friend of mine and ignore me. But after my friend ran off, she turned her attention to me, and we ran off to a room together. She was an energetic and pretty stripper, and I remember being a little offended that she squirted all over my clothes. I encountered her once again when I invited her onstage at a show, then never saw her again.
#61: She was a member of our circle of friends, and we clicked in a lot of good ways. Academics, performers, sex enthusiasts, etc. We had sex three times and it was really sincere and enjoyable. I feel like there's still a lingering "we're both busy people, but the next time our paths cross..." vibe between us.
#62: Welp, this one just cheated on me and dumped me for a second time, so... hmph. Between the two times that we dated, we had sex somewhere around 30 times. Probably not more than 35 times. When I think I'm going to be with someone forever, the tally that I run in my head of the number of times we've had sex gradually shuts off. She was a dancer, which worked out great in bed, but I often had trouble connecting emotionally. Our sex often felt like it was really just for her, and that I was just there to get her off. Which can be okay if that's what you expect, but when you expect lovemaking with a soulmate and get "smash my clit so I can meet my orgasm quota for the week" it can be disappointing. But that might just be a bunch of misplaced angst about other relationship issues. This was the first person I called my girlfriend who cheated on me by breaking major relationship rules about sex with other people. As far as I know, at least.
#63: She and I worked together on a series of shows that I did on the road. Hints were dropped that she was into me, she offered me her place to crash instead of driving hours and hours back home late at night, I convinced myself that she was too negative and unpleasant to spend my time with, then a "fuck it" moment took over. She went back to being negative and unpleasant after we had sex. Big shocker. Still, no regrets.
#64: Another first! Someone I met online specifically for sex! I don't remember how exactly we met up. Maybe Tinder? Something skeezy that felt out of character. We chatted on a webcam and showed each other our genitals, as is apparently customary in this sort of thing. I remember her saying over the video chat that she wanted me to "pound [her] with that". I met up with her at her apartment and obliged. Before sex, we spent some time talking about some difficulties in her life, and I tried my best to reassure her and give her advice. During sex, I remember being surprised that she wanted to kiss me so much, and surprised that I was a bit bothered by that. After sex, I kept in touch with her a little bit, but there seemed to be a tacit understanding that it was just a one-time thing.
#65: Oh my, she was fun. A friend I dig like crazy, who's beautiful and passionate and involved in the community and a joy to be with. Awesome little kickass daughter. Cooldude on-and-off poly boyfriend. Anyway, we were hanging out one night and I think I initiated. She was tiny and thin, so I tried a bunch of rockstar porno moves where I was picking her up and fucking her with one arm on her back and whatnot. I tried fucking her against a wall and it was immediately super awkward. I realized that I didn't actually have a clear idea of how the physics was supposed to work. Like, her back was against the wall, so I mostly had to penetrate her in an up-and-down motion, so then I wasn't sure if I should keep her in one place on the wall and kind of do squats up and down with my legs or what? So I tried for a few seconds and was like, NOPE, BACK ON THE OTTOMAN. She was tiny and I was afraid of pulverizing her cervix, so I told her to tell me if I was going too deep. She replied "Not possible" and I continued with great aplomb. We've only had sex once.
#66: She was a straight-up Asian massage artist / model, which I couldn't help but remember was the description that guys in highschool would always use for a hypothetical perfect fantasy girlfriend. The sex was great, and I was honored to have it twice with her. When I picked her up, she remarked that I was "stronger than [I] look", which gave me a momentary "so you think I look weak and useless?!" pause before shaking it off and continuing. She was the first woman I had ever been with who expressed interest in actually seeing me cum. She took her mouth off of me when I said I was about to have an orgasm so she could hold it and watch with a delightful grin. I really digged her, and we got along great, but a bit of pressure built up and we hit a "wait, which one of us wasn't texting the other enough?" snag that we never recovered from.
#67: Not much of a story. This was a friend with whom I was never really flirty, beyond those one-armed friend-hugs. We hung out one night with friends, then everybody left but the two of us, then she got flirty and I thought it would be a great stress reliever for both of us. I remember it being really hot and sweaty, and her being really distracted by the fact that we were having sex for a long time (well, something like an hour) without me having an orgasm. Like, negatively distracted. She kept apologizing for being bad at sex, and she really didn't need to, and the groove-disrupting apologies were definitely the worst part. Still, not altogether bad. She's a sweet girl, and we're still in touch.
#68: She had just split with her partner and was looking for comfort with me and #30. We had known her for years and ran in the same activism circles. We were just planning on the three of us platonically sharing one big bed, but that went out the window quickly. I'm not sure if it was her or me who started touching and initiating. It was a little weird, being unplanned sex with someone I had known for around ten years. #30 didn't participate, but cheered us on from the other side of the bed. We only had sex once.
#50: With how casual my sex has become, I nearly felt like I was betraying this girl by having sudden, passionate sex with her on a couch after a couple months of tense, restrained flirting. She stirs up familiar, strong, scary feelings in me, and my desire to pour my affection into her physically is at odds with my revulsion to the idea of considering her another casual fuck, or allowing her to resemble one. But for awkward, quiet, someone-sleeping-in-the-next-r
#51: She had flirted with me a few times at shows, then started flirtatiously chatting with me on Facebook. I decided to give her a chance, and we had some pretty fun sex once. When she was going down on me, though, her bottom teeth scraped the hell out of my frenulum, and it hurt for days. I regret that that's what I remember most about the encounter.
#52: She walked up to #30 and me and asked "Would you guys be interested in having a threesome?" She seemed so reserved and shy, so it was a slight shock to hear it from her. We answered in the affirmative the moment the speechlessness wore off and had delightful sex once. I had hoped that it would happen again, or at least cement a more permanent friendship, but she disappeared from our lives soon after.
#53: There was thinly-veiled interest in having a threesome between her, me, and #30, but it only became a possibility after she broke up with her boyfriend. We only had sex once, but it was especially enthusiastic, sincere, and satisfying. She went down on me like she was trying to give me a memorable experience, and it totally worked. The mutual interest in more threesomes continued, but she entered into a monogamous relationship soon afterward.
#54: We had flirted harmlessly for quite awhile before there was any acknowledgement that we could actually hook up. She was a pretty, intelligent, and agreeable girl whom I had known for years, and she had a similar interest in casual sex, so it seemed inevitable. Something about the sex didn't quite work for me, though. Something felt artificial and insincere. I can't blame it on any particular thing or person, and I certainly couldn't describe the sex as unpleasant, but when it concluded I felt like there wasn't any interest in trying it again.
#55: She was my first "swinger" hookup. I had gone to an event at a swing club and felt terribly out of place for most of the evening. After awhile, I figured I might as well start approaching women and attempting to initiate some sort of sex-negotiation. Which felt as awkward to do as it was to type just now. Anyway, she was the principal of an elementary school and caught my eye as especially flirtatious and quite attractive and fit for a middle-aged woman. And, come on. Elementary school principal. As the night wore on and it came close to closing time, I asked her if she was interested in having sex. She shrugged and followed me to another room, unexpectedly summoning her husband. She explained that she doesn't do anything without her husband present, and I feigned being totally comfortable with that. She hopped up onto a table and laid on her back as her husband started fucking her. She fished my dick out of my pants and sucked on it for a little while, then her husband and I switched positions. Something about her husband being there, both of them doing really clichéd "talking dirty", and the whole impersonal nature of the encounter was really unsatisfying for me. I didn't get off and I just stopped having sex and left after it appeared that I had gotten her off.
#56 and #57: Two girls that I fell for but, as usual, couldn't keep in my life. #56 surprised me by kissing me on stage one night. I had assumed I was out of her league, but I asked her girlfriend, #57, if she was actually interested in me, and the next thing I knew we were all naked in their bed, keeping the neighbors up with multiple sessions of sex, and holding a lengthy, impromptu blowjob contest. I had sex with #56 four times and #57 twice. The sex was the best I could ever hope for, but I would have given it all up to have kept everything from falling apart. #56 deserves better than to be trivialized on a list of my sexual encounters, but must be included for the sake of completeness. I just have a bad habit of falling in love with girls that I'm inconsequential to.
#58: I don't really remember what led up to me hanging out with #58 at her apartment, but we had been mildly flirtatious before and acknowledged physical interest in each other pretty quickly. Sharing a couch became holding became snuggling became kissing became WHELP, GUESS WE'RE NAKED NOW became nice, slow, long, comfortable sex, which we only had once.
My first was a co-worker in a factory I was at. I'd like to think she was genuinely interested in me since she seemed to hang around me alot, but in the end she found out that I was a 25 year old virgin and wanted to break me. (Granted, sex for me wasn't really a thing back then because I just didn't care if it happened or not.) We had a slow day at work and got sent home, so she drove me back to my place and we watched Young Guns and ate Pizza King. She got me to give her a back massage which she kept leading my hands down further and further and we wound up on my bed less than an hour later. I remember it being nothing like I had thought it would be and it was over far quicker than I imagined it would be. We had another day off a couple days later and did it again, this time it was everything I had heard about it. The sweat and the smell and the feeling and that climax together at the end. It was amazing. We saw each other and had sex everywhere and when we could for another couple of months until she decided to go back to her ex boyfriend. Three months after that, she called me up again and we decided to start dating. It turned into the longest relationship I ever had. During our 8 years together, I found she was bisexual and she brought many girls over to the house for her to have and share or for me to watch and play with, but not have sex with. (We left that decision to the other party most of the time and I agreed to it. I'm not going to argue over getting to watch two women have sex with each other.) We are now broken up. Long story.
My second was a girl that my first brought home. She was a fiery redhead who was very sensual and the best kisser I have met. After she and my ex had finished getting off, I decided to take a chance and leaned in and started kissing her on her neck. She reciprocated and started kissing me back. We kissed for more than ten minutes that night at one time. That's how good she was. That entire night, we all had sex with each other until the sun came up and we passed out from exhaustion. I woke the next morning with the two of them giving me a blowjob. That was the best night of sex I have ever had. We wound up pulling her into our relationship for over a year. The three of us all being a couple. We would sleep in the same bed and have sex all the time. I've never once had a bad memory of that year we had that triangle going. She left us later on to move back to her parent's because her mom had grown ill. I have always missed her.
My third was a friend of my second. She had just been kicked out of her house and was sleeping on the couch of their place. Somewhere along the line my second and her started having sex together and they were talking to my first about a threesome between them and the possibility of a foursome between us all. She approached me one day while everyone was out of the house and we ended up in bed. She wasn't the best at sex. Mostly just laid there and took it. She had huge tits, though. 44DD if I remember correctly. It didn't go over with the other two well because I wasn't supposed to have her like that without their permission and it caused her to have to leave. I get the feeling there were other factors involved there, but it was never quite clear enough.
My forth was another girl my first had brought home. She came in towards the end of the relationship. She was all of 18 years old when she was with us. Had never been with a couple before and was shy of women. It turned my ex off that I was able to pleasure her more than she was. So it ended up being me and her having sex multiple times while my ex watched. We still talk to this day and we still have sex every now and then when she comes into town.
Number 5 was my rebound after my first and I split up. It was a one-nighter that started as a completely drunken make-out session at the bar and ended up at her place. She was a fire-cracker in bed. Very flexible and knew how to use her body. Only wish I could remember alot more of it than I do. Never saw her or talked to her again after that.
My sixth was a co-worker. She stated to me one day that she would like to come over and I said yes. We talked for awhile before she jumped on me. She was a great girl in bed. We had sex many time after that.
Number 7 was another co-worker who was taking a break from her relationship. She was a very sweet and innocent girl at work and it blew my mind to hear her text me about sex one night. I ran with it to see what she would say and she started coming over to hang out. We finally got to the point where we could start kissing and fooling around, but she never wanted to take it that next step. Finally one day she did. She was an incredibly sensual person who loved to touch and be touched, as I would expect from her knowing how sweet she is at work, yet when we had sex she became a whole new creature that cussed and screamed. It really turned me on. She went back to her relationship, but we both like to joke with each other about our times together and we've been better friends because of it ever since.
Number eight was a good friend that invited me over one night. We had some drinks and watched a movie and ended up having sex. We did it one other night after that. I've never understood what happened with that situation, but since then she has grown more and more apart from me as a friend. I was trying to see if could become more than just friends before we did have sex, and she told me she wasn't interested in that, but I always wonder if that had something to do with it.
Number nine was a girl from Indianapolis I had met online. She is an amazing woman that I am still talking to. The only thing that keeps us from becoming more is the distance between us. She is a very sensual and sexy black woman who I had a great night with only once. I've been trying to get back down to her to have another night like that, but she has been busy alot. I'm beginning to think she isn't interested anymore. Again, the distance between us...
My tenth was another woman I met online. She lives in Marion and invited me up for a night. I didn't know what to expect. We went to a bar where she goes alot and hung out and drank. As she got more drunk, she started becoming wilder and wilder. She took me home and stripped me down and we had ravenous sex. I feel bad because while it was awesome and wild sex, it just wasn't what I was wanting, so I never got off the way I wanted to. There was always something in the back of my head telling me it wasn't right or something wasn't working. I ended up staying in Marion the next night for some reason and I could tell she knew I wasn't comfortable, so she gave me a blowjob when we got home and said she wouldn't feel so bad if we didn't have sex again. We fell asleep and halfway through the night my sexomnia kicked in and we had the most amazing sex of those two nights. I still do not know what was holding me back that first night and I still cannot pull whatever dream I was having when I started getting her worked up that second night, but I was glad that it did. I would have felt bad if I would have left and she would have been unsatisfied that whole weekend.
The first time was everything I'd hoped for and happened in the early stages of a growing friendship. He was the epitome of a cool older guy to me, and for many months I had taken slight offense to his flirting because I didn't think I had a chance. He was my first real kiss, who evolved in a short time to the first guy I fooled around with. He was always sweet and considerate, especially the first time we had proper sex, and continually made sure that I was comfortable with everything going on. When his cock first slid into me, he asked if it hurt. It did, but I liked it, so I said no. I knew that I couldn't hope for him to be my boyfriend, and I didn't have any delusions that giving him my virginity would change that. It just meant the world to me to be so close with him, to feel so wanted, and to truly have all of him for a while. Walking was uncomfortable for a few days and provided an aching reminder of the fun I'd had, like the muscle pain you have for a few days after a good workout. We had sex many times after that over the course of many years and a relationship, and each time left me with a feeling of being totally satisfied with a physical connection to someone I love. I've heard often that girls end up hating the first guy they have sex with. I was lucky enough to give it up to the guy that ended up being my best friend.
The second time was with another close friend. We were both shy and awkward about it, him moreso than me. Weeks of sharing a bed and bags of wine led to kissing, and kissing led to fooling around. I ended up initiating most of our physical contact. We shared a life devoid of money and full of the drama that surrounded us, and our sex reflected a mutual release. We never said we loved each other, though in retrospect I suspect that we did. The first time we had sex instead of fooling around was the first time he took initiative and followed a long, emotional day for me. The times he took the lead are still some of my favorite sexual memories.
The third was a one night stand. I'd known him a few years prior, and he was back in town for a little while. He was sweet and persistent, despite my initial lack of interest. After a week of failed attempts at getting intimate with me, I ended up fucking him in the back seat of his car. It was fun until he said he loved me, at which point I promptly panicked and wrapped things up as quickly as i could. I felt guilty and avoided him for the rest of the time he was in town.
The fourth was kind of a friend and supposed to be a one night stand. When I invited him over, I was uncertain whether I wanted casual sex or not. But as he started expressing interest, I so enjoyed the attention that I decided to go for it. He fucked like he had something to prove, and his insistence on leaving immediately after made me feel like he'd presented a challenge. After many more encounters, I won the challenge and got him to stay the night. Morning sex was awesome. The relationship that evolved afterward was hit and miss.
The fifth was an old friend that I'd been spending more time with. He stayed the night, and we made out while watching some movie that neither of us paid attention to. He asked at each junction if I was okay with what was happening, what I wanted, and what he could do better. Despite the sweetness, it was awkward, and it made our friendship uncomfortable afterward. The snuggling was nice.
#40: Another friend who also engaged in casual sex with mutual friends. It seemed inevitable. She was a bit dull during the two times we had sex, but I remember her having an unusually fantastic pussy. Very well-shaved and... I suppose tighter than usual, or maybe with some unusual texture to it. It just stood out to me.
#41: She had been a friend through college and we had flirted and fooled around a bunch, but her extra-small pussy and my extra-large cock made sex all but impossible until we eventually made a Herculean effort to fuck and succeeded three times, each time only barely before she couldn't handle the pain. I took her virginity and hope that her sexual experiences have gotten better since, hopefully with a more anatomically compatible partner. Poor girl. :(
#42: A friend-of-an-acquaintance, turned friend-of-a-friend, turned full-on friend, turned long-distance occasional lover. Very enthusiastic in bed and adorably whined out "thank you" upon orgasm. Her yoga came in handy in the four times we had sex, half of which were part of orgies.
#43: A very endearing friend with whom my flirting one night began a longstanding relationship that we've yet to fully figure out the terms of. We've had sex four times and it's always been pretty damn awesome.
#44: Part of a circle of friends who make up many of these recent numbers, whom I've never known well or been particularly close to. She suggested it. We did it once. It was good, as far as sex goes. I felt a little strange about there being even less of an emotional connection than usual.
#45: An online admirer whom I got to know and from whom I accepted an invitation to come see her and fool around. We did once, and the sex went on for a long time and was really nice. I think we were both trying to impress each other.
#47: A woman in my circle of friends whom I had encountered a lot over the years, but never really known. #30 was going down on me at a party and she walked up and expressed interest, and all of a sudden she was on my itinerary for the orgy that happened later in the night. Several of the people at the orgy commented that we looked really hot fucking and that I seemed to do a good job with her, which was nice to hear, especially since I was drunk enough to be straddling the line of sexual efficacy. She was lovely and I really enjoyed finally experiencing her.
#48: Part of this circle of friends who watched on jealously as #47 got railed at the orgy and then sheepishly flirted with me. Wonderful body and fantastically tight pussy. Actually, sometimes too tight. I learned in the two times we had sex that I had to be gentle.
#49: #42 brought her to me, and hungrily watched alongside #30 as I fucked her. I had never met her before, and couldn't help but smile when we shook hands and hastily introduced each other immediately before my cock went in her mouth.
#30: Another one of the great loves of my life. Everything was pretty much perfect about sex with her, and I could give her orgasms endlessly. I have also had more threesomes with her than anyone else.
#31: An old friend of mine with whom I had flirted and who all but swore off the idea of having sex with me, despite fooling around a few times. When an opportunity came for her to have a threesome with me and #30, her mind changed.
#32: I met her at a party and hit it off. We sneaked off into the attic to talk, then very gradually started fooling around. I was really cautious about making any moves, since I didn't know her, but she reciprocated, and we slowly progressed to having long, crazy sex until dawn. She approached sex with me like an engineer investigating a machine she had never operated before. She kept capriciously feeding me suggestions of what to do and how to do it, as if she were experimenting with all the different forms our sex could take, and there was something thrilling about having sex with a girl who was so intellectually engaged in the act. I was disappointed that I only got to see her that one time. My friends, who had apparently been listening to us fuck all night, congratulated me in the morning. I may have blushed.
#33: She was a fan. She stuck around after the rest of the audience had wandered away and invited me to a party. After not really bothering to introduce me to anyone there and leaving me to feel awkward for awhile, she spent the rest of the evening leading me into rooms of her friend's house and trying to initiate sex, with her friend finding us and getting angry. Including some child's (unoccupied) room. I felt really icky and manipulated and kind of trapped in a situation that I didn't know if I wanted to flee or stick around for. She eventually got me into a bathroom where I tried to finish the whole thing quickly so I could leave. The first black girl with whom I've had sex.
#35: A friend that had been having sex with several of the guys in our social circle. Since I had similar interest in having sex with attractive friends with whom I had chemistry, it was kind of inevitable that we had sex. Four times, in all. She squirted a goddamn lot. After sex, I wondered if her downstairs neighbor's ceiling was leaking.
#36: I felt very lucky to have attracted this beauty from afar. It wasn't long after we met that we became drawn together physically, and there was an immediate vibe that we connected to each other deeply and would work well together. At least I thought so. We had two threesomes with #30 and then she disappeared completely.
#37: An acquaintance with whom I'd casually flirt and receive much more serious flirting in return. When we had sex, I ended up feeling really manipulated and very sleazed-on. It wasn't even good sex. And she lied about not being in a relationship. And she ended up being a racist. One of the few sexual experiences I completely regret.
#20: I was attracted to and flirting with her friend for some time, but she swooped into my bed before I ever got a chance. I remember her making some astonished observation about the size of my cock (I swear, it's not even that much above average) and then reassuring me in a serious tone, "Don't worry, I can take all of it," with all of the confidence of Rosie the Riveter. We had sex three times.
#21: She was another friend who had actually always been fairly bitchy around me (spoiler: she goes right back to being bitchy after fucking me seven times). I remember her being insistent about licking and sucking my balls, then REALLY offended when I told her it tickled. She scowled at me, said "fuck you," then went immediately back to sucking my cock. Very strange vibe in the room at that moment.
#24: One of the great loves of my life, and another whose virginity I took. I stopped counting our sexual encounters after twenty. Had the misfortune of being especially awesome at fellatio, so my greed for that often cheated her out of sex.
#25: Another one of the great loves of my life. She was fantastically attractive, universally lusted after, and great in bed, but had a lot of trouble ever reaching orgasm, which made me sad. We had sex thirty-three times. Once, covered in sweat in the middle of summer on top of a pile of clean laundry. Her roommate sat in the corner of the room and told us what to do to each other while she masturbated. We took turns seeing if we could actually rape the other while they fought back. We've gotten a hotel room to fuck in three times, and absolutely tore the hell out of one of them. One of my all-time favorite sexual partners.
#26: "I always get what I want, and tonight I want you," she told me. We had sex until sunrise the first time, and I gave myself wicked rugburns on my knees fucking her on her living room floor the second time. We had sex four times.
#29: She was a lovely young girl whom I met overseas who led me into her house so she could have sex with me in her pitch black room while her parents slept upstairs. She didn't moan ecstatic phrases in her native language like one might fantasize, but only wordless whines and squeaks. I wanted to have sex with her all night, but slipped up and had an orgasm after a half-hour or so. I then tried to pretend there was no such thing as a refractory period and awkwardly failed at continuing to have sex with her with a second condom. Our sex was a cross between one of my greatest sexual triumphs and failures.
#10: I met her in college before I ever heard the advice "don't stick your dick in crazy". The sex was good and especially enthusiastic, athletic, and dirty. "Pound me, make my pussy bleed" and whatnot. She squirted, so I could easily count her orgasms. We got to 45 once before calling it a night. She started wanting a relationship, I suggested we stop having sex, and she insisted on still sucking my cock all the time. It was hard for me to refuse the offer. We had sex eighteen times.
#11: She was a redheaded jazz singer who would write notes on herself and then wrap them in clingfilm so they wouldn't rub off before she could copy them. I was rooting for her when she wanted to have sex with my friend, but he wasn't interested. And gay, if I recall correctly. So she took me home instead and had bizarre sex with me on her floor, then in her closet (she was really insistent on this), then up against a wall, then on a different floor. She had gone a few days without any sleep and was deliberately staying awake so she could have otherworldly sleep-deprivation hallucinating orgasms with me. She disappeared from my life shortly after the one time we had sex.
#12: She was a painter whom I had just met. She invited me to her place and showed me some of her art. We started unexpectedly kissing, then quickly progressed right to sex on her couch. After awhile, she had to stop because it was causing her too much pain. I awkwardly asked her to help get me off before we went to sleep, then felt like a tool. We didn't see each other after that.
#13: She was a friend of mine that didn't seem enthusiastic about fooling around with me whenever my largely one-sided flirting got us into a bed together. At a concert, she surprised me by suggesting out of nowhere that we fuck in the bathroom. It ended when someone knocked on the door. She complimented me on my "big fucking cock" in her usual stoic manner and it made my day. We only had sex once.
#14: She was older, taught me a lot, and kind of fucked my world up. We had sex fifteen times, and one of those times was the only time I actually got a complaint. Something along the lines of "That wasn't your best work, back there. Might want to step it up a notch."
#15: She was a long-time, long-distance flirt. We had wanted to take each others' virginities, but we had to settle on me just taking hers. She was fantastic and reminded me what it was like having sex with someone whom I loved and fully trusted. We had sex nine times. Before we did, I remember her implying online that she had worked on stretching herself out so I would fit, which was terribly flattering, in a strange way.
#17: She was a friend's girlfriend who had flirted hardcore with me for some time. I eventually broke down and had one night of really fantastically hot, sweaty, crazy sex with her, then quickly came to regret it. I remember sitting up and struggling to keep a grip on her hips as I bounced her up and down atop me and she moaned something about me being "thick".
#19: She was a good friend, fantastic person, and attractive girl, so I saw no reason not to suggest that we have sex. She saw no reason not to either, and I spent enough nights in her apartment to have sex with her twenty-five times. It was actually one of my favorite casual-sex-with-friend relationships. Or fuckbuddies, but that sounds so vulgar and demeaning. But yeah, fuckbuddies.
#1: My first was wonderful, we were both virgins, and our sex was filled with the usual enthusiasm of teenagers venting their pent-up sexual urges. She could only get off when she ground her clit into me on top. We definitely had sex well over a hundred times, which we calculated from boxes of condoms purchased.
#2: She was a metal singer and had sex with me with a smile and a shrug. She gave me a quick introduction to both casual sex and group sex one night with her drummer and his girlfriend alongside us. "I want to fuck you because you have a cool website" actually came out of her mouth. She wrote a song about me that her band recorded that included orgasm noises. I was present to make her make those noises nine times.
#3: She was a sweet girl with whom I went to highschool and had to very gradually become bold enough to flirt with. She stared slackjawed at my cock the first time it came out and was unsure at first if she could accommodate it. She could, did twice, and shuddered adorably when she had orgasms. She later got really bummed out when she overheard conversation about another sexual relationship of mine and I felt bad that her feelings got hurt.
#4: She was a friend. I had gotten high (very high) for one of the first times in my life and was having an emotional night when our paths randomly crossed and we decided to follow through with the coy flirting that had gone on between us for years. We only had sex once.
#5: She was an anime nerd, as was I at the time. She invited me to her dorm room many times and we had pretty awesome sex twelve times. I told her that she was a classy girl and she promptly responded that the compliment was definitely getting me laid that night.
#6: She was a roleplaying nerd, as was I at the time. We didn't flirt, but she offered me crash space when I was in her town. Crash space turned into sleeping in half of her bed, turned into spooning, turned into, "Hey, wanna have sex instead of sleeping?" turned into sex three times.
#7: She was also in our roleplaying circles, and identified as a lesbian. We had known each other for quite awhile until I casually flirted with her. She quickly decided to take me home as "an experiment" to see if she was still sexually interested in men. She thanked me for my efforts, but informed me that I confirmed for her that she was not.
#8: She was an acquaintance who caught me when I was drunk and feisty in her house after everyone else had left a party. One of the few girls with whom I've had sex that I've really regretted. Just not that great of a person. She screamed during sex, too. Not like "wow, this is great sex" screaming, like "AAAAAAAAAAAAAAA I'M GETTING MURDERED" screaming. I was genuinely worried that a passerby would call the police.
#9: She was an old, old friend of mine with whom I had flirted in high school, and there was a vague understanding that when she was no longer with her boyfriend, that she and I would fool around. We had sex twice, and she told me that I was the first guy on whom she performed oral sex.
My first time I was pretty drunk so I thought the numb feeling was a side effect of that. But with my current girlfriend it's still the same. And I don't have the heart to tell her as I feel like she'd take it personally and think it's something wrong with her when I really don't think it is. Honestly I'd have to guess she's well above average in the sex-skillz department. And that makes it worse-- that despite the fact that she's incredibly attractive and putting in a lot of effort to do some damn sexy stuff to me-- I can barely feel it. I feel guilty about that.
I've decided to be celibate for the next few months. I don't know how far this will go. I love sex, I love holding someone until the morning, throughout the afternoon, feeling them, loving them...but it's a distraction. My ability to concentrate is limited by the consistent desire to enjoy the sexual company of others. With the close of a relationship, I have decided that it is time to take control and take care of myself.
The last time he (my ex boyfriend) was in town, we got drunk and went back to my apartment and it was better than ever before, the sex was just so amazing. The first time it was raw passion, almost violent in its shared desire. Then each time after it was more tender, connected, as if the love never left. He spent the whole 20 hours we were together telling me how much he loved me and enjoyed my company. I don't think we'll ever get back together, but those 20 hours of sex, love making, passion, tenderness and care are enough to sustain me for a while.
1.) I have never made-out with anyone and not gotten them naked in less than an hour from that point. ...that would seem impressively pimp until you learn that i've only ever made-out with anyone 3 times. Basically I haven't really ever kissed anyone and NOT been naked with them within the same sitting...
Always on my mind, I can never get enough. Seems I'm near-constantly wet and horny for weeks on end, it drives me crazy sometimes. Sometimes even vanilla won't cut it, I want it deliciously kinky and it's all I can think about.
But I'm pretty sure I don't like receiving. A.) It just means it'll be over faster so I can't keep doing the one part I do enjoy about it B.) There's all the pressure to keep it up which reduces some of the fun C.) Honestly, out of the admittedly limited sex experiences I have had? I do it to myself better.
So yeah, I think I'm the rare dude who just doesn't want to fuck anyone. And not for religious reasons or anything. Although still mildly fun in the naughty entertainment sense, I find it overall more unenjoyable than I do enjoyable.
The mind wanders. we think about how crappy our day was, and how crappy the next day will be. as long as i can remember i've fantasized about things that i would never do and things that could only happen in my imagination.
Lately i've been playing a game to pass the time before i fall asleep. i try to figure out which of my friends have had sex, which sounds really weird, right? but hear me out. it's really hard to predict such a hidden matter. i have some new friends, but i'm not close enough to most of them to know their past and their intimate lives. i suppose it's just an complex thought to try to wrap my head around when i'm bored.
the sex we have is amazing. i'm a whore for you. we have sex everytime we meet, and i dont even care. if anything i invite it. luckily this time you are my boyfriend. perhaps i'll keep this one. and you are the second person i've had sex with. why didnt i wait to meet you from the begining.
I love sex. I would say I'm addicted. And somehow, in a few instances, this has scared guys off. Being open sexually is important to me, and some people just can't handle it. I'm dominant in everyday life, but In bed I'm extremely submissive....Is that weird? I have a few fetishes. I like being tied up, I like pain being inflicted during sex (biting, slapping, being pushed around) and often find myself saying "Make it hurt". And then there's that one that I've only told 2 people that I've interacted sexually with. A rape fetish. The scenario (like role playing) turns me on majorly. The most out of all of them I'd say, and until recently, I haven't found anyone willing to comply. And I love it, but I already knew I would. I can't help but think that it's weird and maybe makes me a little crazy, but people have all kinds of kinks and that just happens to be mine. I'm enjoying the hell out of it. Fuck what "normal" people think.
the second time was with a boy who had beautiful freckles and a jar full of opiates. one time we got caught in a freak rain storm in the woods by my house and took shelter in a bush and in each other while the river rose. i couldn't tell his tongue from the hot humid summer air.
number three lured me into his station wagon with a loaded pipe and french fries. one night we laid down, sock footed and flying, in the back of his car way out on the plains in the middle of nowhere. inside the garage was a party, but outside, the world was ours, and the lightning flickering on the horizon was just for us. i've never seen a night so beautiful in all of my life. he stopped calling when he went away to college.
number four took me out back during a smoke break, it took six minutes and was caught on camera. he was still bragging about it years later, when i ran into him at a new job. everyone heard about our one night stand. i was mortified.
number six was the most beautiful boy i've ever known. we spent a month together in two week increments. he crawled into my bed at seven in the morning and fell asleep with his hands on my stomach humming stone temple pilots. i was his first. i broke his heart.
i had sex with number seven before i really wanted to, but i needed a distraction. we made love so often that i fell in love. we watched new age movies and fell into a heap on the couch, on his bed, on the arm chair, in the back of his car, sweating, swearing, lost. he hardly ever said a word to me, and i resented him for it.
number eight was to get back at number seven, and to prove to myself that people still wanted to fuck me. after the first time we slept together, he rolled over and told me he was a virgin. i panicked and ran out the door, in a figurative way.
number nine did a lot of cocaine and had long blonde hair and a tattoo of a cross on his shoulder and a broke down blue truck. he was everything i thought danger should be, and i paraded him around because all of my friends thought he was beautiful. he couldn't ever get it up because of the coke.
number ten bends to my fantasies, had the most beautiful penis i've ever seen, and a body like a mannequin. he thinks he's ugly. we find ourselves swept away often, pawing and panting, like adolescent animals or junkies looking for a fix. sometimes we make love... sometimes there's that anger i recognize, well hidden, deep seated, but there none the less.
Sometimes I wonder if I’m a freak. I generally actively seek out men that I think I may be able to have an relationship with. I know how that dating game works. You meet, you hang out for a while, then after you reach a certain level of familiarity with someone, you take them home with you and see how things will work one on one. You watch a movie, sit on the couch, then if everything seems to be working out well you do what the shampoo bottle says and repeat the one on one time for a few dates then eventually someone makes the hit that things should be moved to the bedroom. So there you are in all its awkward glory, having sex with someone new, and about 30 seconds before I know he’s going to make the move from fooling around to having sex, I don’t want to anymore, I’m not sure if that I’m scared, or nervous, what if he doesn’t think I’m good in the sack, what if he’s just using me, what if I’m really just using him? I don’t know, I can remember one time looking up and trying to lock eyes with a guy and then never being able to catch them, as if he was just refusing to look at me, not really wanting to see me in that moment. I’ve had sex, I’ve had the awkward fuck, I’ve made love, and every time I’m still slightly terrified. I turn into a shy little girl looking up at the guy begging with my eyes for some sign of approval, a sign I’ve never really gotten. Even when I was in a long term relationship (about 3years) I never really felt completely comfortable with him in bed. I really wonder why I can’t just throw my head back and give myself over the ecstasy that sex should be, but I guess I’m really just a little scared but I can‘t seem to figure out exactly why.
I'm starting to think that I'll never shake the nagging, instinctive sense of fear and helplessness associated with sex. It's especially frustrating since I almost constantly crave as much affection as I can get from the men I love.
Sex is bittersweet. In the case of people I'm attracted to, I'm probably the easiest person to arouse. Anything from the sound of their laugh, to an erotic touch, to intellectual conversation can have me instantly wanting to turn off the lights and be closer to them. But any sort of near intimate encounter with a person I'm not attracted to turns me into an instinctively unstable, violent person that I'm not fond of. I have, in my past, almost stabbed men in the kidneys for not heeding my whispered requests to be left alone. I have briefly lost consciousness at parties while drunkenly making out with a guy and nearly thrown him out a window upon regaining consciousness to find a hand sliding under my waistband. I almost always catch myself last minute, but not always before cutting people deeper than I really want to or twisting an arm more than I should. I don't really want to cut anyone at all, which is why I don't carry knives anymore. That's the least I can do to encourage myself to deal more rationally with such feelings.
I've had sex with two men, for both of whom I have a strong love founded in logical respect, appreciation, and pity. When I lost my virginity, I had no daydreams of him being "the one" and protecting me forever. I knew then that probability said that we would eventually drift apart, and I knew him well enough to know that any signs of possessiveness on my part would just make that happen faster. So I ignored the part of myself insisting that I couldn't be special to him unless I was his girlfriend, and I contented myself with "just friends".
I'm not sure where to go with this line of thought and will probably rethink, rephrase, and expand later. For now, though, I will close with the comment that I hope to someday be able to have wonderful, passionate, loving sex without having the most vivid nightmares about the past and being half tempted to shrink away from a gentle touch.
...sex is love, in its own way. nothing demonstrates trust and understanding like worshiping each other's bodies, admitting feeling. the connection when you look at each other, and realize that no one will ever make you feel like this again.
Sex... I'm surprised I'm the first to post here. Absolutely central to our functioning as a species. An undeniable constant distraction in our minds. Ever-present in Western media, especially advertising. The most commonly enjoyed activity in all of the world, next to eating and sleeping.
Personally, I love sex, in my limited experience with it, and love that it takes so many forms, flavors, and styles. Despite the fact that my interests generally only lie in vanilla (non-fetish) heterosexual sex, I have a profound respect for the diversity found in sexual practices all over the world, and even in your own neighborhood. I dated and off-and-on lived with a professional dominatrix for roughly half a year, and got a crash course in uncommon sexual practices, as well as the kinds of non-mainstream relationships that people can form. To the surprise of everyone that knew us then, our lovemaking took no kinky, fetishy forms in the bedroom. Perhaps if we had been together longer, it may have, but when we were just getting to know each other and exploring how to fulfill each other's needs, we only had straight, vanilla sex.
My current understanding of my own preferences is that I absolutely prefer the company of people in BDSM lifestyles (and I'll post a BDSM thought later to clarify what exactly I'm referring to there), but have no fetishes of my own, nor any strong inclination to engage in anything but standard sexual practices
Pecking. Holding. Pawing. Squeezing. Kissing. Petting. Stroking. Unclothing. Clawing. Licking. Biting. Scratching. Thrusting.
My first thought is that that makes me boring, but I suppose that there's no reason to fake having interests that I don't really have. My fetish friends will forgive me. And still, I get to have occasional fetish fun with friends and I have a blast, I just never feel a need for it. I suppose that's the secret to life, eh? Learning to enjoy yourself as much as possible without needing anything.
The best relationship ever is a casually sexual one with a close, dear, trusted friend. One that you know that you're never going to grow apart from, but there's no unhealthy possessiveness about the relationship. [Thought continued at poly]
Feeling shallow and ashamed that within a split second of meeting her, I'm plotting out in my mind the moves on the chess board that will get me into her bed to spend the whole night indulging in what a beautiful person she is until the sun rises over our sweat-soaked bodies and morning birds harmonize with our exhausted panting.
Pausing in the middle of lovemaking to brush her hair back away from her face and spend a long moment soaking in every detail that I can of her perfection. I must have the silliest grin on my face... But it just makes me so happy to be this close to you. To be able to occupy the same space as you.
The aggravating awkwardness of the mechanical aspect of sex. Yes, we both want to spend all night having loud, wet, unashamedly wild, epic sex, but my penis is roughly twice the length of your vagina, and it's going to take some measuring tape and a calculator that can do trig to figure out how we're going to pull that off without hurting you.
I don't understand how you don't like having oral sex performed on you. I just look at your tattoos and want to run my hands all over your body and kiss them and make a line down your stomach with my tongue and make you make those noises that I love hearing, but nooo. You don't want people to go down on you. I just can't relate to that.
The imbalance of sex. Generally, guys take a more active role, and girls take a more passive role. This is partly cultural and largely mechanical. When a girl is on top (of me, anyway), it's usually awkward and my penis comes out every so often, forcing a pause before the sex can continue. When I'm on top, sex can continue uninterrupted for hours. I don't have a vagina, but I can only guess that it's hard to use one on top and gauge when the penis is about to slip out. Also, speaking just for myself, it seems like sexually pleasing a guy is very straightforward, whereas sexually pleasing a girl is like solving a fucking Rubik's cube. Any given girl may prefer that you stimulate either her nipples, clit, labia, or vagina, and possibly absolutely hate having any of the others touched. It's hard for guys to understand why it's not "all of the above" because for guys, their only sex organ is "all of the above". So once you've narrowed it down to which of the myriad of erogenous zones are fair game on your damsel of choice, you then have to determine how rough, how much lube, whether any kind of stimulation is okay or if she doesn't want your tongue, hands, fingers, penis, etc. involved, how deep, how many fingers, etc. And I'm not even getting into the complications of the menstrual cycle, how oral sex gets difficult once you've reached a certain amount of pubic hair, and those vaginas that condoms just disappear into like a magician's hat or something. All girls have to deal with is the penis. And it's pretty straightforward in what it wants. There's really no way to go wrong.
Well, let me correct myself. One time I did get a clumsy turbo-handjob that left me with a painful genital equivalent of rugburn, and another friend of mine confessed to getting an awkward and unpleasant handjob once, too. A comedian once said that a penis is like a car with manual transmission. No one knows how to work it as well as the owner, and when someone else tries, they usually end up just fucking it up. I think I'll have to agree that the finesse of a good handjob is hard to get down if you haven't actually had a penis, but that's still a far cry from the prerequisite master's degree in engineering that you're going to need to be Master of the Vag'.
Oh wait, balls. I suppose some girls have to juggle the dick-balls combo to please their respective mans. That's another thing I can't relate to. Mine are about as erogenous as my eyelids. For me, it just feels bizarre and unnecessary when they're manipulated. But for all I know, I might be in the minority here.
I approach sex in two very different ways at the same time. I'd hate to ever have sex in an impersonal way with someone that I don't care about, and the sex that I have is almost always with friends that I've gotten to know and love. Nonetheless, when the actual act commences, my mind slips into a meditative, analytical mode. Yes, there's emotion there, but my engineering mentality combines with my desire to be selfless and tend to the needs of others and turns me into a sex robot, analyzing and correcting angles, rhythms, pressure, etc. several times a second to maximize my partner's perceived pleasure. Tantric meditation has taught me that wonderful trick of having an orgasm without ejaculating, and hence becoming multiorgasmic, and meditation in general has helped me come upon a better understanding of the functioning of the human body and a keener ability to pick up on what drives a particular girl crazy.
I suppose I've accomplished what I wanted. For most of my sexual partners, I've been commended as being good in bed (my last girlfriend flat-out told me that she would reconsider breaking up with me if I just promised to fuck her every day... I declined, and we broke up). But I wonder if I'm missing out on something. I'm very satisfied with how well I've learned to hone my focus and skills in sex, just like any other activity in life, but I feel like sex isn't something that should be treated like an engineering problem. It's not that I see my partner as an engineering problem (hardly), it's that I get caught up in wanting to please her so much that I distance myself emotionally from the act, so much so that I might as well just be playing a video game and controlling a character that's having sex. I focus and completely block out the sensation that I get from sex so that I won't get off before she wants me to, and I end up not really experiencing anything for myself. I don't regret that this is how I've operated, but I have a lingering suspicion that there's something wrong about it.