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Cake day: June 14th, 2023

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  • Too many to count, in all honesty. I was what you might call precocious. I started fairly young, and stayed steadily active from early puberty until adulthood.

    I think the most entertaining story from my actual teenage years was likely to do with my first foray into interacting with a couple

    I made a friend in high school that was dating a particularly feminine boy, or so I thought. Turned out that said boy was what would later be called trans, and thus had female body parts. Friendship with the actual girl of the couple turned into a mutual attraction.

    During that process, I also became friends with the boy. It was rather convenient since now they both had someone that they could take to family functions as a quasi boyfriend. Because of the friendship with the guy, when the girl discussed her attraction to me, he agreed to open their relationship up to allow sex with her.

    While he was not at all interested in me sexually, he did partake in some of the foreplay, including “warming up” the young lady.

    There were, however, some emotional issues with being present for the rest, so this wasn’t a three way thing, unless you count the minor degree of teasing he would do to me, and I don’t. Things like running ice cubes down my spine, or the rare times he would have a surge where his curiosity about cis male anatomy would rise up and lead to some teasing of my scrotum or brief touches of my penis. It was a tad confusing at times then, but looking back I can better understand his conflicting emotions and curiosity.

    But when things progressed past a point, he would leave us to it.

    We also could do our thing when he was at work, or otherwise not present.

    That’s where the meat of the story is, if you’re looking for something more directly sexual.

    She was not my first overall. But she was the first person to suck me. One afternoon, early in things, she and I had teased each other to a state where we were frantic and hungry. We made out, drawing that tension higher until she broke it and said she had to suck my cock. And the way she said it, with desperation and need was an instant kick to my already throbbing libido.

    And gods, she sucked me. It’s fair to say that at that age, I likely would have thought any head was amazing, but this girl was beyond skilled. She sucked my dick like magic would come out of it and change the world. She worshipped my cock.

    That is a very powerful experience, particularly combined with her obvious joy at it, the skill she showed, and the newness of it to me.

    She sucked my cock on the couch, on the floor, on the table, across the floor and against a wall. We weren’t getting up and moving, it was me scrabbling at the carpet in delirium and bucking my hips as she took the root of me deep into her mouth, licked and sucked and screamed around me with her occasional orgasm.

    She would pause now and then to stroke me with her hands until beads of pre-cum would start flowing, only to lick the line of it as it dripped down me, then swallow me whole again. I rode the edge of my own orgasm for an hour or more, and towards the end had my first orgasm without ejaculation. A wave of pleasure so intense I could only scream and babble incoherently hit me, and She cupped my balls, squeezing them gently. She thought I was ejaculating, but didn’t stop.

    As the shocks and jolts of the orgasm faded, I was seeing motes of light and my ears were ringing, but she didn’t stop.

    I screamed until my throat was raw, and that wave crashed into me again, and it was like my soul was pumping down my spine and out of my cock. I pulsed and shook as she drained me, still not stopping. The more I screamed, my arms flailing, she would slow slightly, back off until just the tip of me was embraced by her lips, then surge down my shaft to pull another scream from me.

    Until I begged for mercy. I could barely speak, but I managed to get something said that made sense, and she began slowing, easing up the pressure until I exploded a second time. After that, she kissed her way up my body, the skin of her breasts eventually caressing my still hard and almost painful cock.

    She lay on me for a while before either of us could move.

    When we finally found the ability to move, the curtains were yanked from the wall, the coffee table was empty, with things strewn around the room. Her panties were ripped and hanging off of a plant. The room was demolished

    That was back in 1989. I have still never had head better than that. It has been rare for anyone to even equal it. There was a span of time I would turn down head because how in the hell could anyone match it? It would just be disappointing in comparison.

    Just remembering it makes my balls ache and crave the intensity again.



  • There’s something about a woman that’s wearing something loose (like a silky robe, or oversized shirt, or whatever) and nothing else that’s confident and casual while going about their day.

    Obviously, this is something that tends to be harder to see when it isn’t someone you live with, which also means it will typically be a partner since people that casual around anyone other than a partner are rare. But I have had the good fortune to have encountered it “in the wild” so to speak.

    That kind of casual confidence paired with the hints of their body is exhilarating




  • I’ve never really cared, so long as the person is going at it from a healthy place. It isn’t the number that matters, it’s about whether or not they’re self destructive in their activity (well, and that they use best practices)

    See, vaginas are a self cleaning organ. Unless it’s fairly recent, any previous dick has had all traces wiped away. It doesn’t hurt that I share very well. I don’t share indiscriminately, but I’m not hung up on going first either.

    Obviously, I’m not a stranger to sharing, which means my numbers would be on the high end since folks that enjoy sharing, particularly in group scenes, tend to have more partners on average.

    Unfortunately, I’ve never been able to pin down an exact number in part because of group scenes. I can remember everyone I dated, and even the occasional hookup (though I was never a fan of that whole concept of going out to get laid and never seeing them again as the default outcome)

    I know I’m in triple digits. I think it’s under 300 individuals, though I may be wrong when factoring in partial sex acts. As in, would I count it if all I did was ejaculate on someone, or something like just gagging someone with my cock as part of consensual humiliation? I don’t tend to think of things like that as sex, per se. And would I count people that were present, but I didn’t even touch? If it’s a group scene, aren’t you kind of having sex with everyone? For that matter, how about bdsm play that didn’t involve any penetration or the cases where no genital stimulation was involved; is that sex?

    Would I count people that were watching me do something for their own sexual gratification when I agreed to perform for that reason? I once masturbated for a group of people as a performance specifically to serve as an erotic stimulus. Does that count?

    If I factor in all of that kind of thing, it’s creeping up to the 500 mark, approximately.

    But sex as in my penis going inside someone, (or the extremely rare penis going inside of me), or other forms of genital stimulation; it’s somewhere between 2 and 3 hundred. I think on the lower end of that range. So not any kind of record, but still an outlier.

    With that kind of approach to sexual matters, you can see why a partner having a history of their own doesn’t factor as a negative for me. I’d be more worried about a partner with less than a dozen previous partners that didn’t engage in good use of condoms and barriers.




  • I mean, you’re gorgeous, so damn near anything will look good on you.

    I get the impression you’re actually looking for feedback on the outfit/style though.

    I dig what you’re doing. I might go a little longer with a skirt to accentuate your lines more, and then lean hard into the petite breast factor by going with something that will drape and cling, showing their shape tad more. Maybe something in a light silk if you’re into that particular cut of top.

    A similar type of fabric, but in a button-up you can leave the top three or four undone to give a glimpse of sternum and the very edge of the swell of your breasts, would also walk that line between showy and demure.

    In cooler weather, I’ve seen thin knits do wonders for a lean body type like yours. Surprisingly, flannel does a really nice effect as well. Just have to avoid the usual plaid since it doesn’t accentuate those long, graceful lines of your body type as well.


  • Well, there’s a few caveats to this. First, that I’m not sexually attracted to men, which skews perceptions some. Second, that because of that, my experience with men in this way was exclusively via bdsm play where I was topping them (which allowed me to get around the lack of attraction and get erect (though I sometimes had to use support devices like a cock ring to stay erect).

    Thirdly, that in terms of numbers of partners, I can count how many men I penetrated with my penis, and those I truly fucked; whereas I lost track of how many women I did anal with. So the comparison is limited.

    There are differences. The obvious one is that men are taller and physically larger on average. So positions make the penis go in at different angles sometimes. Since most of the men I fucked were there to be dominated and used, they were bent over for at least part of the act, and you notice the height difference, as well as the more muscled buttocks, when they apply. But even a fairly well muscled and tall woman still has a different hip ratio, so it still isn’t exactly the same.

    Someone else mentioned that men sometimes have a hairier backside, and that is the case for some. You can feel the extra hair when it’s present. It’s scratchy as you’re going in, even with a lot of lube. The hair is also much coarser on average, so even very hairy women, the hair isn’t as noticeable during action.

    I’d also say that men tend to be a bit more capacious. Not necessarily looser, but once they get relaxed and warmed up, they seem to be able to take more girth, and depth, than women before things get uncomfortable.

    A bigger difference shows up when the man is into being fucked, whether or not they’re otherwise bisexual or homosexual in the rest of their life. The men that enjoyed being fucked just responded with more gusto, particularly once things got going and the position was right to hit the prostate. The ones that were only into anal as a form of domination or humiliation were much less likely to really open up and enjoy it, which means they carried more tension if they weren’t all the way broken down before or during the process.

    Even when they were broken down into the right frame of mind, the ones that didn’t enjoy anal per se rarely felt “alive” the way someone that likes it does. But even women that love anal don’t typically respond physically the way men sometimes do. The pulsing of their orgasms feels different for one thing, but just the way men vs women feel inside when they’re being fucked in just the right way for them as individuals is different. There’s an extra bit of something that I find difficult to put into words. Best I can say is that the internal motions feel different as the sex happens.

    I definitely prefer anal with women because I prefer women, but I suspect that if I were bi, I might prefer anal with men. The sensation of it, if you ignore everything else, is distinct, in my opinion, in a way that stimulated my penis more intensely.

    There was a degree of extra fun in breaking a man down with anal though. The men that were gay or bi didn’t often respond to the “threat” of it in as visceral a way. A hetero or very hetero leaning bi man would struggle with themselves more, so I could ride that tension and make the process of making them come by being fucked “worse”, and in the handful of times it happened, their orgasms were intense enough to feel very good to me. Women, for whatever reason it may be, didn’t tend to respond to anal as a tool of dominance and control as viscerally. So, of the ones that orgasmed, it didn’t have that same power to it.

    So it’s one of those things where I wouldn’t seek it out. If I were single and horny I’d go home alone rather than try to find a man to fuck. But, in the context of the scene, I didn’t object to topping men when it worked out that way, and if if that meant fucking a man, it did feel good enough that I would occasionally come as well. Not every time, and there were a few times where I couldn’t stay hard even though it felt good physically. I bring that up because of the caveats.

    A lot of what people tend to feel during sex is filtered through the brain, and the brain is our biggest erogenous zone. If I were bisexual, I believe that my lived experience of fucking the exact same men in the exact same ways would have been different. And, thus, my perception of the physical stimulation likely would have been different as well. If nothing else, I’m confident that I would have had more orgasms myself, and that I wouldn’t have needed support via cock rings, which tend to slightly alter sensation in their own way (not necessarily better or worse, just slightly different).

    I can recommend trying to fuck someone outside of your orientation, btw. I had my kink to bridge over the lack of attraction, so it was easier in that regard. But if someone is somewhere on the gay-bi-straight slider, you can learn a lot about yourself just by making the attempt to cross over your usual attractions. You’d have to find someone willing to help you experiment, but that isn’t a total barrier to entry, so to speak.


  • It’s really about picking the right partner. The details of what to do, how to do it don’t matter much even if you were straight because there’s just too much individual variance in what people like. Yeah, the usual advice of not ignoring the clit applies almost all the time, but beyond that, you gotta communicate before and during.

    Be honest, be open, and find someone that’s both willing to be a supportive guide to their body, as well as understanding that it is an experiment. It’s one of those times when it really should be about one person. If you go into it thinking about what you’re doing to her, you aren’t really going to satisfy that curiosity.

    Instead, think about negotiating a mutually pleasant experience where you can explore, ask questions, and work your way through the experience. Tbh, that’s a great thing for any first experience, but when you’re crossing a major barrier like orientation, it’s damn important.

    For real, you aren’t going to master that pussy your first time having access to one. Nobody does. So focus on finding that partner that’s going into it with a frame of thought that matches what you want out of the experience.

    Now, like others have said, you’ll notice a lot of differences, beyond the obvious. The way pussy feels vs anal is a massive difference, but you might be surprised to find out that a man’s ass feels different than a woman’s, as does oral. The male body responds differently to anal as well. Neither is better than the other, but (or butt, I guess) if you end up enjoying things, and having sex with women anally, you’ll get what I mean.

    You’d also be really well off if you can find a partner willing to let you switch back and forth between positions to really get an idea of why doggie vs missionary can be such a major difference in stimulation and pleasure.

    Now, I can’t say all that without saying that “holes” aren’t actually what sexual orientation is about. So a fair warning that your body may not cooperate because your brain says hell no. I used to be active in bdsm circles, and sometimes topped men in scenes that included penetration. I’m not attracted to men, so it occasionally took assistance to make that part happen. So, if you run into trouble, you may end up needing similar assistance, or to make sure your partner is very masculine while still being a woman. Ymmv, but I had less trouble with very feminine men at least.

    Only thing I can think of to add is that exploring outside of your orientation can be very rewarding on multiple levels. But it can also be stressful, so be prepared for that, just in case.



  • Well, yeah a lot of men are really into it.

    For me, it isn’t a specific fetish, but it does come with a symbolic weight that other actions don’t have. Again, it isn’t something I need or have a strong desire for for. But, there is something a little dejecting when someone spits it out actively. It’s a subtle rejection, though fully understandable. I’ve had semen in my mouth, and I’m not fond of it at all.

    Having had semen in my mouth, I have zero problems with anyone that doesn’t want it to stay there. But it is a lot better if it isn’t done in a way that’s unusually intense. Sure, spit it out, but maybe don’t run to do it, just casually do so. Or just back off a bit and let it hit the front of your mouth and immediately run out, if it isn’t a deep throat situation.

    It is true though, that the symbolic weight of accepting the seed and taking it in matters. Not just to me, I’ve known many men to say the same thing, though not always in those words. It is also true that a partner that enjoys the process of both making a man ejaculate and swallowing (or even spitting after savoring it) feels extra special. Again, that’s not just me, other men have said similar.


  • Multiple times.

    For the most part, it’s like you said: someone changing clothes, or losing them via unintended consequences like jumping into a pool wrong and not realizing it.

    Many years ago, my family went camping to one of our favorite spots. As usual, I set up my tent close to the creek. Every morning after that, and occasionally if I was relaxing and reading, the campers from across the creek would be visible as they used the bushes, but didn’t realize said bushes weren’t hiding anything from our direction, only from their own camp.

    I was young enough that I wasn’t going to say anything because it was a bit of a rush, and I had no clue how to go about letting them know they were entirely exposed as they did their business.




  • Generally, convincing a partner to open a relationship is a bad idea. It’s better to frame it as something you’d like to try, and let them gradually warm to the idea through conversation.

    But since he’s bringing it up, you can modify that. Be honest. Tell him that it’s a turn on. Discuss the boundaries, expectations and benefits. Let it build to a mutual desire, and it’ll happen naturally.

    It’s usually a good idea to be very picky about who is and isn’t an acceptable play partner. Strangers vs friends are a totally different vibe. Men vs women. Emotional bonding okay or not. All the little things that can make the experience go good or bad.

    Back in the era of my non monogamous life, if I was sharing with other men, it had to be a situation of mutual respect. No exceptions, no mistakes on that allowed or I was out and that meant out if the boundary wasn’t enforced by my partner as well. So it was almost always going to happen with friends, or in established groups for the purpose.

    With women, I still insisted on that respect, it was just less likely to go wrong since even unfamiliar women willing to play were also usually all about agreements being done before play. Only ever had to call that rule into things once. Then again, even with men because it was always a mutually agreed process, it never had to go beyond a “hey man, remember we’re all here to have fun, it isn’t a competition” and it would be fine, no need to end the play.

    Really, most guys that are bringing it up, all you gotta do is be patient and be willing to insist everything is hashed out before there’s other dick in you. Which is just as true if you’re all guys, as far as I ever saw, and it holds true if there’s no second dick involved at all.

    I’ve been the second guy as well. So I’d say make sure that whoever you might pick is aware of your boundaries and asks questions that show they understand what is involved, rather than them chasing tail and not caring about anything else. It’s a hell of a lot nicer if you’re the outsider if your new partners are clear about big issues. Like, if the couple want a bit of role play where you’re playing bull, you need to know that. And the reverse is even more important; if there’s something like they don’t want you complimenting or encouraging either of them, you want to know that. It can be awkward as hell to express admiration of someone’s cunnilingus skills and they realize that they don’t want your input like that.

    Remember, all the work it takes/took you and your guy to become happy partners has to be done for the third person, and it has to be right for both of you and for him/her. It’s not just you having sex with the third party, even if your bf isn’t in the room. There’s still three interactions in play. If you’re all in the room, every little dynamic might matter.

    Also, since your question came with a pic, I don’t think you’ll have trouble finding someone, so you can afford to be picky.