First Times

When we share first times, we mainly talk about THE first time you stepped over and tried/experimented/experienced... something. I look at many first times. First time I tried kissing. First time I tried oral. First time I tried penetration. First time... and when we share first times, we hear of others and their first time. But every once in a while, we meet someone with an incredible first time.. good or bad. I recall a friend, telling me about his first time experiencing something sexual. As it happens, he was a bit of a "fem"... so as you would imagine, he took the role of the girl. He enjoyed this role and enjoyed what it brought him. So much so, that his role as a passive or fem, or girl - per se, placed him in a position where he was always positioned as such. His first experience was simple, playful, let see yours and I'll show you mine. Then it grew into trying things seen in magazines, then porn. This is where he learned and began to take some pride in being a good, good girl! Slowly, the challenge or chase became the game or want or what was the prize. Could he get this, get him, do that, have him do that... and over time learning slow, he became good at experimenting; pleasing and being what I would think is "that girl." As we talked, he expressed how over time he would meet guys, friends, etc... and not all, but some would become his challenge. Now this was nothing hurtful, or to do harm, or disrespectful, but more of curiosity. Again, experimenting. And with who. My friend explained how he had a thing for wondering what guys looked like naked and how they came. Some were just one offs, or quickies, but a few became regular "playmates' or as we would say, fuck buddies. Oddly enough, when the encounter was more vers. the fun was not the same - he enjoyed being the girl. There were times he would dream he was a girl, having encounters with various partners. As he was growing, he'd have various encounters, at first being mostly oral - he enjoyed making men get off... with his regulars, he enjoyed their cumming and with a few he went further at times. There was one partner, he told me, who he performed oral sex on and it grew into him swallowing his sperm when he came. Turns out, this was to make less of a mess. Over time, he began to expand more in that he would enjoy being bred - but that would be much later on. Oddly, as his encounters increased, his partners were aged more inline with himself, never really being into older men - but there were a few. There was one thing he did favor, straight men. He did have relationships, that always ended as it was difficult to handle being with one man too long. And as he did get older - he would tell me, he preferred to be intimate with younger men. Nothing illegal or anything of that sort; he actually despised any adult abusing minors. But he did enjoy younger to older relationships. In some ways, it was more that he enjoyed the feeling of being sexual with someone to, in a way, teach them or "rock their world". At some point, it was about making them have the best orgasm possible. In other words, taking their cum. I did ask if he'd been in any orgyies, or taken a group of men.. an he said not. A threesome not and then, but nothing more. He even told me when he would go to sex clubs as a younger man, it was an occasional one on one. Although he did want to try to be a bottom for a group... Somehow I think that was just too inappropriate for him. He told me he had fantasies as an older man to dress as a woman and serve younger straight men, but have it controlled by a "boyfriend" who would monitor the event. I asked him to explain.

He said, he would love to have a 25 year old fuck bud arrange for some guys to come by the apartment. Hang out a bit, smoke, drink, relax... then have my friend brought out blindfolded, dressed as a woman, placed in the middle of the room and allow guests to do as instructed. Each of the male guests would have the option to wear a mask and given a "viagra" to ease their process... And they would pleasure themselves with him in the middle of the room. Added, he's reward each with $100 for each cumshot. Pretty wild I thought, and I also thought it would make one hellove a porn. But this is all fantasy.

He did go on about this and that, and how he'd was happy to play that role.. but never become a woman. To him, the kink of all this was the fact that he was a man and that make it freaky.