I'm new to this site and had posted this under chit-chat. I'm going to repost it here because it fits this category better....I would really appreciate any advice/feedback... I'm a male, early 30s, very good looking. I'm not a big fan of categorizing, but I would say I'm straight. I'm not attracted to other men, though I have been attracted to transsexuals. I'm not sure what that makes me, nor am I too concerned/worried about that part. What has shaken me up a bit is I had got together with a transsexual lady the other night. I don't drink or do drugs, I just happened to be particularly horny on this night. Anyway, we started making out and it got pretty heated. I was going to most likely have intercourse with her, with me being the top (I have been the top before with other transsexual women). But she said she's a top. So she started performing oral sex on me, and one thing led to another and I allowed her to penetrate me. Long story short, I lost my anal virginity. She put her johnson in my rear, not for long, and at the time I didn't mind it. It actually felt okay. I came, mainly because she was sucking me off for so long and I hand't masturbated in some time prior to that. And I jerked off while she was in me. I feel kind of weirded out. I'm not religious, but I was raised catholic (12 years of catholic school), so maybe there's some lingering issues guilt there? I don't think so, though. **I just felt like I did something wrong, and I've been beating myself up about it in my head, dwelling on it. Probably one reason I've been kind of stuck on it is because my butt (sphincter) has been sore since the morning after it happened. Is this common? How long will it hurt for? For the record, we were safe, we both wore condoms, so I'm not really too worried about STDs, though that is a small portion of my whole feeling weirded out...I'm a worrier by nature sometimes, so even though we were safe, given the fact that I alllowed someone I just met to screw me, it adds to this whole thing. Well, that's my story. I'm being about as truthful as possible, and I would really appreciate any feedback or advice from experienced people out there (especially in regard to having it done to you the first time (emotionally) and how long it will linger (physically, the pain from being penetrated by an erection). Thanks so much.
I honestly don't know... In principle there's nothing wrong with not liking to bottom. But, well, were I the world dictator, there would be a law about every guy doing it at least once. And consider: the people who disapprove of it the most would probably find your attraction to transwomen (and their mere existence, for that matter) just as objectionable, while there's plenty of straight guys only attracted to cis women who enjoy receiving anal and do it regularly. As for soreness... Well, if everything is perfect, there's no any soreness at all. If it's not perfect, but generally safe and sane, you may be a bit sore for a while, but not much or for more than a day. From what you tell it's looking that either she rushed things a bit more than is good for the first time, or you ate something that exacerbated the problem. If you plan on going on having sex with her, try more foreplay, more lube (you did use lube, right?) and it would be generally easier as you learn to trust her and be more relaxed about the whole deal. Good diet and hygiene also help. You may try to read Jack Morin's classic "Anal Pleasure and Health." It's still probably the most comprehensive exploration of both physical and mental aspects of anal sex (the latest edition is avaiable in several major eBook formats, if you don't want to keep a physical copy around.) Its "experiences" part (basically a set of exercises that could make you more comfortable with your anal sexuality) might be a bit more than you bargained for, but since you apparently have anal regularly as a top, it may be useful to you anyway as a source of advice.
