First experience with someone other than a genetic girl?

[Rory]

What was your first experience with someone other than a genetic girl?

I was 25 and new to New York City. I had been turned on by 'shemales' for a while. Around 20, I bought my first shemale porn, but they were few and far-in-between.

New York City is a really permissive place, and you don't have to wear a groucho-marx mustache and drive 50 miles to feel comfortable buying shemale porn. Times square has dozens of porn shops, and no one seems to care.

I was in one of these DVD stores, nervously looking at shemale porn, when someone kept excusing himself and walking past me. He was sort of my shadow. It was a guy dressed half as a woman. He had earings and makeup on, and his hair was short, but done up like a woman's. He was short, and his whole look was effeminate.

He started making chit chat with me in a really hushed voice, but I was so nervous and horney about the shemale DVDs, and so naive, that I didn't realize he was coming on to me. I just thought he was weird. By the time it finally hit me, he had fluttered away. I thought about it, and just decided to do it, but now I had to go find him in the store. So I pursued him, and he sort of played hard-to-get for a minute, making me follow him around the isles.

I went up to him and said, in a very hushed, low grumbly voice, "do you want to go somewhere?" He said yes, and I followed him outside. I didn't know where to go with him, so he suggested a little hotel. I paid, and basically shoved him through the door I was so horny.

I can't remember all of the details, but I remember he wasn't soft like a woman, but he was small like a woman. I manhandled him. I remember being disappointed that he was wearing dude underwear instead of panties. We played safe, of course, and he blew me, I blew him for a second (remember the condom tasting gross), and then I fucked him. Or tried. His ass was incredibly tight, and I hate condoms--they strangle the erection. He came within seconds.

When I couldn't fit my dick in his ass I was shocked, because I'm only average size. Pussies are so much looser, and to me objectively feel better, but the concept of fucking someone, especially a tv/ts in the ass is really really hot. I think I came by jerking off on him or something.

He was a really nice, sweet guy, and wanted to be friends/hook up buddies, but I was a little shell shocked and freaked out, so I politely declined.

[Rory]

13 i had a friend who sucked me off on a regular basis and mutual wanking.

Whoa. At 13, that's like a dream come true, b/c you can't even sit down in class for more than 30 mts before getting a hard-on

[canihavu]

Back in high school I had a very good friend who I will refer to as “T”. T and I were both in the 10th grade and we hung out together quite a bit. After school, we were usually at each others houses doing the normal teenage boy stuff. Anyway I have always had a rather round butt and T would always find a way to get his hands on it; either by patting me on it, or “accidentally” rubbing up against or some other way. Well one day we were at his house in his backyard and we decided to wrestle. Well T pinned me to the ground face down and at first I could believe what he was doing. He was humping my ass!!! I don’t know what I found more amazing, the fact that he was dry humping me outside or the fact that I didn’t get grossed out about him doing it. I felt his hard cock through his jeans which actually excited and scared me at the same time. Neither of us said anything about this after if was over.

The next evening I was at house sitting in his living room and he gets up and tells me that he’ll be right back. He goes into his room and comes back out wearing nothing but a t shirt and hard on. I started laughing, not because his cock was small (it was about 8 inches) but because he was walking around like nothing. This was the firs time I had ever seen a cock other than my own. Well walked over to where I was sitting and asked me with a straight face, “Can I get you in the butt”. I burst out laughing again because I though he was joking but he was quite serious. He told me that he liked the way my ass looked in jeans and how he wanted to see how it felt. At first I was like, there is no way you’re putting that thing in my ass but he persisted. After some coaxing, he got me out of my jeans and underwear. He stroked my cock for me (I didn’t touch his). He got me on my knees and used Vaseline for lube. He got the head of his cock against my virgin ass but it would not go in. And trust me he TRIED HARD. Well he had to settle for putting his cock between my ass cheeks and humping me until he came that night. He let me do the same thing to him although I didn’t enjoy it as much as he did. We did that a couple more times.