Rory
02-12-2007, 09:22 PM
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.
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.