First Time TS

casualguy   June 28, 2017   | 154531 Views
My first time with a transgender was not how I thought it would be...... stepmom After many years of imagining just what it would be like to have sex with a transgender female I decided to do it. I searched the local personals website and saw that there was a shemale available on the local strip. When I arrived at the motel , I was greeeted at the door, not by a beautiful TS girl, but a gay black guy wearing a wig. He let me in and went to close the door, I knew I had been baited at that point and simply opened the door and walked out. Later that night I texted the person back and told them that if they had been honest with me on the phone I may have stayed. He apologized for the false ad and explained that most men don't care , they just want to have gay sex. I told him I was looking for a transexual girl.
Now by this point I was so horny I no longer cared, I just wanted to suck a cock. He said that if I wanted to come back, there was a second person there and I could see both of them for a discounted price. I accepted his offer and agreed on a time. When I returned later that night I entered the room and saw a second black gay man laying on the bed already half erect. We said our hellos and I immediatly stripped out of my clothes including my socks. I wanted to be totaly naked in front of these men. They asked me what I wanted and I told them to lay on the bed so I could get them both hard and then they each could take turns with me.
The one lay in front of me , legs spread his cock was totaly soft. I took it into my mouth. The other sat up against the head of the bed with his legs crossed. Both were getting equal attention and were fully erect in no time. As I sucked the cock that was in front of me, my ass was being oiled up by the other guy. It felt good. He lightly slapped my ass and told me to get on my hands and knees, I did. I watched as he placed a condom on his big dick. He slapped his cock on my asshole like men do to women's pussy in a porn movie. Then he started to put it in. Not all at once thank god. I was in pain. I was told by the other guy to put his dick back in my mouth and keep sucking. As I got more loosened up I started to suck his dick harder. Both of them were saying nasty things to me, my ass was being fucked, he kept saying how tight my pussy was. It was degrading being spoken to like that but I knew going there what the atmosphere would be. My cock was rock hard from the prostate stimulation but there was nothing I could do to relive it. By now I had been pushed face down on the matress, his massive cock now getting me full stroke. I could feel his breath on my neck. I could taste the salty pre-cum from the dick I was sucking. He was about to blow. He pulled my head onto his cock, I grabbed his ass cheeks. I had made up my mind going over there that night that I was going to swallow cum from one or both of them. I felt a warm gush in my mouth, a massive load! He could no longer take the sucking because of the sensitivity. I grabbed his ass and forced him to keep it in. He pushed my head away and collapsed onto his back.
The pounding I was taking was almost over, all of a sudden he stopped, I could feel his huge dick throbbing inside me, my man pussy finally overcame him. I ejaculated on the the bedspread from the friction being generated during my topping.
Not much was said as I got dressed, I was given wipes by the one guy so I could clean up the lube that was running down my ass, I watched as the guy pulled the condom off and threw it in the toilet, his dick had to have been 10 inches long. Later that night I showered and looked at my anus in the mirror. It looked bruised and there was loose skin there as where before it was just a hole, it took weeks before it went back to normal. I felt shame for the first few days after that night, but I realize that some things need to be explored.
Score this Story
Add to Favorites
Report Story Add To Reading List
More transexual stories you might enjoy
straight, juicy sex stories 131 Each action has consequences…
Read Story
straight, juicy sex stories 48 THREESOME SEX AT THE BEACH…
Read Story
straight, juicy sex stories 21 Shemale sister enters my…
Read Story
straight, 26 3 14 21 I walked beside the bed where…
Read Story
crossdressing, juicy sex stories Hello readers, hope you enjoy…
Read Story
you need to be a member to score, comment on or flag stories. Please register or login
Erotica books - collections of naughty sex stories by our Juicy members. Get your erotica book featured here

Featured Members

gay, juicy sex stories profile 6
I believe I have reached half way through my life. made some great decisions and some dumb ones. I try…
profile, 26 3 14 3
What can I say?... Gotta love sex. Makes me smile. Makes me shine. Know what I mean?
lesbian, juicy sex stories profile 6
I've always been into girls for as long as I can remember. Love writing erotic stories and would love…
Published erotica author under the name of Jade Melisande; kink, sex & relationship blogger at;…
straight, juicy sex stories profile 119
Why do I smile? Lots of sex that's why. If you get a lot of the good stuff you can't help but smile…