Confessions tagged with 'transexual'.

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#1586

Submitted:

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I was 35 when I finally figured out I wanted to be a woman. Actually, a transexual. My wife left me, and fortunately we had no children. It started when I got drunk and sucked my first cock. I let him cum in my mouth, then a few hours later I let him fuck me and cum in my ass. I confessed to my wife, and she decided it was time to find a new husband.

A few months after she left me I went to see my doctor. I didn't know if the hormones would diminish my cock or not. I still liked to jerk off, and when my tits started to develop I discovered a double pleasure. Not only did my cock still work, I found my nipples were extremely sensitive, and I could actually make myself cum by manipulating only my nipples. What a fucking rush that was.

I have always been rather small for a man, and now I have a thin waist, a big ass and nice developing titties. It usually shocks the guy I pick up at the bar on Friday nights after I suck his cock, then let him put his hand down my pants. When he feels my cock he usually pulls his hand back out and feigns disgust. But after a second blowjob he usually gets into it. It's amazing how many men think they're heterosexual but actually get off on my cock. Sometimes they let me fuck them, but usually they end up sucking my cock. I've been developing a small, but loyal following at the bar. I really don't have to pick up anybody, but just show up and any number of men are willing to trade blowjobs. Sometimes I suck two or three in a night.

A couple of months ago there were two guys who wanted me. One was a large belly, big cock white man and one was a tall, skinny black man. I danced with Damon and got him hard through his pants. I offered him the best blowjob he's ever had if he was willing to bring a third into the bedroom. He said it might be fun. Jimmy was a little more reluctant, but I assured him he would cum at least twice with us.

They each followed me to my apartment, and when we stepped into the living room I could see Damon was already getting hard. I pulled him down and kissed him and fondled Jimmy's cock at the same time. I broke the kiss and got undressed. There was no need to hiding my manhood or my womanhood. I told them both to strip, and they both hesitated, but eventually stripped. Jimmy's cock was massive, at least eight inches when hard and thick. Damon was a little smaller and uncut and I knelt in front of him and took his cock in my mouth. I reached under him and fondled his asshole. I beckoned Jimmy over and took turns sucking each cock. I also played with each one's asshole as I sucked them.

After about 20 minutes of this, with them both rock hard I had Jimmy kneel down with me and guided Damon's cock into Jimmy's mouth. He had sucked my cock before, so I was pretty sure he would do this for me. Damon's cock fit just right in Jimmy's mouth, and while he was sucking Damon I laid down and positioned myself so his cock was at my asshole. He pushed in and I felt him fill me up. "Oh, Jimmy! Fuck me as you suck that big black cock!" He was getting into it as he fucked me and sucked Damon. I looked up and Damon's cum was dribbling out of Jimmy's mouth. I milked Jimmy's cock with my sphincter muscles, and he started cumming, Damon's cock still in his mouth. When he finally pulled out he took his mouth off of Damon's cock.

We all rested a little bit, and I told them it was time for something a little different. They were both still pretty turned on, so they would do anything I wanted. I had them lay down in a 69 position and suck each other until they were both hard. Then I had Jimmy get on his hands and knees and Damon kneel behind him. I told him to put fuck Jimmy, and it took a couple minutes until he was relaxed enough to take Damon's entire cock, but he did. Then I got behind Damon and shoved my cock into his ass. Same thing. A couple of minutes later we were all in a rhythm. I was fucking Damon and he was fucking Jimmy.

After about 30 minutes Damon started cumming. I have the ability to control my cum, so I started cumming at about the same time. They both discovered how it felt to have hot cum squirting into their asshole. They both loved it. After I was spent I told Damon to keep his cock in Jimmy's ass and I scooted around and laid in front of Jimmy and let him mouth fuck me. It wasn't too long and he blew his load in my mouth. I didn't swallow, but held it until he was spent. Then I got up and put a lip-lock on Damon. I shoved my tongue into his mouth and gave him Jimmy's load. I think he may have cum a third time by the way he tensed up and grunted.

They finally left, and all three of us were satisfied. Since that night we have done it several more times, and I have even done the threesome thing with two other groups. I'm the smallest of us all, but I have them all by the balls now.

Last week I quit my job and have informed all six of them that they were to support me financially now. They all agreed, afraid not to. What a fucking slut I am, but what the fuck, it works for me.

#1214

Submitted:

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I had never been sucked off or fucked by a tranny before.

I answered a C/L ad for a TV looking for a man. I figured he was just a crossdresser, a man in drag, so when I actually met him I was surprised. I went over to his place, and he answered the door in a skirt and blouse. We chatted for a minute, then we sat on the sofa. I leaned over and kissed him. He had very soft lips, and when his tongue parted my lips I responded. My dick was already getting hard.

He said, "Let me show you." He took off his blouse and bra, and there were the nicest pair of perfectly formed tits I had ever seen. His nipples were large, with large aeroleas to match. He said they were natural, that he was born that way. I massaged and caressed them, running my fingers around his nipples and finally tweaking and pulling on them.

I leaned down and started to suck a nipple, and he said, "Oh, honey, that's so good. You're making my cock hard." With that I snaked a hand under his skirt to find a very large, thick cock. My cock is about five inches hard, so his seven inches made me feel inadequate. I have to admit my own dick was getting hard. "Suck me, honey," he said. I bent down and took his cock in my mouth. He got rock hard almost immediately.

I've always enjoyed sucking on a nice cock, but never while playing with tits the size of his. He had me lay down on my back with my head hanging off the arm of the couch. He stood up and walked over to my head and put his cock back in my mouth. I played with his nuts, then around to his ass. "You ever been fucked?" he asked. "No, just oral." "Then you're in for a treat," he said. He had me kneel on the floor with my chest on the couch. He knelt behind me and started to lick my asshole. I had never been rimmed before, either. I felt like a fucking amateur. He started to tongue fuck my ass. It felt great. He had my asshole nice and slippery, then got up behind me and put his cock up to my asshole.

I wasn't really too sure about this, especially when he shoved his cock in. I felt the 'pop' when he pushed past my pucker spot. It hurt, but I tried to relax. He held it there for a couple of minutes until the pain subsided. I told him it felt good, and he started fucking me in earnest. Each time he thrust in I felt my own cock twitch. He fucked me for about 10 minutes, then pulled out.

He had me lay down on the carpet on my back. "I want to see your face when I cum in your ass," he said. He pushed my legs up and put his cock back in my ass. I moaned. "Oh, yeah, fuck me," I told him. His eyes never left mine the entire time he was fucking me. He started to stroke my cock in unison to his fucking. He told me to pull on his nipples, so I reached up and took a nipple in each hand. I pulled a bit, and he told me to pull harder. I tugged on his nipples until they stretched no more. He fucked me harder and faster until I felt him tense up and say, "Oh, fuck, I'm gonna cum." I pulled his nipples as hard as I could and he started cumming. "Oh, fuck, fuck, fuck," he kept saying as he filled me with his jiz. When he was spent he pulled his cock out of my ass and knelt down between my legs and started to suck me. He shoved two fingers up my ass as he sucked me. He was finger fucking me while blowing me. I lost control and started moaning. I didn't give any warning, but just started to cum. He clamped his lips around my cock so no cum would escape and took my entire load.

He sucked me until I was totally clean. He then laid down next to me, and for the next 20 minutes we kissed and explored each other's bodies. I finally had to leave, as my wife thought I just went out for cigarettes.

This was a great experience for me, and I look forward to many other nights with Terri.

#1104

Submitted:

""

I matched with well over 3000 guys on tinder (I swear they were hot haha, I deleted guys who were rude and asked for sex off the bat) just to see how passable I am as transgender without ever have taken hormones or shit tons of makeup. They love me and tell me I'm gorgeous and sexy. I confessed to my matches and only a few unmatched me(because "i was really pretty but it was not their thing"). The rest didn't care because I was so pretty to them. I kept a few handsome fuckbuddies from it.

After feeling like I was being recognized in public (in a good way), I deleted my profile...

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