tagTransgender & CrossdressersPoker Night Substitute

Poker Night Substitute


I was an entry level accountant at a bank. The pay wasn't great but it was what I had studied at college and it was a start. To help with expenses I shared the house I rented with Todd, and Trish. Todd was an architect working as a draftsman until he could get something else. Trish was working as a cashier at a local store. We all got along great and the arrangement worked for the time being.

On Fridays we would have several guys over to play poker. It was always a good time although Trish hated to play cards, she liked interacting with the guys. She would dress in a cute little dress or skirt and serve sandwiches and beer. She was definitely appreciated by the perverts we knew. Everything went smoothly until Trish got laid off at the store where she was working and decided to visit her aunt in Colorado for a month. She was planning on coming back but that left four weeks with no one to serve at the poker parties.

The first week was a disaster. Nobody wanted to stay without Trish there. "It's just not the same without someone in a cute dress to serve the refreshments," they said. That sucked. The game ended almost before it began and Todd and I were left to clean up the room and figure out what we were going to do.

"I love our Friday night poker game," Todd said. "Hell, if it came to that I would dress in Trish's clothes and serve beer and sandwiches to the bastards."

Todd's remark made me laugh. Trish was about five foot 6, a hundred and twenty pounds. Todd was six, three and probably went close to two hundred fifty. "What are you laughing at, pipsqueak," he said slapping me on the shoulder. "Hey, that's it!" Todd turned and all but ran into Trish's room. He returned with one of her sun dresses, a pink one. "Strip, Will," he commanded me.


"You heard me. Not naked. You can leave your underpants on, just get undressed."

I don't even know why I obeyed him. Something happened inside me when he spoke like that. A place in my stomach got warm like I had eaten something hot and it was just laying there, comforting me. As I undressed I felt myself responding in another way and I had to fight it. What would Todd think if he thought his rough commanding manner had nearly caused me to get a hardon? I stripped slowly to my white briefs and Todd handed me the sun dress. "Put it on."

Again I obeyed without quite knowing why. It fit perfectly.

"Ha, a shave and some makeup and you might be almost as pretty as Trish," Todd laughed. His look was disconcerting and yes, I now had a full blown boner in my underpants. "I think you should be our serving girl at the next party," he said.

"I have to pee, Todd." I turned and shot toward the bathroom where I closed the door and lifting the dress, I lowered my underpants, sat on the toilet and jacked off. I caught it in a wad of toilet paper and flushed it. I stood, washed my hands and returned. The idea of playing the part of a girl was starting to intrigue me. Heck, the guys would just see it as a joke and go along with it, wouldn't they. "Ok, Todd," I said, "let's try it. Maybe it will save our Friday night games until Trish comes back."

That was that. The following Friday we called all the guys and told them we had a new serving girl. They showed up on time.

Before they all got there I shaved my legs and my face and went into Trish's room and dressed. This time I even put on a pair of her panties. They were pink, sheer material and yes, I got a boner as soon as they touched my cock. There was just something erotic about girl's panties and something even more erotic in actually wearing them. I put on makeup and even found a wig to wear. Thankfully the dress I chose was rather full, and it hid my erection even though it was a bit short. I would have to be careful but I would be standing most of the night anyhow.

The idea was a hit. The guys thought it was funny as hell and said that I would definitely do until Trish returned but that I had to give up my position as soon as she was back. We all had a good time with it. They even flirted with me and one guy, Vinny, actually played with my ass while I was putting his beer and sandwich down. I wasn't exactly homophobic but I also didn't think of myself as gay either. Still, Vinny's hot hand on my ass caused my cock to stand up a little more than it already had.

The only other incident was with a guy named Henry. Henry actually put his hand under my dress and played with my ass through the panties. That's when I began to get really frightened that I might be gay because I nearly came as he touched me. It was a fun night but I was tired when they left and glad it was over with. I collapsed on the sofa and put my tired feet up on the coffee table in a most unladylike position.

"That really turned you on, didn't it, Will?" Todd was standing right in front of me. "You've got a boner that's going to rip Trish's panties soon."

Realizing that I had sat down in a revealing way I quickly put my legs down and squeezed my knees together feeling my erection squeezed with them.

"I think you like dressing in sissy clothes, Will." Todd kept up his teasing. "I know its starting to turn me on." That was the point where I looked at Todd's groin and saw that he was in full erection. It was also the point where I realized that the thought of another man's penis didn't gross me out. No, actually it was attracting me and at that moment that was rather scary.

Why I spoke without thinking is beyond me. "It sort of turns me on, being a girl, Todd." I wanted to suck the words back into my mouth as soon as they were out.

"Yeah, I couldn't help but notice, Will. Heck, maybe if you like dressing like a girl you might like acting like one too. It wouldn't be so bad would it. I haven't been taken care of in over two weeks, I'm ready to explode." Todd reached down and held his balls making his erection stand out more. "C'mon sissy boy, on your knees," he commanded. Again that authoritative voice made my stomach heat up and this time it seemed to travel right to the base of my balls and made my cock stand up even harder.

I looked up at him. "Todd, you won't tell anyone, will you?"

"Hell no, it's just between us two," he promised. "No one will ever know but us. Will, if I didn't miss my guess, you have a look in your eye like you just want to eat me." He walked closer to me and I slid off the sofa and went to him dropping to my knees, caressing his hard cock through his pants and underpants. When I cupped his balls they were heavy and tight and I bent and kissed his shaft through the clothing. I was a girl, all my thoughts were those that a girl would have, being dressed like a girl was making me think and feel like one. He moaned as I blew hot air through his pants onto his cock shaft and began to unfasten his trousers.

There was a musky smell coming from his warm balls and cock and that turned me on even more. His cock was oozing pre-cum and I bent and licked it tasting the warm salty flavor and I went on to explore thick soft head of his raging hard cock with my tongue. My fingers wrapped around his thick shaft and when I squeezed and saw his cock slit open I slipped my tongue inside there and Todd jerked and moaned with exquisite pleasure. My fingers went down to find his packed balls as my mouth took in his boner. I squeezed them and reached up and under them to find his tight little asshole. That was all it took. As my finger pressed into his asshole I used my free hand to again squeeze his wonderful balls and he shot, filling my mouth with his warm, thick man juice. I swallowed hard but it was a lot and then he contracted again and another filled my mouth as much as the first. I felt his balls working in my fingers and the powerful muscles at the base of his cock contracted and again he filled my mouth with his man cum. It was too much and I couldn't swallow it fast enough. I pulled back slipping off his cock and three more times he shot loads, each as big as the last and covered my face with his cum.

I kissed and licked his wonderful hard cock and then went into the bathroom to get a towel and clean my face off. When I returned, Todd said I really turned him on. His cock was still huge and rock hard and he said he wanted me. He took me to his bedroom and pushed me back on the bed and lifted my legs. He pulled my panties to the side and exposed my ass hole and I heard him in his end stand drawer. He was putting Vaseline lubricant on his cock and then in my ass hole and then crushing my cock and balls between us he entered me like I was a girl. I cried out in pain as he filled and stretched me but once he was in the pain gradually became the most wonderful pleasure. He pumped in and out of me and called me his little girl sissy. And I began to return his enthusiasm humping up to meet him.

He howled his pleasure when he felt his balls contract and ready to shoot his first load of sperm into me. It was huge and I felt it like I had the enemas my mother made me take as a kid. The feeling was so erotic and I couldn't help filling Trish's panties with my own cum as I was taken like a school girl there on Todd's bed.

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by Anonymous02/18/19


It began when I got a job at a dress shop, just moving stock around at first, but because I had an almost perfect size twelve body, including a waspy waist (and tits are easy to improvise anyway) I wasmore...

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