tagTranssexuals & CrossdressersMy Boy at The Poker Game

My Boy at The Poker Game

byBig Swede©

Chris was a hot female to male trans guy that loved to please his daddy. My trans boy was 22 and I was 48 at the time. Chris is super hot, 5'6", 120 pounds, blonde and blue-eyed. He had been on T for about five months when I met him. He wanted a daddy to take him in and care for him while I wanted a boy that I could help become a man. I will never forget this experience.

This was my regular poker night with the boys. Chris had never played poker with the boys but wanted to join in this week. I was a bit hesitant as I know the boys thought he was hot, they had told me how lucky I was to have such a hot boy. I was proud of him, two of them didn't know he was trans and two did. He was really cute in a boyish way- all man but had that twink soft way about him that made me love him so. I told him I would only stake him $50 and that was it. I knew that he didn't stand a chance against my buddies and me, we have played poker for years. Jim is really good, lucky and skilled, but that is another story. I taught Chris to play poker by playing for sex favors, but again another story.

When I told the boys that Chris was sitting in right away Bret said let's play strip poker - he is gay and he didn't know that Chris was a tranguy. Chris looked like a high school boy and I think Bret just wanted to see him naked. I laughed it off and so did the other guys, it was a bit awkward but was a nice ice breaker I guess. Chris also played host that night and would go get beers and stuff for us as my boy. Chris quickly lost all the money I had staked him and sat on my lap for a while squirming and getting me hard. He had on a pair of baggy gym shorts and a t-shirt (with binder). I was losing and getting a bit restless when I reached up Chris' leg and into his shorts' opening to feel no briefs, I was surprised but excited. I started to play with him and he was putting his arms around me and kissing me and my neck. One of the guys said get a room. I told him he was jealous and he said hell yes.

I started to get really hard, the whole scene was turning me on, knowing that Bret and Jeff didn't even know Chris was trans and Jim and Red laughing as they knew what I was doing in his shorts. I lost a hand worth $75 and was getting low on my allotted gambling money for the night when Chris asked to get back in the game. I said I wasn't going to stake him, Bret said Chris can play with his clothes. I laughed and said are you kidding me Chris would lose his clothes in three hands. Chris jumped off my lap and said deal -- he winked at me as he got off. I knew then that this was going to be wild night. The arrangement was that if Chris won he got the pot, if he lost he had to take off a piece of clothing and socks didn't count. No matter what was bet he was covered by just one piece of clothing, seemed like a good deal for him as he was in every hand and could win a big bet.

He lost right off and took off his t-shirt, I knew he didn't have on briefs and he wasn't going to start with shorts. I quickly looked at Bret and Jeff to see their reactions when they saw his binder. I wished I would have filmed it, it wasn't a sexy binder just the look of confusion on their faces. I know that Bret had a huge crush on Chris and wondered how he would react. I grabbed the cards and started to deal the second hand, of course, Chris lost again. This time he took off his shorts, again I quickly looked at Bret and Jeff. Jeff didn't seem surprised much, I suspect he knew. Bret on the other hand just mumbled something I couldn't hear. Later, I found out he said to Jim why didn't he take off the top (he didn't know that most trans guys who haven't had surgery are very sensitive about that).

I was throbbing so hard as I watched Chris show off his neatly trimmed "fun bits" he usually called it, I called it pussy and he didn't mind. He had a great happy trail up to his belly button and a lot of hair on his legs, it was so fine and silky I LOVED IT. I don't think any of the guys had ever seen a t-cock before and as I glanced around the table I could tell everyone was really excited, including me. I love my boy's hot body, his t-cock is so big and HOT. Chris broke the silence by saying I am out boys and jumped back on my lap without putting his clothes back on. His bare pussy was rubbing my hard on through my shorts and I LOVED IT. I asked him to go get me another beer and as he left I saw all the guys watch him walk out of the room showing off that perfect ass. It was so small and well-shaped like a great twink's ass. I was thinking as he walked away that from the back you would swear my boy was a cis man.

We dealt a couple hands of cards before Chris returned, I won both hands as the boys were watching the door waiting for Chris. He came back in with my beer and jumped back on my lap. I looked over at Bret and he seemed to be the most excited of them all. Just before Chris got on my lap I stood up and took my shorts off and sat down in my briefs. I could feel that Chris was really wet, super wet, probably the most excited I have seen him. He turned around in my lap and faced the boys while telling me which cards to discard, we were playing straight draw poker. I had a pair of Kings and drew another one so I was pretty excited. Jeff called my bet and raised another $50. I told him I only had $20 left and he said I could throw Chris into the pot. I noticed Chris kind of quiver when he said that. I asked Chris what he thought he said call the bastard. I said wait a minute, I am not going to throw my boy in the pot for a mere $30. Jeff said he would take Chris sitting on his lap for five minutes, Chris yelled call and I said sure.

Well, Jeff threw a full house (sixes over jacks) on the table and Chris started to reach for the pot and I told him we lost. He laughed nervously at the same time he was gushing moisture out of his pussy. Jeff stood up and pulled his shorts down and was about to take his underwear off when I said wait a minute, the deal was Chris would sit on your lap but NO FUCKING. We argued back and forth what the bet exactly was, of course the other guys took Jeff's side until Chris said he would sit on Jeff's lap and he could play with his fun bits but can't take off his binder and Jeff had to keep his briefs on. Jeff agreed with that Chris jumped on his lap facing the table. Jeff had a nice cock, it was pushed off to the side and stretching his briefs to the limit. His cock head was covered in a wet spot where he had been leaking pre-cum all night.

Chris looked so hot sitting in Jeff's lap grinding his pussy down on Jeff's brief-clad cock. Jeff was alternating between rubbing his fingers on Chris' t-cock and thrusting his hips upward trying to shove his cock into Chris's fun bits. Jeff reached around for Chris' binder and Chris slapped his hands away. I knew two things about Chris, he would only take his binder off in front of me and he had an absolute rule on no barebacking. It took two months of dating before he let me fuck him raw and he said I was the first one. In fact, he claimed I was the first cis guy he ever let stick it in his fun bits. He had sucked and been fucked in the ass before me, but I digress. I set the timer on my watch for five minutes and we kept playing cards but no one was really paying much attention. We were all watching Chris' pussy get wetter and wetter -- so much so that Jeff's cock was completely visible through his soaked briefs, they were white and the outline of his head and cock were so clear -- I wasn't sure if it was Chris' or Jeff's juices but boy was it hot to see this big cock stretching a soaked pair of briefs to the limit as it arched up to meet Chris' t-cock with every stroke. Chris was concentrating on rubbing the two cocks together while Jeff was trying to maneuver his cock into the hole. It was fun to watch Chris adeptly slide forward just enough to move Jeff's cock back up to his t-cock.

Jeff was desperate by now as there was only about a minute left and he wanted his cock in that hole so bad, he reached down and Chris grabbed his hand and helped him rub the brief-clad cock up and down Chris' full length ending at his t-cock. Jeff was stronger however as he got the head of his still brief-clad cock slightly into Chris' hole, must have been about two inches I would say, just enough for the folds to open and wrap the cock head. Just then my timer went off and Chris jumped up and came back to my lap. Bret said I want a chance to play for the lap treatment. I was kind of surprised as I knew that Jeff was 100% gay and was never with a trans guy before. I had mentioned something about them once and he said he didn't think he would be interested in pussy. I told him that trans men are more than pussy, they are men who happen to have this sweet hole. Obviously, Jeff had changed his mind as he had placed his hand in his pants while Chris was on Jeff's lap and now was insisting we play for turns with Chris on their laps.

I asked Chris if that was cool and he said sure but he got to keep the money from the pot and same rules. Everyone agreed and to make sure that Chris made some money I kept the betting up there. The first pot he took in $60 as all four guys called. Bret won and you would have thought he won the lottery the way he let out a yell. He pulled his sweats down and he had on these really skimpy silk briefs and a very large cock. What was most impressive was the head, it was huge and stuck out of the briefs. Chris told him to put that thing away "buster." So Bret stuffed it back in his briefs. They were stretched so tight his balls had popped out on both sides of the middle part of the briefs which had now ridden so far up his ass they looked like a thong. Chris this time sat down on his lap facing him and away from the table. All we could see was Chris' sweet ass spread and Bret's balls. It look like they belong to Chris as they were hanging down between his ass. I loved that sight and it got me really hard. His pussy was completely concealed from my point of view anyway. I know how much Chris loves frottage and I am sure he wanted to rub his t-cock on Bret's huge cock head.

At this point, I got up and threw the cards down on the table and went over to get a closer view, so did the other three boys. I got so caught up in the action I forgot to start the watch, Chris reminded me. Chris was grinding his t-cock into Bret's cock really hard. Bret was oozing pre-cum like I had never seen. His briefs were soaked just like Jeff's had become from his turn. Bret's thick head was pressing hard against the silk that was holding it back from "pay dirt (football term meaning a touchdown)." Chris was really getting into it bucking back and forth with his hips moving his t-cock up and down Bret's shaft. Every now and then he would hold it against Bret's cock head and moan harder. I knew Chris was getting ready to cum. Meanwhile, Bret was starting to grind his hips as well. But he was pulling them back in a natural fashion to try to get his cock to plunge into that hot pussy that was massaging his cock. I will never forget the look on Chris' face as he was cumming, he was so into it that he shoved his tongue down Bret's throat holding back his moans. I looked down and saw that Bret's cock had worked its way out of his brief's again and this time was naked against Chris' t-cock. Chris thrust his hip hard down on Bret and I couldn't see anything but Chris' really swollen t-cock.

Thoughts were racing through my head, did Bret just penetrate Chris, what was going on down there. They locked in a clench that was so erotic as they were kissing and moaning like to freshmen that had just found out about sex. My alarm went off and after about 20 seconds of no one saying anything Jim finally said hey let's play another hand. Chris started to get up and I saw Bret's cock throbbing against Chris' hole. It looked like it had been stretched with a cock but I wasn't sure, I know that Bret's briefs were now down all the way to his balls and his whole cock was naked and covered with wetness. He tried to pull Chris back on his lap but Chris was pushing him away. Just then I saw Bret's throbbing cock stiffen and freeze. He was about five inches from Chris' pussy when his first shot hit Chris right square in the t-cock. It was one of the hottest things I had ever seen, it looked like Chris' t-cock had just sent that cum out of his t-cock. The second shot hit up higher on Chris' neatly trimmed bush, the third, and fourth and fifth... splashed all over Chris' t-cock, pubic area and pussy. I was very impressed with how much Bret had cum. His cock was beet purple and thrusting up to try to penetrate Chris but to no avail. When Bret finished he let go of Chris. Chris' whole groin was covered with cum and he took off for the bathroom with cum dripping off his pussy onto the floor.

Bret was flush and kind of collapsed in his chair. I looked over at Jeff, Jim and Red and saw they were all hard with their cocks sticking straight out of their shorts (Red had pants on). Chris came back all cleaned up and jumped back on my lap. I stuck my hand down on his pussy and felt it was soaking wet. Jim grabbed the cards and said next hand. Bret said he was going to sit this one out, so Jeff, Red and Jim all threw in $5.00 for the ante. I opened for $20, I knew after that show they would all match and sure enough they did. There was a $100 in the pot and Chris got this huge smile on his face. Jim stood up and said I bet $100 reaching in his billfold and pulling out five $20 bills. Jeff and I folded, and Red threw in his own $100 and said call. Jim won with two pair -- aces and eights -- I laughed and said a "dead man's hand." Jim said who gives a fuck and grabbed Chris at the same time he was pulling down his shorts. He had on boxers and his cock was sticking straight out the hole in the middle, it was hard to tell how long it was because of the boxers but it wasn't nearly as thick as Bret's.

Chris said you're going to have to do something about that and Jim snapped them back together and Chris told him to stand up and he shifted the boxers to the side so that the hole was now on Jim's thigh and his cock was covered by the boxers completely. He sat back down and Chris pushed Jim's cock down toward his leg and climbed on facing the table. I started my watch and now Chris was rubbing his pussy/cock up and down Jim's boxer-clad cock. I could see much better from this position. Chris was grinding his t-cock into Jim's cock pretty hard, I know Chris is proud of his t-cock it is so big and when hard about 3", well almost. As Chris was grinding hard he closed his eyes and leaned back into Jim. This caused his hips to shift slightly and Jim's cock head slid out the leg hole of his boxers. With every stroke Jim's cock would stick out farther and farther. Now Chris' pussy was rubbing up and down Jim's glistening bare cock. Each stroke his pussy lips would wrap around Jim's cock and stroke it until it would disappear behind Chris' pelvis which was all I could see, then Jim's cock would reappear as Chris stroked back again. Each time I said to myself this is it Jim has entered him, but each time his cock would come back out between Chris' lips until his t-cock was all the way down to the base of Jim's shaft as his cock was completely bare now.

At about the four minute mark Jim's cock disappeared again and this time when Chris was moving forward I heard him let out a moan of great pleasure as I looked down I didn't see Jim's cock head or shaft or anything but Chris' pussy stretched out. Jim shoved his hips up to meet Chris' and before long there was the unmistakable sound of fucking. I was flabbergasted, I didn't know what to think, a ton of thoughts were running through my mind. Chris jumped up and disengaged, but as he did we could all see Jim's really long cock slipping out of Chris' pussy. There was no mistaking this time a cock had made its way into Chris' hole. Chris to Jim he would have to put his shorts back on or borrow someone's briefs. Jim asked if he could suck Chris' t-cock instead. Chris agreed and Jim spent his last three minutes licking, sucking and tonguing every centimeter of Chris' pussy/cock.

Chris climbed back on my lap this time, he was so fucking wet I couldn't believe it. I was playing with him and reached down and pulled my cock out and stuck it in, Chris was unbelievably wet and HOT, literally hot.

Red and Bret said let's play another hand, come on. Bret grabbed the cards and dealt, this time the pot only got up to $100 as the guys were starting to run out of money. Bret won with a pair of queens. Red complained and said it was his turn. I said hey, it is all in the cards my friend and Chris jumped off my lap and back onto Bret's. I thought it was strange how excited Chris seemed that Bret won.

Bret was hard again and his silky hot briefs had cum stains on them. I knew Chris wouldn't allow him to use those, well I thought I knew. Chris jumped right on his lap and started to grind his pussy into that huge cock again. I didn't even set my watch as I was so entranced in what was going on. I felt a pang of jealousy as Chris closed his eyes and straddled Bret again facing him. They started to kiss immediately, Bret's hands all over Chris' body. Perhaps of all the surprises that night the most amazing to me was when Bret pulled Chris' binder up and Chris let him. Chris has a great top and it is very sensitive. I have tried to convince him to enjoy it but I understood his hesitancy. Now, with Bret nipping Chris' nipples and Chris shoving Bret's face into them I was overwhelmed. This seemed more like making love than a sexual act. With that thought I started the clock.

It was still an incredible sight. I looked down at Bret's lap and couldn't really see again as it was a poor angle for people to watch. I got up and walked over and could see between them and it was obvious that Chris was rubbing his pussy and t-cock really hard on Bret's hard cock again. Just from the moans and groans I knew it felt good. I looked at Chris and he was totally lost in the moment and had this huge grin on his face as he kept pushing harder and harder to meet each of Bret's thrusts. As this happened Bret had slide down further and I could now see his cock clearly penetrating Chris' pussy lips, it started with his huge head. I thought thank goodness his cock head is so big there is no way that is going to just slip into Chris. Chris reached down and grabbed Bret's cock and was rubbing the head up and down his t-cock and opening hard. I thought he was going to stop Bret from actually fucking him, then I thought hell isn't this fucking? My heart was pounding in my chest as I stared in amazement as Chris let go of Bret's cock and it slid in all the way in one shove -- Chris let out a huge moan and it was obvious to all of us what just happened. I wondered if Chris knew, he had to know, how couldn't you? I looked around and everyone had their cocks out of their pants and into their hands jacking off. Chris was bucking up and down on Bret's cock as it penetrated him deeper and deeper with each thrust. Bret was meeting every thrust by Chris with one of his own. They both stopped as Chris impaled himself on that cock.

Just then the buzzer went off and Chris leaped off of Bret's lap like he had been hit with a cattle prod or something. Suddenly, I realized why Chris had jumped so high. There was cum dripping from his pussy as he was pulling off Bret's cock. HE HAD CUM IN HIM! I couldn't believe it, Chris seemed panicked. More and more cum was dripping from his pussy onto Bret's still throbbing cock which was soaking wet with juices from Chris and apparently cum. I literally dropped to my knees and opened my mouth. I remember I thought I said something but nothing came out. I looked at Chris and couldn't believe it, this isn't my Chris. His pussy was convulsing like it was grasping for breath with each convulsion pushing out more and more cum. I thought what the hell is with Bret, how much cum can a man have, he just came not more than an hour ago.

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byBig Swede© 5 comments/ 61813 views/ 39 favorites

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