Hired for a Poker Party

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Waitress for a poker party and more!
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I have been chatting off and on with a local man for a few months. A couple weeks ago he asked me if I would be interested in being a waitress for his next poker party and he would pay me $200.00 plus tips.

I got really excited at the thought of doing it. I told him that I had a few thousand questions first! Lol! First was, how many guys would be there? Four, he responded. Second one was, do all of them know that I'm CD? He said that they did, and he had already showed them some of my pics. Lastly, I told him I didn't have a maid outfit. He said to wear anything I'd like.

I mulled it over for a few minutes and finally asked him when and where. He said Friday (the 21st! Yes, this just happened!) night at 9, also he asked me to be there at 8:30. He wanted to meet me first and then greet each guy as they came in. I agreed to everything and told him to text me at 8, letting me know it was still on.

Friday finally rolled around, and I started getting ready. I was so nervous my hands were shaking the whole time. I made sure I was smooth and clean all over. I took extra time with my makeup and hair. Then I picked out my fave little black dress. Matching bra and thong and added black thigh high stockings. Put on black 5" heels to match. After adding jewelry, I did my nails in white. I was ready a half hour early.

Right at 8 I got a text from him saying the party was a go and asking if I was coming over. I told him I was leaving right away and I would be there at 830.

As I was pulling into his neighborhood I noticed that there were some pretty nice houses. I texted him that I was about to pull into his driveway. He said to come to the front door.

I barely rang the bell when John opened the door. He smiled and said I looked great! We took a tour of the house. He started showing me the kitchen, the poker room and a bathroom only I would use. He explained that I would serve drinks and snacks, and asked if I was ok with them feeling me up whenever they wanted? I laughed and said of course! I told him I didn't like pain, so no pinching or hard slaps. Light spanking was fine.

He then looked a little embarrassed and asked if he could get a feel and look before everyone got there. I told him to sit down, and I would give him a lap dance. I told him that he could feel anywhere he wanted! He put on some music, and I started dancing for him. I started teasing him from far away then I got between his legs and turned around and started grinding my butt on his lap. I could feel he was rock hard already! I lifted my dress to show him my panties and butt. He was still shy, so I grabbed his hands and put them on my cheeks! Then I brought his hands to my boobs. After that he didn't need any more encouragement! Finally, I faced him, pulled up my dress and straddled him. Letting him smell my perfume and kissing his neck. I whispered in his ear asking him what he would like to do to me. He cleared his throat and asked me what can he do? I told him, well you're paying me so you can do pretty much anything you want! His eyes went wide open! (I did have to tell him the few things I don't do, which he was more than okay with. He also said he would tell his friends when they got there.)

We had about 10 minutes before the first guests were scheduled to arrive, so I asked him if he wanted the first shot at anything. He asked if I would give him a blow job to start. I just backed up and got on all fours and slowly crawled over between his legs. I started feeling his still hard cock through his slacks while unzipping him. I was having a little trouble so I asked him to stand up and take his pants and underwear down. As his boxers came down, his hard 7" cock bounced into view. I sat him back down and gently started kissing and licking his head. Then just as I was being real gentle I suddenly swallowed his whole cock down to the base and used my tongue to lick his balls! This had the desired effect on him! Lol! I managed to go up and down a few times before I felt like gagging. Then I went back to slow soft gentle kisses and licks while keeping eye contact. Just then the doorbell rang! I asked him to get it so I could go fix my lipstick and hair and would be out to greet the guest in a minute or two.

As I was getting fixed up, I heard three voices. Two guys must have showed up together. I heard them ask for something to drink just as I came around the corner. I said "Hello gentlemen! I'll get those for you!" I grabbed three beers and went over and handed them the beer. I then said "Hello, I'm Robin and I'll be here to serve you gentlemen all evening. And don't be afraid to ask me for anything!" They introduced themselves as Sam and JT. They were both handsome, well dressed men. I gave them both a hug as they introduced themselves so that they could get a good feel as I hugged them. I showed them to the table and sat down with them while we waited for the next guest.

I could feel 3 pairs of eyes lusting after me as we made small talk and waited. John spoke up and said that there was going to be 2 extra guys coming over, so 6 instead of 4 guests. He said, "I know I said $200 but he would make it $300 for the extra two". I smiled happily and said the more the merrier!

I excused myself to the kitchen and tried to stop my hands and knees from shaking! Lol! I got myself a drink while trying to listen to what they were saying. John was explaining my limits to them, then Sam said "So we can feel her up anytime we want?" John said yes, it's ok with her. One of them asked "What about other stuff?" John told them about what was happening when they got here and you guys' better tip her well!

After a few minutes I came back out and stood between Sam and JT putting my hands on their shoulders and asked if I could get them anything. As they both said no, I felt both of their hands meet each other at the small of my back. We all started laughing, so I grabbed each hand and put one on each butt cheek. I said, "I know we are all nervous so let's break the ice". With that I slipped my dress up under their hands so that they now were feeling my bare skin and could see my cute pink thong panties. I bent over the table to give them better access while looking at John face to face. He looked at me and said, "This is going to be a fun night!" I smiled at him and agreed! Sam and JT were now standing up and I had four hands roaming all over my body. Sam was the first to get directly behind me and grab my hips and start grinding his cock against my butt. I started pushing back against him when the doorbell rang!

I stood up and pulled my dress back down and asked John if he wanted me to get the door. He laughed and said "Oh god no! It might be one of my neighbors and not the other players!" I laughed and said "Good point!" saying I'll wait in the kitchen and bring out the drinks. It turned out to be the other three players.

As I heard them all get to the game room, I came in with 3 beers and introduced myself to Ray, Bill and Steve. They all were just the same as the others except for Ray. He was at least 6'5" and just ripped. I'm sure he saw my face blush as I stared at him. I made sure to hug him last. He smiled at me like he knew he was going to push me beyond my limits.

After some more small talk I asked them how long the game usually lasts, they all laughed and John said "Probably 30 minutes tonight!". I said "I'll be out every few minutes or so to see if anyone needs anything", and told them if they need anything just holler. As soon as I got in the kitchen, they all hollered my name at the same time and started laughing. I came back in laughing and said they were very funny. Just before I turned to walk away with sexiest walk I could, I told them this was going to be a fun night.

I got a tray of snacks ready and took them to the guys starting with John, I knew he would feel me up while I was standing beside him. That really started the ball rolling! For the next hour every time I served one of them, they would grope me. Most of the time 2 or 3 of them would feel me up at the same time. I was loving every minute of it! Soon, I started taking turns sitting on their laps as they played. I made sure my dress was up just enough so they could feel my bare skin. I was getting so excited knowing I had six men with hard on's that they were going to use on me!

My biggest problem was Ray! He had the biggest cock by far. I had to make sure I didn't spend all my time on his lap. I felt so sorry for him, I really wanted take his out so he could at least be comfortable!

My third or fourth time out serving, Steve had untucked his shirt. When I came by, he pulled me to his lap. As I was sitting down, he pulled his shirt out of the way. My bare butt came in contact with his bare, rock-hard cock! I made a little gasp and everyone laughed. His cock wedged perfectly between my cheeks and I started slowly rocking back and forth. We did that for a few minutes until I stood up and said that I'll be right back.

I went to the bathroom and took off my thong. I grabbed a bottle of lube from my purse and started lubing up my cheeks and pussy. I wiped the excess off my cheeks and reached into my bag. I pulled out my pink panties that look normal from the front but they split in the back! My pussy would now have full access. I pulled my dress back down and went back out.

As soon as I got back, I noticed almost everyone had their shirts untucked except Ray. He had on a muscle t shirt that wouldn't have hidden his cock. I laughed when I saw this! I turned around and pulled my dress up revealing my crotchless panties and said "Great minds think a like!". I moved right for Ray and sat on his lap facing him. I whispered in his ear that his was the only one that was not out. I kissed his neck and asked him to take it out for me. I stood up a little to give him room and watched as he struggled to get his hard cock out. When I finally saw it I just said Oh my God! This thing was gorgeous! 9+ inches, big head (which was going to hurt at first! Lol!) and the shaft was thick with these beautiful veins!

I asked every body if we could go to the living room or if they wanted to keep playing cards? We all laughed again as they followed me to the living room. As soon as I got there I got on my knees and looked at Ray, begging him silently to be the first to stand in front of me. He was reading my mind. He was pulling his pants and shirt off while walking towards me. He was by far the sexiest man I had ever been with. I stood up and kissed his chest all the way down to his abs running my hands all over him! I couldn't take it anymore! I knelt back down and took that hard throbbing cock in both hands and started kissing it like I loved it. I made sure to keep looking in his eyes as I put the whole thing on my face. It went from my chin to forehead! I slobbered all over it and tried taking all I could in my mouth. I only managed a few times to get my nose to hit his pubic bone but was gagging a lot. Soon I felt hands all over me and cocks being shoved into each hand. I felt another cock bump my face, so I switched to that one. The next thing I knew all 6 cocks were surrounding my face and I was just moved from one to another. This went on for a few minutes until I heard someone say "Can I fuck your pretty little ass?" I said as long as it's not Ray first! Getting a good laugh from all the guys.

John had an ottoman with some pillows on top. They laid me down face up, put a pillow under me and again I was surrounded by big cocks. Sam had been the first one to ask so he grabbed my legs and put them on his shoulders. I spread my cheeks a little with my sexy nails showing (what guy doesn't love that?) as he gently tried to get his cock in. He said "OMG you are so tight!" I asked him to go slow going in and he grunted ok! The third time he popped in and I must have opened my mouth because there was suddenly a cock being fed into it. Sam kept going in deeper each time until I felt his hips meet my butt. He kept saying how good it felt and asked me if he could speed up. I mumbled something that sounded like a yes, because at that time I was going back and forth between two cocks and had one in each hand.

Sam really started going to town on my pussy and I knew he was about to come. He said he was going to pull out and come all over my stomach, it's not like I could say anything at that point. I managed to look down when he pulled out to watch rope after rope of cum cover my stomach. As soon as he moved out of the way JT put his hard cock in me. Two guys grabbed my ankles and held them apart as JT started pounding away as soon as he was in. He soon yelled he was cumming and pulled out and covered my pussy with cum.

From that point on, there was always two guys holding my legs as one was fucking me like they hadn't been laid in years! Finally, after number five was done only Ray was left. He asked me if I was ready for his cock, I said oh god yes. He had me turn over and get on all fours. He started just getting the tip in and then take it back out. He kept this up for a few minutes getting faster and faster, but always just the tip. He kept calling me a good little slut and how my pussy was so good.

Before I knew it, his hips were slapping up against my ass. I asked him to hold still when he was all the way in one time. When he stopped, I started using my kegel exercises on him. He said oh my god that feels amazing! Then I started fucking him back, squeezing on the way out and squeezing on the way back in! He shouted that he was going to cum and where did I want it. I said wherever you want! With that he lunged back in as far as he could and I felt his cock start to jerk. I started the exercises again like I was trying to milk every last drop of cum from him! He fell over on top of me as I collapsed on the ottoman. We lay there panting for a few minutes until he finally pulled out. Someone brought me a towel to clean all the cum off me and I went to the bathroom to look somewhat presentable again.

When I came out everyone was dressed and gave me hugs and kisses before leaving. Ray hung back with John until the others had left. John went to get something, and Ray came up to me and said that was one of the best fucks he's ever had. I told him oh sure I'll bet you say that to all the girls! He said he was serious, and he'd love to see me again. I told him anytime. We exchanged numbers and he gave me a big French kiss and left.

John came back and told me Ray had asked to see me alone. He then handed me an envelope, which I just put in my purse. I gave him a hug and a kiss then said to call me if he has another event he needs a waitress for.

As I was driving home I still felt cum leaking out of me! Once I got in my front door, I looked in the envelope. $760.00! I love poker!

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Adonisblack1Adonisblack17 months ago

Excellent writing!

latinarita4latinarita47 months ago

keep it up! write another story with more character development and arc and i think u'll have a masterpiece! ur mind is so naughty!

Cissy01Cissy017 months ago

Would love to do this as a nice little sideline !

Robincd1126Robincd11267 months agoAuthor

I'm a CD only. (Answering Nude In Maines comment)

NudeInMaineNudeInMaine7 months ago

Good story. But I’m confused. The category is ‘transgender and cross dresser’. So the story makes sense if she was totally TG, ie including the operation to create a vagina. Otherwise, most TG’s are commonly referred to as she-males (having a penis). Which she didn’t appear to be. Nothing was mentioned of her being a TG in the story itself.

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