Cassie and the Poker Boys

Once again, I need to thank Tania Tulle for her help and guidance. I would be lost without her.

Note to readers:

This story was supposed to follow an alternative Cassie story but it's been pending for two weeks. If this story should get published first, it will be fine to read as a stand alone.

Mistress

You know I would never lie to you but I hope what follows doesn't disappoint you too much. Your little sub has been a very bad girl. I could blame it all on my financial situation, but truthly part of me wanted to be slutty.

The weekend after my friend Lisa visited I decided to go out again wearing a sexy short black dress, my new favorite Wolford stockings, lacy bra and panties and 5" heels. I was finally able to walk around in them at least for short periods of time.

I just loved the feeling of putting on my sexy panties and pulling up each stocking on my legs. Glorious!

The clothes felt so fantastic it was all I could do to stop myself from rubbing my hands all over my legs, ass and crotch. I thought to myself, that's someone else's job.

I took an Uber to my favorite bar, liking the way the driver was checking me out. This new me was really starting to grow on me.

I sat down and ordered a drink. I had no real plans, just wanted to get a few looks, see who might be interested.

Another big surprise came when I saw another old friend across the bar staring at me with a puzzled look on his face. It was Mark, one of the very few guys in high school who didn't pick on me. He was an athlete who preferred to hang out with the studious crowd. Very unusual but I was grateful for his friendship.

Looking at him now through Cassie's eyes, I realized how good looking he was. Tall with brown hair fasionably long, muscular but not overly so. Definitely over 6 ft tall and soon I discovered a winning smile.

He still had that look on his face but picked up his drink and headed my way. I was still debating what to say when he sat down next to me.

As he sat down, he smiled and asked if he knew me. I smiled back and said, "no, but maybe we can have a few drinks and get to know each other." I was surprised at my flirting but also proud of myself.

We drank and talked for an hour or so and I was having a great time. But I also realized that I couldn't continue without telling Mark the truth. He certainly deserved to know and I wanted to be honest about everything.

At this point I got very nervous abd chickened out. I told him that I had promised to take a friend to the airport for a very early flight. I didn't want to lie to him but I panicked.

I could tell he was disappointed but he recovered quickly. He smiled snd said," I'll allow it but you have to give me your phone number and agree to have dinner with me tomorrow."

Be still my heart! I was thrilled and quickly agreed. He waited outside with me for my Uber and kissed me goodnight. As I rode home with another driver checking me out, I thought that becoming Cassie was a great idea.

Sure enough, Mark called me around noon on Saturday and told me he had picked out a nice restaurant and had a reservation for 7. I lied again and said I had been called in to work. Since it wasn't far from the restaurant I asked to meet at the bar around 6. I needed some liquid courage and time to confess to Mark.

Since I no longer had a job, I just kept adding new lies. But it did give me plenty of time to decide what to wear.

Mistress, I must be starting to think like a woman because soon my bed was covered with outfits that I had rejected. Finally I realised that I should choose a conservative outfit because of the work story.

I put on a white bra, then pulled on a pair of sheer nudes pantyhose. Just the feeling of the nylon against my skin started to get me hard. I had to pause for a few minutes to let my cock calm down. Then I put on a pair of white panties hoping for a smooth look.

I selected a nice pencil skirt which fit my body perfectly and a nice white blouse which showed just a little cleavage.

Hey, these puppies weren't cheap so might as well show off a little.

I know I've said it before mistress, but I love my new tits.

Finally I added a black suit jacket and 2" heels. Naturally I couldn't stop myself from crossing my legs in the Uber and loving the feel of nylon. The driver kept glancing in the rear view mirror so I guess he liked the view.

I got to the restaurant early and headed straight for the bar. I knew I could use a drink to calm myself. I also needed the time to go over what I wanted to tell Mark.

I was on my second drink when Mark arrived. He gave me a smile and a kiss and I smiled back. Then he said, "I hope you ran a tab because I want to pay for that."

I told him that he might reconsider after we talked. He signaled to the bartender and said, " I'll need a drink first."

I proceeded slowly, beginning with my apologies for any lies I told him. The first couple were easy but then I got to the big one.

I was starting to choke up a little and trying to hold it together. "Mark, I like you a lot, in fact I've liked you for years."

I definitely had his attention now and I continued to explain my transformation from Charles to Cassie. He had a strange stunned look on his face, so I started to reach into my purse for my credit card.

I figured I would pay for our drinks and get away before I broke down sobbing.

Next thing I knew, I felt Mark's hand on mine. Looking up through some tears, I saw him smile and shake his head. "He said, not so fast, I'm paying not you my beautiful friend. Plus, you promised to have dinner with me and you're not getting out of it."

Mistress, I went through such a range of emotions in a short period of time that I needed a moment. I just nodded at Mark and pointed to the Ladies room.

I sat in a stall for a while letting some tear come. Actually I was feeling relieved that Mark didn't hate me. I rallied, fixed my makeup and joined Mark at the table.

We had a nice dinner and Mark shared that he always had a secret thing for trans women. He told me that I was beautiful and he certainly preferred Cassie to Charles.

No surprise mistress but I was loving what he was saying. We talked some more and he paid the bill.

As we were leaving the restaurant he asked if I would join him for a drink at his place.

I certainly didn't want the date to end, so I said yes. We were on the couch making out like crazy and I loved it.

He was getting me very excited and I didn't ask him to stop when he started to unbutton my blouse. The bra quickly followed and his mouth found one of my nipples.

I was extremely excited now and my cock was pushing against my pantyhose, panties and skirt. Mark's tongue was alternating back and forth from one tit to the other. Licking and sucking in a wild frenzy.

My hand reached down to his crotch and felt his big erection. Without thinking I pulled away and unzipped his pants. I pulled them off as well as his boxers. His cock sprung up and I was staring at a good 8 inches and fairly wide. Much bigger than my little sissy cock.

Mistress, I knew what I was about to do was considered slutty for a first date. But I didn't care and actually liked the feeling. Besides, Mark had been wonderful and paid for the drinks, dinner and the Uber. A girl should show her appreciation, shouldn't she mistress?

I started by swirling my tongue around the head of the cock, then down his veiny shaft. Next I spent some quality time licking and sucking his balls. Up and down and back up again until Mark started to moan. I knew I must be doing something right and started to bob up and down on his cock. Trying to take a little more on each try while avoiding gagging. Mark started to moan louder and I picked up the pace. I almost got all of his cock in my mouth before he erupted. Stream after stream shot down my throat with some leaking out.

Mistress, I was extremely proud of my first effort at giving a blowjob. Also surprised at how much I liked it and that the taste of cum didn't bother me.

Mark wanted me to stay over but I told him another time. He ordered me an Uber and we kissed goodnight. As I got in the car I was already starting to miss Mark. Slow down girl, you've got it bad!

Over the next month we saw each other often, dinners, movies, a romantic weekend at a country Inn. I was having a great time and of course sucking his cock regularly. He would also be rubbing my ass and occasionally my cock through my pantyhose.

I know he wanted to fuck me but I was scared of the pain and a big chicken.

We spent a lot of time talking, sharing our experiences, fantasies, dreams for the future. Mark confessed early on that what we had would not be a long term thing. He was having fun but eventually wanted to be with a woman and start a family.

I was disappointed but I did understand and promised myself I would continue to have fun.

I finally confessed another lie to Mark and told him I was unemployed. Adding that I was living on savings but I was starting to run low.

Mistress, what follows is a radical change in my life, one that I never could have expected. I could blame it all on my finances but honestly the slutty aspect also appealed to me.

Mark listened to my problem and offered a solution. He prefaced it by making me promise that if I didn't like the idea I wouldn't be insulted.

He then told me about a weekly poker game he and his friends had every Thursday night.

They hired a woman to serve drinks and snacks during the game. Only five played at the same time, so one guy rotated out and received "special treatment." It pays $500 plus tips for about 5 hours. I didn't have to think about $100 per hour long and agreed to take the job.

If I was going to be a slut, I might as well get paid for it.

He said he would tell his friends about my situation and let me know how they felt.

Mark stopped at my apartment on his way home from work on Monday. He was carrying a small suitcase. He said I will explain the bag after a few kisses from my sexy new poker hostess. I practically knocked him over as I hugged and kissed him over and over again.

Then he told me that he had purchased an outfit for me to wear that would make me look sexier than ever and other proper preparations for my new job. Naturally I dropped to my knees and gave him a thank you blowjob.

Mark gave me the address and the time and we said goodbye. Thursday I had a little breakfast and took a long shower, making sure I was shaved completely. I had found a douche in the bag and used it just to play it safe. I wasn't exactly sure what to expect but the money was too good to pass up.

I laid out the clothes Mark had bought for me to wear. I hoped he knew what he was doing but I was sceptical. There was a lacy garter belt with seamed black stockings.

I was in love with that choice as I rolled the sheer hose up my legs. Wonderful sexy feeling for sure. I followed with a pair of lacy panties that also felt great. There was no bra and I went back to the bag to double check. Nope, I guess Mark decided I should go braless. I chuckled to myself and thought, what the hell, if you got it, flaunt it.

I tried on the dress and gasped when I saw that it barely came down to my stocking tops and my tits were practically hanging out. Bending over would give quite a show. I was very nervous but I put myself in a sub role and followed Mark's orders. Also in the bag were condoms and lube which pretty much told me what was expected. At least he picked out 3" heels thinking I would be walking a bit serving drinks.

I took an Uber to the address and everyone was there already. Mark introduced me to his friends, Kevin, Jay, Lenny, Pete and Craig.

Everyone except Jay wanted beer and he asked for scotch on the rocks. I decided to be playful and said," most bartenders charge extra for rocks but not Cassie. She just helps to get them off."

The guys all laughed and we were off to a good start. Mark was sitting out the first hand and asked me to join him in the bedroom.

Mark took my hand and led me to the bedroom. As soon as we were in he started to kiss me and rub my ass through my dress. I must admit, he was turning me on. He stopped after a few minutes and I was disappointed. He then told me to take off my dress and bra because he needed to suck my tits. I took them off and sat on the bed next to him. He kissed me again and then started to lick and suck my nipples, alternating between them. Oooh, it felt wonderful! These puppies were paying dividends for sure.

Mark instructed me to take off my panties and get out the lube and condoms. He said," I chose to go first tonight so I can take my girl's virginity. Your choice as to whether I wear a condom."

I quickly replied, " no condom necessary for you, just start slow."

He started to lube my ass gently pushing one finger and then two, in and out slowly going deeper. I was starting enjoy being finger fucked and moved my ass back and forth.

Mistress, ever since I opened the bag Mark had brought me on Monday and found the douche, condoms and lube, I knew what to expect today.

I was prepared and relaxed as I could be and thankful that Mark was going first.

Of course none of that meant a thing when Mark started to enter me. It hurt like fucking hell Mistress! But your sissy sub Cassie gritted her teeth and tried to enjoy it.

Sure enough after what seemed to be forever, the pain subsided. What I started to feel next was incredible. Mark's big cock was hitting my prostate and the feeling was extraordinary! My cock was rock hard and even though it hadn't been touched it felt ready to explode.

Mistress, I can only imagine this was how women must feel when they are getting fucked. Just that thought made me smile.

Mark was picking up the pace and I started moving my hips to meet his thrusts. God, I was in heaven! I came before he did shooting ropes of cum on my stomach and some hitting my tits! Mark exploded in my ass shortly afterwards and I liked that new feeling as well.

I knew I needed a good cleanup before serving more drinks and started to head to the bathroom. Before he left Mark was trying to put $200 on the nightstand. I grabbed his hand and told him no way I would ever accept a tip from him. A hug and a kiss would suffice. He grabbed me and gave a great long kiss before leaving the room.

I knew we had taken quite a while and hurried to clean up. Fortunately I didn't get any cum on my garter belt or stockings and just cleaned up my stomach and tits. I touched up my makeup, put on my skimpy dress and heels and headed back to serve more drinks.

I refiiled everyone's orders except for Kevin who was now sitting out and would join me in the bedroom. Kevin was a short guy, maybe 5'6", a bit overweight and seemed very shy.

We got into the bedroom and he immediately grabbed me and started kissing me. He stopped for a second to tell me how beautiful I was. Ok, maybe not as shy as I thought.

We must have made out for at least ten minutes as he rubbed my nylon covered legs, fondled my ass and my tits through the dress. I was surprised he didn't ask me to strip but I let him have it his way. Finally Kevin paused, put my hand on his already hard cock and said, "please Cassie, suck my cock, I am so horny!"

I obeyed and pulled down his pants. His cock sprung out already hard and I started to stroke it. Then I started licking his balls and up his shaft. I already knew that my favorite part of sucking cock was licking around the head and getting the guy excited. Kevin was definitely excited and I started to take his cock in my mouth. He was cut and about 5".

Nothing compared to having Mark in my mouth.

I was easily able to take all of him in my mouth and quickly he really became excited.

His cock pulsated and shot cum into my mouth. Kevin thanked me and gave me a hug and $100.

It was now official mistress, I was a whore!

As I was fixing my makeup looking in the mirror I was suddenly ashamed of myself.

I pushed that thought out of my head because I had more work to do.

I finished my makeup and went back out to serve more drinks.

Kevin replaced Jay at the table and back to the bedroom they went. The scotch drinker didn't mince any words and asked how much to let me fuck you?

Jay was one of the older players, normal looking, nothing stood out as exceptional.

I was wasn't surprised and quickly answered $200, figuring Kevin just gave me $100 for a blowjob.

Jay areed to the fee and said strip down to your stockings and heels. I immediately did as he requested and asked if the garter belt was ok?

Jay nodded and told be to get on my back and grabbed the lube next to the bed. He saw the condoms and asked " another $50 for bareback?"

I nodded and he started to lube my ass and his cock. He climbed on top of me and started sucking my tits. A few quick kisses followed as he edged his cock into me. I could only guess that he was about the same size as Kevin or only slightly bigger. Certainly no pain as he moved slowly into me.

I started pushing my ass back into him saying Cassie is a full service bartender.

Once again he didn't last long and came in a flourish in my ass.

He got up and put $260 down next to me on the bed. He said he didn't have the exact change but I was worth every penny.

As I dressed I was thinking that I was even better than I thought I was or those two guys were very horny. I also had another guilty feeling of what a slutty whore I was becomming.

Back out for another round of drinks and it was Lenny who practically dragged me into the bedroom. " Just sit your slutty ass down and open your mouth."

He proceeded to stick his smelly cock in my mouth and grab my head. Then he quickly started to move his hips while holding my head. I was gagging and struggling to breathe and just when I thought I might pass out, he started to cum. He came a little in my mouth and then pulled out and kept shooting all over my face.

Ss he pulled up his pants he smirked and said, "that's what good sluts should always look like."

He threw a $100 bill down and left.

I quickly got up and ran to the bathroom. I didn't want any cum to get on my clothes. As I was cleaning up and fixing my makeup, I thought that I had experienced my first face fuck and wasn't sure I liked it. I didn't like the feeling of being a cum slut but I was loving the financial aspect. Mistress, please don't hate me for not minding becoming a whore.

I went back out to serve more drinks thinking still two to go and already getting tired.

As I started to get more drinks, Mark said just the four of us at the table. Poker is over, we're just going to play gin rummy while Pete and Craig join you.

Both guys could have been tight ends or linebackers in high school. Maybe 6-3, 6-4 with athletic muscular bodies. Pete with long blonde hair and Craig with a brown crewcut.

Pete threw down $500 and told me to strip down to my garter belt, stockings and heels. "You're about to get double spit roasted."

A mixture of surprise, anxiety and excitement hit me all at once. I admitted to myself that I was already a slutty whore so why not rake in the money.

Mistress, the next hour passed like a blur. I was very tired and these two went back and forth sticking their cocks in my mouth and ass. They were not as big as Mark but bigger than the other three guys. Insatiable would be a good description of their sexual appetite. By the time they finished pounding away at me front and back, I was practically passed out.

As they were walking out they yelled back, "see you next week sexy whore Cassie."

Next week? Could I actually do this again?

I was ashamed of myself but then again, almost $1500 richer!

Mistress I decided to postpone that decision and I managed to get up and clean up at least a little.

Mark had arranged for an Uber to take me home and as I sat in the back seat smiled at the term sexy whore Cassie.

To be continued?