Poker Game Glory Hole Entertainment

There's a point in every voyage when the trip takes on an inertia of its own. Maybe it's the point of no return. The point where you've gone so far and you could turn back, but it seems like going on is the only choice. That's what I found myself thinking as my car ate up the highway miles. As I passed each exit I considered getting off and turning around. I was on my way to meet Ray at his house for the first time. I'm a mid-50s married guy in a mostly sexless marriage. I didn't want to go through the whole affair drama with a woman and my thoughts kept drifting to experimenting with another married guy. I met Ray at a work conference more than a year ago. We ended up in his room drinking beer and watching a football game. One thing led to another and I gave him a blow job. It was my first. I was hooked and started meeting Ray when he traveled for business. We would meet at his hotel and have a few drinks. Then, I would blow him and he would jerk me off into a hotel towel. Over time Ray wanted to mix things up beyond our standard blow-and-go. I bottomed for him a few times. After that, he bought me a set of black lingerie and started having me cross-dress for him. He kept me guessing what each meet-up would feature. I never would have guessed what he had in mind this time.

As I kept driving, exit by exit getting closer to the destination, I concluded I was on the classic slippery slope. It started with watching more porn when the sex in my marriage dried up. Searching for more variety to watch I went from MMF threesomes to shemale and cross-dresser porn. I started to obsess about what it would be like to feel another guy's cock and maybe try giving a blow job. Then I met Ray and discovered I really love giving head. I was hooked. That led to me bottoming for him and the discovery that I liked getting fucked almost as much as I liked sucking cock. The most recent slide further down the slope was cross-dressing for him. At one of our meet-ups, Ray surprised me with a gift bag of stockings, panties, and a bra. So now in addition to sneaking off every other month or so to give Ray a blow job, I was hiding a bag of lingerie at my house, trying them on when I knew my wife would be out of the house for a few hours.

I hadn't heard from Ray for a couple of months, so I was super excited when I got his text. I was confused by the message because he gave me directions to meet him at a coffee shop and told me it would only be a quick meeting. When I arrived, Ray was already sitting at a small table sipping a coffee in a to-go cup and another cup was on the table for me. Almost as soon as I sat down, he stood up. "There's a bag under the table. Everything you need to know is in the bag. Stay here and drink your coffee. Oh and, make sure you're alone when you open the bag."

I did what I was told and drank my coffee before picking up the bag and leaving. The anticipation was killing me. By the time I got home, I had less than an hour to check out the contents before my wife was due home from her book club meeting. I dumped the bag out on my desk in my home office. It contained more stockings, a pair of black pumps, several pairs of thong panties, a "pocket" bra, a pair of breast forms, and a slinky black dress. There was also a wig and a small makeup. Then I found a note from Ray.

"I hope you have been practicing dressing up. Here are some new items to add to your wardrobe. Lately, I have been thinking a lot about you giving head to other guys. I find that thought very exciting. My wife is going out of town next month to visit her mother. I am hosting a big poker game while she is away. I want you to dress up in these new clothes and come to my house that night. I will set up a glory hole for you. That way any of my guests can take a break from the game for a few hands and get serviced by you." the note went on to list the date and time as well as Ray's address. In a P.S. he added that I had to get dressed in the new outfit and drive to his house "fully dressed" for the occasion.

So here I was in a little black dress wearing makeup and an auburn classic fling wig on my way to be the glory hole entertainment for Ray's home poker tournament. As I pulled off the highway I had to admit to myself that being out like this in public for the first time was a huge thrill. A huge thrill punctuated by moments of sheer terror at the thought of getting pulled over by a cop or getting into an accident while cross-dressing.

As I approached Ray's house I saw the line of cars parked on both sides of the street. This was one big poker party! Following his instructions, I pulled into the driveway and drove up to the right-hand garage door, and sent him the "I'm here," text. The garaged door rolled up and Ray waved me in.

Ray assured me that everything would be fine and that I'd like the setup he prepared for me. I was unprepared as he directed me through the kitchen and walked me into the main room where more than 20 guys were setting up the tables and chairs. I put my head down as I felt them all staring at me as I walked through the hallway with Ray. Most of the guys looked even younger than Ray. I did see two older guys. They looked like they could be the dads or grandpas of some of the younger men. My face felt hot and flushed as we made our way down the long hallway to a bedroom on the left.

The bedroom had a small on-suite full bathroom. Ray showed me how he replaced the bathroom door with an old door from the remodel. I saw the real bathroom door leaning against the wall of the bedroom. In its place was an old brown plan door with a circular hole in it. The edges of the hole were meticulously wrapped with duct tape. Ray showed me how the door locked from the inside and wished me good luck.

I quickly closed and locked the bathroom door as soon as Ray left. I felt like I was hyperventilating. I closed the lid of the toilet and sat down. After a few minutes, the panic subsided. I noticed that Ray had the room stocked with beer, bottled water, ice, and a few sandwiches and snacks. There was a small foam pad near the door to kneel on. I noticed that there were three nip-sized bottles of bourbon. I tossed a couple of ice cubes in a cup and poured one of the bourbon bottles. The whiskey started working and I felt myself warm up and relax. I played with the light switches to adjust the light in the room. I found leaving the overhead light in the shower stall on, closing the shower curtain, and turning off the other lights gave me to low soft lighting I wanted.

I added the second bourbon to the cup and looked at myself in the mirror. This was the first time wearing breast forms and I really liked the way they enhanced my total figure. I decided to take the little black dress off and I draped it over the shower curtain rod. I kicked off the pumps too and settled in sitting on the floor to wait for something to happen. I waited and waited. I read my news feed and played video games on my phone. I got up a few times and paced because my legs were getting numb. It had been almost two hours.

I never heard him approach the glory hole. Suddenly a small cock just poked through the hole. I got down on my knees. It was a really small cock, maybe 4 inches and it was completely flaccid. I reached out and took it in my hands stroking and pulling on it. Despite my best effort, it wasn't getting any harder. I took his whole cock into my mouth and started rolling my tongue all around it. I was able to easily go all the way down on him. I heard his heavy breathing and moaning through the door as I continued the blow job. It sounded like he was enjoying it but he still wasn't getting hard. I pushed all the way down on him and turned my head from side to side. Just as I was thinking of trying something else, his cock exploded shooting his load down my throat. I had to swallow a few times in a row to keep from choking on it as each spurt spewed directly down my throat. He pulled his still-limp dick from the hole. I heard him waddle away struggling to pull his pants up as he walked toward the door. Well, that was disappointing I said to myself. He never got hard and I could barely taste his cum. I sat back to wait some more.

It took a long time before I heard another guy approach. I hear his zipper pull down and then the heavy thunk of his pants drop to the floor. He shuffled up the hole and poked his dick in. I was pleased to see it was a rock-hard six-inch beauty. I was on it in an instant. I kissed and licked his head and ran my wide flat tongue up and down his shaft. I kissed and licked the underside of his shaft right where it met his balls. I licked up from there and took him into my mouth. I felt and heard the toes of his shoes bump against the door as I pushed into the glory hole even more. I started to work his cock with my hand and hands. Both hands slid and twisted down his shaft just ahead of my warm wet mouth. It didn't take much of that to make him cum. His throbbing member dumped its load and I swirled my tongue around in my cum filled mouth a few times before swallowing.

After that cocks popped into the glory hole every five minutes for a while. With each blow job, I felt the wet spot growing in the front of my panties. Between blow jobs, I stood up and checked myself in the mirror. I turned and posed over and over thrilled and feeling so sexy. After another long gap, a huge cock slipped through the hole. It had to be eight or nine inches long and as thick as a beer can. I was thrilled to have my first big cock. My excitement was short-lived. I found it nearly impossible to really suck a cock that big. I turned it into mostly a hand job. However, the finish didn't disappoint. When I sensed him getting close, I worked his big smooth cock head into my mouth and stroked his massive shaft with both hands. I thought his spurts of hot thick cum would never stop. I swallowed a few times but he kept refilling my mouth. I couldn't contain it all. Cum leaked from the corners of my mouth and a long rope of cum dangled from my chin.

One of the old guys I saw when I first arrived was the next through the hole. He had much bushier pubes than the other guys and his pubic hair was mostly gray. I paused as I heard him struggle against the door. He worked his balls through the glory hole and pressed his whole body against the door. His sac was huge and hung down from his twitching cock. His balls hung down more than the length of his cock. I fondled his nuts as I started to suck him. His cock was a little on the small side and it had an odd bend to it. I wrapped my fingers around his sack near the base of his cock and began to stroke and tug on them as if I was giving his sac a hand job. The more I manhandled his nuts the more excited he got. He came in my mouth most strangely. His cum didn't spurt out. His cum poured out of his tip like water from an old public drinking fountain. It was so much thinner and more watery than all of the other guys but at least it didn't taste bad.

When the last customer poked through the Glory hole I was tired and my jaw ached. I sucked him off hot and heavy hoping to make him cum quickly. When that didn't work I had to give my aching jaw a break and I switched to just stroking his spit-soaked shaft. A few seconds later his cock exploded. his sperm spewed out in thick gobs all over my face and neck. I kept stroking him and opened my mouth. I was able to catch some but almost all of his load splashed all over my face. It felt fantastic. I instantly started fantasizing about having someone cum all over me, on my face, my chest, and my ass. As soon as he withdrew I stood up to admire my cum-laden face and neck in the mirror. I took my time wiping the thick beads of cum off my face and sucking them off my fingers.

After another long pause, I heard the sounds of car doors and engines starting and I guessed the party was finally breaking up. Ray knocked on the door and told me to come out and that everyone was gone. When I stepped out into the bedroom Ray was standing there with his gray sweatpants pushed down to his knees. His cock was out and he was stroking it. He looked me up and down a few times and then pushed me down to my knees and shoved his cock in my face. I looked up at him and sucked his cock.

"That's right," he hissed sounding very drunk. "Suck my cock. You're my little cock whore, right? I nodded yes without taking his cock out of my mouth. "You filthy little slut. How many cocks did you suck?" I tried to remember the exact number but I really did lose count. I told him I thought it was eight. "You are a filthy cock sucking whore!" he said. He jammed his cock deep into my throat. He grabbed my head with both hands and I felt my wig starting to slip. He forced his cock in deeper and held my head tight. I gagged and sputtered on his cock and struggled to breathe. I felt my eyes well up as he continued to hold me down on his cock. I gasped and sucked in a huge inhale when he finally yanked his cock out of my mouth. My head was swimming and as I was recovering, he dragged me to the bed and roughly positioned me on all fours. I heard the sound of the plastic cap snapping open and I knew that meant he was lubing up to fuck me. I had bottomed for him two times before during our regular hotel meet-ups.

He pushed my head and shoulders down and lifted my hips forcing me into a more ass-up position. He pulls my thong off to one side and rammed his entire cock into me all at once. I literally saw stars and yelped. He had been so careful to start out easy before. Not this time. He immediately started pounding into me. I felt my ass shake and giggle each time his hips slapped against me. Each time his cock plunged deep up my ass it took my breath away. I suddenly realized that it also felt different because he wasn't wearing a condom.

"Your belly is full with all the cum you swallowed so now I'm going to fill your ass too," he said through clenched teeth as he pounded my hole with a piston strong motion. I held on tight to the bed sheets as the searing pain gave way to a better mix of discomfort and pleasure. He grunted and groaned as he continued to verbally abuse me and pummel my ass. "I'm going to breed your hot tight ass," he yelled. I felt his cock throb inside me. I felt each spurt of his cum spew all over my smooth inner walls. That amazing sensation made me cum in my own panties. I pushed back into him as he pumped the rest of his load into my bowels.

Ray slide off me and flopped down onto the bed. I flattened out onto my stomach next to him. I rubbed my cum soaked panties against the sheets and savored the feeling of thick beads of his rum starting to roll out of my throbbing hole. Ray eventually turned over onto his side and I could tell from his breathing that he was already asleep, lost in drunken, spent slumber. I slid in and snuggled my back against him wiggling my ass against him. He draped a heavy arm across my body and I eventually drifted off to sleep too.