Joe Cross Dresses

I knew it was tonight. I just knew it.

I was at a bar, of course! However, what I bet you didn't guess - was I had on a little green dress. Yep. I was the one who seemed to be driving all the men crazy. Who knew?

It all started when two friends of mine invited me to join them at the Florida Keys. I had known Johnnie and Paul (we called him "Hotbunz" - long story) for a while now. Believe it or not, we met online at a horny little website called Underwear Swimwear Guys. We often complimented each other pics of us in very tiny little pieces of fabric, barely concealing a hard dick below! It was fun to post, and we sorta found out we all live in Florida, so we got together a few times.

Johnnie was like me - total show off. He had several pics of him in tiny thongs, cock rings, and just his dick. He was impressive. But Paul only had a profile pic, despite so many members asking for more! He was in a hot little one sided thong. Damn. He looked hot.

So here we were, three buddies on a roadtrip. Now, even though we saw each other's pics, it wasn't like we would get together and give strip shows or just do a big circle jerk. Nope. We were all straight guys as far as we knew. But I had to admit, their cocks looked amazing. And it turned me on a lot.

Plus, I was hardly straight anymore. After a few encounters, I had to admit I was bisexual. I love a nice set of tits. And I adore a hard cock. So yeah, not exactly your normal straight guy. But I only let a few people know. Mostly guys who let me suck their cocks!

We pulled into the dirt lot of a classic 50s style motel. It was perfect! Right on the beach. Tons of sand. And a karaoke bar across the street. Looked fun. And I had to say, some really pretty girls at the hotel. We were all worn out after the drive, so before checking in we decided to go right to the beach. So we grabbed a cooler and off we went.

Now, we hadn't talked about it at all, but I was totally hoping to see some skin from my friends. I was certainly planning to show some.

There were only three chairs open and not all together at the little beach. Everyone was sunning and enjoying the view. My friends sat down on the two benches that were next to each other, and I wandered over to the other open seat on the beach.

As luck would have it, the chair was between a rather dour looking elderly chap, with his eyes closed and soaking in the sun, despite his Santa gray beard.

I did a double take as I looked to the other side of the empty deck chair. This was a very attractive blonde woman. Okay, she was hot. Damn, I couldn't help but stare at her perfect tits in the blue bikini top.

"Can I help you," she asked.

"No, sorry," I stammered, flummoxed by getting caught staring at her tits.

I suavely continued, "I uh, I was just wondering if you.... If you were using this chair?"

She lowered her sunglasses, peered over the rim, "Not mine. Use it." Her voice was deep and sultry.

"Okay, um. Thanks. See you around." God I sucked at small talk. And I was no good at talking to beautiful women. I took the chair and went to join my friends who were already on their second beer.

"Did you get her number, Joe?" chuckled Paul.

"Or her hotel key?" chimed in John.

(*)(*)

After a few beers, and some more banter about how bad I was at getting laid, we agreed it was swim time. Now, we were still in street clothes. Well, beach clothes. It was the Keys after all, and I only planned to wear less as the week progressed.

I stood up first, peeled off my shirt and kicked off my sandals. I was pretty aware that all eyes were on me from the guys. And I knew the other guests could look over and see me as I turned around to peel off my cargo shorts. My ass was facing them all as I pulled down my shorts, bending over to show off (hopefully without being too obvious) my tiny orange thong. I had ordered it just for this occasion.

I was even more aware of being exposed as I turned around to face them. My cock, which was never less than half hard by now) was clearly outlined in the bright orange clingy fabric. This was not a swimsuit. It was a men's thong, taylored to show off my big package.

"You guys coming or not?" I said with a chuckle. I was watching both of them eyeing my cock. I really was liking where this might go.

"I'm in," said Hotbunz striping off his shirt. He stood up and boldly faced us as he pulled down his athletic shorts. His cock was magnificent! He was wearing a bright red side thong. So tight on his huge cock, it showed off every vein and clearly outlined his big cock head.

I saw his gaze to my side, so I turned just in time to see Johnny peel off his shorts as he faced away. Like me, he wore a thong, it showed off his ass nicely. But when he turned around, my jaw dropped. He had this cross cross strap thing, and his big, beautiful shaved cock was proudly on display for the whole beach to see.

"Damn," was all I could say as I stared at his cock.

"You definitely win my man!" Laughed Paul. "Gotta admit, I was afraid I was showing off too much, but wow. You got your whole dick out here for all of us."

Not really saying much, John chuckled and took off for the water. His big dick was bouncing up and down as he jogged. Me and Paul were not far behind.

(*)(*)

After swimming enough to cool us off, we walked back up the sand to our chairs. None of us had thought to bring down towels, we just had not planned it out.

As we drew closer, I had to shield my eyes to see that there seemed to be an extra chair. Turned out to be the hot blonde.

"I hope you don't mind." She said in a low voice. Pretty seductive actually. "The guy next to me is snoring."

"Hi, I am Johnny and he is Hotbunz," said the guy with his penis out on display.

"Why Hotbunz?" She asked looking Paul up and down. I was looking too, and I definitely saw his dick twitch in the shiny fabric of that side thong.

He obliged by turning a full 360 to show her his ass. She smiled up at him.

"Very impressive!" She said with a small whistle.

"And we met," I interjected, hoping for a smile as well. "I'm Joe."

"Nice to meet you all," she said with a pretty smile. "I'm Jenny."

We took our cue and sat on the chairs. Hot was next to her, and I was beside him. I sat in the middle of my seat to get a better view of her. Johnny just lay back and began to soak up the sun.

We visited for a while. Her company had sent her out here for a mini convention where she was selling cosmetics. No doubt she was good at looking hot.

I tried to be a good boy but I kept looking at those nice tits. She caught me more than once I am sure, but she never said anything or even shifted. In fact, I was pretty sure she was being bold showing those big juggs off.

"You guys should come to karaoke tonight," she said after we had visited a while.

"I'm in," chimed Johnny who had been silent this whole time.

"Sounds fun," my Paul said.

"I knew you were fun Hotbunz!" She said as she swung around and stood up, showing off a nice ass, and full long legs.

I was staring at her ass when she turned around to pick up her stuff from the chair.

She had a very tight blue bikini on, and her dick was proudly stretching the fabric. Amazing! This night was just getting better.

(*)(*)

After putting back on shorts, we went to check in at the desk. At the desk, it turned out that the reservations had been messed up by the online service. Go figure. No three rooms were available, but they did have a king suite with a sofa. I think we were all fine with this, so after just enough grumbling to make it convincing, we all agreed to stay in the one room.

Turned out to be great. It was on ground floor, with a grassy patio outside and a path down to the beach. I tossed my bag on the sofa, claiming it for my own, and Johnny and Hot took the king bed. Other than that, the suite only had a small kitchenette, and a dining table with three rickety chairs. Still, not bad for the age of the motel.

Paul took no time at all opening his suitcase and bringing out lots of skimpy things. I was fascinated by his collection of one sided thongs, and held one up. It was simply a strap, looping around.

"How the hell do you wear this?" I asked.

"Like this," he said, sliding down his shorts to show me the one he wore at the beach. "Try it on, you will see how it works."

Well, deciding they both had seen me naked in photos before, and Johnny showing off his cock to the world, I decided it was no time for false modesty. I just peeled off my shorts and thong, standing there naked and casually walked over to take the offered thong from Hot.

I was conscious of how heavy my dick felt swinging as I strolled across the room. This was a first for me to be naked in a room with two men who were mostly clothed. I loved every moment of it.

I took the strap (er, thong?) and stepped in with just one leg. Then I pulled it up over my ass on one side, and it immediately rolled into a length of fabric. Hotbunz laughed as he watched me attempt to unroll the fabric and keep it covering my cock. I was becoming frustrated and he could tell, so he walked over and said, "Here. Let me help."

He deftly ran his fingers down the fabric, and then he grabbed my dick like it was no big deal. He tucked my cock into the fabric in such a way that the thong was held up partly by my hip, and partly by my balls.

"How's that?" he asked as he stepped back.

"Looks hot," Johnnie said in appreciation.

I was sorta dazed, my cock slightly tingling after the casual touch of Paul's hand. I was growing hard and I needed to think of something fast.

"Lets go to the bar," I said, quickly changing back into my regular old thong and shorts. It was funny how "more covered" I felt with a full thong, but wow, I could see why he liked those one sided numbers!

I stated thinking of a way to return the favor to Paul. A sort of plan began to form in my brain.

(*)(*)

At the bar we grabbed beers and sat at a table. It was only sorta crowded, and very laid back. The karaoke stage was set up, but no one was singing yet. We just visited and drank enough to get a pleasant buzz as the first hint of sunset crept into the sky.

Pretty soon most of the patrons began to stroll outside, onto the nice little beach beside the bar. They all took their drinks with them, so we grabbed our bottles and followed to see what was going on.

As we stood there, the people just talked, laughed and sipped on beverages as the sun put on a dazzling show for us. A waitress came round with shots of whisky, and we all grabbed one. Just as the sun was disappearing the whole crowd cheered and took a shot. What a fun little tradition. I was feeling very relaxed as we walked back into the bar, and the music began to crank up the energy in the room.

In no time at all the place was boisterous and loud as people sang out of key to classic rock songs and everyone cheered them on. Jenny came up after a while and greeted us all with hugs, like a lost friend. Her tits pushed into me as she hugged me. Wow.

But she soon wandered off to go around the room greeting ladies at the tables, making introductions and generally doing a good job of making all feel welcome. Many of the guys followed her with their eyes, and I was doing the same.

She was in a little yellow dress, which was somehow both sexy, casual, and dressed up all at once. Her tits were on display being held up with tiny straps. I don't know if those straps were up to the task, but they were holding strong bouncing as she walked around.

I was pretty sure some of the guys knew she had a surprise package between her legs, but it was so casual that I doubted if anyone cared. I love the easy lifestyle of the Keys, where sex is just a part of life, and anyone is welcome to be who they want to be.

Personally - I was very entranced by her beauty. I really wanted to get to know her better, and spend more time with that hot body.

Soon she came back to sit at our table.

"You guys are so nice for coming," she said. "You are gonna look so hot on stage, I can't wait."

"On stage?" I asked with a laugh. "Not me, I'm not singing."

"No silly," said patting me on the leg. (Yes, it made my dick twitch just a bit. Okay?)

"You are in the contest at 10." she said with a flourish at the large sign by the stage. I had not read it, just looking around. Now it was staring me in the face:

"Drag Show and Dance - Friday at 10!"

"Oh no!" I exclaimed. "I am not doing a drag show."

I will admit, this was partly me still hanging onto that straight guy persona I had cultivated so carefully over the years. It wasn't until I was divorced, and had no more kids in the house that I began to really explore my sexual desires.

I experimented with lots of girls. But what kept coming back was my desire to suck cock. I just couldn't help myself. I had to have a dick in my mouth. So I went on Grinder and had a few misses, until one night when a guy came to my back door.... But that's a story for another time.

"Oh come on Joe," said Paul. "It might be fun!"

"I'm in," said Johnny, "but I don't have anything to wear."

"Ohh, you are in luck," she exclaimed. "I will be in your room in 20 minutes. See you soon!"

(*)(*)

So I found myself standing in a crowded hotel room with two mostly naked guys and a tranny, trying on dresses. And, yes the padded bra was the very first thing to go on. I had to admit, the pink lacy bra was kinda sexy.

I was in my tiny thong. It was a different one, since we all had to shower at Jenny's command. She had just marched in with a huge suitcase that turned out to be a wardrobe thingy full of dresses.

"Okay," she was saying as she looked at Hotbunz. He was wearing a little black dress, with one hip cut way up. She said since he liked a side thong, he could get away with showing some hip, and maybe a little ass. "That is perfect!"

Next Johnny. She kept holding up dresses to him, and changing her mind. Meanwhile, he was just standing there in a very tight little thong. It was transparent, so we could all clearly see his dick. But he was a cool customer. He just stood there exposed and semi aroused. Damn, that was a nice cock.

When my turn came -- after fitting Johnny in a little open back red dress that showed off his ass -- I found myself standing in my own little thong as she pulled out dresses to hold up to me. I must admit, all the fabric was very soft, and each time she pulled it across my body she made sure to go slowly. I'm positive she was trying to get me horny. Especially as I was the one who objected at first.

She finally settled on the green dress. I held up my arms as instructed as she slid it over my head. She slid it as low as it would go, which wasn't very far below my dick. Now her hand was technically on the dress, but I felt her fingers brush against my cock as her hand was at that level.

"Hmm," she said as she kneeled down in front of me. Right in front of my cock, which was starting to grow harder each second with her fingers brushing against it.

"This might be a problem," she said as she lifted the dress up to see my dick, then lowered the hem to cover my bulge. "Tuck time." she announced to the room.

"Oh damn!" laughed Johnny. Hot was trying to look away but I could see him laughing.

Why me?

Jenny didn't wait for me to back out. She just pushed up the dress and pulled down my thong in one quick move. Now my dick was out in the open right at her eye level. I couldn't help my soft moan that escaped my lips.

"This is gonna be a challenge," she said, studying my dick as if it were a geometry problem. She reached up and grabbed my cock. The guys were all eyes as she maneuvered my dick around. "I think you are still a bit excited," she said as she handled my penis trying to move it down between my hanging balls.

Then she said the word I had not expected to hear.

"Tape."

My eyes grew wide as she reached into her bag and came out with a roll of white athletic tape. She moved very fast, and pulled off short strips of the tape and put them on my dick. Damn, this was hot and at the same time kinda weird.

"One of you need to give me a hand here," she announced as she bumped my legs further apart. Johnny was on it, kneeling behind me and reaching between my legs to pull my cock down as she taped it. He stroked it a few times just to make it more of a challenge for me to keep it flaccid.

"I'm gonna kill you," I whispered back to him as he smiled and jerked on my dick again. Damn.

(*)(*)

So, here I was. At a bar - of course. In a slinky green dress that I will admit made my legs loot hot. Oh, did I mention she made us all take off the dresses and shave our legs and any remaining hair on our lower bodies? We all three had shaved cocks, but this was a first for all of us.

.

The next stage was predictable, wigs. I reached for the blonde wig out of instinct. Johnny chose a brunette for his red dress. Hotbunz went for the strawberry blonde. It took so much longer than I expected but it was kinda fun in a way.

After, when I put on the green dress, I was made up with pretty blush and what I thought was too much eye makeup. And of course bright red lipstick. I had to admit, we looked pretty. Jenny was a very talented artist.

I felt very conspicuous standing there at the bar in the skimpy dress, tight thong, and my dick all strapped down. But then the bartender placed a Gin & Tonic down, indicating it was from one of the tables full of guys.

I smiled at them, and sipped on the drink. You know, it wasn't too bad being dressed up as a girl. I really did feel pretty, and the attention from the guys was kinda flattering. I had a mix of emotions. But one thing was certain, I was feeling good. I loved the feel of the dress on my body and the way my bare ass was just below the sightline.

Yeah, I was feeling good and slutty.

Just then, the bar all started clapping as Jenny took to the stage and began the contest. She called up the contestants one by one, and give them a chance to wiggle and play to the audience. The winner was to be judged by audience applause.

It was cool to watch. Everyone who got up got a huge cheer. Some really put on a show, and a few were more shy. When Hotbunz was announced, he just walked forward like he meant business. His hips were swaying and his tight dress revealed a solid glimpse at his leg on one side, almost but not quite revealing his package at the crotch. Hot.

Johnny was next. His red dress was so damn sexy, but his wig, makeup and fun eyes really lit up the room. Everyone cheered loudly for his walk.

I heard Jenny call my name, and I took a big gulp of air. I walked up the few steps to the stage, feeling very exposed. Now, to be clear we all had on flats, no way I'd try to walk in heels!

When I stood on the stage, with all eyes on my body, I suddenly felt so sexy. I was really enjoying this. I looked over at the table that sent my drink and gave a big air kiss. They all laughed and applauded me in my green dress.

Well, in the end, Hot took home the prize for best drag queen. But we all mingled around and had a good time bantering and flirting. About a third of the girls were trans, I think. The rest were guys dressing up and having fun. Everyone was having such a good time. It was awesome.

(*)(*)

Some of the guys who were at the bar waved me over. I was keenly aware of the eyes on me as I went toward the group. They had a shot of tequila waiting for me when I walked up.

"Nice job!" a striking man said as I took the shot. "I wish I had the courage to do that." He introduced himself as Ross.

"I never expected to be up there," I said.

"Well you certainly look good," said another of the guys. "I'm Bryan."

We visited and had a few beers, talking about sports mostly. But the subject of the night was cross dressing and how fun it turned out to be.