tagTransgender & CrossdressersDressing for Larry and Friends

Dressing for Larry and Friends


After an encounter with Larry, he suggested that I might like cross-dressing for a future date. That was something I had never considered. Although I am pretty much a total bottom when it comes to gay sex, I wasn't particularly femme nor had this ever occurred to me. However, Larry's suggestion excited me and I tried it and liked it very much. "Dressing for Larry' tells that story. Larry then asked me if I would like to dress for him and a few friends I loved a good gangbang and I quickly agreed.

Since I really didn't know that much about cross-dressing, I did some research on the web. Who knew that there was a treasure trove of how-to videos on YouTube. I viewed about a dozen of these videos which gave advice on make-up, wigs, and clothing.

I then went to the web and started ordering items.

Larry called me one Tuesday and invited me to come over that Saturday when he would have two friends visiting. Both were bi and mostly into being tops. I immediately agreed. The anticipation was nerve wracking and I had a great deal of trouble concentrating on anything whether at work or at home.

Saturday finally arrived and I laid out all my new purchases and began to prepare. I did not have much body hair and I had shaved every bit that I did - legs, armpits, chest, arms. I showered and then spread lotion all over my body to soften the skin. I applied some foundation to my face. My eyebrows were trimmed and I applied mascara to my lashes and painted my eyebrows with it. I used a light blue eyeshadow to my lids and also applied some eyeliner. Next, I brushed in a little blush on my cheeks and put on some lipstick. I could not believe the change in my appearance. My hair is fairly short and I slicked it back so my new jet black shoulder length wig would fit snugly.

I was now ready to dress. I had bought some breast forms and they fit neatly into my new red bra. My panties were also red and a thong. I wore black fishnet stockings as well. I topped it all off with a black cocktail dress. The most difficult part of my outfit was the shoes. How women can walk around all day in high heels, I will never understand. But I wanted the full effect and so I practiced diligently all week walking in my 3 inch heels. Examining myself in the mirror, I was amazed. I thought I looked pretty sexy. I couldn't wait to flaunt it in front of Larry and his friends

Nervously, I walked out of my condo and took the elevator down to the parking garage. One of my neighbors got in on the next floor and just smiled at me. I was unrecognizable. It only took 10 minutes to drive over to Larry's house. There were two other cars parked in front so I knew his friends were there too.

The walk from the car to the front door seemed to take an hour instead of 45 seconds. Larry answered the door bell and his reaction upon seeing me was priceless. "Oh My God! You are stunning!" I was elated and gave Larry a big hug and kiss. He then introduced me to Eric and Ted. Eric was a tall, lanky fellow in his late 40's. He had light brown hair and green eyes that lit up when he smiled. Eric actually kissed my hand. Ted was average height, looked in good shape and had gray hair. He was in his early 50s. We drank some wine and chatted a bit. Both of Larry's friends seemed quite nice.

"Well, guys, I think it's time for the fun to begin." With that, I stood up and unzipped my dress and let it fall to the floor. There were some hoots and whistles from the guys as I stood before them in my red bra, red panties and black fishnet stockings. I strutted my stuff a bit, hobbling along on my high heels, which I soon kicked off. "OK, who has a cock for me to suck?"

Eric got up and dropped his pants, his 8" cock was fully erect. I knelt in front of him and began to lick his cock head and fondle his balls. Slowly I took his shaft into my mouth and worked my way down until it was tickling the back of my throat. Meanwhile, Larry and Ted had stripped and started waving their cocks at me. Ted had a very long but thin cock, it must have been over 9" long. Larry's cock is 6" but as thick as a beer can. I took Eric's cock out of my mouth and engulfed Ted's. I began sucking him and jerking Eric's cock. Larry had gotten behind me and started playing with my ass. I felt his finger start to invade my nether regions while I was taking turns sucking two cocks. I asked Eric and Ted if they would like putting both cocks in my mouth at the same time. I had to stretch my mouth very wide but I was able to get a few inches of each one into my cock hungry mouth.

Larry was continuing to play with my ass and I suddenly felt him applying a generous amount of lube. "Who wants to be the first to fuck me?" Eric quickly volunteered. I bent over the side of an easy chair and soon felt Eric's shaft drilling my ass. Larry stood in front of me and I began to suck his cock. There is no feeling so erotic as having a cock at each end. Ted was standing near Larry and I was able to stroke his cock while I sucked Larry's. Once again I kept going back and forth between two cocks, eagerly sucking and licking.

Eric had worked his cock balls deep and began to fuck me hard. I would pause in my sucking to encourage Eric. "I love your cock in me! Fuck me!" I felt so slutty and so alive. Eric began to pound my ass and even gave it a few slaps - not too hard. That was an incredible turn-on. Meanwhile, I kept sucking first Larry then Ted. I was in heaven. Eric's cock felt so full in my ass and his steady pounding was driving me wild. The taste of two different cocks was also wildly exciting.

Eric started pounding me even harder and said "I'm gonna cum, baby, get ready!"

"Cum for me, darling, I want it so bad! Fill my ass with your juices!" I could feel Eric's seed shooting into me. He shot an enormous loud into my man pussy and it was soon leaking out and running down my legs. I looked at Larry and Ted and said "who's next? I need to be fucked a lot!" Larry deferred to Ted since he had already fucked me several times. Ted slid his long, thin cock into me very easily. It reached areas in my ass that had never been touched before. It did not take him very long to be on the verge.

"Baby, I am close and I want to cum in your mouth!" I was never one to refuse a nice hot load in my mouth. I wrapped my lips around his cock and began to suck. I had never felt such pressure as when Ted erupted in my mouth. After a few squirts he pulled out and said "watch this!" His cock shot a load about 5 feet in a high arc. It was very impressive. Larry told him that it was a great shot but that Ted would have to clean it up.

Now it was Larry's turn. He had the thickest cock I had ever seen, including in porn videos. He had fucked me on two different occasions but it was still slow going for him to bury his cock in my ass. It was still a bit painful but far less than the first time. Once he had his shaft fully inserted I was flooded with an intense feeling of fulfillment. I love feeling a thick cock stuffed into my ass. I needed to be a fuck toy. I loved feeling like a slut. Sucking Eric's cock while Larry fucked me added to my excitement. Larry started out slow. He gripped my hips and began to go faster. He slapped my ass and told me what a good slut I was. I loved hearing that. I wiggled my ass while he fucked me, hoping that it made him feel even better. "Here it comes, sweetie!" he yelled and filled my ass with another load of hot cum. Once again cum was leaking down my legs. I loved it!

I had been sucking Eric's cock for most of the time Larry was fucking me. Once Larry finished, I was able to really concentrate on the task at hand. I fondled his balls and moved my mouth up and down on his shaft. After a while, I felt that he was close. I wrapped my lips around his cock head and massaged the underside of it with my tongue. I was soon rewarded with another big load and I did not miss a drop.

We decided to take a break. After all, we were a group of middle-aged guys and we did not recuperate the way we did in our twenties. I was still wearing my thong. The guys had just moved the thong strap aside to fuck me. The front was saturated with pre-cum. We drank some whiskey at this point. I told them how much I enjoyed sucking and being fucked with them. I blushed at the compliments that were thrown my way in response.

"I need to suck more cock!" I shouted as I dropped to my knees. Ted was the first to offer me a nice hard dick. I sucked and licked with abandon. Larry and Eric positioned themselves on either side of Ted and I reached out and began to stroke their cocks. Once again I was going from one cock to another savoring the taste of three different cocks. I love feeling a hard cock in my mouth. Since everyone had already cum at least once, nobody was going to finish too soon. I slobbered all over each of these three very different but very yummy cocks. After about 20 minutes of alternating my attention from cock to cock, Ted grabbed my head and began to fuck my face. When he shot his load in me it felt like my throat was being assaulted by a fire hose.

Eric was next and he told me that I needed to keep going so he could cum again. I eagerly gobbled his cock, lavishing attention on his cock head with my lips and tongue while also taking it deep in my throat. Eric shot another load down my throat and I licked and sucked his cock until I was absolutely sure there was not one more drop to drain.

Larry was enjoying all this. He had been sitting back leisurely stroking his cock and watching me service his friends. He waited until both were finished and then informed me that he needed to fuck me one more time. Of course, I responded to this idea with enthusiasm. He pushed his beer can cock in me and began to pound me, slapping my ass in rhythm to his thrusts. I pushed back against him enthusiastically. Eric and Ted were too spent to join the fun but they enjoyed watching. After a while, Larry gripped my hips and shot one more load into me. I had been jerking myself while this was going on and I shot the biggest load of the night into my hand. The guys were amused to see me lap it all up.

I had brought an overnight bag with a change of clothes. I showered, washed off all the make up and dressed in male clothes. I rejoined the group and we drank and swapped stories about our sexual adventures. I told them that this was one of the most exciting sexual encounters I had ever experienced. We all agreed that we had to have encore performances.

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by Anonymous

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by Anonymous07/14/18

Nice read

Hope to get in on a hot night like that

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