My CD friend
This story is fiction.
I had been chatting to people on a ts chat room as I had recently become accustomed to do, when I received a private message from a local cross dresser. She asked me where I was from, how old I was etc and we found out we lived a few towns away from each other, both young guys and both really loved wearing women's clothes.
Admittedly she was much more experienced at it than me, having access to girlfriends, s****rs and mothers clothes and had even ventured out fully dressed once!
Eventually after some light chat, swapping dressing up stories and what we liked wearing, he invited me over to his sometime to dress up together in any of the ladies clothes that fit. Obviously this was too good to refuse and we quickly arranged a time and a day when we were both free and discretion would be assured. It turns out his mom was away on business a lot so his house was nearly always empty.
Turning up at the door nervous and excited about the fun I was about to have. I knocked on the door and it opened instantly.
"Hey, are you Shannon?" (my name i had been using for my CD chats) he asked me
"Sure, nice to meet you Sandra" (the name he had used) We shook hands and he motioned me inside. It was a really nice place, obviously his mom did something important to have been able to afford it. She must have some nice clothes to try I thought to myself.
We started chatting and getting to know each other a bit when the conversation eventually turned to the reason I was there.
"So, you want to see what sexy outfits we can find?" Sandra said.
"Sure, I would love to! No chance of us being interrupted is there?" I didn't want to be chased out of a house wearing the female owners clothes, might be hard to explain, he he.
"We have the house to ourselves all night and most of tomorrow too." Sandra reassured me, smiling knowingly at me. "I thought we could give each other a make over, get nice and dressed up all sexy and head out tonight, about 11, 12ish, when guys are all wearing their beer-goggles, and see if we can pass for girls, what do you think?"
Reluctantly I agreed. I wasn't keen on going out dressed, I was sure that I would be in no way passable and it would need to be someone so d***k they could barely walk to think I was a woman. But as Sandra was so nicely letting me play with her for the day, it felt rude to decline.
We went up to the mothers bedroom first, seeing as how we thought she might fit my size better than his s****r. What an amazing collection of clothes! A huge walk in wardrobe, lined with dressed, skirts and shoes as well as a massive draw full of exciting lingerie, with thongs, corsets, stockings, suspenders, garters... you name it, she had it!
"Wow! What an amazing collection!" I said in wonder.
"And its all yours for tonight! Lets see what looks good on you." And immediately we started clothes hunting amid the treasure trove. After hours of bliss trying on a variety of sexy ensembles, we decided on a cute black lacy thong which actually held my cock well, not much of a visible bulge. We found some fake breasts which would do to support a nice matching lacy black bra. I chose some fishnet stockings and black heels to go with it and I felt amazing!
"Wow Shannon, you look great in that! Now lets find you a dress or something to go with it!" Sandra said eagerly.
It took a long time again but eventually we settled on an elegant and sexy red dress which fitted perfectly. I was in heaven!
"When we get some make up on you, you are gonna turn some heads! he he" Sandra laughed a naughty little laugh, I did not know the sort of venue she had in mind at this point or I probably would have left then.
"Thank you honey, now lets sort you out!" I said, about to dive back into wonderland.
"Oh no, its OK, I already have some of my girlfriends clothes I stole last time she stayed a few days. Lets put some make up on and there are a few wigs my s****r has which we can borrow."
So anyway, we did each others make up and to my amazement I looked like a completely different person. Not even my own f****y would recognize me! It kind of got me aroused to know that I made for a really attractive woman, probably more so than as a man.
After having a light dinner and a few bottles of wine, we were ready to head out, fully dressed as ladies. No one would have known what we really were. As we walked into town, we got wolf whistles from groups of guys passing by. It was such a thrill!
We got to a nice looking bar and were let straight in, the bouncer thinking we were girls! When we got to the bar, it was obvious a lot of partying had been done. Booze had been spilled all over the counter and it was pretty quiet. However, there were two guys sitting at the other end, directly across from us and they started to send some drinks over to us. Getting very d***k, Sandra suggested we go and say hi. I was not keen as I knew voice wise I have no chance of passing for a girl.
"Don't worry about it, just let me do the talking!" Sandra said confidently. Her voice was higher than mine and was sure she could pass for a woman.
I was in a tight spot. I was stuck with Sandra. I did not want to get fucked tonight by some random horny bar guy but if Sandra invited them back, what could I do? I was in her mothers clothes, two towns from home with no way back until the morning. The streets were probably even more dangerous than the guys who were offering the drinks, especially dressed as a sexy young lady.
"OK, just light flirting though!" I said, pleadingly. Sandra just winked and said "Trust me!"
We headed over to the guys, who turned out to be in their mid thirties. One was considerably taller than the other and had been eying Sandra up while they chatted. The shorter, muscular one had been staring at my fake breasts all the time we talked and I was getting very body conscious!
"Maybe we had better go..." I whispered gently into Sandra's ear.
"Hey, that's a great idea! You guys want to come back to mine? We have the place all to ourselves and lots of drinks to get through!" Sandra said to the guys. Of course they accepted straight away and before I knew what was happening, my ass was being felt up by a muscular thirty year old as we headed back to Sandra's house!
When we got back, we all headed into the lounge where there was a well stocked drinks cabinet and the drinks certainly flowed. I had stayed quiet all evening but suddenly the short guy said. "We know what you both are. You are very convincing but you are guys."
I was shocked! Sandra was too! How could he have known!?
"It's OK, we love shemales and cross dressers. But as you have invited us back to yours, we will not leave until we have had some fun." He got up and undid his jeans, revealing a huge, 9 inch hard cock. His friend did the same, revealing a similarly huge penis.
The short guy looked at me and said, "You are going to be my girl for the evening. You are going to be his," he said looking at Sandra, "And there is nothing you can do or say to get out of it. Now come over here and suck us off like the little sluts you are!"
I looked at Sandra, she had already raced over to her man for the night and began sucking him off. Seeing her lead I felt I had to do it too. Not that I had a choice. I was roughly grabbed on the back of my head and f***ed onto his cock, where he began to mercilessly fuck my mouth and throat!
Struggling not to gag on his huge member, I just sat there and let him pound away at my face as I struggled to breath. After what seemed like hours he said,
"Get ready whore, I'm about to cum!"
Oh shit! I thought to myself. How did I get into this!?
Suddenly a hot gooey liquid was pouring down my throat and I really did gag, causing his dick to come out of my mouth and spray cum on my face and on Sandra's mums dress!
"First timer eh? C'mon bitch, I'm gonna break you in!" And grabbing me by the wrists, led me upstairs and into the first bedroom he found, which turned out to be Sandra's moms.
Slinging me onto the bed, face down, he spanked my ass hard before pulling up my dress, revealing my sexy black thonged ass.
"Damn you are hot!" He said as he spanked my bare ass!
Then he pulled my panties down, revealing my tight virgin ass hole. Suddenly, I felt a wet slimy thing wiggling around my hole. Oh god! He is rimming my ass! The pleasure and weirdness of the sensation combined and I started to moan.
"You like that slut?" He asked.
I could not answer but he seemed to know, because after a little while, the sensation stopped and was replaced by a probing feeling as his cock was working its way into my ass!
"Oh fuck!" I screamed out loud! The pain of his huge cock entering my tight ass was unbearable! This only seemed to encourage him though because right from the start he began pounding me hard, making the whole bed rattle and creak, seeming to share my agony!
My hole started to widen and get used to it and eventually turned into an amazing feeling as his monstrous cock stimulated my prostate!
"Get ready for it! I've got another load for ya!" And suddenly what felt like gallons of cum exploded deep inside my ass! Sperm filled my hole and the sensation caused me to cum too!
"Oh fuck! That feels so damn good!" I screamed, I could not believe I had said it! The feeling of being completely owned, of being covered in cum with it dripping out of my ass and cumming at the same time meant I was in a world of ecstasy!
"Well we have a long night ahead of us, and a lot more where that came from..." He whispered in my ear, making me shiver with delight and anticipation.
To be continued....