After meeting Chris the transvestite I was soon arranging another meet at my place with another transvestite called Carol, who was about forty years old, fairly experienced and after chatting online very briefly we arranged to meet at my place. Carol liked to dress fully just like Chris had done and so I decided to experiment a little further with my own crossdressing. I bought myself a black stretch minidress and a pair of backless high heeled shoes online and even purchased some makeup and a wig so I could at least try and make my appearance more femme like as this seemed to be what most crossdressers/transvestites preferred.
I had a week to practice my make up skills before my arranged meeting with Carol and spent most evenings doing this and getting dressed in my new dress, heels and wig and couldn't believe how sexually aroused it made me, dressing fully and watching myself in the mirror as I masturbated which usually resulted in me coming very quickly.By the end of the week my makeup skills had improved to the point where I was fairly pleased with the result and I was now ready and willing for my meet with Carol and couldn't wait for the slutty fun to begin.One other thing about Carol was he liked to shave his body smooth all over which sounded very sexy and so on a whim, the night before our scheduled session I spent a couple of hours shaving my legs, upper body and all my pubic hair and around my bumhole so I was also totally smooth all over for our meet.
When Carol showed up at my door the following morning, I felt slightly intimidated by this six foot tall guy, with a confident manner, who simply walked into my flat as soon as I opened the door and asked straight away where the bathroom was so that he could get ready. He came across as a little bit cheeky but thinking about it getting dressed straight away was probably better, rather than sitting and chatting with us both in male attire which tended to lead to nagging doubts about indulging in sex together which was how I felt when I first met Chris.I showed Carol where the bathroom was and told him I would wait for him in the lounge where I would get myself ready. The sheer stockings felt fantastic against my newly shaved legs and my smooth balls tingled inside my silky red panties and I was already very horny as I anticipated another sexy encounter with a transvestite. It took me a while to get fully dressed with the makeup taking up most of that time and when I was finally ready I sat down on the sofa and waited for Carol to return.
Carol returned and started walking around the room, flaunting himself in front of me and I had to admit although he was a little bit over the top he did look really sexy. He was wearing a black basque, black panties and seamed holdup stockings and a pair of high heeled shoes where the heel must have been at least six inches long making him tower over me and he had on very slutty makeup with bright red lipstick and a short blonde wig which all made him look like a very, filthy slut.He kept asking if I liked how he looked to which I replied that I did. He also asked what I liked doing and I told him that I liked sucking cock to which his reply was that he liked to be fucked. The way he said it and just the thought of fucking him in the arse made my cock rock hard. He then wasted no time in asking where the bedroom was and so I willingly showed him the way so that we could get down to some horny fun.
As we walked into the bedroom he turned to face me and asked me to get on my knees to which I willingly obliged. He placed his hands on my head and stepped in close so that his bulging crotch pressed against my face. I could feel his hard cock inside his panties rubbing against my face and as I breathed in the musky aroma, he yanked his panties to one side and his hard cock slapped against my face. It was quite small, but very thick and circumcised. When he pulled my head in closer I opened my mouth and let him slip his whole length between my lips. I started sucking as he thrust his hips, forcing his cock into my mouth but after only seconds he stopped and pulled his cock from between my lips, much to my disappointment as I was really enjoying the way he was fucking my mouth.He suggested that we get on the bed together which we did laying side by side. He started to stroke my hard cock through my silky panties which felt really good and I began doing the same to him, admiring his lovely, long smooth legs which would have made most women very envious.Carol moved down the bed and removed my cock from my panties and started sucking me which felt absolutely wonderful. As he continued sucking me I began to play with his arse which seemed to work, judging by the moans coming from him as I gently inserted a finger inside his tight, smooth hole.
He was very good at sucking and I was a little worried that he was going to make me come too soon but he stopped before I got to the stage where you just can't hold back anymore. He said he was now ready for me to fuck him and the way he said it just turned me on so much. He said he would be back in a minute as he had left the condoms and lube in the bathroom. Waiting for him to return I started wanking slowly realising that I was about to fuck another guy in the arse for the very first time and although I had the obvious concerns about whether anal sex would be messy and not particularly clean and natural I still couldn't wait to experience the sensation of sliding into his tight hole.When he returned he handed me the condoms and as I put one on my cock he lubed up his tight bumhole. He got on the bed on his hands and knees and told me to stand on the floor behind him. His spread bum cheeks and smooth hole looked so inviting and my cock was rock hard in anticipation . I started to rub my cock against his tight, lubed hole and even with the restriction of the condom it still felt amazing and when he groaned loudly and pleaded for me to slide it in I gave one firm thrust and was amazed at how easily my cock slipped inside him. He let out a cry of pleasure and I began to fuck his tight hole, sliding my cock all the way in then back out and the tightness of his hole felt better than any pussy I had ever fucked and I knew I wouldn't be able to keep this up for very long before I spurted my come into the condom. I couldn't help but wish I could fuck him like this without the condom but knew that was too risky with the dangers of sexually transmitted disease.
Before I was able to come as I fucked him he quickly pulled away from me, letting my hard cock slip out of his lubed arse and he rolled over onto his back with his head hanging over the side of the bed. He told me to stand over his face so he could suck my cock, which I did willingly. As my cock slipped inside his warm wet mouth I leaned forward so that I was virtually lying on top of him in the 69 position. His small, hard cock was inches from my face and the head was soaked in precome and so I did the natural thing and took him in my mouth and started sucking him as he did the same to me.The taste of his precome was lovely and as we slurped noisily on each others cocks it became obvious that we were both very close to coming. I heard him moan and felt his cock twitch suddenly, sending a hot spurt of come onto my tongue, followed by several bigger spurts and almost simultaenously I started to come too.I could taste the strong flavour of his heavy come load and although it didn't taste too bad I still bottled out from swallowing it down and let it dribble out of my mouth, down his cock and onto his smooth crotch. He on the other hand gulped down my come as it spurted into his hot mouth and judging by the moans of pleasure he seemed to enjoy it a lot.