His first cock - Sex Stories

His first cock

The ad said he wanted to try sucking a cock but he was nervous and wanted someone who he could get comfortable with first. I told him in my reply that I was his man and he wouldn't have to do anything he didn't want to do and could stop at any time. When he arrived I invited him in and showed him to the sofa in my living room where my 70" television was featuring some hot shemale hypno porn. We sat and chatted for a bit and I made some comments on the hot shemales sucking cock on the videos. He said he really loved shemales, trannies and cd's and that he'd found himself wanting to suck cock more and more but had never gotten up the nerve to actually meet anyone. He'd usually set a date but then end up jerking off and changing his mind. Today was different in that he had jerked a bit but didn't cum yet. I said let's get comfortable and removed my pants and underwear. My cock was still a soft 3" and I'd freshly shaved it and the entire area around it including my balls. I reached over and stroked him through his jeans for a bit and got him hard, I said, "why don't you take off your pants and I'll help you get in the mood?" He said OK and I helped him pull down his jeans and was happy to see that he was wearing women's panties. Some nice silk ones in red. I told him that they looked hot and proceeded to get on my knees in front of him. I stroked him through the panties and he got really hard really fast. He looked to be about 6" erect. I reached up to the waist band and pulled ...

... them down so he was free. I leaned in and licked him from the base of his shaft to the head a few times before taking him in my mouth and sucking him right down to the back of my throat. I sucked hard as I slid my tongue back and forth across his shaft and he suddenly said, "ok, I want to try." I gave him a final suck and kiss on the head then got up onto the sofa and he slipped down and took up position in front of me. My soft cock had some pre cum leaking out and he tentatively took hold of me and gave it a taste. I let him go at his own pace and he shyly kissed the head and licked the shaft. After a few minutes where he still hadn't tried to take me into his mouth, I pulled out a tube of sexy red lipstick I had ready and said to him, "you have such nice feminine lips, I bet they'd look really sexy with some lipstick on them. Girls love to suck cock with lipstick on and guys love it too." He looked up at me without protesting with his mouth open just a little bit. I took advantage of the break to lean towards him with the lipstick and with my other hand took his face by the chin. I applied the lipstick back and forth several times across his lower lip getting a nice thick coating on and then had him lean his head back just a little so I could do his top lips. As I applied the lipstick I saw his cock grow to full length and maybe a bit more! He was into this. He was getting really turned on by the lipstick and as soon as I finished applying it I said to him, "very sexy, such ...