I was about 22 or 23 and it was the summer time. I was already mega into cross dressing and web-chatting for older gentlemen, but only then for the internet. hungry for someone to touch or hold me for real, I began to search craigslist for older men hosting or looking for other men,. I would send them pictures of me dressed in thongs and stockings and await responses. One afternoon, I got this older dude, and he sent a yahoo link as well.,. so I promptly added him and began to video chat. He said he liked my outfit and wondered if I wanted to come over to his apartment, which wasn't far from where I was staying. I said yes. Instant butterflies,. the thought ran through my head what i had just agreed to,. and my heart couldn't stop beating,. I was going to go through with it.

So I quickly threw on some male pants, shirt, and shoes with my stockings garter and panties underneath. It was sunny, warm and peaceful as I walked down through the park to meet up with this guy I found via craigslist, and yahoo instant messenger. As I walked up to his apartment I thought is this the place?,. I didn't have a cell phone and just ran out with his information via email... I was a bit nervous,. I checked the numbers of the building and it was the right one.,. I had the apt number as well,. So I walked into the building surprised it was already propped open, I felt a mischievous element come over me,. I wanted to meet this guy, have him look at me in women's underwear,. grope me, and maybe fuck me,. I had also wondered what sucking a cock would be like,. what would it taste like,. I walked up to the apt door i had been given and gave it a few polite taps.

This grey haired older gentlemen opens the door,. and immediately exclames "i didn't think you'd show up",. and gave a dirty old chuckle,. he directed me into his room as there was another person in his apartment,. I had questions but wanted to see what would happen...

We walked into his room,. it was a light blue color with a large window over his bed,.. it was nice. He asked if I had any porn, I said no,. and removed my clothes,. his eyes lit up,. and said "wow, you do wear women's underwear",. I didn't really know how to respond, but with a lite chuckle,. he removed his clothes and laid on his bed,. I climbed on and began to nuzzle his cock,. I told him I never sucked a real one before,. he gasped,. and said "well,. go ahead",. with a smile.. I began to lick his shaft, on one side and the other,. it didn't taste bad,. I liked it,. began to lick around the head of his shaft and finally sucked a dick for the first time,. I managed to get it all the way down,. I softly gagged and he removed his cock saying "oh baby, you almost made me cum",. My brain went wild deep inside,. I loved the way this felt.

He groped me and kissed me for a moment,. and then asked if I've ever been fucked before,. I nervously said no,.. so with a playful grunt he laid me on my back and spit unto his cock and placed it on my rectum,. he gave it a little stir ,. and I buckled and made a involuntary sound,. I asked if he had any condoms or lube and he pulled out his head from my unfucked hole,. he simply reached over me grabbed a condom and some lube and we were right back in the same position again. Me laying face up ,. legs in stockings pushed up against his chest against my chest,. his cock nearly penetrating me,. making me feel like the sissy bitch I've always wanted to be,. He said something like "oh baby,. you're too ,. too hot?!" and pulled out,. removed his condom and ejaculated all over my face and chest,. he reached over and threw a towel on me, and said to come back later that night,. If i wanted to be properly fucked...

I got up wiped the cum from my face and chest, put my panties, clothes back on ,. he then walked me out of his apt. This all happened in what seemed to be less than a half hour... I was shell shocked and even hornier for my first call out experience,. I wanted more,. but the reality set in,. I had to go back to where I lived and try not to act liked I had just been a whore to some old man. :)