Craigslist Experience #9

My first CD (Cross Dressing) experience: 

So, one Sunday evening, I'm just home watching TV, and drinking some beers, and I decide to check out the Craig'slist posts. I don't even know why. I had already jacked off that day, and really wasn't horny. Craigslist had become "routine entertainment" I guess.

So the first post I see says this.

> NOW - 21 (Comfort Inn by Airport)
> Reply to: pers-nsxxg-1233206119@craigslist.org
>
>
> I am super horned up....non-passable CD that wants my first anal experience NOW....I have given >head before but not to completion....I want to do it all now!!!! I am 21...ddf....non-passable...but >dressed up already for u to come....u come lube me up i blow u fuck my ass you face fuck me, and >give me facial and u leave....u need to be able to come to me hwp....willing to be my first, and DDF >send pic and i will give u my hotel room number!!!!
>

Here is what I responded with:

Hey, I've been drinking beer and hanging out reading these CL posts. I don't know why, but your's gave me a boner.
I'm older, and have topped once, but it didn't work out well,  but it would be cool to give it a go with you. I don't have a big dick, so maybe that would make it easier.
I live close to the airport, so I could make it quick.
What do you say, want to be my little girl?
Jack.


So, he (she?) wrote back:
how big is ur dick, and have u ever been with a man before?
still interested?

So I responded:
yah, I'm still here. I've tried twice to send additional pics, but it's not working...

So he said:
i am waiting on someone else right now to see what he says but u might just get my room number in about 10 minutes!

so u can bring some porn too there is a dvd in my room if you want to have straight stuff going...and one last questions....have u ever fooled around with another guy

And I responded:
Sorry, I had to re-boot computer, but it still won't work. I
have hooked up with 8 guys on CL, but I'm still pretty new. Tried to be a top once.
Be patient with me. Still interested.....

He said:
yeah room 131...i can be patient if u can be ;)

I said:
See you soon. I hope you're wearing something hot and sexy.

His final reply:

From: michelle smith
To: jack

i don't have any porn but would u bring a condom if u get this


I don't know what came over me. I never respond to ads posted by 21 year olds. What's the point? Plus, I am not attracted to cross dressers, and I've only tried to give anal once, and it was a disaster. I guess that I figured since it was his first time, he wouldn't know the difference. When I replied, told him I was older, but didn't say how old, and included a picture. He could guess my age from that.

I got my condoms and KY that I purchased for my first trial anal disaster, and put them in my pocket. I also took a beer and put it in the pocket of my cargo pants.

I found the hotel, and his room. There was a couple standing in the doorway of the room directly across the hall. I sure didn't want them there when a dude in woman's clothing answered the door. Luckily they left, and "Buzzcut" answered the door.

Oh my heck! Buzzcut was cute, and had a great body. Not too skinny, and not at all fat. Black buzzed hair, he wore glasses, but he was cute. He had on a fishnet stockings, a bikini bottom and a swim suit top that didn't match.

What ever floats your boat. Actually, the fishnet stockings were kind of sexy.

I told Buzzcut he looked sexy, and I was nervous, and he told me his limits. No biting and no scat.

 No problem..

I felt him up, got under the top, pinched his nipples and caressed his crotch on the outside. He rubbed mine as well. "lay down." He invited. Take off the bottoms I instructed. He did.

He unfastened my pants and slipped them down. I was getting a boner. I sat back on the bed and adjusted the pillows, and he started to suck me. When things were going good I thought about the fucking part. This time I was going to do something different. I was going to try and stick my finger in his ass first and get it somewhat looser.

I told him to spin around to give me access to his cute brown ass, and told him to hand me my shorts. I think he knew I going was after lube, because he said he had some on the nightstand. I was laying on my back and he was straddling me in a 69 position and while he was blowing me, I poured some lube in his ass crack. Too much. It kind of ran down and got me in the neck. I started rubbing his ass hole pucker, and pressing in my thumb. To my surprise, it went right in. I thought I better go for more than just my thumb, so I then exchanged it for my index finger, and then a second finger as well. All was going along fine. No problem. So I said....are you ready now?

He said he was, if I was. I told him to get a condom from the pocket of my cargo shorts. He did, and he rolled it onto my hard dick. I told him again I hadn't really done this and for him to tell me what to do, and tell me if it hurt or anything.

He got on all fours and stuck his beautiful boy-butt in the air. I had to tell him to lower it. I got the head of my dick at the entrance to his hole and rubbed it around a bit. I could feel it wanting to go in. I kind of worked it in like I was fucking a chick, and when it popped in, he winced, and I asked "Slower?" "Yah." So I went super slow. His butt was so hot. Yes, hot sexy, but hot temperature-wise too. "You can go faster now." He said. In no time at all I was burying it to the hilt. He moaned a littl, said he liked it and stuff like that.

I leaned over and really wanted to bite his neck for some reason, but one of his limits was "no marks" which of course I can respect. So, I nibbled on his ear, and whispered nasty stuff to him, and then reached under and stroked his beautiful dick, as I fucked his ass.

This went on for only a few minutes when he said "I'm gonna cum" It was just louder than a whisper. I said "no, wait, don't come yet" but his hand went for his dick, and I knew he was past the point of no return, so I kept fucking his ass and reached under him, pushed his hand away, and grabbed hold just as he started jizzing all over the bedspread. I could tell he was in ecstasy, and I was doing it to him. I loved that.

If I had my way I would have liked to turn him over and watch him shoot off while I was jerking him, but it was not to be.

I asked him if he still wanted to get me off.

He blew me again, and I mentioned that I had already cum that day.

He soon tired and asked me if it was okay to "just call it a night."

Sure kid, it was fun just the same. I cleaned up, dressed and gave him the extra condoms I brought, as well as the semi-cold beer from my pocket.

As I think about it now, I get the feeling that probably it wasn't his first time. His butt sure accepted my cock a lot better than Elton's. But, whatever. I got to fulfill a fantasy that night, a fantasy that I never really knew I had.