My first Crossdresser - Part One

When she walked in to the restaurant I knew I was in trouble.

It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.

Convincing she was not, a crossdresser without question. But pretty, really pretty. And the way she walked, shit, I was getting hard just watching her. She wore a tight black miniskirt, sheer stockings over sexy clean shaven legs, and a nice pair of heels. And man could she walk. I was in trouble.

The crowd was buzzing, and it was about to buzz a lot more. Everyone knew she was there, and everyone was trying to take a look without being noticed. She noticed, but she played it cool. I waited until she had finished ordering, took a deep breath, and walked over to her table.

Nervous, I introduced myself and asked if I could join her. She nodded, motioned toward the chair next to her, and looked up at the waitress who had just arrived with her drink. I asked the waitress to bring me a vodka and tonic.

"You're really pretty" I said. She looked at me. Silence. "I mean you really dress up nice." Silence. "I figured we might talk a little, maybe get to know each other." Finally she spoke. "You're a nice looking man, and you seem sincere. You DO know that I'm a man too, right?" The ice was broken. "Yes, I know that you're man too. But I mean it when I say that you're pretty. I've always had a thing for crossdressing, and I'm not uncomfortable to say it." She grinned and replied "I come to Vegas twice a year to escape. I work in the post office in Cedarburg Wisconsin. My time in Vegas let's me live out my fantasies." She paused to sip her drink. "Please forgive me for being a little cold, I've never had a man approach me before to talk. If a man approaches me it's usually on a bet from his buddies, and he makes an ass of himself and embarrasses me."

The waitress appears and puts my drink in front of me. I pay her and take a sip. "When I saw you walk in I knew that I was going to come over and introduce myself. I'm very attracted to crossdressers, one of my fantasies. I've never played it out." She was sipping her drink, and without taking her painted lips from the straw, she looked at me and winked. The she picked her head up, cocked it a little to the side and said "Maybe you'd like to play it out tonight?". I gulped and nodded. She follwed with "I'm lonely, and I'm tired of sl**ping with my dildos. I could use a real cock. But, I'm going to warn you, you're going to have to play it my way, and it might get a little difficult." I nodded again and said "Let's give it a try." My dick was as hard as a rock.

To be continued...
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Posted by abend
3 years ago    Views: 1,523
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6 months ago
Nice writing. I mean, you use your words well. I know it's a big world and there must be room for every imaginable conversation, but I was surprised when she said, "You DO know I'm a man too." Mmmm-No; I don't think so. At least, I've never heard that. See, you're writing only your own thrill here; your own fantasy. You have to go for hers, too. So you say to a beautiful girl, "You look wonderful tonight," and SHE says, "Uh, you DO know I'm wearing tons of makeup, right?" Oops.

So then the thrill, or the fantasy, would be gone for the crossdresser. Or not; your call. But consider whether you are requiring both to share the same fantasy, or the same ANYTHING; because they wouldn't be. Yours is clear; hers isn't.

Other tiny hiccups were "everyone knew she was there" which everyone wouldn't; some don't care and some don't see. Only a few deep breaths, more likely. Just a hiccup. And another: "I've never had a man approach me before to talk." Yes, she had. All the time; every time she went out.

Your use of words is really good, but the probability/plausibility isn't so good. I'd never mention it, but you could write a really good story. You have to always and always ask what would most likely happen and stay with that. And you have to BE the person you are writing about. Different ways of speaking; different values; the whole bit. The most probable scenerio here (and most often) is pretty close to nothing at all, so the silences and maybe the awkwardness you describe is great. It is really a lot of fun to question yourself about what she really WOULD say. Does she swear more than he does? Is one tougher than the other? Actually you want to TEASE your reader, so the reader makes up his own story as he reads yours. So now you have the person telling the story, the crossdresser, and your reader: lots of fun guesswork. Not to mention the waitress.

If you want, you can be angry with my presumptuous, unasked-for criticism. Fine; no problem; I'm sorry. But I noticed right away that your use of words is really good; way better than most. That was what made me write all this. Again, my sincere apologies for it if you don't like it. Certainly no offense intended. But you're driving a very nice sports car, and I thought I'd offer some tips about getting its engine smoothed down just a little. :)
Bottom8909
retired
2 years ago
please don't keep us waiting
jacquin001
retired
3 years ago
I love crossdressers thanks
penissucker
retired
3 years ago
I want some!!!!!!!!!!
3 years ago
Really good stuff:)~ will be watching for more!
3 years ago
Waiting for Part Two!