The crossdresser

He is divorced. He has been playing in his x wife's old dresses and lingerie for years. We met on the Clubsissy website. I've always had a fetish for sexy sissy boys. He posted many pictures of him in her wedding dress. His makeup and fixing his hair are very good. He looks innocent, and slutty at the same time. I like that.

We meet at the hotel bar. He isn't a he anymore. He is in she mode. She is in a heavy overcoat. A London Fog sort of thing. Under the hem and between the coattails I can see her white stockings and white 4-inch heels. Her makeup is subtle. Her hair is pulled back with what are probably extensions flowing back over her shoulders. Very feminine. Very ladylike. Very sexy.

I remind her I'm just here for an introduction. Let's see what happens. She said she is cool with that. But she sure looks like this is pretty serious right now. A couple of martinis in, and she is ready to bring me up to her room. The bartender is off at a table. No one else is close by. She opens her coat exposing the full-on wedding lingerie she has on under. Push up bra, corset, girdle with garters, thigh-high lacey stockings, and so on. 

She closes the coat and stands up next to me. She smells really nice. 

"Let's give this a try, sweetie." She offers. I look up, still not sure I'm really ready. She slides her arm around my shoulders and pulls me in close. My face is in her chest. The coat opens again. She rubs my face between the soft, silky bra cups. I can't help but open my mouth and lick the smooth skin between them. The coat closes.

Down the hall to the elevators. She is nearly as tall as me. And I'm 6 foot 3. Into the elevator and off comes the coat. I'm pretty horny already. So is she. My face is pulled into her chest again. 

"Lick me like that again, please!" 

She has my head in her hands. Mine are on her hips. She is moving in and out, rocking. I lick and kiss and suck the soft smooth skin between her pretty bra cups. She smells like a young, sexy girlfriend. Then I move one aside and go for a nipple. She squeezes my head and lets out a sigh. 

"Oh my God!"

Her tiny sissy nipple is erect and sensitive. I'm really enjoying sucking it. She loves it too. 

"Go down for me, baby."

I feel pressure on my shoulders. I'm horny and hot. I'm sucking a sissy boy's nipple. I suppose this is what's next? Not as I planned or expected. But here I am. Getting passionate. Treating her like a sex toy. I'm thinking about all this while I slowly drop down on one knee. She presses my face into the sexy corset. Then down to her white satin and lace panties. 

"Lick those for me baby. Lick them and kiss them just like you were. Please..."

I have two handfuls of her pantie-covered ass, and a mouthful of wet, lace panties when the elevator door opens. The coat flips over my head, hiding me. A guest says:

"Oopps. I'll take the next one."

The door closes and she tells me, in a bit of a stern voice, to get back to it. I continue with the coat draped over my head. Soon the tip of her cock popped out of the top of her panties. Her hand grabbed and pushed my head down as I let her cock slip past my lips, and into my mouth. She makes some moaning and groaning sounds, and before I know it, my mouth fills up with warm wet goo. 

"Don't you let any of it spill out, you little cock whore!"

I choked and struggled and took it all. Her slippery cock was still in my mouth. She wasn't letting it slip out. I slowly let a little bit of cum gather, gulping it down. And then another little glob. Breathing through my nose alone wasn't very easy. It took me a minute to catch my breathe and finish cleaning my mouth of the naughty stuff. 

She pulled me back up on my feet. The coat was covering her again. She had a room card in her hand. The door opened and out we went. 

Finally, in the room, she threw me on the bed and started undressing me. I let that happen. I was hoping for some sex of my own. I wasn't sure what to think when the handcuffs came out. I put my hands up over my head so she could cuff them to the headboard. 

"You were awesome, baby. Let's get you doing a lot more of that."

I wasn't sure what that meant. Except I knew I wasn't going to have much to say about what it was. 

She kissed me with a big, warm wet kiss. She was rubbing her silk and lace corset against my chest. She told me she loved me. She put a nipple in my mouth again. It tasted wonderful. She had my cock in her hands. I was laying back in extasy. All I felt was warm, smooth skin, sexy lace, and satin fabric against my skin. She got on her hand and knees, moving up and over the top of me. Her legs were on either side of my head. She was looking back at me. 

"Open your mouth and stick your tongue out, baby."

Her spread open butt cheeks hit my face. She went down on me in the old 69 positions, with her on top. Her silky nylon stockings were rubbing both sides of my face. She smelled awesome. Very nice perfume. She was licking and sucking the tip of my cock. I was really horny. Her cheeks spread and I could feel the little hole between them with the tip of my tongue. She pushed back, squeezing my face with her cheeks. I was smothered with my tongue inside her hole. She was jerking me off while calling me naughty names. I loved it. 

"Eat me you fucking whore." As she squeezes my cock really hard.

"Lick my ass like you love it more than anything in your life." A wet hand slaps the side of my ass really hard. Whack!

"Deeper, bitch. Lick me deeper or you'll regret ever being born." Her hand is squeezing my balls much too hard!

My face is so fucking deep up her ass! My tongue is all the way inside. I can taste her. Her smooth warm skin was rubbed down with sweet-tasting lotion. Her silky panties rubbing my face. Her warm tasty butt cheeks spread over my face. Her hands stroking my cock and playing with my balls. It's all too much! I can't breathe. I'm gasping for a breathe. Oh, fuck!

I blasted off like a rocket ship. I've never had an orgasm like that before. She pushed against my face even harder. I came eating her ass out. I had a couple more spurts in me. She waited until I was done. Finally, she rolled off me and let me breathe. 

"Seems like you enjoyed that almost as much as I did, sweetie." 

I couldn't speak. Looking at her I couldn't help but notice her hands were filled with my sloppy cum. And down her thighs were several long, wet fresh cum stains. Did she come too? At the same time? What the fuck?

Chapter 2 - on the way soon