Saturday Night Fun

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How I spent a recent Saturday night.
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kayla69
kayla69
12 Followers

This is a true story. Feedback is definitely welcomed!

*****

I made sure that all my body hair was removed. I feel so sexy when my skin is smooth. I had attached my new breast forms earlier, and feeling their weight pulling on my chest is always enticing.

I put on a cute white bra and white cotton panties, then pulled on my favorite "Naughty Kitty" t-shirt and a cute mini skirt. I pulled a loose-fitting pair of jeans and a baggy button-down shirt on over my skirt and t-shirt, and stuffed my red wig into the shirt. Due to my roommate, I can't just walk out of the house in full drag, so...

We had talked earlier on craigslist, and he agreed to meet me outside of the bar around the corner from my house. He was waiting in his truck when I walked around the corner. I walked up to the passenger door and he let me in. He was pretty cute, so I knew this was going to be fun.

As soon as he started moving, I pulled out my wig and put it on my head. I then removed my outer shirt and jeans, leaving my tanned legs and body exposed.

"Is this better?" I asked.

"That will definitely work," he replied.

We exchanged small talk as he drove around, looking for a private place to park. The console in his truck was too large to allow me to pleasure him while we drove. I kept wiggling my bare legs, hoping he'd reach over and rub them, but he didn't take the hint. (I think he was as nervous as I was!)

He finally found a quiet and dark parking area and pulled over. After another few minutes of small talk, he suggested we move to the back seat of the truck. (Finally!) We did so, and after a minute or so, he finally unzipped his pants and released his member.

I leaned in and took it in my mouth. He was completely flaccid, and kinda small to start. As I licked and took him into my mouth, he began to grow. I continued to suck and lick on his penis, and it rewarded me by continuing to grow and swell in my mouth. After what seemed like ten minutes of oral stimulation, he was pretty firm, and moaning encouragement to me.

A few times he started to rub on my back, around my t-shirt and tentatively sliding his hand under it, but he seemed a bit shy about going further, so I sat up and pulled my t-shirt over my head, exposing my white bra, and the edges of my breast forms when the bra shifted. When I returned to my oral duties, he began rubbing his hands over my back, and reaching down to my skirt. After a few minutes, I reached over and unzipped the skirt, so he would have easier access to anything he wanted to grab.

He took advantage of this by sliding his hand down the back of my skirt, first over my panties, and eventually inside of them, even sliding his fingers along the crack of my ass. I tried to wiggle and encourage his hand to go all the way to my rosebud, but he didn't go that far. I continued to worship his member, and I could feel it continuing to grow and swell in my mouth. I thought he might be getting close, but then he shifted in his seat, interrupting my services.

"Are you getting close?" I asked.

"Well, kinda," was his reply.

As I went back to work, I reached around and grabbed his hand, placing it on the back of my head. I really wanted him to fuck my face now, but he didn't seem to enjoy that too much. I then suggested another position.

"Can we stand outdie the truck, and then you can fuck my face?"

"Okay," he said, and then he opened the door and got out onto the driver's side, away from the street.

I climbed out of the passenger door and walked around the front of the truck. As I did, my skirt slipped from my hips, leaving me dressed in only my red wig and my bright white bra and panties! The feel of the night air on my naked skin was exciting, and I wished we could be in a place where someone else could see me.

I walked up to him and thought about kissing him, but decided against it. I decided to try something new, and laid across the back seat of the truck, hanging my head off the side so he could fuck my mouth there. He tried for a few minutes, but the truck was just a bit too tall for this to work, so I dropped to my knees in front of him to continue my services.

After another five or six minutes, I thought I heard someone, and stopped. I suggested that we move to another location, and he agreed. I picked up my skirt from the ground and walked around to the passenger door, then I got in and we left.

We rode around for another fifteen minutes or so, looking for another secluded place. The whole time I was dressed only in my undies, and I felt so sexy :) We finally decided to call it a night, so I began to get dressed as we drove back to my neighborhood. He dropped me off around the corner from my house, and I sneaked quietly back into the house.

Hopefully, I'll get to finish him off on our next encounter...

kayla69
kayla69
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AnonymousAnonymousover 9 years ago

Yes, I dressed, black wig, tennis top and black flared skirt, black tights underneath. I am 48, not new to crossdressing but new to going out in public. I drove to the park and to the tennis court. There was a car parked, I got out, as arranged just as he got out. Tall, he said he was 55 on the web site. He was in tennis gear,shorts, top. He unlocked the clubhouse door, entered, I followed..He stood, I looked at him, his hand on my wig, pushing me down, I lowered his shorts, mm, nice, slowly stroking his cock. I stood up, his hands went to my bottom, a finger pushing at my hole, tights slit strategically, turn around, mm nice tights, ,i turned back around, he fingered my prepared hole as I stroked him. I knelt down, taking his cock in my mouth, fresh,hard, pre cum on my tongue, I wanted to taste him but he wanted something else, turning me around, fingering me again. I heard the door,the second person had arrived, sit on that bar chair, I did facing the back of it, my hands holding onto the rails, my bottom just over the edge. I felt the head at my entrance and then entering, sliding into me, my cock stiffen as he bottomed fucking me, slowly at first but now faster,my insides trembling as he fucked me. There, my cock was tingling, I couldn't stop it as my cum shot out, my bottom clenching his cock, I heard him say aagh and I felt his cock pulse in me and for the second time I felt a mans warm cum enter me. He slowly pulled out, O.k Doug, shes yours, I saw a short solid man, about the same age, grey flecked hair.He moved behind me, I heard gees be careful with that, you might bust her. I felt the head, wider against me, he pushed , opening me more as he entered me, I felt stretched, then as he pushed a bit more, my hole closed around him, moving into me in one slow push, going past where the first guy had been, bigger and thicker and my cock even though it was semi hard started leaking. His fucking was controlled, beautiful, slowly stroking my insides, with each thrust more cum leaked from me. He pulled out, no, I pushed back, lay down on that table, I was dizzy but I did. The other guy grabbed my legs, his cock dangling over my face and Doug pushed back into me also holding onto my legs and fucked me, literally, physically fucked me. I felt him impossibly start to swell, oh shit, your going to bust me. As he fucked he said your a good tight fuck so I am going to make it good for you. When Alice was alive she liked anal like this and he pulled back so the head of his cock was just inside my hole, again I was stretched right open and I felt the first pulses, the warm cum coat just inside me and then he pushed deep, stroking my semi hard cock, fast as he pounded me until what cum I had left bubbled out of me. He slowed and pulled out, I felt open, they helped me up, I was dizzy as I pulled my tights up,they offered me a beer but I declined and walked to the car, my cock still tingling.

AnonymousAnonymousover 9 years ago
Sounds HOT

Hope you can get him to finish, had me hard in my Panties for a Happy Ending.

AnonymousAnonymousover 9 years ago
Same old same old!

Just another "put on a dress and get a blow job" tale. Nothing new here folks! Move on.

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