A one week fling

Posted in: TvTs

Hesitantly I answered the ad — ‘single man wants sissy cd for entire week end of passion and wild sex’. It sounded too good to be true I thought to myself. I sent an email and received one back immediately. ‘Glad to hear from you meet me at my hotel down town’. He said giving me the room number and name of the hotel. But I replied back
‘Should I bring something to dress into? ‘I asked. Once again the response came quickly.
“We will only be meeting to see if we connect then I will tell you, when we if at all will get together.’ I must say I liked his tone, how he was taking over the conversation.
So I went to meet him. I knocked on the door and he opened it letting me in. He was a well built man about six, one or so and not much fat. He answered the door wearing only his pants and explained he had just got out of the shower. He had me turn around and watched me as I did very closely. He then asked me to bend over facing away from him. I did so and felt his hand run over my ass so I pushed it out towards him. ‘No need for that’ he said. ‘If I want you I will have you’ he said self ashore of himself. He asked me to remove my tee shirt so I took it off exposing my shaved bare chest. He cupped my breasts, and then pinched my nipple softly. ‘I like it that your shaved smooth’ he said returning to cupping my breasts. ‘Is your entire body shaved?’ he asked rubbing his crotch.
‘Yes sir would you like to see?’ I ask playfully. He stood and paused for a moment.
‘No. do you do make up and are you passable as a woman when all dressed?’ he asked pulling on my nipples so they would stick further out.
‘Yes, I wear makeup and I am passable’ I told him.
‘I will be in touch’ he said and let me dress then showed me out of his room.
Although the walk home would be very long I decided to walk just to take off the horny feeling I had. I arrived home and found a email waiting for me. ‘I will have you next week here is a list of what to bring — wig, makeup, stilettos, bustier (red if possible) a tight dress to show off your curves (red, black or white with matching stocking) Butt plugs and lots of lube. Anything more is up to you and I hope there is lots more’ Lucky for me I had everything plus some.
I waited at the bus stop as ordered with suitcase in hand full of my clothing. He drove up and I got into the car. ‘Once you get dressed I want you to be all fem OK?’ he asked and I agreed. We drove for a long time ten hours arriving in some small mining town. He had rented a house on the main street. He opened the door to the place and told me to go to a bedroom and change. ‘From here on in your be a women’ I changed quickly applying my makeup and put on my wig. I wore my tight white dress so he could see my red bustier thru it. I wanted to drop to my knees and suck his cock to the end but fought off the feeling. The red stockings ended in my red stiletto and you could see my red thong thru the dress if you looked hard enough. I walked down the stairs to find him naked waiting on a chair in front of a opened window. He sat there stroking his hard cock.
‘Come and mount me’ he said and without any thought I was sliding his hard cock deep inside my ass as we kissed and he moaned at the same time. My feet were able to touch the floor as I slid up and down on his perfect shaft with my thong pulled to one side. He lifted my dress in the back and held on tight to my ass as he pushed upward to make his hard cock go deeper into my ass. After only a few minute he exploded deep inside me making me moan loudly. We could see people outside trying to look in to see us fuck. He had me dismount and lick and suck his cock clean. Something I believe a good slut should do. He then had me undress in front of the window giving the public a good show. I was stopped after I removed my dress then he scooped me up and carried me up to the bedroom. He laid me on the bed, his cock still hard then pulled the top of the bustier down exposing my nipples. He tugged on them and played with them making them erect. He then removed my thong and grasped my balls and gently played with them in his hands. I became hard as he rolled me over on to my front and he pushed his once again hard cock back into my willing ass. I raised my ass up for easy access for him and he grabbed my hips and began fucking my ass all over again. With each of his thrusts I let out a yelp of ecstasy.
‘Oh yes fuck me’ I said out loud. ‘Oh fuck deeper baby deeper’ I cried out and he pushed his cock harder and deeper into me. What I was saying had a effect on him. Soon he stopped and turned me over taking one of my legs over his shoulder and the other leg pushed to the side. His cock slid into my ass without any problem and he began fucking my ass all over. I now wanted to taste his cum, to feel his cum all over me the more he fucked me the more I wanted his cum.
‘You’re a good fuck’ he said
‘I want your cum, please fill me full of your cum’ I begged. He reached down and started to play with my nipples, pulling on them hard and making them stick further out than they ever have before.
‘Come on baby, take my cock. That’s what sluts want isn’t it?’ he said loudly
‘Yes’ I cried out ‘I want your cock, fuck me hard show me how hard you can fuck me’ I said. Then he pulled out of my ass and crawled on top of me making me take his cock in my mouth as he emptied his ball into my willing mouth. After he was done he rolled off me and lied on the bed spent.
‘I was so fucking horny’ he said sitting up on his elbows as I fondled his cock. ‘I bought you something’ he said moving off the bed he opened his dresser and pulled out a shelf bra. ‘Take off the bustier and wear this and the thong under the dress. I did as asked and when I put the bra on it pulled my breasts together and my nipples stuck out over the top of the bra. You could see my tits thru the dress and my nicely shaped ass was held tight by the dress as well. I was wearing a white dress and red underwear with a garter to hold up my stocking.
We went out. It was the first time I had ever been out in public in over ten years. The town looked like it was stuck in the early 1900’s. We went to a small restaurant and sat down for coffee and a bite to eat. The first thing I noticed was I didn’t see any women. The waiter kept looking at me filling my cup of coffee every two second.
‘What do you think?’ my friend asks the waiter. The waiter looks at me even looking under the table.
‘I know a ton of guys who would do her all night’ he said and I looked at my friend and smiled. My friend nodded his head towards the waiter’s crotch. I could see he had a large cock himself as it was rock hard by now.
‘Why don’t you come by the house and take her for a test drive yourself’ he said the waiter just looked at him.
‘I doubt she will make it back without being fucked’ he said filling my cup again. I looked around and saw six men in the place eating breakfast. We finished and got up to leave when the table by the door stood up blocking our way out.
‘Oh did I mention that this is all male mining town and they haven’t see a slut for years?’ my friend says to me with a large smile on his face. I walked toward the men by the door and stood face to his chest. I raised my hands and put them on his large chest as he looked down at my face.
‘Excuse me’ I said in my best female voice. He moved to one side and I started to walk out when another man grabbed my arm.
‘You have to pay to leave’ he said holding my arm tight. I reached down with my free arm and grabbed his crotch.
‘And how big is the toll?’ I asked. He reached for my nipples thru the dress and gave them a good twist.
‘How much can you pay?’ he said
‘Well by the feel of things, the toll is quite small”

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A one week fling, 9.0 out of 10 based on 4 ratings

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