Hotel fun
After a long day of meetings and a late dinner I returned to my hotel room. Being away in a strange city was something I didn’t get to do often but it allowed me to escape my routine vanilla life and enjoy an activity that I did not share with my wife or anyone else. I ran a warm bubble bath and opened my suitcase. In it was my large collection of lingerie, stockings, panties, heels and makeup to name just a few things. A few years back I had dressed as my wife’s twin for a halloween costume party and was so convincing that we actually won first prize. The urge to feel truly sexy and feminine had stuck with me ever since. But opportunities to explore my feminine side were few and far between. Now as I lay back in the bubble bath and meticulously shaved my body smooth, I revelled in the feeling once again.
After drying off I slipped into a pair of black lace panties, nylons and a silky camisole and sprawled out on the bed. Bedside me was a tube of lube and a selection of dildos varying in size from slender to very thick and intimidating. I would spend the evening sipping wine, watching porn on my phone and riding each toy until my ass could take no more.
I dimmed the room lights a bit and put on some soft jazz. I mounted the first dildo on the makeup chair and sat down in front of the mirror. It was tear dropped shaped with a narrow neck and a broad base so it popped in easily and stayed firmly in place as I proceeded to apply my makeup and wig. It would take me about 20 minutes to make myself look full presentable. More than enough time to allow my ass muscles to relax and be ready for what was ahead..
With my transformation complete, I slipped on my heels and walked over to the bed and lay back beside my row of dildos. One by one I slowly worked them into my ass, gently rocking back and forth as my opening stretched and relented.
An hour later I felt a satisfying pop as the head of the largest one slid inside me. I rolled onto my back, lifting my legs up over my head so my dripping cock dangled over my face. With one hand wrapped firmly around my shaft and the other plunging the massive dildo into my bowels, I pushed myself towards an intense orgasm.
My cock jerked back and forth as wave after wave of cum poured onto my pretty face and down my neck. I milked every last drop from my balls and then lay back, completely spent, and stared across the room. It was pitch black outside but as I walked over to close the curtains for the evening, I could finally see through the reflexion in the glass. Across the alley no more than 50 yards away and one storey up was a man, standing in his window watching intently with a pair of binoculars. I immediately froze like a deer in the headlights. He had been watching the whole time. My face flushed with embarrassment and my first reaction was to pull the curtains shut. But he did not flinch at being discovered, and in fact as I allowed my eyes to adjust to the darkness I realized he was stroking his cock. Despite the distance I could see that it was massive and fully rigid. Rather than pull away, I pressed against the glass and watched as he masturbated. I arched my back so he could see my smooth round ass, and scooped the drops of cum off my face licking each finger clean. His stroking intensified and without warning a spray of cum shot from his cock and splashed against his window. Then he was gone…
The next morning I awoke and changed from my lingerie back into my work clothes, washing all traces of makeup from my face and resuming my straight persona. But all day I was distracted, thinking about the events of the previous evening and looking forward to tonight. And I was not disappointed. As darkness crept over the city I slipped into a matching set of white lacy lingerie and positioned the coffee table in front of the window, massive dildo in hand. On queue, I saw the curtains in the apartment across the alley open and there stood the man, this time fully naked with his horse cock dangling menacingly between his legs. He watched me as I pressed the dildo suction cup onto the tables hard surface and then ran my tongue up and down the thick shaft taking as much of it into my mouth as I could until I gagged repeatedly. Then I slipped off my panties and positioned myself on top of it rocking back and forth as I methodically stretched my opening again. This time I could see his cock come to life as he began to stroke his manhood. Then with one firm thrust, I moaned and slid down until my ass cheeks touched the surface, the fake cock now deep inside me. I fucked myself for what seemed like a half hour, watching him bring himself to a full furious orgasm and when he was finally done he nodded and pulled the curtain shut, his cum still dripping down the glass.
I extended my stay one more night and spent the day shopping for a tight sexy little dress. That night I made my self up fully, zipped myself into the new outfit and put on my heels. I sat at the makeup table and began applying my lipgloss and mascara. This time I left the curtains closed. But before doing so, I taped a sign to the window - room 413…
I trembled at the thought of where I was headed, but knew it was what I wanted. When I was finally done I stood up and looked in the mirror. The dress and makeup were stunning and my tall slim build made the charade all the more convincing.
Then, before I could have any second thoughts, a knock came to my door…
After drying off I slipped into a pair of black lace panties, nylons and a silky camisole and sprawled out on the bed. Bedside me was a tube of lube and a selection of dildos varying in size from slender to very thick and intimidating. I would spend the evening sipping wine, watching porn on my phone and riding each toy until my ass could take no more.
I dimmed the room lights a bit and put on some soft jazz. I mounted the first dildo on the makeup chair and sat down in front of the mirror. It was tear dropped shaped with a narrow neck and a broad base so it popped in easily and stayed firmly in place as I proceeded to apply my makeup and wig. It would take me about 20 minutes to make myself look full presentable. More than enough time to allow my ass muscles to relax and be ready for what was ahead..
With my transformation complete, I slipped on my heels and walked over to the bed and lay back beside my row of dildos. One by one I slowly worked them into my ass, gently rocking back and forth as my opening stretched and relented.
An hour later I felt a satisfying pop as the head of the largest one slid inside me. I rolled onto my back, lifting my legs up over my head so my dripping cock dangled over my face. With one hand wrapped firmly around my shaft and the other plunging the massive dildo into my bowels, I pushed myself towards an intense orgasm.
My cock jerked back and forth as wave after wave of cum poured onto my pretty face and down my neck. I milked every last drop from my balls and then lay back, completely spent, and stared across the room. It was pitch black outside but as I walked over to close the curtains for the evening, I could finally see through the reflexion in the glass. Across the alley no more than 50 yards away and one storey up was a man, standing in his window watching intently with a pair of binoculars. I immediately froze like a deer in the headlights. He had been watching the whole time. My face flushed with embarrassment and my first reaction was to pull the curtains shut. But he did not flinch at being discovered, and in fact as I allowed my eyes to adjust to the darkness I realized he was stroking his cock. Despite the distance I could see that it was massive and fully rigid. Rather than pull away, I pressed against the glass and watched as he masturbated. I arched my back so he could see my smooth round ass, and scooped the drops of cum off my face licking each finger clean. His stroking intensified and without warning a spray of cum shot from his cock and splashed against his window. Then he was gone…
The next morning I awoke and changed from my lingerie back into my work clothes, washing all traces of makeup from my face and resuming my straight persona. But all day I was distracted, thinking about the events of the previous evening and looking forward to tonight. And I was not disappointed. As darkness crept over the city I slipped into a matching set of white lacy lingerie and positioned the coffee table in front of the window, massive dildo in hand. On queue, I saw the curtains in the apartment across the alley open and there stood the man, this time fully naked with his horse cock dangling menacingly between his legs. He watched me as I pressed the dildo suction cup onto the tables hard surface and then ran my tongue up and down the thick shaft taking as much of it into my mouth as I could until I gagged repeatedly. Then I slipped off my panties and positioned myself on top of it rocking back and forth as I methodically stretched my opening again. This time I could see his cock come to life as he began to stroke his manhood. Then with one firm thrust, I moaned and slid down until my ass cheeks touched the surface, the fake cock now deep inside me. I fucked myself for what seemed like a half hour, watching him bring himself to a full furious orgasm and when he was finally done he nodded and pulled the curtain shut, his cum still dripping down the glass.
I extended my stay one more night and spent the day shopping for a tight sexy little dress. That night I made my self up fully, zipped myself into the new outfit and put on my heels. I sat at the makeup table and began applying my lipgloss and mascara. This time I left the curtains closed. But before doing so, I taped a sign to the window - room 413…
I trembled at the thought of where I was headed, but knew it was what I wanted. When I was finally done I stood up and looked in the mirror. The dress and makeup were stunning and my tall slim build made the charade all the more convincing.
Then, before I could have any second thoughts, a knock came to my door…
8ヶ月前
