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Crossdressing Journey: Tentative Steps - The Next Day

"Finally, the follow up to my encounter with a new friend in a hotel"

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Author's Notes

"The next morning I didn’t have time for breakfast"

The next morning I woke with a pleasing memory of the previous evening. The thoughts of being played with whilst dressed as a girl were amazing and now a new day had dawned with the promise of more adventure.

I got up and showered and douched in case things advanced this evening. I hadn’t heard from him yet, but I thought I’d go to breakfast in nylons and another skimpy pair of panties under my male clothes. Just as I was slipping on my trousers, my room phone rang. I got excited and ran to it to hear my friend on the line asking if he could come to my room, ‘Of course!’, I blurted down the phone. There was just enough time remove my trousers and to slip on a bra and my stiletto heels before there was a knock at the door.

Again, I cautiously strutted over to the door to let my lover in. He came in and had a look of happy surprise when he saw how I was dressed. I realised that he may be short on time before starting his day, so quickly kissed him on the lips then dropped to my knees, undid his belt and zip and dropped his trousers and pants to his knees. This was all the breakfast I needed and I wanted it quickly. I gently rubbed his semi rigid cock with one hand whilst massaging his balls with the other, I then leant in and licked his shaft before engulfing his bell end with my warm mouth. I flicked my tongue around his foreskin and pulled it back with my hand whilst probing the slit in his cock with my tongue. The groans from him indicated I was on the right track, so I committed to my mission to bring him to completion. He put his hands on my head to face fuck me and as he thrust into my mouth and I could hear his breathing getting heavier and more urgent. I was desperate for his cum and knew he was almost there, so briefly broke my mouth away from his cock to ask him to cum on my face. He nodded agreement and I went back to sucking his lovely cock and teasing his balls.

After a few more minutes, he said he was ready to cum, so I withdrew his shaft from my mouth and continued to wank him right in front of my face. He groaned and shouted, ‘Take my cum!’ And then shot five spurts of it on my face, neck and hair. I put my mouth around his cock again to clean up every last drop, then scooped up some cum and swallowed it before rising to my feet to French kiss him.

I would have been happy if he’d wanted to leave straight away, but he guided me over to the bed, kissed me and sat me down, then knelt down and tugged my hard cock from inside my lacey briefs and proceeded to suck it like a man demented. He only broke away to lick my balls, at the same time slipping a finger into my anus. This was electric and I could feel myself at the point of no return and warned him I was about to cum. He just continued to suck my cock and probe my tight hole until the inevitable happened and I flooded his mouth with my cum. He swallowed some, then kissed me to slip some of my cum into my mouth.

Wow, what a great start to the day. I was going to need to shower again to get the cum out of my hair! As he left, we arranged to meet in the evening and he reminded that whatever outfit I was wearing, the skirt or dress must be short and I had to wear the over the knee boots he’d seen lying on the floor of my room the night before. I was more than happy to oblige. We kissed and he departed as I went into the bathroom knowing that we were meeting at 6:30pm later that evening for further fun. It would be difficult to concentrate at work all day.

I will post further that shortly. Thank you for reading xx

Published 
Written by Crossdresserfan

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