Cross Dressing Fun In My Hotel Room [M]

Before I start the story a little background information. Due to the virus I’ve been staying in a hotel near my work as I am possibly in contact with it on a daily basis and don’t want to give it to my family, this meant I had a whole room to myself and a some free time… recently I’ve been thinking about cross dressing, well as a teen I actually did for a little bit stoped as I didn’t want to get caught so now may be the perfect time… I do look very feminine and all it take is a wig and a small amount of make up to make me convincible…

So as I was walking home from work I passed by some shops and just went for it… my hart was racing so fast and I walked into the store, it was near closing so was pretty much empty. I went straight to the underwear section and picked out a matching set of bright blue panties and bra along with them I picked up some thick black nylon tights. Next was a dress, the section available to me was a lot and probably spent a little to long deciding. I ended up with a tight red dress with black details on the bottom and top. Now finally for some high heels and I knew I was going for some red stilettos to match the dress. The pair that grabbed my attention where the peep toe red stilettos with a nice strap on them… I went straight to the self checkout as quickly as I could and payed for the items.

As I continue my walk home I passed by and adult toy store and curiosity got the better of me. As I walked in I could see the aisles of toys available and was almost turned away but continue in… walking around the available toys I asked myself do I want to try anal or just get something for my cock? As I was looking at the different vibrations I heard a innocent sounding voice.

“Look for a toy for your girl friend?” The voice asked.

Looking round it was a shop assistant and she made me jump a little.

“No myself.” I say almost with out thinking.

“Ow if you don’t mind how will you use the toy?” She asked trying to get an understanding of what I may want.

“Probably on my cock not in my ass.” I reply not realising how open I sounded.

“Well I recommend this.” She said reaching up to a U shaped remote vibrator.

“It’s popular with out guys and what you do is put it in your cock with the elastic band.” She explained to me.

I agreed to to take this toy along with a blond wig and quickly when back to my room. I stripped naked with my new clothes on the bed. I was already clean shaved as I hate body hair. I put the blond wig on and was think about the vibe, picking it up o put it on my cock as the lady explained. Holding the remote in my hand I turn it on by accident, it was strong and made my cock hard quickly, I switched it off and place the remote on the side near the door. Sitting on the bed the pantyhose’s where next and as I slipped my foot into them I felt a rush though my body, my cock was hard but held in place by the panties, as the nylon rubbed my legs going up I fell back on the bed thinking I was going to cum just at the feeling but I didn’t. Next was the dress and it was super easy to get into and I caught myself in the mirror. I looked very good. Finally as I slipped into the heels, doing the buckle up, I heard the door open.

“Room service you order towels?” A female voice explained.

“Yeah just leave them on the side.” I replied in a feminine voice.

She must have released I was wearing a vibe as the looked at me holding the remote… She switched it on and turned it up high, I didn’t release the toy could go so high and on my sensitive stop it was going to make me cum quick…

“Enjoy.” She said as she lightly tossed the remote across the room before leaving.

Trying to walk in the heels was hard but now the the vibe on it was even harder, I stumbled towards the remote feeling the orgasm get close and closer, the closer I got to the orgasm the harder it is to walk… I reach the toy and switched it off, sitting on the chair I relaxed but really enjoyed the challenge so… I got back up nod switched the toy back on and tossed it across the room again… as I began to walk I know I’d very make it and as I got to the edge of the bed I came in my panties… this was a strong orgasm and I felt pump after pump being shot into my panties… I fell on to the bed and had to crawl to you remote, I finally switched it off and decided to just fall on the bed… it wasn’t long before I feel asleep still wearing the clothes…………

Source: reddit.com/r/eroticliterature/comments/ibaknk/cross_dressing_fun_in_my_hotel_room_m