There was a woman I used to meet semi-regularly for highly scripted sessions that I would dream up. These would always occur in a hotel during travel, sometimes with adjoining rooms with full access during the night, sometimes not so lucky.
This particular time she would already be checked in. I would always dream up some sort of means for her to communicate the room number. Might be a simple piece of wadded up paper with the room number 7 digits higher found under the rear tire of her rental car. Or one lobby had books in it, and I told her to leave a copy of the room key between numbered pages of a certain book. Of course I had a backup to find her if it didn’t work out, but it added to the tension.
On this particular afternoon I told her that I wanted her naked in the bathroom, sitting on the toilet, legs spread slapping her cunt when I walked in. I was specific about leaving the bathroom door slightly ajar so I could peep through the hinge line.
I also told her I wanted to see all her clothes that she was wearing when entered the room in a ball on the floor just outside the bathroom door. I told her to bring her cell phone into the bathroom with her.
In this particular case she was told to keep the lock to the outside door unlocked by putting the don’t disturb sign between the door and the jamb. I found the room number as described earlier on a piece of paper under the wheel of her rental car. I had to drive the lot twice to see it. I subtracted 1 from the first digit as agreed.
The door gave easily when I pushed on it, the card dropping to the floor. I locked it behind me, and secured the chain. It was still afternoon, no lights on but the bathroom light. I could see a pile of womans clothing as instructed wadded up like she had just stepped out of them.
I walked quickly past the slightly open bathroom door, just catching a glimpse of her sitting spread legged on on the toilet, looking down, tits hanging and slapping her open cunt. I couldn’t peep through the hinge line and see her though.
I pulled the spread off the bed, leaving only the white sheet underneath. I quickly took my clothes off, nervous enough that I wasn’t hard yet. I went over and picked up her clothes and smelling them, knew that she had made the flight in them as instructed. A silk pull over top, short sleeved. A bra, simple white panties, a slip, and a skirt.
We had played around with my crossdressing before, and in fact she regularly purchased items she thought I might like when she saw somthing on sale that was my size. I had invested in set of silicone tits, C-Sized that I would wear with the bras she bought, and I had of course brought them along.
This would be the first time I had worn her clothes though. I started with the bra. Her’s was a little tight, and I had to fiddle with it to get things lined up before slipping in the tits. Panties next. I looked closely for any sign of wetness, there was none. As soon as I pulled them over my cock, I got hard. The panties were a full cut, no issues with parking my hard-on and keeping it contained.
The full size hotel mirror was not in the sight line of the bathroom door, so I carried over the top, slip and skirt to watch myself dress in the rest. This was the first time I had ever worn a slip. It was a half slip, simple white, and when I pulled it on, I could no longer see my erection under the simple folds. It felt unbelievable for something so simple. I had worn a garter belt and stockings which provided constant stimulation due to the tightness around the legs, but this was so different.
I actually wondered which was supposed to come next, top or skirt and went this the top. The silk glided down over my head, and immediately took shape over my bra and tits. The skirt, just like the slip was simple to put on. I looked at myself in the mirror, felt my tits through the fabric, felt my cock through the skirt. I was aware that she was still in the bathroom, could hear furtive noises, but she had no idea I was dressing up in her clothes. I had on previous occaisons snuck into her adjoining room right after she arrived and was in the bathroom and “stolen” and dressed in the lingerie she brought for me, but never her clothes.
I went to the bed, propped up my head with several pillows and began to feel myself up, started rubbing myself through the panties, and generally edging. I moaned loud enough for her to hear. I wanted her to know I was starting something without her.
I then used the hotel phone to call her cell phone in the bathroom. She knew it had to be me by the area code, and her voice was already husky, like it got when she was about have something new and edgy happen to her. I pretended I wanted phone sex just like I did if I called her at home when I was on the road and in a hotel somewhere about to masturbate. I could tell she struggling to let me go through the delay of coming out of the bathroom and getting played with. I described being on the bed, my hard cock, asking her if I should just cum. Nothing about her clothes.
Finally I told her she was to close her eyes and crawl out of the bathroom to me. She immediately hung up, and I could hear her transition from the toilet to the floor, and I stood by the end of the bed.
She came out as instructed, tits swaying, eyes closed, feeling her way along the wall. I called to her, and when she was at my feet I told her to start sucking me through my panties. This was not an uncommon request, but only when I was wearing my panties, not hers.
I lifted the skirt and slip up and over her, so all I could see was the back of her legs, and feet sticking out. Her hands went up my legs, then there was a pause when she either smelled herself on the panties, or opened her eyes and realized I had her clothes on. I pulled her face into me through the skirt and told her again to suck me through the panties. She started working on my cock, and I started asking her if she liked my cock up against where her cunt was earlier. If she could taste herself along with my cock weep. She started slipping her tongue under the panties and working my balls with her hands.
I stepped back, pulled the skirt off of her head, and let her see me. For some reason this came off differently than I expected. Even though I was fully clothed, and she fully naked, there was a shift in dominance to her somehow. I actually flushed as she took me in. She said later it felt like a huge invasion of her personal space, despite my having fucked her repeatedly, every way imaginable in the past. I felt some shame, like I had been caught doing something I did not expect to get caught doing.
I dove back in to my role though, told her to get up, moved to the mirror, and had her stand behind me and hug me from behind, grab my tits, reach around and fondle my cock through her skirt. I turned around, hugged from the front, ground my cock into her now wet cunt, telling her I was tagging her clothes with her wetness.
Finally, I led her into the bedroom again. We reguarly played with her pegging me in all sorts of scenarios, and I told her to get the strap on and that she was going to have to fuck herself.
While she was getting the harness sorted out, I saw her clip on earrings and glasses on the bed stand, and I put them on, along with her watch. When she turned around, she looked shocked. I stayed in the role and asked her if she was hard yet, and told her to get the lube, very matter of factly.
I lay down on the corner of the bed, and told her to fuck herself. I didn’t help. She had to raise my skirt, raise my slip, and then tug down my panties. I told her to leave the panties on.
It was really awkward, not at all like when she normally pegged me, telling me what to do, making me the whore. I pulled a pillow under my head and looked up at her, as she almost reluctantly pushed the dildo into my ass. I made a point of trying imitate how she climaxed when I ass fucked her. I let my legs rest on her shoulders at one point, and reached down to spread my ass cheeks like she would do at another. I taunted her asking if she liked fucking herself, asking her what she would be thinking everytime she wore these clothes again in the future.
We had the rest of the day ahead of us, so I didn’t want to cum. I told her to stop, acted like a bitchy woman who didn’t get to climax during a fuck. But I couldn’t undress in front of her oddly enough. I felt too much shame, and slunk into the bathroom, took everything off, and came back out like the entire scene never happened.
Source: reddit.com/r/gonewildstories/comments/52zp3j/wore_her_clothes