The realization of my mistake was two-fold. For one thing, paying the hooker took almost all my actual cash, and secondly I had not fulfilled my promise to Carol to pick up her sister, Karen to have sex with her. I quickly dressed and went back to the bar. It was much busier but I did manage to find Karen dressed in a black blouse and a very short black skirt. She was sitting at the bar talking to another woman. I settled...

I had just retrieved the mail from my mailbox in front of the house when my neighbors came out of their house. I waved in greeting and the husband waved back but his wife walked across their yard towards me so I went to meet her. “Hi, Carol," I said, "what are you guys up to today?”  “We’re on the way to the airport to pick up my sister, Karen. She’s coming to visit for a week or so.” “That’s nice,” I said and she looked...

Just shy of three hours later I pulled into driveway of the large hotel chain and stopped in the valet parking space. I waved off the bellman and opted to carry my own luggage inside and less that fifteen minutes later I was in a luxurious suite. I unpacked my suitcase and hung what clothes needed hanging and then placed my toiletries case in the bathroom. I then set up my laptop and spent the afternoon on Lush and a few...

Monica was casually cleaning herself up, using the towel that the young woman from housekeeping had handed her. As I lay there spent from our activities, my mind was frantically trying to come up with something plausible to tell my wife about how I missed my flight. She would not be pleased.I was looking at the young woman from housekeeping.Without my glasses, I could barely make out her name tag. Bernadette… yes, that’s...

Last summer, when I was 23, I was staying in a hotel by myself for work. I had about a week left in my stay at the hotel and decided that I should take advantage of having a room completely to myself. I had always fantasized about giving head to an older man but had never had a safe place to do it and I was always worried about knowing the person or running into them. This was the perfect opportunity to hook up with a guy...

What had I been thinking? I thought to myself as I pulled up to the hotel. Why had I agreed to meet up with a stranger? Well maybe not technically a stranger, as we have been talking online for a few months. Even though I had been promiscuous in my late teen and early 20’s, that had been many years ago. Yet here I sit outside this hotel, should I drive away…should I stay? Was I really prepared to go through with this? Was...

October 2012. Zipping up the cool leather boots to within an inch of my knee always sent a delicious shiver racing up my spine. It wasn’t just the temperature of the soft material against my bare flesh, it was what it symbolised; what it made me. It made me his. Alone I sat, framed between pillars either side of the headboard that was almost twice the width of the one at home. Green irises stared back from the mirror on t...

After getting off the plane and through the business meetings, he was ready for some alone time at the hotel. He took off his suit, shirt and pants by the closet so all were nicely put up, Scot turned to look at himself in the mirror. He liked to wear women’s panties and brought a few on the trip. To make the boring meetings go faster, he would wear soft, silky panties with little coverage. Scot enjoyed feeling the cool m...

Returning to her hotel room after having a few drinks and dinner with the clients, Holly noticed that the lights were out and it appeared Shannon, her roommate for the trip, was already asleep. She turned on the bathroom light so not to disturb her coworker but also allowing her to see enough to get undressed and into bed. Shannon had returned earlier saying that she needed to get a few things taken care of before the nex...

With the alarm going off, Shannon was already awake and in the shower when Holly awoke. Holly could feel the butterflies returning after having experienced mutual masturbation with what Holly could only surmise as a sleep walk masturbating Shannon. What would Shannon say? What should she say? Maybe Shannon really was asleep and wouldn't even remember what had occurred. Getting out of bed took a bit of work, but she finall...