I recently ran across an old picture of a young woman, Lisa, which I spent a night with during a particularly boring work excursion. This was back in the mid to late 80s, when I traveled quite a bit for work. I would try to get with as many women as possible and, if possible, take a photograph as a trophy; most were clothed and done with a Polaroid or a 110 camera that I always carried with me on these trips. She was a very pretty brunette, with lovely green eyes and while not a smoking body, it was sweet with small firm boobs and great legs. She had lovely lips painted with a pale shade of pink lipstick. At the time I was in my mid-30s, single, and in pretty good shape at 6'3" and 195 lbs.
Back then, my hotels of choice were Hiltons or Marriott's; however, this time I was in a low budget place in Northern Maine, which thankfully, had a restaurant and a bar. The place was an inn that had originally been an old farmhouse. Over the years, it had been added onto, tacking on wings for more rooms. It was clean but dated, very dated; the decor was an attempt to look like it was from the 1930s, trying to have a charming colonial feel, but failing miserably.
After finishing with my customers for the day, I went back to the inn. I stopped by my room to change. The walls had really bad brown paneling with old red carpeting on the floor. I changed and headed to the restaurant for dinner. The restaurant was down a hallway past the front desk. On the left of the hallway was the entrance to the restaurant while on the right the door to the bar. As I entered the restaurant there was a large stone fireplace that was burning. I remember it giving off more smoke than heat. I had a leisurely dinner and a couple of beers. After finishing dinner, I paid my tab and left the restaurant. Not ready to go back to my room and the poor reception on the TV, I walked across the hall to the bar. It was no different than the rest of the hotel, dated but not colonial, but still dated. The bar was broken into two parts, an upper and lower section. As you walked in, you were on the upper portion in a sitting area with some very used wooden tables and chairs and a worn but not quite threadbare carpet of some indistinguishable dark color. Several stairs led to the lower level, with a large bar and stools on the left side, some high top tables in the middle and booths along the right side of the room. The booths seats were made of black vinyl and torn in places with some poor attempts at repair. Between the seats were Formica covered tables. The combined effect was somewhat depressing.
I took a stool at the bar, ordered a beer and surveyed the room. Quickly, I made eye contact with a young lady; she must have been about 26 or 27, tall and slender with long brown hair and green eyes. She was a very attractive young lady. She was dressed in a nice business suit. The jacket had a large light blue check pattern with a blue skirt that ended just above the knee. Black patent leather high heels, not too high, probably three inches. The skirt had a slit up the side and no nylons with nicely tanned legs. I made a quick mental note; no ring on her finger.
I made my way over to her booth and asked if I could join her. She said sure, "why not" and I slide in next to her. I learned that her name was Lisa. I introduced myself and we exchanged information about one another. She appeared to be the typical young woman new to the business world. She worked as consultant for a software company, company car (Ford Taurus) and enjoying life on the road. She had a boyfriend. She and a married lady co-worker of hers were there on business and had decided to spend the weekend rather than driving 6 hours home and 6 hours back on Sunday.
I bought her another drink and we continue to chat about why we were there, the other patrons in the bar, etc. I leaned in closer, at first telling her how pretty she was, that she was the prettiest girl in the place and she really was. She just smiled and said thank you. I then told what a beautiful and sexy smile she had. At that she beamed. I continued to tell her that I based how sexy a woman was on her smile and her eyes. She was eating this up. Telling her that I preferred a woman with sexy smile to one with big boobs; that the eyes told me more about a woman than her hair or what she wore. I could tell that I had her full attention. I leaned in closer and told her that a sexy smile and eyes like hers made me hard. She smiled and said "Really?" To which I said of course and asked her to check for herself. She declined but I could tell she was thinking about it. Talking low so she had to lean my way, I told her that the emotional connection between two people made sex so much hotter. I bought her another drink. At this point I pulled out a small 110 camera and asked if I could take a picture, that she had model looks. She let me and I snapped off a couple of shots. I continued to talk about how sexy her eyes and smile were. She let out a sound that seemed like a purr and asked if that is what turned me on. I slid closer and pressed my leg next to hers, nursing my drink and telling her to drink up. She did. I leaned even closer, she didn't lean into me, but she didn't pull away either. Reaching out, I let my fingers trace a line over her hand and up her wrist to where her jacket cuff started. I locked eyes with her and smiled and she smiled back. I continued to tease her wrist and fingers with mine, looking at her the whole time. Her friend had apparently hooked up with a guy and left the bar. I ordered another round. I dropped my hand between our legs and touched her knee. Again, she didn't pull away. I let my fingers slide up her thigh, almost tickling her, up to the point where the slit in her skirt ended. She asked me what I was doing. I told her I was just trying to make her feel nice and asked if it was working. She said it felt nice. I continued to trace a line from her knee to that point in her skirt. Up and back. Then I got bolder and slid my hand under the hem of her skirt near where the slit ended.
She told me, "I don't think that is a good idea."
I told her I thought it was a great idea. She giggled at that but didn't stop me and I didn't stop. I ordered her another drink. I now had the fingers of my hand just inside the slit of her skirt, tracing gentle lines with my fingertips, just trying to tickle her skin. I wanted her to feel goose bumps. When I felt that she had relaxed a little more, I move hand to the inside of her thigh. Sliding back and forth, rubbing gently and using my fingertips lightly on the inside of her thigh. Involuntarily, she parted her legs a little. I asked if her if she liked what I was doing.
"Yes," she said, "but you should stop." I didn't and she didn't move my hand or close her knees.
I started to whisper in her ears, telling her that if she went to my room, she would never regret it.
She answered, "I don't think that would be a good idea."
I told her I wore size thirteen shoes and you know what that means. She giggled again but I caught her glancing towards my crotch, seeing if I was telling the truth.
We continued to sit there, me with my hand between her legs. Every time my hand got within a couple inches of her panties, her legs closed a little. I kept my hand on the inside of her thigh, about three quarters of the way up. At this point she probably had had half a dozen drinks and was feeling no pain. Her eyes were showing that she had good buzz on. Boldly, I took her hand and placed it in my crotch and told to feel what she was doing to me. She rubbed for half minute, staring at my crotch, then looked up at me and said, "Did I do that?" and giggled some more.
I stood up and keeping her hand in mine and guided her to her feet. She followed without resisting. I lead her out of the bar and into the hallway, past the desk and towards the stairs. Once we got to the second floor, I turned to her and wrapped my arms around her and kissed, shoving my tongue into her mouth and sliding my hands down to her ass, grabbing her and pulling her into my now very hard cock. She asked me where we were going, I said my room.
"Nooooooo, I can't," she said.
I quieted her by kissing her again. My hands continued to play with her ass, my fingers tracing the crack of her ass. I took her hand and lead her down the hallway to my room.
"Nooooo, I really shouldn't, I have a boyfriend."
I held her by the wrist and walked her to my room.
"I really shouldn't," she protested again.
I pulled her to me again, kissing her on the mouth and the neck. Kissing her neck got her hot, she started to breathe heavy, an almost silent moan escape her lips. I kissed her neck some more and slid my hand up under her jacket and played with her breast over her blouse.
Pulling my key (yes a real) key from my back pocket, I opened the door and pushed her inside. I continued kissing and licking her neck and worked the jacket off her shoulders and tossed it into the room. My hands slid to her chest, again over blouse. I rubbed and squeezed her tits gently, then played with her nipples. It seemed that she had a sheer bra on underneath and I could feel her nipples. I pinched one nipple and a moan escaped her lips. I pinched some more and started to kiss her throat. She was getting hot. I kept kissing her neck and throat and playing with nipples. Her breath was getting quicker. I moved my other hand between her legs, using it to lift her skirt, and then put my hand on her panties. Lisa reached out and pushed my hand away. So I went back to playing with her nipples. She seemed content to let me play with her tits and kiss her. After a few minutes I put my hand under her skirt again, she tried to push my hand away again but I held it firm. After a minute she stopped trying to move it away. Rubbing her pussy through her panties was making her even hornier. I slid my finger under the elastic band of her panties and slid my finger up and down the slit of her pussy; she was wet! Another moan escaped her lips, this one louder than the others.
Then she said, "Please don't, I should stop." But at the same time she pushed her pussy into my fingers.
