Landlady

When I was at University, I became good friends with Jeff, who was a year ahead of me. He had a well-paying summer job that was about to end when he graduated. However, he managed to get me hired there, and since he was moving out to start his career, I was able to pay rent to his mom and simply moved into his bedroom. I visited there over Spring Break to interview, got the job, and agreed to pay $25 a week for rent. Initially it was for room only, and I would have to buy and prepare my own meals, but within a few days his mom told me she could cook for two as easily as one. I offered to pay something toward the food bill, but she was happy to delay living alone, even if only for the summer.

I wasn’t a wine drinker, but she was, and most nights after dinner she would pour me a glass or two, and we would watch television or sometimes play board games. Her name was Sandi, and she insisted that I call her that. She was probably mid 40s, short, but kept herself in shape. She wasn’t unattractive, nor was she beautiful. We quickly struck up a friendship that was interrupted on the weekends.

She had a boyfriend who lived about an hour away, and he would usually drive there Saturday and spend the night. She made me promise not to tell her son that he was sleeping there. The first night he stayed there, they went out to dinner, and later I could hear the bed squeaking and the sounds they made having sex. It got me going and I masturbated listening to them.

She admitted to me, after a few glasses of wine, that she really didn’t like him all that much, but she enjoyed having him there Saturday nights. I assumed she meant the sex, and later found out that I was right.

Our relationship changed one night while playing a board game, called Sorry. I told her how we had played it as a drinking game in college, where you had to take a drink if you couldn’t move a piece during your turn, and if you got sent back to the beginning you had to remove an article of clothing. There were other rules, but those were the two main ones. The next time she couldn’t move, she said, “I have to take a drink now, right?†She did, and each time it happened again, one of us would take a drink.

I was the first to be sent back to the beginning, and removed a sock. I was only wearing a tee shirt, gym shorts, and socks, so my magic number was four. She was wearing a shirt, bra, shorts, panties, socks, and sneakers for a total of eight.

The game ended with my socks off, and she had removed her sneakers and one sock. Without asking, I set up the board to play again, curious how far this would go. I quickly lost my shirt, but she had quite a few “take a drink†moves and when I send her back she started to remove the remaining sock, but I invented a new rule that said if a person was down to the last article of clothing, they could specify what came off anyone who had to remove something. She was skeptical, but I assured her that it was a rule, and managed to somehow convince her. I told her to remove her shorts.

The mood in the room was very different now. She removed her shorts, and quickly sat down at the table. I could not see anything under the table top, but had a quick view of white panties with a bit of dark hair extending out onto her thighs.

I sent her back again, and immediately said, “Panties!†She protested some, and we compromised. She had to remove two articles if I she wouldn’t follow the rules. Her top and bra came off. Her breasts were small, but kinda saggy, not that I was about to complain. Now it was crunch time. By now we had both consumed a lot of wine, and I was fairly drunk. She was smaller than I and was also pretty drunk.

The game ended without anyone being sent back to start. I was ready to play one more, but she did not want to. Somehow, in my drunken state, I suggested that we turn out the lights, and both remove the last article of clothing. She agreed, and the lights were turned off. There was a little bit of light from outside, so each of us could get a vague view of the other. While I picked up the game, she took the wine bottle and empty glasses out to the kitchen, and when she opened the refrigerator door to put away the wine, I got a great view of her naked body.

I was drunk enough to take a chance, and with our clothes gathered in our arms, we walked to the bedrooms. Outside her door she turned and said, “Good nightâ€, went inside, and closed the door. I dropped my clothes on the bed, and went out and knocked on her door. She took a moment to answer it, and when it opened she was wearing a short nightie. I was still naked, and could see the outline of her body because the bed stand light was right behind her. She was looking at my erection, and reached out and put her hand around it. At that point what was about the happen was a done deal.

She walked around her bed, shut off her light, and removed her nightie. I moved onto the bed, on my back, and she joined me there. We kissed briefly, and I moved my mouth down to her nipples and began to lick them. She started whimpering, and when I moved a hand down her belly she opened her legs for me. I fingered her, and then moved on top of her. I was inside her right way, and her whimpering increased, in volume and intensity. After it was over I got up to go back to my room, but she asked me to stay.

She woke me up twice during the night and I serviced her each time. In the morning I had to go to work, and she had coffee made for me after I showered and dressed. That night we played Sorry again, but this time each of us only had on a tee shirt and shorts, and the game was a quick one. I slept in her bed the rest of the summer.

She called the boyfriend and told him that she was going out with friends Saturday night and cancelled his visit. The next weekend she did it again, and he never called back. We fucked almost every night for the rest of the summer, except for the weekend that Jeff came back home. I slept on the couch both nights. Each morning when he took a shower we had a quick fuck in her bed. As soon as he left Sunday afternoon we were in bed again.

As the summer was coming to a close, and I was preparing to go back to university, the end was looming over us. Sex became more frequent. The day started that way, she’d drag me to her bed as soon as I got home from work, and we’d do again at least twice after going to bed. I left on a Sunday, and she was in tears while I was packing my stuff.

We would talk on the phone a couple times a week. I was about four hours away, and she came to visit over a long weekend, when my room mates were both gone. Lots of sex, and more tears when she had to go. I phoned her on a Saturday night and learned that the boyfriend was coming back again for his Saturday carnal visit. That ended things, but not on a bad note.

I saw her one more time, at Jeff’s wedding. We danced a couple of slow dances, and went to her hotel room after the reception was over. The sex was good, and there were no tears when I left her in the morning.

Still a fond memory.