The summer of my junior year in college I was offered an internship at a Fortune 500 company in Chicago. My girlfriend was from Chicago and was planning on working there for her summer internship as well so we were both very excited about being able to spend the summer together. Although I had developed a really good relationship with her mom and dad, we both were very shocked when her mom made an offer of her own for me to stay with them for free during the summer. My girlfriend jokingly told me that her mom must be up to something because she thought her mom had a crush on me and sometimes talked and acted as if I were her own boyfriend. Her mom had even bought me a pair of boxers once. However it never bothered my girlfriend because she was the only daughter and she and her mom were best friends and shared everything. They even looked alike. Her mom was beautiful - 5-7, 125 lbs and in amazing shape. And to top it off she was a pro at flirting and playing mind games. When I would mention something to her about my girlfriend that I liked she would be quick to reply “where do you think she got it from?”. She was a corporate woman, very observant and intelligent, very tough and a serious control freak. In fact, my girlfriend told me that the key to securing her parents blessing for marriage was to win her mom over and make her happy because her dad pretty much did what her mom said. So I worked very hard to do just that and was so far succeeding, even though it was hard to do at times because her mom was very arrogant and could be very selfish and downright mean at times. Therefore, I accepted her mom’s offer to stay with them to not only save money and be closer to my girlfriend but to also not offend her mom as well and stay in her good graces.
After the first week of staying at my girlfriend’s parent’s house, her parents took us out to dinner. My girlfriend’s oldest brother and his wife joined us as well. We went to a really expensive seafood restaurant and her mom paid for everything. As she paid the bill she leaned over to me and whispered “you do know that nothing in life is free, right?” and winked her eye. Then she said “just kidding” and winked her eye at me again. As I said earlier, my girlfriend’s mom was a pro at playing mind games so I didn’t know how to take this. However, I just remembered what my wife said about keeping her mom happy so I figured I’d play it safe by simply smiling.
It was really late when we left the restaurant and after we got into my girlfriend’s dad car we found that it wouldn’t start. He drove a 1994 Hyundai and had been experiencing problems with it. After getting humiliated by his wife for not buying a new car, he suggested that we ride back home with my girlfriend’s brother and his wife because he was going to call and have the car towed. I asked him if he wanted me to stay with him but he said no and then whispered to me “I’m going to have a friend pick me up so we can go and play poker”. My girlfriend’s brother said he would be happy to take us home but said that someone would have to sit on the floor because there was a box in the backseat that was taking up space where a third person would sit. So my girlfriend’s mother immediately said that I would be sitting on the floor and that they would put the box on the seat between them. Of course I agreed and we piled into the car.
I sat on the floor with my back to the door on the side where my girlfriend’s mom sat and my legs were on my girlfriend’s side. I would have to stay in this position for about an hour as we were that far away from the house. We were not in the city so the initial ride back was dark, with occasional lights from passing cars and streetlights. This was especially the case since my girlfriend’s brother had decided to take a less traveled way back home. It was late so after a few minutes of small talk everyone except my girlfriend’s brother of course started resting their heads to sleep. My girlfriend playfully kicked me and I jumped. Her mother asked what had happened when she felt me jump and when my girlfriend told her what she did her mother replied “he probably liked it.” And my girlfriend, unbeknownst to how cunning her mother was, replied “oh he definitely does”. I couldn’t clearly see her mom’s face because it was dark at that moment but I swear I could see a sinister grin on her face. About 15 minutes after that everything was totally quiet except for the radio playing smooth jazz. And that is when it started…..
My girlfriend’s mom had been shifting her legs occasionally to better position herself for more comfort and apparently found the ultimate comfort position by placing her left foot on my left thigh and her right foot squarely on my crotch. She was wearing black leather pointy-toed stilettos and until then had both feet on the floor by my left thigh. I had been dozing up to this point but was now fully awake. I looked at her to try to see if she was awake but she appeared to be asleep. I had nowhere to move because I was sitting on the floor and I dared not move her mom’s feet so I sat there and took it. Needless to say I became erect and felt like I was about to burst out of my pants! My cock was burning and throbbing from the pressure of her foot and feeling like it was about to explode out of my pants. Her mom continued to shift her feet occasionally, each time grinding my cock into my pants. She was totally comfortable and either she knew what she was doing and simply didn’t care or she was totally asleep and I didn’t exist to her. Then, as if she wasn’t comfortable enough, she removed her left foot off of my thigh and crossed her leg, causing even more pressure to be applied to my crushed cock with her right foot. Now her left foot was resting against my chest and her right foot was squarely resting on my cock as she shifted her body to the right. She wore a size 9 shoe and the left one was now resting on my chest inches away from my chin. They were apparently shoes that had been worn numerous times because I could smell the sweat and leather. She stayed in this position for several minutes and then she uncrossed her leg and returned both of her feet to her original position next to my left thigh and off of me. By this time I was very close to climaxing so it was a good thing she did or I would have blown my load in my pants. However, apparently she returned to that position to take off her shoes because after she had slipped them off she put both stocking feet on my crotch. I could really smell the sweat and leather resonating up from the shoes now as they rested next to my thigh. Her feet were very warm from having been sweating in the leather pointy closed-toe shoes and she continued to shift her feet, this time occasionally rubbing them slowly back and forth and in a rhythmic, up and down pressing motion. Eventually I couldn’t hold out any longer and I blew my load in my pants. I just knew she was going to call attention to it any minute now as I was certain the bottom of her stocking feet were wet but she never did. She continued to occasionally shift her feet slowly back and forth and up and down. About five minutes from the house my girlfriend’s brother announced to everyone that we were almost home and she removed her feet from my crotch while stretching and slipped her shoes back on. I pretended to be in a deep coma-like sleep. Minutes later we pulled into the driveway and she firmly kicked my thigh and asked me “are you ok down there?”. I replied “yes ma’am” and gave a fake stretch. I pulled my shirt out of my pants before getting out of the car to hide my still erect cock and wet crotch area on my pants and walked into the house behind my girlfriend, who was still half asleep, and her mother. After my girlfriend went to bed and I went to my room, her mother walked into my room while I was lying down and said “I’ll bet that bed feels a lot better than the car floor huh?”. I replied “it sure does”. My girlfriend’s mom then moved closer and responded “oh I’ll bet it wasn’t that bad” and smiled at me. I replied “oh yes it was indeed very uncomfortable” and my girlfriend’s mom simply responded “oh I know for sure it wasn’t that uncomfortable for you”. And with that she winked at me and walked out of the room. That was 17 years ago and to this day she still has never admitted whether or not she did it on purpose. However, she has done several things since then that lets me know without a doubt that she did do it on purpose, including several similar events througout that summer. As she said, nothing in life was free and I paid for everything I received that summer. But those will be told in other stories.
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