This happened 40 years ago, and it’s not as hot as it is a life memory. I was 19 and home from college over Christmas. I met high school buds for a beer at a local inn in my very small home town. While there, two older women came in and I recognized them (small town) as the divorcee of my summer job boss and the divorced town manager (like a mayor). She was 38, and my dad’s boss with whom he worked with in the town offices.. We all had a few beers and both of the women were flirting with me quite openly. My buddies were taking note and encouraging me to take it to a higher level. I was kinda shy then and they knew it, and were playing it up. As the evening progressed and the two ladies were getting a bit soused, we realized that it had begun to snow and was really coming down hard and thick. The other divorcee said she had to go before it got worse and she asked if I could bring her friend, the town manager, home, as she lived on a steep hill and she didn’t feel confident taking on that challenge. I of course, in my young male bravado said that I would have no problem tackling the hill, so off we went. S. was getting very touchy-feely in the car, and I was totally hard, and she could feel it as she would slip her hand over the bulge in my pants. I managed to get to the entrance to her long drive without much trouble, but her driveway went steeply downhill and was unplowed. I hesitated, considering the risks of not getting back up, when she full on attacked me, telling me how she wanted me to fuck her all night long. She pulled out my cock, stroking it and kissing me passionately…talk about older women fantasies!!…My dad’s car had a bench seat and she lay back and hitched up her skirt. I was not a virgin, but no woman had ever so openly invited me to fuck her. She was wearing panty hose and lace panties. Man was I ready to go! she had difficulty pulling her panty hose down, so she just asked me to rip them open….as well as her panties…there hardly any foreplay. She stopped me from eating her out, demanding that I just fuck her!…I managed to drop trou and get her feet up with my hands and shoved my raging cock into her pussy. She was so wet and ready and she came almost immediately…shuddering. It put me over the edge and I came deep inside her…she moaned and said something about my wonderful cock. It was over way too soon, and I felt like I didn’t give her nearly what she was looking for. She showed no signs of covering up or getting ready for a trek down her driveway, so I decided to drive down to the house and carry her inside. HA! That’s when things got interesting! When we got to the house, she couldn’t find her KEYS! As she stayed in the car, i walked around the house trying different doors and windows…finally founding a bathroom window cracked open enough for my fingers to lift…and hoisted myself up and in, only to find a very angry dog wondering who the fuck I was. I managed to calm him down, and unlocked the front door. She was nearly asleep and was heavier than I imagined. As I lay her on her bed, she tried her best to convince me to stay and fuck some more. It was 1 AM, and I had my dad’s car…he had to be at work the next morning. I tucked her in and kissed her on the forehead and made my way back outside, locking her front door behind me. Damned if I could get that car up her drive without spinning the tires in the deep snow. I eventually gave up, and broke into her house ONCE AGAIN to telephone my folks, waking them of course, with all that entailed. (no cell phones) I managed to tell them that I had done a good deed by driving my dad’s boss home, but got stuck in the driveway. I made an agreement with my mom to meet me in the town center, and I would walk down the hill. It was a glorious quiet night, not a sound, as I ran down the hill on a post sex high, incredulous that I had fucked my dad’s boss. The next day we retrieved the car and she and I exchanged furtive smiles and winks. We never repeated the sex, but it has burned an everlasting secret memory in my brain….until now!
Source: reddit.com/r/gonewildstories/comments/7tx8w5/im_fucked_my_dads_bossf
Long time coming! This must have kept you going many times over the years. Too bad you couldn’t go back for an encore.