This is a true story. I changed the names of all and many details to further disguise the identities of those in this story. The dialogues are to the best of my memory. It has been more than 45 years since this happened so I hope you will cut me some slack.
To recap: For several months I had been serving as the bull to a hot wife/cuckold couple. The cuckold was my boss Derek, his hot wife was Janet. Our practice, initially, was that I would fuck her Friday nights after their monthly cookouts in their marital bed while Derek slept in a guest bedroom at the other end of the second story hallway. As our affair progressed I started seeing Janet more often.
Janet: mid-30s, 5′ 6″, brown eyes, maybe 130 lbs, short light brown hair dyed blonde. Janet had an athletic build.
Derek: mid-30s, about 150 lbs, 5′ 8″, blue eyes with blonde wavy hair.
I was 25 years old, 5′ 11″, 235 lbs. blue eyes, brown hair. I was working in Derek’s office, assigned for one year.
In early November Janet and I went on our first date. Janet had on a low cut black dress and high heels. She had on red lipstick as she knew that was a turn on for me. She let me in and gave me a big wet kiss in front of Derek. As usual.
I moved a hand up to cover a breast, making sure Derek could see me doing it. Janet told me she was very excited as she hadn’t been out on a date for several years. (They had been married for about 10 years so…) She grabbed her coat, I helped her put it on and kissed her neck. She gave a “Mmm” and we left. No goodbyes to Derek.
The restaurant was situated on the bank of a river. It was multi-storied with floor to ceiling glass windows overlooking the water and a few boats were out there at anchor. We sat in the corner of the upper-most dining area in a booth that somewhat shielded us from the view of most of the other dinners. As we ate and chatted we also kissed and touched from time to time. At one point I had a hand up her dress and was stroking her pussy. She was kissing me and telling my how good it felt.
Janet was in a very good mood. She and her sister had landed a very big account that week and she ordered some expensive champagne to help us celebrate. She was happy and tipsy by the time we left. It was dark as I drove back, Janet was sitting next to me with her head on my shoulder and a hand stroking my hard cock.
When I pulled into their driveway we made out for a while. I pulled off her black panties and put them in my coat pocket. I wanted to give them to Derek as a present and memento of out first date. I then fingered Janet to her first orgasm as we kissed.
We got to their home and went to the master bedroom to change. Janet put on a bed shirt that went to mid-thighs. I had on a long sleeve T-shirt and a pair of gym shirts. We went downstairs and found Derek pretty sloshed in his chair, bleary eyed and looking morose. His eyes were red. I figured he was drinking and crying while we were out together. I gave those black panties to him and told him I took them off of Janet while we were in the driveway a few minutes ago.
Janet and I sat on the sofa and sort of watched TV. I write ‘sort of’ as we were snuggled under a blanket and were touching and teasing each other. She pulled off my gym shorts almost immediately and began to play with my cock. I had her bed shirt pulled up to her waist and was teasing her pussy. We kissed and talked in front of Derek as he played with his little cock.
At one point Janet slid under the blanket to suck my cock. She took her time, savoring my cock. Every once and while Derek would look over at us and I would see his chin quivering. I knew he was upset. I loved it. After about 15 minutes I grabbed her hair and pulled her up to kiss. I told her it was time to go to bed.
We helped Derek up the stairs and into his guest bedroom bed. We took off his clothes and turned out the bedroom lights, closing the door behind us.
Janet and I did not fuck; we made love. We took our time and teased and aroused each other for half an hour. We talked to each other and told each other how much we wanted each other. As we usually did, Janet ended up riding me as I tortured her nipples. She was almost in tears when she screamed “Yes yes yes” and began coming. That triggered me and I flooded her pussy with my cum.
She fell on me and we kissed for minutes. She rolled off and started touching my entire body. She said she was so lucky Derek had brought me to her. I told her I was just as lucky, I never would have thought a woman like her would have been interested in me. We turned out the lights and fell asleep in each other’s arms. The house was dark and quiet.
I woke up around two o’clock to the sound of voices. The room was dark but there was light in the hallway. I got up and looked out the door. The light was coming from the Derek’s guest bedroom. The voices were coming from there as well. It was Janet talking mostly but with an occasional word or two from Derek.
I walked as quietly as possible down the hall. I peeked in. Janet was riding Derek’s face. Her right hand was on the head board, her left hand was squeezing her left boob. Her eyes were closed and her head was down. I heard her say “Do you like that? Do you like his cum? Lick it Derry, lick me”. She rode slowly moving her pussy across Derek’s mouth ensuring she got his mouth and tongue from her pussy hole to her clit.
I heard slurping sounds from Derek’s licking and sucking. He would some times say “Yes” or just give an “Um”. He was just barely able to reach his little cock and was stroking it. I could smell Janet’s sex scent.
I was dumb founded. I was frozen in place. I was also hard as a rock. I started jacking off slowly transfixed by the show. I loved seeing her on top of him forcing him to clean her cunt of my cum. I loved how she dominated him; that made her so sexy to me. I wanted to fuck Janet, take her, make her mine, make her give herself to me.
I watched for minutes as Janet got more and more aroused. She told him I made her cum so hard, how she liked being seen with me, how I was so strong. He was moaning as he jacked off faster and faster. Suddenly he erupted, his cum shooting up a few inches and he groaned. Janet sped up her riding and then she let go with an “Oh yes” while her entire flushed body shook.
I almost came but held off. I wanted her to take my cum. I turned and crept back to our bed. I listened carefully and in a few minutes I heard head Janet close the guest bedroom door. When she came to our bed I was ready to explode. I asked her where she had been. Janet said she went down to check on Derry.
I rolled to her and put one of her hands on my dick. We started kissing as she stroked my cock. I had her get on all fours. I moved behind her and started fucking her hard – I slapped her tits, pinched her nipple and pulled her hair. She moaned and said “Um”. I fucked her as hard as I could, thinking of her riding Derek’s face. I wanted to make this married woman mine.
I felt my orgasm building and gave Janet one final thrust and held my cock inside her. I told her to take my cum and started shooting in her pussy. She screamed my name and began to shake. I pulled her hair hard. I held her there for a while and then relaxed and leaned down on top of her. I began to lightly massage her boobs and kiss her neck.
Janet said “Wow. What got into you”? I just said “I thought you were so sexy tonight”. I pulled out of her and moved beside her on the bed. She put an arm over my chest and kissed me. She said we needed to get some sleep. Just before we dozed off Janet thanked me for being a great date.
Source: reddit.com/r/sexystories/comments/rmesjz/my_boss_was_a_cuckold_first_date_sneaky_snack