[This a repost of a story I put up several months ago. It was removed as Reddit thought is was spam.]
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.
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.
This post is long. The sex stuff starts at ——
Janet and Derek’s September cookout was the last of the year. Janet and I had our usual post cookout night time sex session, morning ritual breakfast and post-breakfast shower and fuck. But before we went downstairs that morning Janet asked if I would like to come to dinner in two weeks. Just Derek, her and I. Dinner and ‘some fun’ later in the evening. That sounded good to me.
That Friday I dressed up and bought some flowers for Janet. Janet answered the door in a pink and white cocktail dress, stockings and high heels. She squealed when she saw the flowers and gave me a big wet kiss in front of Derek. She told me she hadn’t had a man bring her flowers for years as she hugged me. She gave the flowers to Derek and told him to put them in a vase.
At dinner Janet and I sat next to each other like lovers on a date. Derek served us but sat opposite us to eat. As we ate Janet and I talked about what we had done in the last two weeks. We ignored Derek. We would occasionally kiss or touch each other. Derek was grinning watching us and kept asking if we needed anything.
After dinner Janet and I went to the living room. I took off my jacket and tie, Janet slipped off her heels. We snuggled as we watched TV and made out. Derek cleaned up while he had a few drinks. When his kitchen work was done he joined us, already unsteady, sitting in his reclining chair. He had a bottle and a glass with ice . He was going to drink while watching us.
——
As Janet and I were making out, letting our lust slowly leak out. Every once and awhile, when I noticed him watching, I would do something deliberately to show him Janet was mine – squeeze a boob, run my hand up her dress, say out loud how hard she was making my cock. Derek was moaning a little and I could see him rubbing his dick. I finally had Janet stand and I reached up and pulled down her pink panties. I threw them at Derek, they landed on his shoulder.
I positioned Janet across my body with her legs open to my right hand. I touched her running the tip of my middle finger around her pussy hole and pressing it in slowly. Janet inhaled and closed her eyes. She said softly “Derry, his finger is in me”. Janet raised her hips and she let out an “Oh”. She opened her eyes and turned to look at Derek, “Derry, do you see what he is doing to me? Derry”? Derek did not respond, he was staring at my hand moving under Janet’s dress, his hand was rubbing his cock in rhythm with my hand.
I played with Janet, teasing her, getting her close and then backing off. This went on for half an hour. She would look at me, close her eyes, look at Derek, moan, say something to Derek, kiss me. I was fingering her, rubbing her clit between my thumb and index finger and, every once in a while, tease her ass hole. Janet was becoming very wet and her hips were moving up and down. I knew she was close.
I leaned down and kissed her. I whispered “Look at him” and put a second finger inside her. She looked at Derek and told him to look at her. She said “See what he is doing to me? This is what I let him do to me in our bed, Derry. I let him touch me and use me. This is what you said you wanted. Do you like it”?
Derek moved his gaze from her crotch to her face and nodded. I said “Derek, is this what you want me to do to Janet? Say it”. He nodded again and said “Yes, I want you to have her”. Derek pulled out his cock and began to stroke it. I loved hearing him say that.
I started fingering Janet faster, she groaned and told Derek “He’s going to make me cum Derry”! I was slamming my fingers inside her as hard as I could. She began to writhe and jerk, she turned her head to look at me. I told her to look at him and pushed her face toward him. I wanted them looking at each other as I made her come.
Derek’s right hand was moving up and down in a blur, his face was red. Janet was red faced. I was probably red faced, too. She jerked a final time and closed her legs on my hand. She yelled “I’m cumming Derry! He’s making me cum! Derry”!
Janet pushed her hips up and down for thirty seconds or so as she kept saying “I’m cumming”! She turned her face to mine and we French kissed until her climax subsided. She fell back prone smiling, staring at me. She turned her head back to Derek and told him “I love how he touches me”.
Derek stared at us, groaned and said “Janet, no”. Derek shot some cum in the air, maybe three or four inches, with a few squirts. He looked strained, almost in pain and then turned his head away. He regained some composure and took a drink from his glass still looking away from us.
I was still hard. Janet said “I will take care of you”. She opened her legs and sat up. I told her take off her dress and her bra, leaving her only in her white thigh high stockings. Yum. She rubbed her hands over her breasts (she knew I liked watching her touch herself) and pulled on her nipples with her eyes closed.
Janet leaned down, kissed me gently and moved to the floor between my legs. She said “Show it to me”. I unbuckled my belt, undid the top button and unzipped. She pulled my pants and underwear down and took them off of me. She reached out, grabbed my cock and twisted her body to look at him. She said “Derry his cock is always so hard. He says I make his cock get hard”. She turned to me and began to jerk it.
I told her to suck me. Janet was a good cock sucker. She licked the head and then the shaft. She stroked it and massaged my balls. She would tell me how hard it was and how good it felt in her mouth. Twice she said “His cock is so hard, Derry. Not like yours”. I was pulling on her nipples as she sucked. Pinching them hard from time to time. Just to let her know who was in charge.
I said “See how she sucks me? She loves my cock. Don’t you Janet”? Janet said yes. I asked Derek if he liked watching her suck my cock. He nodded and gave a little smile. I asked him if he wanted to watch me fuck his wife. His eyes got wide and nodded.
I grabbed Janet’s hair to pull her off my cock and said “Get on me”. Janet gave my cock a final deep throat and climbed on my cock. She eased down on it and began to ride me slowly. She told Derek how much better my cock felt than his. “Derry, he feels so good in me. He is so hard”. I leaned over and saw Derick smiling red faced and wild eyed.
Janet rode me slow and steady. We kissed from time to time. I played with her tits and worked over her nipples. She liked a little pain while being fucked. She had told me the pain I gave her as we made love would make her pussy ‘get hot’. If we were kissing as I pinched them she would moan and say “Yes” or “Oh”. I liked hearing her say those things.
We made love, not fucked, for 20 minutes. Both of us would say things to Derek as we progressed. I would ask him if he liked watching us. She would tell him how he was a poor lover, how she needed ‘a real man’ in her life. The kicker was when Janet told him how glad she was he had brought me to her. I was looking at him when she said that. He closed his eyes, moaned and began rubbing his little cock again.
As Janet got closer to climax her pussy bouncing sped up, our kissing got more passionate, our hands moved over each other with more force. We forgot about Derek, we were in our own world. Just before Janet went over the edge, I leaned to the right and looked at Derek. His mouth was open and he was breathing hard. He was again furiously stroking his little cock.
I turned my attention back to Janet. Her eyes were closed and she was make the little moans she did just before she would come. I pulled her to me, stuck my tongue in her mouth and held her there with my left hand. I ran my right had to her ass and pushed my middle finger in her ass hole. She screamed in my mouth and started shaking, I let myself go and held her mouth to mine as we shared our orgasms. We kissed and touched for minutes.
Janet whispered “Let’s go to bed” and lifted off of me. She dripped cum on me, the couch and the floor. She bent down and licked and sucked my cock for a short while. She held a hand to me and we started to walk out of the room. She veered to Derek’s chair, I could see cum on Derek’s pants and hands so he must have come a second time.
Janet bent over Derek and kissed him hard for a few short seconds. She straightened up and asked “You like tasting him”? Derek reached up to grab her head and resume the kiss. She said “No, that is all you get”.
She turned and led me upstairs to bed.
Source: reddit.com/r/sexystories/comments/rlw0by/my_boss_was_a_cuckold_he_watches_us_part_3_str8