My boss was a cuckold (the cuckolding begins) Part 2 [Str8] [MF]

[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: This story describes the first time I got together with the wife of my cuckold boss. Janet, the wife of my boss, who had come on to me a month earlier, hinting we would be up to some hanky panky at their June cookout.

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 know this post is long. The sex stuff starts at ——

It was the second Friday of June 1975, warm and humid. Janet was dressed in a sleeveless top, loose white shorts, white socks and white tennis shoes. She looked like what she was – an attractive suburban housewife. As in the previous months, she was friendly with me but did not spend much time with me. Derek seemed to be in an especially good mood. In the previous few days he had asked me several times if I was going to be at the cookout. I told him I was and was looking forward to it. Once he asked if I was going to bring a date. I told him no. He smiled and clapped my back saying “Good”.

The cookout went off as usual. Lots of people, lots of food, lots of fun. I did notice Derek was drinking pretty heavily. I was coming to the conclusion that Derek was a secret drunk. I also caught Janet looking at me several times. Each time Janet smiled, once she waved.

As the cookout wound down, people began cleaning up, bringing food and utensils into the house. Derek was sitting in the family room with a glass and a bottle of liquor. He was still talking but his speech was slurred. Janet’s sister Alice, her friend Connie and I were helping Janet in the kitchen. I overheard Alice, Connie and Janet whispering but could not make out what they were saying. By 9:00 the kitchen was clean; Connie and her drunk husband were gone; Alice had taken Janet and Derek’s two children to her home. It was just Janet, Derek and I left in the house.

Janet turned out the lights in the kitchen and walked up to me. She thanked me for my help and put her arms around me and we kissed. And our kisses got hotter. I moved her to press her back against the counter. My dick was hard and I pressed it against her. We kissed and I reached up to squeeze her breasts. Janet turned her face from me and said “Let’s get him upstairs”.

Derek was slumped in the chair. Janet helped me get him up enough that I could squat down and get him over my right shoulder. I stood up and told her to lead the way. We went up the stairs to a guest bedroom where I flopped him down on the bed. We undressed him to his underwear. Janet covered him with a blanket, we turned out the light and shut the door.

The show was about to begin.

——

I immediately pressed Janet against the hallway wall and kissed her. All I could think of was fucking her in her own home. Janet kissed back and lead me down the hall to the master bedroom.

We kissed standing next to the bed for several minutes, my hands holding her head, her hands roaming my body. Janet unbuckled my belt and undid my shorts. She felt my hard cock and gave an “Mmm”. I started kissing her neck and undoing the buttons on her top. I pushed the top over her shoulders and dropped it to the floor doing the same with her bra. I bent down and kissed and sucked her nipples.

She said “Stop, wait” and dropped down in front of me. She pulled down my briefs and took me into her mouth. Not some of my cock, my entire cock into her mouth. I pulled her head back and told her to lick the head of my cock and to take her time. Janet said “Um, yes” and began to slowly lick and kiss and suck my cock helmet while looking up at me with her big brown eyes. She continued for several minutes making sounds of enjoyment. It was very erotic feeling, hearing and listening to this married woman suck my cock while her husband slept off his drunk down the hall. I was getting too aroused.

I stopped her and helped her up. I kissed her and stepped her to the bed. I gently pushed Janet down to the bed, removed her shorts, socks and tennis shoes; leaving her bikini panties on her. I undressed and paused to take in the situation.

Janet looked ready with her eyes closed, hand moving under her panties. Her mouth was slightly open. Her small nipples were erect. I moved between her legs and began kissing and licking her thighs as she rubbed her clit. I lightly bit her thigh from time to time. When I bit her she would moan and say “Yes”. I could not stand it, I wanted to get my mouth on her. I moved her hand away and told her to play with her tits. I pulled down the bikinis and dove in. I got a little floral scent along with the slightly musky odor of an excited woman.

I licked her tight hole, running my tongue around it and then pushed it inside her. She pushed her pussy to me and said “Oh yes”. I sucked on her rather large labia and tongued her clit while running a finger in and out of her hole. When I looked up I could see Janet lightly touching her nipples which has always been a turn on for me. I heard her saying “Yes” softly over and over. (“Yes” was her go to word while having sex as I found out.)

I began to suck her clit and touch it with my tongue while it was in my mouth. She suddenly stiffened, moved her hands to my hair and pulled my face to her pussy and then screamed “Yes” over and over. Her body began shaking and thrashing wildly. I gripped her hips as tightly as I could and continued sucking and tonguing her love button. After her climax ended she pulled my head away and told me to stop, it was too much.

I moved up to her and we began to kiss gently and playfully. I was touching her nipples and tried reaching down to lightly touch her clit but she stopped me. She said it was still too sensitive. She was cooing and purring, enjoying my touches. She, in turn, was holding and gently stroking my dick. She asked me if I liked “eating” her. I told her I did. She asked what I liked most about it. I said that she tasted so good and and how much she liked me “eating” her.

I added I also liked that she was married and I was eating her “married pussy”. She moaned, kissed me hard and gripped my cock hard. She asked me if I had been with a married woman before. I told her I had been. She kept kissing and asked when that was. I told her the year before. She asked if I was still “fucking her cunt”. (In Janet’s parlance she had a pussy, other women had cunts.)

I told her no. She asked if her husband knew, I said no we were very careful. She whispered “You won’t have to be careful with me. Derry knew we were going to be together tonight. He wants you to fuck me”. I had been pretty sure of that but it was good to hear Janet say that out loud.

We stopped kissing and held each other under the covers for a while. She gave me a light kiss on the lips and slide down my body kissing it as she did. Janet began to suck and lick my cock, focusing on the head of my cock and massaging my balls. I lay still and began to talk to her, telling her what I liked and how good she was. When I was fully hard I told her to stop, I was ready. I got off the bed and got a condom out of my pants. She shook her head and said her tubes were tied. I threw the condom on the table. I moved between Janet’s legs, spread them and pushed my cock into her quickly.

I did not take my time as I wanted to cum in her. I fucked her with a fairly fast steady pace. Janet played with her nipples and kept saying “Yes”. I pushed her hands away and began pinching her nipples and then switched to pulling and twisting them. Janet responded with a gasp and arching her back. I continued to work over her nipples getting rougher as I did. Her breathing got heavier and she started pushing her hips to meet my thrusts and moved her hands to cover and grip my hands. I could not hold back, I made a final thrust, groaned and began cumming. Janet wrapped her legs around me and screamed “Yes” over and over as she shook underneath me.

I leaned forward and we kissed for several minutes. I rolled off of her and she laughed and said “My God that was great”. She lay in my arms for a while then got up went to the door, shut off the hall lights and closed and locked the door. She returned to the bed, we embraced and fell asleep.

I woke with Derek knocking on the door telling us breakfast was ready. Janet groaned and sat up. Her hair was disheveled and looked sexy as hell. She kissed me and said we should go down and eat. She told him we would be down shortly. I redressed in my shorts and shirt. Janet put on a large football jersey. Nothing else.

We went down and Derek had a breakfast laid out for us. Janet sat on my lap and we shared a plate of food. She was playful feeding me bacon, toast and scrambled eggs. Every few minutes she kissed me, usually while looking at Derek. Derek served us making sure we our plate was always full. Janet was chattering about what she and Derek had to do that weekend.

I started to get hard again feeling her ass move around my lap. Having him watch and serve us didn’t hurt either. I worked my left hand up underneath Janet’s jersey and pinched a nipple. Janet gave a little squeal and told me to eat. Derek was watching and must have known what I was doing. He just kept grinning.

When we finished Janet told him we were going to get a shower. She went upstairs and showered taking time to rub and touch all over. I wanted to have sex again but Janet said she had no time today. She said we could get together soon if I wanted to see her again. I told her I did want to see her again, the sooner the better. We kissed and hugged, dried each other and redressed. We walked downstairs and made out at the front door. I could see Derek peeking around a corner watching us kiss and touch each other.

I drove away with her standing in the front doorway waving at me. I could see Derek behind her with his arms around her waist.

Source: reddit.com/r/sexystories/comments/rlj9f8/my_boss_was_a_cuckold_the_cuckolding_begins_part

1 comment

  1. That really is erotic. Very well told as usual. Makes me wish I was there watching as well.

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