Rick & Jane Show Cuckold Bob How It’s Done

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A run-in with his supervisor at the coffee shop that morning became a surprise cuckolding scene by late afternoon, giving Rick the power for a change.

One of our SDC members submitted the following story to our “Sexiest Cuckold Adventure” Erotic Writing Contest. Sign up today to submit your own amateur erotica.

Business travels take me to many places across the country. Three years ago, I frequented Madison, Wisconsin more often than the other cities. At work, Bob was my supervisor. He was a man with few words, meticulous, and very efficient. Being social, I got along well with the entire team. Word got out that I was dating a tall Black office security woman — Keisha. Bob frequently noticed that she waited long after her shift to be with me and ride home with me. At a few of the office parties, he noticed us particularly close together. Some of the colleagues appreciated my relationship with her, with high and low fives. Bob, during the one-on-one quarterly review, brought up my affair with the security guard. He hesitantly said, “Rick, we do not encourage relationships with the work environment.” “Bob, it is my personal life. I don’t think it is affecting the quality of my work. Have you received any complaints?” He nodded negatively, “Sorry I brought it up.” “It’s fine, Bob! If you brought it up, it is important to address it. We will be careful to avoid any unpleasant situations for you.” The next two months went by, and I was very careful with my affair with my Black friend.

Meeting Jane

Winters in Madison are terrible. The lake effect brings the city to a freezing lockdown. Every Saturday morning, I visited the coffee shop near the Capital building. This morning was no different except that as I picked up my coffee, I noticed Bob sitting with a buxom woman. I smiled and walked over to their table. “Hi, Bob. It’s good to see you here.” Bob looked up. The woman next to him subconsciously adjusted her breasts and looked at me with a smile. “Oh, hi, Rick, this is my wife — Jane.” I put my coffee down and warmed my hands before I reached out to shake her hands. I felt her hand tremble in my firm grip. After our initial interactions, I felt I may be intruding on their private morning. “It’s a pleasure to meet you, Jane. Bob, I hope you two have a good weekend.” “Are you leaving us?” Jane blurted out with disappointment. Bob turned to look at his wife. She nudged him with her elbow. “Rick, why don’t you join us?” I hesitated. Bob’s eyes were on me. 

I reluctantly sat down opposite the couple, with small talk on various topics, including weather, sports, food, and movies. Jane adjusted her hair and herself to get my attention. “It’s so nice to meet you in person. Bob does not say much about his work, but he has mentioned you a few times to me.” “Good, I hope.” Jane extended her hand to touch mine, “I can see why you impressed him.” Bob looked on as her hand rested on mine. I casually pulled my hand back and sipped my coffee. Jane lowered her head and neck to expose her cleavage, “Honey, why don’t you invite him to our place?” I could tell Bob was very uncomfortable. I took my coffee and got to my feet, “Jane, Bob! I have to go. It’s good to see you this morning. Bob, I will see you in the office.” Jane looked disappointed. She nudged Bob with her elbows. I walked out of the door. 

A minute or so later, I heard Bob call me from behind. I turned around to see him walk up to me. “Jane wants you over for dinner tonight. You can bring Keisha along.” “Keisha is out of town. Why don’t we meet when she gets back?” Bob hesitated for a second, “Please come by this evening. Jane and I would like that.” “Sure Bob. Text me your address. I will be there around 6 pm.” “Can you be there earlier by 3 pm?” He began typing his address on his phone. “Okay, see you at 3 then,” I said as my phone sounded the receipt of the new message.

A Surprising Turn of Events at Bob and Jane’s

Bob and Jane lived in a gated community. I pulled over to the security guard around 3:15 pm. The guard gave me the directions to the house and slapped a visitor sticker on the car. Parking the car in the driveway, I stepped out with a bottle of cabernet, chocolates, and flowers. Jane opened the door. She was taller than when I saw her this morning. She received the wine, chocolates, and flowers softly exclaiming, “Oh my, I am charmed.” She moved closer to kiss me on my face. 

Jane led me into the living room with a high ceiling. She placed the flowers in the vase and left the wine and chocolates on the table and came by to sit next to Bob on the two-seater, surprising me with a question, “How is it going with Keisha?” She continued, “She is hard to satisfy, you must be good.” Bob looked at me. Jane unbuttoned her top and exposed her breasts to me. I stared at them for few seconds and got up to leave. “Jane. I don’t know what you expect.” She suddenly hid her chest with the blouse, exclaiming, “Fuck, Bob! You did not …” Bob looked sheepish. “Oh! This is embarrassing.” I knew I had the edge, “Besides you are not my type.” She was at the point of no return. 

She pulled open her blouse again and then pushed down her leggings, exposing her naked body to me. “Please. Am I not desirable?” She walked slowly toward me as I stood at the door. I looked at her naked body and then at Bob. He had a subdued look about him. She unzipped me and felt my crotch over my underwear, “My! No wonder Keisha is not letting you go.” She pulled out my thick muscle and whispered, “Let’s show Bob how it is done.” I saw Bob nodding his approval, and I was not going to say no to free pussy.

Showing Bob How It’s Done

She undressed me in seconds, and I lifted her in my arms. She swooned, “That’s it. Take me. Fuck me on our bed.” She directed me as I carried her up the stairs. Bob followed us closely behind. I laid her on the bed as Bob closed the door behind him. The three of us were in the room alone. “Open and show him what I have to play with,” she commanded him. Bob obeyed her by displaying his smaller penis with a pencil-size thickness. My cock was thick and erect

The room went silent as I pushed her legs apart and positioned my cock at her entrance. “Foreplay can wait for later,” I whispered. She opened up her cunt and I pushed in hard. Bob looked on with his erection as I pounded his wife in front of him for the next ten minutes. She was wet and dripping even before the penetration. Bob stroked himself as he watched her scream in pain and moan with pleasure. My penetration was slow and deep. My body was crushing hers in the missionary position. Bob had tears in his eyes, his cock dripping cum on the floor. His wife was exclaiming aloud, “I am cumming! Oh my, you are fantastic. Let’s do it again and again, and often.” For the first time that afternoon, my lips pressed hers and our tongues rolled on each other. We heard Bob say, “Thank you, Rick.” As I lay next to her, she told Bob, “Clean us up, darling. I want him again.”

Rick & Jane Show Cuckold Bob How It's Done

This story was submitted by one of our members to the Sexiest Cuckold Adventure Erotic Writing Contest. SDC announced the winner of this contest on January 15th, 2021. Our editor made minor adjustments to this story for length and clarity.

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