Date Night

Date Night – One of Many

I will try to make the preface as short as possible, but it is somewhat necessary, in order to understand my mindset; My tendencies toward being a cuckold started when I discovered how turned on I got after prying details out of girlfriend who had cheated on me when I was a senior in High School. So the next thirteen years, in broad strokes, amounted three failed marriages before I met Carol (Her real name) who I have now been married to for 33 years. She also had been married three times previously and we were both still pretty young. She was 33, I was 30, we both had children from a previous marriage. She was not what I would call a stunner, but very pretty and sexy even though the years of a, thus far, mildly rough life showed on her. Perhaps that “slightly used” look of experience is what attracted me to her. Needless to say, having both been kicked around a bit, the insecurity and jealousy trap that befalls many new couples were ancient history for us… We easily opened up to each other, both emotionally and sexually. We were not afraid to experiment and approach new territory in our sex life. We had actually met previously but never gotten involved. I was a full time musician back then and she frequented some of the places I had played. This also meant we new many of the same people. True to my history, one of the things that excited me was asking for details of her past sex life. As some time went on, I discovered that a number of my friends had fucked her at some point in the past. Once she realized I did not get jealous, it actually enhanced our sex life and seemed to open many doors. These talks and fantasies led to swinging, which eventually tailed off to mostly MMF encounters with the wife, myself and another man. As time went on, as I did not drink anymore, but she still liked some bar fun once in a while, there were some bar pick-ups and we eventually agreed to her dating. The date nights were some of my favorites… All of my stories are 100% true.


Gary was originally one of the bar pick-ups but evolved into long term dating. He was younger than us. She fucked him the first night they met. She said the sex was great! He came 3 times, once in her mouth, once inside her and the 3rd time on her tits. Although he never reached a point where I was allowed to be there, It just got better for all of us…

Carol frequently dragged her feet until the last minute deciding her plans for the night. It was a Saturday night and I was getting ready to go play a gig about 40 miles away from home. She said she had no plans when I was leaving. I got to my gig, set up and played the first set. On the break, I checked my phone, hoping for a message and sure enough, I had a text saying “Gary called, going to the bar”. Of course I felt that familiar twinge in my cock, knowing well that this meant she would be home late with a well used cunt. I savored the excitement for the rest of the evening and took my time tearing down my gear and getting home because I knew I was in no hurry.

When I arrived home at about 3:45 AM, of course she was still gone. I relaxed for a bit, started surfing some porn, trying desperately not to cum in anticipation of was was yet to come. At about 4:20, my phone rang and she asked me to come get her at Gary’s house as they had both been drinking. Of course, this was a pretty common occurrence. It took me about 15 minutes to reach his house, I pulled in the driveway and sent her a text that I was there. He would never let me come in. They made me wait for nearly 15 minutes before I saw the front door open, The kissed for quite a while as I watched from the car, him still naked with his 7” soft and spent cock hanging down his leg. Carol was wearing only a skirt and the silk blouse she wore to the bar, bra and panties in her hand. the kisses were prolonged and intimate, tongues teasing and lips just brushing softly.I saw her her free hand drop down to his cock and stroke it gently as she turned and looked me in the eye. I was rock hard… after what seemed like a half hour, she finally broke off the kisses and walked toward the car. Once in the car, she leaned over and kissed me deeply, she tasted of alcohol and a faint, salty taste of cum. She smelled of sex and had that familiar glow on her face. She reached down to my hard cock and said “ Oh poor little thing is hard, have you been touching yourself?” I admitted I had and asked her if she had fun. She simply leaned back in the seat, dropped her hand between her legs and produced two wet, shining fingers which she held to my mouth and said “what do you think?” I eagerly sucked fer fingers into my mouth, tasting the intermingling of her pussy and the familiar, salty taste of his cum. I sucked at them hungrily and was disappointed as she slowly slipped them out. I noticed then that Gary was still standing in the door watching this scene intently with a big grin on his face. With that, Carol rolled down the window, waved and yelled “see you soon lover” and asked me to take her home.

The ride home went as usual. She was leaned back in the seat plying with her cunt and telling me how well she had been fucked. When I mentioned the prolonged goodnight kisses, she laughed and said, “You’re lucky, if I could have got him hard again, I would have gone back inside and it would have been longer. Once in the house, she took control. She took my hand and walked me straight to the bedroom and made me undress as she watched. When I removed my underwear, she took notice of my rock hard 5” dick, which is pretty thick, and saw the wet spot in my underwear and the stick line of pre-cum that stuck as I pulled them down. The giggled playfully, but with a wicked tone and told me I had been bad. She then told me to lay on the bed as she removed her blouse revealing a couple bruises on her 38 C Tits and rubbed her nipples, telling me how sensitive they were after Gary had sucked and fondled them roughly. She told me to lay back, straddled my chest and lowered her used cunt to my mouth. The smell was amazing, pure sex… as her cunt reached my lips, I opened my mouth and licked at her clit before slipping it between her lips. As I parted her labia with my tongue, she moaned and said “See what a real man does to me?” “he touched my pussy in places you could never reach, he always does”. “Can you taste him in my pussy?” Just then she moaned loudly and the first taste of his load oozed into my mouth. She ground her cunt into my face and told me to “lick out all of his cum”, “There are two loads in there”, “he came inside your wife twice tonight”. I lapped desperately at her cunt, milking the last drop of his cum from her used pussy. She pulled away from my mouth and laid her head on my chest and said “now you can cum”. I knew this meant she had no intention of letting me fuck her, but rather, I was to jack off while she watched. She would suck pinch my nipples, telling how good Gary’s cock was for her, that he could stay hard and cum multiple times over a few hours and how she wished she had not had her tubes tied because she would love taking the chance of getting pregnant when he shot his seed into her womb. This would always put me over the edge and make me shoot cum all over my stomach, which she would feed to me with her fingers… This would nearly always end in her saying “Now everybody is satisfied, I know Gary and I were”. Then she would say “Good night Bitch Boy” and simply drift off to sleep.

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