Jimmy Cuck Ch. 02

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Eyl 13, 2023 // By:analsex // No Comment

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I’ve always wondered where and how my cuckold fetish stemmed from; even though I’ve known I was a sexual submissive the cuckold fetish has been new desire. After some self-examination I believe I can pin point two distinct experiences where even though I didn’t realize it at the time may have influenced me.

The first was during my time as a sophomore in college and I was dating a girl named Catherine. She was going to a University in Illinois and I went to visit her right before I started my fall semester of classes. Megan was a petite girl, maybe A cup tits, but with a very pretty face and fit body. I arrived at night sometime around 8 pm or so and tried to get into her house she was sharing with 3 roommates. All of sudden, I guy from Catherine’s room start yelling out of her window for me to get the hell out of there and that he was fucking Catherine. Needless to say it was a big blow, and luckily I had a good friend of mine on campus to go visit to cool down. I remember being so angry that my friend Adam and I went out drinking that night and we both got laid. I did meet with Catherine later that weekend, and while she was very apologetic, we both agreed to end our relationship as the long distance thing wasn’t working.

The second instance was with my current wife Ashley. I had just graduated and was working my wife job right out of college. Ashley was 1 year behind me and was still in school while I began my career. The long distance wasn’t all that bad because I was able to visit a lot on weekends but still not the ideal situation. Ashley had 3 roommates and they decided that year for Spring Break they would all go to Florida together. I had no problem with this and even encouraged her to go because she was quickly approaching the “real” world. They went to Florida and were living it up, Ashley was drunk half the time and we had a few phone arguments especially since she told me she and the girls were partying with a group of guys they had met from some school down in the south. Of course this raised my jealousy level but I got over it and she returned when the vacation was done.

Flash forward several weeks to Ashley’s graduation weekend, when 1 of Ashley’s roommate’s boyfriends asked me out for some beer and wings at 1 of our old haunts, we were sitting there discussing everything from sports, jobs, etc. when we got to talking about the girls Spring Break. He sivas escort mentioned that I must have pissed that the girls went for 2-3 days to hang out with the guys they met. It turns out that Ashley and the girls had ditched their hotel rooms, drove 3 hours across the state to where the guys were staying and stayed for several days. This set me off, we got to back to the house and I immediately went off on Ashley. I was considering driving the 3-4 hours home that night but had too much to drink so slept it off. At first light I got in my car and left forgoing the graduation ceremony and breaking it off with Ashley. It was several tense weeks before we ended up getting back together but Ashley assured me she didn’t do anything with anybody ( I think she fucked them) and only didn’t tell me because of she was afraid I would be mad. I guess still to this day I assume that maybe she got some frat boy cock while on Spring Break.

Jimmy Cuck 3

Ashley and I entered the hip Lincoln Park bar/restaurant and I quickly spotted Jeff and Jesse. We approached and I made some quick introductions with the butterflies threatening to overtake my composure. I made the mistake of looking into the eyes of Jesse and could see the glint of the “boy are you fucked look” that both excited and scared me.

I quickly looked down in half embarrassment and for the first time noticed what Jesse was wearing. An even shorter black dress than Ashley with her big tits on display and impossibly long high heels that brought her head to head with my 6 foot height. Jesse quickly took control and said “Jeff why don’t you take Jimmy here to the bar and get us some drinks while us girls get comfortable,” more of a command than a question.

We took the ladies drink order and made our way to the bar while Jesse and Ashley took their seats at a high top 4 seat table. Jeff and I made small talk at the bar and reassured me not to be too nervous that they weren’t going to proceed further than we spoke about, he did want to linger at the bar a little as to give the ladies a chance to talk. It was nice to see when we returned that Jesse and Ashley seemed to be getting along, and we settled in for a night of drinking and light appetizers. The evening progressed to complete normalcy, no outlandish comments and everyone seemed completely comfortable, even when Jesse and Jeff complimented my çorum escort wife on good she looked. The ladies did the usual run off to the bathroom together and even carved out a little space and made their own dance floor when one of their favorite songs came on through the bar. At about 11 pm it was time to leave, especially since we had a decent drive home, everyone said their good byes, and Ashley and Jesse even exchanged cell numbers. To that moment, I didn’t know what if anything had been discussed. I was really hoping for an email later that night or early the next morning from Jeff. On the car ride home, we both agreed that we had a good time and maybe we should hang out with Jeff and Jesse again, Ashley even had a little buzz going which always has proven good for night of action. We got home, went straight to bed, and immediately went at it. I popped an erection immediately recounting the night’s events and what lay ahead, and we went at it. We even invented a new position, where I was masturbating standing on the floor while fingering and spanking her while she was in a doggy position. I don’t have to tell you how unusual this was for us, but I made her cum with my fingers and then moved to mount her in missionary. I was so excited that I came in about a minute and did receive a rather unpleasant “ugh” of disappointment.

The next morning, as customary on the weekends, I headed to the local Dunkin Donuts to buy a few large coffees. Ashley was just waking up, and I brought the drinks up to our master bedroom. She thanked me and we began to chat and cuddle while enjoying the coffee, and that’s when it happened. Ashley said, “Did you know Jeff and Jesse have an unusual relationship.” I assured her that I didn’t and pressed her for more details.

“Well,” she said, “Jesse told me she is kind of the boss of their relationship and even gets to mess around with other guys a little.”

Ashley went onto explain that while we were the bar it came up that Jeff listens and obeys what Jesse says. Jesse was going to start going into more vague detail when we came back from getting the initial drinks. Their conversation had resumed when they went to the ladies room where Jesse had explained that it’s kind of a lifestyle and it keeps their sex life very hot just with a hint of domination, and that she had never been more happy. I feigned confused and shocked denizli escort at first and then kind of blurted out “wow that’s kinda hot,” which is my head was not exactly how I planned on saying it, I guess it just happened naturally.

My response generated a perplexed “hmmm” from Ashley, who as she got out of bed may have noticed the little chubby I was sporting. I jumped out of bed and ran downstairs like it was Christmas to check my email an update Jeff and sure enough I had an email from him in my inbox, which said “seed planted” with a cuckold caption below of a black guy with a huge cock, fucking a white wife.

Nothing much happened for the next few days, it was the middle of the week and we were chit chatting about work and various other mundane subjects when Ashley said, “so I talked to Jesse today, she called me to see how I was an to invite us out next weekend.”

She went on to say that she had told Jesse that she mentioned their conversation and my response. Jesse was pleasantly surprised and Ashley even told her, “He seemed excited by it.”

Jesse even encouraged Ashley and I to play around with it and explore a little. I must have looked flabbergasted, but managed to get out an “I’m game I guess, if you are,” and asked how we would go about starting.

Ashley gave me a quick little smile and said “Don’t worry, Jesse gave me a few ideas.” Ashley let the conversation stew in my head the rest of the night and I dare not ask her again as to not appear over eager.

I even tried to initiate sex at bedtime, which I don’t do very often, which Ashley declined. Talk about a fitful night’s sleep. The next morning I got out of the shower and was ready to begin getting ready for work when Ashley asked “if I was ready to play?” She told me to drop my towel and the mix of emotions with the usual morning testosterone bump was already getting me hard. I agreed and Ashley walked up to me and went on to explain that this game was about control and she wanted to be in charge. She took out a black sharpie from the nightstand, which she must’ve had prepared, grabbed my cock and drew a thick line down the center from my cock head down to the base. When she was finished she gave me a wry smile and told me that from now on I was not allowed to masturbate without permission and that if I played with myself too much the line would smudge and disappear and although she didn’t have any punishments planned that if I disobeyed she would think of something. Needless to say, I had a hard time getting ready but when I finished Ashley added, “You’re also now in charge of making the bed in the morning, have a great day at work honey,” and walked out of the room and off to her job for the day.

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