My Journey of becoming a Cuckold!
Hey. Wanted to write in and explain my journey of becoming a cuckold.
My girlfriend Nicole and I met in college. We were in the same dorm as freshmen but didn't start dating until our senior year. I had a crush on her at first sight but could never work up the courage to ask her out. We had a lot of mutual classes and friends so we saw each other a lot. But I was a pussy and waited until our senior year before even asking her out for coffee.
Before we started dating, I was in constant agony any time Nicole was dating another guy. Even just seeing another guy hitting on her was torture. But I think those experiences over time became the basis for some of my cuckold tendencies. I was so obsessed with Nicole that I started imagining what she could be doing with other guys. I even started masturbating semi-regularly to those imagined scenarios in my head.
Once we started dating though, I tried to put that behind me. We had a pretty normal college relationship. Nicole was just the second person I had ever had sex with but I was her fifth. She was definitely more experienced and confident than me in bed. I know I probably didn't match the performance of all her previous hook ups but we managed a relatively healthy and frequent sex life nevertheless.
After graduating from college, Nicole and I moved into an apartment together. Because we were both broke and jobless, we couldn't afford an apartment on our own so we needed to get a roommate. All our friends had moved away after graduation though so we didn't have very many good options. After a prolonged search, we ended up connecting with a guy named Mike who graduated from our same school the year before us. He had a two bedroom apartment and was looking for roommates for the other room. I didn't know Mike but Nicole had met him once previously because he was in the same fraternity as one of her prior boyfriends.
The first few weeks after moving in with Mike were a bit awkward. Nicole didn't want to have sex when Mike was home because he might hear through the wall. As a result, our sex frequency dropped considerably. Mike was friendly though with both of us and having him as a roommate wasn't as bad as I feared it could be. We started eating together and watching TV together in the living room quite often.
The apartment had just a single bathroom and you had to walk across the living room and kitchen to get to it from our bedroom. At the start, Nicole would bring her clothes with her into the bathroom and then change into them immediately after taking a shower. But over time as we got more comfortable and casual with Mike, she started making the trek from bathroom to bedroom in just a robe or towel. Mike got to see her almost daily in some state of undress.
She also started wearing her pajamas around the living room at night which usually included a t-shirt with no bra and shorts with no panties. The living room had couch and a separate lounge chair in front of the TV. Nicole loved the couch and would often sit in it with a blanket. It was Mike's couch and he had a 'spot' with an ottoman in front of it that he always sat in. That left me to sit separately in the chair beside them. On nights when Nicole was in her pajamas and sitting beside Mike on the couch apart from me, I got a hint of the cuckold feelings that I tried previously to suppress.
Mike was a big sports guy and would watch football games every weekend. Nicole and I joined him regularly and we started making 'bets' on the games. It wasn't anything too crazy to start. It would be something like 'loser cooks dinner' or 'loser cleans the bathroom'. These were things we would have done anyways so they didn't feel too onerous. But Nicole got competitive in the betting game with Mike over time. Mike bet her that if his team won, she'd have to serve us both drinks like a waitress for a night. Nicole then countered that if she won, Mike had to clean the living room and kitchen while wearing a French maid outfit. Mike laughed and agreed to her terms. But just an hour later, his team had lost and Nicole was teasing him while shopping for cheap French maid outfits online.
Mike served his punishment a few days later after the maid outfit had arrived. We both laughed when he walked out of his room wearing it. But he took it in stride and started feather dusting the room without a hint of embarrassment. His confidence in such a ridiculous situation made me feel submissive to him. If I had been his situation wearing the maid costume in front of him and Nicole, my face would have been bright red and I would have felt completely humiliated. As he finished, he joked that he'd get Nicole back next time. Nicole laughed and boasted that he had no chance against her.
From that day going forward, the betting game occurred exclusively between Nicole and Mike and I was no longer included. I wasn't complaining but it did feel like another element of separation between us. For the next bet, the terms escalated between Mike and Nicole. If Nicole won, Mike had to take out the trash to the dumpster while wearing a speedo. But if Mike won, Nicole had to clean the apartment while wearing a bikini and high heels. But luckily, Nicole won once again. The game was tied near the end of the fourth quarter but Nicole's team kicked a game winning field goal as the clock expired. Mike served his punishment boldly once again without a hint of embarrassment. And the speedo he wore definitely showed off a bulge that was hard to ignore. I'm sure Nicole noticed too.
Throughout this time, Nicole was getting even more comfortable in the apartment with Mike. One night while watching TV, she came out of the bedroom wearing just t-shirt and panties, got a drink from the refrigerator, and then walked back into the bedroom in front of both me and Mike. Mike definitely noticed and had his eyes focused on her ass as she walked past us. But despite this increased comfort, Nicole continued to pass on having sex with me whenever Mike was home. Over a few months, we only had sex a handful of times. And due to the delayed frequency of sexual interactions and my budding suspicions of what might happen in the future between Mike and Nicole, my performance nose dived. I could barely last more than a couple minutes inside of Nicole and had to pull out multiple times to avoid an embarrassing premature ejaculation. I failed to give her any orgasms with my dick and had to resort to prolonged sessions licking her pussy order to get her over the edge.
The next weekend, new betting terms were set. If Nicole won, Mike had to sing Britney Spear's Hit Me Baby One More Time at a local bar karaoke night while wearing a catholic school girls outfit. But if Mike won, Nicole had to wash his car wearing a white t-shirt with no bra. Nicole was confident due to her winning streak and agreed instantly to MIke's terms before I could even push back. Unfortunately though, Nicole lost this time. It wasn't even close. Nicole's team was down by 20+ points for nearly the entire game. Mike gloated throughout but Nicole just teased him right back and threatened to get him back even worse next time.
Later that day, Nicole put on a white t-shirt and got ready to wash Mike's car. Even before getting wet, her nipples were clearly visible. But Nicole tried to match the same level of confidence that Mike showed while completing his punishments. We couldn't wash it at our apartment's garage so we went to a self wash center. Mike and I stayed in the car while Nicole got out and did all the work. At first she just sprayed the car down with water but managed to keep herself relatively dry. When she started rubbing the car with a soapy sponge though, her shirt got wet quickly and became nearly see through. I couldn't believe that she was doing it out in the open where strangers could see her. Mike had the best view though, particular when Nicole was struggling to reach the top of his car and pushed her wet boobs against his side window. Though Nicole kept her cool, I was completely embarrassed in the backseat and didn't mutter a single word to Mike the entire time. Eventually, Nicole sprayed the soap off the car and then dried it with an air hose. She asked Mike if he was happy with his car wash and he said yes while rolling down his window and staring directly at her tits. On the way home, Nicole kept her wet t-shirt and Mike was so distracted that we nearly got into multiple accidents while he took every opportunity to glance over at her.
Sore about her loss, Nicole was intent to increase the stakes the following weeks. Mike initially suggested that Nicole do his laundry for the next week if he won. Nicole countered aggressively though and said that Mike had toke photos of himself wearing just a thong and send them to a girl he had been dating on and off for a year with a message saying that he was gay now. Mike instantly recoiled and said there was no way he would agree to that. Nicole teased him and told him to increase her punishment then if he didn't think it was fair. Mike thought about it for a minute and then agreed he would do it if Nicole gave him a blowjob, completely naked, and he could cum on her face at the end. I tried to push back but Nicole shook his hand in agreement too quickly. Afterwards, Nicole consoled me and told me not to worry because there was no chance that she'd lose this time. I had never even given Nicole a facial before and it was crazy to think that Mike might have that opportunity before me.
A few days later, the game was close for the entire second half. In the fourth quarter though, MIke's team pulled ahead. Even before the end of the game, Mike was gloating and teasing Nicole. He told her that she could start her punishment early if she didn't want to wait until the final buzzer. Nicole tried to stay confident but it became more bleak each minute. And at the end of the game, Nicole left the living room and went into the bathroom. She was in there for a few minutes and we didn't know if Nicole was doing. Mike told me to "check on my girl" so I went and knocked on the door. Nicole then opened the door and stood before me completely naked. She then walked past me and approached Mike in the middle of the living room.
Mike clapped and said Nicole was good to follow through on the bet. He stood up, walked around her, and checked out her entire body. Nicole was blushing and felt embarrassed being completely nude in front of Mike. She looked incredible though. I could hardly believe it was happening. Mike told me to sit down and I walked past them to sit in my chair on the side of the room. He then told Nicole that she could begin. She slowly got down on her knees and kneeled before him. Mike made no effort to undo his pants so Nicole reached up, unhooked his belt, and pulled down his jeans. Then after a gulp, she pulled down his boxers as well. His cock sprung out towards her face. It wasn't even fully hard yet but it looked huge. He was definitely much bigger than me and there was no question that Nicole would have noticed that as well. She was almost memorized by it at first and just stared at it. As she opened her mouth, I couldn't help but think about the rarity of blowjobs that I had received from Nicole, especially recently. And she had never gave me a blowjob to completion. It had always just been a 30s foreplay before we had sex.
It was part horror, part fascination as I watched Nicole take Mike's big cock into her mouth. She struggled at first but seemed resolute to provide a good blowjob. It was very standard for the first minute as Nicole got the hang of things. She then branched out though and started interspersing ball and shaft licking in between deeper throat attempts. His cock got fully hard in her mouth and upped the challenge for her to handle his size. She was very engaged and seemed to be enjoying the task at hand. At one point, she even started rubbing her pussy with one hand while keeping her other hand anchored to the base of Mike's cock. Mike noticed and started to take control. He held her hair momentarily before pulling his cock out of her mouth and slapping it on her face.
She took it in stride though and swallowed his cock once again with a moan when he fed it to her. I had an erection the entire time but was luckily seated so neither Nicole or Mike could see. Nicole continued to suck him energetically while rubbing herself. I could tell that she was really enjoying the experience. A few moments later, she orgasmed with his cock in her mouth. Mike chuckled and pulled his cock out of her mouth again. He was jerking his cock in front of her face and Nicole opened her mouth and stuck out her tongue. Moments later, Mike started to cum and shot a giant load across Nicole's tongue, face, and chest. And after he stopped jerking his cock, Nicole took it into her mouth again and sucked him slowly until his load was done. Mike said 'good girl' as she cleaned his cock. Once she was done, she suddenly seemed aware of me again and felt a tinge of embarrassment. She walked into our bedroom and I followed.
In the bedroom, Nicole started to apologize but then saw the erection in my pants and guessed that no apology was needed. She told me to take my pants off and I did so quickly. She then approached and held my cock in her hand. Slowly jerking me, she asked if I enjoyed the experience as much as Mike did. But before I could even verbally respond to her, I came as well and covered her legs in cum. Nicole laughed and recoiled instinctively which gave me a bit of a ruined handjob. She then got a towel to clean the cum off her body and we got ready for bed.
The next morning, Nicole was still naked in bed next to me. As we woke up, Nicole went to the bathroom to shower without even putting a robe on. Now that Mike had seen her fully naked, there was obviously no need but I'm sure Mike was still somewhat surprised to see her walk naked past him in the living room. I'm nervous and excited for what Nicole and Mike will bet for next.
Me & Nicole - mahmiss@tutanota.com
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