Hello,
Love this site. I've just recently become a cuckold and at the hands of my former college roommate. His name is Mike. We got inadvertently paired together as roommates during our senior year. It's a long story but basically our college had to shuffle a bunch of us around after our dorm needed emergency repairs and Mike and I got stuck together.
Mike was a former football player and was very tall and athletic. I also found out quickly that he wasn't afraid to strip down and change clothes directly in front of me. I saw his dick several times and it was huge. One day Mike asked me if I was gay because I never changed clothes while he was in the room. I was perplexed and asked why that didn't make me the opposite of gay. Mike persisted though and explained that it seemed like I was hiding something. A week later, Mike came into the room while I was getting ready to go to the shower and saw me completely naked. He looked directly at my dick and I could tell he was judging its size. I quickly put my towel around my waste and headed to the bathroom in shame.
Mike also had a girlfriend named Lisa. She came over multiple times a week and I had to leave the room while they had sex. Each time coming back into the room afterwards, Mike would strut around in his boxers and boast about what he had just done. I tried to tune him out but it was also a bit of a turn on.
This culminated one night when I came back into the room after one of Lisa's visits. Mike was in his bed under a blanket. I sat at my desk and then Mike got up. I saw that he wasn't wearing any pants and his dick was still semi-hard. He said he was gonna go to the shower but then caught me staring at his dick. He joked that his eyes were up here while pointing to his face. He then said that he knew I was gay but I promised I wasn't. He walked towards me and told me to prove it. I asked how and he told me to suck his dick. I protested and said that didn't make sense. If I sucked his dick, I was obviously gay. Mike then countered that I'd only be gay if I sucked his dick and liked it.
He walked closer to me and his dick was now a foot away from my face. I turned my head and stared at his dick. I felt so submissive in front of it. He then put his hand on my head and guided his cock towards my face. I opened my mouth and started sucking it. Immediately, I noticed a strange taste which I quickly realized was Lisa's juices. I couldn't believe I was doing this and I struggled to manage the size of his cock as it got hard inside my mouth. Mike laughed and said he was right about me being gay all along.
I didn't protest this time though and just kept sucking him. I grabbed the base of his cock with my hand and jerked it while continuing to suck him. Mike told me that it felt good and I picked up the pace. I then felt Mike's cock start to twitch and he came inside mouth. I gagged at first but then resumed sucking him until he was finished cumming. It didn't taste great but it wasn't horrible either. I swallowed and Mike laughed. He said I was even better than Lisa at sucking his dick. He got his towel and went to the shower. While he was gone, I quickly masturbated and then got into bed and pretended to sleep.
After that first experience, Mike would have me suck his dick each time after he fucked Lisa. I strangely started to look forward to her visits. Mike also insisted that I be naked while sucking him because it was weird if he was naked and I still had all my clothes on. This gave Mike many opportunities to see me fully naked with an erection and make fun of my small dick. I was humiliated but also enjoyed it. I was giving him multiple blowjobs a week and getting quite good at it too. In between Lisa's visits, Mike also started to watch porn on his laptop. He told me to kneel under his desk and suck his cock while he did. It was somehow even more humiliating.
Over the course of the school year, I probably sucked Mike's dick over a hundred times. But after graduation, I never heard from him. We both went our separate ways. It wasn't until five years later that I encountered him again. By this time, I had a long term girlfriend named Lauren. We'd been dating for over two years and living together for over a year. I re-encountered Mike when Lauren got a new job at a restaurant where Mike ate frequently. I went to pick her up one night and he was talking to her. I didn't recognize him at first but he had a shit eating grin as soon as he recognized me. Lauren introduced me to Mike and he played coy. He shook my hand and my heart sank in my chest.
A day later, Mike sent me a text message. He said it was good to see his cock sucker once again. I told him I didn't do that anymore and pleaded that he shouldn't tell Lauren. Mike told me my secret was safe with him as long as I helped him out. I asked how and he explained that Lauren was quite attractive. He suggested that I encourage Lauren to hook up with him. I told him no way. Lauren was my girlfriend and I'm not gonna encourage her to cheat on me. Mike then said that Lauren might want to hear more about my cock sucking skills. Deflated, I responded that I didn't want Lauren to hear about that no matter what. But I added that I had no idea how to get her to hook up with him. Mike told me it was ok and he would guide me. As long as I followed his instructions, he wouldn't tell Lauren anything.
I did have a cuckolding fetish and I had told Lauren about it previously. She wasn't opposed to it but neither of us took any actions to make it a reality. Lauren is quite attractive and receives lots of attention from other men in general. I knew she would have no trouble becoming a hotwife, at least logistically. I guess I was just a bit afraid that we could never go back to how things used to be once it happened.
Mike's first instruction was for me to stop having sex with Lauren. He told me to make up any excuses I needed but I couldn't have sex with her until he did. He added that I can lick her pussy but that's it. I agreed. Little did Mike know, this first rule wasn't too much of an imposition. Lauren and I probably had sex once a month or so. Due to my lack of size and skills, Lauren had trouble orgasming when I fucked her and I always felt bad finishing first. As a consequence, I already went down on her often while I masturbated. Other times, we'd lay next to each other in bed and masturbate ourselves side by side.
Mike's second instruction was for me to fake some car trouble the following weekend when I was gonna pick her up from the restaurant. He told me I had to be at least 30min late. I agreed again. I texted Lauren just as her shift ended that I got a flat tire and was at a gas station getting it fixed. I told her I was sorry but I'd be a bit late picking her up. Lauren told me it was ok and she'd just wait for me. When I arrived nearly 45min later, I saw Lauren and MIke sitting together on a bench outside of the restaurant. They were both laughing and had their legs crossed towards each other. I parked and walked over to them. I apologized again to Lauren but she said it wasn't a problem at all since Mike was nice enough to keep her company. With a gulp, I thanked Mike and he just smiled at me. Lauren and I then said goodbye and left.
On the way home, Lauren explained that Mike and her just talked for a long time and got to know each other a bit. I said that it looked like Mike had a bit of a crush on her and Lauren blushed and admitted that maybe he did. She asked if that was a problem. I told her it wasn't and said I liked seeing her being flirtatious with other guys.
Mike texted me later that night and I gave him a recap of what Lauren had said about him. He was pleased. For his next instruction, he told me to tell Lauren that I ran into him randomly at the grocery store. He included a basic script of what to say. The next day, I went to the grocery store and came home to Lauren. Following Mike's bullet points, I told Lauren that I saw Mike while at the store. I explained that we chatted briefly but Mike hadn't realized that we were dating and instead had assumed that we were just friends. She asked if I corrected him but I said I didn't really have a chance. Jumping back to Mike's script, I said that he gave me his phone number and asked if I could give it to you. Lauren blushed but said she was sorry. She added that it must have been awkward. I said it was ok and gave her his number. I said she should text him to be nice and so he doesn't think I threw away his number before giving it to you. Lauren agreed.
Lauren texted Mike and clarified that me and her were already dating. Mike responded that it didn't seem like we were a couple and he thought she was cute so he wanted to give it a shot. He added that it didn't seem like I was opposed to it either. Lauren asked him what he meant and he explained that I obviously wouldn't have given her his number if I didn't want something to happen. Lauren wasn't sure how to respond. After a couple minutes, Mike texted again and said she should give him a chance with one date. He said I could even come along so there is no deception. Laruen asked me what I thought she should do. I told her that I supported her 100% and thought it would be exciting to watch her on a date with another guy. Lauren then responded to Mike and agreed to go on a date. Afterwards, Lauren was embarrassed but admitted that she did like Mike and thought he was hot. She asked again if it was ok and I assured her it was.
Mike gave me another instruction the next day. He said I should take her shopping and get her a new dress and lingerie for their date. We went to the mall later that day and told Lauren that I'd buy her a complete new outfit for her date. Lauren loved to shop and was happy to accept my offer. We went to several stores before she found a black dress that she liked. The skirt wasn't too short but it had a high slit over her left leg. And the top showed off her cleavage nicely. She asked if it was too revealing but I told her she looked great. I bought the dress and we then went to Victoria's Secret. Lauren said she didn't need any new underwear and it wasn't like Mike was gonna see it on a first date anyways. I explained that I wanted her to feel sexy and confident though and maybe some new lingerie would help. Lauren eventually agreed but said I had to pick out what I wanted her to wear. Walking around the store together, I saw a purple lingerie set with see-through mesh on both the bra and panties. Lauren picked out her size and asked if I was sure this is what I wanted her to wear for Mike. I said yes and then bought it for her.
When we got home, Lauren tried on the lingerie. She looked incredible. She posed in front of the mirror and said she hadn't worn anything like it before. She put on the dress too and picked out some black heels to complete the full look. She asked me how she looked and I told her she was beautiful. I took a photo of her and sent it discreetly to Mike afterward.
Mike set the date for the following Saturday. The plan was to go to a restaurant and then walk over to a bar afterwards. That morning, Mike texted Lauren and said he didn't want her to feel any trepidations about me later during their date. Lauren assured him that it was gonna be ok. Mike said if she had any doubts about my commitment, she should make me put on a pair of her panties and wear it during the date. Mike said that if I did something as crazy as that, then my commitment would be beyond question. Lauren showed me the text and I told her I'd do it if she wanted me to. I said this would complete the experience and I agreed with Mike that I didn't want her to have any questions lingering in the back of her mind during the date. She went to her closet and picked out a red thong that she knew I liked. She handed it to me and told me to put it on. I took off my pants and boxers and then slipped it up my legs. I had never worn a thong before. Lauren walked around me and said I looked cute while laughing a bit. She asked if I was really gonna wear it all night and I promised I would. I put my pants back on over the thong and Lauren texted Mike back to confirm that I would wear her panties to the date. Mike texted me soon after with a laughing face emoji.
We arrived at the restaurant later that evening. Mike and Lauren sat together on one side of the booth and I sat across from them. I was silent and just watched as they talked and flirted. The meal went by like a blur. I paid the bill and we walked together to a nearby bar. Once inside, I ordered drinks for everyone while Mike and Lauren stood against the wall. It was quite loud and they had to be close to be able to hear each other. As he leaned in to say something in her ear, Mike started putting his arm around her waist and eventually left it there to hold her against him. I brought the drinks over to them and stood there awkwardly as they continued to talk and MIke explored Lauren's waist and back with his hand. Lauren didn't recoil at all from his touch and instead started to lean into him. We finished the drinks and I headed back to the bar to get another round. By the time I was back, Lauren had her arm around Mike as well and they were loosely hugging each other. Lauren looked really excited and seemed to be enjoying all of Mike's attention. We finished the second round and then Lauren left to go to the bathroom. Now alone with me, Mike told me to show him the panties I was wearing. Humiliated, I lifted up the side of my shirt and pulled the side of the thong above my jeans momentarily. Mike laughed and said he always knew I was a faggot.
When Lauren returned, Mike suggested that we go to his place to chill out a bit. Lauren agreed and complained that it was hot in the bar so it would be nice to go somewhere cooler. Mike drove Lauren in his car and I followed behind them in my car. When we arrived, his house was quite nice. He gave us a quick tour that culminated in the backyard with his pool. Lauren took her heels off and sat on the edge of the pool with her legs in the water. Mike asked if we wanted to go for a swim. Lauren said yes but we didn't have any swimsuits. Mike said it was ok and we could just go in our underwear. He didn't wait for our confirmation though. Mike quickly stripped to his boxers and then dived into the pool. Lauren then stood up, looked at me, and then pulled her dress over her head. Lauren was standing on the edge of the pool in the see-through purple lingerie I bought her and Mike could clearly see her nipples and pussy. And once she walked into the water, the fabric became almost completely transparent. She swam over to Mike and then turned to me. She said the water was great and told me to jump in. Completely humiliated and embarrassed, I took off my clothes until I was only wearing her red thong. I had a partial erection from seeing Lauren in her sexy lingerie which didn't help either. They both watched and laughed as I jumped into the pool.
Lauren and Mike played together while I waited in the other end of the pool. They got to a section that was too deep for Lauren to stand so she put her arms around MIke to hold her up. He wrapped his arms around her too and I watched as their wet bodies pressed together. This continued for several minutes and Lauren eventually had her legs wrapped around his waist as well and he carried her around in the water. And another minute later, Mike kissed her on the lips and they made out passionately while I watched in simultaneous excitement and horror.
Eventually they stopped kissing and got out of the pool together while holding hands. I followed them and Mike led us inside to get towels. He wrapped one around Lauren and threw another one at me. We dried off and then just stood there in damp underwear. Mike took Lauren by the hand again and led her into his bedroom. Once inside, they started kissing again and he unhooked her bra. Lauren then got on her knees and pulled down his boxers. His cock popped out in front of her face and she was amazed momentarily by the size. Mike was over twice as big as me and I'm sure it was the biggest dick that Lauren had ever handled. She took it into her mouth and moaned while sucking him. I got on my knees in the corner and just watched. After several minutes, Mike picked up Lauren and threw her onto his bed.
She shimmied her panties off and spread her legs for him. He then crawled on top of her and guided his cock into her pussy. She moaned immediately and her eyes rolled back in her head. Mike went slow at first but then picked up the pace and started fucking her roughly. They started in missionary but Mike then spun her around and fucked her doggystyle facing me. I watched as she moaned with each thrust. She was orgasming almost continuously in pure ecstasy. Mike started to moan too and pulled out. Lauren laid on her back and MIke then sprayed his cum across her boobs and face. After catching their breath, they remembered I was there. Mike called me over and told me to give Lauren a kiss. As I got close, I saw that Lauren had strands of his cum across her lips. She wasn't sure if I was gonna do it but I leaned in and kissed her on the lips. I immediately got a taste of MIke's cum. I then sat back down and Lauren went into the bathroom to clean off. I went outside and retrieved our clothes. We both got dressed and Lauren gave Mike a long kiss before we both left together.
When we got home, we both stripped down and got into the shower. Lauren explained how incredible Mike felt inside her as I jerked my cock and came on the shower floor. Lauren plans to meet Mike again and hopefully regularly. And Mike continues to text me with various humiliations. For his second date with Lauren, he's already told me that he plans to cum in her pussy and he expects me to eat it out afterwards.
Yetti Yikes - yettiyikes@gmail.com
