Hello,
Hey. First time, long time. Hesitant to share my story at first but thought it might be an inspiration to some others. Five years ago, I was legitimately a guy who just fantasized about being a cuckold but had no hopes of actually becoming one. And today, I'm a very happy cuckold with an incredible hotwife girlfriend. I wanted to tell the story about how my girlfriend transformed over time and made my cuckold dream come true.
So my girlfriend's name is Anna. We first met in college but only started dating a couple years after we both graduated. Anna was definitely a bit shy and insecure. She did theatre in school and could break out of her shell when performing in a play. Otherwise in normal life though, she was quite reserved. I always had a bit of a crush on her and was surprised when she accepted my offer for a date.
Fast forward a few months, we were a couple and Anna had moved into my apartment. We had a great, loving relationship. The sex life though, if I have to be honest, was a bit of a mixed bag. And the problems were entirely on my side. Whenever we had sex, I'd either cum almost immediately in less than a minute or I'd never be able to cum even after 30+ minutes. I was completely in my head. Anna was so pretty that I naturally was excited and would have the urge to cum quickly. But if I fought off the urge and managed to push through by thinking of other things, I'd lose the ability to cum at all.
I told Anna it wasn't her fault and I think she felt sorry for me more than anything. She wasn't very experienced sexually so I wasn't sure if she knew what she was missing or not. Anyways, we fell into a habit where we'd just primarily have oral sex. Or more accurately, I'd go down on her and lick her pussy while jerking off my own cock. She almost never gave me blowjobs. She was happy with my oral skills though and I was able to control my cumming to reasonable time frames while masturbating.
All this time, I had the itch of my cuckold fantasy in the back of my head. I eventually worked up the nerve to tell Anna and she was unsurprisingly not into it at first. We kept talking about it though and she eventually agreed to dip her toes in the water. Our agreement was that she try talking to a guy at a bar while I watched and we'd both see how it felt. Later that week, we went to a bar together and I watched from a booth as Anna sat at the bar. Anna was awkward and anxious. She sat by herself for a few minutes until a handsome guy asked if he could sit next to her. Anna said yes and they started talking. She was cautious at first but eventually started smiling and laughing at his jokes. He bought her a drink and they talked for nearly twenty minutes. Even with this minor interaction, I was completely entranced and already felt a tinge of jealousy and humiliation but in an arousing way.
Anna eventually left the guy at the bar and we headed out together. As we walked home, we talked about her experience. She was blushing a bit and I could tell she was a bit embarrassed but also excited. Anna said the guy was very nice and she enjoyed receiving his positive attention. Asking how I felt, I told Anna that I was on the edge of my seat the entire time watching them together. Anna agreed to try it out again but didn't commit to doing anything more than just talking with a guy.
Over time, this scenario became a bit of a game for us. Whenever we went out, we'd look for opportunities for Anna to interact with other men. It started very innocently, like a dare to just ask a guy to help her pick a thing off a high shelf in the grocery store. But over the course of a couple years, Anna progressed to be much more confident and forward. We'd go to a club and Anna would be dancing with other guys and getting groped by them on the dance floor as I watched.
Another factor that helped in Anna's transformation was her friend Jessica. She met Jessica at the gym and they became quite close. Jessica was much more outgoing and frankly, slutty, than Anna. They started hanging out a lot. Jessica influenced Anna to dress like her with more revealing clothing. And their time together in the gym I think gave Anna more confidence about her body in general.
So for a nearly three year duration, Anna went from just dipping her toes in the water of my cuckold fantasy to being a confident woman who actively sought the attention of other men. She hadn't hooked up with anyone else yet but it felt imminent. Our sex life continued much the same as it had before with me on my knees licking her pussy and jerking my own cock. There was one interesting update though. Jessica and Anna went to a bachelorette party for another friend and all the girls got a dildo as a novelty gift afterwards. Anna was holding hers in the living room and joking with Jessica about it. Jessica noticed me watching and said I didn't need to be jealous. "It's only six inches" she remarked. To my surprise, Anna replied saying "Maybe he does need to be jealous" with a wry grin. They both laughed as I left in aroused shame. That was the first time Anna teased me in a sexual way. I loved it though and told her afterwards.
Later that night, Anna let me watch her use the dildo and I eventually started licking her while pushing the dildo in and out of her pussy. It was so hot. I came onto the floor beside the bed in less than a minute but continued to lick Anna for another ten minutes while she moaned in pleasure and had several orgasms. After that experience, the dildo became a regular inclusion in our play. And each time after using it, Anna had me take it to the bathroom to wash it before putting it back in her bed drawer. Anna kept up the verbal teasing as well. She mostly just made fun of my penis size but occasionally made fun of my quick ejaculations and pondered out loud about other men that she had met recently. She also told Jessica basically everything about our sex life, including my exact dick size, my issues cumming, and even that I tried on her panties once and that I looked "cute" in them. I was so embarrassed.
So that's the basic story of how Anna became hotwife ready, as I like to think of it. But I just want to stress that it wasn't quick and wasn't always easy. It took three years of incremental progress and Anna hadn't even made me into a real cuckold yet. But it felt close and more importantly, it felt like something Anna wanted too. It wasn't just my fantasy. It was our combined ambition for her to hook up with other men.
Around this time, Anna and I moved to a new apartment complex. It was relatively nice and had a pool and hot tub in the central courtyard. A few weeks after moving in, we noticed some other people our age that lived there as well. We'd see them typically on a weekend night enjoying the hot tub. Anna and I were in the hot tub one night when they came to jump in as well. They introduced themselves to us and we invited them in. Andy was the only guy who actually lived in the apartment complex. And then there were two guys and two girls who were friends of Andy.
Anna took notice of the other girl's bathing suits. Anna was wearing a sexy but relatively normal two piece suit. The other girls though had thong style bikinis and their tops showed off a lot more cleavage. I was relatively quiet in the tub and Anna kept the conversation going with them. Andy was obviously the alpha of the group and he paid Anna a lot of attention. I had a half erection watching them together but luckily it was hidden under the bubbly water. Eventually Andy invited us to come to a party at their apartment later that week. Anna agreed for us and we got out of the tub together. Back at our apartment, Anna teased me for being jealous and I had to admit that I was. We got into bed together and I licked her to multiple orgasms.
Later that week, Anna and I went to the party together. There were a surprising amount of people in a small space. It was mostly guys from Andy's old fraternity but there were a half dozen other girls there too. We greeted Andy and he poured us drinks. It was relatively normal for the first hour we were there. We sat on the couch and Anna chatted with another guy and his girlfriend. Andy was serving drinks and talking to a few other guys. Andy then turned on some music and joined us on the couch. There wasn't enough room though for everyone. I moved down and sat on the ground and Anna sat up on the arm of the couch while Andy moved next to her. It wasn't a big arm though Andy told Anna she could sit on his leg if she was uncomfortable. Without a blink, Anna leaned into his lap.
Anna got off of Andy's lap when we got up to get more drinks. We stood in a circle around the bar area. Andy and a group of three other guys surrounded Anna and I remained standing awkwardly behind them. Anna loved their attention and flirted playfully with each of them. The party was wrapping up and the other people started leaving. As they said their goodbyes to Andy, Anna and I finished our drinks. Eventually, Anna and I were the only people left in the apartment with Andy. He thanked us for coming and said we had to do it again sometime. Anna agreed. Andy mentioned that we should enjoy the hot tub again together too. Anna teased him by saying he seems to have a different group of girls in that hot tub every week. Andy replied that he wouldn't invite any other girls next time with a big smile. We agreed to meet him there a few days later.
The next day, Anna went to the mall and got a new swimsuit. She put it on immediately when she got home and modeled it for me. It was light blue and looked incredible. The bottoms were a very small thong and her ass cheeks were on full display. And the top was a tube top that accentuated her cleavage. Anna told me that she planned to wear it to the hot tub with Andy and she hoped he would like it. I told her he undoubtedly would as she continued to pose and admire herself in a mirror. Shamefully, I asked Anna if I could masturbate. Surprised, Anna asked "You want to masturbate right now? Cause I look so hot?". I nodded my head and she said ok but make it quick. I dropped my pants and got on my knees. I started jerking my cock as Anna stood there and watched. After just a few seconds, Anna told me to hurry up. I started jerking as fast as I could. Anna acted like she was impatient and tapped her foot with her arms crossed. I then came into my hand. The entire session had been less than twenty seconds total.
A few days later, we had our date with Andy at the hot tub. He was already in the tub when we arrived. Anna dropped her robe and asked Andy if he liked her new swimsuit. He said it was great and she stepped into the tub. She sat down on the side next to Andy and I sat across from them on the other side of the tub. Once sitting in the water, I realized Anna's tube top gave the illusion that she wasn't wearing a top at all. You just saw her bare shoulders without any straps.
Andy was Anna jokes while I sat a bit awkwardly and struggled to listen over the sound of the water jets. I couldn't see their legs or hands but wondered if they were touching at all under the water. Eventually Anna said she was getting too hot and sat up on the edge of the tub. She wasn't next to Andy anymore but now her entire wet body was on full display for him. Eventually the jets turned off and Andy asked if we wanted to come up to his apartment for a drink before calling it a night. Anna agreed as we all got out of the tub and dried off. I held Anna's towel as she walked in front of us in her thong bikini. Andy was looking directly at her ass the whole time, especially as she walked up the stairs. When we got into the apartment, we threw our towels on a chair.
We were now standing in a circle, Andy and I were shirtless, and Anna was in her tiny bikini. I felt so inadequate next to Andy who was much taller and more fit and attractive than me. Andy passed us beers and we headed to the couch. Andy sat down in the middle of the couch and Anna sat down on the far side of him. I sat on the other side of Andy, separated from Anna once again. We chatted for a bit and drank our beers. Anna had her legs crossed towards Andy and responded enthusiastically to everything he said. We eventually finished our drinks and headed out. Before exiting his apartment, Anna gave Andy a hug and pressed her chest against his still shirtless body. Once we got back to our apartment, Anna stripped off her bikini and jumped on the bed. My head immediately went into her open legs and I started licking her.
Over the next several months, we continued to hang out with Andy regularly. Each time, Anna pushed the limits a bit further and let And touch her or see her in a new way. She knew she was driving both Andy and I crazy with all her actions. It culminated one night while we were at a bar together. Anna was draped over Andy all night and we all got a bit drunk. We found a table in the back corner with just two stools. I sat on one stool and Anna sat on Andy's lap with her arms around his shoulders. She was wearing a skirt with her legs slightly spread.
Andy rested one hand on the inside of her thigh and his other hand around her back. I watched intently while he slowly moved his hand up inch by inch on her thigh. His hand was eventually inside of her skirt and Anna leaned back against his chest and stared into his eyes. They're faces were just inches apart. Anna then leaned in and started kissing Andy right in front of me. They made out for several minutes while Andy seemingly rubbed Anna's pussy under her skirt at the same time. I was floored but couldn't avert my gaze. I couldn't believe it was actually happening after so long.
Eventually they broke off the kiss and we left the bar. As we walked home, Anna and Andy walked several feet in front of me while holding hands and stopping intermittently to kiss and grope more. When we got to our apartment complex, they headed straight to Andy's apartment. I didn't know if I should follow or not. When they got to Andy's door, Anna saw me awkwardly standing near the stairs and ran back to me. In the middle of the hallway, she slipped off her panties from under her skirt and handed them to me. WIth a wink, she said they're a bit wet and she didn't need them anymore. She then ran back, went into Andy's apartment, and he closed the door behind them.
Once I got back to our apartment, I stripped off my clothes and masturbated using Anna's wet panties to stroke my cock. I came almost instantly into the bathroom sink. After cleaning up, I put on Anna's panties as well just to feel more humiliation and excitement while imagining what she was doing with Andy. I eventually fell asleep wearing the panties and Anna caught me the next morning still wearing them when she came back. She laughed and told me to keep them.
I asked what happened and she explained in detail how Andy fucked her quite roughly and multiple times with his giant dick. She said his dick was easily twice the size of mine and it made her orgasm over a dozen times throughout the night. I got hard listening to the story which I think just reinforced to Anna that I was 100% supportive of everything she did. She got undressed to get in the shower and told me I could masturbate as she left the room.
Since then, Anna and Andy continue to hook up regularly. I don't get to watch very often. I did get to see one incredible session when they fucked in the hot tub. I had to keep watch at the gate to make sure no one else came in. I do see them kiss, touch, and cuddle often. They do so openly in front of me wherever they are. I also once saw Anna give Andy a blowjob which felt humiliating. Anna almost never gave me any blowjobs for our entire relationship and she now gives Andy a blowjob almost every week. Anna told Jessica too about her affairs with Andy and Jessica was unsurprisingly supportive. Jessica got to meet Andy and ended up having a threesome with both Andy and Anna later that night.
Anna's Cuck - bythewaychilli55@gmail.com
