This is a story from some years ago involving my long-term girlfriend (no longer together) and our first experience with a deeper cuckold dynamic. She was in her early 40s, and I was in my mid-40s. We had been together maybe a year or so, and mainly had a lot of hookups with random men for sex, meeting from Craigslist, Adult Friend Finder, a swinger club, etc. It was exciting to explore as a couple, and relatively safe from an emotional perspective because these men were just looking for NSA sex.
Free cuckold community
Sign up now!
Our process was generally for me to do the online work, corresponding and screening, bringing men to her when someone looked interesting. If she liked someone, she would meet them alone for coffee or a drink, pretty much like online dating-type meet & greets. We found that men would be a lot more relaxed when meeting her without me, but we were open about the cuckold situation from the start.
One day, a man contacted us from our ad and immediately stood out because he was well-spoken and high-effort in his message. He was a bit older, in his 50s, attractive with a fit body, seemingly successful and smart. He was also very into cuckolding, instead of just the typical guy wanting to get laid. My girlfriend really liked his pics and what he had to say, and he felt the same about her after she shared some face pics with him. They agreed to meet, but he was insistent on taking her out to dinner, instead of the usual coffee/drink meeting. He pretty much established more of a dating dynamic from the start.
I could tell when she got home from that first date that this was very different. She was normally very picky with men, slow to trust and careful. But with this man, she was so excited, already sharing a lot of personal information and establishing trust. She was gushing about him, how he was so handsome, mature, a successful businessman who exuded power. She told me how toned his body felt through his clothes when she touched him. At the risk of sounding cliche, it was as if she had met a god, and it was honestly very intimidating.
They agreed to go on another date, this time to a very expensive restaurant. Her excitement and attention in preparing for her date drove me crazy. I had never seen her have so much desire to impress a man outside of our relationship. I got to meet him when he picked her up. His confidence was overpowering, and I found myself struggling to converse or make eye contact as he put his hand on my back while talking to me. He made me feel almost like he was my dad or my boss. I waited patiently at home during their date, feeling excited when they showed up about 4 hours later.
He didn't stay long, but just matter-of-factly told me that they like each other a lot, so he is going to be dating her as his girlfriend. There was no discussion, no asking how I felt about it – just pretty much telling me this is the way it is going to be. He had his arm around her while he told me, and I was once again unable to make eye contact or say anything clever. I think I just responded "oh…ok" by reflex. She told me in bed that night about how she felt like a teenager again, feeling butterflies, enjoying just making out and "getting to the bases" in his car. They didn't even go all the way, but she seemed more excited just from getting felt up by him and giving him a blowjob. She also told me that he had an amazing cock.
They continued to date regularly and became fully sexual, sleeping together at both his house and in our bedroom. He was socializing her with his friends, as well as taking her as his girlfriend on dinners with business clients. It was maybe a month into their relationship when she came home one night after a date. She was buzzed and got into bed, and I spooned her, reaching around and feeling her pussy. Her crotch was sopping wet and sticky, and I got hard, rubbing my dick against her butt. She pulled my hand away, and I asked what is wrong. She told me that her "boyfriend" wants to talk to me, while she called him on FaceTime and handed me her phone. He proceeded to explain to me that he can be a little possessive, so he gave me a kind of sorry (not sorry) talk about him preferring that I no longer have intercourse with her. He told me I could eat her out and then masturbate myself. My head was spinning, and I found myself just obeying them both as I licked and ate his cum from her crotch while she continued to FaceTime with him. They both watched as I masturbated afterward.
His control grew over time, as she started to dress, do her hair and makeup, waxing, etc., based on his desires, and he started to forbid even my touching or kissing her anything more than a peck on the cheek. One day I walked in the bathroom after her shower while she was naked and brushing her hair. She grabbed her towel and covered up. It wasn't like a game, it was like she truly reacted that way based on her feelings for him. She told me that he no longer wants me to see her naked. He even had another talk with me about it, making me aware that he could take her from me if I do not cooperate.
I felt completely broken by him, and completely controlled by my sexual need to be inferior to an alpha male – like a drug that owned me. This relationship went on for the better part of a year, and involved numerous experiences that I still masturbate to this day. In the interest of not writing an endless post, I may make posts about some of these stories in the future. Just to finish (because I know some will ask), their relationship ended when his living situation changed (involving a new marriage and change of location). They continued to see each other for a while after he moved, but the distance made them naturally grow apart and finally end it.