So this is an extension from something that I wrote about in r/CuckoldCommunity last week after my GF, who I’m back together with after about a 5 year separation. We’d been together for nearly 10 years before breaking up but now, after several years, we’re back together. We’ve both evolved and so when she told me that she has chosen to continue a professional but sexual relationship with her massage therapist I was surprised but willing to hear her out. My memory of her was of a woman who practiced a very conservative sex life. She enjoyed sex and wasn’t shy but kept that aspect of her life private and behind closed doors, to be shared with one partner at a time. This was our experience together in our first go around and it was my expectation when we resumed our intimacy. Her admission was a shock but I discovered that what she had been doing with the massage therapist prior to our getting back together was arousing to me and so, even though she had continued it behind my back for several weeks, I was able to compromise and let the ‘cheating’ go in exchange for a more thorough discussion about our individual sexuality and the agreement to involve each other in future experiences. The discussions have taken place in detail over the last few days. When she seemed to gloss over things, I pushed for details. We came to an understanding and she told me everything. It aroused both of us and we’re using it in our sex, but I also now find myself simultaneously excited, intimidated, anxious, and skeptical about our future. What follows is a synopsis of what she told me about some of her time with one man.
Most of her newfound sexual enlightenment came from a long distance relationship that she shared with a man about 3 years ago. The relationship lasted nearly a year but, due to the long distance nature, they almost exclusively saw each other on long weekend trips that they would take to each other or to a vacation destination. He is a wealthy man who lives on the West coast, while she is financially comfortable and lives on the East coast. She met him on a trip to see family in California and fell for him immediately. Apparently this led her to push her sexual boundaries in order to keep him interested and to pleasure him. It started with sexting, something we’d never done since she didn’t get a smartphone until after we broke up. Sexting turned into webcams. About once a month he would fly her out and they’d spend the weekend together. This led to trips together. She said that she recognized he wanted her to “loosen up” and she decided to, on the verge of turning 40, go for it. Eventually she agreed to go to Hedonism with him for a long weekend. She knew what it was but really liked him and enjoyed allowing herself to test her boundaries with him.
They arrived at Hedonism on a Thursday and were checked into a nice villa on the nude side that had a hot tub on the patio. The neighboring guests, a younger couple, were both sitting outdoors nude next door. She immediately felt intimidated and had a flash of fear that he would see her lack of confidence and stop liking her. This is important because it’s why I believe everything that she’s told me. I’ve known her for nearly 20 years and something that I know for sure is that when she feels self conscious she has the ability to internally create a character in her mind of who she wants to be and then externally act that character out. It’s usually for a business meeting or an uncomfortable dinner. This time it was to be for a weekend. In reality, that weekend has forever blurred the lines between who she thought she was and who she thought he wanted her to be. As she described it; immediately upon arriving they had sex and she watched him go down on her in the mirror above the bed. As it turns out, before the end of the weekend she would look into that same mirror and see three men in bed with her at the same time. She was surprised to learn that she couldn’t walk around on their side of the resort in a bikini. For the weekend she would only be covered during meals. The first night they walked around. She noticed most people were normal people, just nude. As the night got later and the drinks kicked in she noticed men paying more attention to her and a more sexual vibe. Her boyfriend also enjoyed the attention that she was getting. She said that, to that point, it was the most exciting and terrifying night of her life. She wasn’t fearful for her safety but she was unsure of what she would be expected to do and if she could do it. The drinks flowed and she played along, allowing her boyfriend to coax her to spreading her legs while they were by the pool. It was the first time in her life that she had been nude in a crowd. They spent time in the nude hot tube with others but nothing much happened. As they were returning to the room they had to walk past the neighbors hot tub patio. As they approached to within a few feet they noticed the neighbors were having sex with the woman bent over the hot tub. They’d gotten so close that all were startled. This led to a weird laugh but what is important was that she noticed the neighbors erect penis as he pulled away from his girl. She immediately found herself get weak knees. What she remembers is that the neighbors laughed it off by saying “That’s what we’re all here for” and invited them to join them for a drink. They did. The neighbors were both clearly aroused and at this point she was too. Later she found out that her BF was hoping that something would happen. Nothing did. They shared two drinks and the couples got to know each other and got comfortable with each other. The entire time my GF was preoccupied with the neighbors penis, which she described as at least 8 inches when it was hard but also really wide. (mine is 6 and pretty much the definition of average). She was embarrassed because she knows that the couple noticed her glancing at him. After a while they excused themselves and went back to the room. All that was important because it sets up what was about to happen. My GF decided that if she was going to play with someone else, as she knew her BF wanted to watch her do, that she hoped that it would be with someone with a penis that was larger than she’d ever had….like the neighbor. The next morning she heard them outside and walked out, nude, to say good morning. They welcomed her to share orange juice in the hot tub but she declined. As she returned to the room her BF had noticed her out with them and commented on how big the neighbor was and that it was amusing watching her look at him last night. He was a confident man and told her that he wanted her to have fun and to test her boundaries while they were there. They spent the whole day socializing and she experienced a new level of self confidence. She played volleyball nude. She danced with men and women. She played in the pool. She let men and women touch her all throughout the day and she touched a few men and women as well. Playing with women was a first for her. That evening her BF told her that he had scheduled a massage for her for the next day, Saturday, by a local guy who is well known on the resort. She was up for a massage.
The next day they had an early lunch where she had a few champagnes and then he took her back to the room. The massage guy was to arrive soon and her BF wanted to let her know that he’d met the guy before and that he was a good guy. He wanted her to know that he loved her and that she should have fun and to let go during the massage. She said this was odd because she was very familiar with massages. What was about to happen changed her forever. A large local man carrying a massage table and athletic bag came up from the beach side. Her BF welcomed him and introduced her to him. She said that the two had clearly met before and she suspected that they’d discussed what was about to happen. Her BF kissed her and said he’d be back in a couple hours. A couple hours? At that point, the champagne was flowing through her and she was already nude so she just said “I’m in your hands.” She noticed he was probably 6’2″ and muscular. He set up the table and politely made small talk with her. When the table was set up he had her lie down faced away from him. This was useless since there are mirrors everywhere and to her surprise he removed his clothes except for something like a loin cloth which covered his penis. He laid out his oils and began the massage. She felt small in his hands. This aroused her. She had never been with a local man before so it was exciting and felt risky but she knew that she was safe so she decided to relax and enjoy it. The massage started normally enough. He focused on her arms, shoulders, back, and legs. As she suspected, his hands came up her legs and he massaged her butt. She liked it. What startled her was what she felt in her hand. As he bent over her she felt his soft but heavy penis touching her hands, which were palm up, and as he continued she felt him allowing it to linger there. What really shocked her was how big it was. It filled her entire hand.
She didn’t know what to do. She caught herself softly squeezing it, mostly out of curiosity. She knew that any pretense of ignorance was gone. She had a strangers growing dick in her hand and his hands were inching closer to deep between her legs. She decided to go for it and opened her legs wider. She turned her head towards him and got a look at what was about to change her life. As she tells it, he was partially aroused and it was already bigger than anything she had seen. She had looked at porn and didn’t really believe that men this large existed, but they do and she was now engaged to experience one. At this point his fingers were slipping between her legs and she knew he was aware of how aroused she was. She couldn’t hide it. She also couldn’t hide her reaction to his body. She couldn’t play the character but she didn’t want it to stop. She just whispered: “I’m in your hands”. He rolled her over onto her back and then slipped off the cloth that was covering him. He placed his growing penis in her hand for her to stroke. He massaged her breasts and abdomen. Her abdomen is her sweet spot. She said when he put pressure on her belly she moaned and opened her legs. At this point he took over completely and she let him. She felt him stretch her hips. She was fully exposed. As he moved around the table his penis touched her. As he approached her head she opened her mouth. He noticed and offered himself to her. What she was expecting was to feel his penis slip into her mouth but what shocked her was that she couldn’t even get her mouth around the head. She said it was like trying to push a whole peach into her open mouth. Apparently they both laughed and this broke the spell and they both understood what they were there for. They moved to the bed and she proceeded to spend a good amount of time appreciating his penis. (she said that later she tried to gauge how big it was and in the grocery store the closest thing she could honestly compare it to was a Pringles chip can). She let him take over and he slowly pleasured her in every way. She was able to have intercourse with him but it was uncomfortable. Exciting and pleasurable in a way, but it mostly hurt. The condoms he had looked like they would break at any moment so ultimately they discarded those and fell into a 69 that only worked because he was so big. Most of what she remembers from that experience was how this large man with this enormous penis had worshiped her and let her take her time with him. She became addicted to the attention that he gave her. She came three times and nearly passed out. She was embarrassed because she wanted to pleasure him but couldn’t take him so she found a way by talking dirty and asking him to use her however he wanted to get off. He basically put the tip of his penis inside of her and masturbated until he was ready to come. He pulled out and came on her torso. She said that watching him cum on her was enough to make her nearly cum again and that in that moment she scooped up his cum and liked her hand clean. They laughed more and took a shower together. He washed her and toweled her off and then left.
More happened when her BF came back and later that night she was still so aroused from the massage that she welcomed the neighbor and another man to join her and her BF in bed. The neighbor girl filmed it for her and her BF to take home to use while they each went back to their respective coasts. I’ve now seen that video and THAT is a whole other story. This massage story, however, is what I’ve learned is the origin of her obsession with massages. Her current massage therapist isn’t a big man and isn’t that well endowed but he touches her in ways that bring those memories back and that is all she needs. I think I’m ok with that.
Source: reddit.com/r/gonewildstories/comments/emm8fd/fm_2nd_time_around_gf_went_to_hedonism_with_bf