u/Darkchoclentine

I'm 36M, married, but want to be a boy toy for older women. I've been married for 7 years with my partner who is 35F (bi), but I still have a lot of pent up sexual desires up for adventure that wasn't fulfilled yet. I am 175cm tall with athletic body, long hair Southeast Asian. I do not want to jeopardize the relationship by acting out this fantasy until the relationship is at the level to make it open and trust is made between both sides so I'm going with this fantasies.

The names are made up, thanks for reading, I will keep updating... (latest update: June 2026)

1. Moon: My married friend (40F) from running group.
   We hang out around group runs and gym time together, she knows and met my partner, she's fit and funny, it's seeing her in exercise cloths suits well with her body. My fantasy is to rent a mountain resort together, go run, do gym stuff, exchange massages, I confess my long time crush of her, compliment and appreciate her body in both sweaty and showered, hear her out about me, do naughty stuff both in the woods and in the resort. I want this to be more of friends with benefits lifelong, on call invitations.

2. Hulda: A divorced 48F businesswoman and party animal.
   Knew her through friend of friend, she's very disciplined, has dominant vibes, clear of what she wants. My fantasy is that she calls me to please her and pleasure her whenever she wants, being a woman with high sexual standards for satisfaction, from eating her p***y underneath her work desk, sex in the office, hotel dates, social events, business trips, vacations. She knows what she wants, she sets the terms, she pays me, she gives feedback, she compares me to her ex in both positive and negative ways, she berates me if I make a mistake, she lets me know if she calls other men/women too.

3. Kaye: The massage lady (42F) who I hooked up before.
   She is a licensed massage therapist, she is very sweet and cute, she is a great mix of conservative appearance with very naughty/liberated side. I met her during my "naughty massage parlor" adventure while I was having a very rough time with my partner when frequency of intimate time was less than once a month. She was a good massage therapist, great listener, I felt very comfortable sharing honest thoughts and struggles, I've paid her extra for cuddles and conversational time. Her naughty side is that she has so many ways of foreplay, teasing, and getting the dragon straight up hard when I was so stressed, so tired, or just ejaculated. She has a boundary not have me eat her p***y, there is something very attractive with this level of emotional support yet have our private lives apart and physical boundaries. My fantasy is that I get to take her to island trips, mountain trips, exchange massages, and unlock whatever journey it requires about eating her p***y. She will give me massages very often from long traveling, absorb whatever personal life crisis I had.

4. Ann: The SW who I hired for fetish stuff (40F).
   During the sex spree I had, I encountered something very unexpected, she advertised herself as a "mom" and not really my type in both her looks, body, and being a few years older than me, somehow I got intrigued and contacted her. She surprised me with her moves and the ability to try new positions, I got awakened to my attraction to older women from that day and never regretted from exploring, it was a thankless job for being so patient with me when I tried the longest slow/sensual/conversational intercourse and also longest, hardest, loudest fuck I had while being recorded on video. I got to explore my armpit fetish, my dominant and submissive sides, explore my kind of bondage, filming, roleplay, costumes... My fantasy is that I want her to be present when I'm fucking people I'm super attracted to, then bounce to Ann when things get too excited, she will keep my dragon hard and in the calm zone in order to go longer, then switch to the main woman again.

5. The revenge I hope my partner would do when she finds out.
   I hope she gets to explore her fetishes that she did not get from me, the thought of her fucking with other people actually turns me on, I want to hear stories of her fucking other people behind my back being told by her or other people, I want to be in a cucked position to watch her getting pleasured by other men and women, I want to see her in bondage with people does it way better than me, I want to see her DVP with other two men.
   I want to see her screaming other people's name in front of me when she's fucking someone else.
   I want to hear her screaming my name when she fucks with other people.
   I want to hear her screaming other people's name when I fuck her too.
   ***Note: The reverse activities also turn me on such as me being dominant or her in cuckquean***

6. My redemption path.
   In order to redeem myself, my partner would want me to:
   6.1 Confess - confess every sexual and emotional relations behind her back, stating reasons, frequency, and details.
   6.2 Identify - I would be tied up on a bed, blindfolded, have each women take turns fondling me and facesit on me and I have to identify the right woman, if I get it wrong the fondling gets less intense, if I'm correct the fondling gets more intense into BJ, HJ, riding.
   6.3 Take care - Having my blindfold off I get to prove to my partner that I actually care about giving them pleasure, I have to fuck each of them in front of my partner and make sure each of them tell my partner when they are satisfied then I take a nap or move on to the next woman.
   6.4 Outperform - The last woman would be my partner, but I can call for assistance any person involved to help pleasure my partner while I'm the main one pleasing her, from the bondage person to assist her, a guy to do DVP with me, Kaye to wake up my dragon, or Ann to sustain my pace or my dragon.