I was a toyboy for an older woman, and then her friend [MFF]

Oligatory this happened a few years ago, and for now I’ll keep it as short as possible, but happy to expand if there’s interest!

I met Lucy at the christmas meal of my first job, I was 18 and just discovering the world of working in an office (my only guide was The Office lol), Lucy was early/mid-40s, average height, in really good shape, of Italian descent, really big beautiful brown eyes. We’d hardly interacted before but hit it off at the lunch and kept talking into the evening. I was driving a few people home as I was working early the next morning, she ended up being the last prson to be dropped off. I was invited in, and quite nervous given I was a fairly inexperienced 18 year old, and I knew she was married. More talk on her sofa and firm confirmation that her husband wouldn’t be disturbing us that night, and we were in bed together. Whilst my experience was limited, it ended up being one of the nights of my life.

I had to leave early the next morning for my other job, but was invited back that night for more fun and takeaway, which ended up being eaten in bed. We had more chance to talk, and she elaborated that her husband and her had an open relationship – they were still close friends but no longer physically attracted, but kept living together. She showed me that he was at a girlfriends place for the weekend. Lucy also asked if I’d want things to be a bit more formal with us, that she’d always thought about having a younger guy at her beck and call. I was obviously completely in.

Over the next few months we’d meet 2-4 times a week, sometimes I’d stay most of the weekend or we’d drive straight to hers after work. I’d now describe it as a sort of gentle femdom relationship – she’d generally be in charge and whilst we’d try a number of kink and fetish things ultimately it was that I was her “toyboy” and was there to please her. As I mentioned, I was fairly inexperienced but quickly learnt a lot, funnily enough a lot of the tips that get highly upvoted on discussions about what women like and enjoy in bed were things Lucy taught me. I enjoyed giving oral anyway and she LOVED receiving it, and taught me how to really please her. Me giving oral was a central component of a lot of what we did, whether it was just as foreplay to vanilla sex, or that Lucy would sit on my face, or that she’d arrive home from work shortly before me and be waiting on the stairs with her skirt pulled up and legs spread waiting for me to bury my head between her thighs. We also tried a number of more kink and fetish things, she was incredibly open to a lot and always willing to try something, and our limits were quite compatible. In addition part of her staying with her husband was that they were both well off financially, so toys, lingerie (I love lingerie and would buy her items too) and other things (including many a takeaway in bed!) were bought.

After 4 or so months I’d become quite familiar with other aspects of her life, and one of these was a close friend she had – we’ll call her Caroline. Caroline was recently divorced, but as Lucy told me had been subjected to a dead bedroom for a number of years. They were very close (I believe they had met when both having kids so a strong bond over many years) and shared a lot of aspects of their lives. Lucy also mentioned that a few years ago Caroline had spent some time at Lucy’s upon finding her husband was no longer wanting to be with her, and one evening had spent the night in bed with Lucy – they’d only kissed but both had admitted to being in to each other. I was aware (and somewhat turned on) that Caroline knew about our relationship in quite some detail. Whilst talking in bed one evening Lucy had jokingly mentioned that Caroline could do with a relationship like Lucy and I had – she just needed someone devoted to fucking her brains out for a few months, and it was a shame I was taken by Lucy. I replied that she could always loan me out, to which she asked if I’d actually be interested, I replied I was but that I belonged to Lucy, and thought nothing more of it.

A few weeks later I arrived at Lucy’s, was greeted by her in a party dress and heels and swiftly taken to the guest bedroom. She told me she had a surprise for me but that I had to undress, put on a collar and leash and a blindfold. She led me by the leash to her room, to what I guessed was the side of the bed, and said “you can open your eyes to see your present now Caroline”. Lucy then told her that I’d do anything Caroline asked of me, that Lucy would watch and not take part unless invited by Caroline. I ended up spending some time pleasing Caroline before having my hands tied to the bed and being ridden. After that my blindfold was removed, and Caroline told me to fuck her doggystyle, which I of course obliged. Afterwards we invited Lucy to be involved. We ended up having two more threesomes with Caroline, and I also visited Caroline’s once, where we Whatsapp called Lucy.

A few months of Lucy and I continuing to meet and we reached the summer, and Lucy’s daughter returning home from university meant that it was almost impossible to keep going at the pace we had before. We agreed to pause over summer, with the idea that a break would mean come September we’d be more keen that ever to meet again. However I ended up meeting someone over the summer, and whilst we were both disapointed one of the initial agreements was that as soon as I was remotely interested in someone else that we’d end what we had before it did any lasting damage. Obviously the sex element of the relationship was a huge part of what we had going, but I feel that I grew a lot and wouldnt change any of it if I could go back in time – and I’m really glad it ended amicably.

I’m sure I’ll have plenty of people calling BS, sadly I have no proof besides my memories of what happened – and I’m happy to elaborate more if people are interested!

Source: reddit.com/r/gonewildstories/comments/narqwx/i_was_a_toyboy_for_an_older_woman_and_then_her