I [M] was the 21 year old help, she [F] was the 39 year old who persuaded me into her bed. I then became her toy boy. Part 1 [MF]

Sorry if this is a little long. It’s my first post to this sub and the first time I’ve shared intimate details of these events with anyone. I started writing and it has turned into a longer story than I envisaged. Stay with me and I promise it will heat up. In this post, I’m going to set the scene and give you a hint of what’s to come in parts 2 and 3. If you just want the filth then skip to parts 2 and 3 which I will post, if Redditors want to read more.

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So back in the early 2000s I used to do plastering, tiling and general handyman/DIY jobs for friends and family. That is how my dad’s part time P.A. (let’s call her Deb) became one of my customers. I was 21 when I agreed to help her out in return for some cash.

Deb was a real MILF but I hadn’t realised it. Partly because of me being much younger and not having my eyes open in that way. We initially met through my father’s work, 18 months or so earlier. At that time, I was in a long term relationship with my childhood sweetheart who I had been serious with for several years.

Deb was 39 years old, 5ft 6, I guess about 120lb, had curly blonde hair and piercing blue eyes. Long legs, some good feminine curves and pale skin. She was in shape and did occasional rock climbing as a hobby – but she wasn’t the gym bunny type. On reflection, she oozed a feminine and MILFy vibe and I remember being quite surprised to learn she was nearly 40. It was only during my period of working for her that I started to notice how attractive she was.

Being 21, I was still finding my way in the world. However, I was definitely in the best physical condition of my life due to the manual building work and occasional circuit training I had been doing for a few years. I was 5ft 10, 150lb and no fat anywhere. Dark hair, dark brown eyes and well defined abs. I was more tanned that I have ever been since.

I’ve always found it easy to connect with women but that summer I was freshly heartbroken and my confidence was low. My childhood sweetheart had dumped me completely out the blue a couple of months earlier and I was properly heart broken. I was sad, lonely and generally despondent about life. The area we lived was proper country and all my friends had fled to college or the cities long ago – the social scene was therefore pretty limited and depressing. Finding a new girl wasn’t really where my head was at, perhaps because I knew it wasn’t going to happen locally. I also thought I needed time to get on my feet and decide what I wanted to do with my life before looking for a relationship. My family saw my pain and so tried their best to find work for me to get me out the house and doing something constructive.

My dad put me forward for Deb’s tiling job that summer – so I can blame/thank him. Deb was his P.A. two days a week – helping out with all his business (and occasional family) admin. I first met her a couple of years earlier, when she was interviewed for the role. My dad’s business was run from our family home, so over the course of a couple of years I had gotten to see her as a family employee who we could all trust (even if we didn’t socialise).

I was very happy to quote for the tiling job as I had nothing better to do. I had everything I needed to start straight away. I had done a similar job a few weeks before for a mutual friend, so she knew I was able to help. She wanted it doing by someone who wouldn’t let her down, so it fell into place and I got the job.

So I had popped by Deb’s a few days before getting started to check what I was dealing with. I worked out I needed 4 or 5 days to do the job. It was going to be sweaty, dirty, physical work in a basement. Deb explained to me that it was actually her mum’s house and she was going to move into the basement annex when it was done. It was part subterranean and part ground level so it offered her independence and the freedom to come/go without disturbing anyone in the main house. She even had a small fenced garden area for herself. So most of the work was done but I was there to tile all the concreted floor area. It wasn’t a big place but that suited me as I would be working on my own.

It was only later that I learned Deb lived off her divorce settlement and the part time work my father gave her. Not needing to work much (especially if she lived at her mum’s) meant she had a lot of time on her hands, especially when her kid was with the ex. hubby.

I admit that I was initially a bit surprised to learn that a 39 year old – proper grown up – was living with her divorced mum but I figured life isn’t a predictable thing. Also, Deb explained her mum was retired and often away visiting friends (which she was doing that summer) so was actually grateful for her daughter being around and keeping an eye on the house.

So, the next week it was a fairly mundane start to the project. I arrived at hers around 8am the first morning and after reconfirming a few bits about what she wanted, she left me to it. We didn’t speak much that day and she only checked in with me occasionally to see how I was getting on, or to offer me a cold drink. It was bit of a grind in truth but nothing I wasn’t used to.

On the second day of the job I turned up at 8am again and knocked on the door of the main house because I felt like I needed to announce my arrival. I think she might have forgot to set the alarm or slept in because I remember it took her a while to answer the door. I started to think she wasn’t there and was about to crack on when she opened the door. Debs was in her pj’s and dressing gown. I felt a bit uncomfortable as hadn’t seen many woman IRL in that state. There was nothing sexy about it but I think it was then I suddenly realised she was a very real person – with a life of her own – rather than simply my dad’s glorified secretary.

Anyway, after I got started Deb soon brought me a coffee which helped break up the monotony of what I was doing. She also offered to make me a sandwich for lunch – which I accepted. The morning went by as expected but then at lunch she sat with me outside to chat while I ate. I had never really spoken to her one on one before about anything personal before. I remember thinking she was genuine and easy to talk to. She told me she had heard the story of my heartbreak from my dad and said if I ever needed to chat she wouldn’t mind listening. I didn’t know much about her, so asked an open ended question or two to avoid me having to talk much.

Deb told me she she had recently divorced and had been living separate to the ex for well over a year. The divorce only finalised earlier that year and it was something he wanted and she hadn’t seen coming. She had been with him for 18 years (basically since my age), and married for 12 years of that. Her had said he wanted a divorce – pretty much without warning – and she suspected he’d been unfaithful with a younger woman during the time they were married. She was clearly pissed at him and now they barely spoke, except via occasional text, or on the doorstep when picking up/dropping off their 4 year old son who I never met. I think I told her he sounded like a jerk for doing what he did and, I too, also felt very ill-treated but at least there wasn’t a kid involved.

She said she understood what it was like to have been dropped out the blue. We didn’t go too much deeper but it felt like we both really wanted to talk – it was easy. I felt she was more annoyed about her situation (and seemingly less sad/forgiving) than I was about mine. She made me feel like a good human with a bright future, reminding me I was so young etc. I felt a bit sorry for her being a single mum and all. I told her I was going to make sure the tiling was spot on and if she wanted me to help out with decorating or moving furniture then I’d be happy to help.

That afternoon I got back to the job feeling 100% happier for having had an adult conversation with someone who had empathy. I worked a little later that day as didn’t want her to think talking to me would mean the job got done any slower.

At the end of the day, as I was saying goodbye, Deb mentioned a friend of hers was having a big bbq / summer party the next evening. She said there would be lots of people – probably 100 or so and even some of her friends’ kids (about my age & back home for a summer holiday to see their parents) would be there. She knew I was pretty bored and lonely, so if I wanted to go and be social then she would check with the host but expected they would be very happy for her to bring a friend. She even offered to pick me up in the evening and drive me there/back from my place so I could have a few beers and not worry about driving.

It was really tempting but I felt like Deb was taking pity on me a bit. I was a little uncomfortable saying yes straight off – especially because she would drive me and go out of her way etc. But she was right that I needed to let my hair down and be sociable. I agreed she should ask her friend if it was ok that I go and, if it was, I would really like to go. I said I would owe her though and maybe she could let me help her out with furniture moving etc. when the tiling was all done. I think we jokingly shook on it or something.

It was July and the temperature was definitely picking up. On the third day of the job it was going to be a lot hotter. I remember it going above 100f for the first time that year, and the start of a heatwave. Little did I know that it was going to get even hotter due to events that some might think of as predatory (by her) but which I take a lot of pleasure in remembering now.

Something was soon to happen which led to me having the most raw, carnal and unrestrained sex of my life with someone legally old enough to be my mum.

To be continued…

Source: reddit.com/r/gonewildstories/comments/leb06u/i_m_was_the_21_year_old_help_she_f_was_the_39