[M]y oral hookup with a MIL[F]

Recently I’ve been craving to go down on women.
Believe it or not, I’ve made it to thirty without having had the pleasure of doing so. One girlfriend even refused to let me do it and pushed me back up again when I was initiating it on my own… but nevermind that now.

Craigslist isn’t widely used where I live so you get one serious reply every once in a blue moon, and that’s if you’re lucky.

Cue a few weeks back when a reply to my ad – in which I offered to go down south without any recompensation required – flew in. It even had a picture attached, a lovely toned backside of a woman only wearing a thong of sorts.
She outright stated how she may not be what I’m looking for because she was a few years above the upper limit I had listed. She didn’t look like she was in her early fifties however, and after making sure there was no catfishing going on, we agreed to meet at her place. It took me a little more than an hour to get there by car.

When she opened the door I was greeted by the sundress I had asked her to wear. Off to a good start.
We sat down in the dining room and she offered me something to drink. I asked for water and received a pitcher filled with ice cubes – it was a rather hot day and you could still feel the heat during the later afternoon / early evening hours.

A few minutes of chatting passed, we got comfortable with each other. She told me about how she was travelling a lot due to her work and that she had recently hooked up with a local somewhere in South East Asia. After presenting her the massage oil I brought along – in case we needed to ease ourselves into it, she got rather frisky and bluntly told me that we should get started.

She wasn’t shy at all, even less so when I got up and told her I wanted to confirm something – by placing my hand onto her inner thigh and sliding underneath her dress, going straight for her panties. She was wearing a pair, which is what I wanted to find out, and she reacted by letting out a little squeal of pleasure when I rubbed her private parts through her panties.

We were still in the dining room and I had her bent over the table within seconds, her panties pulled aside as I inspected and probed her pussy. First with my fingers – just one, following up with a second, and by god, she was still quite tight – and then with my tongue, for which I kneeled down.
I joked about how tempted I was to just fuck her right there. To this day I fantasize about doing just that, having her bent over, her dress lifted up, panties pulled aside, and just taking her. But that’s not what why we had met.

She led me upstairs to a spare bedroom and we got even more comfortable. She was on her back and I between her legs before long. What a pleasure she was to finger and lick out. Taking my time to get to know that space between her legs, I knew it drove her insane – a guy can tell, especially if she’s pushing your head right into her pussy.

I can’t remember whether I made her orgasm first or if I freed my cock to have her play with it before that. It doesn’t matter much, because she did and she was very eager, even letting me fuck her face a little after I stood over her and asked her to return the wet favor of using her lips and tongue. The way she gave me head was a little too tough for my taste, but she was so eager so why complain?

Briefly after I was fed up and went for my condom. I flipped her over onto her stomach, her knees on the floor, and mounted her from behind. Usually I last a long time, but all that rough treatment must have softened up my cock to the point where I came within minutes. But I kept fucking her as I managed to stay hard.
Once it was no good anymore I dove back between her legs.

We basked in glory of our orgasms, and with her legs spread so casually before me I couldn’t resist, so I went for round two. But not before fetching my massage oil and rubbing it onto her thighs. She loved that!
Pretty soon after, my fingers were back inside her, as was my tongue poking at her clit. It took her right out of her recuperation and back into loud moaning.

Mind you, this was the second time I ever went down on a woman, yet both times I’ve been told how good I am at it.
(The first time was a previous hookup, but that one’s not as exciting to write about. Apart from the fact that she refused to believe me it was my first time.)
I don’t claim that I am a tongue god or anything silly like that, but it’s great to be validated not just by words but also by physical reactions like the one she had for round two.
That one was pure service. I didn’t get hard anymore, and I didn’t feel like getting hard or fucking her a second time either, so I focused on getting her off again. Truth be told, I guess I prefer rough sex only mentally – the idea of rough sex. The thrill of initiating it, like my fantasy of fucking her over her dining room table. Anyway.

It didn’t take her long to reach her orgasm again – something I read previously proved to be golden: if she moans “keep going” or “yes, that’s it” – keep doing exactly what you’re doing. Don’t speed up, don’t slow down, just continue. It does work!

While she tried to regain her breath she let slip that there’d be enough time for me to shower before her husband would return. I had suspected as much, that she was actively cheating, but she hadn’t said it outright before. Flashes of keys rustling and the front door opening while we were lying there naked and panting raced through my mind. I politely declined, not just based on this awkward situation potentially coming through but also because my shirt had already been full of sweat when I arrived, forcing me to shower again once I returned home.

As we got dressed, we openly chatted about her cheating and how the picture of her toned backside had been taken by the guy she cheated with in Asia. I don’t particularly mind cheating – there’s many reasons for it and I can understand a lot of them, but I’d have preferred it if she had told me beforehand. Oh well.

She couldn’t thank me enough for making her orgasm at least twice, and when I arrived at home an e-mail from her was waiting for me, thanking me yet again.
Too bad it was a one-time thing, but on the other hand the risk of getting caught in the act by her husband – who may or may not, according to her, be cheating on his own – wasn’t exactly a turn on.

The experience as a whole was certainly memorable. Now if only I could do it over again and fuck her over that darned table…

Source: reddit.com/r/gonewildstories/comments/55hzte/my_oral_hookup_with_a_milf