I act all masculine in public (I’m an FTM) but in private I fantasise about getting fucked like any other female.

Worst of all is that I fantasise about being fucked back into womanhood by a misogynistic man who wants to put me back in my place.

I lost my virginity in college. Prior to that, I only had messed around with two women, but didn't have actual sex with. First one was my first gf - I got a few hand jobs, and a single, awkward bj, before we broke up.

Now, the second one was something different.

It was the summer before college, and I was spending it at my grand parents house. They lived in a small house, on the Mediterranean, and I would always spend my summers there. Now, this might sound like a confession of a super rich man, to a non European, but my mom originated from this little place, and my grand parents lived there all of their lives. So, not being rich, every summer, I would do kind of a house and yard work, on neighboring houses that are usually rented weekly, you know the drill.

In one of the small, stone houses, there was a woman, with her husband, but he traveled back and forth to the city, being there mostly on the weekends, and she stayed almost all through July and August.

Now, when you are 19, you imagine a 50 year old woman, as this old, wrinkled up granny. No, she was all the opposite of that, slim, petite, beautiful blonde, and she was so obviously a big city woman, you could see it, by the way she dressed, acted, her accent, and peculiar choice of wine she would drink, all day, every day. I thought about her a lot, since, she would sunbathe topless, when I am around, not caring about my gazes. I remember finding that strange, but on the second thought, she was sunbathing on this stone patio, that got out straight to the sea, so people swimming or passing by in their boats, could see her as well. Her tits were very small, but still firm, and I thought about them, as soon as I would go home, and was by myself.

She was giving me attention, only I would think that I was imagining it. She would suddenly have something to do in the house, while I was cleaning, sometimes in a dress, usually just in a bikini bottom. Now, in retrospect, I was a perfect target for a summer fling, I was young, I looked good, from all the work I put on, tanned from exposure to the sun.

I kissed her one afternoon, when she had to go into the cupboard, at the time I was in it, and it was obvious she just wanted to initiate something. We were in the bed, and when I got down on her (only sexual thing I did before and felt comfortable doing, wanting to show that I am not some schmuck, but a seasoned lover), I saw that she had nothing under her dress. Her pussy was bald and perfect, and she came really, really fast.

As I took my shorts down, ready for more, I guess she came to her senses, and asked me to stop. She said she is sorry, but that I have to go.

You can imagine the blue balls I had that day.

Tomorrow, she acted if nothing has ever happened.

The day after, her husband came back.

And that was it. I thought about that woman, for solid five years, at first, every night, then once a week, than monthly. This morning, I remembered her again, and decided to write this.

Finally did it!! I managed to fuck my wife’s sister. Happened at the end of a family party at the sisters house. Everyone had quite a bit to drink and before leaving had to get my wife’s coat in the spare room but made out I couldn’t find it and asked her sister to help me look for it!

She was wearing tight jeans with a top that had multiple string ties at the back include one that came from the front round her neck. Obvious to see she wasn’t wearing a bra! Looked around and eventually found coat, but before leaving I closed the door and asked her if I could see her tits. She told me to shut up and move away from the door! I persisted and tried teasing her by lightly pulling on the top to try see down the front. She pushed me away and stepped back, as I fell seated on the bed. She gave out a big sigh, and then pulled the neck string over her head, holding her tits at the same time. She said it was just a quick flash and dropped her top!! They were beautiful!

She’s 50yo, but her tits are still great, not saggy at all. Nice pale aerola and hard nipples, with some light freckles. My cock was fucking rock hard!

I asked her if I could touch them but she said no, however she stepped forward slightly and took the chance and grabbed her tits. She gasped in surprise, but didn’t step away, in fact she moved a bit closer. I took a further chance and started kissing and sucking on one. She said no and tried to push me away, but I wasn’t for it. Kept going and her protest stopped and she started to lightly moan as she clasped the back of my head.

I started to rub her pussy through her jeans again gasping in surprise and even jumped with the shock! Still sucking her tits I undid her jeans and pulled them down along with her underwear. Her pussy smelt amazing and she had tiny tuft of red hair above her pussy.

I stood up and pushed her onto the bed on all fours with her ass in the air. I spread her ass and starting licking her pussy and ass hole. She was so wet it was amazing. I got my cock out which was flowing with pre-cum and eased my cock into her ass. It was so fucking tight! She told me to stop because it was too painful - her man doesn’t fuck her ass!! She told me to put it in her pussy, which gladly did - it was so wet and hot! I’ll be honest I didn’t last long - my fantasy had come true after 20 years!! She told me not to cum in her, so pulled out just in time and shot a massive load over her ass and back!

She got a towel from the cupboard and cleaned herself up, got dressed and both went downstairs with my wife’s coat - no one else any wiser!