I don't have too many story worthy sexual encounters but I recently went back to the hotel where I had my first job as a barman at 18 and it reminded me of my old boss (who isn't there any more unfortunately).

She was in her early 40s, quite short, kinda chubby and had the biggest boobs I've seen in person to this day. She also had a daughter who was a year younger than me but I never met her thankfully, that would've been awkward.

Because it was a hotel the bar would stay open very late, we would regularly finish at 6am and sometimes later. So some nights when the shift was over my boss would stay in the hotel if she had an early start in the morning. The first time we fucked she asked me to walk her to her room as we were deep in conversation, which I happily obliged, she then invited me in for "tea". We went inside, I sat on the bed and she sat down very close to me, she started taking off her shoes and gave out that her feet hurt, telling me she wished someone would rub them for her. I took the hint and offered to rub them, she was so happy, moaning sexually as I did it, to seal the deal she lifted her foot up and rubbed her big toe against my lips, I didn't even care that they would be gross after a long shift, I opened my mouth slightly and she put her toe into my mouth. I sucked on it happily as she took off her blouse, saying how warm it was in the room, she asked me did I mind if she took off her bra too, which I of course told her I didn't at all. Next thing I knew she grabbed me by my hair and lifted my head up to suck on her tits. I was in heaven!

She was quite forceful, but not dominating. She stripped me down and complimented my cock, saying how big it was, and before I knew it my face was buried between her legs, she was holding my face tight to her pussy with her hands and moaning so loud, she clearly had to blow off some steam. I ate her out for what felt like a long time, she told me she was cumming four times, (I'm naturally gifted with my tongue apparently). Her pussy tasted so good though so I didn't mind. She then returned the favour and took my cock into her mouth, I remember her telling me that it needs to be really wet because she is tight. To this day it is the best bj I've ever gotten. She was licking up and down my cock, taking as much of it into her mouth as she could, she sucked and licked my balls, put my cock between her tits so I could fuck them while she licked the head, it was so fucking good, I miss those blowjobs.

Eventually we got to fucking, which was probably the most boring part honestly, I got on top at first and fucked her missionary, we made out a lot and it was more wholesome for a change, and then she asked if we could do it doggy style. She bent over and I remember being amazed at how huge her ass was, I found it so fucking sexy, I slid my cock into her pussy and started fucking her, she kept saying "harder... harder" and I would oblige. We did this for about 3 or 4 minutes before I couldn't hold it in any longer and I came hard inside her without even asking if it was ok, but then the hottest thing of the whole night happened, she told me it was ok, then she rubbed her fingers on her pussy, scooped up some cum and sucked it straight into here mouth, she then told me something along the lines of, "I haven't tasted a young man's cum in years". I asked her if it tasted good and she told me it did.

After all this she invited me into the shower to clean the sweat off, we made out a lot and just touched each other all over in the shower. Then she thanked me, told me we should do this again and I left.

This was the first of many times we did this, we worked together for 3 years and I'd say we would have a good fucking session once every 2 weeks maybe, sometimes more. We tried a lot of different things, a lot of them being my first time, and every time both of us ended up happy.

As a result of this relationship I have developed a serious kink for older women, chubby women, I can't have a female superior without wanting to take them to bed (an urge I obviously resist), and experienced, confident women who know what they want.

She actually wasn't the only person I ever fucked in that job, but that's a story for another day...

Anyway if you made it this far thanks for reading! I've had this on my mind for a while and I had to get it out. If anyone has any questions or wants to chat about the story feel free to DM me or comment! Also yes this is true, and I didn't embellish any part of the story.