I was a homeless teen for around 18 months. Just as I turned 18 I found accomodation thru a local charity that supported me to turn my life around. Whilst this was very kind of them, I didn't have a steady income to allow me to support myself and to allow myself to keep paying for the accommodation long term..I decided to browse Craigslist for job opportunities, I applied for a range of vacancies, from office work to retail to more risque activities.

I applied for a post that required a naked waiter for a one off party selling Ann Summers toys. I applied with an enthusiastic cover letter, and a photo. I was swiftly responded to by a guy who said sadly you aren't the sort of guy we are looking for. I don't even believe I responded as I felt the sheer cheek of his response didn't deserve a reply. However clearly they found no one else as a few days later I received another email saying, we have reconsidered and wondered if you would still be willing to be a naked waiter at the party this Saturday. I of course said yes, I needed the cash. I was requested to wear a thong and a bowtie. I didn't even know where to buy the latter so I asked them to supply that. I went to a local discount clothing store and bought a thong. It didn't cover very much, neither front or back. Well that didn't actually matter. The first event went so well due to my foolish confidence of youth and many drunk ladies not being fussy, that I ended up with more and more bookings and for around 2 years, this was a job.

Now the specific night I am referring to in the title was only a few months into this job. I hadn't done loads of parties, and whilst things had gone further than just waiting a fair few times, this was where my confidence raised high enough whereby I was ready to say let's go and do this.

It was a make up selling party for a group of women, all around 35 - 65. I would say there were probably 12-15. It was a fairly standard evening, I was waiting, thongless, as had been the case since an hour into the first night. Waiting for 12-15 as the only waiter is quite hard work and after the first couple of rounds of drinks and nibbles. I was taking a break out the back whilst they conversed and got more and more tipsy. That much alcohol in a short space of time went to their head and their bladder and they had to go to the toilet a lot. You had to walk past by setup area to get to the toilet so they all saw me. I couldn't rest that much as I had to be on as they saw me.

This one lady walked past, she was in her mid 50's, she had very short hair, rather impressive boobs under a turtle neck jumper, and a pair of tights work trousers. I turned away getting glasses together as she walked past and she pinched my bum smiling a big smile. This was nothing in the grand scheme of what goes down with naked waiters. She went to the toilet, and then walked straight back out to the party.

I served some more food and drinks and well everyone was tipsy and the lady running this party was selling so much make up by the looks of things. Once the food runs out, I basically kept walking around serving drinks until the drinks run out or the night ends. Now this lady who I mentioned before was flirting a lot as I was serving drinks. She was a little hands on and I playfully touched her leg in return. She was sweet and actually quite hot for her age. She had that naughty look in her eye.

I took the empty glasses out the back and her friend was walking behind me. I assumed to the toilet. Instead, it was to talk to me. She told me, do you like my friend, meaning the lady I mentioned. I said she seems like a lovely lady, nice smile. I found out she had recently recovered from.what was thought to be incurable cancer, (hence the short hair), her husband and her had a horrific row whereby he said Go on leave, no one will have you now. The friend said, so it's nice for her to be flirted with. I made it clear that I wasn't just doing it is my job, but because she is an attractive woman. I decided to show the husband something.

I went out and served more drinks. The lady who had a horrific husband was actually just getting up to go to the toilet again. I served the drinks, flirting with her as.she was stood.up, resting my hand on her ass, whilst joking with her. We both walked out the back together, and I let her go to the toilet. As she came back out, I started talking to her, and flirting, she playfully had her hands on my waist and mine on hers. I slid my hand down on to her ass and said come with me. She came with me to the room where I get changed in advance of the event. I kissed her the moment we got in and she passionately responded. She had her hands all over me, and.i started to strip her, really enjoying my hands on her boobs and ass. She turned around and said fuck me. As if I had any other plan. We fucked vigorously for around 10 minutes as I played with her clit. She came, but I decided to not as it would affect my job the rest of the evening. She got dressed and we kissed bye. She tried to unruffle her hair and went to sit back out till the party ended. I don't know if she told anyone however I feel some knew. This woman came to a few more events in my two years but nothing as exciting happened as that time. I hope it showed her that she was hot, as she really was.