In my last post, only yesterday, I mentioned that I had some things going on that you might be interested in reading about and as one of them is fresh in my mind I thought I would write about it.
As some of you know, among my wide and varied kinks is a love of being used sexually by complete strangers especially when I am never going to meet that person again and I have also developed a fetish for doing “dirty” things, by which I mean things that I find truly disgusting but am inexplicably turned on by doing. (In actual fact it’s not inexplicable I just don’t feel a need to explain it here and now!).
So, bearing the above in mind, I’ve had this recurring ideal (fantasy I guess) about approaching a homeless guy and offering to perform a sex act on him. For me it would be deeply humiliating and disgusting to suck a dirty homeless stranger’s cock and swallow his cum and for him, well, I’m told I give pretty good head.
Just to clarify, the reason for it being a homeless person is not because I believe people who are homeless are in any way “lesser” than myself, it is simply that they are guaranteed to be a stranger (I don’t know anyone who is homeless, yet) and they are likely to be less clean than your average guy which appeals also.
My problem with bringing this fantasy to reality has always been concerns over my safety, he could be a crazy homeless person, those exist and he may try and hurt me or take things further than I want to. Although the latter is another fantasy of mine it is one that I don’t think you could ever safely fulfil.
I was talking with someone about this fantasy online the other day and they suggested a way to make it a little more viable. Basically the plan was to find someone and approach them with a cup of coffee (or other tasty beverage!) and sit and talk to them a little, assuming they don’t seem like a psychopath I would then steer the conversation onto my kinks and eventually make my proposal. The suggestion was made that I also offer them money, this is less as an incentive for them (although I’m sure it would be) and more as an additional humiliation for me, I would actually be paying to degrade myself in this way.
I already had someone in mind that I know sleeps in an alley behind a restaurant on the other side of the town to where I work, it’s somewhere I pass by often enough to know he resides there but not somewhere I have ever been with friends or colleagues so it’s unlikely I would be recognised there in the unlikely even that we were caught in the act.
After the conversation I was horny enough, and had built up enough confidence to put the plan into action so after work I went to a coffee shop and hung around for an hour or so until all the work crowd had headed home then I bought a couple of coffees to go and headed to where I thought I would find my “candidate”.
The man I had in mind had been homeless for at least a year that I knew of, or at least that’s how long I’ve been seeing him around. He looked to be in his mid forties, had brown hair and beard both of which were usually matted and he usually wore dirty clothes and a long coat, he usually has some form of strong alcoholic drink with him. He is who I’d dreamt about before when I’d pleasure myself to the fantasy of being forced to pleasure a “tramp”.
I looked for him first down the alley where I’d seen him sleeping a few times but he wasn’t there so I looked down the surrounding streets and eventually wondered into a small park that is nearby. The man was sitting on a bench not far into the park with a beer can in his hand.
I nervously walked up and sat down next to him, he said nothing so eventually I plucked up the courage and said “here, I got you this” and held out the coffee. He turned and looked at me blankly for a second and then smiled and said “thank you” before putting the can down on the floor and taking the coffee from me, his fingers felt greasy when they touched mine around the cup.
We both took a sip from our drinks, I was hoping he would start talking but when he didn’t I pushed on, told him my name and ask his. He told me and then I just started talking, about the weather obviously, what else do you talk to strangers about?! He started to loosen up and join the conversation, I told him I hoped he like the coffee and that I didn’t know what he liked so just got the same as me, a vanilla skinny latte, he joked that he didn’t really need to watch his weight.He didn’t question WHY had bought him a coffee and come to speak to him but I’m sure he must have been wondering.
He didn’t have to wonder too long though because I was just about getting to a point where I was ready to reveal my proposal to him. My heart was pounding really fast and my pussy was wet as I started by telling him that I was “a bit kinky” and that I liked to do somewhat unusual things that turn me on. I asked him if he knew about BDSM and he said he knew a bit but had never done anything BDSM related.
I was blushing crazily (for those that don’t know I’m a terrible blusher!) as I was telling him this and even more so when I started to tell him that I have this fantasy of paying a complete stranger to allow me to pleasure them sexually and that I would enjoy them humiliating me by peeing in my mouth as well. I don’t know what he was thinking when I was saying all of this, he didn’t speak and just had a sort of knowing smile on his face.
Eventually, after rambling for some time I got to the point, I told him that I wanted to give him £100 and that in return I wanted him to let me give him a blow job and swallow his cum, then I wanted him to piss into my mouth and on my face, then I would leave. He took it almost in his stride, he was smiling and responded with “are you serious”.
I told him I was and we talked a little about the detail of what I wanted him to do, he asked me if I was police and I assured him I wasn’t and that it was just something I’d always wanted to do and it was really win-win for him. He eventually agreed but said that he couldn’t do it that night as he had somewhere to be and that if he was going to do it he’d want the cash in advance. I agreed to those terms and we arrange to meet at the same time the next day in the alleyway where he usually sleeps.
I was pretty nervous about the whole thing the next day, I’d dressed for work in some pale Victoria’s Secret underwear, black tights, white blouse and a grey skirt suit and I was wearing some black heels.
Work went by uneventfully and then I head back to the coffee shop to wait for the allotted time, stopping at a cash machine on the way to collect his payment. I seriously considered chickening out while I waited and then it occurred to me that my car was parked quite a walk away and if I went through with it I’d have to walk all the way through town covered in pee! I decided to go and get my car and park it near to the alleyway and once I’d done that I was out of time to worry about whether I would go through with it or not.
I was half expecting to find the alley empty and at first I thought I’d been right to think that but as I went further down I found him around the side of the large bins used by the restaurant that backed onto the alley. I’m not entirely sure why he chose to sleep there because there was split bin bags on the floor with food coming out of them and the bins stunk of rotting food and rubbish. Anyway he was sat on a bunch of blankets, what I assume was his bed, and looked up as I approach and smiled.
“I thought you were full of shit” he said and I blushed and responded “nope” as he got up and stood in front of me. He was wearing the same clothes as I always saw him in, grubby jeans that were originally blue but were now mostly grey, a black t-shirt with a very faded band logo on the front (no idea which band) and a unzipped hoodie which was originally light grey I think, he also wore some trainers with no laces. He said “Do you have the money?”.
I’d left my bag in the car and had the cash rolled up in my hot little hand, I handed it to him and he took it and counted it while I stood there waiting, blushing. Once he was satisfied he pushed the money into his pocket, at this point I half expected him to tell me to leave, I mean what could I have done? Instead he leant back into the corner between the wall and the big bin and gestured for me to start.
I don’t know what I had expected, I think I thought he would get it out or push me to my knees or initiate it in some way, I guess I’m just used to doing things like this with naturally dominant people who take control from the start, I was certainly feeling pretty submissive and my pussy was already soaking the lace of my expensive underwear.
I took a quick look around to make sure no one was there and then I knelt on the floor and reached up to unbutton his grubby jeans. He made no effort to help or hinder me, he simply placed his hands on the wall and bin and watched me as unfastened the button and pulled the zip down. He wasn’t wearing underwear and there was an immediate smell of…well I don’t know how to describe it, it was just a dirty unwashed smell. I reached in and pulled out his semi erect cock which wasn’t huge but wasn’t small either, it was clearly unclean though.
Gripping my hand around the base of it I opened my mouth and took the whole thing in, closing my lips and sucking as I pulled my lips along his length until only the head was still in my mouth and then I ran my tongue over the head in circles before plunging it deep into my mouth again.
I was so horny now and my pussy was dripping wet, so was he evidently as my attentions caused his cock to grow fully erect and I reached into his filthy jeans and cupped his balls as my other hand ran up and down his shaft and I sucked on the head. He lasted about two minutes before I felt him begin to twitch and I made sure my lips were tight around him as he came in my mouth.
There was a lot of it and I couldn’t help but let some spill out of the sides of my mouth and run down my chin before dripping onto my clothes. When I thought he was done I closed my lips as I pulled his cock out of my mouth and then looked up at him but he wasn’t looking, his head was back and his eyes closed. I swallowed the mouthful of cum and then took his cock in again and made sure I’d left it clean, a lot cleaner than it had been before! Then I used my fingers to push the cum on my chin into my mouth as well.
I knelt in front of him for a good minutes, my hands on my thighs desperate to touch myself but not wanting to do it there. Eventually he spoke, “and now you want me to pee on you?” he asked quizzically, I blushed and nodded. His cock was still out but going soft now, he said “Go between the bins, I don’t want it on my stuff” so I got up off my knees and moved into the small gap between the bins, there was a lot of gross food stuff on the floor so I sort of squatted there but he said “no, put your ass on the floor” so I reluctantly let my ass fall to the floor into the mess and sat there with my legs spread in front of him, I could feel the wetness of the food mess soaking through my skirt, tights and underwear.
I was blushing crimson as I looked at him and opened my mouth ready for him to pee into, he didn’t though. He took his cock in his hand and as he started to pee he aimed it at the top of my head and then moved the stream down my face and my chest and then ended it peeing directly onto my pussy, which actually felt quite good!
When he was finished I was soaked all down my front, my hair, my blouse, my skirt, it was everywhere. I looked up at him and wiped my eyes, I was expecting to see glee in his face but he just looked confused, then he put himself away and disappeared from my view.
I took a moment to compose myself and then stood up and tried to wipe any food waste off my ass. When I walked past him he was curled up in his blankets so I just said “thanks” and carried on walking, out of the alley and to my car. I’d put towels over my seat (always thinking ahead!) so I got in my car, took a breath and then set off. I wanted to get away from there but I was so horny so I only drove for a minute and then parked at the deserted back of a store car park.
Pulled my filthy skirt up around my waist I spread my legs and rubbed myself through my tights and wet knickers until very quickly I was cumming.
I hope you enjoyed reading about this, it is something I’ve wanted to try for such a long time and really scratched an itch I’ve been having recently. I know it’s fucked up but so am I!
Please feel free to comment, I always try and reply and really enjoy reading what people have to say x