Dirty

I was in a hotel out of town (you know a lot of my stories are out of order, right?). I had a time limit due to scheduled activities, but got hit on by a guy who claimed to be beefy and muscular – and the image he used verified that. Slightly older, but nothing undoable. The pic of his cock was nice and fat. I do love girth. His body type seemed heavy but not fat.

Pictures lie.

While the body type was not my type, depending on the personality (and the dick!) I can work with that. This guy’s personality, when he showed, was just overpowering, but not in a good way. He kind of barged in, started making demands and not necessarily sexual ones. He was definitely heavier than he portrayed – much heavier.

The bad thing was, I knew it would not be easy to get him to leave. He was the kind of guy who missed all the social queues, or ignored them. On the right kind of guy, that could be hot (the ignoring them). This was not that kind of guy.

I was trying to beg off, due to my social engagement, but his pants were coming off anyways. There stood his fat, but shorter cock. At least he was erect. He wanted me to go down on him, but I knew it wouldn’t be a good situation. It’s one of those things where I’d have to fight his belly to get his cock. Again, I tried to beg off, saying I misjudged the timing. He was having none of it.

Get on the bed….face down. This is where I know I’m slutty. Where I am just a fucking disgusting pig. I figured it would be easier to live through the fuck and get him to go.

I will give him this. He hit the bullseye the first time out. And he POUNDED. These were cheap mattresses on a cheaper stand. He was moving that bed every which way. The hotel was so sleazy and disgusting that none of this would be out of place. Standard operating procedure here. I lay there, basically taking it like a victim, just hoping it would end sooner than later. My lack of interaction and enthusiasm didn’t deter him in the slightest….if he noticed at all.

He lasted longer than I thought he might. But eventually groaned and shot. Then laid there. I’m trying to say I needed to get ready to go……and he just kind of lingered, on me. Then when he did pull off, he wanted to shower. Lord. I tried to tell him the hot water did not work – which wasn’t a lie. He even brought his own towel. Clearly he didn’t care about the water warning. He took one anyway while I bided my time.

He wanted to chat as he dried and changed. I kept looking at my non-existent watch, pretending to get things ready for my departure. This did not spur him on to make haste. Eventually he finally got out of there…..with his own towel in hand. There he went, clean.

Something no soap and water would do for me the rest of the day.

Pimp

I knew one guy from eons back. We’ll call him “Dick”. We fucked around once with his then partner and we just became friends after that. No more sex. I find I normally don’t have sex with friends. And if I become friends with a sex partner, then the sex usually ceases. Maybe that’s weird, but it is the way I am. Dick ended up moving and living out west.

The other guy, “Ben”, I knew from Scruff. I knew he visited here and had some ties to this town, but didn’t live here. He’d blown me in my office on weekend days twice. Nice mouth. Sub boy – the kind that makes me want to be a dom. He has zero idea I suck cock or bend over for strangers. He thinks I’m the kind of guy who uses guys like that. And in his case, he wasn’t wrong. I only knew him from his Scruff handle: B.

In discussions with Ben, he tells me he “dances” on the side for cash. Prodding further, it goes beyond dancing. Always for cash. Allegedly there is no anal, or at least nothing that is not wrapped. Strangers who hire him out – sometimes for weekend gigs. He claims his husband (or partner?) doesn’t know of these activities. Possible, but harder to explain with overnights and weekends. Granted, I don’t think it’s a full time gig, just something he does for fun, in which he gets paid. I totally get that being a rent-boy could be fucking hot.

When he’d hit me up for chat, I’d ask him about his exploits – just because I was curious.

Somewhere over social media Ben somehow came across my path – him reaching out to me. I’m not stupid enough to accept his ‘friend’ request, but I engaged him via messaging. I asked him specifically if he was still renting himself out. He said yes. Though he was quick to follow-up with, “but I’d do you for no charge”. No shit!, was my reply.

He also said he’d like me to pimp him out sometime.

Not knowing the answer, I asked where he resided. It was Arizona. Tucson specifically. My brain immediately went to work. My friend “Dick” lived in Tucson. My friend Dick now is exerting his dom top behavior. I immediately messaged him and asked if I sent something up with Ben would he be into it? He responded in the affirmative.

I reached out to Ben and told him I was pimping him out. Now. And he was doing it for free. He didn’t hesitate to agree. I knew he wouldn’t. We arranged a way for the two of them to communicate that didn’t involve me as the middle man, yet I was to be told by both exactly what was going on. Not so much as to if it would happen, but I was looking at the different perspectives on this doing.

I know being a pimp isn’t this easy. But fuck, I cannot get my own hook-ups to go this easily, or quickly.

The plan was to meet at a certain time at Dick’s place. As it turns out, it would be the garage. The plan was for a certain time, but Ben was delayed enough that Dick nodded off while waiting on him. That annoyed me, though Ben denies it. I know Dick, I trust Dick, so his take to me was true.

From both accounts, the hook-up was marginal at best. That was sad to say for me personally. I wanted a few outcomes from this, so maybe I should have been more specific – though technically I cannot dictate the entire session. It wasn’t a porn and I wasn’t the director.

For Dick, I wanted an amazing experience. One for which he could take charge and just use this guy. I wanted Ben to give him great head and show him an expert time. For Ben, I wanted him just to feel cheap and used – both at my hand, albeit a thousand miles away, and from Dick, my surrogate john.

For me, I’m not quite done with this concept. I’ve always wanted to be pimped out myself, and there has been talk of it, but no action. I wanted to be different and have action, which I provided. But there is a first time for everything and it’s all a learning experience.

Next time I’ll have a different check-list of what to do and what to avoid.

Semi-Spontaneous 3 Way

I wasn’t planning a 3-way. I wasn’t planning anything at all. Except for the fact that two guys blew me off or ghosted me. Fuckers.

One guy contacted me. A little larger than I prefer. I wasn’t saying ‘no’ to him, and then he mentioned a buddy who wanted to get off too. Hmmmm……a 3 way. Without asking stats, I agreed. I said I needed 10 minutes to get home. He said they’d see me in 15. I replied, ‘no. 10!’. They were there in 10.

Guy 1 was as he stated. 6’1”, but roughly 240. Bald, semi-handsome. Guy 2 was 6’ or so, built. No other way to say it but classically handsome. Both maybe 40. I didn’t, and never did, get the relationship. A ‘buddy’ was used in convo, but there was another aspect to it. More than FWB I think, but I can’t say. Relationships are so fluid these days, I should just give up second guessing anything.

The dynamics were all over the place. Depending on the timing, each of us being more submissive or more dominant than the minute before. Each one directing something going on. I don’t think there was much hiding it, but I was way into #2 than #1. But oddly, with both of them, I believe I was #2. They were into each other, I had the place and the ability to watch or be watched. I was a pawn. I wasn’t thrilled with it, but it wouldn’t be the first of last time.

It is the problem with 3-ways. One person is more into one of the other people and it’s disconcerting and even troubling if you’re doing it with a couple. I learned this eons ago when doing it with a couple – one of whom picked me up without telling his partner. It was awkward, and ironically, the partner became one of my best friends………….and is probably reading this right now! And super ironically, he wasn’t the one I was into in that 3 way.

So, everyone blew each other, at least one. Everyone kissed each other, at least once. The handsome one slapped my ass once. I asked him if that’s the best he could do? He showed me a number of times, it wasn’t.  I fucking do love a firm palm on my cheeks.

At one point I said to the hot guy, “sit on my face”. He didn’t hesitate. I was on my back. Him telling me in great detail HOW to eat his ass. He fucking loved my responsiveness. I fucking loved his ass and eating it. Honestly, it’s been a good long time since I ate a butt like that. He was happy to let me keep going. He even stood and leaned over a desk so I could dive deep.

I was on my knees while guy #1 was close by jacking as I blew #2. He told 1 to cum in his mouth. No way, I thought. I pulled my mouth off long enough to say, ‘cum on his cock while I suck him’. This got both of them hot and bothered. I will say this, #1 had great cum control. It all went on the cock. All of it. Then it went all into my mouth, as the cock became cum-slimy with each up and down motion of my cocksucking mouth.

He was way into telling me to eat his buddy’s cum. I was way into eating it. Showing off. Making #2 harder while I sucked.

But sucking him off was not to be. He said he can’t cum that way. But fucking wasn’t even brought up. “Get on your back, again”. I did. He knelt over me jacking his cock right in my face. I talked dirty. His ‘friend’ talked dirty. Enough so that it got him to bust his nut onto my face, into my mouth, into my eye (ugh!). I ate what I could. I always do.

There was no real discussion about me getting off. I would have deferred anyways. They thanked me and left. Now I’m wondering how to get #2 back here on his own.

Mixed Race Hottie

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Boss

He doesn’t like “Sir”, but told me to call him “Boss”.

This I could work with.

“Bruno” was a guy I had been interested in for years. YEARS!!!!

He’d click on my Scruff profile often and then disappear. I could tell by the frequency that he either dropped off-line for weeks / months, or he only was in town infrequently. And then there were the few times I ran into him at my gym. He’d look at me – and I was never sure he put 2+2 together.

Bruno was and wasn’t my type. Bearded – yes (and very much so). Shaved head – yes. Butch – yes. Height – no, as he stood maybe 5’5”. I know I’m buying into a stereotype, but I find it hard for a guy pushing a foot shorter than myself to be ‘the dom’. I knew I could work through this issue. I’m a professional. One that doesn’t get paid for this line of work, but a pro nonetheless.

So over this holiday season, he was around. I reached out and ‘woof’d’ at him. We started to converse, and while he said he was introverted, it did not take much for him to come out his shell. Soon the conversation turned to him wanting to see me suck his cock……….then get bent over. A little more and he was mentioning his leather jacket and Harley boots. Score!

After a bunch of start and stops, I was over at his place. He wanted to kiss. And kiss. And kiss. Sigh.

I’m all about kissing some guys, but this isn’t exactly what I was expecting from this guy. Or really wanted. It was a lot of tongue action. But I was there for him, so I did what was needed and what he wanted. On the plus side – he was a good kisser.

It took a while but soon his hands were on my shoulders pushing to my knees. I know the drill and went while looking up at him. He had on black jeans, and I undid the belt and opened them, which then dropped around his thighs. I mouthed the mound that had been there since I walked in the door. While kissing, I felt it….and felt it again….and again and again. Now it was the width of cotton away from being in my fucking mouth. I pulled them down exposing his 6”. He trembled when I ran my tongue over the head. He jolted as I made my tongue dance across the underside. He moaned when I took it all in my mouth in one motion.

Then he fucked my face. Hands on head. Hips moving expertly. It didn’t take him long to come out of his shell. Introverted, my ass. I went further down and worshipped his black Harley boots. He liked when I licked the black leather. He fucking loved it when I used my tongue on the soles and when I tried to take the tip of the boot in my mouth. He of little height, still looking down at me literally and figuratively. That part, I loved!

Whenever he would ask me something, the answer would include the word, “Boss”. He liked that, I loved it.

But while all of this was all well and good, both of our pre-discussions determined that this was about my ass. It’s what we both wanted – him to fuck it, me to be fucked.

We went upstairs to his bedroom. I loved the bed, as it was tall and high off the ground even for me, so way big for him. But we got down to it. Big time. 6” is a fine cock size, assuming one knows how to use it – but that true of many sized members.

Boss knew how to use it.

The guy was well versed in how to fuck. We would end up doing it on my side, on my back, on my front, sitting on him facing him and away. He had stamina. It got to the point that my hole was just so open for him. And slick, but not full of lube. More like self-lube. He had me excited enough that I was producing my own wetness.

He loved that I was open. He loved the way my hole felt and kept commenting on it. How silky it was. How great it felt to him and his cock. I started feeling self conscious, as I’m not great at accepting compliments. Ironically, this is not the first time I’d heard that during that same week. So my thought was: one guy saying that is him just being nice. But two saying it, well, maybe it’s true. He said it with such passion and conviction, if nothing else, it was true to him.

When I said he had stamina, I meant it. We pushed the two hour mark just at fucking. Edging. Fucking. Edging……….and so on. He wasn’t going to give up his cum that easily, but I figured that out after way, the 40 minutes.

By now my hole was way open and very accommodating. He loved how it blossomed for him. How it made moist sounds and he fucked. I loved that he loved it.

But truth be told, I did have things to do. He laid back to rest a bit and I took matters into my own hand……and butt. I straddled him, held his shaft in place and slid down on to him. He didn’t resist. He didn’t try to stop me. I rode his cock. Nice steady strokes with no relenting. His face said it all. The glaze in his eyes, the upward turn of his lips. He was happy.

While he didn’t say he was going to cum, there are some things a boy knows. The stiffening of the shaft up the pooper is one of them. His grabbing my hips and pushing me down, holding me there, was another. Actually, that was way more telling. So were the moans and the “oh SHIT”, as he fired his guns. Well, yeah, when he came I knew it, just not sure of the before.

I climbed off….eventually. First I had to milk the shaft, with each squeeze he shuddered head to toe. All 5’5” of him. We will get together again. Timing is a bitch, but when he’s in town, arrangements will be made.