During the time I had started my personal slut journey, I was also still enjoying the company of paid professionals myself. One of these was a regular for me, and her and I talked about the "working" aspect of the nightlife. She was a little shocked that I also "worked" a little on the side. She had asked me about the "clientele" I attracted, and I told her it's been men so far. She excitedly replied "You're bi?? That's SOOO hot!" Apparently she was into guys with guys. I never got to demonstrate for her, but I digress...

I had asked her about any guys she knew of that would be interested in me, and she had directed me to a certain vehicle at a certain place almost every night. She knew he was gay as she tried to accompany him, but he told her he was looking for male companionship. So I said I'd give it a try and see how it goes. This is the story of him.

I walked around that street a few times until that car showed up. Very high-end Cadillac with very dark tinted windows. The passenger side window was down, so as I walked past, I waved at him, smiled, and walked on. I was already hard with anticipation, and the shorts I had on were somewhat tight, and I adjusted myself so I'd stick straight out in front of me to show it off. And I turned sideways in front of his car so he'd have a good view, and I stretched backwards a bit to accentuate the "pointing". I then kept walking away to see his next move, which didn't take long.

He started the car and drove for a bit to get back in front of me, and stopped to park again. I caught up to him, passenger window still down, so I stopped and asked him "Is there something you're looking for that I might be able to help you find?" He looked at me and said "Big dick".

I'll admit, I'm not hung like a horse. Maybe 6 inches on a good day, so I figured I was too "small" for him, and told him so. "I'm only 6 inches, so I'm probably not what you'd want" and I walked off. It was a long section of street, so before I made it to the corner to walk another direction, he pulls up and stops just in front of me again. I look at him and he says "I'm sorry, I shouldn't have said that so harshly. I was actually looking for another guy who usually walks here that I've talked to before." He goes on to describe him, and it is actually a guy I know, and I've messed around with him before, and he IS big. Like 9 inches big. Anyway...

I tell him "Yeah I know him. He's on (such and such) street tonight. I have his number, I can call him for you." So I call that guy and tell him his regular in the Caddy is looking for him. He said he had other plans for the night and wasn't available (I had him on speaker for Caddy to hear and talk to him). So Caddy said "Well, ok. Is this guy here any good?" And niner (I'll call him that cuz of 9 inch cock) says "Yeah, he's a great guy. Damn nice cock if you ask me." So Caddy says "Ok" and I hang up. Caddy looks at me, I look at him, and Caddy says "Hop on in, we'll talk some before I decide anything." I said ok and got in.

He drives around and we talk for a bit. Caddy tells me he's a total bottom, doesn't even get hard, prefers to be treated like a gf, loves giving oral and receiving anal, and he's not afraid to pay for good sex. I tell him I'm a top, but I do suck dick if it's pretty (lol), have been known to kiss too. I then said "Do you want to see it so you know if you'd like it?" He said "Yes please", so I pulled it out and I'm hard as a rock. Caddy looks at it and says "That IS a nice cock! Can I hold it to see how thick it is?" I said "Sure, but if you start jerking, I'll enjoy it and need some dollars lol." He laughed and took his hand and grabbed it to hold it. Hes a smaller guy, about 5'4", small framed, and older. About 60 or so. His hand was so soft, it felt really good. Caddy said "Yeah, I want this. It'll feel really good in my mouth" which made me throb.

We pull into a parking garage and that's when it hit me WHY the windows were so dark tinted. Can't see shit inside at night. We talk a little more after parking and he tells me he's a successful business man, has a big house he owns in a different county, and has loved cock all his life, just never found the right guy to settle down with which is why he "shops around" for company. I tell him about me a bit, that I'm bi and do still love the pussy too. He said he understood. He then asks me how much to suck me off, and I tell him $40, so he pulls $40 out, hands it to me, and I pull my shorts down.

Caddy leans over and rubs his face in my bush a bit (I didn't shave at this time), and rubs his face on my cock. I asked him "Is there anything you want me to do for you while you suck?" Caddy looked at me and said "Could you talk to me like I'm your girlfriend? Dirty talk too if you want to?" So I said "Yeah, I can do that." Caddy said "You can hold my head and all, just don't force it down my throat. I can't deepthroat no matter how hard I've tried." I said "Ok, that's no problem. I'm not into forcing cock down throats anyway. This is just as much for your pleasure as it is mine." He smiled, grabbed my cock, and kissed it all over before licking the precum off that had started running all over myself.

He then started to put me in his mouth, and I swear it FELT like a woman doing it. So gentle, so soft, so "caring" as he took in as much as he could. I couldn't help it and let out a moan saying "Damn baby, that feels really good." Caddy only stopped long enough to smile at me and say "Thank you. I try." and went back to sucking slow and deep. I put my hand on his head, not to force or move him a certain way, but just so he felt my hand there, and he started moaning. And yes, it vibrated me and DAMN. I let out another moan and say "OMG honey, I won't last long if you suck my cock any better. Damn baby." and apparently this took him to another level. He started moaning and sucking like a wild animal which drove me absolutely nuts. I'm moaning and grunting and the dirty came out... "Yeah baby, suck that cock like a good girl. Make your man cum for you." and this made him sexually ballistic. I've never had a blowjob so intense that I stopped breathing. I did on this one.

I'm getting so into it, I'm rubbing his head, neck, and back, and I'm grunting and groaning like a beast telling him "I'm so close baby, don't stop. Be my good girl and suck me dry" and Caddy continued to jackhammer my cock with his mouth and tongue until I said "I'm gonna cum, I'm gonna... ugh UGH" and blew so hard it hurt. My legs shook. And Caddy is sucking it all down. I've got my hand on his head, petting him and telling him "Damn. My god. I don't want to stop cumming" and Caddy never stopped sucking. Finally the last of it was out and I started to get over-sensitive, and then Caddy stopped. He's looking at me while he swallows the last drop, licks his lips, smiles and says "Damn. You really DO have good dick. I'm so glad I gave you a chance" and would lick my tip as any more leftovers seeped out. He looks at me again and says "Thank you for calling me a good girl and baby. I really liked that too."

He sits back on his side of the car, I'm struggling to move properly to get my shorts back on, gave up and said "Guess I'll just sit here with my cock out till I find my brains again. I think you sucked them outta me." And he laughed hard and said "Thank you! That's the nicest thing a guy has said to me in awhile." We sat there for about a half hour just shooting the breeze about our lives, our dreams and hopes, and Caddy pulls out $40 more and says "I want your babies in my mouth again." I looked at him and said "Normally I can go 2 or 3 rounds no problem, but you too good girl, you sucked the life outta me. I'll let you try for free tho if you think you can get me hard again."

And he tried. And he did. It hurt at first, but then there we were, like the first time, all the noises, all the words, and this time he wrapped his hands around my waist as I was about to cum so he could feel my sides and butt flexing with every throb. He really loved it, and I had no complaints either lol. When the last drop came out and he swallowed it, he just looked at my cock close, kissed it, licked it, and said "I love your cock. I wish I could bring you home with me so I can sleep with it on my ass." I said "If I slept with my cock on your ass, I'd probably wind up IN it" to which he smiled and said "God I hope so. I would love for you to fuck me and get me pregnant every time you got hard." And I said "I would definitely try. A lot."

But the hour was late, he had to go, knew I had to stay, so he said "I'm going to come back tomorrow evening. Will you be available?" I said "For you, yes. I'll even take the day off from being with anyone else so I'm full and ready for you." Caddy smiled so big and said "OH, before I forget..." and handed me another $40 for the 2nd bj. "I don't want to take advantage of you, financially anyway. But if I could, I'd tie you to my bed and keep you in my ass for hours!" I said "Damn baby, don't threaten ME with a good time" and we both laughed. He drove me back to the street he found me at, dropped me off, and said "I'll see you tomorrow, sexy." I said "I'll be waiting for you honey" and blew a kiss at him.

This goes a lot longer, so I'll stop here and make a part 2 post to this story. Also, forgive any typos as I don't check often in long stories... I'm too busy writing it down before the details slip away.