Escorts, Hookers & Whores, Oh My!

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Some of my first experiences with escorts.
1.9k words
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Part 1 of the 6 part series

Updated 05/01/2024
Created 04/26/2024
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It's a sad state of affairs when a man reaches a point in his life, usually middle age, and he becomes desperate enough to seek the services of an escort, hooker, whore, or "service provider" as they are often called.

And so it goes that I searched online for escorts, found a site with good looking girls and women and began to hook up with them.

SOPHIE

The first girl who accept my text and arranged for me to visit (for a fee of course) was a girl about 30 years old, brown hair, average looks but with big tits and really nice legs. I had a fantasy of maybe getting a juicy tit fuck sometime with a girl who had tits like that.

Sophie operated out of a hotel room, changing hotels weekly for obvious reasons. She asked for the "donation" before she let me inside her room. Once inside, it was strictly business.

"What'll it be, hand job, blowjob, or fuck? I don't do anal," she said.

"I want to eat you, have you suck on me for a bit and then ride my cock until I come," I answered.

"No problem," she said as she undressed and lay on the bed. I positioned her down near the edge of the bed so I could kneel on the floor while I licked her. She put her feet on the edge of the bed. She wasn't wet when I started licking her, but she got very wet and I'm certain she had a genuine orgasm when I licked her clit.

"That was really good, thanks," she said, which let me to believe that she probably actually did come.

I lay on the bed on my back while she fetched a condom. She played with my cock until it started to get hard, then she slipped the condom on it. To my surprise, she didn't get on the bed but just leaned over and started sucking my cock.

I'd never heard of anybody sucking a cock with a condom on it, but it actually felt pretty good. I let her have her way with me until it was too late and i emptied my load into the condom. She pumped my cock a few times with her hand, then slipped off the condom and dropped it in a trash can.

"Any chance of actually getting fucked like I wanted?" I asked, pretty sure that I knew the answer.

"If you want to give me another donation, I'll give you a few minutes to get hard and then we can do it."

So, I chalked that experience up to another lesson learned and moved on.

DAISY

The second girl I visited was a 27 year old Latina girl. She had dark eyes, long dark hair, average breasts but was very pretty. Her legs were a bit "thick" but she seemed to have a fun personality when we chatted after my arrival.

Daisy lived in her own home, left to her by a relative who recently passed away. As is the custom, I left an envelope containing my "donation" on a table in clear sight before we began talking. When it came time to "take care of business", she led me to her bedroom, and as we undressed, she asked for my preference(s).

"What would you like and how would you like it?"

"I'd like some sex like in porno films," I boldly admitted.

"Like what?" she asked.

"I'd like you to 69 me but don't let me come until you do, or until you pretend to."

"And then?"

"Then I'd like you to mount my cock and fuck me slowly until I come."

"Okay, but no glove, no love, Baby," she warned.

She reached over to the night stand by her bed and retrieved a condom and set it on the bed next to my body. I lay back on her bed and stretched out on my back. She climbed over me on all fours, straddling my body, ready to assume a 69 position.

Her fingernails lightly scratched my scrotum as her mouth literally devoured my cock. I reached for her hips to pull her body down so I could put my mouth on her, but she only let me pull her a bit closer. I could see her vagina but could not reach it with my face.

As I was struggling to get her close enough to lick her, her mouth and tongue were doing things to my cock that I had never felt before. I didn't think that I was very horny, but before I could get her body down onto my face, I came in her mouth. To my surprise, she did not stop sucking, keeping her mouth slamming up and down on my shaft. It was the best blowjob of my life.

She had taken quick control and sucked me off before I could help myself. She licked me clean and when she got off the bed, I asked her to keep me hard and to fuck me.

"Sorry, Baby, one pop and I stop," she said. I tried to tactfully argue with her, but she would not give in, so I got dressed and left. I made a note to myself to make sure I wasn't horny the next time I paid for sex.

MIA

The next girl I visited was black, but actually her skin was a beautiful chocolate shade. She had long hair tied up in braids on top of her head. She had jet black eyes, small tits but gorgeous legs and ass.

She lived and worked out of her apartment. She had a ferret named Moe that rarely was let out of its cage. Mia was a 34 year old proud, poised and confident black woman who liked to travel with her clients. we had a comfortable chat, and when it was time to move into her bedroom, she was very smooth.

"What made you decide to contact me?" she asked.

"You have an incredible body," I honestly answered.

"What are your sexual interests?"

"I love licking and tasting a woman, and sometimes like getting my face in her ass. Oh, and I like being fucked. Not fucking, but BEING fucked."

"You want to be dominated?"

"No, not necessarily but that might be hot."

"Are you here to see what it is like to eat and fuck a black woman?"

"No, I'm here because you have a great body, and yeah, I do want to eat you but as I said, I prefer to BE fucked."

"Do you watch much porn?" she asked.

"Quite a bit, when I have time."

She looked at me for a moment and began undressing. "Okay, get undressed and lie on the bed."

When I was on the bed, she took some scarves from a dresser drawer. She tied my ankles together as she explained what she was doing.

"I can read my clients pretty well, so I know what you really want. Just relax and let me take over; you won't regret it."

She tied my wrists together and then climbed up on the bed, her knees straddling my head. She slid her pussy into my face and I tried to lick her, but she began rubbing her pussy back and forth across my face.

She sat up there, fucking my face, moving faster and grinding down harder. She grabbed my hair and my cock was rock hard. She rode my face for a long time, moaning loudly and then pretended to come. I knew she was pretending because she was hardly wet.

She climbed off of me, turned around and lay down on top of me in a 69, her thighs firmly pressed against the sides of my face. Then I felt her mouth on my cock and she slowly sucked it until I moaned into her pussy with an urgent need to come. She teased and tortured my cock until I jerked my hips and filled her mouth with cum. Her mouth never left my cock until I was done.

She rolled off of me, untied the scarves and explained. "From what you said, I thought you wanted the Porn Star Experience, you know, the typical thing, tie the guy up, sit on his face and come and then suck him off."

"Well, I have to say that I did enjoy that, but I really wanted to be fucked."

"Next time, Dearie, you'll love my tight pussy."

"Can I play with your ass next time?"

"You can smell it, lick it or eat it but you can't fuck it."

I did go back to visit Mia again. I had a great time licking her beautiful black ass. When I asked, she let me drink some of her piss but not from the source. She let me hold a champagne glass while she pissed into it, and then I drank it. She rode my cock and gave me the best fuck of my life.

BRITTANY

The next girl I visited was 29 and blonde, with a cute face and a nice body. She also operated out of various hotel rooms. We had the usual "get acquainted" talk and then we got down to business. It was obvious that Brittany either liked her work or wanted customers to come back. She sat near the head of the bed while I stretched out on my stomach between her legs and licked her.

I took my time and enjoyed it because she got really wet, moaned while I ate her, touched my face and finally came. Her lower body got tense and I felt that she really had an orgasm. She crossed her thighs, pushing my face away from her. "It's sensitive, give me a minute," she said.

I wasn't sure what she wanted but in a couple minutes she opened her legs and pulled my face back into her pussy. So, I ate her some more and she came again. When she was done, she said, "Guys don't usually eat me long enough or well enough for me to come, so I wanted a little more; I hope you didn't mind doing it again?"

Then I sat on the edge of the bed and she sucked on me until I was ready, then she mounted my lap. I asked if she was going to use a condom and she said, "Just tell me when you're gonna come."

I lay back on the bed while she took her time riding my erection, and I felt that I was finally getting my money's worth. When I could no longer hold back, I warned her, and she lifted off of me and got on her knees. She shoved her mouth down over my cock just as I spewed my load.

When I was done, she opened her mouth to show my cum and then spit it on my cock and sucked it some more, sliding my cum all over my shaft and balls. Needless to say, I DID go back to see Brittany several times. The second time, she 69'd me until we both came twice. The third time, she let me lick her ass and I licked her right after she pissed in the toilet, then I fucked her from behind. The fourth time she pissed in my mouth, I licked her until she came and then I fucked her ass.

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