Escorts, Hookers & Whores, Oh My! Ch. 03

It was becoming obvious to me that even though I was spending a ridiculous amount of money on strange women, it was not only fun and enjoyable but was almost addictive. What would each girl be like and what would she agree to do?

I drove to another city to visit a friend in the hospital, and that night in the hotel I decided to try to find another girl for some sex and entertainment. The usual source provided the usual options, and I found one I liked.

STACY

The photos in her profile showed her to be blond and very petite. She claimed to be 20 and very short. I found her in a sleezy hotel and I was worried about security, but I went to her room anyway.

Stacy was indeed very petite, almost childlike. I questioned her real age and she showed me her driver license but covered up her real name. She was actually 20 years old, but looked like she could be 16 and that made me uncomfortable.

But she had a pretty face and wore glossy lipstick and spoke in a tiny, feminine voice that turned me on. Once we got past "the talk", I started with my favorite hobby and discovered that she really was a blond. She moaned and mewed as I licked her and she put her fingers in my hair.

She was quick to reciprocate and just the sight of that glossy small pouty mouth fucking my cock was almost enough to get me off. When I asked if I could fuck her without a condom, she said, "Yeah, just don't come inside me."

She was as tight as any woman I had ever fucked and she played with her nipples as I pounded into her. When I was ready to come, I pulled out and she squeezed her legs together, trapping my shaft between her thighs. She wrapped a fist around the end of my cock as I shot my load.

When I had finished, she licked my cum off her hand while her eyes were fixed on mine. "It turns me on to have a guy watch as I eat his cum," she said in her tiny voice. She was rubbing her pussy with her other hand, but I pulled her hand away and lay between her legs.

I ate her out like my life depended on it and when she came she bucked her little hips up off the bed and held my head with both of her hands. When we first started I had wanted to fuck her ass but she was so tiny I was afraid it would hurt her.

CAROLINE

Unfortunately, this 42 year old woman did not care about nor follow any sport. She visits town only one weekend a month and operates from the same upscale hotel on each visit. The first time I met with her, there was a college football game playing a home game that weekend.

When I texted her for an "appointment", Caroline was pretty frustrated.

"Have only had one client all weekend so far, so you can stay longer if you want."

"Thanks, but I only have budgeted for one hour."

"Don't worry; if we both have fun, you won't go over your budget."

Her profile was different than most. Her photos showed her in sexy outfits, some with black thigh high stockings, black leather boots almost knee high, and a sexy bra showcasing her tits. Rather than the smiling, "Come and see me" face, her photo seemed serious and almost intimidating, and that's what drew my attention.

When I entered her hotel room, she was wearing a long white robe. She was taller than me but very slender. We talked about the football game issue and I told her about some other "home" game dates and she appreciated that. Our "get acquainted" chat took a different path than I had anticipated but it excited me.

"So, why did you want to visit me today?" she asked.

"Well, if we're not being recorded, your photos and profile excited me and I am here to have sex with you."

"What about my photos excited you?"

"There was a certain air of dominance..."

"Ah, so you want to be dominated?"

I wasn't certain how to answer because I wanted to make sure that I would get to fuck her, or be fucked by her.

"I would like you to be in charge, yes, ma'am, as long as we do things I like."

"Tell me exactly what you like, then."

"I like giving oral sex and I like to be fucked."

"Do you expect me to suck you off or peg you, then?"

"OH, NO, no, ma'am, I just like eating pussy and I like for a woman to ride me to orgasm."

I had been sitting in a chair in the room and she had been sitting on the edge of the bed. She stood up, slipped off the robe and stood in front of me, very close. She wore a black lace bra and a black lace thong and black lace thigh high stockings. I stared at her body a long time.

"Do you have any kinks?" she asked. I was still looking at the crotch of her thong.

"I like to lick a woman's ass and sometimes I like to drink her pee."

"Since I am stuck with the hotel bill for a very unprofitable weekend, I might as well have some fun. Will you go along with whatever I want to do to you?"

"Yes, ma'am," I eagerly answered.

"And will you do anything, exactly as I tell you?"

"Oh, yes, ma'am," I answered quickly, although the visions running through my mind were of me getting exactly what I wanted.

She slid her thong down off her legs but left her bra on.

"Undress and kneel in front of me. Stroke yourself but do not come or I will whip your balls until they bleed, is that clear?"

Swallowing hard as I undressed I almost stammered, "Yes, Ma'am."

She was so tall that even as I knelt between her legs on the carpet, I had to tilt my face up to lick her pussy. She had a natural bush, with dark pubic hair. I nuzzled into her pussy, already aroused by the smell. She slid both hands down to hold my face gently in her hands.

"If you are doing something that feels good, I will caress your face, like this," she said. Her warm palms on my cheeks aroused me even more.

"And if you are doing something I don't like, I will do this," she said as she yanked a fistful of my hair. My eyes almost teared up.

"OWWW! YES, Yes, ma'am!"

Tentatively I licked her slit, then nibbling on her outer lips. Her legs were gorgeous and I wanted to please her. I slid my tongue inside her and it tasted so good that I moaned into her flesh. I had good balance but decided to hold her buttocks as I licked her, but she slapped my hands away.

"Later!" she said firmly. "Focus on making me come, and keep stroking your cock!"

It took her quite a while to come and she held my face and pressed her pussy against my mouth as she moaned with her orgasm. I had been stroking my cock slowly because I didn't want to come and get punished.

When she was relaxed again, she was still holding my face in her hands.

"Now, little man, your treat for getting me off. I always have to pee after I come. So, open up and enjoy."

I enjoy the act of a girl/woman pissing in my mouth. Most of the time, I will drink as much as I can, sometimes I just let it overflow my mouth and splash down over my body. I most enjoy it when she tells me to drink and/or swallow it. The taste is almost immaterial.

I was enjoying that she decided to direct things and as horny as I was, I decided to drink what I could. She held my open mouth against her and the first warm jet of her pee hit the back of my throat and went down easily. Then she let my mouth fill and stopped the flow. She seemed to sense that I wanted to swallow it, and I did.

Once she had emptied her bladder into my mouth, she gently pushed me away. "Now, go in and brush your teeth and gargle. You'll find extra toothbrushes and rinse.

When I returned from the bathroom, she was sitting on the bed.

"Lie down, hands over your head," she said. The authority in her voice made me hard.

"I'm going to tease you and use you the way you like, but you CANNOT come under any circumstances. Do you understand?"

"Yes, ma'am."

"That's a good boy." (A phrase that by itself can make me harder.)

She leaned over my body, facing my feet and used her mouth to slowly fuck my cock. I was in heaven but getting dangerously close to losing control. It seemed like forever, but every moment I was in ecstasy, loving the way her lips teased the tip of my aching cock.

I guess she could sense from my shaking legs and loud moans that she needed to stop, which she did. As I tried to get my composure, she straddled my body and eased her pussy down over my cock until the entire length of my shaft was inside her.

She leaned forward on her hands next to my body. Her face was directly above mine. She rose slowly up and down on my erection and the feeling was incredible, my climax building to what I knew would be fantastic.

She watched my face as she fucked me.

"I love to watch a man's face when I make him come," she said. "But I really like the face a man gets when his cock is throbbing inside me and I tell him that he can't come."

The woman was purely diabolical, slowly taking me to the edge over and over. I groaned with pleasure and frustration with each teasing thrust of her body.

"Please," I begged, "let me come?"

Smiling, she slowly lifted off of me. "Get back on the floor and kneel for me," she said.

Hoping for relief, I stumbled off the bed and knelt in the middle of the room.

"Lean back on your hands," she said.

When I did, she stood, straddling my head, facing my feet.

"Get your face in there and show me how much you like licking my ass."

Her buttocks spread on my face as I began licking her crack, seriously considering about asking her to quit being and escort and to marry me.

She bent over and used both hands to squeeze my balls and stroke my cock, still wet from her pussy. She continued to edge me several times as i whined into her ass. Finally, she released my aching cock, stood up and went to sit on the bed.

"Go clean up and come back and don't try to make yourself come.."

When I came back, she told me to get dressed.

"Go home and don't touch your cock. Come back tomorrow at eleven o'clock and bring condoms if you want to come while fucking me."

"Won't you at least get me off? You've spent all this time giving me blue balls!"

"No," she said flatly. "When you get here tomorrow, I will make you come until you pass out. But be thirsty because I enjoy pissing in your mouth. Oh, and call before you leave home; I will order some lobster and champagne and have you pick it up and bring it with you."

To recap the next day, she was true to her word. She sucked me off, then I drank her pee. Then I ate her pussy for a long time until she came, (or at least pretended to). Then she fucked me until I came and pissed in my mouth afterwards. Then she gave me a long and painful hand job until she managed to squeeze out a little more of my cum.

I was so exhausted when I left her hotel room, that I took a nap in my car.