I'd worn a lot of different hats in my life, but none were thinking caps. Starting out knee high to a colt, I was donning my cowboy hat working my mom and dad's ranch outside of Cody Wyoming. It was the white hat of a painting crew after running away from home at 16 and landing in Minneapolis. I left Cody to find fresh meat, having exhausted the supply of cute girls and horny housewives. Yes my balls made all the important decisions for me ever since hair started growing there. They still do. I hitched down to Memphis when it got cold and began wearing a hard hat. The hard luck housepainters, mostly Indians (I stood out with my shock of blond hair) helped get me a fake ID. I was now a very young looking 21 so I could work on a road crew and could drink at a tavern. When I actually turned 21 working construction, I decided to move to Nashville, find me some singing cowgirls and, after getting my GED, train to become a deputy. Again the hat was wide rimmed.
Playing it straight, I gained the respect of my bosses. I had my eye on vice, specifically prostitution. That's where the money was. By twenty-nine the hat was short brimmed, and I was getting bent. On my thirtieth birthday, I celebrated with my favorite Madame and a pretty little filly that she let me break in. The kick backs and hush money was great, but the fresh, sexy meat was better. Unfortunately, I couldn't get enough of the sweet meat of this specific filly. It was love at first taste.
What got me were her eyes.
"Be sure to look into his eyes," said the voluptuous middle aged Mexican Madame Rosa pausing before returning her lips and tongue to my pussy filler. They both were crouched between my thick thighs. Rosa wore a red and black corset holding up her large breasts and not hiding her areola. Sam was naked. Pale white and soft skin held tight over a long slim frame with impossibly large, youthfully buoyant real breasts. Her waist was slim enough to give her smallish hips some shape and her firm round butt some lovely definition. And her black hair, blacker than Rosa's, was another study in contrasts, falling straight down her white back.
Rosa handed my member to Sam and instructed her. Sam was a quick learner. The pressure and motion were just right. The lips and tongue were perfect. "Now, never forget, look into his eyes," said Rosa
Sam's eyes were unforgettable: large and azure blue and complex, a deepness that sucked me in. I went completely rigid immediately. I took pride in my eight inches of woman pleasing flesh. When it filled her mouth her eyes filled with surprise and pleasure.
"Isn't it a beautiful cock? It's the best you'll ever see," said Rosa, inflating my ego if not my flesh, which had reached its maximum. Rosa continued to instruct and Sam continued to eclipse the teacher.
I groaned with pleasure. Our eyes kept contact. Her mouth was full. I could read a smile in her eyes. She enjoyed what she was doing.
"I'm going to cum," I moaned. Usually a blow job just readied me for the fuck, but Sam had me near explosion already.
"If you don't want to taste it, you'd better finish him off with your hand," said Rosa. Sam shook her head and continued sucking.
My whole body stiffened as my shaft let forth several spurts. Sam tried to swallow it all. Her lips let go, and as she swallowed whatever was left in her mouth, I spewed a final couple of gentle squirts on her chin. As she smiled up at me, Madame handed her a napkin. I studied her face as she cleaned off my jism. Not a typical beauty. She had a largish, though evenly shaped Jewish nose, Goldberg, her last name, was a clue to her ethnicity, but to me she was the most beautiful creature I had ever seen.
"Very good," said Rosa as she stood up.
"Thanks," said Sam, still smiling at me.
"Rosa, you've outdone yourself," I said. "She's a marvel. What say you leave the rest of the training in my capable hands? I'll drive her home."
Rosa said, "Of course," quickly dressed and exited the apartment.
We continued to stare into each other's eyes. I don't know if she felt the waves of emotion I felt so I asked. "Do you feel it?"
"Something," said Sam.
"Some sort of cosmic connection, not that I believe in such bullshit."
"Believe it," she said, and crawled up my legs, across my torso and sat straddling me on the bed. Her pussy pushed itself against my limp cock. I felt her breasts against my chest, her quarter inch thick nipples rubbing near my man nipples. Her arms wrapped around my shoulders. We kissed.
I could taste my bittersweet flavor in her mouth, but soon ignored it. Pure passion took over. Our tongues danced in each other's mouths. Her pussy began a subtle rocking motion against my cock. My hands held her ass and assisted the movement, pressing her down and opening her up. The kiss and the friction made me rise again.
She reached down to check on my growing member. It was hard, so she led the tip to her slippery hole, guiding the shaft home.
Reluctantly I ended the kiss. "Two rules," I said. "No kissing the customers and no bareback riding."
"I know, silly," said Sam with her wonderful smile. "I may be young but I wasn't born yesterday."
"So, I'm clean, and I want to feel you naked. Just you, Mr. Policeman." I brushed her hand away from its guiding. "Please," she whined, sounding her age for once.
"First things first," I said, suddenly lifting her up and tossing her on her back on the bed. "I get to taste how clean you are."
She squeaked surprise. Her body was not voluptuous like Rosa's, but it curved just right. Her soft skin slid under my hand from her ankles, across her pussy lips, causing them to lift, over her breasts sagging the tiniest bit revealing their true nature, and to her cheeks. My other hand joined the touching of her face. My body climbed between her legs. For the moment my cock teased her pussy, the bottom of it rubbing her clit.
After another passionate kiss, I began my descent. At first, both hands were involved along with my lips and tongue. But she wasn't going along with the complete tease. She took one hand and forced it on her sex lips. Of course I am quite strong, so there wasn't any resistance on my part. Her hand stayed near mine, pulling and hardening my pussy filler.
I lingered on her ears and her long neck, but her breasts that got the most attention. Mouth and hand circled the targets, feeling the play and the weight of the flesh mounds. Zeroing in, I ravished the nipples. Twisting and sucking, I found the right friction to give the most pleasure, which she sang out.
"Mmm, mmm, aaah," she moaned. She enjoyed it, but not enough. I continued down. Meanwhile my fingers began fucking her. Two fingers slid in and out of her passage. The thumb pressed and released her clit. This got her really moaning.
She added a quiet, "Ooh," when I stopped at her inny navel and drilled it with my tongue tip. I discovered the texture of her well coiffed triangle of black pubic hair before dabbing my tongue over her clit. Her hips rose a foot. When I moved past, she grabbed me.
"Patience, my dear," I said in a devilish whisper.
"No," she complained, but when a third finger found and rubbed her g-spot, she had no reason to complain.
I massaged my fingers and tongue down her thighs, kissed her inner knee, then slipped along her calf to her feet. I spent an extra moment there suckling each toe, spending the most time on the big toes, giving them a mini blowjob.
By the time I licked up to her pussy, she was more than ready. Her hands holding her knees opened herself completely. Revealing her rosebud to me, I speared it with my tongue and rimmed it. She liked that. Then I opened her lips with both hands and gave her a tongue bath, stopping to flick her clit. She was right. She tasted clean, fresh and sweet. Her aroma thrilled. I looked up at her. Her lips pursed. Her eyes went wide. She was getting seriously hot. She was near orgasm.
Climbing between her thighs, I positioned myself for the plummet. She let go of her legs, letting them drape along mine as she took hold of my cock and guided it.
"Yes," she cried as my thick head barely squeezed in. She didn't seem to mind the tightness. I certainly didn't mind. We kissed hard for a few moments, but we needed our air passages cleared for all the heavy breathing. I made my descent, opening her up to more of my pussy filler. Once I hit bottom, I had less than an inch to spare. I slid almost all the way out, and then pushed as deep as possible. The fucking began slowly, but she wanted it faster. Her hand holding my ass guided me to quicker speeds.
"Harder, my darling," she ordered. Once I got the tempo and the force down, she let go and quickly came to a loud, squealing orgasm. She went limp, but I kept at it. When she recovered, her face in full blush, she smiled and grabbed me around my shoulders. Her legs wrapped around my lower back. I got the hint and lifted myself onto my knees. She became a pendulum swinging beneath me, only stopping the swing when another orgasm hit her. After a third cum, I turned us over so she could ride me. She found the perfect angle, about 30°, so that her clit got friction. I loved the sway of her tits as she fucked me. I loved that we could be tight at the groins this way, too, without fear of bruising her cervix. In fact, even though I am a tough motherfucker, I have always loved the female superior position best. My balls felt ready to blow. I pulled her hard against me, lifted her off the bed, and ejaculated my soul into her womb. She pumped against me a couple more times and found her last orgasm. I closed my eyes, enjoying her inner pulses throbbing against my throbbing cock.
.... There is more of this story ...