Where it happened: apartment
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My father was a successful businessman back in the 1950’s in a large Southern city. In that era and place, it was common practice to seal a deal or reward a customer by presenting him with a woman. For that reason, (and he claimed only for that reason), my Dad, a deacon of the Baptist church, had extensive dealings with our city’s best house of prostitution. So when it was time for me to learn about sex Dad set me up with the patient, understanding madam of the brothel to show me the ropes.
One Saturday a month before my sixteenth birthday told told me he wanted me to meet someone. We drove to an upscale apartment building where a woman in her mid forties answered the door. She was a little chunky, wore a blouse and skirt and glasses. She looked more like a librarian than a prostitute. Dad introduced her as Miss Carol and told me she was going to teach me some things. I had no idea what was happening. I thought she might be a math tutor. Dad left and Carol invited me to sit on the sofa. We made awkward smalltalk for a few minutes and then she explained that my father had asked her to teach me about sex and asked if I would like to make love with her. I guess I managed to say yes because Carol kissed me and went into her bedroom for a minute. When she returned the librarian look was gone. Her brown hair was down past her shoulders, the glasses were gone, and she wearing a filmy negligee which clearly showed her areolas and pubic patch. Taking my hand, Carol led me to her bed where she undressed me and laid beside me naked. We kissed some more and Carol put my hand on her breast. I was too intimidated to touch it on my own but now I was all over her boobs.I suppose they had been enjoyed by literally thousands of men (including my father?) but I had never even seen a breast before and I was loving them. Soon Carol pried me loose from her bosom and kissed her way down to my penis. I watched in amazement as she licked and kissed my shaft and testicles, then engulfed my penis. This was long before AIDS and STD awareness so there was no condom between us, just the wonderful warmth of Carol’s mouth on me. I still remember the image of Carol looking up at me and smiling, my phallus in her mouth. I guess I was a typical firsttimer in that I didn’t last long when Carol started fellating me. After maybe a minute of her gentle sucking I felt my orgasm beginning. I warned Carol but to my surprise she kept right on sucking, taking spurt after spurt of my semen in her mouth. When Carol finally released me she gave me a big cum filled smile and then swallowed my ejaculation, licking her lips afterward.
We took a little break then and Carol got me some cookies and milk. Lying naked in bed we ate Oreos and laughed about the size of the load I had just blown in Carol’s mouth. She asked if I had any questions about sex. I asked her a few things and she told me some stories about her career. Then she whispered that she wanted me inside her.
I got on top of Carol and she guided me to her opening. Again, there was no condom as I slid into my first vagina. Carol wrapped her legs around me and coached me as I clumsily plunged away at her. Even though I had orgasmed only a few minutes earlier I didn’t long and soon shot another load deep in Carol’s pussy. As I rolled off her Carol cheered and shook my hand, congratulating me on no longer being a virgin.
During the ride home my father told me that his relationship with Carol was strictly business – I don’t know if it was or not. Then he told me that he didn’t want me spending all my time pursuing girls at my school and maybe getting one of them pregnant. Giving me a phone number, he said I should call Carol or one of her ladies when I needed some relief. At fifteen I had a charge account at a whorehouse!
My first dozen or so sessions were with Carol. She taught me about various sexual positions, cunnilingus, anal intercourse, even a little bondage. One day she had a petite Chinese girl join us and they showed me lesbian sex before we had a threesome. Then Carol began setting me up with the various ladies who worked for her. Usually they serviced me at Carol’s place. Ocassionaly Carol would join in – she really enjoyed the ladies I think more than men. This continued through high school and college until I met Jenny, the girl I would marry. I remained faithful to Jenny until her death four years ago. I know Jenny enjoyed some of the lessons Carol and her ladies taught me.
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