Where it happened: Tina' house
After finishing high school I had no interest in attending college as most of my classmates did. I wanted to make money and explore the world, so I was scanning the job ads in the paper for something suitable.
My eyes stopped at an ad for a position in sales and I called in right away. The pay was good, they needed someone who can drive which I love, only the merchandise was a bit strange – they specialize on lingerie… Not that I knew anything about it, but I could learn, couldn’t I?
To my surprise, on the next day when I showed up for an interview I was hired on the spot. They gave me some boxes with catalogs to distribute and some more boxes with lingerie of all sorts and shapes. I had a look at most of the items so I would know what I had in my van and went on my way the next day.
Initially I had some “No”s at the doors, but not long into the day I was welcomed by a mid-aged woman, probably in her early 40s, in her own home. I told her what I had to sell and if she would be interested in any of the merchandise. She said she was and after telling me her sizes, I showed her some bras, silky panties, and sexy stockings. She took a while to select the colors and patterns she liked and then, to my surprise, asked if she could try them on. I wasn’t sure, they hadn’t told me their policy, but I thought it was probably a bit uncommon to try on lingerie. In any case, I didn’t want to frustrate my first potential customer and so I agreed.
She went into her bedroom and emerged back out again shortly thereafter. But not back in her clothes – she just wore the stockings, panties, and bra she was interested to buy from me! With a smile in her face she asked me what I thought. I hadn’t given too much attention to her so far, but now in this sexy lingerie she look hotter than many young girls would. She was about 5-8, perfect figure, and had short black hair. Her breasts were size 36C and her legs very shapely, her feet quite small and her toenails painted bright red, shining thru the thin black stockings. After a pause I replied that she looked very sexy in these and that her husband certainly would enjoy her wearing them. She came closer and gave me a warm hug and thanked me, and at that point my cock was as hard as a rock and she must have felt that.
We both knew what would come next, although I had never had sex with a woman before, and we walked into her bedroom together. She took off my clothes and gently embraced me, so that I could feel her breasts in her sexy bra against my chest and her panties and stockings as well. She said her name was Tina and stroke my hair, wnet down with her hands on my back and grabbed my butt cheeks, squeezing them firmly. That felt great! Then she picked up one of her small feet and rubbed it against my legs and feet, what a pleasure! Next she kneeled down and started working on my cock with her hands and her mouth. Her fingernails were long and painted pink and they softly scratched the shaft of my cock and aroused me beyond measure. Her tongue played with the tip of my cock very skillfully, it was clear she had a lot of sexual experience. My cock got even bigger and started to throb. Soon I came in her mouth with a massive orgasm and she swallowed all my cum and carefully licked my cock clean.
Now it was my turn to please her, and I didn’t have to worry what to do because she showed my everything and was a very good teacher. I started with caressing her whole body, very gently, feeling her soft skin, then kissing her, first on the lips, the inserting my tongue into her mouth and doing a wild dance with hers. She then led me to her breasts and I massaged them first with her bra on, then took it off and massaged her nude boobs that had dark, erect nipples. She then told me to suck her breasts and nipples and I was a good student and tried my best to please her, being highly aroused myself while doing it.
I went down to her feet and gave them a massage thru her stockings which we both enjoyed a lot, she was even moaning, when I sucked her toes. Then gently stroking her legs, up and down, and then taking off the black stockings and doing the same without them.
Finally my hands slid to her crotch and started massaging her most sensous areas. She took off her panties and showed me where her clitoris was. It was not too hard to find as it was already erect and quite big, but under its hood, She showed me how to massage her clit the right way with two fingers, and she was getting hotter and hotter, moaning more and more. She inserted a finger into her ass and said she’d like a rub from my finger in her vagina. I followed her wishes and rubbed there, too, with everything down there getting really wet. I felt a natural urge to bend down and taste her, licking her clitoris, sticking my tongue deep in her pussy and giving her a real sexual workout. Her moaning and sighing got louder, and she asked me to lay down on the bed, then she grabbed my hard cock and stuck it inside of her pussy. She was riding me like crazy, moaning, sighing, yelling, while my cock grew larger inside of her. Her boobs bounced up and down and I grabbed them and squeezed them, then grabbing her delicious butt, scratching it a bit. Shortly thereafter she came several times in a phenomenal orgasm that lasted over five minutes and she ejaculated on top of me, while I came as well and shot my cum deep inside her. But she was not done and wanted my cock in her asshole real bad, as her husband has never done that with her and it was her fantasy to do this with a man. I started massaging her ass, feeling inside with my fingers, widening the hole and then sticking my cock in deep into her asshole and fucking her hard for many minutes until she had an even wilder multiple orgasm and I shot another load into her.
Exhausted, we fell into each other’s arms, and after a little rest, we did it again and again.
Although I met many women on my tours later that I had sex with, this first time with Tina still remains the most awesome sex experience of my life.