There I sat by the pool at the largest retirement community in Florida. An unfortunate epidemic of STDs precluded the residents from participating in the favorite community recreation, sex. It was a shame. Particularly considering the lovely woman lying on the lounge across the pool who had just winked at me.
My first sexual experience occurred with a friend of my mother's when I was technically jailbait. Her name was Madeleine. She was about forty, very attractive and flirtatious. Mom asked her to check on me one weekend when she had to visit Grandma who was ill. She actually brought a delicious, homemade lasagna dinner for us to share, including a proscribed bottle of chianti.
She wore a blouse that made it impossible to ignore her extraordinary cleavage. As we finished off the wine and I was feeling noticeably buzzed, she caught my eye as I looked up from her bodacious bosom.
"Like what you see, Lawrence?"
I probably stuttered, embarrassed, and scared my mom would find out I was leching after her friend, but she changed the vibe quickly when she grabbed my hand and pulled me out of my chair. I know I was mortified and tried to cover the erection that was tenting my jeans.
"Is that for me?"
"Um... sorry, I..."
"Don't be, it's a compliment. Follow me."
She led me upstairs to my bedroom, reached for my waist, undid my belt, and pulled my jeans and boxers down to reveal my rock hard cock.
"Oh my, that's a beauty." She reached down to take my cock in her hand and stroked it. I couldn't believe what was happening.
"Is this your first time?"
"No, yes.. I mean I do have a girlfriend."
"How far have you gotten?"
"Well, we um."
She dropped to her knees and took my cock in her mouth. I didn't last long in her practiced mouth. She took all of my youthful seven inches easily into the top of her throat. She squeezed my balls gently as I exploded repeated spurts of cum for her.
"Yummy. Now that we've got you over your impatience it's time to begin your education."
She pushed me onto my bed, stripped me, then herself leisurely and seductively which effectively resuscitated my cock.
Three or four hours later I untangled myself from her embrace with an education in the art of love. Despite cumming in all of her holes the highlight of the night, and something that would loom large in my legend was my introduction to the pleasure of oral love. The blowjob she started me off with was great, don't get me wrong, but it was the first taste of her beautiful pussy that formed the man I would become. It also made me very popular with the girls at college and the women I met for the rest of my life.
My reverie was broken when the fetching lady from across the pool settled into the lounge next to me.
"Hello, handsome."
"Back atcha."
Without any further discussion she handed me a folded paper. As I read it a delighted smile blossomed on my lips. It was a form from the local hospital proclaiming that Claire Palmer had tested negative for all STDs yesterday.
"Have you been saving yourself for me since these tests were done?"
"You do have a certain reputation among the ladies here, Larry."
She smiled, "Now that we have the preliminaries attended to, your place or mine?"
"It is my experience that women prefer their own beds."
"Works for me."
She rose from her lounge and walked down the path toward the fanciest part of the complex. My grin grew with every step as I followed her shapely butt along the way.
When we reached her unit she stopped in the doorway to disable her high end alarm system before ushering me inside.
"Refreshment? I'm in the mood for a frozen margarita, you?"
"That would hit the spot."
I admired her grace as she gathered the classic ingredients: fresh lime juice which she squeezed by hand, tequila blanco, Cointreau, blue agave syrup, a dish of pink salt crystals, and a bowl of ice cubes.
"You take your margaritas seriously."
"I don't like half-assed anything."
The blender whirred as she salted the rims of two double rocks glasses. While the blender did its work she brought a basket of chips and a bowl of salsa to set before me on the gleaming polished driftwood coffee table.
She returned to her kitchen, stopped the blender, poured our drinks, and returned to sit gracefully next to me on the supple leather sofa. She extended her glass in a toast.
"To pleasure."
"Mutual delight."
I took a sip of the succulent nectar Claire had prepared.
"This might be the best margarita I've ever tasted."
"Thanks, I'm a bit of a perfectionist."
"You're fairly new here, aren't you."
"Just moved in last month."