I had to leave school at 16 to help my mom out with bills after my dad abandoned us. My Uncle Bob gave me a job at his nursery, delivering plants, laying sod, and installing landscaping in new homes. Hard work, but an honest day's work, and I was young and fit.
My mom remarried to a real estate investor after she divorced my dad, who had landed in prison for DUI vehicular manslaughter.
They flipped houses together and were doing well. One of his fixer-uppers was a duplex; during remodeling, they lived on one side, and my older brother Joe and I lived on the other side.
Joe was a firefighter, and he was gone most of the time, working 48-hour shifts or taking more emergency training courses. I pretty much had the place to myself. Our rent was covered by our new stepfather, Jack; we just paid for food and utilities. For once, I was able to save my checks and spend them on me. I bought a nice used van.
Every day I worked on that van, doing something to it. I was preparing to drive it across the South on my first paid vacation.
One Saturday morning I was changing a tire, and I kept hearing someone do the wolf whistle. Looking around, I didn't see anyone, so I went back to work. Ten minutes later, I heard someone wolf whistle again. It sounded like it came from across the street.
I'd finished changing the tire, and I took off my T-shirt and used it to wipe the sweat from my face.
Once again, I heard the wolf whistle, only this time I happened to be looking at the duplex across the street. Through one of the open windows, I just caught a glimpse of two female faces, and I heard some giggling.
I started walking across the street, but my mom came out from her side of our duplex, and she asked me to go shopping for her.
Almost every night while driving home, I saw a very good-looking, black-haired lady walking her little dog down the main street. She always wore a sundress, and she waved to cars if she saw single guys in them.
I thought, "She's too pretty to be hooking on the side of the road. Her dog was better looking than the typical Sarasota ho on the Tamiami Trail."
Once, I saw her get into a car with a few guys in it.
Bringing in the supplies Mom asked for, I heard the wolf whistle, and once again it came from across the street.
"Somebody must have bought a parrot," I was thinking, "and trained it to whistle."
Sunday morning I went outside to work on my van. I found an envelope with lipstick kisses on the windshield, and it was sprayed with perfume.
Opening it, I found a handwritten note that read, "I've been watching you work on your van. When are you going to take me for a spin? Your secret admirer."
"Oh, come off it, are we back in grade school?" I thought.
The note had me smiling at the idea of some young girl flirting with me, then not smiling at the thought she might be underage or grossly deformed. That would be more my luck.
I installed a new light in my van and took off for the beach. I enjoyed my day off by sitting in the Florida sun and staring at bikini-clad tourists.
Coming back from the beach, I saw the streetwalking woman again. She was wearing a black bikini, sunbathing in a lawn chair in front of the duplex across from ours, smoking and drinking a beer. A man came out; he tried to kick her little dog, then they had some heated words, and he left in his car.
"Time to get to the bottom of this." I thought. I got the note from my desk, then walked across the street to confront her with it.
Mild panic was on her face when I walked over to her.
She looked to be about 30 years old, and much better looking up close.
"Hello," I said, "Would you know anything about this?" showing her the envelope.
"My little sister put me up to it," she said, looking embarrassed.
"Was she the one wolf-whistling at me?" I asked.
"We both were," she answered.
"Where is she?" I asked.
"At her house," she replied.
"I'm Mark," I said.
"I'm Dedrea, but everyone calls me DeeDee, because of these," she replied, holding her big tits and smiling at me.
"Would you like to share a joint with me?" she said.
"I would! But not out here. Let's go inside so my mom doesn't see us." I replied.
"Sounds reasonable to me," she said, so I followed her inside.
Her house was tidy, but stark. Just a few personal things: a couch, a table, and chairs. A picture on her wall showed her marrying the guy I saw leaving.
"That's my stupid husband," she said when she saw me checking it out. "Soon-to-be ex-husband. He works the night shift at the county sewage treatment plant, and spends all our money on whiskey."
"I know how much that sucks, believe me, I've lived through that shit too," I said.
She opened two beers for us, we sat on her couch, and I sparked up the joint. We smoked it in silence, me not knowing what to say next. Should I ask her about seeing her on the street, acting, and looking like a prostitute? Or was she just lonely and horny and looking for company? I hate it when people judge me, so I was not going to judge her.
"Would you like to take a spin in my van?" was all I could think to say.
"Yes, ever since I saw you installing a bed in it," she said, with a twinkle in her eye. "But not now, maybe later."
We finished the joint, and she lit a cigarette. DeeDee got up to put a Barry White album on her turntable and chugged her beer.
Turning to me and putting her cigarette out, she said, "Let's dance."
My mom taught me to do the waltz and some square-dancing moves, so I knew how to move with confidence. DeeDee was impressed.
"You dance better than I expected," she whispered in my ear.
We held each other and swayed to Barry's sexy voice.
"When will your husband be back?" I asked, not wanting to be shot.
"Tomorrow morning at 9:00," she replied.
"He'll stagger in, stupid drunk and mad at the world. He'll try to kiss me, and as always, I'll tell him no; his breath stinks, and he smells like shit.
"Next, he'll stagger to the couch and pass out. The fridge is always empty; he even pawned our wedding rings only to drink and gamble that away too. He hit my boss, and I got fired from my job; now we're broke. That's why I'm going to divorce him."
"I know how shity that is, believe me," I said, trying to console her.
"All we do is argue. I never get sex from him anymore either. He can't get it up now, because he's always drunk. I married him mainly to get away from my parents. I wanted to have sex served with a side of kink, you know? He started strong, but he faded fast. Maybe that's why I'm always horny," she said, laying her head on my shoulder.
It was getting dark now, and cooling off.
I've kissed a few schoolgirls, and we did the heavy petting thing, but I never had a steady girlfriend. Starting at 12, I was working after school and on weekends.
I was very much still a virgin when Deedee grabbed my dick and pulled my head down to her lips. We kissed as she fumbled to take my dick out of my pants. I ran my hands up and down her back as we kissed. She took off my shirt, and I took off her bikini top. Hugging her bare skin next to mine was so sensual and sexy. I felt her breast as we kissed; her nipples were hard, and the rest of her breast felt totally at home in my hands.
Deedee was a great kisser, hardly ever stopping after we started. I was about to find out what else her lips were good at.
DeeDee stopped kissing me long enough to take her bikini bottom off. She took my hand and placed it on her pussy, then she started to rub my cock again.
"Like this," she said, noticing my hesitation. Taking my two fingers, she put them on her clit.
"Now lightly rub it around in little circles," she said, and resumed kissing me.
My pre cum had started to flow, and DeeDee used it as lube to stroke my cock with. Her knees began to shake, and she started telling me she was going to cum, and not to stop.
Moaning into my mouth, I felt her pussy gush love juice as she came on my two fingers. Taking my same two fingers, she put them into her vagina, and said,
" I love finger fucking, don't you? Now, curl your fingers up, um yeah like that. Now move your hand very fast, and press up!"
Her pussy was wet and surprisingly warm, and I could feel her muscles contracting on my fingers when she came again.
Getting her hand wet from her pussy juice, she used it for lube on my cock. Her hands moved faster, her grip got stronger, and I didn't even try to hold back; I just let it fly, coming stronger than I ever had before.
Grabbing me by my soft cock, she led us to her bedroom. We lay on her bed, side by side, kissing and fondling each other, making my cock hard again.
"It's time for me to make a man out of you," she said, mounting me and guiding my cock into her soaking wet cunt.
The feeling was fantastic; much better than I could ever imagine. DeeDee was doing all the work; I just lay there enjoying my first fuck. She fucked me like this until she came again, then collapsed on my chest.
Kissing her, I took the lead and started humping up into her, holding her cunt close to my pubic bone and pounding her as fast and as hard as I could. DeeDee totally enjoyed this treatment and thrashed around on my dick, moaning into my mouth as we fucked. She came strong this time; I felt her pussy juice wetting my crotch.
Turning her over, but keeping my dick in her, we fucked each other; she met every thrust, gabbing me tight with her cunt muscles and moving her hips. Deeply kissing and moaning, DeeDee came once more.
"Let's take a little break, lover," she said, getting out of bed. She lit a cigarette and walked to the bathroom, shaking her hips, knowing I was watching. I lay on the bed catching my breath, feeling my dick was going to explode.
I heard the toilet flush, then water running. DeeDee was standing in the doorway smoking. The backlight accented the cloud of smoke that surrounded her. DeeDee posed in the doorway, her big tits in silhouette. DeeDee cocked her head and sensuously blew smoke in the air. She looked at me, then at my dick standing tall, and asked me,
"Have you ever had your cock sucked?" she said, knowing the answer.
"Not yet," was my response.
"You're going to love this," she said, smiling.
DeeDee sat between my legs and blew smoke on my cock, then she lowered her head and took me in her mouth and sucked on my cock. She repeated this maneuver until she put it out. To this very day, I still get hard when I see a pretty lady smoking.
DeeDee swung around and put her cunt in my face, then started sucking me again. I breathed in her musky scent and saw her wet pussy lips close up.
"Kiss my pussy lips, then suck my clit like I'm sucking your cock," she instructed.
"Ooo yeah, keep doing that, yes, just like that, baby!" She said.
She tasted good, not like anything I've ever had in my mouth. She tasted sweet, sour, salty and musky, depending on where my mouth was. It was fun to suck on her clit, it seemed to grow from when I first started.
DeeDee started moaning loudly again, and I knew by now that she was close to cumming. I kept licking her, and when she came, she flooded my face with her pussy juice. I was not prepared for that; I thought she pissed on me, it was so much. It wasn't unpleasant, just messy, so I didn't say anything.
She stopped sucking my cock and moved up to sit on it. She moved her butt up and down on me, and I had a great view of my cock fucking her.
Suddenly, she moved off my cock, raised a few inches over it, "Put your fingers in my cunt, and get them wet," DeeDee instructed.
She sat on my cock and then said, "Now, take your wet fingers and rub them around my asshole. Mmmm yeah, that's good."
I felt her butthole contracting in time with my fingers.
DeeDee put my cock back in her, but only the first inch, and squeezed me for about five minutes. "Now put one finger in my ass!" she said, panting and sitting down on my cock.
I couldn't believe how much tighter her ass was than her pussy. Her pussy gripped my cock like a vise when my finger got all the way up her ass. I could feel my prick fucking her with my finger.
DeeDee cussed like a sailor, and bucked like a bronco when we both came again. I lost my load, and I took my finger out of her ass before she broke it. She continued to grind me as we cooled off.
DeeDee got up to turn her fan on and came back to bed. We cuddled, and she fell asleep.
I looked at her bedside clock; it said 4:35. We fucked almost all night. Knowing I had to get up for work in two hours, I reluctantly got up and got dressed to go home.
The walk across the street was short, and soon I was in bed. I set my alarm and crashed.
I didn't see DeeDee around her house the next day or the next. Two weeks went by before I came home to see a moving van in her driveway and her husband moving his stuff out. Two more weeks went by, and I started to believe I'd seen the last of her.
When I was leaving for work one morning, I found an envelope on my windshield. It had lipstick kisses on it, and it was perfumed just like the last one. This one read, "I'm waiting for that van ride you promised me. Pick me up tonight on the corner of 14th Street and 17th Ave. at 8:00. Your secret admirer."
We partied in my van a few times, and then she just disappeared without saying goodbye. I still think about her and wish her well, wherever she is and whatever she's doing.
