Publish Date: Sep 5, 2006
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This story is about how I lost my virginity. At the time I was 18, 6' tall, about 190 pounds, with brown hair, dark brown eyes, and a dark tan. I was in pretty good shape. I spent most of my summers working on a farm. So I had a nice body, and although I'm not the biggest guy down there, I have every bit of 8 inches. Most of my size there comes from the thickness of my penis.
Now some people think that my first time is a little nasty, but I disagree. I lost my virginity to a 50-year-old woman. Jill, we'll call her Jill, is my boss's wife. I spent a lot time after school doing odd jobs for Jill. When things slowed down at work, my boss sent me to do yard work or make small repairs at his house. Jill was always there helping me out. If I was working in the yard, she would bring me something to drink. Or if I was working in the house, she would make me a snack.
Jill is 50, but she could easily pass for 40, and if she dress up a little maybe mid-30s. She's about 5'6", 140 pounds, 34-c, with short brown hair(her hair barely comes to the back of her neck), and blue eyes. He breast are still firm, they sag just slightly, but that could be expected for her age. She has smooth perfect legs, and a round little ass.
There were a lot of times I would watch her while I worked. Whenever I saw her bend over I would imagine myself grabbing her hips, and rubbing her round ass. She mostly went around the house in a white t-shirt and sweat pants. She never wore a bra, I know this because whenever she worked in the yard, I could see her nipples pressing through the thin cotton shirt.
She would always flirt with me. I never thought much of it. I just saw it as a woman being nice to a young man that worked for her. I knew her and her husband were having problems with the marriage. My boss had been caught with another woman a few years back. And I could tell by the way he talked about her that they hardly ever had sex. She would mostly joke with me about things. Tease me about girls, tell me how cute I was, or ask me why I didn't have a girlfriend. I just brushed all this off as friendly chatter.
One day after school I was sent to her house to do some work. It was nothing unusual. I did a little yard work, and was organizing things in the garage when she came out and asked me if I would hang a shower curtain for her. This wasn't unusual either. She often asked me to do simple things around the house for her. When we got to the bathroom I could see why she asked for my help, the curtain rod was way to high for her to reach. So I replaced it for her.
After I finished she thank me, and turned to clean up her mess. As she bent over to reach for the curtain wrapper I got a perfect view of her ass. I couldn't help but stare. As she stood up she caught me in the corner of her eye, watching her. I quickly looked away. "I'm sorry," I stuttered. "It's ok...," she said. "Can't imagine why you'd look though." "Well, you still look pretty good to be 50," I answered. "Ohh so your saying I'm old?" She smiled back. "No I was just...saying how you're still in really good shape." "Well thanks," she said. She looked down for a while as I straighted the shower curtain. "Yeah know Alan, I thought a handsome guy like you would be staring at a girl a lot younger than me," she said.
"Well I.." I started. " How often do you stare at me?" She asked. "Truthfully? Just about everyday." I told her. "Oh, is it mostly my behind?" She asked. "Mostly..."I said casually. "Well, to be honest, I've stared at you a few times too," she told me. "And to be truthful Alan, if it wasn't for the trouble with affairs, I'd try more then just staring at a guy like you."
Trouble with affairs? I asked myself, what was she talking about? "Oh, I understand, you can't hardly trust anyone with stuff like that." I answered. She moved a little closer to me, "Can I trust you, Alan?" "Yes..." I answered. "Whenever you stare at me," She moved face to face with me, "Do you ever wanna touch me?" I nodded my head. "Do you wanna touch me now?" She asked.
"Y-yes..." I answered.
She lifted her arms, and put them on my shoulders, "Go ahead." she told me. I slowly wrapped my arms around her and started rubbing her hips, I quickly made my way down to her ass. I rubbed and stroked her ass, squeezing it in my hands.
After a few seconds she started to kiss me, press her tongue into my mouth, and pulling me closer to her with her hands. As our bodies pressed together I could feel my hard-on press into her stomach. "Oh my, a little excited aren't we?" she asked, "Why don't you sit down."
I quickly made my way to the toilet and sat down. Once I sat down she stood over me and began to unbutton my pants. First she slide off my jeans, I lifted my hips helping her pull them off. She started at the bulge in my briefs, then she quickly pulled them off. My dick slapped up against my stomach, as she let out a slight gasp. "My god, that is the prettiest cock I've ever seen." She told me. "Really?" I asked. "Oh yeah, it's longer than my husband's, and it is a LOT thicker!" She answered.
She grabbed it and slowly started stroking it. My sexual experiences didn't go beyond making out. So it was taking everything I had not to explode. She make a few strokes, as my hips started to raise. "Oh," she giggled. "You like that? How about this sweetie."
She knelt between my legs and took my cock in her mouth. I could feel her tongue circling my dick as her fingers rubbed my balls. Before long her head was bobbing up and down my length. Before long I blew my load into her mouth. I felt her lips tighten as I spewed. She sucked hard until she had swallowed most of my jizz. As she looked up I apologized for cumming so quickly, and in her mouth. "Its ok hon, I understand." She told me. "Do you feel up for some more." "That depends," I told her, "What did you have in mind?" I asked.
She stood and began to finger herself. She motioned for me to lie in the floor on the bathroom rug. As I laid down I watched her as she stood over me, rubbing herself. I felt my dick stir as it started to get hard again. She moved down, slide off her sweats, and straddled my waist. "Do you wanna fuck me?" She asked. "Yes," I moaned.
She slowly moved down over me, taking all of my dick into her pussy. As she slowly took me in she started to moan loader and loader.
"God you are so wide!! You are stretching my pussy so much!! God I want you!" She braced her hands on the floor above my shoulders and started riding my dick. I reached up above and started to rub my hands over her waist, ass, and breast. Her pussy felt incredible, with every thrust I could feel her tighten around my dick.
Before long I stared raising my hips with her thrust, matching her rhythm. "That's it, fuck me Alan! Fuck me.....Oh God you are thick! Just like that just like that....Oh god baby, yes! more... fuck me oh god." I started to stroke her breast moving my hands over her chest. "Oh god, pinch my nipples, pinch them....Yes!! God that feels sooo good!.....More! oh I'm gonna cum, I'm gonna cum, Cum in my pussy Alan...Fill me up! Cum in me!!"
At least I blew my load into her. I felt her tighten around me, as she explode. Her back arched back, as she grinded her pelvis into my dick. "Mmm, Alan, you are better then I expected." She smiled at me.
She was great, and we did things together a few other times. I learned a lot from her.
T-Girls - Part Four - Lili Elbe - A Little Danish Please! - So who was this young woman of Danish origin who underwent the first risky and risque operation to be the first transsexual Brunhilda of Bavaria?
T-Girls - Part Three - French transsexuals include the Abbe De Choisy who was not so choosy when it came to male sex partners
The T-Girl - Part Two - The transsexual not only comes out of the closet, but, does so with fabulous flair, honey dripping honesty and penis erecting panache