I'd been hitchhiking for three days when I decided I needed to finally stop and take a break. I was eighteen and just out of high school and it was the summer before I was supposed to go off to college and start a new life. I figured this would be one of the last times in my life that I would be truly free, so I decided to hitchhike across the country and see what America was all about. My parents weren't crazy about the idea but there was nothing they could really do. I was eighteen and on my own and I could do whatever I wanted, and I wanted to hitchhike. I guess you could say I was a little naive. After all, I had only been out of my home state of Indiana twice, and both of those times were school trips into Illinois. To say I wasn't well traveled wouldn't exactly have been an understatement.
From the start I'd been hitchhiking west, heading toward Denver, and having the time of my life. I was meeting new people, exploring new places, trying new things. I was dead tired though by the time the third day rolled around and felt like I needed a good night's rest. A trucker dropped me off on the outskirts of Boulder and it was there I decided I would spend the night. But first I needed to take a break and get some food before I even thought about looking for a suitable hotel. I took a walk toward the main part of the town. It was a typical small town, and more or less was what I expected. I went into the local diner and took a seat at a booth. I unloaded and stretched out as I waited for my patty melt and fries. The diner was virtually empty so I couldn't help but notice when she walked in.
She was an incredibly sexy woman. This despite the fact that she was old enough to be my mother. If I had to guess, I'd say she was about forty, although her body certainly didn't show it. She had long strawberry blonde hair that fell at least six inches past her shoulders. Every strand of hair was perfectly styled, almost like on a girl you'd see on the cover of a magazine. Her lips were blazing red in stark contrast to her slightly pale skin. Her face and eyes were beautiful, if a little worn. She wore high heels and a tight cut miniskirt. Her white blouse hugged her curves perfectly. Her tits were nothing short of amazing. They seemed to defy gravity. Not that I was experienced, but I would have to say they were definitely more than a handful. It didn't end there either. For one, her stomach was amazingly flat, and as flat as her stomach was, her ass was round. And beautifully so. I couldn't help but imagine running my fingers all over her luscious body.
But really, who was I kidding? I was an eighteen year-old boy. I had no absolutely no chance of even kissing such a sexy older woman, never mind sleeping with her. To make matters worse, I was a virgin. I had no sexual experience whatsoever. Sure, I had made out with a few girls, and I even managed to grope a few tits, but I had never done anything more that that. To be honest, I was a little bit embarrassed about some things I won't bother to get into. So needless to say, the fantasy in my head was as far I was ever going to get.
When she sat down at the table across from me I was definitely taken aback. No matter how hard I tried, I couldn't keep my eyes off of her. It seemed like every couple of seconds I was looking her way. After a while I think it became more like a stare. I think that's when she first saw me. I must have been drooling by then. She gave me a quick smile and then turned away. I was a bit embarrassed and tried not to look after that but I couldn't help it. Within minutes I was back staring. It wasn't long before she caught me looking again. This time though, she didn't smile. Instead, she got up from her table and came over to my booth and took a seat directly across from me. I think by the time she got comfortable I was trembling.
"Do you like what you see?" she cooed sexily.
"What?" It was all I could muster. I was completely caught off guard.
"Do you like what you see? Do you like my body?"
My eyes turned downward sheepishly.
"Yes, ma'am."
"What about my tits? Do you like my tits?"
"Yes, ma'am, I love your tits."
"That's good. For a minute there I thought you stopped staring."
"No, ma'am."
She stared directly at me for what seemed like a minute before she spoke again.
"I wanna fuck you."
"Huh?" I said with my voice quaking.
"You heard me. I wanna fuck you. A young thing like you. I bet you could please me for hours."
My mouth dropped open.
"Tell me, when was the last time you were fucked? I mean really fucked. Good and hard by a real woman."
"I've never been fucked, ma'am. Not at all."
A sly smile formed on her lips.
The next thing I knew, I was in her car driving down the road toward her house. I had no idea what was in store for me. The whole experience was strangely erotic. I guess I was kind of like her boy toy. I barely said anything. She basically said let's go and I followed. I didn't even ask any questions. I just went. It's like she cast some kind of weird spell on me.
Her house was a two-story affair smack dab in the middle of a newer subdivision. You could tell she had money by the way the house was decorated. Everything was done with a touch of class. Once inside, she fixed herself a glass of red wine and took a seat on the couch in the living room. I stood awkwardly in the middle of the room, not quite sure what to do. She leaned back and smiled as she watched me move nervously about.
Suddenly she commanded me to take of my clothes. I hesitated at first, but from her look I knew she was in charge. Even though I was embarrassed, I did as I was told. I unbuttoned by shirt and removed it slowly. Next came my shoes and socks. It what seemed like no time at all, I was standing in the middle of the room in only my pants. She watched calmly from the couch.
"Don't stop there."
Once again, I sensed she meant business and I slowly slid off my pants. Now I was practically naked. My white underwear was the only thing between her and my penis.
"Go on."
I hesitated, unsure what she would think, but I knew that I had no choice. With my stomach practically in my throat, I did as she said. Tantalizingly slow, I slid my underwear down over my hips and onto the floor. I found the situation to be embarrassing but incredibly erotic nonetheless. By then, my cock was rock hard and pointing straight at the ceiling. She giggled a little when she first saw it.
"Come here."
I moved closer until I was standing right in front of her. She smiled as she reached out to touch it.
"It's so small."
My secret was no longer mine alone. At a slightly shorter than five inches, my cock had been a touchy subject since I was a teenager. I was embarrassed to shower in front of other men, and up until know, I had never had the opportunity or the inclination to let a woman see it. Yet here I was, standing completely naked in front of a beautiful older woman. I always wondered what this moment would be like and now I knew. Here I stood shaking as this strange woman gently stroked my tiny penis.
"It's beautiful though. So nicely curved. So smooth. So hard."
She looked up at me sly grin.
"Oh yeah, I want this cock to fuck me. I want this cock to fuck me hard."
My body was still shaking. Goosebumps ran up my arms and across my chest.
