The Hitchhiker

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.

"Get down on your knees."

I immediately dropped to me knees and positioned myself between her spread legs. I got a glimpse of her underwear as her skirt rode up when she shuffled in her seat. What came next I certainly didn't expect. Before I knew what happened, I had a leather collar around my neck that was securely fashioned to a short leash.

"Follow me."

The woman got up and started to lead me away. I got up to follow but was quickly rebuffed.

"On your knees."

The woman led me to the back of her house. I followed like a puppy dog down on all fours. The room we entered was like nothing I had ever seen before. It was predominately deep red with a touch of black. Leather was in abundance. Throughout the room were several medieval looking contraptions. As best as I could figure the room seemed to be some kind of torture chamber.

"Up on your feet!"

I immediately jumped to my feet. My Mistress, if you could now call her that, pulled me over toward a contraption near the wall. Before I could utter another word, she had a ball gag in my mouth and both my arms and legs fastened in an "X" to a wooden frame. Needless to say, I was extremely vulnerable. My Mistress giggled as she watched me struggle. That was when the torture began. It wasn't real torture, but more like sexual torture.

My Mistress knew how much I lusted after her body. My cock was aching to be released, but instead of giving me the satisfaction I craved, she teased me even more. Button by button, piece by piece, she slowly she revealed her succulent body. I was whimpering for relief by the time she was down to her black bra and panties. Before revealing her luscious tits, she moved in close to where she was practically touching me. Mercifully, she unhooked her bra and let her breasts fall forth. Slowly she backed away, looking straight into my eyes as she did. Turning around she slid her black bikini bottoms over her hips and down her long, silky smooth legs. She never turned around as she did so, allowing me to see only her firmly toned ass. Now clad in only high heels, I watched from behind and she slowly slid a finger deep into her sopping wet pussy. Turning toward me, but still keeping her pussy out of view, she brought the finger to her lips and teasingly licked it clean.

Finally, she turned around to reveal the part of her body my tiny cock craved. Her pussy was magnificent. Neatly trimmed in a thin vertical stripe. It was jet black in stark contrast to her strawberry blonde hair. She sauntered toward me, her hips swaying seductively. Standing directly in front of me, she again buried her finger deep into her pussy, but instead of bringing it to her lips, she removed the ball gag and slowly ran her wet finger across my lips. I moaned with desire as she did. This seemed to please her immensely.

"So you want to taste my cunt."

"Yes, ma'am," I mumbled.

She looked down at my cock, cupping my balls in her hand.

"What makes you think I'd let the boy attached to this puny thing lick my cunt?"

Beyond humiliated, I stared at the floor. She immediately turned away and walked across the room, returning with a small leather strap like nothing I'd ever seen.

"Do you think you're worthy to serve this body."

My failure to answer brought a smile to her lips. Almost without me knowing, she reached down and tied the small leather strap around my balls. The strap formed a leash so she could pull on my balls, tightening the noose as she pleased. She seemed amused as I jumped with each tug. She reached over and grabbed paddle hanging on a wall nearby. With little effort, she rotated the frame holding me so my ass was now facing her instead of my cock. She fed the cock leash between my legs so she could still pull on my balls as needed.

SMACK!

I felt the sharp sting of the paddle on my ass.

"Do you want to lick this pussy?"

SMACK!

"I said do you want to lick this pussy?"

"Yes ma'am," I stuttered.

"Are you going to make your Mistress cum?"

"Yes ma'am."

SMACK! SMACK!

"How are you going to make your Mistress cum with that tiny little cock?"

SMACK! By now my ass was raw, if not beat red.

"With my tongue."

"Very good."

My Mistress moved closer. She gently massaged my ass, her fingers running up and down my crack as she whispered in my ear.

"Is your Mistress going to fuck you?"

"Yes," I muttered, breathing rapidly.

She backed away.

"Is your Mistress going to fuck you hard?"

"Yes," I softly replied.

SMACK!

"I asked if your Mistress going to fuck you hard?"

"Yes, ma'am," I said a little louder.

SMACK!

"How hard is she going to fuck you?"

"Hard!" I screamed.

"Is she going to fuck your brains out?"

SMACK!

"Yes! Yes! She's going to fuck me until I scream."

With that she stopped and untied me. Tugging on the cock leash, she led me across the room. I stood before her as she relaxed in a chair.

"On your knees."

I positioned myself on the floor directly in front of her. She spread her legs and let me get a good look.

"Do you like my pussy?"

"Yes ma'am. Very much."

"Did you imagine licking my pussy when you were staring at me in the diner?"

"Yes ma'am."

With that, she grabbed the back of my head and shoved it into her sopping cunt.

"Eat me."

She leaned back, arching in her back as she took in the sensation of my warm tongue darting in and out of her pussy. Her breathing increased and she began to moan. Soon her eyes rolled back into her head as the pleasure overtook her.

"Oh yeah, lick my pussy little boy."

Now with both hands on the back of my head, she pushed my face in deeper.

"Oh yeah, just like that."

Her moans grew louder as my pace quickened. I buried my tongue into her cunt as deep as it would go.

"Come on little boy, fuck me with your tongue."

Her breathing grew erratic as her arousal increased.

"Harder!"

She slammed my face into her crotch.

"Deeper! Deeper!"

Suddenly her back arched even further and her thighs tightened around my head. Even with my ears covered I could still hear her screams of ecstasy. I kept licking with all my might, until the grip of her thighs on my head relaxed. Finally, her cries subsided and were replaced with heavy breathing. I kept licking her pussy as her right hand gently massaged the back of my head. When her breathing returned to normal, she tilted my head back so I was forced to look up at her. My face was covered with her juices. She smiled her approval.

"I'm not done with you yet."

Grabbing my cock with her leash once again, she dragged me to the bed that dominated the room.

"On your back."

I did as ordered. Once again she tied me down, my limbs in same "X" position as before, except this time I was on my back. On the bed helpless, I looked up toward the ceiling. Above the bad, the ceiling was covered with mirrors. I saw the reflection of my tiny cock, aching for release. My Mistress saw me looking up.

"Now you can watch yourself as I fuck you hard."

She wasted no time. Before I knew it, she was straddling me while one hand was pulling on the cock leash to keep me in line. Foreplay was nonexistent. My Mistress simply grabbed my tiny little cock and inserted it into her pussy. She smiled as she began to fuck me hard, riding my cock with abandon.

The sensation was overwhelming. Strapped to the bed and being fucked by this incredibly sexy woman was nothing short of amazing. My cock was in heaven, the tight grip of her sopping wet pussy drove me wild. I grunted with each thrust and the view in the mirror only added to the excitement. She seemed to enjoy the effect she was having on me. I was about to lose control when I felt the noose tighten around my balls. She must have sensed my impending orgasm and used the leash to stop it. By this point my cock was ready to explode, but there was nothing I could do about it. My Mistress was in complete control. Instead of grunting with each thrust, the leash had now reduced me to whimpering. My Mistress seemed to enjoy that even more.

She continued to pound away, milking my cock for all it was worth. Once again her breathing was become erratic as she rode my shaft. She was paying virtually no attention to me. She was strictly in it for her own pleasure. Her eyes were closed as she repeatedly slammed her cunt into my pelvis. Soon she was grunting as well, her own body begging for release with each thrust.

Her orgasm must have been fast approaching as she released the grip on my balls. My whimpers returned to grunts. Now we were both grunting, growing louder with every thrust. She was fucking me urgently now, her hips were driving deep into my cock with abandon. Then it happened. Her orgasm began to overwhelm her. Her grunts turned to moans and screams and she seemingly lost control of her body. Seeing her back arch and her body flail wildly sent me over the edge as well. Her pussy clamped tight around my aching cock as I shot my load deep inside her. She never stopped pumping as we came together. I watched in the mirror as the sounds of our ecstasy echoed throughout the room.

Slowly the sounds of our pleasure subsided and our breathing returned to normal. She was still straddling me when she finally opened her eyes. Still trying to gather myself, she looked down at me and smiled.

"I'm not done with you yet."