The Harlot of Owl's Head Inn

The "Owl's Head Inn" stands at a junction where two lonely highways intersect in the middle of a windswept moor. It sees a fair amount of traffic from trappers, merchants, soldiers, local farmers, and the occasional highwayman. Oliver Evans owned it for years, a widower with two daughters -- Elizabeth and Samantha.

I am Samantha. I like to call myself " The Harlot of Owl's Head Inn" because it sounds more romantic than just plain 'whore', which is what my sister calls me. She would know I guess, because she's the one who pushed me into that profession. Under the circumstances you wouldn't think she'd complain, would you?

We were not noble or wealthy by any means, but we were moderately well off and well raised. We were respectable girls who attended church regularly, went to confession, didn't speak to strange men, and all of that. Elizabeth and I even got along reasonably well until Theodore came along, and that's when the trouble began.

Theodore was a good looking young man in the neighborhood who often came over to the inn for a drink. We both found him very attractive, but as Elizabeth was the one who stood to inherit the inn once our father died, she was the one he married. He wasted no time in planting his seed, and my sister was positively swelling with it only months after the wedding. Swelling? Bloating might be a better word. Even her ankles were blown up to twice their usual size.

Theodore seemed unhappy with the situation. He never looked at my portly sister without an expression of regret for the trim little thing she had once been. It did not escape my notice that he frequently turned an interested eye toward me, just as he had done in the days before his marriage.

Unlike my sister, I still had a narrow waist balanced between ample breasts and hips. At eighteen I was beginning to be noticed by plenty of men who came into the inn and there were frequent inquiries about me. Theodore, who was the head of the house now that our father was gone, took it all in stride but usually with a rather frustrated scowl.

It was Theodore who woke my passions. Otherwise I would probably have married some nice farmer and become as fat and frumpy as my sister. It might have been a more respectable life, but not nearly as much fun. And ironically, although my sister meant for it to shame me, my seemingly unrespectable profession led me to a much more advantageous social position than would otherwise have been available to me. That is what this story is about; how an innkeeper's daughter went from whore to lady in the space of a year.

It started one night when my sister sent me to tell Theodore dinner was almost ready. I found him out in the stable, skulking moodily in the loft, staring down at the horses in an absent sort of way. "Elizabeth says dinner is almost ready." I told him.

As it so often did when he looked at me in recent months, his expression became quite wolfish. "She can wait." he said shortly.

"Fine." I answered, and turned to go back down the ladder.

"Wait. Come here." he said, indicating the section of floor right in front of him.

I was sexually inexperienced, but I wasn't naïve. I knew what the look in his eyes meant. I was inexperienced perhaps, but curious, and maybe there was a part of me that wanted to pay Elizabeth back for being the one he married. I closed the distance between us.

He leaned against the wall in an insolent sort of way and looked me up and down. "You're looking pretty good, Samantha."

"So?" I asked witheringly.

"So. Have you noticed all the young men looking at you?"

"I notice you look at me."

"You're better to look at than Elizabeth is these days." he snorted. "And forget touching her. Not that she was so fond of being touched anyway..."

"It's your fault that she's pregnant." I pointed out.

"She's the one that was in a hurry to have a kid. Not me. Come here." He took a step backward into the shadows.

"I don't know if that's such a good idea." I said, starting to turn away.

I was pulled up short by his hand on my arm as he pulled me into the shadows with him and backed me against the wall. "Stay still." he growled, and his hands began roving over my body.

I was suddenly aware of how much larger he was and how far we were from help. "She'll wonder where we are."

"Ha. She'd never make it up the ladder."

That was true I supposed. Meanwhile, his hands were fondling my breasts through my blouse, and I could feel my nipples getting hard. So could he.

"You want it, don't you?" he asked. "You're not like your squeamish older sister. I see it in your eyes -- all you need is someone to wake you up a bit."

At the time I didn't agree with him, but in retrospect, he was right. At any rate, I didn't argue. I just stood there, transfixed. I didn't move as I watched him unfasten his pants and pull out his erection. I'd never seen one before and I was completely fascinated.

He took both my hands and wrapped them around it. I was amazed by how hard it felt.

"Well already you're more generous than your sister." he said wryly. "She's half afraid to look, let alone touch. You know when I really wanted a good time, I'd have sex with the cook's daughter until she was sent away."

"You what---?" I asked in horror.

"People do it, little virgin. They just don't talk about it." Now he was slowly guiding my hands up and down his length. "Honestly....you don't really want to get married not knowing anything, do you? Virginity is overrated. Most men would rather have a woman who knows what to do in bed. I know I would have."

When his hands stopped guiding mine, I'm not sure, but I suddenly realized that I was stroking him all on my own with a firm, two handed grip. He was engaged in the task of pulling the tail of my blouse out of my skirt, bunching it up under my armpits to expose my breasts. I froze as he leaned down and began sucking on one of my nipples. I felt a slow seep of moisture between my legs that I'd never experienced before.

All I was really sure of at the moment was that he was making me feel very good. I stood still, focused entirely on the warmth and wetness of his mouth, the soft rasp of his tongue, and the gentle suction of his lips.

His hands had strayed down my waist, over the gentle curve of my hip, and had begun hiking up my skirt. One of them had found bare flesh and was sliding up my inner thigh. I knew I should stop him, that what we were doing was wrong, but somehow the forbidden nature of it made it that much more attractive.

One of his fingers suddenly slid between the soft folds of my pussy. "Theodore?"

His mouth left my breast and he straightened up, his finger still sawing back and forth inside my slick folds. His spare hand took one of mine and directed it pointedly back to his cock. I didn't need to be told what to do, and I instinctively matched my rhythm to his.

"So sweet, Samantha." he murmured. He pressed against me more closely and covered my mouth with his. I was startled at the feeling of his tongue probing my lips and jerked my head away. "Easy." he whispered. He reached for my other hand and drew it over to join the other. "Do you like how my dick feels?" he asked.

It was a frank question that deserved a frank answer. "Yes." I whispered, face flushing.

A low growl escaped him and he kissed me again with more urgency. This time I let his tongue slide into my mouth. I felt it slip beneath mine and swirl around it in dizzying spirals. He kept going until I kissed him back, my hands pumping his cock more vigorously.

His fingers worked my clitoris more quickly in response. I moaned in wanton pleasure and leaned back against the wall, spreading my legs wider for him. "That's it Samantha..." he whispered. "Do it for me...it'll feel so good..."

"Theodore!" I squealed as white hot electric shot through me. He kissed me again to silence my moans while his fingers kept rubbing until I was so sensitized that it hurt.

My legs were shaking so hard that I didn't mind when he pushed me onto my knees. He was guiding my hands up and down his rigid shaft again, and from this position, it was right in front of my nose. I could see a drop of liquid glistening on the tip.

"Let me see you suck it, Samantha." he whispered urgently. "I've never had a virgin do it before. I want to watch you suck your first dick."

It was a novel concept for me, but I was so turned on that it seemed like a good idea at the time. I gave it a long, slow lick from bottom to top and heard him inhale sharply. Between guiding me into position by hand and whispering breathless instructions, she showed me what I was supposed to do.

With one hand wrapped firmly around the part I couldn't quite manage to take without choking, I slid my lips quickly up and down his length. Glancing up at him with big doe eyes, I found him looking back at me with a predatory, lust filled expression. It was kind of scary, but arousing all the same.

"Oh god Samantha." he groaned, running his fingers through my hair. "You feel so good. Do you like it?"

I paused just long enough to gasp, "Yes!" and then went back to work.

My enjoyment of the situation seemed to feed his arousal. I could feel him tensing up and his cock swelling in my mouth. "Stop." he ground out.

I glanced up in surprise.

"I want you to watch." he said thickly. "I want you to see everything, little virgin. Push those pretty breasts together for me. Good girl....now watch me."

As if I could do anything else. I couldn't take his eyes off him as he fisted his erection and started to masturbate just inches from my face. I was frozen in the position he'd asked me to adopt, kneeling with my breasts cupped in my hands and pressed together. I couldn't stop staring at that hard, thick piece of flesh as he stroked it so hard that his balls bounced.

"Get ready." he gasped.

I flinched in shock as a strand of thick white fluid erupted from his cock and splattered my breasts. It was the most fascinating and arousing thing I'd ever seen. I watched in a lust filled haze as it kept coming, until the last few drops landed on one of my rosy nipples.

"Your eyes are so huge." he said, sounding amused. "Now you know what male pleasure looks like, little virgin."

I startled at the sound of a shout from below. It was one of the hired hands. "Ted? You up there?"

"Yeah." Theodore answered calmly, refastening his pants and going to peer over the edge of the loft. "What?"

"Your wife says dinner's ready. Have you seen your sister in law? She's supposed to be looking for you."

"If I see her, I'll tell her. I'll be down in a bit."

During this exchange I'd frantically pulled my blouse back down and smoothed out my skirt. Theodore looked at me in evident amusement. "We better not both go back together. You go on and I'll follow in a while. Listen -- I want to see you again. Meet me in the root cellar later tonight."

I nodded blankly and made good my escape without another word, too stunned at what had just happened to dwell on it, at least right then. Later that night in bed it was all that I thought about, my mind replaying it over and over in exact detail. It was the beginning of my sexual awakening, but as I lay in bed that night, wrapped in illicit fantasies, I never foresaw that it would lead me into a career of prostitution.

Not that I'm complaining, mind you. There were a lot of perks to that job, and I had a lot of fun, as I'll describe to you later in lurid detail.