The Gupsy

Author: Michael Shuler

Fall is a beautiful time in Vermont. The trees are decorated in all their finest colors, hunters are stalking game in the woods, and the rustic fences and covered bridges create a wonderland for painters. Photographers make their living on the fall leaves in Vermont. I am one of them.

I, a simple real estate agent, enjoy driving in the country, taking pictures, absorbing all the scenic wonders and looking for a good deal on the side. A realtor is a realtor, no matter where he goes. I thought I had seen everything, during my travels in the Northeast. I have seen sheep covered hillsides, snowy mountains, and foggy landscapes which resemble a foreign planet. I have seen stately elk, fish jumping through rapids, and even a bear not long ago fishing from the banks of Long Creek. But on this trip I knew I had seen it all. I pulled up in a little roadside park and saw a Gypsy wagon all nestled into a camping spot. The team of horses were picketed not far away. An old man stood over by the fire, and a beautiful black-haired woman stood with her hands on her hips, looking me over as I pulled in, driving my 20th century version of their wagon, a minivan.

“That’s a strange sight,” I said pointing at their covered wagon with a smile as I pulled in to the adjoining sight. There were only three in the entire park. I noticed no tables, a single toilet, and no faucets for water.

“Why?” the woman asked with a suspicious expression.

“I… your…” I started to explain, but I trailed off under her stern gaze. Were these people for real? There were no Gypsies in this country. Where there?

“Is there any water?” I asked, dying for some real campfire coffee.

“That way,” she pointed into the woods.”

“How far?”

“About half a mile,” she said, wiping her hands on her multicolored dress and turning away. I wanted to talk to her. She was very exotic, and not half bad looking, in an malevolent sort of way.

“C… could you show me?” I asked with a hopeful smile. She cursed under her breath, shook her head sadly, then started off with her own bucket. I grabbed my plastic pail and ran to catch up.

“It’s beautiful here,” I said, following a set of wheeltracks with her. She closed her eyes and took a deep breath. I saw her nipples harden before my very eyes and gasped.

“What!” she demanded, with her eyes flying open.

“You… you looked very beautiful,” I said, turning red with embarassment.

“Why do men always stammer and turn red when they lie?” she asked in disgust.

“All right, damit, I was surprised when I saw your nipples harden. They are very… Erotic in the thin material of that dress.”

“There, now wasn’t that better than lying. It cleared the air and got you one step closer to what you really want.”


“Me,” she said sternly.

“What are you, a fortune teller?” I asked with a half smile.


“Oh. So how do I get the rest of the way?”

“You carry my bucket back to the campsight, and you ask me very nicely.”

In actuality, the three of us ate together. The old man was Fernando, her uncle. We finished eating and Rosanne heated water for dishes. Fernando took up a fishing pole and started off toward the river. I sidled closer to Rosanne when he was out of sight.

“Rosanne, I think you are very beautiful and I would like to make love to you,” I said formally. I was more embarrassed than I had ever been in my entire life. I waited as she seemed to think it over. She moved the dishwater off the fire and stood, motioning toward the wagon. I was so nervous I was shaking. I had fucked dozens of women, what made this one different? I felt like a schoolboy asking my teacher permission to take a piss. Hell, I was 29 years old.

We undressed wordlessly. I gazed around the inside of the wagon in wonder. It was mostly constructed of wooden cabinets inside, formed to fit inside the canvas top. I was tempted to open one to look inside, but her stern gaze stopped me. I lay naked on her bed, which took up most of the wagon. She opened her dress and looked down at me. Her breasts were phenomenal, and I am and always have been a breast man. They were perfectly round, like a mellon cut in half, with small, delicate nipples. I was awestruck. I reached for her, as she knelt above me, but she stopped me.

“This is my legacy, my tie between the past and the future,” she said, covering her pussy. I had half a mind to dress and run, but she was too damned hot.

“I have seen my future,” she said with a vague look, “many different futures. The one I have chosen is the one where I conceive your baby and live alone. You will never see it or me again. Any other future will be terrible and lonely,” she said sadly. “Do you understand?”

“Yeah, sure,” I said hurriedly. All I wanted was a fuck.

“You don’t but you will,” she said offhandedly. She sank down and positioned herself between my legs.

By the time that she touched my cock I was shaking in anticipation. She looked a little like Cher, and a little like every evil bitch you have ever seen in the horror films. Her touch was like magic. I have received many blowjobs, but her hands and mouth gave me a raging hardon so big, it was painful. Maybe she had an amazing talent, maybe she used some kind of magic, but I was in a world of my own. My toes curled as her warm lips moved up and down on my cock. Her mouth was so hot around me. Her gentle touched raised goose bumps all over my body. I watched her slender fingers work along the side of my leg. She was setting me on fire.

“I’m as ready as I will ever be,” I whispered. “Let me do you.”

She pulled her mouth off my cock. She looked so solemn, so serious as she stood, walked forward and squatted on my face. I looked up at her hairless, pink little pussy and I gasped in appreciation. There was no dark stubble from a razor, she was simply hairless, like a ten year old girl. More magic.

I was amazed at the soft pink lips that approached my face. I surged up and captured her pussy in my mouth and sucked, while my tongue explored her trembling flesh. I could feel it move around my tongue like a living creature. I flicked my tongue over her clit and she stiffened and moaned, the first sound she had made since we started. A shimmer of juices coated her baby- like flesh. I licked them and savored her fresh taste and aroma. Every time I licked her pussy it made me a bit hornier. I sucked savagely, making her cry out in pain. I couldn’t help it, she was driving me crazy. She had the most delicious pussy I had ever eaten. And, it was by far the most erotic.

She pulled up off my mouth and I cried out an objection. But she simply looked at me as she backed over my body and positioned herself over my cock. She took my cock in her hand and positioned it just right, then sank down, impaling herself on my long, stiff member. I could never remember my cock being so big. It seemed to sink into her vagina endlessly. Finally she sat with her pelvis pressed against mine. I could feel my entire throbbing length simply waiting inside her. It was glorious. So much heat, so much steamy moisture. Her pussy muscles moved around my cock, squeezing it minutely as we waited.

Finally, as I was about to go out of my mind, she rose up off my crotch and slid her pussy back down again. I was sure my head would explode with the terrible pleasure which raced through my body. What was she doing to me? The simple act of riding on my cock was causing me to squirm like a virgin. The fire was raging and uncontrollable with just that one initial movement. The following movements were less strong, but far stronger than anything I had felt before. Her wet pussy was holding my cock in a death grip. With a terrible pressure it rose and milked my cock all the way up, then slid down and milked it all over again. What was she doing to me? How was she doing it. How could this feel so much stronger than any other woman I had fucked. Was she really a woman?

She started riding faster, then suddenly paused. She sat for a moment, looking down at me, then began turning, while still impaled by my cock.

Once she was facing away from me, but still fully seated on my cock, she leaned forward, grabbed my ankles and began to ride more quickly. I watched her pussy stretch around my cock. It was very erotic. She began to bounce faster. I clutched her ass in a grip of iron and held it, as she bounced on my long penis. It was a wonderful, if strange, fuck. I couldn’t complain, I was getting the best fuck of my life. Why she was doing it, was her business.

As she bounced on my cock, I noticed her tight little asshole. It looked so damned inviting. I had always liked to fuck an ass, but rarely got the opportunity. Maybe if I lifted… She was coming. I could tell by her urgency and the slight moans she was making. I grabbed her ass and pounded her down on top of me. Her cries increased, as did the friction on my cock. It wouldn’t be long now, just a few more…

I came big, at the same moment that she did. We both panted and withered, locked in unison. My cock spurted thick cum up into her pussy, while her pussy clenched and milked my cock. It was so fucking wonderful. I had heard of pussies like her’s, a pussy strong enough to lift a beer bottle from the floor. This was the first time I had felt one. Like a distant heartbeat, her pussy clasped and unclasped my cock, stimulating me almost painfully, as I came inside her. Damned she was good. Belatedly, I fell back and lay panting. She too pulled off me and turned to look down at me.

We rested for a few minutes, then she clawed her way closer to me and took my wilted cock into her mouth again. As she sucked quietly, I grew horny as hell knowing that she was tasting her own juices. I could see them coating my cock. She seemed to like them.

I looked her in the eyes, wondering if she knew what I was thinking. I had a very erie feeling that she did. If so, she would know that I adored her fantastic breasts, her tiny little ass, and her childish pussy. But most of all she would know that I wanted to fuck her in her slender, beautiful ass more than anything. I looked in her eyes wondering if she knew what I thought and a bit fearful of the prospect.

To my amazement, she stood, looked down at my prone body, and sat with her perfect little ass over my cock. She guided the tip of my cock into her asshole and sank carefully down, impaling herself. I hissed in joy. It was as wonderful as I thought it would be. Her ass was so hot and tight around me. She too seemed to be enjoying it.

She cried a little as she began bouncing on my stiffened member. It filled her tiny asshole tightly. Her asshole was stretched thin around my throbbing cock. I could feel the friction of her anus as it rode gently up and down.

“Oh… oh God,” I gasped. She gave me the first smile I had seen on her face. Her face lit like the Vermont hillsides in full sunlight. What a difference her smile made. Suddenly all the foreboding was gone. I gloried in the wonderful sensations created by her ass. I noticed her fingers going down to her girlish pussy and rotating in them as she rode. It felt so incredible.

A board creaked beneath her bed. My cock in her ass made a slick, wet sound. Far away a dog barked and a crow cried in the treetops nearby. The sounds of our panting breath sounded muted in the confines of the wagon. Her ass looked beautiful and unreal as it bounced on my cock. Time seemed to stand still. A burning glow started deep inside of my loins. It grew like a distant light hurtling toward me. Suddenly I gasped and grabbed her shapely ass, driving it down on my cock. She whimpered just once before she came, shuddering and grunting above me. I came in a gush of expelled air and muttered curses. I held her ass in a death grip, while my cock emptied it’s contents into her sweet ass. She wiggled and moaned, then fell silent, panting and limp.

I moaned and rubbed her back. A coyote called from miles away. Rosanne suddenly drew erect, listening.

“We must hurry,” she whispered. “Fernando is returning.”

She was right. By the time I was dressed and seated outside drinking coffee, Uncle Fernando returned. He gave me a knowing look and held up a string of trout. I looked from him to the trout in amazement. We ate the fish just before dark. I went to sleep in my minivan. When I awoke they were gone. I don’t know how they harnessed the wagon and set off in complete silence, but they did.

That night with Rosanne was the most incredible night of my life. I have looked for her since then, to no avail. If you see a Gypsies wagon, and old man and a slender, delicious woman with a baby, will you let me know?

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