Nicole pulled her car out of sight behind the barn. A fast glance at her watch told her that she was running late, so she quickly got out of the car and ran to the back to open the trunk. Stripping off as fast as she could and throwing her clothing and jewelry into the trunk, she reached for her white cowboy hat.
She had just placed it on her head when Annabelle said sternly from behind her, “Why are you late?!”
Nicole yelped and jumped and then sobbed out quickly, “There was an accident, the road was blocked.”
“But why didn’t you arrive naked?!” Annabelle almost snarled. “An accident didn’t prevent that!”
“It was still light when I left my apartment,” Nicole wailed. “People would have seen me! I couldn’t stand that. I was going to stop in the grove and strip off, but I was running late.”
Annabelle frowned at her and then said roughly, “Why four different hats?”
Nicole looked startled, but quickly said, “White means a pleasure night; red means pain; black means denial; and the red and white straw hat means pleasure and pain.”
Annabelle grabbed the white Stetson off Nicole’s head and threw it back into the trunk. “Tonight is not going to be a white hat night,” she said curtly as she picked up the red hat.
“I think I will wear the hats in this relationship from now on,” she said firmly as she put the red hat on her own head. “And tonight just became a night of pain.”
“Will I still get my orgasm? Nicole whimpered, almost begging.
“If you accept the pain like a proper little slave cowgirl,” Annabelle answered curtly.
Nicole looked shocked but said nothing.
“Follow me into the barn,” Annabelle said firmly, “and bring your duffle bag.”
“Yes, Mistress Ann,” Nicole said softly as she picked up her bag and followed Annabelle into the barn.
“I always like to check out other girls’ toys,” Annabelle said sweetly as she rummaged through Nicole’s duffel.
She held up a whip that was made of several wide strips of rough cloth. “What is this?” she said looking at Nicole. She swished it through the air and added, “It doesn’t even swing properly. How could it even be felt?”
“It’s supposed to be wet,” Nicole said. “You soak it in water or oil or even honey. The individual swats don’t hurt that much, but after a while your whole back or ass or legs or whatever starts turning bright red. I used to have one made out of chamois, but I used honey on it and couldn’t get it out.”
“OK. little naked cowgirl,” Annabelle said almost sweetly, “stand against the ladder to the loft and we will try this out. I guess I will have to use water for now.”
Nicole stood facing the ladder that led up to the loft.
“Hands high above your head!” Annabelle ordered. “Grab the highest rung you can reach on your tiptoes.”
Nicole did as she was ordered and then stood there quivering from the exertion of stretching herself up so far. Annabelle stepped up alongside her and began wrapping strips of leather around her hands and wrists.
“These are high quality,” Annabelle said as she wrapped the leather straps snugly around the ladder... and Nicole’s wrists. “Where’d you get them?”
“I have a friend who does leather work for Renaissance Faires,” Nicole replied. “She gives me her scrap leather.”
“Would she make a custom whip or flogger?” Annabelle asked.
Nicole’s cheeks... on both ends... turned a bright red and Annabelle laughed. “I guess you don’t have to answer that one. What was it, a whip or a flogger?”
Nicole looked down at the ground. Her skin became a deeper shade of red. “It was a tawse,” she said very softly. “It’s in the bag.”
Annabelle patted Nicole’s asscheeks. “I’ve never seen a girl who ass-blushed before,” she said almost laughing. Then she rummaged through the bag and lifted the tawse into the air.
“Quality work,” she said as she tapped Nicole lightly on the ass with the tawse. Nicole yelped slightly but said nothing.
It was silent in the barn for a short while. Nicole stood staring through the ladder at the area under the loft. There were a variety of odd-looking machines and other stuff stored there. She heard water running and then a loud “thunk” as a heavy bucket full of water was dropped on the floor directly alongside her.
“How long do you have to let it soak?” Annabelle asked.
“It saturates pretty quickly,” Nicole said, “but it doesn’t hold the water. The chamois one was so much better.”
She then gasped very loudly. Annabelle had swung the wet whip so that it hit on Nicole’s legs just below her ass. Her gasp wasn’t from pain. The cloth whip didn’t hurt on the first strokes, but it was COLD... very cold.
“This has a different feel,” Annabelle said, “but I think I can get used to it.”
She swung the whip rapidly seven or eight times. Strokes seven and eight were directly across Nicole’s asscheeks.
“So, my little naked cowgirl,” Annabelle said, laughing. She laughed again and added, “... my little wet, naked cowgirl. How many strokes does it take before it starts to hurt?”
Nicole mumbled an answer and Annabelle barked out, “Speak up, slave!’
“A hundred,” Nicole stuttered out, “it usually doesn’t start to hurt until around a hundred.”
“That’s a lot of work,” Annabelle scoffed. “Who whips you with it?”
“I used to have a friend in college,” Nicole answered. “We’d make bets.”
“And you would usually lose, wouldn’t you?” Annabelle asked as she slowly pulled the wet whip across Nicole’s ass.
“Not always,” Nicole replied defensively.
“Do you ever use it on yourself?” Annabelle asked as she dunked the whip back into the water.
“I can’t use it in my apartment,” Nicole said softly.
Annabelle laughed. “Way too messy,” she said. “You need someplace like... a barn.”
Her voice got very firm. “Count them, little naked cowgirl. You don’t have to thank me or even say Mistress, but I want a number from each stroke. You understand that?”
“Yes, Mistress Ann,” Nicole answered.
Annabelle stood to Nicole’s side and began flailing with the whip. Each stroke made a loud “splat!” as the wet cloth struck Nicole’s skin. It reminded Annabelle of those couple times when she whipped Lucille with a wet towel in the shower room at college.
Nicole counted every stroke as Annabelle slowly moved up from her ass. When Annabelle reached Nicole’s shoulders, she began moving downward. Every fifteen strokes she would pause slightly to plunge the cloth whip back into the bucket of water.
At eighty-eight, Nicole’s back and ass were turning a bright shade of red and she began grunting slightly with each stroke. At one hundred and thirty she began begging, “Please, Mistress Ann, no more, no more.”
Annabelle’s only response was “Keep the count, slavegirl!”
Nicole continued counting, but she was grunting and whining before each count. When the count reached two hundred, Annabelle dropped the whip into the bucket and stepped around in front of Nicole. She reached up and squeezed Nicole’s nipples. Nicole yelped, and Annabelle gasped very slightly, looking surprised.
“You’re dripping milk,” she said firmly. “Do you have a baby at home?”
“No... NO!” Nicole quickly answered. “It’s a side effect of my birth control pills. It’s kind of rare and it only happens if I’m turned on, but my breasts get bigger and a little milk comes out.”
Annabelle chuckled deeply. “You are a bundle of surprises, my naked little cowgirl. Two hundred lashes with a whip– albeit a cloth whip– and you aren’t screaming in pain. Instead you are turned on enough for your tits to swell up and milk to leak out of those udders.”
“I’m sorry, Mistress Ann,” Nicole said, almost sobbing.
“I’m not,” Annabelle said with a wicked smile. She stroked Nicole’s right breast and said, “It gives me a chance to try out some of my grandfather’s old equipment.” She chuckled again, almost sounding evil, and said, “He was a dirty old man... well, actually he was probably a dirty young man too, but in any case he left me a lot of very interesting fetish gear including...” She pointed to something covered with a tarp in the corner. “... a Hucow milking station.”
She patted Nicole on the ass and said, “You just hang around there while I get things set up.”
While Annabelle was moving some things around, Nicole asked timidly, “What’s a Hucow, Mistress Ann?”
Annabelle laughed. “When I was a really small girl and came out here on weekends, Grandpa used to have this young girl who helped out around the farm. Grandpa called her his little milk-maid. I always felt sorry for her because she had such huge breasts. By the time I was old enough to ask about it, though, she was gone. Grammy said that she had found a bull that would appreciate her. It wasn’t until I found this milking station that the penny dropped and I realized what she had to have been.”
“What was she?” Nicole asked.
“She was a Hucow– a human female who liked to be milked like a cow and had the udders to make it work,” Annabelle answered. She laughed and then said, “You don’t have enough upstairs to provide much milk, but I think you will appreciate what this machine can do for you.” She laughed again. “And I,” she said, still laughing, “can have fun seeing if I can encourage you to produce a little cream.”
Annabelle pulled the tarp off a strange-looking machine and dragged it into the light. It was a bunch of stainless steel pipes arranged like a small box sitting on a large roll-around stand. On one end was a small padded bench. On the other end there were two short posts with leather bands attached. At the base of those posts were round padded areas.
“Let’s get you in here,” Annabelle said brightly, “and then I’ll bring out the milker.”
“Do I have to, Mistress Ann?” Nicole whined as Annabelle began unwrapping her wrists.
“Look at it this way,” Annabelle said, “you won’t be hanging by your wrists. You won’t be hanging at all... well except for your tits. They will be hanging down quite nicely.”
Nicole looked slightly afraid as Annabelle led her over to the strange contraption. “You kneel on that,” she said, “and then you put your hands up there on those round pads.”
Nicole knelt slowly and then tried to put her hands on the round pads.
“You have to reach over the first of the two bars,” Annabelle said roughly. “I think you can figure out where your teats are supposed to go.”
Nicole cautiously put her arms between the two smaller bars which went across the frame. The first bar was slightly curved. It ended up just below her breasts. The second bar had a large padded curve in it that fit under her neck.
“Quick adjustment,” Annabelle said as she moved the neck bar slightly. There was a slight click as it moved into place and then a much louder click as Annabelle pushed the top half of the head restraint into place.
“Can’t have a cow wandering off during milking,” she said with a laugh. Then she began securing Nicole’s arms to the short poles. When she was done with that, she went to the back of the frame and pulled two straps across each of Nicole’s calves.
“Now the fun part,” she said brightly and hurried back under the loft to retrieve a small stand with a piece of equipment mounted on it. Attached to the equipment were two clear tubes with slightly larger stainless steel tubes on their ends. Annabelle plugged in the machine and a soft humming filled the barn. Nicole gasped loudly when Annabelle pushed the first of the stainless steel tubes onto her left breast. She gasped more softly when Annabelle repeated that for the right breast.
“That’s just enough suction to keep them in place,” Annabelle explained. “I set the timer so it should start the actual milking once I have churned your cream.”
Nicole wanted to ask Annabelle what she was going to do, but instead she groaned as Annabelle’s fingers slid through her slit.
“Just priming the pump,” Annabelle said as she continued to massage Nicole’s sex. Once Nicole was moaning loudly Annabelle stepped back and picked up a thin cane. She swished it back and forth several times as if she were waiting for something. Then the sound of the milker changed. Rather than a soft hum, it became a louder almost grinding sound that pulsated slowly. With each pulse, one of the clear lines would rock and sway. Nicole gasped at first, but then began just moaning, “Ooooh, Ooooh, Ooooh” with each pulse.
Annabelle stood behind Nicole watching the thick fluids seep out of her cunt and down her legs. She swished the cane in time with the pumping action of the milking machine and then suddenly snapped the cane across Nicole’s ass. She waited, her head bobbing in time with the machine until the pump had gone from right to left then back to right and again back to left. When the pump went back to the left breast for the third time, Annabelle again struck. This time she was careful to make the full force of the slash crash down on Nicole’s right ass cheek.
Annabelle continued striking every third pump cycle. She would alternate so that the third time the pump was sucking on Nicole’s right teat, the cane would snap across her left asscheek and then the third time the pump was sucking on Nicole’s left teat, the cane punished the right asscheek.
Soon Nicole was continuously keening a high-pitched wail. Her body was undulating as much as it could in the milking stall and she was struggling to free her hands so that she could take herself over the top.
Annabelle laid the cane across Nicole’s back and walked around in front of her. Nicole looked up at her and tried to speak. Her words were interrupted with “Uhs” and grunts as the pump cycled, but she looked up at Annabelle and begged, “Please, Mistress Ann, you said I could have an orgasm. Please give me an orgasm. Please... please... please...”
Annabelle squatted down in front of Nicole and said, “I think maybe I should cane you until you either orgasm or beg me to stop.”
“No, Mistress,” Nicole sobbed. “I couldn’t stand it. I couldn’t stand it.”
“But you came out here wanting to be my naked little cowgirl,” Annabelle said dismissively. “Maybe you should just go back to your apartment and dream about what you could have had.”
“I’m sorry, Mistress,” Nicole sobbed. “I want to be your naked cowgirl. I really do. But I don’t know if I can do it.”
“Maybe you need a trial weekend or two,” Annabelle said. “Come out here next Friday night at eight and be ready to stay for the whole weekend.” She laughed and then added, “Don’t worry about packing anything. Clothing, for you, is going to be optional.”
Nicole nodded her head rapidly and said, “OK, OK, Mistress Ann. I’ll be here next Friday at eight.”
“And arrive naked,” Annabelle said with a smile.
“It will still be light out,” Nicole whined. “I can’t walk out to my car naked in full sunlight.”
“You can strip off in the glen if you want,” Annabelle said harshly, “but you had better arrive naked or I will send you right back home.”
“OK, OK,” Nicole said between grunts. “I will arrive naked.”
“And be on time,” Annabelle said firmly.
“Yes, Mistress Ann,” Nicole replied. Then she whined, “You promised me an orgasm. Please give me my orgasm. Please... Please... Please.” Now rather than grunting slightly when the milking machine sucked on her teats, Nicole was grunting out “Please” with each cycle of the pump.
“You shall have your orgasm, my needy little naked cowgirl,” Annabelle said with a slight laugh. “And so shall I.”
She patted Nicole’s ass and said, “Don’t go anywhere. I need to get something from the house.”
Nicole kept up her steady litany of “Please... Please... Please... Please...” while Annabelle walked out of the barn and over to the house. When she returned, she was naked... except for a large strap-on dildo that hung from her front.
“This is double-ended,” Annabelle said as she centered herself behind Nicole. “There is a short stub that goes into me and a nub that rubs against my clit. I’m going to fuck you until I’m satisfied. And you are NOT going to orgasm until I do. I won’t tell you when you can let yourself go, but if you go too soon, you aren’t coming back next weekend. Do you understand me, my little naked cowgirl?”
“Yes, Mistress Ann,” Nicole answered. Then she gasped loudly as Annabelle slid the huge dildo inside of her.
Annabelle’s thrusts were timed with the rhythm of the pump. It was exquisitely slow pleasure for both of them. Nicole rapidly was panting and moaning loudly. Annabelle remained silent for what seemed like hours to Nicole. It was much less than that, but Nicole had been on the edge of orgasm for some time before Annabelle finally began a high-pitched grunting with each stroke. She was also speeding up slightly.
Finally Annabelle gave a single, loud, high-pitched groan, rammed herself hard into Nicole, and stopped. Nicole waited a moment to be sure and then released the pent-up orgasm that was boiling inside of her. She wailed and screamed and bounced within the milking frame.
Finally she calmed down and almost immediately began screaming, “Ow! Ow!” with each cycle of the pump.
“Please, Mistress Ann, shut it off!” she wailed, but there was no answer. She was alone in the barn. The huge dildo was still firmly in her cunt, but Annabelle was gone.
“No, No, NO!” she screamed loudly and began twisting and thrashing against her bonds. She had physically moved the milking stand several inches when she felt a hand on her hair.
“Now, now, my little naked cowgirl,” Annabelle said gently. “The pump is off. We just need to detach the teat cups.”
Nicole looked up. Annabelle was standing there once again dressed in her denim skirt and white blouse. The red hat was still firmly on her head. Nicole yelped as first one cup and then the other was pulled from her tender teats.
“Not more than a couple of tablespoons of milk,” Annabelle said. “I would have thought someone with your nice rack would have produced more, but I could fix that with some hormone pills.”
“Please no, Mistress Ann,” Nicole begged. “I don’t want to be a Hucow.”
“I won’t,” Annabelle replied. “I don’t get the same pleasure out of milking a woman that Grandpa evidently did.” She smiled at Nicole and then said, “But I did want to see how his machine actually worked.” She shrugged and added, “It’s not that much different than the machines he used to use on his cow cows.”
Annabelle pulled the dildo from Nicole’s cunt and then began unwrapping the restraints on Nicole’s arms and legs. Soon Nicole was standing shakily. Annabelle handed her an old burlap seed sack and said, “You can use this to protect your car seat from all your juices, but you had better leave it on the seat when you go into your apartment. If you don’t, I will know. Do you understand me?”
“Yes, Mistress Ann,” Nicole replied. “I have to go back into my apartment completely naked.”
“See you next Friday at eight?” Annabelle asked lightly.
Nicole nodded and Annabelle said much more loudly and firmly, “And arrive NAKED!”
“Yes, Mistress Ann,” Nicole said as she took the sack and walked back to her car. She could hear Annabelle chuckling behind her as she retrieved her keys from the trunk, placed the scrap of burlap on the seat, and drove home. It wasn’t until she was sneaking into her apartment that she realized she had left her bag of toys and goodies down on the farm.