Ann stood outside the door to my upper west side apartment in a trench coat, her long curly blond hair damp from the November thunderstorm raging outside. She was normally two inches taller than me at 5'11", but the stilettos she wore took her up another 6 inches, and so I had to look up to her in the doorway.
As she stepped inside, she removed her coat to reveal a tight red latex catsuit underneath, her enormous breasts pushed up and exposed above her now tiny waist and perfectly formed ass. It had taken almost six months, but she had finally lost enough weight to fit the costume.
"I'm ready for my training, Master," she said as I closed the door behind her and picked her up.
***
A prosecutor with the city district attorney's office, Ann was just two years out of law school when I met her at a bar near her office almost 8 months ago. I'd seen her across the room and thought she might make an interesting next conquest. Could see through the buttoned up blouse and dull grey suit that there was something in her that wanted to be controlled by a man like me. At 46 years old with a shaved head, heavy muscles from daily work outs, and tattoos over much of my arms, chest and back, I was the one that their mothers warned about.
After debating for 30 minutes, looking at me out of the corner of her eye while I ignored her, Ann had finally come up to me and offered to buy me a drink. I told her no thanks, but I'd be happy to go back to my place and fuck her like she'd never been before. When she hesitated for just a moment, I told her to get the fuck out and went back to my drink.
She shook her head and went back to her corner of the bar, where I watched her trying to figure it out. With my last dozen women, it had taken them seeing me at the bar at least five or six times, and usually nine or ten before they worked up the courage to come up to me. I could tell almost immediately that Ann was special, and had a feeling she would be back soon.
Three days later, she was in the bar again, and this time when she asked to buy me a drink and I suggested we go back to my place, she tossed down two twenties to cover both our tabs and said, "You lead the way."
When we got back to my place I sat down in my soft leather lazy boy and told her to take off her clothes. She had, fumbling and nervous at first but without a word of complaint, and revealed a truly amazing set of firm double D breasts. True she was a bit chunky from too much time eating while sitting at her desk, and needed to do something about the wild patch of blonde bush above her pussy as well, but she had great potential.
I took out my own flaccid cock, nearly 6 inches long while soft, and bade her over to suck it. She got down on her knees before me and began to work my member between lips covered in dark pink lipstick. It grew in her soft wet mouth just an inch longer but much, much thicker. I could tell almost immediately that she was going to have difficulty with the girth. Such a small mouth on the woman.
I grabbed her head and pushed myself down the back her throat. She began making gaging sounds almost immediately, and I could feel her choking around my cock. Eventually her hands went to my torso and she began to push away. I let her up.
"You can be punished for your disobedience or you can leave," I told her as she looked at me with ice blue eyes on the verge of tears. "But if you leave, there is no second chance."
This is where the rubber hit the road. If my instincts had been right, Ann would submit to me now and her training could begin. If I'd been wrong, well, I'd have to find another pupil. I didn't mind. There were plenty of women in the City, but I did take it as a personal measure of failure when a woman I'd brought back to my place rejected my offer.
"What do you want me to do?" She asked, the tears starting to fall from the corner of her eyes.
"Come here across my lap," I replied softly. She got up and laid her torso across my legs. Like me, her skin had that Mediterranean tone of southern, rather than northern, Europe, though I was still several shades darker than her. I was happy to see that her ass hadn't yet lost its youthful perk. It was amazing how fast sitting in an office all day could ruin a woman's butt.
She knew what I was going to do, and when I first reached down to feel her sex, I could tell from the wetness of her pussy hair and the hardness of her clit how much she was anticipating it. I began rubbing that clit with my left hand even as I brought up the right and gave her three hard swats, a small but gentle "ugh." Escaping her lips with each crack.
"Good," I told her after the spanking and she beamed. I then got up from the couch, moving behind her and bending her over it, her hands down on the brown leather and put the head of my rock hard cock at the entrance to her wet pussy, the aroma of it filling the room.
"My name is Vin, and if you submit to me I will bring you pleasure like you never imagined was possible. Do you want that?"
"Yes," she replied with a croak.
"What is your name?"
"I'm Ann."
"Have you ever had a cock as thick as mine, Ann?"
"No, never. It's huge."
"Good," I replied and pushed it into her.
"Unnnahhhaaaghhh," she moaned as she my dick split her pussy.
She was so tight I half expected to find her hymen still intact. Instead, I felt just the intense pressure of the slick walls of her pussy against my shaft as I fucked her. To my delight, she loosened more when I slapped her ass then when I rubbed her clit. She screamed out in orgasm just a couple of minutes later. I stopped my thrusting as she did, allowing for the sensation of her tight hole contracting around me flow through.
"Kneel," I said as she finished her orgasm and she did as she asked, getting down on her knees before me and looking up at me with those blue eyes, no longer in tears.
I stroked my cock with one hand and reached out with my other, sliding a thumb between those pink lips and opening her mouth. A moment later she understood, sticking her tongue out for me as I came across her face, dripping onto her tongue and leaving a thick wad hanging from her chin.
Ann, I thought, was going to work out just fine.
***
As a lightening stroke flickered in my apartment, I picked her up in my arms and took her back to my bedroom, where my best pupil lay naked on a small mat on the floor, a leash leading from the collar she wore around the foot of the bed. Mary was a 5'8" 107 pound Cuban girl with bushy brown hair and tiny breasts just bigger than an A cup. She quickly got to her knees and I gave her head a rub as I lay Ann down on my bed.
Watching Ann fight down the urge to ask a question of me then was exquisite, and it got me rock hard. It was nearly time to book my yearly trip to Hedo in Jamaica, and I needed to know if Ann was going to be able to take this next step. She'd been an excellent student so far, but adding other people into the mix, especially adding others who at my command would be allowed to take total control of Ann, was always tricky, no matter how submissive a pupil had been before.
The time had come to introduce Ann to Mary, who had been my pupil for over five years now and had twice been with me to Hedo. Both times were after another pupil had failed this exam. As the prize was three days of freedom from my control in the New Year, Mary liked to work very, very hard to get my students to give up. And I can't say that I minded when she did. Mary had a wicked imagination and giving up control to her on occasion was delightful. For a few days, at least.
Ann had taken very quickly to the training after our initial session. Whether it was toys, ass-play, bondage or discipline, she'd proven and eager and hungry student for each of my lessons. Now she lay across my bed, her head to the side where I and Mary was, her eyes looking at me and trying not to tear up like they had on that first night.
"There are three questions you are thinking of right now, and I will answer each of them before I make my next request of you," I said as I took up Mary's leash and began to lead her around the bed.
"Number 1. Wasn't this special between us? No. It is not. Though you are special. Perhaps as special as Mary here is."
I took out my cock and Mary obediently began to suck on it, instantly taking it all the way down her throat.
"Number 2. How many other girls are there? Currently 2. You and Mary. Three others I'm waiting to approach me at bars. Seven others before you have failed at some part of the training and are no longer in my life. Eleven have completed their time with me and are welcome back any time they wish. Mary is one of those eleven as well."
I gave Mary a small pat on the head and she pulled her head away from my dick.
"Number 3. What is going to happen now?" I paused after that question and gave Mary a small swat on the ass. "You are going to bring Mary to orgasm by licking her clit and then a second as I fuck her above your face. You will clean my cum from her pussy after I fill her, and you will not be pleasured by either of us while you do this."
Mary jumped on the bed and straddled Ann's face. She bent over, her head resting in Ann's latex covered lap. Mary's young, bare pussy was just inches away from Ann's mouth and I watched her eyes intently.
I'd lost my last pupil prior to Ann at this exact moment, and two others during similar sessions. The humiliation of discovering that I was fucking other women, and then bearing witness to it just inches from their face, was too much for many to endure. Even those who loved everything else we did wanted to believe that they were the only one that I shared this with.
And then there was the fact that this would be the first woman that Ann had ever tasted.
Ann lay motionless for a long few seconds, and then her tongue moved from between her lips and reached out to Mary's slit, running along it until it reached her clit. Mary sat up then, pushing her sex down onto Ann's face, smothering and grinding on it. Ann opened her mouth and began to work Mary's cunt in earnest.
I sat down in the chair across the bedroom to watch the two beautiful women. Ann was now used to having her breathing restricted during sex, and she did not panic when Mary moved her pussy to completely cover her nose and mouth. Instead, I saw Mary lean her head back and begin to moan in pleasure, vibrating her hips below her even faster. After a good minute, Mary finally bent back over, freeing Ann's face.
Ann didn't hesitate, lifting her own head up to continue the tonguing of Mary's clit while also bringing a long arm around her ass and inserting two fingers into Mary's hole. Her hand moved in and out quickly while she suckled and licked at Mary's long clit. It wasn't a fair contest.
Mary began breathing quickly and moaning almost constantly before realizing how close she was and moving back up to smother Ann again. It was too late. A stream of liquid squirted from Mary's pussy as her orgasm intensified, puddling over Ann's latex covered body.
That was my cue to get up from my chair and move behind them. I pushed Mary down into her own puddle of cum on Ann's body, spanked her ass hard and looked down to see Ann, eyes open and tongue still on Mary's clit, look up at me with those cool blue eyes, not a tear in them. I entered Mary's pussy with my huge cock, her lips stretching out as I did, Ann's tongue darting between my shaft and Mary's clit.
