Fall 1999, 19 yrs old
Jackie told me, in no uncertain terms, if I was to learn to pass as a woman, I would have to do everything she commanded. If I couldn’t obey her, I could leave then. If I couldn’t do the work, she’d fire me!
Tracy, a Nordic blonde, built like me, would train with me. She wasn’t a transsexual, she was born female: however, Jackie felt she needed ‘improvement’. The two of us would be available for training every day.
Michelle, Jackie’s buyer, would help train us. We often would meet at Jackie’s place for after hours training. Usually, this involved us fucking and eating each other, and servicing Michelle. We learned many sexual techniques from her.
One evening, Jackie introduced us to Sam, a handsome, sophisticated man about Jackie’s age. Sam would teach us walking, poise, and, social skills. He would have absolute control of our training. If we repeatedly failed to please him, we were ‘out’!
Sam immediately order us to strip. After walking around us, examining us, he ordered us to put on spike-heeled shoes and walk around. Neither Tracy ,nor I, were very coordinated. I usually wore flats, and occasionally, 3 inch heels.
Suddenly, I felt a sharp sting on my bare ass!
“Stand straighter! Take smaller steps! You two walk like cows!”
He examined us, lightly slapping his palm with a riding crop. He noticed our looks and smiled wickedly. He ordered us to stand still and gave each our bottoms a hard swat.
“I will use this learning tool to help you! Do well, and I will reward you. Do poorly, and get swatted!”
Sam put a book on our heads and had us stand still. He left the room and told us not to move. The book felt heavy, and the spikes were taller than I’d ever worn!
We stood nearly thirty minutes under Jackie’s watchful eye. I nearly dropped my book when a beautiful, elegant woman returned from Sam’s room! It was Sam! He was now She!
She walked across the room gracefully in her spike heeled shoes! She wore a tight, below the knee skirt, hips swaying from side to side. She picked up a book and placed it on her head, then walked to us.
“When I’m through, you’ll be able to walk gracefully and sexily in any circumstance. You will be able to bend over and pick a dime off the floor and keep your balance. You will learn to fuck and be fucked while wearing heels”
“I expect you to keep your balance and not flinch when I swat you.” He continued.
“Your butts will be red every day until you learn what I have to teach!
Jackie started to speak, but Sam swatted her ass hard.
“No one gave you permission to speak! I’m the teacher, now,” she stated. “Now, bend over!”
Jackie bent over and pulled her skirt above her full bottom. Sam swatted her very hard many times, bringing tears to her eyes. But I could also see pleasure in those same eyes.
Sam turned to me and commanded me to suck Jackie. I knelt and felt a hard swat across my bottom.
“No one told you to kneel!”
I started to squat, and again came a swat! Sam commanded Tracy to try. Tracy bent over at the waist, hands behind her back, and proceeded to suck Jackie’s cock. Sam nodded approvingly.
“Very good! Not what shall be your treat?” she asked.
“Some hard swats across my ass!” she responded.
Sam looked taken aback! She then commanded Tracy grab her knees.
“Impertinent bitch,” she muttered as she swatted Tracy’s nice pale ass. It was soon bright red! I could tell from her expression she’d come if she could touch her clit.
“Had enough?” Sam asked.
“More, please?” Tracy quietly asked.
Sam was about to explode in frustration when she noticed Jackie’s smirk. I lost count of the number of swats. Sam had a very nice hard on forming in her skirt.
Sam removed her skirt and ordered me to suck her and for Tracy to suck Jackie. They talked about different things as we sucked. It is very difficult to suck cock like this, bent over like this, unable to use your hands.
“Not bad, but practice on Jackie every day until our next lesson!”
As we left we saw Sam swatting Jackie’s ass. Her cock was rock hard!
“I like my asses bright red when I fuck them!” she said.
Over the next several weeks, Sam watched and trained us. He was right: our asses were painfully red after each session. One of us would invariably stay over for extra training. That meant having our asses whipped until bright red and being roughly fucked by Sam and Jackie. Tracy seemed to have to stay the most. I believe she intentionally screwed up just to get the swats.
Sam also started us in ballet classes for adults. We learned flexibility, pose, and strength. It also helped our legs look better. I found I enjoyed these! I also learned to do wide splits! (I’m in my 30s, now, and can still do them, much to my husband’s delight!)
Sam was right. By the time he finished training us, we could pick up a coin from the floor, just bending over at the waist! We learned to bend over so that someone could see our asses and legs. We could carry large items with no stumbling. The sexiest thing we did was to bend over at the waist, adjust a shoe strap, or our stocking, and straighten up sliding our hands up a leg.
Sam never dressed in drag after the first session. He was an entertainer. He would often take us out on the street to practice walking.
One day, Sam took us down town by a construction sight. He waited across the street and watched us. Tracy and I were dressed as very sexy secretaries. She and I walked past the workers, a sexy sway to our hips. The guys whistled appreciatively at us. Tracy winked at a couple of guys and I walked up the sidewalk a short distance.
I bent over, ass towards them and adjusted a shoe strap.
“Damn!” I heard, “Look at that ass and those legs!” and “Honey! Come tie my boots!”
Tracy and I blew kisses and walked on. A couple of real secretaries further up chewed us out for putting on such a show! Neither they, nor the workers, could tell I was transsexual! I was now what was called a “Trap”!
Sam looked at us smiling. “Well done!” he praised. “You’re ready. I don’t have anything else to teach you!”
He turned to Tracy and said, “I think you need to come home with me and practice!”
The next day, Tracy couldn’t sit down at work. She’d just touch her ass and smile!
A few weeks later was the real final exam. Jackie was throwing a party at her place for her friends and business partners. Tracy and I would be maids, serving the guests.
We wore the skimpiest French maid outfits I’d ever seen, no panties. The skirts wouldn’t cover our asses when we bent over. We wore seamed stockings along with our spike heels.
About a dozen trannies, a handful of women, and a couple of men attended. One of us would take their coats at the door. We both served drinks. The bar tender was a tall, handsome, muscular young man who wore a G-string that did nothing to hide his huge bulge!
We had to bend over frequently, our asses close to the guests. I held the pose for long periods as some guests caressed my bottom. A couple even had me back closer so they could kiss or bite my ass cheeks. Many would have me stand in front of them while they played with or sucked my cock long enough to get a taste.
Both of us took cocks of various sizes into our mouths. We were getting quite a workout. It wasn’t long until we were out of the costumes and just wearing the maid's cap and stockings and heels. Someone was always touching us as we went past.
I was collecting drinks at the bar when someone reached around me, arm across my small, round breasts and a hand grabbing my cock. I felt a cock sliding in my ass cheeks. I reached behind and spread my cheeks. A small cock pushed inside and fucked me several strokes, then pulled out. I never saw who it was.
Then it was show time! Brad, the bartender, stood behind me and rubbed his thick 8 inch cock between my butt cheeks. He had me bend over and grab my ankles. Soon his tongue was probing my ass hole. I was relaxing under his ministrations. Unfortunately, that was all the preparation I was going to get!
While I was still holding my ankles, Brad grabbed my hips and rammed his cock past my sphincter! I gasped as my mouth and eyes flew open with shock. The audience clapped and cheered as Brad drove balls deep into my ass and hammered me with fast, powerful thrusts.
He pulled me back against him, one arm holding me close and cupping my breast. He grabbed my cock and stroked it while he thrust up into me. His firm grip on my cock was painful, but I was erect and hard. When I filled his hand with my cream, he raised his hand to my face and smeared it over me.
Brad was putting on a show as he fucked my now tender ass. He continued fucking me, holding me up. Tracy bent over my cock and started sucking. A few minutes later I creamed again!
Brad pulled out of my ass and had me a Tracy bend over, our faces inches away from his cock. He started stoking his cock furiously, then covered our faces with his come. Tracy and I stood up and licked his cum from our faces.
The remainder of the evening Tracy and I were available to whoever wanted us.
Jackie was very pleased at how well our training worked. We had very nice bonuses the next payday!