“Listen, could you come back in a day for your payment?” she asked after a pause. “I just want to rest a bit before I get down to any business. It’s like the Monday after vacation here!”
I nearly let out a sigh of relief. In fact, I was so relieved that I didn’t bother to fight to get paid now. “I can come back tomorrow.”
“Please do, Mark,” she replied. “I want to make sure you’re well compensated for your services. I have a little bonus present planned for you.”
I flashed her a grin as I headed out back home. The week at Amanda’s place had completely transformed me as a person. When I came back to my apartment, I couldn’t believe what I had in my closet. All those hoodies and tattered jeans I had kept over the years looked like a colossal waste of money. I knew I needed cash to buy women’s clothing now that I had lost access to Amanda’s wardrobe.
Perhaps, I could sweet talk Amanda into giving me more work. I knew it was too risky to ever go back to her room and wear her clothing. However, the woman had more money than she knew what to do with. I could make more money working for her than selling potato chips at a convenience store. It would just be what I would need to start my own collection of women’s clothing.
The next day, I drove to Amanda’s house to pick up my payment. To be honest, I didn’t know the exact amount we had originally agreed upon. I had been just happy to stay in a mansion in a week and get paid for doing it. The details didn’t matter much.
I knew that Amanda was making sure that everything was in order before signing a check out to me. Any damages would be deducted from my payment. I had made sure to clean up the house on the last day. Hopefully, her fetish gear wasn’t part of the agreement.
When I rang the bell, she opened the door and greeted me. “Mark? You’re just in time.”
I raised an eyebrow as I followed her. “In time for what?”
Amanda gave me a sinister smile. “Your evaluation.”
Puzzled, I entered her ex-husband’s office. Well, it was technically her office now. In any case, I didn’t know why she was in such a weird mood.
Amanda sat in front of a computer but turned the monitor so that it faced me. “So Mark, I was reviewing your performance over the past week and came across this.”
I blinked in confusion. “My performance?”
That’s when I saw the video playing on the monitor. It was of a woman in a maid outfit. She was going from room to room to clean the house.
No….
It wasn’t a woman. “Wait… that’s me!”
“You’d think I’d let a stranger stay in my house without any accountability?” Amanda said smugly. The blood churned sluggishly in my veins when I heard her words. “The secret security cameras were meant for burglars but they’re also good for checking up on a naughty caretaker. I saw everything, Mark.”
I stammered like an idiot. “I-I can explain!”
She took out her phone and played another video. “I had a livestream that I could view at any time. While sipping coconut water down in the Caribbean, I watched you play with my favorite dildo.”
I was completely shell-shocked. She knew the whole time and had been playing me. “So you saw me…”
“Wearing my clothes, makeup, and dildo!” she finished for me with a laugh. “At first, I thought you brought a girlfriend or a hooker but it was actually you!”
I stared in disbelief at the video playing. Amanda began skipping around in the timeline. One moment, I was putting on hooker heels. The next moment I was fucking my ass with a dildo.
I placed my head in my heads. “Are you going to call the cops?”
“Why would I do that?” Amanda asked rhetorically. “It’s hardly worth having the police investigate. I’m just curious to know why you did all of this. Have you been cross-dressing for a long time?”
I took a deep breath and shook my head. “No, I just had this weird urge when I felt how soft your clothes were. I couldn’t help myself to them. I’m very sorry!”
She stroked her chin. “Interesting. Did you enjoy role-playing as a woman? I saw you do a lot of dress up while I was away.”
“It was like transforming into someone else,” I answered truthfully. “Wearing new clothes and makeup made me reexamine my body.”
Amanda giggled. “Funny, you remind me of my husband.”
I looked up in disbelief. “What?”
She leaned back in her chair and explained. “I originally had the security cameras installed to spy on my husband, Todd. For years, our sex life had gotten cold. I was content to play with my dildo but I suspected that my husband was fooling around with a mistress. To my surprise, I found him secretly using my clothes and my sex toys when I wasn’t around!”
I watched as she turned off the monitor and faced me. “Is that why you divorced him?”
“No, he’s the one who wanted to leave me when I confronted him,” Amanda said with a grin. The pieces were starting to fall into place. “Todd wanted a divorce while keeping everything for himself. He said he had paid for most of it so he should’ve kept it after the divorce.”
That obviously wasn’t how it panned out. “What happened?”
The divorcee leaned back. “However, he couldn’t have his cake and eat it. I had video evidence of him dressing up as a slutty schoolgirl and reaming his ass with a dildo. I negotiated with his divorce lawyer to give me half of everything in exchange for keeping these videos under wraps. The lawyer agreed but Todd wasn’t happy. He made a big hissy fit with his friends here about the divorce. It’s why the neighbors think I wronged him and want me out. Honestly, the man got off easy compared to what I should’ve done to him.”
It was a lot to take in. “Wow…”
“So that brings us back to you,” Amanda said, standing up from her chair. “Like Todd, you’ve been a naughty boy. Better yet, I have video evidence of you dressing up as a girl and fucking yourself with my favorite dildo.”
I sighed. “Look, you can keep the money. I’m sorry about happened I just want to leave in peace.”
“You shouldn’t be sorry, Mark,” she replied, folding her arms. “It was quite an impressive performance. I had more fun watching you than sunbathing with a martini at the beach.”
I wasn’t sure where Amanda was going with this. “You liked it?”
“I loved watching you play dress up,” she explained, reviewing the security footage on her phone. “It was like seeing a living doll change into different outfits in a dollhouse. That maid outfit never fit the others but it was perfect for your body. You looked very sexy using that feather duster.”
“The others?” I replied, still processing what she was saying. If I didn’t know any better, this unassuming woman was a dominatrix. “You’re telling me you had other people dress up for you?”
“Not people, men,” Amanda corrected, lacing her fingers. The look on her face told me that this mild-mannered woman was no stranger to S&M. “I enjoyed watching you, Mark, but I still have to punish you. Using my property without my explicit permission is unacceptable.”
I gulped. “Are you going to do the same thing to me that you did to Todd? Show the videos to everyone?”
“That depends on your response,” she answered sternly. “If you want to keep this under wraps, then you have to do exactly what I tell you to do.”
I didn’t even think twice about this. Having those videos end up on YouTube or some other video website would be the end of my life. “I’ll do anything you want!”
“Don’t be too hasty,” she chastised. “Swear to me and say ‘Yes Mistress Mandy, I swear it.’ Do it with that exact phrasing.”
This was getting stranger and stranger. I didn’t know where Amanda was going with this. At the same time, refusal wasn’t an option. “Yes, Mistress Mandy, I swear it.”
A bright smile appeared on her lips. “Good, let’s get started. First, you’ll need a new name.”
“A new name?”
“Yes, we’ll need somethin
g to call your new, feminine persona,” she giggled mischievously. “How about Maria?”
I didn’t have much of a choice. “Yes that’s fine...”
My new mistress continued. “I’ve left you a set of clothes in the room you slept in. Put on a fresh set of makeup and a nice wig while you’re at it. I want you to look immaculate when you come downstairs.”
“What are you going to do?”
Amanda glared at me. “Don’t speak unless spoken to, Maria.”
I immediately straightened out my back. “Yes Mistress Mandy.”
This didn’t sound too bad of a punishment. I liked dressing up as a woman. Better yet, I now had access to Amanda’s clothing and makeup collection. I was starting to look forward to what she had planned for me.
Indeed, there was a skimpy schoolgirl outfit waiting for me on the bed. The set included everything from white panties to a pair of platform shoes. It looked to have been custom-tailored. I wouldn’t have any difficulty wearing it.
After putting on the skimpy bra and panties, I picked up the shirt. It was semi-transparent and made of a very light fabric. It was a tight fit around my body. It had enough give not to rip but it highlighted my curves. It certainly extenuated my cleavage.
Then, I attached the stockings to my panties with a set of garters. I finished up by hooking the plaid skirt around my waist. I noticed that the cloth was of the highest quality. Amanda had spared no expense in getting this outfit tailored. I wondered if this was meant for someone else. In any case, I fit into it like a glove.
Finally, I wore my platform shoes and fitted my head with a brunette wig. The shoes were quite stylish with a dainty ankle strap. I went to the vanity mirror on the dresser to do my makeup. After a week of practice, I was comfortable enough to apply eyeshadow and mascara without a tutorial.
Once I was satisfied with my look, I went down to see Amanda.
Or Mistress Mandy.
In any case, she whistled in amazement. “My little schoolgirl is gorgeous.”
I kept my eyes to the floor. “Thank you, Mistress.”
“Now, a good schoolgirl does all of her chores before having any fun,” Amanda said, sounding like a strict mother. “You’ll help clean up the master bedroom. I have everything you need to make it spotless. Then, we’ll go over your homework, young lady. You’ll do everything without question or else you will be punished. Understood?”
I didn’t like the sound of that. “Yes, Mistress.”
“Good, I want to see my reflection on the wooden frame of the bed or else you’ll get a spanking.”
I knew a threat when I heard on. “Yes, Mistress!”
I spent the better part of the next hour cleaning the master bedroom. It honestly wasn’t that messy. Most of the clutter came from Amanda transferring her belongings over to the new room. Instead, this was an excuse for me to prance around in a sexy schoolgirl outfit while doing menial tasks.
This stopped being a punishment and started being a bit of roleplay. Dressing up as a schoolgirl was something I would do on my own. I didn’t feel pressured into doing this. Of course, I needed to keep Amanda happy. She could ruin my life by emailing those embarrassing videos to everyone.
It didn’t take long before I was cleaning the place and waxing the woodwork. Once I finished, Amanda came in to examine my handiwork. The woman wiped the bedroom with a finger before looking into her reflection.
“Very good, Maria,” she said, satisfied with my cleaning. I didn’t know if I could go on performing such a boring task. “Let’s go to my room and work on some homework.”
“Yes, Mistress Mandy.”
She smiled like a proud mother. “Good girl.”
My shoes made a pitter-patter sound against the hardwood as I followed her upstairs. Our relationship had undergone a strange transformation over the past week. At first, I thought she was an air-headed woman who had more money than sense. I thought I had pulled a fast one on her. Instead, it was the other way around. Now, she was blackmailing me into dressing up like a schoolgirl. I didn’t know when this would end.
And I didn’t want to stop dressing like this.
Chapter 5
When we reached the top floor, Amanda stopped and said. “Go into your room and change into a different outfit. Yours is a little dirty.”
“Yes, Mistress.”
“Make sure it’s girly like the one you’re wearing now,” she commanded, walking into the master bedroom. “Be sure to touch up your makeup too. I’ll be back in a few minutes.”
I didn’t know what she was planning. By now, I was smart enough to not ask any unnecessary questions. “Yes, Mistress.”
I went into the room and did what she ordered of me. I found another plaid skirt and a see-through shirt. This one was less tight which made it easier to move around in.
When I finished, I wondered what Amanda was planning. So far the experience hadn’t been as harrowing as I imagined it would be. In fact, it was rather enjoyable. Sure, she was stern but it wasn’t anything I hadn’t done before.
That’s when she came in through the door. “Are you ready, Maria?”
Amanda was wearing a revealing set of leather bondage gear. It had cutouts that revealed her breasts and crotch. A set of garter belts held up a pair of fishnet stockings. The woman stood on a pair of massive heels that helped her tower over me.
“Wow… Amanda- I mean Mistress Mandy!” I began, correcting myself. Gone was the bashful recently divorced woman. In her place was a sexy dominatrix. She could seduce any man with casual ease. “You look great.”
As I eyed her massive rack, she flashed me a spine-tingling grin. “Why thank you, Maria. Now get on the bed.”
I immediately obeyed her command. The threat of being exposed as a cross-dresser hung over my head like a sword. It could drop in an instance if I displeased Mistress Mandy.
Amanda continued. “Maria, watching you fuck yourself with my dildo made me so fucking hot. I could watch it for days on end.”
I felt my cock stir at her words. Her outfit was pressing all the right buttons. “Thank you, Mistress.”
She shook her head. “No, I need you to thank me properly.”
The dominatrix went to her secret stash under the shoe rack. After lifting the loose floorboard, she took out her box of naughty toys. I gulped when I saw her take out a massive twelve inch long dildo and a riding crop.
“Carrot and stick,” she said, waving the dildo. Amanda also took out a harness which transformed the enormous dildo into a strap-on. “You’ll enjoy your carrot or it’s going to be all stick.”
I watched as she wore the strap-on around her crotch. “Yes, Mistress.”
I knew she was going to fuck my ass with that thing. It made the other dildo from earlier look like a baby carrot in comparison. I didn’t know how Amanda could get it inside of me.
I almost wanted to run away. However, I started crawling towards the strap-on dildo. It wasn’t like I was even afraid of her showing the world those compromising videos. Instead, I simply hungered to have that dildo inside of me.
Amanda saw the look on my face and joined me on the bed with the strap-on waggling between her legs. “Hungry for my cock, Maria?”
“Yes Mistress!” I nearly yelled. My body was on full autopilot. “I’m hungry for your cock!”
The dildo was monstrously long. It was much thicker than my shaft. It was a rocket pointed straight at me. I didn’t know how or where to begin. Amanda decided to take the initiative.
She brought the dildo to my lips and I immediately began sucking it. It was made of a hard, warm plastic with a bit of give. My lipstick immediately began to mark it with a bright cherry red color. I felt it radiate with heat inside of my mouth. I guessed it had a similar heating mechanism to the dildo I used earlier.
I was having a hard time swallowing it. Its girth was bigger than that of my forearm. For that matter, I didn’t know how I was going to keep this thing inside my ass.
Amanda thrus
t deeper into my mouth and until its tip entered my throat. “Good… swallow it like a good little slut.”
With a burst of determination, I took more and more of her shaft into my mouth. I grasped the base of the shaft to give myself more leverage. Amanda enjoyed watching me thrust the dildo in and out of my mouth. I heard her moan as I ground the strap-on against her clit. “Yes, that’s it…”
I was beginning to actually think of her as my mistress. I wanted her to be happy. I didn’t mind getting fucked and humiliated in the process.
The Trans Ultra Collection Vol 3 Page 12