As I stared up at the ceiling, contemplating my own existence, I couldn't help but retrace the last few weeks in my mind. My girlfriend had just broken up with me, apparently, she had met someone else and had been cheating on me for months.

The same week, I found out that my company was laying people off and I was about to lose my job too. This is how I ended up at age twenty-five, living with my mom again.

It wasn't all bad, I thought, trying to convince myself. My mom owned a long-stay motel, which meant there were no problems in finding me a room to stay, even if my neighbors were mostly down and outs and horny couples.

Most nights, I could hear them through the walls, usually fighting or having sex, making it difficult to sleep. This forced me to spend time dwelling on things, particularly how alone I was.

At night, when all I could hear was the noises coming from the other rooms, I couldn't help but think about my ex-girlfriend. Picturing her with her new lover.  

At night, time slowed, giving me ample time to analyze our relationship, running through the various scenarios in my mind and I couldn't help but think about it. Imagining her being fucked by her new lover as I lay awake listening to the couple having sex in the room next door.

On the other hand, all this time alone was making me feel super horny and allowed me time to jerk off as often as I liked, sometimes up to five or six times a day.

I'd become addicted to trying out new ways of masturbating, occasionally switching things up with some anal play, which made me come even harder.

When I wasn't in my room fantasizing or playing with myself, I was helping out around the motel. My mom only had two maids, so in exchange for not paying any rent, I also helped clean the rooms.

It was a nasty job. The people who stayed in these rooms didn't care about the state they left them in and I would often find come stained bedsheets, used condoms, and worse.

One morning while changing the bedding in room 5B, I noticed a sexy piece of lingerie left carelessly on the duvet cover. It was a faux leather basque with suspender straps that dangled seductively from the black power mesh sides.

As I picked it up, I felt a rush of excitement run through me, feeling the lightly padded cups and shimmering faux leather between my fingers.

My cock became hard and rubbed against my jeans as I imagined how sexy the owner must have felt, wearing this sexy piece.

I began to feel an overwhelming sensation followed by an uncontrollable urge to play with my cock as I held the lingerie, and before I was conscious of what was happening. I was in the bathroom clutching the lingerie in one hand while I frantically jerked my cock.

I could feel my balls clenching, as I began to moan, rubbing the faux leather against my skin as I continued to stroke myself faster. I'd never felt so turned on before, feeling my cock pulse as I slowly brought myself towards a climax; only to have the moment shattered as a husky female voice echoed out from behind me.

"What the fuck are you doing?"

Startled, I turned my head, dropping the basque onto the floor and quickly trying to tuck my hard cock back inside my jeans. I stood there silently, a look of panic on my face as my eyes darted around the room looking for a way out while she stood blocking the only exit to the room.

"Well, answer me!" she snapped, staring back at me.

I mumbled a pathetic whisper of an apology, hoping she would just let me leave, but instead she just continued to stare at me.

"So what are you, some kind of pervert or something? You like playing around with women's lingerie, is that it?" she asked inquisitively.

I tried to reply, but again all I managed to say was a feeble, "I'm sorry."

"Wait a minute, you're the owners' son aren't you?" She exclaimed, a faint smile appearing on the side of her mouth. "Yeah, you are aren't you! I bet she'll be shocked to hear that her little boy is a dirty panty pervert won't she?"

My jaw dropped and my whole body began to shake with panic, Pplease, I beg you, please don't say anything!"

Her smile grew, a sudden realization as an idea that began to fester in her head. After what seemed like an endless pause, she eventually replied.

"You like my lingerie then do you? Well, go on then, put that on!"

"What?" I replied, flustered and bemused by her request.

"You heard me, take your clothes off and put that on!" she said, raising her voice and pointing down at the lingerie.

I felt trapped, my mind desperately trying to figure out this unsolvable puzzle. What else could I do? I thought, sliding my t-shirt over my head and unzipping my jeans.

For a moment I stood, naked, all except for my briefs. A look of pity in my eyes as I looked up at her, waiting hopefully for her to release me.

"Come on," she barked, "and those!" pointing down at my undies.

Slowly, I removed my briefs, keeping my arms in front of me in a desperate attempt to cover my private parts as I reached down to pick up the basque.

Having never worn lingerie before, I stumbled to find a way to put it on, stepping clumsily into it and sliding it up over my legs. The faux leather stretched around my waist fairly easily, allowing me to pull it up tightly up over my chest. When it was finally on, albeit not particularly well, I stood still, waiting anxiously.

She began to laugh loudly, cackling as she pointed at me, placing her hand over her mouth to cover her laugh. "Oh, my God!" she said, finally, taking a large breath. "You look so cute! Look at yourself," she said, grabbing my shoulders and spinning me around so I could see myself in the bathroom mirror.

I noticed what she meant, staring at my skinny body all wrapped inside her gorgeous faux leather basque. My eyes bulged as I stared at my reflection, admiring how sexy her lingerie looked, not realizing how excited this was making me.

"Oops!" She giggled, pointing down at my exposed cock that now stood fully erect on display.

I quickly covered myself, feeling embarrassed by how turned on I was getting at this moment. "I'm so sorry," I said, my face growing red shame.

"It's ok sweetie," she said supportingly. "Is this your first time dressing like this?"

I nodded back innocently.

"Well, you seem to be enjoying it," she said, grinning to herself, her eyes peering down at my small but hard penis which was trembling with excitement.

I looked at her embarrassingly, then nodded in agreement.

"Come with me," she said softly, walking back into the bedroom.
I followed her in sheepishly, then stood nervously in the corner of the room, waiting for her instruction.

While she sifted through her luggage I began to notice how incredibly sexy she was. She wore a tight pencil skirt that accentuated her large round ass and her stunning long slender legs. Her silky blouse hung off her shoulders, clinging to her large pert breasts that swayed as she moved.

My cock was rock hard and I'd begun slowly stroking myself as I watched her moving around the room. I felt so slutty, dressed in her lingerie, and thought I could come at any second.

All I needed was to see her tits and I'd just burst right now all over her sexy basque. She turned around noticing what I was doing, her facial expression tightening with disappointment.

"What are you doing!" she snarled. "Stop that right now," quickly moving closer and slapping my hand away from my cock. "Did I say you could touch yourself?" she said rhetorically. "What's your name anyway?"

I looked up at her, a guilty look in my eyes, "Brian," I replied.

"Brian!" she exclaimed. "That sounds like a boy's name! No, that just won't do now will it! Dressed like that. You should have a girl's name, something like," she paused, tapping her finger on her beautiful voluptuous lips.

"Brianna! Yes, that's perfect, and you will call me Miss Fiona. Do you understand Brianna?"

I nodded at her in agreement, a naughty twinkle in my eye.

"Now go sit on the bed," she ordered.

I did as I was told and sat down, eagerly waiting to find out what was going to happen next. Fiona walked over to me, bending down to ensure I could see her breasts.

My eye fell deeply into her cleavage, entranced by her beauty as my cock stiffened. She picked up a pair of sheer stockings, brushing them gently against my legs as she handed them to me, making me shiver.

"This is exciting isn't it Brianna?" she said softly and seductively in her sexy husky voice. "Put these on, they'll make you feel like a sexy girl."

I did as I was asked and rolled them over my hands, slipping the material over my toes then slowly rolling the sheer stockings up my legs. Fiona pulled at the suspenders, quickly fastening the garter belts onto the tops of the stockings; fastening the basque securely as it tightened around my body.

"I'm so fucking horny Miss Fiona, please let me fuck you. Please!" I begged, my cock throbbing painfully between my legs, as a drop of pre-come trickled out the tip. My body gyrating as my pelvis rocked against the mattress.

Fiona looked at me with a wicked smile. "Oh baby, I don't have sex with little girls. But, I do fuck with them. Besides, we're only getting started."

My whole body trembled, I as pleaded some more. "Please, Miss Fiona, I beg you! I need to come so badly! I've never felt this way before, please!"

"I know, honey, but you must be patient," she said soothingly. "You will get to come, and I promise it will feel so good when you finally do!"

My eyes lit up with hope as I stared up at her. Fuck my Ex-girlfriend! I thought. I'm Brianna now... Miss Fiona's girl. And, if I'm good, she'll help me to come better than I ever did with her.

Fiona looked around the room with a look of disgust. "Weren't you supposed to clean my room?" she asked. "Well, I've seen the other maids that work here, don't they wear a uniform when they clean?"

I nodded.

"Well then. I suppose you should be wearing one too. Where are the uniforms kept?"

"They're in the main office," I replied quietly.

"Good. Then I want you to go and fetch one," she said with a serious look in her eyes.

"I can't go in there looking like this!" I replied with panic in my voice.

"Hmm, I suppose not," Fiona replied. "Well then, just throw your clothes on over the top, but keep the lingerie on."

I stood up, feeling the suspenders tugging against my garter belt as I wandered back into the bathroom. I picked up my pants and shirt, then slid them back on, before heading back into the bedroom.

Fiona was sat in a chair playing with her phone, ignoring my presence. I could tell she didn't want to be disturbed and continued out of the room.

As I opened the door, the sunlight blinded me temporarily. Squinting to see, I was relieved that there was no one else around and quickly raced over to the main office.

I could feel the stockings rubbing against my jeans as I walked, the basque brushing against my shirt, and the sensation arousing me, making me feel super naughty.

When I reached the office, I sneaked into the storage cupboard, quickly grabbing a spare uniform and stuffing it into a polythene bag. Then, hurriedly headed back to the room before anyone saw me.

The entire sequence lasted less than a few minutes, but the thrill of doing something so naughty was exhilarating! The whole time, I kept thinking, 'What if I get caught stealing a maid's uniform? What would I even say?'

By the time I reached room 5B, I was trembling with excitement. Inside the room, Fiona was gathering her things and looked as if she was about to leave.

"I did it!" I said proudly.

"Good girl, Brianna. Now, go and put that on. I'm just going to pop out for a moment, but I'll be back soon. In the meantime, I want this room sparkling clean by the time I return, understood?"

I nodded in agreement, then raced back into the bathroom to get changed. My hands were shaking as I took off my jeans and shirt, carefully removing the uniform from the bag.

"Oh, my God, I can't believe what I'm doing," I murmured to myself, slowly stepping into the maid's outfit and sliding it up over my legs.

My cock was rock hard again, protruding outward from the hem of the dress. All I wanted to do was jerk myself off, right then and there, but I remembered Fiona's words, "You will get to come, and I promise it will feel so good when you finally do!"

For the next thirty minutes or so, I cleaned the room, enjoying the feeling of the uniform brushing against the lingerie as I moved around, completing my chores with a sense of pride.

The sheer stockings made me tingle as the cotton uniform stretched tightly against them, making me drip a little more pre-come. There was something about being dressed like this, performing these duties that made me feel like a real maid.

After a while doing chores could feel my mind-altering, making me feel even more feminine. I was just finishing cleaning and was making the bed up when Fiona returned.

She was holding a few shopping bags and placed them carefully on the side, then stopped to inspect the room. "That's much better," she said gleefully. "I've bought you some treats for being such a good little made."

Her words made me feel all warm and fuzzy inside.

"Come over here and kneel down by feet," she said authoritatively.

I did as instructed, kneeling down, then waiting patiently by her feet. I watched with delight as she put her hands inside the bag and began slowly pulling out my gifts one by one.

First, she pulled out a padded leather collar and leash, holding it up so I could see what it was. Then, leaning forward to fasten it around my neck, gently pulling at the leash to test it.

I lunged forward slightly, almost losing my balance. Next, she picked out a small black silicone cage and a tiny brass padlock, giggling to herself as she placed them on the side.

The next item she pulled out from the bag was a shiny black pair of 4-inch heels that looked to be in my size, placing them in front of me.

"Here," she said, "stand up and try these on."

She eased up on the leash, allowing me to stand as I slipped my foot inside the first shoe. It fit perfectly. I carefully slipped on the other shoe and stood precariously, trying to hold my balance in the heels.

"Don't worry, you'll get used to them," she said reassuringly.

As I stood admiring my new shoes, Fiona reached back inside the bag and pulled out a smooth metal butt plug with a jeweled heart-shaped base and a small bottle of lubricant.

"Now, turn around sweetie and try to touch your toes," she said in her husky tone.

I felt a little scared as I turned around, bending down and exposing my bare bum. My legs were shaking, making me wobble in my new heels. I could hear Fiona lubing the plug behind me and wondered how it would feel inside me. I'd fingered myself before so I figured it would feel similar.

She gently ran the tip of the plug over my tiny hole, spreading the lube around my bum softly and making me let out a quiet whimper. After a few more seconds I felt the plug slowly enter me, causing me to let out an involuntary girlish moan.

"Good girl!" she said supportively. "Does Brianna like her new toy?"

My response was another louder moan, as she pushed the plug all the way inside me, letting go of it and spanking my bum gently as a test. To my astonishment, it remained firmly in place.

Fiona stood up and began to lead me around the room, making me wobble in my heels as she tugged at the leash.

"There, see. You're starting to get it all ready," she said, giggling to herself. "Now, are you ready to begin?"

I had no idea what she was talking about, but I couldn't wait to find out what she had planned for me next!