tagTransgender & CrossdressersMy Halloween Transformation

My Halloween Transformation


It was a quiet Friday afternoon and I was anxious. When I finally heard the horn in the driveway I felt my heart jump in my chest. I tried hard to act nonchalant as my parents carried their luggage out to the waiting cab. It was the Friday before Halloween and my parents were leaving town for the weekend. I couldn't wait until they were finally gone so that I would have two whole days to raid my mother's closet.

I'm not sure when it started or what led to my first time, but ever since I first wore a pair of women's panties I couldn't stop thinking about doing it again. My name is Eric Jackson and I'm an eighteen year old high school senior. With college just around the corner I was usually able to control my urges knowing that I would finally be able to fully explore my sexuality once I left my parent's house, but in the meantime I still took whatever opportunities I could to dress up. Although up until that weekend, dressing up for my meant jerking off into my mother's panties.

I watched my parents pile into the cab, waving them off from the front porch. As they disappeared around the corner I felt my pulse quicken as my heart continued pounding in my chest. Stepping back into the house I closed the door and paused in the foyer for a few moments until my breathing became more normal.

I always got really excited whenever I was going to dress up. Maybe it was the taboo of it or knowing that I was about to violate someone else's most private space, in this case it was my own mother's collection of underwear and lingerie. Whatever it was I looked forward to the thrill every time.

I never considered myself gay, not by any means. I never really could figure out what I was but I knew that I loved the soft touch of panties against my skin. As soon as I pulled on a pair of panties, my cock instantly became rock hard. Usually I would borrow a pair of my mom's panties for a night and wear them while jerking off to internet porn. My favorite porn was pictures of women dressed in lingerie like garter belts, corsets, see-through negligees, and of course tight panties hugging their pussy lips.

At first, I was careful about making a mess but over time I would intentionally rub my cum into the inside of her panties. I learned that if I wiped off the excess I could get away without leaving a stain. Each time I would return the panties exactly as I found them. The first time I left a surprise I was nervous for days, too afraid to even think about stealing another pair. I convinced myself that as soon as she picked them up she would notice that something was wrong.

Instead of raiding her clean panties, I spent the next week carefully checking her hamper searching for the pair that I soiled. Sure enough they eventually appeared mixed in with the rest of her dirty clothes. It was a pair of black satin brief panties with ruffled sides. It had been so long since I had jerked off that I didn't hesitate stealing the pair again and running back to my room for a marathon session.

I was so turned on from both the knowledge that I got away with it and knowing that she spent an entire day with her pussy rubbing against my own cum. That was also the first time that I came into her panties and then licked and sucked my own cum from the silky fabric until it was clean. I can't say where the idea came from, but for the first time I tasted my own cum and it was mixed together with her aroma.

I didn't have a particular attraction to my mother, but her closet was my only source of women's clothes at the time and it provided a seemingly endless supply of silky panties. Everything else I did was just an extension of my own twisted perversions as I saw her as just a woman with a pussy and not my mother.

This pattern went on for weeks until eventually I was certain that every pair of underwear my mother owned had been thoroughly covered in my cum. I knew that every day her pussy was rubbing against my cum and that I would eventually return to her hamper to retrieve the panties so that I could again drink my own sticky cum from her fragrant panties.

This weekend was going to be different for me though. For the first time, I would have an extended period of time to enjoy myself and I planned on taking advantage of every last second. I waited a little longer until I was certain that they were actually gone and then I slowly crept up into my parent's room. The house was dead quiet except for the ringing in my ears from the excitement of what I was about to do.

I pushed open their door and slowly made my way over to my mother's closet. My parent's bedroom had been added as an addition to the house and they chose to separate their closets. My mother's closet was against the far wall and there was a small window inside that bathed the large walk-in closet in natural light. Instead of a dresser, she had built-in drawers and cubby holes installed along the left wall, leaving the back and right walls dedicated to hanging clothes. In the middle of the closet there was a wide changing table that rose to waist level and near the door was her hamper that I knew was filled with panties covered in my cum.

After all this time I had come to be familiar with my mother's organizational system for her panties and knew exactly which drawer held my favorites and usually that is the only place I would go. This time, however, I wanted to finally explore the rest of her wardrobe. I started on the right side and casually sifted through my mother's collection of dresses, pants, and suits. It didn't take long for me to tire of the conservative clothes and move on to the back wall, which contained a mix of her shorter summer dresses and skirts and her lingerie.

In no time I had stripped off my clothes and piled them up onto the changing table. I continued thumbing through her wardrobe fully naked, enjoying the occasional brush of soft fabric against my throbbing cock. I was already so excited that I was leaving a thin trail of pre-cum on every dress and skirt that brushed against me. After making an initial pass through her clothes, I slipped into the same pair of black satin panties that I first filled with my cum and then spent the next hour trying on every sexy outfit that my mother owned.

I was quite a bit taller than her but since we both had long thin torsos, most of her linger fit me especially anything that stretched. One of my favorite items from her collection was an elastic black mesh body suit. The thin, see-through material stretched around me, cradling my naked body. The bra cups stood out prominently from my flat chest and the lace embroidered crotch wrapped tightly around my hard cock. The sides of the bodysuit came high up on my thighs and there were a pair of straps in the front and back for holding up stockings.

The last piece of lingerie that I wore was a loose fitting dark orange chemise with black lace trim and a slit that came high up the right thigh revealing my black panties. It was clear that this outfit was meant to be worn without panties. I couldn't believe that my own mother owned something so overtly sexy. By the time I noticed the box in the corner, my panties were slick with my pre-cum. I paused briefly and rubbed my cock through the thin moist panties while I eyed the cardboard box against the back wall.

Not wanting to allow myself to cum yet I stopped touching myself and reached for the box. It appeared to contain my mother's old Halloween costumes. I guessed that she had taken it out of storage to put together a costume for this year and left it out. Rifling through the pile of clothes I noticed that she had all of the standard sexy costumes. She had costumes for a sexy cop, a sexy cheerleader and a french maid. But for some reason I was drawn to her little red riding hood costume.

One thing I noticed was that I had never seen my mother in any of these outfits. I wondered where she wore these and how she managed to get out of the house without me seeing. There must be a whole other side to her that I never knew about.

I held it up to get a better look at the outfit. It consisted of three pieces; a small white ruffled shirt, a red satin skirt attached to a black lace up top, and of course a red satin hood. I laid out the outfit on the changing table and quickly put the chemise back on the hanger. It took me a few minutes to figure out how to put the costume on but eventually I figured it out.

The shirt looked like a white peasant shirt. It had elastic around the top and edges that ensured a snug fit against my thin frame. It was a modest shirt, that didn't offer any cleavage, and was meant to be worn off the shoulder, which stumped me at first. The skirt was attached to a black lace piece that resembled a corset. It had two wide black shoulder straps and laced up in the front with a wide black satin ribbon.

I stepped into the skirt and pulled it up my body, enjoying the soft material against my soft hairless skin. After pulling the corset as tight as I could I tied it off. This had the effect of bunching up the white shirt enough to allow a full sized woman plenty of room. I thought that was strange because my mother didn't have a very large chest at all. The red hood was attached to a short cape. It secured around the neck with a thin red strap, but it did nothing for me sexually so I put it back in the box.

I stopped to look myself over in the full length mirror. I looked ridiculous. That didn't bother me, though, because I was more interested in how the clothes felt than how they looked. This was the first time I had ever worn anything more that a pair of panties and my poor cock was begging for relief as it strained against my mother's black satin panties.

Since I had so much time on hands, my plan was to pick out a sexy outfit and spend the rest of the night dressed up. Of course I would jerk off as often as I could. Even though the costume fit me I was more than a half a foot taller than my mother, which meant that the red skirt that probably fell to her mid thigh was much shorter on me.

My next step was to pick out a pair of high heels. I've always been a leg man and have a bit of a fetish for high heels. There are few images sexier than a woman lying on her back with her legs spread eagle in a pair of high heels, thigh high stockings and a garter belt. I only hoped that I would feel as sexy as the women looked in those pictures.

It never occurred to me that our feet might be different sizes, but it turns out that there was finally a benefit to my feet being small despite my height. I pulled out a few pairs of heels and tried each one on until I noticed the perfect pair. I pulled out a pair of shiny black heels that would only barely cover my feet. They had a thin sole propped up by a four inch stiletto heel and a small strip of black material that covered the toes. They resembled a pair of high heel sandals.

I strapped them onto my feet and fastened the thin black buckle around my ankle before standing back up. While trying to stand upright I nearly crashed to the floor. Thankfully I managed to grab hold of the changing table in front of me for balance. After a few moments of shifting my weight back and forth I let go and made my first tentative steps in high heels.

My ankles were as wobbly as jello but I managed to do a lap around the closet without falling down. I checked myself out in the mirror again and marveled at the difference that the heels made. I had always been self conscious about the fact that I didn't have any leg hair, but that didn't bother me anymore. The high heels accentuated my calves and gave my legs a truly womanly appearance. I even took a moment to caress my own thighs while I stared at myself, my hands even drifted up under my skirt and massaged my cock while I imagined that I was a woman playing with her pussy.

I decided to put the rest of the shoes away as carefully as I could, and that's when I found it. Putting away the last pair, I knocked a shoebox down onto the floor. The lid fell off and out tumbled my mother's collection of sex toys. Kneeling on the floor, I collected everything back into the box and placed it on the table.

Her collection consisted of several hard plastic vibrators in different sizes and colors, two small battery powered devices with various straps attached, one pink rubber dildo shaped like a cock, and a small bottle of lube. I examined each one until I reached the dildo. It was shaped just like a real cock, except it was longer and thinner. It had a large contoured head at the tip that was thicker than the shaft. The shaft of the rubber cock had several veins running down its length.

Holding it in my hands I felt something unusual cross my mind. Suddenly I felt jealous that I didn't have a pussy so that I could use the dildo myself. I pressed the tip against my lips and smelled the familiar scent that I had smelled in her panties many times before. My tongue slid along the rubber head as I teased my mouth with the rubber cock. I felt my own cock growing against my panties when suddenly it occurred to me. I might not have a pussy, but I do have the next best thing.

After sucking the rubber cock for a minute I repositioned myself with my legs spread wide apart as I bent over the edge of the changing table. Propping myself up with my elbows I reached for the lube and spread it generously on the tip of the dildo. My body quivered with anticipation as I reach around and beneath my skirt. I spread my legs further apart and pushed my panties to the side allowing a cool burst of air to kiss my skin between my legs. I slowly pushed the cold slick tip of the dildo against my anus, teasing it just as I had teased my mouth moments earlier.

I pushed my hips back into my hand as the tip of the rubber cock slowly pushed itself inside of me. I closed my eyes and concentrated on not letting my knees buckle as it penetrated me.

I had never put anything in my ass before, nor had I ever wanted to, and so I didn't know what to expect. The cold rubber dildo felt warm inside of me as it pushed my flesh apart to make room for itself. With a gentle push, I felt it slide further into me making me gasp for air.

I froze, bent over my mother's changing table dressed in her clothes with her dildo buried inside of me. I suddenly felt like a slut. With my feet crammed into her high heels and my legs spread apart I imagined that it wasn't a dildo but instead was a guy fucking me. I don't know where the thought came from but I wanted to be fucked by another man at that moment. I felt like a dirty whore spreading my legs for some strange guy while he buried his cock into my pussy.

Lost in my own fantasy I began to fuck myself with the dildo. My face was pressed against the cold hard marble surface of the table while a mysterious stranger took me for the first time. I felt my cock straining against the thin fabric and knew that I was about to cum. In a single motion I buried the rubber cock as deep inside of me as it would go just as I felt my cock erupting into my mother's panties.

I felt a new sensation as I came. My insides spasmed and clenched around the rubber cock while streams of my hot sticky cum filled the panties and dripped down my thighs and onto the floor.

I didn't move for several minutes while I caught my breath. My hand held the dildo firmly in place as I continued my fantasy. I was a dirty whore waiting for another cock to fuck me.

Suddenly, reality came crashing around me.


My cell phone.

I reached for my pants on the table and pulled it out.


"Yes Mom, I'm still home."

"What? Can't it wait?"

"Ok. When does it close?"

"Six o'clock? Ok, I promise. I'll drop it off before it closes."

"Ok. Have a great trip."

"I love you too. Bye."

The blood ran from my face as I talked to my mother. If only she knew what I had really been up to. She needed me to drop off a package at the FedEx in town. I looked at my phone and saw that it was only 4 o'clock, so I still had about two hours to clean up and drop it off.

It took another five minutes before I finally caught me breath and slowly slid the dildo out of my ass. I grabbed a tissue and wiped it clean, making a mental note to give it a good scrubbing before the weekend was over. I was disappointed that I would have to put everything away and drive into town. That meant that I would lose valuable time dressed up.

While still leaned against the changing table it occurred to me that I might not have to change after all. A plan quickly formed in my head as I raced to flesh it out. Moments later I was springing into action.

I fished through the costume box again and found a blond wig and a padded bra, the same one that I guessed she wore when she wore this outfit. I knew that if my new plan was going to work I would need to move fast. After putting the wig and bra down on the table I carefully pushed the panties down my legs, making sure not to spill any more of my cum onto the floor. I licked the panties clean and then picked out a fresh pair.

My new panties were one of my favorites. It had a red satin triangle suspended in the front by a series of thin black lace straps that wrapped around my hips and two straps that snaked between my legs on either side of my ass crack. The straps converged in the back into a black satin bow positioned at the small of my back. The straps, when seen from behind, formed a butterfly spreading across my firm round ass cheeks, the tips of the wings wrapping around my hips to the red satin covering my cock. I didn't realize that until I took a picture of myself one time and was finally able to appreciate it.

I knew that I had a limited amount of time so I worked fast. I pushed down the top of the costume and managed to strap on the bra. It wasn't easy in the heels, but I was slowly getting accustomed to them. The bra had large silicone inserts that instantly gave me a pair of large perky breasts. I moved the top back in place and thanks to the fact that the neckline came straight across my chest I was amazed at just how realistic it looked. As I moved my body around I noticed that the bra had just enough give to let my new breasts jiggle realistically while still keeping them firmly pressed against my chest.

Next I put the wig on. It was dirty blond with long bangs swept to one side. The sides of the wig curved around my face, framing it in blond wisps. The wig fell just to the tops of my shoulders, leaving much of my long neck exposed.

With my clothes in place I wobbled back to my room, still trying to get used to walking in high heels, and got my laptop. Back in my parent's bedroom, I was still feeling incredibly horny so I retrieved the dildo from the closet and after wiping it off and then reapplying a generous coating of lube I again draped my body across the changing table.

It wan't until my hand had reached around and pushed up my skirt that I realized that the new pair of panties I was wearing, which only barely covered my backside with the half dozen thin silk straps that formed the butterfly pattern, gave me much easier access than before. Two of the straps wrapped from the front of the panties between my legs, flanking either side of my ass crack, leaving my opening fully exposed.

I felt my cock swelling in my panties as soon as I began gently rubbing my lubricated finger against my asshole. My cock strained against the thin fabric as I felt the familiar sensation of the dildo pushing into me, snaking its way deep inside my body. I laid prone on the table for a few moments, again basking in my new fantasy of being one of the women in the pornos that I watched as some strange man fucked me from behind. Feeling the silicone breasts pressing against my chest, as I gently moaned into the empty room, made the fantasy feel all the more real. I was tempted to fuck myself again, but knew that I needed to get moving.

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bycentrum1000© 13 comments/ 207794 views/ 150 favorites

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