Sissy Awakening Ch. 01

- Sex Shop Glory Hole -

"Hey baby, when are you coming home?" the text message buzzed quietly.

Pulling the phone discreetly from my pocket, I type out, "Same time as usual, just after 5, why... what's up?"

It's my lover Sarah, my best friend, and woman I'd known for over 10 years. We were dating and quite a serious item within months of meeting. Everything just seemed to click with her.

"I won't be home when you get off. I'll be out with the girls." my phone buzzed again.

Working construction had given me broad shoulders, strong arms, and rough hands. It started taking its toll on me too. By the time 5:00 rolled around, I was just ready to go home and relax, glad to have some alone time too. Maybe I'd play some video games, or relax and fiddle around with my guitar. I never planned anything super serious.

Walking in the house, I was surprised by the aroma of freshly baked cookies. Sarah only seemed to bake when she was in a great mood and I smiled at the thought of her in a good mood because that meant I'd probably be having sex soon!

Once in the bedroom I kicked off my shoes, dropped my pants, shirt and underwear right where they come off. I relished the freedom from my work clothes and lay on the bed for a moment completely nude. This was something I did whenever I got the chance.

I idly tugged at the skin on my ball sack. Enjoying the tightening sensation on my perenium and the base of my flaccid penis, pinching a little at the same time. This made my cock begin to grow. I lifted it off my lap and threw it toward my thigh. I've always liked a bit of rough play with my dick. Slapping, pinching, and twisting was never off limits. Occasionally I would tie strings around the base and leave it that way while the head of my dick turned a deep pulsating purple, and then I'd go take care of chores or something. It hurt, but in such a devine way.

I was just relaxing. Laying on the bed, playing with myself. I wasn't really trying to have an orgasm but I was certainly enjoying myself and the sensations. Looking around the room I spotted a new Victoria's Secret bag. The pink striped bag was unmistakable!

"Shit, how much money did she spend today?" I thought to myself.

Getting up, my half hard erection swinging weightily below, I made my way to the bag hastily hidden in the closet.

"Let's see what she bought this time!" I thought to myself.

Opening the bag, the thin pink paper obscured it's contents. I had to be very careful to remember exactly how the bag was sitting, how the paper was stuffed in, and most importantly how the lingerie was placed in the bag. This was a practice I felt I'd mastered in the 37 years I'd been sneaking into women's panty drawers and dirty clothes hampers.

Beneath the delicate pink paper, lay one of the most beautiful pieces of lingerie I had laid my eyes on the longest time! My heart skipped a beat as I subconsciously thought about wearing it. Imagining the process of putting it on sent sexy shivers through my body. The teddy was neatly folded at the bottom of the bag, almost beckoning me to touch it, calling out to me in a way that I couldn't resist. Taking a mental picture of how the piece sat, I gingerly grasped the shoulder straps of the bodysuit taking care not to disturb anything resting below. Quickly checking the tag at the back I discover it was a size 14!

"Well... it's not for Sarah, she wears a size 8, so who could this lovely piece of heaven be for!" I thought thumbing the silkiness of the shoulder straps, no one in the house was that big but me!

At the bottom of the bag lay simple silicone breast forms. They almost looked like uncooked chicken breasts. They were nondescript, and void of nipples or any other markings. They weren't huge but definitely not small either. And merely tossed in the corner of the bag, a box of queen thigh high pantyhose.

I was overwhelmed. Standing there naked, holding the most beautiful green teddy I acted without thinking, and stepped into the leg openings of the bodysuit. Pulling the material up my legs sent a slight shiver through my body. I wanted this so unbearably bad. As the back of the teddy nestled itself between my ass cheeks, the front encapsulated my growing cock and balls. Pulling the shoulder straps on I let out an audible sigh. Looking down I admired the front, floral patterned lace laid over a vivid green satin panel that caught the light and accented the curves of my body beneath. Small ruffles of delicate lace trimmed up from the edge of the crotch, snaking it's way to the cups in little scalloped patterns.

The cups looked like deflated balloons resting uselessly on my chest. Grabbing the breast forms, I dropped them into the underwire cups of the teddy. There were little pockets that seem to be made just for insertable pads, and with a little effort, I managed to place each form into the pocket, revealing a mesmerizing striped lace with brilliant green satin underneath. I had to see what I looked like in a full length mirror.

I ran across the hall to the bathroom to look in the full length mirror that hung from the door. My breasts danced with light as I turned side to side looking in the mirror. Pulling the fat from my own chest up, I could give myself the slightest bit of cleavage, and I marveled at the weight on my chest. Looking down, they fooled my eyes into thinking they were real. I wished they were real, as I pinched at the nipple of the breast form, imagining I could actually feel the pinch.

It was already decided. I needed pantyhose too!

Grabbing the box from the bedroom, I pulled at the top of the box. It was taped shut!

"Fuck!" I cussed under my breath.

Struggling to open the box, I tore the top open and dropped my head in defeat. A ripped box meant I might be caught.

"God damn it!" I whisper as though someone might hear.

What's done is done... I may as well keep right on going. Sitting on the toilet, I pulled the stockings up my legs and moaned a sigh of relief as they came all the way up my thighs. The top band was wide and featured a matching floral lace pattern that adorned the teddy, with cute little green bows sewed on at the back and a scalloped top that slightly tickled my thighs. My cock stiffened, testing the thin lace material of its heavenly prison as I tugged them up as far as I could. My toes easily visible through the thin material was stretched tight. I wished to myself that I could paint them a matching color of green.

Clipping the garter straps proved very difficult. It was completely foreign to me the first time I tried in my early youth and even with a little age and practice, I still struggled to get the clips just right. Craning and aching my back in the most unnatural ways I managed to finally clip the backs directly below where they fell from the teddy. It was beautiful, the whole thing! I stood in front of the mirror in the bathroom admiring myself in the lingerie. The only masculine signs were my messy mop of brown hair, a weeks old beard growing wildly as it covered my face and the bulge protruding tensely from the front of the teddy... and the hair covering my body.

Reaching down I touch the thin

material covering my cock and involuntarily tighten my ass, feeling the material bunch between my cheeks. I felt so beautiful, sexy, and desirable right then. Running my hands up the sides of my ass, along my ribs and softly cupping under each of my, maybe size 40D breasts, I imagined wearing this for someone other than myself. Maybe it's Sarah, maybe... a man! I bit my lip at the thought and imagined different scenarios where I might wear something this luxurious. Maybe under my work clothes out in public! Or running errands, or on the yacht owned by some hot stud.

"Whoever this is for is one lucky bitch!" I said aloud while gripping my crotch and pinching at my fake nipple.

"Yes she is..." I heard Sarah reply from just behind the cracked door.

All at once, my mind blew up.

"What the fuck!

How did she get in here?

How long has she been watching me?

I'm so busted!

I have to hide!

Run away, run away!

You can't dummy, you're in a fucking teddy and stockings!"

I slammed the door shut and tried to hide. Standing alone in the bathroom, panicked and scared, I wondered how I'd escape the predicament. That wasn't the first time she had caught me wearing her lingerie, or clothes for that matter, but I thought I'd been far more careful since then. Quickly, I scanned the floor of the bathroom for my clothes, realizing I'd undressed in the bedroom, I only found a tee shirt, and a pair of lace panties shoved in Sarah's skinny jeans that were far too small for my large frame. Grabbing the tee shirt, I covered the obscene protrusion that ruined the look of the lingerie and meekly opened the door.

"How long have you been watching me?" I sheepishly ask.

"Since you kicked your shoes off in the bedroom... you obviously didn't notice the iPad set up on the dresser did you?" She said calmly. She looked quite angry but her voice was hiding her emotions.

"I'm sorry babe, I swear..." I tried to say before she cut me off.

Sarah placed her hand at the small of my back, right where the top of the teddy ended. I felt her hook a thumb inside as her fingers pulled at the material slightly. She ushered me into the spare bedroom. She sat on the bed and pulled my arms until I fell across her lap. She began swatting forcefully at my ass cheeks. The heat of the stinging blows growing and radiating out in agonizing waves. This wasn't one of the playful loving spankings I'd enjoyed from her in the past. This was a 'You fucking lied to me, and need to really be punished' kind of spanking. I tried standing to get away, but each painful swat pushed me back on my face and she had a hand on my head holding me down.

With one final forceful slap on my enflamed ass cheek she yelled, "Don't you fucking lie to me!"

Laying breathless, ass exposed a deepening shade of raspberry. I didn't dare move. I could feel the thin straps from the teddy with the cute little bows attached above the clasp digging painfully into my sore buttocks. I felt more exposed vulnerable and humiliated than I ever have before. Slowly, she began caressing my sore ass cheeks.

"This isn't something new. I've known for some time. When I do laundry and my fucking panties go missing, only to return a day later stretched out, or my hangers flipped in the closet and the buttons on my dresses undone. You've been wearing my clothes for years, haven't you!" She said more and more angrily.

"You need to get dressed, we have things to do!" She said.

I started back toward our bedroom still trying to hide the obscene bulge at my crotch, while slowly starting to unbutton the suspenders from the pantyhose when she slapped my hand hard and said,

"I didn't say one thing about taking anything off bitch, now get dressed!"

I was stunned! She had called me a bitch... I didn't know what to think or do. Dumbfounded, I scanned the room for my clothes, I needed to find something that might cover this silly ensemble up. Pants are fine, but since it was 90 degrees out, I wouldn't be able to wear a hoodie or a coat at all like I initially thought. Grabbing my jeans, I started sliding them up my legs when she ripped them from my hands.

"No you don't! Dirty little sluts don't wear men's jeans!" She said as she handed me a pair of plaid shorts.

Holding them up to my body, I saw a pair of green and red tartan shorts with a very wide front flap. Three faux buttons adorned each side of the flap that appeared to be quite high waisted. Pulling them up my legs and just past my belly button, I discovered they nestled deeply into my ass cheeks, accentuating the size of my ass and when buttoned up, the wide front panel almost painfully smashed my belly pooch flat. My cock bulge was still entirely visible and reaching down, I forced it back toward my anus. Pulling up tightly caused both of my testicles to pop painfully up into my stomach. I had an almost feminine look and secretly smiled inside. I would have never thought to pick a pair of shorts like these. Touching the smooth material covering my ass, I turned side to side drinking in my new look. They barely covered the top of the thigh high pantyhose and if I bent at all, the bow from the top of the hose would break out under the bottom hem. Breaking me out of my trance like state, Sarah handed me a thin white sleeveless blouse with ruffles down the front.

"Are you enjoying yourself slut?" Sarah asked.

I chose not to reply and just took the garment from her outstretched hand. Dropped my head and said, "I'm sorry babe."

Pulling the blouse on and buttoning it up I could clearly make out everything beneath the thin material. My breasts were sticking out lewdly and the green material of the teddy still shimmered slightly. I struggled with the small buttons of the blouse as they are completely backwards and my large rough fingers could barely grasp the miniature buttonholes.

Just as I finished the last button, I felt Sarah pulling at the bottom of the blouse, tying the flaps of the blouse tight around my rib cage into a broad bow set off to the side. The tenderness of the act caught me off guard and I relaxed slightly. Looking into her eyes, I could see love and compassion resting quietly behind her calming anger. Primping the bow she'd just created, a look of satisfaction settled in and she too started to relax.

From the closet behind her, Sarah gently kicked a shoebox along the floor toward my feet. The box contained a pair of the most wonderful high heels I'd ever seen in person. The darkest green top and toe, with almost imperceptible hints of neon glitter infused in velvet, sitting on top of an electric green sole and heel that looked like it changed color in the light, tapered down the 4" length to an almost needle like pinpoint, half the size of a dime. They were beautiful and I prayed they would fit my feet.

"They'll take some getting used to but I'm sure you'll figure it out." She said as she promoted the bow on my blouse once again.

Slipping them on with some effort, I realized they weren't comfortable at all. They fit, but they pinched my toes, and dug into my heels. But they looked amazing! Standing there, feet on fire, ass still throbbing, and cock tucked painfully between my legs, I became mesmerized by what the outfit had done to my body and it's posture.

My calves tightened, and made my legs look toned and shapely. The height of the heels forced my back to straighten, ass to poke out a little bit and my shoulders to fall back slightly. The breast forms and slight cleavage stood on display in such a feminine manner. From the neck down I felt so sexy and feminine. I looked good, not too sexy but definitely not a prude. Small inklings began to form in my mind. I realized first that the shoes were likely a special order item.

I didn't know of anywhere local that sold size 14 women's pumps like these...

A beautiful teddy with pockets for breast forms and a wide front crotch area...

Breast forms...

Fishnets...

Adorable high waist shorts with a flattening front panel in MY SIZE...

And a cute crop top in MY SIZE...

"You bought this all for me, didn't you?" I ask while admiring myself, walking in little steps toward the mirror in the bathroom, that caused pain to shoot up from my toes.

Not giving me time to process anything, she placed her hand at the small of my back and ushered me toward the front door.

"Hey, I cant go outside! Someone is going to see me!" I cried out as quietly as I could.

She is pushing me along and a can't even walk in the damn shoes. Every third step my ankle rolls under me and I almost fall. Opening the passenger door to the truck.

"Get in the truck, or stand here for all the neighbors to see!" She said as she slapped my ass and opened my door.

I was so humiliated. Tears forming in my eyes, I start sniffling.

"Then go inside, take all that shit off and swear you'll never wear any of it again!" She said only an inch from my face.

I knew I couldn't stop. I knew I'd be lying to her if I did say I'd stop. The truth was, I wanted this, I wanted the freedom, I just wasn't sure I wanted it like this!

"If you don't quit crying, I'll drop you off on the other side of town and you can walk your pretty little ass home!" She growled.

I sniffles one final time, and got in the truck not knowing where she was taking me.

We drove just across town to a salon. Her friend works at, so I know the place. She walks around to the outside of my door and pulls on the locked handle.

"If you don't get out of that truck by the count of three, I'll rip you out and spank your ass right here on the sidewalk in front of all these people! Now, one..." she said loudly enough for several people to turn toward the commotion.

I got out of the truck and stood at her side with my head hung low. I was ashamed and humiliated but strangely aroused. I hoped no one could see me or worse recognize me! She grabbed me by the ear like a misbehaving child in tow and headed for the doors of the salon.

"Oh my god, I can't believe you actually got him in here!" I heard from one of the hair stylists.

"Yeah, I walk in and he was touching himself, all dressed up like some floozy!" Sarah said.

I could hear the subdued laughter from the women as they were getting their hair done. This was the worst feeling in the world but sitting in the salon chair, I noticed a stirring under my shorts. My dick was hard and leaking, it was painfully evident by the wet spot forming in the crotch of my shorts. I crossed my legs in an attempt to hide the wet patch but that only put pressure on my hardened cock and made it worse.

"We HAVE to do something about that hair!" Said her friend loudly.

That caused another round of giggles from the room. I knew what they were laughing about. Here I sat, in sexy lingerie, cute shorts and top with pumps, sporting a serious erection, and a full face of beard hair! I was laughable!

"How did I let this happen?" I said under my breath.

"A real man wouldn't have let this happen!" The stylist replied loudly. And several women laughed wildly.

I didn't think she could even hear me.

Two girls came over. One started shaving my facial hair and plucking my eye lashes while the other started weaving hair into my scalp. Apparently I was getting hair extensions. Secretly, I'd always wanted hair extensions, but never had an excuse.

Shaving the sides of my hair into a Mohawk of sorts, the girls teased my hair up in the front and moussed it so it would fall backward in a great swooping wave. I had to admit... it was super cute! The two girls poked, prodded, pinched, and pulled until they thought I was done. 2 hours of shaving, hair and makeup, later I had no idea the full extent of what they had done until they spun me around to look in the mirror.

I didn't even recognize myself. There looking back at me was a completely new person. She was a very tall woman with masculine features hidden by makeup. These cosmetic magicians had worked a miracle on me and I was in awe. I didn't look like some gawdy drag queen, but an elegant looking woman who was set out for a night on the town. It looked as much like I belong on the fashion runways of New York as I did wearing tool bags swinging a hammer on any job site in America. My hair had a fierce feminine look with the sides and back shaved, and the top teased up into a wave but fell back into a lattice design.

Stepping out into the cool air of the night, I felt like something had changed deep inside of me. No more was I just an average guy to work his 40 hour week, returning home and expecting dinner on the table, cracking open a cold beer and watching the game on TV kind of guy.