Feminized Pretty Boy

[angelique127]

Looking for a rather passive young man to be my boyfriend and who is willing to undergo a complete makeover from male to female. Must be willing to play along with my fantasy and become my cherished little sissy. If you ever wished to be transformed or dreamed of being turned into a female for one night of pure pleasure, dressed up in a skirt, soft silky panties, stockings and heels feel free to contact me. I promise to do my best to make you into the perfect female. I have years of experience in applying make up and lipstick and such ! Of course we will have to remove all your replusive body hair, shave your legs and under arms, give you a pedicure and manicure, trim those thick bushy eyebrows. Just think once you look into the mirror how pretty you will feel all dolled up ! Perhaps we can go on a date to my favorite private club. I am positive no one will ever guess you were really a male...

So if you dare to live out your wildest fantasy and be my 'bitch' for the weekend, don't hestitate to contact me here. Must be somewhat slender, passive, with a positive attitude and not afraid to be ruled by a strong, aggressive and beautiful outgoing female !

I am waiting for the right male to come along...and by the way you may address as Miss Isabelle...

 

[angelique127]

Oh please...there has to be at least one male that wants to get in touch with his feminine side and have a complete makeover done by a gorgeous female diva...

 

[angelique127]

Nobody wants to play with me { pouting }

 

[angelique127]

No one wants to play with me ? So no male is willing to worship a goddess and be involved in a female led relationship ? I promise you would never regret one moment of being my panty boy !!!!

 

[angelique127]

May have found a male willing to play with me !!!!

 

[JDrew]

Laundry. I dumped a load of tangled clothes on the bed and started sorting tee-shirts from shorts, jeans from underwear, looking for matching socks—always one missing, chewed up and swallowed by the dryer presumably.

On the TV behind me was a day time marathon of Love It or List It on HGTV. Just buy the new house already, I thought, as the homeowners debated and mulled their options. Hilary never comes up with the space the couple is really looking for—not as much as David finds for them in a new property.

I found a few socks that matched and folded them together. Only two remained that didn’t have a mate. I put them aside for now. Maybe I’d find the match in the next load.

I put my clothes away first; shoving shirts in a drawer and workout clothes on the top shelf of the closet. I took a little more care putting Angelique’s clothes away; hanging her shirts neatly and stacking her shorts in a neat stack in the “shorts” drawer.

Last was her underwear. I laid her bras on the dresser and picked up several pairs of panties from the bed. The top pair; pink silk with black lace, looked new. I tried to remember seeing her in them and came up short. Not a big surprise, she does buy a lot of lingerie. Fine with me. I often jokingly encouraged her to max out her Victoria’s Secret credit card. I was both excited to see her in her sexy lingerie and also jealous.

My boxer briefs were black, basic cotton. Function over form. The same underwear got worn for a night out, a day at work or a workout. I wondered what it would be like to have options. To match my underwear with my outfit or to my mood. I wondered what it would feel like to wear something so soft and fine throughout the day.

I held up the pink and black panties. I looked at the size. I was transfixed with the thought of slipping them on. I looked at the clock. Angelique was at work—she had a Friday late lunch meeting with colleagues and wouldn’t be home for at least an hour. I looked back at the panties and felt silk on my fingers.

The desire was too strong and I slipped out of my shorts and boxer briefs. She can never know, I thought as I pulled up the pink and black panties. They fit well, more comfortable than I expected. I walked around the room expecting my penis to slip out of the underwear not built for a man but the panties held me in place. I liked the feel.

I stood in front of Angelique’s vanity looking at myself in the mirror. My slim figure didn’t look all that out-of-place in panties and it surprised and delighted me. In fact, apart from my hairy legs I thought I looked pretty good, natural. I wondered if I’d fit into any of Angelique’s other clothes but decided that it wasn’t a good time to try it.

I turned sideways wanting to look at my profile in the mirror but instead saw the reflection of the door behind me swing open. My heart stopped.

 

[angelique127]

I was actually relieved when our weekly lunch was cancelled, although I usually enjoyed going out to luch on friday with my mostly male colleagues. Not only did I get the benefit of a free lunch paid for by corporate but I could let my hair down and mingle in a more casual atmosphere with my co workers over a delicious meal after a stressful week dealing with issues in and out of the boardroom. I won't bore you with all the details of my professional life at the moment except to say I couldn't wait to get home and see my boyfriend, Drew. He was so sweet and considerent { and he gave the best foot massages in the world after a week of wearing high heels all day around the office } and I really looked forward to our weekends together. Drew had many talents { like preparing fantastic meals } and I loved the way he liked to spoil and pamper me !

Arriving home, the house was quiet and I thought that maybe he had went out with his friends and I immediately slipped out of my heels and went upstairs to my room. Opening my door, you can not imagine how shocked I was to see my loving boyfriend standing there in front of the mirror, wearing nothing but a pair of my panties !

I blinked my eyes several times surprised at what i was seeing...and for a moment I was at a loss of words...

" Drew ?

My boyfriend looked embarrassed to say the least ! Myself, I was just rather confused...Drew was not a macho kind of guy, in fact he was passive and gentle. But why was he wearing my panties ???

" Drew please tell me why you are wearing my panties ? "

 

[JDrew]

I swung around to face the door as Angelique came in to the room. My face immediately burned with the heat of embarrassment.

“Angelique!” I stammered. “What are you doing … I mean, what time … I didn’t hear …”

I grabbed my shorts and a tee-shirt and dashed into the bathroom. “Give me a second,” I shouted as I closed the door. “I’ll meet you in the kitchen.”

I stared at my reflection in the mirror. My cheeks were as scarlet as the silk in the panties I was wearing. I can’t believe she saw me like that, I thought. How could I have not heard her come in? A million other thoughts raced through my mind: Was she going to leave me? Would she tell her friends? Would she text my friends, emphasizing the word panties with lots of exclamation points and emojis?
Deep breaths, I thought to myself. I pulled on a pair of shorts over the panties and dropped the tee-shirt over my head. After a few minutes I was composed enough to face Angelique.

She sat in the kitchen waiting patiently for me, her legs crossed and one foot bobbing up and down slowly. She didn’t look upset, in fact, it looked like she was trying to stifle a grin.

I grabbed a bottle of Chianti from the wine rack on the kitchen counter, two large red wine goblets and my old waiter’s cork screw. Still without speaking I popped the cork and poured us each a healthy glass of wine.

I still didn’t know what I was going to say when I eventually started speaking. Still, Angelique was quiet, patently waiting for me to answer her question: Drew, please tell me why you are wearing my panties?

I slid her glass of wine across the table as I sat and took a large swallow from my glass. I steadied myself and finally decided that the best thing to do was just be honest.

“I wanted to try them on,” I admitted. “I …I like panties.”

I was like an open faucet after that. Words spilled from me in a torrent. I shared how I like looking at high heels. “Not in a foot fetish way,” I said. “I like the fashion, the styles, the designers: Louboutin, Rossi and Steve Madden. I look at dresses and lingerie and I’m attracted to it both as a man, like in a sexual sort of way, but also with a curiosity. I guess I have a feminine side that got the best of me.”

I paused not sure what to expect. Would she laugh it off? Would she walk on me disgusted.

I looked up from my now empty wine glass for her reaction.

 

[angelique127]

My dear boyfriend had not expected me to come home early it seemed.

Caught in the act and filled with embarrassment, Drew had rushed into the privacy of the bathroom, saying he would meet me in the kitchen. I gave him his space and went downstairs to wait. Actually I wasn't all that upset, it could have been alot worse, I mean I could have caught him in bed with my best friend...or worse with his best friend, I reasoned...

Within minutes Drew came downstairs and into the kitchen where I was waiting, clad in a tee shirt and a pair of shorts. He thoughtfully opened a bottle of wine and poured us a glass. I took a big sip and waited for an explanation...

I listened while he confessed that he liked to wear not only my silky panties but had an appreciation for high heels, dresses and lingerie. Drew explained that he was trying to get in touch with his feminine side. He shared his deepest darkest heart felt secret with me and I was touched by his sincerity !

Once he finished, he looked into my eyes waiting for my reaction. Perhaps some women would be upset or even disgusted by such behavior but I actually thought of it as a possibility for better things to happen. In a way Drew was giving up his musculinity but I didn't mind at all. If I didn't have a career as a probate lawyer, which I found boring sometimes, but was rewarding financially, I would have been a beautician. I loved doing makeovers and hair and had even went to class for it when I was younger and graduated. My younger sister and my friends, including my poor little brother were all subjected to my makeovers and used as my guinea pigs but seldom were dissappointed in the results. I was very talented...

This was almost like a dream come true ! A golden oppurtunity and a way to have some girly fun. To be honest the thought did cross my mind that my boyfriend would make a pretty girl if given a proper makeover...now was my chance !

" Why Drew I understand your feelings. What man wouldn't want to be a female in secret sometimes and we have the whole weekend to play. "

Drew nodded looking relieved.

I stood up and took his hand and we went upstairs to our bedroom together.

" While I slip into something more comfortable baby, why don't you fill the whirlpool. The first thing we have to do is shave all of your body hair on your legs, chest and underarms. "

This was going to be so much fun and we had the whole weekend...

 

[JDrew]

I turned on the faucet in the tub and adjusted the temperature until it was steaming but not scalding to the touch. Was this really happening, I thought to myself. Would I really have admitted all of that to Angelique if I thought she would walk out on me? Probably not. Yet, I would not have expected her to react so … what was the expression on her face? Glee? She was clearly excited to have the opportunity to transform her boyfriend into a girl. And apart from being relieved at her reaction I was equally excited to play along.
I rubbed my jaw and felt three days of stubble on my cheeks—not shaving, just one of the advantages of working mostly from home. But, not a good feature if I expected to achieve a girlish look.

I lathered my face and shaved quickly, studying my features. High cheekbones, my nose, a little long perhaps but narrow and rounded, full lips, an understated, rounded chin, maybe Angelique could make it work.

Not that I didn’t have confidence in her. If anyone could make me look feminine, it was her. She was talented, her make up always perfect: work, a dinner party, a friend’s wedding, she always knew how to create the perfect look for any occasion. Some mornings I'd stir and watch her, with a loving mix of awe and contentment, get ready for the day. “You look beautiful,” I might say as she slipped out the room headed to work. And, of course, I knew that beauty was passion of hers since childhood.

And now I was in her hands. A smile crept across my face.

I rinsed off the remaining patches of shaving cream, pulled off my tee-shirt and shorts, paused for a few second to admire the panties before pulling them off as well.

“I’m getting in the tub,” I shouted. And as I eased myself into the water I wondered what Angelique had in store for me.

 

[angelique127]

I put on my boyfriends favorite sheer see thru nighty, the one that drove him wild whenever I wore it for him along with a matching pair of panties. Perhaps if he was a good boy I would let him wear it later...for now I wanted to tease him unmercifully first.

Drew was relaxing in the whirlpool waiting for his makeover to began. He looked a little anxious but I was confident he would follow through. By time I was finished with him he wouldn't recognize himself ! I was going to transform him into a my pretty little bitch boy !

" Okay baby, lets get started shall we ! Why don't you stand up and put your leg on the edge of the tub so you can shave it. " I told him handing Drew the shaving cream. He did as I requested and began to lather up his calve and upper thigh. Once he was finished I handed him a sharp straight razor and he proceeded to remove his unsightly leg hair. Not that my boyfriend had very much to deal with, especaially on his chest and it didn't take long to shave both of his legs. Next he carefully did his underarms, which were rather hairy.

Once his body hair was removed I had him sit back down while I washed his hair. Drew was blessed with a thick head of hair for a male and it was rather long, although it wasn't long enough to put it in a ponytail it was long enough to wear in a man bun. He looked so cute....I rinsed the shampoo from his hair with my brass pitcher and gave him a fluffy towel to dry off with.

I told him to have a seat at my makeup table in front of the lighted mirror.

" Thank you baby for letting me do this...we are going to have so much fun ! I promise by the time I am finished you will never want to go back and be a male ever again ! "

Drew grinned but looked uncertain.

" Now let me see...I think we shall do your fingernails and toenails in pink polish, don't you think ? " I asked picking up my fingernail file...

 

[JDrew]

Shaving my body felt weird and wonderful at the same time. Angelique apprised my every move, clad only in her see-through nighty and panties. I didn’t know if I should be aroused or strictly submissive to her.

“It’s going to be hard for me to concentrate with you dressed like that, you know,” I said. “I’m going to need a box of band-aids.”

She smiled and simply pointed to a small spot I missed on my calf. When I was done I had removed every bit of hair I had anywhere: arms, legs, chest, pubic area.

Angelique directed me into warm water. I laid back in the tub for her to wash my hair. I relaxed as her fingers massaged my scalp. All the uncertainty I felt earlier was now gone—washed away like bubbly shampoo suds from my hair. I felt pampered. The whole experience felt like a spa treatment.

When Angelique was finished with my hair I stepped out of the tub, dried off and covered myself with a coconut scented lotion. My skin was completely smooth, soft and pink from the warm bath.

“Okay, have a seat right here, baby” she said, indicating the chair in front of her make up table. I slipped into the padded chair and looked at all the brushes, tubes and small bottles neatly organized on the table.

“Ummm, Hmmm,” she hummed and nodded towards my legs. I was sitting upright with legs spread apart, like a man. With a flick of her finger I knew that she wanted me to cross my legs. It took a couple of seconds to get into a comfortable position but I placed my left knee over my right and steadied myself.

She thanked me for letting her make me over and then promised I’d never want to be a male again.

I grinned uncertainly but thought maybe that would be true. Angelique took my hand and started filing my nails, suggesting that we use a pink nail polish.

I nodded.

“You know, I should be thanking you, hon,” I said graciously. “I mean after all, this is my …” I paused, my what? Fantasy? Yearning? “Well, thanks for understanding.”

She twisted open a small bottle of pink polish and started brushing the color on my nails. For the first time in my life I was getting my nails done and I had to smile. I was also a little relieved. When she first took my hand and pulled me upstairs I wasn’t sure how far thing would go. Angelique is not someone who does things part-way and I half thought that she might have drug me to a nail salon to get manicures and pedicures—that she might even have insisted that I get sculpted acrylic nails. I wasn’t ready for that sort of commitment so a little polish was a nice and welcome, first step.

When my hands were done I stretched out my fingers admiring the result. “They look so nice!” I yelled. “Love them!” I waved my hands lazily in the air drying the polish.

Next, Angelique worked on my toes. She popped my toes into a set of purple toe separators and quickly polished my short nails.

“You do such a great job, hon,” I said. I leaned up and kissed her. She smiled at me, clearly happy with herself and the result of her work but something else was in her eyes. A look I’d not seen before, a mysterious, mischievous squint in her eyes.

 

[angelique127]

Drew seemed to be enjoying his makeover so far, which was a very good sign for his future or shall I say our future ! This was my dream come true. By the time I was finished my boyfriend would never want to go back to being a male again !

" Okay perfect...although in the future you need to grow your fingernail a little longer or use some fake extensions if we go out in public and show you off. " I suggested not wanting to rush into this so fast as to make him have a change of heart...little did Drew know that this was only the beginning of his training. One of the things that attracted to him in the first place was his easy going, passive manner. For the most part he treated like a princess and was considerate in public or in private...my boyfriend definately had potential.

" Hmmm...next I think I should do your hair ! Actually it's just long enough to work with and not to short. Don't worry have have lots of extentsions for you to wear...they are alot better than a wig, but first we will need some gel ! " I said running my fingers through his thick locks and kissing his cheek. " Thank you baby for giving me permission to make you over ! I'm having so much fun ! "

Fortunately my boyfriend had blondish hair that more or less match my colored extensions and we wouldn't need to dye it just yet. After picking out certain hair extensions I used my brush and blowdryer before appling the gel. Wanting to keep his attention I stood in front of him, my ample cleavage at eye level, inches from his face while I teased and did his hair, adding the extensions as I did...

 

[JDrew]

Angelique’s breasts were only inches from my lips. Between my crossed legs I felt my penis begin to enlarge. It was uncomfortable and I shifted in my seat. I thought about playfully nibbling on her rose colored nipples, through the sheer fabric of her nighty but was afraid my erection would only get bigger ruining the moment.
In the back of our closet was a box of forgotten, little used sex toys: various sized dildos, nipple clamps, furry handcuffs, a deck of playing cards that featured different sexual positions, a handful of old DVDs, and a stainless steel, male chastity device. Trying to will my erection away made me think of that torturous device, still in its original packaging, hiding in the closet. I wondered if Angelique would threaten to pull it out if she thought I wasn’t able to control myself.

I shifted in my seat again and switched my legs—right over left.

Angelique parted my hair with a long comb, gaging where she needed to clip in the extensions. She moved around me pulling layers of hair, spraying me with hairspray and inserting pins to hold my hair in place. When she had the perfect spot she started adding the dirty blonde pieces. In the mirror it looked like a perfect color match.

She continued to spray and comb and tease my hair until finally she pulled out the pins and my hair fell to my shoulders.

I looked at each side. Angelique held a mirror behind my head so I could see the back. “It’s so perfect! I can’t even tell it’s not real,” I said. She continued to fuss with small strands of hair, patting them in place and then giving me a hit of spray just too be sure nothing moved.

She beamed.

“Baby, this is really amazing. I mean I almost don’t recognize myself,” I said. I tossed my hair side to side to see if it would stay intact, look real.

“Not too much!” She yelled at me.

Smiling, I brushed a few stray hairs out of my face. In the mirror I caught a glimpse of my pink nails against my new, long blonde hair and I felt a jolt of excitement rush through me. My transformation was truly underway.

 

[angelique127]

Let's just say I was very proud of the way my boyfriend was accepting his transformation into a female. The proof was in the pudding sort of speak, I could tell by the way he kept crossing his legs and I was aware that his 'dickie' was getting stiff inside his silky pantie. I have to confess our love life was good, Drew was a very attentive lover who did his best to please me but if I had to find fault it was his premature ejactulation. He could not really last very long, which sometimes left me frustrated...not that I liked too complain too much, I had a solution called a cock cage for all of that and this make over had given me the perfect opportunity to fix the problem. I also planned to throw away all his boring boxers and replace them with a set of silky delicates to wear every day for now on. It would be our little secret...

" From now on you are not to get a haircut without my permission. You have such thick hair for a guy and it's so managable ! " I complimented him as I admired my handiwork...

Drew smiled, seeming to enjoy his make over.

" Okay baby next we can do your make up ! You are going to absolutely love wearing lipstick and eyeshadow. By time I am finished you will not even recognize yourself, I promise ! Why wait into you slip into a brand new pair of silk stockings...but lets not get ahead of ourselves shall we ? " I couldn't help but giggle.

I decided to start with the eyeliner. Drew had rather long eyelashes for a guy...

 

[JDrew]

Angelique clicked her nails over tubes, colored pencils and thin brushes before picking up something that looked to me like a narrow black marker. She explained the differences between liquid and gel pencil eyeliner as she worked. Occasionally she’d ask me to lift my head or close my eyes. I asked few questions knowing that I wouldn’t understand most of what she said anyway. Instead I sat quietly, attentively listening as she explained a little of her process or why she preferred one brand over another. She mentioned MAC, Urban Decay, Clinique, NYX and more. “You’ll learn all about it in time,” she assured me.

My eyes took shape, dark and striking; Angelique’s skills on full display.

She teased me about wearing stockings. I laughed at her giggle but was excited about the idea. Despite my anxious curiosity I wondered how far this was going to go.

Images flooded my mind: date nights replaced with weekend trips to the salon together—hair styled and dyed, nails done, massages, too? What would my future look like as a sissy girlfriend to my …. girlfriend? And while I considered those situations as abstract occurrences, more of a fantasy than reality, her words were starting to penetrate the surreal moment we were sharing: “if we go out in public and show you off,” she had said.

Getting me through the front door dressed as a woman was going to take some serious convincing. With her career as a lawyer, however, Angelique was used to make convincing arguments. She often used those skills against me when we tangled over decorations for the house or where to go out to eat.

Another thought drifted through my mind: Would she expect me to go out to diner or for drinks like this? Surely this fun was just for the two of us.

“Wait,” I commanded. “You said if we go out … in public. You don’t plan to take me out like this do you?”

 

[angelique127]

" Wait, you said if we go out...in public. You don't plan to take me out like this do you ? "

" Why yes silly boy...it will be so much fun ! No one will ever know...I will just introduce you as my girlfriend from out of town ! Wer don't have to stay long baby maybe for just a drink or two ! "

Drew frowned apparently not comfortable with the idea.

" Oh please baby, won't you do it for me ! No one will ever know, it will be our little secret ! I have the perfect pink dress for you to wear...and a pair of heels for you to die for ! " I encouraged him, kissing his cheek...

I could sense his hesitation and I knew I had to be careful not to rush into anything too quickly. On the other hand I couldn't help noticing the way he was re-crossing his legs and his stiffy straining against the silky materail of his panty. A man with a hard on was easier to control.

" Oh sugar don't you want to make me happy ? " I whispered into his ear, " I promise if you do this for me I will make it a night you will never forget when we get home later ! "

Drew winced seeming to think it over.

I licked his ear with my tongue, something I knew he liked...alot.

Not waiting for an answer, I chose a hot pink tube of lipstick and applied it to his lips, making him look pretty...what dear Drew didn't realize that he had already given up his male masculinity and just entered into female led relationship with me...

 

[JDrew]

Angelique pressed her tube of lipstick to my mouth before I could reply. The sensation of wearing lipstick for the first time distracted me. I felt different. I puckered and pressed my lips together and a gentle wave of femininity washed over me. My realization was that I wanted to be pretty.

I tried to picture the pink dress that Angelique had in mind. She had a few—one with large white polka dots—sort of a pin-up dress and I wondered if that was the one she wanted me to wear. But she had others as well. I tried to picture the shoes that would go with a pink dress. Maybe something silver and glittery. She had a pair of rose gold strappy sandals I always loved—but would they fit? Would any of it fit?

I was fit and narrow so getting into a dress wouldn’t be a problem but how would it look on me? Surely I wouldn’t be able to fill it out. Not the way Angelique, with her perfect curves, rounds out a tight dress. She turns heads. Men and women. Her body inspires sexual fantasies. Would I look okay next to her?

Doubt crept back and I shook my head. “I don’t know, honey. I mean … I do want to … make you happy, of course.” I looked at myself in the mirror admiring my hair and full, pink, glossy lips.

I wasn’t too concerned about running into a co-worker. As a freelance copy writer I spent most of my time working from home. I did have an occasional virtual video meet with an ad exec or creative team but the lighting was never good in those meetings which made me think that it was next to impossible that anyone would recognize me in public. But Angelique had lots of co-workers and clients.

“What if we ran into someone we knew? Someone you work with?” And then another thought: “How would you introduce me? I mean, what you call me?” I laughed. “Are you going to give me a girl’s name?”

 

[angelique127]

" Don't worry about running into someone we know sugar, there is this little new club downtown I have been just dying to go too ! No one I work with would be never be caught dead in such a place ! " I informed my boyfriend or should I say my new best girlfriend forever...I didn't dare give him the details about the club yet, in which every night was for ladies only and catered to certain male clientle, mostly middle eastern or north african muslim men. Tall dark and handsome types ! What Drew didn't know wouldn't hurt him...


Next I applied a hint of blush to his cheeks, trying to think of a name for him or should I say her. With each passing minute Drew was looking more like a female and a very pretty one to say the least. I couldn't help but wonder how he would react if a handsome hunk hit on him when we went out because I was making him look so feminine and pretty. As far as a cute name, nothing really stood out which went with Drew...

" Hmmm...I've always liked the name Prudence, like in that Beatles song ! Or perhaps Sissy or even Missy ! I suggested, noticing that he was kind of frowning and thinking it over...

Finishing with his makeup and hair I picked up my mirror and let him admire my handiwork. I had to admit no one could mistake him for a guy unless they looked closely at his adams apple which I could do nothing about ! My boyfriend had transformed into a very pretty and attractive female !

Now for his attire. If he was going to wear my favorite pink dress with white polka dots I thought white stockings would match. Of course to be color coordinated I picked a matching garter belt although no one would know he was wearing one except for me...

" Lets start with this suspender belt ! " I told him after finding one and a fine pair of silk stockings in my lingerie drawer. Fortunately I had several in every color and them some in my vast collection. " Stand up baby so I can put this on. "

I placed it over his slim waist and hooked it in the back. It was a perfect fit since we were basically the same size. The stockings should also fit in the same manner...

Okay sit back down on the chair and put these on next. " I handed him a fine pair of seamed stockings to slip into...

 

[JDrew]

As the silk stockings slid up my legs I felt a jolt of excitement run through my body. Every part of me tingled with the thrill of the transformation. My skin was soft and smooth. I was intensely aware of the make up I was wearing—my eye lashes felt a little heavier with mascara and my lips were coated and glistening. And now, wearing panties, stockings and a garter belt I felt more feminine than I could have imagined.

I moved around the room feeling the stockings cling to me like an extra layer of shimmering skin. The undergarments were a little tight and I figured would take some time getting used to. It was an odd feeling of sexy and uncomfortability. Yet, it felt right.

I squeezed Angelique’s hand. “You probably think that I’m so weird but I am having fun,” I admitted. “And, I love how I look.” I wrapped my arms around her shoulders and hugged her.
“You’re really good at this, honey.”

I leaned away from her. “I still have to see how I look in your dress but I hardly recognize myself. I guess if you want me to go out like this, it’ll be alright. Just for one drink.” I held up one finger for emphasis. “I’m not going to press my luck but I’ll give it a try.”

I made another turn around the room looking at myself in the mirror from different angles.

“This is your creation,” I said sweeping my hands dramatically over my body. “I guess you can name me what ever you’d like.” I grinned at her.

“What’s next?”

 

[angelique127]

" What's next ? " Drew aked seeming somewhat delighted with his appearance so far.

" Well before we put on the dress we have to finish with your underthings. I think I still have it in one of these drawers..." I said rummaging through my lingerie, " Oh here it is ! "

I held up a heavy padded bra that I had saved from my high school days before I had developed into a full breasted woman with natural 36 DD.

Drew didn't protest and just turned around and lifted his arms allowing me to put it on him. The flesh textured gel globes inside the bra were rather life like if you didn't look too close or touch them.

" Nice baby, don't worry no one will ever know our little secret ! Unless, of course you get hormone shoots in the future and grow real ones ! " I giggled not wanting to push the issue just quite yet.

Drew didn't comment but stared at his reflection in the large three way mirror...

" Hmmm baby I'm kind of jealous...I may have some competion at the club tonight with all the guys ! " I couldn't help but tease...

Now why don't you slip into this little ol' pink dress of mine that you like so much while I go find a pair of heels in my closet. Fortunately I have a few pair that may fit you until we can go shopping together to find some in your size ! "

Delighted and hopeful I went into my walk in closet, excited by the prospect of going shopping { my favorite hobby } with my boyfriend for lingerie, heels, clubwear and such and having pedicures while having our nails done. This could be the new beginning of a beautiful relationship where I was in charge of every aspect of it ! Honestly I adored my little beta male ! Finding a matching pair of heels I returned to our bedroom and saw my former boyfriend for the first time dressed as a pretty female !

 

[JDrew]

Unlike the panties and stockings the bra was a little too snug around my chest and back. I looked at myself in the mirror tugging at the underwire and trying to shape the cups. I’ll have to try on a few options to see what fits best for me, I thought. And then I froze staring at myself in the mirror. Was I really thinking about buying my own lingerie?

Images of shopping trips with Angelique filtered through my mind. I pictured us in Victoria’s Secret browsing through the drawers and racks of bras and panties. Before tonight that trip would have meant me patiently trailing behind Angelique, offering my suggestions on what I liked on her. Now, that shopping trip would be a whole other experience. I would be trying on things for myself.

I imagined us sharing a dressing room, helping each other in and out of clothes, offering opinions on we thought might look good paired with other outfits. There would still be a sexual tension between us. I’d still likely be hypnotized by her large breasts and anxious to help her out of a bra so I could see and touch them but I’d be doing so playfully and sensually.

It occurred to me that the nature of our sex life might change after this night, that she might not see me the same way that she did before I decided to try on her panties. What surprised me was: I was okay with that. And for a moment I imagined myself as a beautiful butterfly emerging from a cocoon. I was transforming and I knew that Angelique would not just help me but that she would change with me.

I could hear Angelique going through her shoes in the closet. “Unless, of course you get hormone shoots in the future and grow real ones,” she had said.

“I think this bra would fit a lot better if I did have real boobs,” I said with a snort but only half joking. The idea of real breasts suddenly seemed natural and I found myself wishing I had them, filling out my bra right then.

I picked up the dress and dropped it over my head, carefully trying to avoid my hair. I pulled and twisted and brushed it straight. It was a little retro. Maybe not quite a party dress but I’d always liked it on Angelique and now loved it on me.

Angelique was watching me from the doorway of the closet. “I don’t know,” I said. “I might steal this dress from you.” I grinned.

I stretched out my arms, wiggled my hips and twirled for her. “What do you think?”

 

[angelique127]

" I don't know I might steal this dress from you ! " my boyfriend declared even twirling around to show off how he looked in the dress. " What do you think ? "

" Oh my you look so gorgeous, Prudence ! I definately have some competition ! " I answered delighted, and using his new female name I decided on. " Now you will have to learn to curtsy for me. After you put on these heels of course... "

I thought it best to start out with only a four inch pair until she got used to walking in them first. Prudence had to learn to take smaller steps and sway her hips at the same time, not to mention appear graceful and lady like. It was like a work of art if done properly and practice made perfect !

After donning her high heels I made Prudence strut back and forth in front of me as if she was on a runway model...instructing her to shake her hips when she walked. I had to admit Drew, or should I say Prudence looked very feminine. In fact she was quite natural ! I realized at this moment our relationship had changed for the better. Drew was now my little 'bitch' and I was in control. He had willingly given up his masculinity and this was rather thrilling for me to have the power and upper hand. From this moment forward he was my little pantie gurlfriend to do as he was told !

" Very nice darling...now sit down and let me put a strand of pearls around your neck and matching clip on earring until we can get your ears pierced and we will be ready to go out. " I offered and give her a kiss on her cheek...

 

[JDrew]

Prudence … the name echoed in my mind. I loved it. And I couldn’t wait to be out, hearing Angelique call me by my new name.

But, the shoes excited me most. Most likely I’d look like a giraffe walking in roller skates—legs and knees going in every direction—and break my ankle, but I still desperately wanted to wear a pair of Angelique’s expensive shoes.

She handed me a pair of four-inch, blush, Kate Spade sandals and I anxiously worked them on to my feet. The little buckle was foreign for me and I struggled to get a good fit. After fumbling with the narrow straps for a few moments I got the shoes snug and stood.

Angelique gave me pointers: “Relax your back. Sway your hips. Smaller, shorter steps. Walk on your toes…” I moved around the room, slowly at first, but eventually gaining confidence. “Like you’re a runway model,” she instructed. I tried to emulate the models that I’ve seen on TV. I exaggerated my rolling hips, placed one foot in front of the other. Angelique laughed. “Maybe a bit much, but that’s the idea.”

It seemed like I practiced for an hour but it was actually much less time before Angelique had me sit so that she could adorn me with a pearl necklace and earrings.

I was still nervous about going out but had survived one embarrassment that night, I was ready to take this one step further.

“So, tell me about this bar you want to go to…” I said as we started down the stairs.
“Oh … wait,” I said sheepishly before she answered. “I … would you mind if I took your Coach sparkle clutch? I mean I’ll have to carry my phone and stuff.”

 

[angelique127]

" So tell me about this bar you want to go to...oh wait, I... would you mind if I took your coach sparkle clutch ? I mean I'll have to carry my phone and stuff. " Prudence asked.

" Of course sweetheart, from now on we share everything ! " I answered.

Once Prudence got her little purse we got into our car. Usually Drew drove when we went out together but tonight I decided that I would do the driving. All she had to do was fasten her seatbelt and look pretty ! Besides I knew where we were going...

" To tell you the truth, darling, I have never been to this club. Actually a friend from the firm told me about it. You might remember Jessica from the Christmas party last year, that pretty brunette who is dating that black guy from Nigeria. Anyway it is a rather unique...no white males are permitted to enter under any circumstances...unless of course they are dressed as a female and no one knows otherwise ! " I explained.

Prudence looked unsure of herself for a moment...

" Don't worry baby, no one will ever know our secret. This is going to be so much fun, I promise ! "

Minutes later after finding a place to park I touched up my own make up in the rearview mirror before exiting our vehical. Hand in hand we both approached the entrance wher a big black gentlemen was checking ID's ...

Prudence suddenly looked troubled, the name and photo of his drivers license was of a male !

" Don't worry baby, it will be fine ! " I reassurred her/him squeezing her hand.

The bouncer checked Drew's identification and did a double take and then smirked, " Enter at your own risk. "

" Thank you sir ! " I winked as I took my boyfriends hand and we entered the club. The dance music was loud, the strobe lights flashing and we managed to find a empty table in a dark corner which I preferred. I sat down and crossed my legs, Prudence doing the same, and I observed the situation. The females outnumbered the males but I could care less. Not to sound stuck up or conceited but I usually attracted male attention wherever I went and wasn't worried about the competion...besides this was dear Prudence's big debut !