Feminized Pretty Boy

[angelique127]

I woke up early for a Saturday morning. I usually slept late since I didn't have to go to work on the weekend. How many times had I envied Drew working from home, if you could call tinkering on the computer and cell phone for a few hours a day. Besides it barely paid his phone bill with little left over for our other costs of living. My patience was wearing thin with his lack of initative lately but I kept it to myself. Perhaps I had found the perfect solution since discovering Drew's secret inner passion for dressing up as a female. This could definately work to my advantage...Drew was more or less passive and submissive while I was more demanding if not dominating. I had to confess to being rather 'bossy' at times especailly when on my period.

Drew, true to his gentle nature took it all in stride and did not complain very much. That's when I decided to make him into my little bitch. From now on Prudence was going to play by my rules and become my perfect obediant maid. She would do her chores or else be punished. Of course if she obeyed my wishes and was a good little girl she would be rewarded also. From now on my needs came first and she could begin by getting up and serve me breakfast in bed.

As a matter of fact, today while on our shopping spree I planned to buy that black leather miniskirt and those thigh high boots I always wanted. Oh and a riding crop might come in handy for my new role in a female led relationship...

" Wake up sleepy head...we have a busy day ahead of us. After you make me breakfast and serve it to me in bed and then do all the dishes we are going shopping remember ? "

Drew sighed and turned on his side.

I pulled the covers down and smacked his panty clad ass. " Come on Prudence, get up, I'm hungary. Now lazy bones ! " I demanded, sounding impatient...

 

[JDrew]

“Yes, Mistress,” I said, smirking. I peeled off layers of covers and stepped on the floor immediately looking for long pants and warm socks.

“Tsk … tsk,” Angelique scolded me. As if reading my mind she said: “You’re fine just the way you are.”

“My feet are freezing. I have to at least put on a pair of socks.”

“Fine,” she said plainly. “Here’s what you’re going to do.”

She directed me to my sock drawer filled with brown and black dress socks and a few worn out, white athletic ones, too. “Take them all out and dump them in the trash. They’re ugly and won’t match anything you’ll be wearing from now on, anyway.”

I stared at her for a second. She nodded and pointed at the sock drawer. “Go on.”

I yanked the drawer completely out of the dresser with a somewhat annoyed flourish and marched it to the wicker trash bin by the bathroom door. “Yes, Mistress,” I said as I poured my bundled socks in the trash.

“Now put the drawer back without being such a damn drama queen,” She said. “And open my sock drawer.”

Her socks, bright and colorful, neatly stacked and organized, filled the drawer. “There should be a fuzzy pair of white socks with pink hearts on them. They’ll keep your feet warm. And they’ll look cute too.”

I pulled on the fuzzy socks—and while a little tight—they were warm and I thanked Angelique for sharing them with me.

“Now, breakfast,” she demanded.

Downstairs, in the kitchen, I fished around the fridge for eggs and veggies. I placed a cutting board on the granite counter and grabbed a long knife for chopping. And then looked down at myself. I could just see me splashing egg yolk all over my pink nightie. Hanging on the back on the pantry door was a clean and seldom used apron— ‘I’m sorry for what I said when I was hungry!’ Was stitched on the front in cheerful ruby letters.

I thought of Angelique laying in bed upstairs saying “Now lazy bones!” I don’t think she was sorry at all. I think she was enjoying her new role quite a bit. I wondered how long it would last. Could I really survive in a female-led relationship? Could I serve and cater to her like a sissy maid?

I looked down again at the fuzzy socks and the pink nightie now covered with an apron. Perhaps it was too late to ask those questions.

I chopped the veggies—broccoli, orange and red bell peppers, baby kale. I cracked the eggs and whisked in a splash of milk while the veggies were sautéing on the stove. Finally I scrambled the eggs and placed them over the bed of veggies. I added a piece of buttered toast and sliced strawberries on the plate. It looked like I had run out to a gourmet restaurant, I thought.

I made Angelique a cup of coffee and myself a cup of tea and placed everything on a large serving tray.

“Okay, Mistress,” I said coming back into the room. “Breakfast is served.”

Angelique sat up and I placed the tray across her lap. “Anything else, Mistress, honey?”

 

[angelique127]

Some men are so easily manipulated sometimes. Once you discover their weaknesses and insecurities they are like putty in your hands. Fortunately I had found my boyfriends secret desire to dress as a female and become submissive. Did I plan to exploite it and use it to my advantage ? Of course...all you have to do is take control of their cock. Deny their orgasms. Make sure yours always cum first and train him to please you always...

Really you can have your cake and eat it too ! Certain males will willing to give up their musulinity and give in to their inner femininity. Who doesn't like the feel of soft satin and silk against their skin ? Knowing you are wearing a pair of panties under your pants in secret for your lover...reminding you that you belong to her everytime the silky materail rubs against your penis.

Or even better yet on the weekend when you play dress up with her. She is a goddess and deserves to be worshipped as such. You bring her breakfast in bed and afterward do your chores around the house. You handwash her delicates and are obediant to all of her wishes. Before you realize what is happening, the next thing you know you are shaving her legs and painting her toenails and fingernails, as well as maintaining your own.

In time she may will invite her best friend over and show off your hidden talents. You know the gorgeous girlfriend that you always had a crush on and secret fantasies about...think of all the possibilities !!!

Why would you ever even consider resisting the urge silly ?

Now go and get ready for our shopping trip...

 

[JDrew]

I cleaned up breakfast while Angelique took a shower and got dressed. My anticipation was building. My head was buzzing with excitement and nervousness. Last night I was out in public dressed as a girl. Somehow, in the dark, at a club, it felt right. But being out in the brightness of daylight, with no shadows in which to hide, now seemed like a crazy idea.

Angelique called me from the bedroom. With the kitchen spotless I hung up the apron and returned to the bedroom. On the bed she had laid out my outfit for the day: A black, short, flare skirt; a fuzzy pink sweater and a pair of tights. She was holding a pair of tall boots out to me. “These are a little big for me but they’ll probably fit you,” she said. “Get a shower first and I’ll help you with your hair. Then you can try these on.”

I did as I was told. In the shower I noticed that my shampoo and soap were no longer on the tray—only Angelique’s products remained—smelling of flowers and citrus. As I finished washing Angelique came into the bathroom with a pair of black lace panties. “Wear these,” she said.

Once again I did as I was told and slipped on the panties. We went through a similar routine as we had the night before with Angelique clipping extensions in my hair and quickly styling it. She instructed me on how to apply my make up, now fully expecting me to start doing it myself. I made a mess of my eyeliner which she had me redo several times but I did okay blending and contouring.

“Cute,” she said. “Now go get dressed.”

I squeezed into a bra which Angelique helped me pad before pulling the sweater over my head. And then I sat on the bed and awkwardly pulled on the tights. “How easy are these to tear?” I asked as struggled to adjust the fit around my waist. Finally I got the boots on. They looked good with the outfit but I didn’t know how long I’d be able to wear them. I knew my feet would be killing me within an hour—two at the most.

All dressed I stood for Angelique to critique. “Do I look ready to go?”

 

[angelique127]

Our first stop was going to be my favorite called Pandora' Box. They specialized in sexy dancewear, heels, various toys and lingerie and even had adult movie section. Although we had never watched porn together as a couple I knew that Drew or should I refer to him as Prudence, had joined several websites on the internet. I knew what his tastes were so I decided that tonight we could enjoy it together...of course I would let him pick whatever turned him on ! Perhaps a little femdom would be nice to watch...Oh and the other reason I always came her was the gorgeous little brunette doll salesgirl named Gina. She was so friendly and attentive and treated me like royalty and always made me feel special, if I ever had a girl crush it would be her !

Prudence was absolutely going to love her !

Fortunately no one else was shopping except an older lady so we would have Gina's undivided attention. She smiled upon seeing us enter and rushed over to give me a hug, making me feel like a preferred customer. Not to mention I did spend alot of money buying lingerie and such...what can I say I was a girly girl and loved the feel of silk and satin against my skin.

" Why Angelique, it's so nice to see you ! How have you been ? " Gina asked.

" I'm doing just fine, thank you. I would like you to meet my boyfriend, Drew Hanson. We are out and about and doing some shopping so I brought him here. "

Gina blinked her long eyelashes looking surprised and caught off guard... " Why pleased to meet you... Drew ? "

I couldn't help but giggle at her expression and my boyfriends discomfort. " But you may call him Prudence. Isn't she perfect ? "

" Yes very pretty. " Gina agreed, sizing him up and offering her hand.

Poor Prudence actually blushed, looking too cute...

" We are hoping to find several pair of panties, we prefer pink, and a matching nightie and stockings. Perhaps a garter belt and bustier of his own..." I suggested winking at Gina.

She took the hint and took Prudence by the arm and led him over to a rack filled with delicates...this gave me a chance to go and explore the adult toy section...

 

[JDrew]

Gina gently took me by the elbow and guided me to a large rack of lingerie. She looked me over once again, gauging my size. I was uncomfortable having her eyes roam over my body clearly picturing me half dressed in lace and satin. She squinted and turned back to the rack. I looked over my should for Angelique but she had disappeared beyond the tall shelves of toys and displays with mannequins dressed in leather.

I turned back to Gina who was now holding up a pink bra and panty set with black trim. “This will be perfect for you,” she said. I did like it and I nodded hoping I looked more happy than frightened.

Gina picked out several more skimpy pieces from the rack. “Follow me … Prudence, is it?”

Again I nodded and followed Gina to small dressing room—not much more than a closet with a red velvet curtain draped across the opening. “Try these on. And I want to see each outfit.”

I quickly stripped down and started with the pink and black set. It was sexy and I knew I’d be leaving the store with it in my bag. What also occurred to me was that I was about to reveal myself, dressed in lingerie, to another woman. I was suddenly embarrassed and thought about chickening out. Angelique would kill me! I thought to myself.

“C’mon, let’s see it,” said Angelique from the other side of the curtain.

I took a deep breath and yanked the curtain aside. Both girls were staring at me. Immediately they were adjusting the straps of the bra and having me turn around so they could assess my ass in the panties.

“Cute,” said Gina. “You need tits though.”

“We’ll be working on that,” said Angelique.

Gina turned and disappeared.

“What do you think?” Angelique asked.

“I like it. It’s not quite as uncomfortable as I thought it might be.”

“Gina, knows her stuff.”

“Yes, I do,” said Gina reappearing with two silicone breast forms. She tucked them into my bra, made some adjustments and then stepped back. “That’ll do for now.”

“Let us have a couple sets of those,” Angelique said. “Shoes next.”

My face lit up at the mention of shoes. I couldn’t wait to try on a few pairs of heels. I turned to change but Angelique grabbed my arm. “Nope. I want to see them on you with that outfit.” And she lead me across the store.

Gina joined us with a pair of lacy thigh highs and helped me into them. Then each girl took turns handing me shoes—different heights, different styles—and I walked (awkwardly) around the store trying them out. They shouted instructions on how to look more feminine as I went. Finally we had decided on three pairs. Now that I knew my size though I knew that I’d be buying designer shoes for myself. I loved shoes!

Just as I was heading back towards the dressing room two tall, well built guys walked in. They were thin with thick arms and wide chests. I noticed both girls swing their heads the direction of the newcomers.

We had been in the store for almost and hour without interruption and I had almost forgotten it was still open. I started to quicken my pace for the dressing room but Angelique grabbed me. “Excuse me,” she said to the pair. “I’d like your opinion of my …” she paused and looked me over, smirking, “sissy boyfriend.”

 

[angelique127]

Truthfully I did not expect two handsome hunks to walk into the shop, nor did Gina. Usually most patrons were female, interested in buying lingerie for their boyfriends or husbands. These were not the kind of guys who would be buying lingerie for themselves...

Suddenly feeling impulsive I asked them, " Excuse me, I'd like the opinion of my....sissy boyfriend. "

Apparently the question caught them off guard. They checked us out, doing a double take upon seeing Prudence...

" You have to be kidding me ? That's your boyfriend ? Your dating a sissy ? " one of the guys laughed.

" Well he is kinda pretty ! " his friend remarked, smirking.

" Yeah well I guess he is getting in touch with his feminine side. " his buddy said.

" Now boys don't be so mean. How can I help you ? " Gina interceeded.

" Well I wanted to buy some sexy lingerie for my girlfriend for her birthday. "

" Okay do you know her size ? " Gina inquired.

" No not really...about her size I guess ! " He answered referring to me. " She's perfect, would you mind trying on some lingerie for me ? "

For some reason I blushed. One of my secret most fantasies was to be a lingerie model and pose in front of a camera or even better in front of two big and strong handsome alpha males...

" Well I don't know, " I said, wanting to play hard to get and not too easy, " Most of the lingerie here is very ahh...shall we say, very revealing. "

" That's why I came here, to find something very revealing, if you know what I mean. " The hunk winked at me and smiled. " Oh by the way my name is Dave. "

Dave let his eyes undress me in a bold and confident manner that borderlined on arrogance, and the smirk on his handsome face said it all...I had a feeling Dave was rather the dominant type and usually got what he wanted...

" Pleased to meet you Dave. My name is Angel and this is my boyfriend who likes to go by Prudence. " I introduced us both.

" Prudence ? What a pretty name...for a sissy ! " Dave mocked. " Do you only date guys who dress up like a girl, Angel ? "

" You shouldn't be such a bully...my boyfriend happens to be a nice, considerate, gentle guy, who recently discovered that he has a feminine side. " I defended him.

" Whatever Angel...but I prefer to see you instead wearing and showing off that hot and perfect body in sexy lingerie. "


For some reason I rather liked the idea of modeling for these two alpha males, despite their arrogant attitude. On the other hand I didn't know where this was going and it might be best to just leave now before something dangerous happened...

" Why don't you guys pick out something for me to wear. I'm sure my boyfriend won't mind helping me get ready for you. "

 

[JDrew]

I was shocked at how quickly things turned. A day of buying lingerie and playful toys had suddenly become something more tantalizing and distressing all at once. I was uncomfortable enough being examined by two women but now to have two other guys checking me out in lingerie made me squirm and I shifted my weight, very aware of my awkwardness in heels.

Before I knew it Angelique was saying: “Why don't you guys pick out a few things you want me to model for you. I am sure my boyfriend won't mind helping me to get ready for you !”

It took a few seconds for these words to sink in. I looked at Angelique and she was staring at me, lips pressed together and puffed out in a tight grin. Before I could respond she was grabbing my hand and leading into the small dressing room. “I’ll get ready in here,” she called over her shoulder. “Gina, help these boys find what they need.”

My heels clicked on the linoleum floor as I followed Angelique into the changing room and pulled the curtain closed behind us.

Within seconds Angelique had pulled off her shirt and kicked off her shoes. “Unhook my bra for me, honey,” she said.

I did as asked and she slipped the narrow satin straps down her arms. She pulled the bra free dropping it at my feet. “Can you keep all of my things together,” she said as she began wiggling out of her jeans. “Just put everything on the chair.” She vaguely waved at a small wooden chair in the corner upholstered in pink velvet.

I collected all of her garments as she stripped them off neatly stacking on the chair. Finally she turned to me, naked and beautiful, “This is so exciting!” She kissed me. Her tongue darting in my mouth as she grazed my stiffening cock through the panties I was wearing.
A hand appeared around the curtain holding a leopard print nightie trimmed with pink lace. “Try this first,” Gina said.

“Oh, nice!” Angelique smirked and pulled it on over her head. “Help me straighten this out.”

Just as Gina had tugged at my bra, straightening and smoothing, I tugged on the hem of the nightie and ran my hands over Angeliques tight body.

"You look so good, baby," I said. “Let’s see what they think."

 

[angelique127]

The two hunky neanderthal's were waiting patiently outside the dressing room, sitting on chairs with their arms crossed across their broad chests when I exited in my sheer lingerie. At first I felt self consious being nearly naked in front of two strange men but I soon relaxed, becoming comfortable with showing off my nice shapely body in front of them. Placing my hand on my hips I posed before turning around on my heels and showing my backside. Mind you I have recieved alot of compliments on my round and shapely derriere...

" Now that is a fne peice of ass, don't you think buddy ? " Dave exclaimed.

" Damn, hell yeah..." his buddy agreed.

" Do you guy's really like it ? " I asked, lifting the hem above to reveal my matching sheer thong. Honestly I was becoming rather aroused posing for these guys for some reason...maybe because they were so aggressive and confident while my own boyfriend was so passive and dressed as a sissy girl...

" Nice...now why don't you strut back and forth and let us see the way you walk in those heels . " Dave suggested.

I didn't hesitate and walked up and down in front of him swaying my hips in a very provocative manner...

They both clapped enjoying the show so far...

" Okay I like that ! Now lets see what your boyfriend can do ! "

 

[JDrew]

I was peeking out of the dressing room, watching Angelique parade around the two hunky guys. Gina was leaning against the wall next me also appreciating Angelique’s curves and provocative movements. She was the star of the moment. All eyes on her body. The guys, I’m sure, we’re wishing they could fuck her right there—have her straddle each of them in turn as they buried their faces in her breasts, their cocks deep inside her, their hands firmly gripping and squeezing her round ass.

Gina and I exchanged glances. We both wished we were her.

“She’s so fucking hot,” Gina whispered. Her eyes never leaving Angelique’s “I’d do her in a second.”

I was aroused too. Not just because Angelique looked so damn good but because of all of the lustful attention she was drawing. I was captivated but her confidence as much as her sex appeal.

She strutted around like a exotic dancer on a stage. Playful. Smoldering.

The two guys clapped and one whistled.

“Okay I like that! Now let’s see what your boyfriend can do!” Said one of the guys. I didn’t see which one.

Angelique curtsied and blew them a kiss before turning to me. “You’re up, baby,” she said with a grin.

I stared, all of a sudden frightened. The erection that just a moment ago had been straining against my panties disappeared.

“Don’t be bashful,” cried out one of the guys.

Angelique pulled the dressing room curtain from my grasp and ripped it aside. “You wanted to be a girl … well, be the sexiest girl you can be,” she said.

I stepped forward, unsteady in my heels.

“Damn, I can’t believe you’re a dude,” said one of the hunks. “I mean you could use more curves like your girlfriend but you’re kinda pretty.”

The other one said, “walk around for us. Let’s see how you do.”

I began to pace. Slowly. Carefully. My head was spinning and I was doing everything I could to remember the lessons that I’d learned about walking as a female over the past 24 hours. My hips began to sway, I remembered to point my toes, walk on the balls of my feet and to place one foot directly in front of the other. I felt ridiculous.

“Not bad,” shouted the hunky guy closest to me. “What’s your name?”

“Uh,” I glanced at Angelique. She shrugged and nodded. “Uh, it’s Prudence,” I said once again trying my best to raise my voice out my chest.

“You’d give me a stiffy, Prudence. Good girl.”

I didn’t know how to feel. ‘Good girl!’ I was proud and appalled and excited at the same time.

“Thank you,” I said.
“Show us a few more outfits,” one hunk commanded. He pulled out his wallet and looked at Gina, “I don’t want to take your time for free. Here,” he handed her a hundred dollar bill.

“For her,” he gestured to Angelique, “Let’s see something accentuates those nice big tits. And for her,” he gestured to me, “I want see something sheer. See through, ya know? Like a sexy robe or something.”

Gina snatched the bill and turn to us. “Ladies, you can wait in the dressing room. I’ll be back.”

 

[angelique127]

We retired to the dressng room waiting for Gina to bring more sexy lingerie to model for the guys. In the meantime we touched up our make up and fussed with each others hair. I was so proud of my boyfriends talent of learning to walk like a runway model and having the confidence to perform as a female. Not that Prudence was as busty as I was, of course, but with the help of some hormones in the future she would give me some competiton in that department...meanwhile the alpha males seemed to be enjoying the show !

The door opened and Gina handed us a couple of new outfits, " This is for Prudence and this one is for you. "

Gina had such good taste...

Hmmm one in black and another in white....both were very daring and showed off my full ample breasts. The outfit for Prudence was likewise very sheer and transparent and would do nothing to hide his dickie. I dressed quickly and touched up my lipstick. " I'll go out first and then you follow after a minute or so. How do I look ? "

My boyfriend eyes said it all..." Perfect ! " Taking a deep breath I opened the door and made my exit. Placing my hands on my hips I posed for my audience, turning back and forth to give the guys a better view.

" Whoa baby ...you look so hot, better than a playboy centerfold. "

" Hell yeah...look at those tits ! "

Blushing I cupped my breasts, lifting them upwards to show them off...

" Turn around and let us see your fine ass ! " one of the guys demanded.

In an effort to please I did as I was told, feeling submissive.

" Thats it baby bend over and spread those cheeks for us ! "

Again I did what they wanted...bending at the waist and using my fingers to spread my exposed naked ass cheeks...

 

[JDrew]

I was a voyeur — again watching Angelique display the lingerie she was wearing. My cock throbbed and slipped out of the sheer lace panties I was wearing. “Whoa baby .. you look better than a playboy centerfold,” one of the guys said. He was right, she looked so god damn sexy.

Then she spun, bent at the waist and spread her ass cheeks.

“Oh yeah, honey.”

“Damn girl, my wife ain’t gonna look that good wearing that. If I buy it, I might just have to take you with me,” one guy said with a smirk.

From my point of view I could see Angelique’s breasts nearly tumble out of the bra in her bent over position. I found myself wishing they had. There was something exciting about her being so sexy. Embarrassed but yet still in control. She commanded all of our attention. She knew it.

She stood again and turned to her audience.

“You need a better look at this bra?” She asked the married guy as she slid her thumbs under the lacy straps.

“Well, you’re gonna have to come a little closer than that for me to get a good look, baby.”

Angelique strode to the large guy bending over until her ample cleavage was nearly pressed against his face.

“What do you think?” she asked him. “You think it’s good quality? Like the color? Need to. … touch it?”

I couldn’t see his expression but his hands immediately went to her breasts and I heard him say: “Now they feel nice, baby.”

The other guy, watching his buddy, snapped his head towards me, still peeking out from the dressing room.

“C’mon, sweet thing,” he said gesturing to me.

I stepped out. The lingerie I had on left little to the imagination. I knew he could see my dickie, half hard from watching Angelique.

“Step over here,” he commanded.

I took baby steps, my skin cold, butterflies swirling in my stomach.

“I want to see your ass too.”

I turned and duplicated Angelique’s movement—ass up, cheeks spread.

“You do have a sweet little ass.”

I stood and turned.

“You got some nice lips too. You know where they would look good …?” His hand went to his crotch. “Let me see what you’d look like with your head down here, sweetie.”

I felt Angelique slide up next to me. “I want to see that too,” she said.

I bent at the waist, put my hands on his thighs and lowered my head to his lap.

“You’re too stiff,” Angelique whispered in my ear. “ Lighten up. Think sexy.”

I relaxed my back and shoulders. I tried wiggling my hips ever so slightly.

“Better,” she said.

I continued to move my face toward his crotch. I could see the thick outline of his hard cock bulging against the denim. All he’d have to do is unzip and slip his jeans down a few inches and his heavy cock would be in my face. Against my lips. The thought sent a fresh round of butterflies twirling in my stomach.

Angelique, still in my ear said: “Now bob your head. Slowly!”

I moved my head up and down. Angelique grabbed my hair in her fist and pressed my face against down as the guy thrust his hips upward. My face slapped against his crotch and I made a puckering sound with my lips.

“Oh, now that’s the shit.” He said.

Angelique giggled and pulled me back up.

I wasn’t sure where things were going to go from there. More lingerie? Something more physical? Then Gina stepped in.

“Alright guys. This isn’t that kind of establishment. If these two fine …” Gina paused and glanced at me, “ladies … didn’t convince you to buy something, nothing will.”

Angelique giggled again and pulled me back to the dressing room.

“Nice work, you two,” one of the guys shouted after us. I glanced back and he winked at me as he dropped cash on his chair before following Gina across the store.

In the dressing room, I collapsed on the pink chair in the corner.
“What the hell we’re we just doing?” I asked Angelique with a bewildered laugh.

 

[angelique127]

" What the hell were we just doing ? " Prudence asked laughing, once we returned to the privacy of the dressing room.

" Giving a show like two exotic dancers at a strip show. You are so pretty that you gave those guys a hard on ! " I complimented my boyfriend. " I think we should visit that strip club downtown and get wild after this before we go home ! You know Sugars the one where I used to dance. "

Taking advantage I sat down in my boyfriends lap. " I remember how you loved me to give you and your friends an erotic lap dance. "

Prudence smiled, cherising some fond memories. In fact I was aware that he had a stiffy in his silky panties

" If I remember correctly your favorite was my school girl outfit...with my little plaid skirt which barely covered my ass and exposed my panties for everyone to see. " I teased, kissing his lips seductively...It made me hot just thinking about how wet and excited I used to get dancing in front of everyone both males and females, showing off my body !

We kissed, our lipstick smearing on each other's lips...soon I slipped down, kneeling between Prudence's legs on the floor. I pushed his shaven thighs apart, placing them over the arms of the chair, admiring his erect dickie straining against the sheer materail...

" If you only knew how much I like dressing you up as my little bitch and making your cock hard..." I whispered, stroking it slowly up and down while he moaned with pleasure. I could actually feel his cock stiffen, growing ever harder inside the sheer confines and a drop of pre cum leak from the tip, and dampen his ladies wear !

" Careful baby...you don't want to make a mess in your new delicates when you haven't even paid for them yet ! " I mocked knowing from experience that Drew was getting close to the edge...it was already beginning to throb !

" Don't you dare cum without my permission baby ! " I advised him and took it one step further by using my tongue to softly lick the length of his entire shaft, pausing to flicker the very sensitive membrane underneath the tip...driving him crazy ! " If you do make a mess in your panty I may have to punish you ! " I warned him, wondering how much longer my boyfriend could hold out...

 

[JDrew]

“Careful baby...you don't want to make a mess in your new delicates…”

I squirmed. My legs began to shake involuntarily as Angelique licked my dickie.

She was right but I wasn’t sure I was going to be able to stop myself. Our shopping trip was off to a great start. I was having a ball and was horny as hell. Did she truly expect that I’d be able to hold off?

“If you do make a mess in your panty I may have to punish you !”

As I was last night, I was confronted with the decision to allow myself to cum or face whatever consequences Angelique had in mind. We were in a store that sold adult toys, who knows what she might add to our bag before we left. She might even decide to punish me right here, before leaving.

My face flushed red with the thought of being punished baby Angelique in front of Gina.

My new panties were now soaked with pre cum and I knew that I’d have to pay for this pair and probably buy a duplicate too. These were about to get ruined.

Angelique continued to lightly caress my cock with her finger tips—slowly sliding up and down my shaft. Then circling the swollen head lightly with her nails.

I could feel the pressure building inside me. I knew I was about spurt warm cum in my panties. Still I desperately tried to hold on. With my legs practically vibrating and quiet, deep moans escaping my lips I finally released.

My cum oozed through the sheer, porous fabric of the lace panties. My body relaxed and I closed my eyes. Before opening them I took a breath, imagining Angelique’s disappointed expression at not being able to control myself. But when I finally looked at her she seemed pleased with herself. And she had a diabolical smile.

 

[angelique127]

Drew or should I refer to him as Prudence, always had very little control of himself. I had the talent to make him cum in a heartbeat whenever I wanted too. It had never been an issue until now... however since he had just gotten in touch with his feminine side I decided to do something about it. It was the perfect time to take our little game to the next level...

" Oh baby what am I going to do with you ? It is not very considerate...how about if I wanted you to stay hard for me so I could sit on your lap and have you put your dickie in my wet pussy ? Now it's so soft and useless..."

" Angel I can get it up again if ..." Drew insisted.

" Shissssh" I silenced him, putting my finger against his lips. " You had your chance, I told you not to cum darling ! Now I'm going to have to punish you ! "

" Please give me another chance ! " Drew begged.

" I'm sorry it's too late. From now on your going to have to earn your orgasms. And learn that mine always cums first. "

Drew started to protest but I silenced him with a kiss, using my tongue to explore his mouth. I knew he could recover quickly and get hard again but I was determined to teach him a lesson.

" Lets go see Gina and measure you for your new present ! " I said taking him by the hand.

Gina was delighted and happy when we approached the counter. " First I want to offer you both a free gift for your performance. Those guys left me a big tip besides buying several expensive items ! So whatever you want is on the house ! "

" Why thank you ! It seems that dear Prudence has had a little 'accident' in his panties and we will have to buy them but I am interested in a chasity device to prevent further messes. " I said giving her a wink...

" Oh you must mean one of our cock cages...I have two types in stock for the bad boy, plastic or metal whatever you prefer. "

" What do you recommend ? " I asked.

" Well I think the metal one is better but it's really all about the size and how it fits if you know what I mean. " Gina confided.

" Of course, well then let's try on a few metal ones ! "

Gina picked out several cages from the glass case for Prudence to try on. " Oh and I have some really nice gold chains for you to hang the key on if you like. You wouldn't believe how fast they are selling out these days...oh and those strap ons are a hot item too ! "

Now a strap on was one toy I didn't have in my arsensal, it might come in handy one day in the future I thought as I admired several...

 

[angelique127]

cute outfits for my panty boy

Isn't she/he so pretty ?

 

[JDrew]

You're teasing me!!! Would be so happy to model them for you. : )

 

[JDrew]

They talked like I wasn’t there. Or maybe like I was a doll or play thing. No opinion that mattered.

Gina pulled out several cock cages while Angelique wandered over to the strap ons. I saw her eyeing a few long, thick rubber cocks. Realistic and veiny. I wondered ow that would feel. First pressing against my tight hole and then finally penetrating me. I shuttered.

Gina noticed me twitch and must have thought I was having second thoughts. “It won’t hurt, you know,” She said. I wasn’t sure if she meant the cock cage or dildo. “Once you’re fitted with one the right size it won’t be too bad.”

She held up a cage. Stainless steel, slightly curved.

“Let’s try this one. I think it’ll be perfect.”

Gina grabbed a latex glove from the counter, slipped it on and then cupped my balls and soft cock. She placed the cage over my dickie, fastened it and locked it in place with a tiny skeleton key.

“Walk around for me,” she commanded.

I glanced around the store once again really hoping no one would come in again. I wanted to get this over with and get dressed.

I walked up and down the aisle. The cage felt awkward but stayed in place.

“That looks good,” said Angelique, now standing next to Gina, a strap-on in each hand.

“Yeah, I think that’ll work,” Gina said, looking at Angelique. “Pick out a chain.”

Angelique placed the toys on the counter next to my sexy garments and boxes of shoes. She turned to the glass case and browsed the chains. “That one,” she pointed to a short, thin gold chain. An anklet. On end was a heart, the other end a loop to fasten the key to.

“Oh, nice one,” said Gina. “The key slides through the heart, holds it in place.”

Gina retrieved the anklet, bent down and fastened it to Angeliques leg with the key.

“Get dressed now, honey,” Angelique said. “We have more places to go!”

I went back to the dressing room and got myself dressed back into my original outfit.

 

[angelique127]

I was delighted with all of our purchases and gifts. Prudence has a whole new collection of her own feminine panties and lingerie to wear everyday, as well as a brand new cock cage. I just adored my ankle bracelet that held the key and couldn't wait to show it off in public and close friends.

" My God I am just famished, how about we stop at Maxwell's and have a little lunch ? " I suggested. Prudence nodded, seeming to be content being dressed as a girl, despite the new gift that she was wearing under her skirt. I knew that it would be uncomfortable at first until she got used to it, but I did not intend to make her wear it all the time. The cage was more or less a bargining chip, used for control, and make her agree to my demands.

We pulled into the parking lot and entered the restaurant. Prudence was still getting used to walking in her high heels and stumbled once or twice before the hostess seated us at our table... " The waitress should be with you ladies shortly. Enjoy your lunch. "

I smiled with satisfaction while studying the menu. Drew passed for the perfect girl and managed to fool most everyone. I was so proud !

While we waited for the waitress to come take our order I decided to confide in her. " Baby if I tell you something do you promise not to get mad ? "

Prudence blinked his long eyelashes several times and shook his head. " I promise Angel. "

" Well that aggressive guy in the tank top at the boutique gave me his phone number and asked me to call him if I ever wanted to go out with a real man. You know that I don't like those macho types but he was kind of cute ! "

 

[JDrew]

I squirmed in the thick pleather booth acutely aware of my cock cage pinching my balls. I shifted my weight from one butt cheek to the other, crossed my legs—left over right and then right over left. Nothing quite made the uncomfortableness of the cage diminish and now, on top of that, the realization smacking me in the face, once again, that I wasn’t a “real” man.

And again I had to ask myself … what the fuck did I expect to happen? I was no longer the same person I was when I woke up yesterday. The past 24 hours had changed me permanently. Had changed me all the way to my DNA. I was a girl now. Maybe not physically (at least not yet) but mentally and emotionally I was now Angelique’s sissy boyfriend — Prudence.

I sat quiet for a few seconds letting it all sink in: the erotic dance in the boutique, my new clothes … my new role.

Did Angelique want my approval to call this guy? And considering the situation, wasn’t it my duty to encourage her?

“Really?” I sipped some water and noticed the smudge of lipstick I left on the edge of the glass. A little voice in my head screamed out at me: “Men don’t leave lipstick on glassware. Only women do that.” Just another small piece of evidence that Drew was long gone, replaced by a would be girly girl.

“Yea, he was kinda cute, I guess,” I said. “So, you want to give him a call?”

As the words left my lipstick coated lips I found myself not just curious if she would do it but almost hoping that she would. That strange feeling of erotic curiosity, the same feeling from the night before, washed over me.

And now with more enthusiasm, “I bet he had a huge dick,” I said with a light giggle. “You know if I’m going to be a girl … should I learn how to suck a dick for real? I mean not just in a teasing way? Would that make you happy?”

 

[angelique127]

" I bet he had a huge dick...you know if I'm going to be a girl, should I learn to suck dick for real ? I mean not just in a teasing way ? Would that make you happy ? "

" Oh no baby, that's not what I meant...I could care less how big his cock really is ! Besides you know I don't like those arrogant dominant kind of guys who think they are God's gift to women ! " I lied.

Just then the waitress came to take our order. I pretended to to be engrossed in the menu, thankful that I had a moment to think things over. Of course I adored my boyfriend who I had managed to turn into my girlfriend overnight and help him get in touch with his feminine side. Drew was a very sensitive and considerate guy and we were having fun playing dress up but I didn't know how far this whole thing was going to go...was Drew actually considering being with another man ? Did this mean a threesome was in our future ?

Prudence placed his order after asking the poor waitress a thousand questions, while role playing the perfect female, twirling her polished finger in her hair and fluttering her long eyelashes. I wasn't sure if the waitress knew that Prudence was really a male or not. I placed my order next ordering a chef salad with a side of ranch and a salty margarita. After she departed I took his hand in my mine...

" How did I get so lucky when I met you, baby ? You are so special...patient, kind, gentle, considerate... I think we should wait a little while before we rush into anything. Besides you can look like a female overnight but you really can't become one that fast. Do you know what I mean baby ? "

Prudence nodded, staring into my eyes...

" Besides I just purchased those new toys that I'm dying to use on you tonight !"
You know that little butt plug I bought, we'll start out with the smallest and let you get use to walking around the house without it falling out until you are ready to graduate to the bigger size ! By then you should be prepared and trained enough for my strap on that I have been just dying to use on you ! " I promised..." In fact after lunch I'm ready to just go home and get comfortable. Maybe get into our lingerie and watch an adult movie and be playful...although you do understand that you have a whole week of punishment imposed on you for cumming without permission ! Unless you can convince me otherwise ! "

 

[JDrew]

“…I think we should wait a little while before we rush into anything. Besides you can look like a female overnight but you really can't become one that fast. Do you know what I mean baby ?”

“You’re right … I mean, of course you’re right,” I said maybe somewhat reluctantly. My excitement about being a girl, being out dressed so feminine, got the better of me. And really I had a sense of … relief? Was that what I felt? I wasn’t sure how far Angelique was willing to take this and just when I resigned myself to the idea that she was in charge and it might mean watching her with another guy or I, myself, being with another guy, she downplayed the idea. Thankfully, I thought. I’m not sure I’m ready for that anyway. Toys first.

The prospect of a butt plug and a strap-on was exhilarating. It was all so new and exciting. I knew that we’d have fun.

“...although you do understand that you have a whole week of punishment imposed on you for cumming without permission ! Unless you can convince me otherwise !”

“Yeah, I know.” I said. “You’re going to have to give me a little bit of a break. I mean the whole thing was so crazy and I got so turned on. You know … watching you. You always look so hot but moving around in that lingerie … Damn, Angelique. You looked absolutely amazing. And then me being dressed too. Ugh, it was too much. Couldn’t help it.”

I squeezed Angelique’s hands. “I wan’t to do whatever makes you happy,” I paused. “But I am enjoying this … role? In fact, before we go home, I’d like to stop and get my ears pierced. Just another hour of girl time and then we can go home and play?”

I felt like a teen bargaining to stay up an extra hour to watch TV or talk to a friend on the phone. The truth was that I could spend the entire day shopping, being girly. It was like a dream, like living in scenes from from another life. I felt like I was meant to be this girl I was becoming.

I knew that it wasn’t practical to think I could live my life as Prudence. Not everyday all day. Family obligations, friends, work—at some point I’d have to be Drew. But at home, just the two of us, I wasn’t sure that I’d ever be Drew again.

The waitress returned with our margaritas. We toasted, “To becoming someone new,” I said.

“Cheers,” we both sang at the same time. Our glasses touched and we both a drink of the sweet and salty beverage.

 

[angelique127]

After lunch we visited my favorite beauty salon. Adele was the only woman I trusted to style my hair. Certainly Prudence was in good hands...we decided to do a complete makeover while there. Fake eyelashes, eyeshadow, plucked eyebrows, a new shade of lipstick to chose from. Since we were having her ears pierced we decided on a pair of diamond studs to start with, along with a pair of dangling pearls earrings { birthstone } and a matching necklace.

Adele showed us several wigs in different shades. While Prudence looked good as a blonde, I rather preferred her as a redhead or brunette now and then. So we decided to get both, that way she would have a wig in each color until her natural hair grew long enough to go out in publc. I was so excited how pretty she looked I took several photos on my cell of her posing. In one of the shots I insisted that she lift the hem of her little skirt and show her caged pantied cock. Adele also took a few of us together of Prudence wearing her new wig after her professional makeover ! We all giggled like schoolgirls !

Since we were having so much fun I decided that we might as well stop at my favorite shoe store and buy Prudence a couple of pair of heels and slippers in her proper size. I just loved how the young guys just all competed to wait on me when I entered the store. Maybe it was because I always wore very short skirts and gave a glimpse of my panties to whoever knelt at my feet and helped me try on countless pair of heels...

 

[JDrew]

I was feeling pampered and more feminine than I could have imagined. I was loving every second. Angelique introduced me to her hair stylist, Adele, and she immediately fawned over me. “Oh my God,” she screamed. “You look so good! But! I can make you look even better.”

She listened to me. What I liked and what “look” I wanted. She worked on my eyes and showed me which colors worked best with my skin tones. Angelique also made suggestions. Between the two I was in remarkable hands. I knew that I’d look damn good. By the time we left the salon I forgot all about Drew.

The shoe store was just as fun as I had imagined it would be. I tried on virtually every shoe they had. Heels, sandals, wedges, open toe, closed toe, boots with zippers and criss-crossed laces—I tried them all. Angelique did as well.

We sat as the young men in the store raced around brining us every option we asked for.

“Honey,” I said to Angelique “We are going to need a U-Haul to get all of these shoes home.”

I meant it. I was building a tower of boxes next to me and I wanted every single pair, including a pair of Jimmy Choo’s that were over eight-hundred dollars.

“You’re kidding, right?” Angelique asked me.

“Nope. I’m going to buy them. I have plenty of money saved and I haven’t treated myself to anything in a long time. I would break my heart to leave without them.”

I noticed the salesmen kneeling for a long time between Angelique’s legs. Slowly helping her in and out of each pair she tried on. She gave me a wink as she inched the hem of skirt a little higher on her thigh.

Over two-thousand dollars later we left the store. We each toted two large bags to the car.

“I know this has been one expensive day but … I really can’t thank you enough for it. I mean I really loved it. Every second. I love spending time with you anyway but this was special. I …I hope you feel the same.” I hugged Angelique, holding her close, almost in tears.
When I finally regained my composure I said: “So, I know you suggested going home to try those toys but now that I’m all made up, want to try one more stop? You did say something about that strip club…”

 

[angelique127]

Apparently dear Prudence wasn't ready to go home yet or so it seemed. Who was I to disagree.

She did look hot, all dolled up and ready to play ! I just hoped we were not flirting with danger...

Now was not the time to tell Prudence that I used to be an exotic dancer. Did it really matter ? I didn't think so...

" Why if you really want to go then I think we should ! It will be so much fun ! "

" Really ? " Prudence exclaimed, seeming overly exited.

" Yes baby doll, as a matter of fact I think they are having a beauty contest tonight that we can enter. The winner gets a thousand dollars ! "

Within an hour or so we were both looking pretty and sitting at Pandoras Box waiting for the show to begin hoping to win the prize...