Feminized Pretty Boy

[angelique127]

Why only yesterday Drew was my masculine live in boyfriend and lover and tonight he was a willing sissy named Prudence sucking another mans cock like a submissive little feminized bitch ! And Ryan seemed to be enjoying every moment of it !

" I like the way your boyfriend is getting my big cock hard and ready to fuck your hot pussy ! " Ryan sneered, taking my nipple in his mouth...

When I had invited the stud home for a drink I did not dream that it would go this far...I had never been unfaithful before but this was different and happening before Drew's very eyes and he seemed powerless to prevent it. Ryan was definately a alpha male and was going to dominate both of us !

Not to mention my pussy was dripping in anticipation, and I wanted that huge hard cock in my cunt ! Unable to wait any longer I straddled his hips and mounted him...for a moment I paused, feeling his rigid member press against my delicate slick pink folds before entering me ...

" Oh my God....you are so much bigger than my boyfriend ! " I cried...Please Prudence take off my panties and show your appreciation and lick both of us from behind ! "

 

[JDrew]

I did as I was told. Ryan sat back on the couch, his legs spread wide. Angelique straddled him, taking his thick cock inside of her. I heard her gasp and moan as he slid deep into her.

It would have been easy to feel completely emasculated but I was surprisingly happy for her. I wanted her to feel Ryan’s huge dick pulsating inside of her. It was like a little gift.

I inched up to the couch on my knees until my nose was nearly rubbing against Angelique’s ass. I could smell the sex building between them. I titled my head and stuck out my tongue. Angelique must have felt me behind her and she collapsed on Ryan’s chest, during her head in his neck.

With her body in that position I could see Ryan’s glistening rod thrusting into my girlfriend. His balls were large and loose, bouncing with each forceful movement of his hips. I inched closed, my tongue curled around his sack, and I took in my mouth. I sucked lightly, like I was tasting a delicate candy. Above me, Ryan growled. “Yeah, that’s it sissy girl.”

I pulled on his balls with my lips and I bounced them on my tongue. Angelique continued to bounce on his cock. I felt her ass against the side of my face every time she slid down.

After a few minutes I shifted my attention to Angelique’s ass. My tongue, thick with the familiar taste of Angelique’s wetness, now coating Ryan’s balls, found her tight brown hole.

She lifted up, off my tongue and then back down. I got her wet before deciding to back away and finger her ass ever so lightly with one finger.

 

[angelique127]

0h god it felt soooo good to have my boyfriends tongue tickle my anus while the well hung stud fucked my pussy ! Ryan had taken total control of our household for the time being and was dominating both of us. Ryan's dick was so much bigger and better than Drew's was and I loved every thrust inside my hot pussy ! Never did I think that another man beside my boyfriend would be taking advantage of me right in front of him....

It had happened almost overnight, Drew had been turned into a my sissy ! From now on he/she would be my little submissive willing handmaiden, treating me as a goddess and princess !

It didn't take long before I creamed all over Ryan's magnificent big cock ! Nothing had ever felt so fucking good !!!!! I whimpered in pleasure never wanting this evening to end !

 

[JDrew]

Angelique’s voice was building, getting louder, higher pitched. She sounded animalistic. I knew she was about to cum but I’d never heard her sound that way before. It was terrifying and exhilarating at the same time. I don’t think she’d ever been that loud with me. I wondered if the neighbors could hear her and wondered what they’d be thinking. Call the cops? Or, what a lucky girl she must be.

She came hard on Ryan’s dick. I knew what he must feeling at that moment—a sense of accomplishment, proud that she came for him.

If it were me, I’d stop. Pull out. Give her a second or two to catch her breath. Kiss her chest. Feel her body go limp under mine. But Ryan never pulled out—he quickened his pace, forcing himself into Angelique hard, making deep grunting noises with each thrust. She responded with hoarse whimpers of her own.

I slid away from them. Watching. Listening to their primal sounds. Skin slapping against skin, their primal call and response. I reached to my cock and stroked slowly, transfixed on the scene in front of me.

Ryan repositioned Angelique on the couch, folding her into what looked like an impossible and uncomfortable position. She responded by throwing her legs around his hips, letting him push into her as hard as he wanted.

Finally, Ryan’s body spasmed, tensed, the muscles in his back and shoulders squeezed together in a tight knot and then he released with a wild groan. He never pulled out. He ejaculated as hard as he could into my girlfriend and she eagerly accepted.

I leaned against the couch and stared like I was watching internet porn in my living room. My cock was hard and I was pleasuring myself but without much enthusiasm. I was a tangle of emotions wondering what would come next.

 

[angelique127]

I had lost count how many times our guest had made me gush all over his big magnificent cock...I loved the way he manhandled and dominated me unlike my own boyfriend could ever manage ! Ryan simply made me feel like a total female ! Spent and feeling content I relaxed in his arms..." Oh my God that was unbelievable ! I never had so many orgasms in my entire life ! "

Ryan smiled, holding me in his powerful arms. " You are amazing baby ! I coild fuck your hot tight pussy all night ! "

" Mmmmm yes the night is not over yet ! " I murmered, stroking his broad, manly chest.

" Well I'm dying of thirst, while don't you have your panty boy fix us a drink before we continue ? " Ryan said.

Suddenly I remembered Prudence was sitting there watching us. She looked sort of sad and forgotten...

" Oh baby why don't you be a good boy and fix all of us a drink ? " I suggested.

Does she make breakfast and serve it in bed in the morning ? " Ryan inquired, raising an eyebrow.

" She is an excellant cook ! Prudence makes omelttes to die for and she will if I ask her, won't you baby ? " I offered...

 

[JDrew]

“Of course, Sweetie,” I said. “Whatever you want.” I tried not to sound dejected or sarcastic and headed to the kitchen. As I passed a mirror in the hallway I caught sight of my face. My make up was smeared, raccoon eyes and I had more lipstick around my mouth than on my lips. Most likely from sucking on Ryan’s cock, I surmised.

I felt an urge to fix myself and spend a few minutes alone. I took a detour and dashed up the stairs to our bedroom. Our bed was welcoming and soft as I laid down, breathing deeply. What a turn of events, I thought. When I woke up this morning, as we dressed, I would never have imagined the night ending with another guy fucking my girlfriend only inches from my face. And then me making them drinks to quench their lust fulled thirst.

I began to wonder, what is the job of a sissy anyway? What was I expected to do now?
Downstairs I heard laughter and Angelique squealed with delight. Did I want to know what was happening? Maybe it didn’t matter, they wouldn’t miss me for a few more minutes. I went down the hall to the spare room and sat in front of my computer.

What does a sissy do? I typed in the search bar. I was overwhelmed with the number of responses. There were sissy chat rooms, web sites and support groups. There was sissy fiction, blogs and photo sites. Did Angelique know about all of this? Was she preparing me for this all weekend? Longer?

She found me dressing in her things, I reminded myself. That’s on me.

Wikipedia: the practice of dressing a submissive partner as a woman and encouraging or training a submissive partner to act in a feminine or exaggeratedly feminine (hyperfeminine) manner.

That about sums it up, I thought.

Another article I found was titled: Is ‘Sissy’ A New Sexual Orientation? I saved it to read later. It was too much to take in now.

I stood and staggered away from the computer back to the bedroom. I didn’t have time to research now but knew I’d have to spend some time later and figure out where this was all going.

In the meantime I decided to fix myself. I scrubbed my face and examined Angelique’s makeup still on the bathroom vanity. I tried to contour my face and I did my eyes and my lips. Ten minutes later I stood back apprising my look. Not too bad, I thought. Not for my first time unsupervised. At least better than the horror show clown I looked like when I came upstairs.

Next I decided to find some new clothes. I rooted through Angelique’s drawers and found a pink and cream silky nighty. I didn’t remember her ever wearing it but then again she had so much lingerie it wasn’t surprising. I dropped it over my head and ran my fingers through my hair. I slipped on a fresh pair of thigh high stockings and panties and headed back down stairs.

I found my packages from our day of shopping and decided to try one of my new pair of heels. Four inch sandals with a thick pink satin ribbon that wound its way over my foot and tied around the ankle. I struggled with them at first but once they were on I carefully made my way to the kitchen.

I felt refreshed and ready for a drink myself. I mixed three bourbon lemonades, put them on a silver tray and, with as much confidence as I could, walked back into the living where Angelique and Ryan waited.

“I have drinks for you both,” I announced with best demure smile I could muster…

 

[JDrew]

At your service ...

 

[angelique127]

" I have drinks for you both. " Prudence offered...

I stirred in my new lovers arms where I had been relaxing so contently in my afterglow and I heard Ryan ask..." What in the hell took you so long ? "

Sensing our guests dissatisfaction I hoped to smooth things over as I kissed Ryan's neck " Don't worry about him darling, I mean her, she just propably wanted to go use the potty and freshen up first. "

" Maybe I should give the little bitch boy a spanking ? " Ryan smirked, taking a sip from his drink.

" Oh baby don't be so mean to her, she only means well ! It will take a little time for her to get used to her new role around the house. " I said feeling like I needed to defend my boyfriend.

" Oh yeah, right, I almost forgot the little sissy couldn't even hurt a fly. " Ryan mocked, playing the role of the dominant alpha male.

" Please Ryan, sir, don't make fun of my little ol' boyfriend ! " I pleaded with our guest.

" Don't worry I won't hurt your boyfriend darling ! " Ryan promised, while kissing me on the lips...

" Oh Prudence would you mind sleeping in the guest room tonight ? " I asked innocently...

" And don't forget to serve us breakfast in bed in the morning panty boy ! " Ryan warned, slapping me on my derriere as we went up the steps to my bedroom.

I couldn't help but squeal with delight as Ryan followed me up the stairs...

 

[JDrew]

Ryan changed. Now that he had Angelique wrapped in his firm arms, he had no use for me. He didn’t seem to care that earlier that night I had pleasured him with my lips and my tongue. I was now an after thought. Angelique defended me and I loved her for it. I was doing all of this for her. (Just for her? I asked myself) I knew she wanted this night, I could she the desire in her eyes for Ryan. Her body was open to him—every inch, every crevice, every nook and cranny—she was going to let him use her in whatever way he wanted. He had a an all access pass.

“Oh Prudence would you mind sleeping in the guest room tonight ?” Angelique asked.

I froze but accepted her request with a slight nod.

And then, with a smack on Angelique’s ass they disappeared up the stairs. I heard the bedroom door—my bedroom door—slam shut and I was alone. I began to straighten up the downstairs. I gathered and folded clothes that had been tossed aside in the excitement of the evening. I collected the empty glasses and brought them back to the kitchen, stumbling slightly in the four-inch heels. This was going to take a lot of practice, I thought. Yes, the heels but also getting used to my role as sissy house maid to my girlfriend and her male guests.

I washed the glasses, put them away, and continued to tidy up the house. I checked the fridge to make sure we had enough eggs and veggies for omelettes. I made sure we had bread for toast, butter, juice—it was all there.

There was a loud crash upstairs like something fell over and I almost ran (as fast as I could in heels) up the stairs to see what happened but then heard rounds of laughter and figured everything was alright. Or at least no one was seriously hurt.

Finally, I locked the front door, turned off lights and managed the stairs (slowly - one at a time) and went to the guest room.

The bed was hard—not the soft pillow top mattress Angelique and Ryan were enjoying. I laid on top of the covers—a thin duvet and sheet—and listened to the noises coming from down the hall. Ryan was panting loudly, Angelique screamed out periodically, calling his name in short, breathless cries.

My cock was getting hard and I began touching myself. I imagined the scene on my bed: Ryan spinning Angelique in every direction shoving his massive dick in her mouth, her pussy and her ass. I stroked faster and harder. For me it was a night of sexual repression. I had pleasured Ryan, he had (and was) screwing Angelique into oblivion but I had not come. More noises from down the hall and I found myself on the verge of exploding. I yanked the nightie up to my chest just as I released a stream of thick white cum over my stomach.

With that release, I sank into the bed. It had been a long day, I was tired and before I could clean myself up, I was asleep.

 

[angelique127]

Oh God it was one of the most wonderful nights in my entire life ! Ryan was a total well hung stud who made me cum all over his big beautiful cock so many times I lost count ! He was simply amazing ! I wasn't used to to feeling like a toal female and being manhandled in such a way !

We woke up in each others arms, having slept late. It wasn't long before my new found stud was hard again and eased me on top of him and began to fuck me. Once more I rode that magnificent dick until he made me gush all over it every last inch of his massive manhood ! I was simply in heaven !!!

" Didn't you say your panty boy boyfriend was going to make us breakfast in bed ? " Ryan asked, remembering a promise I made last night.

" Oh yes I did say that. I'm sorry I forgot. You distracted me with your nice big cock. "

" Well darling I am famished if you know what I mean. Why don't you get your sissy to make us something to eat. "

" Mmmmm yes I would love an omelette and some fresh fruit. " I said reaching over to ring the belle, which was emblazzened with the word 'BITCH ' Prudence had gotten me for a joke for my birthday. It was coming in handy now...

" I wouldn't mind bisquits and gravy and some bacon if you have it baby ! "

For some reason I didn't tell Ryan that we ate healthy and preffered a vegetarian diet...I wasn't used to having a red meat eatting male around the house...

 

[JDrew]

It was a the slight jingling of a bell that stirred me. I don’t know how long it had been ringing but the sound was getting louder and more frequent.

I laid in bed, waking slowly. As the bell became more insistent I realized that it might be for me. And then I remembered: breakfast.

I rolled off the hard mattress feeling cranky and sore. My back was achy and I had to stretch every which way to loosen up. My stomach was crusty from coming on myself before I fell asleep. I felt disgusting. Still the bell rang.

I tip-toed down the hall and knocked quietly on the door before opening it up a crack. I peeked inside. Angelique and Ryan were tangled in our soft comforter. They looked surprisingly refreshed despite a night of endless sex. Angelique’s hair was twisted around like a bird’s nest on her hair but she still looked sexy.

They gave briefly gave me their breakfast order. Ryan wanted biscuits with gravy and bacon. None of which we had. I looked at Angelique who just shrugged.

“I need to get cleaned up a bit,” I said before closing the door.

Back down the hall I went to the guest bathroom.

I turned on the shower, cranking up the heat and pulled off my nightie. The hot water felt good and helped loosen up my tight muscles. I felt more like myself and once I was dried off I was able to address the idea of breakfast.

First, I needed clothes. All of my clothes were in the bedroom and I had no interest in interrupting the two of them again. Instead I looked through the closet in the spare room. Angelique kept her over flow of clothes hanging in neat rows. I pulled down a long sleeve, loose fitting dress.

Oh … what the hell, I said to myself and laid the dress out on the bed.

I went back into the bathroom and pulled out some of Angelique’s extra make up from beneath the sink.

I did my best to make myself look presentable. My hair was still a mess, my make up looked uneven — highlighted by bright sunlight streaming through the small bathroom window.

I just had to hope that I wouldn’t run into anyone that I knew.

I dashed down the stairs, grabbed the keys and braced myself for facing the world as a femme boy.

Apart from a few odd looks and smirks, the trip was thankfully uneventful.

I raced home and set to work making breakfast. I cooked, poured coffee and even mixed mimosas. Finally, I put everything on a large tray and headed back up the stairs.

I paused and took a deep breath just out side the bedroom door before pushing it open.
“I have food,” I said in a high-pitched, sing-song voice.

 

[angelique127]

" I have food ! " my boyfriend announced in a high pitched voice, entering our bedroom carrying a tray.

" Well its about time sweetheart, what took you so long ? I'm starving. " Ryan said, " It better be worth the wait. "

I hoped for Prudence' sake that it met our guests approval. Ryan was very demanding and dominant. There was no doubt who was in charge here now...

Ryan sitting up in bed tasted his coffee first like sampling a bottle of fine wine in a restaurant. " Not too bad, although I like it stronger next time." Next Ryan took a bite of the bacon. " Hmmm, if we eatting in a dinner or someplace nice I would send it back. I like my bacon more cooked and crispy ! "

" Well if you like I'm sure Prudence wouldn't mind to cook it the way you like ! " I offered.

" Nah it's okay buy next time when I stay over for breakfast she better get it right. "

Ryan continued to critique the breakfast but ate every bite and then wanted seconds. Poor Prudence looked crestfallen having not pleased him...

" Hey panty boy when I come over I think you should make yourself a little more presentable instead of that unflattering dress you are wearing. You would look better dressed as a sissy in a little french maids outfit, don't you think ? " he asked me.

" Why yes if that is what you prefer ! " I agreed. Ryan seemed to be enjoying humilating my poor boyfriend and showing his masculinity...

I thought it best if I dismissed dear Prudence for the time being at least until Ryan left to go to work soon... " Why don't you go do the dishes and clean up the mess in the kitchen darling ! "

Taking the dirty dishes, Prudence rushed from the room, leaving me alone with our guest. I had a feeling Allen was upset after having been replaced by a bigger and stronger man taking over while he was banished to the guest room...

Ryan smirked and took me by the hair, forcing my head downwards, his big cock was hard and needed my attention before he showered and got ready to leave for work...the guy was amazing, a total stud, always ready and willing !

Once Ryan departed for his blue collar job I went downstairs. Prudence was cleaning the kitchen like a good little obediant girl. " Hey baby...I just want to thank you for a wonderful evening ! " I said giving her/him a kiss. " What do you want to do today ? "

 

[JDrew]

I took mental notes—crispy bacon, strong coffee. I wanted to explain to Ryan that I didn’t have a big wardrobe to choose from this morning but decided not say anything just added French Maid outfit to the growing list in my head. I took it all in stride but one thing Ryan said stood out to me: "next time when I stay over for breakfast…”

That implied that this was going to be a regular thing. Was it? I wondered. Something to talk to Angelique about later but for now I had chores.

I cleaned the kitchen from breakfast and straightened up the downstairs. When Ryan left Angelique came into the kitchen. She was glowing, radiant. I don’t think I’d ever seen her with a bigger smile on her face.

In a weird way I knew that I gave her that smile. Or at least helped to create a scenario which allowed her to have that experience. It felt, oddly, like I had given her a wonderful birthday present. I wondered if she would have had the same gleam in her eyes if I had surprised her with a sexy new car complete with a giant red bow on the hood? I think Ryan’s thick, hard gear shift provided her with more pleasure. I was happy for her.

“Hey baby...I just want to thank you for a wonderful evening!” She said, giving me a kiss. “What do you want to do today?”

I turned to her with a smile of my own, “Well first, I want you to tell me how many times he made you cum. And then I want to go upstairs, have my own way with you —the whole thing kind of turned me on.” I said with a shy grin. “Then get dressed, do a little more shopping, sounds like I still need a few new things—namely a French maid outfit—and then I’m open to whatever you want to do.”

I thought back to the previous night and the computer searches I had started doing. “I mean what do sissies do anyway?”

 

[angelique127]

" What do sissies do anyway ? "

Hmmm this was getting complicated I think to myself...but fortunately Prudence was very passive and willing to learn to be a good sissy which was just perfect for our new lifestyle...

" If you really want to know I lost count of how many times Ryan made me cum last night. To be honest he has a nice big wonderful cock that he knows how to use ! " I admitted and gave him a big kss on his cheek like a sister would.

" Lets go upstairs and get ready to go shopping and buy a maids outfit for you to wear around the house. " I smiled and took his hand and led him upstairs to the bedroom he longer had the privilege to share with me. I sat down and crossed my legs in front of my makeup table...

" Why don't you strip out of your clothes for me sweety. " Within seconds he/she was naked except for a pair of panties.

" I am going to explain the rules I want you to obey. First you will always refer to me as 'Mistress' or 'Madam' and answer to only Prudence in public and private. You will always dress as a female from now on and when I entertain company you shall wear your proper maid's uniform. I expect you to perform your daily chores, cooking and cleaning, doing the laundry since I am the sole breadwinner in this household. Do you understand ?"

Prudence nodded, not looking too overjoyed about his new role in the relationship. I had just stripped him of his masculinity but he would get used to being a submissive and obediant 'girl'...

" Futhermore you are not to have an orgasm without my permission. " I stated while reaching out and fondling his little cock through his femenine panty..." if you do have one when I am present or you are alone and I find out you will be punished. " I informed him as I held up the dreaded cock cage as an example for him to see.

Prudence winced at the thought...

I smiled and continued to play with his little dickie. I felt it begin to stir under my skilled touch ! It wouldn't be long before it was fully erect...not that I was very impressed with his size and I knew he did not have much willpower.

Prudence was putty in my hand ! I waited to hear her beg for release...

 

[JDrew]

Angelique sat on the stool in front of her make up table looking up at me with a wicked, almost sinister, smile. Her hands lightly stroked my growing cock.

I was still processing the new rules: can only dress as a woman, have to serve Angelique and her guests, chores, call her Mistress or Madam … can’t have an orgasm without her say so. It was a lot of absorb. She had mentioned some of this before but I guess I wasn’t taking seriously. Looking at her now, she looked serious as fuck.

It looked like I was getting what I wanted even if it wasn’t in the way I exactly expected.

I nodded my understanding and agreement to her …demands? Requests?

Angelique continued to play with my dick and I quickly wanted to cum. I groaned quietly.

I glanced at myself in the make up mirror. I looked dreadful. I needed to shave. I wondered how this was going work.

I moaned as Angelique continued to stroke and massage my stiff cock.

“That feels so good, hon … I mean … Mistress.”

I wanted to cum, spill my load on Angelique’s delicate hands. My knees were beginning to shake.

“Yes …” I stammered.

 

[angelique127]

I sensed panty boy was about to spill his seed. He really didn't have very much willpower or stamina for that matter...

" Don't you dare cum yet ! " I warned, " I want you to make me proud and show some control for once ! "

It was enjoyable to watch him squirm and suffer. Prudence was at my complete mercy. If he an a premature ejaculation then he \she panty bitch would have to be punished and made to wear the cage until further notice. I was his keyholder and he answered to me only.

I was certainly enjoying myself...my former boyfriend was my little submissive bitch now. I had stripped him of his masculinity. And what could be better than to show him off on socail media to my girlfriends. Maybe I would invite Sheila, my best friend forever, over for a drink. I took a picture of her/ him in his panties with my cell phone intending to download it on -----

Prudy was on the edge and his little dickie was actually beginning to throb ! I knew he was close and could not last much longer ! " Remember sweety if you have a little accident in your panty and make a mess I may have to punish you by making you taste your own sperm ! "

 

[JDrew]

I barely heard anything Angelique said. I was alternately grunting and holding my breath trying to not cum. I thought of everything I could to distract myself, mundane things: washing the car, plots of TV shows, sports, chores—nothing worked. Every image that I used to distract myself turned to me in sexy clothes serving Angelique, making her happy, submitting to her.

She continued to stroke my cock. It was pulsing and purple. My whole body was tense, my jaw was clenched tight. I groaned through tightly closed teeth.

There was no way to hold off.

Finally I came. Hard. I released white, warm cum over Anglqiue’s hands and into my panties.

I let out a long breath and my body shivered. I giggled.

“I’m sorry, Mistress. I know you wanted to me to hold out. I … just. I … tried.”

I realized, as my heart rate settled that in her other hand she held her phone.

“Wait … what are doing? You’re not sharing this are you?”

 

[drobert44]

I barely heard anything Angelique said. I was alternately grunting and holding my breath trying to not cum. I thought of everything I could to distract myself, mundane things: washing the car, plots of TV shows, sports, chores—nothing worked. Every image that I used to distract myself turned to me in sexy clothes serving Angelique, making her happy, submitting to her.

She continued to stroke my cock. It was pulsing and purple. My whole body was tense, my jaw was clenched tight. I groaned through tightly closed teeth.

There was no way to hold off.

Finally I came. Hard. I released white, warm cum over Anglqiue’s hands and into my panties.

I let out a long breath and my body shivered. I giggled.

“I’m sorry, Mistress. I know you wanted to me to hold out. I … just. I … tried.”

I realized, as my heart rate settled that in her other hand she held her phone.

“Wait … what are doing? You’re not sharing this are you?”

lmao

 

[angelique127]

" Wait...what are you doing ? You're not sharing this are you ? "

" Relax baby...of course I am sharing this with my friends ! Why wouldn't I ? They are going to love how I made my boyfriend into my little sissy panty boy ! " I bragged, proud to post his fabulous girly makeover on instagram...

Prudess groaned not bother protesting about it.
" Wait...what are you doing ? You're not sharing this are you ? "

" Relax baby...of course I am sharing this with my friends ! Why wouldn't I ? They are going to love how I made my boyfriend into my little sissy panty boy ! " I bragged, proud to post his fabulous girly makeover on instagram...

Prudence groaned but didn't protest.

" I just want to show off your little dickie in your girly panties, baby it looks so cute ! "

I downloaded several photos, inviting any other females who would like to give their husbands or boyfriends a special make over, maybe start a private club of likeminded local females with passive boyfriends who like to dress up as a lady ! I got interested hits almost immediately ! Apparently tradional relationships were changing and so many women, both young and old, were entering into female led relationships lifestyles !

 

[JDrew]

" Wait...what are you doing ? You're not sharing this are you ? "

" Relax baby...of course I am sharing this with my friends ! Why wouldn't I ? They are going to love how I made my boyfriend into my little sissy panty boy ! " I bragged, proud to post his fabulous girly makeover on instagram...

Prudess groaned not bother protesting about it.
" Wait...what are you doing ? You're not sharing this are you ? "

" Relax baby...of course I am sharing this with my friends ! Why wouldn't I ? They are going to love how I made my boyfriend into my little sissy panty boy ! " I bragged, proud to post his fabulous girly makeover on instagram...

Prudence groaned but didn't protest.

" I just want to show off your little dickie in your girly panties, baby it looks so cute ! "

I downloaded several photos, inviting any other females who would like to give their husbands or boyfriends a special make over, maybe start a private club of likeminded local females with passive boyfriends who like to dress up as a lady ! I got interested hits almost immediately ! Apparently tradional relationships were changing and so many women, both young and old, were entering into female led relationships lifestyles !

Who was going to see that post? That was the thought running through my head. Sure, Angelique had friends—lots of friends—and her phone pinged right away. What were they saying? Was I a joke or something of a novelty?

“Okay, what’s going on?” I asked.

Angelique stared at me.

“Mistress. What are they all saying … Mistress? Do they want to come over and have your sissy panty boy wait on them too? Along with your new boyfriend, Ryan?”

A slight smile touched the corners of her mouth as if she were seriously considering it.

“I’m just kidding, of course.” I said. “I’m not ready for that kind of … exposure. You know I’d be a disaster.”

“Oh, I don’t know,” Angelique said.

I shook my head and struggled to get up and clean myself off. I stripped out of my soiled panties and went downstairs to retrieve all my new clothes from the day before. I snatched my packages and returned to the bed room, throwing them on the floor.

“Am I setting up shop in the guest room?” I looked at the small pile of bags. “If this is all I’m going to wearing from here on out I really do need to get more. And obviously I need a French Maid outfit. Or two. Or three. And whatever else you think I’ll need. Probably my own make up, too. If I don’t have access to yours then I’ll need my own.”

I paused and looked at Angelique who was half paying attention to me and half taping on her phone. I continued: “So, we obviously need to shop again today. Yay.”

Angelique was engrossed with an interaction on her device.

“Alright, what’s going on? What is everyone saying?”

 

[JDrew]

Who was going to see that post? That was the thought running through my head. Sure, Angelique had friends—lots of friends—and her phone pinged right away. What were they saying? Was I a joke or something of a novelty?

“Okay, what’s going on?” I asked.

Angelique stared at me.

“Mistress. What are they all saying … Mistress? Do they want to come over and have your sissy panty boy wait on them too? Along with your new boyfriend, Ryan?”

A slight smile touched the corners of her mouth as if she were seriously considering it.

“I’m just kidding, of course.” I said. “I’m not ready for that kind of … exposure. You know I’d be a disaster.”

“Oh, I don’t know,” Angelique said.

I shook my head and struggled to get up and clean myself off. I stripped out of my soiled panties and went downstairs to retrieve all my new clothes from the day before. I snatched my packages and returned to the bed room, throwing them on the floor.

“Am I setting up shop in the guest room?” I looked at the small pile of bags. “If this is all I’m going to wearing from here on out I really do need to get more. And obviously I need a French Maid outfit. Or two. Or three. And whatever else you think I’ll need. Probably my own make up, too. If I don’t have access to yours then I’ll need my own.”

I paused and looked at Angelique who was half paying attention to me and half taping on her phone. I continued: “So, we obviously need to shop again today. Yay.”

Angelique was engrossed with an interaction on her device.

“Alright, what’s going on? What is everyone saying?”

 

[angelique127]

" ...What is everyone saying ? "

I couldn't help but smirk..." All the girls just love the idea of dressing up thier husbands and boyfriends like a female. It could be the lastest trend ! " If I knew be so easy to give him a makeover I would have done this ages ago.

" Diamond just loves it and can't wait to get come over and see ! She has been thinking of converting her hubby and having a female led relationship herself ! " I informed Prudence. She/he was becoming an internet sensation as we spoke. Already our website ' Males to Females' had over a thousand views within minutes.

Prudence looked crestfallen but she had better get used to it. She was famous now thanks to me ! She had mentioned going shopping but I had planned to have company over since it was a nice day to relax beside the pool and barbeque and show off my new sissy maid ! " Yes I agree we need to get you several maid uniforms for you to wear when we have guests over but I think we can order them online on my favorite wbsite for the time being. For today you can wear the one that I wore for halloween last year to serve our guests. "

Prudence nodded folding her hands waiting for further instructions. " Lets go upstairs shall we and get ready...you can help me pick out a skimpy bikini to wear for the days events before dressing up yourself ! "

It was so nice to have a sissy boyfriend to see to all my needs and entertain me and my friends...

 

[JDrew]

We went through drawers and stacked piles of clothes on closet shelves pulling out several bikinis for Angelique. I knew she’d look delicious in each and every one.

Angelique tried on a few, I gave my opinions—which ones I thought gave her the best cleavage or flattered her ass—but just I expected they all looked great on her. She picked the one she liked best and I couldn’t disagree. She grabbed a pair of wedge sandals and a cute straw hat with a floppy, wide brim.

I enjoyed watching and helping her dress. It was thrilling to touch her body as I helped straighten a strap or bent down to help her with her shoes. With each slight touch I felt like a little kid sneaking a piece of candy—like I was doing something forbidden to me—and I relished every second that I got to feel her.

“Your turn,” she said as she marched down the hall to the guest bedroom—my bedroom. “Somewhere in this closet I have last year’s costume.”

She rapidly slid hanger after hanger of old dresses—I recognized a dark blue bridesmaid dress that she wore to a friend’s wedding the previous year, one that I secretly wanted to wear myself—and party clothes, a swish of fabric and blur of color. Finally she landed on the French Maid outfit and hoisted it out of the closet.

Black satin, white lace trim and adorned with small pink bows—I looked at it doubtfully.

“Angeliq … I don’t know if that’s going to fit me, Mistress.”

She smiled at my correction.

“I guess we’ll find out,” she said as she handed it to me. “Take some time in the bathroom. You’ll need to shave your legs and pubic hair. This won’t leave much to the imagination.”

And then she left the room.

I did as she said. I took a hot shower and shaved every inch of myself before drying off and getting dressed. The outfit was snug but the cups were small enough that the material wasn’t sagging and drooping on my chest. The satin skirt was short and I knew that bending over would reveal all. I’d try my best not to reach for anything on the floor.

When I returned to my room a pair of black high heels were on the bed along with black ace thigh high stockings.

I struggled to get everything on and then teetered down the hall to Angelique’s room.

 

[angelique127]

I smiled when Prudence entered my bedroom. He or should I say she looked lovely in her little maids outfit...the change was simply remarkable. My boyfriend made the perfect girl, who would have imagined that only yesterday he was dressed in a suit and tie and today he was transformed into my sissy maid in panties ! I decided to take some more pictures and post them on my website to encourage other females to feminize their own boyfriends or husbands. It was time that males learned their place in a female led relationship that a woman comes first...always !

" Now I would like you to turn around for me and bend at the waist and show off your pantied ass ! " Her dress was so short that the slightest movement exposed her delicates. " Now be a good girl and lift up your skirt from the front ! "

I liked the way dear Prudence did as she was told and obeyed me without protest. She was the perfect example of an obediant little sissy boy. Today she was going to be our entertainment at our party for my girlfriends !

Sitting in my chair { like a goddess } I told him/her to kneel down and help me into a pair of heels. Of course she did this without hesitating..." And while you are down there please polish my shoes with your tongue and show how much you appreciate me ! " I demanded, having fun humiliating her ! It wasn't like I was being cruel but Prudence needed to get used to doing what I wanted...

Just then the doorbell rang announcing the arrival of one of our guests...

" Okay sweetie, someone is here...why don't you please go down and let them in while I finish putting on my make up...oh and don't forget to offer them a drink or a glass of wine ! " I said dismissing my sissy maid to attend to her duties...

 

[JDrew]

I clung to the arm of her chair as I stood. It took me a second to gain my balance and then I nodded, “Of course, Mistress.”

I wobbled from the room, still unsteady in my heels, and made my way into the hall and down the stairs to the front door.

“And who might you be?” Asked one of the two women standing on the door step when I opened the door.

“Prudence.”

They glanced at each other making no attempt to hide the smirks on their faces.

“I’m Tiffani,” said a slim, tall blonde woman in her mid twenties. She was stunningly beautiful with large, round sea green eyes—like an anime character. Looking at her made me feel a little silly, self conscious.

“And I’m Devon,” the other girl said. “We work with Angelique. I think she’s expecting us.”
I stared at her for a moment, instantly jealous of her long, wavy auburn hair.

“She is. Come on in,” I said. “Angelique will be down in a few minutes. In the meantime, can I get you something to drink? A glass of wine? Cocktail? Something non-alcoholic—I’d be happy to brew you a fresh pitcher of iced tea …”

“Oh yes!” Tiffani said as she marched passed me.

“A glass of white for me, Prudence,” Devon called over her shoulder with a giggle as the pair walked into the living room.

In the kitchen I grabbed a chilled bottle of Chardonnay from the fridge and poured two large glasses.

We had a silver serving tray in a cupboard somewhere. I bent down and searched among cutting boards and large platters. I was reminded of just how short my shirt was when a cold rush of air hit my ass. I wondered how many people Angelique had coming over and how awkward this afternoon might be, how often my ass was going to be peeking out from below the hem of my skirt.

I arranged the wine on the tray and slowly made my way to the two women sitting in the other room.

I smiled and politely delivered their beverages, thrilled that I hadn’t tripped and spilled wine all over the furniture or them.

Clearly amused, Devon spoke up: “So, you’re Angelique’s … boyfriend, are you?”

“I’m her … well … her sissy maid,” I said with as much confidence as I could.

“I love it,” Tiffani shouted. She put her wine on an end table. “Come over here, honey.”

I inched closer to her.

Tiffani plucked at my outfit. She lifted my skirt and ran a finger over my silky panties. “You have a small bulge there, don’t you?” She looked at Devon and giggled again. “Turn around, honey.”

I spun awkwardly in my heels. Tiffani grabbed my ass and then slapped me on a plump cheek. “Angelique really has you trained, huh?”

I shrugged. “She’s a woman who knows what she wants and I like making her happy.”

“She’s fucking brilliant,” Devon said with a grin.

The doorbell rang again.

Angelique’s voice wafted down the stairs from the bedroom: “Prudence … more guests.”

As I walked from the room the two woman called after me: “More sway in your hips,” they said. “Back straight, arms loose.”

I took their advice without turning around and went to the door. Just as I swung the door open, revealing another attractive woman, I heard Angelique’s foot steps softly coming down the stairs behind me.