Feminized Pretty Boy

[JDrew]

I looked around wide-eyed and self conscious. Everyone was attractive—women and men—perfectly styled, comfortable in their tight outfits and narrow high heels. All the women were stunning and I was both attracted to them as well as jealous of their naturally feminine bodies—rounded hips, long narrow legs, breasts—jealous at the ease in which they walked and danced in tall pumps and jealous of their casual, relaxed expressions.

I wondered if the men would look my way. Did I look convincing enough to fool them? And how would a tall, handsome man react once he realized that I wasn’t a woman? Would I get a punch in the mouth?

“I don’t know, babe. Maybe this wasn’t a great idea,” I said glancing around the club. “Are you sure you’re okay being here with me like this?” I tugged at my dress and wrapped my arms around myself.

I was moments away from chickening out and suggesting that we leave when a waitress in a black halter top arrived at our table. Her breasts were pressed together in an impressive display of cleavage. I couldn’t help but notice and she caught me staring.

“I just got these about two months ago,” she said. “Love ‘em.” The waitress looked at me, “Are you thinking about it?” she asked.
I realized in that moment how awkward it might be for me to answer in a man’s voice. Should I talk in falsetto, I wondered. Instead I was silent.

“I am so ready for a drink,” Angelique said, jumping in and saving me from answering.

A drink. Normally I’d order a vodka gimlet or maybe just a beer but what would Prudence order? Certainly not that. Something fruity and sweet? I didn’t know Prudence well enough to decide.

I didn’t have to worry for long. Angelique mercifully ordered for us both.

 

[angelique127]

" I must say your breasts are worth every penny ! But may we have two strawberry daiquiri's please. " I ordered for us both not wanting my boyfriends male voice to give him away...truthfully this was an aspect I hadn't thought about ! She looked so nervous like she wished that she was anyplace else but here...wanting to reassure her I moved closer to Prudence and whispered in her ear...

" Don't worry baby, you look perfect...if anyone asks we will just say you are from Russia and that you don't understand english ! I promise when we get home I will give you a big reward for doing this for me ! " my tongue licked his ear and I did not care if anyone watching us considered us to be gay. I was having so much fun...

My fingers slipped beneath her short dress and stroked his panty encased dickie only to tease it ...and to my amazement within seconds he had a stiffy ! I could tell Prudence enjoyed wearing her silky soft delicates for me in public despite appearing somewhat nervous.

Our waitress returned with our drinks. Once again she bent over to serve us and her big creamy white breasts almost spilled out of her top. She seemed so proud of them but Prudence adverted her eyes. Myself, I didn't mind because my own were even bigger and far more firmer...no way the bitch could compete with me in that department !

" If there anything else I can get you all just let me know ! " she offered ignoring me as if I didn't exist but giving her undivided attention to dear Prudence.

After she left I smiled at my boyfriend, " Hmmmm darling maybe you should dress up as a female all the time if you want to pick up women ! She seems to be very attracted to you. "

For some reason my boyfriends dickie was fully erect inside his delicates. Prudence couldn't deny that dressing up as a female was turning him on...just then this guy of arab descent sat down next to us, uninvited of course. He was rather imposing with broad shoulders, kind of handsome in a dangerous way dressed in a very expensive suit.

" Can I buy you ladies a drink ? " he asked, full of confidence.

" Why, thank you but as you can see my friend and I are enjoying one at the moment. "

" Yes, perhaps you would like to dance with me instead. " he insisted.

" Are you asking me or my friend ? " I asked, being somewhat coy.

" I think I would like to dance with you first...and with your friend later. "

Not that I didn't find the offer quite tempting but I found his manner a little arrogant for my taste. Just the way his bold dark eyes were undressing me, lingering on my cleavage as if he wanted to devour every inch of me made me uncomfortable. It was well known that immigrant males from Africa and the middle east were more aggressive if not dominant.

" Well...I do have a boyfriend and I don't think he would appreicate me dancing with another man. " I said.

He snorted and focused his attention on Prudence. " How about you ? Would you like to dance ? "

" I am sorry, sir, my friend is visiting from Russia and she can't speak english very well. " I interceded on her behalf.

I didn't like the way this dark stranger looked at my boyfriend as if measuring her from top to bottom...if he guessed our secret there could be trouble ! I really had no choice to distract him...

" I think I have changed my mind...I would love to dance with you ! "

" By the way my name is Rufus and I am from Algeria. Pleased to meet you ? "

" My name is Angel...welcome to our country ! " I said taking his hand and allowing him to lead me to the dance floor, after winking at my boyfriend...

 

[JDrew]

I watched as Angelique was led to the dance floor. Rufus’ hands roamed over her body—rested on her hips and grazed her ass. She touched him too—placing her hands on his wide chest and pulling his waist forward so that his pelvis was grinding against hers.

I felt emasculated, watching my girlfriend dance with him. Yet, my cock was still hard watching the two of them. And again I found myself jealous. But, was I jealous because she was dancing with someone else? Or, was I jealous that I wasn’t dancing with him?

Lights flashed on the dance floor. One minute bright colors swirling around the couples, the next moment it was dark and then seconds later, bright strobes. I watched as Rufus spun Angelique. In the strobing lights it looked like they moved in slow motion. He puller her close and kissed her before allowing her to spin away again.

I took a sip of my daiquiri. Could I sit her and let another man kiss my girlfriend? How silly would I look if I tried to be an alpha male now, in a dress and heels?

As I decided what to do, a man slid into Angelique’s seat.

“Do you mind?” He asked, gesturing to the seat but clearly not waiting for an answer. “It’s a shame that you are sitting here all alone.”

I waved my hand in indifference—trying to keep my wrists soft in a way that I thought looked feminine.

“Did your friend leave you?” He asked in a deep baritone that matched his rugged, dark face.

The music was loud and I wondered if thump thump thump and deep bass would mask my voice.

“She’s dancing,” I said. I tried speaking through my nose. I’d rather sound nasally than my normal voice. He didn’t seem to care.

“C’mon,” he said. “Let’s go join them.”

He reached across the table and took my hand. As we walked to the dance floor I began to panic. I knew how to dance—had decent rhythm—but could I dance like a girl? Could I dance only a few hours after putting on heels for the first time?

The dark stranger led me right to a spot next to Angelique. He put his arm around me a pulled me close to him. He smelled fresh and earthy, like breathing in a forest. He turned me and I was facing Angelique.

“Help me,” I mouthed to her.

 

[angelique127]

I had to admit that it was rather exciting dancing with such a handsome and masculine man from a different culture, although Rufus was all hands on and touchy feely. He seemed to like my derriere and could not keep his hands off of it while we were dancing under the flashing strobe lights...I had a feeling Prudence was watching us but not daring to protest given the circumstances ! The next thing I knew there was my boyfriend dancing next to us with some dark stud, almost pleading for help ! Truthfully there was not much I could do to help her, dear Prudence would have to help herself ! Once again I couldn't help but feel my dancing partner grind his well endowed package against my ass cheeks. Rufus didn't hold back and with his fingers entangled in my long hair used it to pull my head back in an act of submission. A thrill passed up and down my spine, just thinking about how this handsome hunk could manhandle me later on.

Poor Prudence was on her/his own for the time being and must fend for himself...

Once the song ended { I was beginning to perspire } we walked hand in end back to our table with Prudence and his partner following. Rufus ordered a round of lemon drops and we toasted each other. Prudence then nodded for the ladies room hinting that we should go there immediately !

" Please excuse us gentlemen while we go powder our noses in the ladies room. We will be back in just a little while. " I promised, smiling. We both strutted away torwards the nearby rest room together...

" Are you having fun baby ? I know I am ! That guy you were dancing with is quite attractive don't you think ? I always liked a guy with a sexy five o clock shadow. I asked re applying my lipstick in the mirror...

Prudence didn't respond but just pouted studying her reflection in the mirror...once I finished with applying my lipstick I suddenly turned and caught Prudence by surprise and pinched her lips together only to apply some more hot pink color to her own lips...

" Have I told you how much I adore you babydoll, thank you for doing this for me, I am having so much fun tonight ! " I whispered before I made contact with her slippery soft lips. A thrill and a shiver passed up and down my spine as we kissed passionately, our tongues intermingling and exploring each others mouth...I found it totally exciting to be kissing my boyfriend who was dressed up as a sexy female in a strange restroom...

" Oh my babydoll ...your cock is so hard ! " I observed, my hand going under the hemline of her short dress and stroking it through his sheer pantie, delighted to find that he was as aroused as I was !

I have to admit Drew did have a problem sometimes with premature ejactulation. I did intend to correct that issue with a cock cage and denial in the very near future. " Honey don't you dare cum until I give you permission, no matter what or I will be forced to punish you when we get home." I warned, knowing the silky soft panties were making it almost unbearable !

If it was up to me we could stay in the ladies room for ever how long it took until I made him lose it, which would be only minute or so but our wild weekend was just beginning...

 

[JDrew]

My cock was throbbing as Angelique dragged her long nails along my shaft through the silky soft fabric of my panties. I knew that I had to hold off from allowing myself to release, a situation that could be very embarrassing in the ladies room. Still, I could feel a small wet patch in my silky panties from an uncontrollable bit of pre-cum.

I backed away from Angelique with a sly smile. “I’ll hold off,” I promised.

I looked at myself in the mirror. I really didn’t make for a half bad looking woman. I had panicked while dancing with my rugged stranger that he would realize my secret. Whether he did or not, he didn’t let on.
“I’ll admit, I’m having fun too,” I said. “I like having this little secret between the two of us. It’s so exciting. But you have to promise that you won’t leave me alone for too long. And if I look too … masculine, give me a sign. It’ll be so embarrassing if they find out,” I gestured towards the door indicating our dance partners but really meaning anyone in the club.

Angelique looked at me and adjusted my hair which had loosened a bit from the dancing.

“Perfect! Let’s go back,” she said enthusiastically, visibly excited at seeing Rufus.

“You look gorgeous, by the way,” I said looking in her eyes. “I don’t know how he’s going to keep hands off of you. Or maybe you don’t want him too,” I added with a short laugh.

We returned to the table and took our seat. Rufus’ eyes were locked on Angelique’s chest. Again I had a small wave of jealousy but oddly found it thrilling as well. I found a certain excitement in seeing other men turned on by my girlfriend.

I sat next to my dance partner and crossed my legs. He immediately rested his hand on my thigh under the table. I thought of all the time Angelique I spent prepping for the night, the hot bath, shaved legs and lotion to help make them soft. I hoped my legs were still soft enough that he wouldn’t suspect that I wasn’t what I appeared.

As strange as it felt to have another man caressing my thigh I let him do it.

“What’s your name?” I whispered in his ear, doing my best to sound both feminine and with a broken accent.

“Cherif,” he said loudly with a smile.

 

[angelique127]

As we made our way back to our table from the ladies room, I was somewhat puzzled by my boyfriends reaction to the events playing out so far since his/her makeover. Prudence seemed to like pretending to be a female...I just hoped that the guys didn't discover our little charade and be angry. Truthfully they didn't look like the kind of males you wanted to mess with...

Rufus stood up like a gentlemen to permit me to sit next to him. I had to admit he looked dapper in his formal grey suit and red tie. Actually I was pleased by the way his dark hungary eyes undressed me...Prudence sat next to the other guy who introduced himself as Cherif. They were both from Algiers and recently immigrated to this country we soon discovered. Of course the club catered to men of middle eastern or African descent, hence no white males allowed...unless you considered my former boyfriend who was now dressed up as my girlfriend.

I did my best to make small talk not wanting Prudence to say much, asking questions about if they liked living here in America and such. Rufus smiled and then I felt his hand touch my upper thigh above my stocking top under my short skirt...all I could do was bat my long eyelashes, feeling so strange that my boyfriend was sitting across the table from me but unable to intervene and come to my rescue. I could only take a big gulp of my drink...and did not dare protest. My legs were crossed but that did nothing to prevent his agressive manner. His fingers slid under my silk stocking and lingered for a moment before moving upwards...

I was torn, perhaps we should have just stayed home and played dress up...on the other hand found it quite exciting to be sitting near a very aggressive and dominant handsome man...

" Do you think I could have another drink please ? " I asked Rufus.

" Is that all you would like ? " he asked his intense eyes focused on my full, firm and creamy white breasts !

I could not believe how much this was turning me on ! This guy was making me cream my panties just by the way he was devouring me with his eyes...

 

[JDrew]

Rufus slid closer to Angelique wrapping one arm around her shoulders, his hand hanging lazily between her breast and her arm. An inch or two to the left and he’d be cupping her breast. His other hand was under the table, his arm moving. I imagined Rufus’ hand making it’s way up my girlfriend’s thigh, sliding under her dress searching for the soft silky fabric of her panties.

He leaned into Angelique, his lips by her ear and his eyes looking straight down at her chest. “Is that all you would like?” He said although not quite a question, more of a statement that implied he knew that she wanted more and he was prepared to provide it.

I help my breath waiting for her to answer yet my heart was beating wildly. I was conflicted with emotions. Feelings of jealousy and inferiority mixed with the excitement and uncertainty of the moment. I half hoped that she’d leap up from the table and the two of us would run out together, laughing at the absurdity of the whole experience.

She glanced at me with a small smile that I knew all too well. She was enjoying herself and the attention from Rufus. That look told me all I needed to know—I was in a pink dress, heels and make up — I was Prudence, not Drew. I was her submissive girlfriend and she expected me to act that way.

Angelique batted her eyes and lowered her chin, tilting her head away from Rufus’ lips, exposing her supple neck. He dropped his head and he kissed Angelique just below her ear. I saw her shiver.

At that moment, Cherif’s hands, worked on sliding under my dress. I snapped back to reality: I had to worry about myself. Cherif inched closer to me as well, mirroring Rufus. His aggressiveness took me off-guard. I wondered if it was always like this for women—men pressing into them, taking liberties after only a few minutes of conversation.

The music changed. The thump-thump-thump of pop songs remixed with house music died down and the DJ played a slow song. Before Angelique could disappear with Rufus I jumped up from the table and reached out for her. “Dance,” I said in breathy falsetto.
She unfolded herself from Rufus and took my hand as we made our way to the dance floor.

“I don’t know what to do,” I exclaimed. “He’s all over me. Should I try and ditch him?” I smiled and looked back at the guys sitting at the table watching us, trying my best to look coy.

And then I had to know: “Are you going to hook-up with Rufus?”

 

[angelique127]

As we made our way to the dance floor I could tell my boyfriend who was dressed up as a female was a little corncerned and nervous to say the least that our secret was going to be discovered...I had to admit I was enjoying the attention I was getting from Rufus, who was a hunk, if not rather aggressive and I was starting to get a little tipsy !

" I don't know what to do, he's all over me, should I try and ditch him ? " Prudy looked sort of panicked but did her best to hide it with a false smile.

Perhaps I had a mistake suggesting that we come to to such a club for his/her first time. The mostly muslim males were known to have a reputation for being very bold and aggressive, used to getting what they want in their home country where men ruled.

" Are you going to hook up with Rufus ? " Prudy asked suddenly taking me by surprise. Had I really been that transparent and obvious ?

" Of course not baby why would you even think something like that ? He is very good looking but so are you tonight ! " I teased, making him blush. Drew wasn't usually the jealous type, and tonight he was at a disadvantage...and he did seem a bit worried about our dire situation.There was no telling how these guys would react if they found out Prudence was really a Drew !

" Don't worry darling, I will take care of this...I am used to handling guys ! " I promised, full of confidence. " Just let me show you how you handle a man ! "

We stopped dancing and I pretended to answer my cellphone...

" Yes, this is Angel... " I said although I knew Rufus and his friend could not hear me over the music. I engaged in a fake conversation with someone for a few moments, appearing to be upset at what I was being told. Soon I pretended to disconnect and we made our way back to the table where our new friends waited.

" I'm so sorry guys but we have an emergency, my sister was in an accident and is in the hospital so we have to go see if she is okay ! " I lied, feeling a little guilty.

" I am sorry to hear this...we were just getting to know each other. Perhaps I can get your phone number for in the future ? " Rufus stood up and asked in his sexy mideastern accent.

For a moment I considered giving him a fake phone number, but for some reason I decided to give him my real one. There was something about him I found very attractive and sexy.

We said our goodbyes and they looked dissappointed buy I had to get Prudence out of there before something bad happened or we caused a scene. Once outside in the parking lot we giggled from the excitement of it all. Drew had suceeded
to pass himself off as a female, thanks to my expertise. I suggested that he drive since I was feeling intoxicated...

" Oh baby wasn't that fun ? You fooled everyone except the bouncer ! Just think we have the whole weekend to play together ! I think tomorrow we should have your ears pierced and go shopping for lingerie for you to wear around the house. " I suggested slipping my fingers under his short dress and stroking his cock. It didn't take long for him to get erect inside his silky panty !

" I can't wait until we get home ! " I whispered seductively in his ear...I didn't mention that that encounter with Rufus had gotten me all hot and bothered, so much that I creamed my panties...

 

[JDrew]

Angelique looked mesmerizingly seductive in the moon light. The pale blue light glowed on her chest emphasizing her beautiful breasts. Without thinking about it I wrapped my arm around her waist and leaned close to kiss her. She tasted sweet from the alcohol and I pushed my tongue into her mouth.

It didn’t occur to me that someone else might see us and what they might think until a couple of young guys walked by and hooted at us. To them, clearly we looked like two female lovers kissing by the car—the stuff of young men’s dreams.

The cheering made me laugh and we ended the kiss. If I had real tits I would have flashed them for fun before diving in the car.

When I climbed behind the wheel I realized that I would never be able to drive in heels. “How the hell do you do this?” I asked Angelique with a giggle. After a minute I managed to get the heels off of my feet and tossed them in the back seat.

As we drove I asked, “You really want to take me shopping for lingerie? … for me?” I was a little surprised and very excited. The whole idea of have a girls day made me giddy. “Ears pierced too?” I already started thinking about a pair of silver hoop earrings. “And you’re okay with me wearing it around the house? Like everyday … You’re sure?”

 

[angelique127]

" And you're okay with me wearing it around the house ? Like everyday...you're sure ? " Prudence asked.

" Of course why wouldn't I ? I am so excited that we are doing this together ! As I said we are going to replace your manly underwear with silky soft panties for you to wear everyday ! And on the weekends we can play dress up, I know you love that little french maids outfit I have in my closet, it would fit you perfectly I think and you would look so adorable in it ! "

My boyfriend also known as Prudence seemed to really like the idea and nodded eagerly. What he didn't know was that after tonight he belonged to me and he was about to become my little obediant bitch. Everyday he would do his daily chores, like handwashing our panties and doing the laundry. From now on she would do the dishes and prepare our meals including breakfast served in bed on the weekends. He /she would vacuum and dust and clean the house. I planned to teach him how to give me manicures and pedicures on a weekly basis as well as other duties. After wearing heels around the office all day I think I deserved a foot massage before bed...what female didn't like to be pampered and waited on hand and foot ?

Once inside our home we went uptairs to our bedroom.

" Why baby why don't you slip into something more comfortable, like my pink sheer babydoll that you like, until tomorrow when we can purchase one of your own to sleep in ? Oh and don't take off your panties I want you wear them to bed...you need to get used to wearing them all the time. "

Likewise I slipped into a nightgown. I loved to wear lingerie, it made me feel so femenine and sexy...I reclined in our silk sheet covered bed and waited for my lover to emerge. Tonight dear Prudence was going to be groomed and learn to improve his pussy eating skills...from this moment forward my pleasure came first before his, if I decided to even permit him to have an orgasm. It was about denial and we had played this game before so panty boy knew the rules !

Once she came out of the bathroom in her pink nightie I complimented her on how good she looked. Prudence looked rather shy and bashful. Not wanting to waste anymore time I snapped my fingers to get her attention...

" Why don't you get into bed dear and worship my feet ? You know how much I like my toes sucked ! " I smirked...

 

[JDrew]

I slowly approached the bed, climbed across the satin sheets and took one of Angelique’s feet in my hands. I massaged the long muscles of her slender foot looking to Angelique for approval.
She purred and smiled at me as worked on her toes.

I lightly gripped her heel and raised her foot to my lips, lightly kissing the tip of each toe. “You have the cutest toes,” I said playfully popping each toe into my mouth and sucking slowly. Angelique settled back into the comfort of the lush, satin covered pillows with a grin. And then: “Legs,” she reminded me.

I looked down and realized that I had one leg propped up, very manly. I changed my position—sat up on my knees, feet crossed at the ankle, and straightened out the pink nightie.

“You know, I do love this nightie. But, it might take awhile getting used to wearing it to bed.”

I dropped one foot and turned my attention to the other. Angelique’s toes were small and smooth and I massaged her heel as I took each toe in my mouth, one at a time.

“Feel good, baby?” I asked.

I ran my hands up Angelique’s sexy, soft legs. My lips followed—kissing the top of her feet, her ankles and shins. I inched my way to her knees and dragged my pink, girlie nails across her inner thighs.

The light fabric of my babydoll brushed against my nipples as I shifted my weight forward sending tingles through my body. Once again that night I wished that had real breasts—full, creamy breasts for Angelique to play with and suck on.

“Whatelse can I do for you, honey?” I whispered.

 

[angelique127]

Grooming panty boy

I loved the attention my boyfriend or should I say girlfriend gave to gave to my feet as he worshipped them. I was so pleased, Drew had finally got in touch with his feminine side and from now on he would be my little submissive pantie bitch. I had him or her, if you prefer wrapped around my little finger ! In the near future I couldn't wait to show him off to my girlfriends, the perfect example of female supremacy and a poster boy of a female led relationship...

" What else can I do for you, honey ? "

" Well why don't you be a good little girly boy and eat my pussy ? You know how much I love it ! " I purred, taking him by the hair and urging upwards while spreading my legs apart...

I had to admit it was rather exciting dominating my boyfriend and having him dress up as a female for me...Drew was now my passive little panty boy and had given up his masculinity without protest ! I was in total control...

" If you make me cum, sweetheart, with your tongue, I may permit you too have one also, using your own hand of course ! " I promised. As I said my needs always come first from this moment on...

...and Prudence was going to get alot of practice worshipping my pussy in the near future !

 

[JDrew]

I nodded at her request obediently and crawled up between her legs. I lightly caressed the soft skin and folds of her pussy. She was wet and I dipped one finger into her, held it, and when I pulled my finger from her I immediately brought my finger to my lips to taste her sweet and salty wetness.

“You always taste so good, honey,” I whispered.

I lowered my head. My blonde hair fell around my face as I brought my mouth to her pussy ready to lap up her juices. First, I teased her with the tip of my tongue and light kisses. As Angelique’s breathing got heavier I began to lick and slide my tongue into her. Her hips heaved upwards, her pelvis pressing full against my face.

I wondered how my makeup would after doing this. I knew I was going to look like a mess. I continued—long, wet licks. And when she lifted her ass I slid my hands underneath, holder her up so that she had better leverage. It was my goal to give Angelique the best pussy licking I had ever given her.

She, after all, had given me quite a night. She indulged my feminine fantasy and even told me that I would be able to continue beyond the night. I was beyond excited at the thought of shopping with her and having her treat me more like a girlfriend than a boyfriend. The least I could do was work hard to please her.

I continued to work her pussy with my tongue. Her hands gripped the back of my head pushing me into the ideal spot her and I knew that she was close to climax.

 

[angelique127]

For some reason my climax was more intense tonight as my boyfriend worshipped my pussy with his tongue, perhaps because I made him dress as a female and submit like a good panty bitch ! Drew's expertise had improved over the last couple of months but I had a feeling he would even impove on his oral skills now that he had got in touch with his inner feminized side.

I couldn't help but move my hips and pussy up and down while I forced his face into my wet cunt. At other times I made him lie on his back as I straddled his head and grinded my pussy back and forth almost smothering him ! No matter in what position Drew loved to eat my pussy and give me multiple orgasms with his talented tongue.

" Ohhhhhh baby...that feels so good ! Please don't stop..." I begged, feeling my climax wash over my whole body, causing my pussy to gush ! Drew knew to lap all of my juices like a good boy or should I say a good gurl !

" Hmmmm that was wonderful baby ! " I moaned, " Now it's your turn. Why don't you lie next to me so I can play with your dickie. "

Of course he eagerly did as he was told. My fingers carassed his cock through the silky soft materail of his panty and he was fully erect within seconds...

You like wearing panties for me and dressing like a girl don't you ? You looked so pretty you even managed to fool those guys at the club tonight ! Now you know what it's like to deal with aggressive men when you go out. Did it excite you ? "
I inquired, noticing Prudence start to slowy move her hips up and down on my hand, wanting more contact...

 

[JDrew]

I laid back, wrapped in the silky, soft nighty and my cock straining against the delicate panties as Angelique slowly caressed me and encouraged my erection through the fabric. I felt pampered in my own little way and it felt magical.

A small, high pitched moan escaped my lips as Angelique continued to play with my cock. The sound surprised me. Not that I was generally silent during an arousing encounter but the pitch, the higher than I expected, breathy sound that I produced was different for me—not a sound from deep in my chest but something lighter. Was it a conscious choice to sound as feminine as I felt? I don’t think it was, it just felt right.

“You like wearing panties for me and dressing like a girl don’t you?” Angelique asked. Even after the night we had it felt weird admitting it out loud. “It was fun,” I said breathlessly. But just the mention of being dressed up and getting to be feminine made my already stiff cock swell.

Angelique smiled slyly as she continued to rub me through the panties. I knew from her expression that she was certain I thought it was more than just fun. At the mere mention of dressing like a girl my twitching cock gave me away.

“You looked so pretty you even managed to fool those guys at the club tonight! Now you know what it's like to deal with aggressive men when you go out. Did it excite you?”

With that question my face filled with heat. It was exciting. And new. There were so many possibilities—so many curious thoughts had raced through my head while we were at the club. I was fascinated and yet jealous of the way Angelique so easily flirted and accepted attention from Rufus. It was exciting to think of her with him. Something else I couldn’t yet admit aloud.

“It was…” I paused not sure how to put so many of my conflicted feelings into words. I left those two words hanging in the air. “It was.”

Angelique’s hand continued to stroke me through the thin fabric. With the newness and excitement of the night I was building quickly to a climax. The clothes, the hair and makeup. Angelique looking so beautiful and acting almost as a guide and mentor to feminization. My new name. The weird sense of excitement at watching Angelique be tantalized by another man—someone who was much more buff and thick than I was. It was stewing around in my head—bit and pieces of the night—flooding my thoughts, driving my excitement.

I wanted to pull down the panties so that Angelique could touch my dickie, as she called it. A new term, something she had never said before tonight and a term that I thought sounded cute.

I wanted her to stroke my dickie until I came on her hands.

 

[Dannibored]

Fantasy cum true

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...

Omg this is my fantasy. Are you anywhere near Chattanooga Tennessee? I have always wanted to be dressed up. I weigh around 155’ and am only 5’3” with little hands and feet. I believe I could be made completely passable. I love wearing a little mini skirt around the house when I am alone. This would be so much fun.
Danni

 

[angelique127]

I think my boyfriend knew how to play the game...he couldn't cum until I gave him permission or suffer the consquences ...

" Oh baby doll look how hard your dickie is ! " I whispered, stroking it with my hand through his panty. I had the feeling he wanted me to remove them but I decided to tease him even more first. I kissed him my tongue exploring his mouth...

" Mmmmm baby...I hope you don't squirt until I give you permission. I wouldn't want my 'bitch' to have to wear that dreadful cage for a whole week or more ! "

Prudence gritted his teeth in frustration.

I pulled his panty down and gently massaged his balls while stroking his erect cock. Drew's cock was starting to throb in my soft hand. I was bringing him to the edge...

" Don't you dare squirt in my hand...you must learn to control yourself ! " I warned, but secrectly wanting him to lose it and explode in my hand. Tonight my little bitch boy was going to learn his lesson once I made him cum.

" Tell me baby...how bad you would like to put your dickie in my wet... tight...and hot pussy right now ? " I whispered into his ear...

 

[JDrew]

Drew squirmed with pleasure, his hips lifting off the bed forcing his cock towards Angelique. His muscles twitched as she stroked, legs vibrating as he concentrated on not releasing.

“Don’t you dare squirt in my hand …” she warned.

He was getting close. Sticky droplets of pre-cum dripped down the head of his cock as Angelique continued.

Drew groaned. A growl. Deep from in his chest. Not the softer, high pitched squeal from minutes ago. Now a full throated desire to cum. But still he resisted. And still she slid her hands softly along his shaft, building friction and anticipation.

How bad could it be to wear that cock cage for a week, he thought. It might be worth it if he could just cum! Hr gritted his teeth and took deep breaths. Not yet. Not now.

“Tell me baby … how bad you would like to put your dickie in my wet … tight … and hot pussy right now?” She asked.

“Yes,” he said in short, panting breaths. “Yes, I want that.” The thought of sliding his cock into Angelique made him flush with excitement. As she continued to rub his cock he heard a squishy, wet sound and knew that he had released another stream of pre-cum. The wetness help lubricate her grip and she quickened her pace. It was almost too much to bear. He wanted to be inside her although her knew that once there he would cum quickly.

 

[angelique127]

I knew that Drew or should I refer to him as Prudence was very close to losing it without my permission. I could feel his dickie throbbing in my hand and could tell he was close. Tonight I was prepared to take our little game to the next level ! By dressing up as a female Drew had given up his musculinity whether he realized it or not and became my panty boy bitch...

" Yes...yes I want that. " Drew insisted, wanting his dickie inside my tight pussy.

" Oh really babydoll ? What makes you think you can handle it ? Everytime I let you fuck me, you cum too soon. Perhaps we need to work on your control issues, don't you think ? " I teased, continuing to stroke his cock, bringing him to the edge...

Dear Prudence shook his head, frustrated and doing his best to maintain control.

" Don't make me punish you baby, you know how much you dread wearing your little cage...oh yes and by the way did I show you the strap on I bought at Adam's and Eve's. It's so big...I can't wait to use it ! " I promised, enjoying the look of apprehension in his eyes !

Smirking I pushed my bitch onto his back on the bed. Before he knew what happened I turned and mounted his face in the sixty nine position. Drew was surprised that I managed to dominate him as I sat on his face, smothering him with my needy cunt...

" Oh God yes ...eat me bitch...now... and don't you dare cum if you want to fuck my pussy. I demanded taking charge and making him submissive to my demands. I pulled his panty down and stroked his stiffy before I took it in my mouth...

 

[rebawants]

omg... I'd luv to be your Bitch... being made to submit...I'll do anything and everything you want!Rebawants

 

[JDrew]

Angelique straddled my head, her creamy thighs tight against my ears and smashed her still wet pussy on my face. I lapped her juices, her wetness coating my lips and chin. I loved licking Angelique but she had never been so aggressive before. She called me babydoll and bitch — terms that should make me feel emasculated but instead her power and control excited me. She pressed her pussy hard on my mouth. I accepted her.

She wrapped her lips around my cock. I wanted to cum so bad and I fought hard to divert my thoughts. What occurred to me was, in that moment, with her controlling my orgasm, her pussy grinding on my face, panties pulled down around my thighs, the soft fabric of the nighty pressed against my chest, that she was in control of me. Completely. She was in charge, she owned me and I surrendered.

I relaxed my body. Angelique slid her tongue along the shaft of my cock, sucked on the head, took me deep into her warm, wet mouth and throat. I couldn’t hold back any longer—I’m not sure she expected me to. I think she wanted me to cum. I don’t think there was an expectation that I’d pass her test or hold on long enough to slide my dickie into her.

The night had been sexually charged from the beginning—the make over, the clothes, the night out dancing and now the threat of a strap-on. “I can’t wait to use it,” she said, her eyes wild with excitement. It wasn’t a matter of if but of when. I thought of myself, bent over, submitting to her. Her, fucking me, slapping my ass and calling me babydoll.

I slipped into the ecstasy of my new feminine reality.

There was no way I could stop myself from reaching orgasm. It was a volcano building inside that could no longer be controlled. My body tensed, my hips heaved upward. Angelique sensed that I was about to cum and took my dickie from her mouth and held it lightly in her hand, still squeezing and pulsating. I squirted warm, white liquid onto my stomach and Angelique’s hand. Immediately my muscles released and I lay spent on the bed, gasping for breath.

As my dickie went soft I wondered if Angelique would make good on her threat to lock me in the chastity cage.

 

[angelique127]

Truthfully I was impressed by my boyfriends stamina and staying power under the circumstances. We had definately reached a positive crossroads in our relationship tonight. Drew or should I refer to him as Prudence had surrendered his masculinity and became submissive and obediant to my every whim and wish. I had brought out his inner female and he seemed more than happy to be my willing panty slave from now on. And I planned to take every advantage of the situation...

As far as I was concerned we were going to have a female led relationship where I was in control and was the dominant one in charge. From now on I made all the decisions...my wish was his command !

" Oh babydoll we are going to have so much fun tomorrow...I can't wait to go shopping and buy you a new wardrobe. And after that we can go to that adult place you like and get some new toys to play with ! "

Drew nodded looking pleased at the prospect. I surpressed a giggle knowing that he knew he had orgasmed without my permission and faced wearing the dreaded cage as punishment.

" Now you know you been a very bad girly boy and had a 'mistake'. But I am quite pleased with your behavior so I am going to give you a choice of punishments...you can wear the cage for the next three days or you can lick up your cum from my finger ! "

I dipped my manicured finger into the semen on his stomach where it spilled and placed it just above his lips...

" I'm sorry baby but you must be taught a lesson for having an premature accident, so whats it going to be ? " I asked with a smile...

 

[JDrew]

I looked from her finger, dripping with warm cream, to her face. She was serious. She was giving me a choice between the two options. There wasn’t a door number three.

“You’re so evil,” I said playfully.

She was right: I was looking forward to shopping. I was giddy at the idea of picking out my own panties and trying on dresses. I didn’t want to do that with my cock locked in a cage. I didn’t mind giving Angelique control of my dickie but I didn’t want to wear it while shopping.

She was looking at me expectedly—waiting for my choice. There was only one option.

“Fine.” I opened my mouth, my tongue stretching out to accept her wet finger. My cum was bitter and salty but not as disgusting as I imagined. Still, I closed my eyes and puckered my face. Angelique giggled and called me a baby before scooping another finger full of cum off of my abdomen and placed it on my tongue. I sucked her finger with a grimace.

I thought of all the times that Angelique allowed me to cum in her mouth—the times she swallowed my creamy emissions with a smile and I knew I had no room to complain.

She brought her finger to my lips again as droplets of liquid fell into my mouth.

 

[angelique127]

I was so pleased that my boyfriend was accepting his new role in our relationship. In my opinion males should be taught their place and realize that females were smarter and better and deserved to rule the roost. Why bother to resist your natural urges when you could discover your inner self now and get in touch with your own feminity ? Drew, or should I refer to him as Prudence, didn't mind giving up his masculinity to me and was willingly under my control.

Yes Prudence was now my willing and odediant bitch boy ! A toy for me to play with however I wished. I absolutely loved the way he eagerly lapped up every last drop of his cum from my finger...

" You are such a good little boy ! Does it taste good darling ? "

Drew nodded yes...

" I think that when you are dressed up as Prudence you should refer to me as your 'mistress'. You should be polite in public as well as when we are in private. " I demanded.

" Yes mistress. "

I smiled with satisfaction. Drew would make the perfect passive male panty boy. I had no doubt that he would do whatever I wanted without question. " Now lets get some sleep shall we ? Tomorrow after you prepare me breakfast in bed we will go shopping and buy you some cute little girly outfits for you to wear ! And since I am in a good mood and pleased with your behavior tonight I have decided not to make you wear the cage tomorrow while on our shopping trip. "

Drew nodded seeming very pleased at the prospect of not being punished and forced to wear the hated and dreadful device on his penis.

" Now what do you say ? " I asked offering him my cheek to kiss...

 

[JDrew]

“Thank you, Mistress,” I said obediently. Angelique smiled and nodded her approval before rolling out of bed and slipping into the bathroom. While she was gone I laid in bed and fantasied about our shopping trip and about my new role in our relationship. It was new and exciting and my cock swelled despite just being drained.

Angelique returned from the bathroom and donned a pair comfy, soft pink PJs. I must have looked at her in her bed clothes with some amount of envy because Angelique shook her head at me and said: “Oh no! You want to be like a girl you must get used to sleeping in nighties. You can clean yourself up but you are sleeping in that.” She waved nonchalantly at the lightweight, silky nightly I was wearing. “And your panties too. Now, go clean yourself up.”

I climbed out of bed and straightened my nighty before disappearing in the bathroom. I stared at my reflection and realized how much had changed in my life since the last time I seared at myself earlier that night. I was no longer Drew. Now I was Prudence.

A bolt of excitement shoot through me. Despite my make up being smudged and smeared from our sexual encounter I felt fresh and in some ways, reborn. I was energized. Once again my cock twitched and grew. I touched it. Slowly at first. Lightly. I didn’t know if there was a rule against masterbating now that I had given myself completely Angelique but I couldn’t stop myself.

I quickened my stroke. I thought of the event of the evening. Everything playing in my head over and over culminating with Angelique’s soft lips gliding over the shaft of my cock.

My legs quivered and with my free hand I steadied myself by grabbing the edge of the sink. Still I worked my cock like I had many times before only now it was different. My fantasy was coming true and I was excited in a way I had never known.

It didn’t take long until I was squirting warm cream onto my hands. I exhaled heavily feeling relaxed and satisfied.

I finished washing my face and returned to bed. Angelique and freshened the covers and I slid into bed next her, quickly falling asleep.