Feminized Pretty Boy

[angelique127]

" Welcome ladies...I see you have met my little sissy maid, Prudence ! " I said decending the stairs like a princess.

" Yes she is so delightful ! What a perfect name for her ! " Devon complimented.

Prudence opened the front door permitting Ginger, a gorgeous red head to enter. She stared at my sissy pantie boy maid in sudden confusion, raising her eyebrows in surprise.

" Now please don't forget to courtsy for my guests sweety. " I warned. Prudence did as she was told, bending over at the waist.

" I hope you girls remembered to bring your bikinis so that we can go sunbathe beside the pool later ! " I said, " In the meantime I would like to introduce you all to dear Prudence, my latest live in maid ! "

The ladies giggled, impressed with his transformation.

" Oh my... did she do her own lipstick ? And those eyebrows... " Devon inquired.

" Yes she is learning to put on her own makeup, but I did pluck her eyebrows yesterday ! "

" Have you put her on hormones yet ? " Tiffani asked.

" No but I plan to do it soon, I think ! " I answered, " But she is still in training ! "

" Well you have done a very good job so far ! " Devon said.

" Yes I think I am going to make my boyfriend into my very own loyal panty boy ! " Tiffini replied.

" It's the lastest rage ! " Ginger giggled...

Darling why don't you lift your little skirt up and show the ladies your panties ? " I suggested...

 

[JDrew]

I was proud when Devon complimented my make up and I smiled at her. It was strange to have three women fussing over me, examining my hair, my clothes and make up. I enjoyed the attention and wondered what I’d learn about being feminine from Angelique’s friends.

“Darling why don't you lift your little skirt up and show the ladies your panties?”

The three women stared at me expectedly but I hesitated. With an audience I suddenly felt self conscious. I was enjoying their positive comments and praise but now wondered if that would turn to humiliation. My cock, which I felt was cute, wasn’t huge.

Clearly Angelique enjoyed drooling on Ryan’s massive, thick rod and even though I knew that the male part of my life was quickly coming to an end I still didn’t want to draw those comparisons.

“C'mon,” Devon said. “Let us see.”

I felt a little heat rise in my cheeks but pulled up my skirt.

“Oh, she’s embarrassed,” Ginger said. “How cute—I love it!”

“I would so love to see my boyfriend in a skirt with rosy, modest cheeks,” Tiffani added. “Angelique, you have to tell how you did this.”

Devon approached me and ran her hands over my panties. “Not too bad but you’re going to have to learn how to tuck that little clitty cock away. I’m sure there are videos online about hiding that small bulge of yours.”

“I bet hormones will help shrivel that little dickie right up,” Ginger said with a laugh.

“Go ahead and pull those panties down, sweetie,” Tiffani said stepping forward.

Again I paused. I looked at Angelique hoping she’d jump in and redirect the conversation. Instead she raised her eyebrows and nodded.

I took a deep breath and pulled my panties to my knees.

“Oh, your cock isn’t that big,” Tiffani said with a smile and a glance at the other women. “You should easily be able to hide that.”

The women circled me, commenting on my ass, the fit of my maids outfit, my smooth, shaved legs and the way I stood in my heels. They gave some compliments, suggestions on how to be more feminine and took notes on how they’d dress up their own boyfriends.

“I might have to borrow your sissy,” Tiffani said to Angelique. “She can show my Thomas how to act and dress.”

“I’d just like to have a maid,” Devon mussed. “Maybe you should rent her out.”

I glanced at Angelique and she looked, for a moment, like she was seriously pondering the suggestion.

Finally Tiffani said: “Panties up, sissy. I’m ready for another glass of wine.”

 

[angelique127]

" Panties up, sissy...I'm ready for another glass of wine. " Tiffani demanded.

Prudence rushed to obey doing her duty to my guests as I thought over her proposal..." Well instead of renting out my new maid, I would be willing to come over next week and help give Thomas a lttle ol' makeover. " I offered.

" Thats not fair, how about me ? I think my husband has shall we say, feminine tendencies too and would make a nice looking female if he only shaved his beard...not to mention he has a little tiny cock also ! " Devon giggled.

" Oh I almost forgot ...yesterday we went to a club after going shopping and David was all dressed up pretty and we met this guy there ! Oh my God, he was a total masculine hunk ! We both danced for him and then I invited him home. It was so wonderful to have a real man around the house for a change, and he was hung like a horse... I didn't even know what I have been missing for all this time ! "

" And your boyfriend didn't mind ? " Devon asked.

" Of course not, that's just another benefit of turning your husband or boyfrind into a submissive sissy ! " I laughed holding out my glass for Prudence to refill from his tray. Prudence dared not meet our eyes and kept them lowered to the floor like a good obediant sissy maid.

The conversation then turned to the new names they were going to call their boyfriends and hubbies and the best places to shop for their new clothes and such.

" Why ladies why don't we go out and sunbath next to the pool while Prudence covers us with lotion ? Besides I can't wait to show off my new bikini that I bought yesterday ! " I suggested, eager to work on my tan.

As the ladies rushed off to change I told Prudence to fetch the scented suntan lotion and keep the drinks flowing like a good little sissy servant...I so loved showing off my new obediant aquistion it was better than I ever imagined...

 

[JDrew]

Upstairs, at the top of the closet in the spare room (my room?), was a woven palm leaf tote bag filled with summer accessories including spare sun glasses and suntan lotion. Angelique had several tubes: Coppertone Glow Shimmer, Hint pineapple sunscreen spray, Maui Babe Browning Lotion and several off-brands scented with tropical fragrances. I grabbed the bag, flung it over my shoulder and headed to the kitchen to load up my tray with another round of drinks.

Now changed in bikinis, the ladies were waiting for me when I stepped outside. They each took a glass of wine from my tray without saying a word to me, as if I were an unknown cocktail server at a dinner party. They continued their conversation, laughing about their boyfriends and husbands, excitedly thinking of ways to use a sissy in their lives.

“Prudence, pull four lounge chairs together for us please,” Angelique commanded. I dropped the tray and tote bag and rearranged the deck chairs for them to sit in a semi circle near the edge of the pool.

I helped each girl into her chair, adjusting the back and leg height to meet their individual specifications. Tiffani made the most changes. I raised and lowered the back, brought her an outdoor canvas pillow and adjusted the chair so that her legs had a slight bend at the knee.
“What a great maid you are,” she said to me.

“You know, it’s getting warm out here and I like my wine chilled,” Ginger said, her face twisted like she’d just eaten a piece of sour candy. “Can you make something cold? Like a daiquiri?”

Angelique snapped her fingers at me. “Prudence! You make those wonderful frozen drinks.”

“Frozen strawberry margaritas,” I said quietly.

“Yes, we’ll have those next. They will perfect today.”

I started to say that I didn’t think I had all the ingredients but there was no use. The decision was made. It was up to me to make it happen.

I started to collect empty glasses and place them on my tray when Devon called out: “Prudence, before you make those I could use lotion on my back.” She starred straight ahead, half her face obscured by large dusty pink designer Italian sunglasses.

I put the wine glasses on a nearby table and pulled the tote over to Devon’s chair. She leaned forward. “Now sweetie, make sure you get my shoulders and the middle of my back.”

I dropped to my knees and reached into the bag pulling out the first tube I felt, a Coppertone product. I squeezed a large amount of lotion into my hand and smeared it across Devon’s back.

I ran my hands over her slim shoulders and the back of her thin arms. She leaned forward even more and I worked the lotion around the thin strap of her bikini, down her lower back.

“That feels great, Prudence. I should have you give me a massage.”

Tiffani’s head perked up. “Oh that would be lovely. After the frozen drinks a massage. But first, I could use my back covered too.”

I finished with Devon and moved to Tiffani. Each of the women had me lather their backs, covering them with a variety of lotions. Soon the air smelled like a tropical beach.

It was hard to not feel aroused—wearing panties and a short skirt, my ass peaking out every time I knelt down to rub more lotion on a gorgeous girl—each girl barely covered, firm breasts and tight asses in my face.

Angelique didn’t seem bothered by my wandering eyes as I worked but my growing erection might have caught her attention. “Now, off to the kitchen and get that blender started,” she said, lowering her sunglasses to give me a stern look.

“Of course, Mistress.” I said.

 

[angelique127]

It certainly wasn't any secret that Prudence was enjoying himself/herself, seeing the little bulge in his sheer panties was all the proof I needed. I wasn't jealous really, she was MY little obediant sissy maid in the making, and devoted to me ! Besides the girls seemed to be enjoying themselves by teasing him, having sissy rub scented lotion all over their almost naked bodies. Finally I had to interrupt the fun because I was thirsty for a frozen margarita...Now off to the kitchen and get that blender started ! " I demanded.

The loyal submissive expression on her face was priceless and without any further hesitation Prudence obeyed, walking towards the kitchen, a rather provocative sway to her hips despite her inexperience in wearing high heels..." Hurry back sweety ! Tiffani urged with a giggle.

Again the conversation turned to the benefits of having a feminized boyfriend...

" Yes my sissy boyfriend will treat me like the goddess I am, " I bragged, " I will make him do all her chores, cook, clean, do the laundry and such. Also he will be responsible for preparing me for my dates if I want to go out ! "

" Really like what ? " Devon asked.

" Oh you know, just helping me get ready...like preparing my bath, shaving my legs, giving me a manicure and pedicure first and brushing my hair..."

" So speaking of helping you get ready to go on a date with a real man, who was this guy you both met last night ? " Tiffani inquired.

" Oh my God he was a total stud ! Not only was he hung like a horse but he knew how to use it. I lost count of how many times he cummed and then got it up again...not like my David who has a hair trigger and no control, not to mention a little dickie, as we all know ! This guy was so much better and better ! Just looking at him made me cream my little ol' panties ! "

" So speaking of helping you get ready to go on a date with a real man, who was this guy you both met last night ? " Tiffani inquired.

" Oh my God he was a total stud ! Not only was he hung like a horse but he knew how to use it. I lost count of how many times he cummed and then got it up again...not like my David who has a hair trigger and no control, not to mention a little dickie, as we all know ! This guy was so much bigger and better ! Just looking at him made me cream my panties ! "

" He sounds fabulous ! Are you going to see him again ? " Devon wanted to know...

" I hope so, the guy is a total hunk ! " I bragged

" I wouldn't mind meeting him, maybe you could introduce us sometime ! " Tiffani suggested.

" Me too...perhaps you could have a little party and make Prudence serve us hor d' oeuvres and cocktails in a frilly apron ! " Devon said.

" Why I do declare, I thought you both were married women ? " I pretended to be shock at the possibility.

" Well its not really cheating if you cuckold them. " Devon stated with a devious smile.

" What is taking her so long ? " I asked feeling irritated. I picked up my little brass bell and rang it, " We could all die of thirst before she got back with our drinks ! "