Omar walked me home from school and he was so sweet holding my hand the entire time. I was wearing my schoolgirl uniform with white tights that day and I had started rolling over the top of my skirt to make my hemline really short. The bottom of my skirt started just below my crotch and showed off my legs. I was worried that a teacher or a principal might say something but they had kind of a lax attitude towards that sort of thing and all of the girls were doing it. I had to be careful to cross my legs or else guys could look up and get a panty shot.
 

The Challenge: Part 8
By Tyler

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Omar walked me home from school and he was so sweet holding my hand the entire time. I was wearing my schoolgirl uniform with white tights that day and I had started rolling over the top of my skirt to make my hemline really short. The bottom of my skirt started just below my crotch and showed off my legs. I was worried that a teacher or a principal might say something but they had kind of a lax attitude towards that sort of thing and all of the girls were doing it. I had to be careful to cross my legs or else guys could look up and get a panty shot.

It was clear that the hormones I had been taking had brought my development as a man to a halt and I was instead maturing as a teenage black girl would. I had the feelings and nurturing instinct of a girl and my dad and brother were experiencing the same changes. My dad had had a "second-puberty" had had been turned into a woman. My little brother was only just beginning to turn into a man when he was flooded with estrogen and transformed into a cute black girl.

"I can't wait to take you to the dance," said Omar.

"I can't wait either," I replied.

"Well," said Omar as we walked up my driveway, "You're home."

"I'll see you tomorrow," I replied coyly.

"You don't mind if I give you a kiss," he asked?

"Of course not," I said. And with that he bent down and stuck his tounge in my mouth. It was my first french kiss. He reached under my skirt and grabbed my butt with his right hand, and he put his left hand on my breasts. After it was over I was glowing. Carefreely, I waltzed into the front door. Kendra and dad were already home. I smelled dinner on the stove. Dad was wearing a short black dress with black tights and an apron.

My breasts still felt sensitive after Omar had touched them. Since I had grown my own, I would get an erection every time my mammaries would get stimulated.

Just then, out of the corner of the living room, I saw my sister and my mom sitting on the couch. "Oh my god, sweetie," she said, "I can't believe it is really you?" She got up and gave me a hug.

"Oh mom," I said, "It is so good to see you. It has been so long."

"I can't believe what a job they did on you," mom said, "I would never guess that you were a boy. Your hips and face are so feminine, and your boobs...."

"DoubleDs," I said proudly.

"Yeah Mikey, or should I say Brandy," said my sister, "You look absolutely amazing."

"Well," said mom, "Your father and brother are totally beautiful. Who would have thought that this was possible."

"It is weird seeing my little brother in a skirt and tights with big boobs," said Julie.

"What do you mean," I said petulantly, "I used to dress up in your clothes all of the time."

"So that is what all of those mysterious white stains were inside of my pantyhose," said Julie.

"Who was that guy you were with just now," inquired mom, before I had a chance to defend myself?

"His name is Omar," I replied, "and he's taking me to homecoming."

"Yeah," chirped in Kendra, "Brandy has a boyfriend."

"He's not my boyfriend," I blushed, "We are just friends."

"Than what were you doing kissing him?"

"Oh, you saw that," I replied.

"Well, we might be more than friends."

"Yeah," said Kendra, "Who knew Mikey was really gay?"

"Now now sweetie," said mom, "It is perfectly natural for a teenage girl to get a boyfriend. You're just still probably too young to feel that way."

"Oh no," I replied, "Kendra had a date for the last dance we went to."

"Yeah, but Brandy made out with her date," said Kendra.

So we spent the rest of the evening laughing like old friends. Fiona decided to just let us relax and give us a break from any lessons. After dinner, mom asked me, "So, I would love to see you model some of your outfits. You look so much better as a black girl than as a white boy."

"Oh mommy," I replied, "There is nothing that I would enjoy more."

"Will you let me do your hair," she asked me?

"Sounds like fun."

"Wait a minute," said Monique, "You girls can't keep Mel all to yourselves."

"Relax dad, you'll get to spend all night with her after we go to bed."

"I was so excited to get to be with your dad as Monique," said Mom. "I missed him so much."

I was literally bouncing up and down with excitement. Kendra seemed happy to see mom again.

"Come on girls," said Mom, "Lets go spend some time together. You too Julie."

The four of us went up to Kendra's room. This was my first chance to see some of the outfits that she had. I thought that her clothes might be a little bit tight on me but I was sure that they would fit. Kendra and I were about the same height but I was about 10 lbs heavier. Julie went over to the closet and started looking at some of the dresses over there.

"Okay girls," said Mom, "get undressed and lets see what we are working with." Julie turned around and watched. I stripped off my blazer and blouse, revealing my enormous breasts. I was wearing a pink bra and my mom could see the top of my tights over my skirt. "My god Brandy," said Julie, "You are huge. And Kendra is not far behind."

"Yeah," I said as I took off my shoes, "I grew quickly and I didn't need breast forms after a couple of weeks." I took down my skirt.

Julie had stripped down to just her bra and panties. She said, "Wow Kendra, you have some cool clothes in this closet. OMG, she screamed, you have playboy bunny outfits in here!"

"Wow," I said, "I want to be a playboy bunny."

"Do you have sheer black pantyhose, Kendra," asked Julie?

"Of course I do," she replied, "It is in the top drawer."

Julie took off her bra and pulled a longline bra out of Kendra's drawer; that way the straps wouldn't show over the strapless leotard. She put on the bra and then grabbed a pair of sheer hose out of the drawer. She tossed two more pairs of pantyhose over to me and Kendra and told us to put them on. "I can't wait to see how we look as bunnies."

I pulled down my white tights and threw them on the bed, and I was only wearing my pink panties. I had on a kotex underneath. The reason I was wearing Kotex was because Fiona had had me plan my periods a while back and it was my time of the month. Even though of course I couldn't actually have a period I still had to go through the motions.

"OMG," said Julie as she slipped her legs into the tights, "why are you wearing a Kotex?"

"Fiona has me simulate periods," I replied.

"That is crazy," replied Julie. She had her tights up to her thighs and soon she had pulled them up over her panties. It was weird watching my sister dress. Kendra had her hose well on her way.

My mother had stripped down to her lingerie and had picked a lime-green prom dress out of Kendra's closet. She took the balled up white tights that I was wearing and began to pull them on. She got the tights on quickly and efficiently and with one motion slid them all the way up her thighs and straightened the waistband. She stepped into the dress.

"Its easier to put them on when they've already been worn," she said. I thought that my mom and sister looked cute in hose. I noticed my sister's long blond hair and well-formed breasts and thought that I would want to look like her as a white girl. I liked the short-pageboy style cut of her hair.

I got the black pantyhose on and had opted for the black bunny suit. The little leotard had a poufy white little bunny tail. I also had a matching set of ears to wear. I was ready to put it on but mom called me over and had me help her zip up her dress.

Julie had a pink bunny suit and she stepped into it. Then, she went to help Kendra get into her red bunny suit. We all put on our ears and then we went to model in the mirror. I put the feet through the holes of the bunny leotard and wiggled it up over my breasts. Fortuantely my tits were big enough to where I didn't have to worry about my top falling down. My hosed legs looked long and sexy coming out of the bottom holes and my crotch was very smooth. All of us stepped into stripper platform heels that had the effect of pushing up or butts.

"OMG," said Julie, "We are so fine." I had to concur. We al struck poses in the mirror.

"Damn straight," I said. I loved how the leotard molded to my skin and showed off every inch of my curvy physique. "I used to always want to be Hugh Hefner, now I get to be one of his bunnies." I felt like the sexiest girl alive.

"Well Brandy," said Mom, "You looked really pretty doing your little ballet dance the other day."

"You were there for that," I said with some surprise?

"We were sitting behind the mirror at the studio," said mom. "I loved how you looked in your little ballerina outfit."

"Oh mom," I blushed. "I feel like such a pretty girl. My maleness is gone."

Just then, there was a knock at the door. Monique came in wearing a short pink dress and white tights. "My god girls," he said, "I have three cute little playboy bunnies." No one would ever have been able to guess that the three black girls in there really had penises.

"Hey dad, or should I say mom," said Julie flirtatiously.

"I don't know if I like my 18 year old daughter dressing like a porn star," protested Monique.

"Oh dad, we're just having fun."

"Mabye it is just my kotex riding up my butt," said Monique. "Fiona has been really tough on me lately."

"Dad," said Julie, "You are such a pretty woman."

"Oh thank you dear," he said as he gave her a hug.

Mom was spinning around in her little green dress. Julie took her iphone and started snapping some individual and group photos of us in our outfits. "I want to remember my sons as little black girls," said mom.

"Wait a minute," I said, "Dad didn't tell you that we were thinking about staying female."

"Well," said mom, "I could hardly blame you."

"Hey mom," I said, "Do you want to see my costume for the ballet recital."

I ran to my room to get my tights and tutu. It was hard to run in heels so I took small, dainty steps, and I felt my ass sway back and forth. I came back with a garment bag. Quickly, I kicked off my heels and took down my corsetlike bodysuit. Then, I dropped my sheer pantyhose. I took a pair of white tights out of the garment bag and sat down on the side of Kendra's bed to pull them on. I pulled the tights up over my panties and kotex. Embarassingly, I had developed a huge erection since everyone was watching me. The feeling of my male member in tights always did this to me.

"Its all right," said mom, "Its just a natural reaction."

"I wish I didn't have a penis," I said, "It is really like my quivering pussy."

"Brandy has a vagina," taunted Julie.

"I just don't want to make a mess inside of my underwear," I replied.

"Yeah," said Julie, "like those messes you used to make inside of my tights."

"I couldn't help myself."

"Your kotex should sop that up," replied mom. "Thank god Fiona thought ahead. And Julie, stop teasing your sister."

"Fine, Mom."

"It feels like wearing a diaper," I replied.

I got the tights on and then pulled on my leotard. I took out the tutu and stepped into it. Quickly, I slipped on my pink ballet slippers. I always loved the feeling of putting my legs and feet covered in soft cool white tights into dainty, feminine, pink ballerina slippers with little bows. Mom said to me, "Sit down at the vanity and let me do your hair and put in your tiara." Mom brushed my hair into pigtails and put a couple of braids into my "do." Then, she put the little princess tiara onto my head. Mom touched up my makeup and it was great watching my face get prettier and prettier. It felt great sitting there in the pink chair in my leotard and tights, with all of the girly attention being lavished on me.

I stood up and looked into the mirror and saw the gorgeous black ballerina that I had become. "Wow" said Julie, "You are the prettiest black girl I have ever seen." I did some little poses and spun around. A cool breeze blew against my tighted crotch. I loved how the tights made my legs looked long and sexy and my boobs looked really prominent. The leotard and tights assisted with my body's freedom of movement and the tight nylon felt orgasmic. I did little arabesques and pirouettes.

I blew kisses at dad. I was the feminine center of the world. Julie thought it was funny how ruffly my butt was and she would slap my exposed under my tutu. She would take her hand and lift my tutu and play with my little ruffles. I would bend over and show my butt, laughing the whole time. She tickled my crotch a little bit.

I don't know if dad/Monique was happy standing there watching his "son" be feminine. What could he really do. "Well Melanie," said dad, "We have raised three wonderful daughters."

Kendra was still hanging around in her bunny outfit and she said, "Hey mom, can you do my hair like Brandy's?"

As we relaxed and chatted away like girls in our pretty outfits, Fiona came into the room wearing three packages. "Relax," she said, "We are all ladies here."

I had no idea what else Fi could possibly have in store for us. The packages were three small mysterious cardboard boxes. She handed one to me, one to my brother, and one to dad.

"Open them up girls," she said. Our hearts were pounding with anticipation. Dad and Kendra opened up their boxes and looked inside.

I ripped open the box and pulled out what appeared to be a brown pair of panties. I was curious as to what they were actually for. I turned the garment around and saw in the front what appeared to be a feminine looking vagina with a patch of hair. "Oh my god" I thought, "Is this what I actually think it is." I saw the look of shock on dad's face as he saw the realistic pussy. We were going to become complete women. Now we could make love to guys and they would never be able to suspect anything.

"These are vaginal panties, ladies," said Fiona. "This is a completely realistic, functioning vagina with an entry depth of nine inches. If you wear them and stick something up there, it will actually stimulate your male member to duplicate the feeling of a female orgasm. It will feel just like you are having sex or masturbating as a woman. Also, these are designed to let you and force you to sit down to pee." We studied them carefully. I could tell that dad couldn't wait to get his on, but Kendra looked a little nervous. It was provoking some anxiety knowing we were taking another step forwards in our development as females.

"Well ladies," said Fiona, "Get on your pussy panties. You have to wear them all of the time now." Mom and Julie snickered.

Kendra said, "No, I am a boy and I won't wear this."

"Nonsense young lady," said dad, "You are a girl and you will be a girl."

"Oh fine," said Kendra. She took down her red bunny leotard and black tights. She kicked off her stripper platforms and took down her shaper panties to reveal her manhood. Mom helped Kendra get the pussy panties on and straight. When she had them on, Kendra looked like a complete black girl from head to toe. All signs of being a boy were gone, and there was no bulge at the crotch. It was crazy. All she had on still were her bunny ears.

"Oh my god," said Kendra, "I have a pussy."

"We all will have pussies," said Dad. Dad took the pink dress he was wearing off of his shoulders and dropped his tights and panties. He was standing there wearing nothing but a red bra. He took off his old shaper panties and pulled on his pussy panties to make him look like a real woman with a functioning vagina. I pulled my white leotard and tutu off my shoulders and threw the nylon garments on the bed. I shedded my tights, panties, and kotex. Dad helped me get on my vaginal panties and pull them up over my penis.

"Wow, dad," I said, "I'll finally be able to be a real girl. It is like I have a real vagina." I thought about all of those times I had dressed up in my sister's clothes and I had never imagined that one day I would get to be an actual girl, and a black girl nonetheless!"

"Of course sweetie."

Mom helped Kendra get her black tights back on. Kendra stepped back into her corset leotard thingy and looked just like a cute little playboy bunny model. Actually, she could have probably passed for 18. Once Dad was satsified that his new vagina was on satisfactorally, he got his heels, tights, and dress back on. I rolled my tights back up my legs and stepped back into my white leotard and tutu. All signs of our male bulges were gone and it would take a very close examination of our private areas to see that we were really male. By now, our feminine secondary sexual characteristics(wide hips, breasts, voice,) were totally developed. Fiona pronounced that we were finally done with the physical aspect of our transformation to women.

"You girls will be able to make love now," she said.

My dad couldn't wait to try it out and raced to the bathroom to pee sitting down. "It works," he announced.

We spent the rest of the night trying on various outfits. Julie and Fiona took some pictures and videos of us and I am sure that the hidden cameras in the house were having a field day. We all put on a mini-beauty pagent and we had the time of our lives wearing dresses and shaking our hips provocatively. It was a great family reunion.

Julie changed into a pair of white tights and a pink leotard and we practiced some ballet moves together.

A couple hours later, I kept on my white tights but pulled on my Pocohontas leotard so I could show it off to mom. I felt much more comfortable and confident with the vaginal underwear as opposed to my shaper panties, in the sense that I didn't have to worry about my male bulge. Dad was in his pink dress and I asked him to help me put my hair into a ponytail.

"Isn't it great having real girl parts," I asked my dad?

"Of course it is honey," said dad, "We are real women."

"Yes," I said giddly, "real girls. I just love being in tights and leotards and having a vagina."

"That is the truth, sweetie," said dad as he brushed my hair.

"Now now," girls, said mom, "Don't get too sweet during this girly bonding moment. Save him for me."

"Mommy," i said petulantly, "My name is Brandy and I am a teenage black girl."

Not to be outdone, my dad said, "My name is Monique and I am a sexy, voluptuous black woman in her pretty pink dress and white tights."

----

As we were wrapping up the night, I changed into my cheerleading outfit to practice some cheers for mom. I pulled on sheer hose and my cheer briefs and my cheer jumper. I grabbed my pompoms and went through some of my routines.

Mom looked at the package of pantyhose and she said, "I see you girls are getting Brown Sugar hose."

"Yes Mommy," I said coyly. I shook my pompoms in the air and sang, "I'm sexy, I'm cute, I'm popular to boot." I loved how the short skirt of the cheer jumper showed off my sexy legs. Afterwards, I got naughty and pulled on some stockings and lingerie that my dad had. I didn't know if he would object or not but he just turned a blind eye.

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Despite appearing to the world and my family as a black woman named Monique, I was thrilled to see my wife and daughter after being away for so long. I was worried that they would laugh at me, but they were so understanding. It felt weird when they first saw me slaving over the stove dressed as a woman but they ran up to greet me like nothing had happened. I was still the same guy underneath. We were just acting out parts in a play. Mel and Julie commented on how pretty I was and all I could do was curtsey and blush. I didn't know how they would take it that I was actually enjoying myself as a female, but they were very compassionate and accepting.

Earlier today I had sat down to watch TV and I had put on a football game, but Fiona disapproved and made me watch soap-operas. Mel promised me that she would support me with whatever "major life decision" I made.

So now I had my vaginal panties on under my tights and panties and I couldn't belive how I could sit down to pee. It was hard to say how these things actually worked but it was 21st century technology. I noticed when I stuck my finger inside I would stroke the underside of my penis.

My "sons" were out there prancing around in dresses and hosiery. I wanted to look good for Mel so I touched up my makeup. This was our first night back together and I wanted it to be special. She looked so pretty in that lime-green dress. I was in my pink-dress with cap-sleeves that I loved. I put on another coat of lipstick and touched up our mascara. Soon it would be time for bed. I made sure that my new vaginal panties were keeping me smooth and in check and I made sure that my tights were straight.

"Monique," said Mel, "I just can't get over your new look."

"Well thank you sweetie," I replied.

"I want you," she said, "Tonight. I have never made love to a woman before."

"But I am still Joe, your husband."

"Face it," she said, "You are Monique."

"We should get the girls to bed."

The girls were sad that this fun night had to come to an end. Brandy had gotten into my lingerie and was wearing a corset, garterbelt,and stockings. Kendra and Julie had respectively pulled on a Pocohontas and Little Mermaid princess leotard and were wearing white tights underneath. Julie went to sleep in the spare bedroom, and my black girls went to their rooms for the night. I had no doubt that they would experiment with their new undergarments.

Melanie took me up to my room. Slowly, she pulled off my pink dress and hung it up in the closet. She pulled down my tights and panties and stuck her finger into my vagina. I stroked my breasts.

"Tell me you don't love being a woman," said Melanie. "I always dreamed about being with a black woman."

"I love it so much," I replied. I felt like I was already ready to orgasm.

Melanie stopped what she was doing and she took off her dress. She was wearing nothing but her white tights. She came over and pulled off my vaginal panties revealing a hard cock. She began to perform some oral movements on me. I moaned.

"I love you as a woman," she said, "Much more so than as a man. You must stay as Monique."

She put some lotion on her hand and began to stroke me. I lay down on the bed with my tights gathered at my knees and just enjoyed it.

"Just let me take care of you tonight," she said. "You're still my manly man deep down. Tonight I will treat you both as a man and as a woman."

She played with me until I was ready to cum. But I wanted to try something different. "Wait," I said, as she stopped with a look of surprise.

I stood up and pulled my vaginal panties back on. I walked over to my dresser and pulled out my black dildo. "Use this," I said.

"Did Fiona give you this?"

"Yes," I said, "Now pleasure me like I am a woman." She stuck the dildo into my pussy and it felt great, like I was being screwed. I had pangs of ecstacy.

After I had been satisfied, Melanie let me use the dildo on her and take her from both the front and the back. Then, I had her use the didlo on me in the rear.

"I like you much more as a woman," said Mel, "So I don't mind doing this new stuff with you. It is much more erotic for me this way."

"Me too," I said.

"I don't think that you are a sissy," she said, "You are just a man doing what he has to do to survive. If that means becoming a black woman, than so be it."

"I'm glad you understand," I said. We both pulled our white tights back on and we cuddled.

"How do you think that the boys will do as girls?"

"Just fine," she said confidently. "They are so feminine and convincing already."

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Meanwhile, I was in my bedroom and I "experimented" with my new vaginal underwear. Fiona was right, these things really worked and I felt just like an actual woman. I took my dildo and stuck it all the way inside of me and pleasured myself repeatedly. I heard moans and bumps all night from the room next door and knew what was going on with dad and mom. So I guess we were one big happy family of girls.

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SORRY ABOUT THE WAIT!!!!