Jennifer Nicole Evolves

Jennifer Nicole Evolves- Now There Are Four

You have recently been introduced to Jennifer Nicole. The chapter continues focusing on the beginnings of Jamie's double life. Her sisters Melissa, Megan and Amanda helped Jamie start his journey as Jennifer Nicole. This story contains sexual activities and situations between consenting adults. All characters are above the age of 18. If there is any similarity to any person, living or dead or any location, then that is pure coincidence, it was not intended. Your comments and feedback are greatly appreciated.

As I reflect on this day, I cherish how my sisters, and ultimately my family and friends have accepted Jennifer Nicole. They always let Jamie be Jamie, now we are embarking on Jennifer Nicole being whoever she wants to be.

I have had different stages in my journey. Throughout this life trek, I have adopted and adapted many different personas, whether it be Jennie, the budding female trying to fit as the new girl.

As Jen, I became just a college schoolgirl. I could dress in cute little outfits that embodied my innocence. I loved the role Jennifer played in my evolution. She has always been the sophisticated, charming woman showing confidence in all situations. Jennifer is always charismatic.

This story is another chapter, at this point in her life's journey.

The four of us for the first time chatted as four sisters. Amanda sat next to me holding my hand; we have always been close. As she listened to Melissa and Megan, bringing her up to speed she was almost more excited than I was. I sat there in silence, taking in what's just happened this morning. First getting caught, embarrassed, then how genuinely my sisters were willing to transform their little brother into their little sister.

The excitement of my situation was overwhelming. My legs were now shaved as well as all my other body parts, my lips were moist, my face was that of a young lady, and the sensation of being in my nylons made it difficult for me to focus on the conversation around me. I really love this femme side of me more than the vanilla male side.

Melissa speaking up, she got my immediate attention. "We have made great strides this morning. This afternoon, Sis, we are going to work on female mannerisms, what's expected from you as our sister and a few things every female must learn. We are going to try on more outfits this afternoon. The four of us are going shopping tomorrow. We will be getting you your own outfits you can wear around the house, but since you don't have a lot of money you will be responsible for all the housework. Perhaps even the meals too. Of course, you will be expected to perform all your chores in female attire. "

Looking directly at me, Melissa sternly said, "Do you understand me, Jamie?" I nodded affirmatively.

Megan had prepared salads for lunch. I was told to grab a tray in the kitchen, load up bowls of salads and cutlery, a pitcher of iced tea, glasses, straws and napkins. I did, then started setting the table. Melissa stopped me, showing me the proper way to do the little things, including the placement of plates and cutlery. I filled each glass with ice and poured tea in each glass. I then sat down to sip my tea without a straw. Melissa stopped me again, saying, "Look Sis, you always drink your beverage from a straw. You don't want to mess up your lipstick.

As we finished lunch, Melissa continued, "Tonight, will be a little chilly, so I'm thinking of a little ceremony, ritual if you may, involving your male underwear. Amanda will help you gather up your male undies. So. you two can get started upstairs. Megan and I will clean up. We will join you in a few minutes. "

As Amanda and I scooted upstairs, I overheard Melissa whispering to Megan, "Jamie, let's call her Jennie now, why don't you text Aubrey to stop by unexpectedly after 7. We need to get Jennie some friendly exposure outside of her sisters. She doesn't know it yet, but she is shopping as Jennie tomorrow. Then after shopping tomorrow will give Jennie and my boyfriend John a little surprise. It will be her baptism into sucking cock.

As we reached the second floor, Amanda and I ran into my room. I was frightened, "Did you hear Melissa? I don't know how to suck cock." Amanda shushed me, "I will help teach you this afternoon. It's fun sucking cock!" I looked back at her, "You do? Teach me."

My sexual identity has become confusing to me. I have enjoyed my male sexual side with a few girlfriends. I am attracted to women, but what was confusing, I was also attracted to the hunky, athletic type men. I know I am bi-curious, but sucking cock will be new to me. Just thinking about sucking cock, I could feel my sissy clit pushing the thin fabric that encases my clitty.

Amanada brought me back to the moment at hand," Melissa told us to gather your male underwear, but first show me your little pink outfit. You look so cute." I twirled, did a little pose, then flashed my panties. Amanda licked her lips, squealing, "Oh, you are yummy! I really love how you fit into the lace thong too!" Looking me straight in the eyes, smiling she squeezed my clit," Your little sister wants a taste!" I flinched, diverting the conversation, "My undies are in this drawer."

We filled my clothes basket with the contents of my undie's drawer. We set the basket on my bed. Melissa called for us to join her and Megan in her bedroom. We both obeyed.

Throughout the afternoon I tried on many different outfits. I must have tried on every dress, skirt, blouse, pants, shorts, jeans that Megan and Melissa owned. Melissa kept saying we are trying to develop Jennie's style. No one addressed me as Jamie. I wasn't the only one trying on clothes. We giggled and laughed all afternoon.

The sexy lingerie flowed out of their drawers too. I wore thongs, briefs, hipsters, boy shorts, g strings, cheeky, bikinis, and tangas. I was overwhelmed, I didn't know there were that many styles. Then the bras. Since I was flat chested, I mostly tried on push-up styles. Melissa remarked at one time, that we needed to get me breast forms.

Throughout the afternoon, my sissy clit became semi-aroused. Megan and Melissa, were always handing me a tissue to wipe my pre-cum. No stains remember. More than once, Amanda would catch a drip on her fingers, she would either lick her own finger or finger-poke my mouth to lick my juices off her finger. She giggled each time, I smiled back.

Although I had seen pictures of girls in camisoles, Camis, corsets, garters, I never really knew what they were called. What boy didn't hide the VS catalog. My sisters gave me an education today. Then there was silk, satin, lace, spandex, cotton-ugh, nylon, sheer, stretchy, and mesh. My head was spinning. Then pantyhose, stockings, thigh highs, anklets were rolled out. It was an exciting afternoon.

Everyone was in a state of dress/undress all afternoon. I must admit, I had witnessed glimpses of my sisters in their bras and panties, bikinis, but never had I witnessed this display of immodesty. Each one sported a bald pussy.

Melissa glanced at her watch, then she spoke up, "Ok girls, it's time. In honor of the occasion, let's all get dressed in a sexy lingerie set. We have a little ceremony to perform to welcome Jennie into our circle of sisterhood." Melissa, completely naked, now spotted a pair of black lace panties, wiggling her booty into the garment as she found a matching lace bra. She pushed her DD sized boobies into wired cups. A pair of sheer black thigh highs were rolled up her gorgeous legs, then she slipped into the pink wedgies I wore earlier. She excused herself, saying she was going to get the fire pit set up.

Megan sorted through the lingerie pile on the bed. She wiggled her generous boobies into a red lacy bustier, with slipped into a matching G-String. Looking for shoes, she left the room, mumbling that the pair she wanted was in her closet. That left just me and Amanda. I was standing on a stool in the middle of the room, she looked up at me, saying, "I think it's appropriate that you wear white." She stood before me completely naked. I admired her poise and her firm body. All the Madison girls had nice, full boobies. Amanda's nipples were pink and perky. Her gorgeous legs met at her bare V. Her booty confirmed that she spent time at the gym. I had to remind myself that she was my younger sister.

She found me a sexy, lacy white corset, with a push up bodice and satin garter straps. I slipped in the garment as she buttoned up the back to tighten the corset. I stepped down, she handed me a pair of sheer white seamed nylons. I sat on the edge of the bed, rolling the stockings up on each leg. We clasped the top of the stockings to the corset. The slight pulling of the stockings was unbearably stimulating. I had to calm my heavy breathing. We found a pair of red 3" platforms heels. They were much easier to walk in. I stepped back on the stool.

My sissy clit was fully aroused now. Amanda simply said, "We need to do something about that!" She ran her lips up and down each side of my shaft, stopping at my balls. She gently squeezed them. As she moved her mouth to the sissy clit head, she immediately guided my shaft deeper and deeper into her mouth. My body tensed up as she slid her mouth all the way down my shaft. I rested my hands on her shoulders, I stuttered, Amanda's name, to no avail. I filled her mouth with my load. She sucked in all my juices, swallowing as much as she could. She rose to kiss me, trading my own juices with me. It was not a sisterly kiss.

All, I could say was, "Wow, yes you need to give me lessons!" Amanda went to Melissa's dresser, finding a pair of scissors and a spool of blue ribbon. She clipped a piece of ribbon from the spool, returning with a white lace string bikini that matched the corset. She then licked my sissy clit clean, tying the ribbon in a bow around my shaft. I then stepped in the string bikini fitting it snugly over my sissy clit and up the crack of my booty. I looked at the floor length mirror. I couldn't imagine that the image in the mirror was me.

My day was amazing and there was more to come. I stood there in a daze, waiting for Amanda to get dressed. She astounds me with her talents. She slipped into a black satin bustier with a hint of lace, her thong pantie matched the bustier. She looked for a pair of thigh highs but opted not to, instead slipping her feet, one by one into red 3" slingbacks. Her tanned athletic legs were breathtaking. The entire ensemble complimented her blonde hair and her perfect round booty. All the Madison women, including me, have been bestowed with perfect booties.

We returned to my room to get my basket of underwear. I heard the front door open, as we walked, together, down the second story hallway to the stairs. I overheard Megan whispering to someone. By the time we reached the top of the stairs, Megan was at the foot of the stairs alone. She looked up at me and Amanda, smiling, "Come here my sexy little sisters." She gestured for us to join her and Melissa outside in our courtyard. The are five plush comfortable chairs that surround the propane pit table. Melissa has the fire blazing. It's very cozy in our private setting. I set my basket to the side. She has champagne flutes on the table.

Melissa remarked on sexy outfits that each one of us were wearing, expressing, "If only our mother could see us now. Her four daughters all sensually attired in stimulating lingerie. She will be proud of us all." I looked at her perplexed. "No Jennie, she is not joining us today, but were have a good friend that will be here shortly!" As my mouth opened wide, Aubrey sauntered out into the courtyard. She was addressed aptly in a blue silk camisole adorned with sheer cobalt blue thigh highs. The camisole snapped at the crotch. Her ankle strap matching 3" heels completed her outfit. Aubrey is very stunning woman.

I took a deep breath, staring at Melissa in shock. Before I could say anything, Melissa stopped me. "Jennie, Aubrey's presence here today is very fitting, and you know it!" Taking another deep breath, I shook my head yes. Without question it was. She is a good friend of my sister Megan and Aubrey Taylor Murphy was my first real crush. Well, more than a crush, as we explored being boyfriend/girlfriend at one time. We have since progressed into friends with benefits. Sex between us has always been terrific. Aubrey, based on her ATM initials, is often known by her nickname Cash.

Cash smiles directly at me, "This little situation doesn't surprise me. I always wondered what was happening to my sexy panties. I bet you have a hidden stash that includes my stuff upstairs in your closet." I just snickered. "Well Jamie, I must say, you are now a stunning female! I am more than a little jealous."

My sisters were snickering, then Melissa spoke up, "Her new name is Jennifer Nicole. Let's just call her Jennie for now." Turning to me, "Jennie dear, let's get our little ceremony started!"

I gave each sister and of course Cash, a handful of my male undies. I kept a pile for myself. As if on cue, we each tossed my male undies in the fire pit. I gasped a little, as they slowly they started to burn, then burst into flames. No turning back now. All five of us cheered. A calmness took over my body. Melissa interrupted with a toast to my sisterhood. Megan left then returned with some cocktail snacks. Melissa reminded me that I was to take small feminine bites.

Melissa and Megan brought Cash up to date as to what's transpired today. In doing so, she explained my new role around the house, emphasizing that all my duties would be done dressed as Jennie. She then made a surprise announcement, at least to me, that she will be moving to Annapolis to live with her boyfriend John in a couple of weeks. She immediately turned to Cash, smiling, "Cash will be moving into the fourth bedroom next weekend." That was certainly new news for me, perhaps even a bit awkward.

Amanda perked up, speaking directly to Melissa, "Does that mean I can move into your bedroom, sooner than the Spring?" Melissa nodded affirmative, then gazed at her at her cell phone pinging. "Oops my plans have changed for this evening; I am now meeting John in Annapolis tonight. I will be back in the morning, for our Jennie shopping spree." Megan interrupted confirming that she was leaving for the evening shortly, too. That left me, Cash, and Amanda. We looked at each other, giggling. Melissa looked at me sternly, "Jennie you will clean up first!"

Megan and Melissa scooted upstairs to finish dressing. Amanda was tidying up the courtyard around the fire pit. Cash helped me with assistance in the kitchen. Cash squeezed me gently on my bare right cheek, saying, "Jamie, you are so stunning as a girl. You are radiant. Tonight, you look like an innocent bride on her wedding night." Grabbing my hand, "We have some unfinished business upstairs, so let's go!" We sprinted up the stairs directly to my bedroom. We tumbled on the bed, kissing each other uncontrollably. We have been sexually intimate in the past, however, tonight was to be quite different. We were in intense heat.

Neither one of us heard Amanda enter the room. She crawled on the bed, sitting quietly beside us. We eventually discovered her presence, bringing her in to embrace us. Cash wiggled down to explore my sissy clit, discovering the blue ribbon tightly tied around my semi aroused clit. Obviously amused I heard her chuckle. Cash began sucking my sissy clit through the thin lace, then moving the fabric away, freeing my sissy clit so she licked both sides of my shaft, tonguing my helmet, then returning down the shaft.

Meantime, Amanda broke away from our embrace positioning her lower body directly in front of my face. I know you are my sister, but the sweet aroma of her satin covered pussy overtook my cautious senses. My lips instinctively started kissing her inner thighs, with my tongue and lips working its way to kiss her pussy through the satin.

Cash, turned me on my back, releasing my sissy clit from G stringed pouch, she then mounted my fully aroused clit, easing her vagina down my shaft. Her body fit comfortably over my mid-section enabling her to control the movement up and down my shaft. My sissy clit became engulfed by her pussy. By reconfiguring my body, my mouth slipped away from Amanda's sweet pussy. Not satisfied with that, Amanda removed her damp thong, positioning her pussy on my face. As my tongue entered her vagina, Amanda was grinding her pussy in face. My face was soaked from her juices. She moaned with each flick of my tongue.

I maintained a steady pace with Amanda's movement while I tried to match Cash's thrusts on my sissy clit. I whimpered with each downward thrust. I no longer had control. I heard Cash scream, followed by a louder scream of excitement than a full shake of her body. Shortly afterwards, I could feel my sissy clit explode. Not to be outdone, Amanda moans quickened, my face became wetter as her thighs tightened around my face. My sissy clit remained hard in Cash's pussy. Then our bodies collapsed in a pile.

Gathering our composures, we were all giddy. We sat there acting like schoolgirls, that not far from being the truth. Cash pressed me wanting to know more about my transformation today. I told my story. I was captivated by the fact that my whirlwind day had been so breathtaking. I was thrilled that Jennifer Nicole was finally out in the open. Cash sat in the middle. Both Cash and Amanda hugged me. Cash turned my head to face her, as she leaned in to kiss me. I kissed her back. We embraced. I felt that it was more than just a sweet kiss.

Then surprisingly she turned to Amanda. Kissing her full on the lips. Amanda kissed her back, pushing her tongue deep into Cash's mouth. Cash reciprocated.

I was captivated by the realization that I was now kissing and hugging two beautiful females that are so scantily clad came to the foreground. It produced goosebumps throughout my body bringing me back to reality that I too was dressed as a sexy female. I took a few deep breaths. My mind shifted again, one was my sister, and one was my former girlfriend, that would soon be living with the same roof. It has been an extraordinary day!

What will happen tomorrow?

To be continued

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