Shopping Spree with Sisters and Cash
Jennifer Nicole continues to evolve. The chapter focuses on the early beginnings of Jamie’s double life. Her sisters Melissa, Megan and Amanda helped Jamie start his journey as Jennifer Nicole. His ex-girlfriend, Aubrey, also known as Cash, has been invited to participate in Jennifer Nicole’s transformation. This story contains sexual activities and situations between consenting adults. All characters are above the age of 18. Any similarity to any individual, living or deceased, or any location, is purely coincidence and unintended. Most of her family and close friends, with the benefit of being able to comprehend and appreciate her exploits, are aware of and love her. Nikki is very cognizant of the importance of safe sex. She uses a highly effective preventive medication that reduces her and her partners’ risks for disease.
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. This stage of journey my persona evolves into Jennie, the budding female trying to fit as the new girl; then As Jen, I became just a college schoolgirl. I could dress in cute little outfits that embodied my innocence.
My story continues.
The three of us were exhausted, so we decided to get some sleep. Amanda jumped off the bed, running into Melissa’s bedroom. She recalled seeing the sexy nightgowns, from the afternoon Jennie fashion show. She returned with three gowns, a sheer black mid length, a red satin full length gown and a blue baby doll negligee. She handed Cash, the sheer gown, keep the red satin for herself, then tossed me the baby doll, perfect for my new sissy self. It was a short, sleeveless, loose-fitting nightgown, short, sleeveless, and loose-fitting nightgown.
I wiggled into my gown, then the three of us pulled the sheets down. Cash was in the middle, snuggled in the curvature of Amanda’s back, I cuddled next to Cash, placing my sissy clit in the crack of her booty. Last night I slept alone, tonight, I slept in the same bed,with two sexy women as a woman. We fell asleep.
I woke up early, my head spinning. I reflected on yesterday. I was pondering how I got to this point. I know that whenever I have worn sexy lingerie, whether a bra, or panties or whatever some of the items I wore yesterday my sexual hormones have skyrocketed. I enjoyed doing it, I relaxed and yes it gave me pleasure. I yearned to repeat it, often.
This morning I kept questioning myself. I kept repeating the questions and my answers in my head. Yes, I have I always liked women’s clothing? Yes, women’s clothes are more beautiful than men’s? Yes, I have been influenced by my sisters and my mother. Yes, I feel sexual pleasure when dressing like a woman. Yes, I like the feel and touch of female clothes on my body. No, I really do not feel shameful, guilty, or remorse dressing as female. Yes, it is stressful, trying to hide it. I always feared getting caught. I was caught yesterday.
Yesterday was quite remarkable. The joy of being female attired is still uplifting. Will the enjoyment of being female, and that’s more than just dressing female continue? I am sitting here, in my blue baby doll nightgown aroused and desiring more. I want to have my own bras, panties, stockings, garters, skirts, dresses in my daily life. I want it all. When I look in a mirror, I need to develop a feminine personality, even if Jennie and Jamie are distinct individuals.
My thoughts refocus on my sisters and Cash. They have been very accepting. I have been awakened by their actions. A lot to take in on this reflective morning. My former girlfriend accepted Jennie, without any reservations. I also learned yesterday that she is bisexual. That’s a marvelous discovery. I also learned that my younger sister was too. She is also more sexually active than I was aware.
My sexuality is yet to be determined. I do have a lingering unanswered question. Is it possible to become successful by dressing like a woman yet still living as Jamie? Today I may find that out.
My reflections came to an abrupt halt. I heard the front door open; Melissa was home. She yelled, “Where is everybody?” Not hearing a response, I heard her quickly climb the stairs. She flew through the doorway into my room. She stopped in her tracks. Looking around the room, she smirked, “So here you are!”
Amanda and Cash were still in bed together. They popped out of the covers, hearing her enter the room. Then she saw me in the chair. Seeing the bed disheveled, she remarked, “It appears that all of you shared the same bed last night. I assume that the three of you had a fantastic time last night. That’s fantastic!” Looking at her watch, “It’s time to get dressed. We have shopping to do! Is Megan back?”
I got up to put on a pair of jeans and t shirt. Melissa stopped me. Turning to Amanda and Cash, “Both of you help Jennie dress. She is shopping for Levent travesti female attire, so she will dress as a woman, no ifs and or buts girls!” My jaw dropped. Ignoring me, she left the room and headed for her bedroom.
Amanda and Cash turned to each other, in unison, “Ok, let’s do it.” Cash, dropped her sheer gown to the floor, grabbing my hand, “Let’s get in the shower.” Amanda said, “I will get her an outfit!” She left the room.
In the bathroom I removed my baby doll negligee, then stepped into the shower. Cash joined me. She grabbed the liquid soap, squirting it into her hands, she began lathering my body. The shea soap and a razor were still on the shower shelf. Cash squeezed my sissy clit to remind me who was in charge. She used the shea soap and razor to touch up any areas we may have missed yesterday. Happy with her results, she tossed me the soap, “Do my back!”
I gladly obeyed. Her body is exquisite. I lathered her back; her booty, then turned her around to soap up her boobies. Running my soapy hands down to her bare vagina. I slipped a finger between her lips, clearly getting a reaction. She reciprocated by squeezing my sissy clit again. I was now fully aroused, smiling she said, “We’ll take of this later. We now need to get dressed.” I was disappointed. We grabbed towels to dry off. I shaved my face, trying not to miss any area. Cash left the room, to retrieve her purse and makeup.
Amanda came back holding a short pink pleated shirt, white blouse and matching bralette/pantie set. Cash returned with her purse and brown shopping bag that Melissa had given her. Cash remarked that Melissa had stopped by the fetish store on her way to see John. In the bag she found two boxes. She pulled one box, that contained adhesive breast forms that fitted to my upper chest covering my nipples. Looking at the bra, she smirked, “It looks like your new boobies won’t fit into this bra!” She then turned to me. “Jennie dear, in your lingerie stash, I am sure you can find one of my bra and pantie sets that you took from me?”
Without hesitation I rooted through my stash that I had hidden in one of my suitcases. I held up several sets. Cash took the pink lacy pair from my hands. “I remember these!” She tossed me the bra. I started to clasp it at my stomach, turning it around, to snugly fit it to my new boobies. I smiled as I caught a glimpse in the mirror. Cash kneeled, to help me roll the panties up my legs, I wiggled to help her, but she abruptly stopped. Amanda had been examining the other box. She tossed it to Cash. She left to get dressed herself.
When she opened the box, out popped a pink silicone chastity. I gasped! I knew exactly what it was. Cash grinned.” Melissa said we need to put this on you. We can’t have you staining any clothes you might be trying on today.” I gasped again, realizing I would be trying clothes on, not just buying them today.
Cash fumbled with the cage, trying to picture how it fit. She found one of the rings that fit snugly around my balls. She squeezed my sissy shaft hard to break down my semi-aroused clit. She did it again. It worked so she fit my shrinking shaft in the tube. She securely locked the rings and the shaft with the small lock. She kissed my cage, saying “Perfect! Okay let’s do your makeup!” I rolled up my pink panties, snugly fitting my sissy caged clit into them.
She kept the keys, sliding them down her gold neck chain. The two keys fit nicely, if I may say, as they dangled between her splendid globes. I sat at the chair in front of the mirror as Cash, naked, began applying my makeup. I could feel her heat. She leaned in more than once, rubbing her body against me, teasing me. The entire time, I tried to focus on my transformation in the mirror, not her toned body next to me. My sissy clit strained in my chastity cage. I tried to calm myself with deep breaths.
Amanda, dressed in her short red skirt, white and red blouse and wedgies, came back into the room. She had wedgies for me. Also, short sheer lacy socks, or as she explained to me – anklets. They are cute and made me more feminine. Amanda smiled. Cash, left to find an outfit to wear. She returned in a short blue skirt, low cut white blouse. She also wore wedgies.
Melissa was calling for us, so we all twirled in front of the floor-length mirror. Happy with what we saw, we hurried downstairs.
Melissa met us at the door. He said Megan might join us later, but it would be just the three of us. She looked at Cash, “Is she caged?” Cash nodded yes, then pulled her gold chain up, showing the dangling keys to Melissa. She dropped the chain back between her boobies. Melissa just grinned.
We headed to the Northern Virginia suburbs, to an expansive mall that had an assortment of clothing stores. One store was the infamous VS, that every young man yearned to visit. My hormones always ran wild either looking through their catalogs or walking through the mall stores. We arrived at the mall. My heart was racing. Cash, Levent travestileri sitting next to me in the backseat, was holding my hands trying to calm me. I took many, many deep breaths. I was nervous, mumbling what I had gotten myself into. I was second guessing my decision, everyone one of them.
Cash squeezed my hand a little forcibly this time, staring at me sternly, “Look girlfriend, you can do this. We are four stunning women shopping the mall. Yes, four stunning women. You definitely will be looked at as a woman, not as a man. Trust me no one will know the difference!”
She continued, “Every guy that stares at us will be trying to figure out how he can get into our panties, then which one. You included. Every woman will be saying to themselves, how can I look as good as they do. No one will have any idea. Do you understand, sweetheart? So, open your door and let’s go shopping!”
I opened the door. We strutted together into the mall.
We went into many stores, a few national chains, a few trendy stores and of course the classic clothes outlet stores that all women can’t resist. If I had to try anything on to see how it fit me, one of the girls went in the dressing rooms with me. Occasionally a clerk would hover outside the curtain, but either Melissa, Amanda or Cash would protect me No one suspected anything. We slipped into an outlet shoe store. I stopped counting the number shoes I slipped on and how many I just couldn’t live without. I could become a shoe whore. It was exhilarating.
At many of the stores we were buyers and sister did we buy. Melissa told us not to worry, as the bills were her responsibility. Our goal today was to get me outfitted. It was fun and I learned a lot.
I had many new outfits. Mostly casual, skirts, dresses, leggings, tight jeans, a variety of blouses and tees. Even a few pieces of jewelry. We also bought a variety of different styles of shoes.
We did stop for a brief bite to eat; we didn’t stay long at the restaurant as we had more shopping to do. Then we were standing outside of the infamous VS. Melissa had saved the best for last. She held my right hand; Amanda took my left hand and Cash gabbed Amanda’s. We walked in hand and hand. I looked around not knowing where to start at first. I was a kid in a candy store, but actually I was now a new, young woman.
An attractive clerk approached us welcoming us to the store, introduced herself as Naomi, then asking How she could help. Melissa alluded that I was they cousin from France, by doing so, she thought I could avoid talking. We were both surprised, when Naomi looked directly at me, speaking fluent French. “Bonjour, enchanté! Luckily, I had almost twelve years of French in school. I answered back in French, “Bonjour, Je parle un peu anglaise.” to also allude that I did speak a little English.
I glared at Melissa. Thankfully my conversational French was adequate. Melissa asked Naomi to help me with my measurements. The aim was to alter the conversion to American sizing. I was fortunate, that Naomi did not discover my caged clit. With the sizes in hand, we split up to cover the store.
Amanda, then headed for the bra and pantie sets, the single table of panties, and assorted bras. Cash went straight to the sexy lingerie sets, garters, stockings, pantyhose, corsets, bustiers, camisoles and tank tops. Naomi took Melissa and me to the night gowns and sleepwear section. Everyone understood that cotton was not an option. Since outerwear was not an objective at VS today, we all concentrated on sexy undergarments. Everyone’s arms were filled, as we converged at the dressing rooms. Naomi found a table nearby where we could sort out the various garments.
We grouped the garments in separate piles. Lingerie sets were set aside; stockings and pantyhose packets were stacked to one side; corsets, bustier, tanks and camisoles were set aside as these undies needed to be tried on; panties one at a time were held up for a thumbs up or thumbs down. The sleepwear also needed to be tried on. Melissa then held up the lingerie sets in front of my body for all to see. She was looking for colors that match my exposed skin. As we separated the garments into yes and no piles, Naomi took the yes items to the counter behind the registers.The no’s were set aside.
Melissa’s cell phone pinged again, she excused herself to take the call. Cash and I gathered the ‘try on’ lingerie then proceeded to the dressing rooms. Amanda joined us. I had never been in the dressing area in a store like VS, so my heart was pounding again with excitement. Cash and I stepped into one of the changing stalls; she pulled the curtain tight, giving us some privacy. Amanda stood guard, so to speak, immediately outside. Knowing the drill, from our other stops, I dropped my skirt to the floor, and took off my blouse. I stood before Cash again in my bra, panties and of course my chastity cage.
I tried on several gowns, we selected four in different styles Travesti levent and colors. She sat our selections on the bench. Naomi returned, standing outside the dressing stalls. Cash parted the curtain, to hand the yes garments to Naomi. She took them back to the register. I then tried on several corsets. We both loved one of the black lacy ones, but it was too small. She handed the corset through the curtain to Amanda, asking her to find one a little larger. She scooted off.
Next, I tried on a red laced bustier top, but with the breast forms, it too did not fit right. Cash opened the curtain to hand this one Amanda, but only Naomi was standing there. Looking over Cash’s shoulder she saw everything. I was in my breast forms and chastity cage. I quickly moved my hands to covering my caged sissy clit, by doing so I left my breast forms exposed. I think Naomi was as embarrassed as I was, she exclaimed, “Oops, sorry!” grabbing the garment as she dashed off. Cash turned to face me, “Sorry girlfriend! We’ll deal with it.”
Amanda, returned with the corset and bustier, handing them to Cash, saying,” Naomi told me you needed this bustier too.” Cash, recognized that I was agitated, calmed me down. We finished trying on the garments, I dressed in my ‘street’ clothes, then took our selections to the checkout counter. Naomi and Melissa were at the counter waiting for us. We added our selections to the purchase pile. I tried to make eye contact, but Naomi would not look directly at me.
She completed the purchase, then inquired if anyone was a member of the VS club, if so, if you can receive a discount. Melissa interjected, “Let’s add Jennie, nodding at me to give her my cell phone number, email, and address. I did so, but Melissa interjected again, “Her full name is Jennifer Nicole Madison.” Naomi completed the purchase, applying the discount, then bagged all the garments. We had numerous bags, she walked around the counter, giving several to Cash and Amanda, handing me two bags.
Naomi smiled directly at me, ” J’ai eu le plaisirde vous servi, Jennifer Nicole. Profitez de votre lingerie! Reviens Bientot!” I responded, simply, “Au revoir!” As I took the bags from her, Naomi’s hand lingered on mine. I smiled back a little bit awkwardly. As we were leaving the store, I glanced back, Naomi was standing in the same place, still smiling.
Leaving the store, Amanda, pulled on my arm, “What did she say?” I grinned back at her, saying, “That Naomi said, It’s been my pleasure to serve you, Jennifer Nicole. Enjoy your lingerie! Come back soon.”
We loaded the car, filling the trunk with all our purchases, I jumped in the backseat. Traveling home, I had very mixed emotions. I was extremely excited about getting new clothes. I loved everything. I was grateful to my sisters and Cash for accepting me for who I am and who I will become. I was also humiliated being seen in my chastity by the VS clerk, Naomi. Cash, sitting next to me, sensed that I was in deep thought. She knew me well. She placed her hand on knee., saying to me, “Are you overwhelmed Jennifer?”
I nodded, feeling a tear drop sliding down my face. She stopped the drop, then kissed me, remarking, “I’m always here for you Jennifer!” She then cupped my caged sissy clit, looking back at me, “Do you need relief?” I nodded yes. She pulled her gold chain over her head, unclasping the hook, removing one key, handing it me. “Unlock yourself Jennie!” She then replaced the gold chain, with the second key over her head. The sole key dangled between her boobies. Pushing my pink pantie aside, I clumsily unlocked the chastity. Lifting my sissy clit, out of the ring, I took a deep breath. It felt good to be free.
Cash, holding her long locks with her left hand, reached to hold my sissy clit in her right hand, she leaned down kissing the tip of my clit. She ran her tongue around the helmet, inching her mouth down my shaft. I leaned back, whimpering. She gaged slightly, lifting her mouth off my sissy clit, then returning her lips tightly on my shaft. She quickly consumed my sissy clit. My whimpers turned louder moans. I was fully aroused. I felt my body tense, I attempted to warn her, only to explode heavily into her giving mouth. Cash does know how to suck. Wiping her lips, swallowing my load, she remarked, “Do you feel better Jennifer?” Taking a few deep breaths, I simply said, “Thank you!”
Arriving back at the house, the girls helped me take my packages to my room. I was engulfed in a sea of packages. Thinking to myself, where do put everything. Cash and Amanda left me sitting on my bed looking overwhelmed. Megan, having returned to the house, checked in on me, commenting, “Sorry I missed the shopping trip. Jennie, it looks like you did quite well today.”
A few minutes later, Cash and Amanda returned having checked out Cash’s new room. Cash mentioned that she and her Amanda were leaving to girl chat over a couple of lattes. I wanted to go, but I could detect the increased giddiness and sexual tension between them all day. Cash kisses me good night, I kiss her back. She smiled back at me, saying, “Jamie, I’m so happy that we have turned into good friends with benefits. I ‘m excited about expanding the benefits with Jennie!” Amanda kisses me on the cheek, they leave holding hands.