Jennifer Nicole's Coffee Rendezvous

Rendezvous for Coffee

The chapter continues the evolution of Jamie's double life. Her sisters Melissa, Megan and Amanda helped Jamie start his journey as his alter ego Jennifer Nicole. The weekend turned into the beginning of Jamie's transformation as Jennifer Nicole. We now will embark on the dual life as Jamie and Jennifer Nicole. 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. In this stage of the Jennifer Nicole 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.

Jamie attends classes at the University as a male. Jennie, or Jen, his alter ego emerges, almost daily outside of Jamie's school responsibilities. In this chapter Jennie will go on her first date with a fellow University student.

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. Jennifer Nicole 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.

So, the life story of Jennifer Nicole Madison's Kinky Adventures continues by adding yet another chapter, at this point in her life's journey.

I woke up early. I was enthusiastic, not because I had college classes this morning, instead the excitement was that my first public date as Jen was this afternoon. I had a lot to do, so I needed to get my day started. As I hopped out of bed, I realized that I was wearing a sheer black nightgown. A tingling sensation engulfed my body. Without thinking I headed downstairs.

I left my bedroom, started down to the first floor but abruptly stopped in my tracks. Melissa was at the front saying goodbye to her boyfriend John. He had spent the night and was now presumably off to work this morning. He really doesn't know about Jennie, but Jennie knows about him. Jennie, last night, while John was blindfolded and tied to a dining room chair, was initiated into the art of being a good little cocksucker. John will find out about Jennie, but not this morning.

When Melissa closed the front door, she waved to me to come downstairs. I enthusiastically ran down the steps. I needed to tell her about the texts with Naomi last night. Melissa motioned me towards the kitchen, I joined her at the counter. She was also in a sheer sleeping gown, showing off her almost perfect boobies. I started to speak, but Melissa stopped me, saying, "Jamie, err Jennie, I must remind you about our agreement. You do remember, don't you? "I nodded affirmative! She simply said, "Coffee please!"

I went to the coffee machine, to pour us both cups, handing a cup to her., she said, "Okay sister, what are so excited about?" I sat down to tell her about the texts exchange late last night with Naomi the clerk at VS, that she was also University student, that she wanted to meetup and our coffee date at 4 o'clock today, with me dressed as Jen. Melissa grinned, "Do you honestly think you are ready to pull this off?"

I gulped, shaking my head no. I did everything I could not to cry. I looked back at Melissa, blurting out, "But I want to! I need to!" I then told Melissa about the incident in the dressing room, revealing that Naomi clearly knows about my secret, but still wants to get to know me better. I emphasized that the "get to know me better as Jen,' were Naomi words. Megan, also in her sleepwear, although it was a little more modest gown, joined us at the counter. I fetched her coffee. I brought Megan up to speed. All three of us talked as sisters again. I am still amazed by the support my sisters have given me.

Melissa was soon off to work. Megan and I both had classes this morning, so we agreed to meet back at the house around 2 o'clock. She would help me with my makeup, my outfit, and of course support and encouragement. I returned to my bedroom, showered, shaved my body as best I could, donned one of my new satin thongs, then dressed as Jamie to go to class. I have two classes this morning.

During the entire time in speech class, all I am doing is thinking about seeing Naomi. What will I say to her? How will she view me? I tried to stay focused. After my speech class, I went to the Student Union for a snack. A few friends from high school were hanging out in the Baltimore Room. The group today included my senior high prom date Karen. We were never really a high school thing; we just didn't want to miss the prom. I am not sure who asked who. If only she could see me now. Two guys, Robbie and Steve were also hanging out today. I have known both since grade school. We chatted briefly about Sports and this weekend's big game.

I moved on, heading across the Quad to my Marketing Strategy Class. I sat in the back in case I wanted to skip out early. Staying until the end of class, I rushed off to catch a shuttle bus on Route One. The scheduled shuttle will drop me close to my house. After a short walk, I dashed into the house. Megan was waiting for me at the doorway, pointing towards the second floor saying, "Let's go take a shower Jennie!" I tried to balk, but Megan stopped me, remarking, "I have laid out a couple outfit options on your bed, but I want to make sure you are hairless everywhere you need to be!"

I went straight to the bathroom, removing my male clothes along the way." My sissy clit was a little aroused, as I hopped into the shower, I then felt Megan's naked presence behind me. I was a little startled, but calmed down slightly, as she began scrubbing my back. Turning me around she soaped my chest, moving down my torso. She stopped at my stomach.

Along the way, she was inspecting any parts that needed touch up. I was aware that my body was silky smooth, but her inspection calmed my apprehension towards my upcoming date. As she moved in closer, my now aroused sissy clit pushed against her naked body, she smirked at me, "What have we here, Jennie?" She reached down with her right hand, squeezing my shaft. At her touch, I moaned. "We can't have you sporting a hardon on your first date." With her hands filled with soapy suds, Megan began rubbing my sissy clit.

I began to tense up, my legs weakened, I abruptly dropped my load in the palm of her hand. She brought her cupped palm, filled with my juices to my mouth. "Lick my hand clean little sister!" I quickly slurped my juice from her hand, gagging as I swallowed, on juice intertwined with the soapy suds. Megan, chuckled, "You need better control of your sissy clit Jennie dear!"

Megan used the spray wand to clean off the suds, I stepped out of the shower, feeling a little humiliated being jerked off my one of my older sisters again. I toweled off sitting in front of the makeup mirror, Megan helped me with the steps; moisturizer, foundation, concealer, highlighter, then using the brush she deepened the contours. She finished with the eyes, keeping it light, since it was an afternoon rendezvous with Naomi. Megan taught me how to apply the make up as well as the use of the brushes throughout the process. We selected pink lip gloss to finish up.

Stepping back, Megan proudly said, "You are beautiful Jennie! I am a little jealous!" Staring back into the mirror, I smiled widely, as I didn't recognize myself. I agreed that I looked lovely as a female. I am so fortunate to have the support of my sisters.

Looking at the clock, we both hurried back inside my bedroom, I slipped on my adhesive breast forms, I then clasped my pink underwired satin bra highlighting my bustline. I wiggled into a pink satin thong. No longer aroused my sissy clit fit snugly. Megan stood by helping me dress, smiled at me then squeezed my clit tenderly, making sure I was indeed soft. We selected a hot pink wide waisted pleated skirt, matching it with a white mock neck satin blouse. I found my favorite wedgies. I stood up, twirled in front of the mirror, smiling back at myself, I was more than pleased. Megan agreed, asking me if I was mentally ready. I took a few deep breaths, commenting, "Yes, I think so, hope so!" I gave Megan a peck on the cheek.

I looked at my cell, it was time to leave. I was quite anxious, shaking a little in anticipation. I found my purse, filled it with money, wallet, and car keys. Megan tossed me the lip gloss. I ran as fast I could in my wedgies down the stairs and out the door, headed for my car. I was so excited, I didn't even think about anyone outside that might know Jamie, now dressed as Jennie. The coffee shop was not far away, but I did not desire to exceed the speed limit. I didn't want to be caught speeding dressed as Jennie.

The drive to the coffee shop took about 15 minutes. It dawned on me that it might be too close to campus, so I hope that I am not recognized. I couldn't do anything about it now.

Naomi sent me a text saying she was running ten minutes late. I texted back a smiley face. When I arrived at the shop, I parked, facing the shop entrance, so I could see when Naomi arrived. My heart was racing. I took a few deep breaths, trying to calm down. I told myself, I wasn't backing out now, but I wasn't going in the shop until she got here. Was I nervous, you bet I was.

A white sports car sped in the lot, parked quickly, Naomi hopped out of her car in gray spandex leggings, that highlighted her perky booty and her gorgeous athletic legs. Her turquoise blue crew neck blouse complimented her casual look. When she entered the coffee shop. I noticed her looking around the store, assuming she was trying to find me seated somewhere, hoping I am sure that I wasn't a 'no show'.

I took two more deep breaths, hopped out of my car, then walked hurriedly to the entrance. I saw Naomi retreating to the counter, I hurried to her side, whispering, "Naomi, are you looking for me?" Naomi turned, saying "Yes, Jen!" We embraced. "Sorry I am late." We ordered our lattes, then found a table off to the side.

Still feeling incredibly nervous, and cognizant of who eyes might be strangely looking at me, I mumbled, "I am happy that you are here." Sensing my anxiety, Naomi reached to hold my hands, commenting, "No, I am so happy that you have the courage to meet me, Jen. You are looking gorgeous today! Hot pink is a great color for you. "I smiled back, thanking her for very kind compliments, saying, "I love your smile. I was so nervous in the store yesterday I did not realize then how beautiful you are. Thank you for reaching out to me last night! "Small talk followed. I have never been good at it.

Naomi was gorgeous. She is olive skin toned; her smile radiates, and her eyes are riveting. Looking closer, one eye is blue; the other eye is green. As we talked, she held my hand. Her pearl manicured nails are perfect. Someday, I will have pearl nails. Naomi indicated that she has an Italian American heritage. She grew up in Potomac, Maryland with her siblings, both older; one brother and one sister. She is also a sophomore at the University. Her desired major is Art and Design: she commented that she may transfer to a design college in New York, California or perhaps Baltimore. Her close friends call her Mimi.

We exchanged more information on our upbringing. I indicated that she had already met two of my three sisters nd of course my former girlfriend now a good friend. I emphasized that again. Since we both grew up in the DMV area, I was from nearby Anne Arundel County that provided us with a common bond.

Our conversation has been both intriguing and enjoyable, but we haven't yet addressed the pink elephant in the room. I was trying to determine how to break that barrier. I had no idea where this conversation was headed but I do know my sissy clit was now semi aroused just being with Naomi. I needed time to think, so I stood, picking up both cups, I asked Naomi if she wanted another latte. She nodded affirmatively. I could feel her eyes on my boots, so I wiggled a little. It was breathtaking to be dressed in my short pink skirt.

Returning with our drinks, Naomi was talking to a hunky young man. He was carrying a backpack. I recognized him as being a fellow student in one of lecture classes. When I returned to our table, Naomi introduced me to Josh, remarking that Josh and she graduated together from the same high school. She, of course, introduced me as Jen, her new friend from school. Josh looked at his watch, excusing himself, saying that he needed to get to work. I was relieved that he didn't seem to recognize me.

When he left, I took a very deep breath. I am doing that a lot lately. Naomi softly blurted out, that Josh thought I was cute and wanted my cell number. I took another deep breath. Naomi quickly added, "No I didn't give it to him, and yes he is unaware of your surprise!" I told her that she was in one of my lecture classes. Naomi gasped. With the pink elephant now out in the open, we began to talk about me being femme and her attraction to the femme me.

Naomi started first. She favored her comments, saying she felt obliged to set the stage as to why she was attracted to me. Naomi stated that she has waited on men at the VS who said they were shopping for their girl friend or wife. She added that their secret was always revealed when they knew too much about lingerie. A dead giveaway she stated. On other occasions, a couple, male and female, would be shopping together, although she never could completely determine their relationship. It did come to the surface when the sizes they were buying were not the size that would fit her.

Another time, a guy handed her a list of items he was sent to purchase. She read the list; it was signed Mistress Brianna. She said it was entertaining assisting him that day. She knew who he was shopping for, but he didn't know she knew. She then took a deep breath, apologizing for the long-drawn-out assumption of her affection for me as Jen.

She stated that assisting me on Sunday was captivating and highly stimulating. I tried to ask a question, but she squeezed my hand to stop me, quietly saying please let me finish. She went on, saying, "Jen, you completely fooled me. I didn't quite believe the story of you being French, but I played along with you and your sister. The dynamics between you and the other three women with you also didn't not fit into a visiting French girl. I did, however, take it that you were all women, French or American or whatever. She stopped talking as she smiled directly into my eyes. I felt mesmerized.

She pushed my hand tighter, continuing, "When I saw you naked in the dressing room, wearing a chastity cage on your cock, I was amused but also excited. I was so stimulated; I felt my pussy leaking, so I hurriedly left the dressing room. Once I composed myself, I knew it was essential to my self-being to know more about you!" It was her turn to breathe deeply. It was my turn to squeeze her hand.

Naomi tried to continue, as I reached out to hold both of her hands, saying it was my turn to talk. Taking a breath, I talked about my weekend. I was so excited to finally dress as a woman; I was relieved to no longer conceal my secret. To finally be able leave the confines of my own room dressed as a female. How my sisters and Cash showed support for me as a person, not how I was dressed. My truth was now in the open. That was a very calming experience.

Naomi interrupted stating that the camaraderie between the four of us was an overriding reason to reach out to me last night. I surprised myself, as I started to show some emotion. Naomi used a napkin to wipe a tear from my eye. As we talked a question kept resurfacing. I needed to ask her, but I struggled to understand how to do it, so I blurted it out anyway," Naomi you say I intrigued you, that I am brave, but why so?"

Naomi simply smiled. "I enjoy being with a masculine man and I enjoy the affection of other females. I am aware that I am bisexual. That's being true to myself, I firmly believe I will find my happiness when I live my truth. I see that in you, too. I find beauty in the feminine body, although I enjoy pussy, but I don't want to limit myself. A female body with a cock is a magnificent vision. That's you Jen!"

I clutched her hands, I was overwhelmed. I can't believe this is happening in a coffee shop, dressed in a short, pleated skirt. I could feel my sissy clit fully harden in my pink thong.

Naomi resumed talking, "Jen, talking with you today, wants me to know more, to learn more. I'm willing if you are, to explore a friendship. I believe I want to know Jamie too, but I know I want to know more about Jen. "I beamed, staring directly into her eyes, saying, "I do too!"

Feeling the emotions of the moment, I motioned that I needed to use the restroom. Standing I picked up my purse heading to the back of the shop, thinking it's a good thing that rest rooms here are unisex. Hearing footsteps behind me, I noticed Naomi was trying to catch up, "Do you mind if I join you?" I grabbed her hand. I opened the door, letting Naomi to go through the door first, turning to lock it behind us, Naomi's hand was on my shoulder.

She turned me to face her, at the same time pushing me back against the locked door. We embraced, I closed my eyes, then instinctively tilted my head to my left side. I gently pressed my lips against hers intending to hold my kiss for a few seconds. Naomi forced her tongue into my mouth. We became aggressive, both showing a lot of passion. If we were anywhere else, we would both be naked. My hands went down to caress her booty through her gray leggings. I pushed my aroused sissy clit into her abdomen. We both moaned passionately.

Naomi found the hem of my skirt, trying to find my sissy clit. Discovering how hard I was, she immediately dropped to her knees, pulling my pink thong down my legs. She lifted my skirt, pushing her face and mouth sucking the tip of sissy clit, twirling her tongue around the tip. I tried focusing on anything else besides her tongue on my sissy clit. Naomi momentarily pulled back, her head still under my skirt incoherently mumbled, "Jen you taste so sweet, so warm! I want your precious dick."

I tried to calm down. I didn't want to release my juices prematurely. I tried raising Naomi off her knees. She resisted, forcing her mouth back on my shaft, while clutching the lower end, she was making slurping sounds. My sissy clit went deeper into Naomi's mouth. She wrapped her lips tightly around my shaft, I tensed, whimpered loudly as I filled her mouth with my juices. Her mouth loaded with my cream then she rose to be face to face with me. Naomi leaned in to kiss me, opening our mouths, we shared my sweetness. We both swallowed my cream.

We collapsed into each other's arms. Doing so she pushed me back into the locked door, making a loud noise as we pressed against it. We then heard a shake of the handle, then a female voice saying, "Is everything ok in there?" Naomi answered, "Sorry, I'll be right out." I pulled my thong back up my legs, tucking my shaft between the fabric. I straightened out my rumbled skirt. Naomi picked up both purses from the floor. She glanced at the mirror, shrugged her shoulders, turned, and grabbed my hand, saying "Let's go."

No one was standing immediately outside the rest room door, so we hurried down the short hallway, we passed a young woman sitting at the first table. She looked up from her laptop, commenting, "Next time invite me, I am always up for a good time!" The coffee shop was not filled, as we rushed to reach the exit all eyes were staring at us. It appears that we were louder than we thought.