Meet Aubrey Taylor Murphy aka Cash Transgender & Crossdressers


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Meet Aubrey Taylor Murphy aka Cash

Aubrey Taylor Murphy is a good friend of my sister Amanda and 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. between us has always been terrific.

So, the life of Jameson and his alter ego Jennifer Nicole Madison continues by adding yet another chapter, Aubrey aka Cash has played an important role in my journey. This contains ual 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. Jameson and Jennifer Nicole are very cognizant of the importance of safe .

The Summer of Lust

I have known Aubrey since my first year in high school. We hung around with the same crowd. We were never an item. In fact, I don’t think she really cared for me. She didn’t dislike me. We just never clicked in high school. There was no chemistry or attraction. At least we didn’t think so. We soon found out differently.

That summer after graduation were just looking for some fun and action. There were about ten of us who hung together that summer. We all were starting college in the Fall. I was headed to the UMD in the Fall, so was Aubrey. Others were too, some were headed out of state to attend college. We needed a place to hang, sow our wild oats, so the Madison Compound became our unofficial headquarters.

My parents, Abagail and Henry, own a huge house and adjoining property along the Scenic Severn River in Annapolis, Maryland. A guest house and pool are situated on the property. Our private pier was easily accessible. My sisters and I affectionately called the property the Madison Compound.

A perfect hang out for the Gang, the Gang of Ten is what we called ourselves. Most of us had turned 18. Me included Aubrey too. Every day someone from the Gang was at the Compound, either using the pool or the skiffs docked at our pier. None of the Gang of Ten were in serious relationship. No one was exclusive. At night, we watched some TV, and hung out for a bit, do some necking or heavy petting. You know, Hang out Buddies. It was all casual. We ate a lot of pizza that summer along with a few adult beverages.

Aubrey was at the Compound almost every day. My younger sister Amanda would hang with us too. Aubrey and Amanda became friends. So did Parker Barlow, another friend of Amanda’s. Parker and Amanda would be Seniors that September.

Aubrey and I became friendlier, but it was more casual; gowiththeflow so to speak. We kept things light and lowpressured. At least I did.

That summer is when Aubrey and my relationship unexpectedly blossomed. Aubrey is the one that stepped it up a notch. One day, she showed up sporting a y red barely there string bikini. My eyes popped when I saw her. I thought to myself where had she been hiding this body. I was immediately infatuated.

Aubrey’s body is summer bronzed, athletic and fit. Her round perky booty is almost perfect. You could tell that she has been working on her glutes. Her boobies are natural with a nice shape, size, and are almost flawless. They have been on display all day to day. I have stared at them more than once, if not fifty times.

When you look into her eyes you are captivated, then she smiles, you become mesmerized. Her smile is radiant. I am amazed that it took me nearly a month to figure this out. Why should I be; I am still a clueless young man!

Aubrey’s playfulness has really come to the forefront this summer. Most of the summer her brunette hair had been in a ponytail. Not today.

If the wearing of the red bikini was intentional, so be it, but from this summer day forward I started paying lots of attention to her. We exchanged the subtle and notsosubtle signals all day. She stayed late; we grilled some burgers along with some other snacks. I must say I don’t remember. It was just the two of us that night. We watched the sunset over the Naval Academy and the city of Annapolis. It was a romantic evening.

The night air was chilly. We lit the fire pit. We talked; we opened up to each other. On the lounger, we snuggled under a blanket together to get warm. And did we get warm.

In One Summer Day, We Became More than Just Casual Friends

Aubrey removed her top. She placed my hands on her full breasts. She was clearly taking charge tonight. I caressed each boob. My cock was aroused. I slid under the blanket. I kissed her tiny areolas and perfect nipples. I kissed my way up her body, to the crook of her neck. Then her chin and finally a full kiss on her lips. I have never been so aroused. And the heat of her body told me she was too.

Her hands were exploring my upper torso. Mine were on her lower torso. My hands were on her booty. I discovered the strings of her bikini. I loosened one side. Her hand touched mine, gently saying not yet. She pressed her lips harder into mine. We were in heat!

Aubrey slid her torso down my body, kissing and licking my nipples, my stomach. She tugged at my bathing suit, pulling the suit down my legs; my now hard cock popped out, swinging side to side on its own. Aubrey kissed the head of my cock. I gasped. Aubrey’s lips engulfed the head, as she kissed and sucked my precum. I whimpered. Aubrey pushed her mouth over my cock head, she gagged, then giggled. She spoke for the first time,” You taste so good Jameson.” I was in heaven.

Her mouth felt so good on my cock. I continued to moan. Her hand tightly squeezed my shaft at the base. I gasped again. She kissed her way down my shaft, squeezing my balls with her other hand, then she kissed her way back up my shaft. She licked the head of my cock again, still firmly holding the base of my shaft. She knew what she was doing to me. Aubrey was in complete control.

This was the best blow job of my entire young life. By now, the other girls would be jerking my cock, no longer sucking or licking but Aubrey was licking and sucking my cock like an allday lollipop. She was enjoying my hard cock. And I was enjoying her mouth, tongue and lips on my cock.

My body was tense. I could feel the pressure building up within me. I was trying hard to control my ejaculation. Aubrey sensing the same released her grip on my shaft. I screamed, “I’m cumming, I’m cumming.” Her mouth was still sucking on the head of my cock. I exploded intensely; my load was much more than she expected.

She couldn’t keep my throbbing cock in her mouth. Aubrey tried to swallow as much as she could, but my cream went everywhere. All over her face and chin, my stomach and the lounger. Aubrey licked the cream off my stomach, then raised her body to kiss me. She had not swallowed my cream, so with her tongue she parted my lips pushing her tongue and my cream into my mouth. She then used my fingers to remove my cream from her face, she guided my fingers into her mouth, licking my fingers dry.

She smiled at me, with her magnetic smile, then spoke softly, “Thank you Jameson!”

I embraced her, then replied, “No, I should thank you Aubrey!” I paused, then added, “Where did you learn how to suck cock? “

Aubrey snickered, “I watch porn!”

I giggled, “Well we need to watch it together now… and often!” We embraced.

She then whispered, “Jameson, can I spend the night?” I nodded.

Since it was late, Aubrey texted her mother, Leslie, who was also a friend of my mom Abagail. Our parents belong to the same clubs, etc. She told her Mom that she was spending she night at Amanda’s. And that she would be back home in the morning as she had to work for a few hours at the Boutique in Severna Park. Her mom sent back an emoji thumbs up.

She then immediately texted Amanda to tell her that if anybody asked that she Aubrey was spending the night at her house…. with her!

Amanda texted back, ‘An emoji thumbs up, then be home soon.’ Aubrey returned a text with ‘thumbs up, adding, “I am staying in the guest house.’

Amanda’s text reply was ‘An emoji Happy Face with red hearts for eyes.’

Seeing the text exchange, I just chuckled to myself, I was the last to know I was getting seduced today. I am not complaining. We cleaned up the fire pit area, then walked hand in hand into the guest house. We went straight to bed and snuggled all night. We drifted off to sleep.

Aubrey woke up early, kissed me on the forehead, then off she went home and to work. I woke abruptly, realizing she had already left. She left a note on her pillow.

I read it and reread it again. ‘Thanks for being you Jameson. See you this afternoon. ‘

Could The Summer Get Any Better?

Not really! Aubrey was my first real crush. I didn’t know how to act, I was smitten. I so much wanted someone to be attracted to me. Aubrey is authentic and true to her word. What I did learn from Aubrey was to be myself. We talked about everything. We were vulnerable together. That summer I learned how to really talk to girls. I was no longer an adolescent boy.

I taught her how to sail, how to jet ski and she taught me how to lick and suck her genitals. Giving pleasure to your girlfriend, your significant other is the best gift. It is not just about giving; it is about being perfect at cunnilingus. I was clumsy at first but under Aubrey’s directions I got much better. She showed me where to put my mouth, my tongue, my fingers. She taught me when to be gentle, when to apply pressure.

We experimented for the rest of the summer. And yes we did watch porn together. We sucked and licked each other. We shaved each other’s body. I trimmed her pubic hair. She removed mine. I was shaved and smooth all over, so was she. We perfected giving each other oral, or so we thought we did. Truthfully we did give each other good head. Of course we didn’t know any different. Her orgasms weren’t fake. My cream was everywhere.

Our infatuation became more intense transforming into a real connection between us. Before the summer was over we became an exclusive couple.

Aubrey slept over a lot. Amanda was always good cover. They were terrific friends anyway. We stayed in the Guest House, At the end of the summer the Gang of Ten had dwindled to mostly a Gang of three of four.

But no intercourse yet. We were both a little scared. We weren’t timid or fearful. We just wanted to be safe. Then one day Aubrey quietly informed me that she was on the pill. She said she started yesterday. She giggled, “You have five days Jameson!”

The Fifth Day will come in the middle of my relocation to College.

Aubrey Taylor Murphy Becomes Cash to Her Friends

By the end of summer, Aubrey always seemed to be going to the Bank to get cash, the ATM mostly, forty dollars, forty dollars the next time. Always forty. She just liked to pay cash for everything. She always paid her own way. One day, on the way somewhere, Aubrey said she needed to go to the ATM, she needed cash again. Amanda and Parker were also in the car, and it hit us all at the same time. Cash, ATM: Aubrey Taylor Murphy. ATM! Aubrey became Cash going forward. To this day, she answers to Cash normally before she does to Aubrey. Aubrey is her business name.

The Endless Summer Turns to Fall

Classes started two weeks after Labor Day.. It was time for me to move to be near the College Park Campus. I moved right after Labor Day. Henry and Abagail had purchased a fourbedroom house in nearby University Park. It was a perfect off campus housing location for us. A terrific longterm investment for our family. Melissa and Megan, my two oldest sisters were already living in the house. A third bedroom became my room in my Freshman year. The fourth bedroom was rented to Dawn, a College Senior who was a friend of Melissa’s.

Cash helped me move my clothes, laptop, sports equipment, and a bunch of other stuff to the University Park house. We also did grocery shopping. She was moving into her sorority house next week. She was a pledge.

We walked around campus and through the small downtown area in College Park. Stopping at Ledo’s, a hometown College Park pizza joint, we picked up a pepperoni, sausage and pineapple pizza. If you are a local you will love it. If not, you are probably not a local. A Ledo’s pizza has a sweeter red sauce than most. The pepperoni is thick not thin. Its square not oval. Pineapple fits with the sweet sauce. There were adult beverages in the fridge.

Alone at the house, we watched TV, again no idea what we saw, ate our pizza and necked on the couch. My hands were all over Cash’s body. I held her head in my hands, we kissed. Then very abruptly Cash stood up. As if I did something wrong, I looked up at her awkwardly.

She gave me that irresistible smile of hers. Then unzipped her black micro shorts, letting them drop to the floor. Stepping away, she pulled her matching tee above her head, then tossed the tee at me. I caught it. She removed the claw clip from her ponytail, shaking her hair so it flowed down her neck. She stood before me, in a red lace Cami bra and matching thong. The modesty panel has been removed from her thong. Her pussy was hairless. With her eyes, she said without speaking, ‘Jameson why are you still sitting on the couch!’ She held out her hand.

As I leaped off the couch all I could say was ‘”Wow!” I lead her up the stairs to my room. Red is her color; she is well aware that y red on her body turns me on every time. Stopping at the bedroom door, I tried to be romantic, I lifted Cash into my arms, but clumsily carried her to my bed, we fell entangled onto the bed. It was awkward but it didn’t really matter. Cash was prone underneath my body as my knees were firmly implanted to the sides of her torso. Cash sat up.

Our First Time… Yes It was Better than Expected!

She glowed in her red lingerie, but I was fully clothed, but not for long. I pulled my tee over my head, as Cash unbuckled my pants, then tugged off my jeans. I was naked except for my blue short, boxer brief. I was already semi aroused pushing my hardness against the pouched front. Cash helped me wiggle out of the briefs. My hard shaved cock flopped in her face. She kissed the cock head, then fell back prone on the bed. She pulled me down with her.

She finally spoke, “Jameson, I want you inside me, now!” We kissed, then I started to kiss and pecked my way to her chin, her neck, her collarbone. Cash began to whimper. Her body was twisting underneath me. She spoke again with a little urgency, “Jameson I need your cock inside me, now!” She always called me Jameson, never Jamie.

I pulled her thong to the side revealing her open vagina to me. I inserted two fingers; Cash was indeed very wet. My cock was rock hard now. I hesitated, then I got that mesmerizing stare, I gently pushed the head of my cock between her pussy lips. She squealed, then squealed even louder as I pushed in further. I began a slow rhythmic thrust; Cash paired each thrust with the movement of her hips and lower body. She then screamed, “Faster, faster, faster Jameson!” I quickly heightened my thrusts. Her body and my cock were in sync.

She shrieked, “Oh, oh, I’m ready!” then her entire body shook. I could feel the tensing, spasming, and the pulsing as her orgasm came in waves, then the calmness. As Cash was slowing down, my cock was throbbing inside her, I sent three quick spurts of cream inside her pussy. Cash clasped her hands around my neck, pulling me down on top of her. My heavy breaths turned to stillness. My body entangled on top of hers became motionless. My hard cock was still inside her.

We stayed in this position in silence for what seemed like an eternity but in reality it was probably not more than 30 seconds. I rolled my body off Cash, to lay prone on my back next to her. My cock was still aroused.

Cash climbed on top of me, pushing my hard cock back into her vagina. She started rocking her hips from side to side. My cock became hard again. Ah to be young again.

Looking up from my prone position, Cash’s skin on the chest and face is a glowing red. I hold her hips as she slowly rocks back and forth. Cash softly spoke, “Jameson I have waited all summer to be fucked by you. It was worth the wait.”

I chuckled, “Truth to be told Cash, I have wanted to fuck you since the first day you revealed that red bikini.” I paused, then added, “Yes it was worth the wait!”

Cash smirked, “Do you have any more cream inside your balls?” She then giggled, “BTW that’s not a question!” She rocked back and forth the side to side, as she slid up and down on my hard cock. I placed my hands underneath my hips pushing my lower torso upwards to match her thrusts.

We slowly brought each other to orgasm again. I quietly came first, followed by Cash. Her moans and screams weren’t as intense, but neither was she quiet. She rolled off me, snuggling and kissing my neck. I held her tightly. Cash stayed that night. I was on the top of the world. I felt like a Superhero.

This was Cash’s first time to have vaginal , but there was no pain or light bleeding. Cash is very athletic, so her hymen had already been stretched open from bike riding, sports, or other everyday physical activities. I know I took her virginity. She took mine too.

Our Relationship is Solid But

Cash and I were inseparable during our Freshman year. She is living in a sorority house on Fraternity Row, but she spends a lot of time staying with me. She is studying Government and Politics; I am in Business AdminMarketing. Our Freshman year was really fun and exciting time. We discovered more about each other and how we relate together. During her time at the UP house Cash gets to know Melissa and Megan and they get to know her better. Melissa was been helpful to Aubrey. We also spent a lot of time studying together.

We were getting caught in the excitement of our connection, but I don’t believe we were on the same page. We were still exploring our uality. They were hints from both of us that we wanted to dabble with others. Out of the blue one day, but once you get to know Cash, nothing is out of the blue, she hinted about a threesome, inviting another partner to our bed. I was surprised but was not negative to the idea. I was silently excited. My idea of threesome was two females and one male me.

Cash admitted that she didn’t care either way. We didn’t immediately go forward since neither of us could come up with an acceptable third person. We openly felt that we were more interested in someone we knew, not a stranger. Cash did openly admit that she wanted to explore her biuality more…. key word there was more. I said I was bicurious but had no clue as to how to move that fantasy forward.

What I do know is that I was more than curious about her bra and panties and other lingerie. What she wore and how she handled herself. If she left any lingerie at my house, from time to time I would try them on. Then hide her misplaced clothes in my closet. So, in actuality, is I stole them. You know finders keepers. I think she knew or at least suspected.

Throughout our relationship one of us would be ready to move forward, but the other laid back; then the relationship or commitment switched. We couldn’t maintain a balance. We both were aware of the imbalance.

We Remain Friends

The semester was coming to an end. Both of us were studying for finals. We weren’t together that often. Cash was headed home to spend the summer. Not that Annapolis was that far away. I was staying in College Park. I was taking two summer classes. One night over pizza and a glass of wine, we entered into a serious conversation. We both agreed to that we wanted to explore others outside of our relationship. We agreed drop our exclusivity at least for the summer. We both emphasized just for the summer.

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