Catching Up

byRedHairedandFriendly©

Author's Note: The following story is based on a fantasy that a Litster posted on the Fetish and Sexuality Central Forum. I spoke with the Litster, gained permission from them to write the story, as well as discovered they would enjoy reading it in 1st POV. I told them I would try writing it in 1st/3rd person POV – if that's the right way to say it? I do hope you enjoy this fantasy of Mike's. He's taking a chance with his friend Mark, but remaining true to his other side – Victoria. Voting if desired is welcomed – only one vote per reader, but most importantly, I appreciate your feedback and am glad to have made the Litster happy. Thanks muches ~ Red.





It was with mixed emotions that I listened to the message on my voice mail. It was the familiar sound of Mark, a long time friend whose call I had missed earlier that afternoon. Now as I heard it, for the third time, I felt my stomach slowly relax from the uneasy twist that had taken hold the minute I had heard his all-knowing chuckle.

He was in town, hoping to catch-up on old times and share a few beers. He left me his number and I had written it down, during the second replay, but after I closed my cell phone, I wasn't sure if I wanted to see him. Isn't the past better left alone? Hadn't we drifted apart for a reason?

I picked up the scrap of paper that had his hotel information on it as well as his cell number and tucked it into the front pocket of my slacks. Heading upstairs to shower and shave, as well as take care of any unwanted hairs on my smooth flesh, I thought about Mark and the last time we had spoken.

Spoken was such a lame term, seeing as it had been via an email not a face-to-face encounter. The last time we had actually looked upon the other, had been ten years ago maybe more.

Under the heat of the shower water, I began to wash away the sweat and dirt of the day. My thoughts unexpectedly returned to Mark. I saw him with his lazy smile and wavy blond hair; he was all bunched up in Arctic gear as he headed off to the slopes. He loved the outdoors, especially winter. Mark was like a kid when it came time to embrace the cold and welcome Old Man Winter to the hills.

Mark and I had lost track of each other when he had succeeded in making it to the Olympics and had developed a plethora of fans and endorsement deals. He still called me and we chatted. He told me about a few lovers he'd had, and I shared with him my experiences.

In time though our phone calls began to lesson and soon we were only talking once every other month. Emails replaced phone calls and texting each other – well that never happened. Eventually an email went unanswered and to this day I honestly don't know who had sent it.

It didn't matter though, all of that was in the past and now he was in town and reaching out. How did I want to handle it? I had changed. I was more open with my desire to embrace my more feminine side.

There were various clubs that I could frequent without being harassed or assaulted; some were mixed sexes, some gay bars, some simply for the ladies. No matter what type of club or bar it was, I always went as Victoria, a stunning brunette with long legs, an easy smile and warm welcoming eyes.

Mark was the opposite of me. He was straight – always had been, always would be. He dressed in fine suits, tailor made for his athletic physic. His jeans and shirts came from some of the more notable of stores; his shoes were made to order and his persona spoke of confidence and male testosterone. It would still be nice to see him again, to touch base, catch-up on all times, and rekindle our friendship.

I laughed softly as I stepped out of the shower and dried off. Friendship, that's all it had been with Mark and I, though I had often imagined us in that happily-ever-after scenario that is normally reserved for women, but in truth, our friendship meant too much to me; I never crossed the line.

I walked naked, back into my bedroom and looked at my phone, lying on the bed alongside my pants. I sat down, dug the paper from the front pocket of my slacks and stared down at the script. My other hand reached out for the phone and I pressed the corresponding numbers on the keypad.

Mark's voice came through loud and clear.

"Hey there!" he said as if he already knew who was on the other side of the phone.

"Got me all dialed in, do you?" I asked.

"Yeah, saved your number as soon as your parents gave it to me," he admitted.

I grinned.

"So, Mike, are we hookin' up tonight?" Mark asked me.

I took a deep breath and looked at my reflection in one of the mirrors in my room. "Of course," I told him. "You're just in town for tonight right? I think that's what your message said."

"Yeah, just tonight," he confirmed. "I need to head out tomorrow morning just before noon, so we'll have tonight and tomorrow morning together. It'll be fun."

"I'm sure it will. Do you want to meet at the hotel bar, or at a club?" I asked.

"A club sounds good; there's one just down the road from where I'm staying. If you want we can meet there," Mark said.

"I know where you're staying and I know the place real well. You'll like it there," I told him.

"Is it safe?"

I smiled. "Yes, it's safe and it's open to everyone. I go there often, but thanks for worrying about me. You should know something though... ." I hesitated for a moment, while my mind gathered courage and then I said, "...before you agree to be seen with me."



"What's that, you dressin' like a chick now?"

"Yeah," I answered.

Silence greeted me and I knew in my gut, the catching up was caught up and Mark was back-peddling fast.

"That's fuckin' hot," he whispered into the phone.

My jaw dropped as I sat there stunned.

"Seriously?" I asked.

"Yes, seriously; you've always been drawn to that side of your life. It's about time you openly expressed it. I'm proud of you, man. Do you go by a different name when you're dressed up?" Mark asked.

I was stunned that Mark was so accepting of this new me – well, the old me for me – the new me for him. "Yeah, I go by Victoria."

"Sexy name --- Victoria."

Mark's voice seemed to purr over the phone and if I was the type to read into things I would have sworn his voice dropped several octaves when he said it. My heart skipped a beat. "I like it," I admitted.

"What do you wear?" he asked me.

My cock twitched. I tried to ignore the flexing muscle. "Skirts, tank tops, a little make-up."

"Stilettos?"

I laughed. "You're really getting into this aren't you?" I asked.

He chuckled. "Nah, just wanting you to know I think it's great and I look forward to seeing the new you."

"Cool," I answered, feeling somewhat dejected. "How does eight o'clock sound?" I asked him. My cock no longer twitched, nor did it send any tantalizing signals to the rest of me.

"Sounds good, I'll look for little Miss Victoria," he said just before he hung up and left me feeling disappointed and foolish for hoping he had taken a walk on my side of the track.

I shrugged off my feelings and instead tried to focus on the night ahead. With Mark knowing and accepting my desire to dress up when I hit the clubs my mind turned to more intimate thoughts. My focus however, was not on Mark and I, but on the possibility that I might find someone else to spend the evening with.

Mark was a handsome man, or had been the last time I saw him. He would most likely pick up a beautiful woman and take her back to his hotel; sure we'd chat, catch up on old times, share some laughs, but in the end we'd both be going home either alone or with someone. I knew after gazing at Mark all night, I would want and need companionship, even if it was only for a quick fuck.

In my closet hung a new outfit, one I hadn't yet worn. I pulled it out, stared at the black material that glimmered when the light hit it just right. The skirt was short, very short and the matching black top that tied behind the neck would hug my chest, allowing my nipples to protrude slightly once aroused.

I saw Mark in my mind and wondered what he would think when he saw me. Would he really be comfortable looking at me all dressed up? Would he open his arms and embrace who I had become? Or would he make excuses to down his beer and run out the door?

As much as I wanted to stand there and contemplate the evening, time was slipping along and I knew I had to get ready. As was customary when I went out, I prepared myself for the possibility of hooking up with a lover. I returned to the bathroom and though I had showered and washed, I took the necessary steps to prepare myself to take a lover. Afterward, with the aid of a butt plug and my finger I applied a liberal amount of lube into my anus.

The gel was thick and the plug helped to push it higher than my finger could. My cock stiffened slightly from my intentional penetration. I groaned, removed the plug and felt a small dollop of lube slip along the rim of my ass. With one finger I massaged it around the opening, rolled some back into the deep tight entrance and then washed my hands.

Still in the bathroom, I went to work transforming myself from Mike to Victoria. My hair was slightly damp, so I finished drying it with a hair dryer, then applied a protective cream to the locks before flat ironing them. Once I was satisfied with my hair, I ran the tip of my lipstick across my lips, smacked them together and smiled.

There was Victoria. I smirked at her.

As I applied the smoky shades of eye shadow, which would make my eyes pop, I found myself once again thinking of Mark. Was I wrong about the way his voice had sounded when he said my female name, "Victoria"?

I could almost hear his voice in my head. Wasn't that a soft whisper, a gentle caress of words, hadn't he purred my name? Or was I just wishful thinking? I laughed at myself, applied my blush and flounced my hair. Victoria looked back at me and I knew it was time to get dressed, to become one with myself.

Back in my bedroom, I rummaged through my dresser drawer until I found a black garter, stockings, and matching thong. I paused at the closet again, this time taking a moment to pick out a pair of stilettos that would go great with my chosen outfit.

I placed everything on the bed and checked the time. The digital numbers on the clock showed that the minutes were slipping away. A quick call to the local Taxi Company was placed. I wanted no excuses as to why I wasn't drinking the night away, nor did I want to drive home if I had a lover willing to play in the car with me.

Secretly, I hoped Mark would call a cab too, just in case. As soon as I thought the idea, I chastised myself for my wishful thinking. I erased all thoughts, or tried to, and quickly moved to get dressed.

I pulled on my thong, adjusted my cock so it laid hanging naturally to the right and eased the back string into position so I wouldn't be forced to tug and play with it all night. It had taken some getting used to, wearing the tiny panty, but eventually I discovered exactly where things needed to lie so I wasn't constantly shifting in my seat.

My reflection caught my eye. I looked at myself, turned sideways and admired the hair-free figure I cut in the mirror. My body looked great. My 5'8" frame would be enhanced by several inches once I put on the stilettos, bringing me almost eye level to Mark's 6'2" one.

We were both built, though he probably was a wee bit more in shape than I, seeing as he was the Olympian, not I. But at 32 years of age, I didn't look too bad at all. "Pretty sexy, Victoria," I said to myself, before turning back to slide the garter and stockings on.

Once the belts to the garter were secured within the elastic tops of the stockings, I pulled on the little skirt and shimmed it over my ass and hips. The material fit like a glove and the small strips of thin silver sparkled, just like I knew it would.

The top was next. I lifted it carefully, pulled it over my head, my arms went through and it rested bunched up around my chest. I adjusted the fabric, settled it in place and tied the strings around my neck. The hem of the shirt rested just above my belly button, leaving a two inch gap between the bottom of the blouse and the top of the skirt.

Lazily I trailed my fingers across my abdomen. A sliver of heat skated across my skin. My cock jerked in response to my own touch. I licked my lips before blowing myself a wicked little kiss. When I left the house, I was five inches taller, and my stilettos clicked across the sidewalk as I walked toward the cab.

The shoes were sleek and made my ankles look trim and feminine. I loved the shine and sparkle that the string of rhinestones created as they lay across the black stockings. As the cabby drove where I instructed, I looked down and played with the soft fabric that encircled my legs. Beside me rested my clutch, it was silver and had a few sequins strategically placed. Inside were the pieces of jewelry I wanted to wear.

Some of my friends find it odd that I wait to don the jewels after leaving the house, but for me, it was my way of keeping up the pretense. A pair of tear drop earrings rest comfortably in my ears; they dangle back and forth as I shake my head. I clasped a choker around my neck; the silver and stone insets will catch the light and bring attention to my smooth skin. A matching bracelet and anklet helped to complete the look. When I stepped out of the cab I was Victoria and it felt wonderful.

I looked around, noticed a few regulars that waved at me. I waved back. A few folks looked at me strangely, but I shrugged it off. I'd told Mark the truth, this place was safe for me, and not everyone knew it welcomed all sexual preferences, but the newbies would learn.

I waited to gain entry and when I did I breathed in the scent of varying fragrances and colognes. My own choice, a vanilla scent, was subtle and would only be breathed in by someone if they were up close and extremely personal.

My gaze shifted from those close to me, to other bodies that were further away. Some individuals leaned against the bar, a few more had already staked out a spot in dimly lit corners. A few tables and chairs remained empty, but not many. The dance floor was slowly beginning to fill up, and the band piped music through speakers that had been placed inconspicuously throughout the club.

"Hey, gorgeous."

I turned and smiled at the familiar voice. Mark grinned back. He looked amazing. His smile was just as I remembered; his blond hair still looked thick and soft. His eyes were full of humor and seduction – the former was something I often saw on him, the later was something I always wanted to be aimed at me. My smile faltered slightly. "Hey Mark," I said.

He pulled me into a manly hug, then stopped, softened the embrace and pulled back. "Sorry, forgot you're in chick mode."

I chuckled, but inwardly thought how thoughtful he was. He placed his hand at the small of my back and led me through the club. We stopped a server, placed an order and Mark pointed out where we'd be sitting.

I'm not going to lie – I was in heaven. Mark seemed to have instinctively taken over the role of leading our, catching up, date. I didn't mind, in fact I appreciated it, though I admit, it was going to be hard to not react to his friendly banter.

We sat down and Mark studied me. I felt slightly uncomfortable, but knew this was the first time we'd seen each other in years, and the first time he'd ever seen me as Victoria.

"You carry it well," he suddenly said, jarring me from my personal musings.

"Thanks. It was hard in the beginning. I took baby steps, jewelry, shoes, ladies pants, blouses, eventually though I found where I could be me and where I couldn't," I told him.

"And this is where you can be – you?" he asked.

I nodded my head. The drinks arrived and we began go over the past several years. I learned about how he had managed to put away some money, make a few investments, do a few interviews and eventually found himself curious as to what more was out there for him. He didn't focus too much on past relationships. I sensed they were sore subjects for him, so I opted not to press. I know I may occasionally dress like a girl, but I am still a man; no matter if we're bi, straight, or gay, we still have a hard time expressing disappointment and loss.

When Mark took a break, I squeezed in a few key details about my life. I mentioned my past employers, as well as a few past relationships; they were few and far between, which was good for me in some ways, bad in others.

I liked knowing I hadn't been playing the field so long that I knew what I liked and what I wanted. I hated having so little experience and that I was still nervous about how to choose the right lover.

Sometimes I wished folks ran around with signs over their heads saying "I'm safe" - "I'm cool" - "I'm the one mom warned you about" – yet there was nothing like that, so it took me a while to really open up and bring a partner back to my place. I hoped that tonight I would. It was obvious to me that Mark had already captured the eyes of several pretty young women.

A few times during the evening our conversation lulled and I could tell we were both searching for something to say. Mark looked somewhat uneasy and I felt as if he wanted to talk to me about something, but no matter how much I tried I couldn't compel him to share. Eventually I took the hint and began perusing the crowd, much like he was.

A young woman was the first to approach our table. Her gaze shifted briefly over me, and I felt the hairs on the back of my neck rise. She was here for Mark and Mark alone. Her smile was big and bright. Her gaze was full of mischievousness and obvious desire. I leaned back and watched Mark being led out onto the dance floor.

I kept my eyes on him, allowing myself to imagine it was me he was dancing with. It was my hips his hands were resting on, my neck his breath was caressing as he pulled me closer. Yet, there I was sitting at a table, alone, while Mark dance provocatively with the little redhead. I so wanted to be her.

A cough from another club attendee brought my mind back to reality. I turned and eyed the young man who was looking down at me. He was tall and thin, with black hair and dark eyes. He wore a pair of black jeans, a T-shirt and sneakers. His gaze drifted lazily over me and I saw his brows rise in interest. I grinned, and waited for him to ask me to dance. When he did, my pulse raced.

I stood up and together we moved onto the dance floor. It wasn't long before I was in the mood and swaying seductively against the stranger. It also wasn't long before I was bump from behind and almost pushed into the young man's chest.

"Whoa, sorry," a voice reached out to me, grabbing my waist as I tried to regain my footing.

I felt two firm hands on my hips. At first, I thought they were the man's, the one that had asked me to dance. When I looked up, I saw it was Mark. He held me, and stared down into my eyes. I saw the look and knew what he hadn't been able to tell me at the table. My chest tightened as his hands held me more firmly and pulled me toward him.

We moved together as if we had been partners for years. I felt his fingers glide up my back, while one hand remained on my hip. We swayed and moved around in a slow circle. The man who had taken me to the floor walked away; the young girl, I saw her roll her eyes, turn and find another good looking guy to gyrate against. Eventually everyone else in the room faded away.

"Mark." His name sounded so right, coming from my lips.

"Hmm?"

"I can't do this, not unless you're sure," I told him.

"Sure about what?" he asked. His breath caressed my skin as he whispered in my ear.

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byRedHairedandFriendly© 7 comments/ 29704 views/ 13 favorites

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