tagTranssexuals & CrossdressersTrailer Trash Tranny Ch. 08

Trailer Trash Tranny Ch. 08

byTravel_by_day©

Chapter 08: Epilogue

It had been 10 years since that trip I made to Omaha where I ran into Jeannie, the young blonde transsexual living in a trailer park. I'd thought of her frequently after my first trip, but over the years I'd thought of her less and less, but sometimes I'd wonder what happened to that beautiful, blue-eyed, blonde haired t-girl, what kind of woman she had grown up to be.

Soon after my business trip to Omaha I got a new job where I moved to Hong Kong. After years of living there, and then in our branch office in London, I finally returned to North America, working in my company's New York head-quarters. I got myself a nice loft in Tribeca which cost buckets of money, but after London it somehow seemed affordable.

Across the hall of me lived Scott. Scott was in his late 40s, an absolutely stereotypical flaming homosexual and seemed to do little than sleep during the day and host parties for New York's artist community at nights. Scott's grandfather had invented some indispensable piece of daily life like the zipper, fridge magnets or oxygen that had made the family wealthy beyond any sort of comprehension by normal people, even those like me who could afford multi-million dollar Tribeca lofts.

Scott invited me to every party he had, which meant that I was receiving invites four or five times a week. I would occasionally go to the parties, if for no other reason to see how a whole different side of New York lived. The parties were always filled with a strange assortment of folks. There was Scott and his other trust-fund-baby friends, a few up-and-coming artists or fashion designers, a bunch of nouveau rich folk trying to gain credibility by being a "hip" patron of the arts, a few con-artists that were looking for plays on the rich at the party, and me. Mainly I just stood in the back watching the action.

And for those nights I didn't go, luckily the old converted warehouse I lived in had thick walls, so I couldn't hear any of the noise from the parties.

After a few months, I was going to Scott's parties less and less. I almost didn't go to the party on that Wednesday night, having a 10 o'clock meeting the next morning that I really wanted to be sharp for. However, I had a shitty day at work and felt like a drink or two could take the edge off, so after dinner I walked across the hall to Scott's place.

I wandered in and grabbed myself a gin and tonic, a habit I had picked up hanging out with British ex-pats in Hong Kong, and one that only got reinforced living in London. Scott was playing social butterfly and match-maker, flitting around the room dragging people out of conversations and depositing them in other conversations.

Scott saw me, and waved. He grabbed a woman in a long, floor length dress from a circle and pulled her over towards me.

"Holly, you have to meet the only real, normal person I know," he said, dragging the woman with him, as she tried to finish a conversation over her shoulder with the people she had just been talking to.

Scott looked at me and said, "you have to meet Holly. Holly Hepburn is the hottest new designer in SOHO right now, and in three years she will be so famous that she won't even deem to return my calls. Holly, this is..."

At that point Holly turned her head towards me, having finished her conversation with the people Scott had dragged her away from and surprisingly said, "Bill."

Scott looked over at Holly and raised an eyebrown, "Good guess, are you psychic, dear?"

Holly was a thin woman with dark hair and a very pretty face, but I didn't place her as someone I knew. Surely I would have remembered a name like Holly Hepburn. "Do we know each other?" I asked.

Holly stood in silence for a moment with a shocked look on her face, but then seemed to snap out of it. "No, no. Scott said your name before," she said, and reached over and gave me an air-kiss on each cheek.

Scott pursed his lips, saying, "I don't recall saying Bill's name, but perhaps I did. Too bad, I was looking for some sort of good gossip about past romances, perhaps one of you throwing a drink in the face of the other one. A little drama always helps keep the party lively."

I took a good look at Holly, and realized that despite my initial feeling, there was something about her that looked familiar. I was about to suggest that perhaps we had met, but before I could Scott pulled Holly away, saying something over his shoulder about her "having to meet this artist from Chile who paints using nothing but menstrual blood."

I couldn't place Holly, but she was gone and I took up my usual position standing by the bar and watching the strangeness at the party. Some hippy looking artist was currently using a hummus dip to paint the portrait of some CEO's wife on the floor. I was enthralled with watching the artwork in progress, that I didn't hear anyone come up behind me. I was a little startled when I felt the tap on my shoulder. I turned around to see Holly Hepburn holding a martini glass.

"Ah, Ms. Hepburn, sorry our conversation got cut short earlier," I said. "You know, your face strikes me as familiar. Are you sure we have never met?"

"Is that the line you use on all the women?" she asked.

"No, seriously, you do look familiar to me. You didn't happen to go to college in Texas, did you?"

Holly smiled at me. "I did lie when I said we hadn't met before. I'd be a little disappointed if you can't remember where, though."

I looked at Holly for a minute, and then it hit me. The face was a little different, it was a little fuller and more feminine, the hair was dark instead of blonde, and the body had filled out, both in the chest and the hips, but the eyes. It was the blue eyes. I looked at them and saw that girl from back at the trailer park in Omaha.

"Jeannie," I said.

Holly wrapped her arms around me and gave me a kiss. "Oh Bill, you did remember. I was afraid that you weren't going to."

"It took me a while; you've changed a lot... In a good way, I mean. You look absolutely stunning now."

Holly's face turned red. "Thank you," she said, looking down. "You know, I've thought of you a lot. That weekend we spent together, it meant a lot to me. You were so sweet."

Now it was my turn to blush. "Really, I always felt bad about it. I felt like I took advantage of you, and all for nothing more than a bottle of vodka, a pack of smokes and a dinner at a greasy spoon."

Holly laughed, putting her hand on my chest. "Don't feel bad about that. You were cute, I would have had sex with you even if you hadn't bought that bottle of vodka. Hell, back then I slept with guys a lot worse than you for a lot less than a bottle of vodka. It wasn't the sex I was talking about. It was the way you treated me when we weren't having sex. You were the first person that treated me like a woman. Everyone else up to then had looked at me like I was a faggot in a dress. You treated me like I was a female."

I blushed even more. I was speechless. All I could think to do was to hug Holly. We embraced, and held the embrace. I breathed in deeply. Holly smelt like peaches and baby powder.

Holly and I pulled away. Holly's eyes were a little moist. I gave Holly a cocktail napkin that I had been carrying with me, and she daubed her eyes. Finally she said, "so, living in a million dollar loft in New York, I take it your not out cruising trailer parks for trannies anymore?" She laughed.

"No, no. Haven't been to a trailer park since we meet. Wouldn't want to ruin my fairy tale impression of the places. I work in banking, Senior VP of Retail Banking. And not to brag, but it's a MULTI-million dollar loft. So, what about you, I take it you're not having sex with dudes cruising trailer parks in exchange for bottles of Vodka anymore?"

Holly laughed and held up her martini, "No, I think the martinis I drink in the bars now are worth more than that whole bottle of vodka you bought me back then. I got out of the trailer park and got into fashion."

That's when Holly told me the story of how see got out of the trailer park. How she made money by sleeping with guys at truck stops, strip club parking lots and hotels. How she made a movie for an online porno site. How she hitchhiked her way from Omaha to New York City, finally arriving in Greenwich Village after a thrilling and trying journey. The stories I have told you here.

After arriving in New York, she realized she needed to make some money, so she turned to what she knew, sleeping with guys in exchange for money, but she stayed away from the drugs and other problems that can drag someone down in that business, and enrolled in fashion school. She got an internship at a design house, and after that finished, held a couple jobs with different designers. All the while, she was making her own designs, at first selling them at outdoor markets and into small, independent shops, and then finally starting to get some decent orders. Just a year before the party she had set out on her own, investing all her savings and finding a few other investors who believed in her.

It was an amazing story, I was enthralled by it. From her beginnings to arrive at where she had in such a short amount of time really showed an amazing strength of character.

"So, are you seeing anyone," Holly asked as she finished her story.

"No, I've only been in town for 4 months and haven't really had much chance to get out and see people. Work keeps me pretty busy," I said. "And you, are you single?"

Holly nodded. "Yes. My business takes up most of my time," she said.

"So, you are single. I am single. Perhaps, you'd like to go out sometime?"

"I'd love it," Holly replied.

"Listen, not to pry, but are you... I mean, do you still..." I asked, blushing. "I mean, have you had any surgery?"

"Well, I've had some surgeries, but I assume you are thinking about one specific one, and no, I haven't had that one yet. It's expensive and I'd need time to recover, both things that I can't do right now because of my business. Once things get off the ground, then I will look at getting in, maybe in a few years. So, you still want that date?" Holly asked.

"You bet I do. I'm pretty open this weekend, if you're available."

Holly put her hand on my arm and said, "actually, I was thinking of something a little sooner. You want to get out of here?"

I nodded. "Sounds great. I know a perfect little place that has a nice bottle of white chilling, an available spot on a comfortable couch and a DJ who will play anything you want to hear. Best thing is that it's right across the hall from here."

Holly leaned in and whispered in my ear. "Why sir, are you suggesting that I would go to your apartment unescorted? That could damage my reputation." She then laughed, grabbed me by the arm and said, "let's go."

We left Scott's party and cross the hall to my apartment. Holly flipped through my CD collection as I got a couple of glasses and a bottle of wine from the fridge. I sat on the couch and opened the bottle. Holly put on a CD of soft jazz and joined me on the couch. We sipped the wine and Holly told me about her fashion design business.

I noticed that as Holly talked, she was massaging her neck. "Everything okay?" I asked.

"Yes, I've just been working hard and it's a bit tense. My neck is just a little stiff."

I put my hands on Holly's shoulders and started rubbing her neck. "Oh, that feels really good," she said. I could feel that her neck muscles were knotted and worked on them for a few minutes.

"I have a Jacuzzi tub in the bathroom. Why don't you go have a soak? Then when you come out, I can give you a full massage," I said. At first Holly said no, but eventually I convinced her. She went into the bathroom while I lit some candles in the bedroom and lay out a towel on the bed.

Holly was in the tub for about 20 minutes. She emerged from the bathroom with a towel wrapped around her body. She came into the bedroom.

I pointed to the bed. "Lie down on the bed. I'll give you a massage." Holly dropped the towel and lay on the table face-down. Before she lay down though, I got a good look at her body. Her body was more feminine than the one I had seen in Omaha. She had a nice pair of breasts, and her hips had more of a curve. Her soft cock was hair free.

I had some baby oil which I rubbed onto her back. I spent a good amount of time working on her neck. Soaking in the tub had released some of the tension, and my hands removed the rest. Once her neck was relaxed, I started moving down her back, working my hands deep into her muscles. I reached her buttocks, but only quickly ran my hands over them. Holly shivered at the touch of my hands on her ass, but I decided to make her wait. I moved down to her feet and started to massage them. I slowly worked my way up her legs.

Once I reached the top of her legs, I started to gently work on her buttocks and inner tights. Holly started to breath a little heavier. With my left hand, I started to massage her ass, running my index finger up and down the crack of her ass, applying a small amount of pressure on her asshole as I passed it. With my right hand, I reached between her legs and underneath her, and started to massage her balls and cock. She was already partially hard, and continued to grow as I rubbed her shaft.

Holly turned over and I moved up to kiss her. Our lips met. Her hands started moving over my body, pulling my clothes off. Once I was naked, we continued to kiss, our naked and hard cocks rubbing against each other.

Holly reached down and took both of our cocks in her hand, and started jerking them. There was a small amount of baby oil on her cock that got transferred to her hand and my dick. The two cocks, greasy with the baby oil, slid easily in her hand.

My hands explored Holly's breasts. They were firm, and her nipples were long and hard. I ran my fingers around and over her nipples. Holly moaned with pleasure, and started jerking our cocks faster.

It was a very different experience than what we had shared 10 years previous in Omaha. Omaha was purely physical. That evening with Holly was passion, both physical and emotional. More than just my cock was into what was happening, my heart and my head were engaged as well.

Those feelings combined, physical and emotional, to a mind blowing orgasm. I quivered as my semen came flowing out of my cock. Holly's orgasm quickly followed mine, her come splattering on our torsos and mixing with mine.

We lay back and kissed, recovering from the experience for a while before falling asleep.

Now, the rest of the story you should all be aware of - the dating, the courtship, the engagement, and now, today, the beautiful wedding. Some people may look at what I've said tonight and think to themselves that this isn't a typical wedding speech, but I wanted you all to know how special this woman is. She has come through a lot, and I am privileged that she has agreed to allow me to continue with her on this journey as she grows.

So please, all raise your glasses and toast my beautiful bride, Mrs. Holly Hepburn.

Report Story

byTravel_by_day© 0 comments/ 26266 views/ 13 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartking281, DVines2011 and 11 other people favorited this story! 

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel