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Shanna Takes Manhattan

Shanna leaves the quiet country life for the big city
After driving all night, I was now somewhere in the middle of West Virginia. Daddy called frequently, but I did not take his calls. I was determined to start a new life for myself in New York City, away from conservative redneck Tennessee. My phone rang once again, but this time, it was my friend Monica.

"Girl," Monica said. "Where have you been? I've been trying to reach you all morning?"

"I'm somewhere in West Virginia right now," I said.

"What the hell are you doing there?" Monica said.

"I'm moving to the city. Listen, girl," I said. "You're breaking up. I'll call you later."

Actually, I could hear her just fine. I just didn't want to have to explain.

A short while later, I heard an awful sound coming from the engine, followed by a plume of steam. There I was, a tranny girl in the middle of redneck country with a car that was about to break down. I had very little money and hundreds of miles left to go.

Luckily, I pulled off of the highway and into a small family-run service station. My first instinct was to call Daddy and ask for help. But then I would have to explain why I had run away from home. I couldn't do that.

I walked into the door and the smell of diesel, grease, and cigarette smoke instantly assaulted me. A pair of deer antlers hung on the wall above the cash register. The counter was covered with hunting photos. An older man, his clothes covered in grease, greeted me.

"What can I do for you today, ma'am?" he asked.

I leaned over the counter, threw my hair back, and flashed him a seductive smile.

"I don't know," I said. "I think my car's broken down."

The man smiled at me, his mouth resembling a jack-o-lantern. Then, he spit tobacco in a cup he was carrying.

He was utterly gross. But I had very little money and needed to get out of there. So sometimes, a girl's gotta do what a girl's gotta do.

"Well, if you wanna give me your keys, I'll have my boy Jesse take a look at it," he said. "By the way, my name's Terry."

I smiled sweetly at him.

"Hi Terry," I said. "I'm Shanna. I hope you can take care of me. And maybe I can take care of you."

I set my purse down on the chair and then bent over to reach into it to get the keys. I made sure he could get a good view of my ass that was hidden underneath the denim cutoffs I was wearing.

"Here you go," I said, as I handed him the keys.

I sat and waited in the small, filthy waiting area for the verdict as to how much it would cost to repair my car. As far as Terry could tell, I was a small, petite, pretty young redhead who didn't know anything about cars. He was in a position to really take advantage of me if he wanted to. If the repair bill were to be in the hundreds, I would have no choice but to call Daddy. Hopefully, my charm act would work to my advantage.

About an hour later, Terry came out with the verdict.

"Looks like you've got a blown head gasket and a broken rear differential," he said. "With parts and labor, you're looking at about a grand."

I started to cry, turning on the water works in hopes that would help bring the price down.

"Listen, Terry," I said. "I'm a single lady trying to get to New York, running away from an abusive boyfriend. I don't know how I can afford that."

"Well," Terry said. "We take Visa, Mastercard..."

Then, he smiled.

"...or if you'd like to step into my office, we can discuss additional payment options," he said.

I stood up, threw back my hair, and followed him to his office. We walked through the shop, where his son Jesse was working on my car.

"Hey, Jesse," Terry said. "Let's get to work on this pretty young lady's car,"

"Sure, Dad," Jesse said.

We walked into Terry's office, and he shut the door behind him.

"So here's the deal," Terry began. "How 'bout you show me a good time, give me a lay I'll never forget, and we'll call it good?"

"I think you got yourself a deal," I said.

Oh yeah, the transgender thing. I wasn't sure how to deal with that part.

"So how 'bout showing me that pussy?" he asked.

"Sorry, no front door," I said. "Just a back door."

I was afraid where this would be the point where he would tell me to take my piece of shit car and get the fuck out of out of his shop. He thought for a minute.

"Well then," he said. "I guess I'll just have to drill your ass, now won't I?"

"So, baby," he said. "Show me what you got."

I slipped off my shirt and displayed my breasts to this abominable creature. I caressed them and pinched my nipples to give him a sample of what I had to offer him.

"That ain't all you got, is it?" Terry said, becoming increasingly aroused.

Then, I stood up and took off my shorts and sandals. I was completely naked in front of him, except for the black thong g-string.

I never wanted to see this man again. So at this point, I really didn't care if he saw my boy parts. I slipped off the thong and showed him my small vestigial cock and shriveled up balls that were largely hidden under my pubic hair. Then, I turned around to show him my ass. I allowed him to play with my soft, smooth butt cheeks. I ground my hips and threw my hair around as he pleasured himself with my ass.

"Now, how 'bout you give me a big, wet one right on the lips," Terry said.

Oh God, what a horrible and hideous thought. He had three or four yellow teeth, and for all I knew, a nasty chaw buried in his cheek. I wanted to puke.

So I turned around with a smile, closed my eyes and kissed this foul man on the lips. I quickly withdrew, before he had a chance to share his disgusting mouth contents with me.

"Hey, baby," he said. "You call that a kiss?"

He took hold of the back of my head and pulled me close to his noxious face. Then he pressed his lips against mine and slipped me his putrid tongue!

The rank contents of his mouth filled mine, his toxic tongue bathed my teeth with God-knows-what. It was a truly awful experience.

But it was that or be stuck in the middle of West Virginia.

With that thought, I leaned into his kiss and allowed him to assault my mouth until he had his fill. Thankfully, we broke away from that disgusting kiss and I gave him the sweet seductive smile that earned me this awful gig to begin with.

"Now that's more like it," he said with a grin. "Don't you think?"

I giggled, teasing him.

"'re not too bad there, mister," I said, lying through my chewing tobacco and bad-breath-tainted teeth.

Then, as I was bent over, naked, on all fours on his desk, he stood up to undo his belt. He pulled up his shirt, revealing his pale, stretch-mark-laden spare tire covered with salt-and-pepper body hair. He smelled like diesel, motor oil, and dirt. Then, he unzipped his pants and pulled out his wrinkled, uncut five-inch cock. A layer of smegma permeated the gap between his foreskin and his head. This was the dick that he wanted me to put in my mouth.

I took hold of his cock and took it in my mouth as I was expected to do. I gagged on the stench and taste and nearly vomited. But I held tight as I blew him, showering his foul cock with my saliva.

Terry pulled his cock out of my mouth. At least my sucking him off cleaned it up a little bit. But that disgusting smegma was still there.

He jerked himself off before shooting his come all over my face.

A short while later, after Terry was kind enough to let me use their bathroom to clean myself up, it was time to go.

In the waiting area, Terry handed me the keys to my car.

"You're all good to go," he said.

"But do me a favor," he continued. "Don't come around here again."

I smiled back at him.

"Don't worry," I said. "You're not even close to being my type."

With that, I walked outside and got back into my car to continue my journey. The most disgusting sexual experience that a human being could possibly endure was now over.

Even so, what I learned through this ungodly experience was that I was willing to do whatever it took to achieve my goals. Thanks to my ability to satisfy these creatures, I was now on my way to make my dreams come true. This world is full of t-girls who couldn't have pulled that off, much less for a thousand bucks.

I got back on the highway and headed east. Several hours later, I drove through the Lincoln Tunnel and arrived in Manhattan.

Watch out, New York...Shanna's arrived!


That night, I stayed at the YWCA, where I cleaned myself up, both inside and out. That West Virginia auto repair shop was now a fading memory. My life was to begin anew the following morning.

I found a small basement apartment in East Harlem advertised on Craigslist. It wasn't very big, but for the small amount of money I had, it was what I could afford.

I met with the landlord, who showed me the apartment. When I walked in, it looked more like a jail cell than an apartment. I would not be able to decorate the walls due to the water pipes that covered them. It had a kitchen, a bathroom, and the remaining floor space was about the size of a large closet: maybe large enough for a twin bed and a television, but not much more.

"It's going for $800 a month," the landlord said in a Middle Eastern accent, "I'll need an answer now, because I guarantee tomorrow morning, it will be gone."

I flashed him my seductive smile.

"Can you take $500 now?" I asked, flipping my red hair back.

He thought for a moment and then smiled at me.

"Five hundred and it's all yours," he said. "Give me three hundred by the end of the week."

I handed him the cash and suddenly, I was home.

A few days later, my first job interview. I had applied for a job as an advertising consultant, and, thanks to degree in advertising and my superb resume doctoring skills, I was called to interview for a prestigious advertising firm on Madison Avenue.

There I was, in a large, beautiful office with a window that allowed an exquisite view of the Empire State Building and the New York City skyline. Across a giant marble-top desk from me was Fiona Charles, President and CEO of Charles Advertising Group.

"Shanna, I'm very impressed by your skills and experience," Fiona said. "I've reviewed hundreds of resumes and you not only have the right qualifications, you have just the attitude, and quite frankly the appearance that we're looking for. I would like to welcome you to Charles Advertising as an ad consultant."

"Thank you, Miss Charles," I said.

"It's Fiona," she said.

"You'll report directly to me. And I should warn you, I have very high expectations of my associates."

"I promise I won't let you down, Fiona," I assured her.

"I'm not looking for promises," she said. "I'm looking for results. I'll know the first day you report to work whether you're a good fit for my management style."

She opened her desk and pulled out a stack of papers.

"I'll need you to fill out these forms," she said. "The usual. Your W-2, your I-9, your confidentiality agreement, and your non-compete agreement. Also, we will need you to take a drug test. Will that be a problem?"

"No," I said. "Of course not."

"Good," she said. "Because we have a zero-tolerance drug policy and we do random testing. I'll also need your driver's license and your social security card."

"Sure," I said, reaching into my purse to hand her the documents.

Fiona walked over to her photocopier to make a copy and then stopped.

"Shanna," she laughed. "Your driver's license says you're a man. How did they mess that up?"

I chuckled. Unfamiliar with local laws regarding discrimination, I decided this wasn't the best time to tell her that I am a trans woman.

"Well, you know, it is Tennessee," I said.

"When you go to apply for your New York license, just be sure to take your birth certificate with you so they can fix that," she chuckled. "That would be embarrassing, I would think."

In a few short days since leaving home, all the pieces of my new life seemed to be coming into place: I had a place, a job, and all of this all in a city full of things to do and people to meet. Now, all I needed was that special man in my life and I would be set.


Following Fiona's advice, I went to the DMV to apply for a new driver's license. After hours of waiting for my number to come up, I finally went up to the counter.

"I need to change my gender on my driver's license," I said. "Tennessee made a huge mistake."

"Oh, that's no problem," the young man behind the counter said. "Do you have your birth certificate?"

"No," I said.

Then, I leaned over to whisper so that the entire room wouldn't hear my business.

"You see, I'm a male-to-female trans woman," I said.

"That's no problem at all," he said with a smile at full voice volume. "Do you have the letter from your doctor showing that you've completed your reassignment surgery?"

Other people turned around to look at me.

"Well, no," I said. "This is kind of embarrassing to talk about in front of all these people. You see, I'm pre-op. But I brought letters from my doctor showing my hormone prescription and gender dysphoria diagnosis."

"Hmmm..." he said. "We'll actually need to see the letter showing that you've had surgery before we can change the gender on your license."

At this point, I didn't care who heard me speak.

"Look at me," I said, raising my voice. "Do I look like a male to you?"

The security guard took notice.

"Hey," he said. "If it hangs, you're a man as far as the law is concerned."

He was right. After all, he was just a low-paid public servant. He didn't write the laws. I dropped the subject and continued with the process of getting a new license. When finished, he handed me my New York driver's license with "male" displayed as my sex. I was disgusted. Disgusted in large part because most people are never put in a position where they must discuss their private parts with complete strangers in public.

I walked away from the counter and went to use the ladies' room. Then, the security guard stopped me.

"Excuse me, sir," he said to me. "You need to use the men's room."

"Excuse me, rent-a-cop," I said. "I am not 'sir.'"

With that, I left the building.

I walked outside, only to find a parking ticket in my window. The meter had expired . I took the ticket out of the windshield wipers to read it.

Just then, a young man approached me. He was gorgeous, probably in his early to mid twenties, well-built, blond, and sported a deep five o'clock shadow and a Yankees baseball cap.

"That just sucks, doesn't it?" he said.

"Tell me about it," I said. "I've only been in the city for a week and already I'm getting parking tickets and trouble with the DMV."

"Really?" he asked. "Where are you from?"

"Watertown, Tennessee," I said. "I'm Shanna. Nice to meet you."

He shook my hand.

"Hi Shanna. I'm Matt," he said. "Nice to meet such a beautiful lady."

I smiled at him.

"Are you flirting with me?" I asked.

"You just now noticed?" Matt said. "So, what do you say we go have coffee or something?" he asked.

I looked at the parking meter, realizing that the expired time continued to grow as we introduced ourselves. He reached into his pocket, pulled out a credit card, and paid the meter.

"I insist," he said.

"Well, in that case," I said. "Lead the way."

Matt and I walked down the street to a small neighborhood coffee shop, where we sat and conversed.

"So you came all the way from Tennessee to start a new life?" he asked.

"That's right," I said with a laugh. "And you have no idea what I had to go through to get here. What about you? You from here? What do you do?"

"I'm from Iowa," he said.

"Oh nice," I said. "Handsome, corn-fed farm boy."

Matt laughed.

"Don't know about handsome," he said. "But other than that, guilty as charged. I moved here to go to CUNY and now I work on Wall Street as a stock broker."

"I just got a killer job as an ad consultant for Charles Advertising," I said. "And I'm a T-girl."

He gave me a puzzled look.

"Of course," he laughed. "'T' for Tennessee."

"'T' for Tennessee, yes," I said. "And 'T' for transgendered."

I never allowed conversations to pass for too long without this being made known. If he was going to walk off in disgust, I would rather he do it now instead of later when I started to develop attractions and feelings.

"Oh," he said, his smile turning into a frown. "Okay."

"Thank you for coffee and conversation," I said. "It was great to meet you, Matt."

Then, I got up to leave.

"Wait," he said. "Was it something I said?"

"No," I said. "It's something you haven't said yet."

He laughed.

"Sit down," he said. "How do you know what I'm going to say?"

I sat back down, more than slightly embarrassed.

"I'm sorry," I said. "Knee-jerk reaction I guess."

"It's not like you're a Red Sox fan or something," he said. "Please tell me you're not a Sox fan."

"Isn't that a football team or something?" I asked.

Matt laughed.

"Have you ever been to a Yankees game?" he asked. "That's baseball, by the way."

"No," I said. "Can't say that I have."

"Well, I've got two tickets," he said. "Can you be ready by five?"


Matt and I went to the Yankees game later that evening. Then, we went to dinner, and then back to his place. Having spent most of the evening with him, I came to discover he was exactly the type of man I longed for: good-looking, strong, athletic, boyish charm, and boy-next-door innocent. He was well-mannered and treated me like a lady.

But, as always, I kept waiting for the shoe to drop, so to speak. This was such a typical part of the movie: the part where boy meets T-girl and boy is curious about T-girl. Now came the part where boy fucks T-girl. And sadly, I knew what the scene following that would be.

I tried to give him the benefit of the doubt. After all, he showed no discomfort with the disclosure about my gender identity. But then again, neither did Kyle until after we did the deed.

I walked into his Lower Manhattan apartment, which was on the twenty third floor and provided an excellent view, very different from the stunning view of water pipes in my East Harlem pad.

"The game was great," I said. "First time I've ever enjoyed watching sports."

"Just stick around for a while," Matt said. "We'll make a Yankees fan out of you. Until the Giants start playing. And that is a football team, by the way."

"Haha!" I laughed.

"Can I get you a drink?" he asked, walking into his kitchen. "I've got Coors, Budweiser..."

"I'm a girl," I laughed. "I like foo-fooey drinks."

"Water?" he asked.

"That's fine," I said with a smile.

He then joined me on the sofa.

"My daddy tried to get me to play catch when I was a boy," I said. "He'd throw the ball to me and I'd just let it drop and then go back to playing with my dolls and my easy-bake oven."

"So, you've always been a she-male?" Matt asked.

"No, I'm a 'she'," I said. "There's never been anything 'male' about me."

"I'm sorry," he said. "I'm learning. Hey, you thought the Red Sox were a football team."

"True," I said.

"So, what do you prefer to be called?" he asked.

"Just call me a girl," I said. "If you have to be specific, you can say T-girl or trans girl...just whatever you do, never refer to me as a 'he' or a 'him' or 'sir.'"

"Have you ever thought about, you know, going all the way?" he asked.

"You mean surgery?" I asked. "Yeah, someday I hope to finally become a complete person."

For a moment, there was silence. Matt looked at me with his beautiful blue eyes and boyish yet very masculine smile. I only wished I could read what was hiding behind that. I was hoping, deep in my heart, that maybe this time it was the real deal and that this princess had finally found her prince. But only time would tell.

"I can't even begin to imagine what that must be like," he said. "You know, to live in a body that doesn't match your mind or your heart."

I laughed.

"It's a real bitch," I said.

Matt took my hand. Then he held it up and caressed it, quietly studying my skin and fingers.

"You know what I like about you?" he said. "Your womanhood is something you've worked very hard for and it shows. You know, call me old-fashioned, but I like a girl who compliments me as a man, rather than one who tries to compete with me. Most girls go around acting like they wish they had a pair of balls. They get offended if you open the door for them. They get pissed if you look at their boobs while talking to them. They want to control you, they want to be in charge. But not you. You don't take those kinds of things for granted. You seem to like a man who likes to take the lead. And girls like you are pretty much impossible to find."

I smiled brightly at him.

"Good answer," I said.

Matt gently put his arms around my waist and leaned over to kiss me. He opened his mouth and slipped his tongue into mine. He was beautifully clean, his mouth tasted sweet like minty mouthwash. His light facial hair was just abrasive enough to tease and tickle the smooth skin on my face.

Then, he broke away and rested his forehead against me as he smiled.

"You wanna stay the night?" he asked.

"I'd love to," I said.


I lay down on his bed. His sheets were flannel and absorbed his musky scent, which turned me on greatly. He took off his shorts, revealing his huge cock. He wasn't that long-- maybe six or seven inches, but he was thick. Too thick, in fact, to be able to penetrate me without generous lubrication.

Then, he laid down on top of me, pressing most of his 230 pounds down on me. He was six foot four, and most of that weight was bone and muscle. I put my arms around him as he kissed me. I felt completely consumed by this gorgeous hunk: my motionless body under his weight, his tongue buried in my face. I felt his huge, hard cock pressing against mine, which was only barely erect under the g-string.

After he kissed me for several minutes, Matt moved down to kiss my neck and chin. Then, he moved down to suck on my nipples. An electrifying surge of heat shot through me, finally causing my cock to go into full erection, which I soon lost.

After he was done with my breasts, he kissed my stomach and licked the inside of my navel, and with his tongue, played with my navel ring.

Then, he stopped. He wasn't sure how he wanted to address the one piece of clothing I continued to wear. I was sure that as a straight man, he had no interest in sucking my cock. And, of course, I didn't want to go there either.

The g-string that I wore was as much to hide my boy parts from myself as it was to hide them from him. You see, revealing my cock was a very ugly reminder to both of us that I was not like other girls. I had no vagina for which to pleasure him. No clitoris for which to pleasure myself. All I had was that awful male appendage that I wish I had never been born with. And while Matt or Kyle or any other guy I was sleeping with might put it out of their mind once we were done with the deed, it was I who had to live with it. That was the main reason I kept it concealed.

"Do you mind if I keep that on?" I said, referring to my g-string.

"No, not at all," he said with a smile. I'm sure this came as a welcome relief to him.

With the g-string covering my boy parts, I could at least forget for the short time I was making love with Matt that there was a stubborn biological male standing in the way of the complete woman I desperately longed to be.

Skipping my groin area, he moved down to kiss the inside of my thighs. This was the closest I was sure I come to the experience of having him go down on me. He then kissed my knee, then my calf. Finally he took my feet and rubbed them before sucking on my toes.

"I wanted to kiss you from head to toe," he said with a smile.

"Skipping certain parts, of course," I said.

"Oh yeah," he said.

With that, he raised my legs, placed a pillow under my back, and then moved his mouth to my crotch. Then, with my thighs over his shoulder, he put his face to my butt pussy, pushed aside the string, and began to give me one hell of a rim job. In this position, I was able to see his beautiful face as he paid special attention to my most private of areas. I felt his tongue caress my butt pussy.

Matt's rim job on my pussy was heavenly. I reached down and touched my cock through my thong so that I could masturbate as he continued to bathe my anus. I hated that I needed to do this, but at the same time I wanted to experience an orgasm with Matt.

"Don't come just yet," he said.

Then he got on top of me, his groin touching my face so that he could introduce his thick cock into my mouth. Then, with his face against my nether region, he continued to lick my butt pussy. There was just enough room for me to continue jerking off my tiny dick as we had the most amazing 69 going on.

Matt's cock filled my mouth and his weight shoved it down into my throat. He started thrusting in and out of my mouth. His mighty balls banged against my nose. There was certainly no way his cock was going inside me without some good lubrication.

His tongue against my butt pussy felt like needles pushing into my skin as I began to go into orgasm. I let out a orgasmic scream as my thong became soaked with my juices.

Matt withdrew his cock from my mouth and stood up against the edge of the bed, preparing to fuck me.

"I don't suppose you have any lube?" I asked.

"No," he admitted. "Not something I usually have any use for."

As a matter of fact, most straight guys didn't use lube and gay guys would, of course, never fuck me. So having sex with a man often meant either being fucked with as much lubrication as saliva could provide or being fucked dry. Neither option would suffice in this case. He was just too big around.

"I've got lotion," he said.

Not ideal, but I guess it would have to do. He took a bottle of lotion and applied a dab of it to my anus. This, coupled with the scented oils I wore, provided just the amount of lubrication for an amazing fuck.

"Go slow," I said. "You're way too big to just shove it in me."

"I've never done this before," he said. "You know, in a girl's butt."

"It's okay," I said. "I'll tell you what to do."

Then, he lifted my calves up over his shoulder and rested my ass on his thighs to give himself the perfect angle for penetration. I looked into his eyes, which revealed very excited but also very nervous thoughts. I smiled back at him, ready to allow this very beautiful and awesome man to enter me.

"Ready?" he asked.


With that, he took hold of his cock and very lightly pressed it against my butt pussy.

"You can push a little harder," I said.

He gave a good push, and his head penetrated my sphincter. There was immediate pain, and he took notice. He pulled out.

"You okay?" he asked.


He penetrated me again, this time stopping once he could tell the pain had set in.

"Keep going," I said.

He pushed in a little more. By now his exceptionally thick shaft had made its way into me. The worst part was over. Now I just needed this awful pain to subside.

"You're tight!" he said with a huge smile. "That feels awesome."

"No, you're thick," I said. "That feels awesome."

Then, the pain slowly started to fade. My muscles relaxed and I was ready to take the pounding.

"Fuck me," I begged.

With that, he began to fuck me with full force. His big, thick cock moved in and out of my butt pussy as I looked up and gazed into his face. His smile was to die for. He was having a totally new sexual experience and he seemed to be enjoying it with a vengeance. I felt him thrust his cock into my belly, his pelvis and pubic hair banging against my groin.

Once again, I reached for my member and stoked myself as he fucked me.

A short while later, his body went into a spasm, he let out a groan, and his pelvis pounded hard against me. Then, he stopped. I felt his cock throb inside of me before shooting his load into my belly.

When he finished ejaculating, he resumed pounding my butt pussy so that I could come. A short while later, I ejaculated as well.

Afterwards, we wiped ourselves off and laid down to cuddle. Matt held me tight in his arms until I fell asleep. This was the best sexual experience of my short twenty-one years.


A few days later, it was time for reality check. He hadn't called or texted me, nor did he return my calls or texts. Sound familiar?

I was at work one morning, trying to learn the ropes.

"I need you to redo this report," Fiona barked. "Knight Athletic wants it yesterday and they're just about to walk. Work through your lunch if you have to. But I need it pronto."

"I'm on it," I told her.

As Fiona walked away, my phone rang. Oh my God! It was Matt.


"Shanna, it's Matt,"

"Matt! Hi!"

"Listen, can you meet me for lunch?"

"I think I might be able to break away for a few."

"Nice. Meet me at the little cafe at 48th and 9th."

"Can't wait to see you!"

With that, I hung up.

I walked into Fiona's office and tried to think of an excuse to leave.

"Fiona, I forgot to pick up the mail this morning," I said. "Won't happen again. I promise."

"Can't it wait?" she said. "This account is really important."

"It has to do with the account."

"Okay, but make it quick. I mean it."

After that, I left for the cafe where Matt told me to meet him. My heart raced. This was the first time I can remember a guy calling me back after sex.

I walked into the cafe and saw Matt sitting by himself in the corner. Strange that he chose a booth with no one nearby.

"Matt!" I said.

"Hi, Shanna," he said. There was no smile on his face. This was scary now.

"I made up a lame excuse to get off work," I said. "It's been so hectic and Fiona's breathing down my neck and..."

"I won't take too much of your time," he said.

"What's wrong?"

"Shanna, I don't know how to say this," he said. "I don't think it's best that we see each other anymore."

"I figured."

"Look, someday I want to have children. It's important to me to have them naturally."

Of all the lameass excuses I had heard, this was probably the most pathetic.

"Listen, Matt," I said. "You're twenty-three years old. I'm twenty-one. We shouldn't even be thinking about kids. So try again."

"Okay, fine," he said. "The fact is that as much as I tried to be okay with the whole transsexual thing, I don't know how I can introduce you to my friends or my family. And the sex matter how much I tried to ignore it...below the waist, you're a dude."

I was disgusted. But at least his honesty was raw, even if brutal. I wanted to scream at him. I wanted to slap him.

Instead, I stood up and gave him a hug and a kiss.

"Thank you," I said.

"For what?" he asked. "Dumping you?"

"No," I said. "For having the guts to tell me what no guy wants to say after he just stops taking my calls and blocks my number."

But I didn't want to hear anymore. With that, I just left.


After that experience, I tried to forget about guys and dating. But the depression that I felt after the experiences with Kyle and now Matt were consuming me. I could never have a true, loving relationship with a man until I took care of the problem below my waist. From that point forward, it was my mission to do whatever was necessary to have my reassignment surgery. I would never feel like a complete woman, let alone a complete human being, until that was done.

Unfortunately, that painful depression was taking a toll on everything in my life. I was afraid to go out and make friends. I was terrified to date. The only men who seemed to have any interest in me were men who were looking for a girl "with a little extra."

At work, my personal struggles became apparent. A few months after starting work, Fiona called me into her office for my performance review.

"Shanna," she said. "I like that you're learning things. And that Knight Athletic account was a good save. But I get the impression that there are things going on in your personal life that are affecting your work. I'm going to have to place you on probation."

Well, at least I wasn't fired.

"Thank you, Fiona," I said. "I'll do everything I can to make sure you don't regret hiring me."

"That's what I like to hear," she said. "Now get back to work."

Later that evening, I sat alone in my dank, dingy East Harlem apartment that might as well have been a jail cell. My life was sliding into despair. My love life was a mess. I had no friends. And now, even my dream job was in trouble. Maybe moving to New York was a big mistake.

Suddenly, my phone rang. It was Kyle. I didn't want to talk to him, so I let it ring and hoped that he left me a message.

A few minutes later, I heard the ringtone that told me I had a message. I called my voicemail to listen.

"Hi, Shanna, it's Kyle," he said. "I know what I did to you was pretty nasty and inexcusable. But if you come back to Tennessee, I promise I'll do everything I can to make it up to you. I know you probably don't believe me, but I miss you, babe."

After listening to the message, I thought for a moment about packing up and leaving.

"Too little, too late, Kyle," I said as I deleted the message.

No, I had it wrong. Leaving New York and moving back to Tennessee would be a mistake.

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