I knew my best friend had been fucking her dad.
Her mother had passed away recently. And during the celebration of life for her mother, Monica and her dad never left each other's side. They smiled at each other, flirted with each other, and for a half hour during the party, neither were anywhere to be seen. Yes, I knew what was going on.
During that same party, I hooked up with the son of one of Monica's father's closest friends. Kyle was surprised to learn that I am transgendered. But that didn't stop us from going up to Monica's room and getting our freak on. It had been a week since that night, and Kyle had disappeared from my life as quickly as he had arrived. I tried to call him a few times, but he never returned any of my calls. My text messages went unanswered. And that morning, I tried to call him one more time, only to find that my number had been blocked.
This was how things typically went, sadly. The story could have been written like this: Boy meets T-Girl. Boy and T-Girl fuck. Boy thinks fucking T-Girl makes him gay. Boy runs scared and never wants to see or hear from T-Girl again. Sequel repeats the story with next Boy. I was used to this. But it didn't mean it didn't hurt me just a little more each time that movie played.
Back to Monica...
I needed to know the truth. I'm nosy like that. So I went to the house she shared with her dad one afternoon and met up with her as she was relaxing in the jacuzzi.
"Hey, girl," Monica said.
"Hey," I said.
"So what's the deal with you and Kyle?" she asked. "Spill."
"There's nothing to spill," I said. "Since your Mom's celebration, he hasn't returned any of my calls, hasn't answered my text messages, and just a little while ago, I see he blocked my number."
"Girl," she said. "Believe me when I say you are so much better off without Kyle the Pile in your life."
"He's had this crazy obsession with me since I was sixteen," she said. "He tries to cozy up to my friends in hopes that they will convince me to sleep with him. He's a stalker and a creep."
"He probably fucked me as a way of getting back at you or something," I said.
"Oh my God!" she said. "You fucked him!"
"Yes, at your Mom's celebration," I said. "We snuck up to your old room. Hope you don't mind."
"That room got all kinds of action that night," she said.
"What are you talking about, girl?" I said. "Did Monica get some action, too?"
"You could say that," she said with a smile.
"Oh my God!" I said. "Who?"
"Oh, please," Monica said. "It's not like you haven't figured it out."
I knew her secret. And Monica knew that I knew.
"Your daddy?" I said.
"What can I say?" she said. "Now you know my deepest secret."
"Oh my God, girl!" I said. "That's so hot!"
Monica removed her sunglasses and looked directly at me.
"Really?" she said. "I wasn't expecting that."
I took off my shoes and sat on the edge of the jacuzzi.
"So, let me ask you something," I said. "If I wanted to try and seduce my dad, how would I do that?"
"Oh girl," Monica replied, thoroughly shocked. "I've always wanted a partner in sin! This is great!"
"Well," she said. "First, you need to remember that every man fantasizes about his daughter. That's rule number one, number two, and number three. Second, you need to feel him out, make sure he's ready to make the jump, if you know what I mean. Then, you do something that leaves no doubt you want to get down and dirty with him. I dropped my robe one day and let him see everything I had to offer."
"Well," I said. "I'm sure that works great if you have a pussy."
"What you do is wear your g-string, you know, to hide your boy parts," she suggested. "Drop the robe and stand there long enough for him to see your titties. Then, quickly turn around and show him that awesome ass of yours. Bend over to pick it up and make sure he can clearly see your hole."
"And something else you have to remember about men," she continued. "Every guy in the world would kill for a girl who will take it in the ass. Since that's not a problem for you, you're already ahead in your game."
"That sounds so hot!" I said.
I felt my vestigial cock begin to get hard under the g-string I wore under my shorts to conceal it.
"Believe me," she said. "Your daddy will be your easiest catch. And I've always told you that if I were a guy, I'd fuck you in a heartbeat. You've got assets, girl. So use them to get what you want."
I went home that afternoon, ready to work my thing. Mom had gone out with her girlfriends for the day and it was just me and Daddy.
Daddy was a very handsome man. He was 43 years old with a fit and athletic build. He was very healthy for his age and took good care of himself. He had beautiful blue eyes and a full head of platinum-silver hair. He had begun going gray at an early age. Daddy didn't drink, didn't smoke, and worked construction, which kept him healthy and in shape.
This was the most striking difference between myself and Monica. She liked bad boys, men who drank, smoked, got in fights, spent time in prison, wore tattoos, and rode Harleys. I preferred boy next door types. I liked a healthy, fit, strong man with a beautiful smile, who had an old-fashioned sense of right and wrong, the kind of guy who would stop and help a stranded motorist in the middle of a snow storm. And Daddy particularly fit the casting call.
I was a little afraid to attempt Monica's drop-the-bathrobe trick she had used on her father. Instead, I chose to use my power of manipulation to get Daddy to give me the fuck of my life. But I wore my bath robe for good measure.
"So, is this what you plan to do now that you're out of college?" Daddy asked.
"What?" I asked.
"Sleep till four in the afternoon and walk around the house in your bath robe?" Daddy said.
"No, I went over to Monica's for a little while," I said. "Then I came home and took a nap."
"What about your chores?" Daddy asked. "And when are you going to go look for a job?"
"Don't worry, Daddy," I said. "I'll have the bathrooms clean and the vacuuming done as soon as I get something to eat."
"Just make sure you do it," Daddy said. "Your mother's been in a grumpy mood lately."
I sat down at the kitchen table and changed the subject.
"I think I might need to go to the doctor to get my hormones increased," I said.
"I told you to be careful about that," Daddy said. "You're already taking more estrogen than a C-girl your age produces."
Daddy was well familiar with the lingo. "C-girl" stood for "cisgendered girl," which is the term for a female who was born with female parts.
"I don't know, Daddy," I said.
I stood up and walked over to him. Then, I pulled back my bath robe to show him my naked breasts. He was shocked.
"Sweetheart!" he said.
"Daddy, come on," I said. "It's nothing you've never seen before."
"Anyway, tell me if you think they feel fake," I continued.
"Shanna," he said. "I feel really weird about this."
"Feel my nipple," I said. "Does it feel right to you?"
Hesitantly, Daddy reached over and touched my nipple. This drove me absolutely wild. My cock suddenly became rock hard. Daddy's finger on my breasts was truly electrifiying.
"It feels just fine, sweetheart," he said. "Stop worrying."
"I guess," I said, pulling my bath robe back over my breasts.
I sat back down.
"Daddy," I said. "I have something really juicy to tell you."
"What's that, sweetheart?" Daddy asked.
"So, I'm at the party, you know, for Monica's mom who passed away," she said. "And Monica and her dad are getting really flirty with each other, right?. Well...it turns out she and her dad are actually...doing it!"
"And how do you know this?" Daddy asked.
"I figured it out," I said. "But then she told me all about it when I saw her today."
"Well, you know," Daddy said, "sometimes that sort of thing happens."
"I guess," I said. "It's just a little weird, that's all. Monica's always been so innocent, so...goody-goody."
Daddy leaned over the table and looked me straight in the eye.
"And what about you?" Daddy asked me.
"What about me?" I asked.
"Are you trying to get your dad to sleep with you?" he asked. "I mean, I know how you look up to this girl."
By now, I was blushing. Big time.
"No," I said with a laugh.
"Well," I continued, after an uncomfortable pause. "I don't know..."
"Maybe," I said, as I brushed back my long red hair and gave Daddy a seductive smile.
"You really want me, your own father, to fuck you?" he asked.
"Well, I've read on the internet that every man has secret fantasies about his own daughter," I said.
"Shanna," he said. "You shouldn't believe everything you read."
"Have you ever fantasized about me, Daddy?" I asked.
Daddy was silent.
I got up and took off my bath robe. The only stitch of clothing I had on was the black g-string thong I used to hide my boy parts. Then, I walked over and sat on his lap. I gently put a finger on his lip.
"Your silence says everything I need to know," I said with a seductive smile.
As I sat on Daddy's lap, I felt the cock under his jeans expand to fill the crack in my naked ass. Daddy picked me up and carried me to the bedroom.
"I can't believe we're doing this," Daddy said with a nervous laugh.
Once in the bedroom, Daddy sat me down on the bed.
"If we're gonna do this," he said. "We've got about two hours before your mother gets home."
"I know, Daddy," I said.
Daddy took off his shirt, revealing his well-defined pecs and muscular arms. The carpet of hair he wore on his chest was as silver as the hair on his head. He was tan from working outside in the hot sun.
He walked over to me, unbuckled his belt and unzipped his pants. Then, he pulled down his underwear and revealed to me his hard, cut 7-inch cock that was dripping with fluid. I took hold of it and stroked him as I looked up and smiled at him. He smiled back at me, signaling to me that he was definitely into this.
Daddy's cock was warm to the touch and throbbed as I held it in my hand.
"You wanna suck on it?" he asked.
Daddy pulled down his pants to his knees, allowing me to take his cock in my mouth as deep as I possibly could. I put my lips to his mighty manhood and teased his head with my tongue before sucking it into my mouth.
I let out a moan as he set his hand on my head, guiding it into his groin.
My tongue played with the veins and ridges of his cock that burned in my mouth. Daddy let out a guttural grunt as I continued to suck him off.
Daddy's cock was huge, well-developed, and a symbol of his manhood. His balls, covered with his silver-gray pubic hair, were large, warm and intimidating. In contrast, my boy member was barely developed, and my balls had shriveled to almost nothing due to the hormones. I worshipped Daddy's cock, which I swallowed deep into my throat.
"I'm gonna come if you keep that up," Daddy said, gently withdrawing his cock from my mouth.
Then, he put his hands on my breasts and squeezed them. I felt his fingers tease and play with my intensely erect nipples.
"You've got nice boobs," Daddy said. "You don't need to worry about taking more hormones."
I assumed the position on all fours, exposing my pussy butt under the g-string to Daddy. I made sure that I applied my sweet-smelling oils, both to lubricate myself and also to give my posterior a nice, feminine smell that would turn Daddy on.
As I raised my well-oiled ass in the air, I felt a hard, firm finger penetrate my behind. The sensation was phenomenal. A second finger violated my tight canal.
Daddy stretched my ass enough to relax my sphincter. Then, he applied some K-Y jelly and prepared to fuck me.
Like a cat in heat, I arched my back and raised my ass in anticipation of the assault on my rectum that was to come. Finally, I felt the head of Daddy's cock push into me. It hurt like hell at first as his thick dick pushed my sphincter apart. Daddy pushed slowly and gradually until he felt my ass open up to let him in. Then he pushed himself into me as deep as he could.
I moved back against his pelvis to signal to Daddy that I was ready to be pounded with full fury. And he delivered.
My entire body violently shook back and forth as he took control of me with every thrust. Daddy's mighty cock commanded my submissive ass with each stroke back and forth. My boobs helplessly swung back and forth from my chest.
Finally, Daddy shot his cum into me, letting out a huge groan as his semen streamed into my thoroughly-ravaged ass.
Then, Daddy pulled his cock out of me and lay down on the bed. I lay down next to him and kissed him.
The small bit of testosterone that my body was allowed to produce gave me the sex drive to have this awesome physical experience with my daddy. But now, the estrogen was taking over. This was where things began to turn sideways.
"Daddy," I said. "I'd like this to be a regular thing."
Daddy sat up to put his pants back on.
"What do you mean by that?" he asked, buckling his belt.
"Let Mom go," I said. "I don't want to have to share you with her."
Daddy put on his shirt.
"Sweetheart," Daddy said. "What we just did was amazing. And yeah, I'm up for more of this. But I'm not leaving your mother."
When he said that, I was finally hit with a dose of reality. His true love was Mom. I was the afternoon delight. The dirty little secret.
Humiliated, I walked back to the living room and put my bath robe back on.
A short while later, Mom came home. She walked over to Daddy and planted a huge kiss on his lips. Then, she turned to me.
"Shanna," she said. "Are your chores done?"
"No," I said. "I was a little busy."
"Busy? Doing what?" Daddy demanded. "You promised your mother you'd have the house vacuumed when she got home."
This made me utterly sick. Daddy covered his ass by throwing mine under the bus. Not cool.
Later that evening, Mom and Daddy went to bed. My bedroom was across the hall from theirs, so I could hear almost everything that went on behind their door. I began to hear the sound of Mom moaning like a wild animal in heat, along with the sound of the bed squeaking as Daddy fucked her. It was clear to me: Daddy and I could never be our family's version of Paul and Monica.
I couldn't wreck Mom and Daddy's marriage. They had been together since they were teenagers. I was their love child. Indeed, their only child. An afternoon of naughty fun wasn't going to change that. I knew that when I made the suggestion. Still, I wanted Daddy to myself, just as Monica had her daddy to herself. I longed for my daddy as my lover and soul mate. And that made listening to them fuck in the bedroom across the hall unbearable. I couldn't live in this house and watch Mom and Daddy be intimate and loving toward one another while Daddy and I sneaked away to fuck whenever Mom's back was turned. I deserved better.
I packed up as many of my belongings as would fit into my little Mazda. That wasn't much, but I took all of the essentials. I left behind a photo album of myself as a boy. And then, in the middle of the night, without any warning, I left home and headed for the Big Apple.
After driving all night, I was now somewhere in the middle of West Virginia. Mom and Daddy called frequently, but I did not take their calls. I didn't want to go home and "talk about this," as I knew they would beg me to do. I didn't want to have to tell Mom that I did the deed with the love of her life. My phone rang once again, but this time, it was 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," I said. "Let's just say things didn't go very well with Daddy,"
"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. "My boy's a hard worker. He's a good kid and a good son. But I think he's a little light on his feet if you know what I mean. So how 'bout you show us a good time with your womanly charm, give me and my boy lay we'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 me and my boy each take a hole?" he asked. "You into that?"
"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 we'll just have to take turns coming in the back, now won't we?"
"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.
"Hmmm...you'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.
At that moment, Junior came through the door.
Jesse stood there, in complete shock, as his nasty, disgusting father was being blown by a young beautiful thing.
Not that Jesse was a much more attractive prospect. He wore filthy jeans that were covered with motor oil and dirt. His hands were blackened from working on cars. I couldn't tell if his gray shirt had been white at one time, but it was almost totally black now. A cigarette dangled from his lips, which were attached to his oil and dirt-covered face. I didn't even want to see the hair that was hidden under his dirty cap.
Nevertheless, compared to his father, he was a dreamboat. In fact, in any other setting, he might even be cute if he were cleaned up a bit.
"If y'all are busy...." he began.
"Actually, Bubba," I said with a big smile. "We were hoping you'd join us."
Jesse shut the door and took off his shirt, revealing a chest that actually wasn't too unattractive, considering. But those filthy motor oil-stained hands were just seconds away from touching my privates.
As I continued to suck Senior's cock, I shook my ass to invite Junior over to play. Jesse walked up to my ass and put his oil-soaked hands on my ass. Then, I felt his finger work its way down my crack, along my butt pussy, and down toward my balls. When he touched my balls, he realized immediately that I wasn't like other girls.
"Hey, you're one of them she-males!" he said, groping my male genitals and smearing motor oil all over my cock.
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.
"And you're one of them really observant hillbillies," I said to Jesse.
I turned around to lay down on Terry's desk so that I could show my boy parts to Jesse to allow him to play with them.
"Never fucked a she-male before!" Jesse said. "You mind if I play with it?"
"Be my guest, you big stud."
He looked at my dick with curiosity, taking notice of the fact that although it was able to get erect, it did not stay hard for long. My scrotum was bright red and had a prominent ridge down the middle. These were the effects of the estrogen I was taking. Jesse's fingers moved through my pubic hair, teasing my cock and balls and soiling them with motor oil and grease. Normally, I would never allow a man to do this to me. But again, I had no intention of ever seeing him again. I simply didn't care, as long as we got done with this awful sex as soon as possible.
Jesse put out his cigarette and put his face to my crotch. He then took my cock in his mouth and sucked me off. Terry stood over my face and reinserted his old dirty cock into my mouth.
Jesse's tongue moved up and down my very hard cock. But moments later, I lost the erection. He continued to suck me anyway. I smiled at him and took Terry's cock out of my mouth for a minute.
"You like that, don't you?" I said to Jesse.
He didn't answer. He just kept sucking me. I resumed sucking his father off.
Terry let out a series of groans before pulling his cock out of my mouth.
"We're gonna take turns and I'm gonna go first," he said to Jesse. "Come on over here."
Oh my God, I thought. This was the signal that I was about to take this man's nasty, filthy cock in my ass.
"You got a condom, by chance?" I asked him.
"Sorry, baby," he said with a smile. "No rubbers here. It's not every day a purdy little thing like you shows up."
Great. He was going to fuck me raw.
Terry and Jesse switched sides and I resumed my position on all fours on Terry's desk. Jesse took off his pants, revealing his long, thin needle dick. He had a large pink head that was much too large for the rest of his cock. But there was a stench that radiated from his groin. It was the smell of body funk from someone who hadn't showered or bathed in days. Jesse stroked his cock with his grease-covered hands before putting it into my mouth.
I felt a horrible finger run along the crack of my ass and butt pussy with a dab of a greasy substance that I hoped was Vaseline.
I sucked on Jesse's smelly cock, which tasted like the closest thing I could imagine to someone's ass before wiping. Then, I felt Terry penetrate me. Like most men not experienced in anal sex, he shoved his cock in me without allowing me to adjust to the assault on the sphincter. At least he was small enough to not hurt enough to scream.
I sucked on Jesse's cock as Terry pounded my ass from behind. With each thrust from Terry behind me, my body pressed Jesse's cock deeper into my mouth. Jesse reached down to play with my titties as they bounced back and forth.
Terry soon came in my ass, shooting his vile load into me. Then, he pulled out. This was the signal that it was Jesse's turn.
"Get on your back, sweetheart," Jesse instructed me.
Doing as I was told, I turned over and lay down. Jesse took hold of my legs and put them over his shoulder. Then, he took hold of his cock and slid it into my ass, which was relaxed enough for penetration, thanks to the pounding I had just taken from his father.
Jesse looked down and smiled at me as he fucked my ass. Then he reached down and played with my cock. He pounded me with fury and vigor for about ten minutes, jerking my cock off as he fucked me. Finally, I came.
Jesse, however, wasn't ready to come. So for the next several minutes, I let him pound my ass as I was post-orgasmic and my muscles were beginning to tighten. Finally, my body could take no more and my ass finally ejected his cock.
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."
I continued to walk toward the door, but I decided I wasn't going to leave without a parting shot.
"Oh, and Terry," I said with a huge, bright smile. "I agree. Your kid is definitely queer."
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 c-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 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?"
"Cherry Valley, 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?" I asked. "You from here? What do you do?"
"I'm from Iowa," he said.
"Oh nice," I said. "Handsome, corn-fed farm boy."
"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."
"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.
"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 23rd 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."
"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 21 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,"
"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.
"Shanna, I don't know how to say this," he said. "I don't think it's best that we see each other anymore."
"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 23 years old. I'm 21. 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 thing...no 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, Daddy, 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 waste. From that point forward, it was my mission to do all I could 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 jail cell that passed for an apartment. 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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<a href="http://www.lushstories.com/stories/incest/shanna-takes-manhattan.aspx">Shanna Takes Manhattan</a>