I saw Frank come out after changing in his room. I had to admit he looked rather handsome. He wore a dark dress suit with a black tie. On his hand was a small coat. “Here, wear this, Mary. It’s little breezy out today.”
I took the coat. “Thanks, let me just get one of Magda’s old purses. No woman is complete without one.”
Frank looked like a new man. It seemed this little charade had breathed me life into him. Much of his ailments had been mental rather than physical. I was glad to see him in good spirits. Arm in arm, he escorted me to a rather ritzy French restaurant.
I had to admit I was nervous heading out of the front door. The cool breeze hit at the same time I realized what I was doing. I had never gone outside while cross-dressing. My appearance may have fooled Frank but it was not battle tested. However, he was so confident that a bit of it rubbed off on me.
I felt like a real woman being treated out to a date. Frank held my coat and opened doors for me. I even began to forget I was Mark. I was now Mary.
When we arrived at the restaurant, it was buzzing with activity. It provided some much needed cover. I didn’t have to worry too much about someone focusing on me.
At the same time, I worried that someone would recognize that I was a man pretending to be a woman. I kept my head down and tried to be as discreet as possible. However, I still got my fair share of glances from the waiting staff and other guests.
On the other hand, Frank played it cool as he checked in. “We have a reservation. A table for two.”
The hostess smiled as a young waitress came in. “We were expecting you.”
“Right this way,” the waitress said, guiding us to our table. As we walked, she turned to me and said. “That’s a lovely dress. I’d love to have one like that.”
I blushed as Frank chuckled. The disguise seemed to be working. “Thank you. I got it from him.”
My date added. “I knew I had to get it for her the moment I saw it.”
The waitress flashed me a smile. “Lucky girl.”
We sat at a nice table in the corner. It was such an elegant event. The waiting staff treated me like royalty. I felt so blessed to have this dinner with Frank.
Over a three course meal, we bonded in a way we never could as nurse and patient. I always had to keep my distance from him when we were working together. I just checked his vitals and cleaned up his house.
Now, the barriers between us were gone. He knew my secret. In return, I knew he liked to see me dress as a woman.
After we finished dinner, Frank drove us home. No one had guessed that I was a man. Hell, some of the waiting staff described me as Frank’s lucky date.
Indeed, the man seemed enamored with me. At the restaurant, he had hugged and kissed me. I placed my head on his shoulder as he us drove home.
Frank didn’t need to tell me how beautiful I looked or how happy he was. We found a way to communicate without words. Well, he did place his hand on my leg. I didn’t think too much of it until I felt his fingers touch the top of my stocking.
It made my cock harden.
The rest of my body stiffened as well. For months, I had been Frank’s nurse. Now, I realized how much closer we had become after he had caught me cross-dressing.
Frank noticed my reaction and took his hand away. “Sorry, I just haven’t been intimate with anyone.”
I giggled. “It’s okay. Me neither.”
When we got home, I went to Magda’s room to undress. I stopped when I got down to my undergarments. I didn’t want to change back to being Mark just yet. I felt so comfortable as Mary. I knew Frank preferred me that way as well.
Still in my undergarments, I reapplied my makeup and lipstick. Then, I took out the new nurse outfit that Frank had given me. Before long, I looked like the sexiest nurse in town.
I went out and saw Frank sitting down in an arm chair and nursing a scotch-whiskey in one hand. He had taken off his tie and jacket. When he saw me, the man whistled and said. “Hello nurse! Looking sharp.
He handed me another glass of scotch-whiskey. “Thanks.”
I sat on his lap as he reclined in the chair. Man or woman, I couldn’t recall the last time I had been so intimate with someone. It may have been Frank’s birthday but I felt like it was my sweet sixteen. It was as though I were being treated like a princess.
I almost forgot I was even a man. I had been transformed into Mary. The alcohol certainly helped me get into the mood. I finished off the glass in a few swigs.
Frank chuckled. “Ease up on the drinks, nurse.”
I giggled as he slipped his arm around me and kissed me on the cheek. I felt a chill run up and down my spine. My cock grew hard under my skirt.
I turned to face Frank. He looked so handsome with his unbuttoned shirt. He had always been a strong, virile man. Most of his problems had been emotional rather than physical.
I couldn’t help but place my lips on his.
His eyes widened in surprise as my tongue entered his mouth. Frank relaxed as we kissed. His hand went under my skirt and caressed my thigh. I shuddered at the wave of pleasure that pulsed throughout my body. I allowed his fingers to explore me as I suckled his tongue.
My ears were ringing as I parted my thighs. His hands gently explored what was hidden under my dress. It found the head of my cock under the soft fabric of my panties. Under my skirt, I could feel his shaft harden as well. It poked my backside as I sat on his lap.
Finally, Frank broke his kiss and said. “God, I’ve missed this. You won’t believe how you’re making me feel, Mary.”
I looked deep into his eyes. “Me too…”
“I love you.”
“But I’m not a real woman, Frank.”
He planted a kiss on my lips. “You’re more woman than I could have ever hoped for. Hell, half the men at the restaurant were ogling you. They saw a beautiful girl and her lucky date.”
I returned his kiss. “I love you, Frank. I always did but I do more so now. I want to be your woman.”
He smiled. “Good, you can start by getting off of me. My cock feels trapped under you!”
I giggled as I got off of him. “Sorry!”
As I stood up, Frank unzipped his slacks and pulled them down. His boxers soon followed and his massive prick sprang up. My jaw dropped at its sheer length.
It was much longer and thicker than mine. Its head was engorged like a mushroom. I didn’t know where to begin.
However, I knew which parts were sensitive from experience. I grasped the base of his erection and worked my way up its soft underbelly. Frank returned the favor by sliding his hand inside my panties. I felt his fingers touch the tip of my cock. Then, he slid the silky panties down my legs and removed them.
Staring at his erect cock, I couldn’t help but get on knees and plant a soft kiss on its head. I could see pre-cum dripping from its tip. My tongued darted out to taste the clear fluid. Frank shuddered when I tasted him. I continued to lick his head as he moaned in delirium.
Frank placed his hands on the back of my head and moaned. “That’s it, Mary. Suck my cock like a good little nurse.”
He thrust his shaft into my mouth. It stretched my lips and went deep inside my mouth. He kept pushing harder and deeper into me. My lipstick stained the length of his prick as he fucked my face. I let instinct guide me as I suckled him.
Soon, I fell backwards from the force of his thrusts. We were both ecstatic from the blowjob. However, I knew Frank wanted to go further.
He caressed my face and asked. “I need you, Mary. If that’s what you want…”
I kissed him and replied. “I do! Make me a real woman.”
I wasn’t sure how this was going to work but I wanted it. Thankfully, Frank took charge. He raised my skirt and hiked it up so it exposed my buttocks. Finally, he took off my panties.
Suddenly, I felt soft kisses on my buttocks. I turned around to see his grip my erection and stroke it. Again, I felt his mouth on my ass. His tongue plunged past my track and lick
ed my rosebud.
God, it felt so good.
My body gyrated from the sensations I felt. My ass was slick with Frank’s saliva. Soon, his tongue penetrated my rosebud and entered me. I shuddered at first before relaxing. His tongue probed me as his hand stroked my cock. I experienced such overwhelming pleasure.
Frank pulled me back underneath him. I felt his massive prick slide between my ass cheeks. Its huge head made its way past my crack.
I cried out when he entered me. “Ahh!”
However, I began to relax when I got used to the intrusion. Frank steadied himself by grabbing my hips. Slowly, he entered me with the entire length of his cock. I body shivered as he inched his way into me.
Frank groaned as he shoved his cock deeper into me. “Oh… you’re so damn tight. It’ll get easier…”
I moaned as he buried himself to the hilt. I couldn’t believe how much of him I had taken in. Frank’s cock felt as hard as steel as he impaled me. At the same time, my prick was getting just at hard.
I felt his hands tear open the buttons of my blouse, slip past my padded bra, and pinch my nipples. I felt him stroke them with his thumb. I was trapped between his forceful instruction and his playful teasing. I was lost between these two extremes. I couldn’t stop my body gyrating under him as he thrust into me.
Gripping my hips, Frank began to wildly pump into me. My body bounced up and down his shaft. “Oh yes… Mary. That’s it! God, you feel amazing!”
We were both approaching our end. Frank erupted inside of me. He cried out as his hot cum filled my buttocks. He planted his seed deep inside of me.
Likewise, I was spurting my load onto the floor. I was as hard as I had ever been. I didn’t want this union to end. However, neither of us could ever go on any longer.
Frank took me into arms and kissed me. “That was quite… therapeutic.”
“Get ready for another round of treatment,” I said, with a laugh before returning his kiss. “Nurse’s orders!”
Nothing came without a price.
I learned that the hard way when the mob offered to pay for my sex change and hormone treatments.
I suppose I should start from the very beginning.
My name is Alex and I used to be your average teenage boy. I lived a comfortable life in the suburbs in a two story house. Those days now seem like a distant memory. As much as everything about me has changed, at least my name is still the same.
My family was upper-middle class. I was an only child and got on okay enough with my parents. We weren’t especially close.
There wasn’t much else to say. I went to school and got decent grades. I didn’t have many friends. My life was boring as boring could be.
Well, that is until I decided to be a girl.
As expected, my parents blew a gasket at the idea. They thought I was born a boy and I’d stay that way until I hit the grave. However, I just wasn’t happy being a boy. I read about changing my sex to that of a girl. I knew I couldn’t afford the treatments and operation without their help.
Worse, my parents wanted to send me to a military academy as a form of discipline. They wanted me to man up and get back to being normal. They thought this strange phase was just a bug in my system a good year with a strict drill instructor would fix. I wasn’t as keen on the idea.
That’s when I packed my bags and left. It wasn’t easy at first. I ran out of money real quick and had no place to stay. There was no way I could pay for medical treatments if I couldn’t even afford a roof over my head.
Soon, I found myself in a homeless shelter. I had nowhere else to turn to. Thankfully, they gave me a bed and bowl of food. The people there seemed so nice. I didn’t have to live on the streets or worry about when my next meal would come.
I told them who I was and where I came from. The people in charge of the place were very understanding. I felt like I could tell them everything about myself. Eventually, I confessed that I wanted to be a girl.
To my shock, they not only supported my decision but also offered to pay for my sex change operation. It was a dream come true. They felt more like a family than the one I had been born into.
However, they were not good people. Their generosity was just an act. The homeless shelter was a tax shelter for the mob. The place was also a honeypot for young, vulnerable people like me. They lured desperate people in before making them indebted to the mob.
They were the lowest of the low. These men sold everything from drugs to guns and people. Yes, they traded people like they were cattle. They wanted to sell me as a prostitute.
By the time I learn this, it was all too late.
I got my sex change but it came with a heavy price. I had to pay off the debt I owed them. I would work as a prostitute to pay them back.
People like me attracted a certain kind of clientele. I knew it made them more money than that sex change operation and hormone treatments were worth. However, it didn’t matter to them. I was their slave. If I tried to leave, they would kill me as a warning to the other slaves.
As much as my body had changed, so had the rest of me. I loved my new body. Unfortunately, so did many of the mob’s clients. They had a fetish for people like me.
Transgender girls like me were rare in this type of business. Clients were willing to pay top dollar for a night with me. I had become a plaything that was sold from one man to next. They could use me in any way they wanted.
I knew I made good business for the mob. It was more than enough to cover my debt. However, I didn’t dare bring up this point. They could get rid of me if I dared to step out of line.
I met all kinds of horrid people. They would use and abuse me. I knew many of them were important politicians and government officials with close ties to the mob. They paid handsomely for a woman like me. Men like them came to me since they couldn’t get the same thing on a dating website or a regular brothel.
One day, I found myself in the mob’s showroom with a few other girls. I was the only transgender one of the bunch. Nevertheless, we were all the property of the mob.
The men here were ruthless killers. They would slit their mother’s throat for something as little as a nickel. Some of the hitmen the mob hired were even worse. I swore never to get on their bad side.
In the backroom of the showroom, I waited for the inevitable. By now, I had gotten was used to the routine as much as a person could. They would parade us in front of prospective buyers before the clients made their decision. It was something I had done for years. Yet, it never got easier.
I knew I had to stay strong and not give into fear. These men looked for any sign of weakness to exploit. Yet, I buried the despair deep within myself and held onto whatever shred of hope I had left. I knew it was foolish to hope for freedom in a place like this but I still did.
Soon, I overheard the men arranging the auction show. They said I would be the most expensive one and over half my price would be paid up front. I would go as much as $5,000 for a weekend. It was a small sum for some of our clients. Nevertheless, the mob bosses were delight to have such good business.
When so much of your worth is assigned to dollar figure, it’s hard not to think of yourself as a product. I tried not to think about the money I made my captors. It was enough to buy my freedom several times over.
As the men prepared me and the other women, I could look down the small window of the room and look at the parking lot. I took every opportunity to see the outside world. I saw that the parking lot was full of expensive cars that weren’t an unusual sight around a mob hideout.
There was a motorcycle in the parking lot as well. It was unusual since most of the mob and their clients preferred to arrive in four door luxury cars. Thankfully, one of the mob’s lieutenants, Tony, answered the mystery of the motorcycle. “Son of a bitch, it’s that damn hitman. Get the girls ready to do business.”
My body shook in apprehension of what was about to occur. As far as the mob went, hitmen were last people you wanted to meet. They were
killers for hire that weren’t associated with any one mafia family. Instead, they only worked for the highest bidder.
These hired killers even made other mobsters nervous. I hoped none of them were interested in buying me for a night. Whatever they wanted, they got.
We were corralled into a large living room. I and four other girls were lined up in front of a row of chairs. We wore short, sheer robes that were made to be dropped on the floor in a split second. It was like some perverse take on a Miss Universe contest.
As luck would have it, I was the only transgender woman in the lineup. I still had my cock with a new set of breasts to go with it. Rather than repulse men, this combination had its fair share of attractors.
The Trans Ultra Collection Vol 1 Page 16