At sixteen I was far from the cute transgender slut I am today. I had never experienced a kiss or a boyfriend. No one even knew I was transgender except for me. I hid it from everyone. To other people, I was a pretty boy, a feminine, gay sixteen-year-old who secretly dressed as a girl in private.

I hid that I was transgender because my family was not supportive of me being a gay fem boy and would have freaked if I came out as transgender.

My family consisted of my mother, my stepdad, and my older stepbrother.

For the past few months, I have been taking birth control pills for estrogen. I was planning on coming out as transgender when I was eighteen and starting HRT, but in the meantime, I wanted to get a “head start”. I got the pills from my friend Amber. She got them at the health clinic and sold them to me.

I had not been taking them for long, but could already see the effect they were having. My skin seemed to become smoother and I no longer had any facial hair. I was happy with the results they were giving me.

I was innocent and naïve about sex. While I often masturbated about being fucked like a girl, having sex terrified me. I was afraid it would hurt badly, even though in the transgender porn I watched and masturbated to. The girls seemed to enjoy it.

A few times I even tried putting a finger in my ass when I jerked off, but I could only put the tip in, although I generously lubricated my finger. Having my boy-pussy penetrated scared me.

I was openly gay. There was no way I could hide being gay. I had always been a feminine boy in my physical appearance, my mannerisms and my feminine voice. I have a skinny, feminine body with no muscle tone and a cute, skinny butt.

My black hair is not as long as it is today. At sixteen, it was short and came down just to my ears and the nape of my neck. I didn’t do much to style my hair, I just brushed it straight down. I had a cute, feminine face that some people called pretty like a girl’s.

My first lover was my married, thirty-seven-year-old neighbor, Mr. Johnson. I never thought of Mr. Johnson sexually until the day he kissed me. I jerked off in front of him, and I sucked his cock.

My affair with Mr. Johnson started on a late June afternoon. I was on my way home from a local comic bookstore in a strip mall about two miles from my house. I was pushing my bicycle because it had gotten a flat tire. The sound of a car horn suddenly startled me and then a large pickup truck pulled over in front of me.

I relaxed when I saw it was Mr. Johnson. He and his wife and two kids had been our neighbors for the past five years. He rolled down his window.

“Hey, Nathan, do you need a ride home?” he asked me.

“Yes, please,” I answered without hesitation.

Mr. Johnson got out of his truck and placed my bicycle in the truck bed as I removed my Power Puff Girls’ backpack, placed it in the extended cab behind the seat, and got in the passenger side of the cab. Yes, I had a Power Puff Girls’ backpack. The Power Puff Girls are awesome!

“I have a few errands to run first, if you don’t mind,” the man told me as he got in the truck.

“Sure,” I answered.

Mr. Johnsson made his stops for his errands and as we rode in the truck, the man made conversation with me. It was mostly just small talk.

“Do you have a boyfriend, Nathan?” he asked.

The question caught me off guard. It was not that he asked if I had a boyfriend. Everyone knew I was gay, but I didn’t expect him to get personal.

“No,” I answered.

“Why? You are a pretty boy, like a girl pretty, and it’s hard to believe some kid at your school had not snatched you up yet,” he told me.

I blushed. “The boys I like don’t like me,” I blurted out.

“Oh, I can’t see why not,” Mr Johnson said.

“Because they are straight,” I admitted.

There were a few boys who I had crushes on, but they were straight boys and would never give me the time of day.

Mr. Johnson chuckled. “Yeah, teenage boys can be stupid sometimes. They worry so much about being labeled as gay and don’t see a good thing that’s right in front of them. Some grow out of it. I did.”

It suddenly hit me that Mr. Johnson was flirting with me. He had been flirting with me as soon as I got into his truck. At first, I didn’t realize it because no one had ever flirted with me before. I liked being flirted with and flirted back.

“Well, I never had a boyfriend. I never even kissed a boy before,” I admitted, and pouted. I never engaged in any flirting and I hoped that my admission would be seen as such.

“How old are you now, Nathan?” he asked.

“Sixteen.”

“Sixteen and never been kissed. That’s a shame,” Mr. Johnson told me, glanced at me, and smiled.

I giggled. “I think so too,” I told the older man.

Mr. Johnson continued to talk to me, told me several times how pretty like a girl I was, and flirted with me. I flirted back.

When we got close to the street where we both lived, Mr. Johnson passed the street turnoff and kept driving. I thought he had more errands to run. I didn’t mind. I had nothing to do when I got home, anyway.

When Mr. Johnson pulled into the parking lot of an abandoned grocery store that was long closed, I got curious. I was not scared. I knew he was not going to hurt me. I didn’t know him very well, but I knew that about him. Plus, plenty of people saw me in his truck and if he did do anything bad to me, the police could easily trace it back to him.

“Where are we going?” I asked when Mrs. Johnson drove to the back of the store and then down a dirt road path that led to the woods in the back of the abandoned building. I was now getting scared.

Mr. Johnson didn’t say anything until we drove down the path further. He then stopped and put his truck in the park gear.

“I think you are a sexy little thing,” Mr. Johnson told me. “Don’t worry, Nathan, I am not going to hurt you or do anything you don’t want, but I would like to give you your first kiss.”

I swallowed hard. I did believe when he said he was not going to hurt me or do anything I didn’t want to do. I looked at the older man.

Mr. Johnson was attractive for his age, but not the type of man I was attracted to. Mr. Johnson was a large man. He was well over six feet tall and burly looking. He had a large chest and a slight beer gut. He had large biceps and forearms that reminded me of Popeye the Sailor. Mr. Johnson worked a manual labor job at the power plant and looked like it.

He was married with kids, but that didn’t concern me. I didn’t care about that. He would be the one kissing another person besides his wife, not me.

I bit my lower lip and nodded. “Ok,” I told him.

I never had some fantasy about my first kiss or how perfect it would be. I just wanted to be kissed and here was my opportunity.

Mr. Johnson leaned his head toward me and I moved mine towards him. When his lips pressed to mine, I kept my eyes closed as well as my mouth. I had never kissed anyone, and I was clumsy and not good at it.

Mr. Johnson moved his head back, looked at me, and smiled. “Relax, Nathan, this is supposed to be fun,” he told me.

“Sorry,” I muttered and blushed at my naivety.

We kissed again, and this time I relaxed, and we were soon making out.

Mr. Johnson’s kissing was passionate, intense, and forceful. I liked how forceful he was and I was making soft whimpering sounds as we kissed. My young cock was rock hard.

I moaned out when Mr. Johnson started kissing my neck and wrapped my arms around him. When Mr. Johnson started to tug at my tee shirt to pull it over my head, I didn’t stop him.

Once the shirt was off of me, the older man looked at my body as he ran his large, calloused hands up and down the front. He caressed my stomach and up to my chest. I watched his hands slide up to my hard nipples and gasped out in pleasure when he started to tease them.

“You have such a sexy body, Nathan,” he told me as he gently rolled my nipples between his thumbs and forefingers.

I closed my eyes and didn’t say anything as I enjoyed him touching me. I was extremely aroused. My nipples were painfully hard and taunt, my cock felt like it was going to burst out of my girls’ boy short underwear and my denim shorts. My breathing was rapid, and I was making gasping whimpering sounds.

“I want to see your cock, Nathan,” Mr. Johnson told me in an authoritative voice.

“I…I don’t know,” I answered. I was suddenly afraid. I was afraid Mr. Johnson was going to try to fuck me. He could easily overpower me and take what he wanted. The authoritative tone in his voice excited me.

“Show me your cock and I’ll show you mine,” Mr. Johnson promised as he kept fondling my nipples. “Would you like to see my cock, Nathan?”

I bit my lower lip and nodded.

“Take off your shorts,” the man told me in a commanding voice that again excited me.

“You said I could see yours also,” I reminded the man.

Mr. Johnson chuckled. “You will, I promise.”

“Ok,” I told him and started unbuttoning my shorts.

I dragged down my shorts and then my underwear. My erect penis sprang up and I blushed when I saw Mr. Johnson looking at it.

“You have a nice cock, Nathan. It’s bigger than I thought it would be,” he told me.

My cock is a little above average size, but it does look larger because I have a thin, feminine body and like the rest of my body, my crotch is hairless. I shaved my pubic hair and used hair removal on the rest of my body.

At sixteen, I wished it was smaller because to me it would have made me feel more feminine. As I got older I came to appreciate the benefits of having a slightly above average size cock.

I waited for Mr. Johnson to pull down his khaki work pants so I could see his cock, but he didn’t.

“Touch yourself, Nathan,” he ordered me instead. “I want to watch you jerk off and see you cum.”

I was embarrassed to masturbate in front of the man, but the way he ordered me and the tone of his voice made me feel I had no choice and it also aroused me. I didn’t look at Mr. Johnson as I slowly placed my hand on my erect penis and started to stroke it slowly.

Out of the corner of my eye, I saw Mr. Johnson lift his short-sleeved work shirt, unbuckle his pants, unbutton them, and pull his pants and underwear down to his knees. I then looked at his hard cock jutting up from his crotch.

I thought his cock looked sexy. It stood straight up from the dark pubic hairs and was about the same length as mine, but was thicker than mine. Seeing his penis made me more aroused and I started stroking my cock harder and faster.

Mr. Johnson leaned over and started kissing me again, and I kissed him back as I jerked off. The man soon kissed my neck and once again played with my hard nipples. I was moaning and gasping in pleasure as I stroked myself harder for him.

I let out a loud, gasping moan when Mr. Johnson lowered his head and started sucking my nipples. While he did so I kept my eyes focussed on his hard cock. It felt so good and I quickly felt myself about to cum.

“I’m going to cum,” I told the man.

Mr. Johnson pulled his head up and looked down at my cock. I made gasping, moaning grunts of pleasure when cum started shooting out of my cock. I had never ejaculated that much fluid before. It spurted out of me in thick, string-like loads. Cum landed on my shorts, the car floor, the seat between my legs, and my belly.

I was panting after I orgasmed. “I…I’m sorry it got everywhere,” I told Mr. Johnson.

“You should be,” he told me. “You need to clean it up and clean your hands. Lick it up, Nathan,” the man ordered me.

At first, I thought he was teasing. I had no problem licking the cum off my fingers and hand. I did that all the time when I masturbated. I liked the taste of my cum. But licking it up off the truck seat and the floorboard would be humiliating.

“Do it, Nathan,” Mr. Johnson ordered me again.

I swallowed hard and nodded. He was scaring me again and I thought he might hit me, or worse. I started by licking my fingers and hands clean, then I moved the seat back, got down on the floorboard, and licked the seat clean.

“That’s being a good sissy boy slut, Nathan,” the man said to humiliate me more.

I got suddenly aroused again by his words. He kept calling me a sissy boy, a slut, and a twink whore. The verbal degrading aroused me and I started licking up the cum more eagerly.

Once the seat was clean, I got back in the seat on my knees and bent forward so my head was near the floorboard. I then started licking the cum off the floor mat. I did not even care my skinny, femboy ass was exposed.

I gave a yelp of pain when Mr. Johnson smacked my butt and then moaned in pleasure as he started caressing it.

“Fuck, boy, you have such a nice skinny ass. I like how you don’t have any body hair,” he told me. “Kneel back up in the seat and put your hands on the dash.”

I did as he told me, and Mr. Johnson started caressing my butt cheeks. He then ran a finger down my butt crack. I became so aroused again my penis was once more erect.

“You can jerk yourself off again, Nathan,” the man told me.

I started stroking my hard cock once more. My body stiffened when I felt Mr. Johnson’s finger touch my butthole. He started making a circular motion with his finger around the outside of my tight hole. It felt so good and I let him as I kept jerking my cock.

Mr. Johnson removed his finger from my hole and brought his hand to my face. He then placed his fingers on my lips.

“Suck them, Nathan,” he ordered me.

I parted my lips and started sucking two and then three of his fingers. I gagged when he shoved his fingers deeper into my mouth, but I didn’t care and kept sucking them. Mr. Johnson kept pushing them deeper into my mouth, pulling them out, and pushing them in again. I was gagging and slobbering over his fingers.

“That’s it, boy, get them all wet with your spit,” Mr. Johnson said.

After several more moments of Mr. Johnson fucking my mouth with his three fingers, he removed them and once again ran a finger down my butt crack. It was wet with saliva. He pressed his finger against my hole.

“No, please don’t...please, Mr. Johnson,” I whined out as I let go of my cock. I knew what he was going to do.

“Just relax, Nathan,” Mr. Johnson told me.

I managed to tell him no one more time before I felt his finger enter my butthole.

“Ugh, fuck,” I grunted out as his long, thick finger entered me.

I grunted out again and then again as he pushed his large finger into me, but I was no longer telling him no. I was surprised it didn’t hurt and I felt slight discomfort, but I also felt another, more powerful sensation. I felt an odd pleasant sensation. I felt a great deal of pleasure. It felt so good that I pushed my butt back to have Mr. Johnson’s finger go even deeper.

“Ugh, God....ugh fuck...ugh,” I grunted out as I pushed back and then moved my hips forward and pushed them back again to make Mr. Johnson finger fuck me.

Mr. Johnson didn’t move his hand as I kept pushing back and forth repeatedly, going even faster and harder. God, it felt so good!

“Cum again for me,” Mr. Johnson told me.

I stopped thrusting myself back and forth, took my erect cock in my right hand, and started masturbating once more. Mr. Johnson began finger fucking my butthole. He pushed it deep inside me and began making circular motions. Fuck, it was incredible!

“You like that, don’t you?” he asked. “You like that tight, boy-pussy fingered, don’t you, boy?”

“Ugh, fuck...yes...yes,” I grunted out. I also liked how he referred to my butthole as a pussy.

It didn’t take me long to cum again. Just like the first time, I ejaculated an abundance of cum, but this orgasm was more powerful and made me dizzy. It lasted longer and I could feel it in my testicles. It felt like my balls were being drained. As I was cumming, Mr. Johnson fucked my boy-pussy with his finger hard.

After my orgasm ended, I placed my head on the dashboard, panting heavily, and grunted out as the man pulled his finger out of me. He placed his finger against my mouth. I didn’t hesitate and opened my mouth and started sucking his large finger.

“That’s it, you sissy slut, taste that boy-pussy,” Mr. Johnson told me as he started fucking my mouth with his finger.

I liked him calling me a sissy slut and forcing me to suck his finger. I didn’t care that it had just been in my ass.

He took his finger out of my mouth and gently caressed my cheek. He ran his fingers through my hair. It felt nice. I started licking my hand and fingers clean.

“Now I want you to suck my cock,” he told me.

“What...what about the mess I made?” I asked as I looked down at the cum on the vinyl seat and floor mat

Mr. Johnson chuckled. “I’ll clean it off when I get home.”

I positioned myself to sit in the seat. I moved my body to the side as Mr. Johnson slid his seat back to give me more room.

“I…I never did this before,” I admitted.

I didn’t tell the man that as an excuse or a way to try to get out of giving him a blowjob. I wanted to suck his cock. I told him so he would not expect me to do a good job with it and to let him know I had no oral sex experience.

“I am sure you will do fine, boy,” he assured me. “Hell, my wife stopped sucking my cock years ago, so any blow job will be a good one.”

I giggled at that. I lowered my head and took his cock in my hand. It was rock-hard and warm. I parted my lips and moved to put the man in my mouth. Mr. Johnson placed one hand on the back of my head and one cupped my chin gently. He forced me to look up at him.

“Not so fast, darling, tease it some, lick my balls, run your lips up and down the shaft, and enjoy your first cock,” the older man told me in a gentle voice.

“Ok,” I told him.

I was excited about sucking his cock. I wanted Mr. Johnson to enjoy it, so I would listen to his instructions to make him feel good.

Mr. Johnson let go of my chin and gently pushed my head down. I started licking his scrotum, and then ran my tongue up his shaft. The man left out a masculine moan. I kept running my tongue up and down his shaft and over his testicles for several more moments.

“Fuck, that’s good. Now put it in your mouth,” he ordered me.

I took his cock in my mouth and started sucking on the tip, causing the man to moan out again. I liked sucking the tip and kept my attention on just the head of Mr. Johnson’s cock for a while. Mr. Johnson wanted more, and he pushed my head down.

I started gagging and choking, even though I only had about four inches of the man in my mouth and down my throat. This was my first blow job, and I didn’t know how to suck a cock very well.

The much older man chuckled at my distress, but did allow me to remove my mouth from his cock so I could catch my breath. Other than the gagging and choking, I was enjoying sucking his dick. I liked how it felt in my mouth.

“Use your hand also,” he told me. “The more dicks you suck the better you will get at it and learn how to relax your throat.”

I smiled and nodded. I had not been giving Mr. Johnson a blowjob for long, but just in that short period, I discovered I greatly enjoyed sucking cock and planned on doing it a lot more. Provided I could find someone who would let me do it to him.

I started sucking his cock again and used my hand to jerk him off at the same time. I soon got into a nice rhythm and was proud of myself for not gagging when I took about four inches of the man in my mouth and down my throat.

Mr. Johnson kept his hand on the back of my head but didn’t push me down on him. He let me do all the work. I enjoyed hearing his masculine moans of pleasure.

While I was giving my first blowjob, the older man would call me a sissy slut, a sexy fem boy, and a sissy whore. He didn’t use the word sissy when he called me a whore. He used the same word English people used to refer to a cigarette. I was not offended when he used that word. It turned me on.

It took Mr. Johnson about fifteen minutes to cum, but I didn’t care. I was enjoying what I was doing so much that I thought I could suck his cock for an hour.

“Uh, fuck, you sissy bitch, I’m going to cum,” the man moaned out.

Mr. Johnson pushed my head down further, and I again started gagging and choking as he forced me to deep throat him. I then felt his cum in my mouth.

His cum exploded in my mouth and I felt it shoot down my throat and fill my mouth. I did my best to swallow it, but I was still gagging and choking. Cum and saliva ran out of my mouth and down my chin. When I coughed, saliva and cum sprayed out of my mouth over his thick, black pubic hairs.

When Mr. Johnson was done cumming, he let go of my head and I raised up, still gagging, coughing, and gasping for air. But I wasn’t done. The man’s warm, thick fluid tasted so good and I wanted more. Once I caught my breath, I lowered my head back to his crotch.

I licked the cum off his coarse, short hair and then took his now semi-erect cock back in my mouth. I used my hand to milk more cum from him.

Mr. Johnson chuckled at me, but let me coax as much cum as I could from his cock. Once I could not get any more, I raised my head, wiped my mouth, and picked a few of his pubic hairs from my mouth. I then looked at the man and grinned at him.

“You liked that, huh?” he asked.

I nodded my head rapidly. “I...I can do it again if you want me to,” I told him hopefully.

The man laughed. “Well, aren’t you a greedy slut,” he said, and I giggled. “Maybe another time. I need to get home or the wife will think I am cheating on her.”

I pouted as I watched Mr. Johnson pull up his underwear and pants. I then pulled up my underwear and shorts and put on my tee shirt.

We didn’t talk much on the way home. I don’t know what Mr. Johnson was thinking about, but I was thinking of what I had just did and had done to me. I loved it and wanted more.

His comment about his wife thinking he was cheating on her didn’t go unnoticed by me. I guess he thought he didn’t cheat on her because he didn’t see me as a girl and maybe he thought just a blowjob was not cheating.

Me? I thought he cheated on his wife and the thought of me being the “other woman” turned me on. I liked the idea of being a married man’s mistress.

Once we got to his house, Mr. Johnson helped me get my bicycle out of the bed of his truck and I teased him and told the man anytime he wanted his cock sucked again to let me know. He laughed and said he would keep me in mind. We then parted ways.

It would be almost two weeks later before I sucked Mr. Johnson’s cock again. But I thought about it a lot every day before then and jerked off, often fantasizing about being his mistress.