Tranny and Twink Ch 1

My name is Alana and I am a transexual female who is currently thirty-five years old. I have lived with my forty-five-year-old boyfriend for the past year. We both enjoy a healthy sex life that does include several kinks and fetishes including other people joining us for sex.

While I am about ninety percent a bottom girl, I do have a fetish for topping young femboy, twink-type younger men and letting them fuck me as well. This is a true story that took place when I was thirty years old and seduced a seventeen-year-old gay, pretty, twink, fem-boy. It is also a story of how two other young boys found out about our affair and blackmailed me into being their transexual whore.

I knew Trevor for about six months before I seduced him and we had our affair. Yes, I knew he was only seventeen, but he was too pretty not to have. I lusted after the boy for months before I seduced him.

His age was a reason why I never tried to seduce him before. I had several short inconsequentials with him before and maybe even flirted with him. Trevor was shy and would blush when I flirted with him.

I knew a little about the boy and some other teenage boys and girls who lived in the same small apartment complex. The complex only had about fifteen units and you came in contact with almost everyone who lived in the one-story apartments on occasion.

What I knew about Trevor was that he was quite, shy, and didn't hang out with the few peers of his that lived in the complex. Trevor was into skateboarding and I often saw him riding his skateboard around the complex and home from the local skateboard park. A few times I had given him a ride. I also assumed he was gay or maybe even bi-sexual. I thought that by the way he acted, carried himself, the feminine pitch of his voice, and the way he looked.

The boy was feminine-looking and beautiful. Trevor had a thin, feminine body with a butt I thought was sexy. It was skinny and he had narrow hips but his butt protruded slightly behind him. He wore his dirty blonde hair almost to his shoulders. The boy had incredible blue eyes and alabaster skin.

About a month before I seduced him, he started consuming my masturbation fantasies. I was not dating or seeing anyone for months and started masturbating often as of late. I would either use my hand or my Fleshlight sex toy while I either fingered my ass-pussy or used a dildo in my ass-pussy.

I started thinking more and more about Trevor when I got myself off. Thinking of sucking his cock, tasting his cum, having him wrap his full lips around my girl-cock, and fucking his tight boy-pussy or him fucking me. I would fantasize about how he sounded when I fucked him; his moans and whimpers of pleasure as I pounded his ass. I would imagine his feminine grunts of ecstasy as he fucked me.

I lusted so much for the boy that I could not take it anymore and started thinking of ways I could seduce him and thinking or hoping that he was not as gay not to be attracted to a transexual woman.

It was no secret I was transgender. I didn't go around advertising it and I am pretty enough for people to think I was born in a girl body, but people in the complex knew I was transgender and I knew they talked about it. I even overheard how some of the other teenage boys talked about me behind my back when one would comment how they would fuck me and another would remind him I had a cock and laugh.

I was born in Turkey and my family moved to London when I was twelve. When I turned eighteen I came out to them as transgender and being the strict Muslims they were, my family disowned me. When I was nineteen I moved to the US to live with an aunt who had rejected her Muslim upbringing and was more accepting.

One afternoon on my way home from work, I saw Trevor riding his skateboard home from the park and offered him a ride. It was that afternoon that I could not take it anymore and just had to have the seventeen-year-old boy and decided to try and seduce him.

Trevor happily accepted my ride and we made general conversation on the short ride to our complex. The boy had become less shy with me lately. I did notice that he kept looking at my legs. The skirt I wore to work that day had ridden above my knees and halfway up my thighs. I wanted him so bad and didn't care he was only seventeen. I just needed to think of a way to get him into my apartment.

"Do you know a lot about computers?" I asked as I pulled into the entrance of our complex.

I had to ask him again because the boy looked out the window and seemed lost in thought. I looked in the direction of where he was looking and smiled.

Trevor was looking at two other boys who lived in the complex. David and Kevin. They were playing basketball on the small half-court the complex had. David had his shirt off. I suspected it was David who Kevin was staring at and I could not blame him.

Kevin and David were still in high school like Trevor was, but a year older. Both were masculine boys and David was a hottie! They didn't hang out with Trevor and both were jocks. I smiled because the way Trevor looked at David was a look of desire.

I repeated the question, Trevor turned to me and blushed. "Somewhat."

"I have been trying to find a way to get Google to save my passwords on my laptop when I clean my browsing history and cookies, but I can't get it to work. Do you think you can take a look?" I asked.

"Sure. I can look at it," he told me.

Trevor lived with his mother and I knew she worked the second shift at her job and would not be home until after nine in the evening. I had plenty of time to try and seduce him. I was not one hundred percent confident I could and was somewhat nervous about it. If he rejected me I worried about the consequences.

When we got to my apartment I told Trevor to make himself at home and he sat on the couch. I went and got my laptop, handed it to him, sat close next to him, hiked up my skirt to expose my panties, and leaned over him as I pretended to watch what he was doing.

Trevor was nervous and shaking slightly as he used my laptop. I did notice he glanced down at my thighs and between my legs to look at my black, cotton, bikini-cut panties.

The boy went into my settings and set them not to erase my passwords, something I did know how to do.

"That should do it," he told me in a shy voice. "I guess I should go now."

He started to stand up, but I placed my hand on his arm.

"You don't have to if you don't want to," I told him.

Trevor shrugged his shoulders and sat back down. I moved closer to him until our legs were touching. He glanced down at my thighs again and blushed when he saw me looking at him.

"Sorry," he told me.

I smiled. "I don't mind, Trevor. If you want I can show you more."

"More?" he asked me and shifted his lower body. I knew he was trying to hide his erection.

I didn't answer verbally but instead raised my skirt even higher. The boy looked down again. You could see a slight bulge in my panties from my hard cock. Trevor kept looking at it.

"Is that OK?" I asked. "Do you like looking at it?"

He nodded and looked up at me. "I...people...so it's true, you are transgender," he stated the now obvious.

I smiled and reached out and ran my hand through his long hair. He didn't pull away. "Yes. Does that bother you?"

He shook his head. "No...I...I'm gay," he exclaimed out. "I like looking at cocks online and gay porn. I never watched transsexual porn though."

"Would you like to see it?" I asked.

"Serious? You... you're not fucking with me, are you? Not like teasing me or anything like that?"

I leaned closer and kissed the beautiful boy's full, pouty lips. Trevor's body stiffened but he soon relaxed and started kissing me back. I put my arms around him and he put his around me and we started making out.

His kisses were clumsy and awkward at first and I suspected I was the first person he ever kissed. I didn't mind his innocence at all. It turned me on. It was not long before he relaxed more and his kissing improved as our tongues entered each other's mouths.

We made out for several more moments and I started kissing his neck. The boy gave a feminine, moaning whimper of pleasure.

"I want to suck your cock," I whispered in the boy's ear.

Trevor's body went stiff again and he pulled back and looked at me. "Really?" he asked in a surprised voice. I smiled and nodded. "I...I never did anything like this before," he admitted.

"That's OK, baby, I don't mind. I know how to make you feel good," I told him.

"OK," he said. "What do I do?"

"Just relax, darling, and let me take care of it. We can make each other feel good," I told him.

"OK," he told me and grinned.

"Let's take off your shirt first." I reached over and started taking off his tee shirt and he helped me lift it over his head.

I tossed his shirt to the floor and took a moment to admire his body. His chest was void of any hair and his naturally, slightly tanned body was smooth. Trevor's upper body was feminine looking and he had almost no muscle tone. God, he was so beautiful and I told him he was. He blushed.

I leaned over again and started kissing his neck then down to his chest. Trevor again moaned out in pleasure and then gasped as I started sucking his nipples and going from one to the next.

"Oh, fuck, Alanna, that feels so good," the boy told me as I ran my tongue over his hard nipples.

I looked up and smiled, "You are so sexy and beautiful, baby."

Trevor had his eyes closed and his head back. I don't think he heard me because the boy was enjoying what I was doing to him. I giggled and started removing his shorts as I kept sucking his hard, light-brown nipples.

Trevor looked down at me as I got on my knees between his legs and pulled both his shorts and underwear down. I again looked up at him as I took his hard cock in my right hand and started stroking it slowly.

"You...you really are going to suck my cock?" he asked as if he didn't believe I was going to.

"I want to, but only if you want me to," I told him.

The seventeen-year-old boy nodded. "Yes."

I didn't care that he was only seventeen and I was thirty. I should have felt guilty and even perverted for seducing a boy so young, but I didn't. Trevor was just too lovely and sexy not to have. I wanted to suck his cock, have him suck mine, fuck his tight, sissy boy ass, and do many other things to him. But I knew I needed to go slow. This was his first time and I didn't want to scare the beautiful boy. If things went as I planned, there would be plenty of time to make the sissy, feminine boy my bitch.

I looked down at Trevor's cock and liked what I saw. It was average, about six and a half inches long, and beautifully shaped and smooth. His pubic hairs were a light brown like the hair on his head. I liked pubic hair on a masculine man who fucked me but preferred the twink, sissy boys I fucked to be smooth-shaven. I would get the boy to shave his pubic hair later or maybe do it myself if he wanted us to keep fucking after that first time.

I bent down and took his cock in my mouth, teasing it with my tongue as I put about three inches of it into my mouth. Trevor let out a sexy, feminine moan of pleasure. I teased him for a while and then started sucking his lovely cock.

Trevor leaned back on the couch and gave moans and whimpers of pleasure as I gave him a blowjob. The boy didn't last long and I didn't care. It being his first blowjob I suspected he would cum quickly.

His body stiffened his hands clinched the couch cushion and his hips thrust up into my face.

"Oh, fuck...oh God, Alanna, I'm cumming," Trevor grunted out loudly. I started sucking his cock harder.

Trevor's cock exploded his cum into my mouth. I swallowed the warm, sticky, thick, delicious fluid. Trevor had ejaculated an abundance of cum into my mouth, but I swallowed all of it. I looked up at the boy, who was grinning and panting slightly. I wiped my mouth and picked a few of his pubic hairs from my mouth.

"Did you like that, baby?" I asked.

Trevor nodded. "That was fucking incredible."

I smiled and got back on the sofa and started kissing the boy again. Trevor didn't hesitate and started kissing me back. As we kissed, I took his right hand and guided it under my skirt and to my hard cock. Trevor began to run his hand over my panties. I moaned into his mouth as his fingers tightened their grip and ran up and down my shaft.

"I...I want to try and suck yours," the boy told me.

I pulled my head back and smiled. "I would like that, baby, but let's go to the bedroom. We can have more fun there and do other things if you want."

Trevor gave me a look of surprise. "You mean like, umm...well...fucking you?"

I smiled and reached out and ran my hand over his beautiful, smooth face. "If you want to, baby, we can do that."

I would like the boy to fuck me, but I wanted to fuck him more. When I had sex with my younger sissy boy gay lovers, I enjoyed them fucking me, but much preferred to fuck and dominate them. As opposed to when I got fucked by masculine men. I preferred my masculine male lovers to be dominant and fuck and dominate me.

I didn't tell Trevor I wanted to fuck his sissy boy-pussy. I didn't want to scare him. I would try to go slow and passionate the first time or the first few times. If the boy and I continued to have sex after that evening, I would slowly introduce him to the pleasures of being a sissy fuck toy like I enjoy being too masculine, dominant men.

I got off the sofa as Trevor started pulling up his underwear and shorts. I smiled when I saw his young cock was still hard.

"You won't need those back on, baby," I told the boy.

"Oh...I guess not," he said and gave a nervous chuckle that was more of a feminine giggle.

Treover stood up and kicked off his shoes and then his underwear and shorts. I reached out and took his hand in mine and led the naked boy to my bedroom.

Once in the bedroom, I stopped and turned and started kissing him again. I pushed him away gently and started unbuttoning my blouse, removed it, and then removed my bar. Trevor glanced at my exposed breasts but didn't pay much attention to them. Most of the twink gay boys I fucked didn't pay much attention to my breasts. They wanted to see and touch another part of my body. I was more than eager to show it to my new, young lover.

I reached behind my back, unzipped my skirt, and let it fall to my feet. I then stepped out of it, turned my back to Trevor, and walked to my bed. I could sense his eyes on my butt cheeks, which were exposed by the black thong I was wearing.

I sat on the edge of my bed and gave Trevor a seductive smile. "Come here, baby, and get on your knees," I told him.

Trevor gave me a nervous nod but didn't hesitate. As he walked to me, I removed my thong and exposed my cock to him. Trevor was looking at my hard penis as he got on his knees.

"It's small," he commented.

He was right, I do have a small cock. It's only about five and a half inches long and thin. I didn't mind having a small penis. I liked that it was below average in size.

"You can touch it, baby," I told him.

"I...I've never done this before...never gave a blowjob before," the boy reminded me of what I already knew.

"It's OK, darling, it's not hard to do," I assured him. "But don't do it if you don't want to."

Trevor reached out and took my small, hard cock in his hand and started stoking it. I let out a moan of pleasure as I watched his hand go up and down.

"I want to," he told me. "It being so small will make it easier I guess."

He sounded disappointed I had a small cock, but I ignored it. I moaned out again when I felt the sensation of the boy's warm, wet mouth around my cock. I placed my hand on the back of his head. I was tempted to force his head down and thrust my hip up and make the beautiful, sissy, twink gag and choke, but I resisted it. Hopefully, there would be many chances later to make the boy my fuck toy.

Trevor started moving his head up and down slowly and it felt so good. I had not had a blowjob in so long. The last guy who fucked me was months ago it was a one-night, random hookup with a man I met online and he want to even touch my cock. He just had me suck his and fucked me hard and rough several times that night. Oh, it was great being treated that rough and like a whore, but I do enjoy having my cock sucked.

As Trevor sucked my cock, I placed one hand on his head and ran my fingers through his soft, fine hair, and played with my nipples with my other hand.

"Oh, baby, that feels so good," I told the young boy. It did feel good.

Trevor seemed to be encouraged by my words and started sucking my cock faster and harder and then used his hand on my short shaft.

"Oh, fuck, baby, that's it...uh God that feels good," I moaned out.

It was not much longer when I started to orgasm. My hand tightened on his hair and I started pinching my nipples harder.

"Fuck, Trevor, I'm going to cum, baby. Keep doing that, darling," I moaned out.

I groaned out several times as my cum shot into the boy's mouth. My cum was thinner and not as abundant as his due to my hormone treatments, but the feeling of cuming was amazing. Trevor swallowed it all and after I finished cuming he kept stroking my shaft and sucking my cock to coax more cum out of me.

I gently pulled his head back looked down at the beautiful boy and grinned as I ran my fingers through his hair.

"That was great, baby. That felt so good," I told him.

Trevor looked up and smiled as he wiped his mouth. "I liked doing it. Your small cock makes it easy," he told me.

The boy stood up and sat next to me on the edge of the bed and we started kissing again. I reached down and took his young, hard cock in my hand and started stroking it.

"Can...can you suck it again?" he asked me.

I smiled. "Baby, we can do all kinds of things with each other. I like sucking your cock, but I can make you feel even better."

"How?" he asked.

"Get on the bed and lay on your stomach and I'll show you," I told him.

Trevor nodded and did as I told him. I got between his spread legs and took a moment to look at his sexy ass. I wanted to fuck him badly, but I knew I had to go slow. I didn't want to scare him and I needed time to get hard again.

I reached out and started caressing his soft butt cheeks and then leaned down and started kissing and licking his ass cheeks. Trevor squirmed and tried to turn over but I held him in place.

"I want you to suck my dick again," he told me, and sounded as if he was almost begging. His begging voice was sexy. I liked hearing him beg. "I want to cum again."

"Patience, baby, I promise I will make you cum again," I assured the boy. "This will feel good also."

Trevor relaxed and I ran my tongue down his butt crack, spread his cheeks apart, and looked at his sexy boy-pussy. The area around his tight hole was void of any hair and it puckered on slightly. The shade of skin around the hole was a light brown and looked sexy in contrast to his pale skin.

Trevor looked over his shoulder. "What are you doing?" he asked in a nervous voice.

"Relax, baby, I am going to make you feel good," I answered in a soft, seductive voice.

I leaned closer and started circling my tongue around his hole. Trevor moaned out in pleasure.

"Do you like that, baby," I cooed.

"Yes, it feels real good," the boy answered.

I giggled and started licking his boy-pussy again and then drove my tongue deep into his hole. Trevor moaned out again.

As I had my tongue deep in the boy's butthole, I reached under him and started gliding my fingers over his hard cock. I then pulled it down so it stuck out below his spread legs and started running my tongue over it. As I did that I slowly put a finger into his now wet hole.

"Oh fuck, Alanna, that feels great," he said after he let out a feminine grunt.

Encouraged that Trevor enjoyed what I was doing, I started licking his cock as I finger fucked his ass. The boy was squirming and making sexy whimpering moans of pleasure.

"Fuck, Alanna, please...please make me cum again. I can't take it anymore," he begged in a high-pitched voice.

I giggled and kept teasing him with my finger and tongue. My cock was hard again and I was ready to take the boy's virgin sissy-pussy.

I moved my body to lay on top of his and placed my small cock between his ass cheeks. I brushed his hair to the side and started kissing his neck as I moved my hard cock between his butt cheeks.

"I can make you feel even better if you want me to," I whispered in his ear.

The boy's body stiffened. He knew what I wanted to do. Trevor turned his head to look over his shoulder at me.

"I...I never did that," he told me what I already knew.

"Would you like to?" I asked.

"I...I guess since your cock is so small it...well, it may be good for my first time," he answered.

"I promise to go slow," I assured him. "And after you can fuck me."

"OK, but if I don't like it you have to stop."

"Sure, baby. I promise. Now turn over while I get some lube. I want to look at your beautiful face when I fuck you for the first time."

"The first time? You want to do this again?" Trevor asked in a surprised tone.

I kissed the boy's neck again. "Baby, if you like what we do we can do it as many times as you want," I promised him. "Even if you don't like me fucking you we can suck each other's cocks and you can fuck me."

Trevor seemed enthused by the idea of having thirty-year-old transgender women willing to give him sexual pleasure. I know I was excited about making the boy my fuck toy. I was sure he would like me fucking him and like he said, I had a small cock so that would make his first time easier for him.

The first time I fucked him I would go slow and passionate and make love to the boy. But soon I would be more dominant and fuck his tight sissy-pussy hard and brutally. There was so much I had planned for Trevor as I turned him into my sissy bitch.

As I got off the bed, Trevor turned over and I just had to look at his beautiful cock again. I got the lubricate out of my nightstand drawer and got back in bed. I started sucking his cock again. I just had to have it in my mouth. I couldn't resist it.

I sucked his cock for a few moments and then kneeled between his legs as I spread lubricant on my hard penis.

"Just relax, baby, I promise this will feel amazing," I told him.

Trevor nodded.

I spread the boy's legs lifted them and then lay on top of him. I started kissing him as I guided my cock into his sissy, boy-pussy. Since I have a small cock and I made sure it was well lubed, it slide in easily. Trevor gave a gasping moan as I pushed about two inches into him.

"Are you OK, baby?" I asked.

"Yes...it...it doesn't hurt at all. It feels good," he told me.

"Do you want me to stop?"

"No," he told me.

I started to slowly fuck Trevor, making love to the twink boy. His sexy grunting moans and whimpers of pleasure made it hard to not just fuck him hard, but I did manage it. As I made love to him, I kept kissing him and whispering into his ear how sexy he was, how beautiful he was, and how tight his boy-pussy was.

Trevor would occasionally whimper out an "Oh, God", and tell me how great my cock felt inside him. He would tell me how good I felt and not to stop.

I fucked him slow and passionately for about ten minutes before I felt I was going to orgasm again. Normally it took much longer due to the hormones and that I had already orgasmed once, but the sexy, beautiful feminine boy turned me on so much.

"Ugh fuck," Trevor grunted. "Go faster...ugh...ugh...harder, please." the boy moaned out.

I started fucking him harder and soon had an orgasm. I ejaculated my cum, which was thin and clear because of the hormones, into the boy's tight sissy-pussy. My fluid may not have been thick and abundant as it was before hormones, cumming still felt great. I was glad that never changed.

After my orgasm ended, I lay on top of the boy and we started kissing again. My small cock became flaccid and shrank so much that it easily slipped out of Trevor's butt.

"Did you enjoy that, baby?" I asked as I got off of him.

Trevor was panting and looked over at me. "That was amazing. I never knew it could feel that good."

I smiled. Glad you enjoyed it. You can fuck me if you want or I can suck your cock again."

"Can I really fuck you?" he asked.

"Baby, you can fuck me as much as you want," I told the beautiful boy.

Trevor grinned and moved to kneel between my spread legs. He picked up the bottle of lubricant and looked down at me.

"How much do I use?" he asked.

I smiled again. "I'll put it on if you want me to."

Trevor handed me the lube and I squirted some on his hard cock. He moaned out as I used my hand to spread it over his penis.

"It's ready, baby," I told him.

Trevor didn't waste any time losing his virginity. While I enjoy dominating sissy fem boys and was planning on turning Trevor into my sissy bitch, I do love to get fucked and allow them fuck me on occasion.

Trevor was not very good, but it was his first time and I knew he would improve. He fucked me as if he didn't care about my pleasure, but I did get pleasure from it. He fucked me hard and chaotic.

As he was fucking me, I kept telling him how beautiful he was and how good his cock felt inside me. The boy was so focused on his pleasure, that I don't think he paid attention to what I was saying.

Trevor didn't last long and was soon shooting his thick, warm, cum into my ass-pussy. The feeling of his cum going inside me felt so good!

After the boy was done, he rolled off of me and seemed embarrassed. I turned to my side and cuddled up to him.

"I...I'm sorry," he said.

"For what, baby?" I asked.

"That it didn't last long."

I kissed his smooth, hairless chest. "It felt good, darling. It felt really good. Did you like it?"

Trevor shrugged. "Yes. I liked when I came but...well...I...this may sound dumb, but I liked when you sucked my cock and fucked me better."

I giggled. I understood that. While I like fucking other transgender women and sissy, gay, twinks, I much prefer to get fucked by masculine men. I did like hearing him tell me he much preferred when I fucked him because that meant he would be a bottom boy and would make turning him into my sissy-bitch much easier. Oh, I would have him fuck me again from time to time, but I had such perverse plans for the beautiful, sissy boy.

I looked over at the clock on my nightstand and saw it was still early into the evening. I wanted to play with Trevor some more and maybe fuck him again before he had to leave.

We did just that. Before he left to go home we sucked each other's cocks again, fooled around, and I fucked him from behind. I asked if he wanted to fuck me again and he said no. I was disappointed by that, but there would be many more occasions to mold the boy into what I wanted him to be.

As he was getting dressed to leave, Trevor asked when he could see me again and repeat what we did. I smiled and told him anytime he wanted just to come over. My affair with a seventeen-year-old sissy boy started and I started to turn him into a sissy boy, slut.

I found out about a month and a half after we started our affair just how much of a slut Trevor became. But that's in the next chapters of my story.