Falling for my Sister's Boyfriend 01

Part 1

All characters are age 18+

*

What was happening to me!?!?

My name is Andy. On a normal day I was just an average teenage guy. Kind of thin, a little awkward, super self conscious. You know, the usual.

However, lately I have been noticing some.... changes...

Where my friends were developing strong masculine bodies I seemed to be staying still. On top of that the Dr says I have a condition called gynecomastia.

Staring in the mirror all I could do was curse the tiny protrusions on my chest.

At this point they were hardly breasts. My nipples were a little bigger than normal and there was a little ball of fat behind each one.

It was still enough to make me embarrassed to be seen shirtless. Of course my mom just had an awesome new pool installed in the backyard.

I could go out there alone, but my older sister Kelly and her boyfriend, Jason, were constantly using it, and she was always teasing me about my chest.

As the weeks went by I noticed the balls of fat behind my nipples spread and disperse more evenly giving me small but definite breasts.

I'm not sure what came over me, but one day when my mom and sister were out, I took some of Kelly's old clothes from the back of her closet.

I was shaking as I put them on. I slipped my arms through the straps of a training bra, then I reached behind me and clumsily fastened the hooks. Posing in the mirror I felt so feminine. After I finished off my ensemble with a tank top and a pair of yoga pants, it was hard to tell I wasn't a girl when I looked in the mirror.

I went back to Kelly's room to see what else I could find in the back of her closet. I was bent over looking through a tote when I felt a firm slap on my butt.

I froze...

As I turned my head I was horrified to see Jason, my sister's boyfriend, standing there. His grin was slowly disappearing as the realization of what he had done hit him.

"What the fuck Andy!" Jason yelled.

"I...I..I'm...s...s...sorry...." Was all I could get out.

Jason continued. "I thought you were Kelly, what are you doing dressed like that? You actually look pretty cute"

He seemed to regret that last statement as a puzzled look appeared on my face.

Now he seemed nervous. "Ermmm, sorry, you just look a lot like Kelly dressed this way...

Ummm look... I won't say anything about this if you don't...deal?"

I nodded my head and ran to my room.

Ch2

As the spring turned to summer, I continued to sneak my sister's clothes. I also decided to let my hair grow out more. My chest had grown a little more and I was comfortable in my sister's old A cup bras.

One afternoon I was alone and decided to use the pool. I was wearing a t shirt and swim trunks. As I emerged from the water I heard girls laughing.

Kelly and her best friend Miley were standing there in their bikinis pointing and giggling.

My shirt had clung to my body and was practically translucent.

Kelly let out, "nice tits little faggot!"

I was horrified. I stumbled out of the pool and ran inside.

I was crying hysterically as I plunged my face into my pillow.

I tore my shirt off and screamed pulling at my chest as if I could just rip it off and throw it away.

The only thing I succeeded in was hurting myself and now my chest was irritated and swollen.

I hated my sister. Why did she get to be so perfect? She was beautiful, slender, sexy, handsome boyfriend....wait...why did I say handsome?...anyway...

What do I get? I'm a skinny guy with little boobs, no girlfriend, never even kissed a girl.

I went to the bathroom to splash water in my face, and stared at my reflection in the mirror.

My hair was wet still and tickled my shoulders, I had a cute face with delicate features, slim feminine shoulders, perky A cup breasts, a thin waist.

Holy fuck, I actually make a pretty cute girl.

In the moment I became super aroused.

Despite this, my cock was still mostly soft, it was only about 2 inches long and only as thick as my pointer finger.

I gripped it between two fingers and started to jerk it furiously.

I was growing frustrated.

A realization hit me as I reached up and grasped my breast from underneath.

Oh yeah, I have these to play with.

I maintained eye contact with myself in the mirror only breaking it to look down at my hand groping my little tit.

I had never been so turned on. My little cock grew hard.

I could feel my orgasm building as I went back and forth on my small dick.

I pinched my nipple hard, and with a very high pitched scream I orgasmed cumming all over my hand.

Panting I watched the girl in the mirror. One hand still tightly gripping her right breast, the other hand, covered with cum, rising up in front of her mouth. I stared intently as she slowly licked the cum off of her fingers. Paying special attention until each one was licked clean.

I sat down on the edge of the tub trying to make sense of what I had just done.

I was very confused, but I knew for certain I wanted more.

Ch3

The next morning, I awoke with an absolute distain for my sister. I had to get back at her, but I wasn't quite sure how to go about it.

Then one afternoon an opportunity presented itself.

I walked in the kitchen and I heard a splash coming from outside.

Looking out the window over the sink I could see Jason, alone, swimming in our pool.

I thought back to our awkward encounter. How he said I looked cute...

I'll give him cute. I ran to my room and grabbed a two piece bikini that I stole from Kelly. I put it on and took stock in the mirror.

The cups of the bikini had a little gel padding in the bottom of the cups giving my small breasts a little boost. I was already super horny just looking at the hint of cleavage it gave me. Despite my arousal my small cock was practically invisible in the bikini bottoms. My legs were shaved smooth and looked somewhat shapely.

I grabbed an oversized t shirt and put my hair in a ponytail.

Time for revenge.

Jason was swimming laps as I walked out onto the patio. As his head emerged from the water he wiped his eyes and did a quick double take upon seeing me.

"Oh..hey Andy..." he stuttered

I gave a little wave.

"Um want to come in and throw the football or something? "

I could feel my nervousness returning.

"Hmmm, I don't know...."

*Remember your revenge plan stupid*

"Yeah, sure!" I said trying to sound girly.

Jason got out to get the football. He returned to the pool and stared as doubt crept into my mind.

"You coming or not?" Jason said as he tossed the ball to himself.

Well... Here it goes.

"Yeah, sorry...I just... Um"

Jason looked at me with a confused expression.

*C'mon Andy! *

Suddenly I could hear Kelly's faggot comment on repeat in my head.

I'll show her.

I confidently pulled the ponytail holder out of my hair. I leaned my head back and tried my best to look seductive as I sorted out my long hair.

I snuck a glimpse of Jason. He no longer looked confused, but he was still staring.

Now for the big reveal.

I grabbed the bottom of my shirt. I slowly lifted it up and off exposing my bikini clad body.

After my shirt hit the concrete I adjusted the cups of the bikini locking eyes with Jason while doing so.

"You ready to play?" I said in my most girly voice as I lowered myself into the cool water.

Ch4

After a few silent tosses Jason broke the silence. "You...ahhh...I....I like the new look"

I could feel myself blushing.

"Thanks" I got out behind a slight smile.

A few more silent tosses.

"Sorry Kelly is such a bitch to you" Jason blurted out.

Taken by surprise, I lost concentration. The ball hit me right in the face.

"Oh sorry! Are you ok!?" Jason rushed over to me.

My eyes were teary and my nose was sore.

"I'm ok, thank you for checking"

I was now looking up at him. My face mere inches from his.

There was another minute of silence.

"You know, you are quite beautiful" Jason said as he gazed into my watery eyes.

I just continued to look up at him. My eyes following his chiselled jawline, up to his stubble, his mouth.

Each moment weighed heavy, and I could feel my body get hot and flushed. I became hyper aware that I was wearing a skimpy bikini in front of my sister's boyfriend, and terrified that I wanted him more than anything in that moment.

Why did I want him!?

Before I could think of what to do next, Jason leaned forward slowly, and pressed his lips against mine.

After a brief hesitation I let my lips part and I felt Jason's tongue slide across mine.

*Oh my god! I've never kissed anyone before, and my first kiss is Jason!*

Not knowing exactly how to kiss I decided to follow Jason's example, and let my tongue slide into his mouth. As my tongue met his, our lips collided. My head was spinning. I could feel my mouth being lightly sucked against his. Our lips parted with a sultry smacking sound and I leaned in more, repeating the motion. Each kiss lasted longer, each breath became deeper.

I let my hands rest on either side of his face. Jason broke our kiss. I watched nervously as his gaze drifted down to my chest and back up to my eyes.

I was a bit startled when I felt the strings on my bikini loosen from around my neck.

I should have run away, but I couldn't. As my mind raced, Jason flipped down the cup of my top. Before I could protest, I felt his lips wrap around my nipple.

A rush of pleasure went through my body as I grabbed the back of his head and pressed his face into my...breast.

Jason swiftly grabbed me behind my legs and I wrapped them around his waist. I could feel his hard cock through his trunks grinding against my ass.

He reached down and tugged his shorts down, and then I felt my bikini bottoms loosen.

It all happened so fast.

I soon felt pressure against my asshole. A quick adjustment and I felt his dick penetrate my ass.

"Oh my fuckin g.... Fuuuck." I blurted out.

I couldn't believe it. My sister's boyfriend was fucking me in the pool, this was equally amazing as it was weird.

Jason's breathing became labored as I felt him tense up.

Was he cumming in me!?

He let out a deep moan and grabbed my small tits hard.

I could feel his cock pumping into me. I screamed as I felt my little dick leaking cum into the water.

We were both breathing heavily as I felt him soften and fall out of my ass. He looked at me and smiled.

"Damn Andy, you are so fucking hot"

I felt a beam of pride and I leaned in and gave him a peck on the lips.

Ch5

After a couple of weeks of secret phone flirting with Jason, I had noticed that my chest had stopped developing. I still looked cute, but I began to worry about my body possibly becoming masculine.

I went online and ordered a hormone blend for trans women. The site was sketchy, and of course I didn't have a prescription.

I was surprised when the package showed up just a couple of days later.

I didn't quite know where I wanted this to go, but I did know I wasn't done looking like a girl.

I think my initial plan of revenge had turned into me genuinely falling for my sister's boyfriend.

Ch6

Despite being on the hormones for a couple of months, my breasts stayed roughly the same. My ass and hips on the other hand...damn, they looked amazing.

I had been following a diet and exercise routine from YouTube, and i truly look like a model with my trim waist and toned legs and butt

Seeing Jason with Kelly was making me sad and extremely jealous. We had many nighttime texting chats, but we had yet to be physically intimate again.

One Saturday morning, my mom and Kelly were going to a Drs appointment. Kelly was going to get implants for her birthday.

I'd be lying if I said I wasn't jealous.

The surgeon was a few hours away, so I knew I'd have the house to myself.

I texted Jason.

"You know I'll be alone all day... 😉"

He responded,

"I'll be there in an hour d84;a039;"

I was shaking with excitement.

I decided to dress seductively...

I put on the sexiest push up bra I had, a tight tank top and a tight pair of workout shorts to show my developing figure.

I put on a pair of fake glasses to complete the look. I once overheard Jason tell Kelly that the nerdy look was hot.

An hour passed and Jason was at the door.

Before I knew what had happened his lips were glued to mine on the couch.

His hands were all over my hips and ass, and I could tell he was enjoying my improved physique. It was so bizarre to have something there to squeeze.

I rolled on my back with my head against the arm rest.

Jason's hand sneakily crapt up my shirt.

I could feel my nipples harden as his hand slowly made it's way up my flat tummy.

Instead of groping my waiting tit his hand stopped on my stomach, his long fingers just barely grazing the bottom of my breast.

I gasped with anticipation. I looked up at him longingly with my mouth agape.

My hips were involuntarily moving back and forth against his thigh.

Fuck, I needed this!

His piercing eyes were stealing glances at my writhing body. He was so damn handsome. I wanted to bite his chiseled jawline, I wanted to feel his stubble on my lips.

Just as I was about to make a move, Jason's hand crept up another inch.

I was in heaven.

I reached out and pulled down on the waistband of his athletic shorts.

His cock was so big compared to what I had.

I was enamored with how long and hard he was. Especially knowing that I made it that way.

He followed and pulled down my shorts.

I was a bit worried he would run away after seeing my little dick, but he didn't seem to notice.

A pinch on my chest brought my attention to his hand gripping my small breast.

Damn I wish they were bigger...

Jason held on tight as he tried to use his free hand to guide his cock in my ass.

Without lube it this was going to hurt.

Sensing my discomfort, Jason remembered the lube in his bag.

Luckily it was in reach.

With his cock now glistening, he entered my tight ass with little resistance.

Looking down was quite the shock.

Jason's dick was inside of me!

I have tits! (Albeit small ones)

My dick is barely an inch long now!

What has happened to me!

Just as my thoughts were starting to take over, a rush of pleasure swept over me.

"Oh god, fuck me Jason!

Make me your little slut!"

Did I say that!

Was that my voice?!

I was in such a fog, I could feel my hands reaching and scraping at Jason's toned chest and stomach.

I could feel my orgasm building...

Oh!

Oh!

Yes!

Ahhhh!

My head was throbbing, my eyes rolled back, I reached up and squeezed my little tits as my body filled with the biggest orgasm I had ever felt.

I could barely hear Jason over my own screams.

He was moaning deeply and I felt him pull out of my ass, as warm streams of cum hit my chest and stomach.

We were both panting. I know I looked a hot mess.

Just as my high started to subside, I heard an ear piercing

"WHAT THE FUCK"?

Ch7

My mother stood there, mouth agape. Jason and I scrambled to get covered up.

Just as he was about to run for the door my mom stopped him.

Despite her initial reaction, she had calmed down and spoke diligently.

"Kelly is just outside in the car. I will not say a word to her, but we are definitely having a conversation when we get the chance" she said, her eyes piercing into mine.

She spoke again, "I'm going to grab my purse I forgot, get back in the car, and drive off. I suggest that you go home shortly after we leave". Her eyes now glaring at Jason.

After a few loud clicks from my mom's heels, and the sound of a slamming door, I looked up at Jason.

Whatever magic we both felt from our session of lovemaking had vacated the room. Instead of looking at me with lust, he almost had a disgusted look on his face.

He finished dressing, and exited the front door without saying anything.

I sat on the couch realizing I still clutched a blanket over my naked body.

I went to my room and the tears began to fall. I couldn't believe what my life had become. I was embarrassed, ashamed, and I felt used. On top of it all my mother walked in on us.

I got up and went to the bathroom. What little makeup I wore was a splotchy mess.

As I looked at my reflection I no longer felt cute and feminine. I looked like a clown, and to top it off I medicated myself with sketchy drugs I bought online.

I looked down. My penis was practically nothing now. I haven't been able to get an erection for weeks. My testicles were almost non existent. I could probably never have children. What have I done to myself!?

I cleaned up and put on a baggy sweatshirt and sweatpants before laying down and crying myself to sleep.

Ch8

The next few days passed. I had completely turned on my feminine side. The image of Jason's disgusted face haunted me, and after talking with my mother I decided to get my small breasts removed. She was able to book an appointment at the same plastic surgery center and date as Kelly's augmentation surgery.

While i still hated my sister for the constant ridicule, I was no longer jealous. She can parade around with her big tits all she wants, and her cheating boyfriend. I just want a normal, simple life as a guy.

I didn't see Jason again until the day of our surgeries. We didn't speak, but for some reason I could tell he still had feelings for me. I caught him staring at me a couple of times while Kelly laughed and babbled on about going shopping for new clothes after this.

As I lay in the hospital bed, all of my old feelings were flooding back. Feelings for Jason, feelings for my femininity. Oh no, had I made a mistake?! Before I had the courage to speak up, the anesthesia was kicking in. I tried to scream, but everything just went black.

Ch9

As I awoke, I just looked blankly at the ceiling. My head was cloudy, and the weight of my decision was creeping slowly back onto me.

As the sights and sounds around me were becoming less muffled, a nurse appeared at my side.

Her mask was pulled down, and she displayed a bright smile as she spoke. "Everything went perfectly sweetie, they look amazing! Dr. Stevens will be back in a few minutes to check on you". I tried to speak, but my mouth was so dry I couldn't get it out.

Who is Dr. Stevens? I wondered.

I was regaining sensation, and looked down at my bandaged chest. I was more confused as the bandages looked like they were stacked really thick. I tried to adjust but was greeted with a sharp pain.

The nurse returned with a cup of ice chips. Her bright smile returned as she began writing on the dry erase board toward the foot of my bed.

"Ok girl, you did good. I'm clocking out for the day so Sarah will be your nurse". She flashed another smile and a wave before heading out.

Did she just call me girl? I looked at the board she was writing on. It was tough to make it out. I could see clearly where she had erased her name and wrote Sarah in bold black ink.

I squinted at the top of the board. Next to "Patient Name" it was hard to read...HOLY SHIT!... did that say Kelly!?

What was going on?

My mind raced as I laid there alone. The once loud sounds of a busy surgical center became distant and muffled.

As I reached for the "call nurse" button I noticed the band on my wrist. Sure enough it was adorned with the name "Kelly Bradford".

I pressed the button.

I was still in a loopy state. I almost didn't notice the nurse come in the room. Unlike the one from before. Sarah, I presumed, looked nervous and shyed away from eye contact.

"What happened"? I muttered weakly.

Sarah stammered and fumbled her words until she was saved by a young man who i later found out to be Dr. Stevens.

Before I could say anything the Doctor spoke in a careful tone.

"Andy...there has been a slight mix up"