My High School Bully Fucked Me

I ran into my HS bully at a bar while dressed as a woman and ended up going home with him.

As a kid I was bullied by just about everyone in my school. I was the weird kid and still am to this day. Somehow it had gotten out that I liked to dress in women’s clothing, and everyone already knew I was bisexual. When they found out I wore women’s panties under my boxer shorts every day, it was social suicide to say the least. However, no matter how bad I got bullied I never stopped doing what I was doing. It was the only way I felt comfortable.

Chris, was the guy that bullied me the most. He lived about 4 houses down from me as a kid and would always follow me home and torment me. Of all the bullying, his hurt the most because we were friends in grade school but as soon as I got to high school and my personality changed, he began making fun of me ruthlessly. It also hurt because as bad as he made me feel, I was secretly attracted to him.

Fast forward to me in my early 40’s

I was bored and particularly horny last weekend and my dildo just wasn’t sufficiently getting the job done, so I got dolled up and went to my favorite gay and trans friendly bar.

I am a cross dresser in my early 40’s. I am a big; weighing a few ticks over 300 lbs. I am completely hairless, I have a big ass and all natural man boobs. I’m also packing an 8” cock!

My outfit for this night was; black satin panties, matching black stockings and heels. I had a red dress on, and I chose a long black wig. I’m usually a blonde but tonight I felt a bit wicked so I finished the look with some dark eyeshadow and black lipstick.

I’m a regular at this particular bar and pretty much have it scoped out. This night I happened to notice a man around my age sitting by himself at the end of the bar sipping a drink. I didn’t recognize him at first but as I approached him I immediately knew who it was. Chris!

We made eye contact as I passed by but neither of us said anything. Most definitely he didn’t recognize me. I’m dressed as a woman and I’m much bigger than I was in high school. Plus, we haven’t seen each other in over 20 years.

I sat at the opposite end of the bar and watched him for a few minutes. Periodically he would glance in my direction but nothing was said.

“This is for you, Sam. Compliments from the gentleman at the end of the bar.” The bartender said handing me a drink

As I took the drink from him I glanced up and Chris was approaching me.

“May I sit next to you, Samantha?” Chris asked

“Of course. How did you know my name?” I asked taking a sip from the martini glass

“The bartender was kind enough to tell me.” He answered

It was clear he had no clue who I was. My heart was already racing to begin with but now the thrill of him not knowing made it all the better.

We shared a few more drinks over the next hour or so and had a really nice conversation. I had almost forgot how horrible he made my life. The truth was, that despite all that I was having a nice time and I was definitely attracted to him.

Chris was wearing a dark blue suit with a red tie. He still had the same curly hair from when we were kids but it had a little gray in it. His beard and mustache were short and well groomed also with a touch of gray.

By the end of our 5th martini, we were pretty drunk and full on flirting. Chris got up to use the bathroom and as he walked away, I got up and unknown to him, followed him. I stood quietly behind him as he urinated and checked to make sure we were alone. Chris was shocked when he turned around and saw me. I gestured for him to join me in the stahl, then grabbed his tie and pulled him.

As Chris closed the door and locked it, I sat on the toilet and began unzipping his pants. I quickly pulled his clock out which was about 6”, and put it in my mouth. Chris’ head fell back and he let out a sigh of relief. It wasn’t long before his hand was on the top of my head and he unleashed a hot batch of cum down my throat. It was a heavy load that just kept coming. I swallowed every drop.

He quickly zipped his pants and we casually exited the bathroom. To our knowledge, no one saw us but we were intoxicated so who knows and more importantly, who cares.

“Do you want to go back to my place?” Chris asked

“Absolutely!” I answered perhaps a bit overzealous

We made it back to his apartment safely which was only a mile or so from the bar. We stumbled up a few flights of stairs, flirting and talking dirty to each other along the way.

As soon as we got inside his apartment, we headed to the couch. At this point we couldn’t keep our hands off each other. He was a really good kisser and had strong hands squeezing my ass.

Chris ran his hands up my legs, under my dress and lifted it over my head and threw it on the floor. Then he grabbed my panties and yanked them down to my ankles. Before I could kick them off, his mouth was wrapped around the tip of my cock. He had one hand cupping my balls and the other desperately trying to remove his own clothes.

Feeling a bit frustrated, Chris stood up and dropped his pants. We had surprisingly good chemistry. As he tossed the last of his clothing aside, I laid down on the couch. He immediately laid opposite of me and we began 69ing. It was like he read my mind.

Enjoying the chemistry so much, it didn’t take long for my control to disappear. I suddenly shot my load of cum in his mouth.

When I finished cumming, Chris stood up. He laid on top of me and started licking and nibbling on my nipples. Not many of the guys I’ve been with have done that, but I absolutely love when they do.

After the nipple play was done, Chris stood up. He rolled me over onto my stomach and bent me over the arm of his couch.

“I cannot wait to fuck this big ass!” He groaned squeezing my cheek

I felt a drop of spit hit my asshole then his tongue began swirling around the outside of it.

“Oh goddamn that feels good!” I cried

Chris got up behind me, grabbed my hip with one hand and pressed his dick against my eager hole with the other. His cock slipped in quickly and he didn’t wait to begin thrusting.

“Oh shit! Fuck me! C’mon daddy, fuck that ass!” I begged

His hands gripped my hips tightly as he thrusted his manhood in and out of me. My warm inviting hole spread effortlessly for him. His cock slid in and out of me with ease.

*SMACK*

“Yeah, smack my ass! It’s all yours daddy!” I moaned

“I’m gonna cum so hard! I’m gonna put a baby in you!” Chris grunted increasing his thrusts

“Yes! Yes! Fuck me daddy! Cum inside me! Get me pregnant!” I yelled assisting what seemed to be his fantasy

I admit, the pregnant thing was new, but it did really turn me on as well!

Chris let out a loud groan. His left hand had a death grip on my hip and his right was smacking my fat ass. His body tensed up and his toes curled. His body convulsed as he released another hot batch of his baby goo inside my ass.

My hands squeezed the arm rest of his couch and I screamed into a pillow.

“Yes daddy! Pump me full of your cum!” I screamed

As he settled, he pulled his throbbing cock from my ass and collapsed on the couch. I laid down next to him, both of us out of breath and covered in sweat. I could feel his cum leaking from my ass and I didn’t care.

“You wanna spend the night?” He said still trying to catch his breath

“Of course!” I replied

Once we were breathing normally again, I got up and took a quick shower. When I got out, his room was dark and I could barely see my way. I eventually climbed into bed and we kissed for a few minutes. It was enough to make my dick hard again but nothing happened which was probably good because I didn’t have my makeup or wig on anymore and maybe he would recognize me. Instead we both fell asleep almost immediately after.

I woke up around 6am. It was still dark and Chris was sound asleep. Truthfully, I still wanted him to fuck me again when he woke up but I decided to quietly leave without waking him. I wrote my number in lipstick on his bathroom mirror before I left.

Chris called that very night and we are going on a date tomorrow. He still doesn’t know who I am. I may have to tell him, but not until he fucks me at least once more!

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