Roommate - Huge Changes Ch. 01

Story Info
A man starts his journey towards his love for cock.
3.4k words
4.31
45.6k
62

Part 1 of the 3 part series

Updated 06/10/2023
Created 08/10/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Eikmoo
Eikmoo
165 Followers

A pounding headache woke me up way to early in the morning. My eyes were sore from all the crying I did last night. There was even a little wet spot next to my pillow from all the crying. With a sigh, that almost makes me feel like I sunk into the bed, I look around my room to locate my phone. It's on the nightstand underneath a glass of water. At least yesterday me was kind enough to remember to get me some water.

"Fuck my life..." I mumbled and chugged the water.

So there I was yesterday at the local watering hole, with my roommate Daniel and his girlfriend Sarah, having a fun time and a bunch of drinks. The bar was dark with mood lighting and smelled like sweet, alcohol and tobacco. Daniel works at the same IT department as me and Sarah works in accounting. Daniel is a little shorter than my 6'2 but unlike my scrawny build he is muscular. He's practically a gym rat. Quite cocky but he's kind and helpful.

"So what about her, Ray?" Daniel whispers to me with a breath that smells like vodka.

He's obviously pointing at the brunette bombshell at the bar. She's tall and curvy. The tight grey dress sits on her like spandex and you can almost see the outline of her thong but no bra is visible underneath the grey tight fabric. A smile is on her face but she is sitting alone at the bar stirring her drink with a tiny drink umbrella. A knot started forming in my stomach.

"I-I don't know, man. It's still too early for me." I stammered while trying to focus on the ice in my drink.

"Oh c'mon! It's been over 6 months since you and Jessica broke up!" Daniel bellowed as he slapped me in the back.

I almost spilled my drink. My back was searing from the impact of the slap. I turned my face towards Daniel with a plastered smile on my face. He was handsome. Dark hair like charcoal, blue eyes that gave you trust, and a jawline that could cut glass.

"Thanks Daniel. I know you invited me to get me out of the apartment. I'm not gonna be looking for a new relationship just yet. Let's just have fun, ok?" I said with some faked confidence.

"I'm not talking about a relationship! You just need your pecker wet." Daniel stated while yet again pointing at the brunette at the bar.

"I. Don't. Want. That. Yet." I pushed out between my teeth.

"Fine. Fine! I just know what I need to get over an ex. I was just trying to help." Daniel pleaded while trowing his arms up in the air.

"I know. Hey Daniel..." I looked him straight in the eyes "t-thanks for being good friend." I wheezed while trying to hold back some tears.

"It's ok, bro. You're a good friend too. Forget I said anything! Let's get hammered!" Daniel exclaimed.

"Let's get hammered!" A deep female voiced chimed in from our right.

Turned my head to the left and there was Sarah walking towards us with a pitcher of beer in each hand. Her light auburn hair had red streams of red dyed into it. She was wearing a red dress that fit her curvaceous figure quite well. A looong cleavage was showing. Sarah was more then a head shorter then me but carried at least two heads on her chest. She was three things. Short, beautiful and STACKED! Her J-cups were almost spilling out of her dress and with each step she took towards us they heaved and bounced. My heart sped up as my eyes were transfixed on the jiggling behemoths.

"Here's the next round, boys!" She chirped with a smile on her face. "Hey Ray! Eyes up here!" She requested as she pointed at her eyes.

"Y-yeah sorry..." I stammerd while trying to focus my eyes on the pitchers instead. I felt warmth on my face and could feel my cock getting harder.

"Oh that's ok Ray. I havent worn this dress in ages. I'm partly at fault. " She cooed with a wicked smile on her face.

She sat down next to Daniel in our little corner booth and bent forward towards him and gave him and audible kiss on his cheek. I could smell her sweet lavender perfume from the other side of the booth.

"You're in no danger my dear. Our little Ray is not on the hunt tonight. So let's just have fun!" Daniel proclaimed and lifted his glass high above our table.

"Cheers to alcohol!" Daniel cheered.

"Cheers!" Me and Sarah chimed in as we all clincked our glasses together.

After a couple of hours, of us chatting, laughing and drinking, Daniel and Sarah left towards Sarahs apartment. They were probably going to dance the horizontal tango for the rest of the night. I said I would stay and finish of my beer but I ordered a new drink and sat myself back in the little corner booth and tried to drown my sorrows in alcohol. I don't remember how I got back to our apartment but I remember what I thought of when I got back.

Jessica had been my childhood sweet heart and I had finally gotten into a relationship with her last year. She was tall and athletic. Fit like an amazon. She had abs carved from granite and was probably way stronger then me. We had met at this very bar which Daniel usually went to and sometimes dragged me with him. It had started out well. We went on dates. Had fun double dates with Daniel and his then new girlfriend Sarah. Long nights just the two of us infront of the TV watching series.

We hadn't taken our relationship to the physical level yet. We kissed and made out but we had agreed to take it slow. Jessica had just gotten out of a long relationship which I was thankful for. Because I was a virgin. I lacked confidence which didnt land me a lot of women. The source of this was my below average penis. It was about 3.5 inches erect. Which with my height made it look even smaller.

I had gotten plenty of compliments on my looks. My short light brown hair and green eyes were also as they said handsome and cute. But I had still a lot of fright of not preforming well and also trauma from the boys shower room in my childhood.

Eventually we both got desires to move forward. I asked with a weighted heart if she wouldnt love me anymore if I had a small penis. She reassured me plenty of times as we kissed deeply. I thought the sex was great while she said it was nice. After a month we had sex twice although there were several times were I gave her cunnilingus. Which I enjoyed A LOT. Having her squirming at the touch of my tongue was great. But things changed.

She grew distant and bored of me. Then one day when I came home early. I found her emails on my laptop. She had left them on full display while she was in the shower. Messages with another man. Saying how she loved his huge cock. How much pleasure it gave her. How much she craved it. I was in tears. My heart hurt and my chest felt like someone had kicked it. A started to sob and cry loudly. Spit and tears were streaming down my face.

I heard the shower turn off and the thump of each step as she ran towards my bedroom. She looked with horror as she realized what had occurred. Me lying on the floor crying. Her laptop open on the bed.

"I-I'm so sorry..." She whimpered. "It wasn't supposed to happen.." Tears started to stream down her cheeks.

She crouched down and the towel, she had partially covered her amazon body with, dropped as she reached towards my shoulder.

As soon as her fingers hit my shoulder I shouted! "DON'T TOUCH ME!" She flinched and slumped down on the floor.

"I'm so sorry..." She whimpered again.

"Just leave..." I said lowly after I gasped for air.

"I'm sorry, Ray." She whispered at an almost inaudible level.

"Just leave!" I cried.

The rest was a just a blur. I was gasping for air on the floor and crying while she packed up and left. Then Daniel came home and picked up the pieces that was me.

I blocked her on every social media I had. Told her friends to never contact me. She had come to the apartment once after that. Knocked on the door. I saw her through the peek hole on the door. Never answered. Never opened the door. Just snuck back to my bed and ignored the knocks and when she shouted my name. I stayed in my bed room for a long time after that. I only came out for food or when I had to go to work.

My performance at work dropped a lot but thanks to Danny boy the slack was picked up. He was there for me. He was very blunt but kind. I was jealous of him. I wanted to be him. He had everything. Beautiful girlfriend, confidence and probably a huge cock.

So here I am sitting on my bed with sore eyes and a headache that could kill me. I glanced at my phone. "11.36 AM. Well at least I don't have to work today." I mumbled. The smell of my breath was heavy with alcohol. I stumbled out of bed almost knocking down the bedside table. I sauntered slowly towards the door that lead into the shared living room.

Me and Daniels apartment was on the seventh floor. The entry way led into the living room if you went straight and the kitchen if you turned left. There was a huge window behind the TV in the living room so you could see the beautiful view of the city as soon you entered the apartment. And once you entered the living room my room was to the left and his was to the right. We both had private showers and bathrooms only connected to them.

I walked slowly towards the sofa facing the TV. I could feel the pulse of my heart in my head. The nausea was getting heavier and I could almost feel the bile coming up my throat. I slumped down on the sofa. It was soft and different from my bed. I turned on the TV and lowered it to a slight whisper. Then I passed out once again.

I felt someone touching my shoulder.

"Hey Ray. You alright, man?" Daniel said at low tone while shoving me a little.

"Yeah dude. I'm fine. I'm fine." I groaned as I streched out on the sofa.

"Hey it's 3 PM, man. Haha! You gotta get up before you get physically attached to that sofa!" Daniel chuckled as he jumped over the back of the sofa and landed on an empty seat.

"Shit! Already?!" I gasped as I sat up in the bed.

At least my headache was mostly gone but my stomach was churning almost growling. I was starved. Daniel looked at me with surprise. He must have heard my stomach complaining.

"Hey Ray. How about I order us some pizza? My treat!" He insited with a big smile on his face.

"Sure sure. Sounds good." I said flippantly as I changed the channel.

Fast forward to 20 minutes later. Daniel rushed to the door and brought back some pepperoni pizza with stuffed crust. It smelled heavenly. It was steaming and hot. The cheese was forming strings as you lifted a slice. As we got half way through the pizza, Daniel looked at me with a very concerned look.

"Hey, I was meaning to tell you yesterday..." He muttered and paused.

"Mmm.*gulp* Tell me what?" I inquired as I was stuffing pizza in my face with glee.

"Me and Sarah is working really well together. Like I think she might be THE ONE! My precioussss!" He exclaimed with a very bad gollum impersonation at the end.

"Haha! Good for you Daniel. Just be sure not to tear that ring of hers!" I chuckled and threw a pillow at his face.

"Hehe. Not a chance, man! I mean I might be big but not that big!" Dan hollered as he threw a pillow right back in my face.

I grabbed the pillow that was stuck to my face and held it down onto my crotch. Just the idea of Daniels cock got my face flushed. I could feel my dick twitch.

"So yeah. That's why I wanted to talk." He said in a more solemn tone.

I could feel a little bit of pre leaking from my now hard penis. I was red with embarrassment. Heart was beating so fast. Whats wrong with me I thought as I turned my head towards the TV instead.

"I will be moving in with her..." He murmured and slouch down a little bit resting his elbows on his knees.

My erection faded very fast. It was like a pit had formed in my stomach and I could feel the blood draining from my face.

"Don't worry, man. I have barely been here the past weeks. I have practically already live at her place already and we're not getting any younger. We're already 30." He chuckled.

I sat there in silence. Just looking straight at the TV. Trying not to panic. My thoughts rushing through my head. What's going to happen with me? I can't afford this apartment on my own! I can't move back to my parents. We hadn't spoken in ages since the big fight.

"Hey Hey. Before you panic. I will still pay my share until you either find a new place or a new roommate. So take a deep breath. And just reeelax." He coached as he motioned his hand downwards as if to calm me.

My face started to regain some color. I felt the knot in my stomach relax and unravel.

"That sucks. I mean that's great for you... but still sucks." I said as I shivered.

"Relax, bro. I will help you find a new place or roommate." He assured.

We finished the pizza and started watching a new series on Netflix. After a few episodes he left with a box of his stuff. Said he would be back for the rest of his stuff later.

As I sat down by myself on the couch my head was swimming with thoughts. I could still smell the pizza lingering in the room. I look the place on the sofa where Dan sat. Did I have feelings for Daniel? What was I supposed to do with the apartment? Was I gay? Should I find a new roomie?

Well I still have the hots for Sarah. An image of her fat tits popped up in my head and I could feel my loins stirring. Maybe I was bi? Fuck! Leave that for later.

You know what? Fuck the other problem as well. I have had enough of the self-pity! Yeah! I can do this!

I rushed towards my bedroom and almost fell off my computer chair as I jumped infront of my computer.

*Whirr* The fans started spinning as I hit the big start button on my desktop. As soon it was booted I quickly clicked open my web browser. For the rest of the night I put up ads of roommate availability on every site I could find.

First new roommate and if that didn't work I would find something else and I want to do it on my own. No more relying on Daniel. I gotta fix this on my own!

As I got off the computer I laid down on the bed with a sigh and a smile.

"I can do this!" I howled as I shook my hands towards the ceiling.

I slowly drifted of to sleep as I was coming off my buzz.

*PING* A loud ping from my phone woke me up. As I shoved my covers off my body I yawned. I opened up the message that just arrived while I was rubbing my eyes with my other hand.

"Hi I'm Anna. I was wondering if the room was still available? :)" The message read.

Really? Already? Wait. Anna? A woman. I had listed the ad with my age and gender I did not think a woman would respond. My heart started to beat. I felt excitement building up from my core.

"Yes. It is still available. I would like if we could me in person. So I know if we're a right fit and if you like the apartment?" I hit the send button and then nervously waited for a response.

*PING* I jumped a little and almost dropped the phone. Damn I should've lowered the volume a bit.

"Yeah! That sounds like a great idea :D How does 6 PM sound?" The response read.

"Today? Or did you mean another day?" I typed into the message. Waited a bit before I hit send.

"Yeah! Today would be great! This is awesome :D Thank you so much." The message made me feel all giddy.

"Great! so I will se you at 6 than." I typed in and hit send so fast that I left typos.

There was no further response from Anna. So I got up out of bed and hit the shower as fast as I could.

After the shower I called Daniel with the good news before I had taken a step out of the shower. Danny boy hurried over and we cleaned and I helped him move the last of his stuff over to Sarah apartment... well their apartment.

Then he dropped me off at our apartment. I walked through the front entrance and took the elevator up to the seventh floor. Looked at my watch. 5:30 PM. Great, I still had 30 minutes to spare!

I took of my jacket and grabbed a soda from the fridge. Noticed we had forgotten to close the door to the laundry room in the kitchen. Before I even reached it the door I was interrupted by the doorbell.

My heart made a somersault and I put the can down on the kitchen table. I fiddle with my hair. Trying to fix a mess that wasn't there. I walked over to the door and opened up the door.

"Hi. My name is Reynold. Welcome..." I said and stopped when I didnt see anyone.

"H-Hi!" Stammered a sweet melodious voice came from my right.

I looked to my right and down. There stood a young woman. Sky blue eyes were staring right up into mine. Quite a young looking face. Beautiful blonde hair cascaded down her shoulders. She was quite short. A little bit shorter than Sarah. She had a beautiful flowery dress with a poofy skirt on. She had at least D-cup breasts hidden underneath those beautiful flowers. While I was looking at her, her full lips curved into a smile. She was a goddess.

"H-Hello." I stammered as I looked into her eyes.

She scrunched her nose, squinted her eyes and made an even bigger smile. She reached out her hand for a handshake. Her face shifted in to a bit more nervous smile.

"I-I am Anna. Nice to meet you Reynold!" She sounded a bit shaken but happy.

I reached out my own hand and clasped it into hers. Her hand was soft like silk and and very small in comparison to mine. But it was so warm. I shook it softly and we both let go at the same time.

"Nice to meet you! My friends call me Ray. And I would love it if you called me that as well." I uttered with faked confidence in my smile.

"Well Ray. I am A-Anna Hughes. You can call me Ann." She stuttered.

She seemed nervous or excited. And shyly looked down towards her shoes.

"Reynold, Ray, Smith. Nice to meet you Ann." I said with a little bit less faked confidence.

"Please do come in." I continued while opening the door and turned around and walked into the hallway.

If I hadn't turned around so fast I might have seen it. She adjusted something large and thick under her poofy dress and walked slowly through the door after me.

Eikmoo
Eikmoo
165 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
AnonymousAnonymousover 2 years ago

Fajny interesujący początek i bardzo wciągający, już czekam niecierpliwie na kolejne rozdziały.

Może w pełni odnajdę siebie w Rayu (bo już widzę siebie w tej osobie).

SissyBoy z Warszawy

FemRyderFemRyderover 2 years ago

A good start and I look forward to how it continues :)

stockingguy78stockingguy78over 2 years ago

Great start, looking forward to chapter 2!

AnonymousAnonymousover 2 years ago

good story. I hope at least Anna will have monster chicken 2 feet or more and also there will be size comparison between the two. Anna was supposed to be dominating and humiliating Ray. It would definitely look amazing, although I honestly wish Anna had a better body. such as height and giant breasts or with pronounced muscles. so he would look like a bodybuilder instead of Ray. that's it, can't wait to see the second chapter

JoannePareJoannePareover 2 years ago

This is a very good beginning of yoru story, hope you have many more to tell us about and especially how feminine Ann is. Eager to rea much more.

Joanne

XO

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Bet Hung girl wagers that Billy will love her cock in his ass.in Transgender & Crossdressers
Futa House A boy unwittingly discovers a gold mine of girlcock.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
More Stories