What If?

Going to an all girls’ college, I never thought twice about the gender of my
roommate. She seemed to be a bit tomboyish but was still cute in her own way. She was
from Thailand but spoke with no accent. She had a tanned face, a rounded nose, a small
full mouth, and two deep brown eyes. She had shaggy layered black hair that I always
longed to run my fingers through. Little to say I was attracted to her from the day I met
her. Her daily attire consisted of baggy shirts, whether they were long sleeved or t-shirts,
and baggy pants, jeans mostly. She also had a couple pairs of ratty sneakers. I didn’t
dress much different so we shared clothes a lot.

I didn’t find out the truth about my roommate until the day my bed broke. We
were sitting on it while doing our homework and we started messing around. She had just
pinned me to the covers when we heard a distinctive crunch. Suddenly, my bed frame
was on the floor and we were panting. We looked at each other questioningly and got up
from the broken frame. We went to find our floor manager and told him what happened.
He said he would order me a new bed but until it came we would have to share. We didn’t
mind and went back to our room to get my covers and other things from the mangled
woodpile. We helped our floor manager remove the pieces of wood and put them in the
garbage.

When we went back to our room we arraigned my blanket and extra pillows into a
small sitting area on my side of the room.

“You don’t mind sharing a bed with me?” she asked.

“Of course not,” I answered. She seemed a bit unsure but smiled. That night she
went to change in the bathroom like she always did and I changed in our room. We then
got into the same bed, snuggled under the covers and went to sleep.

It wasn’t until the next morning that I knew something was up with my roommate.
As I sleepily opened my eyes I realized that I was sleeping with my back to my
roommate. What I felt pushing back against me wasn’t the straight front I expected, but
the distinct feeling of someone aroused. My roommate sighed and rolled onto her front,
giving me a clear view of the bulge in her pajama pants. I looked at the bump a bit more
before I hesitantly reached out my hand and lightly touched the top. I knew almost
instantly that it was an actual dick. My roommate was actually a boy! I softly gripped the
sides of his pajama pants and slowly slid them off his hips. His erection bounced to life in
the air, an event he seemed unaware of. I gently reached out my fingers and touched it.
My roommate moaned a bit but didn’t wake up. I stroked my digits up and down the silky
shaft, eliciting delightful sounds from my roommate.

I didn’t notice that his eyes were starting to flutter open.

“What are you doing?” he asked groggily.

“Playing with your cock,” I answered. His eyes sprang open and he was
fully awake. He sat up on his elbows and saw my hands on him. “Why did you pretend to
be a girl?” I asked as I stroked the sensitive head.

“I liked the school. I wanted to go here so I pretended to be a girl,” he
explained.
“What’s you’re real name?”

“Please stop stroking me. My name is Pirat.” I put my fingers under his
chin and lifted his eyes.

“Do you want me?” I demanded. He slowly nodded and I brought his head
to mine and we kissed. As I pulled away he flipped me over and pinned me under him.

“Do you have class today?” he panted at me.

“No,” I answered. With that he smashed our lips together and our tongues
began to duel. I stroked my hand down his chest then up under his shirt. He pulled it up
for me, exposing his tanned firm belly. He came down again and I sucked one of his
caramel colored nipples into my mouth. He moaned and dropped his head to my
shoulder. I languidly used my tongue to caress the nub and the plane of his nipple,
enjoying the smooth feeling. He cried out a bit as I nipped it gently.

I felt him lower his lips to my neck and begin sucking on my flesh. He used his
tongue to sooth the abrazed areas. Soon, he was trying to pry off my shirt, which I gladly
helped with. I watched as his eyes gazed at my small breasts lovingly. He came back to
my face and he kissed me again. It was not rough but sweet and sensual. His tongue
gently caressed my own as he ran his long fingers through my hair. He looked into my
eyes then went down my body and softly lapped at my nipple. My body jerked
underneath and he smiled. He then sat back on his knees and looked at me, his dick
harder than before.

“Shall we continue?” he asked. I could feel the moisture running down my
thighs as I nodded. He smiled again and seductively started to pull down his pants the rest
of the way. Naked, he was quite beautiful. I could tell that the stain forming on the front of
my tight shorts was exciting him. He gently touched the damp mound between my legs
with unbridled joy, the smile on his face widening. He gripped the top of my panties and
slowly started peeling them off my body. I couldn’t help but moan as he slowly ran his
finger along my slit as he pulled off the fabric. Once the damp panties were off he
unceremoniously threw them across the room and turned back to me. He lifted and
spread my legs then, using his pointer finger, carefully ran his finger over me a few more
times. Before I knew it, one of his fingers had found it’s way inside of me and was
cautiously exploring. I could tell that he liked the feeling. Another finger joined the first and
he started to stretch and stroke me. I had to suppress my moans by turning my head into
the pillow. He took his fingers out a couple of minutes later and went over to his desk. He
opened a drawer and fumbled around a bit until he pulled out a box of condoms. He
threw the box back into the drawer and slithered his way back to the bed, only stopping to
open the condom and through away the wrapper. He crawled onto the bed and straddled
my hips. I watched as he fitted the condom onto himself and lifted my legs up over his
hips. “Are you sure?” he asked me.

“Yes, just be gentle at first,” I told him. He nodded to me and stroked my
cheek. I gasped as I felt him enter me. He seemed to completely fill me, a comfortable
fit nonetheless. He fit perfectly inside me, not too big and not too small. He waited a bit
before he started to move inside of me. The feeling was electric; it pulsed through my
skin and made me hum all over. I think he felt my excitement because he leaned down
and kissed me. What we experienced together in those twenty minutes will remain one of
my most cherished moments of college. The feeling of his hot body pressed against
mine, our sweat mixing together is something that I only wanted him to experience.
We’ve been together since that time and even though my bed has been replaced, I still
tend to spend the night in Pirat’s.