Jackie's First Anal
By: DamonX (email@example.com)
I don't quite remember when I started to become attracted to Jackie.
When she first moved in, she was just another roommate, and I figured
she'd be gone in a few months. But as the months wore on, we began
hanging out quite a bit. That is, whenever her extremely jealous
boyfriend wasn't around. She wasn't the best looking girl in the
world. Then again, she wasn't exactly ugly either. But it was those
legs that first got me. She was getting ready to go out jogging one
day and I caught a glimpse of those fine muscular stems. They were
tanned and well defined and right away, I wanted them wrapped around
me. And I knew she was attracted to me too. I saw the way she looked
at me when she saw me come out of the shower wearing just a towel. Our
harmless conversation soon turned to flirting, and before I knew it, we
hanging out every night.
We remained only friends, however, and I was even demoted from that
position whenever Johnathan, her significant other, came for a visit.
I didn't like him and I knew he didn't like me. He was a snobby
arrogant prick, and I really couldn't see what Jackie saw in him. He
was the kind of guy that would want to stay home on weekends and watch
reruns of "Law and Order" on TV. She was the kind of girl that you
could take to a bar to drink beer and watch the game. She was very
athletic, and I think that made me even more attracted to her. I
couldn't help but stare whenever she came back from the gym in her
little sports bra, glistening with sweat. I knew she noticed me
checking her out, but she never said anything.
One night the two of us were sitting around watching TV, when Jackie
suggested we open a bottle of wine that she had been saving since
Christmas. I wasn't much of a wine drinker, but I accepted out of
courtesy. After a few glasses, the topic of conversation turned to
sex, as it often does when alcohol is involved. We shared a few past
experiences, although Jackie was doing most of the asking.
"So, Jackie." I said, taking another sip of wine. "What is your wildest
She let out a laugh.
"Wildest fantasy??" she asked. "What kind of question is that?"
"Come on." I replied. "You have to have something buried deep down
inside that you want to let out. Let's hear it."
"Well... there is one thing..."
I sat patiently waiting.
"No!" she said finally. "I can't say. It's embarrassing!"
"Oh, come on! How bad can it be? Believe me. If it's that dirty, I've
probably done it."
Jackie let out a laugh and refilled her wine glass. I was staring at
her. The alcohol was starring to get to me and she was looking better
and better. She was only wearing a pair of sweat pants and a t-shirt,
but somehow, she still looked sexy.
"Okay!" she said finally. "You'll probably just badger me until I tell
you anyway, so I might as well just say it."
"Well," I said. "I'm waiting."
"I...I want to try it... you know. From behind."
"You mean doggie style?? That's your big fantasy?"
"No!" She cut me off. "In the other place. You know... The back door."
My dick went hard almost instantly. I was speechless.
"Really?" I stammered.
Usually I had to beg girls into letting me do them in the ass, and here
was one that actually wanted it!
Jackie was blushing a deep shade of red.
"So.. Why don't you do it? I asked.
She took another large swig of wine.
"Johnathan thinks it's gross."
"That figures," I muttered under my breath.
"Every time it gets mentioned he rants about how perverted it is."
"Well that's the point!" I said with a grin.
"Have you done it?" she asked.
"Oh yeah. I love it. I'd fuck every girl in the ass if I could."
"So you must be pretty good at it then huh?"
I was surprised at how curious she was.
"I guess so."
"Does it hurt?"
"Sometimes. If you go too fast, or if you don't use enough lube."
"Well, aren't you just the anal sex expert!" Jackie said sarcastically.
"I do what I can." I replied with a smile, before draining the last of
my wine. "So if you ever need a lesson..."
"You perv!" she said, punching me in the shoulder.
"Hey," I replied. "You're the one that wants a dick in your ass. Not
We both had a bit of laugh, before she put her glass down.
"I think it's time for bed." Jackie said, as she stood up.
"Sweet dreams," I replied as she walked to her room.
The next day I kept thinking about our conversation from the day before.
I would have never thought Jackie was the kind of girl that would want
it in the ass, although the thought of her doing it turned me on to no
I didn't see her the entire day, until she came back from work and
started to get ready. it was Friday and that meant she was going to go
to Jonathan's place for the night. I wanted to tell her that I felt
sorry for her, but I decided to keep my comments to myself. She
didn't say much either. I think she was still a little embarrassed
about what she had told me the night before. Either way, I was in for
a lonely night alone watching porn and jerking off while Jackie would
be watching her loser boyfriend play scrabble on the internet.
She said a quick "Bye" and hurried out the door. I sat back and tuned
on the TV. A few minutes later I was asleep.
I woke a few hours later, and looked at the clock. It was 1:00am! I
wondered how I could have slept for so long. Shaking my head, I got up
to go brush my teeth. I then staggered to my room and crashed into my
bed trying to get back to sleep. I watched the clock and the time
drifted by. There was no way I was getting to sleep now. I tossed and
turned but it was no use.
Suddenly I heard the front door open and close. "Jackie?" I thought to
myself. Why was she home so early? She usually stayed the night at
I listened as she walked round the apartment for a while. I wondered
what she was doing.
Then there was a soft tap at my bedroom door.
"Damon," she whispered. "Are you awake?"
She pushed the door open a crack.
"Yeah, it's okay." I replied. "You can come in."
She walked in and closed the door behind her. I could see the
silhouette of her body moving across my bedroom as my eyes adjusted to
the darkness once again.
She sat at the end of my bed, and I sat up.
"Is everything okay?" I asked, starting to get little concerned.
"Yeah, everything's fine."
I could tell she had been drinking a little bit.
"So what's up?" I asked.
She just sat there quietly. She was wearing the same sweat pants that
she wore the night before along with a tiny little t-shirt with a happy
face on it.
She turned and looked at me.
"Remember our conversation last night?" she asked.
"Of course. How could I forget?"
"Well, I've been thinking..."
"I want to do it."
"Yes. I want you to fuck me in the ass."
My mouth dropped open.
"But what about..."
"Right now I don't really care."
I was surprised at her bluntness, but I certainly wasn't complaining.
"Did you guys have a fight or something?"
"Kind of. I told him that I wanted to try it in the butt, and we got in
this big argument. I felt so embarrassed, I had to leave."
I just sat there trying to take in this sudden turn of events.
"It's not like I'll be cheating!" she said suddenly. "I mean... We
don't have to kiss or anything. I just really need to try this."
"Not cheating?" I thought to myself. I wasn't about to argue, but if my
girlfriend let some guy stick it in her ass, I'd think otherwise.
"So what do you say?" she asked with a cute little smile. "Will you be
It didn't take me long to answer.
"Of course I will."
"Good. So how do we start?"
I was still a little shocked.
"Ummm, I guess first we have to get these off." I said reaching over and
inching down the waistband of her sweatpants.
Jackie pulled her feet up on to the bed and helped me slide her pants
down those smooth tanned legs. damn she looked cute. Sitting there
wearing just a t-shirt and a pair of panties. I couldn't resist. I
leaned down and planted a soft kiss on her thigh. I felt a shiver go
through her body, and looked up to see her smiling down at me. I
brought my face up to hers, but she stopped me.
"Uh uh," she said quietly. "No kissing."
I nodded and went back to her legs. First I kissed the inside of her
thigh, and then the outside, moving around to her hip. I pulled a
corner of her panties down and kissed her there, before coaxing her
onto her stomach. Jackie sighed as she rolled over. I ran my tongue
in small circles around her lower back, before moving down to her ass.
I planted gentle, wet kisses along the areas of skin that were
uncovered, before running my tongue along the fabric of her panties.
Jackie moaned quietly as my tongue traced its way along the crack of her
firm, muscular ass. I then took her panties and began pulling them
off. She raised her hips off the bed and I slid them down her legs. I
was now staring at her perfect ass, lying on my bed. I lowered my head
again and kissed her at the beginning of her crack. She let out a soft
giggle and I continued. Back and forth I moved from one cheek to the
other, kissing and licking her soft skin, getting closer and closer to
my final destination.
"Move up," I said, pulling her hips up off the bed.
Jackie raised herself up to her hands and knees, making her ass look
even more irresistible. Gently, I pried apart her taut cheeks. I
could see her cute little pink asshole staring back at me. Like the
rest of her body, it was perfect.
I ran my tongue along one cheek and down into her crack moving
"Damon..." she started to say.
Her words were cut short, however, as my tongue flicked across her
"Oh my god." she moaned.
I knew she liked it and I was willing to give her more.
I teased her a little, by licking around her tight little hole, but
never actually touching it. I knew it would drive her crazy.
"Don't tease me." she said in a cute little voice.
Jackie almost collapsed with pleasure as my tongue touched her tiny pink
bull's-eye again. I stabbed at it with my tongue, trying to wiggle my
way inside but her ass was too tight.
"Relax," I said.
I then resorted to swiping her butt hole with my tongue, wetting it with
saliva with each pass.
"That feels so good," she moaned.
When her ass was nice and wet, I pushed my face right into her. I
planted a deep kiss on her butt hole and forced my tongue inside her.
My lips were massaging her outer rim as my tongue wriggled inside her
like a snake. I then straightened my tongue and started sliding it in
and out. I was actually tongue fucking my roommate's asshole!
When Jackie was nice and loosened up, I began to massage her hole with
"Oh my God Damon!" she exclaimed. "I had no idea that would feel so
I smiled to myself and slid a finger in slowly. I watched as her tight
little ass swallowed up my finger and gripped it tightly in place. I
could tell she was eager, as her ass was clenching and unclenching
around my finger. All the while I was driven on by the sounds of
Jackie's sexy moans.
"How does that feel?" I asked.
"So fucking good!"
"Do you think you can handle another finger?"
I pushed in another finger and started sawing back and forth. Jackie
buried her face in my blankets as I continued finger fucking her virgin
asshole. I lowered my face and started to lick around her rim as my
fingers penetrated her depths. I pushed my fingers in up to the
knuckle and I knew she was ready.
"Put your dick in me now, Damon. I want to feel it."
I gently slid my fingers out of her ass and pulled off my boxer shorts.
My cock was already as hard as it could be, so I didn't need any
preparation. I leaned over the bed and slid open a drawer. I rummaged
around for a while before I found what I was looking for. I took the
bottle of lubricant and flicked it open. I squirted a little into
Jackie's crack, and she shuddered.
"It's cold." she said.
"Sorry," I replied, leaning in to breath hot air over her exposed
My finger were soon back at work, rubbing the lube into her hole. I
dipped one, the two fingers into her, getting her nice and primed. I
then squirted some into my hand and coated my dick with the gooey
After tossing the bottle to the floor, I pulled Jackie's ass apart and
began to slide my slippery cock up and down her crack, before coming to
a stop at her tight little hole. She was holding her breath as I began
to push. Her ass was tight and didn't give much, but I managed to
squeeze my head in with a pop.
"Uhhhggg," she groaned as her tight muscular ring clamped down around my
cock, imprisoning it within the confines of her virgin asshole.
I stopped and just let her get used to the feeling. After a while she
began to relax a little more and I began to move my hips around,
swiveling the head of my cock around in her ass. I then pushed forward
a little more. It was very tight and hard to make any ground. I
spread her cheeks and stared at my cock, half buried in her ass. I
also noticed she was starting to play with her pussy.
"Keep going." she urged. "I want to feel all of your dick inside me."
I reached around and grabbed the front of her thighs, pulling her back a
little. She moaned louder as her ass slid down my lubricated dick.
After a few more minutes I was completely buried in her tight hole.
The feeling was amazing and I started grinding my hips into her ass.
My balls were pressed firmly against her pussy lips, and I could feel
the vibrations from Jackie playing with her clit.
"It feels so full." she said. "I love it!"
As I withdrew, I could feel that tight ass grabbing at my cock, trying
to hold me in place. I pulled back almost all the way out. My dick
head was gently tugging at her muscular ring, threatening to pop out.
I then pushed my way back up Jackie's asshole, this time a little
"Oh my fucking god!" she exclaimed as I bottomed out again.
She was squeezing her ass tightly around my dick. and I was having a
hard time even moving it. The site was so perfect I wished I had a
camera. The way her perfect ass was raised in the air, accepting my
cock. Her narrow little waist, bending low before rising back up to
her shoulders. I don't think there's anything sexier on Earth than a
woman in that position.
"Faster, please," she moaned.
I started fucking her at a medium pace, trying to control myself.
Jackie was actually pushing her hips back at me. I stopped moving and
she increased her pace, thrusting her firm ass backwards. She dropped
her head into the blankets and screamed into the sheets as she roared
through her first anal induced climax. I could feel her ass clenching
and unclenching around my cock as she tried to milk it with her
asshole. The feeling was incredible! I wasn't even doing anything.
Jackie was fucking me with her ass!
"Yes, it's so good! Keep butt fucking me Damon!"
She was turning me on! I grabbed a hold of her hips and thrusted
forward, feeding my cock into her greedy little asshole.
"Uhhhhh!" she groaned loudly.
I pulled out again before drilling her tiny hole with another hard
"Yes! I love it! I love your cock in my ass!"
Every time I heard that cute little voice of hers say something dirty I
thought I would blow my load. I restrained myself, however, since the
experience was way to good to be rushed. I was fucking her ass now. I
was pounding that small hole, driving her hips down into my bed. I
almost got carried away , but stopped before I went over the edge.
Jackie turned to look at me.
"Can we try it in a different position?" she asked.
"Sure," I said, pulling my cock free from her slippery butt hole. "Get
on your back and pull your legs up to your head."
I had never tried it that way so I was eager to experiment. Jackie did
as she was told. As she rolled over I stared down at her cleanly
shaven pussy and wondered if I would ever get the chance to try that
Pulling her legs up to her head, her hips raised off the bed. I moved
forward and slipped my cock back into her waiting asshole. This
position was even better. I stared down at my cock moving in and out
of her body, then up to her face. Her eyes were closed in pleasure,
and a quiet moan was resonating from her lips. I knew I wasn't going
to last much longer.
"Jackie, I'm going to cum soon."
She looked up at me. "Okay."
I was guessing that she didn't care if I pulled out of not, so I just
kept fucking her. I started going faster and faster as I felt the cum
rising inside me. With a groan, my cock spasmed and unloaded a massive
torrent of hot jism deep inside Jackie's well fucked asshole.
"Ohhh," she squealed. "That feels good!"
I kept my cock firmly embedded in her ass for a few moments, before I
pulled out. As my dick slipped from her ass, it was followed by a thin
trickle of my cum. I collapsed back on my bed, fatigued and sleepy.
Without a word, Jackie slipped her panties back on.
"Thanks Professor", she said kissing me on the cheek. "That was
With that, she snatched up her sweatpants and walked out of my room. As
she left, I stared at the ass I had just fucked. There was a small wet
spot forming in her panties and I knew it was from my cum dripping out
of her freshly fucked hole. She turned, gave me a smile and closed the
door. One thing was for sure. It's going to be a lot more interesting
living here from now on.