Jackie’s First Anal

Jackie’s First Anal
By: DamonX ([email protected])

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
fantasy?”

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!

“Yep.”

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.”

“Really?”

“Yes.”

“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
me.”

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.