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My girlfriend Cathy loves when I slide my finger in her ass
while we're fucking or when I eat her. But she's always been
hesitant to let me fuck her in the ass.
"I don't know," she always says, "it looks like it hurts."
No matter how much I persuade her, I stil can't convince her.
She has two housemates, while I have my own place. As a
result, we spend more time at my place. One Friday night, we
didn't feel like going out, so I rented a couple of movies. We did
as we always do, watched the straight movie first, sipping wine and
nibbling take out. Then, after the movie, we put on a porn tape
and followed our inclinations.
Well, the movie we rented was pretty hot. One scene showed
a really hung stud working his tool into the tight backside of a
sweet young thing. Cathy stopped playing with me and sat rapt,
watching. The guy slowly worked his cock into the girl, while she
obviously liked it. By the time the guy had fourteen inches in the
girl's butt, Cathy was breathing hard. She bent to blow me, one
finger working into my asshole. I worked her around on top of me
and began eating her.
I slipped one finger in her wet pussy, then worked it into her
ass. Her checks clenched around it and she ground her pussy into
my face. I worked another finger into her ass and her mouth went
into high gear on my cock. Say what you like about anal sex; Cathy
gives the best head I've ever had.
Her pussy was wet and slippery, but no matter how I pleaded,
she wouldn't let me slide my cock in her ass.
"You saw that guy. I'm nowhere near that big."
"It'll hurt."
"I'll be gentle. I promise. If it hurts, I'll stop."
"No, please, Doug. Please." She redoubled her efforts on my
cock, her finger twirling in my asshole. I worked both fingers as
deep as I could in her ass and concentrated on getting her off as
hard as possible.
"Stop," she said.
"What?"
"You're doing that on purpose. You never use two fingers."
"They fit. That's how big my cock is."
"No. Just no."
"But you like my fingers..."
Some guys I know would force her. After all, if she likes two
fingers, she's gonna like your cock, right? But I'm not that kind
of guy. Besides, even a finger in the ass hurts if you fight it.
You've got to open up and relax or it's painful.
"Doug, you're not mad at me, are you?"
"I just really want to do it, that's all. I'll do whatever
you want to do."
"I'm sorry. I'm just scared."
"It's ok, honey."
She swung around and kissed my mouth. "Come on my face," she
said. "You like that."
It's true. Watching my come dribble off her lips, it was hard
to stay angry.


The following Friday, Cathy called me at work and invited me
over. "Donna and Sherry are away. We'll have the place to
ourselves."
So, at 7:00, I found myself ringing her doorbell, a bag of
take out Chinese food steaming in my hands. She met me wearing a
tight pair of jeans and a white silk camisole I'd bought her.
I should describe Cathy so you'll know what looking at her did
to me. We're both in our late 20's. Cathy is about 5' 6" and
slim. She has dark brown hair, so dark it's almost black, and
really small breasts, which make her self-conscious. "I'll bet you
never went out with a girl as flat as me," she once said. She
never believed that it didn't matter.
But it doesn't. I'm an ass man, and her ass is pure poetry.
Two firm cheeks, long legs, and a pussy mound that juts proudly
out. Dark, dark pussy hair and a clit that, when it's erect,
sticks out of her pubic hair. In jeans, I come near creaming just
watching her walk. And she knows it. She loves camisoles because
she thinks they hide the fact that she's flat. So, jeans and a
camisole meant Cathy was feeling randy tonight.
She kissed me and locked the door behind me. "Put that away,"
she said. "We're not hungry."
"Oh, I could eat something," I told her. She laughed and led
me into the living room.
She had put a bunch of pillows on the floor and set up the
VCR. She turned off all the lights except for one blue light. We
both like blue light because it's real "night time" illumination
instead of red, which is kind of tacky. Anyway, she put her hands
on my head and drew me to her. She kissed me, thrusting her tongue
between my lips, while her pussy ground against me.
"Let's put on the movie," she said. When she started it, I
was surprised to see it was the same movie from the week before.
And it was cued to the ass-fucking scene. She stripped my pants
off and, licking my belly, dropped to her knees and took my cock
into her mouth. I stroked her hair, feeling my balls tingle. God,
the girl loved to suck dick.

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"Sit down," she said, "I bought you a present."
I sat beside her, while she reached under the couch.
"K-Y jelly?" I said.
"You don't like it," she said, sounding hurt.
"No, sweet. I'm surprised is all. You know what you use it
for, right?"
"That's why I bought it. All week I kept thinking that if she
could do it," nodding toward the VCR, "so could I. But go slow,
ok?"
I stroked her hair and kissed her lips, nose, both eyes. "I
promise. If it hurts, just say so and I'll stop."
"You want me to suck you off first. You know, so you won't
be so hot?"
"I think I can handle it." What can you say about a woman
like that?
I drew her to me and slid her jeans to her knees. Her clit,
when I touched it, was stiff and her pussy was dripping wet. I
slid my finger up and down the slit. Cathy moaned and bobbed her
hips in time to my finger.
"You're so sweet to do this," I said.
"I want you to be happy," she said.
"You make me happy."
I slid her pants all the way off. I kissed her breasts
through the camisole, pinching the nipples between my lips. I
lifted it and licked her belly, following the faint dark line down
to her mound.
I laid her back and, cupping her ass in my hands, began to
lick her. Cathy usually has several orgasms to my one and i wanted
her as relaxed as possible. I slid one finger in her pussy, in and
out until it was slick with her juices, and then touched her
asshole. She jumped.
"I'm sorry," she said, "I'm just nervous."
"Not to worry, I'm here." I spread her cheeks slightly and
slid my finger just into the opening. Leaving it there, I licked
her clit, slowly. Her pussy smell got stronger and my mouth got
wetter and wetter. She started to clench her ass cheeks on my
finger.
I worked the finger deeper into her ass, past the muscle. I
slid it back and forth in time to my tongue. She began to buck.
"Oh Doug. Doug..." she whispered. Her cheeks grabbed my
finger so tight I couldn't have pulled it out and she rocked up and
down on the finger as I licked the tip of her clit. She sighed,
froze, and relaxed.
"Slip it out," she whispered and I started to curse myself.
Now that she had come, she was going to regret her offer.
"You don't want to..."
"No Doug," she said. "Please. I want you to."
I put some jelly on my finger and touched her hole. She
jumped. "It's cold."
"Not for long." i slid it all over the hole, then pushed my
finger inside. Lubricated by the K-Y and by our previous playing,
it slipped deep inside.
I took it out and put some K-Y on the tip of my cock. I put
her on her side and, using my hands to open her cheeks, brought my
cock to touch her hole. She shivered and pushed back on my cock.
It took a little working, but the head of my cock slipped into
her ass. I stopped to let her get used to the feel, then spreading
her cheeks wider, slid my cock in deeper. It hit the muscle and
she jumped.
"It hurts," she whispered.
"Just relax. I'm not going any further. Just relax and get
used to the feeling."
I stroked her side, then her belly. I kissed her neck and she
arched. "Mmm," she said.
I rubbed one hand against her pussy mound. She raised one leg
slightly, and I slid a finger against her slit. "No hurry," I told
her. "We've got all night."
"Deeper," she commanded.
I slid my cock deeper in her ass. She gasped, then I popped
the ring her ass muscle and my cock slid in. In. I was in my
honey's ass. The thought nearly made me cream.
"I'll wait," I said. "Just relax and it'll be fine."
She rocked slowly back and forth, my cock sliding in and out.
"Don't move," she said, "I want to try this."
She curled up, making her ass open and grab my cock. Her
cheeks touched my body. "That's it," I whispered. "That's as far
as it goes."
"Good," she said. Her voice had that faraway sound it
sometimes gets when she's really into her own pleasure. She opened
her legs and put one leg behind me. It made her pussy open up and
let her use her leg to lift herself on and off my cock. Again and
again she lifted, each time getting a little higher. Finally, she
lifted so high, my cock slipped out of her.
"Oh," she said. "Wait." She reached under and pointed my
cock at her hole. With a swift motion, she sat on it. "Whew!" she
said.
She started rocking on my cock, squeezing her ass cheeks. Her
breath started to come ragged and she slipped one finger to her
pussy. "Doug," she whispered, "do it, fuck my ass."
I started rocking in time to her own rhythm. God, she was
tight. I could almost not move anyway, and when she squeezed, it
nearly stopped me cold. Her finger twirled around her pussy and
her rocking started to get more spasmodic.
"Come," she whispered, "oh come in my ass."
"I will. I'll come with you," I said, kissing her neck.
"Yes...now," she said, each word coming slow and distinct.
She fingered herself furiously and her hips rocking into mine got
faster and faster. "Doug...I'm...going...to..." She squeezed my
cock so hard I froze, the come beginning to explode in my
testicles. "...come!"
With a violent shudder, she pushed back on my cock. Her
cheeks suqeezed and squeezed. Her body shuddered with wave after
wave of coming. My own orgasm started to rise and I was blind with
frenzy, pumping her her ass again and again. With a final thrust,
my come pumped deep in her asshole, again and again. The force was
strong enough, I felt it shoot back against me, leaking around my
cock out of her asshole.
We collapsed that way, my cock throbbing and her cheeks
clenching and unclenching for a long time. We both shivered as the
waves of our coming subsided.
Finally, it was over. She twisted, and my cock slid out of
her ass, followed by dripping come and K-Y.
"That was nice," she said. "It really was."
"I'm glad. I loved it. Did it hurt?"
She sat up. "Yes," she said, smiling. "Let's eat and then
you can make it up to me."