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First Time Anal
by Druid Knight (druidtx001@yahoo.com)

***

A girl's refusal to give up her anal virginity is 
"kidnapped" by her long-time lover, who binds her and 
teases her into submission until she willingly grants 
him entrance to her final untouched realms. And, she 
finds out she loves it. (MF-teens, reluc, anal, bd, 
rom)

***

My girlfriend Cathy had been promising me her anal 
cherry for months. But every time I'd get close to 
sticking my hard cock into her tight, 16-year-old ass, 
she'd freak out and stop me.

I decided, finally, that I wasn't going to take no for 
an answer any more. I wasn't planning to rape her, mind 
you. I just made up my mind to get her so turned on 
she'd consent to anything and everything I wanted.

A little about us: I was 19 at the time, 6'5" tall, 
weighing in at 250 pounds. My job loading and unloading 
trucks, combined with frequent visits to the weight 
room at the local YMCA, kept my body lean and hard. I 
kept my balls shaved and my pubic bush trimmed, which 
made my 8-inch long, very fat cock appear even more 
imposing.

Cathy, as I said, was 16 at the time, though she'd lied 
to me when we started going out and I though she was at 
least a year older. Her parents knew how old I was, 
though, and didn't seem to mind. There was no way they 
could have thought we weren't sexually active and they 
never caused any problems about a supposed adult 
fucking the hell out of their little girl.

She stood about 5'4" and weighed about 125. She had red 
hair (natural) and I'd convinced her to keep her pussy 
lips shaved and her bush trimmed into a neat little 
arrow, pointing straight down to her clit. Small 
(probably 34B) tits, combined with her shaved and 
trimmed pubes, made her look even younger than her 16 
years.

I waited until a weekend I knew her parents were going 
to be out of town. I booked a room at a sleazy adult 
motel in a nearby town, knowing from experience the 
beds there were equipped with everything I needed. 
Namely, a way to securely tie her to the bed and have 
my way with her tight young body.

I picked her up for our regular weekend date Saturday 
afternoon. She'd expected an afternoon of hot sex in 
various locations around her parents home. Hell, we'd 
done it before, me taking her on her bed, her parent's 
bed, spread out on the living room floor or couch and 
even, once, tied face down and bent over the dining 
room table.

I had other things in mind today, though. As soon as I 
got her in the car, I secured her wrists behind her 
back with a length of soft rope. She got that look, the 
one she got when she was turned on. Her eyes started to 
glaze over and I could see the tips of her tiny nipples 
poking through the material of her bra and the tight t-
shirt she wore. I pressed her back in the seat, secured 
the seatbelt across her chest and pulled it tight. To 
top it off, I tied a bandana around her head as a 
blindfold, shutting her off from the outside world.

"What are you doing?" she asked as we pulled away from 
the curb. "Where are we going?"

"Quiet," I said. "It's a surprise."

In addition to the t-shirt that was doing little to 
hide her hard nipples, she was wearing a short denim 
skirt and sandals. I decided it was time to start 
teasing her in preparation for the main event.

I placed my hand on her thigh, gently stroking with 
just the tips of my fingers from her left knee, up to 
just below the hem of her short skirt. I felt her leg 
start to tremble, the muscles of her thigh tensing and 
releasing as she tried to hump her ass further down in 
the seat to get my fingers further under her skirt.

Every time she got close, however, I slid my hand back 
down her leg. Within 10 minutes, about halfway to our 
destination, she was panting in her seat, humping her 
ass against the seat, trying to get some pressure on 
her hot little pussy. Every few second, I'd let my hand 
trail up her body to pinch and pull on her hard, ultra-
sensitive nipples before slipping my hand back down her 
body.

At one point, I pulled her skirt up to expose a very 
revealing pair of sheer white panties. The crotch, 
soaked with her arousal, did little to hide her shaved 
lips. I pulled the material tighter, stretching the 
gusset until it was nestled in between the folds her of 
teenage pussy. It was a good thing I had her 
blindfolded. That way, she couldn't see the lustful 
gazes of the truckers we passed.

Cathy was about as turned on as I'd ever seen her, 
humping her hips against the air, straining at the 
seatbelt, trying anything she could to increase the 
stimulation of her over-heated flesh. Finally, as we 
pulled in to the rough gravel parking lot of the motel, 
I lodged my finger between the lips of her pussy, 
pressing hard against her clit.

She almost came unglued as the motion of the car over 
the ruts and groves in the parking lot vibrated my 
finger against her clit. But she made the mistake of 
telling me she was getting close. I paid special 
attention to her as she moved to within a fraction of 
an inch of orgasm. I pulled my finger away just before 
she could peak, leaving her gasping in arousal as I 
pulled up in front of the motel office.

"We're here," I said. "Be right back."

I shut off the car and left her, exposed and 
frustrated, bound and blindfolded, as I entered the 
office to pay for our room. Fortunately, I'd locked the 
car. When I returned not five minutes later, there was 
an older guy standing outside the passenger window, 
staring openly at my half-naked girlfriend. The 
cleaning cart parked nearby told me he was the motel 
janitor. I could clearly see his hard cock straining as 
he fisted it through the material of his dirty 
trousers.

I walked around to the driver's side door, grinned at 
him with a, 'That's mine and you can't touch' look in 
my eyes. I climbed in, started the car and began 
hunting for our room.

I parked in front and, again, left Cathy tied in the 
front seat while I carried some stuff in from the trunk 
and readied the room and, particularly, the bed. More 
than half expecting the janitor to come around for 
another look, I pulled her t-shirt up and over her 
head, leaving it wrapped around the back of her neck. I 
also pulled the cups of her bra up and off her tits. 

I took one last look through the passenger window as I 
passed. There was my little darling, naked tits clearly 
on display with her panties pulled far enough between 
the lips of her pussy she might as well have been not 
wearing them at all.

It took me about ten minutes to attach the restraints 
to the bed frame and set up a set of video cameras I 
hoped would be enough to capture her anal deflowering 
for all time. I turned the cameras on, surveyed the 
room one last time, and went outside to retrieve my 
prize. 

As I'd expected, the janitor was back at the passenger 
window, staring at Cathy. This time, however, he felt 
bolder, I guess. He'd opened the fly of his pants and 
was openly stroking his wrinkled cock while watching my 
girlfriend.

I chased him away again, promising that if I saw him 
one more time, no one would ever find the body. 
Cursing, he shuffled off, intimidated by my youth and 
size. I secretly loved the fact that he'd been staring 
at my half-naked girlfriend. I was sure she'd love it 
too. She was something of an exhibitionist and, as I 
opened the car door and began freeing her from the seat 
belt, I told her exactly what had been going on.

"You mean the janitor was staring at me and you caught 
him jerking off?" she asked as I led her into the room. 

I hadn't bothered to pull her shirt or skirt down. I 
caught, out of the corner of my eye, the old janitor 
once again peeking around the corner of the block of 
rooms, staring at Cathy's mostly-nude body. I chose to 
ignore him. But I did tell Cathy he was watching again.

"God, that makes me so hot," she said as I closed the 
door behind us. "Fuck me. Right here and now."

I'd set up the cameras to pretty much cover the entire 
room: Three showing close-ups of the bed from each side 
and from the end, one attached to the mirrored head 
board with a wide shot looking down and another wide 
shot, covering as much of the room as possible. I 
stopped Cathy in front of this last camera and pushed 
her to her knees in front of me.

I was so turned on. My cock was rock hard and aching 
inside my jeans. I had to have some relief now so I 
could control myself during the rest of the afternoon. 
I wanted to tease Cathy until she was screaming and 
begging me to fuck her ass. I knew that, if I didn't 
blow a load right away, I'd loose my self-control and 
fuck her before she was ready. Or, should I say, before 
I decided she was ready.

I let my jeans drop to the floor and stepped out of 
them, my hard cock slapping against my stomach as I set 
it free. I pressed the head against her lips, smearing 
them with precum, before I pushed it into her mouth and 
down her throat. I buried about half of my cock in her 
mouth on the first thrust. She moaned as my shaft 
stretched her lips and the head speared into the top of 
her throat.

I pulled back until just the head remained trapped by 
her lips. I just about came as she swirled her tongue 
around the crown, sucking the precum from my piss slit. 
I exerted what control I had at the moment to stop the 
rising orgasm and keep myself from painting her tonsils 
too soon. I wanted a little throat fucking on film 
before coating her face.

I wrapped my left hand in her hair and started slowly 
stroking her mouth. She was moaning like crazy. My cock 
went deeper and deeper into her oral cavity until, 
finally, I felt her lips wrapped around the base of my 
shaft. She started swallowing with the head buried deep 
in her gullet, her throat muscles massaging the head 
and shaft of my rampant cock.

I deep-stroked her throat a few times. I loved watching 
her lips stretch around the base of my shaft each time 
I bottomed out. In less than five minutes, though, I 
could feel myself reaching the point of no return.

Cathy loved swallowing my cum. Depending on how aroused 
she was at the time, I'd seen her cum just from feeling 
the first shot of cum splash against the back of her 
mouth. I didn't want to take any chances on her getting 
her nut too soon. And I wanted to cover her face in cum 
for the camera.

I pulled my cock away just as I felt my first orgasm of 
the day start. She moaned as my dick head popped free 
from her sucking mouth. She moaned again, louder, as 
the first shot of cum rocketed from the tip of my cock 
to coat her face from forehead to chin.

Four more shots of cum later, Cathy's face was covered 
in my jism. It was dripping from her cheeks and chin 
and collecting in her ears. The blindfold had five 
distinct strings of cum clinging to it and soaking in 
to the material.

"Why didn't you cum in my mouth?" she asked me. "You 
know I can cum from you shooting in my mouth?"

"I know," I said, as I pulled her to her feet and led 
her toward the bed. "I'm going to untie you for a 
minute. Don't touch the blindfold for now."

I unbound her wrists and rubbed the flesh to restore 
circulation to her hands. I finished stripping her, 
pulling the shirt and bra down her arms before removing 
her skirt and, finally, her soaking wet panties. Her 
sandals came last, leaving her naked except for the 
blindfold.

I led her to the bed and stretched her out on the 
mattress. I straddled her naked body, my semi-hard cock 
resting between her tiny tits. I pulled first her left 
arm then her right up and over her head and secured 
them by the wrists using the restraints I'd placed 
earlier. I slid down her body and repeated the actions 
with her ankles, first left, and then right, I pulled 
her body taught until she was stretched between the 
head and foot of the bed.

I climbed off the bed and surveyed my handiwork. There 
was my love, Cathy, bound hand a foot. Her tits were 
stretched so tight they hardly appeared to be there, 
just the slightest of mounds on her chest, capped with 
rock-hard nipples pointed at the ceiling. Her fiery red 
bush was wet and matted from her prolonged arousal. The 
labia were swollen and appeared as red as her pubic 
hair. Her moisture was literally dripping from the wide 
spread lips. I could see her clitoris, standing proud 
and swollen at the top of her slit.

And, just peaking out below it all, my prize - her 
virgin asshole. Light brown with just a hint of red 
hair dusting the rim, my gaze focused on her back door 
as I explained what was going to happen.

I pulled a chair up next to the bed and sat down, 
taking my hard cock in my hand and stroking lightly as 
I spoke.

"Cath, I love you," I started. "And I've loved you and 
you've loved me just about every way we could. Except 
one."

I watched as her body tensed. She knew what I was 
talking about.

"I'm going to fuck you in the ass today," I said.

She started to protest. But I cut her off.

"I'm not going to force it," I continued. "This isn't 
going to be a rape. You are going to beg me to fuck you 
in the ass before this day is over. You're going to 
remain tied up and I'm going to tease your body until 
you do. I'm not going to allow you to cum, until you 
do. 

"Once you do, once you beg me to take your anal cherry, 
I promise you that you'll have the best orgasm you've 
ever had, bar none. I'm going to bury my cock in your 
hot, tight ass and fill you with my hot, steaming seed 
until it flows out of you like a river. And if, after 
I've done that, you didn't like it, I'll never ask you 
to do it again."

I watched her. Her nipples had gone completely slack 
when I'd told her what I was going to do. But, as I'd 
continued my explanation, they grew again until they 
were as hard as before and again pointing toward the 
sky.

The talking done, I moved to the side of the bed and 
started slowly stroking her body. I ran the tips of my 
fingers over her arms and around her face, tracing the 
shape of her lips before sliding down over her chin to 
caress her neck. I ran my hands down over her chest, 
bypassing her nipples, and down to lightly tickle her 
stomach.

I traced my way through her red bush and down her legs, 
again bypassing her dripping pussy. It took me about 10 
minutes total to completely stroke every inch of her 
skin. By the time I reached her feet, she was moaning 
again and thrusting her hips, fucking air. 

I reversed my stroking, moving slowly back up her body, 
again bypassing the most sensitive areas, until I once 
again reached her mouth. I traced her lips with my 
fingers, then leaned in and replaced my fingers with my 
lips and tongue.

I started kissing and licking my way down her body, 
bathing her super-heated flesh with my tongue and lips, 
making her skin tingle and moans escape her body as I 
sucked and nibbled at every inch of her skin. I suckled 
each nipple briefly, making them harder and wet with my 
saliva. I then continued licking and biting my way down 
her body.

After 45 minutes, I'd completely covered her body with 
fingers and tongue twice. I had her stretched as tight 
as a guitar string. Every muscle in her body was 
straining as she thrashed about on the bed, pulling at 
her bonds, trying to get her legs together to put even 
the slightest pressure on her up-to-now neglected 
pussy.

"Fuck me," she gasped. "Stick your big hard cock in my 
pussy. I can't take your cock in my tiny ass. Please, 
fuck my pussy."

I decided it was time to ramp it up to the next level. 
Leaving the straps wrapped around her ankles, I 
released the ends of the restraints from the foot of 
the bed. I stretched her legs, one at a time, up and 
over her head, securing them next to her hands. Her 
beautiful pussy and tight little ass were now pointed 
directly at the mirror on the ceiling above the bed.

I grabbed a couple of pillows off the other bed and 
placed them under her, supporting her ass and hips, 
taking some of the strain off her lower back. I then 
began teasing her again, running my lips, tongue and 
fingers around her ass, stroking her sides. Eventually, 
it was time to go for broke.

I started tonguing her pussy. I watched carefully her 
state of arousal. I stopped each time I thought she was 
getting too close to cumming. I brought her to the edge 
five, ten, fifteen times, backing away each time to 
leave her thrusting her hips, humping at my face which 
was no longer between her thighs.

During this lingual assault, I dipped occasionally into 
her tight ass, teasing the tip of my tongue around her 
sphincter; lubricating it and teasing the muscles open 
slowly. I worked the tip of a finger gently in and out 
of her clenching ass until I had her moaning and 
panting, again nearing orgasm.

I was determined I was going to pop her anal cherry 
today. I was further determined she was going to love 
it, cumming harder than she ever had in her life, and 
was going to become a certified ass fuck lover, begging 
me to fuck her ass for the rest of our lives together. 
And I could tell from her responses that she was 
getting closer to where I wanted her to be.

I could tell from her body language, she was again 
approaching orgasm, this time from my attentions to her 
ass. Again, just as she started to peak, I ceased all 
stimulation. I left her, hanging on the edge yet again, 
thrusting at the air.

"Fuck me!" she cried. "God, please fuck me!"

"Where?" I asked, running my hand gently through her 
sweat-soaked hair.

"Fuck me!"

"Where?"

"Fuck me!" she moaned. "Fuck... Fuck my... ASS!"

There it was. 

"Fuck me in the ass," she cried. "Stick your big, hard 
cock in my tiny little asshole, you bastard! Take my 
ass cherry! Make me your ass whore!"

I picked up a bottle of lube from the bedside table. 
Generously coating my fingers, I squeezed a large 
dollop onto her steaming asshole. She cringed away 
briefly from the cold gel, but came back quickly as I 
started probing her back door, working the lube inside.

"Oh, God, yes!" she said. "Stick your fingers in my 
ass! Get me loose and slippery for your cock."

As I lubed up her ass with one hand, I spread a 
generous amount around the head and shaft of my rock-
hard cock. I positioned myself between her upturned 
legs and started teasing the tip of her clit bud with 
my tongue. I wanted to give her the massive orgasm I'd 
promised.

I planned to impale her with my cock just as her orgasm 
peaked. Cathy was thrashing about on the bed, pushing 
her hips up, and pressing her pussy against my tongue 
and my fingers deeper into her ass. I had her open; her 
ass muscles relaxed enough for penetration. Still I 
teased my tongue around her clit, bringing her closer 
and closer to the orgasm I'd denied her for more than 
an hour.

I felt her peak, her ass clenching around my finger.

"I'm going to cum!" she announced. "What ever you do, 
don't stop again. Please! Don't stop again! Let me 
cum!"

Instead of stopping, I replaced my tongue on her clit 
with my fingers, playing her like a violin as I 
repositioned myself with the head of my cock poised at 
her slick asshole. With my free hand, I reached down 
and finally removed the blindfold. She blinked as the 
light of the room hit her eyes, her first vision the 
mirror on the ceiling, before her eyes settled down on 
my face.

I looked directly in her eyes, silently questioning. 
She nodded, biting her lower lip as the head of my cock 
began probing at her ass. Then, her eyes rolled back in 
her head as her orgasm overtook her. All the muscles in 
her lower body tightened then relaxed, including her 
ass. Her sphincter opened slightly and the head of my 
cock surged into her bowels.

Her eyes flew open as the first two inches of my cock 
came to rest inside her virgin ass. She cried out, 
first in pain at the sudden penetration, then in lust 
as she adjusted quickly to the intrusion.

"God, that feels different," she moaned. "Give me a 
second."

I continued strumming the bud of her clit. I felt her 
climbing the walls of orgasm again, this time with half 
of my cock buried in her ass.

"Fuck me," she started moaning. "Fuck me, fuck me, 
fuckmefuckmefuckme."

I continued pressing forward until I was buried 
completely in her ass. Cathy was cumming almost 
constantly now as I slid out and set a slow, gentle 
rhythm, my fingers constantly playing across her clit 
as I plumbed the depths of her ass.

Louder now: "Fuckmefuckmefuckmefuckme."

She was chanting like it was her own personal mantra.

"Fuck me, fuck me fuck me fuckmefuckmefuckme!"

I picked up speed as her ass muscles relaxed more and 
more. Soon, I was sliding the entire 8-inches of cock 
from tip to base in and out of her ass as she chanted: 
"Fuckmefuckmefuckmefuckme!"

"I'm cumming again," she cried. "Cum with me! Cum in my 
tight, teenage ass! Fill may ass with your hot cum! 
Give me your cum! Cum! Cum! Cum"

Her mantra changed as I picked up speed, pounding her 
into the mattress. She'd cry out every few seconds as 
another orgasm wracked her body.

Finally, I couldn't take it any more. I buried my cock 
deep in her ass for the last time as I felt the cum 
rocket from my testicles, through the shaft of my cock 
and out the tip to coat her bowels.

She screamed at the top of her lungs as the first 
scalding shot of cum painted the inside of her ass.

"I feel it!" she said as my cock lurched in her ass, 
shooting a second stream of cum deep into her gut.

"I feel your cock throbbing in my ass," she said. "I 
feel hot cum shooting in my ass. God, I love it! Fuck 
my ass! Cum in my ass! Fill up my ass!"

Her final orgasm hit and it was the biggest one yet. 
Cathy's still tight ass clamped down hard on my cock, 
so hard the muscles squeezed off my semen, trapping it 
and preventing any more from shooting out of my cock. I 
thought my head was going to explode as cum backed up 
in my balls. I could feel the pressure rising until, 
finally, it became too much and burst past to clenching 
ring of her sphincter around the shaft of my cock.

Three or four shots worth of cum fired out the end of 
my cock at once in a massive spurt, filling her ass to 
overflowing. It coated her insides and I could feel the 
excess squirting out of her asshole and over the shaft 
of my cock, coating my balls in our combined juices.

Finally, Cathy collapsed on the bed, limp in her bonds, 
all but unconscious. My erection slowly subsided, my 
balls drained of every drop of cum. My limp cock 
slipped out of her asshole, followed by even more cum. 
It flowed down her back to pool on the bed.

I rolled to the side and collapsed next to my well-
fucked girlfriend. After a few minutes, I gathered the 
energy to untie her ankles and wrists, leaving the 
restraints where they were for now. I took her in my 
arms and pulled the blankets over us.

I woke a couple of hours later to the feeling of a warm 
washcloth cleaning the shaft of my cock. I looked down 
and there was Cathy. She threw the cloth aside and took 
my cock into her mouth. As my eyes focused, I 
recognized the old janitor, behind my girlfriend, 
working his cock into her from behind as she sucked me 
back to a throbbing erection.

God, I thought. I've created a monster.

Good for me!

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Kristen's collection - Directory 48