First In: Femdom Stories of First-time Strap-on Sex (5 page)

"You're not having second thoughts, are you?" she
purred wickedly. "Come on, babe... you know you want it."

Did I? I wasn't sure, but I did know I couldn't resist it.
The taste of her musky ass filled my mouth; with each stroke of my tongue my
cock had throbbed harder, my lust for her tight virgin asshole growing. I
locked eyes with my girlfriend as I glorped lube out onto my fingers and began
to massage it into her asshole.

She was snug, even with the long strokes of my tongue; by
the end there, my tongue had been deep into her back door. But just one finger
made her gasp, and the snug cinch of the sphincter around my middle finger sent
a wave of hot desire through my body; Christ, I wanted to fuck Carrie's ass so
motherfucking bad...

I withdrew my finger.

"I can't," I said.

"Is it the music?" she asked. "I've got David
Bowie--"

"No, I just can't," I said.

"Can't?" pouted Carrie. "But my ass, Jack...
my virgin tight ass..." she wriggled her perfect apple cheeks back and
forth, clenching, releasing, slipping one middle finger down to caress her
crack; then she whimpered as she began fingerfucking her own ass, and --

"Fuck it," I said, and lurched forward.

"My sentiments exactly," said Carrie, letting me
nudge her finger out of the way to replace it with my own, rubber-clad, slick
with lube, gently working her open to be quickly replaced by a second, which
made her gasp and hiss and whimper, rocking her hips as she pushed herself onto
me.

"Cock, baby," she moaned softly. "I want your
cock."

      "We're supposed to go
slow."

"Then I want your cock slowly."

"You're getting it." It wasn't so much that I
worried about hurting my girlfriend -- I did, but then Carrie was very much
capable of letting me know if something didn't feel right. Quite the contrary;
I worried -- no, best not to think about that now.

I worked in a third finger, and Carrie pressed back onto my
hand, sliding rhythmically back and forth like she was giving a lap dance. Her
muscles clenched tight and I let her relax as I worked all three fingers in
deeply, till they formed a little heart-shape, holding her asshole open
stretched and eager.

"I think I'm ready," she said. "I want your
cock."

"Do you want a condom?"

She made a disdainful noise and a sour face. "Fuck no.
We're tested, remember?"

"Wouldn't it be smoother?"

"Than your cock? I don't think so," she said.
Then, deep, hot in a low, sensuous purr: "I want your cock naked inside
me, Jack... put it in already, will you?"

I leaned firmly forward. My cock, still wet from her spit,
slid easily into my grasp and as my fingers went softly slurping out, I felt
the snugness of her asshole up against my naked cockhead.

"Breath in deep, and then--FUCK!"

She gave a little push back onto me, whimpering. My cockhead
popped in, and she made a bestial sound as she pushed her snug ass slowly down
my shaft, looking over her shoulder to make sure I saw the rapturous expression
on her face as she took me into her virgin
hole.          "You were
saying?" she asked me.

My eyes rolled back into my head. I fumbled the wet rubber
glove off of my hand and threw it on the floor. I let her snuggle down onto me,
and gradually acclimate herself to the bulk in her hole. She started
clenching-releasing, clenching-releasing, each time relaxing more. I felt a
quick rubbing and realized she was stroking her clit fervently, 
periodically dipping two fingers into her cunt. When she did that I could feel
her ass tighten, even feel the pressure, a little, of her fingertips against my
cock.

"Bolero" rose in mounting rhythmic fuck-sounds;
things were getting serious.

"All right," she said softly. "Now fuck
me."

I started slowly, gradually, working in and out inch by
inch, shocked at how different ass felt than a cunt. As I came partway out, she
smeared lube on me with the hand that wasn't on her pussy. Then,
"Harder," she begged, and I gave it my best, thrusting deeper until
her asshole was around the very base of my cockshaft, then drawing back until I
almost slipped out. I leaned forward, pinning her down so I could get more
leverage with my hips. I started thrusting, slowly then quicker, quicker,
quicker, as Carrie squirmed under me, the thrusts getting easier with each
stroke. I was close -- fucking close, fast as hell since her ass was so tight
and the turn-on was tangible.

"Um -- I'm ready -- you want it --"

"Yeah, yeah, up my ass," she said irritably, breathlessly.
"Come in my ass. Wait -- not -- not yet --"

She rubbed harder, almost violently; I struggled to hold
still while she went at it. Then she let out a low keening wail and her ass
tightened rhythmically; she gave a yelp of surprise as my cock popped smoothly
out.

"Back in," she pleaded, and I worked it back in.
Her ass was still spasming as I drove deep inside her and started thrusting. In
another moment I started to come, giving a girly little whimper as I gripped
her hair and pounded her ass. Borne into the bed by my weight, Carrie lifted
her ass to meet my thrusts. Her ass went slick with my semen.
"Bolero" screamed its final whining cacophony, yowling to its violent
end.

I grunted. I finished. Her cunt and ass were still
twitching, little "Oooh" sounds escaping her lips as she felt the
afterglow of her orgasm. After a time I rolled off of her, lay on my back
panting. Affectionately, she snuggled on top of me.

The CD started again: Bum, da da da, ba da da da da da bum
da da da... Christ, was Carrie really going to tell people for the rest of her
life that she lost her anal virginity to the strains of motherfucking
"Bolero"? Adding insult to perversion, though I admitted the rhythm
was mildly soothing, however much my ass-cheeks were clenching.

She must have read worry on my face; she gave a broad grin,
giggling evilly.

"Oh, don't be nervous, baby... it was my first time,
and tomorrow it'll be your first time." She laughed.

"Tomorrow? I thought we said 'some time.'"

Carrie gave me her best innocent face. "Come on, baby,
you're not going to make me wait, are you? I didn't make you wait... well, not
very long, at least. Please?"

"All right," I said. "I guess so. If you're
sure it won't--"

"No, it doesn't hurt, baby. And you know you want it.
Or at least you know you're curious about it."

I shrugged, trying to play cool.

"Don't give me that," said Carrie, and kissed my
chest wetly, with lots of tongue. "Of course," she breathed, "I
would never want to do anything to you that you weren't totally into. You can
always puss out... and go back on your word... and get your girlfriend to give
up her ass, but be chicken to --"

"Forget it," I said. "I'll make good on our
bargain."

Carrie gave her most mischievous grin, her whole body seeming
to hum with excitement from the prospect -- or maybe it was that she just got
fucked in the ass.

"Would you... show me?" I asked.

Carrie looked surprised.

"I mean, you already bought it, right?"

"Yeah, but I thought... I figured we'd wait until..."

"Please? I'm just curious."

"Sure," she said. "That's hot. You don't
want..."

"Tonight? No. I just... I'd just like to see it."

"Maybe suck it a little?"

"Suck it? That's weird." I grinned.

"Men," she said, smiling. "All right. Fashion
show. You wait right here, baby." She got out of bed.

Carrie's campus apartment has shared baths between each pair
of bedrooms. She seized a black plastic bag with a dog-collar logo from the
decrepit particleboard laminate wardrobe, and paused at the door.

"Don't go anywhere," she said, and shut the door
behind her.

I rolled over onto my belly, felt immediately self-conscious
-- since that put my ass in a direct line-of-sight from the bathroom door. I
rolled onto my side. My cock ached from the fuck; Carrie's asshole was tight,
and the heat of my first anal fuck was as hot as the excitement of taking
Carrie's anal virginity.

But with Carrie, nothing is ever simple; what's more, she's
fantastically persuasive. When I'd made my thoughts clear -- that anal sex was
fucking hot, and I couldn't wait to do it -- she conceived of a bargain. She'd
never done it before, but she would. I could be the man to initiate her into
the pleasures of back door love. If I'd offer her the same consideration.

Oh, don't get me wrong. I played hard to get. I blushed,
hemmed and hawed, wasn't sure I could do that -- still wasn't. But the night
she suggested it, fuck! how my cock swelled and throbbed.

Ever since then -- three weeks, now, long enough for her to
buy a strap-on and me to read three neurotic books on safety, tips, guidelines
and precautious -- I'd been half-obsessed, careening wildly between imagining
Carrie's tight ass snugged around my slick cock, and her cock, buried deep --
motherfucker, I couldn't even think about it without popping a hard-on, which I
did, and before I knew it I was stroking -- my cock wet with lube and Carrie's
ass, my ass feeling suddenly hungry. My cock was sore, the tip stung slightly,
and still I fucking stroked it, reaching back to touch my own firm cheeks --
good God, was I a pervert?

"Baby?"

"Patience!" she cried back. "This thing's not
sweats and a god damn T-shirt, Jackie Boy, and it's not attached to me!"

"Sorry," I said meekly.

I went back to stroking gently, almost hyperventilating. I'd
decided: Why put off until tomorrow... my cheeks clenched. I squirted lube and
reached back there.

I was tight -- tighter than Carrie. Two fingers took some
work to get in. Three was almost impossible at first. Four -- well, once I'd
done three, four seemed like an awesome idea, and then I was fucking, wetly,
eyes rolling back into my head. I was clean, I'd seen to that, knowing this was
a possibility -- since my vivid fantasies had me doing just this, fucking
Carrie's ass and then... oh fuck. I thrust fingers deeper, pumped my cock, felt
my asshole relaxing...

"Bolero" was pulsing louder.

"Baby?"

"God damn buckles! Just a minute."

I watched, panting and stroking, as I waited for the door to
open. The CD had started over before it did; she sashayed out adorned and
gussied; I stared gape-mouthed as her eyes flickered over my lube-slick cock.
I'd slid my fingers out of my ass, and was caressing my prick with both hands.

"You like, I guess," she said.

"Those boots!"

"They match the harness," said Carrie.

"Expensive?"

"I hope my Dad doesn't check his credit card statement
this month. I'm just saying."

Her hand went gliding slowly down her body, fingers nuzzling
her tits, her belly, then circling the big flesh-colored cock jutting out of
her harness.

"It looks so real," I said, sitting up on the edge
of the bed.

She stroked her cock as she made her way across the bedroom,
spike-heeled patent-leather knee-high monstrosities spearing lube packets and
discarded comic books. "I thought... you know, smooth, purple or
something, that'll be less, er, real. But then... you know, there's something
hot about how it looks like a real cock. Isn't that kind of hot, Jackie?
Jackie? Oh, my..."

My mouth engulfed the head of her cock and I felt a powerful
charge of excitement go through me. Oh, fuck, I was actually going to do this.

I took her cock down easily to the back of my throat, my
head bobbing up and down as she ground her hips forward. It wasn't just the
anal sex books I'd learned from; never having seen her strap-on before, I had
already gauged the angle of the base. Line drawings can be so helpful. I
calculated its proximity to Carrie's clit, which, let's be frank, I knew the
location of pretty god damn well. I started sucking, hand around the lower
portion of the shaft, got the base of the dildo tight against Carrie's clit,
and -- drunken sailors never moaned so loud when street whores' throats went
tight around their cockshafts.

I felt wires, but didn't think twice about them; I was too
fixated on sucking Carrie's strap-on. I started working fervently, my hand
around Carrie's firm body, gripping that perfect ass I'd just fucked and
pulling it hard against me cock down my throat. She held me, her crotch against
my face, her hands gripping my hair as I struggled to keep her down as deep
inside me as I could.

"I've been practicing," I rasped when I came up
for air, which was not for a good long time.

"You little whore," she said. "You've been
playing hard to get."

Don't make me beg, I thought. I'll puss out.

But she didn't she just let me suck and suck, my own cock
throbbing, until I looked up at her with big wide eyes and she gave me a little
push onto the bed.