First In: Femdom Stories of First-time Strap-on Sex (13 page)

I go slowly. I want her, but I
force myself to wait, teasing her.

It isn't long before Jenny gets
impatient. "That's good, Kendra," she says. "You're ready, now.
Put it in. Put my cock inside you."

It seems too big; there's no way I
can take it. But I know that I have to.

I whimper as I push myself onto
her cockhead. The fullness of her big black cockhead is almost more than my
asshole can bear. I feel my hole stretching. I feel her cock opening me up,
punishing me as I force my way onto it.

I push myself onto her cock,
gasping in pain as my asshole is violated.

I moan wildly a moan as I finally
force myself past the cockhead. Now the huge cock is embedded in my body, and
Jenny whispers, "Shhhh," into my ear. "Stop whining and let
yourself feel the pleasure. Come on, baby. Show me how you like it."

I push myself further onto Jenny's
dick -- forcing her cock up into me until it the wider base stretches my hole
even more than the mammoth cockhead did.

I'm breathing hard, in big,
gasping shudders, whimpering, moaning.

I fuck myself onto her, picking up
speed as the agony dissipates. Jenny starts fucking me. Harder. Still harder.
My hoop earrings brush against my shoulders as I rock my head back and forth in
response to waves of pain and pleasure.

I howl as she fucks me.

Soon, Jenny's pounding her cock
into my asshole harder than I've ever fucked her -- harder than even
Mike
has fucked her, I bet. It's all I can do to hold on for dear life, digging my
fingers into the pillows.

As she slams me forward with each
thrust, my dick smacks against the sheets. Jenny reaches around me and caresses
my cock. She doesn't jerk it -- not at all. Rather, she just
teases
.

"You want that handjob I
promised you, baby? You want it while my dick's inside you?"

I nod furiously, begging her.
"Please, Mistress, please, Mistress--"

Jenny viciously digs her
fingernails in to the flesh of my cock. I moan. She doesn't jerk me off. She
just holds my cock still and pulls back again.

"Come on, baby. Fuck your
asshole onto my dick."

I obey her, with great difficulty.
I'm stuffed full, and my cock and balls hurt like hell. Nonetheless, I fuck
myself onto her cock. I can feel the cockhead hitting what must be my prostate;
little flashes of extreme pleasure blast through me as her cock hits its
deepest point inside me.

Jenny reads my thoughts.
"Feel that? Feel how good that feels? I'm hitting your G-spot, baby. My
dickhead is hitting your G-spot. Show me what a horny bitch you are. Show me
what a slut my little sissy cunt fucktoy is. Show me what a little
panty-wearing cockwhore you want me to make you. Show me how much you love
dick, Kendra. Show me how much you love to fuck."

I ride her cock desperately. I
pump myself onto her until, suddenly, white hot pain and pleasure mingle in my
tortured dick.

Hot streams of built-up cum
explode from the head of my cock as Jenny dis her fingernails deeper into my
flesh. The pressure causes pain at the jizz blasts out -- but she won't let me
stop. She hisses, "Keep going, baby. Keep fucking yourself."

I wail in pain and pleasure,
feeling the spasms of my painful orgasm as my asshole contracts around my
wife's cock.

Half of my jizz seems to have gone
into Jenny's cupped palm. While I keep fucking myself onto her cock, Jenny
shoves her cummy hand into my face. She pushes her cum-slick fingers into in my
mouth.

She doesn't have to tell me what
to do. I suck them clean.

When I'm utterly spent, I can
barely even move.

It's Jenny's turn again to take
the active role - no longer making me fuck myself onto her. Now she just wants
me to be a limp little bitch. She pulls her cock out of me and pushes my legs
up high, bending them over her shoulders.

My soft little cock sits there
underneath her gorgeous body, tucked against my belly and drizzling cum.

Jenny looks deep into my eyes and
starts to fuck me.

Panting, she asks me, "How do
you like missionary position, Kendra? We're almost like husband and wife,
huh?"

I hear the buzzing of a vibrator;
at some point Jenny has reached down and turned it on. The egg-shaped device
sits on her clitoris -- and as she fucks her cock into me, each thrusts causes
pressure against her.

Jenny looks into my eyes as she
starts pounding me viciously...fucking me harder than any guy would need to fuck
a woman to cum.

But Jenny needs to do me hard and
deep to get herself off.

It takes a long time for her to
fuck me till she cums. She's been teasing herself as well as pleasing me -- she
needs to cum
bad
. When she finally gets off, Jenny cries out in
pleasure, moaning as orgasm floods through her.

Jenny finally pulls her huge cock
out of my ass. Obediently, I help her get the harness off. She caresses my face
and smiles.

"You know what's next,"
she tells me.

I nod, shamefully.

I get out of bed and go to the
dresser.

I bring her my chastity tube

Now that my dick has been utterly
spent, I'm soft enough to put it on.

But Jenny wants to do the honors.

She makes me get on the bed and
spread out in front of her. She fits the plastic device around my cock. The
spikes don't prick me, since I’m entirely soft. But before she closes the hasp,
she makes me put my finger in the device, so I can feel how sharp they are.

"That'll be your incentive to
think like a girl," says Jenny.

She fits the tube around my cock
and closes the padlock with a click.

#

Once my cock is locked away, Jenny
breathes a sigh of relief.

I'm exhausted, but Jenny doesn't
care. She rolls onto her back and spreads her legs.

"Put on
your
harness,
Kendra. I seriously need to get fucked." She grins. "And I'm not like
you, baby. I want the
big
cock." She caresses her pussy.
"Mike's really opened me to new experiences, baby." She laughs at her
pun.

Jenny caresses my chastity-locked
penis.

"Do you think your clit could
do that?"

Eyes down, I say, "No,
Mistress."

#

I feel strangely peaceful
strapping the harness to my body and fitting the biggest of the dildos into it.
I almost feel like a girl.

Dripping sweat and exhausted, I
mount my spread wife. With the huge strap-on dildo, I penetrate her for the
first time in months. I feel that exultation of first penetration as Jenny
gasps, struggling to take it. Then I feel suddenly humiliated... it's not my
dick that's inside her.

Or is it?

I feel the base of the dildo
rubbing against my pubic bone as I fuck her. It's not an unpleasant sensation.
I feel Jenny riding my cock underneath, fucking herself up onto me as she talks
dirty, telling me all about how good this feels -- how my cock is bigger than
Mike's, all I needed to be a real man was for her to make me a girl. I feel the
escalating pleasure of dominance as I fuck Jenny harder and harder, even though
I'm seriously winded and pouring sweat.

Jenny's dirty talk really gets me
going. She coaxes me into fucking her harder.

It turns me on more and more. As I
pound her, I feel a strange, growing pain.

My cock is swelling.

I try to stop; I try to pull out.
Jenny wraps her legs around me and pulls me hard onto her. She pins me from
underneath, holding me down on top of me and working her legs so I don't have a
choice. She fucks herself up against me.

She whispers filthy words into my
ear, telling me all about how she loves getting fucked, what a man I am, how
I'm bigger than any of her boyfriends.

It turns me on more. My cock gets
half-hard. It continues to swell.

The spikes dig in.

"Please, baby," I
whimper desperately. "Please, ow, it hurts--"

Jenny laughs at me, wrapping her
legs around my ass and pulling me onto her. When I panic and try to get free, my
wife flips me hard and comes down on top of me. My cock has slipped out of her
-- my strap-on cock, that is. My boner continues to swell, and the spikes of
the chastity tube cause a screaming pain as Jenny spreads the lips of her slit
and fits them over the thick head of my strap-on cock again.

My wife moans as she fucks herself
onto me.

Arching my back, I claw the sheets
in pain.

Jenny's hot breath flows against
my neck. She growls in my ear as she rides me.

"Do you love me, baby? Do you
like this? Is this everything you've ever wanted? Did you always want this?

She pounds her body against mine,
laughing as I squeal in pain.

There are tears in my eyes as I
moan, "Yes, Mistress!"

My wife rides me harder with every
thrust.

"Come on, boy. Come over here and tell Daddy how much
you appreciate his hospitality."

I take the cigar out of my mouth and smile at him.

Lounging in the armchair, I reach down and unzip my leather
pants. I pull out my cock and start stroking it. My boy looks at the big, thick
shaft of my cock and licks his lips.

Then he goes down on his knees and plants his mouth on the
head of my cock. He takes my shaft into his mouth until the head nudges the top
of his throat. Then, without hesitating, he swallows, forcing the shaft down
his throat without even a hint of a gag reflex. That sends a shudder through my
body; I can feel my pussy aching. He starts working on my cock, sucking it like
an expert.

I don't look much like any daddy I've ever known. The tight
leather pants, big black boots and Harley Davidson T-shirt could belong to a
daddy, sure. But there's no disguising my broad hips or the way the pants hang
so low on them, revealing my flowery tattoos and my navel ring. And I haven't
strapped down my tits, which are big enough to stretch the T-shirt and, even
with a sports bra underneath, show my nipples as they get hard in response to
the sight and feel of my boy's mouth on my cock.

But it doesn't matter, because I'm a daddy; I've got the
big, thick cock to prove it. Silicone, yes; maybe not as sensitive as a real
daddy's cock. With this daddy's cock, it's not just a matter of licking and
sucking around the head or teasing the underside of the shaft. Sucking this
cock is a lot more work. My boy has to push and work his head around and suck
my cock harder, pushing the base of the dildo against my clit to make my pussy
throb in response. But I don't care and my boy doesn't care, either, because my
boy knows I'm his Daddy. I've got the cock to prove it -- and the armchair.

And a boy is exactly what he is, tonight. Torn jeans, so
faded they're almost white, hug his lithe body, showing off the big bulge in
his pants, swept to the right and getting bigger as he sucks me. His tight
white T-shirt, so tight it's almost see-through, shows off his perfect chest.
He looks like some boy hustler I picked up on the street, offered a place to
stay in return for a blowjob. The big white athletic shoes are a decidedly
adolescent touch.

The whole package makes my pussy so wet I can hardly stand
it.

And when he looks up at me with his mouth around my cock,
there's no question that this is my boy, servicing me.

"Come on, boy, suck it better than that. Earn your
keep."

He launches more eagerly into it, his mouth pumping down on
my cock and forcing it deeper into his throat. He's obviously a skilled
cocksucker; he doesn't even hesitate when the head of my cock presses against
his throat. He just swallows, knowing that's what I want. I want to feel him
take it all the way, feeling it in his belly, just like he will when I put it
up his ass.

His eyes turn back up to me and I grin down at him, flicking
ash off the end of the cigar. "I think it's time you sucked a little ass,
boy."

I pull him off of my cock and turn around on the armchair,
pulling my leather pants down over my hips. When I've got them down around my
knees, I bend over, pushing my ass out for him. He leans in and obediently
presses his face between my cheeks, his tongue sliding into my ass. I have to
stifle a gasp that I know will sound way too feminine, and I barely manage to
replace it with a manly grunt as I reach back behind me to grab his hair and
push his face more firmly into my ass. His tongue works its way deeper into my
asshole. He alternates between teasing the entrance with big long swirls of his
tongue and pushing hard into it like he's fucking me with that limber little
organ. I want to reach down and rub my clit; I want to come so bad it's driving
me crazy. But instead of rubbing my clit I reach down and begin to jerk off,
stroking my cock, pumping it hard up and down, and that only makes me want to
come even more. When I push the dildo down I can feel the base against my clit,
almost direct enough to make me come, but not quite. God, I want to fuck him so
bad.