Being his assistant was more demanding
than just being one of his lovers.
Setting aside the leather harness as she sat
down on the bed again, he shook his head
and walked over to his sex toy drawers.
When he returned, he handed her a thick
and squat black silicon dildo with deep
grooving on the sides for her to look over.
The rounded head and smooth surface of
the material contrasted with the squared off
edges of the shaft’s furrows. When she was
done rolling it back and forth between her
hands, he offered her a second dildo. This
one was long and fleshy, a pale skin tone
shaft with a slightly pink glans, and it was
clearly meant to be a man’s cock despite
the overt thickness and length. It bowed in
her hand as she squeezed the two toys to
compare their firmness. She set the shorter
black dildo down and stroked the length of
the phallus before swapping to explore their
surfaces with her fingertips. The black
silicon was blatantly rigid and inflexible,
and it promised to be very demanding. The
realistic cock was flexible enough to
slightly crush in her hand, but it was
clumsy and constantly moving due to its
length and weight.
She was thinking through how they might
feel against her lips when his persistent
gaze interrupted her thoughts. She looked
up to him, and he smiled with a nod.
“Choose,” he requested.
He usually wore his moods on his sleeve,
but he’d been holding back something all
day. She knew him well enough to be
cautious of his request. “Why?” she asked
slowly and deliberately while determining if
it was something that she had done or just
something that he needed.
Gesturing with upraised palms, he
reiterated details that he’d been whispering
to her for weeks while she was in the
throes of orgasms. “For the next couple of
months, we will train your pussy to
perceive one of these as the cock it prefers
and craves.” He shrugged. “We’ll keep
going so when you handle a cock, when
you feel a cock in your sex, when you see
a cock… then you will compare it to the
pleasure and sensations of the toy that you
choose today.” He was being completely
logical which was never a good sign.
She took the time to examine the toys
again, setting them side by side and noting
the differences in their thickness and
lengths. Her hands caressed the surface of
their shafts, and she knew that it would be
easy to immediately tell them apart even in
the dark. Despite its more jagged shaft and
thicker girth, she judged the black silicon
sex toy to be much easier to start with than
the long soft cock. Mostly decided, but
pondering his state of mind, she looked up
asked, “How?” He liked explaining things,
and it was a good chance to uncover his
motives and expose the emotions that he
He pointed toward the harness that they
had been fitting to her pelvis and hips
earlier. “The plan is to have you regularly
fuck and wear the dildo you chose. With
orgasms as rewards, frequently playing
with your cock comes with great
incentives. The harness will hold it in place
so you can also enjoy it thoroughly and
passively while you’re home. We’ll keep
working on your double penetration
training but with your cock in your pussy
and me in your ass. We’ve made good
progress and will keep pushing forward on
hollowing out your vagina, but with your
cock inserted before and after.” He stepped
closer and sighed while running a hand
over her bare thigh. “Open, wet, and
fucked, my lovely assistant. And using one
of these will assure me that you are being
fucked properly and often even when I’m
She suspected that he wasn’t be honest
about his intentions. Despite occasional
requests to know what she was enjoying
while he was working in other cities, he
didn’t really seem too concerned about her
other male partners so long as it didn’t
interfere with his fun. “Do I have other
options?” Sometimes he was very
inflexible, and she wasn’t always clear
why. Maybe this was just a test of some
His smile turned into an evil Cheshire grin.
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