Jenny Roark had been with her boyfriend, Darryl, for
six years. They had dated since high school and
survived a long distance relationship during college.
When they got back together and after graduation there
was something different.
Jenny knew that Darryl hadn’t been loyal, nor had she
for that matter. During college, she figured, it was
permissible to explore your own sexual identity. She
had many sexual encounters, with men and a few women,
but she always kept her heart focused on Darryl.
Darryl, she guessed, hadn’t returned the favor.
After the honeymoon months that followed graduation she
started to notice a different side of Darryl. He was
more sexually explorative, often asking her to shove
her finger up his ass during sex. She felt obliged
because she wanted to please him, but things got more
perverted as time went on.
Darryl got a job in another city and they decided to
move there together. As much as Jenny was suspicious of
Darryl’s inhibitions, she couldn’t deny the love she
still had for him. He would spend late hours at work
and she would grow more doubtful about her motives for
leaving her home.
She found a job as a copy editor and Darryl’s career
grew quickly. The conversations between them became
scarce but the sex life intensified. He would come home
occasionally with a black bag and a wild smile. The
first time he pulled out anal beads. That night he had
Jenny suck him off while filling his ass full of
increasingly larger beads. When he was about to cum he
yelled at her to pull the beads out and while being
emptied he filled Jenny’s mouth with his spunk. There
was no thank you or cuddling, no returning the favor or
massage, he just passed out. Jenny was so turned off
she tossed the beads on the floor and went to sleep.
His next surprise was a butt plug and vibrator. He told
her the vibrator was for her but he kept asking her to
use it on him. After buying those toys he never went a
sex session without first plug in his ass. Once he told
her to lick his asshole then slide the butt plug into
him. She was a bit revolted, but she figured she was
going through a hard time with Darryl, being in a
foreign setting with no family to rely on, so she
swallowed her pride and stuck out her tongue.
Darryl anticipated her acceptance and was on his knees
on the bed with his ass in the air and his face buried
in a pillow. She started licking along his crack and
tickling his perineum and balls. He would squirm but
kept positioning his ass closer to her tongue. She
finally gave in and started to lap around his
He gasped like he had been holding in his breath all
those months they’d been together since graduating. The
musty smell and foul taste to Jenny was almost made
tolerable by the amount of pleasure she was giving to
Darryl. She sucked it up and got into the activity. She
tongue fucked his ass, slipping her firm, protruding
tongue as far into his anus as she could. She reached
under him and started tugging on his cock in time with
her pumping tongue.
Before she was able to get him off he rolled over
telling her to stick it into him. She grabbed the butt
plug but he quickly told her that the butt plug
wouldn’t cut it and to get the vibrator. She hesitated
but seeing the look of need in his eyes won her over
she fished the vibrator out of her drawer and turned
the base bringing it to a whirring life. His eye
widened in excitement, more excitement that he had
shown towards her in years.
He scooted to the head of the bed and brought his knees
over his head, bringing his back perpendicular to the
ground. He held onto the head board to gain his balance
and she crawled up to him. Kneeling beside his upturned
ass she was about to massage the perimeter of his
pucker but he took a hand from the bed board and gently
led her hand holding the vibrator towards his slightly
He stuck out his tongue and ran it over the entire
shaft of the vibrator. He lubed the head very well and
let go of Jenny’s arm. She took the clue and placed the
head right against his brown star. She turned the
vibration down and pushed it into him. His hips
responded with a gentle roll, much like she would do
when she wasn’t that moist for his entry.
The tip passed through the sphincter with relatively
little resistance. His breathing was erratic and his
moaning grew louder. She kept putting on the pressure
until the vibrator wouldn’t go any deeper and then she
started to pull it out. His tight ring clung on and
seemed to follow the shaft out. She found it
interesting but not quite a turn on. He on the other
hand was in paradise.
He worked his ass with her efforts like a pro. She
decided to turn up the juice and get the vibrator
humming in his bowels. She slowly turned the power up
and watched his face glow in pleasure. His discomfort
waned and he began to roll his hips. She countered with
slowly bringing it in and out with an increasing pace.
She held the vibrator like an ice pick and stabbed it
into his welcoming ass.
A fury grew in her and she pounded away with a renewed
vigor. His hips stopped rolling and his body grew
stiff. His moans grew into screams and his flushed face
turned a shade of purple. Without even having his cock,
so much as touched he began to ejaculate in thick
ropes. Having his crotch positioned over his head sent
his cum splashing onto his neck and face. His screaming
mouth was wide and several globs scored home. Jenny
noticed him swallow the glob down and open his mouth
letting another drop land in his throat.
His next surprise was a strap-on for Jenny. The dildo
was a realistic latex complete with veins and balls. It
attached to a plastic mounting on a leather holster.
Jenny tried to fake her excitement while opening it in
front of an excited Darryl. She teased him and said
that now she could finally have her vibrator back.
Darryl didn’t like that comment. “What, do you think
I’m crazy about getting my ass stuffed? I only buy this
shit because it’s the only way to get your frigid ass
into having sex. You can’t blame me for your failures
in bed.” He stomped out of the living room and into the
bedroom of their cramped apartment, slamming the door
behind him. Jenny heard the click of the lock as her
tears rolled down her cheeks.
She stayed near the door hoping to talk with him as
soon as he came out. She had the key but wanted him to
make an effort to come to her. For an hour she sat
beside it until she heard her vibrator hum to life in
the bedroom. Bringing her ear to the door she heard the
muffled moans of Darryl’s filtering between the hinges.
For some reason she grew frantic. She stripped herself
naked and went to the black paper bag and retrieved and
fastened the strap-on. With the firm cock jutting out
before her it led her into the kitchen area where she
pulled the vegetable oil from a cabinet. She poured a
line over the latex cock and spread it around until the
entire pole glistened.
She walked back to the bedroom door after grabbed the
key. Turning the lock slowly, she opened the door
without as much as a creak. She saw Darryl with his
elbows holding his knees back, jamming the humming
vibrator deep into the recesses of his anus.
Jenny was jerking off her glistening and slick cock.
She walked up to the corner of the bed and finally
Darryl’s squinting eyes made out her lithe silhouette
created by the light from the doorway. He let his knees
fall and the vibrator slip from his ass.
Slowly bringing one knee at a time she mounted the bed
and pivoted her way to Darryl. Her cheeks were still
moist with tears but she took her slimy hand and wiped
it over Darryl’s gaping hole. He just closed his eyes
and lifted his legs. She took a pillow and placed it
under the small of his back, to keep his ass in the
proper position. Using one hand she took both of his
ankles and raised them high as she guided the well
lubed prick to his ass. She smeared it up and down his
crack bringing sighs of pleasure deep from Darryl’s
This was the role he found that suited him. Jenny now
understood that and knew perfectly well that she
couldn’t please him without sacrificing her own
pleasure. That didn’t mean she didn’t love him it just
meant that she couldn’t be sexually fulfilled with him.
It was over but she’d give him one last thrill, one
more ride to show him she cared, and then she’d say
She leaned forward, feeling the base of the shaft press
into her own mound. The head of the strap-on was much
wider than her vibrator. The mushroomed helmet met with
the resistance of his sphincter despite the liberal
amount of lubricant. His excitement didn’t help matters
and his raging hard on accented his tightened ring.
She pivoted her hips back and forth, managing to sink
the head in one millimeter at a time. Darryl never
opened his eyes but he did hold onto Jenny’s hips,
helping her add pressure when the feeling in his ass
was just right. Their combined effort earned the reward
of the firm latex head passing through his tight
asshole. Darryl responded with a gasp. The remainder of
the shaft slipped in relatively easy but still left
Darryl writhing in simultaneous pleasure and agony.
Each time the head would rub along his prostate he
would grunt as though a tiny lightening bolt had struck
him from the rear.
This was all bitter sweet to Jenny. She was fucking her
boyfriend of six years. His college days had corrupted
him. The clean sex she knew in high school was more a
myth than a memory. Maybe Darryl had now corrupted her?
She tried not to focus on anything beside the moment,
desperately trying to push out the questions that
plagued her mind. She tuned in to her rhythm, the
creaking of the bed, the moans soaring up from below
her. If only she could live in the present, no problem
would exist between them. But the past had left regrets
and missed opportunities. The future brings with it
climaxes and falling action. She wanted only the
And so it came and with it Darryl’s cum. It shot far up
his chest, forming pools between his pecs and six pack,
collecting into a milky puddle around his navel. He
cried out, no name, no words, just a guttural,
primitive croak-one that would’ve set hounds howling.
It had accomplished enough and forced those waves of
pleasure, building from the Snap-On’s base slamming
against her clit, crashing over her and sending her to
join Darryl in oblivion.
Flashes danced before her eyes as she continued to
pound into Darryl. Her moans doubling in volume with
each thrust. Darryl persisted in pulling her hips into
his ass. The energy surpassed the threshold of her will
and she bucked uncontrollably in ecstasy. The cock
slipped out of Darryl’s ass without her knowing and it
glided up and down from Darryl’s numb hole, up his
crack to his balls. She finally came to a stop with the
strap on lodged beside his own withering pecker.
Darryl lay there with his eyes closed breathing deeply.
Jenny asked herself if he knew what was to come. There
never is a guarantee what comes next, only an argument
what happened before.
Darryl was asleep. Jenny decided to give him a proper
cleansing. She leaned forward and lapped the pools of
cum that had formed over his body. Once she loved this
taste, it was the rare pleasure that spiced their
otherwise content lives. Somewhere along the lines
Darryl grew dissatisfied. She licked him clean. The
only evidence of their last activity would be Darryl’s
She took off the strap-on, got dressed and packed her
things. After calling a cab and dragging her luggage to
the door she stood beside Darryl’s bed to give him a
last good-bye. His sleeping body still reminded her of
when they first explored each other’s bodies while
making out between passing periods. Her tits were still
small and his shoulders were still weak, but it wasn’t
their flesh that had made the difference rather it was
She leaned over and kissed his cheek causing him to
roll over, his cleansed body looking unmolested. She
smiled to herself, “maybe when I’m nothing but a myth,
he’ll love me again.” With that she walked out.