My moms boyfriend is my sissy

He seemed like a slut to begin with, who knew he really was.

Divorce often times traumatizes the children, but in my case, it set me free from all their arguments.
Dad signed the papers and walked out the door on my seventeenth birthday; it was the best present
he could have ever given me. I was finally free, I could go to parties and hang with guys. Mom was
the lenient one who was always gone on some major trip. I was cool with it until she brought home a
Coming home from Europe, my mom walked through the front door, shouting, “I’m home, and I
brought a man with me.”
Those words scared me instantly, I was enjoying my freedom; I didn’t want some lame boyfriend of
hers to ruin my fun, but she sounded happy so I figured why not. I should have known she would drag
home a guy that screamed, “Slut!”
One look at him and I decided to make his world living hell. Walking right up to him, I shook his hand
and asked, “So who do you fuck when my mom’s pussy isn’t good enough?”
My mother stared at me in horror, how could the angel of the family be so disrespectful. Saying
something like that, with a smile on her face. She shouldn’t have worried though, the guy just laughed
it off saying teenagers. That didn’t sit well with me so I continued, “Oh, so it’s teenagers that you like
when you’re tired of fucking my mother. Thanks for telling me, I’ll be sure to tell my friends, should
they ever need a slut.”
That was the last straw, my mom began yelling at me, “Just because you’re eighteen and think you
know everything, doesn’t give you the right to treat respectable people so horrible. Go straight to your
room, missy; I’ve had it with your snobbish acts. You will not get lunch or supper today! Now leave my
sight before I decide to do something I will regret.”
Turning my back on them, I smiled and headed for my room. It wasn’t often I riled my mother’s anger,
and I wasn’t going to pass up the opportunity of having my freedom. She said go to my room, she
never said I had to stay in it.
There was a party going on this evening and I was determined to go, just to get away if anything else.
Yet, just as I was about to hop out of my window, I heard the front door shut. Peeking out to the
street, I found my mother hurrying to her car, off on another adventure.
Knowing I was more likely to get away with sneaking out, I braced myself in the window frame,
readying to jump, when a knock sounded on the door. Having not been expecting it, I fell backwards
into my room with a shriek. My stupid mother left her boyfriend in the house!
Standing quickly, I rushed to my door and opened it, only to find something that nearly killed me. My
mother’s boyfriend had found some of what I assumed were her clothes and was dressed very
feminine, and to be honest, hot. Gulping at the sight, I asked, “What the hell kind of slut are you?”
He smiled and stepped into my room, invading my privacy. “I’m the kind of slut that wants you to treat
me like your little bitch. I’m your sissy and you are my Mistress. You did want to know what I liked did
you not? So own up and give it a try.”
I swallowed again and stepped back, what he said was ridiculous, but at the same time, it spiked my
curiosity and I wanted to humiliate him. “Very well, but not tonight! I need to find supplies and steady
my mind. Tomorrow will be soon enough, but whatever you do, you are not to touch your cock. Do
you understand?”
“Yes Mistress, I will be a good slut and not play until you say I can.” He smiled down at me, a thrill
lighting his eyes, knowing that I had every intention of dominating him, showing him how much of a
sissy he was.
“Good, and tomorrow you are to wear more see through clothing as well as some nylons,” I said,
getting into the role.
“Very well Mistress, I will work to look my sluttiest for you,” he whispered with his head bowed.
Closing the door on him, I went about preparing for bed, hoping that I would at least sleep some after
what had just transpired. I needed not worry; the moment my head hit the pillow, I was out, dreaming
of everything I would do to him.
Early the next morning, I arose well rested and ready to hit my favorite adult bookstore. Dressing in
black stockings, black mini skirt, red t-shirt, and my knee-high, red boots, I left in my blue sports car,
careful to follow the speed limits in my rush to get what I wanted for tonight.
Reaching my destination, I slid out of my car and strutted straight through the door. Finding a cute
clerk, I went up to him and requested what I wanted, not caring to take the time to search. Seeing my
urgency, he wasted no time in finding everything that I listed. He went even to great length to retrieve
the colors I wanted.
First, he found me a long, thick, black strap on. Then came a studded pink collar with a matching
leash. Next followed the KY jelly. Following that was the purple crop I wanted. Last but not least, I
requested their largest vibrating butt plug. It turned out to be black with diamond studs on it.
Pulling out my credit card, for those emergencies my mother worried about when gone, I paid and
quickly grabbed the bagged supplies, exiting the store. I couldn’t wait to get home and try it on my
mother’s boyfriend and my slut. He was going to be in for a treat.
Speeding through town, I was grateful to find no cops out, as I pulled into my driveway. Shutting off
the car, I sat for a few minutes, contemplating that I was actually going to do this. Smiling, I knew I
had no intention of backing out. He had looked mouthwatering in my mother’s clothes and I wanted
him more for it.
Sliding from the leather driver’s seat, I strolled to the front door, bag in hand. Turning the key in the
lock, I opened the door. What awaited me was my beautiful slut, down on his knees, in what
appeared to be netted, black stockings, a red, see through thong, black, calf-high boots with a heel,
my netted black shirt finishing the outfit. Dressed in female clothing, I desired him all the more. I even
took notice that he had applied eyeliner, mascara, blush, and a sinful red lipstick.
Seeing this, I dug quickly through the bag, pulling out the pink collar and leash. I clamped the collar
around his neck, causing him to moan out for more. Taking the bag in my left hand and the leash in
the other, I told him to lead the way to my bedroom. His ass waggled as he moved in front of me; the
sight of him in such a position instantly had me wet between my thighs.
Reaching my bed, I yanked him to his feet, pulling on the leash until he came stumbling towards me
and our lips melt. The lipstick mixing with his saliva as I rammed my tongue deep into his mouth; it
was intoxicating. Breaking the lip lock, I shoved him roughly into the bed, telling him to stroke his cock
through the soft panties. He eagerly complied, moaning out as his hand pushed the material into his
stiff manhood.
Smiling, I went back into my bag, taking out the KY jelly as well as the vibrating butt plug. Going over
to him, I told him not to stop as I moved the string of his thong out of his ass crack. He gasped as I
poured KY jelly over his ass, letting it run into his little hole. Watching his hole wink as the cool jelly hit
it, I pushed my finger into it. He moaned and thrust his hips onto my finger, taking it deeper.
Mad that he made such a move, I immediately removed my finger and went back to the bag, coming
back with the crop. Slapping it down on his inner thigh, I glared at him, “You will do nothing unless I
tell you to, got that?”
His reply came quickly as he moaned, “ Yes, Mistress. I will do as you say, when you say it.”
Smiling at his easy acceptance, I shoved two fingers into his wet asshole. His body jerked as he
worked to fight his instinct to ride my hand. Happy that he was working his hardest to appease me, I
shoved another finger in, causing him to yelp in pained-pleasure. Laughing at his reaction, I removed
my fingers, receiving a whimper. He needed not worry, I replaced them with the vibrating butt plug.
His ass swallowed it in greedily, as it buzzed inside him, making him wither.
Reaching forward, I pulled down the thong, letting his cock spring free while the fabric continued to
cover his balls. I instantly began playing with his balls, watching as precum ran from the tip of his
cock, coating it and wetting the panties as it went. He seemed to be in ecstasy as vibrations ran
through his ass, tickling his prostate as my hand pull and played with his balls through the soft
Within moments he was begging to cum, but I shook my head, removing the butt plug. I went back to
the bag a final time and yanked free the strap on. Seeing it, his eyes glazed over in lust as he
watched me put it on. Coming back to him, I leaned in until my lips were inches from his chest, my
tongue coming out to flicker over his nipples through the netted shirt. Pulling on the leash, I soon had
his nipple in my mouth, sucking on it through the fabric as my fake cock slid into his well-lubed ass.
His body arching as the cock continued to go in deeper, stretching his pucker hole.
Starting with slow deliberate strokes, I made sure to work towards his prostate each and every time.
He continued to beg for his release. I constantly shook my head no, reaching over for the crop when
his begging became over zealous. Snapping it hard very close to his cock caused him to yell out in
pain, before it was a moan as my hand wrapped around his cock and began pumping in time with my
His cock began to pulse beneath my hand, and I knew this time, no matter how much he wanted to,
he wouldn’t be able to hold back his orgasm. Sliding forward, I whispered into his ear, “Cum for me,
let me see you shoot your load all over your chest and face. Cum now!”
Directly on my command, his hot semen shot rope after rope over his chest and face, leaving white
streaks of cum zigzagging over the black netting. Smiling at what a beautiful sight he made, I began
licking the cum off him, enjoying just how good he tasted. I couldn’t wait for tomorrow, knowing we
would play again. With a final kiss on his red lips and a dribble of shared cum, I left to go take a
shower, leaving my crossdressing slut to take care of himself.

3 thoughts on “My moms boyfriend is my sissy

  1. I am at a loose for words, that wouldd be my dearest dream CUM true, then she needs to start pimping me out at the ABS and bars

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