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Most of what I write are true events from my past, lucky for me most occurring in a time before video surveillance and camera phones. As a man who lives life as a man spending a decade married to a woman and having multiple girlfriends before, after, and during my marriage I have never been able to stop Crossdressing for any length of time so when I do dress up I turn into a slut.
I live in a apartment complex and we recently got two new maintenance men a father son duo that I've been seeing around lately.
This story thought is a fantasy that has been filling my head after seeing these two men almost daily in my complex.
Here's My fantasy,
I live upstairs and often walk around my apartment dressed up in women's clothes, feeling the soft silky material against my skin has always excited me so I wear it often while cleaning my apartment.
I keep my blinds open to give sunlight to my plants which adds to my excitement of possibly being watched, the only way anyone can see me from the ground floor is when I'm near a window. I get a rush every time I look towards one of my windows waiting to see one of my neighbors in a upstairs unit looking at me which hasn't happened yet or if maintenance happens to be on one of the roofs of a nearby building where they could see inside my apartment.
I often like dressing up in lingerie to do housework and this day was no different. Thanks to Amazon it's become easy to purchase clothes, heels and sex toys using the internet unlike the old days when you had to go to the store to buy them which can be difficult and embarrassing at times being a man.
I'm walking around my apartment dusting and cleaning dressed up in my favorite color black wearing this sexy black front lacing corset that has four garters per leg.
First I have on nude pantyhose that I cut the cotton panel out with scissors before putting them on to hide my light blonde leg hairs, then I pinch a tiny bit of pantyhose right in front of my dick just cutting the tip with my scissors before letting go, the pantyhose snap tight to my skin with my cock and balls sticking out perfectly from the nylon material.
After I'm wearing the corset I put on a pair of black lacey designer thigh high stockings pulling them high up my long leg attaching each of the eight garter straps to it's proper position holding the stockings in place. Even though I'm alone I need my outfit to look perfect.
Once I have my corset with stockings on I pick out a pair of five inch black stilettos, thanks again amazon again that have two thin straps over the top of my foot with two buckling straps around each ankle, no platform but five inch thin spike heels that have me walking around on my toes but look amazing.
Now walking around in the heels on my tip toes has my hard dick swinging side to side so I need to bind it. I use a leg cut from a pair of silky pantyhose first wrapping it only around my balls pulling my sack away from my shaft I wrap the stocking around a few times constantly adjusting them to reduce the pain squeezing my ball sack tight which pushes my two testicules into a ball hanging a few inches below my dick then continuing to wrap the stocking around the base of my shaft at the same time before trying a loose knot to secure it.
With my cock and balls tied up by the stocking my hard cock is even harder, my balls a bit swollen from the lack of blood flowing freely and forced into a more restrictive area I slip on a pair of black satin panties the feeling of the silky material against my bound cock brings me close to cumming but I control it, riding the little waves of orgasms instead of letting myself go. If I was to cum now my fun would be over.
As I walk around the house everything settles into place with a little adjustment to the multiple wraps of stocking around my dick, by now a wet spot has appeared in my panties from precum escaping the binding.
I then spend time trying on different slips, nightgowns and slinky black dresses while I clean, all of this time wearing sexy ladies clothes building up to my normal explosive orgasm that I refrain from as long as possible, for hours I can bring myself to the edge of cumming and back away.
I'm running the vacuum in the living room watching lets make a deal, Tiffany Coynes long legs and tight body walking around stage when a hard knock startles me.
KNOCK... KNOCK!
KNOCK... KNOCK!
I shut off the vacuum but afraid of who might be there so I hesitate to answer when my door suddenly opens and the taller young maintenance man comes walking right in, standing in these heels I'm 6'4" tall and this young man stood taller than I as he stepped in with his dad in tow walking right in behind him. The two men stood right in front of me as I stepped back they closed the door.
I froze, I couldn't move or speak as the two men stood looking me over, the older dad was standing eye to eye with me making him about 6'4' and the son stood taller at about 6'8", both tall and thin with a dark milk chocolate complexion and bald.
I was speechless and embarrassed when the dad reached out putting his hand on my shoulder adding pressure to push me down, I know what they want, I've been here before so I submit like a good sissy kneeling down onto the floor in front of them, the view of the outline of both their cocks hypnotizing me when I see the size of their package underneath their matching work overalls.
I begin to run my hands up their legs one hand on each of them from the knee up the thigh touching each of their massive dicks hidden under the overalls they wore.
In unison they seemed to drop the bibs of the overalls at the same time as the baggy heavy material dropped to the floor exposing two of the biggest black dicks I have ever seen an I have had some extremely large bbc over the years. The two giant cocks hanging like a pair of two foot summer sausages with a pair of oranges hanging underneath.
The dad took a handful of my hair pulling me on my knees while he took a seat on my couch while the son slipped some disc from his pocket into my Blu-ray causing my tv to instantly switch to a porn video.
The dad took full control without saying a word, he had me on my knees between his legs in awe over the size of his cock, the thing was massive, veins the size of pencils weaving and winding around the meat stick, the only normal looking part was the small dark pink head with a slit running halfway up to the pee hole. With hands twice the size of mine he gripped his dick rubbing it to my lips before I opened my mouth to take it in barely fitting the head into my mouth I attempted to suck on it as best I could.
I couldn't do it, in no way was I going to satisfy these guys with my mouth and we all knew it which is when the first words were spoken.
"Son.... find us some kind of lube and get something to throw on the floor." the dad tells his son as he keeps my mouth stuffed with the head of his dick, guiding my head with the handful of my hair wadded up in his fist.
I'm hearing different women screaming in agony coming from my tv mixed with loud groans and moans of pleasure but I couldn't see my tv since I was being held with my face in the dads lap as I did my best to lick him with my tongue.
The son returned with a couple options for lube he told his dad while opening a blanket onto my floor behind me before closing the blinds in my living room.
When the men stood me up I could see that it was the two of them in the video fucking different white girls absolutely destroying their little pussies and assholes.
The son then removes my black nightgown pulling it up over my head exposing my full lingerie attire making a comment about how sexy I looked before he pulls down my panties, my rock hard nylon bound cock springs out bouncing around in freedom.
When they see how I have my cock tied the dad tells the son to find more pantyhose to tie me up, with those instructions he heads off as I tell him right where to find them so he doesn't search through everything to find them.
The son returns to find that the dad has positioned me over a bar stool putting my ass at about the right height to their crotch. Now the son held me in position while the dad tied me to the stool. He tied my ankles and knees to both sides of the tall stool with my bound cock pointing to the floor, he then tied a satin robe belt around my waist to the stool keeping my ass locked in position before telling his son to tie my hands to the back of the stool as far down as I could reach. I was locked in place.
They spun me around so that the tv screen with them fucking these different women was right in my face when the son stuffs a pair of panties in my mouth.
"That's so you can't scream like those whores!" he says to me.
"Flip for it dad?" the son ask his father to see who goes first.
"Not this time!" the dad replies.
I'm breaking this one in right.... so we can always come back in the future." he added which had my head spinning both in fear and excitement.
The two of them began spanking my ass each with their own cheek to slap for a moment before ripping my pantyhose wide open exposing my tight white puckered hole. Using vegetable oil they poured it over my ass and their cocks with the son stuffing two of his eight inch long fingers deep into my ass moving them around and pulling my hole open stretching it side to side while pouring more oil into the hole as his dad took position behind me adding a finger of his own pushing it into my hole. With three long black fingers twisting and turning inside me they pull my hole apart to open it up, stretching it open for them to fuck.
Im watching this twenty year old little blonde girl smashed to the floor with her little ass in the air screaming as the son forces his huge dick into her ass while the dad is holding her down.
Just as I watch the son begin to stuff his way inside her the dad pushes his bbc into my ass, thank god for the panties in my mouth because I would have screamed loudly it was so intense, once he broke the ring of my sphincter he continued to push his entire dick into me as if it was his arm. The intense pain with pleasure was taking me over as I seemed to collapse, my body going limp to allow the monster cock to slide inside ending my resistance.
It felt as though it would never end rearranging my entire insides to fit his giant limp black cock as I submitted to him. I had no choice.
"I told you dad." the son says "told you this man was a crossdresser." he added as his dad continued to stuff my ass with his hardening huge black cock. With two hands he pushed and stuffed his thick semi hard cock into my hole, pushing, moving, pushing some more he continued trying to stuff his cock into me when it finally broke my tight sphincter ring instantly feeding a foot of his big black cock deep inside me. Unable to move tied to the stool I have nowhere to go as the giant pole makes it's way inside my body rearranging and moving anything in its way as I begin to cum.
He begins to pull back just a little maybe two or three inches then pushes back in with power to force himself deeper into my throbbing burning asshole as I tried my best to relax my hole to let him get deeper in me without ripping me open. The son let go of my butt cheeks now that his dad had a foot of his growing cock settled inside me now able to slide it in and out of me with longer deep strokes of about six inches or so while not allowing me to push him out.
The feeling of his big long chocolate cock sliding in and out then slammed hard into me trying to get deeper had me in a hypnotic state it felt so good. I was starting to really relax enjoying the feeling and not attempting any resistance as cum flows freely from my tied dick.
When the son moved in front of me and for the first time I see his dick, it was massive in width and length, rock hard like a kids baseball bat, one of the straightest dicks I've ever seen and it was HUGE!
For a moment I didn't feel his dads giant dick fucking me because the site of this guy's black dick took my breath away until his dad slammed into me so hard that when his big ball sack slammed into my tied up balls I almost past out it hurt so bad, not sure if it was from his balls hitting mine or the head of his dick punching my heart either way it was extremely painful bringing my attention back to him. With his sons cock right in front of my face, my mouth stuffed with panties I watched the guy pour cooking oil into his huge hand before rubbing it up and down his cock making it wet and shiny looking, stroking it up and down while he twists and pulls it, looking like two sixteen ounce coors can stacked together in his hand he pours more oil down the length of his staft and steps out of sight.
On the tv I'm watching these two men pounding this petite brunette milf with the dad underneath the woman his cock stretching her pussy wide open as the son is slamming her ass from above with incredible stamina when the dad finally pulls out of my ass for the first time since he began stuffing his cock inside me quite some time ago.
With my ass gaping open the cool feeling of air way up inside me I was able to catch my breath when I feel this hard pole pushing into my gaping ass already stretched to the limit now opening me up even more.... It was the son.
For a moment my hole tried to fight but the 6'8" man was too powerful bursting me open as he plunged in deep without mercy he rammed his fat steel rod in deeper than his dad in one powerful thrust as he laughed telling his dad "No hole is too tough for our stuff." as I heard what sounded like a high five as they both had a laugh.
The kid was using such long powerful strokes I blacked out mentally, over and over pumping in an out of me with the stamina of an athlete. I was cumming so hard, my orgasms and convulsing anal cavity only flipping a switch on the kid as he doubled his speed pumping his two foot cock into me rapidly with powerful thrust for what seemed like an eternity before pulling out of me sounding like a fist being pulled out of a watermelon with a loud squishy sound.
My body and asshole spasming from the assault it just received, the feeling of emptiness was only a temporary relief.
Then the dad went for a second round only this time he was also rock hard, driving his hard fat dick super deep into me on the first thrust again punching my guts without mercy.
"Watch the video.... it's gonna be you soon." the son tells me as the stockings they used to tie me binding me to the stool began to become painful like they were cutting into my skin from the force they were both using to fuck me.
Like it was a competition between father and son to see who had the most stamina, who had the deepest thrusts and so on these two men didn't let up.
As I watch the tv screen I begin to fade out from the continuous orgasms I'm going through while the two men take turns rapidly fucking me. Each man taking turns in unison using deep and powerful thrust to destroy my hole rapidly fucking my ass then instantly switching positions to let the other have a turn, back and forth from father to son and back again like a two person tag teams rapid marathon not leaving my ass any time to clinch up before the other man was again pounding away continually adding oil to my hole as they pumped into me.
I watched these women on the screen having their asses and pussies opened up so much gaping so wide and deep you could fit a beer can inside them without touching the sides. I watched segment after segment a compilation of these two guys totally destroy the holes of these women and the ladies loved it.... and my ass was next.
Hope you've enjoyed my fantasy because I sure have.
I wish that I had artwork to accompany my fantasy, I guess I need to learn to draw.
Do you think they filmed me like they filmed the women?
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