Published 5 months ago

I was sitting on my knees in front of my mistress.
She was completely nude except for her shiny black stiletto pumps…
positioned on the edge of her large bed, she was looking down on me smiling like a predator when it sees his prey…
next to her stood a man I only knew as “John”.
A big muscular man of about 30 years, ten years my younger…
he stood next to her with his Strong arms behind his back staring in front of him like a good soldier.
A dim light was shining on his naked body making it stand out in the bedroom of my mistress.

“look at it, my sweet sissy boy” my mistress whispered to me
“look at it’s size while still flaccid and wonder how big it will get when at full attention.”

my gaze went from the dark eyes of my mistress to the flaccid penis of John.
It was quite big for a still flaccid penis, but in my mind that doesn’t mean anything.
It seemed thicker than most flaccid penises i had seen so far and i must admit it look very good.
The dark tip of the penis was hanging about an inch underneath a pair of big balls and the whole package was shaven completely and it appeared shiny in the dim light, probably due to some massage oils…

the hand of my mistress went from behind john’s back in between his legs and grabbed the penis and balls by the base. John didn’t move a muscle…
she pulled the whole package slowly but firmly down stretching it at least another inch or two…

“isn’t it just wonderful, my sweet sissy boy?” my mistress whispered to me while starting to do a slow pull and release massage on the package of john.

My eyes fixed on her hand, seeing it twisting and pulling the penis and balls firmly wishing i could get the same treatment.

“ah, look, my sweet sissy boy, it’s starting to grow now…. Soon it will be ready…. Not long now...”

indeed the penis was slowly growing due to the firm massage it was receiving. While at first the thick flacid shaft was pointing downward, at the moment it had grown at least 2 inches in length and even a bit in width. The head now pointing more towards me.

The hand between the legs of john now grabbed just the big balls and started a firm soft massage whil with her other hand my mistress slowly started to jerk the shaft up and down. Making it grow larger and thicker and more and more upright.

“look at that. My sweet sissy boy. Look at that big mushroom shaped head. Look at that thick long shaft and look at thes big, full balls. Oh yes… we’ve been saving up for this evening, john and me! I told him you would be his prize if he could wait a week… it must have been an easy week for him but now… oh, how full are these” whispered my mistress as she pulled those big balls down.

During the entire massage John hadn’t moved. I had not dared to move either but my own penis stood up at full attention.

When she noticed it she smiled her predatory smile again…
“yessss… my sweet sissy boy, i see you enjoy this, probably wishing you were standing here….”
“another time maybe, when I have grown tired of John, you might be able to take his place once in a while…. But not now. No, no, no…”

She continued her massage a little while longer until she was satisfied she could get any better results. Abruptly she stood up.
She took to steps towards me and stood in between me and john. Curvy naked body so close made my penis start to throb a little, I was almost tempted to move forward to try to kiss, lick or taste any part of her I could reach, but I stopped myself on time.

I could smell her sweet scent… after months of being used for her pleasure I recognized that scent anywhere… I knew instantly that massaging John’s penis and having me watch that had aroused her and would turn her into the deviant mistress I had given my body to long ago.

“ah, you can smell me, can’t you sweet sissy boy? You can tell now when I’m aroused and that means you can tell what I expect from you...”

she bent over in front of me, taking one step back so her large breasts were hanging before me and she grabbed the leash that was hanging from my collar to pull my chin up. Her face not even half an inch from my face, breathing her sweet breath on me she whispered to me:

“while you think being so close to me is almost as good as touching me, you will know that at this moment the tip of john’s big headed cock is now pressing wonderfully against my wet little pussy. My gift to you my sweet sissy boy, as you will soon discover more fully….”

she let go of the leash and i noticed she was moving a little bit by the gentle swaying of her large breasts… it appeared she was wiggling her soft round hips a little to stimulate Johns penis a bit extra with her pussy.

“enough!”she exclaimed suddenly loudly. And grabbed my leash again only to pull me f***efully towards john. He still hadn’t moved a single inch and was still staring to the wall in front of him.

She put the leash between the legs of john and slowly pulled me towards him.

Knowing full well what was expected of me i obediently followed her lead and crawled towards john, making sure the leash would not grow slack between my collar and the hand of my mistress.

She actually let my nose touch the shaft of Johns big penis before she stopped pulling. I was now so close I could see all the veins in his penis, and once up close like this, I must admit it was enormous. Length wise I had probably seen a lot bigger online, but i don’t recall having ever seen anything so thick. The huge had was dark and purple, and completely covered with the sweet scented juices of my mistress.

“my gift to you, my sweet sissy boy. you may sample the tastes of your mistress through the big cock of john. but first you must start by showing your gratitude towards john for saving himself for you this past week.”

I knew my tasks well, I had been trained for this and I had been trained well…
without the use of my hands i moved in. Like a thirsty a****l who has been allowed to drink I grabbed his balls with my tongue as sucked one into my mouth immediately.
I sucked it in and twirled my tongue around it gently but fast making a low humming to sound make a vibrating sensation at the same time.

As soon as I had sucked in one of his big balls John let out a soft moan. The first movement I had noticed and it made me proud to be the cause of it.

I did everything I could to keep hearing the occasional moans of john. I alternated often between balls and sometimes sucked both of his balls in at once while humming louder and pulling them down.

“good work my sweet sissy boy” i heard my mistress whisper in my ear. “I have taught you well it seems. Take your time servicing Johns big jewels, for they hold your final reward...”

i sucked, hummed and licked as best as I could, his thick shaft pressing against my nose, my saliva dripping from his balls and my chin while John moaned softly and my mistress whispered sweet encouragements in my ear…

“you want more john?” my mistress demanded loudly “do you want my sweet boy to give you more?”

john appeard to nod a yes because my mistress bend down towards me and whispered in my ear:
“now give him pleasure, my sweet sissy boy. Show him everything i have been teaching you these last months… take my gift for you, the sweet gift I left you on the tip of john’s thick hard cock”

I didn’t need any more than that! My mouth flew towards the big head of Johns thick cock and closed it around it. it barely fitted he was so thick but the taste of my mistress made me stretch my mouth as far as i could to get it in. Sure enough there was the distinct taste of Johns thick pre-cum as well, but the overpowering taste of my mistress was all the reward I ever wanted. I tried to twirl my tongue around his thick head as fast as i could, taking in all the sweetness of my mistress.
My teeth softly grabbing his shaft right under the head as to keep him locked in my mouth.
After a while the sweet taste of my mistress was overpowered by the salty taste of john’s pre-cum. While not as intoxicating as my mistresses juices it was still enough encouragement to keep up my oral stimulation of john’s powerful thick cock.

Slowly i felt john’s hips starting to make a thrusting motion towards my head. Understanding his needs like a pro, I just opened my mouth, put my tongue out under his shaft and let him slide his thick shaft slowly in and out of my mouth.

“oh wonderful” purred my mistress softly “you’re doing better than I imagined, my sweet sissy boy. I have trained you well. Look at you taking that thick cock like a pro.”

Johns moans were constant now, not loud and more a deep panting, but an exclamation of excitement nonetheless…

“I can see we might be arriving at the final reward a bit sooner than expected” said my mistress softly “but that’s what you get when you train a sissy so well. I will allow you to use your hands as well now, my sweet sissy boy. Show use you’ve mastered the skills of giving pleasure!”

No more encouragement needed! My hands shot up. One towards his big, full balls firmly grabbing them and massaging them while the other closed tightly around his thick shaft rhythmically jerking it up and down while my mouth was doing the same with the top part. Covered with saliva and pre-cum his thick now shone brightly in the dimly lit room. I fulfilled my duty as sissy with pleasure and determination. I licked john from the big round balls to the tip of his thick head, sucking him in as deep as i could, jerking him fast and hard or slow and gentle. For a few moment my only purpose was pleasuring that thick hard cock. In the distance i could hear the sweet encouraging whispers of my mistress and the deep grunted moans of john, this was what I was trained for! It was intoxicating and heavenly!

Then all of a sudden I heard john’s voice for the first time ever:

“it will have to be now, my lady, I can’t hold much longer” he exclaimed in a deep, low voice.

It startled me a little, which went unnoticed by the both of them as my mistress pulled me away from the cock at almost the same instant.

“you hear that, my sweet sissy boy? You are doing such a good job we’ve reached the moment of your final reward ahead of schedule”

Not expecting an answer other than complete obedience she pulled me up and directed me towards the edge of the bed.

“assume your position, my sweet sissy boy” she commanded sternly now.

Not having expected anything other than giving oral pleasure, i hesitated a millisecond before understanding and complying to the commands of my mistress. She noticed and pulled the leash roughly.

“there is no time to waste now, sissy boy. Assume your position, now!” She barked harshly.

I knelt on the bed, legs far apart feet sticking out. I put my face down on the bed facing the chair of my mistress as i was taught and I put my arms next to my legs in case they needed to be tied together.
I felt the head of my still erect penis stick in the flesh of my belly which was a pleasant feeling that diminished a bit the dreaded feeling i started to get when i thought of what was coming next.
I had been anally stimulated before and my mistress had prepared me for penetration with various instruments for a long period. Johns thick hard cock was in all aspects bigger than anything i had ever had in me though.
Although the session up to now had excited me in ways i had not experienced often before and made me really ache for some anal stimulation, I was a bit overwhelmed by the idea of johns cock doing the actual stimulating…

While these thoughts flashed through my head I felt two lubed fingers of my mistress plunge in my ass and that helped a little. At least I was being properly prepared by the one person I had come to trust the most.
She twisted her fingers around inside me a few seconds and declared that I was ready earlier than I would have liked.
Before she went to sit down in her chair, she whispered in me ear:

“you ARE ready my sweet sissy boy, you have been ready for a while. Remember, this is HIS pleasure and YOUR reward. He might not be gentle but HE must feel the pleasure of your well prepared but still tight boypussy. You will receive your first proper breeding and I have chosen the perfect bull. Make me proud, my sissy boy, make your mistress proud!”

As I watched her walk towards her chair I became once more determined to please my mistress no matter what. If she thought me ready, I’d be ready! Anything for her!

As she sat down in the near dark i could only see that she had put one hand on one of her large soft breasts while the other rested somewhere between her thighs. My mind went almost blank, safe for one thought: ‘anything for my mistress’

“whenever you’re ready john” I heard her say.

He was! I felt him coming up behind me. I felt one hand on my hip while with his other hand he directed his thick cock firmly towards my waiting ass. I relaxed as best is i could, how i was trained to do int this position. ‘I am ready’ and ‘anything for my mistress’ flashed through my mind as I felt the tip rub against my anus. A little trickle of excitement shot through me at that very moment when i realized I was fulfilling my purpose. I didn’t tighten when I felt his tip touch my tight ass, but maybe I should have for just a second…
it appeared that my training had been good, so good that my unchanged state of relaxation in my anus was taken as a sign by John… not one I had wanted to give him…
with the tip now pressed firmly against my apparently inviting anus, he grabbed my hips firmly with both hands.

Expecting him to slowly push his huge head inside me, to brake me in slowly as my mistress had done every time she had upgrade the size of her stimulants, i relaxed completely, waiting for the soft delicious pain of stretching…

In hindsight I did good, at that exact moment and the one following I should have done differently.

In one single blow he rammed himself inside me! Hard, deep and without any mercy!

I screamed and had i not been held firmly in place by john himself would have probably jumped forward to get away from his cock.

I could hear his low deep grunt of pleasure, followed by a soft ‘oh yes, that’s the stuff’

from my mistress I heard a soft “wow” and then a satisfied “that’s my sissy boy”

I was split in two. My head was spinning and I could literally see stars in front of my eyes… the pain was unbelievable… I hardly felt him pull back a little before i did feel him ram his thick cock all the way home…. I felt his balls slam against mine with such a f***e that it would probably have hurt if he hadn’t just destroyed my ass. A just screamed again…

again he slowly pulled back before he rammed himself home again. I screamed again…

again…. Again… again…. And again…. Over and over…. As hard as he could, or at least so it felt to me… he got verbal now and grunted loudly ‘yes, yes, that’s it little slut, take my dick, take it deep inside that tight little ass of yours. Scream for me my little slut!’

When at least the soaring pain subsided a little I got more into it. with his big balls slamming into mine constantly and my own dick getting slammed against my belly hard and quick there was some pleasure peaking through… as I got used to his enormous thick cock gilding in and almost out of my ass like a jackhammer at full speed I began to feel the thick veins on his cock actually stimulating my anus…. As i relaxed my body again to cope with the endless pounding of my stretched out hole i felt his thick cock head ram against my prostate when i would arch my back a little making the experience starting to feel more and more pleasurable!

John was a machine! I had no sense of time at that moment but he was on a rampage… he went so hard and so fast that even when his cock occasionally slipped out it was right back in without ever skipping a beat. He was in a zone now… his pace was incredible, his strokes were deep, deeper than i had ever felt… I heard his voice now panting but strong: ‘that’s it little slut, take it all in… no more screams huh, you like it now huh… that’s it you little fuck slut… i’m plowing that ass good and you like it… all the way in, balls deep…. Remember those big balls you sucked rearlier? They are going to fill you up, you little fuck slut… I’m going to breed you and then you’re mine… that ass will always be mine…’

it was exciting to hear his words spoke like that… i started to encourage him a little by moaning and grunting… sometimes i would say things like : ‘oh yes, like that’ and ‘come on, harder and deeper’ or ‘my god you’re big’ followed by ‘take me as you want big boy’

all of a sudden he grabbed my arms and lifted my upper body of the bed, pulling me up. This stopped feeling of my own cock getting slammed against my belly but made him ram against my prostate more often which was actually a better feeling. I felt a huge pressure build up quickly in my underbelly and while i was previously mostly moaning as encouragement and maybe a little of pleasure, my moans were noe purely of wild excitement of the coming orgasm. My mistress noticed immediately.

“she’s ready to cum now john, you should hurry up too… she won’t last long...”

“good” i heard john grunt “I have been holding back a little to get her here… you know me…”

He grunted in my ear “as soon as my pounding sends you over the edge i can ride the waves of your orgasm to my own, you dirty little whore! I will fill your ass up with my cum, you little bitch.”

In one sweep he actually lifted my up on his cock! He restrained my arms behind my back with his arms so i was impaled on his cock with my weight pushing down on him. He used his hips to just bounce me up and down on his cock some how making sure he never actually slipped out. I could feel the huge head of his cock sliding through my anus, sometimes almost popping out before my own weight made his shaft disappear completely inside me again. It took me just a few minutes before my moans became a long scream of ecstasy… I came hard!

Thick strands of cum flew from my cock on the bed some even hit my own face!
I felt my orgasm everywhere and with each burst of my cum my anus gripped johns cock tightly.
Then I understood what he meant by riding my waves… he had no problem timing it… every time my anus gripped his cock he had his thick head in the opening, making it slide to the tightest hole i had the whole session. This not only seemed to get him to his own orgasm but also prolonged my own… what a sensation i felt a wave of my orgasm simultaneously with his cock stretching my anus with the thickest part of his cock when it was the tightest before he would plow into my insides and ram my prostate….

And then he came…. Oh my god how he came… i could feel every burst of his semen splashing against the walls of my boy pussy…. He came at the point of my last few spasms of my own orgasm making the deep powerful thrusts he used to fill me feel slightly painful again.

The Noise he made as he came though… oh my… he was a wild a****l! He was the bull who was breeding me… the only thing i could do was encourage him to shoot… so i did… i told him to fill me up completely, to breed me, to own me…. And he did…

with his last few deep strokes he rammed home every drop of his cum, deep in the place that seemed to be designed for him now…

he collapsed on the bed on top of me, breathing hard….

From the chair i suddenly heard:

“bravo! that’s how you breed sissy and that’s how you take a breeding! Now before anything, my sweet sissy boy, you know what to do!”

“yes mistress” i said “cleaning!”

as i got up from underneath john, I felt his thick cock slide out of me with probably quite a load of his seed… I squeezed my hole shut making sure I would not loose anything else and i turned john over on his back. His cock started to get soft, ideal for cleaning… a thick glob of his seed was lying on the bed so i licked that up first to taste both his juice and mostly to familiarize myself with the taste of my bull. Then i cleaned him from the base of his cock to his cum drenched balls and the still oozing tip of his cock, I cleaned him good, just like i was told to do… never waist anything!

And as i cleaned him and softly played a bit with his half hard cock i felt good! I liked my bull! My mistress had chosen well… but then again she is my mistress… and I am her sweet sissy boy!

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Published 5 months ago

So I had remarried when I was 27 to a hot little chick and the sex was great, but many times I found myself daydreaming about cock and reminiscing about Charlie and the other cocks I had sucked. I was faithful to my wife for most of my marriage, but one time after a visit to an adult bookstore with all those gorgeous cocks starting me in the face I picked up a gay magazine and it had personal ads in the back. This was before the internet so I rented a p o box and started writing to several guys, sharing our experiences back and forth and would always wind up jerking off as I read and then wrote a reply. One guy lived nearby and we planned to meet, but I chickened out at the last minute, my nerves got the better of me and I didnt want to cheat on my wife.

So I took a new job about 30 miles from home, working from noon til 9 pm or later with overtime. Some of the guys from work would go out after work on Friday night to the local watering hole near work and I would join them. Typical guy stuff. I usually stayed til about midnight and since I knew the wife would be asl**p when I got home I would stop by the adult bookstore on the way home, go into a booth, play a hot video, usually a shemale video and jerk off onto the floor. So this one night I stopped as usual and they had the same old videos over and over and I was getting bored. There happened to be another adult bookstore just across the highway and I decided to see what they had to offer. I drove over there and went in, found a booth, dropped some change in and was scanning the vids, most of them were gay men, none of my favorites, which were shemales. Then out of the corner of my eye I noticed the hole in the wall. I wasnt naive, I knew what it was there for. As I'm watching this video of 2 guys in the gym sucking each other off, I could tell someone entered the booth next to me by the change of light. I wanted to see a live cock, wanted to see some guy jerking off. So I waited a minute and then I squatted down from my seat and moved as far back against the other wall as I could, so as not to be seen and peeked thru the hole. I could hardly see anything, so I moved just a little closer to the hole, still trying not to be seen. It was so dark, but I could just barely see that he had his pants undone and was yanking on a hard and fat 6 incher. I've always loved the sight of a hard cock whether in a magazine or up close and personal and love seeing guys jerking off too. I felt my cock swell up as I watched this stranger jerk his. I started to undo my jeans and wanted to jerk off right there as I squatted down and watch him jerk his hard dick.Then my stranger turned towards the hole and took a step closer. The next thing I knew his cock began to peek thru the hole and was actually in my space. "OMG, I thought. I havent done anything with another guy in years, what should I do"? I reached out to touch his cock. ohh it felt so good to have a cock in my hand again, so hard, the skin so soft and velvety just like I remembered. I stroked it a little bit and he shook it. I knew what he wanted and I didn't disappoint. My knees were shaking as I leaned in closer and licked the head. This made him moan and I then opened my mouth and let it slide down his rock hard shaft all the way to his balls. My own cock was as hard as its ever been and I started jerking off as I bobbed up and down on this anonymous cock. He didnt last real long and he shot into my waiting mouth. And it was just as it always had been, just flowing out of his dick in one continuous stream. I swallowed it all. I watched as he zipped up and left, and I sat back down to jerk off.

Not 30 seconds passed before that booth next to me got a new customer, and after another 30 seconds I did the same thing, trying not to be seen, wanting to watch him jerk off. Apparently I wasn't hiding very well as this guy stuck his cock thru the hole also. He was about 7 inches and a little thinner and I immediately put my lips around it, bobbed up and down for a good 5 minutes and he also came in my mouth. Again, I sat down to finally jerk off and make myself cum when lo and behold the next booth became occupied again. I did the same routine, looking while trying not to be seen. This cock was soft and within seconds was sticking thru the hole as well. This was the first time I was ever faced with a limp dick, which I dont find attractive at all, but wondered what it would feel like in my mouth. Yes I leaned in and took it, trying my best to work it up and down. It began to get a little firmer, but never hard and he wound up cumming in my mouth with it still being limp. I was getting ready to go, thinking I would just go home and wake up the wife and pound her pussy real good. I zipped up and waited for the video I was watching to end before opening the door. I was proud of my accomplishments, sucking off 3 different cocks and their varying sizes.

Just as the video was scrolling its credits, I had a new neighbor. I really didnt want to suck another as I knew it was getting late, so I just sat there, I didnt try to get a peek or anything, and the next thing I knew, this cock started to appear thru the hole. Im beginning to wonder, "what is there, a sign out there pointing to my booth saying, "cocksucker here" or something". My video had stopped and I figured the management would not take too kindly to people in the booths without putting money in the machine. It was too dark to make out the outline or anything of this new cock and I kind of wanted to suck it too, but I also wanted to go home and bang the wife. "what the hell, I thought, I need to at least see it and maybe just jerk him off". I dropped some more change in the machine, and when the video came on it gave me enough light to see this cock sticking thru the gloryhole into my booth. Once I got a good look at it, I saw that it was a black guy, his cock wasnt real thick, but OMG was it long. It was at least 9 inches, I had never seen a cock that big, and never seen a black cock other than magazines and videos. I just had to touch it, to feel it in my hand. I wrapped my hand around it and pulled til his balls were pressed up against the wall. I was mesmerized by the size and beauty of this hot cock. I wasn't sure if I was ready to suck a black guy or not, not prejudiced or anything, just not sure of the tabooness of it. I was perfectly content just stroking this big cock, but then he kept shaking it. I assumed this was the sign meaning "I want it sucked". I didnt know the protocol, this was my first time at a glory hole. "ok, I thought to myself, its so gorgeous I just have to see what its like". I got on my knees on the hard floor and wound up kneeling in some dried cum, apparently from one of the other guys I had just sucked. I put my lips to it and started to take it in my mouth and he pushed it further. I gagged. I had never had a cock this big in my life. I wrapped my hand around the base and blew him up and down. I was loving how this huge cock felt in my mouth. I blew and I blew for what seemed an eternity. My own cock was dripping precum onto my leg and I started jerking off as I sucked. He must've fucked my mouth for a good 15 to 20 minutes before I felt him tense up and finally I tasted his salty cum. It wasnt a very big load, but it was oh so thick and creamy. I could take no more and I jerked feverishly as he pulled his cock back out from the hole, and I shot a huge load right there on the floor.

I cleaned up and pulled my pants up and wiped my face on my sleeve, but I could still smell the odor of cock on my mouth. I exited to head home and when I got in my car I looked at the clock, it was almost 3am. "Oh God, I had been in there for 3 hours"!!

I felt guilty on my drive home, contemplating whether this was considered cheating on my wife or not. In the ensuing days, the more I thought about what I had done, the hornier I would get. Long story short, I was back at the gloryhole the following week and then again every chance I got. And yes, I did suck more black guys.

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