chriswinters2022

[chriswinters2022]

#235

This is a direct follow up to Story #210.

“Joey, it’s so fucking good to see you again. I’ve been thinking of you the entire last months of my divorce. Here come on in and check out my new home. Yeah, I had to sell my home I had with Cathy. Don’t miss it, or her....

“Hey, when you come into my house, you are to strip immediately. When you are done, come over here and give me some much-needed head. I’ve been thinking of nothing else but you naked and in front of me. When I had lunch with your dad and mom today, all I can think of is shoving my cock into your cunt. As your mom was going on and on about how great you are and will make a fine husband, I was thinking of you eating my shithole from under a rimseat while your cunt is being pounded by my biker buds. As your dad was drinking his wine, I was thinking about you drinking my piss out of a water bottle.

“Now I am bringing up my lunch with your parents because you need to know what else we talked about. By the way, has your dad called you? No? Good. Good. During dessert, I was mentioning that I just bought this house just north of the university to get away from the expensive center city. I was saying that this will be the first time I will be alone and that I may take on a roommate, maybe even a student. But I worry who would move in. That’s when your mom said, ‘Joey could move in.’ Your dad even said that you will be a great roommate and that you won’t to worry about drinking or have girls running around looking to get their MRS degree. I chuckled at that one.

“I said that I would feel funny about taking money from him. Your dad said that you will work for me, doing what I say. He’ll make sure that you are obedient. All I can think of is that my backhand slapping you upside your face does the same thing. So here your dad and mom are offering you up to me as an obedient cunt.

“Just think, we used to have just the one weekend a month to go up north on one of our bike runs and fuck and fuck. Now every night, every day, every weekend I will reserve the right to fuck your cunt, piss down your throat, plant my shithole on your tongue, slap your face, lock up that pecker, gang bang you, whenever and however I want. Faggot, you have been begging me for more time with me before I had to cut it off due to the divorce, do you remember what I told you? Don’t answer that, your mouth feels good with my cock filling it up. It would feel better if my cockhead was deep in your throat. Atta boy.

“I told you that one day I will take ownership of you. I’m doing that now. Faggot, you are now mine. We will move you in as soon as possible. I have a special room for your school stuff downstairs. You will need to pull out A’s. I will be tying you to your seat with a dildo shoved in your cunt while you study.

“I know school starts in a week. So we are going on a drive. There’s a vista point a few hours away which gets crazy at night. There’s a glory hole or two that you will spend some time at along the way. I want you dripping of spooge from both holes. I want you covered in piss. I want your face to reek of the rank of the asses of real hard working men. And I want your cock to be completely ignored.

“This is your new life—no, our new life together. We will figure out when to tell your parents, but we will one day. But first, I need to dump my load. Turn around and impale yourself. I hope you are clean. If not your mouth will clean it up.”

[chriswinters2022]

[chriswinters2022]

[chriswinters2022]

[chriswinters2022]

Life Lessons - Epilogue (Preview)

On Monday morning, January 6th, Alan was ready to start a new stage in his life as part of his recovery journey after the pregnancy and the delivery of Max’s nine babies. He entered a multi-use studio room he’d meticulously designed over the last few months to balance his roles as a father, an anatomy professor, and a wildly popular OnlyFans content creator. The room combined academic professionalism, paternal touches, and hints of kink-related activities.

The room had sleek bookshelves and a wide desk with a computer and textbooks on it, alongside softbox lights, tripods, and a cushioned bed with embroidered pillows. Across from Alan’s work desk sat a wide rocking chair—cushioned and reinforced to accommodate Alan’s body—beside a bassinet packed with soft toys and burp cloths. It was Alan’s center of operations after returning home to his wife and older boys, with the newborns and Max.

Alan slowly settled into the plush seat at his desk in front of his large monitor. He adjusted the webcam’s angle to capture only his shoulders and head—nothing below the chest, where his massively swollen body resided. The university he had worked for until a year ago now had him back on their payroll, but only for online lectures. They had recently started the online modality, and for Alan, it had been a blessing considering the current state of his body.

[chriswinters2022]

[chriswinters2022]

[chriswinters2022]

#333

“Look I ain’t interested in conversation with you.  I answered your ad because you promised to eat ass for a long period of time.  Nothing else is going to happen.  I’m not looking for a finger, or worse, a dick to go in my shithole.  I have no desire to stick my dick in a fag’s asshole or in its mouth.  It’s just going to be me sitting on your face for a few hours.  You got that?...  Good!...

“Your ad said that you have a portable rim seat on legs for me to sit on.  You better have brought it.  Good.  Go ahead and set it up down below.  I have a spot for you to set up.  I want to look out while I enjoy my scotch, a cigar, and an eager tongue slurping my shithole.

“You are the first fag I have ever been with.  Two years after I had a whore from Amsterdam eat my shithole right, I have been searching for any woman to do it with such enthusiasm.  I even dumped my girlfriend because she wouldn’t spend more than one minute total back there.  I’ve seen pornos, lots of pornos.  So I know that those bitches exist.

“Right here.  Set up the seat right here on the edge of the step.  You are going to lie behind me; I don’t want to see any part of you.  I only want to feel your moist tongue going in deep.  Put the seat right up against the edge.  From what I have seen in porn with these seats is that the men sitting on them have to stoop down low to sit and it looks totally uncomfortable. 

“Here’s a bandana.  Put it on as a blindfold.  I saw this done in a porno ‘Cuck Husband 3: Eating My Wife’s Lover’s Ass’.  That’s where I first watched a fag eat a man’s shithole.  This is where I got the idea to use queers.  Yeah, that husband was a total fag actor.  He hardly ever did anything with the women.  I’ve seen him in other cuck videos.  He’s always slurping on some big brute’s shithole.

“Get under the seat.  Keep that bandana covering your eyes.  You don’t get to see my cock and balls resting on your forehead.  Hell, you won’t even get to see my shithole you will be tongue fucking.

“Fuck you look like you were made to be under that seat, that your life is to lick other men’s shitholes.  Open your fucking mouth….  Now the other thing that brute did to that cuck in the porno was this….  A piss-soaked bandana will make sure your eyes remain closed.  And I don’t care that some goes into your mouth.

“…And it appears that you don’t either.  Well damn faggot.  You really are nasty.  Doesn’t surprise me considering your tongue is going to spend a lot of time inside the hole I shit out of.

“Get ready, this is the moment you have been waiting for.  In your e-mail from the other day, you asked me not to clean up after work today.  You wanted to eat me out ripe.  Well, I stopped cleaning it up from that moment on.  Here’s my three day ripe ass.  Get that tongue in there.

“Fuuuuck.  Jesus fuck!  Oh hell yes….  Mmmmm….  Oh that fart slipped out….  Damn, none of this phases you.  That Dutch whore has nothing on you….  And you can do this for hours at a time?  Faggot, the job is yours.  When I say we are done, we’ll work out a schedule.  And we’ll get a more permanent chair installed, one that is more comfortable for me to sit on for hours.

“Until then, I’m going to enjoy this cigar, my scotch, and watch the sun set listening to the sounds of you slurping and sucking on my shithole.”

[chriswinters2022]

[chriswinters2022]

🏳️‍🌈 beach buddies

[chriswinters2022]

[chriswinters2022]

#323

“Tollinson, get over here.  Get in the passenger side now….  Shut up.  You ain’t waiting for anyone else; you are waiting for me.  I’m the one who responded to your ad.  Now get in….

“What? You looked shocked.  Can’t imagine your math teacher on one of your hook-up apps?  Well, here I am.  For the past three years you have been drooling over me in my front row.  Don’t think I didn’t notice it.  Some of you fag boys are so fucking obvious.

“Now that you graduated and turned 18 last week, I finally get to respond.  Drooling over my bulge in class wasn’t the only thing I noticed about you.  I know you frequent the bathrooms on the football field.  I know you saw my dick at that one game when you followed me in and took the other urinal.  I saw your head turn slightly to check me out.  I’m 6’5”, you are what 5’7”?  It was easy to see what you were doing. 

“After you saw my dick, I know you went into the stall to give it a tug.  I know, because I saw you come out five minutes later with a wet spot in your trousers.

“I hope you like cigars.  If not, I don’t give a shit.  I always have one going when I drive, and when I’m at home.  It turns me on.

“Did you lust after any other teachers?...  Or was it just me?...  No?  Not even Mr. Lange in Chemistry?  I know for a fact his dick is big, not as big as mine.  Then again I haven’t found the man whose dick is.  You probably enjoyed gym class with Coach Thomas, strutting around the locker room naked hoping that he would catch a glimpse of you showing off your ass.

“Of course you did that.  You are a fucking fag teenager with raging hormones.  Your profile confirmed to me what I always suspected, that you like the older men.  Am I right?...

“It’s no longer ‘Mr. Clark;’ it’s ‘SIR.’ 

“How many men have you been with?...  Answer me boy!...  This is going to go smoother if you don’t hide things.  I don’t give a shit if you have never been with a man before or if you regularly get gangbanged behind the local biker bar.  I just want to know what I am dealing with.  How many men?...  None?...  That’s hard to believe.  Your dad ever touch you like that?...  Your brother?...  Uncle?...  Cousin?...  Priest?...  Mailman?  What about playing with other boys?...  Good, so you do have some experience.  What did you do?...  Handjobs?...  Blowjobs?...  Did he suck you, you suck him, both did each other?...  So you are naturally a cocksucker.  What was his name?...  Again. What. Was. His. Name.?...  Really?  Interesting, I wouldn’t have expected.  Did he cornhole you?...  Good lord!  Do I have to explain everything?  Did he stick his cock in your asshole?...  No?  Anybody ever fuck you?...  So you are a virgin back there?  That’s going to be changing pretty soon.

“You don’t have much experience, how the hell did you write that profile?...  You read it on the internet and watched videos?...  Shit!  Seriously.  That’s a lot more than I had for me.  In the Army another soldier and I messed around a few times.  Then he introduced me to a bunch of his friends.  It was all underground.  If I had drooled over one of my teachers like you did me, I would have been taken behind the school and beat up.  Things have changed indeed.

“Here’s my house.  When the garage door closes in a few seconds,... I want you to get out of the truck and stand by the door.  Take just your dick and balls out, then look down at the cement floor....

“...Your pecker is rock hard.  My dick will take some time to get going. Remember this slab of meat?  Look at it.  This is the exact same pose as when you saw it at the urinals.  Huge isn’t it.  Your pecker is rock hard, and it doesn’t even come close to mine semi-hard.  Reach over to it.  Take a hold of it in your hands.  Go for it.

“That’s a real man you are holding on to.  Hold on to my balls too.  Those balls are what really give me my bulge.  When you are with a man, not another boy, you need to focus on what the man wants.  His cock should always be your focus.  Whether you are casually stroking him, or taking him in your throat, or up your ass, you make sure that you put his pleasure above everything else.  You should never touch your pecker unless he says so.  Leave it alone.

“Why don’t you get on your knees and look at it up close.  You are going to spend a lot of time with it controlling every part of you.  Feel how hard it’s becoming?  See that pre-cum starting to leak out?  Go ahead and taste it.  It’s going to have an awkward taste, but you will learn to love it.  You swallow the other boys’ loads?  No?  Bitch, my load will go wherever I want it to go: down your stomach, deep in your ass, or all over your face.  You never refuse a man’s load.

“Stand up and strip.  I want to see what I get to play with….  Don’t get shy on me, now.  We are going to be naked soon with my cock going in your ass.  No time for shy.  I’ve already seen your tiny pecker, nothing else to be shy about.  There you go. 

“You are going to be spending a lot of time over here with me.  You are going to be naked any moment you are in my house.  When Lange and Thomas come over to hang, you will be naked around them.  Oh yeah, they are going to know that you are my fag boy.  Don’t worry their own fag boys will be naked alongside them.  Yeah, they both are like me.  We like young men.  The thing is that we don’t do current students or anyone under 18.  We don’t need those problems fucking up what we have.  They are going to shit once I have you parading around naked.

“Boy, don’t know what you are embarrassed about.  Decent body.  It’s clear you don’t work out, but that’s ok.  I do enough of it for both of us.  This is all mostly muscle under these shirts.  It’s nothing for me to pick you up like this and throw you over my shoulder….  Quit fidgeting.  We are going into my bedroom, I’m going to take what is mine, that cherry.  No, this is not up for discussion. 

“Hold on.  Duck your head a little.  A few steps and… you are going to be so easy to toss around.  Now I want you to witness what you have jerked off to for so many years, me getting undressed.  As you sat in your desk looking up at me, when you were staring at my crotch, I knew you were wondering what I was like under my clothes.  Well I’m a 52 year old math teacher.  You would expect me to be chunky with a huge ball sack.  But I’m not.  I work out for an hour twice a day every day with three hours on the weekend.

“Look at me.  Look at this chest.  I spend a lot of time to get my chest built out.  I’m going to be plowing you in just a moment.  You are going to be overwhelmed, but I want you to focus on me and my pleasure.  Run your hands all over my chest, through the hair, and focus on my nipples.  My tits are wired to my cock.  You roll my nipples through your fingers applying a small amount of pressure and you will get my dick going, and it won’t take long.

“You know what this is?  This is lube.  I’m going to put more than I usually do because you have never had a cock up there, you are on the small side, and my cock is fucking huge….  It’s cold isn’t it?  Slippery too.  Feel that?  That’s my finger going in deep.  Feels strange hunh?  Wait ‘till my cock gets buried deep in there.  I’m just checking how clean you are.  And it appears that you are.  Open up your mouth.  Clean off my finger.  No. No.  Your mouth is a great hole to clean off whatever comes out of the other end.

“If you repulsed about this, wait until you eat my ass.  Heh heh.  Yes, your tongue will not only lick my sweaty ass crack, but it will go inside.  Trust me you will love it.

“Ok scoot backwards and raise your legs.  Give me that pillow.  This will keep your ass at the right height.  Now place your ankles on my shoulders.  This angle gives my dick the best thrust.  It also allows you to open your hole up.  The following is the most important advice I can give you.  Push your asshole out, as if you are going to take a shit.  It will lessen the pain in your hole.  This is going to be painful, and it needs to be.  There is a fine line between intense pain and ecstatic pleasure.  There will be a point where it shifts from one to the other.  I can feel that change happen to you by how your hole surrenders to my cock. 

“In your head, you will start to realize just how much pleasure you can get out of it.  It is at that time that for the rest of your life, you will yearn for a cock in here.  A real man’s cock.  I have never had a boy who didn’t crave my cock once we were over.

“Feel my heavy cock at your hole.  You ready?  I don’t care if you’re not.

“Scream fag, scream!  No shit you are a virgin!  Push out.  I know it’s uncomfortable with your knees by your ears, but man does this position feel so good.  I can feel your inner sphincter open up.  The way that it is massaging my cock head, boy, I am not going to last long.  Play with my tits like I told you.  A little bit harder. 

“Fuck yeah fag.  Fuck yeah!  You ready to get your guts flooded?  Stop pushing out and clamp down.  Oh yeah.  Fuck.  Here it comes.  Here it comes.  Fuuuuuckkkk!  Uhhhh!  Uh!

“Fuck fag.  That was intense.  Don’t move a fucking inch.  I’m going to let your legs go, but keep them up in the air until my cock falls out of your cunt. 

“Oh yeah, it’s now a cunt.  Cunts are holes thaT men use and abuse for release.  You better believe that I am going to be using this hole regularly.  This cunt belongs to me.  That by default makes you a cunt too.  You belong to me now.

“Let me put my cigar down.  You ever get kissed by a man?  Not a peck, but tongue action?...  You’ll get used to the cigar taste….  You’ll crave it. 

“…Wow.  I’m going to fall asleep for a nap with my cock in my new cunt.  Try to keep it inside you as long as you can.  Enjoy how everything is tingling at the moment.  While I am asleep, think about after these past years how your fantasies finally came true.  I know I’ve been waiting for this too.  Shhh shh.  Time to sleep.”

[chriswinters2022]

[chriswinters2022]

[chriswinters2022]

[chriswinters2022]

#128

“So why are you contacting me? I mean, we live across the country from each other. Yes I am a controlling son of a bitch. I control everything in my life....

"I have a boy and two slaves, each knows about the other. I don’t allow jealousy. They all serve and service me in their own way. What gets me off is knowing how they sacrifice for me. They sacrifice their comfort, their well being, and their thoughts to pleasing me.

"When I get home from my business trip, my boy greets me with a gift. Every time is different. Every time I’m impressed with how thoughtful it is. He’s always putting my needs first. He longs for monogamy from me, but he understands I will not be. He knew from day one that he would give up all other men for me. Yet, in fact he surprised me by finding the service slave.

"When I return from my business trip, my service slave takes my suitcase and puts everything away. With the exception of my dirty underwear, my clothes are immediately washed, folded, and put away exactly how I want it. He thrives on keeping my house spotless and orderly. All I have to do is nod approval to something he did to send him soaring.

"My dirty underwear is presented to my bathroom slave to clean in his mouth. He’s the one that greets me at the door offering to drink my piss. He lives to sacrifice himself by drinking my piss, cleaning out my foreskin, eating my rank ass, sucking my underwear clean, giving me a pedicure with his mouth, and whatever disgusting thought crosses my mind. He’s also a great cook, and dinner is prepared by him with the service slave assisting as needed. They do this so I can spend my time with my boy and my gift. My slaves wait on us. Later on that evening I will probably fuck my boy, usually with my slaves in attendance ready to act on any need I might have. I know they both long for the passionate sex I have with my boy. All they get is the savage fucking when I need to be brutal.

"My question to you is, what are you offering me? It’s clear you need someone who will control you, to put you in your place. You need a real man to provide you a focus to your life. You want me to control you, but why should I? What are you offering me from across the country? And don’t give that bullshit of ‘I will do whatever command you give.’ I mean, how does that benefit me? That’s usually selfish fags who are looking to get themselves off. If I want a sexual activity done, I have three bitches that will do what I want right there in front of me on my command, not 3,000 miles away. So what do you offer me to make my life easier, more comfortable? My business has me traveling all over the country. I have four more years until I retire. You want to help? Figure out a way to get that time down.

"Right now, the only thing I can think of for you to do is to pay tribute to me. And the amount needs to be a real sacrifice on your part—no casual pathetic twenty dollar tribute. I want you to offer an amount that requires you to work longer, or harder, or anything you can to earn extra money. And when you are working those extra hours I want you to keep saying to yourself, ‘This is for SIR and HIS pleasure and comfort.’ That thought should dominate what you think about. I want you to get hard thinking about how your extra work will please me. Your sacrifice to me should be like a drug—the more you do it, the more you need to do more.

"I will expect to see your finances, all of your finances. You will be put on an allowance. When I come out to the East Coast, you will be my slave to be used the way that you crave. And you will give up all other men. No other man will interfere with your paying tribute to me…. Unless,…

"No, I have a better idea of what you can do. You are a handsome 22-year-old fuckhole. I want you to be a whore, a true whore. You will charge other men to use you. I will receive all funds, and I will give you a portion of it that I feel you have earned. I want you working out every day. I want you eating well. I want you in top shape for men to pay the big dollars to fuck you. And when the ugly fat sweaty men are lying on top of you brutally shoving their tiny dicks in you, or some muscle man is shoving his thick arm painfully deep in your cunt, I want you to remind yourself that you are doing what I expect and that it pleases me. No request will be turned down, no matter how disgusting you feel it is. Instead you will thank me for the opportunity to serve me as you submit to doing something so vile with another man. Your selfless service to other men will bring me comfort and much wanted funds. That’s what I want from you. For now, being my whore will be in addition to your current job, but as you get a reputation built, we will transition you into daddy/boy porn. Over the next month, I want you to install cameras throughout your apartment so I can see you being used like a fucking whore should be. Until I accept you permanently as a live-in slave, this is how you will sacrifice for me. And that sacrifice starts now. Send me your on-line bank access. I want to see what I am dealing with. Otherwise piss off.”

[chriswinters2022]

#225

“Are you Skylar313? Did you do everything I told you? Good. Strip. Completely naked. Right here, in broad daylight. You hesitate, and I’m leaving you here. Good. Fold your clothes in front of me. As you do your shorts, hand me the contents. If you have any last minute reservations about doing this, now would be the time to walk away. I went over this in our on-line chats. Just give me a nod, and your old life is over. Ok, done….

“I will be in full control for the next six days, after which you will belong to The Agency. I see your wallet is kinda empty. Driver’s license. You’re almost nineteen. That’ll bring a good price for you. Shit! Your name is Skylar Jayden Cassian Jackson? No wonder you want to leave your life. For fuck’s sake. Your new name is Cunt. It’s much simpler. It’s easier for me to give the name of Cunt to all the fagmeat that comes through my rig. Then I won’t get too attached when I finally deliver you at the end of the week. Two credit cards. They will be maxed out; probly a few hundred dollar dollar limit..

“Come closer. Three day stubble after full body shave. Turn around and let me check out my new cunt and crack. That is one pretty cunt. Pink pussy lips that look almost virginal. You’re not a virgin right? That’s right, you sent me a pic of you taking it up the cunt by some guy with a very thick dick. Very little hair, that’s good. Turn so you are in the sun. Hold still. I need to take a pic. Close up of your pubes too. The agency will decide if you should keep your naturally blonde pubes. If so, I will have your hair permanently removed tomorrow night. I have a bud that will meet us. He’s going to take you back to his place for the night and rape you and permanently remove your hair. You’ll keep the eyebrows, as fags look stupid without them. Bend the fuck over and pull apart your cheeks. They also need to see this perfect cunt hole. Now hold still. Got it. Damn, this cunt is picture perfect.

“Stay in that position. I got to send these pics off. If any man should come around, graciously offer both holes. I’m gonna be up here sending those pics. Looks like you have your first customer, and it’s an old friend of mine. He and I used to team drive, procuring fagmeat like yourself…. Hey Charlie! Got a prized one. Check out the cunt’s cunt. Go ahead and fuck it. It’s not a virgin. You got lube? Use some lube. While I love hearing fagmeat screaming from being fucked, we are not in the best situation for that. I’ll be down in a few. I just sent the Agency its pics….

“What was that?… Like a velvet cunt? Hunh. I’ll be down in a few moments…. Ok…. Just heard back from the Agency, and Cunt spin around and clean off Charlie’s cock. I’m going in…. Fuuuuck. Smooth. Velvet’s a good word…. Charlie, I know that look on your face. You want this cunt? Heh heh heh. You haven’t changed. The Agency is paying 20% more than fair market collection price….

“Hey Cunt, spin around, I want to try your pussy mouth. All the way down. All the way down. Atta cunt. What’s your offer?… Double? Fuck! Who would pay double?… Really? I haven’t heard his name in years. He’s still building up a harem of gelded fags, and he wants a fair skinned ginger hunh? Wow….

“Hey CUNT! Get back into place. This discussion doesn’t concern you. You gave up all rights to your body not ten minutes ago. Now spin the fuck around. I want more of that hole. Will he pay the 20% buyout fee from the Agency?… He will? Without you even consulting him? Damn he trusts you. We got a deal.

“Cunt you hear that? You were just sold. Fastest sale in a long time. I’m ready to nut…. I’m not pulling out until either I nut or the funds transfer. Until then the Cunt still is mine. I’m about to shoot. Oh yeah! Oh the fuck. Oh man, this hole is truly like velvet. That was a huge load for sure. Cunt, clean me off….

“Charlie, until I hear that funds have transferred, he’s not yours. Get your phone out and start the process. And Cunt, face me and get on your knees. Jack off. Now! I know the man that just purchased you, and you are going to be castrated. Charlie is under strict orders to not let any acquired slave to touch itself let alone cum. So this will be your absolute last time you can erupt. Have at it. Suck on my cock if that will help. I want you to see what a last load shooting looks like.

“You are close aren’t you? Faster Cunt. I can see it in your eyes; I can feel it on my cock…. Oh that tone on my phone indicates…. yes the transfer went through. Get your mouth off my cock. Cunt it looks like you are about to… Damn! Interrupted by a steel toe boot to the balls from behind. Those balls have got to hurt. Don’t worry, that pain will be taken care of pretty soon. Charlie, it is all yours. I’m gonna get some rest.”