Daddy Milks a Straight Boy

Disclaimer:

Hey everyone! My first story on this new account, it's based off of a Daddy fantasy I have. A little dark given the 'noncon' category of this, always ask consent, no means no, and this is very much a FANTASY. I don't profit from this of course, I just like writing these things out. This is a fantasy I have of getting dominated and turned by someone older than me. If this isn't your cup of tea, please don't read this so that you aren't at all triggered or given any bad feelings about this story.

Any way here's the story!

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My name is Cory, I'm about 5'11 and am starting on finishing my college degree. I'm about to be 23 now, and I'm a little scared of graduating. I don't have a lot planned out and I've only got a few internships under my belt. Regardless though, I'm happy for the experience and am still a little excited to get out of a roommate situation and settle into my own place.

My roommate, Tom, is around my age, we've been at the same off-campus apartment now for a year or two. Inflation's been a bitch and my job on campus isn't paying the bills anymore, luckily Tom is already working a steady office gig and I don't to pay as much on rent (he got the master bedroom). Either way though, I'm jealous. Stress is really starting to set in.

Only thing I could do in these months leading up to true adulthood was distract myself. I downloaded a dating app and hoped that maybe some flirting and dating would take my mind off things. I'd been single a while and maybe I just needed to be back on the market.

One night while on the dating app I got matched with a woman WAY out of my league. Her name was Stacy, and immediately messaged me. I was shocked, and didn't respond at first, assuming it was some kind of bot. It wasn't... holy shit why is she talking to me???

Stacy and I were talking back and forth for days on end, Tom even had to ask me to get off my phone at a certain points. However, after a while she finally asked me the question.

Stacy: Soooo, I see you're into older women...

Me: Haha, yeah ig so lol

Stacy: What else are you into??

Me: Like sex-wise and stuff? Uhhh let me think haha.

Stacy: Cuz I'm really into younger boys... cute and effeminate like you...

Effeminate? I mean yeah I can't grow any body hair and people have complimented my ass before... but... well yeah damn I guess I am...

Me: Sounds like I'm a good fit then haha, you into anything else?

Stacy: I hope it's not too much, but I'm really into domination, love strapping down boys like you and showing them a good time.

Oh wow, can't say I'm opposed to that at all.

Me: I can be into that haha, I haven't ever really tried stuff like that before. Honestly, I'm really into anything I don't have a preference at all.

Stacy: Oh perfect, what about butt stuff?

WOW

Me: Haven't really tried it... not opposed but I'm not gay so...

Stacy: Oh baby it's not gay at all, it'll feel good I promise, but we can do whatever you're comfortable with...

Me: Sounds like a plan then lol, you want to meet up sometime? We can go somewhere in public if you want to make sure I'm not some weirdo first haha.

Stacy: I only do this stuff to straight boys btw, I love making you straight little college boys squirm under me... I can meet, but let's just do mine, I'll send my address over.

Me: Sounds good lol

Stacy: God you're so perfect baby, I can't wait to get my hands on you. I'll strap you down and milk you dry, make you beg for me by the end of the day.

Holy shit! This woman's freaky.

Fully erect, I jacked off that night, running through all the fantasies and what she could possibly do to me. I'd never played sub before so this was a whole untapped gold mine of fetishes I was waiting to explore.

I messaged her again the next day, and we picked a time about a day or two in advance, her condo, no dinner, no small talk, just right into the action. She sent me paragraphs of the diabolical things she'd do to me and my dick. Sucking, tying up, inserting, exploding, the verbiage was insane. I'd never been so aroused before a date.

.........................

The night of... I arrived at Stacy's condo, decent neighborhood, pretty average looking building. I get a text from her with the room number, telling me to come in while she freshens up.

I arrived at her floor and opened the door slowly. What I saw was a decent brown carpet floor, a small kitchenette, nice and undecorated balcony, plain and boring furniture, the shower running in what looks like a quilted white bed. Not what I'd expect of a kinky cougar's abode...

I heard the shower screech off as I closed the door behind me.

"Hello?!" I called, "I'm here, shoes off?"

"Wherever you want baby..."

I froze, that voice was a lot deeper than I thought it'd be. I turned in horror, there was in fact not a sexy cougar waiting for me in the doorway to the bedroom.

The man was fat, hairy, and old, roughly in his later 50's possibly a little younger. A towel was wrapped around his waist, a cocky smile on his face as his eyes drifted up to me a little. He was just shorter than me. He was clearly balding, and not what I'd describe as handsome.

"...Just in time baby..."

He took a step towards me, I stammered, no idea what to even say in this scenario.

I took a step back, "Wha...who-, is this some cuck thing? I'm not sure I'm into that man."

"No no boy, I think you're misunderstanding, I'm Stacy, I'm gonna be your new daddy."

"You're... you're a man..."

"Oh that, I guess I forgot to mention it."

He dropped his towel, his hairy belly hanging down slightly, not far enough to cover the thick bush exposing his massive cock and big set of balls. My jaw dropped, I had rarely ever seen another man's dick, I was in shock at the situation but his size as well, far bigger than me and my five inches.

"Yeah keep looking boy, you sure you came here hoping for a woman tonight?"

"I-I, I uh, I really should go..."

"Already? We can still have fun tonight straight boy, how about you come to the couch and sit on Daddy's lap. Nobody has to know except me and you... I see the way you're staring, you're curious aren't you."

I stammered again, not able to admit he was a little right, something about this situation... something about him doing the things that 'Stacy' said she was going to do to me... it sparked something in me. My adrenaline kicked in though, I've never been with a guy, let alone been interested in one, and my first time with a guy won't be with a fat older man.

I stopped thinking and sprinted out the door, not looking behind me, sprinting down the stairs to my car. I drove off without looking back.

......................................

The next day...

I came out to the shared kitchen to see Tom making coffee.

Tom gave a half-smile, "Hey man, how'd your date go?"

"Uh... not well... I got catfished..."

"Ah shit dude, for real? Didn't look like her profile?"

"Kinda... it was an old dude actually."

"Woah! Damn that's a twist, you gotta be careful man. You alright? He try anything?"

"Sorta, just flashed at me and then I went out the door."

Tom gave a light chuckle, "Damn, he packing? You liked what you saw?"

"What? No dude, no, too soon man come on..."

"You're right, you're right sorry, not the time. Well as long as you're okay, careful on those apps though."

"For sure dude, can I have some coffee?"

"Yeah of course, use the rest of the pot, I gotta dash anyway."

"No worries, appreciate it."

On his way out the door Tom stopped and looked at me.

"What."

"You know if you're gay you can tell me right? Like seriously it's cool if you are, I don't care."

"Dude! I'm straight! Drop the subject! I like women! Okay?!"

"Alright alright... All I'm saying-"

"GO!"

Tom shut the door behind him, I gave a deep sigh. Alone in the apartment.

A few hours of me watching TV passed, I checked my phone in the meantime, remembering rent was due in a few days and I wanted to see how much money I'd have left. It didn't look good, I'd have to be eating from the microwave for the next 6-weeks. My parent's won't help me, and I can't ask Tom to cover rent. Stress began to pollute my mind again.

I calmed down eventually, and opened up the dating app, and began swiping. I realized I missed some new messages from 'Stacy'. Curiosity got the better of me, and I opened them just to see what he said.

Stacy: Hey boy, looks like I startled you, guess I came on a bit too strong. Saw you ogling my cock though, thought I'd give you this as a gift.

Below was an image of his erect hairy dick, a long veiny member that stood amongst his nests of hair and belly. Thick as my slender wrist, but about as long as my forearm.

Jesus this guy doesn't give up.

Stacy: Like what you see? I wasn't completely lying boy, I can do everything 'Stacy' can, and more... Don't worry I won't fuck you or anything... yet. I just wanna play with you first. You were clearly thinking about it last night, I saw the tent you were pitching before you left...

I was? I didn't even realize it...

Stacy: Think about it boy, my door's open always.

Me: Not interested dude. I don't know what you saw but it wasn't that. I'm gonna block you now.

Almost immediately after I sent the message and made my finger towards the block button, he replied.

Stacy: What if I paid you?

I paused.

Me: Yeah right.

An image came up immediately, a wad of 100 dollar bills between his thick fingers.

Stacy: 3k, just for a handjob, I make you cum once and then you're out the door.

I froze. I really need the money... I'm just getting a handjob it's not like I'm really trying anything new...

Me: And if I don't cum?

Stacy: Another 3k until you do.

Fuck.

Me: Okay. Fine.

Stacy: Fuck yeah boy. Come over right now. I'm so horny.

Me: And you're not gonna fuck me or something right? I'm straight I don't want to do any gay shit okay?

Stacy: Course not boy, I'll give you the money first just as insurance.

Me: Fine.

Stacy: See you soon boy.

...............................................

One hour later...

I arrive back at 'Stacy's' place. I knocked on the door and opened to the cocky smile of the older man, looking up at my bright red face.

"Come in boy, make yourself comfortable."

He opened the door and I entered, feeling his stare burn into the back of my head, and the back of my ass.

Almost immediately I feel his hand on my back, and the other grabs my waistband, stopping me from moving.

"Not so fast boy." He turned me towards him and put a wad of cash in my waistband, "Don't get so eager you wanted money first right?"

He kept his thumb looped under my waistband, his thick thumb slowly caressing my side.

"Unless you want to negotiate for some more money, if you want to try some more things today..."

His hand slowly slipping past the waistband and stroking my upper thigh slowly under my shorts.

"You'd look so fucking hot with your cute little ass around my cock while I fuck a load out of you. Bouncing up and down..."

His hand moved to my cock and balls stiffening rapidly while he began to harshly rub his hot palm up and down my shaft.

"N-no, I'm good for right now thanks..."

"You sure? You were fine with 'Stacy' doing just the same with a strapon weren't you? Just close your eyes..."

He gripped my hand around my cock, giving a hard tug before I stepped away, releasing his hand from my pants.

"Let's get this over with please..." I said looking away, unable to hold eye contact.

"Of course." He sneered, "Let's get you on the table..."

"Table?"

He walked into the other room, a spare bedroom that was behind a locked door. He pulled out a key from under his brightly colored polo. The door opened to a soundproofed room with racks of sex toys. A computer hooked up in the corner, and different series of furniture folded and leaned against a wall for space. There was a gynecologist chair, a doctor's observation table, and another table that was pulled out into the middle of the room.

The table was black leather and shaped like a person, clearly meant for me to lie down in, cock up, and my hands legs to be strapped down. My legs and arms meant to splayed out in a starfish position.

He grabbed my shoulder, massaging it slightly, "On the table boy, I'll get you strapped in."

"Can we do it without the bondage? I don't want you trying anything while I'm that vulnerable."

"I'm a man of my word boy, well minus the 'Stacy' bit"

His hands slipped under my shirt and slowly pulled the cash out of my waistband.

"Unfortunately though I'll need to take this back unless you get strapped down." His hands lingered, fingertips under my waistband still.

"W-what difference does it make?"

"All the difference baby. I'm more of a giver, and if there's one thing I love it's strapping down straight boys and making them cum until there's nothing left..."

His body pressed against my back, his one hand sunk back down my pants and began lightly squeezing my bare ass, the other reaching up my shirt to my right pec and rubbing it, his fingers slowly gliding on my skin and around my nipple. His mouth right in my ear.

"I love making them squirm while I just milk them endlessly, just going and going until they're just quivering by the time I'm done. Giving these straight boys the time of their lives, making them realize what they really wanted. You sure you don't wanna stay longer? Become a Daddy's boy?"

His tongue licked up my neck, shuddering as he dragged it up to my ear, diving it inside, squelching with hot moans and breath in between. I couldn't move, I couldn't hide the erection I was sporting. This is so weird, this is so gross, I hate this I hate this I hate this.

He gave me wet kiss on my ear, "Now get on the table boy, because I think you'll find soon enough that I'm not some desperate lonely old man who pays boys for sex. You're here for me..."

He pushed me forward, ass first, his hands slipping out from under my clothes. I turned to him, gulping, my heart beating out of it's chest.

"Just one hand job right..."

"Of course boy, only if you want more. Which you will."

I pulled off my clothes, and nervously got on the table, looking up at the ceiling, stark naked. My dick half-mast.

He came around and began tightly strapping my wrists and ankles down.

After I was secured and fastened unable to leave or escape, he licked his lips. I was caught and there was nothing I could do, he could do whatever he wanted to me and I couldn't do anything to stop him. His musk was overpowering as he brought himself closer, not saying a word and beginning to remove his shirt and pants. Now completely naked.

"Just wanna get comfortable." He breathed. His hands immediately on my body right after, rubbing me up and down, as he began to groan and moan with lust.

"Fuck you're just so perfect, such a tight, young, and hot body. I bet you've done it so many times. Fucking some random girl at parties, and now you're here... I can do whatever I want now, but lucky for you I'm a nice guy, and I'm true to my word..."

I was silent, I wasn't giving this guy any reaction or any satisfaction.

His hands moved on either side of my head, I tried looking away but he forced my head to make sure I was staring deep into his hungry gaze. His thumbs rubbing my cheeks slowly. One wandered over to my plush lips, rubbing the lower and then inserting it into my mouth.

"Suck on it."

Not part of the deal, but fine. I closed my mouth as began drawing it in and out of my mouth, slick with saliva. He did this for another minute or so, his thick thumb exploring every corner of my mouth.

"Such a hot mouth."

He pulled out his thumb with a POP, wiped the saliva on my face.

"I'll throw in an extra three hundred if you let me kiss you right now."

"Can we get the hand job over with please?"

"Whatever you say boy, the offer's there."

His hands traveled down my body, as he began to kiss my chest and belly. His right hand finding my dick, that was already erect.

"Uh oh, someone likes it... A bit dry though."

He moved his mouth down to my erection, and out of nowhere sucked it into his mouth! I gasped.

I had no time to realize he had my dick in his mouth before he began bobbing up and down my cock with expert method, his tongue tightly wrapping and working my cock while he applied suction, I'd never experienced a blowjob this good in my life! I couldn't help but moan... loud. Loud enough for him to stop, a trail of spit as he popped his mouth off my member.

"Yeah you like that don't you boy. You like when your Daddy get's you nice and wet. Don't worry I'll make sure to give you a proper blowjob once we're done... only if you want of course."

"Hu-hurry up, come on man..."

He grinned ear to ear. His hand now working my shaft, his hands were thick and warm, soft, and now wet with his own spit. I hate to admit it but I was already losing it. He was a pro, and he wasn't kidding it definitely wasn't his first time doing this. It was all I could do not to keep moaning. He spat on his hand again then kept working my dick with his hand, his eyes locked into mine the whole time.

Fuck! Stop looking at me! Why is it turning me on more?!

"Yeah you're gonna give me a big load aren't you? A big fucking load for Daddy."

Holy fuck why was this working, if I saw this man at a bar or the street I'd never EVER imagine myself turned on by him, but now, good god what's happening?! This old fucking pervert is giving me the world's best hand job!

His hands were like machines, his right pumping up and down with slick and wet squelches, twisting and tugging on me firmly but not hurting me. The left cradling my balls, rubbing them together. Occasionally his middle finger was brushing my taint, making me lurch a little each time until his fingers were rubbing my taint up and down while my balls were cupped in his palm.

His dirty talk wasn't helping me either.

"Look at you straight boy, getting a hand job from a dirty old man, gonna cum a lot huh? Gonna shoot a big fucking college boy load. Yeah I know how fucking horny you little college boys get, you're gonna shoot a big fucking load for me right?"

SQUELCHSQUELCHSQUELCHSQUELCH

He was picking up the pace now, the room echoing with the wet hand job going up and down on my dick, his hand now making sure my tip was getting love. In fact he began to focus on the head a lot more, making me spasm, he laughed each time I would lurch my hips, my sensitive tip couldn't take it.

I felt it then, the feeling in my lower abdomen, I was going to cum, really fucking hard, I was about to prove this old fat pervert right. Nonononono! NO!

He sensed it too, seeing my expression change he smiled even wider, and began moaning as if he was enjoying it with me. His pace picked up even faster, the wet squelching going faster and faster, starting to send me into a frenzy.

"Ugh ugh ugh, yeah boy, fucking cum for me, cum all over Daddy's hand, show him how much you love this."

"Oh my-... Oh my god!"

FIP! FIP! FIP! FIP! FIP!

He was furiously fapping away at me now, I was about to cum, my balls began to tingle, and my body began to quiver.

"You wanna cum?"

I couldn't say anything.

"Say it!"

I didn't respond, just as I was about to climax, he grabbed the base of shaft, coming to a halt. I gasped, almost in pain as my balls began to seize.

"NO! PLEASE LET ME FINISH!"

"Say it. Say it boy, Say you're gonna cum for me."

"I'M GONNA CUM FOR YOU! I'LL DO ANYTHING PLEASE JUST LET ME CUM!"

"Say you're gonna cum for Daddy."

"I'LL CUM FOR YOU DADDY! PLEASE DADDY!"

"That's a good boy."

He rapidly stroked by cock with both hands, immediately bringing me back to climax.