Diapers are the Best Gift on Valentine's Day (Patreon)

“I just don’t like you that way, Sam; I’m sorry.” Holly smiled uncomfortably and handed the flower back, “You’re cute and nice, but you’re just not my type; besides, I’m dating someone…” Sam held the flower in his hand unsure of what to do or say next. He hadn’t thought asking Holly to be his Valentine would go well, and now that it hadn’t he wasn’t sure of what to do next.

“Well can you at least do me a favor?” Holly looked uncertain, but she eventually nodded in agreement, “What do you not like about me?” Now she looked uncomfortable, “Listen, Sam, sweetie, it’s got to do with me, you, and the person I’m dating; these are all legit factors that I have to consider.”

“But what’s wrong with me?!” Sam sat back on the bed and covered his face with his hands, ashamed of his being on the verge of tears. He could hear Holly sighing from across the room. He watched from between his fingers and she stood up and walked to the bed. Holly was wearing Valentine’s Day colors, and from his point of view he could just barely see the pink lace panties poking out from underneath her red and white tutu. By the time she sat next to him, Sam could feel his cock stretching against the denim of his jeans. Part of him hoped Holly would see and beg to suck it; in fact, that’s what he usually daydreamed about.

“Well for one, you’re a crybaby,” Sam immediately put his hands to his sides, surprised that Holly would talk to him like that, “and you’re always coming here, try to sneak peeks at my underwear, and I can always tell when you do it, ‘cause your tiny little dick gets hard and you always act so smug and act like I should get on my knees and blow you.” She emphasized the word ‘tiny’ by pushing his cock down with her index finger. 

“No no no no no—,” Sam barely had any warning before his cock began to twitch and fill his underwear with cum. He felt his face redden and tears start to well up in his eyes as he watched his penis slowly pump its load into his jeans. He looked at Holly, who looked halfway between a laugh and a sigh. 

“Were you really that horny just from looking at my panties, or were you imagining me fucking you when you had your face covered?” She then did something that surprised Sam; she reached over and unbuttoned and began to lower his jeans. “W-what are you doing, Holly?” 

“What, you don’t like what I’m doing?” She lowered his jeans further down to his ankles and crouched in front of him, “Isn’t this what you always daydream about?” Sam’s eyes widened and he felt like the happiest man in the world, “Y-yes! So you didn’t mean all that stuff you said?” Holly now stood and laughed, “Of course I did, Baby-dick. Now hold still; I’m going to ask my S.O. what to do with you.”

“What to do with me? What do you mean?” Holly just smiled and took a picture with her phone, “Alright, give them a few minutes to text back and your fate will be decided.” Sam sat stunned on her bed for a bit. He was glad Holly wasn’t freaking out; in fact, he was somewhat aroused by how she was handling the situation. He didn’t like the idea of some other guy she liked deciding what would happen to him.

“I think I’ll go now…” Sam stood up and reached for his pants only to find them missing. Holly sat at her computer, Sam’s pants sitting in her lap, “I think you’ll stay put, unless you want everyone at college to see that pic. It’s not like you can leave in these anyway; they’re covered in your accident. 

Sam didn’t like the way he called his cum his ‘accident.’ It made it all feel so juvenile; Holly calling him a crybaby and a baby-dick earlier didn’t help either. “Do you really think I have a baby-dick?” Holly looked over lazily from her email and looked Sam up and down. With an audible sigh she stood up and walked over to Sam; grabbing his boxer-shorts, she lowered them and held his cock in her hand like she was weighing a piece of produce, “It’s smaller than my pinky, crybaby. How old are you again?” She laughed now as she toyed with it in her hand. Sam tried to pull away to regain his dignity, but she held it firmly, “Ah ah ah. Where do you think you’re go--,” a buzzing sound cut Holly off and she looked at her phone, “Oh my god this is too good!” Sam leaned forward to get a glimpse of the phone but a sharp tug on his dick forced him to stop, “Behave.”

Sam looked up at her face hoping to catch her intentions in her expression. Strands of blonde hair hung freely in front of her forest green eyes. Her glasses held the reflection of her phone screen, but the image was too distorted for Sam to make it out. “Well Sam,” Holly pulled him by his cock over to her chair; she sat down with a huff and set her glasses and phone down on the desk, “looks like you and I are going to be Valentines today.” 

Sam stood there dumbstruck for a moment, “W-what?” Holly let his cock go at this point and patted her lap. Sam sat down facing her, his cock growing hard again in the space between their legs. Holly put her finger on it and applied pressure, watching it bounce as it rose, “My S.O. seems to think that you’re cute; in fact, I would say that your little dick is the only reason you’re here right now.”

“R-really?”

Thank you genetics

“Yeah, she had a thing for cute guys with tiny dicks.”

“She?!”

“Yeah, she. Aren’t you grateful? Let’s tell her thanks by sending her a cute pic,” Holly stood and walked to the center of the room, taking Sam with her, “Get on all fours; make sure your ass is perked up.” Sam was too horny argue or refuse any request from Holly.

From his place on the floor he had a great view of Holly’s panties. He could feel the head of his cock rubbing against his lower stomach, “Look forward; I’m taking the picture from behind.” Sam did as he was told; making sure his ass was perked up for the picture, “Your butt is pretty good for a guy; you don’t have too much hair either.” Sam continued to wait obediently on the floor, “Are you going to take the picture soon?”

“Sorry, my S.O. just got here. I'm just chatting with her real fast. Actually now that she’s here we don’t need to take a picture, she can just see you!”

“So I can move?”

“I wouldn’t say that.” Sam turned at the sound of an unfamiliar voice. In the doorway, next to Holly stood a tall, dark-haired woman; she had her arm wrapped around Holly and was kissing her neck softly. “Sam, this is Victoria, my girlfriend.” Victoria dressed older than she looked, especially when compared to the juvenile clothing her girlfriend would wear. On her shoulder a large pink bag hung, looking stuffed to the brim.

Victoria left Holly’s side and crouched behind Sam, “Is this the little baby-dick that had an accident earlier?” Sam gasped as he felt his cock being grabbed. Victoria was the second person ever to grab his cock and, despite his position on the floor, he felt like today was turning out to be the best day ever in terms of his sex life, “Certainly feels like the one; Holly, sweetie, help little Samantha here out of her shirt while I get more comfortable.

Sam ignored the name and waited with excitement as Holly approached, “Lay on your back, Sam.” Holly’s breasts bounced as she tugged on the fabric. Sam made sure his shirt took a while to come off as he drooled over the b-cup breasts in his face. Once off, Holly moved to her bed where she too took her shirt off. As Sam’s vision went from Holly’s pink lace bra to the stripping Victoria, to his own tiny, erect member, he felt as if he was in heaven.

“Go ahead and get completely naked Holly; I’ll take care of Samantha here.” By this point, Victoria had already removed her bra, exposing her d-cup breasts. Her heels had been kicked to the side and all that remained now was the skirt. Sam’s vision darted to Holly who now watched him from the bed. Her naked form made his cock ache and he wondered if he could handle the both of them.

Victoria was now on top of him. She pinned his arms above his head with one hand, and fiercely gripped his chin with the other, “Now Samantha, I’m sorry but I forgot lube. I’m going to need you to drool in my hand to make up for it.” Sam was surprised that the two would be so unprepared but he did it none-the-less, “Don’t spit Samantha, drool.” Sam wanted to ask why she insisted on calling him Samantha and why he needed to drool when spitting would make the whole thing easier, but he heard Holly moan and immediately felt himself comply. 

Holly eyed him with such lust he had never seen. She sucked her thumb as she watched, her other hand busying itself with her wet pussy. 

“Good girl, Samantha.” Sam watched as Victoria sat on her knees, moving her drooled in hand to Sam’s crotch. Sam bit his lip hoping he wouldn’t cum as soon as he was touched, but he knew his body well.

At least it’ll feel good…

He closed his eyes and waited for her to stroke him…

…

“W-what are you doing?!” Sam’s eyes opened to reveal Victoria gently pushing her 7-inch, lubed dick into Sam, “What does it look like, Sissy? I’m having a little fun before we get on with the Valentine’s Day celebrations.” Sam made to move away but she held him down firmly, “You were right Holly, the crybaby’s pretty weak.”

Sam looked to Holly for help but instead found her lost in her own world. Her legs spread and raised, her eyes firmly locked on her girlfriend’s dick as she fingered herself, “Do what Victowia seth,” Sam couldn’t tell if her speech was being slurred by her thumb or her own pleasure, “We’ll have fun after…twust me.” She moaned aloud and seemed to lose interest in consoling Sam. 

Sam’s eyes went back to the cock currently waiting at the cusp of his asshole, “Is Samantha going to behave? Should I wait till my cock is less lubed?” Sam bit his lip and looked over at Holly.

Is it worth it if I can fool around with Holly…

Sam looked back at Victoria. Her long dark hair hung in front of her face. Her breasts heaved with each breast, their nipples erect.

“D-do it…”

“What was that sissy? I want to hear you say ‘Fuck me Mommy’ loud enough so Holly can hear,” Sam hesitated, his eyes wandered back down to the cock that was over three times the size of his, “Pwease Sam? I’ll be so gwateful.” 

Victoria watched him, hunger clearly in her eyes as she traced his asshole with her cock.

“F-fuck m-me Mommy.”

Sam breathed in sharply as he felt Victoria enter him. “There there little sissy,” Victoria stroked his hair as she pushed in further, “Let’s make you more comfortable.” Sam cursed as he felt her remove herself from his ass, “Let’s see you in that pose you had earlier, the one for the picture.” Sam found it harder to get motivation to allow himself to be fucked the longer this went on, but Victoria didn’t seem to mind.

“There we go! But let’s change one thing.” Sam yelped in pain as she pulled his arms behind his back, “There; I hate to be so rough with a delicate little crybaby like you Samantha, but you need to be properly punished for hitting on my Holly all the time,” Sam almost bit his tongue as he felt Victoria slip back into his asshole, “Once you’ve been properly disciplined…” she slowly began to pump in and out; despite the situation Sam felt his cock growing hard again, “…I’ll let you have some fun. Would the sissy like that?” Sam stayed quiet. His head had been forced down and the only thing he could see was the panties Holly had been wearing earlier; they were his only solace as he felt his ass growing more and more accustomed to the large cock inside it, “I asked the sissy a question!” Sam yelped as he felt Victoria push herself deep inside him.

“Yes Mommy! I would like that!”

Victoria slowed her assault and laughed, “You hear that baby girl? Samantha takes her training well.” Sam could hear Holly giggling from the bed. It made him feel ashamed that the girl he had crushed on for so long was seeing him like this; however, that didn’t prevent the strange feelings from his ass from causing him to moan.

Lost in the moment, Sam began to speak, “I’m going to cum H-Holly.” He felt his ass moving in time to Victoria’s cock; his cock began to twitch.

“That’s not who you need to be talking to!” Sam cried out as he was spanked. He could hear Holly moaning behind him, the sound of her pussy being fingered being drowned out by his own humiliating fucking, “When you cum little baby, I want to hear you say: ‘Baby make cummies,’ over and over, understand?” Sam nodded his head fiercely, desperately trying to keep from having an orgasm.

“Howwy make cummies Mommy! Howwy m-make c-cummies!”

Sam lost it. The cock inside him was too much, and Holly’s enthusiastic orgasm took him over the top.

“B-b-baby make cummies. B-b-oh god—,” Sam felt Victoria cumming inside him. The feeling of the hot semen shooting inside his ass felt so good he couldn’t control himself as he lay in his own semen. He moaned as she pulled out and didn’t even bother to move as he felt the rest of her cum dripping on his ass.

“Good enough, Samantha. We’ll have to train you to be a bit more obedient, but that’ll come with time. You two certainly made a mess though.” Finally free to move his head, Sam looked up to see Holly sitting up in the bed looking drained from her orgasm. Victoria stood nearby, softly stroking her hair.

“Now that’s out of the way, let’s get to work on getting you two ready for your Valentine’s Day dinner.” Sam felt content to watch from the floor in the pool of his own cum. Victoria pulled the large pink bag up onto the bed and began to lay its contents out neatly next to her. “You’re roughly about the same size as Holly, aren’t you Samantha?” 

“Why?”

Victoria didn’t bother to respond, but instead continued to pull out more and more from the bag. From where he was, Sam could only make out the tail end of excessive frills and the sounds of soft rustling and crinkling. What he did have a clear view of was Victoria’s still dripping semi-hard cock. Victoria looked over at him on the floor and smiled, “Is the baby still hungry?” Victoria grabbed her cock and bounced it up and down; it looked even larger in her feminine hands, “Come over here and finish the job then.” 

“I think I’m good.” Sam could barely believe he had just taken it in the ass; sucking the cock that had just fucked him was too humiliating.

“Says the pathetic little sissy. Tell me little sissy: does it feel good to lie on the floor in your cum after being fucked by someone with an actual dick, and not that little nub you have between your legs.”

“Hey fuck you bitch. Why do you keep treating me like this anyway? I’m leaving.” Sam made to leave before all the confidence he had just mustered sputtered out, but Victoria was quicker. She straddled his chest in a flash, her cock flopping about in Sam’s face, covering his chin in cum. 

“Holly, hand Mommy one of your special pacifiers. Little Samantha needs to be punished.” Sam desperately kept his mouth sealed as he could feel Victoria’s cock hardening anew. Holly crawled over, still naked from the bed; she sucked on a large red pacifier with straps that hung down from the side. She offered a similar, pink one to Victoria and waited patiently as Victoria strapped the red one around her head. 

Victoria’s cock was now fully hard and she looked at Sam with such lust that he was unsure if he would make it out of Holly’s house without swallowing semen. “You see little Holly here? She’s a good girl,” Victoria tugged on the pacifier in the girl’s mouth; Holly leaned forward in response, her breasts on full display, their nipples erect. “If you want to get anywhere near her today, you’re going to learn to be a good girl too, understand?” Sam looked at Holly’s glistening body and felt his cock stir again. 

Victoria held the pacifier above him, “I’m going to keep her nice and horny from now on; no more orgasms for her unless I say so. If you behave yourself, I might let you be involved. If you don’t…” a smile spread itself slowly across Victoria’s face, “…I just might change your name to ‘fuck toy’ and use you like one.” Victoria rubbed her dick along Sam’s lips, her cum smearing all along the way, “You choice: obedient sissy, or fuck toy I keep tied up in my closet. Hell I might even let my guy friends use you. I’m sure they’d appreciate a tight little hole like yours.”

Sam had never felt more in a pickle in his entire life. He stared at the pacifier dangling above his head; the nipple was large and shaped like the head of a penis. Regretting every decision leading up to this one, Sam decided one more bad one couldn’t hurt. His lips parted and he pushed his tongue forward, the taste of semen hitting his taste buds.

“Obedient sissy.”

Victoria frowned, “I was beginning to think I had a free fuck toy; oh well, at least Holly has a playmate now.” Sam kept his mouth open and watched the pacifier lower.

Once it’s in, she’s going to strap it on and I’m stuck…

He closed his eyes and felt the head slowly begin to enter; but it didn’t end there, soon the shaft was making its way and the taste of semen filled his mouth. Sam opened his eyes in shock as Victoria’s balls bounced against his chin as she began to fuck his mouth. She laughed with delight, the pacifier still dangling above his head.

“What’s a matter Samantha? My cock too much for you?” Sam did his best to find a way to expel the cock but Victoria’s knees kept his arms pinned easily. His mouth, in an effort to force the cock out, betrayed him and found itself sucking in time to the intruder’s thrusts. “Little sissies earn their pacis, got it? You show me you can suck like a good girl and I’ll let you have it.”

Sam began to feel like coming to Holly’s today was a mistake; however, Holly didn’t seem to think so. She was already in the middle of cumming by the time Sam could focus on anything but the cock in his mouth. He could see how wet she was between her legs; he could hear her moaning sporadically behind her pacifier and wished that at the very least she was the one doing this to him.

Sam did his best to focus on other things so that his forced cock sucking could end sooner, but every time he managed to focus on something he could feel the cock go deeper, “Pay attention little sissy; Mommy is almost c-clo—oh g-good girl. Good girl!”

Sam’s mouth filled with semen. Victoria sat back on his stomach, her cock dragging a line of semen with across his chest. Sam quickly made to spit, but found his mouth stuffed yet again by another cock, this one being the head of the pacifier he was promised. Holly held it firmly but didn’t attempt to strap it.

Victoria breathed heavily, a smile plastered on her face, “Good girl, Holly!”

“As for you little sissy, you should know better than to spit,” Victoria leaned forward and moved Holly’s hands, quickly working to strap the humiliating thing into Sam’s mouth, “Now you’ll swallow all of Mommy’s load, won’t you?” Sam looked first at Holly, feeling betrayed, then at Victoria. Seeing no other options, Sam swallowed the cum as best he could trying not to gag around the cock pacifier in his mouth. 

“Good girl, Samantha! Now I think it’s time for a treat for good little girls.” Victoria reached over to the bed and dragged a stack of clothes down. She set it to the side and then lifted the first one off the top to show Sam: a thick, pink rectangle covered with hearts of varying sizes. Victoria spread it open into a large hourglass shape and then placed it next to Sam.

Is that a…

“Holly, sweetie, hand mommy the wipes and powder.”

A DIAPER?!

Sam immediately began to struggle against Victoria. He did his best to speak behind the pacifier but quickly found out that the only response he could give was a muffled: “Mmmph!” 

“Oh, what’s a matter? Do you see all the cummies you made on the floor? You clearly need this! Besides…” Victoria ran her finger across the head of his still erect penis, “I think you might have another little ‘accident’ soon.” Sam continued to struggle, even though he knew the woman was clearly much stronger than him, “Do I have to spank the baby’s bottom? Holly’s already seen you get fucked like a bitch twice today, now you’re about to be put in pampers like a baby. Would you like to worsen your image by crying and being spanked? Is that all you are? A little crybaby?” 

Sam slowed his struggling and sulked as Victoria looked down satisfied at her prey, “Good girl! Holly likes it when you’re a good girl; don’t you Holly?” Holly handed off the powder and wipes to Victoria and looked down at Sam, she nodded and ran her hand along his stomach, stopping just before his shaft and giving it a soft pat.

Sam looked away from his humiliation. He twitched as he first felt himself cleaned by the wipes, “Baby, look at Mommy she has to clean her cum off your little chin.” Sam did as he was told. Soon he was powdered and he watched as the pink, thick, disposable humiliation was taped around his waist.

The thickness of the diapers forced his legs apart, and each small movement he made caused the diaper to crinkle loudly. He sat up and watched as Holly was powdered and diapered, clearly enjoying the situation far more than he was.

He could see himself in the floor length mirror Holly kept near her closet. The thick diaper, large pacifier, and red face made him look exactly like the large crybaby Victoria claimed him to be. His cock was still hard inside his disposable prison and it was obvious just how small he was by the tiny lump it made in the front of his pink diaper. He turned back to Holly to see her writhing on the floor in pleasure, rubbing her diapered crotch and gleefully sucking on the pacifier in her mouth.

Victoria returned her attention to Sam, grabbing him by the waist and pulling him into her lap. He watched in the mirror as his blond locks were pulled back into pigtails, “Does this make little Samantha happy?” Victoria gently kneaded his dick through the diaper, “It certainly seems like it. And it looks like you’ve gotten used to sucking on your paci like a good baby.” 

Sam was shocked to realize that he had indeed been absentmindedly sucking on the cock pacifier in his mouth.

She’s turning me into a big baby! I need to put a stop to this soon…

“I’m really glad you’ve decided to embrace your baby girl side. If you hadn’t, I would’ve sent you on your way dressed just like this; although, I wonder if you would’ve preferred that? Dropped off in the middle of your college campus, bawling your eyes out in a messy diaper…” Sam breathed in sharply as she continued to rub his crotch, “But don’t worry little one! You keep doing what me and Holly tell you to and I’ll make sure your love of cock and diapers remains a secret,” Sam began to moan now.

Being her baby isn’t so bad…at least I’m with Holly…and I don’t want to be humiliated in the middle of campus…

“I can tell just from how you’re relaxed in my arms that you’ve decided to be a good girl. That’s so very nice Samantha; but before we can go further, I want to make sure you remain a good girl.” Victoria reached over to the stack of clothes and laid something soft and pink in Sam’s lap. The fabric was light and little teddy bears decorated it. It was designed like a pair of panties, but they looked too large for Sam and a small piece of ribbon ran all the way around the top leading to a small, heart-shaped lock.

“These are your good girl panties, Samantha. Mommy is going to slide these over your diaper and lock them in place. Once on, only Mommy can take them off; meaning, you need to behave yourself. If you don’t…” Victoria locked eyes with Sam in the mirror, her lips softly grazed his neck, “…I’ll make you behave, understand?”

Sam’s head was still clouded by his stiff member, so when he nodded enthusiastically he had no idea how short lived his enjoyment would be. 

Victoria grinned from ear to ear as she stood, lifting Sam by the armpits with her, “Let’s get you dressed and I’ll let the baby make cummies, okay?” Sam didn’t care anymore; his eyes were locked on Holly’s breasts and his cock strained against his diaper. He gladly stepped into the locking panties and he sucked eagerly on the pacifier as a frilly pink dress was pulled over his head. His hands migrated to his crotch but were quickly slapped away.

“Looks like the little girl is a little excited; you’re in diapers now princess, only Mommy can say when you make cummies, understand?” Sam just nodded his head, still not caring.

He allowed his hands to be put in locking, pink mitts. He gladly wore white tights and light-up, pink sneakers. He even sat perfectly still as a white lace choker with the word ‘Baby Girl’ on it was put on him. His nails were painted shades of pink and as a finishing touch Victoria put pink ribbons in his hair.

He was placed in front of the mirror and the pacifier was removed from his mouth. “What does the baby think?”

The overgrown infant looking back at Sam was not Sam; in fact, she barely looked anything like Sam. His eyes wandered all over the cute baby girl looking back at him and he had to admit that the sight made him hard. 

A soft pat to his rear returned him to reality, “Come on little girl, tell Mommy what you think.”

“I l-like it.” Sam watched, red-faced as Victoria reached forward and tugged upward on his diaper. He breathed in sharply; he was the closest he had been to orgasm since diapered, “That’s not how a baby talks; try again, and remember if you make cummies without my permission, you will be punished.”

She tugged upward again. Sam couldn’t take it anymore; using the last of his dignity he desperately tried to comply as he felt his cock begin to twitch, “I w-wike it Mommy-y-y-y ohh…”

He bit his lip as he felt cum fill his diaper. His eyes began to water as he imagined the various punishments Victoria would inflict upon him. 

Victoria just laughed, “Naughty, naughty girl. At least you know how to talk now; but you clearly need to be punished for that little accident you just had.”

Thinking fast, Sam responded, “B-but mommy babies sposed to make acceedents.”

This is getting ridiculous…I can’t believe I let this happen…I need to stop thinking with my dick…

“True, little girl; I’ll keep that in mind when I punish you,” Victoria replaced the pacifier in Sam’s mouth and tightened the strap, “Now, be a good girl and go stand with your nose in the corner.” 

That was a punishment Sam hadn’t received in a long time. He hesitated at first, but a quick swat to his diapered rear got him moving. 

“Now, Holly baby, sit up so Mommy can dress you.”

Sam waited for a good while, listening to the sounds of what was going on behind him. At first only the sound of crinkling and rustling, then some cooing and baby talk, then for a while nothing. 

“Alright Samantha I’ve decided on your punishment; you can turn around.” 

Holly was dressed a bit more grown-up than Sam. Her outfit consisted of a pair of red short-alls and a white shirt with pink hearts all over it. She wore similar sneakers to Sam and her hair had been pulled into matching pig-tails. Victoria had changed into more casual wear; just a pair of jeans and a sweater. The contents of the diaper bag had been replaced and she now sported the heavy thing on her shoulder.

“We’re going to a nice little restaurant for Valentine’s day. My friend owns the place and she’s been informed about the big babies that will be tagging along. She’s also been informed in detail about you.” 

Sam felt his face flush, sweat pouring from every spot it could.

This can’t be happening…

“I’ve got the car running and I’ve brought the strollers, figured I could do a couple errands while we’re out too. Maybe if you’re a good baby, you’ll get a treat! Doesn’t that sound nice, Samantha?”

Sam suddenly felt very self-conscious of the thick diaper forcing his legs apart. The cute girl he had seen in the mirror was about to be in the public eye; meaning, that cute girl was him to everyone else. 

Despite himself, Sam began to cry. Victoria just laughed as she took him by the mitt and pulled him out of the room. As he walked downstairs and outside he hoped his dress was long enough to hide his padded shame.