SPH-THEMED EROTICA STORIES

“We need to talk. We can’t keep fucking like this. I have a very small vagina, and your dick is shredding me inside. It hurts.”

“Well, it’s not like I’m big; I’m only five inches hard.”

“Why do guys always know their dick size?”

“We measure it; it’s a lifelong competition.”

“If you want to compete for me, you’re gonna have to make your dick smaller.”

“How about I just enter the tip?”

“You’ve said this before, and then you get all horny and hump me like a poodle.”

“What if I just rest the tip inside you? I won’t even move.”

“No more whining ‘just the tip’. You don’t keep your promise.”

“What do you suggest, then?”

“Funny you ask. I’ve been doing a lot of research about how to shrink a man’s penis. Even though yours is only five inches, it’s too big for my tight, hot, sexy pussy. You do agree my pussy is deliciously tight, right?”

“YES.”

“And you want to keep it that way, right?”

“Yes.”

“Awesome. Then you need to start taking these ‘Penis Shrinking Pills.'”

“Where did you GET those?”

“A friend. The pills are all natural. Completely safe. Shrinkage is only temporary. When you quit the pills, your five inches return.”

“The label doesn’t say shrinking is temporary…”

“Well, your other option is prolonged chastity. And I don’t mean abstinence. I mean we lock your cock in a chastity device for maybe six months. I hold the key. But the research isn’t conclusive that atrophy will set in.”

“I can’t do that; I have to be able to cum.”

“Well, you DO release sperm in chastity. Just absolutely NO contact with your shrinking penis.”

“Then how in the hell do I cum?”

“Based on your tone, you don’t want to know. Let me get you some water. It’s time for you to take your pill.”

“If I’m cock locked, do I get to cum or not?”

“It’s called ‘milking.’ I massage your prostate and coax your sperm out once a month for your prostate health. In six months, I will unlock you. If your penis has shrunk enough, you might get to fuck me. Open your mouth. It’s time to swallow your pill.”

He caved. He was so pussy whipped he swallowed the “penis shrinking pills” faithfully every day for weeks.

Quickly, he could see his penis was smaller. And each time he showered, chunks of his body hair disappeared down the drain.

At two weeks, his flaccid penis appeared uncircumcised. The shaft had shortened so much his penis head disappeared like a turtle retracting its head.

He summoned his girlfriend for an inspection and to announce he was ready to fuck.

“Awww…your dinkus looks so cute, all tiny and shriveled.”

“Where are you going?!”

“To grab a tape measure, silly.”

He stroked and stroked, only to achieve a semi-erection.

“Almost three inches!”

A scrotum inspection found marble-sized balls where walnuts used to live.

He wasn’t shrinking everywhere; his nipples grew from dimes to half dollars. And they were extended and puffy.

“You’re going to need a bra for those.”

“Can we please fuck now?!”

“You’re pretty soft. Do you think you can penetrate with that little thing?”

He tried; boy did he try. His girlfriend’s pussy was so tight, he couldn’t get in.

She tweaked and pinched his soft, puffy nipples. They were so eroticized they signaled him to orgasm. He squirted sperm all over her impenetrable slit.

She suppressed a giggle and went to her purse; she retrieved a cock ring and a butt plug.

“Let’s try again using these toys to help.”

“The ring will trap blood for erection assistance, and the plug will awaken your prostate.”

The toys worked. His rectum felt oddly full, and his puny penis was legitimately hard.

“Now stick that golf pencil in me!”

It was her most pleasurable fuck ever. She diddled to orgasm. Her tight pussy clamped down so hard with each spasm it ejected his small shaft from her inner walls.

Her labia encased his softening shaft so well only his penile head was visible as he continued to thrust.

He was humping the folds of her skin on the outside of her pussy, unable to penetrate her vagina. Intercourse became outercourse.

With just a few twists on his puffy nipples, he helplessly came again.

“I need to get off of these pills.”

“On, no! Honey, you are just getting started.”

*****

Hollis was pussy whipped in the worst and most unusual way. So beaten that Tatiana convinced him that to get his dick wet with her pussy, he had to shrink his penis to fit in her very hot, tight bald vagina. He reluctantly swallowed Penis Shrinking Pills for several weeks. And the pills worked. By his calculations, his penile length had shortened by more than forty percent. But there was more. The pills came with additional side effects: he was growing small breasts, his nipples puffed out, his pubic hair fell out in clumps until his groin was bald, and his formerly five-inch penis was less than three at its hardest. That is, when it could get hard. A real boner was becoming rare. He needed a butt plug up his ass and a cock ring around his scrotum for any chance at a stiffie. When his penis was soft, it looked like a thumb with a slit at the tip. His testicles were now the size of marbles.

After faithfully submitting to three weeks of Penis Shrinking Pills and the emasculation journey that came with it, Hollis’s second attempt at sex with Tatiana was more humiliating than the first.

INTERCOURSE BECOMES OUTERCOURSE

Even with the butt plug and cock ring, Hollis was mostly limp. When he was semi-erect enough to penetrate Tatiana’s exquisitely tight shaved pussy, her sexual arousal squeezed out and physically ejected his little penis. Not only was her vagina tight, but it was also strong. Adding to his humiliation was the bra she had him wear so ‘his small feminine tits’ wouldn’t bounce around when he was thrusting along her slit. He was humping her slit because he couldn’t properly penetrate. Intercourse had become outercourse.

Tatiana could and would decide exactly when to make Hollis shoot his load. She’d just take each of his large puffy feminine nipples in her fingers through the soft satin bra and turn them like keys in a doorknob, and he’d start squirting. Because Hollis wasn’t able to stay penetrated, his only option was to hump her vaginal folds. Tatiana’s tweaks erotically ‘forced’ Hollis to dribble and then eject sperm all over her bald pubic mound. She called his puffy nips “gasmic knobs. Turn left or right for instant success.

Tatiana was horny; she wanted to be licked. Her desire found Hollis slurping in and around his own jizz, swallowing his sperm while sucking on her clit.

BOY, DOES HE LOOK GURLY

When their ‘coupling’ was over, Hollis went to the bathroom to pee. He was embarrassed to see himself in the mirror. He sat to pee to avoid holding his minuscule shrinking tool in between his thumb and index finger.

His body looked like a girl’s with a penis, especially with Tatiana coercing him into a sexy beige satin bra. His tiny shriveled penis had a cock ring around it, and when he turned around, he saw the base of the massive butt plug she securely embedded up his ass. The plug was huge. Massive. Likely larger than any man’s cock he figured. He felt so full down there. Rectally stuffed.

He decided he was done with the Penis Shrinking Pills. He couldn’t continue this humiliating ‘feminization’ journey any longer. Tatiana wasn’t worth this. No woman was. But Hollis wanted a third attempt at fucking Tatiana for all his efforts, so he pretended to swallow the pill, hiding it in his lower gum like a pinch of chewing tobacco.

HOLLIS IS FUCKED

But the third attempt went even worse than the second. Hollis’s tiny penis was limp the entire time. He was unable to get an erection, even a three-incher. Tatiana’s solution was to stimulate his prostate more. She removed his butt plug and replaced it with a seven-inch dildo- which Hollis wondered why she even owned in the first place. Tatiana had Hollis get on hands and knees, and she worked the dildo in and out of his ass. He was embarrassed Tatiana fucked his ass; he felt like a woman.

“Let’s see if this does the trick; it works for some guys,” she coaxed.

Hollis wished he hadn’t glanced over to look at Tatiana’s full-length vanity mirror. He saw his hairless feminine figure getting fucked in the ass. He saw Tatiana’s grip at the base of the huge phallus working the cock in and out of his ass like she was scrubbing a toilet. He saw his long, soft, flowing hair covering his face and the strap of his beige bra. If he hadn’t known it was him, he would’ve thought Tatiana was working her dildo in and out of a sexy woman. He was getting semi hard from the butt fuck. Secretly, he enjoyed how good it felt despite the humiliation at his girlfriend’s hands. But each time she paused to see if they could fuck, he quickly became limp.

“I have another idea!” Tatiana boasted excitedly as she positioned the suction cup dildo on the wall and crawled underneath Hollis, who was positioned on all fours. “You ride the cock and fuck yourself in the butt while you try to fuck me! It’ll be fun for both of us!”

Why was she so excited, he wondered. He blushed when she playfully said, ‘fuck yourself.’ At this point, his embarrassment outweighed his pleasure.

“I’m done with your ideas, Totty. Can I please just rub on your slit? Maybe I’ll get hard that way.”

Totty was Hollis’s affectionate nickname for Tatiana.

“You DO want to enter my tight pussy don’t you?”

“Yes, of course.”

“Come on, you little sissy, give my idea a try!”

“I suppose it’s worth a try, but this is really embarrassing. It seems kinda silly.”

“Well, your silly sissy penis obviously enjoys it.”

Hollis had not heard her call him a sissy before but still reached around and guided the fake cock into his ass. He felt pathetic that he’d willingly insert this rubber cock up his own hole while trying to give Tatiana the intercourse they both wanted.

As Hollis tried fucking Tatiana, each unsuccessful downstroke failed as he slid almost completely off the large rubber dick. Then each time he pulled away from Tatiana’s sexy slit, he essentially drove the dildo deep up his ass. He moaned each time because it felt good.

From humiliation, not pleasure, he decided he just couldn’t continue.

A HUMP TO EAT CUM

“Please. Can I please, please just rub on you? I can’t get in, and I need to cum.”

“This is fun! But okay, Hollis. But when you squirt on my mound, you’re gonna lick it up like last time. Sissies eat cum.”

In the end, it was just more submissive sexual humiliation for him. Tatiana ordered him to lie on his back. He had to thrust and hump her crevice like the opening of a banana peel. It was hard work. His limp, less than three-inch penis had no chance of vaginal entry. None. Tatiana just straddled over him and watched his workout.

Hollis bucked and thrusted upward. Tatiana giggled at his hopelessness. When she got bored, she raised the elastic band of Hollis’s satin beige bra and grasped each nipple between her thumbs and index fingers.

They both knew what turning the knobs would do. Sperm trickle time for Hollis. Sperm spitting time for the little sissy penis. He noticed he no longer squirted cum with force; it was better described as oozing secretions. On cue, he came, coating Tatiana’s entire bald Mons Pubis with sticky, cloudy sperm. The volume of sperm was impressive. Tatiana inched forward to straddle her body over Hollis’s open and ready mouth and served Hollis a large and full serving of his own cum. Hollis circled his lips to slurp up a sperm chunk. He lapped her belly for more. He cleaned up every slimy drop. Tatiana suddenly stood up.

A SPIT IN HIS STOMACH

“You need to take another pill right now!”

She sensed something was amiss and called him on it. Tatiana watched Hollis closely place the Penis Shrinking Pill in his mouth, making it difficult for him to hide that he wasn’t planning to swallow it. If he wasn’t mistaken, this was the second time he thought she might be rubbing herself while he submitted to his feminization pill. When he said he was done and tried to ‘go to the bathroom,’ Tatiana had caught him in the act. The pill was still in his mouth.

“Lie on your back and open your mouth,” Tatiana ordered. “Let me help you enjoy swallowing.”

He always did what she said.

“Here’s some lube for your pill.”

Tatiana puckered her lips outward. A small drop of clear saliva formed and cascaded down into his open mouth. Weirdly, this turned him on. Tatiana produced several clear streams of saliva that trickled down to his open mouth. Upon receiving enough lubrication, he gave in and swallowed the pill. His penis twitched from the submissive experience.

But even though he swallowed, they got into a verbal spat.

BREAKING UP CAN BE HARD

“I knew something was different!” She said, pissed that Hollis was cheating on his penis-shrinking agreement.

“Tatiana, you don’t understand. Taking the pill is making my penis limp. Our sex is worse, not better,” he tried to explain.

“Well, we’re done fucking; you’ve lost the competition.”

And that was that. Tatiana kicked him out right then and broke up with him. She kept saying he ‘cheated on her’ by not taking his pills.

PUFFY NIPPLES AND FRILLY PANTIES

Hollis’s outlet was his buddy Preston. He’d confide in Preston to mentally unpack what was happening with Tatiana.

It was a shocking conversation for two dudes to have.

Some of the dialogue went like this:

Hollis: I had to break up with Totty; I really had no choice.

Preston: Bro, I am still trying to grasp what the fuck you just told me.

Hollis: My ex, Tatiana, was so pissed that I stopped her pills; I had to bail.

Preston: Dude! You took Penis Shrinking Pills?!! Isn’t that what you called them?

Hollis: Yes. I Fucked up, I know. And they made my dick shrink really small.

Preston: That’s really messed up, man. What the fuck were you thinking?

Hollis: And the pills made my nipples puffy!

Preston: I did notice they were lookin’ weird. Like a girl’s nips, to be honest.

Preston reached out and playfully twisted his friend’s puffy extended nipples through his shirt. It made Hollis’ dick twitch.

Hollis: Hey. That’s not funny!

Preston: Dude, you need a bra!

Hollis: It’s even worse! All my pubic hair has fallen out!

Hollis lowered his shorts to show his buddy that his pubic area was completely bald. He forgot he was wearing her rhumba panties, Tatiana’s. Preston unexpectedly laughed when he saw the smallest penis he’d ever seen while catching a glimpse of the frilly outlines of what were obviously women’s underwear.

Preston: Whoa! Bro!! That’s fucking crazy. You shave now?

Hollis: NO! I’m bald from those fucking pills!

Preston: Those rhumba panties are a bold move.

Hollis glanced down to recall his underwear choice while blushing from embarrassment.

Preston: Why the fuck did you let her talk you into this? You shoulda said no.

Hollis: Dude, you see how hot she is. She’s the hottest fuck I’ve ever had.

Preston: I thought you told me you slipped out?

As the conversation intensified, Hollis’s tone grew increasingly desperate, while Preston’s demeanor grew increasingly masculine.

Hollis: Well, I did penetrate her! Uh…Once!

Preston: Bro, you slipped out. It ain’t a true fuck unless you came inside her. Sorry, brah.

Hollis: It was her hot, muscular, tight vagina that ejected me. Dammit. I fucked her!

Preston: Ok, whatever, buddy. You didn’t cum in her. Just sayin’. Now, what the fuck is up with your tits?

Hollis: It’s those pills. They’re doing more than shrinking my dick; they’re feminizing me!

Preston: Hmm. Okay. Not even gonna ask about your panties.

FEMALE DOMINATION

Hollis didn’t want to tell Preston that Tatiana made him wear a bra. Or the last time he attempted intercourse Tatiana basically fucked his ass with her dildo. Or that he was feeling like a submissive girl in sexual situations with a dominant woman. Or that the humiliation also actually turned him on. A Lot.

Preston: Well, it’s simple enough. You quit the pills. You quit Tatiana. Fuck her.

Hollis: I tried. And now she says I won’t compete for her because I’m not on her pills.

Preston: You mean she is fucking other guys? What does ‘compete for her’ mean?

Hollis: I dunno. Apparently, Totty claims any guy who gets to fuck her has to shrink their penis on account of how tight her little hole is.

Preston: Bro, that is soooo fucked up. But I see it now. I get it. She’s a femdom.

Hollis: What’s a femdom?

Preston: Never mind. A super hot woman like Tatiana just hasn’t met the right guy. She just hasn’t been given a proper fuck. That’s all. You’re better off without her. Except, dude, seriously…you really need to make some wardrobe adjustments.

Hollis’s body looked like a male transitioning to female.

Author’s Note: At this ‘transition’ point in the story, Hollis’s pronouns become she/her. Hollis’s name will be intertwined with her female persona name Holly.

A GURL NIGHT OUT

Holly had small natural breasts with puffy extended nipples the size of dollar coins. Her waist was thinner, and her hips were wider. Her butt from behind looked like it belonged to a hot fit girl–fleshy yet firm. There wasn’t a single hair on her body. With her long flowing mane and androgynous face, Hollis could easily pass as Holly, a sexy, alluring female. With eyeliner, eyelashes, lipstick, heels, and a dress, she would be sought after by men anywhere. And sure enough, she was.

To ease the ongoing transition tension, Preston took Holly to the Pink Pony Night Club for a relaxing night out. She was getting checked out by guys immediately. Maybe it was because of the lip gloss she wore that she used like chapstick. Or maybe it was the tight lime-green tank top that accentuated her chest, making her look like a nineteen-year-old college girl. Her perfect ass in jean shorts would be reason enough. Perhaps it was her braided ponytail. Holly claimed she didn’t intend to look like a super cute college girl, but she did. Preston acknowledged the wardrobe changes; he thought she might have taken him too seriously. The glances–stares–came from all directions. Why do college guys like skinny feminine bodies that look 19? And a fit round ass with petite little breasts? Large boobs are overrated; apparently, many young men want small.

Several guys at the Pink Pony surely agreed, and Holly’s free drinks were the proof. Guys kept buying her next round.

“Preston, could you please tell those guys I’m a dude? For goodness sake.”

“Sure, bud. I’ll tell them. But with that top, you should’ve worn a bra.”

“That’s actually funny. Tatiana says the same thing.”

Preston laughed. They both did. He was highly entertained by it all. That his friend seemed to be undergoing a feminine transition at the hands of a now ‘ex-girlfriend’ was weirdly fascinating. And she looked legitimately attractive. Hot even. Preston’s attempts to explain that his friend was actually male didn’t fly. A guy approached their table.

HOLLY GETS HIT ON

“Hi, my name’s Brad. You from around here?”

“Didn’t Preston tell you? I’m a guy, Brad. Thanks for the drinks, but tell your friends I’m not interested in men.”

“Oh, okay. What are you interested in?”

“This is weird because I feel like you are hitting on me. And your group keeps buying me drinks.”

“We were just trying to save your boyfriend some cash.”

“He’s not my boyfriend.”

“Nice. So you’re single then?”

“Yes. Well, technically yes, my girlfriend just broke up with me for…wait…I’m single. I’m single for women. I’m not a single woman,” Holly was struggling with an explanation.

“Well, your ex has great taste. You are by far the hottest looking woman in the bar, and we were just curious if you were free.”

Holly was momentarily speechless. She didn’t know what to say or do. Having a guy say ‘the hottest looking woman in the bar’ caused a twitch in her little penis.

“Free? Free for what?” Holly hadn’t meant to sound open for this next reply.

“If we promise not to hit on you, would you come to our place for some casual poker? It’s just guys. Nickel, dime, quarter. Harmless. We don’t bite.”

“You…are inviting me…a stranger…over to your flat for poker? Why?”

“We need more players. Preston could come.”

Preston was in. The two agreed it would be more fun than just sitting at the Pink Pony getting more hammered.

POKE HER

The mindless poker hands wore on for a while–with the main topic being the recent World Cup–when Carlos upped the stakes to a tequila shot for the lowest hand of each round. Thirty minutes later, everyone was now ripped. Two guys departed. There were only a handful who hadn’t left: Preston, Holly, Brad, Carlos, and three other guys–all the same dudes from the Pink Pony earlier.

Holly started losing more than anyone else. Losing poker hands and losing her composure. Like, she would twirl her ponytail with her fingers and sit with her hairless legs spread wide. Like, her crotch was an open invitation.

“I cannn’ttt dreenk uhnutter drop,” Holly said with slurred speech.

“Maybe a drop of clothes instead of a drop of alcohol?” One guy asked.

“Strip Poker?!” Another enthusiastic guy asked like a statement.

“Strip poker with all dudes, that’s weird,” Preston interjected.

“It can actually be more intense—more fun. Guys don’t like the humiliation of losing and having to show their junk. What? You all afraid?” Carl had been thinking all evening about what to say when the game got to this moment.

“Fluck No, Lessss Go!” Holly combined the word ‘fuck’ and ‘let’s’ to slur a new word: fluck.

There was a pending problem, though, that would soon surface.

Holly forgot she was wearing Tatiana’s lacey panties. She gave Holly several pairs–before they broke up–that worked better to hold her little penis and tiny balls in place than any manly briefs.

Preston was looking out for his friend but also wanted to see how this would play out. Weirdly, he wanted to get a better look at how feminine his friend’s body was too. This would be a way for that to happen. Then he’d get them out of there. It would be time to bail.

FULL DISCLOSURE

Holly got on a win streak and was the last player with a shirt on, but when she lost the next hand, it was time for her to bare her breasts. With all the male interest in her petite female body, she was self-conscious about baring her sexy, budding breasts and erecting puffy nipples. Surprising everyone–even herself–she stood up and dropped her shorts, obviously forgetting she was wearing Tatiana’s lacey panties.

She was pin-up sexy. Sexual teasing sexy. Panties and tight top sexy. The kind of sexy that men scroll X looking for and find themselves rubbing one out to. The outline of her little penis and tiny balls were clearly visible through the thin lacey material.

To onlookers, Holly was full-on trans female. The erections under the table voted unanimously. Preston included.

Holly’s penis stiffened at the noticeable attention. She even felt her hardening little penis drip a seminal drop of approval, forming a small wet spot that appeared at her tip and soaked through the lace. Everyone noticed; no one said a word. However, plenty of gasps were audible.

Holly tried to act as if nothing was out of the ordinary; everyone is wearing women’s panties nowadays, aren’t they?

“Uh Fellas. We need to leave,” Preston stood up.

“Ah, come on. At least one more hand,” Brad coaxed.

“One mo hannnd,” Holly stammered. “Buttt that’s it.”

She was sitting there with her stiffening pantied penis between her legs like a raised hand waiting to be called in class.

SISSY BOYS MAKE THE BEST GURLS

When Holly had nothing to show in her hand–the worst on the table–she had everything to show from losing again. Her top came off. If brain wave orgasms could be measured, every boy in the room exploded. Everyone got what they wanted. What they came for. Perhaps, even Holly. Preston wondered if she lost the hand on purpose.

Her breasts were the perfect 34a with puffy nipples, for those who like that sorta thing. Every guy here did.

The perfect woman. Topless with a hardon in underwear.

And when she stood up to pull on her shorts to leave, Holly turned away from the table to hide the growing quarter-sized wet spot forming on the front of her lacey panties.

“Pardon my rudeness, but that’s the hottest ass I have ever seen,” Brad said when Holly turned around. “Really appreciate you both coming over. You made our night.”

DO YOU THINK I’M SEXY?

On the Uber ride home, a very, very drunk Holly asked Preston an unexpected question.

“Do you think I’m attractive?” she was still slurring her speech.

“As a man? Or as a woman?”

“I…guess…as a woman. Like…why do you think a guy would want to fuck me?!”

Holly was drunk and perhaps speaking her inner truth.

“Why would you ask me a question like that?” Preston wondered aloud.

“Cuz Tatiana fucked me. She fucked my ass. I liked it. It felt real good,” Holly admitted, feeling free from too much booze to expose these details to Preston.

“Oh…my. Wow…Hmm…Okay. Well, let’s put it this way, I can see why guys would want to fuck you.” Preston diplomatically responded.

Author’s Note: Hollis temporarily presents male the next morning.

ALL LOCKED UP AND NO PLACE TO GO

Hollis woke up straight and sober and struggling with the duality of masculinity versus femininity. One side was convinced he needed to get back into the competition. He texted Tatiana begging for another chance while he was still (meekly) trying to blame her for his three-inch penis. He told her his penis was permanently shrunk from the pills–even though the label said the effects were temporary. And since it was her fault, he should get another chance to fuck her. Subconsciously, perhaps he wanted another chance to be fucked BY her.

He left out the part about the strip poker with the boys last night and perhaps ‘forgot’ about the conversation in the Uber on the way home.

“None of the other guys’ penises stayed small. That’s on you. I didn’t force you. You wanted to compete. You took a risk. You’ve changed–for the better–and you know it. Don’t call me until you can admit who you are. Just a horny fuckin’ sissy.” Tatiana’s accuracy and confidence were both intimidating and spot-on. “Then–and only then–will we talk about my hot, tight pussy.”

In his confused state, he said he was ready now. Tatiana didn’t believe him. She gave him an ultimatum. I offered you this before, but it didn’t seem to work out. So I’ll offer again. No more pills, but you lock your little dick in chastity for a month and give me the keys. As a consequence for turning me down the first time, you’ll sleep in a bra and panties, sending me a compliance picture every night. I want to see your little penis caged and pantied and waiting–YEARNING–for my pussy. That’s my offer.”

The phone line was quiet.

He said yes.

WET DREAMS

He was Hollis all day and then Holly each night. She sexted Tatiana a caged penis picture faithfully every night. Overnight, Holly often dreamt of being taken. Rectally. And enjoying it. Although she wasn’t sure, the dried cum stains in her panties one morning reminded her of the vivid dream of relinquishing her anal virginity. The scene in her mind where Tatianna watched Holly being taken up the ass and encouraged her turned Holly on so much that she called in sick from work.

A VEGGIE NAMED REGGIE

Holly was feminine all day. When she went to the fridge for lunch, she fixated on the large cucumber in the vegetable bin. She thought to herself, ‘I can’t be THAT desperate,’ while recalling the famous quote about desperate measures. When she put her hand around it, it felt good. Her penis twitched. She couldn’t imagine what came over her.

Yes, she could. She wanted something hard up her ass. She recalled being taken in her wet dream by ‘Reggie.” She could pretend THIS was Reggie. Besides, she couldn’t imagine going to a sex shop today. What if someone saw her? And she couldn’t wait for online shopping. She needed to be fucked in the ass right now. Today. And Reggie was hard and available.

Holly scrubbed Reggie clean, admiring the large tool, and rolled a condom over him that she had no use for anymore with her small penis. Vaseline was her only lube choice. She realized her sexual life was changing and she needed to make a shopping list for later: KY Jelly, Rubber Phallus (2), Vibrator, cock ring and maybe even a butt plug.

Her sexual transition battle in the bedroom was over, at least temporarily, for today.

She had solo sex with Reggie’s hard ‘cock’ up her ass; penis stimulation was not part of her enjoyment. She grasped her marble-sized balls in her hands and rolled them around in their scrotal sack. Man, that felt good.

When she ‘just couldn’t wait any longer’ to have an orgasm, she knew what she needed to do. Turn the nobs and her volume would rise many decibels.

She took each nipple between a thumb and an index finger and twisted and turned her puffy nips. She was riding Reggie’s rock-hard cock by sitting and raising with her shins flush to the floor and her quads lowering her hungry ass on her new fake ‘boyfriend.’ She closed her eyes and imagined herself in a ‘reverse cowgirl’ position. She thought of her sex dream.

And similar to Tatiana’s tweaks, she dribbled clumps of sperm into and out of her tiny caged penis, moaning so loud that she worried the neighbors would hear.

She wanted this; she seized this. She got her ass fucked, and she came in chastity.

And sure enough, someone knocked on her door asking, “Is everything okay in there?”

Yes. For Holly, Yes! Yes, it is.

SHE WILL DO ANYTHING

It was only the 17th day. Holly broke the month-long deadline and called Tatiana.

“Well, this is interesting. How’s my gurl? You must be a very horny sissy.”

“I’m calling to ask…okay beg…for sex. This weekend.”

Holly used the term ‘sex’ on purpose. Whether Hollis attempted another useless limp fuck or Holly took Totty up the ass. She knew Tatiana would deliver what she desperately needed.

“Orgasm denial can really fuck with your brain, right?” Tatiana teased.

Holly’s barely audible response changed the direction of the conversation.

“Err…I…um…Uh…”

“Woah. Gurl! You did it! Didn’t you? OH MY GAWD. You had a sissygasm!” Tatiana finished her exclamation as a statement of fact, not a question.

“I…I…I…”

Holly wanted to say it was an accident. A wet dream. No way would she mention a cucumber. Or a Reggie fantasy. It would be mortifying to go into that.

“Well, I didn’t say you couldn’t cum. BUT the goal WAS complete submission. And the cage is in place for orgasm denial. You sneaky little sissy bitch,” she said playfully, “You’re not submitting properly, are you? Care to explain?”

Tatiana’s tone was now femdom condescending mixed with respectful, humiliating control.

“It’s too embarrassing. Just tell me what I have to do… need to do… so I can come over. Totty, please. I’ll do anything.”

It’s never a good idea to tell an ex-girlfriend you’ll do anything.

“To start with, obviously, you are not gonna fuck me anymore. Not that you ever did,” Tatiana laughed at her own humor. “Your penis is too small, and you are undeserving. Besides, my tight little pussy is a bit more loose now. I’m only fucking guys with average size cocks.”

Hollis momentarily surfaced.

“Average! Average! What’s average, Totty?!”

“Careful, sissy. You’re not striking the proper tone. Five inches.”

The previous response marked the last time ‘Hollis’ existed around Tatiana. In the future, it was all Holly.

Holly wanted to call bullshit. She wanted to remind Tatiana she WAS five inches before submitting to the Penis Shrinking Pills. She knew better.

“What am I supposed to do now?” Holly asked. Pleaded really.

“About what?”

The phone confrontation was peaking. Holly spoke freely, but carefully chose her words.

“I transitioned to look and feel like a girl for the chance to sleep with you. I shrunk my penis to be with you!”

“Kind of short-sided, don’t ya think?” Tatiana purposely said short. “But I knew what you needed. Look at the plusses. You’ve tapped your feminine side and probed, actually. Clearly, you like anal sex. You’d rather be a girl than a guy…at least in bed. So, it’s not been all bad. It’s okay, gurl. Don’t fret. Do an AI search for sissy. It’s why I require boys to take Penis Shrinking Pills. To separate the men from the boys. I knew you were a girly boy. It’s really no big deal.”

“So, that’s it then. Are we really done?”

“Hmm…I’m thinking out loud here. Since you admire my tight pussy so much, maybe, just maybe, you could lick me clean after Preston fucks me. That is, if Preston is okay with it.

Holly lost it.

“YOU’RE FUCKING Preston NOW?!!

Click.

Tatiana hung up.

SISSY HOLLY IS HERE TO SERVE

Holly called and texted. Days & Days. Tatiana didn’t answer until the original goal of a month–for Holly’s little sissy penis to stay locked in chastity–was reached.

When Tatiana finally did answer a call, she made it crystal clear that Holly better not say a single word. Tatiana explained the ground rules. It went like this.

Tatiana would text Holly how to earn her keys back to her penis cage. And unless Holly only responded to every text with: ‘Yes, Totty, sissy Holly is here to serve,’ then Holly would need to find a locksmith.

The text exchanges went like this:

‘Buy a ten-inch strap-on dildo.’

‘Yes, Totty, sissy Holly is here to serve.’

‘Only use your mouth on it until I fuck you with it.’

‘Yes, Totty, sissy Holly is here to serve.’

‘Suck my cock for 30 minutes every night for the next month.’

‘Yes, Totty, sissy Holly is here to serve.’

‘You can come over and beg me to fuck your ass after 30 MORE days in chastity.’

‘Yes, Totty, sissy Holly is here to serve.’

‘Check your texts every hour for the next month for further instructions’

‘Yes, Totty, sissy Holly is here to serve.’

CRYSTAL CLEAR FUTURE: TO SUCK & SWALLOW

And then, just to confirm Holly was completely on board, Tatiana sent two more texts:

‘You want to suck a real cock in front of me, don’t you, Holly?’

‘Yes, Totty, sissy Holly is here to serve.’

‘You want to swallow another man’s sperm, even if it’s Preston’s. You do, don’t you?’

‘Yes, Totty, sissy Holly is here to serve.’

Holly got out a calendar to mark the count for each passing day. In the meantime, she’d go shopping. She’d get everything she needed to enjoy herself while waiting. She recognized now she wanted to be a sexually submissive sissy gurl and was ready to give in. Fully submit.

The End.

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