Becoming His Sissy Pt. 01

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Disclaimer: This story contains strong language that could be offensive. As always, if it isnt for you, theres plenty of other stories to read.

The silence filled the house, a sense of anticipation washed over Grant, despite his indecision of how to busy himself for the evening. The desire to do something wasn’t matched with the overflow of ideas, and the ideas that came to mind weren’t convincing him to take action on them. He’d sit for a few minutes, then pace, going room to room looking for some activity that would call him into action. Still, his creativity didn’t match his anxious nature at the moment. Each pace around the house would be filled with several gulps of a strong beer, before the can emptied and then replaced with another.

A light buzz came over him. The kind of magical spot that quelled the restless beast, slowed him down just enough to not constantly retrace his same steps, and instead accept his fate: that whatever pleasure he may find this evening, it wasn’t going to come from any of the activities he had already considered and rejected. It was the type of buzz that gave a steady calm, but not cooked by any means.

With a spark of decisive thought, Grant threw on his jacket, grabbed his keys, and hopped in his car to grab a drink at the pub just down the street.

Grant typically wasn’t the bar type, or at least not anymore. In his youth, he had spent way too much time and money at such places, but these days preferred too pay less for the same beer, and enjoy the comfort of his own space. In contrast, his space, this evening, hadn’t offered much for his current state of mind, so he had decided grabbing one or two and people watching, or at least having small talk with the bartender would give a little break in the monotony of his last few hours.

The Soggy Raccoon wasn’t a particular special pub by any means, and wasn’t a local hotspot by any means, but a comfortable, down to earth place with a good tap list. Stepping through the door, Grant’s eyes sifted across the scene before him. It wasn’t crowded, but apparently he wasn’t the only one struggling to find something better to do. Scanning for a place to insert himself, his eyes rested on five open seats at the far side of the “U” shaped bar.

As he waited for the bartender, a middle aged woman, standing around 5’5″, blonde hair, bluish-grey eyes, a fit but slightly curvy body and solid thighs, he glanced around at the demographic. A few women roughly in their forties joked and laughed loudly on the far side, having a girl’s night, probably offloading their vents from this week’s work, the stresses of getting “young billy” to his soccer game while juggling “Sally’s” dance schedule and planning meals as if they were some schedule juggling protagonists in their own stories. A few seats from them two jocks, gorged themselves of some cheese filled fried food, drinking cheap beer, indiscernible from watery piss and hooting at the game on the screens along the top banister of the bar (not something Grant ever found interesting.) Add a random touch of lonely old guy, a few quiet conversations between two friends, a few couples, a few young men and women probably taking a break from studies over a few… Nothing exciting, but being out of the house and taking down a beer was a nice change.

“Can I get you a drink to start?” The bartender asked.

“Yeah, I’ll have the Two-hearted.”

“Ordering food, or just drinks?” She asked fingering the menu below the ledge of the bar.

“Just drinks.”

A minute later he was sipping at his beverage, a slight bitter bite to it, and a smooth finish.

It’s amazing how small you can feel in the world, as it buzzes by you. A glance there, a shift, an aversion…

And another round….

The second beer always tastes better. Two beers in and the scene is losing it’s appeal. Perhaps he just needed a smoke. He didn’t particularly feel like returning home yet.

Taking his beer to the patio, he fidgeted with his other hand in his pocket, feeling for his lighter and smokes. He found his smokes. Pulling one and putting it between his lips, he continued now with both hands searching his pockets… and ***flick**** a bright flame in front of him…

“You look like you could use one of these,” he said, whoever he was. Grants eyes were still adjusting to the light behind to whomever he spoke.

“Oh, yeah…thanks…much appreciated…” Grant felt caught off guard. The man, probably a few inches over 6ft.

“No problem. Wild night, huh?” He jested…

“Oh yeah,” Grant chuckled, “super.”

“Eh, it’s early, it could get better.”


The man sipped at his glass, which looked like it had bourbon in it. ” The name’s Alex, yours?” He said as he extended his hand toward grant. It practically ate up his much smaller hand completely, with a much firmer grip.


“Nice to meet you, Grant. “

“You as well.”

The air was warm and the patio a cozy sort of scene, empty aside from the two bodies sucking down their death sticks.

“This beşevler escort drink is just about finished, and looks like you’re in need too… Care to grab another with me, my treat?”

Given Grant’s night had been this boring, and wouldn’t get any more exciting at home, given his girlfriend was out of town, “yeah, sure, sounds good.”

“After you,” Alex extended his arm towards the door opening it for his new found conversationalist. Grant passed the large, in shape man, feeling kind of silly as they were an odd pair. Alex, taller, broader, looking like he could squeeze the liquid out of a rock, with his smaller friend. Grant was about 5’7, thin, much more dainty, lacking muscles and weighing in at about 140 with dark hair and eyes, while Alex had blue eyes and sandy brown hair. Grant kept a beard on his face, but this man kept a clean shaven face.

They strode to the bar again, as Alex waved down the bartender. “I’d love two shots of tequila, and get this boy two as well,” he spoke as he slapped Grant on the back. It seemed strange to be called boy, but, he didn’t take offense given the tone and the generosity.

“That’ll make this night better,” he laughed as the 4 shot glasses hit the counter. “You should probably bring him training wheels, just in case,” he said pointing to his smaller friend. The limes were delivered on a napkin with a shaker of course salt. “Perfect, thank you doll,” he chuckled sliding them towards Grant.

Alex then smiled towards him and nodded his head as he picked up the first shot glass. Grant appreciated the thoughtfulness of his friend as he poured salt on the meat of his thumb, grabbed the limb and the shot in his other hand. Lick…down the trap, and bite…the limb filled his mouth with a much needed flavor.

With his baritone voice, Alex said, “So tell me about yourself, Grant… what brings you out to drink by yourself? Bad night? Breakup? New job, and celebratory drink?”

“Honestly, my girlfriend is out of town, and the house was just to boring and quiet. Plus, been a long time since I’ve grabbed a drink at a bar. Sounded like a nice change of routine.”

“Ha, you dog…out of town huh? Decided you’d come in hope of finding some nice piece of side chick?”

“It wasn’t really my plan. Just needed the scenery to change for the night.”

“Ah. Yeah, can’t say the pickings are to great here right now anyways.”

“No…not really.”

“Good thing you found company. Some of these asses here probably are sneaking glances at ya, with thoughts of their own, not realizing your the girlfriend type.”

Grant was taken back by his new friend’s comment, but let it be. “Yeah, it makes the night more interesting I suppose,” he said with a chuckle.

Alex picked up his second shot glass, and raised it, “To making new friends,”

A salting, a clank of the glasses, “To new friends,” and down the hatch.

“So what about you, what brings you here to drink alone?”

“Guess I’m just trying to get used to it. Divorce is a pain in the ass, in and of itself, but it comes with a variety of adjustments, including going out alone.”

“I’m sorry to hear that. I can’t imagine…”

“It’s quite alright. I had grown pretty tired of the old bitch and her constantly nagging. Reality is: we just grew apart over the years, and things have a way of going stale with time. But on the bright side, I get to meet good people like you.” He then shifted his gaze to the bartender again, “another round like the last babe.”

“Man, you are ready to make it a party tonight huh?,”Grant said glancing at the drinks placed before them, another napkin with a lime presented to him as before.

“Oh this, this is just a jovial start to the night. It’s still young, I don’t have to work tomorrow, and conversation and company is a prized thing for me these days. Plus, it probably takes more for me than it does for you, just to be honest,” Alex guffawed a bit with the last line.

“That makes sense. I’m no lightweight, but in terms of pounds…”

“Makes you a cheaper date,” Alex laughed and raised the glass again.

“Well you never asked me on a date,” grant said with a chuckle, “but I do appreciate the generosity.”

Grant then stood up, ” I need to take a piss.”

“Enjoy the little boys room”

Perhaps slightly lost on Grant, as the alcohol was creeping up on him, “oh I will.”

Grant entered the bathroom, which gave him some strange sense of anxiety, warranted or not. Grant used a stall, why? Why was anyone’s guess, but he felt safe there, contained. No one pointing out his inadequacies, not that he had to worry about that from a statistical standpoint. But a general sense of smallness loomed over him.

His stumble back to his seat was indicative of his state. He wasn’t drunk by any means, but slightly off in the calculations of his movement. The journey seemed longer back to his stool, than the path from it, and the awkward resetting of it for his reclaiming. He took a deep breath, pulling himself cebeci escort upon the seat to find himself greeted by two more shots.

“I was worried you fell in, but since you made it back from the treacherous voyage, we should celebrate” Alex chuckled raising the glass once again.

“To a safe voyage and It’s completion!”

“Here! Here! “

Lick, swallow, bite…the juice of the lime coated his bottom lip.

“I’m glad I met you grant. You’re good people. You know

what would make this better though… a good bong rip.”

“Oh god, yeah, that sounds good.” Grant’s enthusiasm betrayed him as he was typically more reserved in such situations.

“I’ve got some really tasty stuff if you want to move this venture elsewhere.”

“I could definitely be down for a toke.”

“That sounds so good right now.” Alex raised his hand again beckoning the bartender. He was forward, demanding perhaps. “I’d like to settle up.” The check came, the quick exchange happened, a signature and…viola…

“So should I follow you, or do you have an address I can put in the map?” Grant excitedly planned his demise, stumbling one step in at a time.

” you sure you’re good to drive? “

“Yeah. I’m good,” Grant answered, questioning whether he was good to drive, and yet confidant he’d reach his destination.

Alex sent him the coordinates.Luckily the drive was a few minutes away. Grant fell behind, arriving a few minutes after his new found companion. Alex stood in the driveway waving him in.

“Welcome!” Alex exclaimed as they entered his abode, a nice suburban home. Again Grant faced a door opened to him and was followed by Alex. A quick look around told Grant that his friend must be pretty successful, based upon the location, the size and the decor of the house.

Alex opened the fridge, “Beer?”


“Take your pick.”

Grant walked up seeing quite an array of different kinds, and leaned in trying to decide which one would be his victim. As he did he felt a large hand rest against the small of his back, but once again, didn’t really think or make anything of it. Grabbing a beer he stepped back, and Alex leaned in to grab one himself then proceeded around the corner, ” be right back…grabbing the stuff. Make yourself at home.”


A minute passed before Alex returned with a bong and a bag. He immediately started packing it on the kitchen island.

Grant, looking around, said, “Nice place you have here.”

“Thanks, it’s probably more than I need for just me, but I’ve been successful in my career, so I guess I could splurge a bit.” Alex responded, then passed him the bong.

“I really appreciate this,” Grant said before taking out his lighter and took a rip.

“Not a problem. Beats sitting here alone in the quiet, or hanging out a bar that just isn’t happening.”

Alex then took the bong himself and gave himself a nice hefty hit, pushing it back over to Grant.

The next rip was probably bigger than Grant needed, and after he cleared it, stood up leaning over the and coughed up a storm. Alex walked up behind him, giving him a good few slaps on the back…”ha, that bong will do that to you. It’s easy to underestimate the size of that chamber.”

“Ahem,” Grant was still getting his bearings, “I guess so!”He took a deep breath in, and closed his eyes for a second, feeling the weed already starting to hit him after his coughing fit. “That’s probably all I need for a minute. See where that gets me.”

Alex took one more himself and pointed to a sliding glass door and said “I think I’m going to have another smoke if you care to join me.”

“Good idea,” Grant responded.

“But first, let’s do another shot.”

Perhaps Grant should’ve known that this decision was a poor one, but in his haze, such thoughts had left the building, so he replied, “Sure. That sounds good.”

Alex opened his liquor cabinet and pulled down a decanter of tequila, setting it on the counter. Then he proceeded to grab two large shot glasses, definitely larger than a single, and the shaker of salt. “I even got the fixings for you,” he chuckled as he reached into the fridge and from it produced a lime slice.

“Man, you spoil me.”

“I figure it’s best if I make it go down nice and easy, ” Alex winked at him, then raised his glass,” To good company!”

“To good company,” he replied, clanking the glass, lapping the salt up, dropping it back, and feeling a sour cringe spread across his face before grabbing the lime and taking a big bite. “Whooooo-weee”

Alex just laughed in response and motioned to the glass doors. They stepped out onto a large stone patio without any lights illuminating it. They both drew their cigarettes, but Grants face made it obvious as he searched his pockets, that unintentionally his lighter was still inside. Before he could make a move, Alex’s large hands brought a lighter up and sparked it for him. “Second time tonight,” he smiled.

“Thanks, ” Grant said as he took a puff and a sip of kolej escort his beer, that he was making pretty quick work of. He gazed blankly at the night sky above. It wasn’t a super clear night, so the star view was pretty sparse. With his head tipped back, he stumbled backward, only to be caught by the wall of man behind him, his arms wrapping around him and resting against his stomach, causing him to let out a surprised little gasp. He could feel the bulge of what felt like a substantial package pressing against his back, his mind racing in that split second, as he gathered himself.

“You okay?” Alex asked him as he stepped back now that his new companion had seemingly got his footing.

“Yeah, thank you,” Grant said, still feeling awkward from the event.

“Don’t want ya hitting your head on that stone. That could be bad for both of us.”

“No, definitely wouldn’t want that.”

Alex raised his beer “to keeping skulls intact instead of cracked!”

“Absolutely,” Grant clanked the can and took a big swig, finishing off his beer, and taking a long hit of his cigarette leaving a long burning cherry. Alex noticed and laughed.

“Looks like you could use another beer! But let’s do one more shot,” he said, extinguishing his smoke.

“I probably shouldn’t, but fuck, I can’t say I have any pressing matters.”

“Easier making new friends when a boy is loosened up.” Alex said before taking another bong rip and pouring another double shot in the large shot glasses. He didn’t fail to pull out another lime slice and slid the salt towards Grant, who had just finished another decent hit of his own.

” a productive night!” Alex raised his glass.

Grant’s tongue dragged against the skin and salt, tossed his drink back and shoved the lime in his mouth.

“Less bite and more suck, the more inebriated you get, I guess” Alex’s eyes studied Grant’s mouth.

“Yeah, the lime is a life saver at this point.” Grant said after removing the dried out slice that he had drained the juice from.

“Completely understandable. Little guy like you is probably feeling double what I am, and I have to say I’m feeling a bit warmer now.”

“Funny how that happens.”

“Do you mind if I use your bathroom?”

“I do….,” he left a pause just too make it awkward,” but seriously, if you hang a left down that hallway it’s the second door on your right.”


“Of course.”

Grant found the bathroom a bit echoey. He pulled his, for the most part, shriveled cock out, feeling unimpressive and stood there listening. After a minute he finally let his piss flow, hoping he didn’t make too much noise, or just enough noise, in case someone would make assumptions.

He made his way down the hall with a left and then a right…success!

Alex already had a cigarette in hand, and Grant was game, so once again it moved outside.

Alex slid the door open gesturing for Grant to go on through, before following and sliding it shut.

“Well this night turned out better than I thought it would,” the larger man said as he sipped his beer.

“Agreed,”Grant said, the warm fuzziness of the alcohol washing over him as he gazed upwards. For a moment he became such a space cadet that he dropped his smoke. As he bent over to pick it up, he was suddenly surprised to feel Alex’s bulge pressed against his little ass. A thousand thoughts racing in his head in that split second.

Grant considered himself straight. Sure, like most guys he occasionally watched gay porn, or tranny porn, even a sissy hypno here and there, but never had he acted on or sought out anything other than girls.

Startled, he stood back upright but before he could say or do anything, Alex’s arms were around him sliding down his waist, and both hands cradling Grant’s crotch, pulling his small frame into the big man’s pelvis, kneading Grant’s growing bulge.

“I’m not…”

Alex cut him off,”You can think whatever you want, but right now your cock is telling me you like being handled like a little bitch.”

Grant’s mind was screaming. Part of him wanted to push the man off and dash out the door, though he was worried he may be too drunk to drive. He had a girlfriend and what if…

“Don’t worry, no one will know,” Alex whispered in his ear, one large hand still on Grant’s crotch and the other sliding up to his chest, squeezing his pectoral and pulling him in harder to the big man’s body. Compared to his own hands, Alex’s covered so much of him. His cock felt dwarfed by the size of his palm.

Despite all the torrent of panicking thoughts Grant was having, all that came out was a soft little moan.

“Have you ever been with a man?” Alex asked as he nibbled down Grant’s ear and down his neck.


“But you want it. All little bitches like you love to have a big, real man turn them out, treat them like a little slutty girl, make them feel hot…you want that don’t you.”

“I’m not sure I can…”

“Oh you know you can. I can feel your little boy cock straining against your jeans, begging to be handled.”

“Mmm” another soft moan escaped from Grant’s mouth, betraying him.

“You like that boy don’t you,” the voice buzzed in Grant’s ear and vibrated through his body, until it reached his dick causing it to twitch under Alex’s palm.

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