Becoming His Sissy

Days had passed since Grant faced the biggest conundrum of his sexuality. Conflicting emotional swirls of self-question, inadequacies, desire, pleasure and humiliation raced through his mind. Grant, no question, still loved his girlfriend, and definitely loved fucking her. However, the sheer taboo pleasure of his night with Alex shook him to his core.

Though Alex had given Grant his phone number, Grant's insecurity had kept him from calling or texting. Part of him craving to feel that way again, part of him, ashamed to admit it.

It was a Friday night, and Grant sat on the couch watching another "typical" show with the same overused theme and storyline from several shows premiering a few months before. Despite their lack of substance and originality, they filled time, and were mindless distractions to a tired and overly active mind.

A click of the lock was followed by Tricia coming in to the house.

"Hey babe, " Tricia set down her things, grabbed Grant's face and gave him a kiss on the lips and took a seat beside him.

"Mmm, hey love."

"How's your day been?" She asked.

"Overall good, got out of work early, so I beat you home. figured I'd take the time to just veg a bit. How was your day?"

"Oh, just the typical b.s. and busywork. Not bad. Hope you aren't to tired...." Her hand traced down his leg.

"Oh yeah... and why's that?" his hand traced down her neck playfully.

She took his hand, "how about I just show you.." and led Grant to the bed, pushing him down on it. She pulled her top off, and unhooked her blue lace bra that supported her beautiful D cup breasts tossing them to the side. Kicking off her leggings, she exposed a light blue pair of cotton panties, that perfectly clung to her cute little ass and hugged her swollen pussy. A little wet spot formed and darkened the fabric where her little slit was.

"Mm, I like this idea."

"I bet you do," she said as she pulled his shirt over his head and pulled his pajama pants down exposing his now hard cock, risen to the occasion.

Stepping so her cunt hovered over his dick, she pulled the crotch of her panties to the side, and lowered herself on to him.

"Oh fuck you're tight."

"Oh god, your cock feels so good stretching my little pussy. Does that feel good baby? You like stuffing my little cunt? Do you feel how wet I am?"

"Fuck yes," he groaned in pleasure, as she squeezed her muscles around the base of his cock, then raising her hips up, until it squeezed the head, teasing her pussy lips, pulling out and sliding his cock head against her clit and back down, sliding him into her again.

Grant's eyes hungered at the sight, but couldn't help but think how how those wet, little light blue panties looked on his girlfriend...and wondering how they may look on him..."Ooohhh," he cooed as she bottomed out on his cock again, now grinding herself on his cock with a slow serrated motion, rocking herself on him.

"Mmm, I've been missing this."

"Me to, " his hands glided up to her tits cupping them the best he could. Suddenly the thought popped in his head, that Alex's hands could probably hold them completely compared to his smaller hands. He moaned again, squeezing the soft plump flesh. Her nipples were hard and poking out.

Tricia was about the same height as him, with pale skin, sandy blond hair, a cute little button nose, 36D breasts, a soft but toned stomach, and an small ass that sat on long skinny legs.

Pulling herself off, she got on her hands and knees at the edge of the bed, said,"Get behind me."

Grant scrambled to his feet, got behind her and positioned his 7 inch dick with a slight upward curve against her wet panties, pressing into them slightly, before pulling back and pulling the crotch of them to side, again. Sliding his dick in he began thrusting his hips slowly. Tricia's hand was down the front of her panties, making circles around her clit as he plowed her from behind.

"Ohh fuck yes baby," she moaned, "That feels so good, you feel so good inside me."

Grant watched his dick slide in and out of his girlfriend's pussy, the muscles inside relaxing some, the wetness making him slide easier in and out of her.

Listening to her moan as she pushed harder into him and she increased her speed of clitoral stimulation, he couldn't help but think about how she would moan if Alex's dick were pumping her little fuck hole. Would she be bucking and moaning harder? Would she even be rubbing her clitty? The thought of hearing her getting fucked by a superior dick made his cock jump. He wondered if he were watching what she would say? Would she talk dirty like the hot wives in the porns he'd seen? Would she get off telling him how that big dick stretched her hole so much better? Would she make fun of his thinner, shorter cock, telling him how useless he was? Did she ever secretly desire that? Would she force him to tongue her pussy while that long, fat cock owned her little cunt or get his cock wet with Grant's mouth to lube it for her?

Suddenly she let out a whimper, her body spasming, the muscles of her pussy quivering on his cock, causing him to convulse and start unloaded his cum into her pussy, shot after shot. His heart slowly reduced it's rate, as he slipped his cock out of her pussy, the cum running down the lips and out her expanded hole, almost dripping.

"Fuck that felt good...someone apparently needed that," she said.

Grant's eyes were still glued to her sloppy cunt leaking his seed. Part of him just wanted to dive in and start tonguing the cum out of her and sucking on her pink swollen cunt. Part of him imagined it was Alex's load. Part of him wondered how it would feel to put his smaller cock in after a big dick had just owned his girlfriend, to feel his cum as lube, to feel how much more it stretched her than him. He wondered if she'd even feel him, would his cock even touch her inner walls after a superior man had fucked her.

"Grant?" She snapped him from his dazed stare.

"Mmm, that was amazing, baby." He said as he flopped down next to her and kissed and caressed her.

"You came really hard," she smiled.

"That's what you do to me," he chuckled wondering what she'd think if she only knew what he had been thinking.

The relief had eased Grants mind for the day, reaffirming to himself that he was still "straight," and loved fucking his girlfriend...or mostly "straight."

As the days passed, Grant would often find his mind wandering late at night, after his girlfriend had passed out (something she usually did well before him.) He'd scroll through porn pages, often finding himself watching videos of trans, cross dressers, fem boys, sissies....something he didn't, typically, watch often. He found it becoming much more frequent. He'd even started searching jocks, panties, hot little corsets, stockings, and garters and wondering how he'd look in them.

He'd look at wigs and makeup tutorials, wondering if he did it well, if he could be passable. Usually he'd wank, and then try to forget such silliness, but such silliness has a way of hanging on somewhere in the depths of one's mind.

One night, after a few to many beers, Grant found himself ordering a pair of cotton blue panties like Tricia had, with white trim, and a pair of thigh high white stockings. But it didn't stop there...a green jock with black elastic bands, a spandex pair of light pink sissy panties with a open ended sleeve for a cock..."fuck, what's wrong with me?" he thought as he cock quivered in his boxers and thoughts of whether Alex would think them cute on him, filled his mind.

The day came for his packages' arrival, and anticipation rose minute by minute once they were there. He couldn't wait until Tricia passed out, so that he could try them on and check himself out in the mirror. Part of him excited, part of him ashamed that he was so excited.

To be continued....