A gay story: Becoming His Sissy Pt. 04 *All characters, names and entities are all fictional. this story contwins cheating, sph, bi suggestions, and other potentially offensive subjects. Read the previous chapters to decide if it is for you.*
The night had been a bit of a blur for Tricia. What started as an innocent work party had led to a bit more drinking than she had intended prior to the draw of social fun.
She was wearing a professional but sexy navy blue dress that accented her beautiful creamy skin. Her long hair hung down her back between two exposed shoulders. A tall glass of a sweet tasting mixed drink with a orangish hue, was held in her small delicate hands.
In these in between moments she wished that Grant had accompanied her. It always helped to not feel like you were alone. Grant had always been a bit less of a social gathering kind of person. Sure, he liked parties, but the work party thing came with more anxiety as he felt like it was just putting on a show for her coworkers, as he wasn’t in the loop of most of the conversations.
Having just left one conversation she sauntered across the large dimly lit room. Pausing and surveying the scene for her next bit of entertainment. Suddenly, she was jolted forward as someone backed into her. A large hand then rested on her shoulder, and a baritone voice rang out, “Oh, I am so sorry. I didn’t mean to bump you there.”
Tricia turned around and looked up at the tall broad man before her, looking down at her with kind blue eyes.
“I hope I didn’t spill your drink,” he said apologetically.
“Oh, just a little, but it’s ok, none ended up on me.” She smiled, trying to place the attractive man that just shoved his way into her scene. She couldn’t remember seeing him in the office before. A tiny bit of her drink dripped from her fingers.
“Here,” he extended his strong arm with a napkin in his massive hand.
“Thank you, how kind.” She wiped off her glass and hand.
“I’m Alex,” he said, offering a handsome smile.
“Tricia.” She smiled back, starting to reach out to shake hands, and then laughed awkwardly, as she realized she was holding the wet napkin in one hand, and her drink in the other.
Alex laughed, “Looks like you have your hands full. Allow me, ” he reached out and gently took the soggy napkin. He took a few steps away and tossed it in the trash can nearest to them. Then strode back to her. “I guess we can try this again,” he extended his hand, “Alex.”
She reached out and shook it, her tiny hand completely enveloped by his, “Tricia.”
“So Tricia, are you accompanying, or part of Wimco team?”
“Oh, I’m part of the ever exciting billing department at Wimco,” she chuckled, shifting and placing her free hand on her hip. “I haven’t seen you around the office, are you a Wimco employee?”
“No, but I do offer legal assistance to the company through my firm. Guess they always invite us in hopes of getting a discount,” he laughed.
“Well of course, got to keep the bonuses flowing,” she joked.
“Well, nice to meet you, Tricia, billing extraordinaire. Did you bring a ‘plus one?”
“No, unfortunately he’s not big on these things.”
“That’s a shame. He’s not worried you’ll get swept away by some dashing executive?” He cocked an eyebrow.
She blushed a little, “I guess not, but so far no one’s whisked me off.”
“And how surprising that is,” he said, stepping next to her and gently placing his hand on the small of her back, “Care to accompany me for a refill,” he lifted his empty glass for show, and gestured to the bar.
She felt herself get warm, and perhaps a bit flushed, as this gorgeous and towering man touched her. A little jolt ran through her. For a moment she considered making some excuse, but figured, “what’s a little bit of harmless banter,” especially since Grant had kind of left her on her own with this.
Grant welcomed the alone time at the house. Things had been pretty busy the last few days and a little breathe time sounded good. Tricia would be gone several hours and that gave him plenty of time.
Considering what first, a pull, like a magnet, drew him to his drawer of ‘secrets’ upstairs. His dick jumped a little at the beckoning of it’s contents.
Pulling out the drawer a little, his eyes were immediately drawn to the pink spandex panties with the sleeve. A little blood pumped, a little glint of excitement rose, and he pulled them out. He also grabbed the white thigh high stockings. Having not gotten off for a few days, a naughty little feeling was building in him. A hungry little desire grew from within.
First he ran a bath, making sure the water was just the right temperature, grabbed a fresh razor, and some of Tricia’s shaving cream.
Tricia made a “why not” face, said, “Sure,” and let Alex lead her, hand still resting just above her cute little butt, to the drink table. She sipped at her glass along the way, deciding to empty it so that she could start a new one, getting to know her interesting novel acquaintance.
As she sipped, she mis-stepped causing her to trip on her heel. Alex quickly shifted his arm around her, grabbing her just above the hip. With one arm he practically lifted her off her feet with ease, glass still in his other hand, “Ohhhh, are you okay? Thought you were going down there,” he laughed, his blue eyes sparkling a bit, or so it seemed to her.
Impressed by his stature and strength, she couldn’t believe how easily he had handled her. If it had been Grant, he’d have probably toppled down on top of her, trying to catch her and both would’ve been covered in their drinks.
“Good reflexes, and thank you,” she laughed.
“Why thank you, I do aim to please,” he replied heartily, his hand still on her hip.
Tricia couldn’t help but like the feeling of the wall of a man holding her into him as they walked to the bar.
The bartender asked them for their requests, served them, and Alex pointed to one of the sofas that scattered the area. It was conveniently separated from the rest, in a shadowy nook. A little candle rested at the coffee table in front of it. “I don’t know about you, but I could use a sit-:down.”
“That sounds fantastic, especially after my potential catastrophe back there,” she giggled, now definitely feeling the warmth of the alcohol coursing it’s way through her. She had lost track of how many she had taken down at that point.
Grant toweled himself off, reveling in the tingling sensation of his smooth legs. Having not had sex, it seemed that Tricia hadn’t noticed his new delight. However, he still hadn’t made up a good excuse in his head to explain it if she did.
His cock had shrunken to a shriveled unimpressive state from the cold air. He gently slid on the pink little bottoms, carefully running his fingers along the edges so nothing was twisted and his ass cheeks were perfectly held by the fabric. Next he shimmied his pecker through the sleeve, which in it’s current condition, didn’t even extend out the opening. “What a good girl, with her cute little clit all wrapped up,” echoed in his head, as he admired himself in the mirror before pulling on the long white socks.
Grabbing his phone off the vanity, he took a picture, and saved it in his hidden album.
Strutting around the house to the kitchen, on full display, given the blinds were drawn, he poured himself a sweet girly cocktail, stirring it, and taking a taste to make sure it was just right.
Tricia was thoroughly enjoying the chat with her new friend as they playfully discussed the scene around them and the office demographic. Without conscious intention she had turned her body towards Alex, and her thigh was gently resting against his.
“So, what about your ‘plus one?'” She asked. Her curiosity, and maybe a little bit of desire swelled in her, as did a moist spot on her panties.
“Well, the position seems open at the moment,” Alex said calmly as he sensed her inhibitions being lowered slowly, and her tone a little more playful.
“Oh, I would surely think you’d have no trouble filling it,” she said, has her hand subconsciously came to rest on his knee.
“Well I’m going to take that as quite the compliment,” he said as his eyes traced up her legs, her beautiful bust, over her lips, which she seemed to almost be gently biting a bit, and then straight into her eyes.
Tricia gazed back in his, silence hanging in the air for a moment as if time stopped, butterflies hovering in her stomach…and then, a hint of sober reality tried to work itself back into her brain. She shifted back, looked away, chuckled, and removed her hand from his knee.
In a bit of an awkward tone, giving away her inner desire “I think I’m going to use the restroom and get another one of these,” she stated, glancing at her glass and raising it a bit. “Would you like me to grab you another?”
Alex leaned towards her slightly, took her hand with one of his while his other still rested just above her knee, “How about you go, I’ll finish this, grab one for each of us, and we meet back here for some more enthralling conversation?”
A small breath escaped Tricia’s mouth, as she was titillated by the feeling of his large hand holding hers, while goosebumps ran over her skin. A witty response had evaded her compromised brain that sensually overloaded.
“Okay,” was all she could push out.
She stood up and could feel his eyes following her. She swayed her hips, liking the feeling of being watched, of feeling hot and admired.
A vibration jolted Alex’s attention away and to his pocket. He pulled it out and glanced down, opening the screen.
Two pictures appeared in his texts. Both from Grant. The first was a shot of him in his cute pink little outfit with a tiny little cock hiding in the cave of it’s sleeve. The second was it jutting out the end, hard, throbbing, and leaking a string of precum from the adorable little head followed by “I hope daddy likes what he sees.”
Alex quickly replied, “Oh, daddy definitely likes it. Unfortunately I’m wrapped up with some work stuff tonight, but make sure to take some more and send them my way.”
Carefully and slyly, Alex adjusted his semi erect python in his pants and then grabbed both glasses, proceeding to the bartender.
The bartender gave him a grin as he poured their drinks again, “Someone looks like they’re going to have a good night.”
Alex laughed, “One can only hope.”
Tricia was walking his way. She had clearly adjusted her hair, makeup, and applied a little more gloss. A seductive half grin crossed her face, then she looked over at him, and offered a full warm smile. Her amazing tits bounced ever so slightly in her dress.
Her eyes dropped to the floor for a moment, and as she lifted them, they went wide, as the outline of Alex’s manhood was outlined in his suit pants, just right from the lighting and the angle. She had to double take and catch herself, then go back into an attempt at composure from the sight of such an amazing specimen of….
“Why hello. You survived,” Alex joked.
“Small wonder,” she said, “that place was a crowded pit of vipers.”
He offered his arm, she took it and they walked back to their untouched corner of solitude. She looked for an opportunity to cast another glance downwards, only to have her calculations reaffirmed, as the wet spot on her panties doubled in size. Again she bit her lip for a moment, but consciously stopped as he looked over at her right before assisting her into the seat. Sitting back down, close enough that their legs lightly rested against each other.
Alex took a big swig from his glass. “Ya know, I really can’t imagine why any man would turn up the opportunity to accompany such a beautiful woman as yourself to a party.”
Grant’s fingers circled against his tight boipussy, with his panties pulled to the side. Using the mirror behind him he clicked another shot and hit send.
Alex felt his phone buzz in his pocket. He pulled it out, angled just enough that the screen was hidden from Tricia’s view, and then placed it back in his pocket.
“Get anything important.”
“Nothing substantial enough to require my attention currently.”
“I do wish Grant felt more pressed to be here to support me,” going back to his previous statement, “but I do understand these things tend to make him anxious and a bit awkward.”
“Hmm, well, to have scored your affections, he must be quite the man,” Alex replied, testing the waters.”
“Well,” she hesitated, but then continued with eyes downwards at his hand on her leg, “maybe not in the traditional sense, but he is always so sweet and kind,” she trailed off with a bit of guilt evident in her face.
His hand came off her leg and he lifted her head, meeting eyes with hers, “I know it’s not my place to say anything, but I think you deserve a man who is a man to you in every sense of the word.”
Her pupils dilated, pure want visible in her eyes, her tongue grazing the inside of her lower lip. He smiled looked at his glass, finished it, grabbed her hand, and lifting her with ease once again, said, “Hey, I want to show you something.”
“Ooooh,” she exclaimed, caught off guard with his reflexive action. She followed holding his hand tightly, probably tighter than she knew she should. Alex led her out of the giant room and into a series of hallways that were unlit. He then opened a door and pulled her in. Shutting it behind them he pressed her against the wall, grabbed her ass and lifted her. Instinctively she wrapped her arms and legs around him as he began to kiss her. His tongue invaded her mouth and danced with his.
She cooed, feeling his incredible and substantial member pressing against her moist panties through the fabric of their clothing. Adjusting his hold on her, he took one hand and grabbed her breast, cupping it completely with his long fingers. He began kissing down her neck as she dragged her fingernails across his back.
“Ooooh fuck you are so fucking hot,” she moaned, and began unbuttoning his shirt, exposing his amazing chest. She ran her fingers over his hard pecs, as he undid his trousers, letting them hit the floor, and unleashed his long, fat cock. Using it to push her soaked panties to the side, he then slowly pressed it against her dripping little hole.
“Oh god, you are so tight,” he growled as he carefully and slowly entered her, as her pussy clenched offering so much resistance.
“Ffuuuuucckkk, your cock is….fucking huuugeee….,” she panted
He pressed into her further, and she pulled tried to stifle a scream of pleasure as one hand climbed the wall behind her and the other slipped the strap of her dress off her shoulder. He peeled her bra down freeing her breasts.
Slowly he invaded her vagima with the last portion of his cock, filling her in ways she had only imagined. Every ounce of her felt full and stretch, gasping, moaning and clawing uncontrollably…
His rhythm increased in speed, pummeling her insides.
“You fucking like my big fucking cock owning your tight pussy? Has your boyfriend ever fucked yoh like this, filled you, stretched you the way I am?” He growled.
“Oh god no, he could never fuck me like this. He could never reach the spots that you are stretching, his little cock doesn’t have any chance of doing what you are doing to me…right ….noooooww…
“Oh fuck yes. You like my hard fucking cock better than his pecker. Tell me you never want his fucking prick again. Tell me this is all you want from now on…”
“Ooohh, fuck yes…his tiny dick will never satisfy me again. I just want you to fuck me over and over…”
Her pussy was assaulted hard and fast, opening beyond a size she knew it could, until she cried out and shook in an orgasm unlike she had ever known. Her body shook, twitched, and her pussy spit drenching his stomach and cock, as his grip on her ass intensified to the pulsing of her inner muscles and began spewing hot cum into the depths of her canal. A flood of hot jizzz filled her pussy,as their breathing eventually slowed.
They embraced tightly as he held himself inside her, feeling her heart beat around his cock, and his own inside her.
His pants buzzed on the floor again.
“Hooollllyyy shhhiiiiittt,” Tricia exclaimed, still reeling from the overwhelming sensations pulsing through her trembling body.
“That was so fucking hot,” Alex said, before kissing her passionately again.
He started lifting her slowly off his gradually deflated pole. His thick white seed oozed out her pussy onto the floor below.
As her feet hit the floor, so did her heart. Guilt began to replace the pure ecstasy. She grabbed her panties and slid them over as they collected an ungodly amount of his semen dripping out of her snatch.
“You okay?” He asked as his hand touched her cheek.
“Yeah…I just…I shouldn’t have…”
“It’s okay, he doesn’t need to know. This can stay between us. It’s not wrong to have needs,” he tried reassuring her.
“I just…I need to just go…”
She hurriedly put her clothes in order the best she could, and in a disheveled state hurried down the hall, out of the building, and to her car.
Alex, slipped his pants back on, fixed his shirt and sighed in satisfaction of his night. Reaching into his pocket, he saw a video message.
When opened, it showed Grant bouncing on a long thick purple dildo, moaning, and his cock spitting cum onto the screen.
“What a good little sissy you are for daddy. That’s so hot,” is all he wrote back.
When Tricia pulled in the driveway, she sat for a long time, trying to process her mistake. How could she ever…how could he ever…why did she…she knew better…she loved Grant…
It was late when she walked through the door. The lights were off and all was quiet. Making her way into the bedroom she saw Grant asleep, looking so serene.
Stripping off her clothes, she crawled into bed next to him, and began stroking his chest, left uncovered by the sheets. She could see the tent underneath them responding to her gentle caress.
Grant’s eyes slowly opened a little as she climbed on top of him, in his sleepy stupor. Taking his stiff minuscule erection in her hand she guided it into her gaping cum coated passage.
“Oooh,” he moaned, still waking from his deep sleep.
She could feel him so easily slide right in and she took him all the to the base immediately. While it felt good, she could feel the stretch out insides that he couldn’t reach. She could feel how small he truly was compared to Alex.
Grant whispered, “Holy fuck, baby, you’re so wet.”
Determined to bring herself to orgasm, just to prove to herself that she could still find pleasure in Grant’s penis, she began riding him hard, bouncing like a maniac on his member, trying to bring herself to that point. The sound of her sloppy pussy inhaling his thin mast filled the room. In her sense of urgency to make it feel better she began rubbing her clit furiously.
Grant wondered what had gotten into her as she treated him like a trampoline, slamming hard down on him, exerting an insane amount of energy. He never remembered her being this wet, but he liked it, even if it made her feel like she wasn’t near as tight. Usually he could feel her squeezing his dick so firmly inside her.
The sensations of clitoral stimulation began to drive her toward the edge. She clenched her muscles around Grant in hopes it would make her feel him more. She held them as tight as she could trying to close the gap that was left from her night.
“Oh….I’m getting… close,” he said, his voice soft…
She started letting her mind wander. That feeling, it entered her head, and it took over.
Her circles on her clit and her thrust against him became more calculated, she squeezed, drew upwards,and again….First slow…. Then a buildup, then slow and strategic…and again,.. she could see the massive piece of man wrapped around her, could imagine the unfilled space in her being replaced by something that did the job…
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“Oh fuck, Alex,” she spoke and immediately recoiled. Did she say that? Did he hear it? What if he did?
“Huh?”
Baby, I want you to just cum for me.”
For Grant, a button had been pressed, a trigger tripped, and the floodgates released.
“Oh fuck, I’m cumming, oooooohhh my fucking…I’m cumming…,”.
His load squirted up into her, filling her with even more cream coating. It tried to fill the empty space, but it didn’t quite do so.
She finished herself off on him prior to lifting herself off his deflating unit, went to the restroom and passed out.
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