Becoming His Sissy Pt. 05

Grant woke up feeling hungover. He definitely had a few too many as he dressed, played with, and fucked himself. It was almost too easy to come up with an excuse for some alone time.

His morning wood had caused him to wake, and he was in an alternating state between sleep and awareness. He remembered his debauchary, as well as Tricia coming home and unloading on him.

He laid there, and then time passed? His eyes opened to a little more light, and he just wanted a little more sleep. And did he hear her say, "Alex."

His dick ached, and then the effects of his decisions whisked him off to the dream world again.

It felt like he was awake every ⅔ of every hour for 4 hours.

Tricia's head hurt. The morning felt like a blur. Images from the night before became more clear the further she woke up. She struggled with the urge to pee, and finally left the comfort of her bed and warm covers to venture towards relief.

Tricia crawled back into bed but the ramblings of her mind wouldn't afford her further rest.The shameful choices assaulted her conscience but her sore pussy was pleading to be fucked again so completely.

She reached over, feeling Grant's erection, and started to caress it. Precum dribbled in copious amounts out the end of his penis. Using it as lube she stroked him, trying to program her brain to focus on him.

She couldn't help but think his cooing and soft moans were almost feminine in nature. Such a small delicate man, delicate hands, soft skin, and an completely acceptable dick...

"Mmm, that feels good."

"Does my baby boy like that."

"Mmhmm..." he nuzzled into her arm while the other kept pumping him.

Thoughts of stroking Alex's impressive cock kept creeping into her train of thought, despite her attempts to recalibrate.

For a second she expanded her hands grip, just to imagine the width difference, but tightened again to fit around Grant.

She could feel him tensing, and knew he would soon be finished.

"Are you going to be a good little boy and cum for me," she said it without realizing the condescension in it. But Grant didn't seem to respond negatively, instead his mast got harder and swelled.

Grant let out a few more effeminate "oooohs" and then blew his wad on himself. Tricia reached for a towel and handed it to him.

"Such a little bitch," popped in her head. She felt guilty for thinking it. She had never thought such things of him, but for some reason her brain wanted to spew that out.

Tricia had never once been dissatisfied with Grant's dick before now. Being a decent size, it almost always did it for her. However, this new experience, the new comparison, it just illuminated how much a couple extra inches could do.

She told herself it would be ok, and that given a little time, they'd move on like it never happened. Grant would never find out, and it was definitely best that way. She could only imagine how it'd crush him.

The week passed in a pretty normal way. Tricia's mind seemed to settle as it focused on the mundane tasks of the workplace.

Thursday rolled around and Tricia was happy that the weekend was quickly approaching.

It was around 10:45am. She was typing away at her keyboard when her heart jumped from the sound of a familiar baritone voice. She looked up from her computer and there, walking towards her desk, was Alex.

He wore a dark blue suit, and a light pink button up dress shirt.

Alex placed his large hand on her desk and leaned over, "I was hoping to catch you here."

Tricia felt the conflicting feelings of dread and excitement. He was brazen to show up.

"You'll have to excuse my surprising you at work, but since I didn't have your contact info, and you were in a hurry out the other evening, this was my only route forward. That said, I was hoping you'd consider getting lunch with me."

She felt cornered. In her mind, she knew she should turn it down. She knew it was a bad idea and shouldn't even entertain the thought.

"Sure, that sounds good," was what came out instead.

"Great, here's my number, give me a call or text when you are free," and with that he placed a business card on the desk and walked away, as quickly as he had appeared.

Tricia couldn't believe what she had just said yes to, and now her mind was wrought with turmoil. She reasoned with herself that she'd use the opportunity to apologize, explain she was committed, and shut any presumptions that this would continue.

11:45am came around pretty quickly. She pulled out the card with his contact info on it, and texted.

"I was about to head out of the office for lunch. Where did you want to meet?"

"I'm sending an Uber to pick you up at the front door while I wait on a table. I'm at Roosevelt's."

"Oh, ok."

"See ya in a few. I'll text over the ride info."

The information popped up on her screen promptly. She made her way down to the front door, saw the black car pull up, and hopped in confirming the destination.

About 5 minutes later it pulled up to the curb at Roosevelt's. Roosevelt's was a pretty upscale restaurant. She stepped in and the hostess greeted her.

"I'm supposed to be meeting a friend..."

"Oh, yes, and your name?"

"Tricia."

"Perfect, right this way."

The young woman beckoned her to follow and led her through a slalom of tables and walls until she came up to a warmly lit booth in the back corner of the restaurant. Alex glanced up, and then stood to greet her.

"You're server will be with you in a moment."

They both sat, her leaving some room between them.

"Thank you for joining me. The other night just ended in such a rush," Alex said, perfectly composed with a warm smile.

"Yes, it did, and I'm sorry for that. It wasn't anything you did. I just..." he interrupted her.

"Are with someone, felt guilty, despite how much you enjoyed it, and panicked."

"Um," caught off guard by how candid he was," yes. I just shouldn't have let myself go there. I had plenty to drink that night, and let my..." again he cut her off.

"Let yourself have a little fun? Don't get me wrong, I know you are in a relationship, but I'm guessing you've had a hard time not thinking about it, wanting to feel that again."

Just then the server arrived, and took their drink orders, pausing the conversation.

Once they left, she responded, "Look, don't get me wrong, it was intense and phenomenal, and under any other circumstances I'd have probably wanted to keep doing what we did."

"So you want it again don't you. Just admit it, your boyfriend can't make you feel that way, you even practically said so yourself. When I was fucking you, you made fun of his little cock not being able to do that to you..."

He could see her getting a little flustered. A mixture of her getting hot at the thought, and then trying to reason her way out of it.

"Don't get me wrong, I'm not going to push it on you, but you can't deny that even right now, you're thinking how nice it would be," he said as his hand touched her thigh.

A jolt of sensation spread across her body from his touch, and she could feel her panties dampen.

"You aren't wrong about any of that. But I can't do that to him."

The server returned with their drinks and took their orders.

"Well, I won't press that any further then. We can just enjoy the meal and make good conversation."

So they did. Tricia did enjoy his company, and he was quite the looker. If only...

Time passed quickly and with the meal finished and him paying the bill, they stood up to ready themselves for her return to work.

"I sent for another Uber for you. It should arrive in 2 minutes to get you back to work. It was really nice seeing you again Tricia, and if you ever change your mind, you know how to reach me."

"Thank you, Alex. I'm really sorry."

"Don't be. Who knows, that card may just burn a hole in your pocket, even if it's just for a friendly conversation."

Whether she wanted to admit it, it did seem to do so. All day, it was all she could think about. The image of her pressed against the wall as he thrust into her in that dark conference room kept creeping into her thoughts. His large cock impaling her, kept her soaked below.

She felt like she was on autopilot at home that evening, going through the motions.

"Everything alright?" Grant asked her as they watched a series on their television."

"Hmm?" She responded having been so out there she missed what he said.

"I just asked if everything was alright? You seem distant."

"Yeah, sorry, just a space cadet."

He kissed her cheek and snuggled into her.

She fell into the moment and her mind was calm.

The next day was, as always, a race against the clock to get out of the work grind. Tricia was definitely ready for the weekend. The lunch break always welcomed a celebratory mark of partial completion.

At 1:12 pm her phone buzzed.

"I was going out for a drink or two tonight, care to join me" Was on her screen from Alex.

A few seconds passed, "if you don't have better plans, it could be fun."

She imagined her night as pretty mundane, and her panties had been wet all night and day. It was so fucking wrong, but it sounded so good.

"Sure." Her heart jumped a bit as she replied, and for a moment she wanted to take it back. It felt so weird compartmentalizing her emotional draw to Grant and her raw sexual desire with Alex, but she did.

Grants phone buzzed: "hey baby, think I'm going out with Susan and Mina this tonight. That okay with you?"

"Yeah, that's all good, love," Grant replied, seeing the opportunity in the moment.

He pulled up Alex's number and texted, "So I should be free tonight, if you'd want to get together..."

"That sounds hot, but I've already committed to hanging with some friends. If you'll be game for it, I can always send you a text when I'm heading home."

"Yeah, just let me know."

Tricia came home from work, kissed Grant, and announced her agenda of getting showered and made up for a girls' night out.

Grant's dick sprang to attention as he planned his evening of grooming himself for his descent.

Tricia picked out her clothing carefully. She wanted to feel sexy, she wanted to feel like a delicacy to be savored.

When Tricia exited the bathroom, Grant did double take, she was fucking gorgeous. Her hair done carefully, her face gently accented with makeup, her body adorned with a dress that hid none of her assets.

Part of him wanted to deny her the evening and just keep her to himself. She wore a red dress with a high riding slit along her left thigh,

"You are fucking hot babe," Grant spewed out.

"Aww, thanks. I was just about to ask if I looked okay." She found satisfaction in his compliment, still emotionally separating her intentions, no less.

They embraced and kissed, ritualistically. Then she exited the door.

Grant set into motion his plan. He pulled out the anal douche, his red pair of lace panties as well as his white knee high socks, and put a fresh razor on the shaving tool.

The bath water beat against the tub as it quickly reached temperature. Grant plugged it allowing it to fill, and dropped a little of Tricia's soap in creating an intoxicating smell and bubbles in the water.

Trisha sat in the back of the Uber, figuring it was better than driving after a few drinks. Her fingers anxiously kneaded at each other as she watched the lights go by from her window.

She had texted Alex letting him know she was leaving just before getting out of the bathroom earlier. He sent the destination and his ETA back to her..

Grant took his time ensuring he was smooth all over, as he enjoyed the serenity of a hot soak. He wanted to make sure he took his time so he didn't overexcite himself and blow his load too early.

Trisha's ride arrived at the destination. It was a fun looking little place in the next town over. She had never been to this establishment.

The sounds of voices flooded the room she stepped into. To the left was a cozy little bar area made with solid wood. To the right, separated by a wall, were a series of pool tables, high tops, and a couple sofas. The lighting was soft.

Looking around, she didn't see Alex, and wondered if he was late. She was almost sure he'd get there first.

She walked slowly to an empty space at the bar, noticing several patrons eyeing her up and down. While she didn't entertain them with further attention, she did find it kind of sexy to feel checked out by so many men in the room.

The bartender approached her, and took her order for a drink. She was reaching into her purse, fumbling through it for her phone, when she felt a strong hand rest gently on her shoulder. She turned her head to see Alex, freshly shaven, and smiling down at her.

"Wow, look at you," he said, as his eyes drank her up like a glass of water in the driest desert. "You look stunning."

She blushed and batted her eyes, saying, "Thank you. You clean up pretty good yourself."

Alex was wearing a white button up with the collar loose, under a light tan sweater. It showed off his large toned body. A pair of nice grayish blue jeans snuggly packed his considerable bulge and nice strong ass cheeks.

"I see you've already ordered." His hand caressed her shoulder just beyond the strap of her dress.

"Well, I would've considered letting a guy buy me a drink, but what's a girl to do when she's left all alone at a bar."

"Ah, sorry, I needed to visit the men's room, and when I came back out, you were already here. However, the night is young and I'm sure there will be more opportunities to treat a lady."

Grant had toweled himself off, admiring his smooth skin in the mirror. His cock shrunk in the cold air, as the freshly shaven skin off his balls tightened and tingled. Turning around he checked out his ass in the mirror.

Strutting to the bedroom he gazed over the adornments he had set out for himself. Picking up the lace panties, he gently slid them up his legs, enjoying the sensation over his skin. His flaccid dick fit so nicely into them, and twitched a little as the fabric tickled him. He traced the outline of it with his small soft hands, almost hearing Alex's voice in his head, "Good girl."

Picking up one of the thigh highs he slowly pulled them up his leg, letting them tickle his skin as they glided up. Then he slowly did the other. Grant walked in front of the full length door mirror and looked at this package tucked then turned around and wiggled his booty.

He gave his package a quick slap, gasped, and felt the blood rushing to his member.

"It's really not all that interesting, but it pays well," Alex was replying to Tricia about his work.

"Has to be more exciting than billing. Luckily I don't have to do all the phone fun."

"Yeah, I think I would run fast if that were the case." Alex chuckled.

She was sitting on the stool, while Alex hadn't yet sat. He had remained standing for the initial part of the conversation.

"There's no way I could be a call center person. I'd lose my temper way too quickly dealing with all the assholes."

Alex waved at the bartender for another drink before saying, "I figured you were a spicy one," gently pulling her hair back over her shoulder and behind her ear as he said it.

"You could say that," she said in a seductive way, enjoying his brief and subtle touch.

The bartender came over, fetched them fresh drinks and then went to attend to others.

"So, I could really go for a cigarette about now, care to join me? There's a nice little patio where we can take our drinks."

"I'd be down for it, if you have a spare."

"Of course," he replied.

She stood up, and he placed his hand on the small of her back and guided her to the patio.

"You know, you are so absolutely stunning."

"Thank you," she acted coy, "I'm glad you think so."

Alex considered making a little jab at her boyfriend, but decided against it, lest it send her line of thought in an undesired direction.

He opened the glass door for her and removed a pack of cigarettes from his trousers. Putting one between his lips and handing her one, he then pulled out his lighter and cupping a hand for wind lit her smoke for her. The flame lighting up her face in the darker space.

"Thank you."

"My pleasure. So you smoke?"

"Sometimes. More so socially or when drinking. You?"

"Probably more than I should, but hey, we all have our vices."

"I suppose so."

He lifted this glass, "To vices," he chuckled.

"To vices," she giggled softly, lifting hers to his and clanking them. They held their gaze for some time both taking a long steady sip.

Grant found himself impatient and fidgety. Pacing around the house, unsure of what to do with himself as his dick dribbled little bits of precum from anticipation. He checked his phone. Nothing yet.

Tricia and Alex made their way back in through the door. Seeing there was an empty pool table, Alex asked if she'd care for a game.

"I'll play, but don't laugh. I'm horrible at this game."

"Oh, I won't. I'll even take it easy on you."

"Are you any good?"

"I like to think I've got a knack for filling empty pockets," he chuckled.

"I suppose you do," she laughed, her eyes falling subconsciously to the front of his trousers. Catching herself, she glanced towards the pool stick rack.

Alex racked up the pool balls centering them, and invited her to break.

Tricia tried to put her serious face on as she plotted the most successful break in her life, and instead horribly failed.

Alex walked up for his turn and was quite effective, knocking in one solid. "I guess I'm solids." He took a swig of his drink, looking over at Tricia, and enjoying the sight of her hard nipples pressing through the fabric of her dress.

He surveyed the table and walked around it running his hand over the small of her back as he went by her. He positioned himself for his next shot, giving her a good view of his nice ass perfectly framed in his pants. She licked her lips.

He took his shot, which she was pretty sure he missed on purpose, and said, "Well, I guess it's your turn."

"Are you ready for this?" She joked.

"Show me how it's done." He chided back.

As she leaned over the table and studied her next shot, she felt him behind her, pressing into her ass. She could feel the length of his member resting between her cheeks. His hands ran down her arms to her hands, causing a stray breath to leave her lips.

"Try positioning your hand like this," he said, placing her fingers and sliding the pool stick slightly between them. She could feel him swell against her, letting out another wanton sigh.

She took the shot, sinking the 5 and 7 balls. She jumped up in excitement and wrapped her arms around him in celebration. Then it hit her, that she was hugging him and time slowed for a second. Their eyes lingered, his hands rested on the top of her little perky butt, and they leaned in, sharing a gentle kiss.

Tricia found herself speechless, as she was wrapped up in the moment. The feeling of guilt rose in her for a second. She had come out to meet with a man she had fucked at a work event. She opened herself up to this. She flirted and drank with him, and she had just now kissed that man.

He pulled her tighter into him, "Hey, don't let yourself think too much. We're having fun. Let's just enjoy it," and kissed her again. "How about you see if your streak continues."

She turned around and positioned herself like he had shown her. He gave her a quick spank on the ass. Then she took the shot, just barely missing the pocket.

"I'm going to grab another drink, you want me to grab you one," she asked.

"Yes, I'd love that. Thank you!"

He took another shot while she ordered the drinks, asking for an extra heavy pour on each.

The pool game was close and well battled. It was speckled with gentle touches, caresses, and glances. Their glasses, slowly becoming emptier.