Two Days Earlier
Brian was frustrated with the negotiations with A.J. Robinson. This was a potentially big account for the company, and he wanted to land it. He was desperate to land it. Even though Jim insisted that Brian was a vital part of the company, he felt like he wasn't doing his share. Brian was not the strong, manly man that Jim and his crew were. Far from it.
All his life, Brian had been called a sissy and other derogatory names from the bigger boys. He'd have been beat up a lot if not for the fact that Jim was bigger than most of them and protected him. If he was lucky, girls might let him hang out with them in order to get him to do their homework or whatever, Otherwise, they would laugh at him too. Oddly enough, their teasing never bothered him. In fact, it made him happy.
One of the girls in high school even took it further. He came to her house and helped her with her homework. She got a good grade. Unlike some of the girls who might use him this way only when a good grade was needed, Lisa was different. She identified him immediately as a sissy. In fact, he confessed to dressing up in his older sister's clothes to her.
Lisa's teasing only made him want to be in her presence more. Even for a ninth grader in high school, she was developing quicker than the other girls. She told him in no uncertain terms that as long as he did as he was told, he could be her sissy. That was when Brianna really came into existence.
It started with her allowing him to wear her panties and a bra when he did her homework. It escalated to full dress up and make up and an occasional trip outside. An element of excitement was introduced to the equation when Lisa began dating Jim a year later. He was on the football team and she was a cheerleader. Brian was helping them both, though Jim knew nothing about the sissy element in all of this.
Lisa would tease him about how his best friend was fucking her, and how she sucked his cock. Then, she would tease him with comments like, "I bet you would like to suck his cock too, wouldn't you Briana?"
He tried to deny it, but she never quit teasing him. As was always the case with Lisa, she found a way to take it to the next level when she got a new boyfriend. Brianna was an attractive sissy, thanks to Lisa's help. The time finally came when she arranged for Brianna to suck her boyfriend's cock. It was a setup.
Briana had done Lisa's homework that day, in full dress and makeup while Lisa was the only one home. Brianna hadn't a clue what was going to happen. Lisa went to her neighbor's house, and her boyfriend showed up and let himself in, It very quickly escalated to him insisting that Brianna give him a blowjob. "Come on, " he said. "Lisa told me you were a good cock sucker, and I know you want it."
Brianna was freaking out on the inside. What if he found out he was really Brian? He resolved to suck his cock and get him out of there. As he was about to cum, Brianna figured she'd jerk him off the rest of the way, but he grabbed the sissy's head and forced him to swallow every drop. Not so much as a thank you before he left.
Lisa came back and acted surprised when she heard Brianna's story. He was freaked out, but Lisa's comments, such as, "good girl" and "that's what sissies like you are here for" made him feel alright. Brianna thought for sure that he'd been spotted, but Lisa insisted he had not. "Sweetie, you're more girl than boy."
It was during those times that gender identity became an issue with Brian, but he only dared explore the expression of his gender with Lisa. By senior year, Lisa had moved on from him, and he was left trying to find a woman who would help him along. Eventually, he started contacting Professional Dommes, which led to his relationship with Mistress April.
He was putting a lot of pressure on himself to deliver the big contract to the company, because it meant they could expand. Jim's unwavering support and encouragement made Brian feel more pressure, and he was spending a lot of time online with Mistress April. A revelation earlier in the afternoon had Brian debating what to do, though he knew what Mistress April's answer would be.
He prepared himself by slipping into his prettiest pink babydoll nightie and matching panties, full makeup and sexy pink heels. He made contact with Miss April, who was dressed in black. Her long black hair was tied back in a bun and she wore glasses, giving her a look of authority. She gave the hint of a smile through her red lipsticked lips. "What do you want, sissy?"
Brian's head was down. "I'm sorry Mistress. I know how important your time is."
April chuckled. "You're lucky you are my favorite little sissy bitch, Brianna. Otherwise, I wouldn't bother with your little whiny, needy ass."
The chastity cage was just too tight for Brian as he heard these words. "I'm sorry, Mistress. Did you get my gift?"
"Yes I did sissy, " she said rather sternly. "While it was nice of you to make such a big gesture, don't think that you can just buy me off like that."
"No.. Of course not, " Brian replied . "I simply wanted to do it because you are such a Goddess to me. I don't deserve your attention."
"That's why your my favorite sissy, " she said with a hint of approval in her voice. "If you moved closer, I might even have a place for you as my sissy maid. I have a hunch you could handle it."
"I could come visit you, Mistress. If I could just be in the same room with you..."
"We'll talk about that later sissy, " April interrupted. "What do you want?"
"You know I am trying to get this deal done for the company."
April laughed. "You know what I find sad, sissy? I bet that partner of yours would gladly take you as his sissy bitch if you just came out to him, but instead you hide and come crying to me every day."
"Please Mistress."
"You know you'll get honesty from me, ' she looked at her watch. "Don't come to me if you don't want to hear it. Now, can we hurry this along?"
Brian was red with embarrassment. "Well, Mr. Robinson, A.J. and I have been corresponding back and forth mostly. We've met twice, and I'm supposed to meet him tomorrow."
April sighed impatiently. "Yeah, so?"
"So, um , he sent me an e-mail from some group called Men Who Like Sissy Girls with a picture of a sissy. It was meant to be forwarded to somebody else, I'm sure. In it, he talks about the things he'd like to do sexually to her."
"So?"
Brian pouted "Mistress, I don't know what to make of it?"
April laughed. "Oh my God. Just because you're wearing a blond wig doesn't mean you have to be so dumb."
"What are you saying?"
She took off her glasses. "Look, the answer to all of your problems is obvious. What more do you need, sissy? Somebody to come knocking on your door?"
"Are you suggesting I get dressed up pretty for Mr. Robinson just to make this deal and let him have his way with me, " Brian asked, already knowing the answer?
"What are my rules when it comes to you and guys, Sissy Brianna?"
Brian's cage hadn't gotten any looser, and he was looking down as he replied. "I'm supposed to please any cock that is offered to me."
April nodded. "Very good, my pet. Now, if you need me to spell it out for you, I expect you to go meet with with him and do what you were meant to do. Get dressed as sexy as you can, please him in any way he asks and get the deal done. That will make your precious Jim happy with you, and you want to make him happy, don't you?"."
"Yes Mistress."
"Is that all?"
"Yes, and thank you Mistress."
"Contact me after you follow through with it." April shut down her camera.
"Shit. I was gonna ask her if I could get out of my chastity, " Brian whined,
Brian had arranged a meeting with A.J. Robinson at his downtown office on the 12th floor. It was rare that he got out dressed up. He was just too shy to dress up as Brianna during the day, even though he could still pull it off. Plus, how would Jim and the guys at the company react to it?
Brian liked the blond look, so he went with it. He settled on a red dress that was fitted and went just above the knees. He chose red heels. He did full makeup, including ruby red lipstick. He grabbed his purse and headed to his car. His mind was racing. He couldn't believe he was actually going through with it.
He settled on the strategy of surprise, which might backfire on him. To A.J., this was just Brian coming by for final negotiations. The end of their most recent conversation let him know he was on thin ice when he was told, "You should know I have other companies wanting to do business with me. If you can't show me what makes you so special tonight, the negotiations are over."
There was a female receptionist at the front desk. She chuckled when asked who was coming to see Mr. Robinson, and he responded, "Brian" in a not feminine enough voice, though his look was good.
"Not bad sweetie, " she said. "A little heavy on the makeup, but not bad. It's the 12th floor. Go on up. He's waiting for you." He walked away and heard her add, "Don't do anything I wouldn't do, hun."
It seemed like the longest elevator ride of his life as his nerves were getting to him. He got off and walked down a corridor, past an empty secretary's desk and to the office. Brian stood outside the door. He took a breath. "Here we go."
A.J. was an older man in his late 50's with salt and pepper hair and a goatee. He was only slightly overweight, but in good shape. He wore a Navy blue suit as he stood at the liqueur cabinet. "Ah, Brian." He poured a couple of drinks. "Right on time, I see." He did a double take as he saw the woman in front of him. "What the?"
Brian nervously cleared his throat as he saw A.J. looking him over. "You asked me what I could do that the others can't. Well, I can, um , be your personal sissy."
"I see, " A.J. took a big drink. "Well, you'll understand if I want to see proof of that."
Brian was blushing. "Yes. If we do business, I'd be willing to be your sissy once a month for the next year."
A.J. grinned. "How about two years?" Brian downed his drink and said nothing. "No. One year, twice a month with three additional weekends of my choosing and an option to continue our arrangement for an additional year."
Brian said nothing for a moment before slowly nodding. "Okay."
A.J. extended his hand and they shook on the deal,. "I'll have my people draw it up."
"Wait, what?"
A.J. poured them another drink. "Oh, you're a secret sissy? In that case, we'll keep that clause out of the public papers, but it will still be binding."
"Okay."
"Pleasure doing business with you, " he said as he raised his glass. Brian joined him in downing his drink. "Of course, I'm gonna have to see how you perform, sissy Brianna."
Before Brian could answer, A.J. had him in his arms in a kiss. Brian accepted it, kissing him back. He also became aware of something poking him.
A.J. undid his pants and the impressive bulge in his underwear had to be eight inches. "Okay, little lady. Lets see how you suck daddy's cock."
Brian was quickly on his knees with a hard cock pointing at his face for the first time since high school. He instinctively kissed the tip, leaving a trace of lipstick on it. He gently grabbed it and started licking it all over, especially underneath.
"Lick my balls sweetie, " he instructed. Brian could smell his manly scent as he began licking his hairy balls. He gently took each one into his mouth and started sucking it. "Outstanding, Brianna. You have potential."
Hearing the name Brianna made Brian feel weird for a moment. He never heard a man call him that before, and the gay thoughts came to mind for a moment. They went away quickly, because he didn't feel like Brian sucking a cock. He was Brianna. His cage was tight again, and he could not deny he liked this.
Without being told, Brianna started sucking the cock slowly. No rushed job here. She wanted to make sure A.J. enjoyed the experience. She wanted to get the deal done. More importantly, she wanted to please this man. "Take it deeper, " he insisted. "I want to see you gag on my big cock."
Brianna was doing as told. She felt the cock at the back of her throat and pushing further. Her gag reflex kicked in, and she came up for air before going back for more. This went on a few times as A.J. had a cock coated with the sissy's saliva. "Okay, I'm gonna fuck your face."
A.J. grabbed Brianna's head and started thrusting in and out as she simply sucked and concentrated on keeping his cock inside her mouth. "Yes, I think I'm gonna like having you as my sissy slut."
This went on for just a few minutes before it happened. A.J. took his cock out of her mouth. "Sit right there, " he said as he jerked off in her face. Soon, jets of his cum shot out, covering her face in a creamy mess. "Yeah. Suck it some more."
She sucked him clean. When he was satisfied, he pulled her up to her feet. "Don't clean your face, Brianna. You look good that way."
Brianna was taking in the moment. She had just been used by this older man. A.J. went to the liqueur cabinet again for a refill of their drinks. He handed her one. "Thank you.":
"Let's take my private elevator to the roof, " he took Brianna's hand. "It's a beautiful view."
In the elevator, Briana was wiping her fingers on her face and licking them clean. "Can I ask you something?"
"I don't see why not."
"What is your attraction to sissies?"
A.J. grinned. "Oh, that's easy. I've found that girls like you are more eager to please their boyfriends. I don't know a lot of women who would do what you just did."
They got off the elevator and onto the roof. Brianna looked around. There was a helicopter landing pad, though no copter was present. There were a couple of buildings taller than this one, but it was an amazing view. The sun had gone down, and lights lit up the city to the sound of traffic. Further off in the distance was the ocean.
"What did I tell you, " he asked as he downed his drink? "Beautiful view, isn't it?"
Brianna nodded in agreement as she downed her drink. "It is. It's breathtaking."
"You know, if you keep building your company the way you are, you guys could have office space here in the city."
"I think I'd like that."
A.J. kissed Brianna again. "Plus, we could meet more often for some fun."
Brianna felt his hardness already poking against her again.
"You know another thing I like to do Brianna, " A.J. had the biggest grin?
The sissy smiled demurely. "I can only imagine."
"I like to fuck a sissy right on the railing of the roof. In fact, I'd like too fuck you on the railing. How about that?"
Brianna was still very nervous. "If that's what you want."
He nodded. "Oh, I definitely do. Why don't you take off that dress there, darling?"
Brianna complied as he helped her with the zipper in the back. She stood in her red bra and panties and heels. "Now, take off your panties." Brianna stood facing him and revealed the pink chastity cage she wore. A.J. laughed. "Another thing I like about you sissies. You keep your little clitties locked so you can learn to take pleasure from being fucked by a real man."
He grabbed the little pink chastity cage. "Is it tight?"
Brianna nodded. "Yes, it is."
"That's the only way you sissies learn to stay limp." He teased her by pulling on the cage and releasing his grip. "Nobody wants anything to do with your itty bitty clitty."
"Are you gonna fuck me, " she blurted out?
"That depends. Are you gonna ask nicely?"
"Please fuck me, daddy. I need your big cock inside me."
He pointed to the railing. "Lean against it "
He stood behind her and laughed as he noticed the plug. "Sissies. I love them." He pulled it out. "We'll, damn. That's a big plug. I guess you want a big cock, don't you?"
"Yes. I need big cock fucking me."
He positioned his cock at her open sissy hole and pushed in. "Ask and ye shall receive, " he said as he pushed in without much resistance. He was thrusting in and out. "Relax, darling. You won't fall off the roof."
The strangest feeling overcame Brianna. She closed her eyes and for a moment, she pictured Jim behind her, probing her deeply. "Oh God, yes, " she moaned before realizing she was talking. "Fuck me."
"Push back against it, " he instructed. She began pushing back against his cock and coming back up as he let her do the work. "That's it, darling. You know what Daddy likes."
Brianna opened her eyes and looked at the city view as she gave up her girlie virginity in what still amounted to a business deal for the company. It felt good as he began to touch her in just the right place with his big love muscle. In all honesty, all thoughts of being a man in bed vanished on this night. Brianna had found her calling.
A.J. pulled out. "Darling, lets go over to the picnic bench."
"Okay, " she took his hand as he led her to the bench.
"Hop on up there and lay on our back, darling, I wanna look you in the eye when I make love to you."
It was the strangest feeling, but it felt right. Brianna lay on her back with her legs in the air as A.J. again entered her sissy pussy. She was making eye contact with the man who was making a proper sissy girl of her. He was fucking her at a steady pace as her chastity cage moved around and she moaned in intense pleasure.
Brianna had experienced the bliss of sissygasm through instructions from Mistress April on how to use her toys, but this was a real man's cock. For an older man, A.J., had incredible stamina, and Brianna soon found herself in the throes of her first orgasm with a man. It built up and slowly let loose.
When it stopped, A.J. was still pounding her hard. "You are one hot piece of ass, Brianna. "One of a kind."
This continued for several minutes, and Brianna was delirious with delight as she felt a second orgasm building. A.J. recognized the look. He touched her cage and teased her. "Cum for me darling. Come for daddy."
The pleasure continued to build and tease her before she let loose again. A.J. leaned down and planted a deep and sensual kiss on her. "Are you ready for daddy's seed?"
She tilted her head up, bit her lower lip and nodded. 'Uh huh."
A.J. began to pick up his pace and soon he emptied his love fluids deep into Brianna's sissy pussy. He kissed her again with his big cock still penetrating her. "You may be the best I've ever had."
He helped Brionna off of the table. She smiled. "So, does this mean we have a deal?"
He kissed her, "Best deal I've ever made." He held her in his arms. "Twice a month for a year with three weekends with an option for a second year."
"Yes, as long as we're doing business."
He kissed her again. "I'd like to hook up with you occasionally outside of our deal."
She laughed as she reinserted the big plug and put her panties and dress back on. "We'll see."
"I'm serious, Brianna. You and I could be great together."
She grabbed a mirror and some wipes out of her purse to clean up her face. "Let me think about it."
"Okay, but don't make daddy wait too long for an answer." He was almost begging at this point. "I can take real good care of you. Clothes, salon appointments. Whatever you need."
She was reapplying her makeup and listening to him without answering. "Did I mention I have a yacht and a private jet?"
She finished her makeup and kissed him. "We'll see, sweetie. Let's get the paperwork done and signed first."
"You'll have it tomorrow. I promise."
She went to the main elevator. "Okay, just send it to the office. You know the address."
"And then we can talk about hooking up some more, " he asked? "We could go out to dinner. Wherever you want."
She stepped into the elevator and turned around and smiled at him without saying a word. "Can I call you, " he asked as the doors shut?
With the doors shut, reality set in. "Oh my God. Did that just happen? What if Jim finds out? I can't let him find out. Oh crap. What if A.J. blabs to him? No, he won't unless I don't honor the deal. Did I really just make that deal?"
Brianna stepped off the elevator and into the lobby area. It was quiet in the room, and the receptionist was the only one there, apparently watching TV. She stood up when Briana was walking by. "I'll give you credit, honey. You really rocked his world. I don't think I've ever seen the old man beg before. Impressive"
Brianna was blushing. "Excuse me"
The receptionist motioned to the TV. "Security cameras, sweetie. Even on the roof."
Brianna started to panic. "Oh my God."
The young, attractive receptionist walked over to Brianna. "Relax, I'm not telling anybody.'
"Thank you."
The lady smiled. "So, did you make a deal?"
Brianna nodded. "We did. A very good one, but I had to work for it."
The young brunette giggled. "Well, obviously. That's the price a girl pays to do business sometimes."
"I suppose so."
The receptionist walked Brianna to the door. "Oh please. If I could ride Mr. Robinson's cock to get some place in this company, I'd be all over it. I don't care. It's just unfortunate for me that I'm not his type of girl. I guess that's another thing you have going for you."
"I suppose so." Brianna walked out the door. She was still in shock over what she had done. She wanted to go back home and tell Mistress Alice all about it. She felt sure that her Mistress would be proud of her. That thought made her smile
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