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Brent Lets Brenda Go Out And Play

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Brenda walked into the bar area of the restaurant. As she strolled through, several of the guys at the bar just stared. She looked ravishing in a black cocktail dress, her three-inch heels, and long flowing red hair. She headed directly towards a table where another man and woman sat sipping drinks.

As she approached, the man stood up and gave her a hug and kiss that would’ve started a small fire in the forest. Then before sitting down, she leaned over and gave the woman a kiss that would’ve just fanned the flames. She finally settled herself into the only other vacant chair at the table.

The woman looked at Brenda, saying, “Damn, you look absolutely stunning tonight!”

“Well, Devin baby, you are pretty fine looking yourself,” she replied.

The guy chipped in, “I agree with Devin; you are looking top shelf tonight.”

“Well, Alex, I guess you should know since you hang out with Miss Gorgeous Thing over here,” she tossed her thumb in the air, pointing to Devin.

Alex laughed before saying, “You two are quite the pair. So, what is on the menu for tonight, dinner and dancing, or back to our place for drinks fun?”

Devin rolled her eyes before saying, “You got to be kidding us, of course, dinner and dancing, we ain’t wasting these outfits by just going home. You can wait a few hours before trying to get us out of them.”

As the ladies wanted, they had dinner and went dancing for a few hours before heading back to Alex and Devin’s place. They walked in and went into a sunken living room. The ladies sat down, and Alex fixed everybody a drink. He handed them to Devin and Brenda, then sat down in a chair across from them. He sipped his drink as the ladies drank theirs and chatted.

Devin was the first to make a move. She sat her glass down on a ledge behind the couch that she and Brenda were sitting on. Leaning in, she kissed Brenda. Brenda reciprocated by kissing her back. It wasn’t long before they were locked in a dance of tongues, pulling each other closer with hands starting to roam.

Alex just continued to sip his drink as he watched the ladies. Before long, Brenda had slid the straps of Devin’s dress off her shoulders. This allowed her to tease Devin’s bare nipples while they continued kissing. Brenda pinched, pulled, and stroked Devin’s nipples until kissing became almost impossible with the moans escaping Devin.

Devin’s hands hadn’t been idle either. She had unzipped Brenda’s dress and had let it fall open. Brenda, giving Devin room to pull her dress up and off of her body, leaving her there in just her bra, panties, stockings, and three-inch heels.

Although Devin had pulled Brenda’s dress off, it was Brenda that was still controlling the action. She had pushed Devin back on the couch and was now lying on top of her. She was sucking a nipple as she continued to play with the other. All Devin was doing now was moaning at various levels depending on what Brenda was doing to her nipples.

Alex continued to watch from his chair across from them. As he sipped his drink, he watched Brenda work her way down Devin’s body. She kissed and licked her way as she pushed Devin’s dress down her body. Finally, Brenda knelt and pulled Devin’s dress the rest of the way off, pulling it out from under and down her legs. She then dropped it on the floor where hers had landed already.

She then went back to kissing and working her way to Devin’s now bare mound. Alex smiled, knowing his wife hadn’t been wearing panties. She had been ready for the night with Brenda. As Brenda made it to the fuzzy little patch above Devin’s mound, Devin moaned out loudly. Alex knew this was Devin’s 'please quit fucking around' moan.

Brenda took the hint to quit fucking around and ran her tongue over Devin’s clit as she worked her way down her pussy, splitting her lips as she went. It wasn’t long before Brenda was lapping at Devin’s pussy like she was dying of thirst. This sent Devin into a fit of moaning.

Brenda smothered her clit with her mouth and sucked it hard as she thrust two fingers deep into her pussy. She alternated sucking and teasing Devin’s clit as she thumped her fingers in out of her pussy. Devin was starting to moan uncontrollably and thrash as Brenda pushed her towards an orgasm.

Alex watched on as Devin was pushing herself against Brenda’s face and fingers. He could see the orgasm building until suddenly she cried out. As he watched, he could see Devin unleash a torrent of juices into Brenda’s mouth and face. Devin had always been a squirter, and Brenda had a knack of really bringing it out of her.

Brenda held onto the thrashing Devin as she flooded her with juices. She continued to pound her pussy with her fingers all the way through the orgasm. Brenda had only let up on her clit to catch as much of Devin’s juices as she could.

Finally, both of them settled down on the couch, catching their breaths. Brenda had lain back on the couch opposite Devin, with one leg on the couch and the other resting on the floor. After catching her breath, Devin scooted around until she was lying between Brenda’s legs.

She started running her hands over Brenda’s panties, rubbing her. Brenda was getting excited and was beginning to moan. Devin slid her fingers into the waistband of Brenda’s panties and pulled them down to her thighs. As she did, Brenda’s hardening cock flopped out.


Brent discovered at sixteen that he enjoyed wearing feminine clothes. He grew up with two older sisters. During a game of truth or dare, one of the sisters had dared him to put on her bra and panties. He took the dare and dressed up in her bra and panties. Once he felt the satiny feeling against his skin, he was hooked. From that day forward, he would sneak pairs of their panties to wear as often as he could.

As he went through high school, he hid his fetish for women's underthings from his friends, although he played sports. He even managed to hide it from his sisters and parents. Although the younger sister did catch him with a pair of her panties, she just thought he was whacking off into them. He let her think that.

Then things changed during his freshman year in college. As a pledge prank, he was forced to dress up as a girl and go to a club. Being on the slimmer and more feminine looking side in body shape, it was very easy for him to do. He had been wearing his sisters’ panties and bras but knew he had to dress from head to toe as a woman.

Well, when it was all said and done, Brent had far exceeded his fraternity’s expectations. After his freshman year, he was accepted into the fraternity. Yet Brent’s problem was he now had discovered he enjoyed dressing as a woman. All through his four years in college, he’d sneak off for weekends. He would go to neighboring towns and live out his alternate life dressed as a woman.

It was during one of these weekends that he had his first sexual experience as Brenda. Brenda was the name he had adopted as his female persona because it was so close to Brent. He had been at a club populated mostly by women. What he hadn’t known was the club was the area hangout for the lesbian crowd.

While there, he started getting hit on by this stunning blonde. She came up and started chatting him up. Brent wasn’t quite sure what to do. Although he passed well enough as a woman, he surely wasn’t equipped as one. Things were only getting worse as she started sliding her hand up his leg while they talked.

Her hand was all the way up under the hem of the dress he was wearing and almost discovering the truth of his sexuality. He placed his hand over hers, pressing it into his thigh to keep her from moving it. He took a deep breath and told her he was a guy. She let go with a trilling little laugh before telling him she already knew, but that was okay.

She took him home with her that night. No sooner than her door had closed, she was under his dress, pulling his panties aside. Not long after that, she had him cumming down her throat. She then led him back to her bedroom. He had spent the night learning how to please a woman the right way without ever fucking her once.

Their relationship continued off and on for most of a year. During that time, she had shown him how to become even more feminine, but more importantly, had opened up his sexual experiences. The first time he had ever had anything in his ass was the night she fucked him with a small butt plug as she played with his cock. It steadily progressed into pegging sessions until the night she had invited a male friend to join them. It was the first time Brent had given a guy a blow job as Brenda.

A month later, he had taken his first cock up his ass. He discovered he liked to be fucked as Brenda. The whole idea of sex as Brenda was exhilarating to him. He had learned a lot about sex and himself with her. Then, unfortunately, they went their separate ways when she got a promotion to another city.

Brent was hooked, and being Brenda brought him so much more excitement than being Brent ever had. He added to what he learned and was an amazingly beautiful woman as Brenda. After graduating from college, he got a top job making great money. He used his newfound wealth to buy the best clothes and accessories for Brenda. He had laser hair removal over his entire body. He never needed to shave and, thanks to a very thorough skin regimen, kept his skin silky smooth all over as well. He had a fake set of breasts made that, when placed in a bra and applied to his chest, were almost impossible to know they were fake.

Now ten years later, Brent had truly become Brenda. He was only Brent at work these days. People would probably freak if they knew under his five-thousand-dollar custom-tailored suits, he was wearing women’s undergarments. At home, he spent more time as Brenda than Brent. Being her just felt natural to him. He had accepted he was a man in every sense but loved being a woman as well.

His relationships varied from women to men as he explored himself. He discovered it was a huge turn-on for him to be picked up by a guy and treated as a woman. He had varying experiences with them, as well. Some had been a blow job, and others he had intimate sex with shared both ways.

Women, on the other hand, usually got turned on by the whole experience or completely turned off. It was his experience that within the lesbian crowd, it was easier to find a woman who would accept Brenda with her unique offerings than it was in the bisexual world. Yet there were exceptions there as well.


Speaking of exceptions, Devin was devouring Brenda’s cock as she moaned out her pleasure. Devin sucked her cock deeper until her lips were around the base and the tip was pushing into her throat. She would hold it there before sliding it out until she was taking a breath around the head before plunging back down. Brenda was moaning and pushing her hips up at Devin.

Alex had been sitting in his chair peacefully, watching the action and sipping his drink. That changed when Devin knelt between Brenda’s legs and started sucking her cock. He finished his drink and stripped out of his clothes.

Once naked, he moved up behind Devin and knelt behind her. He watched his wife suck Brenda’s cock as he stroked his own. He was already hard, and now he was rigid with desire. As Devin was bent over Brenda, he lined his cock up to the exposed pussy; with a powerful thrust, he plunged his cock into her pussy.

Devin felt his thrust, and she moaned around Brenda’s cock but never stopped sucking it. As she continued, Alex started working his cock in and out of her pussy with deep strokes. This was forcing her to concentrate on both her pleasure and that of Brenda’s.

Alex was fucking her harder and harder. He leaned forward close to her head. He started talking to her, telling her to make Brenda orgasm. Alex continued, “Yes, Devin, make this slut cum down your throat. I want you choking on her cock as I fill your pussy full of my cum.” He kept going on and on like that, all the while pounding her pussy.

Brenda was moaning with the effort Devin was giving her cock, and she heard Alex’s words to Devin. Devin went harder on her cock but was being rocked back and forth by the pounding Alex was giving her. Brenda wasn’t sure how much longer she could last or Devin or maybe even Alex with his exertions on Devin’s pussy.

The answer to Brenda’s wondered question came quickly, and it was she who gave up first. Reaching down, grabbing Devin’s hair, she forced her cock deep as she could into Devin’s mouth before unloading squirt after squirt of her seed. Alex was next, filling Devin’s pussy with his seed. He rammed his cock deep into her pussy. Being filled with cum from both ends pushed Devin into her orgasm. She was flooding her juices around Alex’s cock in no time.

The three of them eventually untangled, with Devin crawling up next to Brenda and Alex slipping beside Devin. They all knew this was just the opening to a night of carnal pleasure. Once they had caught their breath, the fun would continue for hours.

Brenda to Brent

Brenda dragged herself through the door at noon the next day. As she walked into her bedroom, the transformation began. The dress fell to the floor, shoes kicked off and left lying. Then came the bra but with much gentler care because of what it contained. Then sitting on the edge of her bed, the stockings were rolled off.

Standing up, she walked towards the bathroom, shedding the last of Brenda. A half-hour later, clean and refreshed, Brent walked out into the bedroom. As was his custom, he never bothered with dressing after a shower. It allowed his skin to dry naturally. He crawled into his bed to catch up on the sleep Brenda had not gotten.



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Copyright © 2021
All works published under the author's name of Road_Runner are entirely of my own work. No part of this material may be reproduced or transmitted in any form or by any means, mechanical or electronic, or used in any other fashion without the express permission of the owner.

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