Three Cheers For Sissy Brittany
Brian showed up at Mr Davis's house to do some yard work. He was still at work. The teen boy was grateful for the opportunity to make a few bucks, and there was always something that needed to be done around the yard.
Brian always had need for money. It wasn't just that he had a video game habit, but he had another habit that he didn't tell other people about. He liked to dress up in girl's clothing, and he had gotten into trouble for stealing his mother's clothes before. It didn't go over very well.
He resolved to start buying his own clothing, starting with bras, panties and nighties, but soon he was progressing to full outfits and even make up. He had gotten good at putting on his own makeup after watching several tutorial videos on YouTube. When Mr Davis paid him at the end of this week, he was going to get a prom dress.
He didn't have the nerve to actually wear the dress at the prom, but he wanted to have it so he could at least imagine what it would be like. He had the dress and the heels picked out, and it was on layaway. All he needed was one more payment, and it was his.
He went into the garage to get the tools and noticed a box out of the corner of his eye. There was a gold, blue and white outfit sticking partially out of the box, and he recognized it as a cheerleading uniform for the Fillmore High School Bulldogs.
He went to the box for a closer look. The uniform was only part of the contents in the box. Several of Mr Davis's daughter's clothes were in that box. Stacy had gone away for college. He picked up the cheerleader's outfit, remembering how beautiful Stacey looked when she wore it. She was totally out of his league.
He held up the outfit, noticing the pom poms in the box. His better judgment was telling him to put everything back in the box and get to work, but he wasn't thinking clearly on this day. He figured he would just put the on outfit for a few minutes, maybe do a pretend routine or two and then get to work. What would be the harm?
Hastily, he stripped down to his pink panties and matching sports bra. He put on the outfit, which was just a little bit on the snug side but still fit him. There was no mirror to look at himself, so all he could do was imagine how he looked. He picked up the pom poms as thought to himself, "What was that cheer that I saw the girls do before?"
He thought for a moment. Stacy and the other girls had done this one routine. He jumped up, moving his arms and kicking his legs. "We are are the Bulldogs mighty and proud, we'll fight until the end. We'll fight with everything we have, and we are gonna win."
"Was that right," he asked himself? "Close enough." He got into the routine, quite sure he was doing the kicks and the jumps right. While he was doing the cheers, he didn't hear Mr Davis' his car pull up. Brian was getting just a little bit carried away. He looked at the closed garage door and kept cheering. "I could totally be a cheerleader," he thought proudly to himself as he kept going.
After several minutes, he heard somebody clear his throat behind him, and looked to see M. Davis with his arms folded, looking at him curiously. "I must say, you do those cheers about as well as my daughter."
Brian was startled out of his cheering routine. He turned around to see the older, still attractive man with salt and pepper hair. "Mr Davis, I was just. Let me get."
The older man walked up to the teen. He put his hands on his shoulders. "It's okay. In fact, why don't you come in the house with me."
"But I, got work," the boy stammered.
"Don't worry, you'll be paid for your time. Come on." He took the boy's hand. Nervously, Brian held his hand as his palms began sweating.
"You know, that outfit looks cute on you. If I didn't know better, I'd say you like to dress up in women's clothing now and then"
Brian stammered. "No, I was just." The older man wasn't interested in the teen's people excuses m
Mr Davis led him to his daughter's bedroom, where there was a makeup desk with several of Stacy's things still sitting there. "Would you sit down and make yourself pretty for me? I know you know how."
"But I might," Brian begin explain.
"It's okay," he reassured him with a gentle squeeze of his hand and a smile. "I know about your dress up time at home. I've seen you. Remember last weekend when your parents were out and you we're running around your house and decided to go outside?"
"You saw me?"
The older man nodded.
"But I, it was dark. I didn't think."
Mr Davis motioned the teen to the chair at the makeup desk as Brian instinctively sat down. "It's okay. I'm not judging you. Make yourself pretty for me. I want to see how you look wearing makeup and my daughter's cheerleading outfit. She won't mind you using her makeup. She's not here anyway."
Brian suddenly realized that it would just be he and the older man at the house as his wife was out of town.
Nervously, Brian began doing his makeup as the older man watched. "You do that quite well. It looks like you have the skills of a woman."
Brian blushed as he applied a little bit foundation, a blue smokey eye look with mascara and eyeliner, just a hint of blush and ruby red lipstick with gloss.
He looked in the mirror, impressed with himself. Brittany was back. He turned to face the older man. "How do I"
Mr. Davis leaned down and kissed the sissy boy on the lips in mid-sentence. "You look lovely. I can't call you Brian when you look like this, so what's your name dear?"
"It's Brittany."
"Cute, you sort of look like a Brittany with your blonde hair. You should let it down instead of keeping it in that ponytail." The older man reached out his hand and took Brittany's hand.
"Where are we going?"
I want to show you my room," Mr Davis said with a smile. Brittany nervously followed into the bedroom. It was a big, with a king size bed. There was a pastel pink motif to the room. "The decor was my wife's idea. It's a bit feminine, but the bed's comfortable. Have a seat."
He sat down without questioning the older man. It was almost like she was mesmerized by him. Brian was becoming Brittany in the presence of this older, confidently dominant man.
Mr Davis removed his shirt, revealing his hairy chest, and just a hint of a belly. Next came his trousers, and Brittany's eyes went wide at the sight of the bulge in the man's underwear. Mr Davis stood in front of him. "Have you ever seen a man's cock before?"
Brittany shook her head, but the man continued. He pulled down his underwear, and a hardening 8 inch cock popped out. It was hairy and not trimmed. The man stood in front of the nervous sissy, cock inches away from the his lips.
"I'm not going to make you do anything you don't want to do dear," he said confidently. "But I will tell you that anything we do here will be just between us. I'll pay you for your time. I know you came here to do my yard work, but I don't think it's fair that we do what we're about to do when you came here to work for me."
"I'm not a, I mean I don't do it for money."
"But you do it," the older man arched an eyebrow and curiosity?
This sissy shook her head nervously. "No sir. I've never done it before"
"It's okay if you want to touch it," he said with a smile of optimism, flexing his penis in front of her as it went up and down a couple of times. "It's just between us."
Brittany reached out her delicate sissy hand. Yard work hadn't done much to change that. She was still a bit of a dainty little fairy. She gripped it and leaned in and kissed it. She opened her mouth, taking the tip in and gently sucking.
"You're doing good sweetie," the older man encouraged. "Go ahead, just suck it. I think you know how to do that."
Brittany would never admit that she had been watching sissy porn at home and knew very well what to do. She began sucking the older man's cock. It was already quite rigid, and she could taste what she presumed was his precum.
The older man ran his hands through the sissy's hair, and the sissy began getting a bit more confident as she sucked him deeper. She noticed his body tensing up a little bit, and his breathing got a bit more rapid. With a grunt, it happened. He unleashed his manly seed inside the sissy's mouth. It was a taste she wasn't prepared for, but it didn't stop her from taking it all.
"Oh God," he moaned as he thrust forward. "Good girl. Very good girl."
There was a lot of cum, and Brittany did her best to keep in her mouth, swallowing without giving it much thought.
The older man froze for a moment, as if thinking about what he had just done. He knew it was wrong, but the sissy didn't seem to mind. He helped her to her feet and gave her a big kiss. "Just like a girl. That was amazing."
it was almost like time stood still, and Brittany was overwhelmed with many emotions. She melted into his kiss, unsure of what to do next. She was putty in his hands.
The older man led her to the kitchen for a quick drink. They made small talk at first, and then it was about how Brittany looked in the cheerleader's outfit.
"I have a bunch of outfits," she bragged, "and I'm getting a prom dress with the money I make from doing your yard work today."
"I'd love it if you'd model it for me."
"Really? You would?"
"Yeah, I would. And maybe you could let your hair down, and you could go somewhere with me. Just so you could get out. I doubt you'll get to wear the dress at the prom."
The sissy frowned and shook her head. "No sir. I won't."
"Then it's settled. You'll model it for me when you get it. When do your parents go out of town again?"
"This weekend. But I don't have the dress yet."
The two finished their drinks. "Don't worry about it dear. You'll have the money." The older man led the sissy back to his bedroom and laid her on the bed.
Brittany suddenly realized what was about to happen as the man laid on top of her and began kissing her. His hard cock was already pressing up against her. She didn't fight it. She didn't quite know what to do other than kissing him back. She felt certain it was going to happen one way or the other.
Mr Davis propped some pillows underneath her ass, keeping her on her back as he reached over into the nightstand drawer for the lube. He began lubing up the sissy's until now virgin hole. The toys she had played with were nothing compared to what was about to happen. First went one finger, then two and then three. When Brittany begin moaning, he knew it was time.
Mr Davis, not breaking eye contact, began pushing against Brittany's tight hole. It was a battle at first, but the hole surrendered as his big cock entered her slowly. The sissy moaned loudly. "Sir, it hurts."
He leaned down and kissed her, a few inches of his cock inside of her. "It's okay. Just relax. Daddy's going to take care of it."
There was still a bit more pain as more of Mr Davis's cock entered the sissy's tight hole. Soon, he managed to get most of it inside as he kissed her again. Brittany got used to the feeling and it became more pleasurable.
Mr. Davis began fucking the sissy, the tightness of her rear passage feeling amazing against his cock. Admittedly, his wife hadn't been giving him much sex lately, and it was incredible to take the virgin hole of his sissy neighbor. His thrusts became steady and a bit quicker. He reached between the sissy's legs, grabbing her four inch cock and stroking it.
The two continued making eye contact "My special little sissy," Mr Davis said. "Our little secret. Just for you," he proclaimed upon his inward thrust. "Take it all my dear."
The sissy's loosening hole was receiving everything that Mr. Davis could give it, and she was feeling the pleasure just from being invaded from behind. The fact that he was stroking her cock made it more exquisite. She began leaking a little, but she still hadn't cum yet.
Recognizing that sissy Brittany was close to the edge, Mr. Davis let go of her cock and begin thrusting harder inside her hole as she moaned loudly, echoing through the house. "Yeah, daddy's little slut," he said has he kept trusting harder. "You like this, don't you?"
"Uh huh," she replied as she panted and moaned loudly, having trouble keeping eye contact as her eyes wanted to roll to the back of her head.
"Daddy's going to cum in your bottom young lady. Are you ready for it?"
She panting and moaned a faint "Yes."
"This will change things between you and I my dear. Here it comes." The older men kept thrusting hard and grunting and moaning. Without being touched, the sissy began spasming cum out of her hard cock, and the sensations of her body contracting and her anus tightening sent the older man over the edge as he came inside of her ass.
Mr Davis released his seed inside of Brittany's ass. He leaned down and kissed her, still cumming.
His popped out of her asshole as he lay on the bed beside her, holding your hand. The sissy was staring at the ceiling in a mental daze, and for a moment the older man questioned what he had done. He knew it was wrong, but it felt so right.
For a while, they laid on the bed holding hands, staring at the ceiling before Mr Davis finally spoke. "Are you okay Brittany?"
"Uh huh."
He turned and kissed her before getting out of bed. "Under the circumstances, I think it's best if you don't worry about working today. Let me pay you what you were going to get."
He handed the sissy a $100 bill, significantly more than she had coming to her. She looked at him in disbelief. "Sir?"
"You earned it. Buy yourself something nice."
"Do you mind if I take a shower," she asked?
"Go right ahead," he motioned to the shower.
Brittany stepped in, getting the water just right as she reached for the soap. Moments later, Mr Davis joined her, and they lathered up each other's bodies, kissing and caressing each other.
Mr Davis stood behind the sissy, his already hardening cock positioned at her tight hole once again. Brittany whimpered, thinking she knew what was coming next. The older man turned her head for a kiss. "Not yet. Next time my dear."
The two got out of the shower and got dressed. Brittany was back to Brian again, and Mr Davis escorted him to the door. He stopped before opening it, giving him a kiss. "Now remember, I want to see you in your dress when you get it. And we'll do something together oh, okay?"
The sissy nodded nervously. "Yeah, I'll let you know when I get my dress and my mom and dad are gone."
Mr. Davis opened the door. "This weekend would be perfect. Helen's not in town until next week, so you and I can spend the night here, if you want?"
"The whole night," the sissy asked?
He nodded. "The whole night. We'll sleep together in my bed."
Brian blushed and smiled. "I'd like that." He turned and walked out the door.
Sissy Brittany Makes A Sale
Brian was feeling a little bit bitchy. His sister was in the Girl Scouts, and it was time for selling cookies again. Sales weren't be as going as well as her mother would like, so Brian got enlisted in selling the cookies. It's not that he minded doing something that was a big girly. It was the fact that his mother paid more attention to his little sister than him.
He was knocking on doors and making sales. Maybe it helped that he was a bit effeminate and was a good talker. Maybe it was the fuchsia panties and sports bra he was wearing underneath his boys clothes giving him confidence. Whatever the case, he was making quite a few sales.
Darnell and Trayvon were sitting on the couch and enjoying some beers as they watched the basketball game. Trayvon was feeling just a bit horny, his massive cock tenting in his shorts. "Hey man, you want to go down to the club?"
Darnell looked at Trayvon. "What? That gay bar across town?"
"No man, I'm talking about the sissies they have there that dress up like girls."
"Come on man, why don't you just call a hooker?"
Trayvon shook his head. "Hookers cost money bro. I ain't trying to pay for it."
Darnell laughed. "I ain't never paid for it in my life. You must be losing it."
There was a knock on the door. Trayvon got up to answer it. Standing on the other side of the door was a blonde haired boy, wearing a baby blue shirt and matching shorts. It was Brian selling cookies. He went into his sales pitch.
"Yeah man, we'll buy some cookies," Trayvon said with a smile. "Come on in."
Darnell shook his head. "No way Tray. I ain't buying any. I got plans for my money right now."
"Hey, didn't you say your sister was trying to get practice for her final exam?" Trayvon looked at Darnell with a plan forming in his mind.
"Practice," Darnell asked before realizing what his friend was getting at? "Oh, no way man. No."
"Just Do It. Go ask her."
"I ain't asking her shit," he replied flatly. "You do it."
Brian watched the two, wondering what they were talking about. "If I caught you at a bad time, I can just go, he said as he turned for the door.
Trayvon took her hand. His big black hand dwarfing the feminine boy's hand. "No man, come with me. We'll buy some cookies" He led Brian down the hallway to a bedroom where the door was open. There was a pretty black woman sitting in a chair at a makeup desk. "Hey Sophia, I got somebody you can practice on."
"Where did you find this one," she asked with a grin?
"Never mind that, go ahead and give her the works. I'm going to go talk to Darnell. By the way, you want some girl scout cookies? He's selling?"
She nodded and looked at the sissy boy. "Yeah, put me down for some mints." She led the effeminate boy to the chair and shut the door behind him. "So, you want your makeup done?"
"I was just coming here to sell cookies," he stammered
"Well, you made a sale, but how about you help me out? I'm studying for my final exam at the beauty school and I could use somebody to practice on."
"Beauty school?" Brian squirmed in the chair.
"Yeah, in fact," she reached for her camera and took a picture of Brian when he wasn't ready. "That's the before picture."
"Before what?"
She smiled. "Trust me girl, you'll be amazed." She reached for a pink robe in her closet. "Why don't you put this on and take off your clothes."
Brian hesitated. "I, I don't know about that."
"You have to," she insisted. " This isn't just about your face. I want the whole look. I'm going to put you in some different clothes and I think I have something that'll fit you. It's just us girls here. Go ahead and take it off. You ain't showing me nothing I ain't seen before."
Brian stripped down to his fuchsia bra and panties, and Sophia snickered. "Oh, I see. Those are cute."
"i just," Brian blushed.
She touched him on the shoulder. "I understand. Just put on the robe and have a seat."
Sophia was a nice lady, and she talked about her plans to open her own salon and how she would be doing nails and makeup and hair. She could do it all. Brian found that out as she had his hair in curlers in no time and was working on his makeup.
"You got good cheekbones," she said. "Anyone ever tell you that before?"
"No," he replied as he watched her go from one makeup brush to another.
"I would love to put fake eyelashes on you," she explained, "but they don't want us using lash enhancers. I think you got enough to work with here."
"So it's obvious you dress up a little bit honey," she said casually as she applied the blush. "I know a few girls like you. You got a name girlfriend?"
"It's Brittany," the sissy nervously replied.
"That's cute. I want to do something different with your eyes. Try a few different colors, but it's totally going to pop with your blue eyes. Trust me," she reached for her eyeshadow case.
It didn't take Sophia long to get the makeup done. It was a more about getting the curlers out and she also applied fake nails and painted them with a hit pink quick dry polish that had an amazing shine to it. The time just flew by, but it had been about an hour.
Britney stood in front of the full length mirror next to Sophia. "What do you think girl," Sophia asked? "Do you like?"
Brittany believed she did make up pretty well, but Sophia nailed her look. She almost wished she was going out somewhere, instead of trying to make a sale and going home. Sophia handed her a pink skirt and blouse. "I don't have any shoes that'll fit you, but those sandals look cute enough. Those aren't boys sandals, are they?"
Brittany shook her head as she got dressed. "No, but they aren't too girly, are they?"
Sophia grinned. "A little bit, but that's okay. It's perfect for what you're wearing."
Brittany stood there nervously looking at her reflection in her new outfit with her face all made up. Could she make sales dressed this way, and what would the neighbors think? She didn't have long to think about that when Sophia took her by the hand and led her out of the room.
"Boys, let me introduce you to Brittany."
Trayvon stood in front of the Sissy and smiled. "Damn babe You look cute."
"So how many cookies are you going to buy," Brittany asked?
"Yeah, we got it covered," Darnell said from the couch, flashing a $50 bill. "Why don't you come sit next to me."
Trayvon leaned in and kissed the sissy on the lips as he guided her to the couch.
Sophia looked at the two and shook her head as she headed back to her room. She was laughing. "Don't hurt the poor girl."
"We ain't gonna hurt her," Trayvon said as he took the sissy by the hand and sat on the couch with Brittany between he and Darnell. "We going to take good care of her."
In no time, Darnell had his cock out of his pants, and Brittany gasped at the size of it. Her neighbor had an 8 inch cock, and this one looked like it could be 10 inches
"Kiss it baby," Darnell said with a smile. She got on her hands and knees in the middle of the couch with her head over his big cock.
She felt her panties getting pulled down by Trayvon and then something wet against her asshole. She realized Trayvon was licking her.
Brittany suddenly realized that she was about to be fucked by two big black men. She hadn't even had an opportunity to see what Trayvon had between his legs. She was busy trying to get as much of Darnell's monster cock as she could in her mouth as he pushed her head down on it.
Brittany had practiced her gag reflexes on her toys and had gotten good at sucking her neighbor's cock, but it was challenging as she tried to regulate her breathing while sucking the big black cock. Her eyes teared up. If she had been looking at herself in a mirror, she'd have been thankful that Sophia used a no run mascara.
Trayvon started fingering her tight hole with one finger, then two. When he got the third finger in there, he smiled. "Yeah, she's ready for it," he said as he removed his shorts and got behind her, his monster cock pushing against the sissy's tight opening.
Without much warning, Brittany felt Trayvon pushing inside of her. It hurt, and she let out a loud moan, muffled by Darnell big black cock. Darnell laughed. "Do that again bro. That felt good."
Trayvon laughed. "You should feel it from my end D." He kept sliding in, and the tightness was incredible. Trayvon loved sissies because usually their asses were tight and it provided the friction he needed to give him in a huge orgasm.
Darnell was enjoying what Brittany was doing with his cock, mainly deepthroating it. He was starting to get harder and leaking a bit of precum. The taste was overpowering to Brittany. It was something she never quite experienced before, but she craved it. She wasn't thinking at this point, just moving on instinct.
Darnell kept pushing her head on his massive shaft, and she did what she could to keep him happy. His moans and his encouraging comments let her know she was doing it right. Trayvon had picked up the pace, but her ass was somehow getting adapted it to his massive shaft thrusting in and out of her.
How long the scene went, she didn't know. Her jaw was starting to hurt as Darnell still hadn't cum inside her mouth yet. Trayvon was the first to let go. With a thrust and a grunt, he exploded inside of her ass. "Yeah, that's it baby, take it," Trayvon said proudly.
"If you're through, I need to finish off in her."
Trayvon smiled. Be my guest. Darnell took the sissy by the hand and led her to the kitchen table, where he lifted her on top of it and put her legs over his shoulders and pushed his cock against her hole. Her cum lubed ass received him eagerly is he bent down and kissed her. "You one hot white bitch," he said as he thrust in and out.
He began thrusting hard in the sissy's ass and he grunted in pleasure. It was Brittany who finally released her orgasm all over her own stomach before Darnell tensed up erupted inside her ass. Her second load of black cum for the day.
Darnell pulled out of her, and Brittany suddenly felt quite empty. She lay on the table, trying to compose herself as Darnell went into the kitchen to clean himself up. Trayvon kissed her and handed her her panties, which she put on, feeling cum leaking out of her ass onto the back of her panties.
She made the sale. $50 worth of Girl Scout cookies. "What about my clothes," she asked nervously. "These are Sophia's clothes."
Trayvon kissed her. "Don't worry baby. You can come back and get them later."
"Come back?"
"If you want to," he smiled hopefully. "I mean, I think we can have a lot of fun here when we got more time, you know babe?"
Sissy Britney took the money and her cookies and left, suddenly realizing that she was dressed as a girl. She would have been relieved to know that her makeup was still good, but how the neighbors would have seen her, she didn't know.
Her neighbor, Mr Davis, was home. Though she thought about going to see him, she wondered what he would think about what she just did with the two black men. She went into her backyard and climbed through her bedroom window, trying to avoid her mother and her sister. She had to figure out how to remove her makeup and get back into her boys clothes.
Fortunately, he had makeup remover hidden in his room. When the coast was clear, he headed from his room into the bathroom and cleaned up. His mother was none the wiser. She was just happy that so many cookies were sold.
After giving his mother the money, Brian retreated to his bedroom, where he lay on the bed in a euphoric state. It seemed like cum with still leaking out of his stretched and slightly sore ass as he stared up at the ceiling. What was he becoming? The real question is, did he like it? He smiled as he drifted off to sleep
