Joey Finds a New App

Joey exited the car and went into work to see what his boss was going to say to him about what she had witnessed. As expected, she was waiting in the hall near the locker rooms and when Joey arrived, she looked at him directly. Joey stopped and waited for the verbal assault he assumed would happen. His boss was no-nonsense when it came to her employees and work. She wasn't a bitch, but she also didn't pal around with anyone either and mostly just intimidated people with her silence, as she was doing to Joey now. Then curtly, she said "Come with me before you get ready for work, Joey. We need to talk. "Joey followed her to her office up the back stairs. She unlocked the door and let Joey in as she followed behind him, shutting the door. She pointed for Joey to sit in front of her desk as she took her seat and then calmly folded her hands on the top of her desk.

"First, I won't insult you by asking if you know why we're here. I want to know what compelled you to allow your boyfriend to perform oral sex on you in the back of the grocery store lot," she inquired in a still calm voice.

"Well, he's actually not my boyfriend uh, I'm not gay. I just uh, find myself uh, kind of hooking up with guys sometimes," Joey tried to answer intelligently.

"So, what you're saying is on any given day you might be out back with a boy or a girl performing oral sex on you?" she inquired in an exasperated voice. "Why did you think it was OK to do that here at work?"

"I'm sorry, Ms. Katy. He kind of begged me to let him and I thought it would be safe back there," Joey said apologetically.

"Clearly, it wasn't. Not only did I see you there, but Frankie the bagger saw you too. Now he is visibly flustered, and I had to help him calm down after witnessing his co-worker getting a blowjob at work," she said to him.

"I'm so sorry, Ms. Katy. Please don't fire me. I like working here and I'm sorry Frankie saw me. I promise not to do that kind of thing here anymore," Joey continued apologizing.

"Hm," she said as she stared at Joey through her glasses with her lips held tight. "Well, technically. You were not working at the time of the incident, so I am not forced to call HR and report it."

"Oh my gosh, Ms. Katy. Please forgive me. I won't" Joey continued begging.

"I'm not finished!" she stopped him with her hand up. "First off, I was surprised that you were there with a boy. I had always thought you to be straight and a nice boy. Secondly, from what I could see it was obvious why boys and girls alike might be looking to 'hook-up' with you, as you say," she continued as Joey listed quietly waiting for the next shoe to drop. "I might have a need for you to help me, outside of work of course, with a couple of things. I need to think about it a bit. Lastly, I'll need you to go find Frankie and apologize for upsetting him," she said with raised eyebrows now prompting Joey to respond.

"Of course, Ms. Katy. Anything I can do to help, thank you for not firing me. I promise you won't regret it," Joey said innocently.

"Well, before we jump to assumptions and conclusions, I'll need you to come over here and let me inspect the goods," she commanded.

"Uh, Um," Joey stammered.

"Just come over here, Joey. I need to see what we're working with and see if it will be adequate for my needs," she said more forcefully.

Joey stood and quickly walked over to her desk as she turned to face him. She reached out and pulled him closer to her where she pulled down his shorts and briefs, dropping them to his feet. With a sure and firm grip, she picked up Joey's hanging cock and lifted it up. She moved it from side to side and up, then down before leaning it and smelling his manhood with a deep slow breath. She moaned slightly, then tentatively reached out with her tongue and tasted the tip of dick, before closing her eyes and swashing her mouth as if tasting a wine. She just as quickly let go of his cock, then waved him off and returned to facing her desk.

"Yes, Joey. It appears you will suffice for what I need taken care of at home," she said to him as he collected himself and returned to his seat.

"Ok, Ms. Katy. Whatever I can do," Joey answered.

"I know you are working this weekend. What about Saturday after work?" she inquired.

"Sure, Ms. Katy. I'm free. Do you want me to call you?" he asked.

"I will pick you up after work and we'll head to my house," she stated.

"OK. Sounds good," Joey said somewhat worried what was in store for this visit.

"OK, then. Go find Frankie, apologize and you may begin your shift after that," his boss said curtly.

"Thank you, Ma'am," Joey said humbly as he left her office.

Joey went and got dressed for work and walked around the store looking for Frankie. Frankie was a young, effeminate boy who started at the grocery store a few months ago. Joey was pretty sure he was gay but hadn't got to know him well enough yet. He was very small in stature and with his long blond hair he appeared very feminine or at least a very slight male by any measure. Joey found him in the produce section where he was washing vegetables and cleaning up the fruit tables.

"Hey, Frankie. How are you?" Joey asked quietly as he approached.

"I'm OK, Joey. What's up?" Frankie said nervously.

"Hey, I'm sorry you found me in the back lot eh, doing things before work," Joey said sheepishly. "I thought it was a good place to do that sort of thing, but apparently not."

"Joey, I'm so sorry if I got you in trouble. I was coming into work, when I noticed you and I couldn't stop watching. Ms. Katy caught me watching you guys and told me to scram," Frankie explained.

"Well, I didn't get in trouble so to say, but she told me to apologize to you. I'm sorry if it upset you or anything," Joey said.

"No, Joey. You didn't upset me. I was just surprised. I didn't know, you liked uh, guys like that," Frankie said quietly.

"Actually, Frankie. I didn't know I liked that either until recently. I guess, I had a couple of encounters that maybe suggested I think certain guys are kind of hot," Joey explained hesitantly.

"Oh," Frankie responded quickly. "I er, so what kind of guys do you think are hot?"

"I don't know, Frankie. I haven't put it all together yet. I guess, like the guy I hooked up with today. He's small and kind of feminine, I guess. I have a friend too that recently started being feminine too, I mean like wearing dresses and stuff. Hot!" Joey explained. "I have another friend who has a trans brother or sister uh, I'm not sure how to phrase it, he was a boy, but now he's very much a girl, except for the genital part," Joey said.

"So, you like femboys, then?" Frankie responded.

"Uh. I'm not sure," Joey replied. "I have to say it's all a bit surreal right now," Joey offered. "I guess I've just been going with the flow, but I'd say that's true."

Frankie stepped closer to Joey, smiling up at him. "You know, Joey. If you ever need help with that tool of yours, I'd be delighted to volunteer."

Joey smiled down at Frankie and noticing how feminine he really was. He had a small face surrounded by slightly curly blond hair that was back in a ponytail. His neck was slender and draped into his small body. He wasn't anywhere near as curvy as Steve or Adam was now but resembled their size and shape before this week. Joey winked at him, "I'll keep that mind, but we might want to avoid getting in anymore trouble around Ms. Katy. At least I better avoid it anyway if I plan to keep my job here."

They both laughed a little and Joey headed up front to check where he was stationed today. He worked his four-hour shift like normal, occasionally fielding glances from Frankie and Ms. Katy as they passed by his section, otherwise his shift was uneventful. Towards the end of his shift, Adam came it with his bag of clothes and told him he'd meet him outside. Adam was wearing red skinny-jeans and a tailored black and white checkered shirt that clearly showed off his curves above and below. He left Joey with a soft kiss on the cheek and a couple of admirers across the store. Joey turned and saw Frankie smiling at Joey with a knowing look and as he wrapped up his section he was approached by Ms. Katy.

"So, I take it you apologized to Frankie for your lewd behavior earlier?" she inquired.

"Yes, Ma'am," Joey replied.

"OK, then. I'll be seeing you Saturday after work," she said with a very slight smile.

"I'm looking forward to helping you, Ms. Katy," Joey said imagining his boss under him. She turned and gave Joey a full view of her curvy ass and long legs. Shaking off the distraction he went to the locker room to get changed. Joey started undressing down to his briefs and pulled out the clothes Adam delivered and while he was getting dressed, Frankie came in.

"So who's the lucky, well-dressed lad that gets Joey's company tonight?" Frankie asked smiling and watching as Joey removed his pants.

"That was my brother, Adam. He came to pick me up. We're meeting a couple at the club tonight. It's ladies' night and we were hoping to catch up with a couple friends there," Joey answered as he refreshed his deodorant and adjusted his package to go down the inside of his leg. Even with his extra-long boxer briefs, the head of his cock peaked out the leg.

"Holy crap, Joey! Is that what your car date was swallowing today?!" Frankie asked as he stared wide-eyed at the cock snaking down Joey's leg. "Phew! I don't know how well that boy was servicing you today, but I'd love to be in a competition to try. Mm Mm. That just looks delicious!" Frankie continued without waiting for a reply from Joey.

Joey laughed and smiled as he pulled up his tight black jeans and put on his black dress shirt. He threw his casual clothes in the bag and closed his locker. As he walked up to a mesmerized Frankie, he smiled at him saying,

"Now that would be a fun competition!" Joey leaned in close to Frankie and continued teasing him, "But you might have a hard go beating out my brother on that one." Joey winked at a now shocked Frankie and left calling out, "See you Saturday, Frankie."

Adam drove Joey over to the club and sure enough it was busy. Joey had never been to this club, nor had he been to any of the younger crowd clubs as they were mostly college aged and young adults. He wasn't really into dancing, so he didn't pursue clubs and such during high school. This time however he was excited to see Mrs. Tyler and Principal Jones together. They were getting hot and heavy at the office and Joey imagined given the opportunity, things would escalate to scolding hot.

They entered Legends and didn't even bother trying to get a 'drinking band' while Joey paid the cover and they looked for Mrs. Tyler. It wasn't hard to find them out on the dance floor being one of the only female couples dancing together. There were groups of dancing adults all over. Most appeared middle-aged or older and while there were a few couples, most were in small groups, likely co-workers or old friends. He and Adam watched as Principal Jones, who was dressed in a short black leather dress and boots, danced against Mrs. Tyler's back. They were shaking and grinding into each other, clearly enjoying themselves. Adam reached for Joey's hand and led him out to the dance floor and started dancing right next to the girls.

"Wow, brother. I didn't know you liked dancing," Joey said surprised.

"Yeah, I do actually. I'm not really good at it, but it's fun anyway," Adam said.

"Hi boys!" Mrs. Tyler called out when she noticed them. She was flushed and working up a good sweat from dancing.

Principal Jones walked directly over to Adam started dancing with him. "You got here just in time. I think I wore my friend out a bit," she said winking at Mrs. Tyler.

Joey took the hint and reached for Mrs. Tyler's hand while they walked her off the dance floor. "We're over here," she said while leading Joey to a dark corner table. They sat down and Mrs. Tyler reached for her cocktail and drank it down right away. "Oh, Joey. I'm having such a great night. It was so much fun to go out with Penny again. She's so wild when she's not at work!"

"Well, I've never seen her the way she is around you lately," Joey replied. "She certainly appears happier."

Joey slid closer to Mrs. Tyler and put his arm around her while watching Principal Jones and Adam dance. The waitress came by, and Mrs. Tyler ordered another cocktail for her and Principal Jones while Joey ordered two Cokes. Joey looked down at Mrs. Tyler who was catching her breath and sighed deeply at the dancers. She noticed Joey watching her and smiled up at him, "What?"

"You seem happy tonight too, Mrs. Tyler," Joey said appreciatively.

"Thanks to the help of my studly admirer," she replied while reaching for his thigh and stroking the length of cock slowly back and forth. She sighed again and leaned up for a kiss from Joey. As they were kissing, Joey felt someone brush up against him and looked over to see a smiling Principal Jones scooting right up next to him, followed by Adam.

"Guess I better not turn my back on my date tonight?" Principal Jones said raising her eyebrows at the two of them. "I think you tried to distract me with your cute little brother so you could move in on my date," she suggested.

"Penny! Stop it. You know I'm all yours," Mrs. Tyler said flirting. "However, if I know you it won't be long before you get your fill of this young stud," she said while pulling her friends hand to Joey's hardening crotch.

"Oh my! Now that's something to think about," she responded while sliding her hand all the way down the length of Joey's cock. Her eyes were wide with lust and wonder, just as the waitress came by with their drinks. "Ooooo. Thank you, Mary. Things are heating up in here and I need to cool off," she said at the smiling waitress.

"I was wondering if you had some playth er, dates coming tonight," the waitress said while serving the drinks.

"Mary, is anyone using the lounge? Maybe we could go cool down in there for a while?" Principal Jones asked.

"Anything for you, Honey," she replied. "You guys' head in there. I'm pretty sure it's open the rest of the night. There was a dinner in there earlier. I'll bring you another round in a few minutes," she said while waving and returning to the bar.

Penny and Adam slid out of the booth together as did Joey and Mrs. Tyler and they all carried their drinks near the rear of the club to a set of closed French doors. Principal Jones opened the door and guided everyone inside before closing the door behind her. The room was furnished with numerous types of furniture including stools and hi-top tables, large leather chairs and loveseats with tables. There were large screen TVs playing music videos and sporting events mounted around the room with music from the club fed from speakers placed throughout the room.

Joey sat next to Mrs. Tyler on a couch, and she immediately cuddled up next to him with her drink. Next to Joey, Principal Jones sat in a large chair-and-a-half pulling Adam onto her lap. The waitress came in shortly after and took orders for more drinks after openly flirting with Principal Jones. Joey noticed that when she exited, she hung a sign on the door reading 'RESERVED', leaving them presumably alone in the club.

"Dawn, I don't know about you, but I had a fabulous time dancing tonight. I missed our outings," Principal Jones said to her friend.

"Well, I'll admit to having a lot of fun too, but all this dancing has got me pooped, and worked up," she replied suggestively looking up at Joey.

Joey smiled, leaning down and softly began kissing her. He extended his tongue into her mouth enjoying the playful tangle. They both sighed and moaned quietly as they became focused on each other's pleasure. Joey was excited to get his hands on her body since seeing her in that sexy dress. His hands explored her curves over the soft fabric creating a very sexy image in his mind's eye while he kissed her. For her part, she immediately laid her hand on Joey's hardening tool and stroked it through his tight pants. When he reached a full erection, he was aching inside the tight jeans and longed for Mrs. Tyler to unleash his cock.

"Oh my! Some girl is going to get lucky," Joey heard Mary say as she set the drinks down on the table in front of them.

"Oh, sorry. We got a little carried away," he apologized.

"That's why you're in a private room, young man," Mary said amused at Joey. "Only staff can badge in while the door is locked. We use this room for private parties that sometimes get a little edgy."

"Well, thanks Mary," Joey said smiling.

"I'll come and check on you guys in a bit. In the meantime, if you need some help with that snake in there you just call me with that button over there. No tellin' what'll happen if that gets loose," Mary said eyeing up Joey's huge bulge as she turned to leave.

Joey looked over at Principal Jones and was shocked to see her cradling Adam like a child and him sucking on her tit. She had the thin leather strap pulled down over her shoulder and was holding her tit in Adam's mouth as he sucked and looked to be drinking breastmilk.

"All this dancing gets my juices flowing. It's nice that I don't have to waste it tonight," she said looking at Joey and Mrs. Tyler watching her.

"She's never stopped making breastmilk ever since I can remember," Mrs. Tyler offered quietly to Joey. "Never really asked her why. She doesn't have any kids that I'm aware of, and she never explained. I used to help her express milk sometimes. It always fascinated me, and tastes good, too," she said flirting with Joey.

"Wow, Mrs. Tyler. You guys really were a thing, huh?" Joey said amazed and excited about the thought of seeing the two ladies together.

Joey watched his brother suckle Principal Jones breasts a few minutes longer noticing that she was also taking time to explore the curves of his brother's body. He then returned his attention to his date and began kissing her some more. After a heated kissing session, she began to undo Joey's belt and pants which required his assistance due to how tight they were. She stood up and bent down in front of Joey to remove his pants and briefs which she pushed down, assisting him with the shoes as well. Joey sat with his now raging hard on in full display which captivated Mrs. Tyler's attention. She then knelt facing Joey with her knees on both sides of his hips, rolled her already short dress up over her ass revealing she had no panties on. Joey looked on at her fat, hairy pussy and could immediately smell the arousal coming from his friend. She reached for his aching cock and lined it up with her wet lips and immediately started to sink down.

Putting her elbows on Joey's shoulders, she leaned in and whispered, "Take me, Lover. Fill me up please."

Sliding down, Joey's cock went easy as her pussy was soaking wet. He could feel the walls of her pussy contract and squeeze him as he entered her. She moaned loudly catching the attention of her friend who belted out, "My goodness, Joey. You'll tear her in half with that thing. I couldn't miss it in your pants the other day, but that thing should require a permit to use on women," she remarked while watching her friend sink down deeper and deeper.

"You need to try this, Penny. I just can't get enough of it," Mrs. Tyler said while rolling her eyes back grinding her hips into the last few inches. "Joey, I need you to fuck me before I go crazy"

Joey began lifting his hips along with hers to keep his cock going deep with each thrust. Her pussy seemed bottomless as she took his entire length of cock inside her. She began yelping with each stroke, which had drawn the attention of both Principal Jones and Adam who were watching her ride Joey's dick. Principal Jones pushed and guided Adam between her legs, opening them wide and revealing her trimmed wet pussy. Adam got right in position and began servicing her while she watched her friend ride Joey's fat cock. He looked down and saw the thick streaks of cream she was leaving on his cock, almost as if he had filled her with cum. He briefly wondered whether she had been fucked before coming out to dance. To her knowledge she left work with Principal Jones, but then he remembered her saying she was going to learn some dance moves with Julian today. It intrigued him that she was fucking other men along with Joey and he made a mental note to inquire tomorrow during the in-service day.