Joey Finds a New App Ch. 57

Joey and Roxanne spent a few minutes holding each other and kissing before he had to head to homeroom. He was attentive to her and in conversation inquired about future dates with Dan.

"Well, I won't lie and say I haven't been thinking about our last date," she started. "He texted me this weekend and asked when he and I might go out again. I replied that I'll let him know soon."

"Where are you on this?" Joey asked. "I mean, if you don't mind me asking."

"Honestly, I'm not sure, Joey," Roxanne replied. "I'm excited about our last couple dates. I can't stop watching the videos on my phone and cloud account for goodness's sake. But, after this weekend I feel, I don't know, spoken for, I guess. Does that even make sense with all that's happened?"

"I think it does," Joey answered thoughtfully. "I think of you as my girlfriend and while we both have a lot of stuff happening outside our relationship, I would feel weird keeping stuff from you. Is it OK that I think of us as a thing? I never really asked you out."

"Being that our first date preceded my two dates with Dan, I'd say there is much to be defined," she replied. Based on my time with you this weekend, I'd say that our relationship is going to be fairly progressive and will require us being open-minded and upfront with each other. "

"Agreed," Joey nodded thoughtfully. "I like being your committed lover and confidante if that's OK, but I don't think either of us are ready to be monogamous. It sounds kinda cheap coming from just me. Am I assuming too much?"

"Not at all, Joey," she replied quickly. "I wasn't sure how to handle my ongoing fantasy of reliving the group sex I had last week with the basketball team. That was like something out of a porn movie."

"So, do we agree to just BE with each other for now?" Joey asked. "Do you want to define things further?"

"I think we are both exploring our new-found sexuality and it would be unwise to shut off that desire in the name of some old-fashioned thinking," she answered. "That being said, I would be crushed to think I was hurting you by being with anyone else, so can you just agree to always be honest with me about where you stand?"

"Me too!" Joey exclaimed in reply. "If you want to change things up, please just be honest."

They sat at her desk for a few minutes more just holding each other before a light knock broke the silence. Roxanne went to answer the door and welcomed a gleeful Mrs. Tyler to their quiet space. Joey was immediately taken aback by her outfit and general look. She was wearing a blue lettuce trim short sleeve V neck smock dress with elastic nipped waist with white thigh high stockings and heels. Her hair and makeup were done up elegantly along with the cheerful and peppy disposition.

"Good morning, young lovers," she said after Roxanne shut the door. "Ooo, how I've missed you two this weekend."

Mrs. Tyler shimmied over to Joey and wrapped him in a luxurious kiss and embrace, moaning while caressing him. She then sharply turned back to Roxanne and marched to her for a quick kiss on the cheek and hug.

"I guess I wasn't the only one excited to get back to school today," Mrs. Tyler said suggestively. "You two are here quite early. The buses don't even get here for another half hour or so. I take it your weekend was well?"

Roxanne smiled and took to answer for them both, "We had a great weekend, Mrs. Tyler thanks to your encouragement. We both spent time together and with our family. Might I say how beautiful your outfit is today? Sexy even."

"Thank you, Sweetie," Mrs. Tyler blushed in response. "I went shopping with my friend and she helped me pick out a few outfits. It's been so long since I felt sexy in my clothes."

"I'm sure Joey would agree, you are hot stuff in that outfit," Roxanne added.

"Well, it's a good thing," Mrs. Tyler replied. "I'm off to my dance lesson this morning before the day starts. I'll see you later, you two," she said as she blew him a kiss and headed for the door.

Roxanne sexily walked back and slid in front of him sitting atop her desk and slightly opening her legs. Joey could see the bulge of her toy stuffed in her pussy and even caught the scent of their recent tryst. Roxanne knowingly bent down and kissed Joey again holding his face to hers.

"Case in point?" she said after their kiss.

Nodding, Joey replied, "Indeed."

They spent the next half hour or so together before the buses began arriving and Joey bid her goodbye for the moment and went off to homeroom. He had a good thirty minutes or so before first period and thought he'd catch up on his app which oddly enough has been escaping his attention.

He was in homeroom before anyone else and sat to see how his app was surviving the addition of Kevin. The first thing he noticed was the addition of Kevin's parents and Mrs. Vamvakos, all read-only to him.

Mrs. Vamvakos: 5'2", 210lbs, G cup. Liberal personality, Fetishes - Cheating, big cock, size queen, cuckolding, femdom.

Lisa: 5'9", 159 lbs, C cup - Conservative submissive, fetishes - anal

Antonio: 6'2", 225 lbs, 8" cock - Conservative dominant, fetishes - anal

He was surprised to learn about Mrs. Vamvakos fetishes and to be honest her measurements as well. With her being so short, she is a large woman, but her breasts are as Kevin said, huge. Clearly, she loved sleeping around on her husband even at 70 years old. He found himself intrigued about her and imagining what sex would be like with her. According to Kevin, she was a fiend for his cock at this point.

He was not so surprised about Kevin and Kellys' parents, however. He knew they were reserved at least on the outside. They were both very athletic for being middle-aged and worked out regularly. Kevin's mom was very fair skinned, and his dad was a darker complexion both with typical facial features making for a very sexy couple. Interestingly enough, Joey couldn't see any scheduled updates from the read-only view. He figured he'd talk to Kevin about his parents and Mrs. Vamvakos later or at lunch.

The morning bell rang, and announcements started bringing Joey out of his own thoughts. He prepped his bag and books while waiting for first period which for him was English being an 'A' day. Joey wondered how Billy would look this morning after his week of 'transition' just a few days ago. Almost on queue with his thoughts, Billy texted him.

Billy to Joey - Do you think it would be OK if I sat next to you in the back today? I'm a little freaked out being here at school like this.

Joey was intrigued about what 'like this' meant and couldn't wait to see how his former bully / feminized boy presented. Seeing him in those girly clothes over the weekend was awesome and made Joey's cock ache thinking about fucking him again or better yet sharing him with Kevin or Coach.

Joey to Billy - Absolutely! Did you dress sexy for me again?

Joey thought taking ownership of Billy's changes was helpful to his efforts and decided to encourage him further.

Joey to Billy - You know how much I like that thick ass of yours. Don't go getting filled up by any boy in school without me. I want to watch you eat cum and sit on dick all day.

Billy to Joey - I won't. I guess I owe you this though if you really want to watch.

The next text was a link to a cloud account with an embedded video link. Joey put his earbud in and hit play, being sure to angle his screen away from anyone else. The screen showed a close-up of a hand setting the phone so that it was angled catching Billy fully dressed up as he was on Sunday kneeling down alongside a bed. It did not look like the bed Joey saw on Sunday when he dropped in on Billy so he assumed it was either his brother or father's room. He assumed this because coming in from the other side of the video was a long, hard cock. It was an even pale shade from tip to balls and surrounded by a bush of strawberry blonde pubic hair. The male brandishing the heavy thick cock was muscular with thick thighs, tight abs, and ass. It was hard to say if it was his brother or father as they both were similar in size and build. But Joey need not worry as coming in from the other side behind Billy was a mirror reflection of the huge cock now in front of him except hairier. Both men were equally fit with similar sized cocks which appeared rock hard and close to a foot long. As expected with the changes Joey implemented on Friday, they were leaking pre-cum excessively. Billy looked nervous as he shifted to the center of the view and reached out for both pulsing and leaking shafts.

"That's it, Little Sister," said Billy's brother, Jake. "Show your brother and daddy how much you love big dick."

Billy looked as cute as he had on Sunday when Joey took him to the mall, so he assumed he cleaned up before this video was taken. When Joey laid him down in his bed, he was a bit of a mess with dried cum in his hair and dripping out of his ass. His make-up had been smeared and he was busy eating Joey's cum out of his sister's pussy. His sister didn't go into detail with the text, but maybe this was how his night ended after he got caught.

"Little girl," his dad, John started. "You done made Daddy's dick so hard and big I'm not sure you'll be able to handle it."

Apparently, they hadn't experienced any of Billy's new capabilities because he could easily handle the two huge cocks in front of him. Joey watched as Billy started in on his brother's dick collecting the long string of pre-cum and swallowing first. Using his newly developed oral skills he made his way down the long shaft easily swallowing it into his throat. By the time he bottomed out on his brother, both men were hooting and complimenting Billy.

"Holy shit," exclaimed Jake as Billy took the final inch into his throat. "Look at sexy Billie go!"

"Daddy's little girl looks to be really good swallowing big dicks," John observed. "Make your Daddy proud and show me how it feels for my daughter to suck dick."

Billy pulled himself from his brother's dick and now looking completely flushed and breathing heavy, started the same on his father. Scooping the pre-cum with his long tongue, then working the thick long shaft into his mouth and throat. When he bottomed out his dad gripped some of Billy's hair and jammed him against his hairy groin.

"I wonder what other secret skills my little girl has been holding back on," John said.

"I don't know, Dad but with a fat ass and thighs like that, I can't wait to take her for a ride," Jake commented.

"Age before beauty, Son," John added. "I think my little girl wants to sleep in Daddy's bed tonight."

This comment triggered a moan from Billy and a short laugh from Jake. John released Billy's head and let him start to bob his head up and back on the long shaft, easily swallowing it in its entirety. Billy's face had grown severely flushed now as he sucked his father's dick, then moved to his brother's. Jake picked up the camera and brought it in for a close-up POV view allowing Joey to see Billy with his skirt, stockings, and small heels on. His hips and ass pushed the skirt out allowing Joey to make out his budding breasts as well. Jake did as his father during his blow job and pushed his head down against his groin, holding him there for nearly a minute while grinding into him. When he was released, Billy pulled back while John stepped closer bringing both huge dicks close to each other. Billy brought both dicks together and started sucking them both into his now wide mouth. Because of the angle he could only get half of their cocks in his mouth, but it was no less impressive. While sucking both, he ran his tongue back and forth between the two shafts as if to jerk them off.

"Dad," Jake said urgently. "I'm gonna blow here soon. Can we cum on her face?"

"How about it, Baby Girl," John asked teasingly. "Does my sweet little girl want her face covered in Daddy's cum?"

Billy nodded quickly and urgently before both men pulled their shafts from his hungry mouth and began jerking off over his face. Billy was breathing heavily, and his eyes darted between the two dicks. Jake released first immediately covering half of Billy's face, followed shortly by John. They both grunted incoherently while stroking full streams of cum on Billy's face and in his mouth. As it had been with Kevin, Coach and Joey, they easily covered Billy's face with cum and he happily swallowed what landed in his mouth.

Once finished, Jake kept the camera on Billy while he scooped cum into his mouth eventually filling it. He showed his mouthful of cum to the camera before swallowing it, then slowly and methodically cleaned each cock.

"Wow, Little Sister," Jake said in a breathy voice. "You and Bro are going to have some fun this week! I'll send you this video so you can think about my big dick all the time."

John reached down and turned Billy's face up, now adjacent to the huge semi-soft cock and said, "You're my good little girl and I can't for you to show Daddy some lovin' tonight. Now you go git washed up and I'll see you at bedtime."

The video ended there, and Joey realized he was hard again from watching it. Joey shook his head quickly shaking off the growing anticipation of Billy's feminization or as coach called him a sissy boy. In the time he spent watching the video announcements had finished and the bell rang. Most of the students exited to head to their first period which for Joey was English. He made his way to Mr. Smitski's class sitting in his usual seat next to Kevin and Stevie in the back. Having arrived first he sat and waited as Kevin entered with a huge smile on his face shortly, followed by Stevie who came in looking cute and sexy. Stevie was wearing a pink tank top with some puppy graphic and small, tight denim shorts. This was accompanied by knee-high striped stockings, pink sneakers, and a loose grey hoodie.

Kevin took his seat then leaned over and quietly said to Joey, "She loves my new size, Dude. Plus, when I mentioned that my good friend Joey and her former student was also well endowed, she came twice asking me about how we would fuck her. You let me know when you're ready and we can meet her together. I'm telling you; do not knock doing it with an older woman. She is wild, Man."

Kevin's attention was drawn to Stevie who sat down on the other side of Joey smiling and looking more timid than normal. Joey took a second to check out his friend's curves and smooth thighs, then remembered he had spent the morning with Coach and Stacey.

"So," Joey started with eyebrows raised. "How was your morning with Stacey and Coach?"

"I was just about to ask the same thing myself," Kevin chimed in.

"I'm glad we came in early," Stevie began. "We met Coach in his office, and he talked about some crazy stuff. I mean I know we've been doing some wild stuff since last week, but Coach says some couples do this stuff their whole life together. He talked about how when the man is not, er, big enough; the couple can have what is referred to as a 'bull' to take care of the sex part." Steve appeared surprised by this revelation and continued, "I mean they get married and have a bull do the sex part for their whole time together."

"Yeah, I'm learning a little bit about all this myself," added Joey. "My boss talked to me about how she is in a relationship like that. Wild, huh?"

"Well, I guess it's better than cheating. At least both can be involved. Like you and Stacey did this weekend," Kevin said.

"Woah," Joey interrupted nodding towards the door. "You gotta be kidding me."

Billy walked in and went to Mr. Smitski to say something quietly as Joey, Kevin and Stevie looked on flabbergasted at the look Billy was sporting. Billy was wearing a form fitting v-neck pink t-shirt, with a short black skirt and thigh high black socks with a triple white stripe at the top. He had black patent leather shoes with thick heels, a black choker and what looked like black straps holding his socks. His hair was longer and dyed black with a white strip over his left ear. He was wearing makeup and frankly looked sexier than when Joey saw him the day before. Smiling shyly, he walked and sat in the seat in front of Joey, mouthing a quiet 'Thank you' as he sat down.

Joey exchanged glances with Kevin and Stevie who were still in a state of disbelief at the transformation Billy had experienced inside of a week. Billy was fully embracing the physical and sexual transformation and if Joey was being honest, looked hot doing it.

"Looking hot, Billie," Joey said quietly.

Billie looked back and smiled flirtatiously at Joey, then glanced at Kevin and Stevie before turning back around and starting to text on his phone.

Billie to Joey - Thanks for letting me sit here. My dad told me I couldn't dress as a boy anymore and took all my clothes last night. My sister is supposed to take me shopping after school today.

Joey to Billie - Well, thank your dad and sister for Kevin and I cause we're enjoying the view. Are you OK? Video was sexy too. Can I share it with Kevin?

Billie to Joey - I'm OK. A bit nervous, but OK. You can show your friends if you want. Please don't post anywhere. My brother would be mad.

Kevin was hovering now and asked Joey to share his contact so he could text him too. Joey shared Billie's contact card with Kevin and Stevie who both texted him before class started. Mr. Smitski started right in once the bell rang, but Joey was distracted throughout class thinking about all the sexual changes he's experienced in just over a week. He couldn't believe he had fucked almost ten different women and more than half that of feminized boys in as many days. He was confident the Master PC app was boosting his sexual stamina but it's like he has become a magnet for sexual partners. Joey wondered whether Kevin would experience something similar over the next week or so. He was brought out of his own thoughts by a text from Billie.

Billie to Joey - Can we meet before your next class? Private if that's OK.

Joey to Billie - Sure. Wait outside the classroom.

Joey put his phone away and focused on class for the rest of the period and when the bell rang Joey told Kevin and Stevie to go ahead and he'd catch up with them at lunch. When he left the class, Billie was waiting, and Joey nodded for him to follow. He led Billie to the back hallway and up to the band room where he discreetly entered then guided him to the bench.

"What's up Billie?" Joey started as they both sat down.

Billie slid right next to Joey, sat with his hands in his lap and his knees together and nervously said, "Thanks for meeting with me, Joey. I don't really have anyone I can talk to about this stuff."

"I get it," Joey said putting his arm around Billie gingerly.

"Yesterday when you left my sister and I," Billie started. "My dad and brother came home from work and caught me in the middle of cleaning my sister. My dad sort of freaked out. When my sister left for work, both he and my brother came in to talk to me. He asked me about what was happening and why my body was changing. I didn't really know how to answer him either. I told him about you and said you were supporting me. I didn't mention Coach or Kevin. I hope it's OK, I told him about you and I."

"You didn't say we're boyfriends or anything, did you?" Joey asked.

"No, no, no," Billie replied quickly. "I just said we did things together and that you sort of liked the new me. He was surprised that I was hanging out with you again after all these years, but that's all I said. He and my brother talked with me for a long time. Then before I knew it, my dad had me clean up and I was making that video."

"Wow," Joey said. "So, crazy night, huh?"

"You're not kidding. While I was showering before the video, Dad emptied my drawers and closet of any male clothes. He said I had to wear the girlie stuff all the time. He said if I was going to be a girl, I had to be the sexiest girl ever. He said he and Jake would help me be the best girlfriend ever."