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At the end of the school day Jack was getting ready to leave when he walked by Matt and Emily.
“Hey” she said “we should get started on the project tonight. Since Matt’s not doing anything now you two can go get started on it. I have to go run some errands first before coming over but it shouldn’t be a problem. Matt can give you a ride home too, can’t you Matt.”
“Yeah sure” Matt replied not paying attention to Emily but staring at Jack.
“Great I’ll see you guys later.” Emily walked away leaving Jack alone with Matt.
“Let’s get going, I plan to use your house to fuck Emily, and while we wait for her to get there you can entertain me.”
Jack started to panic because he knew his mom would be home. “You can’t my parents will be there.”
Matt just stared at Jack before saying “then you better find a way to distract them.”
It only took a couple of minutes to get to Jack’s house and when they walked in his mom was there to greet them.
“Oh who’s this? Hi I’m Lisa ” His Mom asked, surprised to see someone with Jack.
“Mom this is Matt, we’re in a group together for school” Jack said.
“Hi Lisa” Matt couldn’t stop staring at Lisa at her chest. Lisa was absolutely gorgeous. She had gone to college majoring in psychology but with every intention of finding a husband that would let her live an easy lifestyle. That’s were she met Jack’s dad, Henry. She noticed him because he always seemed to be studying in the library. She started to flirt with him and strung him along for a couple years making him play the nice guy. She always made sure he was studying every weekend while she went out and partied. Towards the end of their college career they made it official and got married soon after she “accidentally” got pregnant. Henry immediately got a high paying job that required him to work a lot but Lisa didn’t mind, although she did miss her active sex life.
Lisa naturally had a big butt that she sculpted by years of hard work but unfortunately didn’t have the boobs she desired. Soon after she was done with her pregnancy with Jack she made Henry pay for breast surgery. She spent most days working out and shopping with friends as she didn’t have to work.
Lisa had just returned from working out before Jack got home and was just wearing a sports bra and shorts that hugged her ass. She noticed Matt staring at her and smiled, glad to be receiving attention that she usually didn’t get from her husband. “Jack why don’t you go get us drinks while I get to know Matt.”
Jack quickly went and got some water bottles out of the fridge not wanting to leave Matt alone with his mother. When he got back they didn’t even notice him as they were already deep in conversation. Jack felt uncomfortable that his mom was acting like all the girls in school around Matt.
“Uh Mom we have to go get started on our project” Jack said.
“Oh yes, plus I’m probably boring Matt over here and I have to take a shower, there’s cookies out in the kitchen help yourselves” with that she left the two of them alone.
Matt turned to Jack and said “wow you really can’t wait to suck my cock again can’t you?”
“What no!? I thought we were going to start the project.”
Matt laughed “yea right, we both know that’s not what we’re gonna do. You got rid of your own mom so you could hurry up and taste my cock again.”
Jack face started turning red as he glanced down at Matt’s privates and licked his lips. Just then Lisa walked by wrapped in nothing but a towel while carrying her dirty clothes. “Sorry boys, I just wanted to drop these clothes off in the laundry room before my shower.”
Matt seized the opportunity, making no effort to hide checking her out, “don’t worry about it Lisa, Jack will take care of those” he looked over at Jack “be a good boy and go get your mothers clothes.”
Jack feeling uncomfortable shuffled over and took the clothes from his mother. Lisa looked at Matt staring at her, she was pleased that the thin towel was giving her the attention she wanted. “Thank you Matt you’re very considerate. Jack here has trouble sometimes being a good little boy, it’s good that you’re here to tell him what to do and help him out, you must come over more often.”
“Oh I certainly will” Matt replied.
As Lisa turned to leave her towel slipped and fell to the ground. Jack’s eyes went wide as he gazed upon the first naked woman he had seen.
“Oops” Lisa said making no effort to cover up as Matt walked over and picked up the towel handing it to Jack.
“It’s okay Lisa, you’re absolutely stunning there’s nothing to worry about. You should probably get another towel though since this ones’s dirty.” Matt said.
“True but there’s no rush though. Since you’ve already seen me naked there’s no need to stay modest.” Lisa replied not taking her eyes off Matt.
“Mom this isn’t appropriate” Jack yelled.
Jack winces as he felt pain on the back of his head as Matt slapped him “that’s no way to talk to a lovely lady like your mother, this is her casino oyna house and she can do what she wants.”
Lisa glared at Jack angrily “he’s right, while Matt’s being polite and complimenting me, you’re being immature and yelling at me. You should thank Matt for disciplining you before I did. Go ahead and tell him thank you.”
Jack lowered his head and muttered “thank you Matt.”
“No problem, Lisa let me know if you ever need help with him.”
“Oh I will, but for now I’ll leave you two boys alone and go take my shower now” Lisa said walking away swaying her hips.
Matt turned to Jack “Let’s go up to your room, bring her clothes.”
As they entered the room Matt told Jack to take his clothes off and get on his knees.
“Dude why didn’t you tell me you’re moms so hot.”
“She’s not” Jack said uncomfortably.
“Yes she is, and you think so to otherwise your dick wouldn’t be hard.” Matt smiled and looked down at Jack “why don’t you put her used panties on and model for me.”
Jack could still feel how damp they were still from his mother’s workout as he slipped them on, his dick already hard. He stood up and slowly turned around as Matt laughed at him.
“God you’re so pathetic, who’s bitch are you?”
“I’m your bitch Master.”
“Say it louder, yell it.”
“I’M YOUR BITCH” Jack yelled, hoping his mother couldn’t hear.
Matt chuckled as he pulled his cock out “crawl over to me.”
Jack crawled over and put his face right in front of Matt’s cock. He took a moment to admire it, it made his own cock look so small in comparison as it barely stuck out from the panties. Jack knew he would never be more than a man than Matt. He started to lick from the base of the Matt’s shaft all the way to his head. Savoring the taste as he looked all over.
“That’s a good boy, get me nice and hard for when Emily gets here.”
Upon hearing this Jack started going faster, feeling jealous that Emily was going to get Matt’s cock instead of him. He hoped that if he went faster he could be the one that got Matt’s cum instead of Emily.
“Woah slow down there, it’s not a race. Here relax your throat and let’s work on you being able to deepthroat me.”
Jack relaxed his throat and took as much of Matt’s cock as he could. He felt it hitting the back of his throat and wanted to gag and throw up. He backed up a little bit then tried again, this time determined to get it all the way. He felt like throwing up again but kept going until his nose was pressed against up against Matt.
“There you go, just keep doing that over and over. I bet you want me to fuck your mom too. I could tell how cock hungry she was as soon as I saw her. “
Jack kept taking the full length of Matt’s cock into his throat for what seemed like forever. Jack never wanted it to end and was loving every second of it. The power Matt has over him as he slid his entire cock in and out of his mouth made his dick harder than last time he sucked Matt’s cock.
They both jumped when they heard a knock at the door and heard Lisa say “Jack there’s a girl here waiting for you two.”
Jack’s eyes went wide with fear because he didn’t want his mother to open the door and see him wearing her panties and Matt’s cock in his throat. He tried to take Matt’s cock out of his mouth but Matt used his hands to keep him there.
“We’ll be right down Lisa, we wouldn’t want to keep two beautiful women waiting.” Matt yelled through the door.
“Okay I’ll be downstairs” Lisa replied.
After they heard her walk away Matt finally let go of Jack’s head. “Get dressed but leave the panties on” Matt said quickly getting dressed leaving Jack there.
Jack used a towel to wipe off his face and put his clothes on. When he walked downstairs he saw Matt sitting in between Emily and his mother on the couch.
“Jack come sit with us, I’m getting to know your friends better” Lisa said, never taking her eyes off Matt.
“But Mom there’s nowhere for me to sit”
Matt looked up and said “it’s okay you can sit on the floor in front of me.”
“Good idea, that way you can be close to us” Emily chirped in.
Jack went over and sat by Matt’s feet. As soon as he sat down Matt put his feet on top of Jack. “I hope you don’t mind, it’s just my feet have been killing me all day and it’s more comfortable this way.”
“It’s no problem” Jack replied, hoping his mother or Emily would say something.
“Oh Jack you’re such a good friend” Lisa said, “I know, why don’t you give Matt a foot massage since his feet hurt.”
“But Mom” Jack whined
“Do it now Jack, you heard what your mother said” Matt sternly told Jack. At this Emily broke out laughing and took a picture of Jack on her phone.
Jack gulped and took one of Matt’s foot into both hands and started to massage it. His face was burning red but he was happy he was sitting down so no one could tell his dick was hard.
“Oh Matt” Lisa said, putting one hand on Matt’s shoulders, her other hand rubbing canlı casino on his thigh, “I really will have to come up with a special thank you for helping Jack be a good boy. It’s not everyday such a big handsome man comes and helps me with this…” Lisa looking down at Jack “boy. How about I run to the store and pick us up some wine, you two have to stay for dinner and after we can take a dip in our hot tub out back.”
“That would be amazing Ms Lisa” Emily replied, smiling at her.
“Just Lisa is fine honey, and no problem it’s the least I can do.”
“But Mom they didn’t bring any swim suits” Jack said.
“We’ll go naked then, I don’t mind showing off.” Emily said.
“It’s settled then” Lisa said cheerfully. “I’ll be back soon. Matt can you do me a favor and watch Jack while I’m gone?”
“Absolutely I’ll make sure he doesn’t get in any trouble.”
“Thank you so much.” Lisa said turning to Jack who was still massaging Matt’s feet “Jack make sure you do whatever Matt says. He’s a lot more mature then you are and is in charge until I get back.”
“Yes mam” Jack said hanging his head.
“And make sure to thank him for watching over you”
Lifting his head and seeing Matt’s smug smile “thank you sir for being in charge of me.”
“Okay I’m off to the store.” Lisa walked out to the garage and drove off.
As soon as she was gone Emily jumped on top of Matt and they started making out. “Let’s go up to Jack’s room so we can get more comfortable” Matt said taking a break from kissing. They all got up and made their way upstairs and when they entered the room Matt got completely undressed.
“Emily I want you to get undressed slowly” Matt told her.
You could see the smile on her face as it was obvious she liked showing off her body. She slowly raised her shirt over her head and walked over and sat on Matt’s lap, allowing him to kiss her neck before she reached behind her and unhooked her bra. Once unhooked she guided Matt’s mouth onto her dark colored nipple. She started to moan as Matt started sucking and nibbling on her breasts as she humped against Matt’s cock.
She then got up and turned around so Matt could see her ass as she took off her pants and panties in one motion. She then got on her knees and expertly started sucking Matt’s cock.
Jack stood there in amazement, both Emily and Matt hadn’t said a word to him. He started to rub his own dick through his clothes. He still couldn’t believe he got to see his first two naked woman in his life thanks to Matt today. He moved around to get a better look at the action when Matt seemed to remember he was there.
“Emily stop for a second, you’ll enjoy this. Jack why don’t you show Emily what you’re wearing underneath your clothes.”
Jack turned bright red as he started to undress. Emily broke out laughing when she saw him wearing his mother’s panties. “OMG that’s so pathetic, who’s are they?”
“They’re my mom’s, she was wearing them earlier when she was working out but Matt made me put them on” Jack replied, his face red but his cock hard as a rock.
“They look good on you, especially since you don’t have a real penis do you?” Emily said, a devious smile on her face.
“No, I don’t have a real cock.” Jack replied leaking precum.
“You can’t even call it a cock, that’s reserved for real men, not sissies who wear panties. It’s more like a nub or even a clit. That’s what we’ll call it from now on, clit.” Emily told Jack.
“Thank you Emily” Jack said.
“You know, you don’t look half bad wearing them. With a little work I could pass you off as a girl.” Emily then turned her attention back to Matt “this is making my pussy so wet, what else can we make him do?”
Matt smiled “sissy why don’t you crawl over here and show Emily what we were working on before she got here.”
Jack crawled over, determined to deepthroat Matt on his first try. He grabbed hold of Matt’s cock, giving it a kiss on the head gently licking the slit before he took all 8 inches down his throat.
“This is so hot, he’s such a bitch” Emily squealed before starting to suck on a Matt’s balls.
They both started to work on Matt’s cock together. Jack would instinctively hump the air every time his tongue would touch Emily’s tongue, the closest he’s gotten to a kiss with a real girl. Jack reached down and started jerking off his own member.
“Jack stop touching your clit, you don’t get to cum until we both do” Matt said.
“Yes master” Jack replied before hungrily going back to sucking his cock.
Emily let out another moan before Matt told her “Emily get on the bed it’s time.”
Emily laid down on the bed and looked at Matt “make sure you go slow at first, I’ve only given blowjobs before so I’m still a virgin.”
“Who would of guessed I would be in a room with two virgins” Matt said. “Jack how’s it feel to be this close to pussy because of me.”
“Thank you sir, I wouldn’t have gotten this experience without you.” Jack replied still on his knees looking kaçak casino at the two of them.
Matt looked at him and said “you know what, since you’ve been such a good boy for me I’ve decided to give you a reward. Why don’t you pick which one of us is going to take Emily’s virginity, you or me, your choice.” Turning to Emily “you don’t mind do you Emily?”
“For you Matt I’ll do anything” Emily said in a state of lust.
Jack felt his spirits rise as he stared at Emily’s pussy. This was his chance to finally have sex, and the opportunity to take Emily’s virginity. Not many people got the opportunity to say they were a goddesses first. His cock was so hard as he stood up and got on the bed. Leaking precum as he knew this was the day he finally lost his virginity and became a man.
Then he saw Matt’s cock. Still wet from the blowjob he couldn’t take his eyes off it. He felt his mouth water as he saw the veins on Matt’s thick cock pulse. He knew Matt was more of a man that he would ever be and that he himself was destined to always be a sissy. Looking at Matt, Jack replied “I want you to take her virginity, Emily deserves a man with a real cock, not a clit like mine.”
Matt smiled “spoken like a true cuck. Why don’t you make sure this is what you want by putting my cock’s head in her.”
Jack grabbed Matt’s cock and lined it up with Emily’s pussy, running it up and down her folds to get her more wet. Emily shivered every time he rubbed over her clit. He then held Matt’s cock at the entrance of her hole and watched as Matt’s cock slowly disappeared inside of her.
Emily started grunting in a pain but Matt didn’t stop until he was all the way inside her. She was still experiencing discomfort but Matt reached down and started rubbing her clit while slowing going in and out, giving her the chance to get used to his size. Her moans changed from ones of pain, to a mix of pain and pleasure. Jack couldn’t help but watch as Matt skillfully turned this virgin into his own whore.
Matt started to pick up the pace as Emily’s moans increased “God don’t stop fucking me, I was so wet before we started. I loved humiliating Jack now I have your big cock in me, it’s like a dream come true.”
Matt just started fucking her faster when he heard this. Bending over to kiss his way up her neck.
“Omg don’t stop I’m so close” Emily yelled out.
Still kissing her neck, Matt kissed his way up until he started nibbling on her ear.
“Yes don’t stop I’m cumming” Emily yelled out, wrapping her legs around Matt. Furiously humping him in an attempt to go faster, digging her nails into his back. Matt couldn’t take much more and as he felt her pussy convulse he started slamming into her, cumming deep inside her.
To Jack it seemed like they were cumming forever before Matt slid out of her and rolled over on his back. A string of juices trailed from his cock and her pussy. They both took a moment to catch their breath before Matt looked at Jack and told him to clean his cock off. Jack quickly licked up all the juices off Matt’s cock still leaking precum from his own clit.
“How do we taste?” Emily asked.
“Amazing” Jack said, at this point delirious from not cumming yet.
“Well I have a whole pussy full of it so why don’t you come over here and clean me up too.” Emily said.
Jack layed down staring at her pussy before starting to eat it.
“No, not like that, lick all around before you go in, yesss like that” Emil moaned. “Now you can start eating me out.”
Jack stuck his tongue in, tasting both of Matt’s and Emily’s juices mixed together. This was the closest he had ever been to a pussy and didn’t care that there was cum in it, just happy he was making Emily moan.
“God having you eat my pussy with a real mans cum in it is hotter than getting fucked, you’ll definitely be doing this a lot.”
Jack smiled because this meant he would be able to see Emily again.
“Yes I’m so close don’t stop” Emily stopped talking and started moaning. Putting her hands on the top of Jacks head as she started to cum again. Jack didn’t stop licking her until she shoved his head away “that’s enough for now” she said with her eyes closed, tired from cumming twice.
Jack looked over at Matt who had been watching this whole interaction. “Sir may I please cum now? I’ve been a good boy for you two.”
“Yes you have been, but before you I let you cum there’s one more thing you have to do for me.” Matt replied
“Anything.” Jack quickly replied.
“I have to piss but don’t feel like leaving the room yet so you’re going to be my bathroom. I’m going to piss on you, whether you drink it or not depends on whether you want your bed smelling like piss, once I start to pee then you can cum.”
Matt stood up over Jack, as Jack put the head of Matt’s cock in his mouth and was ready to cum at any second. As soon as Matt started to pee Jack started to jerk off. He tried to swallow it all but there was to much and it started going over his face and in his hair. He couldn’t hold back any longer as he started to shoot his load all over his hand as he felt the warm liquid hit his face and hair.
“Look he only let out a dribble after all this time” Emily said laughing.
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