Frat Initiation

Frat Initiation 

By Victor

“Don’t you look sexy as fuck,” Jack teased Riley.

Riley looked at him with a very irritated, serious expression, a sneer on his red lipsticked lips. “Fuck you, Jack.”

“Hey, hey, hey now. Is that anyway to talk to your man, sweetheart?” he asked defensively but also taunting him.

“Don’t call me sweetheart,” Riley snarled. He knew he shouldn’t insult Jack when his chances of joining the frat was held in Jack’s hands. Riley was scared at first that he was assigned to the president of the frat to be his ‘Big Brother,’ the nick name given to each pledges mentor, while the pledges were known as “Little Brothers.”

When he saw how upset Riley was, Jack snapped out of his authoritarian role as president of the frat and back to his “big brother” role to console him. “Riley, dude, it’s just one night. It happens every year. Hell, even I had to do it. It’s just part of the frat initiation.”

Riley scoffed, “You mean hazing.”

“Call it what you want. It’s just a few more hours.”

“Everyone keeps smacking me on the ass and calling me slut, or bitch. I hate it,” Riley said almost whining.

Riley still looked pissed and irritated. Jack sighed and said, “Bro, all you have to do is serve drinks to all those assholes and do what you’re told. Then you can change.”

Riley stood there looking at him, pouting. He crossed his muscular arms over his muscular chest. When he did that he heard a seam rip somewhere. The dress was skintight on his jacked frame, and without a lot of stretch. He rolled his eyes. “This fucking cheap dress better not fall apart on me,” I mumbled angerly.

Jack laughed and patted him on the shoulder. “If your body wasn’t so jacked it wouldn’t rip. If it’s any consolation, you look really good. How you can make a slutty maid outfit still look masculine and feminine at the same time is a mystery.”

Riley snapped his head to looked at him with a warm feeling inside. Riley didn’t know why but he always got a tingly feeling up his spine whenever Jack complimented him. For some reason, he wanted to make Jack proud. He was Riley’s superior and he responded well to authority figures.

“I don’t feel very masculine,” Riley mumbled looking down at his dress, but absent mindedly running his hands over the slick material over his carved abs.

“Those fishnets actually make your legs look more muscular,” Jack said with another reassuring tone and sincerity, but hitting on the boy’s good attributes to calm him. He knew Riley was narcissistic and loved his body. “The whole outfit makes you look more muscular.”

Riley didn’t want to admit it but earlier when he was sliding the fishnets on, he spent a little too much time in front of the full-length mirror admiring his ass and legs. Jack was right, they did make Riley’s legs look incredible but has ass, damn. He had a sizable muscular ass thanks to hours of squats over the years and playing football. The netting was stretched wider over his ass, but the outline made it look more curvy and full.

Riley cleared my throat after he looked up at him. “You... you think so?”

Jack grinned that huge, white, toothy smile he’s know for. “I just said they look good on you.”

Riley cracked a smile. “So, you do like them?” he said meekly which is NOT his usual way of speaking to anyone. He’s anything but quiet and meek but around Jack, he turned into a little bitch. Appropriate given what Riley was wearing.

Standing next to him always made Riley feel small even though he’s probably more muscular than anyone in the house. Jack was three-inches taller, but his alpha energy dwarfed my Riley’s when Jack was around. He was just such a man’s man, masculine and rough even though he was so handsome. “Ugh, there I go again,” Riley thought to himself. “I keep noticing how handsome he is.” Riley had never done anything with a guy but sometimes, he thought about it with Jack. Riley sometimes could hear him fuck girls through the thin walls of the house and Riley always want to be that girl so he could experience what she is experiencing, being dominated, and even fucked by a real man. Riley played the tough guy football player but when he was alone, when he was jacking off, sometimes he fingered himself when he thought about Jack. He didn’t know why. He hit the button inside or him and cum buckets. He didn’t think he was attracted to dudes in high school. Of course, he recognized an attractive dude, but he didn’t recall wanted to bone one. Although, there was the wet dream he had about his high school football coach. The man was attractive, just out of college a year or so. He was young, in insane shape and always touched Riley when he spoke to him, a hand on his shoulder or on the small or his back. He was alpha as fuck, and he could put you in your place with one look. But with Riley, he’d always had nice to things to say, always taking time to talk to him, giving him pep talks before games. He was like a big brother figure to Riley, and the kid just wanted to make him proud. Riley envied him and loved being in his presence. And, of course, he was enamored with the man’s physique which make Riley hit the weights very hard, modeling his body after his coach’s.

Riley realized he was starting to see a pattern: authority figures, alpha, muscular, athletic, and attractive men have an effect on him.

“Riley, I like them on you,” Jack said quietly, reassuring the kid. “Not that it should matter what I think,” he said with a smile. “Unless it does matter to you?” he asked with a gleam in his eye, a half smirk, never dropping eye contact.

Riley was quiet for a few seconds. “Of course, it matters to me. You’re the fucking man, Jack. You’re my ‘big brother’ AND you’re the president. I don’t want to wash out during hell week.” Riley was sincere. He was always paranoid he was going to fuck up and get kicked out.

“So far, you’re doing the best out of any pledge here. But then I wouldn’t expect anything less from any ‘little brother’ of mine. You’re smart as hell, you’re funny, you’re a stud, Riley. I picked you for a reason. You make me look good. So far you haven’t embarrassed me. You won’t get kicked out unless you do something really fucked up,” he finished laughing.

Riley suddenly became self-conscious. “Like... like what?”

Jack shrugged his big powerful shoulders. “Disobeying me,” he said deadpan. “Do what I say, you’ll be fine.” He put his hand on Riley’s shoulder and massaged it lightly. “Trust me, you can do no wrong in my eyes.”

Riley nodded. “Cool, cool. Well, I hope I don’t embarrass you tonight, bro,” he said adjusting his stockings, straightening the seam on his developed hamstring.

Jack watched him intently and then chuckled when Riley looked up. “Believe it or not, Little Brother. You look the best out of any dude here dressed like a French maid. You’ll make me proud just walking around,” he laughed slapping him on the back. “Bro, I’m ok saying that you really do look hot. I’d smash you,” he said deadpan and then laughed again with a wink.

A bolt of electricity shot up Riley’s spine and his cock twitched. He blushed and looked down embarrassed. Then Jack said the strangest thing to him.

“Are you wearing the panties?” he leaned in and asked quietly.

Riley raised an eyebrow in confusion, then he absentmindedly reached back under his dress and and felt the part of the thong strap that emerged from the top of his ass. Earlier when he was getting dressed, there was a separate bag with a black lace thong. He was horrified as he stood there and looked at it, a pit in his stomach. But when he reluctantly slipped it on and looked at his ass in the mirror, he was very pleased with what he saw. Two plump, round cheeks connected to powerful hamstrings.

“Uh... yeah,” Riley replied embarrassed.

Jack recoiled in surprise. “You are? Good boy.”

Riley liked Jack calling him a good boy even though the last thing he looked like was a boy. Riley looked at him confused. “I thought it was part of the costume. Why wouldn’t I?”

Jack leaned to the side and looked back at Riley’s ass. The he leaned back and grinned. “Sorry, it was a test. None of the other newbies are wearing them.”

Riley’s heart sank. “What?” he stated sternly. “Are you fucking kidding me?”

Jack laughed. “It wasn’t required. I did it to see if you would do it. It was a test of your loyalty to me. I wanted you out of your comfort zone,” he said in a congratulatory manner squeezing Riley’s shoulder and leaving it there with a firm hold.

“Jack,” Riley looked at him with a mixture of irritation and pride that he had passed the test. He shook his head and started to jokingly insult, “Jack, I swear...”

“Uh, uh, uh,” Jack said wagging his finger. “Careful what you say to me, Little Brother.” That made the kid shut up immediately. He couldn’t afford to get kicked out of this frat. Three generations of Riley’s family belonged to this frat. He had to keep the tradition going. “I can make you wear that outfit all night,” Jack said. “Or all week,” he added with a wink.

Riley rolled his eyes and pouted again. But he thought Jack was sexy when he winked. And then once again, Jack did something totally unpredictable. He reached down around the back of Riley’s dress and lifted it up exposing his fishnet clad ass. Riley looked back at him in shock. “What...”

Then Jack whistled. “Whoa, damn,” he said quietly. Riley was frozen. He didn’t know what to do or say. Jack continued, “Look at those cakes, bro. I swear you fill out stockings better than any girl I know.”

Riley was so stunned. “What do you say to that?” he thought. Was Jack flirting with him? Did Jack bat for both teams? Riley’s heart pounded suddenly. He was having flashbacks to his thoughts about having sex with him. Being under him, taking his cock, the big man breeding him.

“And you shaved your legs?” Jack asked with a smirk.

Riley wasn’t sure if he was in trouble for going above and beyond but he wanted Jack to approve of his effort. “Well, yeah. I shaved everything. I didn’t think it would look good to have hairy legs with stockings.”

Jack was getting more and more excited. He leaned in and quietly asked, “How are the heels? Do they hurt your feet?” he asked with concern as he look down at Riley’s 4-inch high, shiny, black, patent leather stilettoes.

Riley looked down and shrugged. “Not right now they don’t. We’ll see.”

“Did you practice walking in them or something? I’ve been watching all night and you seem like a natural.”

Riley was so uncomfortable talking about this with another dude. He hesitated because he didn’t want to answer the truth, but he had to. He and Jack have a “no lying” rule.

“Yeah. I wore them in my room for a week. I walked around in circles, back and forth and...” Riley paused again. His face was flushed with embarrassment. But he had to tell him the truth. “I watched some YouTube tutorial videos made by drag queens. It was actually very helpful.”

“No shit?” Jack said with a grin. “Little Brother, you went all out! I like that.” Jack place his hand on the back of Riley’s neck and squeezed lightly. In a serious tone he said, “You take orders well.”

Riley swallowed and then shrugged. “I don’t do anything half-assed. I always go one-hundred-percent.” It sounded like bragging, but it was true. “I want to make you look good. What I do and look like reflects on you.”

“Wow,” Jack said quietly, still staring at Riley’s blue eyes, Jack’s eyes occasionally flickered down to Riley’s biceps and then back to his eyes. He made no effort to hide what he was doing. Riley felt special and felt closer to the frat president.

Then Riley remembered something that would make Jack even more proud. “Oh, and my makeup,” he added. “I did it myself.”

Jack’s jaw dropped. “Really? You did this yourself?” He reached up and lightly ran the side of his index finger knuckle along the boy’s cheek. “Looks so good! I thought maybe you had a girl do your makeup.”

Riley shook my head. “No way, bro. I don’t want some chic watching me put on makeup. I watched YouTube videos. There’s this influencer kid, some flaming pretty boy who wears makeup all the time even in fucking high school! Anyway, he’s fucking good. So, I just did what he said to do.”

“Now, YOU’RE the pretty boy,” Jack laughed. “But not flaming... which I like,” he said with a wink. He smirked. “Did you do all this for me? The panties, the high-heel tutorials, the makeup?”

Riley didn’t even have to think about it. “Of course. That’s my job.” When he said that, he could swear he saw Jack shiver.

“That makes me happy, Riley. I think you’re the best Little Brother I’ve had since I’ve been here.” Jack said with a serious look.

“Thanks, Jack. I feel honored to be yours.” Riley paused realizing what he just said. He quickly added, “Your Little Brother, I mean.” To that Jack smirked again, gave him a pat on the cheek and winked.

“By the way, the red lipstick... looks hot,” Jack added in a sultry voice. Riley was having all kinds of foreign sensations from the flirty compliments. It confused him but at the same time excited him. “Am I crushing on a dude?” he asked himself.

“You better get back out there,” Jack said. “I don’t want anyone to think you’re a pussy for hiding out.”

“Yeah. I get it. See you out there.”

Jack watched the pledge walk away, impressed with Riley’s big, wide back and bulbous shoulders. The kid’s muscular body navigating perfectly in high heels, a little sway to the boy’s muscle ass. The dress just barely covering the bottom of his ass cheeks. But the fishnet stockings turned Jack on the most. They made the kid’s legs look so fucking sexy and that seam running down the back followed the lines of his legs and also looked so slutty on him.  It made Jack’s dick hard. Since day one he knew Riley was the one. From the second they met; Riley had that look of worship in his eyes that Jack craved. He hung on Jack’s every word and the boy’s eyes tended to linger, scanning Jack’s six-foot-four, muscular body. Jack didn’t get a gay vibe from him but definitely a submissive, easily influenced vibe that could easily lead to some experimentation. Being the president of the frat, he got first pic of the pledges to mentor. Riley was the hottest, most muscular, most impressive. Jack knew what he was doing, it wasn’t his first time. Every Little Bother he mentored ended up with Jack’s cock inside them one way or another. Being a psychology major, he recognized guys who may be easy to manipulate. Maybe they were in denial of their sexual preferences, or had daddy issues, or were bisexual but didn’t know it yet. Riley clearly had a thing for authority figures and was probably confused by his attraction to certain men.  He knew Riley would be open to suggestion from Jack and having his first gay experience.

Jack grabbed a beer from another pledge carrying a silver tray with beer. Jack’s eyes followed the gymnast, the pledge was cute, lean, and muscular, looked great in the maid’s costume, blonde hair and had a pretty face. He was no Riley, though. No one here held a candle to Riley. Jack watched the room as the guys taunted and teased the newbies. He chuckled with a grin.

“What the fuck are you laughing at?” Jack heard the voice beside him. He turned to see his best friend, Trip.

Jack laughed, shaking his head. “It’s like taking candy from a baby.”

“A baby?” Trip asked although he knew where Jack was going.

“A two-hundred and ten-pound baby with a jacked body,” Jack said as he nodded towards Riley who was fending off slaps to his ass as he walked through the room.

“Damn, bro. That bitch is sexy as fuck. Look at that fucking ass,” Trip commented in awe.

“Bro, I CAN’T STOP looking at that ass,” Jack said. Both men staring at the muscular eighteen-year-old and both picturing him down on all fours taking dick from them. Trip was another senior Brother who was beautiful, muscular, handsome, and olive skinned with jet-black hair. He also was one of Jack’s fuck buddies.

“Now I know why you’re president. This was a fucking genius idea. I can’t believe the frat executive members agreed to this,” Trip said as he tapped the lip of his bottle to Jack’s bottle.

“What the fuck are they gonna do, say no?” Jack sneered. “I lied to Riley and told him we do this every year.”

“I’m jealous, Jack. Your boy is hot as fuck. Every gay guy here wanted him as their Little Brother,” Trip said. “So, what do you think? What’s the verdict? You gonna turn him out?”

“I think my boy will be my girl by the end of the night,” Jack replied with confidence and cockiness. “I have him questioning himself and he worships me.”

“What’s he think of his little outfit?”

 “Oh, he likes it. He likes it because I like it. He pretends he doesn’t, but I know he does. That muscle bitch wants my approval for everything. Like I said, he worships me. He’ll do anything I tell him.” He paused. “Bro, he’s wearing the panties,” Jack said with a raised eyebrow and a smirk. “I told you he would.”

“No, bro! Really?” Trip was in shock that a big masculine dude like Riley would even consider panties. “The thong?”

Jack nodded. “Oh yeah.”

“How do you know?”

Jack scoffed, “Because I lifted up the bitch’s dress and looked.”

“Fucking Christ, you are fucking bold,” Trip said shaking his head.

“Dude, his ass is so fucking cake. The fishnets looked like they were gonna fucking explode from stretching to fit his ass. When I saw the top of that thong coming out of that ass, dude, I wanted to cum. It was all I could do to not throw him against the wall, lift that dress and fuck him.”

Trip casually adjusted his stiffening cock in his pants. “Bro, stop. You’re going to make me fucking shoot in my pants.”

“Fuck you. You’d watch, you perv,” Jack said calling out his buddy.

“Fuckin right I would watch!” Trip downed his beer. “I need to go find my boy. Scare him a little bit. Joey is hot but scares easily,” he laughed. “What’s your plan?”

“I PLAN on being dick deep in muscle pussy by the end of the night. Even if I have to slip something in his drink. But that won’t be necessary.”

“Damn, that’s so hot,” Trip said with a grin. “YOU’RE hot, buddy” he added.

“I know,” Jack said with a wink. “Now, go find your boy. Dawson is molesting him,” he said nodding at Trip’s Little Brother being pawed by a huge, muscular, blonde powerhouse who was part of Jack’s inner circle of down-low fuck buddies.

Trip perked up and looked over at his boy Joey. “Shit! That big fucker better not try anything with Joey. I swear to God I’ll punch him in the throat.”

“Hey, is Joey into dudes?” asked Jack who was laughing.

Trip sighed. “No. But who knows what will happen with some alcohol and weed.” Trip took off in a slow jog towards the man molesting his boy.

Jack’s wandering eyes found Riley. He couldn’t take his eyes off the boy. His body was so amazing, so perfectly proportioned, so ripped. At one point, Riley’s eyes met Jack’s. Jack held his eye contact. Riley nodded to him and smiled. Jack didn’t nod back, he just continued to stare. He looked like a warden looking down at the prisoners. It made Riley have goosebumps. He held Jack’s eye contact for a few more seconds until one of the brothers pinched his ass. Riley turned and grabbed the guy’s hand and bent it back. The guy yelped. Everyone in the room stopped and were quiet.

“Try that again,” Riley growled at the older frat boy who was wincing in pain.

“Or what?” the guy hissed.

Riley bent the hand back slightly more. “I’ll break every fucking bone in your fucking hand.”

“Ok, ok!” the guy yelled. Riley let go. “Jesus Christ you little bitch! I was just joking with you.”

“I’m getting pretty fucking sick and tired of this,” Riley said loudly to the whole room. He paused when he looked up at Jack who was quietly, stoically watching. They stared at each other; Riley was waiting for approval. Jack just nodded. Riley continued, “If any of you assholes touch me one more time, it doesn’t matter if I’m a pledge or not, I’ll fuck you up.” The room remained quiet. Riley looked back up at Jack. Watching Riley assert himself, his body flexing, his anger making him look even sexier, made Jack’s dick hard. He nodded at Riley again, giving him a look of pride. That look made Riley very happy.

“Jesus Christ, I want to fuck that kid,” Jack said to himself.

The night went on. All the guys were trashed including some of the pledges. Riley had become so accustomed to walking in the heels and doing his best to keep his stockings straight, primping in the mirror and Jack even walked in on him fixing his make up in the bathroom. He stood and watched Riley holding a tube of red lipstick as he leaned close to the mirror, and carefully applied the lipstick to his full, red lips. Riley’s bicep was flexed, his thin waist and flat stomach pressed against the lip of the vanity, his ass sticking out making the dress pop out.

“Hey, sexy,” Jack said suddenly scaring the boy. Riley fumbled with the tube, juggling it, and then catching it. Jack closed the door and locked it.

“Fuck, Jack! You scared me,” Riley said, his chest heaving from the sudden scare. “You should have knocked.”

Jack laughed and walked up behind Riley. He stood behind him and looked in the mirror. The two men noticed the height difference and how handsome they were standing together. He put his hands on the boy’s muscular shoulders and lightly massaged. Riley looked up at him in the reflection, his big blue eyes held the man’s eye contact. Riley’s heart was racing.

“Sorry, I didn’t mean to scare you,” Jack said quietly. “And for future reference, I don’t need to knock. There are no secrets between us.”

“Uh... it’s cool. Thank God it was you that found me and not one of those assholes out there.”

“You are doing a great job tonight not letting those assholes take advantage of you,” Jack told him while increasing his grip. Riley closed his eyes and rotated his head feeling the relaxing massage. He felt the power in the strong hands on his body. This man took what he wanted, and Riley felt like it was him the man wanted.

“Sorry,” Riley said very nervous.  “I was just getting sick and tired of it. Plus, some of those dudes pinched me so hard that they fucking left welts.”

“They did, huh. Let me see,” Jack said as he reached down and lifted the back of the boy’s skirt. Riley froze not wanting to protest. Jack saw the welts on the kid’s big ass and boldly ran his fingers over a few. Quietly, just inches from Riley’s ear he huskily whispered, “You’re right. Those are nasty welts.” Riley swallowed hard; his heart was pounding. “But how could they resist?” he kept whispering but now looking at Riley in the mirror. Jack flattened his hand against the hard, muscled ass cheek. He felt the coarseness of the webbed stockings against his hand as he slowly rubbed the boy’s ass. Riley was so stunned at what was happening. He stood there and let the frat president feel him up.

Riley cleared his throat and his voice cracked when he said, “Jack...”

“Shhhh...,” Jack said into the kid’s ear. Riley felt the warmth of his breath and shivers ran up his spine. “You made me so proud tonight.”

Riley felt a wave of warmth in his body. “You’re welcome,” he whispered back, staring at the two of them in the mirror.

Jack continued to massage the boy’s plump ass. “Yeah, you’re a good girl,” he whispered, his lips toughing Riley’s ear. Riley heard him call him a good girl and he didn’t know how to feel about it. Maybe Jack said it because Riley was dressed like a girl, and he was teasing him. Riley liked the feel of Jack’s lips on his ear.

“So, I’m your good girl now?” Riley asked the man with a joking tone.

Jack put both hands on Riley’s ass now and squeezed. “Don’t you want to be my girl?”

Riley’s voice seemed trapped in his throat. He could only croak out, “I don’t know what I want.”

“I do. You want me. You weren’t sure at first. You thought it was respect and admiration. But I know it’s more than that.”

Riley leaned forward more as Jack became more aggressive in playing hard with his ass. Jack noticed the move and pressed his hard dick in between the boy’s cheeks. “Am I right?”

Riley took in a deep breath. He wanted to answer but he was scared. Jack rested his chin on Riley’s shoulder. “Look at me,” he commanded. Riley raised his head and looked in the reflection at Jack’s handsome face. “Do not lie to me, Riley. Am I right?”

Riley was hesitant but then nodded his head slowly. “Yes.”

“Good girl,” Jack whispered again and this time lay kisses on Riley’s thick, corded neck. “You’re so sexy,” he said between kisses.

Riley reached up behind and wrapped his hand around the back if Jack’s neck, he closed his eyes and laid his head back on Jack’s shoulder. He was scared, confused but he wanted this to happen. He felt Jack put his hand on his cheek and turn is face and met him in a soft kiss. Riley was surprised at how good it felt to kiss a dude. Jack’s lips were soft. Jack kissed him again, open mouthed and then Riley felt Jack’s knee between Riley’s legs as the man spread his legs apart. Riley arched his back, his ass stuck out more, he felt the hard cock sliding up and down the cleft in his ass.

Jack released the kiss and looked at Riley in the mirror. “I bet your pussy is tight.”

Riley lost his breath for a moment. The man had just called his hole a pussy. The way he reacted surprised himself because he moaned quietly.

“You going to let me in that pussy, baby girl?” Jack asked before kissing his neck. “Fuck that wet pussy.”

Riley was finally getting what he dreamed about. He was going to know what it was like to be a woman under Jack’s control. He would know what the women felt like looking up at that handsome face while being fucked.

Riley slowly nodded his head. His body was trembling. He pushed his ass back against Jack’s rock-hard cock.

“Say it,” Jack commanded.

Riley spoke so quietly that Jack could barely hear. “I want you.”

“You want what?”

“Uh.... I want you to fuck me.”

“Good girl,” Jack said soothingly. He turned the boy around and they embraced in a deep kiss. Riley was in erotic heaven. Jack felt the boy’s hard muscles and couldn’t hold back. 

He turned and aggressively grabbed the cross-dressed kid and sunk his tongue down the pledges throat. As they made out, Jack reached down and lifted one of Riley’s legs under the knee. He held the boy’s leg up at his side: a sign of dominance. Riley liked the aggressiveness of Jack’s strong hand holding his leg up, he felt the man’s hand run his hand back and forth over the nylon clad thigh. Jack took complete control of the muscle boy ramming his tongue in and out of Riley’s throat. At first, Riley thought it too aggressive and thought he couldn’t breathe from lack of oxygen, but his hormones finally gave in and succumbed to his mentor’s control.

Riley opened one eye and looked in the mirror. The site of the big, muscular, frat president was so hot. The man’s wide back and thick traps, his lats protruding at the sides, the man’s thick, dark hair was so intoxicating. This is the kind of man that Riley wanted. The kind who could take control, take what he wanted, use Riley’s big, powerful muscular body any way he wanted.

Jack broke the kiss. Riley looked as if he were in a trance. Jack caressed the kid’s square jaw. “You’re so fucking beautiful.”

Riley blushed. He lay his palms flat on Jack’s plated chest. He looked up at Jack with awe. He put his thumb on the older man’s lips and gently swiped. “I got lipstick on your face.”

Jack replied, “That’s ok. It will be the first of many.”

“It will?” asked Riley, his voice filled with hope and wonderment.

Jack grabbed hold of Riley’s muscular globes under his dress and squeezed. “Yes, sweetheart. You’re my girl.”

Riley’s heart skipped a beat. “Fuck,” Riley whispered in anticipation.

“I have to be inside you, babe,” Jack whispered back. “I need to put those beautiful legs over my shoulders, so you can look up and see your man taking you. You can see what you really are and what you’ll always will be; a jacked-up sissy with a warm, tight cunt.”

Riley swallowed hard. He just got a glimpse into his future. His dick was hard in his small panties. He took a new step forward and his hand grazed down Jack’s body. He wanted to see if Jack was as aroused as he was. He felt a Jack’s rock hard, thick beer can dick dressing left. He squeezed this cock, shocked at how big the muscle man’s cock was. All he could think about was that huge tube going up his ass. “Fuck,” Riley whispered.

“Feel that power, sweetheart? That’s what you live for now. That’s going to be in your warm, wet pussy all the time for the next year.”

Riley moaned quietly. He kept staring into this new caretaker’s eyes. “How did you know?”

“Easy. Just because a guy is jacked, masculine, cocky and alpha doesn’t mean he doesn’t want to be another man’s pussy. You were easy. You’re wandering eyes gave you away. You’re attachment to me was instantaneous,” Jack said while he brushed a loose lock hair off Riley’s forehead, slicking it back into place.

“I know. I couldn’t help it. I don’t know why I’m feeling this way.”

“It’s ok. You know now. You’re my new girlfriend from now on.”

“I am?” Riley asked with a smile.

“You’re my boyfriend in public but my girlfriend in private. Sorry to drag you out of the closet but this is the way it has to be. Tomorrow everyone will know you and I are a couple.”

“God, that sounds hot,” Riley answered with shivers up his spine.

Jack took his hand. “Come on, beautiful. We’re going up to my room.” He led the freshman out the door. There were other frat brothers roaming the halls and Riley was self conscious because they had to know what was going on. Jack was parading him through the hall.

“Jack,” one of the guys said nodding to them as he passed. The guy’s eyes lingered on Riley’s, telling him the frat boy knew damn well what was about to happen. Jack nodded back, holding tighter to Riley’s hand.

Jack opened the door for Riley like a gentleman, ushing the French maid into the room. Riley walked in and looked around. He had been in the room before but not this late at night. It was spacious since Jack was the president. The bed was a king and was made up, unlike most of the brother’s room were always messy. Once more Jack turned the boy, embraced him, and engulfed him with his mouth. The kiss was aggressive yet passionate.

“I love your body,” Jack said in a sultry, gruff whisper. “It’s so hard, fucking muscles everywhere.”

“Thank you. And I love your body. I want to feel every inch of your perfect body.”

“Take off the dress,” Jack ordered.

Riley slid the straps off his shoulders and pulled it down so he could pull his arms through. The top of the dress rolled down to his waist. He then hooked his thumbs in the waist and slid the dress down his legs letting it fall to the floor, and he stepped out. He then hooked his thumbs in the waistband of the fishnets and Jack stopped him.

“Whoa, whoa, what are you doing?” he asked as if Riley had broken a rule.

“I thought you wanted them off.”

“I didn’t say that. I said to take the DRESS off. Leave everything else on. You have to learn to listen to me, babe.”

“Sorry,” Riley said meekly.

“Hey,” Jack said caressing Riley’s jaw again. “It’s ok. You’re learning.”

“Ok.”

“This is the new you when we’re in private, baby. You’re my big, strapping, muscle-head boyfriend in public but my sexy, muscle girl in private.”

“Ok,” Riley agreed.

Riley stood in the middle of the room naked from the waist up but wearing fishnet stockings, panties, and tall stilettos. His smooth, tan, ripped torso made him look like a god. From the waist down he was a sexy, muscular whore. His face done up with makeup.

“You’re so gorgeous, sweetheart,” Jack said as he stepped up to the muscle sissy and kissed him. “Lay down.”

Riley laid back on the bed. Jack crawled up on top of him, their dicks pressed against each other. Riley’s legs automatically spread, and Jack took his rightful place between them. They kissed and felt each other’s bodies. Riley couldn’t believe this was happening, Jack knew it was going to happen, just like it had before.

Jack whispered into Riley’s ear, “I want you to have my baby. Would you like that?”

Riley was in shock at what he heard. He never dreamed a man would ask him that. It shocked him but aroused him.

“Yes,” he said back to Jack. “I’ll do anything you want me to do. I just want to make you happy.”

“Good girl,” Jack said with a smile. “Let’s start tonight. I want you pregnant by the end of the semester.

Obviously, Riley knew he wouldn’t get pregnant, that was part of the role he would play. Being treated like a woman was his dream and it was happening. The role play was perfect. He knew what it really meant was that he was going to be filled with cum all the time.

Like Jack told him, Riley found his muscular legs on Jack’s shoulders as Jack eased his way into Riley’s lubed hole. Riley winced and endured the pain of first penetration. “That’s it, baby. You’re doing fine. Let me slide in, baby. Good girl.”

Finally, something snapped and in plunged the thick cock into his new pussy. Riley gasped and clenched Jack’s biceps which the man found hot as fuck to feel the power in Riley’s hands take hold of his biceps. Jack watched the boy’s eyes snap wide open, his teeth clench, his face flush red.

“Jack!” Riley called out. “Oh, fuck, Jack!”

“Shhh, baby. You got this,” Jack reassured him. But Riley called out again, this time with a yelp and a scream. Jack smacked Riley across the face. “Riley! I said shut the fuck up!” he growled at the boy using his real name, breaking role play to get him to calm down. “I don’t need the whole house hearing you screaming like a bitch.” He knew the guys all knew what was going on in the room, but Jack was a private person.

Riley felt the sting on his face and slammed his mouth shut. For the first time in his life, a man had hit him, and Riley didn’t hit back. He’d broken a few noses in his time and never thought twice about it. This time, he would never dream of hitting Jack back. Riley tried to relax his hole, he took deep breaths and saw the pain as a challenge to overcome. And when Jack had hit bottom, Riley felt full and satisfied. He looked up at Jack and the look on his face was pure pleasure. Jack was taking pleasure in Riley’s body, his hole.

“Oh, God, oh, God, oh, God...” Riley whimpered over and over again.

Jack kissed him on the neck as he slowly pulled out to the tip and slowly slid back in. Riley’s eyes rolled back in his head, the intense sensations almost too much for him.

Jack’s mouth fell open, a slow moan came out as he sawed in and out of the boy’s pussy. “Fuck, Riley. God fucking damn it. Best pussy I’ve ever had, babe.”

Riley heard that and voluntarily tightened his hole around the cock inside of him. That made Jack gasp and stop fucking, hoping to stay off cumming for a few more minutes. He looked down at the gorgeous jock and suddenly wanted to melt into him. He felt the fishnet on his boyfriend’s legs. He reached up and wrapped his hands around Riley’s stilettos and held them out wide. Riley saw his legs splayed wide; his pointed toes aimed at the ceiling.

“Flex those quads, babe,” said Jack as his hands moved down to Riley’s thighs. “Flex them for daddy.” Riley flexed his muscular legs, the muscles popping, the stockings adding depth to his corded muscle.

“Fuck, babe. I don’t think I can hold off much longer. Your pussy is making me cum, baby,” Jack said as he sped up his fucking,

“Cum inside me, Jack! Cum inside my fucking boy pussy,” Riley pleaded quietly.

Jack tensed up and tried to stifle a roar. “Fuck! RILEY!” he bellowed as he came inside the boy’s warm, tight hole. Seeing this, Riley couldn’t hold back and started to shoot without touching himself.

“Fuck! Jack!” he finally yelled out before Jack collapsed on top of his chest. Riley wrapped his legs around Jack’s waist, locking his high-heels together.

“Fuck, Riley, God damn it,” Jack said as he panted. “I mean... fucking amazing hole, Riley. I mean it.”

Riley caught his breath and said, “You’re fucking incredible, bro. Fucking God you are amazing. I never knew it could feel that way.”

“Get used to it, babe. There’s going to be a lot of this every fucking day and night.”

Riley smiled. “You make my pussy wet, bro.”

“And you make my dick hard, you hot fucker. Fuck!” Jack was so elated, it was the best fuck he’d ever had even though it didn’t last long. “Kick off those heels, babe. Climb inside the sheets. I want to wake up with you in the morning.”

Riley kicked off his pumps, slid in under the covers. “Should I leave my stockings and panties on, bro?”

Jack chuckled. “I love it that you call me bro while you’re wearing panties and stockings.”

“Oh. I didn’t notice I did that. Do you want me to call you something else?”

“No, babe. I don’t might the bro-talk. It’s hot when you’re dressed like a sissy.”

Riley laughed. “Sweet. Thanks, Jack.”

“For what?”

“For everything you did tonight. I feel fucking free.”

“I knew you would. You just needed to be shown the way. Come here.” Jack spooned up against him and pulled him close. “Night, Riley.”

“Night, Jack.”