Sorority Boys - Chapter 1 - The Panty Raid

The mission was simple: infiltrate the Theta Iota Theta sorority and get out with a pair of one of their panties. Bonus points would be given if you found a dildo/vibrator.

Caleb scaled the side of the Sorority House using the trellis system. He climbed onto the landing of the second floor and peeked into the nearest window. The lights were off over the majority of the house. The girls must have been out for the evening. Maybe at another party or whatever event girls do. 

Caleb did a quick scan through the window to make sure the coast was clear. He said a quick prayer that the window would be open so he didn’t have to literally break in. 

He lifted the bottom of the glass, feeling it stick. Fuck. He thought, sighing. He thought about what he could use to break the window, but didn’t see anything. So he decided to give it one more attempt at opening. 

This time he put a little bit more muscle into it, and the window actually budged, creaking loudly as it slid up and opened. He cringed at the sound, if anyone was inside, they’d surely heard him. He waited a couple of seconds to make sure the coast was clear before slipping inside. 

The room was a typical girl’s dorm decor. Lots of pictures of girls making duck faces with their hands on their hips, butterflies and random foliage hanging on the walls, and of course, a sign that said ‘Live, Laugh, Love’. 

Caleb scoffed as he inspected the room. Looking for an area where the owner of the room might keep her panties. He thought that maybe it might be somewhere in the closet with the accordion doors. But then he saw the large dresser at the corner of the room. 

He smiled as he made his way over and started rummaging through the top drawer. Inside, there was a vast assortment of panties of all different colors, cuts, and cloth. 

He sifted through the mosaic of skimpy fabrics. Probably lingering a little bit too long, but he was enjoying himself. He scooped up a pair of black boyshorts and gave them a quick sniff. What was the harm? He returned them and grabbed another pair of pink lacy’s. Then his rummaging hand hit something stiff. 

Jackpot. 

He grabbed the smooth, jelly-like object and pulled it out. It was a long, blue, rubber dildo!

The guys of Delta Iota Kappa said that any pledge that came back with panties and a dildo would get the top prize!

He was too busy thinking about the possibilities and praise he would get to notice the noises coming from the closet. 

“Now!” said a girl’s voice.

The doors of the closet flung open and out swarmed several girls with flashlights beaming directly at him. 

Caleb felt like a deer in the headlights. Standing stock-still with the dildo and panties in his hand. The girls rushed him, trying to tackle him and bring him down. Caleb finally registered what was happening and dodged their attempts. Wriggling free of their grasp. 

He made a break for the window, clambering through as the girls scrambled after him. When he got to the edge of the roof, he looked down at the grass below. There was no way he could climb the trellis going down without getting caught. 

So he jumped.

It was only a 10 foot drop, but it sent shockwaves up his ankle when he landed. 

All of the outdoor lights came on at once, and that was when he saw the other Delta pledges—with the panties they stole in hand— making a break for it. 

There were girls everywhere. Caleb realized they must have been waiting for them.

This was a set-up. 

One guy tried to make a run for it but tripped on a stone from the landscaping. He squealed as the girls pinned him down and handcuffed him with pink fuzzy cuffs. 

Someone had a whistle, blowing it and directing them to where the other Delta boys were running, panties in hand. 

A small group of boys were cornered, trapped. The girls circled them as they surrendered themselves, cuffing them and hauling them off. 

Caleb heard footsteps behind him. Another group of girls was coming after him. He made a break for the wooden fence. If he could just hop over it he would be free. 

He placed his feet at the bottom beam and jumped, grabbing the top with the panties and dildo still in hand. But the rubber cock kept him from getting a firm grip. His arm slipped and his body fell backwards. 

The air was knocked from his lungs when he hit the ground. He was in a daze as several figures appeared over him. 

“Gotcha you little perv!” They said, as several hands grabbed him and turned him over. 

Caleb felt the weight of several knees press into his back and appendages. He felt his arms wrenched behind him, and the cold clasp of fuzzy cuffs slap around his wrists. 

“Is this the one that was smelling them?” One of them asked. 

“Yep!” Another girl replied. 

“Gross!” She scoffed. “I swear the pledges get more disgusting each year!”

The girls lifted him up with ease. Caleb tried to struggle and free himself, but it was no use. There were too many girls and the cuffs were too strong. 

Other boys were being led through the warzone with him. 

The lights were all on in the Sorority House now. Caleb squinted as he was pushed inside. 

The house was huge, 3 stories tall and expanding into several wings. 

He was taken to the center of the building where everyone else seemed to be. Girls slowly bringing in their prey of a captured panty thief. 

Caleb was pushed down on his knees onto the hardwood floors. He glanced around to see more than a dozen other boys in the same position next to him. Some protesting more than others. Caleb couldn’t help but notice that they were all a pretty similar build as he: shorter, more petite, skinny, and what some might call ‘feminine’. 

“Looks like we got a good haul!” a woman with long auburn hair said, stepping forward and strutting back and forth along the line of cuffed thieves. 

“1…2…3…4…” she counted each boy until she got to the end of the line. “15! We got 15 this year, girls!” The crowd of Sorority sisters all clapped and cheered in excitement. They stepped forward and began poking and prodding the boys. Taking a sharpie and writing a big number on each of the boy’s foreheads.  Caleb, being last in line, had the number 15 stamped across his head by a very attractive blonde girl. The women pushed them forward and started searching their pockets for their wallets. They pulled out their driver’s licenses and snapped pics of it as well as of the cuffed captive it belonged to.

“Now listen here you bunch of pigs!” The leader said, addressing the boys on their knees. “My name is Lauren, I am the Head Sister of this Chapter. All of you are guilty of breaking and entering, as well as theft and perversions for trying to steal our panties. We now have pictures of you and all of your information. So if you don’t want us to call the police or the dean and have you arrested or expelled, you will do EXACTLY as we say from here on out. Do I make myself clear?”

All 15 guys nodded or muttered in reluctant agreement. Some were actually shaking in fear. 

“Good.” Lauren smiled, nodding to the sisters, who collectively circled the boys and began uncuffing them. They all stood up, awkwardly, like a bunch of skittish animals not sure of what their captors would do to them.

Lauren smirked at how smoothly this was going so far. “So the first thing we want you to do is put on a little show for us…” the guys side-eyed each other. Lauren nodded to a girl near a set of speakers. The girl smiled as she tapped on her phone. Birthday Cake by Rihanna started playing.

“We want you to strip for us!” Lauren called over the music with a smirk. She took a drink from one of her sisters and the girls collectively sat down on the long couch of the showroom floor. They kicked back their legs and their beverages to enjoy the show.

Again the boys looked back and forth at each other uncomfortably. Standing stoically as the music bumped out the lyrics “cake cake cake cake oh baby I like it, you so excited, don’t try to hide it, I’mma make you my bitch”. They all failed to see the irony and foreshadowing.

Finally, the one labeled #3 started bobbing his head. His name was Brad. Brad figured undressing in front of a group of beautiful girls couldn’t be the worst thing in the world. After all, what if it leads to a little something...more?

The girls ‘whoo’d’ and cheered as Brad stepped forward, gaining confidence. He tried to bust out his best Magic Mike moves as he pulled his shirt over his head and twirled it like a lasso, tossing it into the crowd.

Other boys started joining in now that someone broke the ice. Their nerves dissipated a little as this all seemed like good fun, the panty stealing forgotten. Shirts started coming off, and #1 (Aaron) started unbuckling his belt. 

“Number one is trying to be number one!” a girl catcalled. Lots of cackling ensued as most of the boys dropped their pants and were down to their undies.

A girl named Sarah pointed and laughed at #8 “Who still wears tighty whities?!” The boy, Matt, flushed in shame from the ensuing humiliation. 

Soon, all the boys had their pants off, now dancing awkwardly to the song. Others stopped dancing altogether, unsure what to do next.

“Well?” Lauren the leader said expectantly, raising her eyebrows and holding her hands out as if it were obvious, “We said ‘strip’! That means everything!” The rest of the girls clapped in agreement.

All of the boys flushed now. Not wanting to get that naked in front of all these people.

But again, Brad #3 was the first to be brave, internally hoping it would get him laid with one or more of these girls. He grabbed the waistband of his boxers and pulled them down to his ankles. He expected a chorus of ‘wow’s’ and applause, but instead was greeted with a raucous of laughter.

“Not all that impressive is it?”

“Not unless you consider ‘below average’ impressive!”

“My parents didn’t like my grades being below average, and I don’t like dicks to be that way either!” one of them quipped. The girls thought that was the 2nd funniest thing that just happened.

None of the boys seemed eager to go after that. Other than Aaron, who was #1, or at least, he thought so in his head after he saw what Brad was working with.

“Still disappointing,” one of them said after Aaron pulled his own underwear down. 

“You would think someone pledging to Delta Iota Kappa would have a better DIK!” Sarah roared.

Eric, number 13, took offense to that. He dropped his boxers and exposed his cock proudly. 

“Now that’s more like it!” the girls whooped. “That’s almost 5 inches and he’s not even hard!!”

Eric smiled triumphantly. But the girls quickly moved on, starting to chant to others who were still reluctant.

Dropppp ‘em! Drop ‘uhm! Drop ‘uhhm!

The remaining guys looked at each other, gave a united nod, closed their eyes, and pulled them down. The room erupted in a chorus of laughter and cheers.

The guys quickly covered their junk up with their hands, but the girls didn’t seem to mind as they poured more drinks.

“Now…” Lauren announced, quieting the crowd, “I think it’s time to get to what the boys really want!!”

Both the guys and girls smiled and nodded at that. The boys thinking they were about to do something wild and crazy with the girls, but the girls having a completely different plan in mind.

They got up off the couch and grabbed their panties, tossing them to the respective thief that stole them. The boys had to remove their hands cupping their balls and shrivelled penises in order to catch them.

“Since you guys like getting into our panties so much…” Lauren explained, “We think it’s time you do get into our panties!”

That caused a bit of excitement in the boys, until the girls started laughing.

“Put them on.” Lauren clarified, switching tones.

All of the boys protested at that.

“Na uH!”

“No way!”

“Are you crazy?!” They shouted, almost in unison.

“Need I remind you…” Sarah chimed in, holding up her phone “..that we have all of your information and incriminating evidence on this right here. All it takes is one little phone call to ruin all of your lives!”

The rest of the girls crossed their arms and nodded deliberately. The boys gulped, knowing they were a bit trapped at the moment.

Donald, #2, seemed convinced, and decided to fan out his pair of purple panties and step into them.

“That’s more like it!” The girls clapped, resuming their cheering and the music. Shania Twain’s Man, I Feel Like a Woman provided the soundtrack to their transition. 

“Look! One of them is getting hard from this!! Hahahaha!” 

Chris’ cheeks turned the same shade of red as the cheeky panties he put on, you could barely see the #7 on his forehead through all the shame.

Eric’s big dick had a hard time fitting in his black thong, but the girls seemed satisfied with it dangling out the side uncomfortably.

“Smile!” Sarah said as the girls collectively held up their phones and started snapping pictures before the boys had time to even protest.

“Even more blackmail to send if you decide to act up!” Lauren threatened, clapping her hands twice expectantly.

Around the corner, a large structure was being wheeled into the room. The boys turned around to see what looked like an Olympic-sized balance beam rolling in.

Caleb wondered what was going on, were the girls going to perform gymnastics for them?

But his hypothesis was quickly proven false as the wheels of the beam were locked and anchored in the middle of the room. The girls stood up and herded the boys to line up alongside the beam. The boys looked like a bunch of confused lambs being led to the slaughter as they were bent over the beam at the waist, their outstretched arms touching their shins. The girls grabbed their wrists and yanked them behind their calves, handcuffing them there so that they were forced to stay in the bent-over position.

“Allow me to explain how this is going to work,” Lauren strutted in front of the quivering boys, “You will no longer be pledging to the Delta Iota Kappa fraternity. Instead, you will be pledging to the Theta Iota Theta Sorority! You will be pledging to no longer be a bunch of filthy fucking perverts! So over the course of this semester, you will stay in this house. You will follow our rules and regulations to the letter for every day that you are here. But not to worry...You see...we can be gracious. All you have to do is take part in our little ‘Sissy Game’!”

The boys protested pathetically, as if they were in any position to do so.

Lauren continued over the sound of their groveling, “You will all compete in a series of competitions over the next few months. If you win? You get set free. You can go back to doing whatever sleezy things you did before you got here. Though--after what you’ll be put through--I highly doubt that you will.”

The boys seemed to sigh in relief at that. It seemed simple enough, until they watched through their pantied legs what the girls were doing.

They each had a long, wooden paddle in their hand, decorated in a variety of colors and glitter and glamor.

“Oh my god! Yours is so pretty!” One girl complimented another. 

“Thanks! I spent a lot of time on it! Yours is great too!” the other replied cheerfully.

“So for our first competition…” Lauren continued, “We’re gonna figure out which of you are a bunch of babies!”

The girls started lining up behind them. Picking the one they thought looked cutest in their panties, or the one they wanted to inflict the most pain on.

“If you want us to stop, we will at any time, we don’t want to hurt you,” Lauren said mercifully, “All you have to do is say the ‘safety sentence’, and we will stop your spanking. But as a loser of the competition, you will be forced to stay here and move on to the next round. Whoever can hold out the longest and endure the most pain will get set free and can go home. Are we understood?”

“What’s the ‘safety sentence’?” #11 asked. 

Lauren smiled wickedly and looked to the girls to answer that question.

They all laughed and said together like they were in a choir: 

Wahhhh!! Wahhh!! I’m a wittle cwy baby!! I can’t take it any more! Wahhh!! Wahhh!!!

Lauren smiled at the flushed faces of the boys. Their silly pride always kept guys like them from admitting they were weak. That they couldn’t handle a little pain. 

“The last ‘man’ standing will get to go home tonight. Back to the filthy frat you came from, or back to your Mommy’s house. I don’t really care. Are we understood?”

The pantied boys all nodded with trepidation. 

“Good,” Lauren nodded to the girls, “then let the games BEGIN!”

**********

The girls cheered as they took their places behind their respective captive. Hefting their bedazzled paddles that were all painted and pretty. The boys squirmed as they anticipated their first spank. 

One of the girls counted off “3…2…1!” and they all collectively swung at the same time. 15 paddles whacked, and 15 pantied boys squealed simultaneously. 

Caleb clenched his teeth and both types of cheeks. He didn’t expect it to hurt as bad as it did. His ass felt like it was on fire, and that was just the first one. He secretly wished he would have stolen panties that were more conservative, covering more up, as opposed to the pink lacy thong which did little to cover anything. 

It didn’t help that the girl behind him was a little bigger than the others. She must have played softball in highschool, because that first swing had some power. 

“3…2…1!” THWACK!

Another smack with the paddles and another collective cry from the captives. 

Caleb already considered tapping out at that point, but another sissy beat him to it. 

“Wahhhh!! Wahhh!!”  Came a cry from down the line. It was #12, “I’m a wittle cwy baby!! I can’t take any more! Wahhh!! Wahhh!!!

“Of course the one with the baby dick would be the first one to cry like a baby!” Lauren jeered, and the girls laughed as they started uncuffing him, “Take him down to the basement and get him in his new attire! I’m sure he’ll find it fitting!”

#12 was still whining as he was led by his paddler and some helpers to a door under the staircase, his cries could be heard even after he was led down into the dark room. 

“Now where were we…” Lauren redirected. 

The spankings resumed, one after another until the line of boys started to dwindle. One by one they let out the ridiculous ‘safety sentence’, and were dragged helplessly down to the basement. Some sobbing like the cry babies they were forced to admit they were. 

There were four left: #1 Aaron, #3 Brad, #5 Tyler, and Caleb, #15. 

Brad, the guy who claimed to be such a macho man, was pleading with the girl behind him. 

“N-no more! Please! Stop!” He begged. His voice was so high-pitched and pathetic. The tears streaming down his cheeks and the panties around his waist didn’t do much for his “macho” persona. 

“Just say the words…” the girl behind him said as she reared back for another. Lifting his feet off the ground as she struck him across the ass. 

Brad squealed like a pig as he blabbered the safety sentence and was hauled off downstairs. 

Caleb’s cheeks felt like they were on fire. He looked over at the mostly empty bar now. Only Aaron and Tyler remained. 

Tyler had tattoos running up and down the majority of his body, he had the stature of an athlete, and only let out slight grunts with each swat of the paddle. Aaron was wriggling uncomfortably. Yanking on the cuffs behind his legs as he kicked them in pain. 

The next hit caught Caleb by surprise. He must not have heard the countdown, or they were foregoing it now. Because the hits came faster, even though they were in unison. The girls had a rhythm like an olympic row team. The collective ‘crack’ of the paddles were steady as a metronome. 

The paddle of the girl behind Caleb actually broke from her hitting him so hard. Caleb thought that would give him a reprieve, but another girl handed her her own as a replacement. 

The next hit made Caleb almost falter, but Aaron beat him to it. Making the little baby cry while he was hauled off. It was just Caleb and Tyler now. 

Tyler was hissing in pain now at each thwack. But Caleb was worried he was about to bleed. He was crying in pain, but he hadn’t said the words yet. The softball girl reached back, and gave a final blow that sent Caleb reeling. 

“Waaaahhhh!! Wahhhh!! I’m a wittle baby!!! PLEASE! Just stop!!” Caleb screamed. 

And that was it. Tyler’s threshold for pain must have been higher. The girls congratulated him as they uncuffed him. Tyler stood up, massaging his cheeks and wrists. He looked around anxiously, unsure of what to do until the girls parted like the red sea and pointed to the door. 

“Do…do I get my clothes back?” Tyler asked. 

“I think you should be happy with what you have on.” Lauren stated, “but you’re free to go.”

And without another word, Tyler scampered out of the house in nothing but his teal colored panties. 

The group of girls collectively turned to Caleb. “Time for you to join the others downstairs!”

He was drug through the room and to the door of the basement. The stairs were dark, but the room below was anything but. It was well lit, and decorated with bright, pastel colors. 

Caleb could still hear some of the boys crying and sniffling from their spankings, and as he got to the bottom of the stairs the crying boys looked even more ridiculous. All of them had lost their panties. Instead, they were now donning a very large diaper. 

They stood in a line whining and whimpering. They might have been louder, if not for the very large pacifiers shoved in their mouths with a ribbon around their heads to secure them. To complete the look, a large pink bonnett was tied around their head. 

“Looks like #15 just missed out on his chance for freedom!” One of the girls attending to the grown babies called. Aaron was still on the concrete floor being held down by two girls as another was taping a big fluffy diaper around his flailing waist. He squirmed and tried to avoid the large paci being pressed to his mouth, especially when he realized the nipple of the paci was shaped like a penis, but his efforts were futile, and his cries were muffled once it was shoved in and tied tight. 

“Your turn, #15!” The girls said after Aaron was lifted up to join the other adult babies.

Before Caleb could protest he was pushed down onto the mat. Girls on either side of him grabbed his arms and legs as he wriggled and whined. 

Sarah, the girl attending to him, snickered as she removed his panties. Caleb’s cheeks were still burning from the blistering bashing he just received, so he was a little relieved when she applied a cream to his skin first. 

“Does that feel better, wittle baby?” She teased as the girls laughed and took pictures. Caleb nodded his head as the tears rolled down, realizing how pitiful he must have looked. 

The sisters lifted his legs so Sarah could slide a big, crinkly diaper underneath his burning bum. 

All of the attention from the girls must have gotten Caleb excited, because his cock started to stiffen. 

“Another one getting hard!!” one girl exclaimed. 

“Bunch of pervs this year!”

“That’s like 10 out of 14!”

Sarah smirked as she applied liberal amounts of powder to Caleb’s lamentable little region. Caleb cringed as the crinkly diaper was brought up and over his twitching tee tee, and then taped securely on each side. The girls holding his arms put his hands in large, locking mittens. He must have been so focused on the other parts of their outfits to notice this little addition. A big rubber penis came into view and pressed against his pursed lips. One of the girls squeezed his nose tight until he was forced to open his mouth for air, and the 4-inch paci was shoved inside. The ribbon was tied around the back of his head before the bonnett was tied under his chin. 

He was hoisted up onto his feet. The bulkiness between his legs immediately apparent as he was shoved to join the line of the rest of the new adult babies. 

“Smile!” Lauren said to the line of diapered delinquents. None of them did as hundreds of pictures were captured of the captives. 

“I’m sure you boys saw where you will be sleeping while you’re here!” Lauren called, gesturing to the back half of the basement. Caleb’s view had been obscured by the crowd, so he just now noticed the many baby cribs behind them. 

They were the same size as a regular baby crib, hardly enough room for a grown man. Except when he took a tally of the total number of beds, he counted only 7. 

“You will have to double up until more are set free.” Lauren explained to the dumbfounded boys gaping behind their dummies. “But at least you’ll really get to know your cohorts!”

The boys made feeble protests as they were pushed forward to the cribs. One side of the railing dropped down and Sarah patted the plastic mattress inside for Caleb. “In you go, 15! You will join #7 tonight!”

Caleb was shoved into the crib and set on his side as Chris, the one with #7 on his forehead was pushed in with him. They were forced to lay on their sides facing each other as their mittened wrists were secured to the opposite corner of the crib. Caleb could feel Chris’ hot breath on him as they were forced to hug while their ankles were secured as well. Both of them struggled to get comfortable in the awkward position as the railing was lifted and locked and the girls did the same to the other boys. 

“Sleep tight babies! You have a big day tomorrow!” Lauren said as the girls double-checked the restraints and made their way up the stairs. The lights were turned out and the door to the basement slammed shut and a series of locks followed. 

The boys were left squirming and crinkling as they tried to get comfortable. Muffled whines and “whut the ffffkkkss” were spoken around the paci’s. Some were yanking on the metal bars of the crib, trying to get their mittened hands free. All it succeeded in doing was making a really loud clanking noise. “Shhut uhh furrkk urpp” someone said, until the clanking eventually stopped. It was cold in the room, and the pampered pledges were wearing nothing but their diapers. No shirt, no blankets. They practically had to get as close as possible with their crib-mate to stay warm.

Chris was doing a lot of wriggling next to Caleb. It took him a second to realize what was happening through the padding of his own diaper. Caleb could feel a stiff member inside Chris’ diaper. A little poking as Chris ground up against him. At first Caleb thought he was trying to get in a relaxing position, but the rhythmic movements of Chris told him the opposite. He wasn’t shivering from the cold, Chris was humping him! Avoiding eye contact as he breathed heavily around his paci.

“Wha’re’ooo’dooing?” Caleb tried to say, but it just came out stifled. He glared at Chris with his eyes, but Chris was avoiding eye contact as he handled his business. 

The crib creaked and the diapers crinkled as Chris’ grunting intensified. All Caleb could do was lay there and take it, trying not to get hard himself as his crotch was pressed against Chris’. 

Finally Chris let out a pitiable little moan as he spasmed against his crib-mate. Sighing softly and deflating a bit as the relief and shame washed over him. Chris finally met eyes with Caleb, who was wide-eyed with anger and disgust. Chris apologized with his eyes and looked away. Embarrassed at what he just did in his fit of horniness.

But that didn’t stop him from having another go at Caleb’s leg and crotch 30 minutes later. In fact, Caleb got very little sleep that night, as Chris’ insatiable need to cum seemed to crop up every hour or so. Caleb absentmindedly thought about how quickly his life was spinning out of control as Chris made his 5th or 6th sticky mess in his diaper against him. This day was hell, and from what he knew about pledging, there was usually at least a whole week of hell waiting for him…