Trevor stood on the side of the road, anxiously wringing his hands as he waited. Trevor was a 21-year-old college student who grew up in a small town in the center of the USA. He was now living in the big city (well, the big city for a country bumpkin). However, the main reason he had come to this large town and even larger university was just pulling up in a 2018 Honda Civic: Jessica, or Jess to her friends.
Trevor grew up as an only child, but he had never felt that way, since at the age of three, he had met Jess, and they had been connected at the hip ever since. It turned out that Jess was only a month younger than Trevor and his next-door neighbor. Even as they began to age and Trevor turned into a scrawny teen who never grew above 5'4", and Jess grew into a 6'3" redheaded goddess, she never left Trevor behind. She would never let the other kids bully him. In fact, when a new kid arrived during their sophomore year of high school and tried to bully him, the extremely popular Jess stepped in and made sure it never happened again. Jess had also been responsible for Trevor coming to this particular college and even helped him make some friends. Not surprisingly, as she was the most popular girl wherever she went, Jess joined a sorority.
Jess's joining the sorority became a turning point in their relationship. First of all, he started seeing Jess less often, and it had now been over a month since they had hung out, which would have been unheard of in the past. That was until yesterday, when he got a cryptic text from her asking him to be on this corner at this time and saying that she wanted to take him somewhere special. So here he was, standing on the corner, wringing his hands as Jess's blue Honda Civic pulled in front of him. He opened the front door and stepped in, and there she sat, as radiant and as beautiful as ever. As he stepped inside, Jess spoke:
"Hey Trevor, long time no see. I'm so sorry I have been AWOL for the last month. I'm really sorry—I've been super busy, but I promise I will make it up to you this evening. I have a huge surprise for you that I can't wait to share with you!" she said excitedly.
Trevor found his annoyance and anxiety shedding away. This always happened to him when Jess was involved. He found himself responding excitedly.
"That's okay, Jess. I don't mind. However, I'm super excited about your surprise!" he said with the big goofy smile he always got around Jess.
Let's be honest, Trevor had been in love with Jess since they hit puberty. He had never had the guts to ask her out, and there was another issue.
"Great, then let's go! We aren't far away," she said as she got back on the road.
She was right; they didn't drive for long, as they soon arrived on Greek row. They traveled down the entire street until they came to the very last house, an Old Victorian Style mansion with ΑAΩѰ on its front. However, Trevor noticed that the Ѱ was turned upside down.
"Is this your sorority? Why is the Psi upside down?"
"Yep, this is my sorority, and you will understand the Psi later, but for now, let's go inside, and I'll show you around," Jess said as she parked in the large garage.
She then led Trevor up the porch, through the massive double doors, and into heaven. As they walked through the double doors, he found ladies walking around, all almost as beautiful as Jess. All were tall, large-breasted bombshells.
"These are all my sisters, and I'll be happy to introduce you to them later. But first, there are some really important things I want to discuss with you, and I think my room is the perfect place for us to chat, so follow me."
"Okay," Trevor said with stars in his eyes.
As he followed behind Jess like a happy puppy, he couldn't help but notice all the women ogling him as they went. They went up the stairs to the second floor and to the third door on the right. Entering the room, it looked just like what Trevor would expect from Jess's room. It was full of vibrant colors and soft things, but Trevor didn't get much time to admire the room because as soon as Jess shut the door behind them, she pressed Trevor to sit on her bed. Trevor once again marveled at the height difference between Jess and him, especially with her standing above him. He was about to speak, but Jess beat him to it:
"Great, now that we are alone, we need to talk." Her tone had completely changed, now taking on a domineering tone that Trevor had not heard from her before.
However, before he could ask her about it, she spoke again, "I KNOW that you are in love with me and don't bother denying it. Luckily for you, I am also in love with you, and have been for as long as you have. That is why I have never had a boyfriend."
Trevor just sat there, jaw on the floor, as Jess, the girl of his dreams and the love of his life, confessed to him, but it seemed she wasn't finished.
"I also know about your secret. In fact, there's nothing about you that I don't know. I know that when you look at porn, you look exclusively at anal porn, but not just anal porn, but futanari on male porn. I know that you own a collection of dildos that you like to stick up your butt."
Now Trevor was sweating, all he could think about was how the fuck did she know that? He was about to stutter out an explanation, but once again, before he could, Jess started speaking again:
"Now, before you go and try to give me a bs explanation, don't bother. I didn't tell you all this to upset you. No, I told you this to help explain why I haven't been around for the last month. You see, this particular sorority has a secret—a secret I want to share with you. Do you want to know what that secret is?"
Trevor nodded enthusiastically, not sure what was happening but not wanting it to end.
"Great. However, you know what? I think it will be better if I just show you," Jess said with a sly smile, before turning around and starting some music on her phone.
She then began dancing, casting a mesmerizing spell over Trevor. However, what she did next truly took Trevor's breath away and made him pinch himself to make sure he wasn't dreaming. She started stripping.
Tantalizingly slowly, she lifted her shirt over her head, revealing swaths of bare skin. Even at her slow pace, it wasn't long until she started revealing a bright red lacy bra with little black stars scattered across the fabric, including strategically placed ones over her nipples. While keeping the music's rhythm, Jess then turned her back on Trevor before slowly pulling down her sweats. Eventually, she let them pool upon the floor, revealing a matching pair of lacy panties. Glancing over her shoulder to make sure she still had Trevor's complete attention, which she definitely did, she reached behind herself and released her bra before letting it fall to the floor.
For Trevor's part, he thought he had died and gone to heaven. Here he was sitting in the room of the girl he was completely in love with, and she was stripping for him. Not only that, but she knew all his secrets and didn't seem upset. In fact, she seemed excited! His heart nearly stopped as Jess turned around, her hands in the air, giving him his first look at the pair of breasts he had had so many wet dreams about. They were just as perfect as he had always imagined they would be. They looked to be size D, capped with large, pointed nipples that were just begging to be sucked. However, after letting Trevor have a good, long look, Jess started using her arm motions to direct Trevor's eyes downwards, where he got the biggest surprise of the night so far. There, clearly outlined by her red and black panties, was a COCK.
Trevor's mind was sent reeling. Was Jess wearing a strap-on? That could be the only explanation, right? Since it had to be a strap-on, it had to be the largest dildo Trevor had ever used. Now, Trevor was a bit of a size king, but this thing was huge.
Smiling wickedly at Trevor's reaction, she started to pull down her panties slowly. Within moments, the panties were pooled around her feet, causing Trevor to let out an audible gasp. That was the most realistic dildo Trevor had ever seen; it bounced up just like a real cock would, it looked like it was oozing pre-cum, and Trevor would have sworn he saw it twitch on top of all that. Trevor couldn't see where it was attached to a harness or see any harness at all. But the only other explanation Trevor could think of would be Jess having a real cock. However, that was impossible; Trevor had seen Jess naked when they were really little kids, and she had definitely been a girl back then. On top of looking real, it was absolutely massive: it had to be over a foot long and easily as thick as his wrist. Trying to wrap his head around what the fuck was going on, Trevor stared back up at Jess's smiling face, and right before he could get the question out of his mouth, she spoke once again.
"Now you see the secret that is ΑAΩѰ, they have found a way to turn their members, my sisters, into Futas. I can't tell you how they do it, as that is a closely guarded secret, but I can tell you that it is just as real as yours. In fact, the only real difference between mine and yours, other than my size, is that I cum much harder than men, and I have no refractory period. That means I'm like the Energizer Bunny, I just keep going. You know, I did this all for you, because I love you, and wanted you to be happy."
Trevor felt tears running down his face as he spoke, "Jess, I love you and will always love you, but I didn't need you to do this for me. I love you just the way you were. Was I too chicken shit to ask you out? Yes, I was, but you didn't need to go this far."
Jess let out one of her beautiful melodic laughs before saying with a huge smile, "I know all of that, but I wanted to do this. This cock was completely my choice, and I have zero regrets. In fact, the only thing I have been able to think about since getting this beauty is fucking that oh-so-cute ass of yours and making you cry out my name in pleasure! So there is no need for tears, unless they are tears of joy. Now, instead of worrying about me, wouldn't you rather feel my girl in your hands?"
Trevor only nodded before he refocused on Jess's beautiful cock. If she wasn't upset about it, then neither would he be. However, before he could take it in his hand, Jess spoke once again:
"You know, before you get started, don't you think it is a little unfair that I am the only one naked. I think it's time for you to strip for me. You don't have to make a production of it as I did; in fact, I think the faster you get naked, the better," Jess said as she stepped away from him.
Agreeing wholeheartedly, Trevor sprang to his feet and stripped naked in a record time, his decent-sized seven-inch cock springing from his boxers. As he stripped, Jess grabbed a strange-looking vial from her countertop. It looked like a vial out of one of Trevor's fantasy RPGs that he loved so much, with a real cork stopper and pink liquid inside.
Handing Trevor the vial, Jess said, "This is another Sorority secret that will make taking my girl so much easier for you. I know my girl is huge, and so I don't want you to get hurt when I jam every last inch up your tight ass."
Taking the vial and trusting Jess with his life, Trevor uncorked it and drank it in one long gulp. To his surprise, he found it tasted like strawberries.
As he drank it, Jess had gotten on her back in the middle of the bed and said, "Now get that cute ass over here and let's do a little 69 before we get to the main event. That will let you get better acquainted with my girl, and I'll show you what I can do with yours."
Without skipping a beat, Trevor complied. Unfortunately, the height difference between the two was so great that Trevor wasn't certain it would work, but Jess pulled him until his crotch was even with her face. In this position, Trevor found that despite the height difference, there was still plenty of cock that he could reach. With that in mind, he took that massive shaft into his hand. It felt warm, soft, and yet hard at the same time, nothing like a cold dildo. He could feel strong veins pulsing just beneath the surface. There was nothing fake about this. He also quickly realized that his hands couldn't wrap all the way around her shaft. However, he got distracted from his investigation as Jess took his cock into her insanely wet and warm mouth.
"Holy shit, Jess, that feels amazing!"
"You think that feels good, just wait until you feel this," Jess responded before taking Trevor to the root, making him moan out in pleasure.
As she continued to pleasure him with her fellatio skills, she reached over to the bedside table and grabbed a plastic syringe that she placed against Trevor's puckered brown star. Trevor felt the small intruder pressing against his hole and relaxed, letting it enter him. He found it incredibly easy to do so; that must be a side effect of the drink Jess had given him. He then felt a slightly warmed-up gel being squirted into his ass.
Along with the warming sensation, he felt an ache deep in his ass, a feeling of emptiness that drove him crazy. He had felt this sensation before, but never to this extent. The emptiness felt like exquisite torture. At the same time, Jess's incredible blow job was bringing him closer and closer to his peak. However, right as he was just about to go over the edge, Jess pulled his cock from her mouth and spoke.
"How does it feel?" she asked innocently, as if she had no idea what she was doing to him. However, Trevor had known her long enough to know she knew exactly what she was doing to him.
"Amazing!" Trevor gasped out. "Please don't stop, I am so close to cumming!"
"Oh, I know, but don't you think it would feel even better to cum with something long and hard shoved balls deep up your ass?"
Damn it, Jess was right. That damn ache was driving Trevor nuts; if he didn't feel something up his ass and soon, he was going to go insane with lust.
"Yes, Jess! Please shove your massive cock up my ass and make me cum. I'm begging you!" he begged.
"Now, how could I refuse such a heartfelt request. That would just be cruel of me!" Jess responded with her innocent smile.
"Then please stand up."
Trevor immediately did as he was told, with Jess standing as well. She then grabbed a pillow and placed it in the middle of the bed before speaking again:
"Now please lie on your back with your hips on the edge of the pillow and your legs spread wide."
Once again, Trevor complied without hesitation. He then watched as Jess kneeled onto the bed and began crawling towards him until she was directly between his spread legs. She then hefted her massive cock and placed it next to his own. It was in that moment that Trevor truly comprehended just how much bigger she was than he was. Her humongous shaft made his above-average dick look positively small. She left it like this for a few moments before shifting backward and placing her giant mushroom tip against Trevor's aching hole. However, before she started pressing forward, she spoke:
"Oh god, I have been waiting for this moment for so freaking long, and now that it's finally here, I'm not sure I'm going to be able to stop once I start. I promise to go as slow as I am able, but that is about all I can promise. Are you ready, my love? Are you ready to be filled with my love stick? Are you ready to become mine now and forever?"
"Yes, Jess, I'm ready. Please fill me with your love stick. Please make me yours! I've dreamt of this for just as long as you have! So don't make me wait another moment."
As those words left Trevor's lips, Jess pressed forward. Trevor instantly felt his hole respond, beginning to part for her intrusion. Whatever was in that drink and syringe that Jess had given him was truly amazing because within moments, Trevor felt his hole expand around the thickest part of Jess's mushroom tip before swallowing it whole and contracting tightly around her thick, pulsing shaft. The sensation was unlike anything he had experienced before.
Normally, when Trevor would stick a dildo inside him, there would be a few moments of pain, no matter how much lube he used, before the pleasure would come. However, this was not the case; instead, he only felt an almost overwhelming pleasure. In fact, it provided so much pleasure that, despite coming off the cliff earlier, Trevor found himself cumming just from the penetration. Trevor had never had an anal only orgasm before, much less one from only being penetrated, and yet here he was covering Jess and himself in his cum.
Jess was ecstatic about this turn of events. Her sister had told her that, with the right connections and preparation, this was possible, though unlikely. Well, she knew they had the right connections, so for her, it all came down to preparation. Turns out all of her blowjob practice on dildos had paid off. However, as happy as she was, the drive to fill Trevor was becoming all-consuming, and so she slowly began to press herself forward. Staring down at where their bodies were connected, Jess watched in fascination as inch after fat inch of her cock disappeared inside of her very best friend and now lover.
Despite trying to go slow, Jess found herself buried balls deep within Trevor in under a minute, and the resulting pleasure was so much better than she had ever imagined. The way his muscles clenched around her shaft and the heat of his hole were almost overwhelming. Luckily, Jess had been trained for this and was able to take a couple of deep breaths to regain control. Meanwhile, Trevor felt like he was floating on cloud nine.
Never before had he felt so full and yet in so much pleasure. As Jess had been penetrating him, she had pressed directly into his prostate, causing an eruption of pleasure throughout his body. Once Jess had buried herself to the hilt, Trevor found himself instinctively wrapping his legs tightly around her, as if he never wanted to let her go. He nearly came again when Jess leaned forward and captured his lips with her own. They kissed for a few minutes as Jess continued to grind her hips against Trevor's. Eventually, Jess broke their kiss and whispered into his ear.
"I love you, and now I'm going to FUCK you," she said, emphasizing the word FUCK, before she pulled about half of her cock out of Trevor's quivering asshole, before she thrust all the way back in.
Her thrusts started slowly, but then she had Trevor hold his legs up so she could really give him the pounding he had always dreamed about. Over and over she fucked him, soon getting herself into a steady rhythm of pulling out until only her mushroom tip was still inside Trevor before slamming her cock back in. Trevor could only hold his legs and take her massive pounding as her cock head pounded an upbeat tempo directly on his prostate, which sent massive jolts of pleasure throughout his body. It was when Jess curled him up into the Amazon position and kicked her tempo into overdrive that Trevor lost it and had his second of many anal orgasms of the evening.
Jess managed to keep her tempo consistent despite the increased grip of Trevor's orgasm. She was absolutely loving watching the man she had loved for so long come completely undone by her onslaught, and it made her want to keep going for as long as she could; this first load wouldn't be her last of the night. She wasn't sure whether she or Trevor would get much sleep tonight. Not that she minded, nor did she think Trevor minded either, not that he could really think in his blissed-out state. Jess continued her pounding for close to ten minutes before her strokes started getting more and more erratic, and she came to her inevitable close.
Letting out a howl of pleasure, Jess pounded into Trevor one last time before her orgasm finally overcame her. As Jess's cock got even larger before flooding his bowels with her seed, Trevor was sent into his third orgasm. His only lasted about 20 seconds while Jess's lasted over a minute and released over a liter of cum deep into Trevor's guts. Jess had never experienced indulgence of this magnitude before and nearly toppled over as her entire body seized up with pleasure. Eventually, she came down from her high to find Trevor staring up at her with the goofiest-looking smile she had ever seen. She smiled right back at him. Jess also noticed that her cock, despite having just cum, was still rock hard and ready to go. Trevor also noticed this, since it was still balls deep inside his ass.
"I told you, I will last longer and won't go soft after my first orgasm," Jess said, breaking the silence, "Let's do doggy style next!" she concluded, before pulling out.
"Yes, ma'am," Trevor responded as he got on his hands and knees.
He was surprised to find that, though a little of Jess's cum dripped from his used hole, he found most was staying deep inside him. Jess wasted no time, getting behind him and resheathing her massive sword in his gaping sheath. She then leaned forward, her large breasts pressing into Trevor's back, and said:
"I hope you're not tired, because we aren't going to be getting a lot of sleep tonight."
"I'm good to go, now fuck me!" Trevor responded.
"Your wish is my command," Jess said before taking Trevor right back to Pound Town.
~~~~
Many hours later, Jess was lying in bed, cuddling a cum-bloated, happily sleeping Trevor. Their marathon sex session had lasted most of the night and had ended with Trevor eventually collapsing and falling asleep from sheer exhaustion.
The last thing Jess thought as she joined him in sleep was, "Trevor is just going to love tomorrow."
------X------
Trevor awoke the next morning to the oddest feeling; it wasn't bad, just strange. His asshole felt full, as if he had left one of his toys in after his session the night before. However, he would never do that; he always cleaned up and put away his toys when he finished, and would never leave them overnight. Additionally, his brain registered another sensation, something warm and soft was pressed against his back. It was at that moment that the events of the night before came flooding back to him:
How Jess had picked him up after he hadn't seen her in forever, how she had taken him to her sorority house, and then dropped bomb after bomb, before dropping the mother of all bombs on him. Not only did she love him, but she also knew about his anal fetish and had found a way to get a real flesh and blood monster COCK, after which she had spent the majority of the night fucking him silly with said monster COCK until they had both collapsed in a heap on her bed. That meant that it was Jess's cock that was currently not letting his asshole close, and to his delight, it didn't bother him one bit. Instead, he found himself cuddling deeper into her embrace.
"Good morning, sleepyhead. I hope you had as great a night as I did," he heard Jess purr from behind him.
"Last night was a dream come true for me. It was amazing!"
"I'm so fucking happy to hear that!" Jess squealed excitedly, her hips automatically thrusting into Trevor's gripping ass as she feathered light kisses onto his neck.
They lay that way for a couple of minutes, Jess thrusting at a consistent, unrushed pace.
Eventually, Jess spoke again, "I have another question for you, and before I ask it, I want you to know that it is okay to say no. I won't love you less or change my feelings for you because of your decision."
Trevor could hear the nervousness in Jess's voice, which set him a little on edge.
However, instead of freaking out, he took a deep breath and focused on the pleasure radiating from his ass before he responded, "Oh Jess, there is no need to be nervous, you know you can ask me anything."
"Would you mind joining me in participating in a traditional initiation ceremony for the sorority?"
Trevor could tell there was more to this ceremony; he wasn't stupid. If it were just a simple ceremony, Jess wouldn't have any issues just coming out and asking.
"So what aren't you telling me?"
"Well, the ceremony would involve you being in a chastity cage and having sex with the rest of my sisters. I promise I will be with you the entire time, and you will have an amazing time. Oh, by the way, whether you agree or not, you are now my boyfriend moving forward, and I will brook no argument on that."
"So you're saying that I get to have sex with a bunch of beautiful futas and still get the love of my life to be my girlfriend?"
"I guess that is exactly what I'm saying, though I have no intention of ever letting you go, and one day fully intend to marry you."
Trevor couldn't believe his ears; all his dreams were coming true. He instantly knew his answer, without a shadow of a doubt:
"Yes, Jess, I will participate in your ceremony!"
Jess literally squealed with delight before she reached around and started jacking Trevor off.
"Jess, if you keep that up, I'm going to cum," Trevor said breathlessly.
He also noticed that although Jess was jacking him hard, she hadn't changed the pace of her fucking.
"Great, that is exactly what I want you to do. I want, no, I need you to cum for me, baby. Let all of your sweet seed out. Give it to me!" Jess exclaimed.
The feel of Jess's hard cock fucking his ass, while her soft hands jacked him off, combined with her begging for his cum was all too much for Trevor to handle, and in his mind, far too soon, he found himself kicked over his edge into orgasm.
"Oh GOD, I'm cumming!" he wailed as cum started shooting all over Jess's sheets.
Throughout his orgasm, Jess continued her onslaught, while she whispered sweet nothings into his ear. Eventually, and far too soon for Trevor's liking, his orgasm came to an end, and his depleted cock returned to its flaccid state. To his surprise, as soon as he finished, Jess pulled out of him and sprang from the bed. He watched as she grabbed something small from one of her drawers. Turning back to him, he found she had a pink penis cage in her hand.
"Would you mind wearing this for the ceremony? Once again, you can say no, but I would love you to do it. I think it will only enhance the event."
Trevor had seen plenty of men wearing them in videos, so he knew exactly what it was. If he was honest with himself, he had never gotten the appeal for them himself, but found he couldn't say no to Jess. This wasn't new; he'd never been able to say no to Jess since they were little.
Slightly reluctantly, he responded, "Yes, but only for you."
"Oh my god! Trevor, you're the absolute best! I love you so much!" Jess said excitedly, before giving him a massive hug.
Afterwards, she knelt and attached the cage around Trevor's softened cock. Trevor felt a sense of finality as she finished by clicking a small heart-shaped lock, locking the small cage into place. As she stood, Trevor noticed that she was wearing a golden necklace with a small key nestled between her breasts.
Jess must have noticed him looking because she said, "Yes, this is the key to your cage. This way, you always know it's close to my heart."
"I only have to wear this for the ceremony, right?"
"Of course," Jess replied, though Trevor got the distinct impression that Jess was going to try to get him to wear it again after the ceremony. However, before he could clarify more, Jess spoke again, "Now, I need to go get ready for the ceremony. Would you please stay in my room until someone comes to retrieve you? I promise you won't have to wait long."
"Sure, Jess, I can wait here."
"Great, you really are the best!" she said, before kissing him and skipping out of the room, completely buckass naked.
Left alone, Trevor wandered around the room, investigating this and that—some things he recognized from Jess's room back home, while other things were new. The massive dildos just sitting out in the open on her bookshelf were definitely new. However, he was surprised to realize that he recognized over two-thirds of the toys there, since he owned them himself. Jess really did know everything about him. He also discovered that Jess had her own bathroom, which he took full advantage of. Eventually, after just over twenty minutes, Trevor heard a knock at the door. Trevor quickly realized that he was still naked, and his clothes from last night were nowhere to be seen. Seeing no other option, he opened the door a crack, so only his head could stick out. He found a man of his age, dressed in a red robe, waiting for him. He was holding a silver tray with a granola bar that Trevor didn't recognize and another vial, similar to the one Jess had given him last night, only bigger, in one hand, and a white robe in the other. As he opened the door, the man spoke,
"Good morning. Mistress Jessica asked me to deliver these items to you. She asked that you put on the robe, eat the bar, and drink all the flask. She said you are not to wear any clothing other than the robe."
Trevor took the robe gratefully and wrapped it around himself. He found the material to be incredibly soft, and it felt great against his naked body. Once he had tied the band around his waist, he took the granola bar. Taking a bite, he discovered he felt ravenous and scarfed the entire thing down in a couple of bites. To his surprise, he felt quite full after he finished. Finally, he moved on to the vial, found it to be the same liquid as the following evening, and drank it down. The man, who hadn't introduced himself, had stood there passively without speaking while Trevor did these things. As soon as he finished, the man spoke once again:
"Now, if you would please follow me, I will lead you to the ceremony."
Without waiting for a response, he turned on his heels and started walking down the hallway. Trevor felt a bit stunned by the dude's abruptness, but quickly snapped out of it and hurried after the retreating figure.
Trevor followed the man through the hallway and down the stairs to a closed door. He was surprised that he didn't see anyone as they went, but figured that was because they were involved in the ceremony. Once they reached the door, the man stopped and turned towards Trevor before speaking again.
"Mistress Jess asked me to tell you that this is the point of no return. You can still back out now, feel no shame, and still be her boyfriend, but once you enter this door, there is no turning back."
"Have you gone through this ceremony?" Trevor asked his guide.
"I'm sorry, but I am not allowed to speak with you other than to say what I was asked to say. This is a decision you must make on your own."
Well, that explained why he hadn't been speaking. So, it was time for the final decision. Luckily for him, Trevor was a man of his word, and he had already told Jess that he would go through with whatever this was.
Therefore, taking a deep breath and centering himself, he said, "I've made up my mind, you may open the door."
Without another word, the man gave a small bow and opened the door. Trevor was met by stairs illuminated by dim flickering light from below. As Trevor started down the stairs, he heard the door closing behind him, cutting off the bright light from above and leaving him in near darkness. He found the lights from below provided just enough light for him to see the stairs. Once he reached the bottom, the stairs opened into a circular room. However, due to the lighting in the room, Trevor couldn't really tell how large it was. That, and the fact that his eye immediately went to the center of the room, where, from what he could tell, the room's sole occupant sat. For there, sitting in the strangest looking throne Trevor had ever seen, sat Jess.
She looked just like she had when she had left him early in the morning, with the only real change being that she had clearly put on some makeup that seemed only to enhance her natural beauty. She sat on a golden throne, which, though very ornate, had clearly been built with the occupant's comfort in mind. However, the strangest part of the throne was that there were medical leg stirrups attached to each armrest. Large candles surrounded the throne, illuminating Jess in an ethereal light.
As Trevor stepped forward, Jess spoke, "Welcome to these hallowed halls, Mr. Davidson." It had been a very long time since Jess had called him by his last name. In fact, he couldn't think of a single instance before now where she had. "Before we start the ceremony, I am required to ask you a few questions. Please respond with as few words as you can. First question: Are you here under your own volition?"
"Yes," Trevor replied, trying to respect Jess's wishes.
"Have you been coerced into joining us today?"
"No, I was not."
"By agreeing to be here today, you realize that you are about to be fucked by multiple women, all of whom have been cleared of any STDs. Please acknowledge that you consent to this."
Trevor still wasn't sure how that was going to happen, but he couldn't deny that he couldn't wait to find out.
So he said, "I consent," without hesitation.
Jess then gave him a wide smile that turned wicked, "Then get that cute ass over here and come sit in my lap," she said, gesturing towards her rock-hard cock.
Without really thinking about it, Trevor replied, "Yes, Mistress," before approaching.
As he advanced, Jess spoke again:
"Ensure you sit facing away from me."
"Yes, Mistress," he replied as he clambered onto the throne.
He wasted no time, turning himself and then lowering his ass until it once again came in contact with Jess's monstrous mushroom head. However, he didn't even pause, feeling a burning desire to have his Jess buried inside him once again. He pressed himself downwards, feeling his asshole easily spread and swallow her mushroom tip. However, he didn't stop there either, continuing to press downwards until he was fully seated in Jess's lap, his asshole once again wrapped tight around the base of her immense shaft. Shifting himself into a more comfortable position, Trevor watched as another person in red robes entered the candlelight. Though this person didn't speak, based on their curves, Trevor could tell they were a woman. They walked towards the throne with their heads bowed, grasped his left leg, hoisting it, placed it in the left leg stirrup, and strapped it into place. She then repeated the process with his right leg. The new position forced Trevor to lean back, his head now nestled between Jess's bountiful breasts, his asshole, still wrapped tightly around the base of Jess's shaft, now fully exposed. As the robed woman departed back into the surrounding darkness, Jess wrapped Trevor in a bear hug and whispered into his ear.
"Now the real fun is about to begin. I hope you're comfortable because we are going to be stuck like this for quite a while, oh, and please don't speak unless you are spoken to."
Trevor found that he was actually quite comfortable and whispered that back to her. As he spoke, out of the gloom eleven robed figures stepped forward. However, unlike the others he had encountered so far, these all wore pink robes that nearly completely hid their figures beneath. The figure in the middle then spoke, her voice musical, with a hint of a Scandinavian accent that Trevor couldn't quite place.
"We, the Sisters of ΑAΩѰ, have held our secret for over two hundred years, and today we gather to accept another Sister into our fold. Please present yourself to the other Sisters."
"I am Jessica Thorton, and I am honored to become your newest sister. This is Trevor Davidson, my boyfriend. He has agreed to participate in this honor ceremony with me."
"We welcome you, Sister Jessica, into our sisterhood. We welcome you, Trevor, and are honored you would join us in this ceremony," the robed figures said in unison.
Then the figure in the middle spoke again:
"Very good, now Sisters, introduce yourselves to our newest sister." As she finished, the figure on the far left stepped forward (It was clear to Trevor that they had rehearsed this entire thing before he got there) and undid the belt that held up their robe before letting the robe fall to the floor, unveiling a beautiful Asian woman standing there completely naked.
"I am Sister Mei-ling."
Then the lady on the far right stepped forward, revealing an equally beautiful and very naked African-American woman.
"I am Sister Nia."
Alternating again, a Latina beauty was revealed.
"I am Sister Isabella."
Next came a lady of Eastern European descent (Trevor wasn't sure which country).
"I am Sister Matea."
Followed by a lady who Trevor thought looked to be Japanese.
"I am Sister Sakura."
On and on they went: "I am Sister Amina," "I am Sister Aveline," "I am Sister Anastasia," "I am Sister Marisol," "I am Sister Rachel," until they finally reached the figure in the middle, a tall blond lady of Scandinavian descent.
"I am Sister Freya, Chapter President of ΑAΩѰ."
Trevor sat in Jess's lap, jaw dropped as he stared at possibly the eleven most beautiful women he had ever seen. They all possessed unique body types, although they each shared three things in common: They all stood over six feet tall, they all had large breasts, and they all had massive, hard cocks. Each of their cocks was humongous, easily as long and fat as the monster currently buried in Trevor's ass.
As Chapter President, it is my honor to be the first to welcome Sister Jessica into our Sisterhood," Sister Freya said as she stepped forward, her massive fourteen-inch-long cock leading the way.
She continued onwards until she stood directly between Trevor's spread legs, her massive cock mere inches from his occupied hole. Trevor watched in amazement as she reached down and grasped the base of her cock, moving her head so it was against his asshole, and it was at that moment that Trevor realized what was about to happen. Freya, this blond goddess, was about to shove her cock inside his ass while Jess was still inside him. They were about to fuck him double anal. Not only that, but she was just the first; he knew every sister would take a turn. He had watched plenty of double anal videos, but never had he imagined he would be on the receiving end of it, much less with eleven beautiful women.
He then heard Jess whisper into his ear, "I see you figured out what is about to happen. Don't worry, I promise you can take it, and it will feel incredible. Are you ready? There is no backing out now."
There was no way he would try to back out now, though he had a sneaking suspicion that if he really wanted to, he could, but he didn't. Instead, he took another deep breath and did his best to relax before nodding for them to proceed.
Taking this as her cue, Sister Freya began pressing forward. Trevor began to feel pressure building at the edge of his filled hole. As Sister Freya pressed harder, the pressure continued to build until his hole could no longer take it, and the head of Sister Freya's massive cock popped inside Trevor's ass.
To Trevor's surprise and delight, he didn't feel any pain from her entry; he just felt beyond full. In fact, the pressure from her trying to gain entry was far more uncomfortable than the actual insertion. Freya, for her part, now waited, with only her cock head inside Trevor's stretched hole.
This wasn't the first time she had conducted this ceremony. Though she knew Trevor would feel no pain despite Jess and her size, it had been drilled into her head by the previous president that, as the first, it was her responsibility to make sure Trevor had time to adjust. Not that she minded, Trevor's asshole felt wonderful wrapped tightly around her mushroom tip, and she could feel blood pulsing through Jess's achingly hard cock below her. Honestly, Freya loved being first, especially with the guys (though they occasionally got a freaky lady who only wanted it in her ass). Yes, Jess got to take his anal virginity, which was only right; she was his girlfriend, and one of the very strict rules of Alpha house was you never overtly tried to steal someone else's toy. Second, you never abused a toy. Finally, the strictest and most important rule of all: you never do anything without clear and concise consent. In fact, breaking one of the first two rules would get a Sister's gift removed, and get them exiled from the Sisterhood, while breaking the third rule resulted in something much worse.
It had only happened once in the five years Sister Freya had been part of the Sisterhood. It had been her freshman year, and she had only been an Initiate when it had happened. Just thinking about it sent a shudder through Freya's entire body. It was not something she ever wanted to revisit, so instead, she banished the dark thoughts from her mind and refocused on the beautiful couple in front of her. Her musing had definitely been long enough for Trevor to adjust, and now it was time to move forward, literally in this case.
Taking each of Trevor's thighs in her hands, Freya started inching her way onwards and was rewarded with a small moan of pleasure from Trevor's lips. This portion was all about going slow and steady. Her eyes were glued to the point where her cock met Trevor's straining asshole. She absolutely loved watching as her beautiful girl disappeared inside an overstretched asshole. On and on it went. Well, when you have fourteen inches of cock to bury, and you're going at a snail's pace, it takes a while to get to the hilt. Trevor was in absolute bliss; he had never had anything like this before. Never had his toys come close to the pleasure he was feeling now, and when Freya's head pressed Jess's cock hard against his prostate, he nearly came despite being in the chastity cage. Meanwhile, Jess was in her own special hell.
Jess had been in heaven ever since Trevor had sat in her lap. The feeling of his asshole wrapped around her cock was pure bliss. At least she thought it had been pure bliss until she learned what pure bliss was, and that was when Sister Freya had added her cock to the mix. Her entry had caused Trevor to tighten even harder around her shaft, and now, feeling Sister Freya's soft, hard shaft rubbing against hers was sending her right to the point of orgasm. Unfortunately for her, she knew the little ring that was wrapped tightly around her ball sack would prevent any orgasms, resulting in pure torture. Her pleasure would only continue to rise with no release in sight. She knew all her fellow sisters had endured what she was going through and that this was the final test of her mental fortitude, but holy fuck, it was going to be hard to make it through eleven of these without a break.
While Trevor knew nothing of Jess's struggles, Freya knew all about it, and she really didn't feel too sorry for Jess. They had all gone through this, and she knew that this was her final test. In fact, when Freya had gone through her test, there had been fifteen other sisters, so Jess was lucky that there were only eleven. As these thoughts were going through her head, Freya watched as Trevor's hungry asshole devoured the last of her cock, about thirteen and a half inches (you could never fully hilt yourself in an asshole that had another cock in it, but this was good enough). Once again, she rested, allowing Trevor a couple of minutes to adjust before the fucking began in earnest. Little did he know that this would be the last bit of rest he would get; if he could see around her, he would see all the other sisters already in line, awaiting their turn.
Trevor couldn't believe what was happening. He had done it; he had taken two of the largest cocks in the world entirely up his ass at the same time. Whatever liquid they had given him was truly amazing. Staring at this midsection, he could actually see a bulge in his stomach. Reaching down, he rubbed the bulge, causing Freya to groan in pleasure above him. Looking up, he saw her staring down at him and found his gaze captured by her beautiful blue eyes. Then, without saying a word, she pulled just over half of her cock from his gripping ass before plunging it back inside. Over and over, she repeated the action as she started getting into a steady, hard rhythm. Her actions caused pleasure to explode from his deepest reaches and reverberate through his body. He never thought anything could feel so good. On the other hand, Jess was experiencing something similar and yet entirely different.
Yes, she was experiencing incredible pleasure, but at the same time, that pleasure was causing exquisite torture. It felt like someone was jacking off half her cock while the other half was being gripped in a soft, hot vice, all as her need to cum kept getting ratcheted up higher and higher. All the while, Freya was settling into her groove.
Freya knew she couldn't go as long as she would normally; ten other sisters were waiting their turn. Therefore, after only about ten minutes of solid fucking, she started accelerating her pace. Faster and faster she went, pounding Trevor as hard as she possibly could as she raced toward her release. Finally, after only fifteen minutes (normally, Freya could easily go for over half an hour, and her record was an hour and fifteen minutes), Freya reached her peak, burying herself to the hilt one last time before she exploded deep in Trevor's quivering ass.
It was at this moment that Trevor experienced something that few men had ever experienced, a cum-less orgasm, caused by only being fucked in the ass. The pleasure was indescribable, and even years later, he struggled to describe the experience. The best he could say was that it felt like fireworks of pure pleasure exploded throughout his body. However, he would always insist that this description didn't do it justice. All the while, Jess had her exquisite torture ramped up another couple of notches.
Eventually, Freya's orgasm petered out, and she leaned forward and kissed first Trevor, then Jess, and said, "Welcome to the Sisterhood."
Then she withdrew her cum soaked cock from Trevor's gripping asshole before she stepped aside. It was at this moment that Trevor truly understood what was happening, because there, standing in a line, with cocks in hand, were the rest of the Sisters awaiting their turn.
As soon as Freya had vacated the space between Trevor's legs, a full-bodied, black haired lady, who Trevor remembered had introduced herself as Rachel, stepped forward. Without giving Trevor a second to rest or his asshole a moment to close, she pressed her tip right inside him. Trevor was amazed at how easily she entered him: there was no pressure or delay; she just popped right inside. Then again, it did make a certain amount of sense when he thought about it; he had just been thoroughly fucked and now had a bunch of cum-lube aiding her entrance. Unlike Freya before her, she didn't waste any time sheathing her entire length inside him. Once fully sheathed, she only waited a couple of moments before she got down to business. She proceeded to give him a hard pounding for around twelve minutes before she sheathed herself one last time and emptied another massive load deep inside Trevor's ass.
Once finished, she once again kissed Trevor and Jess before saying, "Welcome to the Sisterhood."
After her, it was Sister Marisol, then Sister Anastasia, on and on it went. Penetration, fucking, cuming, kissing, and "Welcome to the Sisterhood." One after another, in the order that they gave their names, never giving the couple a break. A couple of times, a red-robed figure would appear and give the couple water, although the fucking never stopped. They all had such big loads, and there was so little time between sisters that none of the cum inside him had a chance to escape. By the fifth sister, Trevor noticed his stomach begin to round. By the time the final sister unloaded inside him, Trevor was beyond tired, sweaty, and looked to be nine months pregnant. In fact, he was amazed that he was still conscious considering how long of a fucking he had just received, and yet despite being tired, Trevor felt completely awake and alert. In reality, he felt fantastic; he felt really stretched and like he really needed to cum, but otherwise, he felt great. He did worry when Sister Mei-ling pulled her cock out of his ass that he would shower the floor with all the cum in his ass, but once again, he was surprised as, instead, his ass quickly gripped itself around Jess's shaft with only very little leakage.
Now, Jess, on the other hand, was a completely different story. Her exquisite torture was becoming unbearable, and her need to cum was nearly causing her to become delirious. She was doing everything in her power, every exercise the Sisterhood had taught her, just to endure. Luckily for her, her torture was about to end as the Sisters had rejoined their semi-circle after they had finished.
Now that they were all back in their positions, Sister Freya spoke once again, "Congratulations, Sister Jessica. You have successfully completed your final trial. All your sisters know what you have endured, as they have all gone through it during their own ceremony. However, before you are released, please release Trevor from his prison so he may join you in this special moment."
"As you wish, Sister Freya," Jess responded, a clear tremor in her voice.
It was at this moment that Trevor realized that up until this point, Jess had yet to cum. Holy fuck, she must be going through hell. He watched as Jess, with shaky hands, unlocked his cage and let it fall to the floor. Within seconds, his cock rose to full mast, and Trevor found himself at the edge of orgasm. Jess then took his cock in her hand and started stroking. At the same time, he heard an audible click as the ring around Jess's balls was released. Within seconds, Jess went crashing over her peak into by far the largest, hardest orgasm of her life. A fountain of cum erupted from her slit deep inside Trevor's cum filled ass as pleasure exploded throughout her body. It was so intense that shudders were sent throughout her body, and Jess's eyes rolled up into her head. Simultaneously, Trevor experienced his first cumming orgasm of the ceremony, which sent waves of pleasure crashing throughout his body. It was so intense that he closed his eyes and rode the waves.
When his orgasm finally concluded, he found that his legs had been released and naked sisters surrounded Jess and him. The sisters gently pulled him from Jess's deflating cock, his asshole closing tightly, keeping the vast quantity of cum inside him. Then they carefully carried the exhausted couple to a waiting bed where Trevor and Jess fell into the most contented sleep of their lives while cuddled in each other's arms.