Chapter 9

"Unnnnh," groaned Catherine that afternoon as Jeremy finally popped the butt plug in through her anal bud and assured himself that it was seated properly. "Thanks, Lover; whew, it only gets a LITTLE easier each time, though."

Jeremy grinned at her as he wiped the lube off his fingers with a wet wipe. "You know, you should have started the enema and this butt plug drill over an hour-and-a-half ago, when you got back here around three. That way, you could have had more time in preparation."

He lifted Catherine up and hugged her naked body close to his own and looked at her with obvious and undisguised affection. "I want you to be fully prepared, Roommate; and I mean fully. I don't want you to be hurt and I want you to enjoy all of this experience."

Catherine gazed into Jeremy's eyes for a moment. "Hey, Stud! You aren't getting mushy on me, are you? You know that we all need to keep warning each other about getting too deeply involved one-on-one with our Pledge partners. It complicates things now as well as later."

She did not want to tell Jeremy that she was already starting to have the very problem she was describing. She was fighting with her mind and heart right this very minute to keep from getting any more emotionally involved with him.

Lee had been great last week. Hell, ALL these guys were just great! They were all becoming just so dear and special to her. But Jeremy had a certain--well, something. Hell, all the Pledge guys did to some degree; she had to admit to herself. Maybe things would stabilize in her heart and mind when they re-did the pairings for next week. But, Jeremy...

"No," Jeremy replied. "It would really be easy, though. You are a real babe and just plain NICE; and fun to be around." Then he grinned and chuckled. "You really are a great fuck, too. It's awfully hard to find that perfect combination in a woman these days."

Catherine laughed right back with him and hugged him close, not letting him see the moisture beginning in her eyes.

"Ladies," began Todd when they had all finished with supper and drinks. "Tonight is your night. Tonight we will ensure that you are all ... Wwwwatertight!" He said this last with the vocal flourish of a circus ringmaster or TV game show host, bringing applause and some laughter.

"But!" He then put on an overdone look of mystery and intrigue. "We are not leaving the Pledge guys out entirely. They get to participate ... to some extent ... as well in all of this!" This brought on another round of applause and catcalls and some high-fives among the male Pledges.

"Tonight, we will use the fuck benches that the guys used on Monday ... and which Andi helped us put to good use as a cheering section of sorts last night," he waved in Andi's direction and the elder member Brothers all cheered loudly as Andi smiled and did a mock curtsey.

"This should not take too long for the formal portion tonight. After we have certified all the Pledge ladies, then the Slut Altars and the fuck benches will be available for anyone to use for ... recreation. Of course, the drinks and food will be available until nine and the pool is open. We remind everyone that tomorrow IS a class day. So, be sure that you break out of here any time after the formal event if you require any more studying tonight. Remember, we are all students first!"

Out of the corner of her eye, Tylea saw movement at one of the tripod-mounted digital cameras. Sister Dolcy was checking for angle and focus. The other two fixed cameras evidently had already been checked. Brother Dennis had the roaming duty tonight with the hand-held camera for capturing the close-up action.

The five fuck benches were already arrayed by the pool. The elder member Sisters all formed a ring around the array of benches. Five of the elder member Brothers moved to them and lay down on their backs, stroking their erections to full strength and stiffness, a couple of them receiving playful fluffing licks from the nearby elder member Sisters to help them stiffen up.

Todd asked the male Pledges to lead their lady Pledge roommates over and get them situated. The lady Pledges were instructed to mount the cocks of the reclining Brothers in the classic cowgirl position of girl-on-top facing the reclining Brothers.

The Pledge ladies moved into position to straddle the already reclining Brothers. Brooke grinned and took a lick of Brother Rick's erection before notching the head into the lips of her already-wet pussy and descending while letting out an, "Oooh."

The other five elder member Brothers began to lube the anal openings of the lady Pledges as the ladies leaned forward over the reclining Brothers. They worked one, and then two, and then three fingers into each of the assholes of the Pledge ladies over about a ten-to-fifteen-minute period. All the while, they encouraged the ladies with gentle words and directions as to how to make the experience more enjoyable. Many a racy comment kept everyone laughing and upbeat.

Finally, all five of the Brothers behind the Pledge ladies gently popped the heads of their lubricated cocks into the well-lubed anal rings and the penetration began slowly. Once the Pledge ladies all assured the Brothers that they were reasonably comfortable with the presence of the cocks in their pussies and the ones buried balls-deep in their assholes, the teams began to move slowly to assure the proper amount of lubrication in all orifices. Only two required additional lube. Then the ladies and their partners began to move for a short while to determine and establish a good rhythm for them in order to assure a pleasurable double-penetration fucking experience for all.

Once everyone had settled into a comfortable motion, the male Pledges were brought close so that they could insert their cocks into the mouths of their respective lady roommates, who were by now all smiling and ready. Catherine grabbed Jeremy's cock and made a production of twisting her mouth all around it before beginning to move her lips along his shaft while he began the rocking motion of fucking her face gently.

From that point on, it was just a matter of good timing and stimulation that brought everything to a satisfactory conclusion as all five of the ladies were fucked concurrently in all three of their sexual orifices. All the guys got off, filling one orifice each with hot cum. All of the triple-penetrated girls experienced at least one orgasm. Brooke surprised herself by experiencing four!

Once everyone had dismounted his lady, and his bench, Todd announced a twist to the conclusion. "Now, for cleanup, we have a special procedure just for tonight. The Pledge ladies will now lie down and raise their legs so that they do not drain too quickly." Once this had been accomplished, Todd continued.

"Now, the MALE Pledges will clean the cocks of the BROTHERS. Immediately after that, the duty of cleaning up the pussies and assholes of ALL of the ladies goes to the one who did NOT meet all the requirements of Three-Timer Tuesday ... Trevor!"

The male Pledges had groaned and their eyes had popped at this announcement. Shit! Todd and Jack had told them last week that there would be some things about this training that the guys would definitely NOT like! I guess this is another one of those things, thought Jeremy.

Trevor glowered at being singled out. Lying on her back and looking up, Brooke saw his expression and said softly, "Trevor! You can do this. It's just an exercise in discipline. I know you can do this!"

Aaron got the guys moving by kneeling in front of the two Brothers who had helped him in filling the holes belonging to Dee. He looked at another man's cock from an angle at which he had never looked at one before. He looked at Dee once, worried about what she or any of the others might think about his putting his lips to another man's cock. She looked back at him and, seeing his concern, simply smiled and nodded. "It's okay," she mouthed silently.

With that, Aaron sighed and leaned in to take a man's cock into his mouth for the first time in his life. He tried to console himself with the idea that he was just licking pussy juice from Dee; it just happened to be on another man's cock at the moment. While not getting completely comfortable with the idea, he got through it without balking or gagging. He went through the motions with cleaning off the other cock that had been in Dee's ass without gagging or balking as well.

When Aaron looked around, he could see that the other guys were not necessarily looking as if they were enjoying themselves, but they were at least complying. The only dark look seemed to be on the face of Trevor. Trevor was DEFINITELY not a happy camper.

Quickly enough, though, each of the male Pledges had completed the cleanup of his two allotted cocks and stood. As he did so, an elder member Sister would approach, offer him a sip of water from a bottle, and hug her naked body to him and deeply tongue kiss him; then she would smile and say that it was okay; they said they knew the guys weren't bi or gay; it was all part of the training and the initiation. Even Trevor seemed mollified just a bit by this kissing and reassurance from the lovely naked ladies.

Trevor was then led by a smiling Sister Marta over to the end bench to begin his pussy-licking and ass-sucking chore with Andi. Andi raised herself up to give him a big kiss on the lips and a word of thanks and encouragement after he went down on her pussy and her asshole to lick and suck the sperm belonging to two other guys out of her body. Jay and the other male Pledges, along with each Pledge lady on whom Trevor finished this drill moved down the line with him, encouraging him and even joking with him as he performed his chore.

Jay even said to Trevor, "Damn, Trev. Looks like you get to eat ALL the quality pussy tonight."

Trevor ended up with his own roommate for the week, Brooke, who smiled affectionately at him and tousled his hair as he went about his cleanup duty on her. She even moaned once in what might have been a small orgasm, but neither she nor anyone else was sure. She just knew that it all felt wonderful.

Everyone gave Trevor a cheer and a round of applause when he finally stood up after cleaning Brooke with his mouth and tongue. He was still scowling a little as he stood up, but even he could not go that long without smiling when confronted by the smiles and kisses of all his female fellow Pledges. The cameras kept pace with the action as all the Pledge ladies surrounded him--at the instigation of Catherine--and as they held their naked bodies against him and laughed and kissed him.

Todd got everyone's attention. "Ladies and Gentlemen; Pledges of both genders; and, finally, Brothers and Sisters. I declare that the Pledge ladies for this year are now officially certified to be ... Wwwwwatertight!"

Cheers and applause followed as everyone began to move around toward the food or drink tables. One or two dived into the pool to relax. Conversations broke out all over and everyone seemed to be enjoying a comfortable evening, despite the fact that everyone was naked.

Despite the availability and willingness of many naked members of the opposite sex, the fuck benches and Slut Altars were only used sparingly by a few of the elder members for the rest of the Watertight Wednesday evening, and that was mostly oral sex. No overt sex acts by the Pledges took place out back for the rest of the evening. It was just simply a nice time had by all ... with one possible exception.

As they held each other before falling asleep that night, Brooke was feeling a bit anxious for Trevor. He had been unusually quiet and coldly distant since the end of the Watertight Wednesday event. No amount of smiling, caressing, or joking had been able to get him out of the mild funk into which he seemed to have fallen.

"Trevor, everything is okay. Nothing has changed," she whispered to him as she kissed his chest as they lay there together facing one another. "We're all still in this and we are with you, no matter what."

"Um-Hmm," was all that he said. But at least he squeezed her and kissed her forehead once before turning over to try to get to sleep, facing away from her for the first time this week.

"Hey, Babe!" Andi heard the answer to her call from her cell phone shortly after she and Jay had entered their Suite for the evening. Her husband, Dean, seemed to be in remarkably good spirits for nine o'clock at night, Andi thought.

"Well, you sound mighty chipper for this time of the evening," Andi teased.

"That just might be because I finally did what you recommended. You really are a genius, you know," he responded with a smile in his voice. There was a giggle in the background on Dean's end that brought one of Andi's eyebrows down for a second. Before she could say anything, Dean chuckled and said, "Here, let me put this thing on speaker."

"Hey, Andrea!" came the happy and distinctive voice of April, Andi and Dean's live-in housekeeper and Andi's longtime friend. "I finally tackled Dean and wrestled his pants off, like you told me to!"

Andi continued to hold the cell phone to her ear and laughed out loud, causing Jay to look over at her with a curious expression. Lying on the bed across the room, he could not hear what was being said on the other end of the conversation, but he could see that she was definitely amused. Andi was sitting naked in the chair at her desk, while Jay, equally naked, was lying on his side in the bed.

"So, you have finally finagled that," pause, "man of mine into bed with you while my back is turned, haven't you, you little hussy?" Andi said with a humorous, overly-done tone of indignation and without any real rancor in her voice, followed by a giggle. She had to be careful with her words, as Jay was able to hear her end of the conversation. She had to avoid words like 'husband' and 'housekeeper' if she were going to maintain her charade as just a somewhat typical blonde college coed with a weird twist, instead of being married to a kinky millionaire.

"Yep! Just like you told me to. We only got as far as getting naked and Dean's bringing me off twice with his tongue in my pussy. I had to suck one load of cum out of him to take the edge off when he got in from the plant earlier. We were just now relaxing with some wine before we got to the real fucking when--wouldn't you know it? Some witch from over at the college calls and interrupts!" April snorted a bit. She had evidently enjoyed more than a little wine this evening.

"Well, I told the both of you to take advantage of the opportunity whenever it presents itself and whenever I'm not there. Hell, you can even do it when I AM there. You know that!" Andi smiled to herself and even felt her nipples harden, imagining April and Dean in a threesome with her.

Andi saw that Jay was getting a prominent erection across the room. He was picking up on the obvious sexual nature of Andi's phone conversation with ... whomever.

Through the tiny speaker of her cell phone, Andi heard Dean say, "April, would you go get us some more wine? I need to take this off speaker and talk to Andrea about something for a minute."