Alistaire Too Ch. 01: Jenn

The story of Al becoming Alistaire was such a big hit, I decided to go ahead and write a sequel series with all the seeds I had planted but never germinated in the original. These tales will be a little more chronologically disjointed, while still forming their own narrative arc. Please understand that while a few things in the early parts of each entry in this second series may overlap each other, the endings are arranged in order.

I make no effort to recap any prior happenings in these stories. If you are coming to this series without reading the first series, Alistaire, you may be very confused. I suggest you read that first. People seem to have liked it quite a bit.

I'd like to make a special shout out to the readers and commenters who responded so wonderfully to Alistaire's first cycle. His further adventures are dedicated to you.

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THE ONE WITH JENN

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Beth and I had discovered doggy style. And we were having one hell of a time indulging in it. She grunted as I rammed into her, panting as she reveled in what she had called earlier the 'raw, animalistic nature' of getting fucked from behind. My hands clenched her spectacular ass and my eyes were riveted downward on its perfect, flexing curves, watching as my long shaft slid in and out of her pussy. My belly slapped audibly with each impact as I slammed against that backside.

That ass was why I loved doggy so much with Beth. Oh God, did I love that ass...

I backed off my ferocious pace and slid slowly in and out of her now, letting both of us catch our breath. Her firm, wet walls caressed me enthrallingly as I slid through her. The tiniest of quivers raced up my balls, reminding me that this session would not last forever, but I was becoming pretty good at prolonging mutual enjoyment. I relaxed and settled back into an easy, lasting rhythm.

"Oh, that is so nice," Beth said, catching her breath fully and relaxing.

"Nice?" I scoffed.

"Okay then, if you prefer, I feel transcendent, you magnificent stallion," she snarked back. "Continue for ever!" she demanded in noble tones. "Is that better?" Beth added archly, smiling back at me, her face flushed.

"Much," I panted, still a little winded from the earlier frantic pace. At the moment, I very much wished I could literally obey her.

After a few more companionable thrusts, Beth tugged her ponytail off her back and down over her shoulder. "Tell me," she said, as if in a normal conversation, "do you really think Ben is interested in me?"

I'll freely admit that this was not a subject I would have included in those likely to come up under the current circumstances. I will boast that I did not skip a beat in my easy rhythm, however. My vocal response was less impressive. "Uh... what?"

Beth looked over her shoulder at me again, this time with a puckish grin, and shrugged, waiting for my answer.

I gathered my thoughts. "First, I am very sure he is, though he has never said a word to me about it. Second, why the hell would he not? I mean, look at you," I said easily. I punctuated that last bit with two much more powerful, though still slow, penetrations. "And third, any particular reason that you bring it up now?"

"Jealous?" Beth teased easily.

"You know I'm not," I replied, a lie that was surprisingly tiny. I was really only jealous that she was thinking about him right then.

"I was thinking about how much I like getting screwed like this," Beth confessed, meaning the doggy style. "And it just occurred to me that even if the guy wasn't hung like you, Mr. Circus Freak, I'd still feel really full this way."

"Hey!" I exclaimed, bizarrely moved to defend my bro. "What makes you imagine that Ben is small?"

"Nothing. I hope he's hung. But we both know that he ain't hung like you." Beth pushed her ass back against me, indicating she was wanting me to up my efforts again. But she had started the conversation. I was going to finish it. I only sped up a little.

"Maybe he is," I prodded playfully.

"Alistaire," Beth said, pushing back harder now, "if there were two cocks like yours in one school, the whole place would have collapsed into some giant penis singularity or something." She still found ways to further pump up my ego...

My dick throbbed with renewed stimulation as I started really going at it once more, the slick, wet sound of my passage in and out once more punctuated by soft slaps of my belly against her ass. Fuck, it felt good.

"Still," I grunted, while I still had breath to talk. "Once I'm done prodding you, do you want me to actually go prod Ben into making a pass?"

"Would you?" Beth panted back. "Though don't prod him the same way as you are me!" I snorted. "Unless you want to give me that threesome with the two of you that I want," Beth added wickedly.

I slapped that perfect ass.

*

"Walk with me," I said to Ben as we left the dining hall.

He shrugged and fell in beside me as I led us outside after dinner and into the really nice evening. It had been a formal night and we both looked painfully preppie in our khakis, blue blazers, and ties.

"What's up?" Ben asked.

"Let's talk about Beth."

"Hey! I have never told anyone! Not about anything, but especially not about the whole twins thing," Ben declared in sudden anxiety.

"Easy dude. We know. And I always knew you could keep your mouth shut anyway."

"Thanks, but if you remember, Beth was most persuasive," Ben chortled, a little apprehensively.

"It is that first part of her persuasion I want to discuss," I said, "not the threat part."

Ben's eyes got a little dreamy. "Oh dude, you have no idea how hot that was..."

"You went and beat off the second you left my room, didn't you," I taunted quietly.

"Dude!" Ben cried, punching my in the arm.

I just laughed, "I thought so." Ben could apparently blush too. But he was not happy with me. Time to distract him from my asshole-ish comment. "Well, I think you should ask her out, because I'm pretty sure that she'd be receptive."

"You think so?" Ben asked quickly, suddenly enthusiastic. I went in an instant from a dickhead to the bearer of glad tidings. "What makes you think so?" he enquired, getting a hold on himself.

"Dude. It's Beth," was all I said. He knew how good friends we were. If anyone would know, I would. Still, it wouldn't help to pile on the incentive. "She didn't crawl onto your lap like she did just to keep you quiet. The threat would've done that."

"No kidding," Ben shuddered.

"Besides, she has started talking about you lately," I added. "Not a lot, but at the damndest times..."

"Oh man," Ben said excitedly. "I've got talk to her more, but I almost never have the chance. Let's invite her to join the D&D campaign!"

I laughed in his face. "Dude, Beth may like you. I suspect she really likes you. But she doesn't like anybody enough to play Dungeons & Dragons, even if he had a nine inch cock!"

I knew that last for a fact. I had already asked.

Ben and I both laughed at the very idea of a nine inch cock...

"That bad?" Ben asked idly, trying to imagine other avenues. "I mean, Bridget likes D&D okay."

"Man, let me clue you in," I said, "Bridget fucking loves D&D, now that she has learned to play. But Bridget loves The Lord of the Rings and Marvel movies. Beth likes fucking RomComs and dramas and shit."

"Then how can I figure out if she is actually into me, if I can't hang out with her?"

"How the fuck do I know," I complained. I was being somewhat sincere, actually. "I'm the guy who had never had a date until a month and a half ago, remember? You should be advising me. You run into her all the time, right? It's a small school. Instead of waving and continuing on to wherever you were going before you saw her, stop and just talk."

He rolled his eyes at me.

"Hey! It has worked pretty well for me," I said, shrugging elaborately, "in my limited experience."

Ben snorted. "I know about your 'limited experience'."

"Some of it," I could not help but murmur. Fortunately, Ben missed the comment, or at least the implication.

"I should be so lucky," he shook his head.

"You don't think Beth is up to their standards?" I asked, a little sharply.

"Oh fuck yeah," Ben said hastily. "But in case you haven't noticed, I haven't had so much as a shred of the famous luck of yours with Beth yet... if I ever do!" I suppressed a laugh at his unknowing double-entendre.

"Have faith, my friend," I said instead, clapping him on the shoulder. "I wouldn't have talked to you if I didn't think you had a shot."

We walked companionably, Ben with a dreamy look on his face. It occurred to me that things might get sticky though... I knew all too well the potential disaster secrets could lead to. I felt a little transparency was in order.

"Still," I added after a few strides in silence, "fair warning... Even if you do get lucky, you will not be the only lucky guy in the picture. Actively in the picture. Beth does what, and who, she wants to. If you do get with her, I can tell you for a fact that you won't have her all to yourself."

Ben digested that. "Who?" he asked at last.

"Can't say that I know," I answered very carefully. "And it wouldn't be for me to tell you if Beth keeps it a secret. Her life, right?"

I watched him carefully. If he took my heads-up any number of potentially unfortunate ways, I might have to warn Beth.

Ben shrugged at last. "You are not wrong," he said amiably. "You are not normal either, but you are not wrong." And with that, he went back to trying to get me to help him out. Screw that. I'd already given him more help than his mangy ass deserved.

*

I probably would have left Beth and Ben to work things out on their own, instead of providing the help I just had, but I had my own agenda. I had long since come to the conclusion that the girls' teasing me about trying to bag either of our classmates Jenn or Poppy was in fact a stupendous idea. They were both very pretty, and I had been in loads of classes with each in the four years we'd all been at school. But while I may not be 'normal', I am at least normal enough to know that haring off after yet another female seemed... presumptuous. Even if the girls were the ones pushing it, or least trying to tease me about doing it.

If one of them were to go off and hook up with another guy, especially one of my friends... I'd probably look better, doing what I wanted to do. I'd certainly feel better about it.

As Ben wandered off to change out of his 'formal' duds, I elected to lean into the jacket and tie. I suspected I looked less like a string bean in the coat, and I wanted to go see if I could 'run into' either Jenn or Poppy.

As I entered the hall of the main building, it was crowded with underclassmen. With less than half an hour until Study Hall, they were all socializing before lockup. I may not be the tallest guy in the student body, but I'm plenty tall enough to see over the general crowd. Or, tall enough at least to hope to see either of the girls I was looking for in time to steer myself their way, and put into action the advice I'd given Ben. That advice had actually sounded good to me when I had made it up on the spot...

Sadly, I did not run into either of them, but I did see another girl who might be good to simply practice on, though not actually pursue. It wasn't because Petra wasn't attractive—she certainly is. At average height, with brown hair so light it is verging on blonde that she wore in a, whatchacallit, page boy style, Petra's face had that Eastern European or Russian look where her skin seemed pulled extra taut over her facial features, accentuating all the sharp angles. On some girls, like that Sophomore, Tasha Animosova, it looks kind of mannish. On Petra, it looks striking and exotic. I wasn't terribly interested, however, in a girl generally known to be not-so-secretly lesbian, and more to the point, one who had sort of gone out with Bridget not once, but three times! Bridget had herself directly characterized at least one of these occasions as a date.

Bridget never volunteered a word about Petra, so I was sure as hell not going to pry with the girl directly. But I was afire with curiosity. Was Bridget full-on bisexual? Or was she just curious and exploring Petra's vibe? Maybe I could get a hint from chatting with Petra.

Also, Bridget was my friend, probably my best friend. And despite the fact that we were having sex slightly more often, if anything, than I was with Beth (or Carla), my primary concern for her was as that friend. I barely had been in one class ever with Petra, which was unusual, and I kind of wanted to check her out and see if she was 'suitable' to toy with Bridget's emotions and sexuality.

Check her out as a person, guys.

You pervs.

I steered into her path and said, "Hi Petra! How are you doing?" Then I stopped to indicate I actually wanted to listen to the answer, incidentally blocking her way enough to slow her down.

"Good, um, Alistaire," she answered. I wondered if she was as confused by my sudden, last-semester name change as most people were. "What's up?"

I had arrested her progress. Was it really this easy if you were just confident?

"Nothing, just enjoying the home stretch and dreading the APs. Where are you going to college? I don't think I've heard," I added. It was a question everybody asked everybody.

"BC," she answered, smiling.

"Noice!" I congratulated her.

"I think it is my best fit," Petra said. Then she added, more defiant than glum, "Harvard apparently also felt that Boston College would be my best fit..."

I winced politely. Inwardly, I liked this girl. There are three basic responses people have when they go for the big brass ring of an Ivy and miss it. Most just never speak of it again. A few get all whiny and look for sympathy. A few, like Petra apparently, wear their Ls on their sleeves proudly, and defy anyone to make something of it.

"You father's checkbook probably agrees, " I said firmly. She smiled. We stood awkwardly for a bare moment. I didn't want to extend things and waste the introduction I'd made. I could talk to her more later. "Well, thanks for telling me. And seriously, BC is awesome."

"Yeah," she agreed casually, as if she hadn't probably spent the last four years focused like a laser on getting into Harvard. We started to head off in our opposite directions, when she stopped and said, "Hey, Alistaire..." I paused. "You are friends with Bridget, right?" Petra added hesitantly.

"Sure, since freshman year," I said blandly. Interesting to have her to be the one to bring Bridget up...

"Well, you and she... anyway. Does she say anything about me?" It was almost a challenge. And not a completely friendly one, I thought.

"No," I replied cautiously. The thing was, everybody kind of knew that Petra was a lesbian, but while she obviously wasn't all closeted or something, she also wasn't ever exactly Out and Proud like the other LGBTQ+ students we had in our class, either. "I mean," I added hastily, "I know you guys have been, uh, hanging out a bit lately. But I've never asked about... anything. And she doesn't... anyway."

Smooth, dude. Smooth.

Petra didn't seem to be either definitely relieved by that, or definitely pissed by it either. No wonder she seemed to confuse Bridget a bit. She sure confused the fuck out of me. She obviously wasn't interested inme, but she seemed as interested about me, as I was about her.

"Cool. Thanks," she said at last, and we went our separate ways. Did she actually sneak a peek over her shoulder at me after we parted?

Did she see me sneaking a peak over my shoulder at her?

The conversation had achieved precisely dick-all to tell me if I needed to worry about her with Bridget.

*

Still, the whole Just Talk To The Girl part of the experiment seemed to work. I just needed to engineer enough chance encounters to develop a rapport, right?

It was fairly easy with Jenn. She was an artist and spent a lot of her free time coming and going from the school's big art studio that always stank of oil paints.

Jenn was average height and seemed to have a pretty nice bod. She virtually always wore loose corduroy pants and knit turtlenecks, no matter the weather or season. You never got a good look, but it was impossible to miss that she had a nice pert ass, and the contents to fill the front of those turtlenecks quite impressively.

I took to using the north stairs to reach my dorm room. It was out of the way, but went right past the art room on the second floor. Sure enough, I almost immediately achieved my goal of running into Jenn. I was coming down when she appeared from the art room, heading for the stairs in the same direction as me.

"Hey Jenn!" I said cheerily. "What's up?"

Two months ago, I think that she might have jumped out of her skin to discover that this shadowy walking bean pole was capable of social interaction outside of a classroom. But I think she, like most people, had lately gotten used to the idea that I was a living, talking person instead of a piece of mobile statuary. But I hadn't talked to her as much as I had other people, especially other girls, largely because I kind of had desires for her and that complicated things.

It was time to just take a deep breath and simply see what happened.

"Hey, Al," Jenn said easily, but with her head down a little. She often walked like that. "Or should I say Alistaire? I hear a lot of people calling you that now. Did you change your name or something?"

I laughed. "More like I had it changed for me. But you can call me whatever you like, Jenn. Been painting?"

"Yeah, I have two canvases left for my AP portfolio," she replied as we went down the stairs briskly. That made her boobs bounce around bit somewhere under her turtleneck and I can't say that was a bad thing...

"Isn't that due already?" I asked, some actual concern in my voice. Those deadlines were inflexible.

"Tomorrow," she replied. "I just can't stop fussing with those two pieces, though. How'd you know I'd just been painting?"

"Well," I drawled, "the facts that you had just left the art room when we ran into each other, and that you are a really pretty good painter led my Sherlock Holmes-level deductive powers to come to that conclusion."

Jenn actually smiled at that and murmured, "Duh, I guess."

"Also," I added, "you have a fresh little spot of vermillion paint on your temple."

"Vermillion?" she said, confused. She felt for the dried spot beside her eye and scraped it off easily. Looking at it, she said. "It's Crimson #4, actually. But very good getting that close. I didn't know you painted. I've never seen you in the studio."

"SAT word," I said, explaining everything. Prep school kids are obsessed with getting into college, which means they are obsessed with the SATs, which means they are obsessed with vocabulary. Even our jocks walk around with speech full of five-dollar words.

"Well, thanks for telling me," Jenn said. "I might have sat through dinner with that on my face."

"Come on," I said. "I was just the first person to see you. It was a pretty bright blob."

"Alistaire, you know people usually don't like to look me in the eye."

"I do not," I replied honestly. "Why the hell not?"

She stopped in the hall and turned to me. She stared me in the eyes, a wry grimace on her soft, delicate mouth. "Look at me, Al," she said after a moment. "I'm the zit queen of this school. People don't meet my eyes because they don't want to be embarrassed by looking at my face."

Okay, Jenn had always struggled with her complexion. It had cleared a lot since we were freshman, but she did still have way more zits than was fair. But so the fuck what?

"So the fu... so what?" I asked. "I like looking at your face. It's really pretty. You have that little pointed chin like an elf, and... how about your crazy blue eyes? They are really big, you know." Her eyes were indeed large, and very pretty, and they widened slightly more at my words. I occurred to me that I was suddenly being effusive. (That's another SAT word, folks)