Alistaire Too Ch. 03: Poppy's Mom

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Our Hero takes a leap for Poppy, lands on her mom.
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Part 3 of the 6 part series

Updated 01/17/2023
Created 06/02/2022
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Publius68
Publius68
2,513 Followers

The story of Al becoming Alistaire was such a big hit, I decided to go ahead and write a sequel series with all the ideas I had but never used in the original. These tales will be a little more disjointed, and jumbled up chronologically. Please understand that a few things in the early parts of each entry in this second series may overlap each other, the endings are arranged chronologically.

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.

This entry is a little different, but hey, you have to have one of these in a hung nerd harem series, right?

—————

THE ONE WITH POPPY'S MOM

—————

As the final week of Track practices and meets ran along, I found myself dropping by the tennis courts almost every day on the way up to the track. I was very much wanting to see Poppy in her tennis outfits, and wanting to be seen by her as I cheered her. By the end of the week, she had definitely noticed that I was around an awful lot all of a sudden, and mostly around her. This resulted in us meeting and talking in the halls a good bit too.

We had even met up and I had sat with her in the Tuck one night, just the two of us. That had been going well until my boys Ben, Tres, and Alex all rolled in and sat down with us, driving Poppy away. On the plus side, she was happy to talk to me, but not them...

But there was definitely a problem. She wasn't... I mean... Look, I'll just say it. Poppy seemed disinclined to just fall on my penis as soon as she realized that I was interested in her.

Yeah.

I have become a very, very, spoiled little boy. It is ridiculous, I know.

Grumpy as I sound, the news was not all bad. I had known Poppy since freshman year. We had been in a shitload of classes together, especially English. I had had to endure reading a ton of her essays that were often... let's just say they were better than mine, okay? She had never looked right through me like most girls, but she did mostly treat me as a fixture on the wall. The good news was that this Spring, after a couple of weeks paying as much attention to her as I could randomly achieve, she did appear to at least be dimly aware that I was in fact a human. I think she even surmised that I was the kind of human most likely to have a penis.

But she showed no signs of succumbing to that dude Alistaire's intense gaze or anything. I was beginning to worry whether I had time enough left in the year to manage to be with this gorgeous creature, with her long black ponytail that she always had up hanging over the back of a tennis visor.

But I wasn't going to give up. It was fun, and Poppy was fun to both listen to and look at.

So I kept putting in appearances at the tennis courts. Almost every day, I would find time to swing by on the way up to run—usually for not more than ten minutes, sometimes less, sometimes a little more. And I tried not to watch just her. I like to encourage anyone who is being competitive. Moreover, I thought it was important to not seem like I was overtly stalking her. And it wasn't like there were not other cute girls on the team...

When Poppy's mom was not feeding balls for practice, I'd usually chat with her. She almost always had her eye on Poppy, of course. And frankly, when I was there and couldn't see Poppy at the moment, her mother was a pretty damned gratifying substitute.

The problem with that was that it was a lot more problematic. When we were talking, she was right next to me. That made it hard to hide that I was staring at her, though I tried. It was a unique opportunity to use the skills I had perfected before this spring, such as checking out girls without being caught. But that was much more difficult since the last two months of events had kicked off—my body had begun to train itself to be anything other than restrained when staring at a beautiful girl or, in this case, beautiful woman.

Beth called it 'eye-fucking her', and it usually resulted, with her and with other girls I was interested in, in my actually fucking her. So eye-fucking Poppy's mom seemed just a bit fraught. Worse, while eye-fucking Poppy didn't seem to creep her out, neither did it make her want to jump my bones.

It all made my bone very frustrated.

All this led to me being pretty sure I was busted on the mom-ogling front. Poppy's mom had shown up in a new tennis outfit that she must have just bought. She usually sported these really hot little outfits with tight, short-sleeved tops that she wore with the collar popped up, and short skirts that were pleated and flared. It was pretty much the same style of outfit that Poppy herself wore for practices, and in them, each was lucky to look as good as the other.

But this new tennis dress was... It was the super form-fitting type you see on the professional tennis tour these days, usually being worn by a Russian with more curves than talent, and it fit her body like a glove. It was the kind of outfit that has a low, scooped neckline that both shows some cleavage and lets you get a good look at the underlying sports bra, in its coordinating color. The skirt was tight and flat against her thighs, and short enough that all she had to do was bend her knees to feed a ball and everybody could glimpse panties in that same, coordinating color as the bra. When I saw it, I immediately looked for Poppy. I'd have killed to see her in that dress. Alas, she had just a usual, run of the mill, super hot outfit on. It was a downer.

It also meant that even with Poppy right in front of me, I was sneaking way too many glances at her mother. At one point, I was tracing her curves with my eyes as she stood beside me, and as I went upward, I found her eyes looking back at me, instead of the court.

I swear, she just turned her shoulders right and then left, drawing my eyes right back down, involuntarily to her tits. Like I said—probably busted.

"Well, I gotta go," I said hastily. "Time for practice, and I think I see some friends going up now," I added, pointing past her as if that was where I had been looking. I caught Poppy's eye and waved, then jogged away up the hill hastily. I could hear Poppy's mom laugh as I ran off.

Probably busted... right?

*

And then, something unexpected happened.

I saw Carla walking in the hall ahead of me after the last of the only two classes I had that day. After the AP tests, the classes preparing for them were dismissed for the reminder of the year. This really was the home stretch for those of us Seniors who took mostly AP courses. I ran and caught up with her.

"Well, hello there," I said, in my best Joey Tribbiani. "How you doin'?"

Carla laughed, like she usually does, but not as long as she usually does. And definitely not as lasciviously as she normally does when I say that. I was pretty much asking if she wanted to sneak off somewhere and horse around a little.

"Hey, Alistaire," Carla said. "Um, can we talk?"

I was, of course, aware of the meme that 'can we talk' is never good news. But, since I had never had the phrase directed at me before, my antennae did not shoot up like they ought to have.

"Sure, what's up?" I asked, casually sauntering along, waving back at a girl who waved at me. Jeez, what was she, a Sophomore? Yikes.

"Hey, I don't know if you know, but Ron Brookwood asked me out."

"Cool. He passes the chill test," I said. Ron actually was more than just chill in my book. He wasn't a friend, but his behavior toward me the last three years had him in my good graces. I immediately hoped he and Carla would hit it off.

"Yeah..." Carla said, trailing off uncertainly.

"Not sure where it is going?" I asked, interested and utterly oblivious.

"Um, I'm not sure where it is going, or how far, or when..." Carla said, a little tartly.

"Well, we all scatter to the four winds in a couple of weeks," I observed, though it was a subject we all tended to avoid. This was all going to end soon. I don't mean just my sex-drenched Spring with all sorts of girls, but my four years at this amazing, I begrudgingly admitted, school. "You might want to get on that while you can."

Carla cocked her head at me. "You do know that Ron is going to Chapel Hill?"

Oh.

Oh!

Carla was going to UNC, Chapel Hill as well. Her parents had about shit with pride. And Ron would be going there too.

My mind spun. That upset the whole, eat, fuck, and be merry applecart we had all been living.

"Look, Alistaire, it's just that..."

"I get it," I said with as much warmth as I could muster, which was a fair amount, I was proud to note. "You really don't know where this might go, or for how long. And it might be just a tad awkward if things progress as you hope they might and you are still fucking your Track buddy."

She looked at me. "Yeah," she sighed, and looked down.

"Hey!" I said sharply. She looked up involuntarily. I could still command her...

"Look," I said. "Go get him." I held up a fist. She bumped it, and turned off in another direction. I watched her go. I really needed to stop looking at her like that.

So.

It wasn't a gut punch, or anything, but that was one fucking hell of a reality check. A beautiful, fun girl had just punched out of my life prematurely. Or at least I felt it was premature. But after graduation, they all would be punching out. We were going our separate ways—none of them to a college anywhere near Los Angeles. Sure, I hoped to see them again in the future... Hell, I hoped to fuck one or two of them in the future. Lots of people came back to our school for Alumni Day each year. But they would be out of my life in any regular or meaningful way.

I wandered down the hall pensively. With Track over, I had my whole afternoon free. There were several girls I might seek out to spend some time with, but I wasn't feeling it. Introspection sucks when you are a teenager.

But I was not going to just sit in my room on such a beautiful New England spring day.

Oh, well, if I didn't want to look back at what I already had, and was losing, I might as well see if I could still see something new. I sauntered out toward the tennis facility, earlier than I usually do.

I, of all people, really had no excuse to be glum.

*

"Well, hello Alistaire," said a soft alto voice behind me. Poppy's mom. And she had snuck up on me.

"Oh, hello Mrs... I mean Miss Fields," I said hastily, caught off guard.

"It's Manning now," she reminded me yet again, drolly. "I doubt you are going to get it straight this late in the game, Alistaire. Just call me Sloane, why don't you?"

"Sloane?" I said, surprised. Calling an adult woman by her first name was not a new experience for me, but calling the mother of a friend, or at least an acquaintance, by her first name, was.

"Yes, Sloane. Do you like my name?" she asked sweetly.

"Well, yes, I guess," I said. She had me off guard to begin with by sneaking up on me, but that wasn't my only problem. On court, Poppy had apparently borrowed her mother's dress from the last time I had been at practice, the ultra-tight athletic one. On her... it actually fit better, I thought. It wasn't as tight, well, anywhere, though only by a little bit. But the fractionally looser way it sat on Poppy's body just let the fabric slide over her form the way I guess it was supposed to. It was hard to watch Poppy warm up and not wish I was caressing her sweet, round ass and tasty breasts like that dress was. She did have on different underwear, but it was still meant to be seen. So, it was damned hard not to keep my eyes locked on her.

But.

Miss Manning... Sloane, was standing next to me, and talking to me. I'm polite, and like to give my attention to someone with whom I am conversing. The problem with that was that she might have not been wearing the new, painted-on dress, but I was still instantly aware, the moment she surprised me, that she was still way hotter dressed than was her average. Her red skirt was not as short as the dress had been, but it was just as tight and stretchy. And her top was... I realized that she didn't have a top, she was wearing a body suit under the skirt. It was made of a white, vertically-ribbed fabric with a widely scooped neck and short sleeves that only served to accentuate her sleek, lightly muscular shoulders.

So, I was trying to have a conversation with Miss... with Sloane, while trying not to just outright eye-fuck her to her face. That would have been fun in the abstract, but I was here to eye-fuck Poppy. And in that dress, Poppy desperately needed to be eye-fucked.

"You are here early," Sloane observed, as all this ran through my mind, and my eyes tried to find somewhere safe to rest.

"Now that APs are done, I don't have many classes," I said. "And Track already had its last meet, so my afternoon is free until dinner."

"So, you intend to spend your afternoon watching Poppy and her friends hit balls?" she smirked.

"I wanted to take a walk. It's a beautiful day," I said defensively. But, dammit, if she was going to poke fun at me, then my new conversational patterns, the ones that were serving me so well, demanded that I poke back at least a little, even if Sloane was a parent and a coach. "That said, I walked over here because the view is better than the one of the groundkeepers' hut."

She laughed knowingly, the wench.

"For the record, when I got your last name wrong, you had just caught me off guard. And I knew your first name already, too," I said defiantly. "I Googled you yesterday."

"Did you Google me hard?" Sloane replied archly. Christ, could I just get Poppy to flirt with me half as hard as Sloane was teasing me?

"You lied to me," I said with a smile.

"Excuse me?"

"You took a game off of Steffi in that match—on Arthur Ashe."

"You did Google me," Sloane said in surprise.

"Why did you lie?"

Sloane shrugged. "It was a routine waxing. Saying it was a double-bagel at least makes it sound epic."

I snorted, finally warming to a conversation that let me concentrate on something other than tits and legs. "You won a game against possibly the best female player of all time."

"Serena is better," she replied, almost automatically.

"Maybe," I said. "But great as Serena is, a lot of her success comes from just flat out intimidating the opponents she has. Are you going to tell me that Steffi, or Monica Seles, or Navratilova would have let her push them around like that? No. They'd have all just punched right back."

"How do you know so much about women's tennis?" Sloane asked with genuine curiosity, though not in agreement.

"Tennis is the one sport, as far as I'm concerned, where the women's game is at least as compelling, if not more so, than the men's," I said. Then I deliberately looked right at her. "Even when you discount the scenery."

Her eyes widened, and then she laughed. "I have to go feed balls. Feel free to watch. You might learn something."

*

"Hey Poppy! Hello, Miranda," I said. I had just run into Poppy and her tennis teammate in the corridor on the way to my only class that entire day.

"Hey Al," said Miranda, whom I barely knew.

"Alistaire," said Poppy. "Hey, did you watch our whole practice yesterday?"

"He did?" Miranda asked, puzzled. Apparently, I was still invisible to her. It actually comforted me that that phenomenon still existed in some cases. It made my life seem at least slightly contiguous.

"I did not," I replied. "I sat around for about 45 minutes of your practice. This whole, no practice, and almost no classes is not all it is cracked up to be," I added. "I'm getting a little bored already."

"You didn't seem bored talking to my mom."

"How is it having her be your coach? I assume she has taught you all her life," I asked, deflecting her comment.

"Mostly she is cool," Poppy began.

"Except when she wears your tennis dresses," teased Miranda. "Poppy was so pissed the other day. She went home and repossessed it."

"The purple one?" I asked, without thinking.

"You noticed it?" Poppy asked. "On both of us?"

"For the record, it looks a bit better on you," I said.

"Ooooo," said Miranda.

Poppy seemed unprepared for the compliment, and did a little deflection herself. "But it looks good on my mother?"

I shrugged. "Better on you." And I turned and walked away with a cheery wave. I had finally gotten Poppy off-balance. I wanted to leave her that way.

After a moment, I looked back and caught both Poppy and Miranda looking back at me as they walked off themselves.

Apparently, I was no longer invisible to Miranda either. But more importantly, I had finally disrupted Poppy's natural poise, if only a little.

*

The next day, the girls actually had a match, which was cool. The downside was that the school's tennis uniform was not nearly as hot as the outfits that Poppy and a few of her teammates usually wore. The upside was that I had a good excuse to be there the whole time. And how bad can any short skirt and teeshirt look on a hot girl?

I waited before heading up so I wasn't there for the beginning of the match, not because I wanted to miss the doubles, but because staying for the entire match might seem a lot, and I hoped to find a way to wander back afterward with Poppy.

The singles matches were well under way when I arrived, and I settled in on the far side of Courts 1 and 2 to watch. Poppy was playing really well, but so was her opponent. They went to a tie-break, and were the last of five courts to finish the first set.

As I said, the school uniform was not terribly attractive, though Poppy certainly looked good in hers. Heck, for that matter, Miranda down on Court 4 looked pretty fine too. But Sloane was not constrained by the uniform requirements. She could have dressed in street clothes, since she wasn't going to be on court, but she had on a simple, white, loose tennis dress. It should not have been sexy, but it was achingly so anyway. It was certainly short enough to show off her firm legs, and while the sleeveless top of the dress had a neckline that was miles from showing any cleavage, it was fitted so beautifully that it practically screamed 'great tits inside', without pulling tightly anywhere.

I'll admit it, I found my eyes following Sloane's movements as much as Poppy's. They were both totally delicious, and Sloane was just so much better packaged that day.

I watched most of the second sets from the far side before I just got bored sitting alone. Anyone else at school who wanted to watch sports that day was probably down at the Boy's Varsity Lacrosse game. It was a pretty important matchup. I got off my ass and wandered around the courts to the other side, where the coaches were prowling. The opponents' coach was pretty old, maybe fifty or something. He mostly just stalked back and forth and shouted platitudes at his players.

Sloane wandered straight over to me when I came around. "Hello Alistaire," she said with a grin. "You've been at this match a good while now. Have someone you especially want to watch?"

Oh, so we are going right back into this, are we, Sloane? "The boys' lacrosse uniforms don't show as much skin," I said mildly, staring at Poppy as I spoke.

Sloane just snorted and went back to paying attention to the match.

Three courts were done after two sets, and our school was up 2-1. Poppy had split, as well as Miranda, and both were into their third sets.

Poppy had seen me, of course, there weren't that many spectators, but she had not done much more than wave. She was very focused on her match. Miranda was getting her ass kicked all of a sudden.

I should have been focusing on Poppy. She was the hot one. She was also the one who the team's hopes rested on, because Miranda was going to lose, it looked like. But Sloane was down by Miranda's court, showing support. And I just kept staring down that way at her. I just couldn't help it.

Publius68
Publius68
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