Chapter 28
by
Tonyrolo
What's next?
Three is a Crowd
Andy was still buzzing as he made his way down the two flights of stairs from Sara's room to Elaine's. If all blow jobs felt as good as that one had, he hoped to receive many more during his lifetime.
He was, however, also feeling bad about rushing from one girl's bedroom straight to another's. He both cared about and respected Sara and, under normal circumstances, such behaviour would be unforgivable. But time management was such a key aspect of this experience, and he rationalised that, by keeping his options open, he was giving himself the best possible chance of eventually breaking out of the loop with whoever the right person turned out to be. Knowing this entire week would be erased everywhere but his own memory in around twenty four hours time also helped to ease his guilty conscience.
He knocked on Elaine's door, but had barely managed to introduce himself before Leah had come rushing over.
"ANNNDYYYY!"
She hugged her former classmate almost possessively, before introducing him to Elaine herself, with her arm still wrapped around his waist.
"Elaine, this is my friend Andy. He's coming inside to join us" she announced before turning to him "Aren't you?"
"Um, yeah if that's okay"
"Oh God, you're THE Andy!" Elaine asked excitedly "This one here won't shut up about you!"
"Hey, that's a massive exaggeration!" Leah pouted, looking a little embarrassed, as she gave Elaine a slap on the shoulder.
"Sorry , gorgeous, you're right, I was exaggerating"
However, as she brought Leah in for a hug so her back was turned, Elaine clearly mouthed the words "I wasn't" silently at Andy while giving him an encouraging wink.
--
As before, the gathering had soon dwindled to just Andy and the two insanely hot women.

It was an already near perfect set up that, this time around, was about to get even better.
"Those chairs are horrible. Why don't you sit on the bed with us?" Leah suggested.
"I'm not sure there's room for me on there"
"Of course there is, as long as you don't mind me sitting on your lap"
Andy didn't mind Leah sitting on his lap, so she was soon perched on top of him, one arm draped around his neck while the other was used to helpfully insert the spliff into his mouth whenever it was time to move it from her lips to his.
"So were you two close before you came here?" Elaine asked "Did you date or anything like that?"
"That's the funny thing, we barely even spoke" Leah admitted "Andy never paid me any attention"
"What? Are you blind, Andy?"
Leah's claim wasn't entirely true. Andy had been more or less fixated on her from the onset of puberty. He had been fantasising about her the first time he had an orgasm and, though he didn't keep a tally, Andy was confident thoughts of Leah in various imagined sexual scenarios had inspired more subsequent wanks than all the other girls he knew combined. That probably wasn't a counter argument worth making here and now though.
"We just didn't run in the same crowds. But maybe some higher **** had a plan for us to connect here instead"
That sounded like exactly the kind of shit Leah went for.
"That's so true!" she cooed as she began stroking his hair "It's like we were brought together at exactly the right time. When we were talking at dinner the other evening, I felt this amazing sense of familiarity with you that I couldn't account for, considering how little we'd spoken in the past. Then you said all those amazing things about astrology and it turned out you were a Virgo, which is exactly what my psychic mentor has always said I need in my life to balance me"
She seriously has a psychic mentor?
"Jesus, will you two get a room that isn't mine?" Elaine joked.
The conversation became a little less charged after that, though having Leah Caldwell sitting on his lap still made it feel intense to Andy.
"Another one?"
Elaine reached into her bedside cabinet and produced a second joint after the first had been stubbed out.
"Not for me, I'm about ready to turn into a pumpkin" Leah declined as she jumped off Andy's lap, stretched and yawned.
"Yeah, maybe you're right, I should probably call it a night too" Elaine agreed, placing the spliff back where she had just retrieved it from this time.
"Andrew, would you kindly escort me back to my dormitory" Leah asked in a mock posh accent "I understand floor four can become quite perilous for a young woman travelling unaccompanied at this time of night"
"Uh, sure.."
So, it didn't look like Andy would be impressing Elaine with his mind reading trick tonight. Still, he was presently posing as a Virgo, and this was clearly a Leah run, not an Elaine one.
The pair made the twenty metre long trip from Elaine's door to Leah's, and Andy was ready to hug his long time crush turned friend goodnight when...
"I'm not really tired, I just don't like to smoke as much as she does"
"Oh"
"Do you want to come in? I've still got some beers from before, and you and I can hang out some more?"
Andy felt a wave of nervous excitement rush through his body that took great effort to keep hidden. There had been a few false starts and close shaves since this experience began, but it finally felt like something truly momentous was about to happen. Why else would Leah be inviting him into her bedroom at one in the morning if not for sex? She had hardly been subtle about her interest in him that evening.
As long as he managed not to fuck anything up at the last minute, Andy was about to lose his virginity to his high school crush. He could hardly think of a more poetic way for it to happen, however bizarre and fantastical the circumstances.
"Sure" he smiled back as Leah opened her door.
What's next?
Groundhog Lay
If at first you don't succeed...
A nerdy, socially awkward virgin fails dismally to get laid during his first week at a University full of hot, single girls. Luckily, he gets to keep re-living the week until he experiences the perfect fuck with the perfect woman, no matter how many enjoyable, but less than perfect, sexual encounters it takes for him to get there.
Updated on Jun 12, 2026
by Tonyrolo
Created on May 22, 2026
by Tonyrolo
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