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Chapter 22
by
Tonyrolo
What's next?
Career Opportunities
"Welcome to my humble abode" Leah announced ironically "Do you like it?"
All the rooms in this place were virtually identical, save for the few lucky folk who had an en suite bathroom. Leah wasn't one of those, and Andy found himself briefly daydreaming about her in a communal shower scenario with Elaine. It was bound to have happened, since the pair were so close and practically neighbours. Still, he didn't need to be concocting yet more Leah Caldwell masturbation fantasies right now - he was literally in her bedroom.
She sat herself on the bed, but enough to one side to let Andy know he was welcome to place himself next to her, rather than having to take the uncomfortable guest chair that all rooms came equipped with as standard. He took her up on her unspoken invitation.
"So how was your day?" she enquired.
"Pretty good, I went bowling in town with a friend"
Andy decided it was wise not to volunteer any more information than that.
"Oh, and why wasn't I invited?" Leah asked accusingly, before breaking into laughter at Andy's immediate awkward reaction "Relax, I was messing with you. Bowling really isn't my thing, and I also spent the day with a new friend. You'd like her, she's really hot. She's a Libra though, so I wouldn't get any ideas"
"I won't"
That threesome with Leah and Elaine that Andy had been dreaming of was starting to look impossible, with one of them only liking Virgos and the other considering herself incompatible with them.
"Wanna beer?"
"Sure"
Leah reached into a cooler she had next to her bed, grabbed a couple of cans and passed one to Andy, shuffling her body up closer to his as she did so.
"it's Freshers' week but I'm feeling lazy, so I propose we stay here in my room for the rest of the evening and get drunk together"
"Okay"
Andy was more than happy with that arrangement.
Leah opened her can and held it towards her former classmate for him to clink his own against.
"To old friends who weren't really friends but now are" she toasted.
They then talked happily while they drank, Leah actually being very easy for Andy to converse with. Although they hadn't known each other well at school, they still had a lot of shared memories and reference points to bond over. Also, Andy was a pretty good mimic, and his impressions of some of his old classmates and teachers, which would have been completely wasted on anyone else in town, were consistently cracking Leah up.
She then decided the conversation should get more serious.
"So, I have this kind of dilemma at the moment. It would be good to get your take on it"
"Sure"
"Did you know I do modelling part time?"
"No, but I can easily believe it from your Insta pics"
"Well, my question is related to that. I'm kind of looking for career and life advice rolled into one"
"I'm not sure I'm qualified to give you either" Andy warned her
"Sure you are, that stuff you were saying about astrology being a science was so astute I was literally telling my new friend about it earlier today. Plus, Virgo's are practical thinkers and great decision makers"
Leah's faith in anyone who happened to be born between late August and late September was almost worrying.
"Okay then, ask me whatever you want I guess. I'll give you the most honest answer I can"
Leah finished the sip of her beer she was in the middle of taking, then came right out with it.
"Do you think I should do nudes?"
The question, posed so casually, almost made Andy spit out his own drink.
"Err.."
"Let's be clear here, I'm not talking porn. These are tasteful, artistic shots, but you can see my whole body and I'm not wearing anything. My agent persuaded me to take some to test the water, and I've had an offer for, like, a lot more money than I usually get. It's easy cash that could really help me with my student debts, I'm just not sure if I'd be comfortable having the photos out there, y'know. My agent is kind of pushing me to sign them over, but he obviously wants his cut and doesn't give a shit about the consequences for me. I don't know what to do, and could really use a second opinion from a trusted friend"
"Err..."
"Here, I'll show you the kind of thing I'm talking about"
Andy could suddenly feel his palms sweating. Before he came to this University, the fact that Leah was talking to him and knew his name would have been an exciting enough prospect. Now he was in her room, huddled up on the bed next to her, and she was about to show him a nude photo? Surely this was a fake out?
It wasn't.

"See, tasteful, right?"
Andy could almost feel his heart leaping out of his chest, not to mention his dick shooting up to attention in record breaking time. Leah had passed him her phone, on which was a rear view, full body picture in which the girl next to him was indeed wearing less than a single stitch of clothing. Her perfect arse was on full display and the star of the show, but she had also turned her body just enough to show some undeniable side nipple.
He also couldn't help but realise there would be other, probably even more revealing, photos to be devoured no more than a finger swipe away. He wasn't going to do it, but just knowing he could was intoxicating.
"So, what do you think?"
"It's a stunning photo" Andy blurted out, finding himself unable to take his eyes off it "You look incredible"
"Thanks, but I meant should I give permission for it to be used?"
Oh yeah. That was the question.
"Most of the photos are full body but not rear view" she added tantalisingly, as she rested her chin on Andy's shoulder and gazed down at the picture with him "this is one of the milder ones"
Andy was struggling not to salivate by this point, but he knew, if he ever wanted to see that body outside of a phone screen, what his answer had to be. Plus, as crazy as the thought still felt, he could end this experience with Leah as his girlfriend and, if that were the case, he certainly wouldn't be comfortable with the idea of other guys jerking off over nude pictures of her.
"Honestly Leah, while the photo is easily good enough for you to do this professionally, and I get that we all need money, I feel like you might end up regretting signing these over. Once you do that, you've lost control of them forever, and who knows where they could end up? You are really smart, and will be able to pay off your debts eventually without taking a risky short cut like this"
Leah smiled and gave Andy an appreciative kiss on the cheek.
"That's kind of what I was hoping you'd say. I'm glad I asked" she told him, warmly "Thanks for looking out for me and not being a sleaze. I'll text my agent tomorrow and say I'm not gonna ever do nudes"
Andy felt like a traitor to his own gender for giving that advice, but he could practically see his high school crush's affection level for him rising in real time as she took her phone back and passed him another beer.
Any hopes he had of the evening getting even raunchier were soon dashed though when Leah, likely not much of a drinker outside of Freshers' week, started to become very sleepy very quickly. Andy therefore had to make do with rubbing one off the second he got back to his room, the image of Leah Caldwell's naked body now burned indelibly into his mind.
This run had already become way more intense than the last, and in the best way imaginable. The crazy part was, Andy hadn't even reached its midway point yet.
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 10, 2026
by Tonyrolo
Created on May 22, 2026
by Tonyrolo
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