Chapter 31
by
Tonyrolo
What's next?
Eventually, it Happens Naturally
Andy's hands were trembling slightly as he typed the digits he had memorised into his phone. This felt like crossing a line, but he couldn't think of any better ideas, and this whole week would end up being erased from history anyway, so no real damage could be done.
"Hello, is that Mrs Grant?"
"Speaking"
"I'm calling from the University of Mansfield. This is regarding your daughter, Gemma"
There was an uncomfortable pause on the other end of the line before the distinctly terse response came.
"What about her?"
"It's come to my attention that Gemma failed to register for any of her classes yesterday. We've also been unable to contact her through our usual channels. Is there a reason for that which you are aware of?"
Again, the silence almost felt painful.
"She's at home with her family. There has been something of an emergency"
"I trust everyone is okay?"
Andy felt confident from Gemma's manner after her return on previous runs that was the case, but needed to be sure he wasn't intruding on anything genuinely troubling here.
"Everyone is fine"
"I'm relieved to hear that. It's very important your daughter is back with us as soon as possible though. It could have a significantly negative impact on her time here if she misses too much of her orientation week"
That sounded about the right level of seriousness without making any kind of threat, Andy thought.
"I see" there was a slight hesitation before "Okay, I can have her back to you today. It should take her about five hours to travel up from Brighton. Does that work for you?"
Fucking get in!
"Yes, that should be an acceptable resolution" Andy told her in what he considered his most professional sounding tone "It would be appreciated if, short of any genuine emergencies, Gemma's time here was disrupted as little as possible"
"Of course, I fully understand. This was my fault, so please don't let it count against my daughter. She's a great kid"
"I know. I won't. Thank you for your cooperation"
So, that felt like a success, even if it didn't sound particularly great when he ran through what he had just done his head.
Why did you phone someone posing as a University staff member and intervene in their family emergency?
Because I wanted to fuck their daughter.
However, he was utterly convinced someone he cared about was being unfairly used as a crutch during her parents marital crisis, and having her university experience disrupted in the process. His actions were justifiable, in his mind.
That slightly awkward task out of the way, there was someone else he was hoping to catch up with.
---
"Hello?"
"Hey, I'm Andrew. Wanna go ice skating?"
Tamara looked at Andy in confusion as she stood in her semi open doorway. Then she broke into a smile.
"That's so random! I absolutely love ice skating. But without wanting to sound rude, do we know each other?"
"No, I'm asking you out because I want to get to know you"
Tamara paused for a moment. Andy had literally framed this as a date. Had he pushed too far too soon this time?
---
"So have you been skating before?"
"No, I'm hoping you can teach me"
Andy was also hoping this excursion wouldn't be wrecked by the paparazzi as their last skating date had been. Their Tuesday bowling trip hadn't been intruded on during the previous run, so maybe Tamara would be allowed to enjoy herself properly on this occasion.
As they stepped onto the ice together, Andy immediately felt more at ease than he had before.
"Wow, you're actually very impressive for a first timer" Tamara enthused "You're posture and balance are great, most people don't make the adjustment from regular walking when they start out"
"Thanks, I still feel like I could fall over at any moment though"
"That's okay. Just follow my lead. We'll start slow, but you'll get there. Eventually, it happens naturally"
Andy felt less like a child being guided around by his mother this time and more like someone on a date, albeit he realised Tamara was having to hold herself back immensely not to exceed his level. Nonetheless, it was obvious she was enjoying herself. To his surprise, based entirely on unfair preconceptions he had of people of her class, Andy had a more natural rapport with Tamara than nearly anyone else. Even if he still disliked ice skating, he was having a great time regardless.
After a while, thanks to the safety net of being expertly guided by his vastly more experienced companion, Andy began to believe his skating abilities were significantly greater than was actually the case. That eventually resulted in him losing his balance and tumbling onto the ice. He brought Tamara, who had been linking arms, down with him, and she landed on Andy.
Thankfully, rather than get annoyed at his incompetence, she burst out laughing, while remaining laid on top of him longer than she needed to. Seizing the moment, Andy leaned upwards and kissed Tamara. She kissed him back for a few moments, closing her eyes as she did so, before opening them again and climbing off him while scanning the venue. She was looking for photographers, he realised.
"We shouldn't do that here" she told him "You're welcome to join me in my room back in Halls though? In fact, I'd really like it if you did"
---
Andy always felt a strange but exhilarating sense of breaking unwritten rules when he was making out with Tamara. Was there any chance at all of him coming out of this loop with her at his side? Within the university bubble they seemed to work surprisingly well as a couple, but outside of it? Tamara was no snob, but Andy felt sure her family would be. Her father was literally the Earl of Rutland. That didn't sound like someone who would want his only daughter associating with a working class lad from Bristol, let alone falling for him. Even if they did get together, the pressure on Tamara to ditch Andy for someone deemed more suitable would be immense.
As he lay on her bed, kissing and caressing her, there was no need to worry about that in the here and now. All Andy needed to be aware of was how beautiful, flawless, and classy Tamara was - and that, for some reason, she seemed to genuinely really like him. He wanted to push further with her now than he had before. Tamara claimed to be more reserved than most girls her age, and Andy had tried his best to hold back with her, despite how lustful she always made him, as it felt like the proper thing to do. But he was horny as hell now and knew her affection level was high.
He began tugging at the bottom of the top she was wearing. Unless it was very discrete, she didn't seem to be wearing a bra underneath it. He really wanted it off her.
Tamara seemed to consider whether or not to go with the flow for a moment or two, before helpfully lifting up her arms and allowing Andy to pull it from her body. There had been no subtly hidden bra underneath what she had been wearing, so her tits were now out in the open. Like seemingly everything else about Tamara, they were pretty much perfect.
She smiled up at Andy as he pushed her down onto the bed.

This was a perfect example of affection stacking working beautifully in Andy's favour. What he was doing now should have been impossible on the same day that he met the stunning young aristocrat. Even after two largely successful dates on the previous run, she had very deliberately cooled things down before he had the chance to begin undressing her. This had been well worth braving the ice a second time for.
Andy leaned down and kissed Tamara's nipple, causing her to giggle cutely.
"You're so fucking incredible"
Andy had just blurted the words out, incapable of keeping that thought to himself.
"Oh gosh, don't say that. There's nothing worse than being put on a pedestal"
"Sorry"
"You don't need to apologise" she smiled and stroked his hair reassuringly "It was a nice thing to say. I just mentioned it for future reference"
Okay, well that was noted then. It was difficult not to gush over Tamara though, which is probably exactly why she'd had enough of guys doing it.
Rather than say anything else, he leaned back down and began making out passionately with Tamara once more, this time fondling her bare boobs as he did so. It really felt like life couldn't get much better than this.
Except, it could theoretically.
Andy began delicately running his finger down her abdomen, tracing a line from her navel to the hem of her trousers. He was hoping she would allow him to remove those from her as well, but instead of further compliance, he felt her hand being placed delicately, tactfully on top of his.
"I think we've probably gone far enough already for today" Tamara told him gently but firmly as she sat up and pulled her top back on "I would never normally do that with a guy I only just met. I just feel this really natural connection with you that I honestly can't account for in such a short space of time"
"I feel it too"
"I'm happy to hear that" Tamara smiled, running a hand through her hair "I don't see any reason to rush things, though. We'll both be here for the next three years after all. I hope we'll be spending more time together soon. You can be my date for the end of week social if you'd like?"
That particular event was going to become an increasingly difficult hurdle to negotiate, Andy realised. The last one he made it to, which he had attended with Gemma as his date, had turned into a pretty tense affair. That was only going to intensify as his bonds with all the girls he was building affection with deepened. To romance one girl and then show up at the social with another was the behaviour of a cad, Andy realised. However, the temptation to take the cowards way out and Pittsburgh past it was overruled by the knowledge that, if it went well, it could raise the affection level of whoever his date was very quickly.
As far as this run went, he wasn't about to pass up the opportunity to take the beautiful and, whether she liked it or not, famous Lady Tamara Sutton-Campbell to the social as his date. He would just have to deal with any fallout from that decision if and when it happened.
"It would be my honour to take you" Andy started, before jokingly correcting himself "Sorry, no pedestals. Sure, whatever"
"Perfect" Tamara laughed as she gave Andy a kiss on the cheek "Then it's a date!"
---
Andy felt like he was getting closer and closer to living the perfect life during the week he was effectively trapped in. Perhaps he should never leave it? After getting hot and heavy with Tamara during the day, he was keeping his evening free for Elaine. In the meantime, there was someone else he needed to check in on.
He knocked on the door three times.
"Hang on a moment! I have a slight nudity situation going on here" Gemma's voice called out tantalisingly from inside her room "Just give me thirty seconds to throw a t-shirt on!"
Okay, so now Andy was going to be greeting her with an erection.

"Oh, hey, It's Andy isn't it?" Gemma beamed when the door swung open to reveal her.
Was she wearing anything at all underneath that t-shirt she had found?
"Sorry, you caught me just before I jumped into the shower. I had a long and sweaty journey back to campus today"
"That's why I knocked. I wanted to check if everything is okay"
"Oh God, that's so sweet of you!" she sounded genuinely touched "Yes, all good. It was a wasted trip really"
Well, that was a relief to Andy. Whatever his motivations, he had done the best thing for Gemma.
"I also wondered if you wanted to grab that coffee we were going to get tomorrow?"
"Wow. Yes, definitely" Gemma nodded with an enthusiastic smile "After missing the first two days I was slightly worried everyone would have formed their social groups already and I'd be stuck as a recluse for the next three years"
"There's no chance of that on my watch" Andy reassured her.
"Well, that's a relief. Maybe call here for me around midday? If you'd like, we can turn that coffee into lunch and get to know each other better"
As Andy left Gemma to her shower, pleased that had gone about as well as he could have realistically hoped, his phone buzzed.
It was Leah. He had his fingers crossed her message was about a certain Libra buddy of hers.
What's next?
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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 18, 2026
by Tonyrolo
Created on May 22, 2026
by Tonyrolo
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