The Deal

This is a sequel to my story in Transsexuals & Crossdressers, 'Rush', but reading that probably isn't that necessary to understanding this.

~

When one of the Delta U seniors had texted Matt that morning to let him know that the pledges next task would take place this afternoon, and it would involve streaking the campus, with the fastest finishers winning the best chance of advancing towards full initiation, Matt decided that he'd had enough. Delta U always started pledge season with way more guys than they planned on having join and there was no way Matt was putting up with any more of this crap. He might have tried the task and dealt with the humiliation if he thought he was likely to get into Delta U by doing so, but Matt had never been much of a runner and he reckoned at least half of his fellow delta U pledges were faster than him, and there were several more he was unsure about.

The thing was unlike most of his peers, Matt wasn't stuck with the initial frat he'd allowed his family to convince him to rush. And so Matt stood in the office of the president of alpha phi, and told their president, Oliver, that he was seriously been considering the offer of an expedited membership with Alpha Phi that Oliver had tacitly made him the previous day when he'd been caught sneaking around at the suggestion of a Delta U senior Oliver knew.

Matt wasn't entirely sure where he stood with Oliver, his decision to answer Matt's attempted theft from him with a hand job and the offer of a place in his frat was a baffling one. But Oliver had been friendly and accommodating, not to mention flatteringly convinced that, with the aid of Alpha Phi, Matt could go far. A mystery, but a better option than the pointless trials and humiliation offered by Delta U. It was time to make the trip he'd been considering for several days now.

*

"You understand that you'll be technically equal to all of the other pledges? We both know that you're by far my personal favourite, but personal favour from me isn't a part of being in the frat."

Matt nodded, Oliver couldn't be unfair in his duties as frat president, personal favours needed to stay personal, and likely be repaid in kind.

"You also understand that since you've skipped most of the initiation you'll need to comply with whatever extra tasks I set if you want to hold onto the place I'm offering?"

Matt hesitated, wondering if he ought to try and negotiate exactly what these tasks would entail, but he remembered Oliver's words from their last meeting. Oliver was a mystery, but he also seemed fair and respectable, Matt felt he could trust that the bargain would be fair. He nodded his acquiescence.

"Great." Oliver smiled. "First order of business, get yourself out of those jeans."

Matt tugged off his jeans, having to kick off his sneakers to get then past his ankles, and then in a burst of inspiration and confidence removed his shirt also so he was stood before Oliver in just his underwear.

"Not dressed up for me today?" Oliver asked, looking disappointed.

Matt shook his head, feeling irrationally guilty.

"What I was wearing last time..." he said, "...Well I could hardly take them down to the laundry room in the dorms."

"No," Oliver agreed, before continuing, "putting them in a machine might damage them, they'll need washing by hand and I can hardly blame you for being too busy for that right now."

Matt felt his face heat at the idea of standing at his dorm sink, holding the panties in his hands, and scrubbing at the dried come. There would be no way he could do that without remembering how they had gotten stained in the first place, Oliver's strong hands rubbing the satin against Matt's cock, and Oliver fully dressed but hot and hard against Matt's back. Yeah, that would be fun to explain to his roommate.

"Anyway," Oliver said. "Since they aren't adding anything to the view you ought to take them off." He pointed to Matt's boxer briefs.

Matt only hesitated for a moment. While Oliver hadn't seen Matt fully naked last time the panties hadn't hidden much, especially not once Oliver had gotten his hands on Matt. If anything total nakedness, even half hard just from taking, was more normal than clothed only in fancy women's under things.

Oliver eyed Matt with a grin. "Has anybody ever told you that you're lovely?" When Matt shook his head Oliver laughed. "Aren't people stupid? Come and sit just here now, will you."

He gestured to his desk and Matt obeyed. But, before he could get settled, Oliver pulled Matt's hips forward so that he was not so much sat on the desk as perched with his ass hanging off the edge of it, sprawled back, half laying down, with his weight on his forearms. Matt lay uncertain as Oliver looked at him appraisingly for what felt like an age, before crying out embarrassingly loudly when Oliver dropped unexpectedly to his knees and licked a long hot stripe up Matts cock. He bucked his hips a little and Oliver slapped him lightly on the inner thigh, something which embarrassingly did exactly nothing to diminish Matt's erection.

So focused on Oliver's tongue on his cock was Matt that he didn't even register what Oliver was doing with his free hand until he felt the light press of what had to be Oliver's finger pushing into his ass.

It was a comfortable fit, barely physically noticeable except for the strangeness of it, but Matt still squirmed, pushing up on his hands to be able to address Oliver properly.

"You... I'm not sure..." Matt began, voice falling off as Oliver's finger moved, shifting it's angle in Matt's hole as Oliver stroked his inner passage.

Stroking the inside of Matt's ass Oliver said, "Relax, I'm not planning on doing anything you won't enjoy. Trust me."

The strange thing was Matt sort of did. He wondered if Oliver's powers of persuasion were innate, or if they were learned. And if the latter, if he could convince Oliver to teach him whatever the trick was.

Right now though he was quite happy to let Oliver keep his mouth occupied as it was, his tongue flicking at the head of Matt's cock and distracting him from the bizarre feeling of the finger in his ass.

As if he had some way of knowing that Matt was starting to feel settled, a second of Oliver's fingers pressed up against Matt's hole. But before protest could even cross Matt's mind, Oliver stopped the teasing licks and instead took Matt's cock into his mouth, the hot, wet heat of it making it so Matt was too focused on the pleasure of his dick to even really notice the stretch of a second finger in his ass.

Oliver sucked him down, and then pulled back so Matt felt a second of exposure to the cool air before Oliver bobbed his head again and the overwhelming pleasure returned.

The sensation was too much for him to continue to hold himself up with his arms so he lay back on the desk and embraced the feelings as Oliver added a third finger.

Matt realised with surprise that he was not just thrusting into Oliver's mouth, but also down towards Oliver's hand, pressing Oliver's fingers deeper into his ass. Despite his expectations, Oliver's fingers inside of him felt just as good as Oliver's mouth on his cock. The stretch was new and a little peculiar but the feeling was good enough that he almost wouldn't have minded if Oliver stopped blowing him as long as his fingers kept working at this unfamiliar spot he'd found within Matt.

He felt his thighs start to shake and shut his eyes, gasping as he came. He felt Oliver swallow and the fingers slip out of his ass as he held onto the desk and took slow, steadying breaths.

As the pleasure daze faded he realised that Oliver had his own cock out and was jerking it with the same hand he'd just fingered Matt with, his eyes hungry.

Oliver gasped and Matt felt the warm spray of Oliver's come across his ass cheeks, and then, stranger still, felt some of it sliding down to drip into his stretched open hole. He clenched in surprise. It was a faint feeling, the drops of Oliver's come only slightly warmer than the friction heated lube, but the idea was in some ways more penetrating than three of Oliver's large fingers had been.

He clenched his ass against the disquieting sensation as he got to his feet. He was fairly certain that only a small amount of Oliver's come was inside him, but the idea that it might drip out would have made him flush if we weren't already blushing to the fullest extent his body was capable of.

He looked up at Oliver, who was calmly tucking himself back into his trousers, only the slightest haste to this breath giving away that he was anything other than perfectly calm.

"So we have a deal?" Matt asked trying to keep his voice steady and his goal in mind.

Oliver nodded and Matt couldn't help but grin, despite how overwhelmed he was by the situation.

"God," Oliver said with a smirk, "The things I could do to you..."