A Favour

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Matt helps Oliver do a favour for a sorority president.
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emari
emari
19 Followers

Follows my story The Deal, but can stand alone.

*****

The outfit wasn't Matt's first choice in clothing, but he didn't see why a sorority girl would kick up a fuss and refuse to wear it. The band of the lacy white bra dug into his ribs a little sure, but he figured a girl would be used to that sort of thing. Anyway, he suspected the bra and matching panties had been Oliver's choice, surely the average sorority didn't pick out its members' underwear. But other than the bra, the clothes weren't so bad. The white blouse wasn't that much different from a male dress shirt, although the fabric was thinner and it was clearly cut for a more curvaceous body type than his own, and the floaty pink skirt was almost demure, it came to mid-thigh on him and so on an average girl it would be almost knee length. Its only flaw was that the cloth was so light that he suspected that things might get a little draughty if one were to wear it outdoors. Baffled by why such a big deal had been made over clothes, Matt tugged up the white knee socks, the last of the item that Oliver had laid out for him, and stepped into the low heeled black pumps that Oliver had borrowed, presumably from an unusually large footed girl.

He was wobbly in the heels, but he figured that it was unlikely that he'd need to do much walking, so he'd cope.

Matt walked into the room where Oliver was waiting, sprawled on a luxurious looking couch. Sat next to him was a glamorous looking and elegantly dressed girl who could only be Amanda, the sorority president Oliver owed a favour to. Opposite them was a couch upon which sat an embarrassed looking girl in an ill-fitting men's suit.

Oliver grinned. "This is Amanda," he said, gesturing to the girl next to him, "Who I mentioned we're doing the favour for." He waved Matt in the direction of the free space on the sofa opposite them and so Matt walked over and sat next to the girl in the suit.

"Oh hello," Amanda said, grinning at Matt. "I see what Oliver meant..." She pointed to Matt's seatmate. "And that," she added, "Is Lexie, our troublemaker."

Lexie flushed, ducking her head.

Amanda pointed at Matt with a nod. "Look here, Lexie, Oliver has brought us an excellent example of how you're supposed to dress. It's not hard is it Mattie?"

Matt shook his head sheepishly. "Not really... Uh my name is actually-"

Amanda cut him off. "Has Oliver explained exactly what it is I want from you?"

Matt shook his head and Amanda rolled her eyes. Oliver looked unabashed.

"Don't worry," Oliver said. "You're here to be a good example for Lexie. Just follow Amanda's lead and Lexie will follow mine."

Matt nodded, that didn't sound too hard.

Amanda grinned. It made her look like a particularly classy shark. "Sigma Rho prides itself on being a sorority of ladylike girls," she said. "And, when the occasion calls for it, knowing how to please men. Since Lexie here won't act like a lady, I figured I'd indulge her wish to act like a man, with Oliver here serving as an example of proper gentlemanly conduct." Matt nodded, this was making sense so far. He was beginning to see how he was going to fit in, although he wasn't sure how he felt about it. "You," Amanda continued, "Will be playing Lexie's girl, since I could hardly ask a sorority lady to do it."

Matt frowned. "Look I know..." he gestured to his outfit and shook his head. "Despite appearances, I'm not exactly an expert on ladylike conduct."

Amanda laughed. "Don't worry too much Mattie, honey. All you need to do is follow my example."

"Anyway," said Oliver. "This is really about Lexie. You're just helping out, nobody is gonna care if you aren't perfect, as long as you do your best."

Matt nodded, reassured by Oliver's statement. He had the feeling Amanda wasn't somebody he wanted to piss off, but if Oliver said it would be fine, well, Oliver hadn't lied to him yet.

Oliver turned to Lexie. "Watch and learn," he said. He slid an arm around Amanda's shoulders, gently turning him to face her and leaning in to press his mouth to hers. They made about for a few minutes, while Matt and Lexie watched. As Amanda got increasingly into their make out session, Oliver slipped a hand down to rest on her leg and then gradually inched it up her skirt. Matt felt the early stirrings of arousal. He was getting into the show, when Oliver pulled back sharply and turned to Lexie and said, "Well, follow my lead."

Lexie startled and little and nodded, dropping her arm awkwardly across Matt's shoulders. Oliver rolled his eyes and turned his attention back to Amanda. Remembering how easily Amanda had followed Oliver's hints, Matt turned his head towards Lexie and allowed her to kiss him. For a moment, they were still, their mouths pressed up against one another without movement, before Lexie seemed to remember that Oliver had taken the lead with Amanda, and began to kiss Matt in earnest. It was still awkward though, Lexie was clearly not experienced with being the leading partner and her kisses were awkward and halting. Matt turned his gaze to the other sofa, where Oliver was doing a much more impressive job with Amanda. While he'd been kissing Lexie they'd moved so that Amanda was lying on the couch with Oliver leaning over her.

Matt tensed as he felt Lexie place a hand on his knee and then slide it up his thigh, under his skirt, so that her fingertips were brushing against his panties. She's moved much quicker that Oliver and the whole thing felt strange and abrupt. Matt had expected to be more into having a girl's hand so close to his dick but, Lexie's small, soft hand and the brush of her ill-fitting suit sleeve held little interest in favour of the show that was Oliver and Amanda.

Oliver had used the hand that wasn't occupied under Amanda's skirt to unfasten her blouse and front clasping bra and was stroking at her breasts, her nipples teased to bright pink peaks.

Lexie had clearly noticed this and was using her free hands to fumble with Matt's buttons. He hadn't been paying enough attention to know if Amanda had helped Oliver with removing her shirt, but decided he'd help Lexie out, because she was clearly struggling to unfasten his shirt one handed. If Oliver hadn't had Amanda's help it was all the more impressive because he was clearly splitting his attention between the hand on Amanda's breasts and the hand up her skirt, the shift of his arm indicating movement where Lexie had simply left her hand resting limply on Matt's thigh.

Amanda had sat up and pulled Oliver's shirt over his head, leaving his hair elegantly dishevelled and his lightly muscled bare chest on display. Matt swallowed and reached up to do the same for Lexie, but the shirt caught on the bun where she'd tied her hair back to add to the masculine look, and he struggled to get it over her head. She wasn't wearing any bra, which made sense with the masculine outfit, and also probably wasn't necessary with her small breasts. Still, although they weren't big, Matt had expected to be more excited by a bare female chest, instead he found himself drawing unflattering comparisons between Lexie's soft curves, and the hard, flat look of Oliver's abdomen, the dipped v of his hipbones and the trail of hair between them.

Oliver tugged Amanda's panties down her legs, where she kicked them onto the floor, and pushed her skirt up so that it was ruched up around her waist. Then he unfastened his trousers and pushed them and his boxers down, kicking them off elegantly as he stepped back into Amanda's space, and with one hand guided his cock into her.

Lexie clumsily copied Oliver's movements, tugging the panties down Matt's legs, the sound of tearing fabric making it clear she'd done a less than spectacular job before she finally got them over his heels and let them drop to the floor. She then unfastened her trousers and stripped bare herself, at which point Matt saw the answer to a question it hadn't occurred to him to ask about how this was going to work.

Strapped to Lexie's groin was length of flesh toned plastic. A dildo. Matt swallowed. He supposed that made sense. Clearly Amanda meant for this to be a thorough lesson. On the plus side, at least Amanda hadn't felt the need for Lexie to be generously endowed, the artificial cock was of a moderate size, probably smaller than Matt's own.

Amanda clearly needed no prepping, but Matt didn't have the same advantage. As if realising the same thing, Lexie fumbled in her pockets and pulled out a narrow tube of lubricant, the sort that could be found for free at the student health centre. She flipped off the cap, but Matt held out a hand to stop her, taking the tube. He didn't know how Oliver and Amanda had planned for this to go, but Matt didn't trust Lexie's fumbling hands and sharp looking nails with this.

He poured some of the lubricant onto his fingers. He'd experimented with this a little in the privacy of his dorm in the hours when he was certain that his roommate would be in class, but he'd failed to achieve the sort of enjoyment he'd felt when Oliver had done it, although he wondered if maybe it was simply the fact that it wasn't accompanied by a blow job when he did it to himself that meant it was less pleasurable. He kept his attention on Oliver and Amanda as he stretched himself open, working as fast as possible and trying to ignore the uncomfortable feeling of Lexie's anxious gaze. He'd worked his way up to three fingers, when Oliver glanced over at him and smirked. Matt felt the blood rush to both his face and his cock as he was reminded sharply of why he was doing this. He removed his fingers and nodded to Lexie, who gulped and lined the rubber cock up with Matt's hole, taking a slow breath before pressing in.

He shut his eyes and tried to keep his breathing even, the stretch wasn't much more than his fingers were, but it's still more than he's ever felt before. To distract himself he looked over to the other couch where Oliver was clearly doing a much better job. He was thrusting hard into Amanda, who was arching her back and meeting his movements halfway, gasping as she did so. Matt could feel his dick firming back up as he watched them. He wondered if following Amanda's lead meant he ought to fake pleasure, but this lesson was for Lexie not him. Lexie's rubber cock felt strange inside of him. The lack of heat was disconcerting and though she'd began to move her hips, her thrusts were weak and erratic, he could feel the rubber cock shifting inside of him, but it wasn't hitting anything that might give him pleasure.

On the opposite sofa Amanda shrieked, throwing her head back with her eyes shut, and a few moments later Oliver's motions subsided as he lay gasping atop her. Matt wonder if this meant that the exercise was over. Lexie clearly wasn't getting any pleasure of this, Matt was pretty sure Amanda hadn't intended her to, and neither was he, so there was no point them attempting to imitate this conclusion.

Instead, however, after a few moments rest, Oliver stood up, walking to stay behind Lexie and wrapping his hands around her hips. Lexie paused, turned her head towards him but Oliver said, "Shush, just follow my lead." He used his hands to guide her hips, her thrusts becoming straighter and faster under his direction. Matt kept his eyes locked on Oliver's face, feeling his stomach tighten at the faint rush of pleasure that Lexie's improved technique had unleashed.

For several more minutes Oliver directed Lexie's thrusts, until Matt found his breath getting short, as Lexie fucked him with improved technique. Then Oliver removed a hand from Lexie's hip and used it to grab the girl by the hand, guiding her to wrap her hand around Matt's cock. It was a strange experience, to feel the soft touch of Lexie's small hand stroking his cock, but to see Oliver's more familiar hand guiding her motions, his much larger hand rendering hers invisible. Matt bit his lip and bucked up into Oliver's, no, Lexie's grip. It seemed Oliver had taught Lexie well, as she was continuing to fuck him soundly even as Oliver instructed her on how to jerk Matt off. Matt wondered if she'd never given a hand job before, or if it were simply that Oliver was confident that his technique was better. Regardless, it did not take long before he found himself gasping to completion.

He didn't have time to savour the feeling before Lexie pulled out abruptly and turned her attention to Amanda, who was reclining naked on the couch. He felt strangely empty, clenching his ass in an attempt to avoid the sensation that he was gaping, and sat up. Oliver smiled at him. Lexie and Amanda were talking but he ignored them, sitting up and pushing the skirt down to cover himself a little. Oliver placed a hand on his knee. "Not bad," he said. "What did you think of Lexie's lesson?"

Matt wondered if he meant the lesson Amanda had been trying to teach or Oliver's lesson in fucking, so he just shrugged.

"You were very helpful," Oliver remarked, "And I hope you didn't mind doing all this for me."

Matt shrugged. "It was fine... a bit strange but interesting."

Oliver nodded. "You'll get used to that. Part of being in a fraternity is extra-curricular education, broadening your horizons, as well as helping people out. I knew I was right to admit you."

Matt felt a rush of pride and nodded.

Oliver looked over to the couch, where the girls were making out, and laughed. "I'm pretty sure Amanda is done with us," he said. "C'mon, let's get back to the house."

emari
emari
19 Followers
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AnonymousAnonymousalmost 7 years ago
Skirt

Dress me in a skirt and I will always submit.

cali_fraecali_fraeover 9 years ago

I read this twice, once on its own & then again after rush & the deal. Reading it the latter way was more enjoyable as I was able to get more from the charecters. I,m really starting to enjoy how the sensetive & naive Matt is being guided & moulded by Oliver & that theres a warmth to how he does this, I'm sure most aspiring girls would love to have such a gentleman in their lives. Please continue writing this series but maybe think about putting them togeather as chapters of the whole story x

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