Riley wasn't the luckiest guy in the world. He didn't have good genetics like Gary or Daniel, being the definition of a late bloomer. His parents weren't rich like Sean's. Hell, he couldn't even luck out and have an interesting hobby. Well, a hobby that was interesting to anyone other than a/v nerds and middle-aged guys who did nothing but rant about how things were better 'back in the day'.
As Valerie took him by the hand and led him up the stairs, however, he felt like the luckiest guy in the world.
Valerie, for her part in escalating things, was unphased by the situation. For the most part. She drew Riley up the stairs and he followed wordlessly, eyes still wide in disbelief over how his gamble had played out.
Daniel, Gary, and Sean followed with the former two scrambling up the stairs, and Sean, himself, only following out of a sense of curiosity.
No one had asked Sean how he felt about things. Whether he had an opinion on it at all was something he decided was best to keep to himself. His friends had fantasized about this for years. While Riley had always been the least vocal about his attraction to Valerie - often admonishing Gary and Daniel for their lewd comments - he was just as attracted to her. In fact, he would take advantage of his short stature to have his face pressed into her bosom when 'hugs' went out.
That being said, he was as clueless as they came when it came to sexual matters. He didn't have the benefit of Daniel's experience with the girls he hooked up with at house parties; Gary might have been a virgin, but he had at least gotten a little bit of attention from girls who considered him the sensitive type; even Sean had engaged in a Summer fling two years prior and had a story to tell.
Riley, by comparison, only had jerking off to vintage porn flicks. Under normal circumstances, that would be nothing. But when one of the hottest porn stars of the previous era was about to suck him off, it seemed like he had been training for this moment for years.
He allowed Valerie to pull him into her bedroom. There wasn't much else Riley could do. Should he take the lead? Should he even make a suggestion? His heart was racing and he couldn't decide whether he should do so much as speak. He felt as though opening his mouth would make this golden opportunity disappear. The situation played out like a dream and he had too much experience with getting overly invested in wet dreams, only to wake up right before the good part started.
Well, Riley's wet dreams didn't involve his friends gawking as he got his first blowjob.
It couldn't be helped, though. Valerie didn't lock the bedroom door or anything. Perhaps she should have. In fact, the thought hadn't so much as crossed her mind. This fierce attitude of hers was something she had long buried and dug up now to put these obstinate boys in their place. Veronica Vixen was more than a stage name; Veronica was a persona, and she wasn't shy to perform in front of an audience, no matter who happened to be watching.
When Riley stumbled into the Lawsons' bedroom, it was like stepping over a threshold. He had been in there as a younger boy but, somehow, as he got older, it seemed almost taboo. Now he stood only a few feet from Mama Val's bed, the woman herself having promised to fulfill what would have been Riley's wildest dream.
"Well," she said with an eyebrow raised, "what are you waiting for? Whip it out Mr. Windham!"
Riley hesitated. "R-right away?" he stuttered. "Right now?"
"What?" Valerie laughed. "Were you hoping for foreplay? Where's that rude attitude you put on earlier?"
Riley blushed. The redhead's unfortunately pale complexion made it practically impossible to hide how flustered Valerie's words had made him. Valerie, on the other hand, pounced on his hesitation. She could push him but knew this was Riley's breaking point. Would he man up or buckle under the pressure? If she were to hedge her bets, Riley was a few seconds away from bolting right out of the bedroom door. It's why she hadn't locked it, after all, and the little audience consisting of his best friends provided an additional bit of pressure that didn't hurt her position, either.
"But," Riley muttered, "everyone's watching."
"So?" Valerie said in a low, seductive tone. She stepped towards Riley, speaking to him not only as the motherly figure he had known all these years, but as a woman. "Afraid you can't perform, little man?"
Riley gaped, not saying anything at all. He couldn't, not with how Valerie suddenly tugged on the front of his jeans. He usually wore them with no belt, giving his waistband quite a lot of give.
"Come on, Riley!" Daniel hissed. "Stop being such a little pussy!"
"Shut up, Dan!" Riley groaned.
Gary said nothing, and neither did Sean. In fact, Sean seemed less phased by the situation as a whole than either of his two friends.
Valerie hooked three fingers behind the button of Riley's jeans and tugged. She tugged hard. Riley's slight build could hardly resist, especially since he was in no way prepared for the aggressive maneuver.
"Whip it out, Riley! This was your idea!" Valerie teased. "Unless Daniel is right," her voice dropped low, "and you are a little fucking pussy after all."
Gary's eyes went wide, as did Daniel's. Unlike Sean, the other two had never heard Valerie swear before. Especially not in such an aggressive tone of voice. Aggressive, commanding, and equally seductive.
Riley's brow furrowed. Something about the way Valerie had spoken didn't sit right with him. It wasn't the Mama Val he knew - and loved. Her words stung, even though he knew that, on some level, Valerie did not mean what she said. Nonetheless, her taunting resonated with Riley. Really, it reminded him of all the teasing he had endured throughout his childhood - both from within his group of close friends, and without.
Valerie saw Riley's resolve waver. Of course, he would falter, even after she had dragged him into her bedroom and did all but plant his feet where he needed to stand. She smirked, satisfied that he had learned his lesson. "If you're not going to perform," she started but found her words caught in her throat and Riley's hands moved to the button of his jeans.
Her eyes opened wide as Riley's slender fingers fumbled at the front of his waistband. He didn't wear a belt. It was a habit; a bad one that had gotten him pantsed in the school hallway on more than one occasion. Beneath his jeans, Riley wore a set of checkered boxers - blue squares with black stripes - the kind of underwear that made it obvious his mother still bought all his clothes.
Valerie glanced down, almost taken aback at Riley's - could she describe this as audacity? His jeans slipped down around his slender hips, finding absolutely no purchase on his boyish figure, and fell past his knees before bunching around his calves.
Riley didn't know what to do with his top. Somehow, he felt insecure in taking off his t-shirt in front of his friends, but the hem of it managed to frustrate him so much as he attempted to slip his thumbs into the waistband of his shorts that he finally gave in and lifted it.
He expected Daniel, at least, to make a comment. But no one said anything. Even Valerie waited wordlessly as she looked on and, finally, Riley dropped his boxers around his hips.
Valerie, to her credit, had seen many men's penises in her life. It was natural, given her history; she had seen uncut cocks and cut ones; colors ranging from pale, to olive-toned and dark ebony; perfectly straight cocks as well as those with the most wicked curves that dug into her flesh. And, yes, she had seen some short ones and monster dongs that made her wonder how they'd fit inside anyone, much less herself.
Still, for all her experience, she had never seen a man drop his drawers as Riley did while the extent of his shaft still remained nestled behind his boxers. A feat made all the more impressive by the fact that Riley was still soft.
"Well," Valerie stammered as Riley reached between his legs and pulled his tool free. His short stature was responsible for most of the illusion. If she were to guess, Valerie would imagine that his semi-erect member was just past six inches long. "Well aren't you packing...a surprise."
Around the base of Riley's shaft was a halo of fiery red pubic hair that grew over his pubic region. His organ was impressively thick, and even more so as it was still barely halfway to being considered firm in any capacity. His face was flushed scarlet as the real cause of his hesitation was revealed: Riley found it incredibly difficult to achieve an erection, given the circumstance.
Valerie was not phased, however. Or, rather, she understood perfectly well. A virgin, and with his first time consisting of such an intimate audience. It was no wonder that Riley struggled to get it up. Still, seeing that tool stirred something within her; a feeling that was once familiar, now long forgotten, grew again within her. A tightness that nestled just below her midriff, deep within her most feminine parts. A wicked curiosity, if she were to describe it.
Riley bit his lower lip nervously. His fingertips bounced the throbbing meat, almost as if he were begging his piece to wake up and stop embarrassing him. The mounting pressure he placed on himself did not help.
"Huh," Valerie said, wondering out loud. She tilted her head to the side and only then realized that she had been staring. "Can I," she started, "can I touch it?"
"Yeah." Riley answered almost instantly, his voice cracking as he did. "Y-yeah," he coughed. "Please...do..."
Valerie reached a fingertip towards Riley's wrist. One of her legs bent at the knee as she shifted her weight. She felt silly. She was a middle-aged woman but the situation felt mischievous. It made her feel as though she were young again. She glanced to the door as she touched the inside of Riley's palm, over the pad at the base of his thumb, and her finger lingered dangerously close to that organ.
