His Moms Toyboy

As bad ideas went this was the worst that Ryan Ward had ever heard off, it made Hitler's invasion of Russia seem like a smart move and Icarus seem like a bright guy, but it was too late, he was committed. Beside him his Mom was opening the car door and greeting one of her old school friends who she hadn't seen for near twenty years. He remained sitting for a moment, as the two women gabbled excitedly beside the car, but even as they were talking he could see the other woman looking through the window curiously at him, so he forced a smile onto his face, like he was excited to be here, and undid his safety belt.

"He is handsome Brandi" the woman said as he exited, "How did you snag someone so young?"

His Mom grinned proudly and slid her arm through his, "You wouldn't believe we met in a coffee shop, Claire. I'd been served his latte by accident and we clicked at the counter as we were both returning them to the barista." It was so obvious a lie that he was surprised Claire didn't burst out laughing. Keep it simple, he had said to his Mom. It has to be romantic as well as believable, she had replied. Now Ryan wasn't sure it was either.

But it seemed to work as Claire nodded sagely, "He looks so young and handsome," she admired him like he was a Greek statue in a museum and he felt himself blushing. It was even worse as his Mom hugged him tighter, which would have been fine if she'd been acting as a possessive Mom trying to stop a cougar getting her hooks into him, but less so when she was playing the part of a cougar who had him in her claws and the other woman was a rival large cat eyeing the captured prey for herself. "So virile," she purred, her eyes moving up and down him, mentally undressing him.

"He's at college," smiled his Mom. Another lie, though a smaller one, as he had just finished High School and was going to college in the Fall, however his Mom had thought it'd be easier if they made he'd left home already rather than having to field questions about what his parents thought about him being away at a wedding with a woman literally old enough to be his mother.

"I'm sure he's getting an education," Claire's laugh left little doubt she was not talking about the learning you get in classrooms. "He can't be much older than your son, what's his name?"

"Michael," his Mom said. That was true, even though as he'd been named after his Dad's favourite uncle as soon as the man had left, sixteen years old, his Mom had reverted to his second name, Ryan, which is what everyone knew him as. "Slightly older, Michael's away this weekend with friends, though he's cool with Ryan, isn't he lover?"

"He's a great kid," said Ryan, unable to stop himself from going even redder

Especially as his Mom couldn't resist a little joke at his expense, "A little immature sometimes, though, not like my stud here." She squeezed his arm tighter, but then luckily, deciding she'd spent enough time teasing him and artfully moved the conversation onto Claire's children and husband (who sounded like he was close to sixty and very wealthy). After a few minutes his Mom glanced at her watch, "We better book in and change, it's been a long drive. Will we see you in the bar?"

"I'll be there," said Claire, winking at Ryan and making it sound like she spent a fair amount of her evenings in hotel bars.

He was already heading to the car, "I'll get our cases," he said as his Mom finished her conversation with her friend. Getting them out, he was already at the entrance by the time his Mom said her goodbyes after exchanging some gossip.

"She hasn't changed," she said as she joined him, "Always on the look-out for other girl's guys, even if she had one herself."

"I'm your son," he reminded her.

"Not for this weekend," she grinned and slid her arm through his again, "Lover," she teased.

"I can't believe we got away with it," he continued, looking around briefly to make sure no-one could overhear. "When we're standing next to each other, didn't she notice the family resemblance?"

"You look more like your Dad," she replied and shrugged, "People see what they want to see. I said you're my boyfriend, that's what everyone is going to believe. Anyway I've not seen anyone here for close to eighteen years, if they ever saw you it was as a baby."

"It's only a wedding," he had said, "No-one's going to worry if you go without a partner."

However, she wasn't having any of it. It was the second marriage of one of her old cheerleader friends from High School and the whole team would be there, for the first time since they'd graduated two dozen years ago; and they were a bunch of judgemental bitches who wouldn't believe she was just going through a fallow patch since she'd broken with her last boyfriend. "You could go," she had suddenly suggested.

"Sure," he had replied, not sure how taking her son would solve the problem of being thought to be a singleton.

"As my boyfriend," she added, "Everyone would die if I turned up with a toyboy." Immediately he knew it was a bad idea and said no, except his Mom could be very persuasive, especially when she did her 'poor little me' routine and fluttered her eyelids like she was a blonde in distress.

So here he was, a whole weekend of pretending to be his Mom's lover, it was made no better by the fact she seemed to be enjoying the whole deception, a fooling her old friends seemed to be immensely appealing. He couldn't believe he had agreed, but now they were here he'd just have to go along with it and hope they could pull it off. His Mom was at the reception, booking them in and taking the key. He picked up the holdall and then took the handle of the suitcase, just the one -- they were sharing a room, a double at that -- his Mom pointing out everyone would be suspicious if they had separate rooms or even a twin. He had suggested he sleep on the couch, but she had said that was dumb and not good for his back, there was nothing wrong with them sharing a bed; they'd done it lots of time when he was younger, so what was the difference now? He didn't tell her.

Once inside the room Ryan let out a sigh of relief as he closed the door behind him; in the room, safe from prying eyes he could relax -- it had been more stressful than he had imagined, though his Mom still seemed pretty laid back, as if it was something they did every weekend. She was unzipping the suitcase and getting out their clothes. "I talked to the girls earlier," she said as she slipped one of his shirts onto a hangar and putting it in the wardrobe, "Katie..."[that was the bride] "...is eating with her family, so the rest of us are grabbing some food in the hotel bar about eight and she'll join us for drinks about ten."

He nodded, resigned to an evening when his Mom pretended to flirt with him and he pretended to enjoy it, and sometimes flirt back. Not that his Mom was unattractive, not having put on much weight from her cheerleader days, except perhaps around her bosoms -- which were larger than average but not excessively so and whose hair remained blonde without needing any additional help. More than one of his friends had let their gaze linger a little too long when she'd knocked on his room door and come into to deposit his laundry on the side board. How she was so unlucky with guys was a mystery, but not one it was his job to solve.

"You want to shower first?" she asked.

"Shower?" he asked, as he hadn't thought about it.

"Yes, we've been in the car for six hours, as much as I don't mind your aroma, it's probably for the best we don't let my friends smell it, Claire isn't the only cougar," his Mom replied.

"Okay then," normally he'd get changed in own room and walk down the landing to and from the shower. But that was when his Mom might see him for two seconds with a towel wrapped round his midriff, it was different when he'd come out and into the room she was in. He'd have to get changed in the bathroom, which meant that his shower could only be lukewarm if he didn't want to leave his clothes sopping from the steam. He gave an inward sigh and reached into the wardrobe to take out a clean shirt.

"Don't worry about using all the hot water," his Mom said brightly.

It didn't take him long to shower, shave and do his teeth and hair, before getting back into his jeans and the new shirt. Stepping outside into the room, he said, "Shower's ready." His Mom looked at the clock and nodded, putting her cosmetic bag on the dresser next to the double bed, before vanishing into the bathroom.

Sitting on one of the couches Ryan flicked through the TV channel on the remote. He was vaguely interested to see there was an 'adult movie', which he'd have been tempted to watch if a) it wasn't pay per view and it'd come up on his Mom's credit card and b) she wasn't showering just a few feet away. Instead he settled on a repeat of vaguely funny sitcom; it wasn't what he'd have chosen for the weekend, but, he supposed, he'd soon be leaving for college and so spending time with his Mom now would make up for lost time later.

The shower went silent. Surprisingly the door opened only half a minute later, as Ryan had expected his Mom to follow his example and get changed in the room (though now he noted it, she hadn't taken in a change of clothes). Out came his Mom, clad only in towel wrapped round her upper body, down to her thighs, her long blonde hair dripping wet down her back. He blushed and tried not to look, though his Mom seemed impervious to his embarrassment, but instead took a seat nearby and plugged in the hairdryer, "You don't mind, do you?" she said and without waiting for an answer switched it on, drowning out the TV.

It was definitely unfair; with the show on he could have concentrated on it and ignored his Mom, without it, she was the only thing in the room. He tried to look at the paintings on the wall, but they were only bland pictures of bowls of fruit or sunsets and the view out the window was only of the parking lot and beyond that the highway. As much as he tried to avoid it his eyes kept coming back to his Mom. If she hadn't been his Mom he'd have said she was attractive, sexy even, especially as her towel kept slipping threatening to expose a bosom and she had to keep heaving it up as she first dried her hair and brushed it and then started on her make-up.

Eventually she put away her cosmetics and stood up, moving behind Ryan as she walked over to the closet. Ryan could hear the door opening and the scrape of hangars along the rail as she decided what she'd be wearing tonight, which would need to be different from what she was wearing tomorrow and the morning after the wedding. "What do you think of this dress?" she asked and Ryan had no choice but to turn around to look. She was still in her towel, but was holding a black dress over her body. It was one Ryan recognised, she often wore it when she was going out to a bar with girlfriends as a singleton. It wasn't hard to see why, as it was both short and low cut. "Think it'll do for tonight?"

"I don't know," he replied, not sounding too sure, "What do you think?"

She laughed, "You're supposed to be my boyfriend for the weekend, get off the fence and tell me."

"Um, yes," he said, not sounding any more certain than before.

It was enough however for his Mom, "I'm going for it," she replied, "Show everyone I've still got it, a hot body and a hot boyfriend." She grinned at her blushing son, "Turn away," she laughed, "I need to change."

He did so quickly. Behind him he heard the soft crump of the towel hitting the floor and then the swish of material on skin as his Mom slipped into the dress. "You can look again," she said and he automatically turned. "Ta-dah," she posed, her arms outstretched like she was modelling. The dress was even tighter and more revealing than he remembered; no wonder she wore it when she was out when single, and she was single now, even if she wouldn't show it tonight (at least he hoped not, if there was anything more embarrassing than pretending to be your Mom's lover, it was pretending to be her lover whilst she flirted with another guy). "What do you think? I come up pretty sexy don't I?"

"The sexiest," Ryan replied, it was what she wanted to hear and was also true, even if, as her son, it was theoretical to him.

She grinned, "You look pretty hunky yourself, I'll need to keep you close tonight if I don't want anyone to steal my toy boy away." He blushed, whether it was the compliment or his Mom's forwardness he couldn't tell -- perhaps it was a mixture of both. She adjusted the dress a little, pulling it down so that it covered more of her thighs whilst exposing more of her cleavage, "Anyway let me finish getting ready and we can go down to dinner."

It didn't take long for her to finish, brushing her hair some more and putting on some earrings and necklace, as well as a dark jade coloured bracelet.

Several of his Mom's friends were already at a table with their partners, more women than men he noticed and his Mom introduced him (again as her boyfriend) introducing her old cheerleader squad in a blizzard of names he mainly forgot and leaving it to each woman to introduce a guy she was with. He sat down next to his Mom and she very deliberately placed her hand on top of his as soon as he laid it on the table, "Order what you want honey," she drawled, "Wine as well."

That was a bonus, whilst they weren't teetotal, his Mom seldom drank when he was around and it was difficult to get into bars unless he had some decent ID and his last card had been confiscated by a bouncer as not been good enough. The drink soon arrived, beers as well and the conversation was flowing as well as the food. Ryan remained mainly quiet, only speaking if asked a question, but the other men were in the same position as he was and also remained in listening mode. Luckily the women had a lot to catch up on and whilst they'd seen each other individually over the years, it was the first time they'd all been together as an old squad since graduation. It seemed the intervening years had resulted in a number of marriages, several divorces (which helped explain the male/female imbalance) and one coming out as a lesbian (which also help explain the ratio) and multiple children of varying ages (from toddlers to teens). It was definitely strange, when they were talking about their kids, to hear his Mom talk about him as if he wasn't there and use a name hadn't be used since he was knee-high. It was even stranger to hear her talk about his ex-girlfriends (she turned out not to think most of them were good enough for him) and his football skills (which she exaggerated tenfold) as well as how she was going to miss him when he went to college (she squeezed his hand tighter as she said that, but no-one else but him noticed).

The food came and more wine and beer, coffee afterwards, though more than one person had it Irish, including his mother, which surprised Ryan as he hadn't thought she was a hard liquor drinker. He skipped it himself, he didn't want to get too drunk and accidentally say 'Mom' instead of Brandi. The conversation continued and they went to the bar, with various rounds being charged to their rooms. Luckily he found himself with his Mom on a couch, where she was able to slip an arm round his shoulders without getting too close, as some of the others had ended up on smaller chairs and on each other's knees.

Gradually the others slipped away until all that were left were Ryan and his Mom, Claire and another woman, a hot Latino called Megan. The three women were definitely the wrong side of tipsy and whilst Brandi was pushing up against her son, so he was squashed against the rest and she had two thirds of the sofa, the other two were getting close and giggly... very close and very giggly. Ryan watched as they moved nearer and nearer each other, their hands slipping over each other and their thighs rubbing together. His Mom was leaning her head on his shoulder also watching, though she seemed to have seen it all before, "Go on," she said with a girlish laugh, "Dare you to make out with tongue."

"What do you think?" Megan said to her friend, running her tongue over her bright red lips.

"A dare's a dare," replied Claire.

Ryan watched, literally open mouthed, as the two women came together and began to kiss passionately -- as his Mom had dared their tongues darting forward and into each other's. He'd certainly heard cheerleaders could be wild -- though given the cheerleaders at his school were all desperate to get good grades and go to a high class college, he felt it might be an urban myth. But certainly these two were and from the way his Mom was urging them on, she certainly had a side which he had never seen.

"Mmnn, how was that?" giggled Megan, it was unclear whether she was talking to Claire or Brandy, as both seemed entranced.

"Let's try again," giggled Claire, "And this time you can grip my boobies."

"W..." said Ryan trying to formulate a word.

"You go girls," his Mom laughed, squeezing his leg as she pressed against and over him, "You've not lost your touch."

The two women separated again, looking at each other with obvious desire before Megan stood up, "I'm calling it a night Brandi, see you tomorrow Ryan, Claire you coming with me?"

The other woman stood up, turning to smile at Ryan and his Mom, "See you tomorrow lovebirds, don't stay up to late." She took Megan's proffered hand and followed her out the bar.

Brandi drained her drink as well and Ryan quickly saw his opportunity, "We should go to our room as well."

"Spoilsport," his Mom giggled, "but yeah that enough drinkies for tonight, we need to keep something for tomorrow."

She stood up and as soon as he followed her, slid her arm through his and laid her head upon his shoulders in a less than familial way. They walked across the lobby and whilst she may have drunk too much she was still steady on her feet and as she spoke her words were clear and unslurred, "Enjoy tonight? What did you think of my friends?"

"Yeah," he led her into the elevator, "They were fun." He punched in their floor, though as it was only a couple up they could have easily taken the stairs. "Very open."

His Mom giggled, "I know what you mean, you naughty boy, the lesbian floor show."

"Um, yeah, that kinda threw me," he admitted, blushing slightly -- talking about watching hot women making-out was not something you normally discussed with your mother, especially when they were her friends.

His Mom didn't seem to mind, however, "Cheerleaders are very friendly with each other" she said smiling. The door pinged open and she stepped out. "We all used to be very friendly when we were at school."

"Um, are you saying...?" he wasn't sure whether she even knew what she was she saying or whether she was just drunkenly burbling -- not that she seemed out of control drunk, just merrily tipsy.

She giggled some more and broke away from him to look conspiratorially down the corridor as if she was checking whether they were alone, "Are you asking if I've been pussy to pussy with another woman?" she giggled. He blushed and so she answered for him, "You are, you dirty boy," she smiled as she spoke, before slipping her arm back through his. "It's not the thing a Mom should tell her son," she added with obviously mock sincerity, before breaking apart in peals of laughter.

"Okay," Ryan said.

"However as you're my lover this weekend," she continued, "and it's the type of thing women can tell their younger boyfriends..."

"You don't have too..." he began.

But it was too late as she continued, "I have. In my senior year I fucked both Megan and Claire, and the bride, and Sally, the fake blonde who has put on weight, she used to be really slender and up for anything. One time me and Sally had a foursome with a couple of cheerleaders from another school, I've never done anything like that again. I did a few more women in college and a couple more since. You remember Mrs Baynes, the hot divorcee who lived down the street when you were ten? I had a short fling with her, she was adventurous, whew, she was something." She stopped by their door still giggling and ignoring the fact that Ryan was blushing a deep red as he fished for his key, "Nothing too serious though baby, I prefer cock."