An Older Man Experience

“Have you heard about Ross, Lorna and Ross’ wife at lunch?”

“No, Cindy, what happened?”

“I interrupted them having a threesome in Ross’ office.”

“Gee, too bad it wasn’t me. I would have loved to see that.” Young Natalie blushed as she spoke to her friend, the office receptionist. Nat was a mere twenty-two year old summer student, handed a job because her Dad owned the company which Ross the Boss ran. She had instantly bonded with Cindy, who was only a few years older, but was the permanent receptionist. Cindy also had entertained Nat with true stories of her boardroom romp with Ross and Elena, a reserved but excitable older office worker. Nat had refused to believe Cindy’s claims.

“I bet you would have loved to do more than watch,” Cindy replied.

Redness travelled down Nat’s throat, colouring her upper chest, plainly visible in the deep V of her T shirt. She spoke quickly, breathlessly trying to cover her excitement, but really just highlighting it.

“Well, you know how sexy I find Ross. I think it’s an older guy sort of thing. My own Dad is so powerful; any guy my own age seems very pale in comparison. Especially my boyfriend, Ryan. He’s incredibly good looking, has a cool car and his folks are as wealthy as my Dad, but, every time we make out, as I give him a hand job, I think to myself ‘is that all there is?’. Somehow, we never get past that point. Not only does he not have what I think of as a big cock, but he comes in about three seconds. And I figure if he’s not better at fucking than he is at fingering me, it’s just as well we never get past third base. I need to learn from someone experienced, so I can teach Ryan. Or find out if he’s a keeper.”

Cindy leaned in close to Nat, crowding her in the little store room. “You know I’m experienced.”

Nat felt her friend’s sweet breath warming her tiny titties. For a second she hoped Cindy would just end the flirtation and reach up to cup those breasts, rip them free of the supporting uplift bra, and make them her snack. Instead, Nat said, “if only you had a cock, dear Cindy, I’d fuck you right here right now.”

“Oh, sweetie, I have a nice rubber cock right here in my purse. And two or three others in my desk if you don’t fancy this one. I left my strap on at home, or I’d be able to fuck you for real right here right now.”

Cindy opened her purse with one hand as her other slid up Nat’s miniskirt, stroking her quivering thighs. Nat was almost unable to stand; her knees were shaking so much. Cindy’s fingers reached the warm center of Nat’s desire. On the verge of melting and succumbing to her first Sapphic experience, Nat recovered and said, “I need real meat, not rubber.”

Cindy chuckled, her palm now cupping her friend’s pubes. “If that’s how you feel, Ross is a great choice. He has great meat, and knows how to put it in motion. I’d ask to join in, but I think your first time needs to be straight up. We can always try a three-way later.”

“What? Are you kidding?”

“Not at all. There’s a fax on my desk for Ross. He’s in his office working. Lorna’s at lunch. Take it to him now; you’ll have lots of time before she gets back.”

Cindy abruptly ran her hands up under Nat’s shirt, deftly unsnapping her bra. As Nat, without conscious thought, cooperated by shrugging it off, Cindy reached down and hiked the straps of Nat’s thong above the waist of her skirt.

“Make sure you bend over and give him a really good view. He won’t be able to resist.”

Nat felt the resistance flow out of her as Cindy tweaked her nipples to full erection. “The final touch,” Cindy laughed. “He’ll never be able to take his eyes off these puppies. Even though his wife and I have big boobs, his favouring Lorna and Elena means that he like firm little titties. Yours put theirs to shame.”

Nat started to shrug, but found herself proudly thrusting her chest out. She was always embarrassed that she barely needed a bra. The boys at school, and even some of the mean girls, always teased her. Ryan basically ignored her boyish breasts. Cindy’s tender caresses and encouraging words suddenly warmed Nat to the reality of their potential as weapons of mass seduction. Or at least, the seduction of one older boss.

Cindy’s ‘final touch’ reference left Nat shocked when her chum quickly bent forward and briefly suckled each nipple. “Now you’re ready. Totally irresistible,” Cindy giggled, and then she slapped Nat on the butt and swept her out the door into the hallway. “Go get him, girlie.”

Nat grabbed the fax and, emboldened by Cindy’s support, floated to Ross’ office. The door was ajar, but Nat knocked anyway. Ross invited her in. She was unsure whether to close the door behind her or not. Ross must have sensed her unease, “Leave it open. We can’t have anyone thinking I’m up to anything with the Big Boss’ daughter.”

Nat blushed, but quickly recovered enough to shoot back. “Up to something? What sort of girl do you think I am? That’s sexual harassment just saying something like that. And I’ll have you know I’m still a virgin, so my reputation is very important to me.”

Remembering Cindy’s coaching, she leaned forward slowly, teasing Ross with a leisurely peep down her shirt. Despite what she had heard about Ross the Boss being randy, the rapid response as his penis grew rock hard still shocked her. She turned away a bit rapidly, trying to hide her embarrassment. She was excited that she could trigger that sort of reaction from a man old enough to be her father, indeed her Dad’s right hand man. Fortunately, Nat’s twirl drew Ross’ attention to the bands of thong displayed high on Nat’s slim hips. He admired how they met at the small of her back, just below a tattoo of a Chinese character.

“What is that symbol?” he asked, buying time to look at the way the lace strips met, merged and disappeared under Nat’s almost non-existent skirt.

“I was told it was ‘Friendship’. But I’ve always wondered if it really means ‘Foolish Drunken White Girl’ or something.”

“Foolish Drunken Tart?”

Nat turned back to meet Ross’glare. “I am not a slut, so quit acting like I am.”

It struck Nat that perhaps this was not how Cindy would have advised her to seduce a man. Time to regroup.

Ross meanwhile was more wary than ever about the risks he was running here. His chance encounter with Lorna had lead him on a series of adventures, but sometimes he worried about company policy, and the law. Was Nat about to be his undoing? The very word ‘undoing’ though just made him think of undoing her clothes – not that they looked like they had buttons. From where Ross sat, it looked like they would just easily slide off. Or he could leave them on her and slip his hands…. He shook his head, trying to clear those images out of his brain.

Nat looked at his swollen member and grinned again. “Is this a new plant?” she asked, turning towards the window and bending over to smell the flowers. Cindy may have meant for Nat to tease Ross with the top of her thong, but this manoeuvre treated Ross to a full on look up Nat’s mini skirt. In the reflective glass, designed so Ross could see out but no one could see in, Nat saw Ross instinctively cup his balls, his fingers brushing the length of his cock. She confirmed that Cindy was correct – Ross had quite enough meat to suit her. He certainly had Ryan beat.

She turned, grinning. “If you walk around the office sticking out like that, you might break something.”

Now it was Ross’ turn to blush. He recovered well and quickly. “By the looks of the points drilling through your shirt, I’m not the only one bursting out of the office dress code.”

“Maybe we should help each other out with our violations?”

“I would hate to have to punish you.”

“I think you should. I’ve been a naughty girl. Daddy used to spank me if I dressed like a slut.” Nat pouted. “He says I’m too old for spanking now. Is that what you think, Ross?”

She turned and flipped her miniskirt over her waist, steering her tiny panties almost to his nose.

“Never too old, especially with a tender rear like yours. I think it’s been neglected too long.”

“Do it.”

“What?”

“I’ve been naughty. Spank me.”

Ross reacted tentatively, rolling his hand gently around the bare curve of Nat’s bum. He was not really experienced in spanking games. Adding this hot young dream to the mix almost scared him off. Only thoughts of how Lorna, or his wife, Molly, would respect him more if he took charge drove him forward. He sharply smacked Nat’s right buttock hard enough to raise a red welt. She grunted and threw her hands against the desk as the sudden blow almost knocked her over.

“Again. Harder.”

Ross slapped the left side. This time, Nat was braced to receive the blow, but still arched her back in response.

“Look how hard that’s made my nipples. I’m afraid you’ll have to punish me harder than that.”

Ross reached forward. Left hand on her hip, he tore her thong away with his right. He stuffed the wet panties in Nat’s mouth. “There, now no one will hear you scream.”

Quickly he slashed his hand across her buttocks once, twice, thrice. Each blow drove a grunt through Nat’s gag. Tears stained her face, mascara ran down her cheeks. If she had entered Ross’ office with romantic notions of an ‘older man experience’, she was learning about a whole other sort of sex. This was raw and animalistic, but still ritualized by the discipline play aspects.

Ross pawed at Nat’s swollen sex, his hand getting drenched by her wetness. He roughly spread her labia with his fingers, drawing his hand along her cunt and down around the curve of her thighs. His baby finger tickled her anus as he brought his fingers to his lips. Natalie watched his reflection in the window as he methodically licked each ounce of ooze off his hand, even licking at the webbing between each finger.

“You taste sweet for a naughty girl. And you are very bad if you are so wet.”

Meanwhile, Ross ran his left hand up under Nat’s shirt and mauled her breast, pinching the nipple hard enough to make her jump back. Her rear bumped against his erect cock, which he had freed from his pants just in time.