Hots for the Boss

Lisa spend the early evening planning, her mind was all over the place. Part of her mind felt a little horny, but that was mixed with a little feeling of guilt, but overriding all that was a feeling that she wanted to take this all a lot further.

While watching TV after tea, she had persuaded Pete to take part in a little roleplay. He was the boss and she was the naughty secretary that couldn't get any job right. As she walked towards Pete sitting on the bed her mind was full of excitement, but also a thread of worry that this might turn out badly.

"I'm sorry, sir. I have never been good at taking dick," Lisa said, she had more amusement in her voice than she wanted.

"It's called taking dictation, Miss Wolfe," Pete said. "I think that you need some serious punishment."

"If you think that is best, sir," Lisa said, trying to keep the excitement out of her voice.

"I do," Pete seemed to be getting into it. "Remove all of your clothes, and stand there." He pointed to a spot just in front of him in the bedroom.

Lisa, as slowly and as seductively as she could, first removed her top and bra, and then her skirt and knickers. Although Pete was in front of her, she was imagining Al, as she turned her back on him and bent from the waist to remove her socks, giving him the best view it was possible to create of her pert and tight arse. Pete almost purred at the sight, and that excited her more.

She turned back and faced him, feeling the moisture between her legs grow, and her head down looking at the floor. Pete rose from the bed and walked around her, examining her body.

"Very nice, Miss Wolfe, you keep yourself in shape," Pete said. "You will need those tight muscles to withstand the punishment I have planned."

"Yes, Sir," Lisa replied.

After circling a couple more times, Pete sat on the edge of the bed, knees together. He took Lisa's hand and guided her until she was laying across his legs, bottom raised. Lisa's legs were outstretched and he pushed them in, creating more of a right angle at her bottom, and a bend at the knee. Considering they had never done anything like this before, he seemed to know what he was doing.

Pete didn't seem to mind where her hands were, and so her right slipped across and between her legs, she was rubbing her clit when the first slap landed on her arse, with a loud, "slap," and a sting. She yelped, as she dug her fingers into her clit.

Before they had started, they'd agreed, "Japan" was the safe word, and Pete paused like he expected her to say it, but she didn't. The next slap landed, and she yelped again; her bottom was stinging, and she was grinding her fingers into her clit, but she was imagining Al spanking her. As the next one landed, she said, "That's it, punish me. I have been so naughty," adding, 'Al' inside her head.

Pete's hand fell on her cheeks again and again. He had never spanked her like this; in the back of her head, she was wondering where he learnt it. But the main part of her mind was living out the fantasy of Al spanking her, punishing her pert bottom.

Lisa felt her clit sing back at her as she rubbed, tingling running through her pussy now. She was getting very excited. Just as the electrical energy of an orgasm started to fire, Pete landed a hard spank, and it tipped her over the edge. Muscle spasms shot through her body as she climaxed; not controlling it like in the office, she gasped and moaned.

Pete had stopped spanking as she orgasmed, and as her breathing started to calm, he said, "That was quick; I was hoping to use this." He held her large wooden hairbrush up.

Lisa still had her hand over her clit and dug her fingers back in, as she breathlessly said, "Do it."

The image of Al swinging that brush at her bottom filed her mind, although Pete seemed to pause. After a moment the brush smacked into her arse cheek, with a very satisfying 'whoop' sound.

Lisa cried out, "Jesus fucking Christ!" but she did not say the safe word.

Pete whispered, "You ok?"

"I've been very naughty, Sir. It is what I deserve," Lisa replied, as if he hadn't asked, and remaining in character.

The sting was intense now, but she craved the idea of Al landing that brush again, and Pete obliged and brought it down onto the other cheek, another deep wooden noise filled the room as Lisa yelped again. Her body was responding; another orgasm rising as her fingers worked magic and her mind transposed Pete for Al, punishing her little bottom. Pete was clearly into this; two more slaps landed and she let out a yelp with each that was definitely becoming more carnal in sound. Her bottom was on fire, and the pain was getting quite intense now, but she wanted more, wanted 'Al' to ensure she could not sit down. Under her body, where her arm was squashed between her and Pete's legs, she could feel his erection growing. As her arm moved, rubbing her clit, it banged into his cock more and more.

Another hard slap landed and Lisa orgasmed again. The yelp that the slap forced from her was mixed with the moans and panting of cumming. Pete paused and she lay across him, breathing heavily, caught between wanting him to spank more—she wanted Al to spank more—and wanting him to fuck her hard, rough, make her feel his displeasure.

Pete had clearly been weighing the options too, as he picked her up and half-placed, half-threw her onto the bed. She remained in the same position, her top half laying across the bed and her waist bent to hang down the side, her knees an inch off the floor and her lower leg spread apart and mainly on the carpet. Lisa looked around at Pete as he removed his boxers, his cock springing out. It was long, a good eight inches, but very slim; it was probably the thinnest cock that Lisa had ever seen. However, it always felt good when that full length went in; she enjoyed being fucked with it, even if she had never cum from penetration alone.

"I've been so bad, Sir. Make me regret it," Lisa almost purred.

Pete did not speak, but he grabbed her hips and positioned himself; his cock was pressed maybe a centimetre into her pussy lips, just enough for him to be certain he was lined up right. Lisa was excited with anticipation, waiting, and he made her wait, teasing her with tiny movements. Then, in one fluid motion, he thrust forward, and at the same time pulled back on her hips. At a pace, Pete's cock forced its way into her; she gasped as it passed the point that most dicks would run out of length, but Pete's kept going until his balls slapped her pussy lips and the top of his legs crashed into her red cheeks, making them sing to her with a warm sting again.

Lisa moaned as Pete pulled out all the way, then thrust back in hard, and fast. As he pounded quickly, Lisa started to rub her clit again, his cock squelching as he thrust. Lisa moaned as he went; her mind had Al, thrusting into her, making her regret being naughty. She imagined his belly bouncing off her arse.

"Harder," she moaned. "Pull my hair."

Pete said nothing, but moved his hands from her hips and grabbed two massive handfuls of her hair, and pulled back on them hard as he thrust in with a force Lisa had not experienced before. She half-moaned, half-yelped, but followed it up with, "Yes, that's it. Teach me a lesson."

Pete started to thrust into her so hard it hurt. Every movement, pull, thrust seemed to her to have anger in it and caused a small amount of pain. It was exactly what Lisa wanted, her mind thinking of Al, pounding her hard, telling her she was a 'naughty little slut.'

For a long moment, there was nothing in Lisa's head, only the pain of this fuck, and the image of Al dishing it out, making her feel repentant for naughty thoughts. She moaned, and grunted as she was pounded.

"Jesus, yes, that's it, make me pay," she heard herself say, but it was like in a dream. But she knew it wasn't, as Pete responded, taking her even harder, if that was possible.

Lisa said, "Yes, Al," and as the second word came out realised what she was saying and changed it so what was said was a very strange sounding version of "Yes, oh yeah." Pete's movements did not change; she got away with it. She started to cum again, and this was a deeper, more intense orgasm. She felt her muscles tense, and the electrical fizz spread from her clit. Her pussy tightened as best she could, on Pete's thin dick. She squeezed his cock, the raw emotion of it escaping her lips in a carnal howl.

Pete thrust into her the hardest yet; it was painful, as two strokes seemed to almost rip her in two. Then he stopped, his cock deep in her. Lisa felt the spasms of his cock, then that lovely moment when cum sprayed into her.

Panting and exhausted, they collapsed onto the bed next to each other. They lay there for a couple of minutes just recovering.

A wave of post-orgasm guilt washed over Lisa. She had not been thinking about Pete at all during that; it had all been Al. What was wrong with her? Before she could think anymore, Pete said, "Wow, that was amazing! Please can we do that again?"

Lisa could tell from his voice that he expected her to say no, it was a one-off, but she had loved every moment of it and, if anything, wanted to experiment with more spanking, and maybe even something a little more painful, so she replied, "I suppose we can," not wanting to seem too eager.

Pete got up and walked to the toilet, and as he peed, Lisa decided to bite the bullet of her guilt and asked, "Do you ever think about other women when you fuck me?"

She looked over at Pete and could tell the answer from his sheepish-looking face. "I have, on occasion," his voice unsure. "Not often, though." If possible, his face went even guiltier and he said, "I probably think about you being fucked by other men more often."

They looked at each other in silence for a moment, then Pete said, "Sorry, but why?"

It was Lisa's turn to look guilty as she said, "Don't be sorry. But I asked because I thought about another man for the first time ever, tonight." She paused, and then continued, "Well, actually, it was earlier today, first."

As Pete returned from having his pee, he looked at her, smiled, and said, "That doesn't bother me; you shouldn't worry about it." He paused, then added, "Providing you enjoyed that as much as I did?"

Lisa felt relief, and said, "Oh, god yes, I loved it. I want to investigate what else we can do like that."

Pete beamed, and then asked, "So who was it?" Lisa looked away. Pete had met everybody she worked with at the Christmas party last year. He had actually had a couple of drinks with Al, and the pair of them had been laughing hard. She sucked in a breath, and looked Pete in the eyes and said, "Al, from work," her face going red; she could feel it burning.

Instantly he said, "Don't be embarrassed. He is a nice guy." She smiled back at Pete, feeling a little of the heat disappear from her cheeks, before Pete continued to speak, clearly emboldened by the honesty.

"Some of the women I have thought about are way worse; I think there is something hot about it being somebody completely inappropriate." He paused, as if gathering some courage for the next thing, then said, "I would quite like to see Al spanking your bottom, think that would be great fun."

Lisa threw a pillow at him for that, but he batted it away, and said, "No, seriously, if you wanted to, I would love it." It was Pete's turn to go bright red; he clearly felt he had just over-shared.

Lisa took at moment to process, she knew that a lot of men fantasized about their girl with another man, but never in her wildest dreams would have thought that included Pete. But after a few seconds, decided to play along. "OK, tomorrow, I am going to flash him my knickers, see what happens."

She planned to add to that, but before she could, Pete blurted, "Cool. You got to tell me about every detail."

Lisa sat for a moment, then said, "OK, but as well as telling you that, I think we need an honest talk about our sexual fantasies tomorrow night."

"Deal," said Pete, looking far more pleased than Lisa thought he should.

Pete turned out the light, and they cuddled up together. Lisa drifted off to sleep, thoughts of Al in her head. Her first dream was of Al whipping her with a crop, and she was loving it. Pete watched her as she slept with a huge smile on her face, and her hand between her legs.