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Lisa’s Pain and Pleasure

"A manager entices a member of staff to have sex in a hotel and is disciplined by a Police Officer"

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Competition Entry: Boobies

Lisa came out of her office and looked across the main area. She saw Petra at her desk and smiled as she made her way over to her. Although Lisa was the Department Manager and Petra an Assistant Manager in the Accounts Team, they were a secret item. 

Lisa was fifty-one-years-old and had worked at the Company for nearly fifteen-years and had been the Manager for the last seven-years. She was wearing her usual white short-sleeved blouse and dark blue skirt which she always felt made her look the part of being a senior member of staff. Her dyed dark brown hair sat on her shoulders and made her look a good ten-years younger than her real age. It was summer, and she had bare legs.

Petra was twenty-nine-years-old and had been at the Company for just over three years. Whilst in a junior role she didn’t have all that much to do with Lisa other than at Departmental meetings. However, she had always admired Lisa and fancied her albeit from afar rather like a schoolgirl having a crush on her teacher. Today she wore a red short-sleeved long t-shirt with black leggings just as most of the women who dressed down for work. Her long dark light brown hair flowed down her back. 

More lately, now that Petra was an Assistant-Manager, she got to spend more time with Lisa. It was a month earlier that Lisa and Petra had to travel to one of the overseas offices together. Lisa had said it was a mistake but when they got to the hotel they were booked in to a double room and as Lisa opened the bedroom door they both saw there was a double bed.

That evening the two women were cautious and even when changing to go down to dinner they were careful not to display their bodies. Lisa didn’t really mind as she fancied Petra and was going to make a play for her, and, although over fifty she had the most gorgeous body which for her well-toned arms and legs was down to the gym. Her full breasts were a real wonder to behold and it was well known around the office that almost every man, and rather a high proportion of the women, ogled her as she walked by in her tight blouse.

To be fair, Petra’s breasts were also shapely and turned plenty of heads, but she had to admit hers were not as full and perfect as Lisa’s. 

The two ladies had had a tiring day in the overseas office going from meeting to meeting and were so glad to get back to the hotel. They had booked dinner there together and started to relax.

Petra was the first to mention the ‘B’ word. “Did you see how Karl gawked at you when you leaned across the desk to pick up those papers?” she asked grinning.

Lisa smiled wickedly, “I heard he was gay and thought I would find out. He might be, but you are right that he did look very closely at my cleavage.”

The women chatted happily, and all the while Petra was glancing at Lisa’s breasts. She didn’t want to be thought of like Karl but she was a lesbian so what was the worst that could happen she told herself with a smile?

Lisa did notice Petra’s glancing looks and didn’t mind at all. She was seen as a tough cookie in the office and she supposed that led everyone to assume she was straight and there were plenty of comments made saying how sympathetic they were towards any boyfriend of hers and how they reckoned he would be trod on all the time by the domineering Lisa.

In fact, they were wrong as Lisa was also a lesbian and it was only after meeting with Petra several times she thought she sensed that Petra might be the same. So, when it was time to go abroad Lisa opted to take Petra using the reason that she thought she would be getting promoted again pretty soon and it would be good experience for her. In fact, she fancied her.

So, Lisa took Petra along hoping she was right and that she was also a lesbian and, so she arranged the bedroom so-called mix up and the double bed.

After dinner, the women did go to the bar and added a couple of glasses of wine to the bottle they had split in the restaurant. Lisa focussed on making Petra relaxed and certainly succeeded and so after their drinks in the bar they decided it was time to go to bed and made their way upstairs.

Petra was quiet in the lift remembering she and Lisa were going to share a bed. 

Lisa was the more relaxed of the two but well aware of Petra’s more reserved manner but retained her a desire to encourage Petra to cuddle up and hopefully rather than that more when in bed.

Once back in the bedroom Petra was told to use the bathroom first. She removed her makeup and showered and got in to her nightdress which being summer was a very slinky thing. Of course, she didn’t know that she would be sharing a bedroom when she packed.

Lisa then got ready for bed. She came out of the bathroom wrapped in a towel and looking embarrassed said, “Whoops, I left my nightdress on the bed.”

Petra looked up from her kindle smiled at Lisa as she walked around the bed and she was still looking at her as she inadvertently let the towel drop to the floor as she bent to pick up her nightdress. 

As Lisa had hoped though, Petra was wide-eyed as she looked at her full breasts swaying just a few feet from her face. “Sorry,” Lisa said although she had dropped the towel on purpose.

“No problem,” Petra replied and in fact her feelings of arousal were reawakened when she saw those gorgeous boobies which were so kissable and suckable.

Lisa smiled at Petra as she slipped her shorty nightie over her head and pulling back the sheet lay down and picked up her phone to supposedly check emails and the like. She didn’t look sideways but could tell that Petra was stealing glances at her as she had deliberately left most of her breasts on show.

Petra was licking and biting her lips as she glanced sideways at Lisa’s cleavage and could feel herself getting damper and damper.

Lisa waited for a few minutes and deliberately leaned across to show Petra something on her screen. “What do you think of this swimsuit?” Lisa asked.

Petra looked at the screen but could not miss that Lisa’s nightie had got tangled up and now both of her breasts were fully on show and just inches from her face and, so she didn’t even look at the screen as her eyes were glued to Lisa’s breasts.

Lisa knew she was right and that Petra was a lesbian or bi at worst, so she just smiled at Petra.

Petra still couldn’t take her eyes off Lisa’s breasts and saw her nipples were taut, just as her own were. It took several moments before she realised that Lisa was smiling at her clearly seeing she only had eyes for her boobies.

Lisa beamed and said mischievously, “You can kiss mine if I can kiss yours.”

Petra gasped at the direct approach but as she fancied Lisa so much she nodded her head and manoeuvring slipped her nightie over her head. 

Lisa quickly pulled her nightie over her head and edged across the bed, so their bodies were touching.

Most times Petra would have got the admiring looks at the size and perfect beauty of her own boobies but not today although Lisa did say, “Nice,” as she leaned down and encircling a nipple with her lips sucked and kissed as she put a hand on Petra’s thigh. 

Petra caught her breath at how good it felt and not waiting to be asked leaned across and gently squeezed one of Lisa’s nipples before taking it between her own lips.

Neither woman held back. They kept the light on, so they could see the others body as they kissed and cuddled and licked and squeezed each other’s breasts as well as the others face, neck, tummy, inner thighs and of course her pussy. They revelled in edging their tongues inside the others pussy lips and as their groans increased so they each had their first ecstatic orgasm of the night.

It only took a few moments of gentle caressing and kissing the others inner thighs for their desires to return and both took erotic pleasure in sucking and licking the others taut again nipples. The women delighted in each other’s bodies and especially the others’ breasts and nipples. Even Lisa had to admit that Petra’s were probably the loveliest nipples she had played with for some time. 

By the morning both women were so at ease with each other that they happily walked around the room naked and kissed as they passed by each other making a point of fingering the others’ breasts and pussy.

All was well until there was a knock on the door. Lisa looked through the eyeglass and saw it was a woman standing there. She didn’t look like a member of staff and she eased the door open carefully so the woman could not see that she and Petra were naked still. Lisa asked formally. “Can I help you?”

The woman gave a hard smile and replied, “I have been next door all night and couldn’t get to sleep because of your antics.”

Lisa was taken aback by the complaint but before she could reply the woman pushed the door open and making Lisa back away stepped inside and closed the door.

“What are you doing?” Lisa demanded and then ordered, “Get out immediately.”

It was Petra who noticed the bag she was holding, or rather it looked more like a sports bag.

The woman didn’t seem overly flustered as she stood her ground and looking at both Lisa and Petra said in a rather friendlier tone, “Well I can see why you got on so well. You both have the most wonderful breasts. In fact, I noticed you first because of your full breasts and was jealous of them. I sat at the table next to you at dinner and thought how delectable you both were and then when I heard you together all night I knew I was right. It was just bad luck for me that I kept hearing you having such a good time together and I got very jealous.”

The almost affable demeanour of the woman calmed Lisa and Petra down. Their calm changed though when the woman took out a badge and showed it to them saying in a more officious tone, “My name is Katrina and I am the local Police Inspector. I think that you need to be taught that keeping occupiers of adjoining rooms awake is not nice and should be dealt with.”

Lisa swallowed hard and asked, “What do you mean by dealt with?”

The woman replied flatly, “Punished so you won’t do it again.”

“You are not serious?” Petra asked in a surprised tone.

Lisa said in her manager’s tone, “I don’t care if she is serious, but we are not going to take any more of this nonsense.”

Katrina smiled before her look changed to a glare as she stated confidently, “You do realise that I can have you taken to the Police cells?”

Petra was now worried as she said to Lisa, “I bet she can, you know.”

Lisa had also heard stories about how the Police here had powers that didn’t exist at home, so she asked more contritely, “What do you want to do?”

Katrina smirked wickedly and said, “That is better. Well it is simple. I love playing with lady’s breasts both directly and indirectly.”

Petra asked in a more inquisitive tone, “I don’t understand.”

Lisa said, “I think I do, Petra. I think she gets off with squeezing nipples really hard and then spanking the woman and watching her breasts sway as the pain intensifies.” She looked at Katrina with a, ‘Am I right?” look.

Katrina smiled as she replied, “Yes that is exactly right,” as she picked up the sports bag and put it on the bed and unzipped it. She lifted out a flogger and a cane and threw them on to the bed.

Petra looked in horror at the implements and said a very worried, “Oh my goodness.”

Katrina shrugged her shoulders but didn’t back down. 

Lisa said almost reluctantly, “I have experienced some things like she says. It might be okay if not too hard?”

Katrina replied looking at Lisa. “Oh, it will be very hard, but I think you know that. Also, I think that you should be the one to suffer the punishment as you are the boss lady and from what I could see at dinner most likely forced this young lady to have sex with you.”

Lisa didn’t rise immediately to the suggestion she had coerced Petra into sex as that was right, although by the end of dinner she reckoned they both wanted to. However, Lisa didn’t mind being the one to take the punishment as she was in to submission in rather a big way although no one at the office knew that. “Okay,” Lisa replied with a tone suggesting bravado which was put on for Katrina’s sake.

Katrina said with a superior tone, “It saves time that you are naked already.”

The comment reminded Petra she was naked and covered her breasts and pussy with her hands. She noticed the smile on Katrina’s face as she did so.

Katrina smiled with satisfaction and looking directly at Lisa ordered, “Lie on the bed on your back with your hands grabbing the metal rail of the headboard so your breasts are ready to be flogged.” 

Lisa gasped as she had never had her breasts flogged before. However, she had heard that it could be sensuous and thought that if it was anything like having her bottom spanked or caned, which were things she had experienced many many times, then it might be rather erotic. So, Lisa lay down on the bed grabbing the rail of the headrest, so her arms were well above her head and knew her nipples were already taut in anticipation.

Petra and Katrina both watched as Lisa got herself in to position and both saw how Lisa’s oh so beautiful boobies were not just ready but that her taut nipples told them both she was thinking sexual thoughts.

Katrina got a gag from the bag and smiled wickedly as she placed it around Lisa’s head and across her mouth said in an officious tone, “We don’t want to make more noise than we have to.” 

Once happy the gag was secure Katrina picked up the flogger and looking at Petra said sternly, “I will show you what to do and then you will flog your boss lady.

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Just make sure it is as hard as I do or else you will be next to lie on the bed.”

Petra really didn’t want to hurt Lisa but equally didn’t want to suffer her own flogging. She watched carefully as Katrina took up her position and letting the dozen or leather fronds of the flogger rest on Lisa’s boobies stroked her breasts a few times.

Lisa was tense as she knew the flogging would hurt but as always found the sweeping movement sensual. It was usually a sweeping movement on her bare bottom cheeks with a hand hairbrush or cane, but she soon saw that this gave similar erotic feelings. It didn’t last though as she saw Katrina hold the ends of the fronds in one hand and the handle in the other and pull the whole flogger straight before swinging it above her head and with a sweeping movement bring the flogger down across her breasts. As expected it hurt although she was pretty sure the lashes would get even harder.

Katrina was obviously well experienced in using the flogger as she didn’t pause and followed the flogger through swinging it down from the other shoulder, so it landed again criss-crossing, and then repeated the motion time and again making sure each lash was harder than the previous one. 

As the lashes continued and the pain in her boobies intensified Lisa squirmed arched her back and gasped just as she did when being spanked or caned. 

Katrina landed the flogger a dozen times before stopping and looking sternly at Petra ordered, “Your turn.”

Petra took hold of the flogger and twirled it around in the air just to check the method and then stood looking down at Lisa’s breasts which were already tinged red. She loved the sight of them and so wanted to kiss them again but knew she had to flog them instead. She glanced at Lisa’s face to see how she was feeling.

Lisa looked up at Petra and knew that she was hesitating and didn’t want to flog her and so to make her feel better she nodded her head and grunted, unable to actually speak because of the gag.

Petra saw the nod and the approval in Lisa’s eyes and steeling herself held the ends of the fronds in one hand and the handle in the other pulling the whole flogger straight just as Katrina had done and then in a downward motion lashed Lisa’s unprotected breasts. 

Lisa grunted and gasped as her breasts were flogged time and again by Petra and every bit as hard as Katrina flogged her. Once again, she arched her back and wriggled trying in vain to avoid the constant lashes as tears filled her eyes. The stinging pain continued to intensify, and she certainly didn’t feel aroused but then she didn’t get aroused when spanked or caned and so wasn’t surprised. It would be her feelings a few minutes after the flogging was over that she was looking forward to. In the meantime, though, her boobies were hurting like never before.

Petra kept the lashes coming with swing after swing criss-crossing Lisa’s breasts which were now much redder than when she had started. She saw the pain of each lash etched across Lisa’s face and tears in her eyes so knew the lashes were stinging her and asked whilst continuing to land lashes asked Katrina in a pleading tone, “Enough yet?”

Katrina made Petra six more lashes before replying, “Okay, enough.”

Petra sighed with relief as she stopped swinging the flogger and put it down on the bed hoping the ordeal was over.

Katrina picked up the flogger and put it back in her bag but then picked up the cane and swished it. She glared at Lisa who was still grabbing hold of the rail above her head and ordered, “Stand up boss lady. You have the cane coming as well.”

Petra put her hand over her mouth and gasped as Lisa let go of the rail and swung her legs off the bed and stood up.

Katrina looked at Petra and ordered, “Sit on the bed.”

Petra didn’t know why but did as she was told.

Katrina looked at Lisa and ordered, “Bend over with one hand on either side of her thighs so your boobies swing in front of her face.”

Lisa reckoned she knew what would happen as she did as she was told and loved how her breasts swayed against Petra’s face. However, she knew that it wasn’t the end of the pain for her breasts.

Katrina ordered Petra, “Take each nipple between your thumb and finger and squeeze hard. When I cane the boss lady, you make sure she doesn’t stand up. Okay?”

Petra took Lisa’s nipples between her thumbs and fingers and squeezed. Once again, she loved the feel of Lisa’s nipples but would have preferred to be sucking and kissing them.

Katrina took up her position behind Lisa and rubbed the cane backwards and forwards across her bare bottom cheeks.

Lisa had been caned before quite often receiving as many as three dozen strokes in one go, but never with her nipples clasped as they were now. She had seen it done to another woman at a S&M party who said afterwards that it was especially painful at the time but that after a few minutes of the caning ending became so aroused when her breasts were stinging so erotically.

Katrina said in a threatening tone, “Hold those nipples tight. If you let, go you get caned afterwards.”

Petra heard the warning and reckoned Lisa was on her side again as she squeezed her nipples hard and could see the pain in her eyes. Next moment the cane landed on Lisa’s bottom and Petra could feel how Lisa was pulling upwards and squeezed her nipples even harder as she saw her head fly upwards and she grunted through the gag.

Lisa found the stroke very painful and knew she would throw her head back and that that could make it difficult for Petra to hold on to her nipples. However, she did control her movement by forcing herself to keep her head as still as possible and it worked as Petra kept hold of her nipples as her head dropped back in to place.

Petra saw the cane come down again and heard the thwack as it hit Lisa’s bottom. She squeezed Lisa’s nipples just as she had before and kept hold of them again as Lisa grunted so closely to her face, and Petra reckoned that she knew the pain Lisa would be feeling both across her bottom and her nipples.

Lisa held her head in place again with the third stroke and was now coping better with the pain. She grunted again but focussed on staying in position which she again succeeded in doing.

Petra was so upset with the pain that Lisa was suffering even as the fourth stroke landed. She so wanted to hold Lisa in her arms and help her recover and promised she would do, so long as the awful Katrina let her of course.

Lisa struggled with the fourth stroke and as it bit in to her bottom she hit the bed with her palm and stamped one foot to try to quell the mounting pain in her bottom and her boobies. It didn’t help much as she forced herself to stay bent over.

The fifth stroke must have been harder as Petra struggled more to keep hold of Lisa’s nipples, but she did although Lisa’s breasts stretched far more than with the previous strokes. Petra was thankful Lisa had such large breasts which at least allowed so much more movement than if Lisa had had more pert breasts or was flat-chested. She wasn’t though and although Petra wanted to laugh at the thought she didn’t have time to as the sixth stroke landed, and Lisa’s breasts stretched even more than last time as Petra strained but just managed to hold on to both nipples.

Petra reprimanded herself at her thought about flat-chested women although she knew that she definitely didn’t ever think that bigger were better. She remembered her very close friend who was flat-chested and she had spent so many happy times sucking and licking her taut nipples and giving her friend finger and tongue sex and all those orgasms, and was given her own orgasms by her in return. She knew it was the person rather than the size of her breasts that made the woman.

Katrina decided that six strokes were enough and flexing the cane between her hands enjoyed seeing Petra still holding Lisa’s nipples. After another few moments Katrina said, “You can let go. The boss lady’s punishment is over.”

Petra was so relieved as she let go of Lisa’s breasts. 

Lisa eased herself up and undid the gag and threw it on to the bed and then her hands rushed to her bottom and she rubbed furiously. Her breasts swayed up and down and side to side much to the enjoyment of Katrina, and even Petra was in awe now the punishment was over.

Katrina watched for a few more moments and then put the cane back in to her bag. She zipped the bag closed, picked it up, and went to the bedroom door. Turning, she said to both Lisa and Petra in a dismissive tone, “Just remember not to make so much noise next time you stay at a hotel.” She walked to the door and turning again added, “Nice boobies, both of you,” and with that she opened the door, walked out, and closed the door behind her.

Petra held out her arms and said, “Poor you,” as she threw her arms around Lisa’s neck and pulled her closely in to her, both only just remembering they were still naked.

Lisa let out a relieved sob as she put her arms around Petra’s waist before remembering her stinging bottom and let go of Petra’s waist and clasped her own bottom cheeks and rubbed them again.

Petra kept hold of Lisa’s neck and was so conscious of their breasts pressing against each-others as she kissed Lisa’s neck and lips.

Lisa kissed Petra passionately realising that her stinging breasts matched the stinging of her bottom she loved so much to experience after a caning or a spanking

Petra returned the passion thinking how she had enjoyed flogging Lisa’s so beautiful breasts and wondered what it would be like to cane her as Katrina had done.

Lisa edged towards the bed and moments later they were lying together caressing kissing licking and sucking the others taut nipples tummy’s inner thighs and pussy’s. Their tongues edged inside the others wet pussy’s and licked the others taut clit as their passion intensified. 

As Lisa expected it only took a few moments of Petra kissing and sucking her breasts in particular for her to have the most wonderful, orgasm. She groaned louder and louder as Petra’s lips intensified the stinging and as she came so she almost shrieked with the passion. 

Petra felt the warmth of Lisa’s nipples thinking that at least some of the warmth was caused by the flogging, and was happy that Lisa had cum hoping that it would allow Lisa to push the punishment to the back of her mind.

In the event as Lisa calmed down after her orgasm she smiled at Petra and said, “You did what you needed to do, and you did it well.” After a moment Lisa continued smiling, “I have an admission. I love to be spanked and caned and punished with all sorts of implements. I wanted you to come with me as I reckoned you were a lesbian like me and you have such an erotic ‘Do as I say,’ tone of voice I thought you would also happily discipline me. I was going to ask you just before Katrina came in to the bedroom.”

Petra smiled as she listened and although surprised had to admit that if Lisa was turned on by what happened then she would be more than happy to do it again at home. “I also have an admission. I have looked at your bottom lots of times and fantasised about spanking you. I have masturbated having those thoughts as well. Now, though, I can add the equally erotic flogging of your beautifully full and perfect boobies to my fantasy knowing that my fantasy will come true time and again.”

Petra then replaced her smile with a stern look and said, “So when we get home you will buy floggers, canes and wooden-backed hairbrushes. Oh, yes, and you will buy some nipple clamps and chains as I will fasten them to a chair and when I cane you your breasts will stretch just like today and so your breasts and bottom will both sting. Next time though you will also give me an orgasm. Understood?”

Lisa was elated with the tone of voice that Petra was using on her. “I do understand, Petra, and want to submit to your authority”

Petra leaned in and kissed Lisa. “I will control you when we are together although not at work where you will still be the boss lady,” she said mimicking Katrina, adding, “Even though you will know I am the boss lady of you.”

Lisa kissed Petra back and said, “That will be so perfect, Petra. I’ll be your toy to punish and no one in the office will know.”

Petra kissed Lisa again and still smiling said, “My toy who will have stinging boobies and bottom cheeks.”

So, as Lisa stood today by Petra’s desk no one else but the two of them knew that Lisa’s boobies were bright red and stinging after being flogged this morning and that Lisa’s bottom had twenty-four welts following her caning, nor that after the pain of the punishments Lisa and Petra had given each other orgasm after orgasm before coming to work. They both knew that their relationship started when Petra was made to flog Lisa’s boobies and hold her nipples tightly as Katrina caned her, but it gave both the courage to express their true feelings about submission and domination. 

Thank goodness for Lisa’s perfect full boobies, they both thought.

Published 
Written by SusanHarper
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