Car Trouble Ch. 02

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Emily and Katie get their second punishments for car damage.
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Part 2 of the 4 part series

Updated 11/15/2023
Created 03/18/2023
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Drover60
Drover60
146 Followers

Car Trouble 2

In the week after the sexy punishment escapades with Emily and Katie, every day seemed to last forever. Time dragged for me like I was a young child, counting the days, hours and minutes up to Christmas Day. I kept re-living the events of the evening over and over in my mind but when I mentioned anything about it, Emily was rather sheepish about the whole situation and changed the subject rapidly. It seemed that the events of the evening had overwhelmed her. I assumed that she had got carried away and had ended up doing things that she would not normally consent to. The atmosphere around the house was a little tense and all my sexual advances were shunned, so I satisfied myself with the two pairs of musky-scented white panties that I had earmarked for just such occasions!

I did remind Emily that the punishment scenario was all of her own making, as she was the one who had suggested it, and I was merely following her lead. After all, it was her who had got Katie involved in the proceedings. I would have been more than happy punishing my own wife, however Katie's sudden appearance was an unexpected bonus. She had also promised to receive her fair share of the spankings and cane in the next three weeks, dressed up as a naughty schoolgirl, to fulfil my some of my fetishes.

Katie had separated from her partner over a year ago and had gone through a few short-term relationships with some 'absolute bastards' (her words not mine), so she was understandably a little bit 'anti-men' at the present time. She had been doing more 'girly stuff' and going out more with my wife and her other girlfriends. As I have always secretly fancied her, I wanted to push some boundaries to see how far I could get whilst I had this unexpected chance.

When Friday eventually arrived, at about 6.00pm Emily disappeared to get ready and I waited, tense with excitement to see what would unfold. At 6.45pm the doorbell rang and Emily rushed downstairs to answer it. I could hear Katie's voice, so was relieved to know that she hadn't backed out of the agreement she made last week. After a few minutes there was a soft tap on the bedroom door so I asked the girls to enter.

Although they were wearing the same sexy schoolgirl uniforms as last week, I wanted to take my time to admire them. This was my dream situation and I wasn't going to let it pass without creating some lasting memories. Two hot women dressed as sexy schoolgirls wearing stockings and suspenders were standing in my bedroom, waiting for me to punish them! I had to pinch myself to make sure it wasn't a dream!

"Hello Katie, how did you enjoy last week's little session?" I asked.

"W...Well... it was very intense, but I fully deserved what I got for crashing your car.... I did kind of like it though. The spanking was, well...... quite yummy, but the cane really stung my bum."

"Well, that is the general idea of a punishment!" I replied.

".......afterwards my bum was really red and hot and the stripes took a couple of days to fade, but I'm still back here to support my friend Emily and accept what I deserve."

"Good girl!" I smiled.

"You have both made up for a quarter of the damage that you caused to my beloved TR6, so this evening the total will go up to 50%. So, who wants to be first for their spanking?"

Emily raised her finger. "Me, I'll go first and get it over with."

"Very good, but first I would like you to see you both stand together and slowly lift up your skirts so I can see your naughty schoolgirl panties."

The girls looked at each other, puzzled that weren't going to be spanked straight away but reached down for the hem of their pleated navy- blue school skirts. Together they slowly lifted their skirts up until their stocking tops and black suspender clasps were just exposed.

"Stop," I ordered. "Now I want you to both turn around."

They obliged so I took my time and studied their long shapely legs covered in black silky stockings. Katie's had black seams, which I loved. It was a sexy image which I needed to capture, so, with their backs turned I sneakily got out my digital camera and took a few snaps of the naughty schoolgirls for my "wank bank."

"Ok now lift your skirts higher, up to your panties."

They carried on until I could see two pairs of tight white panties covering two sexy bums. I took a few more shots.

"That's it, keep your skirts nice and high girls!" I commanded as I approached them and ran my hand over their bums. I could feel Katie push and grind her into my hand while Emily remained passive but compliant. She did not appear to be as receptive to my advances as she was last week. I thought to myself that I would soon help her to change her attitude!

I hooked my fingers in the waistband Katie's white panties and drew them down to just below her bum, but above her lovely black stocking tops. I did the same to Emily. I couldn't resist giving each bum a soft caress as I did so.

"OK now spread your legs wider and use your fingers so I can see some pink!" I ordered.

The girls shuffled their legs as wide apart as they could with their panties around their thighs.

"Now bend over, I want to see more of your lovely pink pussies!" I repeated.

Katie was the first to reach a hand down and give herself a little rub, forcing her swollen pussy lips to part. Her other hand was needed to keep her skirt raised. Emily was slower to react but eventually followed suit. When I could see two shaven pussies being held agape, I grabbed the camera, zoomed in and captured the scene. Short skirts, stockings, suspenders, red nail varnish and glistening pussies. Yum!

"While you are in this position, pull your bum cheeks apart. I want to see your tight little bum holes!" I ordered.

"You have got to be joking!" Emily protested in disgust.

"Damaging my car was no joke either!" I retorted. "Now flip your skirt up onto your back, bend over and show me both your holes!

After a small hesitation, fingers left pussies, skirts were flipped up and bum cheeks were parted for my pleasure. Once again, I took a few sneaky pictures of the girls fully exposing themselves to me, just keeping enough self-control to resist thrusting my hot wet tongue into any one of the four lovely holes!

For the two weeks I knew had the upper hand and decided that I would push my luck as far as I could take it, as I may never have this opportunity again. I quietly got out a bottle of lube and two stainless steel butt plugs with jewelled ends that I had bought in preparation for the evening's events. I knew the Emily would strongly resist, as she has always refused me any access to her bum, so anal sex was never on the cards!

I coated the smooth stainless steel on the pink jewelled plug with plenty of lube and then squirted a large blob on my fingers. I thought it would be better to start with Katie, so I gently pushed two of my well-lubed fingers into Katies pussy. She gasped in pleasure and there was no resistance, and they slipped straight into her hot sex. I flexed my fingers inside her and then used the flat of my thumb to tease around her bum hole, pressing and probing gently. When she had got used to the sensation, I withdrew my fingers from her pussy, squeezed more lube straight onto her anus and used my index finger to wiggle its way past her sphincter muscles. Once it was in there, it left me free to introduce the silver plug.

When I placed the tip of the plug on her puckered bum hole she froze momentarily, but as I slowly pushed it in she relaxed and pressed back, eager to feel it inside her.

"Oh my God. Oh my God," she gasped.

I gently rotated the plug as I pushed until it went fully in leaving only the pink jewel base, glinting in the light.

"Oh, I feel so full. That feels nice," She gasped.

All the time I had been plugging Katie's arse, Emily had no idea what was happening behind her so was not expecting what was coming. I assume that she thought I was playing with Katie's pretty pussy. I decided that there was no point in being subtle, so I lubed up the other butt plug and went straight for my target before she could protest too much. I squeezed a large blob of cold lube straight into her tight virgin bum-hole, so she would know what was coming.

"Fuck! No way!" Emily exclaimed as she tried to stand up indignantly.

I put my hand onto her back and held her firmly in place. I put the butt plug in front of her to show her that it was not all that big.

"Katie has taken hers without any fuss. Now be a good little schoolgirl and stay bent over. Remember, this is all part of your punishment so relax, I'm just going to loosen your arse up a little."

Reluctantly Emily bent back over and opened her bum cheeks as wide as she could to try and make it as easy as possible for me to penetrate her forbidden hole. I gently massaged around her puckered anus, slipping the end of my index finger into her up to the first knuckle. Her sphincter immediately tightened around it. I left it in place for a few seconds while she got used to it then pushed and probed a little deeper. I gently rotated my finger to make sure the lube was well distributed.

"Oh fuck, that feels so good," she moaned.

"Your sexy little ass is so fucking tight," I cooed.

"Oh baby, it feels so good. I can't believe I never let you do this before. It feels like I'm on fire."

I rubbed the tip of the butt plug gently up and down her pussy, spreading the wetness to her arsehole. When I was sure she was properly lubed with her own juice, I removed my finger and started to slide the end of plug inside her tight little hole. She moaned as she felt herself open up.

"Try to relax, it will be easier," I said soothingly.

She tried to concentrate on relaxing her arsehole but she cried out in pain. I stopped pushing the and let her get used to the feel of the little bit that was in. I reached down and started making slow circles against her clit with my fingers. I wanted this to be a good experience for her, so I tried to make her concentrate on the pleasant feelings on her clit rather than the short-term discomfort in her arsehole. My ulterior motive was to make anal play something I could experiment with in the future and hopefully one day fuck her arse. Happy days!

After a few moments she started to relax so I started gently pushing the plug inside her again. When it got to the thickest part of the plug I rubbed her clit harder and faster, which set her off moaning even more.

"Good girl," I comforted her, to which she just moaned more.

Once she had taken the wide part, the rest of the plug slipped in really easily and my cock throbbed at the sight of my wife's plugged arse which I never thought I would see! I continued rubbing her clit as her breathing quickened.

"I think I want to cum," she managed to breathe.

"Not yet," I said and she moaned, clearly needing the release.

Using my spare hand, I pulled on the butt plug, pulling it out slightly and then pushed it back in. I began to fuck her arse with the butt plug and she began to enjoy it.

"Please" she begged, "please may I cum?"

"Not yet," I again replied.

Her pussy was starting to drip by now.

"You are such a dirty little whore, letting me fuck your arse in front of your best friend like this," I teased. She moaned in desperation.

Barely coherent now, I could just make out what she was saying.

"Please, please, please let me cum!"

I decided that this scene needed to be captured on the camera. Two sexy girls bending over with jewelled butt plugs fully embedded in their tight little bum holes!

Once I had taken the pictures, I pulled their white panties back up. Katie moaned in frustration so I ran a finger down her bum crack and giving plug a little jiggle making her purr in satisfaction. I reached further under her legs and pressed harder, rubbing up and down her damp panties over her slit, causing her to emit a soft moan.

I asked them to turn back around to face me and could see a tell-tale wet patch at the bottom of Emily's pussy where she had leaked some juice. I thought that I had broken her resistance so decided to push my luck even further!

"So, girls, that was just the pre-curser to today's punishment proceedings. Last week you were spanked and caned, this week you will be spanked and cropped with your butt plugs in place to increase the sensations and to make you think about what did to my car. I will expect you to wear the butt plugs for the last two punishments."

I placed a large pillow in the centre of the bed asked Emily to lift her skirt and lay over it so that her bottom was raised nicely for her punishment. When she was in the correct position, I produced two sets of bondage handcuffs and cuffed each of her wrists to the wrought iron bed head. I also slipped a blindfold over her eyes so she was totally at my mercy.

There she was, my wife dressed in a school uniform, handcuffed and blindfolded with her pleated little schoolgirl skirt raised up. Her black suspender straps framed her tight white panties to perfection and her black stockings made her legs look great, even when she was laid down. I could see the outline of the butt plug through her panties, so gave it a bit a few sharp taps to try and get a reaction from Emily as Katie looked on with a smile on her face.

I took my time and started to caress and hand-spank my wife's bum. I made sure that I gave the butt plug a little wiggle after each smack. At this stage there was not much of a reaction from Emily so I upped the strength of the spanks. They were slow and deliberate, but harder. The hard slap, the caress and the butt plug wiggle were beginning to take effect and Emily started to try to tense her cheeks in anticipation of the smacks. She was also becoming more vocal.

"I think it is time for Emily's panties to come down so can you please do the honours, Katie, I nodded.

Katie looked happy to oblige and made a meal of inching Emily's white undies over her lovely bum while Emily lifted her body and I took more pictures. This looked great on camera!

Katie pulled her panties all the way down Emily's legs and over her black heeled shoes until they were off. I could see Katie look at the wet crotch.

"Would you like a taste?" I asked her as I took them out of her hands.

"Smells nice," she replied, but without answering my question.

I arranged the garment so the damp crotch was in may palm and the pressed it up to Katie's mouth. I could feel Katie's tongue licking the panties as I held them for a few seconds before withdrawing them. Katie looked disappointed.

With my wife waiting, I resumed her spanking, but now on her bare bum. Access to the butt plug was now unrestricted so I made sure that it got a good manipulation after each hard spank. Her bum was crimson and Emily began to alternate between panting and crying out for mercy. I allowed my fingers to tease her outer pussy lips, but did not penetrate any further (just yet). I loved teasing her. I love bringing her up to the verge of orgasm and then letting it subside, before repeating. It seems to make her eventual cum, more intense.

When I was happy that I had Emily held at boiling point I held up the trusty cane and silently offered it to Katie. She looked confused so I put in in her hands and gestured for her to stand by the bed. She then realised that I wanted her to actually cane Emily. She gave me a massive grin and nodded her head. She was relishing this opportunity, but Emily did not know.

"Okay Emily, now the spanking is over and it is time for six of the best with the cane," I said.

I got out the camera again and nodded to indicate that Katie should give her the first stroke. Katie did not hold back and lifted the cane before delivering a swish-crack stroke right across the centre of Emily's bum. Emily screamed out, but could not escape. I jumped in and gave her bum a rub, making the white impact line turn a bright red. Katie was keen to continue but I held my hand up to stop her for a few seconds. I could not resist taking advantage of the situation, so dropped my jeans and boxer shorts to release my throbbing erection. Katie licked her lips suggestively, but I signalled for her to stay where she was. I climbed onto the bed and positioned myself in a kneeling position in front of my wife's head and rubbed my cock against her lip-sticked mouth until it opened and received my hardness. I gently rocked backwards and forwards, effectively fucking her mouth as she lay in her restraints.

I nodded to Katie, who tapped Emily's bum with the cane to find her range, then let another cruel stroke find its target with another Swish, crack. Emily was not expecting this as she had my cock in her mouth and gave a gargled scream. I held her head so my cock was firmly held in her mouth. Katie continued with the cane as I took full advantage of Emily's mouth. Tears started to stream down her face, was it the pain or the humiliation of being caned by her best friend while she was forced to suck me off?

The count of six was reached and I luckily hadn't cum in my wife's mouth, which meant I was good to go again with Katie!

I released Emily from her shackles and looked at the criss-crossed reddened mess that was her arse. Katie did not have to be asked to jump on the bed, so the handcuffs were applied and her skirt lifted. I didn't bother with the blindfold as she knew the drill by now. The spanking was equally as hard as I gave Emily but once I removed her panties Emily snatched the cane out of my grasp.

"Fair's fair. I should cane Katie just as hard as she caned me!" Emily stated matter-of-factly.

I left my wife to her task and climbed on the bed once again to pleasure myself, but this time in Katie's wet, receptive mouth. Emily made sure that she got her revenge and laid down six scorchers on Katie's lovely bum while I thrust in and out of her mouth. Katie moaned with each hit, but didn't deviate from sucking my hard cock with all her concentration. Unfortunately, I still had not managed to shoot my load by the time Katie's punishment was finished so I reluctantly released her. I then asked the two girls to stand by the side of the bed and drop forwards until their torsos lay on it.

Standing between them I teased them by twisting and playing with their embedded butt plugs at the same time. I found that if I hooked my fingers under the jewelled base, I could pull them out just far enough so that they stayed in, but if removed my fingers they slipped straight back in again. I could butt-fuck two girls at the same time! The pleasurable sensations they were getting built up and I sensed that Emily was about to cum.

"Alright, now cum for me you dirty little fuck slut!" I commanded.

And with those words, her body shook violently as the orgasm took over her. I continued to fuck her arsehole and rub her clit until the orgasm subsided, and then slowed to a halt. I took my fingers away but left the plug inside her.

"Can I take the butt plug out now?" Emily asked.

"Yes, but Katie must do it," I replied.

"Okay, it's starting to get uncomfortable now," she replied.

"Then stay bent over the bed and Katie will pull it out........" I said.

"With her teeth!"

I pulled Katie over to stand behind Emily and asked her to kneel so her mouth was in line with Emily's reddened bum. I then pushed her head forwards so she could get the end of the butt plug in her mouth. Katie deliberately made a meal of the situation and kept flicking her tongue around the jewelled end and of course around my wife's arse.

Katie eventually pulled the widest section of the plug far enough out for the whole thing to slide out. I took the plug from Katie's mouth and while she was in position, I pushed her head forwards and back into Emily's arse. Katie then used her probing tongue to lap Emily's bum hole until I pulled her away and asked them to swap places.

Drover60
Drover60
146 Followers
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