Jill’s Spanking


“Do you ever think about fucking me?”

Dam that was one question I never thought I would here her ask me. She’d been my best mates girl for over 5 years and suddenly out of the blue she asks me that.

Of course I had thought about fucking her quite a few times over the years but to hear her ask me that in the pub when her boyfriend, my mate was only 30 feet away from us caught me completely off guard.

“If I’m totally honest, of course I have, many times.” I said.

“Good cause I have thought of fucking you too, but I have another fantasy that I want to try out and I think you’re the one I want to try it with.”

“What’s that?”

“Remember not long after we all met and you slapped my ass in the pub for spilling Johns drink?”

I remember it well. We were all out together as we normally were on a Saturday night, three lads, three girls having a few drinks and listening to a band. Jill had watched Michael refresh Johns drink by tapping the top of his glass with his own a little later Jill tried to do it herself only when she did Johns glass broke and spilled the contents all over his pants. I had playfully slapped her ass, she turned and looking at me said “Call that a slap?” And raised her ass a little higher making it a nice target especially as her jeans were tight across it. “You asked for it!” I said as I swung my arm back and let fly. The sound was great at my hand made contact as was the yelp that came from her. I think most of the pub heard it. According to Michael my hand print was still on her ass a few hours later when he inspected it.

“Yes I remember, who wouldn’t.”

“Well I want you to spank me before you fuck me.”

“Hell Jill! How long you been thinking about this?”

“Since that night.”

“Wow. Now you want it to happen?”

“Its all I have been thinking about for the last few months. I really want to try it. The whole naughty school girl thing.”

“How the hell are we gonna get away with that?”

“You know he goes away with work next week he’ll be gone for the whole week and weekend too. We’ll have time to do it and for my bum to recover before he gets back.”

We had to stop our conversation there as Michael made his way back with the drinks. It was hard acting normal after what had just gone between us but we managed it. A little later Michael went to play darts leaving Jill and I alone again. I didn’t know if I should bring up the subject again but I needn’t have worried as soon as he was out of the way she brought up it up. “So you up for it?” she asked, “yeah I’m up for it. How do you want to play this?”

(I think at this point I better give you a little back ground I’m 40 and Jill is 23, Michael and John are 25 and the other girls are 22 and 23. Michael, John and myself had met when we had all worked at a local club Michael met Jill when she and her friend attended a private party in one of the clubs function rooms and from that day on we she and her friend became part of the group).

“Well you pick me up and we’ll go to yours and we’ll just do it.”

“you gonna dress up as a naughty school girl?”

“Yeah, I still have my old school uniform and I can still fit in it just about!”

“So you gonna do the white knickers, bra and socks too?”

“Yeah if you want me to.”

“Hell yes.”

My cock was getting uncomfortable straining Escort Bayan against my jeans, I couldn’t get up as it would have been obvious to everyone I had a hard on. I told Jill this she just giggled and took a quick look.

“So when do you want to do this?”

“Tuesday, he goes away on Monday and I want my bum to have the maximum time to recover before he gets back.”

“Take it you want me to pick you up as usual.”

“Yeah I will have a bag with my stuff in it, cant exactly walk out dressed as a school girl in front of my mum.”

“Ok what time?”

“Half six like we would if we were going out for tea.”

Our conversation was stopped there as Michael came back to the table and I went for some drinks. The night went on like most Saturday s from there on and just after 1am we all went our separate ways Jill giving me a wave and a wink as she left the pub. I couldn’t wait for Tuesday to come.

I spent the following day making sure everything would be alright for the fun on Tuesday, put aired clean bedding ready to put on in the afternoon. I deliberately left my bedroom curtains closed so not to arouse the neighbours. Closing them shortly after Jill had arrived would have got a few curtains twitching however they were used to seeing Jill at the house as we would park the car up after going out for a meal and then shortly after go to the pub for a drink or two till Michael picked her up and took her home.

Tuesday morning came and I decided that I would take the afternoon off from work and finish getting things ready. I still wasn’t sure that this was going to happen. We had exchanged a couple of txt messages on Monday and everything was set but I still wasn’t sure that she would go through with it. I txt her again about 4 to make sure that she was still up for it she sent me one back telling me her knickers were wet in anticipation of what was to come.

Everything was right the wine was chilling in the fridge along with the glasses the room was clean and tidy and aired, clean bedding made the room right for what was to come. I pulled up outside her house at 6.30 on the dot, I didn’t have to wait long she came out carrying a bag climbed into my car and off we went. The ride to my place was short but we passed the time just talking about the day like we always did. As I parked the car up she let herself into the house and went straight to the bedroom to change. I shouted up to her, “don’t get changed yet I’ve got some wine here and we need to chat about what were about to do.” She came back down and sat opposite me I poured us both a glass of wine and said, “How far do you want to go with this?”

“I told you I want you to spank me then fuck me!”

“I know but how far do you want me to go with the spanking? You want me just to get your bum red or to the point were your crying? Think about it for a minute, once you have decided you can go up stairs and get yourself ready, one more thing if at any time you want to stop just say horses ok? Everything will stop then if I’m spanking you I will stop and even if I’m fucking you I will stop ok?”

“Ok.” She said. She took a mouth full of wine and sat there thinking for a minute which seemed to me to be hours. “I want you to spank me till I cry then I want you to fuck me till you cum inside me.”

“Your sure about that?”


“You Bayan Escort want me to wear a condom?”

“No I want to feel you cum inside me.”

“Ok, take your wine with you and go get ready, shout me when your ready and we will begin.”

She went upstairs to my bedroom and I took another mouthful of wine, my cock was straining in my pants I knew if I were to be able to do this I would have to change into some looser pants. I shouted up to Jill to throw out my ¾ swim pants, I heard my door open then close and went and retrieved my pants and then to the bathroom to change into them. Once changed I shouted to her “are you ready?”

“Yes Sir” came the reply, I wasn’t expecting her to call me Sir but it fitted with the fact that she was now dressed in her old school uniform. I couldn’t wait to see her in it and walked to the bedroom, and opened the door. There she stood in her school uniform, white blouse, navy blue knee length skirt white knee socks and black shoes, every inch a school girl. My cock grew hard just looking at her, I couldn’t wait to see if she was wearing white cotton school girl knickers but there were things I had to do first. “ok my girl you’ve been very naughty, you disobeyed your teachers and haven’t done your homework! What have you to say to that?

“Sorry Sir!”

“Is that all you have to say?”

“Yes Sir, it wont happen again Sir!”

“That might be so, but you have to be punished for your actions today, you know what the punishment is don’t you Jill?”

“Yes Sir, a spanking Sir!”

“Yes but this wont be an ordinary spanking Jill your attitude has been so bad that your going to suffer the ultimate spanking, bare bottomed.”

“Yes Sir, sorry Sir.”

“Now get over her and across my knee!!”

Jill jumped at the tone of my voice but came across and placed herself over my knee, I moved her around a little to get myself comfortable and her bum in the right position. “Jill I want you to count every spank if you miss one I will start again, understand?

“Yes Sir”

“Good. To start with I will spank you 10 times on each cheek with your skirt still down. Don’t forget to count now.

I lined myself up with her right cheek and started to spank, “one, two, three” she said as I gently but firmly started to spank her. Having reached 10 I gave her a minute to readjust herself on my knee then lifted her skirt up her back revealing her white cotton knickers, my cock got even harder at the site of them. Keeping one hand on her back which also kept her skirt in place I told her that this time I was going to spank her 20 times and slightly harder. Again I lined my hand up with her right cheek and started to spank. “One, Two, Three, Four and so it went on when I had reached 15 she started to move around a bit on my knee and the occasional ouch came out, by the time I reached 20 her legs were coming up on each spank and the ouches were after each spank. When I finished I let her get a little rest on my knee, I opened her legs slightly and rubbed my hand over her panty covered bum I could feel the warmth radiating from it. I also ran my hand between her legs to find that her knickers were already wet. My cock was bursting to get out of my pants but I knew I had to make her cry before I could get it out of my pants and fuck her for all I was worth, I just hoped she didn’t say Escort “horses” before then.

Having let her rest for a few minutes I told her to stand up for a minute, she did as she was told and I reached up the side of her legs till I reached the elastic of her knickers and slowly pulled them down to her knees. I then positioned her back over my knee and lifted her skirt from her bum. The sight was amazing, her nice round firm bum was red all over from my earlier spankings. This time I didn’t tell her how many spanks I was going to give her we both knew she wanted to be made to cry so having positioned her again over my knee I again started to spank. The feeling of her flesh against my hand as it struck he bare bum for the first time sent a shock through me right to my cock, I would have to watch it or I would end up cumming in my pants and I didn’t want to waste any of it, I was saving that for her pussy and her bum later. About 20 spanks in she started to quietly cry, by thirty she was sobbing vocally. Her bum was red and you could see my hand prints on her cheeks. I stopped spanking her and held her for a moment before I started gently to rub her bum. Again I slipped my hand between her legs to find her sopping wet pussy, I drew my finger between her lips, when I touched her clit her bum cheeks tightened and relaxed she was still crying but as I played with her clit and pussy soft moans came from her lips. I slipped a couple of fingers into her pussy and let my thumb play with her clit. Her moans became a little lauder so I eased her of my knee and onto the bed with her legs dangling over the edge, I helped her out of her skirt, blouse, and bra but left her knickers in place around her knees. As my hand rubbed her bum my fingers again started to play with her clit, I got down on my knees behind her and drew my tongue across her lips, then between them finally I started to fuck her with my tongue, she was loving it, she got wetter every time I entered her with my tongue, she was ready, I undid the sting on my shorts and pulled them down, my cock was rock hard and ready, it was already leaking precum which I trailed across her bum, having teased her by rubbing it across her pussy lips a couple of times I slowly pushed it deep inside her. I fucked her slow and hard at first letting my balls bang against her clit as I felt her reaching her first orgasm I quickened my pace, she screamed as it hit her but I kept pumping in and out of her at a steady pace, I could feel her coming down from that one but I too now wanted to cum. Again I quickened my pace only this time I spanked her on each cheek on the out stroke, this made her cum again and harder as she reached the peak of her orgasm I exploded inside her after three squirts inside her I pulled out and emptied the rest of my cum over her bum. We were both tiered by now so I rubbed my cum into her red bum then left her there to recover while I ran her a cool bath, when it was ready I returned to the bedroom and gently picked her up and took her to the bath and lowered her in. I left her there to get cleaned up while I went back down to get us both a glass of wine. I gave her, her wine and sat on the toilet while she lay in the bath. “Was that what you wanted then Jill?” I asked.

“Yes and more, I have never orgasmed that hard ever before.”

“I’m glad you enjoyed the experience as much as I have. Maybe you’ll try that with Michael when he comes back.”

“No this is just between us.”

“Well I’m glad you enjoyed it. If there is anything else you’d like to try let me know.”

“Well there is one thing.”


“I want to spank …..”

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