Mentoring Britney

After Britney left the bar I took a little longer than usual shutting up. Not only did I have to sort out her shelf stocking and the like but I had to be a bit tidier with the books – the landlord was back on Saturday. Driving back home I reflected that my life was soon to become very boring again, no pub to run and no nubile young body to play with.

I wondered if I could manage a real relationship again, but came to the conclusion that I had absolutely no chance of finding anyone to approach what I had experienced over the last few weeks. I would just have to content myself writing about it, which had worked for ages.

I parked up at home and saw that her bedroom light was still on, not surprising she had only been back for a little less than an hour. I went and got some coffee and sat down and did a bit of surfing. I had hardy settled when I heard them coming down the stairs, again one of my favourite sounds – the click of high heels. I thought that was quicker than usual, but had no complaint with that.

They spent awhile in the hall saying goodbye, but I then heard a taxi sound his horn outside. Shortly after the beautiful Britney walked in, still wearing her denim mini dress with her heels, and looking very pleased. "Hello darling, I don't feel any different, do I look as though I have changed in any way?"

"Well you are looking very pleased with yourself, definitely a 'just fucked look' but that is not unusual of late." I guessed what she was getting at but said nothing.

"Yes, I should look as though I have just had a good fucking because that what he gave me, twice in fact. We did talk before about the difference between doing it for fun and charging for it. I still had a very satisfactory fuck the only difference is that I collected enough to pay my airfare to Canada. I don't feel any different knowing that I am not just a slut but a prostitute as well."

"That innocent young lady I met a few weeks ago has changed a lot; you say you are off to Canada first, what then?"

"I picked Toronto first because an old friend from school moved out there; I will look her up and then go on to the States. I want to do New York and California and you never know, I may even see if I can get a job in Nevada for a while." The last comment was accompanied with a caress of my crotch.

"It's a shame your guardian angel can't come with you, I am sure you will need one, real life and fantasy are very different things."

"I was talking to my Tom today, he is in India at the moment, and we agreed to meet in Japan in six months time. In those six months I may get all the fun I need and see if I can settle down with him."

"Of more immediate interest what are you going to do tonight, I hope you still do freebies?"

"Oh yes, I have plans for you tonight, I was going to stay the weekend with you but my flight leaves Friday night so we only have tonight and tomorrow. I had a lovely chat with my Dad today; he was very frank and wished me the best of luck. His one bit of advice was that I did not take the crop with me – he said it was not safe to let loose on most men but he thought I knew someone who knew how to use it." I gave her a cuddle and said, "I think you Dad sounds as though he might have been good at my role of mentor if you had got talking earlier."

She blushed a little and said "Dad has surprised me in the last couple of weeks; he seems to like to see me enjoying myself like I have been. I am sure that no one could have done the job as well has you have, so are you going to use the crop on me again?"

"Why do you want one of our last sessions to be me hurting you?"

"Because you used Dads crop so efficiently, if you don't I will have to pack it and find some brute to use it on me. If you give me a hard session with it now I will leave it in Dads garage."

"You are a nasty, but beautiful, blackmailer; I should punish you for that – but if you want it hard perhaps I will relieve my frustrations caused by you showing me so much pleasure and than running away. Come on up to your bedroom, I don't want blood on the kitchen floor." My attitude was designed to get her worried but all the silly girl did was grab my hand and pull me upstairs.

This lovely, naked, body was pulling me up the stairs – her superb ass and legs accentuated by her highest heels. She took me into the bedroom and I asked, "I want to know just what you expect me to do to that absolutely perfect young body of yours?"

She went and picked up her crop and used it to rub her own pussy and said, "My mentor neglected to get me to have any tattoos or piercings done to give me a permanent reminder of the best few weeks in my life. Do not give me any permanent markings with this but I am sure I can take a few welts that will last for a fair proportion of my world trip."

I just shook my head, "Silly girl your perfect body needs absolutely no additional decorations, your mentor can only suggest a piercing for your belly button. If you insist on a tattoo, just something discrete between your hip and pussy – but it is a little late for you to mention the idea. Now, can you please be more specific about what you want me to do to your lovely body."

Britney then came up and pushing her tits into my chest and wrapping a leg behind my bum sunk her teeth into my neck. After what was a painful bite she worked her mouth up and started sucking my ear, playing her tongue inside it. "Before I tell you what I would like do you promise that you will follow my instructions?"

"Even with you working on my will power like you are I will only promise to try and follow your instructions, I will however listen to your guardian angel when he pops into my head."

She then stood back and said "We are wasting time, in about half an hours time I want to be lying, snuggled up to you, only just conscious from the overdose of both pain and pleasure you have given my body. I want to wake up in the morning, just managing to stand up and look in the mirror, I then want to say 'I am a stupid bitch' seeing all the marks on my body."

She continued, placing a finger on my mouth, "First my boobs need marking, then go for my pussy and finally my ass – I will remember the code words but I think the only one I am likely to use is 'black'. No more arguments, just remember unconscious, and plenty of marks to show for your efforts."

I knew it was pointless arguing with her, "Right, you asked for it, I am not sure half an hour will be enough and you must promise that you will leave the crop with your Dad." She did thank me and promised to leave it. "Now turn around, and shut your eyes. I have got to fetch something from my room."

I returned and told her to put her arms behind her back and wrapped one of my leather belts around her wrists and pulled it tight. I took a second belt and did the same above her elbows, again pulling it painfully tight. Grabbing a handful of her hair, I turned her around and told her to open her eyes. "There, that has got your tits forced out nicely, now stand still what ever I do to you."

Her reaction was just to give me a smile and blow me a kiss. I then landed a nasty, harder than I had intended, strike on the outside of her right tit, and then a back handed strike on the outside of her other tit. She swayed away from each stoke and had a very pained look on her face as two red marks spread across her flesh. I said, "That got rid of your smile, I said stand still." She stood up straight again forcing her proud tits out; her eyes followed me around to the side as she took deep breaths.

For the next strike, I needed to stretch up on tiptoe, landed across the top of both her tits. It was a hard swing but I stopped just as it made contact, it left a mark on each of her lovely globes, and she yelled and lent forward. I quickly gave them a similar hit coming upwards onto the softer undersides, and said "Please listen, I said stand still." She again stood straight, her panting was now quite rapid, sweat was pouring from her brow, and her eyes were full of tears.

Britney's lovely nipples were both standing up looking as hard as I had ever seem them so my next targets were a strike on the tip of each breast, just missing the nipple. I then stood in front of her and used the crop to, gently, play with her pussy lips – it was very moist down there. I dropped the crop and knelt down and used tongue and lips to play with her clit and pussy, very quickly, she had an orgasm soaking my mouth with her juices.

I stood up and cuddled her saying, "That's more than enough on your lovely breasts, none of the foreigners will be able to enjoy them for ages as it is. Can we now cuddle up in bed and have some nice simple sex?"

She snuggled her head against my neck, her arms were still painfully bound behind her back, and said, "You can have your pleasure when you have finished the treatment you promised, you are doing fine so far. I would like to see how much more my boobs could take but you are right, I will probably need to display them soon."

I turned her around and released the belts, her upper arms had nasty blue/yellow bruises where the belt had dug in, – I had not noticed how tight I had bound her. She flexed her arms a few times and said "Please give my ass some serious treatment now, I will be specific, start with six at least as hard as the ones on my boobs and then six even harder. Do not pause until you have finished, I will then tell you how to continue."

I took one of her nipples between a finger and thumb and gave it a firm squeeze and twist, saying "You utter idiot, if you want a good job on your ass we had better go down to the kitchen table again, it is a lot easier to aim with you up higher."

She actually pulled me down on the bed and said, "Perhaps that could wait until the morning, your work on my nipple feels marvellous. You have not got out of beating my ass but for now a good fucking would be nice."

I positioned her hand between her legs and sucked one nipple into my mouth and used a hand on each breast to give them some serious pummelling. The crop had left a definite welt with each contact and they must have been sore but my squeezing was having a very noticeable effect. She arched her back and rubbed her clit frantically as I got rougher and rougher with her tits. I ended up gripping each nipple between thumb and finger and pinching as hard as I could while twisting them from side to side.

She had a shrieking orgasm, which I followed up by quickly sinking my cock into her pussy and pounded away as hard as my poor old body would allow. I was, unfortunately, finished all too soon but it was in time to give her yet another climax. I sank down beside her and we had a long cuddle. "You even made me hurt you with that one, lets go to sleep now and you can wake me up with a nice gentle blow job."

It was a marvellous feeling having her firm young body pushed into me as she slept. I did not appreciate it as much as I might have, I found it very difficult to get to sleep thinking that this was the very last time I would have the pleasure. I must of finally dozed off as I was woke up with two beautiful eyes looking up at me while her tongue lapped around the tip of my, very erect, cock. She said, "Good morning darling, just stay still and enjoy."

She then administered what was the best blowjob I had ever experienced; she kept up exquisite treatment taking me to the edge on numerous occasions. Each time I was close, she eased off and squeezed the base while I relaxed and then went at it again. I had to give in eventually and squirted into her mouth, she sucked as much out of me as she could until I had gone completely limp.

She then came up the bed, the lovely body rubbing against mine and gave me a long kiss and said, "Thank you so very much for all you have done for me, it really is such a shame you are too old for me, it just does not make sense me moving in with you."

"I know it makes complete sense you finding someone your own age, although make sure you get a fit one, he will have a major job keeping you satisfied." I did actually agree with the logic, as nice as it had been she deserved a proper life partner she was such a great girl.

She pulled me up and said, "Come on we will have a shower together and then I will have to go and lay the kitchen table." The silly girl had not forgotten the outstanding treatment with the crop. While we showered, I tried to convince her that it was silly but she again blackmailed me by saying she would have to take the crop around the world with her if I did not. The previous session had left an individual mark from each stroke; three in particular leaving raised welts, which were very tender when I pressed them.

We dried off and went down stairs; the only clothing between us was her nice high heels, tapping down my stairs for the last time. She quickly got the foam and sheet spread on the table and taking a cushion under her belly jumped onto the table and wiggled her lovely ass at me. I said "Sorry darling, not yet roll over so I can see those lovely boobs, fold your arms behind your head please."

When I took the crop and started gently rubbing each nibble in turn rather than the expected worried look she just smiled at me. "I won't bother with a blindfold, or a gag, but please shut your eyes, and keep them tight shut." I continued to play the tip of the crop across each nipple until they were both very erect. I walked over to one of the kitchen drawers and made plenty of noise playing with the cutlery telling her to keep her eyes shut. Finding what I wanted I went back over to her and she only flinched when I ran a cold blunt dining knife along one of her tits. The silly girl she was far too trusting, her nipples were still standing up which were my target. I took one of the pipe cleaners I had found and twisted one around the base of her left nipple, leaving the two ends available for later tightening. Repeating the same on the other side I told her to keep her eyes shut and gave a twist on the ends of the cleaner, which constricted the base leaving a raspberry like tip to the nibble. Tightening up the other side I told her to keep her eyes shut and picking up the crop I gave a couple of light taps on each bound nipple.

"Open your eyes now and you can roll over and I will start on your bum, assuming that you still want me too – I know silly question."

"You bet that was a silly question, the nipples feel good that was a nice idea. Now it's my turn to tell you what to do, six good hard strokes to begin, more instructions will follow." I did as I she told me, held the crop on the middle of one of her cheeks, and gave it a good hit ensuring that I only made contact and did not sink in. Five similar ones alternating between cheeks followed, they each left a visible red line, but I was sure they would not satisfy her.

"Umm, that was a pleasant massage; very relaxing now would you like to use the crop on my ass." I did not want to hurt the silly girl but I knew she would keep pestering until I did. I targeted the fold where her cheek met her leg and gave a, harder, whack followed by two more and then three on the other side. These all had her bum flesh shaking and left nasty red marks, her reaction was a sort of grunt with each contact. Her grunts got loader with each hit, when I paused; she yelled, "Yes, yellow, do it again."

I adjusted my position so I could strike in the same area but land on both cheeks simultaneously. After the first stroke, I waited while her cheeks stopped rippling and then hit again, repeating the treatment a total of six times. The marvellous, but idiotic, girl started an orgasm after the second hit and was still shaking when I finished. She shrieked "No. don't stop, black, black please." I was able to keep her on a high with slightly lighter and slower strokes, she was yelling all the way through with what sounded vaguely like a drawn out 'yes' but it was hard to be sure.

When I finished she just lay breathing deeply, her whole body was red, and in particular, the nasty welts I had left on her cheeks. When her breathing got back to normal, I gently turned her over to inspect her nipples. They had both turned a deep red, almost purple colour; it was definitely time I released them. To take her mind off them I picked up the crop and ran the tip along her pussy and clit while using my teeth and one hand to remove one of the pipe cleaners.

As the blood, rushed back in she leapt with the pain and yelled "Oh fuck." I took the nipple into my mouth and gently sucked it while tweaking the other, still bound, one. I was right thinking her body would appreciate the attention, yet another little climax. Swapping my attention to the other nipple I took off the cleaner getting less of a verbal reaction but after sucking it into my mouth she achieved yet another climax.

After regaining her breath, which took some time, she draped her arms around my shoulder and gave me a kiss saying, "That was unbelievable, you are nearly convincing me to stay, almost every time we try something you take me to even higher levels of pleasure. I do have one serious complaint, what is the point of agreeing code words before a session if you completely ignore them?"

I gave her a kiss on the neck while squeezing one of her purple nipples and said. "I did not notice any complaints at the time."

"That was the wrong answer Mister, I wasn't sure how coherent my request for you to go harder had been, you have now admitted to hearing it." She jumped off the table and told me to go and find a mirror while she had a drink of water. I went and removed the mirror from the wall in the hall and took it into the kitchen.

She got me to position it so she could see the damage I had done to her ass, the whole lower portion was already looking a purple/yellow colour with lots of nasty red welts standing out. She looked in the mirror and, gently, touched the abused area and said, "Look there are more white areas than bruised; I think you will now have to do as you were told and give me a harder session. I know you do not like the idea but it is my last chance, perhaps ever, and I would very much like you too, please."

"You are a complete and utter idiot, please be careful in the big bad world, I care greatly for you and wish you no harm at all. If you make these sorts of requests to a very large number of men, you will be lucky not to get permanently disabled, or even worse. You have given me the best month of my life so I will do as you ask, but I really do not like the idea." There was no point in me refusing, although I did think I had done far too much damage already. "Take this wooden spoon and bite on it, this session is going to hurt, like you have been stupid enough to ask me to do. I will not take very long, they will be quick and painful, and my intention is to hurt you so you will get the ludicrous idea out of your system for good."

She smiled, gave me a long cuddle, and said thank you. "I will lay the crop on your ass with a few gentle taps to get my aim right, then six very hard ones. You must then immediately turn onto your back with your legs wide apart; I hope you will then manage to scream 'red'.

She started climbing onto the table but said, "Good boy, that sound pretty good but how about six like earlier and then the six really hard ones that will warm me up better."

I knew she would not be satisfied until I did as she requested, she lay as instructed with the spoon in her mouth and that lovely ass offered up to me. I pushed the crop into the fold at the base of her cheeks; exactly where I had already caused damage and said "Ready?" she grasped the edge of the table with both hands and nodded her head.

I gave a swing, aiming to stop just as the crop made contact and said "One." Her cheeks wobbled, presumable sending pain through to her pussy area, which her mind must have translated as pleasure. "Two, three." She was now sweating, but each time her body was pushed down, she lifted her ass up for more. "Four, five, six." She was shaking with orgasmic pleasure all through this treatment; saliva was dripping from around the spoon in her mouth.