Mentoring Britney Ch. 06

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Barmaid's S&M gets a bit harder, but still fun.
4.3k words
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Part 6 of the 8 part series

Updated 10/02/2022
Created 05/14/2006
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The beautiful young Britney again drove back to my house well ahead of me and by the time I had parked up and got in she had already been busy. She had put the foam pad onto my kitchen table and was just spreading a sheet over the top. At some stage she must have removed her thong as it was an unclad ass sticking our from under her tartan mini, as she lent across adjusting the sheet.

"You are even more eager than usual, are you going to tell your ex mentor what you found to play with today. By the way your ass looks good."

She jumped up and sat on the table. "As I said I apologised to Mum and Dad for waking them last night, and offered to help Dad to clear out the garage as penance. We were chatting away while filling bin bags with year's worth of rubbish, when I found a riding crop. Dad must have noticed me caressing it, when he looked at me I blushed. I told him that it was a shame to throw it away it looked expensive."

"I really did colour up when Dad said 'I haven't used that on your mother for ages, here take this oil it will need softening up before you can use it'. I could not think of a thing to say, fortunately it was nearly time, so I said I had to get ready for work. Dad said 'don't forget to use the oil on it; we won't expect you home tonight'. I was so embarrassed; I have never talked about anything vaguely sexual with my parents."

"I was in my bedroom; the getting ready involved much more preparation of the crop than getting dressed. I was thinking that we could have some fun it looks much better than your ruler."

She gave me the crop; it was a work of art, a short handle with a tight braided leather shaft ending in a fold of leather around the size of a 50p piece. "This is indeed a tribute to the craftsman's skill, just right for encouraging thick skinned horses, not ideal for tender titflesh."

"Come on, you can experiment on my bum and then go for the tender bits." With that, she slipped out of her skirt and top and stretched out on her stomach.

I held the crop in my right hand and gave it a hard swing onto the table, very near her ear. It hit with a tremendous thwack, easily sinking thru the sheet and foam. "How many like that on your ass would discourage you from playing silly games?" She just smiled at me. I was very unsure of my ability to play with this toy safely, and decided to take it very slowly indeed.

"You are going to have to bear with me, I have got to get the feel of this weapon, do not expect an orgasm for a while." I went to her bum and did a few tentative swings just kissing the tip against one of her cheeks. I then went in with a harder one ensuring that I just made contact, a sharp thwack, and her butt rippled and I had left a red square the size of the tip. I asked her for some feedback.

"That stung, not too bad somewhere between yellow and black."

I then did one more on that cheek and two on her other cheek trying to exactly repeat the force used. She now had four red patches on her lovely white skin. "Assuming you were alright with those I have got the tips obvious power understood, I will now try the shaft."

I knelt down and took a swing trying to ensure that I landed on both cheeks simultaneously and that I did not let the tip make contact. Whack, her skin shuddered from the impact and she let out a loud yelp, there was now a red line on both her cheeks.

"This is a nasty toy beautiful, it could do you serious damage, how was that last one?"

She rolled over onto her side and said, "I suppose that was only a yellow, I'm not sure that I could say black to that until I was more excited, then probably. I just cannot imagine my Mum and Dad doing this sort of thing – spooky. Do you want a practice on your favourite bits now, and then we can get down to some serious action."

I went into the lounge and grabbed a couple of cushions; I placed these under her back, which had her stomach higher than her head. "That gives me better access to the undersides, you will still be able to show some cleavage tomorrow if I concentrate there."

She laughed, "I said they were your favourite bits, you did not like them covered than?"

"The overall package is my favourite; every thing about you is perfect. I am not sure I want to use this vicious thing on you soft boobs but I know you will insist I try." I then gave several taps, just using the tip of the crop on the lower curve of one of her breasts; each stroke was a little harder. The first just kissed her skin, the next shook the area where it landed, and the next shook her whole tit.

None of them did any harm, the last one leaving a red mark and causing Britney to have a sharp intake of breath. I decided that I had got correct level of force for her tits; I did not want to go any harder, I asked. "Right darling, knees bent and as wide apart as you can get them." I then tried some very light taps on the inside of her thighs and then one on to one side of her pussy. These had her squirming but not marked.

I then put down the crop and said "Jump off the table, we are going to have a coffee and cigarette and talk about what we do now." She looked a little disappointed but swung her perfect young legs off the table and wrapped her body around mine.

"What's to talk about, you have been so careful practicing, I know you won't do any damage just give me some pain to enhance my pleasure?"

I lit us both a cigarette and she poured us some coffee and I said "That thing is vicious; I want you to tell me exactly what you want me to do with it."

"All of your practice strokes would have got a yellow, in the heat of a session they would have all got a black – just listen to innocent little me, I used to need your encouragement to do anything. I think I would like you to gag me, tie my hands and have a good go at all three areas you practiced on, and then fuck me good and hard." Her hand was shaking a little as she said that and took a drag on her cigarette.

"No gag, I may get carried away; you must be able to use the safe words – and lay off the black. I do not really like the idea of tying your hands, I am not your master, just a friend helping you enjoy. Finish you cigarette and when you are ready jump back on the table, on your back and we will make a start."

She stubbed out her fag, and stood up and grabbed my erect cock saying "He seems more eager than you are, don't worry I know what we are doing – let yourself go I am all yours." She then jumped up and lay down presenting those perfect boobs and her exposed pussy to me."

I stood at the foot of the table and bending over slipped my curved tongue into, a very moist, pussy. My intention was to warm her up which apparently was not necessary, as soon as my nose made contact with her clit she had a little orgasm. I said "Wonderful little slut!" and standing up went to the side of the table.

Her nipples were standing up as hard as I had seen them, even her areolas where looking hard with many firm bumps looking like little nipples. My practice strokes had left just one slightly red patch so I started with some fairly light taps, using just the tip of the crop. I was getting the feel of the crop by now and was able to land rapid strokes, on each breast, and just leave a little red glow each time.

I told her to use her own finger to stimulate her clit, which she readily obliged. As she worked her clit we both increased our speed, I was getting a little harder although not enough to leave more than the red mark. As she tensed up, just prior to another orgasm I gave a fairly hard wham right on the tip of each engorged nipple. She let out a very load and drawn out scream and she literally gushed juices from her pussy soaking the sheet.

She took several minutes to regain her breath; I just gently stroked the crop along her breasts and even around her pussy. When she settled and opened her eyes, and gave me a smile, I said, "Caress your poor red boobs now please." I knelt down to enable me to get the correct angle and started a rhythmic tapping of her outer pussy lips. I was not hitting hard but the continuous small hits had the area glowing nicely.

Again with perfect timing I watched as she gave her boobs an extra hard squeeze and arched her back, 'whack', 'whack' right on her clit. Her legs shot out and she let out a long continuous scream and lay there quivering for a good minute. She was then very still and the sweat was pouring out of every pore on her body, she skin was nearly the same colour red as the marks my crop had left.

I went around, kissed her lightly on the forehead, and asked "Had enough darling, you have not said a word?"

Her eyes fluttered open and she said "Sorry, you took my mind to some other place, and it was nice there. I was not thinking about whether you were too hard or anything, it was just perfect. I would love one more session, on my ass, but don't be surprised if I then go to sleep until the morning."

Britney turned onto her stomach and wiggled her ass at me. I grabbed the lube and gently used a finger to work plenty into her little hole, and onto my cock. This attention had her saying "That's a lovely idea; you need some pleasure as well." She was so pent up that the attention of my finger had her shaking with a small orgasm.

I laid the crop across the fold where her beautiful butts met her legs, giving a couple of dummy swings to ensure my aim. I then gave a fairly hard hit, holding the crop against her skin as it wobbled; she tensed her whole body and said "Ouch." This had left a deep red stripe across both cheeks, but I gave two more rapid strikes in a similar area. This seemed to have the effect she desired, a long scream and very obvious climax again. I just dropped the crop and climbed onto the table.

My well-lubed cock slid easily into her ass, I gave a few gentle ever-deeper penetrations to give her time to adjust and then started humping as hard as I could. The lovely body under me was not resisting, in fact she was pushing back matching my rhythm. Again I am sure she drew out her orgasm all the time I was pounding, she was not very vocal, just a long continuous grown.

I gave a grunt as I emptied deep into her bowels, I could feel several good squirts shooting out. As I withdrew, she was still shaking and making a very faint noise, which sounded like 'yesss'. I jumped down and got a cloth to wipe my cock, she was lying so still I think she had indeed gone off to sleep, worn out by her exertions.

I just stood and looked at the gorgeous young creature; she was sleeping peacefully, absolutely soaked in sweat. Each of her ass cheeks had three very red lines; they were bound to turn into bruises, and be very sore, by the morning. I had to wake her it was a very uncomfortable place for her to spend the night.

I did wake her, but she was not really fully conscious as I took her up to bed. I got her to lie in bed and jumped in beside her. Without saying a word, she wrapped her arm and leg around me and was instantaneously asleep. When I woke up in the morning she was in exactly the same position – I could not believe my luck; I had this wonderful woman to wake up to, at least for now.

She did eventually stir and gave me a good morning kiss, before shooting off to the toilet. She soon came back, I was pleased to see that her boobs, although looking red had not been bruised. She said, "I see you looking at my boobs, they are fine but my ass is sore as hell." She then turned around and showed me a very bruised bum, Christ I thought, I had been too hard.

I said "You wonderful girl, that is not a toy it is a weapon, be very careful who you let use it on you in future. I thought I was been gentle and you know I don't want to cause you any harm, but I hurt your bum even so."

"Yes it is painful, one hell of a burning sensation all the time, but in no way would I have missed that experience even if I knew what it would feel like now. You are so good at giving me new experience, each time is better than the last – thank you. I had better get dressed and go home soon, go and make us a coffee while I shower."

She did disappear home after a quick coffee and I did not see her until she turned up for work as usual. She was wearing her jeans, heels and a nice white t-shirt displaying bare arms and a nice bit of cleavage. She gave me a cuddle and I said "Hello, looking sexy but where are your lovely long legs?"

"I said earlier in the week that I still had two thirds of my assets available, I am afraid that's down to just one, my ass is very sore. As nobody is going anywhere near it tonight I thought jeans would look nice for a change. I must tell you what my Dad said as soon as he saw me this morning, 'You look as though you had a hard night last night, if you let a guy use that crop and you can still stand he must be extremely fond of you, he must be a keeper'. I coloured up completely, it was so embarrassing, and I just gave him a quick kiss and went up to my room."

She was her usual, wonderful, self all evening chatting away to the few customers, and me although she was moving rather delicately. There were no obvious guys for her to play with but I do not think she was too disappointed. We both went home separately; I did not even get to inspect the damage I had caused.

The next evening, Thursday her last shift of the week, she arrived still dressed in her jeans but with a white frilly blouse and a black push up bra. I gave her a cuddle and said, "I take it from the jeans that your bum is still sore, but that cleavage tells me my little slut is feeling randy yet again."

She smiled and said, "My mentor is very perceptive, bum is improving but I think two holes are still going to be out of service until Sunday. I do not think I will be able to extend my circle of friends this weekend. I might well come to your place once or twice though."

I told her, obviously, that that would be nice and we got down to work. It being a Thursday, we were quite busy and I actually had to help her out behind the bar for an hour or so. It was far to busy for her to chat up anybody, but nearer closing time if did start thinning out and she was flirting with a couple of young guys. I quickly went into the office and grabbing a couple of condoms I went up behind her and slipped them into her hand. "As a reward for being such a nice girl, no wrong word, such a sluttish girl, take them out to the alley together."

She, very blatantly, said, "Come on boys lets see if they live up to your description of them." The three of them went off out the back door together watched by the other six or so drinkers. It was a good twenty minutes before she came back in and resumed serving, she was very chatty to the customers but I did not think any of them looked nice enough to deserve a trip out back with her.

When we shut up she said "You only let me play with those two guys, remember I only have you to satisfy me this weekend, I do like a bit of variety you know."

We agreed that we would meet up the next day, I would take her for a meal, and she offered to spend the night with me. I could leave the bar to look after itself; we had three staff on a Friday night. Before she left I said, "I will take you to a nice restaurant, you won't embarrass me by slipping under the table and sucking me off will you?"

"If you don't want to take out the new me I will just dress like I used to, nice sensible flat shoes and a long skirt. Good night, I will drive around to yours at seven."

She arrived, right on time, and was not dressed as she usually did for work. She looked fantastic in a grey silk dress. It had a very tight and short skirt with the top a rather loose crossover, leaving both her arms and her lovely cleavage on display. Nice grey court heels and a small silver clutch bag; her wearing her hair up and a narrow grey choker around her neck enhanced the effect.

We had a lovely meal at the very best hotel just outside town, every guy in the place must have spent most of their meal either glancing at her or more blatantly ogling. There were a similar number of women who spent the same amount of time either glaring at Britney or at their partners. She had made many guys very happy but probably done serious damage to several relationships.

While we were eating, I said, "It's a good job I am not in to making you humiliate yourself in some way, like walking around in here without a bra or without knickers. For one thing, you haven't got either on and you would probably enjoy it anyway. Before you ask, no you cannot get under the table and give me a blow job."

"Hey, I'm not a slut all the time, this dress would be spoilt if I had anything on underneath – all the other guys in the room seem to appreciate it." I obviously told her how much I liked it, and filled up her wine glass yet again.

We had a superb meal and both thought the company was great; I drove home although we had consumed two bottles of wine I had not had very much to drink. Britney was merry but not drunk perhaps staggering a little as she got out the car and took her lovely body into my house. I asked her what she had in mind for the rest of the evening.

She said, "Well my pussy is still messy and my bum is still sore, although both are available if you want to. My only fully fit hole is my mouth and throat, perhaps you could see how deep, and hard you could fuck that. Remember each time your try something new you take me to an even higher level of pleasure."

"There are two problems with that, if I take you to a much higher level of pleasure you will self destruct, the other is your choice of hole. I admit it will be good for me if I can manage to pump a load right into your stomach, but your enjoyment will be no better, in fact, certainly less than the other holes."

She took me into the bedroom and striped off her dress. "I better put my dress out of the way, it cost me a weeks pay. Right, our fun together is not going to last much longer, you just said it would be good for you to fuck my throat. I have had enough to drink to dull the pain so I want you to use my mouth as if it was my ass, just fuck it. Don't worry if I am sick, turn blue or anything else, fuck it as you would my ass."

By now, she was stretched out across the bed with her head slightly over the edge looking up at me and licking her lips. "Oh yes, like I am going to hurt you, choking you will not give you the same sensations as the pain and pleasure you get from the crop."

"I have been doing what you tell me to do for weeks now it's your turn to do as you are told, fuck my throat now."

My cock was pretty hard with the discussion so I put it against her lips and she immediately sucked it in a couple of inches and used a hand to caress the rest of the shaft. She sucked and licked it in this position for some time, it was very pleasant, and she was generating lots of saliva, which I thought would act as a lubricant. By now she had made my cock very rigid, she pulled it out and said "Now, go for it, remember don't stop until you are right in and shooting into my stomach."

I slipped back in slowly, I gently went deeper and deeper, and no problem I could feel her tongue running along the base of my cock pulling it even further in. I saw her chest rise as she took a deep breath and I pushed a little deeper. By now, she should have been gagging but she was actually acting as so she was swallowing it, her throat was drawing it in. It was a marvellous sensation on my cock as she rhythmically contracted her throat muscles around it.

I only had a little more to go, which with a light push was in, with my ball sack against her chin. I did some slow in and out motions although her swallowing action was pumping my cock very efficiently. Each time I pushed in, I could see my cock bulging out her throat, it was well in. Britney put her hands behind my bum and started pulling me in and out harder; I was very close.

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