Mentoring Britney Ch. 03

While she was in the shower I sat and had a cigarette, thinking what I could 'push' the beautiful Britney into next. I knew she had liked my fantasy stories, and even liked the hardcore videos I had given her. She had read about all the extreme sexual activity and made no comment about anything being off limits, now she was saying 'push her harder'.

In just one week, she had progressed from virgin to what can only be described as a slut. I had lost count of the total number of guys that had given her pleasure, it was well over the dozen already. Despite my best efforts to decline, I was one that had given and received pleasure.

The next target was, as I expect she realises, her equally virgin ass. I would perhaps take things slowly for a few days, to make sure she is still keen and then set about her little hole. I had just come to that conclusion when the lovely young body was standing in front of me again. She was completely naked, except for her heels, she is a very attentive slut realising what pleases a particular man.

"I hope you are not standing there expecting me to leap on you again, you need enough energy to work this evening. You should go home now and I will see you when we open up." She agreed and got dressed giving me a huge thank you kiss and cuddle on the way out.

Britney arrived at work as usual, looking nice in her short denim mini and tight white blouse that showed her nipples off well. We opened up and had a very slow night, just the odd older fellow, or two coming in having a quick pint and leaving. It was getting close to closing time and I, and possible Britney had given up hope of any action. Just in time in came a guy on his own in his late forties, she started to chat away to him and caught my eye and smiled.

The little slut, I was not going to suggest him, but she seemed to like the idea. I went into the office and opened my gross carton of condoms, it was silly buying them retail so I had ordered bulk supplies from the web. Taking one out I went over to her and whispered, "You look as though you need this, use the alley, and let him have your pussy."

Having entertained him and closing up we sat down for a drink and cigarette. She said, "He cut that a bit fine I was thinking I would not get any action tonight, nice guy." I obviously caught her mood correctly.

"Don't you think you have managed enough action this weekend, I was going to ignore him until you looked at me so eagerly?"

She stood up preparing to go and looked a little reluctant when she said, "I thought I was due to be pushed harder tonight." She then gave me a quick kiss and left.

Monday evening she turned up, early, dressed in her denim mini dress, looking as sexy as usual. "You naughty pupil got checked over at the clinic, so problems, still in full working order. They did get a bit personal both with questions and with my body, if I need to go again my mentor will have to tell me to, I do not fancy doing it again. They tried to horn in on your job, gave me four sample condoms but no instructions on what I supposed to do."

"If you did not like the experience there is a simple answer to that, either give up your game completely or don't get too drunk and forget the condom. You had better keep your four samples for emergencies."

"So, what would my mentor like me to do tonight?"

I took her hand and asked, "What has the beautiful Britney got in mind?"

She just looked at me and after a lengthy pause said, "No, it does not work like that; my mentor has to give me instructions."

"Come into the office with me, I have something to show you." I had a box containing a large tube of lube, a rather small size butt plug, and a disposable enema kit. Her lovely face turned rather red as she picked them up and put them back in the box and picked it up.

"I have got to go off to the ladies for a while, can you open up for me please. Thank you my clever mentor." She, still blushing, gave me a kiss on the forehead and rushed off.

I had opened up but no customers had arrived when she came out of the toilets and walked across the bar towards me. She had on her highest heels but I do not think that was the cause of her delicate walk. "How long have I got to keep it in, I have got to work you know?"

I smiled at her and got a very worried look when I said, "Just as long as you like, I have a larger one to replace it when you want to take that one out."

She did not say anything else and came around behind the bar just as three customers came in. She served them in her usual friendly manner and was moving around apparently without difficulty. For early on a Tuesday business was brisk and she was kept rather active.

After a little over an hour, she whispered to me "Please may I take it out and apply some more lube, it is a little sore. I have to admit to plenty of lubrication in my other hole though." I just told her she could go and take it out; I would let her know what was next later.

Britney disappeared for a few minutes and came back in looking quite relieved, she continued behind the bar for another hour or so. I then noticed she was talking quite happily with a guy in his late thirties. I called her into the office and handed her a condom and said "It's pouring with rain; I think you had better bring him in here."

She took it but was looking very worried, in fact, she was trembling slightly. "Don't look so worried, just give him your pussy, here have another condom and see if you can suck out another load if he deserves it."

She went back out and after a few minutes asked me to look after the bar. I know she is extremely attractive but it was surprising that every man she had propositioned had accepted, so far. After a rather extended session, they came out, the guy bought another pint from me, and she went and cleaned up. She then took over and was chatting to him as a normal customer; he actually remained until closing time.

When we were sitting down for our end of evening chat, she said, "Thank you for that, I was not ready to go any further. I did get a nice fuck and some pleasing mutual oral from him in the office. He was a bit clingy talking afterwards though,"

I gave a little grin "I think you have a clue how things are going to progress, if you want to. For homework take the plug home and slip it in, using plenty of lube, do it a minimum for six times at different sessions."

With that, I got a kiss and we both went home. My moral position was slipping; I was trying to figure out how, if any one was going to, it could be me to take her virgin ass. I would have to make sure we kept the training going until the weekend.

Britney arrived for work wearing her white denim mini dress, looking as ravishing as ever. I asked her if she had followed instructions. "I always do as you tell me, once last night and five times today. I admit to using my fingers for a little stimulation around and in, my other hole at the same time."

I thought, it's only Wednesday and she is getting into it a little too fast. "I think you ought to slip it in for a bit longer this evening, tomorrow me will try the larger one." She said Ok and went off to the toilets.

She was quickly out again and walked behind the bar showing no sign of discomfort at all. Before any customers arrived, I did go and push her cheeks together and asked if she was comfortable. "Very nice thanks, especially when you do that."

A few customers came in which she served very happily but we both noticed her conquest from the previous evening arrive. I said to her "He could be trouble, quickly remind him that it was a once in a life time opportunity." She had a quite chat to him while serving him a beer and things seemed all right, in fact, he left after downing his pint.

She had a steady, but not busy, flow of customers for the next two hours until I suggested that she should go and take her toy out. She said thanks as it was a bit awkward working with it in. The rest of the evening presented no possibilities for her pleasure and it was nearly closing time when the guy came in again.

Britney said, "I will have another word; I may need your help though if I can't get rid of him, at least he does not look drunk." I watched as she went and talked to him, she did not get him a drink. I could not hear the conversation but he seemed to be polite and she was talking to him normally although it did involve her shaking her head 'no' rather a lot.

I then watched as he counted out, slowly, four twenty pound notes onto the bar in front of her. She blushed, and stood looking at him, lost for words or contemplating the offer? This was entirely her decision, not one for her mentor.

They stayed looking at each other for long enough for me to conclude that she was thinking over the offer. She did look in my direction several times but Britney saying, loudly "Get out, and take your money", ended the silence. He did leave without any fuss and even said sorry.

He was the last customer, but Britney did not seem eager to talk to me and busied herself sorting out the bar. Before she closed the till, I bought a beer and a vodka ice and went and sat down at our usual table. She finally came over, sat down, and said, "I think he enjoyed his experience last night."

She was not mentioning the money but I wanted her to tell me her thoughts "I am sure you could say that about any gentlemen that has the opportunity to use your body."

"I did make the right decision; I am a slut not a prostitute."

I took her hand and squeezed it saying, "I am a little surprised that you say you had to decide between being a slut and getting paid for the same thing."

She blushed again and replied, "You have just summed up the problem; both choices give me a good fucking; only one leaves me with money. With that £80 I could have bought a couple of new outfits."

"Sorry, that decision has nothing to do with your mentor's job, as far as your guardian angel is concerned, prostitution is a dangerous game."

She smiled, but still blushing said, "I think I had better leave now, but I will say that the danger is no different taking a guy into the alley and getting paid or doing it for free."

"I think we had better end this conversation, perhaps if you had been fucked this evening you would not be thinking stupid thoughts."

She did give me a kiss and leave without further comment. I thought I had done my guardian angel role rather well, although she did raise the same point as I was thinking.

She arrived for work the following evening, her last shift of the week, in a nice tartan mini skirt and tight blouse. We did not mention the last discussion but she was obviously still wanting some action. "I have a new present for you, a new plug; it is both wider and longer but made of very soft material. Would you like to go and, using a lot of lube, slip it in place?"

With a "Yes sir" she immediately disappeared and was back after about ten minutes saying "Thank you for my present, it was a little difficult getting it in that last bit, but once it snapped in the final bit it feels nice."

"I hope we can find you a guy, or more, for tonight – perhaps someone for you to invite over tomorrow night."

As she went over to start preparing for work, she just said, "I hope so." It was a very busy evening and she was kept on her feet all the time. I gave her the opportunity to go and either take it out or if she preferred just reapply, some lube after an hour or so. Her little hole was obviously nearly ready as she took the second option. Sometime later she indicated a guy who she presumably fancied, around thirty although possible older.

I whispered to her, slipping her a condom. "Go and remove the plug and invite him out to the alley. Only let him use your pussy, but if you want to, invite him to take you out tomorrow evening." After a rather long time, with me having to work hard, she came back looking very happy. She did whisper to me that she had generated rather a lot of lubrication of her own and should she put the plug back in, I said no.

After we had cleared up and were sitting having our drink, she said, "I have had a nice evening, was feeling very randy walking round with that thing in my ass. The guy relieved me very nicely, I was dripping. I take it my mentor would like me to drop around to his place tomorrow afternoon?"

I said, "Yes that would be nice, we could have a coffee." She gave me a kiss and agreed that a coffee would be nice. We obviously both had more than coffee planned.

Just after lunch the following day the beautiful young girl arrived on my doorstep, she was wearing the same tartan mini skirt but with a blouse tied under her boobs showing off a large expanse of belly. I told her she looked more attractive every time I saw her.

"Aren't you going to put the kettle on, I thought I had come around for some coffee?" She then wrapped that fantastic body around me, gave me a long kiss and said, "I know my mentor will not suggest it but the obvious next stage of my journey in sexual experience is too lose my anal virginity. You have prepared me enough to have the courage to ask you to take it. You deserve it and from your expertise last week I am sure that it is best for me."

"Thank you, I am only here to please, have you got the plug in now?" She looked rather fluster and told me she had not and apologised. "Don't worry you silly girl, I will just have to spend a little more time preparing things, which should be enjoyable for both of us."

She took me into the kitchen and put the kettle on "I will make the coffee, I know you will try, but please be gentle I am actually dead scared." The poor girl was actually shaking a little. We sat down and had the coffee and a cigarette.

"Don't worry, I know by the fact you are here that you want to experience it, and I think you will admit that I did not hurt you last week. You seemed to rather enjoy the experience as I remember."

She jumped up took me by the hand and pulled me into the bedroom. "You are so very right, I did enjoy your attention last week, it was the very best I have experienced. Come and show me some new pleasures please." Heaven, what more could a dirty old man wish for?

"While it would be more erotic for me if you left your clothes on, that gear is so sexy, I think you better strip off. Would I be correct in assuming that you had an enema this morning?" She admitted she had and offered to kneel up on the bed. "I think perhaps we will start with a few warm up exercises, just sit on the bed with your legs apart." Some lengthy working on her clit with my tongue and a couple of fingers exploring her pussy was rewarded by her having a very demonstrative orgasm.

I did not let her settle but told her to lay back with her legs drawn up and to hold them apart with her hands. Lubing up my fingers I then did some lengthy massage concentrating on the area around her cute little hole and the space between it and her pussy. One, then two fingers slipped into her pussy seemed to be appreciated and I had no problems. Using my other hand I gently, although with little resistance slipped a finger deep into her ass.

I gently rocked my two hands in and out, squeezing the fingers together with just her thin wall between them. This seemed to be appreciated so I added a second finger to her ass and twisted them around to spread the lube. The addition of a third finger was achieved easily and with no adverse reaction. I had intended to use the plug but the ease of entry so far indicated that I could just go for it.

I did some more pumping back and forth, now with three fingers in her ass and two in her pussy. As I asked her how she was feeling her body answered me with another short orgasm. "Ok, beautiful it's time to kneel up for me now". I was now presented with the sight of an extremely attractive youthful ass waiting for me to use, nice.

I knelt up behind her and soaked my cock in as much lube as I could and gently placed it against her puckered ass. My old body was doing me proud, it was rock hard. I slipped it in a little without difficulty; she did let out a small grunt. "Your turn now beautiful press back on it so you take it at your own pace. She approached this task with some vigour; I had to brace myself as I sunk further in.

When she had forced it half way in I told her to hang on there to get used to it. With a little bit of difficulty I reached down and slipped a finger into her pussy and finding her g-spot gave it some serious rubbing. This got an almost instant reaction, she tensed up, screamed, and my hand was soaked. Of more relevance to the task to hand, her muscles tightened around my cock almost painfully. She then forced herself further onto it and I assisted until it was fully in. I held it there for a moment but then pulled out a little and started fucking with slow short strokes.

My consideration was unnecessary she was virtually fucking me; I speeded up with deeper faster strokes. The gorgeous slut had yet another orgasm as I pounded away. I am sure it lasted for the whole time I managed to pump away before depositing my cum into her bowels.

Britney collapsed out on the bed and I lay down beside her. She reached over gave me a kiss on the neck and caressed my now limp cock. "You have been a very helpful mentor but you are an absolutely fantastic fucker, thank you."

After both having a shower we sat around and chatted until it was time for me to drop her off for her date. She had been very pleased with her introduction into anal and said she felt comfortable; I had not done any damage. I gave her three condoms and said, "There you are, one in each hole tonight, have fun. Remember although unusual he may not fancy anal, not all guys do."

"It is not like he is paying for it; I am doing him a favour so he can do it exactly where I tell him to do it."

I took her down to the town centre and dropped her off; she dressed just as she had been in the afternoon. Her sluty apparel did not make her stand out from the majority of girls of her age but she had a much better body than most. I had left her at eight o'clock and went to check on the pub.

Getting home at half eleven I saw they were already home, once more the attractions of the bedroom had outweighed that of the clubs.

While I had a coffee, I heard some activity from her bedroom, and after I went to bed, they had a very noisy session. I dropped off to sleep and it was early the following morning that banging noises from her bedroom woke me up. Lucky bastard, he must have been good she kept him all night. I got up, dressed and went down stairs and made some coffee.

It was a good hour later, after more noisy activity, that a taxi sounded its horn outside and the guy came downstairs and left. He was closely followed down by a sweaty Britney with her hair out of place but looking radiant, she was just wearing her short dressing gown, and her high heels. "Good morning my mentor, your allocation of condoms was not enough, I had to use two more from my reserve supply. Thank you for the anal preparation, I put it to good use last night and again this morning."

She perched her bum on the table beside me and lifted up a leg, opening her gown a little and running her hand along her thigh said "Look my juices ran all the way down my leg, do you really want to send me out to find a lunch date today. I expect we could find something interesting to do instead."

"I think your requirement for a mentor has come to an end, you don't seem to need any encouragement. You kept your last victim for your pleasure all night and I don't think you have in mind us sitting down and watching daytime television."

She then opened the top of her gown a little and said, "Perhaps some television, maybe one of your videos, would be in order, but a little later on. You could kiss this better for me; he seems to have marked my breast with his teeth. Regarding mentoring your brothel story had twelve chapters, I am still on chapter one."