Sex Lessons for Six Naked Schoolgirls Pt. 04

John rang Ruth shortly after she and her five schoolmates had visited his surgery. He spun a tale to her that he was doing some research on relationships and, after their previous meeting, felt she could be of great assistance to him. Would she mind coming back to his surgery one afternoon at 5pm to help him with his research?

Naturally she was pleased to do so.

John fanaticised about what might happen that afternoon.

He really wanted to get into her pants and, knowing that three other guys had previously fucked her, he decided he would ask her if she would agree to the pleasure of having his manhood up her posterior love tunnel.

No doubt it would be a new experience for her. Even he himself had only experienced the pleasure of anal sex a couple of times when Rebecca had finally plucked up enough courage to say 'yes' to his repeated requests to enter her from behind.

He was sure that Ruth's gorgeous little bottom would be delighted to receive something similar to what its neighbouring vaginal area was so enjoying.

John thought he would ask Rebecca on Sunday to again accept anal. This would give him just that little-more rear-end practice prior to Ruth's arrival the next day.

And he would ask Rebecca to instruct him in how to maximise her pleasure whilst receiving his erection up her 'love tunnel no. 2'. He would then be able to ensure that Ruth would leave the next day feeling totally elated - and not just with a slightly sore first-timers' anus.

If only Rebecca realised how valuable she was to John! Not only was she allowing him to give her a weekly fuck (which, in a few months' time, was likely to become a much more frequent - perhaps even nightly - fuck), but she had allowed him to deflower her anally, and she had given him the vital information that ultimately enabled him to take Grace's virginity, ...and now she would be unwittingly instructing him on the best way to most pleasurably anally dilate Ruth!

'Rebecca, you're a gem,' he thought.

...When Ruth arrived at 5pm on Monday, John lied to her again: 'I've had a shit of a day. Would you mind if we went back to my apartment and talked there, so I can have a beer? It's just a 3 minute walk down the road.'

...John helped himself to the beer and Ruth accepted a glass of white wine. John left the opened bottle nearby so she could refresh her glass whilst they talked and she relaxed.

The first half hour was spent 'helping' John with his 'research.' John actually found it quite interesting as Ruth provided a female perspective about some things that John had not previously considered.

He was particularly interested to learn how teenage girls - or at least one teenage girl - thought about sex. Yes, it was an integral part of being in a relationship, or was likely to become an integral part of a developing relationship, but it was also something that girls themselves obviously enjoyed - and wanted to enjoy - in its own right, and something they enjoyed sharing with guys...and they used it to 'reward' guys for paying them appropriate attention.

John was pleased that girls were now taking advantage of the freedoms that contraception provided, but couldn't help wondering why so many girls still had unprotected sex only to discover they had become pregnant...too often leading to the acute psychological trauma that resulted from having a termination or having to resort to the 'morning after' pill. He again wished he could offer every 18 year-old girl a free contraceptive implant.

John hadn't realised how crucially important it was for a girl to be in a relationship until he had the conversation with Ruth that afternoon...and how being an active, integral member of a female group served as a 'surrogate relationship' when a girl wasn't currently in an active relationship with a guy (or, for some, another girl).

And suddenly he realised how much more impactful it was for a girl to be 'dumped' after a relationship - bringing back memories to him of how he had simply 'dumped' two girlfriends without any explanation when he felt their relationships had run their course.

When asked, Ruth divulged that she was not in a current relationship...and, although there was no immediate prospect of acquiring a new boyfriend, Ruth indicated that she hoped that situation would not last long. This confirmed to John the importance to females of being in a relationship.

The conversation then turned to masturbation.

Ruth had been masturbating regularly since at least puberty. And she really enjoyed it - frequently bringing herself to orgasm.

She told John that she had been advised that masturbation was something that was not good for her, and this attitude may have even been impressed on her since early childhood when her mother and father had told her to 'stop touching yourself, stop playing with yourself down there.'

But from around puberty she had ignored the advice - the pleasure was too great to ignore! - and she now wondered why so many girls and women apparently still did not masturbate.

John asked Ruth to describe how she masturbated or, if she was willing, to show him exactly how she masturbated.

She agreed, and they moved to the bedroom where she climbed onto the bed, having removed her jeans and panties - exactly the same ginger panties she had worn when on that school visit to his surgery!

This was one sexually comfortable, sexually confident young lady, he again thought.

Once again, John could barely take his gaze away from those attractive, whispy, ginger pubes and that come-hither female valley that ran down between her legs.

Ruth moved her hand to between her legs - then suddenly sat up and unbuttoned her top before removing it and then removing her bra. She dropped both onto John's floor.

Now John had something extra to attract his attention. A pair of pert, well-rounded teenage boobs each surmounted by a darker, taught, tender bud.

They were VERY enticing. Ooh, how John wished he might caress them between his lips...or, at the very least, be fingering each of them.

But John was distracted. He could feel something becoming very erect between his legs!

He wondered if he should drop his pants so that both he and Ruth were similarly attired. But he wasn't immediately given any time to do so.

'Sorry,' Ruth said. 'If I'm going to try to come to orgasm I'll need to involve my tits. I usually find it helps if I give them a bit of a pat before I start playing with my clit. So they needed to be freed from my bra.'

Ruth lay down again and closed her eyes. John decided he would just watch...still thinking he might have an ejaculation, thereby wetting his pants.

So he quietly undid his pants, letting them drop to the floor and then, quickly, pulled off his undies. A hand towel was conveniently close at hand, should it be needed!

He was amazed at how erect his penis had already become.

Ruth began by cupping both her breasts and visibly squeezed them gently down against her chest a few times. She was enjoying the feeling of how soft and smooth her tender young mounds actually were, whilst imagining that John would soon be tempted to continue their massage for her.

Then her fingers fondled her now-erect nipples, occasionally pinching and pulling them and twisting them between her thumb and her forefinger. How good that felt!

It was not long before Ruth slowly moved her right hand down between her legs. The fingers on her left hand continued to arouse her left nipple.

John noticed that Ruth's index and middle fingers immediately disappeared into her love tunnel - he thought perhaps to sample its wetness, but actually it was to retrieve some of her natural lubricant - before both emerged and moved up the length of her clitoral slit, moistening it as they did so, before they began circling her love bud.

John was amazed how rhythmically, how long Ruth worked this area. She just kept circling her clitoris, circling her clitoris with her fingertips.

Occasionally she ran her fingers over her clit or gave it a slight flick - as if instructing it to 'stand up straight...be a good girl.'

And she seemed to be doing it ever so gently...and enjoying every minute of what was happening.

Then, quite suddenly, her left hand left her breast and two fingers were plunged into her hole. They were soon working with a different, increasing urgency...helping things happen as Ruth willed herself to a climax.

A soft, satisfied moan from Ruth was the first indication to John that this had been reached.

Ruth then tilted her head back on the pillow and relaxed, her eyes still closed, clearly just savouring a diminishing sensation...and thinking she could lie there for hours alternately relaxing and masturbating. For Ruth had just brought herself to a particularly intense and enjoyable orgasm!

'It's easy when you know how,' John had thought. And Ruth certainly DID know how - probably aided on this occasion with the knowledge she was being watched!

John had never watched a young girl masturbate before - other, of course, than having briefly witnessed those twelve visiting schoolgirls fondling their very-female areas which were normally hidden under their panties and between their legs.

He was fascinated. And he was unbelievably close to ejaculating!

John would undoubtedly now ask Rebecca to masturbate for him one evening after she had moved in. She had never masturbated in front of him before, but John was sure she would happily agree to do so.

'Oh My God,' Ruth said when at last she opened her eyes and finally became aware of John's hard-on.

'That's the most impressive erection I have ever seen. And it's just from watching me? You surely must be about to cum.'

'I am,' replied John.

'You've watched me bring myself to orgasm, so now it's my turn to watch you cum,' Ruth suggested.

She moved over on the bed, allowing John to lie down - his erect member pointing skywards. He had grabbed the hand towel as he did so.

John moved his left hand to cup his balls, then gave his right hand a good lick and clasped his penis with it.

His hand moved rapidly up and down, up and down the length of his shaft. Ruth could see he was also squeezing his erection...until he came.

It had taken longer than John thought it would for him to finally cum. So obviously he was in top physical condition sexually.

Most of his cum was captured in the towel.

But he had held the towel a few centimetres above the tip of his penis so that Ruth could witness each involuntary ejaculation. So a few white droplets fell down onto his pubic hairs and onto his stomach.

Ruth saw this and moved across to playfully massage them into John's stomach region.

And then she popped her middle and index fingers into her mouth, sucking on them as though she was enjoying a cooling icy pole.

'Another man I've tasted,' she remarked.

This prompted John to ask Ruth about having oral sex.

Ruth told him that guys just expected girls to give them blow jobs and girls usually obliged. Ruth also revealed she sometimes swallowed the cum (not always out of choice) and that, whilst she did not particularly like this, 'it was simply a part of what we just have to do for you guys.'

'And do you accept oral from guys?' John enquired.

'Oh, yes, I've had a few come and dine at the Y,' she replied. 'Which would be all right if they just tongued me, but they often also get a bit rough with their fingers down there, so it's not always that satisfying.'

'Frankly, I get far more satisfaction from masturbating myself than having them play down there...and I'm also not pressured into then having to hoover them because they think I owe them something in return for their having pleasured me by playing with my vagina.'

'And how about purely vaginal masturbation?' John enquired.

Ruth explained that she masturbated vaginally less frequently - probably because she was still receiving so much satisfaction from her clitoral masturbation and because she felt it was slightly less messy.

But she revealed she really did know where to find her g-spot (this was no surprise to John!)...and received considerable satisfaction playing down there.

'Have you ever squirted, had an ejaculation?' John then asked.

'No,' she replied.

'Would you like to see if you can have one now?' John enquired. 'I'm told by girls who have squirted that it's much, much more satisfying than simply having an orgasm.'

'I've heard the same,' Ruth replied. 'So, of course I'd love to give it a try...particularly if you can show me how.'

John explained that he had helped other girls to squirt, but he could give no guarantees of success. He also explained to Ruth that it was not something she was likely to achieve immediately, and that she could expect to feel a little vaginal discomfort as she moved towards ejaculation.

They then adjourned to the dining area with its parquetry floor. 'It's much easier to clean your ejaculate from there, because it may go everywhere, than from off my bedroom carpet,' John explained. And he removed his shirt, anticipating he might also cop the spray from between Ruth's legs.

Ruth was soon lying flat on her back on some beach towels that John had positioned on the floor, her legs again spread apart, with two of John's fingers well inside her love tunnel. They had moved to her g-spot area and were gently, rhythmically rubbing over the ridges that they had located there.

John knew that inducing Ruth to squirt would take time. So he had coated his fingers liberally with gel. He wondered whether she would squirt first or whether his fingers would simply become too tired to continue. After all, bringing a girl to ejaculation was something he had only done twice and both times he had discovered it was hard work - much harder than simply filling a girl with his cum.

And it did take some time. John just continually massaged her g-spot with those two fingers and stroked her clit with the fingers of his other hand. Ruth simply focussed on the sensation and tried to avoid having an early orgasm.

But they finally achieved what they wanted - with Ruth squirting a huge spray of ejaculate well into the air between her legs...and experiencing the most mind-blowing feeling of euphoria.

When she eventually recovered, Ruth could not thank John enough for what he had just done...but John knew he had now put her into a position whereby she would feel she 'owed him a favour.'

Even though John was thrilled that Ruth had orgasmed and Ruth had ejaculated, this was not what John had planned would happen this evening.

Simply, he had just wanted to take her anal virginity.

So he moved their conversation slightly - to her defloration.

'You are a very open, very honest young lady and what you have told me has been very helpful. I wonder, therefore, if you might now also tell me briefly about losing your virginity - what you thought about it, what sort of memories you now have about the occasion?'

'John, I hate to tell you, but I'm still a virgin,' Ruth replied.

'I've been ready to lose my virginity for some time and I've done things like get on The Pill in preparation, but somehow it's just never happened.'

John was astounded.

He could hardly believe what Ruth had just said.

It took him some time to respond.

'Oh, fuck me, if you'll excuse the French,' John said. 'I'm sorry for assuming you are no longer a virgin. I'm really embarrassed.'

'The other day one or more girls indicated they had lost their virginity and I somehow assumed you were the most likely to have done so. And there was nothing in what you have said to me today about relationships, about masturbating and about giving oral sex that made me think otherwise.'

'I'm really just so sorry because suggesting to a girl that she is sexually active, when she isn't, must be one of the worst things anyone can say to a girl. I'm just glad I said it to you alone, and didn't suggest it in front of someone else, or say it to someone else - not that I would ever think of discussing your sexuality with anyone else. Ruth, I'm really sorry, I'm really embarrassed and I do apologise.'

'John, it's no big deal and there is no necessity for you to apologise,' Ruth replied. 'I had intended to have lost my virginity by now, and as I explained to you I have taken steps like getting a contraceptive with the intention of doing so. But it just hasn't happened.'

'If anything, what you have just assumed, and what you just said to me, will now give me a hurry-along. I suspect many others also think I have already lost my virginity and am now enjoying an active sex life...as are many other girls of my age.'

'So much for the idea of having my hard-on right up her sweet little virginal arsehole tonight!!' John thought to himself.

John was thankful, though, that he had had that experience with Rebecca the previous day.

Rebecca's 'love tunnel no. 2' was certainly not as naturally accessible as her 'love tunnel no. 1,' but the extra effort it took to get in, right in, had been well-rewarded yesterday when she had bucked a little as she achieved orgasm.

And that was Rebecca's first anally-induced orgasm...an orgasm so pleasurable that Rebecca immediately indicated to him that she would probably now want to accept his manhood in her rear hole more frequently.

John looked forward to that.

And he wondered if Rebecca might one day agree to be made airtight. THAT would be a REAL experience!

'But if Ruth agrees to what I am about to suggest, I'm sure it will only be a few weeks until she also discovers what it feels like having her first full-anal dilation and what it feels like receiving her first load of cum well inside her rear passage,' he thought to himself.

'I'll give her what she immediately wants - her first fuck - and, once she is satisfied with having received that, I'll follow it with the offer of the rear-end penile insertion. And then I'll work on her, like I did on Rebecca, until she is pleading for more. More anal, that is!'

'I don't want to seem crass or be prying, Ruth, but how soon would you ideally like to lose your virginity?' John asked.

Ruth was a bit puzzled. "Why do you ask?' she enquired.

'Well,' said John. 'If you had said very quickly, and you were willing to do it with a slightly older man, then I might say there is a bed available in the room over there and there is a little man, who you have already seen and you have had some contact with, who just might be able to grant your wishes.'

Ruth thought for a moment. The few seconds pause simply teased John - would she, or wouldn't she?

John knew what HE wanted - and it wasn't just to be given another look at her magnificent ginger muff!

'Yes, I'll say "very quickly",' she finally said with a smile. 'But, if you don't mind, not right now because you have left me a little sore down there - not that I'm complaining at all!'

'So how about Wednesday or Thursday?' she suggested.

John's manhood already had a firm appointment to be inside Grace again on Thursday afternoon (and there was no way he was re-scheduling that!) so he and Ruth agreed to meet again at his unit at 5.30pm on Wednesday.

'I promise you, I'll have a permanent hard-on until then,' John added.

'And I think, considering how much you have masturbated and what I have felt with my fingers down there today, you will find losing your virginity next Wednesday will be extremely pleasurable. I'd be most surprised if you experience any of the pain or any of the bleeding that some girls get the first time they have intercourse.'

'And no masturbating between now and then!' John added with a chuckle.

It was turning out to be a busy sexual week for John: anal with Rebecca on Sunday, multiple erections and masturbation with Ruth on Monday, Ruth's defloration on Wednesday, Grace's regular romp (definitely vaginal!) on Thursday, who-knows-what with Rebecca on Sunday (maybe vaginal, maybe anal, maybe oral, or maybe she would ask for all three!)...plus perhaps another visit from Ruth, who would probably want to quickly confirm to herself that Wednesday was not just a one-night stand with some opportunistic male bastard.