Sex Lessons for Six Naked Schoolgirls Pt. 06

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Debbie's first-time penetration…its pain…its pleasures!
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Part 5 of the 8 part series

Updated 06/07/2023
Created 12/12/2015
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MrsJ
MrsJ
343 Followers

Debbie is not the prettiest girl on the block. She's not ugly...just plain. A fairly ordinary brunette with unremarkable shoulder-length hair. Unfortunately, she is also a bit overweight -- well, let's be frank, fat! Not obese -- but those extra pounds she is carrying are not doing her man-appeal any favors at all.

But she has a big clitoris.

An unusually big clitoris!

One that's like a mini-penis, peeping out prominently from between her labia. Permanently. Presumably looking to be loved!

And Debbie is still a virgin, as I had recently discovered.

What a waste, I had thought. Young ladies' cunnies are made to be shared with guys!

She has a clitoris -- a sizeable clitoris many other girls would surely 'die' to have -- one that's just made to be fingered, sucked, stimulated. I believe she has a g-spot (I'd helped her, as a schoolgirl, locate it when she was lying, pantie-less, on the examination table in my surgery)...a vagina that, I imagine, would enjoy being repeatedly penetrated...and she would probably delight in the experience of being filled with cum.

She is female, after all!

She should no longer be a virgin. Debbie should be sharing her body, in the same way as most other girls of her age are doing. She should be enjoying twenty-something's female sexual pleasure to the max.

Debbie, of course, recognizes this. That's why she was in my surgery that day having her second contraceptive implant inserted.

I again asked her why she was still a virgin, considering that she has visited me some years earlier to receive her first contraceptive implant. I had expected she would have lost her virginity soon after that visit to my surgery.

Her response will, I am sure, resonate with many other young girls.

Debbie acknowledged she was not the most attractive girl available. But she had received attention from a young man -- who she knew was no virgin, because he had apparently previously shafted one of Debbie's girlfriends.

Debbie had allowed his fingers to play inside her panties on numerous occasions, she had sucked his cock, and -"YUK!"- had even accepted a mouthful of his cum.

She desperately wanted to be "one of the girls" at that time and lose her virginity...but on her terms, and on an occasion that suited her.

And this had led to her seeking that original contraceptive implant, as she then had the intention of soon surrendering her virginity to that young man.

She admitted that, perhaps, she too-romantically expected her defloration would be a fairy-tale event and that, perhaps, she had said 'not today' to this young man on a few too many occasions.

Anyway, one night he became insistent and when Debbie, again, suggested 'not tonight' he suggested to her that 'I'm getting the distinct feeling you are frigid, and you are just a shitty prick-tease,' before he then stormed out on her.

Being accused of being 'frigid' really cut Debbie to the core.

There-and-then she decided that, if the young man felt she was 'frigid,' he could never be the man to pop her cherry. And, no other young man had shown similar interest in her since that time.

She even subsequently wondered if that guy had said derogatory things about her to his mates, contributing to the lack of attention she had then received from other local men!

So, quite simply, she had remained a virgin.

But now, not for much longer!

* * * * *

When Debbie arrived at my home that evening I checked that she was intending to spend the night in my bed. And we got talking, over a glass of wine -- mainly about her, as I wanted Debbie to feel I was interested in more than just the opportunity that her little hole between her legs was offering to me.

I'd wondered how it must feel for a young girl to go to a guy's home -- to see a guy who she barely knew, and in this case a significantly older guy -- with the sole purpose of allowing him to take her virginity. Perhaps it was like going to a hospital for an operation -- hoping that all would go well, expecting pain and discomfort, leaving 'cured.'

"You must feel a little like a bitch on heat tonight," I suggested to Debbie. "Eagerly willing to accept whatever is offered?"

She smiled. "Not exactly," she revealed. "I'm feeling a bit relieved, a bit apprehensive, and quite elated."

Her anxieties were normal. Will I have any troubles entering her? How exactly will it feel? Will my penis be too big for her vaginal cavity? Will she bleed? If so, how much? How painful will it all be? Would she enjoy it? Might she even orgasm?

I assured her that she probably would experience pain -- most girls do. Some girls experience just a little, a few find their 'first time' an excruciating experience. And there was no way to know in advance how she would react to that first penetration.

But, surprisingly, even if they felt they had been torn apart and had bled, girls -- all girls -- rapidly bounced back, just wanting and seeking 'more'!

Debbie reminded me that she had sucked my engorged penis during that excursion to my surgery as a schoolgirl and remembered it as being 'huge'.

She was not wrong. My erection is a little longer, a little wider than perhaps three-quarters of other men's. So she would most certainly feel it whilst losing her virginity!

"Well, your job tonight will be to get it very much bigger, much more erect than that - so it can penetrate you deep, deep down, as far inside, as possible!" I kidded her.

I then told Debbie I needed to take a shower, and invited her to join me. I hoped it might be a bit of fun, hoping it would help relax her, before the serious business of -- perhaps forceably -- expanding the diameter of her virgin love tunnel.

"It will give me the chance to have a good look -- and a good feel -- of your entire body, and you'll be able to see and touch all of me," I promised.

In general, her body didn't turn me on. But I played with her nipples, squeezed her butt, ran my fingers down the length of her ass-cleavage (and elicited a bit of a 'don't you dare go there' reaction!), paid specific attention to her pudendum...and, planted a big kiss -- and I mean a real kiss! -- on her lips and mouth. And soaped her up, from head to toe!

I think she enjoyed feeling my 'little man' -- perhaps apprehensively knowing what he would soon be up to!

Debbie had shaved her pubes for the occasion. All she now had was a neatly trimmed patch that sat above her pubic bone -- which I actually enjoyed rubbing with my fingers. She, quite obviously, had prepared for tonight.

But her clit intrigued me.

I so wanted to play with it. I so wanted to suck it. I so wanted to see if I could engorge it to become as stiff my little man would be when he brushed down the side of her clit and travelled down her love tunnel.

My interest in physiology overcame me. Once on the bed, and having sucked and fondled her clit for a bit, I asked Deb to show me what she did with her clit whenever she masturbated. "It's so I can ensure I pleasure you properly," I explained.

Deb then admitted she wasn't a big masturbator. She was still suffering from having been told, as a very young girl, 'don't do that,' and, even more, from crazy religious teachings that it was somehow morally wrong to pleasure yourself sexually.

"Poor girl," I thought. "She really does now need to be given a really good screw!"

But still, she showed me how she would occasionally tap her clitoris, rub it, stroke it in an upwards direction, stroke it sideways, and told me how she would push it hard against things like the back of her hairbrush. And how she derived some pleasure from this.

So I spent time playing with it, as I simultaneously inserted a finger to find her g-spot.

Needless to say, whilst doing this I developed a significant hard-on...and started to think that it was time this lady underwent her long-overdue defloration.

And, I too, started to wonder how difficult the task was likely to be, whether she would bleed, how much pain she would have to endure.

Of course, it's every man's dream to be giving a young lady her very first fuck. I knew I was up to the task! And Debbie certainly wasn't the first girl I would be deflowering -- or even the first girl in her school class that I was to deflower! Not that she realised that!!

I'd explained to Debbie that I would act slowly and be as gentle as possible getting the head of my erection into her vagina. I'd probably then push down reasonable quickly and thrust as deeply as possible into her, before withdrawing and repeating entry and deep penetration several more times to ensure that she was 'fully opened'. Then we'd try to make love to ensure she received her first-ever deposit -- and a good generous deposit -- of cum.

Debbie knew what to do. She submissively lay on her back and spread her legs.

Allowing me to climb on top.

By now she was very wet inside, obviously quite eager (if very apprehensive) to receive her first prick.

She helped position the tip of my now well-engorged shaft at the entrance to her love tunnel...and I started, ever so slowly, to push it down.

I could feel her tensing. She let out the slightest of yelps. Debbie was obviously feeling something!

I dropped myself a little further. "Aah!' she responded.

I reassured her that she was doing well, and in seconds would no longer be a young virgin.

I withdrew my erection a millimetre or two then pushed it down slightly. Again, I could feel her tensing and she yelped some more. So I held everything steady for a few seconds.

Then I drove my shaft rapidly downwards...and pushed down hard on the entrance to her love tunnel.

I was fully in...

And, for the first time ever, I felt what can only have been her clitoris pushing against my groin just above the base of my penis. How unusual that felt.

But how refreshingly erotic it felt!

As I held my erection deep down inside Debbie (suddenly realising the Doctor had just Done Debbie!), I fleetingly wondered if Debbie would, whenever she would be having sex, receive a little 'something extra' from having been blessed with that oversize clitoris.

I completely withdrew from her love tunnel and, unnecessarily, announced "well, your virginity has gone!"

A glance down at my erection revealed some blood. Not much blood. Just a trace.

"And you've bled, which is good," I whispered to Debbie.

I'm not sure why I had added that 'which is good' bit -- other than to confirm to myself that I had -- without any doubt whatsoever -- just stripped another young girl of her virginity.

I thought about wiping the trace of blood onto the sheet...and then, in a traditional manner, hanging the sheet out for the neighbors to view. But I didn't, thinking to myself that displaying bloody sheets after one's wedding night was really an outdated cruel practice -- surely, for the young women involved, a psychological trauma equivalent to the physical trauma of being subjected to something like a ritual infibulation.

"I'm coming back in again," I quickly informed Debbie. "Ready?"

She was. Her legs were still well-spread, she was willing to guide my erection back to the entrance to her vagina. And she seemed happier this time as my erection penetrated her still-taut tunnel.

Thrusting followed. Quite a bit of thrusting, as I was determined to hold my ejaculation until I was well-and-truly satisfied that Debbie had received a 'really good first fuck.'

There is no way Debbie could have come away from that first fuck not appreciating what it feels like to be inseminated. I absolutely exploded inside her -- uncontrollably squirting, squirting, squirting cum where nature intends it to be deposited, and undoubtedly leaving Debbie with that wet feeling that females, I am told, so enjoy.

So Debbie must have been a reasonable fuck. But, there again, to any guy, deflowering a young virgin is always the most enjoyable of pursuits!

As we lay in my bed afterwards, I gave Debbie a huge hug. Partly for allowing me to be the one who had bled her, partly because I felt sorry for what had happened to her in her past.

I also asked her if she was sore between her legs. "Not really sore, but I can feel something down there," she replied.

"That's probably the muscles around your vagina that have been stretched for the first time trying to relax again," I advised. "Like all muscles in your body they should be regularly exercised, so my suggestion to you is that you now try to work them as often as possible...if you know what I mean. And I suspect you'll really enjoy that!"

Debbie had promised me that she would rapidly follow her sexual initiation with a session in bed with some other young man. So I suggested that, before dawn, she practice on me what she would be saying to that young man: "I need you to do a favor for me. Please, will you give this girl a fuck!"

She didn't quite say that. "John, I'm ready for more," were her actual words!

Once again she lay on the bed in submissive pose, legs splayed.

I had to explain that it didn't quite work like that. She would first have to help transform my little man into a stiff, much bigger man...and together we would have to ensure she was made really wet from the anticipation of what she was about to receive.

I suggested that perhaps both of us should engage in a little oral. So she gave my symbol of manhood a good sucking while I took her most feminine part into my mouth and did what I could to pleasure it with my tongue.

As my entering her did not have the same urgency as it had had earlier in the night, I also played with her clitoris and fingered her g-spot for some time.

I started with her clitoris which, after a short while, I could distinctly feel had significantly engorged. I had been taught the name for this aroused condition is priapism, that in some women it can occasionally persist -- painfully -- for some days, and, had light been available to me at the time, I should have also noticed a darkening of Debbie's labia and clit, and an engorgement of her labia.

"Your coochie is a lot bigger than it was, as I hope you can feel," I remarked. Her response was a simple "Mmm!"

And, as her clit was engorging and erecting, I imagined Debbie -- or should I say a very much lither model of Debbie -- walking towards the female dressing room of a swimming pool in one of those wet, sheer, body-hugging swimming costumes with the outline of her priapismic clitoris clearly evident through the just-wide-enough strip of fabric that runs down between her legs. What a contrast (and an eye-attracting contrast!) this would have been to the other nubile girls whose swimsuits down there usually give just a hint (an attractive hint, I must admit!) of their varying sized female slashes and labia.

I thought that, at some later time, I should ask Debbie if she felt there were disadvantages of having an obviously oversized clit.

I particularly enjoy engorging girls' Skene's Glands by simultaneously providing clitoral and vaginal stimulation, and then squeezing the fluid that has accumulated out and into them -- helping fill the girls with additional warm wetness as a prelude to penetration. So I continued my play inside her, around there.

Debbie was fairly quiet as I fingered her. There were no "ooh, that's nice" or "keep going" types of comments from her. But she did, involuntarily, buck and twitch a little as I stimulated her, making me wonder at one point whether I had actually brought her to orgasm or, if not, how close she had actually come to experiencing one.

Having got her really wet again, it was time to re-enter Debbie.

I again positioned myself above her, and she helped direct my now very-erect penis into the entrance of her love tunnel.

Debbie was still tight, but the passage in was very much easier...and, quite obviously, very much more pleasant for her.

Again, I could feel her clitoris connecting with my body just above my penis, so I tried pushing hard against it as I completed each downwards thrust into her vagina. She didn't object and, from what I could tell, seemed to enjoy the added stimulation she received from this whilst we were coupled.

Then, for the second time that night, I gave it to her: a good, deep load of cum.

Debbie seemed satisfied, and particularly satisfied that she had, at long last, lost her virginity. And she told me she was pleased with this...and, that her first experience of sexual intercourse had been "not too bad."

I'd been pleased, as guys' put it, that Debbie had now been 'cured' of her virginity. And, ego-wise, I was delighted that I had been asked to do the deed.

But, to be quite honest, I'd much preferred the 'popping her cherry' experience I had much earlier had with Debbie's classmate Grace...and, as far as enjoyable fucks are concerned, I've yet to find a more satisfying fuck than those now provided by Rebecca, another of Debbie's schoolmates.

And, strangely, there was something else I couldn't get from Debbie because of her protruding clitoris.

I really enjoy the experience of being able to cup my hand over a girl's pudenda, just to feel the completely smooth but taught skin that runs down between her legs, and being able to rest the palm of my hand there for a few short seconds, in a way that sort of shields or traps her little box...and, then, following this by slowly retracting my hand upwards towards her belly button having first dropped my middle finger slightly into her clitoral cleavage. This is a real turn-on because, as you've probably guessed, the silky smooth, yet tautness, of a girl's skin in that area and the gentle gradual feminine curves in that area down between her legs is, to me, the most enticing, the sexiest area of a girl's anatomy. And, as a result, I 've certainly had Grace and Rebecca's twats cupped in the palm of my hand, and the areas up to their clitoral hoods being slightly stretched by my middle finger, on many an occasion!

Had Debbie been a little more sexually appealing to me, I might have suggested we re-engage regularly, and that I become her sex tutor to ensure she became more sexually proficient and be introduced to some other different ways of receiving 'it'. But she had (or I hoped had) a date with another guy -- so there was really no reason at all for me to currently pursue that possible opportunity.

We ended the night having a shower together, giving me the opportunity to once again fondle and gently squeeze her unusually prominent little 'female erection'...the one thing that will remain as my most vivid memory of that one-night stand, during which 'unremarkable' Debbie had sought - and accepted - her very first fuck.

Debbie, though, might not have been so pleased that I would most remember her because of her distinctive box!!

* * * * *

But talking of dear Grace, as I was. A few days later I received a phone call from her. Could she come around on my birthday (in a couple of weeks' time) to help me to celebrate? After a lot of thought and research, she had decided to share something very special with me - as this year's birthday treat - that I had been asking her for, for quite some time. I immediately said "yes!" And I'm presuming it will not be a birthday cake with a cherry on top!!

MrsJ
MrsJ
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Lee2012Lee20129 months ago

Poor Debbie. All guys should realize that even “homely”, or just plain, girls need a good bonking from time ti time. You could get lucky by finding one so appreciative, she’ll fuck your brains out. Took one to her senior prom, had a blast dancing and rubbing on the floor. This chick had a killer body that she kept hid and surrendered her virginity and kept me ‘up’ all night. 4* only because of Debbie

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