"Sincerity - If you can fake that, you've got it made." Attr. George Burns. 1896 -- 1996.
Any and all caveats you can think of, and those you can't, apply.
Although the following can fairly be described as 'An explicitly, possibly clinically, detailed shagfest it does take its time getting to the meat, so to speak.
This story was written by a Brit OAP coffin-dodger, it contains a sprinkling of Brit slang and specific Brit references. I hope that these do not seriously disrupt any under 40/non-Brit readers. Google is your friend.
----- Present time -----
Tap, tap, tap. The sound jolted Paul out of his reverie and threw him back into reality.
"It's happening, it's really happening!" thought Paul "There's no backing out now; I've got to answer the door." But Paul was frozen like a Deer in the headlights, his brain urged him on but his legs refused to cooperate.
"I'll ignore it and she'll go away and I'll tell mum that she didn't turn up. But she'll never believe me and ..."
----- 12 days earlier -----
Jean, Paul's mother, mentally girded her loins and knocked on Paul's bedroom door. "Just a minute!" came the expected response followed by sounds of furtive fumbling and muttering. Finally the sound of the computer monitor being switched off preceded the opening of the door.
"What is it mum?" muttered a red-faced flustered Paul "I'm busy right now, can't it wait?"
"No Paul, it cannot" said Jean, "We are going to discuss sex, or rather the lack of it in your case, whether or not you like it" and so saying she pushed her way in, locked the door and faced her son who, for once, was struck dumb.
Jean continued "We can do this one of two ways, either I can have my usual rant and in the end nothing will change. Or, and this is how it's going to be; we can have a grown-up discussion by me stating what has brought this situation to a head, agreeing exactly what the problem is, how it affects both of us and what we are going to do in order to sort it out. Do I make myself clear Paul? A one word answer will do."
Paul was totally nonplussed, he had never heard his mother talk in such a way before, and especially mention the word 'sex'. He did not know how to reply so Jean said "I'll take that as a 'yes' then.
"Believe me you are not going to like the first couple of points but stick with it because you might, just might, like what follows. You can have your say when I have finished.
"Let me start by saying that I accept that you have a very deep-seated shyness, a value of perceived self-worth hovering around zero and a level of confidence that is well below the horizon. When combined these three conditions not only reinforce one another but have reduced you to a virtual hermit. Apart from attending school and the occasional visit to the dentist you spend the rest of your time locked in here trawling the Internet for porn and wanking yourself stupid."
This last remark produced a distinct change in Paul's demeanour. Initially he was outraged that his mother was haranguing him about such personal and private things and also using such words as "wank", but deep down he knew that the essence of what his mother was saying contained more, much more, than a grain of truth. Whilst he desperately wanted to retort, perversely he also wanted, no needed, to hear more."
Jean continued "You are a healthy, good looking and virile young male who is surrounded at school by healthy and sexually attractive females, you should be all over them like a rash. I see them parading themselves in public, showing off big tits in crop tops, and bum cheeks hanging out of their hot pants. Rhetorical question -- why do you think they are doing that? To attract a partner for the purposes of sexual gratification is the answer, and if I were a male of your age I would be up there like a rat up a drainpipe shagging each and every one of them that showed the slightest interest in me. Thoughts?"
Paul had enough between his ears to know that things like 'You don't understand me' or 'You're just making it worse', in fact any form of prevarication, would just not cut the mustard so he decided to look his mother in the eye and address the elephant in the room.
"There are two things that I can't do" Paul replied "Firstly I cannot disagree with a single word you have said and secondly I have really struggled for a long time to try and sort myself out but with no luck at all. Every time I have approached a girl either I find myself unable to speak or if I do say something then the girl just laughs at me and neither of those outcomes tend to lift my confidence, I am in a downwards spiral and I don't know what to do. I take it that you have a possible solution?"
Despite her happiness at progress made so far, Jean knew that the ball was now well and truly in her court. "Before I tell you what my plan is I think I will have to tell you a secret that must not leave this room, do you understand?" Paul nodded and Jean continued.
"I left school at age sixteen, by nineteen I'd persuaded Grandma into lending me a fair amount of money to go into partnership with another girl to own and run a brothel. After about five or six years and a lot of work we had a high-class successful Escort Agency that made us, and the girls, a lot of money. Then I ..."
Paul interrupted his mother by saying, in a low incredulous voice "You were a prostitute?"
Jean wasn't sure if she would have been happier if Paul had thrown a fit and shouted and yelled at her, but there was no way back now so she ploughed on. "No Paul, neither my partner nor myself ever made our bodies available for sexual services. There is a lot more work involved in running a good Escort Agency than you can possibly imagine, we would never had the time for that even if we wanted to. Let me finish, then I met the man who became your father and things had to change, after a bit of haggling my partner bought me out and apart from the occasional email and phone call we split company".
"I hear what you're saying" said Paul "But how does all of that relate to your plan?"
Jean did not know whether or not Paul was being deliberately obtuse, not that it really mattered because she knew that the point of 'shit or get off the pot' had been reached.
Taking a deep breath she said "My business partner always had an excellent eye for the girls that were willing and able to cater to a niche market, the 'wham bam thank you ma'am' trade is the bread and butter that very few agencies are able to ignore, but the jam is in the area of specialities. During the last couple of years of my stay our agency built up something of a reputation for servicing the 'inexperienced' boys and girls, all of legal age, who needed safe, guaranteed, practical and uncomplicated guidance in all sexual matters, you could call it Sex Education on steroids. You may think you are unique in having sexual problems, believe me sweetheart, you are one of many.
"Even today with the advent of the Internet and all it supplies there is no substitute for hands-on experience. Young girls wanting to explore lesbianism with no comebacks, young boys like yourself desperate to gain knowledge, confidence and experience, but for various reasons are having real problems.
"I propose that for your 18th birthday I arrange for you have a hotel room and an escort girl for twenty-fours hours, what do you think?"
Paul's 'gast' was, not to put a too finer point on it, completely flabbered. Stuck for words he just stared open-mouthed at his mother. Although his mouth wouldn't function his brain was working at light speed creating imaginary scenes and incredible possibilities.
As if she could read his mind Jean forged on "I'll make sure that she is very pretty and has really lovely big tits. She won't be much older than you but she will be very experienced in encouraging young boys to enjoy the female body, also showing you how to make sex satisfying for the girls, because the better the sex for them the better the sex will be for you.
"I know that losing your virginity is something that should happen naturally but if you can forget that she is a prostitute, let your mind wander upstream and just concentrate on all the wonderful things you can do together. A warm, willing, firm, young female body and a mind that knows what you want to do and will ensure your enjoyment, also do things for you that will blow your mind."
Without waiting for any reply Jean said "I've had my say and you've heard my plan, take it or leave it, the choice is yours."
Paul was within a nanosecond of exploding with rage at the outrageous suggestion that he should go with a prostitute, but then inside his head he replayed just two words recently spoken by his mother, 'BIG TITS', and he was instantly transported back in time to an incident that happened six months ago.
He was walking along a corridor in school that was deserted save for himself and a girl looking at a notice board and taking down some notes, the girl was Helen Foster. Although Helen did not have a face like a welder's bench and had not hit every branch when she fell out of the ugly tree, she had come into contact with more than a couple of fairly robust twigs, however, and it was a very big however, she had the most magnificent pair of breasts in the entire school.
All red-blooded males and not an insignificant number of females took every available opportunity to scrutinise the miracle mammaries at close quarters that jutted from her chest. The consensus of opinion was that they were D cup that gave, because of her slight frame, the appearance of DD/E cup. This was confirmed by a girl in Helen's class who had accepted a suitable bribe to supply all information regarding Helen's bra. Apart from cup size, extra details provided stated that it was not underwired or padded, was of fairly insubstantial construction and made out of flimsy material that was unlikely to provide much, if any, in the way of support or uplift.