A Damascene Sexperience

"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.

Once the technical details of the bra were made common knowledge a fierce and prolonged debate began concerning fake vs. real. The cohort of females who were made up of the 'fried egg' brigade were adamant that they were bolt-ons. In the main B cups were ambivalent and C cup and upwards tended towards 'no comment'. The vast majority of males, including Paul, couldn't care less, real or fake they just wanted to maul them around, and/or motorboat, and/or tit-fuck etc.

As Paul got nearer to Helen he slowed down wanting as much time as he could get in order to drink in the side-on profile of her stupendous bosom. Although Helen had not been dealt the best hand in life she knew how to maximise her assets. Everything she wore above the waist was always skin tight and her back was always ramrod straight, so much so that she made a Grenadier Guard look like the Hunchback of Notre Dame. Combined with a hardly perceptible twitch of her hips every walking stride she took that produced a subtle hypnotic shimmy/jounce of her breasts, and you had a spectacle that regularly reduced a busy noisy corridor to a deafening silence with all eyes fixed on a solitary person.

Legend has it that a teacher, Miss Carson, who incidentally had a figure that would make an ironing board look positively voluptuous, once approached Helen and suggested that perhaps she might consider wearing less flattering upper clothing, Helen said nothing and stared fixedly at Miss Carson's chest. When asked what she was looking at Helen replied "Nothing, nothing at all" and walked away.

Whilst the inevitable report that landed on the Headmaster's desk did not fall on stony ground, it was certainly kicked a fair way into the long grass.

As Paul drew level with Helen she turned away from him and took one step forward, slipped and fell backwards, arms outstretched right into Paul's path. Acting purely on instinct Paul caught her just above the waist, as gravity kicked in and her body slipped a little further down Paul's hands were perfectly positioned to cup her breasts.

Paul experienced the most exquisite three seconds of his life thus far, his hands were full to overflowing with firm pliable female flesh that he gently squeezed. And then it was over, Helen pulled herself out of his embrace and facing him said in a cold and hate filled voice "Thank you for saving me from falling, but I'd rather be in hospital with concussion and a fractured spine than have my tits pawed at by a miserable fucking pervert like you."

Paul barely heard what Helen said, his mind was still replaying those fleeting moments when he held the best tits in the school. This was going to be the most valuable item that he had ever stored in his very sparse wank bank.

"EARTH TO PLANET PAUL, ARE YOU RECEIVING ME, OVER!" Shouted Jean.

"Yes mum" said Paul "I hear you, but it's a lot to take in, and how can you be so sure that she will ... and that her, you know ... will really be big?"

At this point Jean knew that if she handled the next five minutes correctly that although it would not exactly be 'a walk in the park', she was confident that Paul would agree to her plan.

Choosing her words very carefully Jean said "Losing your virginity is a very important event, depending on who your partner is it can be a wonderful experience, but also it can be something of an anti-climax. Of course it is better if both parties know and have some level of affection for each other and that things reach a natural conclusion, but there are cases, and I believe that you are one of those, where nature needs a helping hand.

"Can I absolutely guarantee that you and the girl will click and that she will deliver what you need and how you need it? Of course I can't, but I do know that in all walks of life there are girls that positively thrive on taking virginity, their sexual gratification is not solely physical, in the main it is mental, not only knowing that they are your first but that they are in control of the pleasure you are getting, and the more pleasure you get the more pleasure they get. It's win-win really.

"It is not an everyday occurrence that a 'V-girl' takes up prostitution, but when she does, and gets a good reputation she becomes a valuable commodity in the paid sex world, she can earn a lot of money and get her rocks off in the way that best pleases her. So you would meet a girl who, in an odd sort of way, you can supply her with exactly the sort of sexual experience she craves, and she gets well paid for the privilege. It is very unlikely that she would deliberately upset you.

"As for the size of the girl's tits, I take it that you would like them to be natural and big? Well I can guarantee D cup minimum, more likely DD/E, is that Ok?"

"When you put it like that it does sound like a plan" said Paul "But if there were any other way ... What do I do if we don't get on or something goes wrong?"

"You tell the girl to leave and you come home" replied Jean "It really is not your problem. So are we good?"

After a long pause Paul replied "We're good."

"Great." Said Jean and opened her phone.

"Sarah, it's Jean, You wannabe old prossie how are you? ... good to hear ...

[ A couple of minutes of chat ]

"Are you free on Thursday at around eleven O'clock? ... I want to talk something over with you, how about if we meet at the greasy spoon on the corner of Lyle street? ... I'll tell you when I see you ... Of course I'm paying, you tight-fisted cow, see you. Bye."

"Right" said Jean unlocking the door "I'll keep you posted."

----- 10 days earlier -----

After a bit of catching-up and general chat Sarah looked Jean in the eye and said "Jean, we parted company amicably a good few years ago. I have no problem with that, there were very good reasons for doing so, then out of the blue I get a phone call from you inviting me out for lunch, so my question for you is, why am I here?"

"Before I answer," said Jean, "I have a question for you, are you still in the business?"

"Well," replied Sarah, "I didn't see that one coming, but to answer you -- Yes, well and truly still in the business. From what I can make out you're not exactly destitute so why do you ask?"

"I don't ask for myself but for my son Paul, and it doesn't concern him wanting to join the business in any way shape or form, but rather to do business, or to be more precise for me to do business on his behalf," After a slight pause Jean continued, "To be blunt I want to hire the services of a prostitute for my son."

Sarah was a bit taken aback, "You are full of surprises Jean. You certainly have my attention, but I need to know a bit more before we can continue, and why contact me? There are hundreds of agencies and many independents who would be more than happy to take your money. So firstly, why me?"

"You hit the nail on the head when you said that agencies and independents would be willing to take my money," stated Jean, "I've been out of the trade for nearly 20 years and so I have no clue who are the goodies or the baddies anymore. Money is not the problem, as you rightly said I'm not exactly destitute but my concern is that my son is not ripped off with poor service and does not get the proper attention he desperately needs. Why you? You're the only person that I trust and has the ability to find the girl that you know will fulfil his needs."

"Ok, I'm flattered, that's the basics out of the way," replied Sarah, "Now for a bit, or rather a lot, of relevant information. Why does your son need a prostitute? Why can't he just chat up a civilian girl and get his rocks off in the usual way? Does he want some specialised services that aren't usually available? Is he handicapped in any way? Come on girl spill the beans, all of them."

Jean sighed and then braced herself. "I want you to believe me when I say that these are not the ravings of an over protective mother. My son Paul is eighteen years old, or rather will be eighteen in just under ten days' time and is a guaranteed virgin. He is a typical male teenager with raging hormones and wanks at least five times a day.

"He is handicapped but his problem is not physical, his bed sheets are proof of that, it is purely mental. He is painfully shy, and I really do mean painfully, around anybody, but even more so around girls. He is starting to stammer, refusing to go outside his room and I fear that self-harm is next on the list. He is in desperate need of a girl who can show him that not only do girls have as much interest in sex as do boys, but more importantly also give him confidence and self-esteem around the opposite sex.

"We have talked around the subject of sex and he was desperate enough to open up a little, but quite naturally he is only willing to go so far down that track with his mother."

"I'm so sorry to hear about what your son is going through," said Sarah, "But are you really sure that paid sex is the right way to go about sorting out his problem? You know as well as I do that things can go wrong, even badly wrong, and what does Paul think about all this?"

"After a long pause Jean replied "If I'm being honest then I have to admit that it is not the best answer but I really think that I have to do something, and I know that you can get me the best girl for the job, it will be the least worst solution. However, I'll come clean and say that I have already set the wheels in motion.

"I had a long talk with Paul a couple of days ago, not something that I would want to do again, but on the plus side a lot of air was cleared, on both sides. He owned up to having a problem, a real problem, and eventually he agreed that although my proposal was not exactly the perfect answer, it did address the problem head-on."

"Well" said Sarah "No pressure then huh? I'm going to need some intimate details concerning requirements, the more detailed the better, and I don't need to tell you what they are."