© March 2002
I drove thoughtfully westward in the gathering dusk of a winter's evening, windscreen wipers beating a steady rhythm against the light rain that was falling. I let my mind cast back to the start of the events that would culminate later that evening.
It had started with an e-mail from a married couple who had found and read one of my earlier stories. We exchanged letters over several months and it became apparent that they were very keen to explore having a third person in their relationship, even if only once.
I remembered some of the letters that had gone back and forth.
I warned them that a threesome could be dangerous, but they insisted that they had weighed up all the pros and cons and still wanted to give it a try. They went further and asked for help in the scenario.
It quickly became apparent that Jack and Sheila had covered a lot of the problems and still believed that the situation could be managed safely. Very simply, Jack was turned on by the thought of another man making love to Sheila while he watched. Sheila felt that she loved Jack enough to allow this to happen. They both, foolishly or otherwise, believed that this was a situation that they could control as they wished. I was not so sure.
Somewhat to my horror the first candidate Jack considered for Sheila's lover had been a co-worker who had tried to hit on her more than once in the past.
Patiently, I explained that he was probably the worst of all choices--if it all went pear-shaped they would be unable to avoid each other. They quickly decided that the tryst would be with a carefully picked stranger.
About this time Sheila started chatting by e-mail in her own right. She wrote that she was curious as to how, as a writer, I would set up a similar assignation in one of my stories. I had taken a deep breath and just written the reply to both of them off the top of my head.
The e-mail looked like this:
Still in the same town but a lad, 19y/o, has 'copped on' to Sheila a couple of times when we have visited the same venue.
Now this might seem more interesting, you did tell me I think, but I can't recall your age?
Seems very shy and unsure of himself. Sheila has 'felt' that he was interested her.
Wondered if, perhaps, I gave them some time together, without me? and then introduce him to the fact that I would like to be involved.
LOL - but not unkindly. If he is a little shy, you may scar him for life if you do that. Unless Sheila wants to 'break in' a virgin (?), someone with limited experience, although interesting might be a little frustrating.
Would prefer to be with her, on this first time experience.
I think in your shoes I would view that as not 'a prefer,' but would want it to be 'a must' unless it was unavoidable. As much as anything else it is 'safer' for Sheila. Horny young men can be difficult to persuade that you meant to say no. The presence of an SO would reinforce the word a lot!
Difficult, is it not?
Yes - prudence suggests you must be there, practicalities of trying to persuade some one of that age to participate may well mean that you find him very worried about your presence. I know you have told me that MM doesn't interest you Jack, but MF(M) is very close and could well frighten him off.
It really is only in fiction that a horny young man appears like a knight in black armour and is available, willing and knows not only how to participate, but also when and how to exit the situation.
Suggestions, any little help?
Rather than trying to use subterfuge or luring him into a situation, there is another way, another alternative.
The three of you sit down over a drink and you put a 'proposition' to him. Sheila wants to be in a situation where she has a heavy petting session, maybe leading to a bedroom/wherever occurrence that might even lead to a full-blown sex session with a third party while you watch. Explain it as just a whim, just a kink that she wishes to try and perhaps experiment with. You are happy to go along with this as you love her sufficiently to do so. Stress the maybes' and the let outs so that if either you or Sheila become sufficiently unsettled then everything stops.
No penetration without either full assent from both of you or without protection being worn at all times.
Lay careful and detailed ground rules and stop signs between you, Sheila and him, so that there is no ambiguity and can be no unpleasantness.
I would suggest that any alcoholic loosening up is limited to a bottle of not too strong wine. That gives a couple of glasses each, without either harming performance or getting so pissed that control of the situation is lost.
The last thing is more important and what made the previous scenario with someone you knew so potentially difficult/dangerous. You do NOT meet at your house/flat/residence or whatever. That way he does not know where you live and cannot cause problems or difficulties in the future. Buy yourselves a room in a motel for the night. They come with a double and single bed, TV, warmth, shower with unlimited hot water towels and so on. They also are anonymous - you to him / him to you - and the staff, once you have paid for it in advance, couldn't give a damn what you're going to use it for. Only you know that, and only you need to book, sign in and pay for it Jack. It is also neutral ground so no-one gives a toss about territory.
If we had decided that the three of us were to be involved, then that is precisely the scenario I would have suggested to you.
Sheila--I appreciate that I am probably the same age as your parents so I can understand that not being a dreadful turn on. Doesn't mean that I couldn't either try the suggestion out (older men just might be a turn on!) or that it's a rule out for the future. A more mature person with nothing against other males - while not a homosexual the scenario of two men and one woman is one I find interesting.
Jack mentioned, I think, the situation where he might be involved in helping the other man enter Sheila or whatever - most red-blooded males I can think of would find that both off-putting and worrying if not a direct turnoff, as would/will most folks in a threesome anyway. That thought or idea doesn't bother me. Someone once said if you shut your eyes and someone gives you a blowjob you would be hard-pressed to tell who or which sex was the giver.
Don't know as up to this point in my life I haven't tried that yet - but it sounds a pretty factual statement to me!
For what it's worth that's my two cents. But by sitting down and talking things over before hand you, in setting clear rules of engagement (military style!) are in full control of the situation right from the start. For both protection and safety I think that is the only way to go. As well as that if the other guy doesn't like it, you say 'fine' and walk away without harm being done, an evening being spoilt or wasted or the threat of physical harm being threatened because "effin hell I didn't know that's what you wanted to do!"
Sorry for the nasty language Sheila - but you know what I mean.
Jack, Sheila - I think that makes sense. I think it is a relatively easy way to progress. I think it has the maximum potential to be fun, because every one knows where they stand and I think it exposes both of you to the minimum amount of risk.
And NO! Before you ask I have not done this in the past! I have just given it a little thought in case you called my bluff and invited me. It is what would have minimised the risk to all three of us in that situation.
I can't think of anything else, but that doesn't mean that there isn't something I may either not of thought of or that you may want to play differently. The only thing that I would insist upon is the the Motel style accommodation. I only suggest that because I know the size, style and cost of the room in advance. Given that there is room for you to sit well in the background Jack, it might be the best fifty quid you ever spent.
With much love and thought for a safe outcome - and I insist you let me know both in advance and that you also recount things, either individually, or with a joint letter on both your feelings afterwards.
All had then gone quiet and I assumed that a decision had been taken not to proceed. Then I got a terse note to say it had failed.
Not a lot else, so I had asked for a little more detail, 'if they cared to share things.'
They had. The note had came back almost by return:
As best as I can relate the fiasco of Saturday 21st November.
Unfortunate that the 19 y/o is also called Jack -- perhaps we will refer to him as 'the lad' to avoid confusion.
We had a nice meal at home, retired to the lounge where, before long, Sheila and the lad were in a sort of cuddle. It is this that had persuaded Sheila and myself to carry on. He seemed to have no problem with kissing and cuddling Sheila in my presence (Great!!). It has always turned me on seeing them at this stage.
So, Sheila and the lad cuddling, I then said I had to send off some e-mail.
Went to the study, where I just stood and shook, imagining what might be happening. It is a feeling which is quite indescribable.
About 10 minutes later, Sheila came to me and said that the lad was going home. And he went home!
Gathered from Sheila, later, that he had touched her breasts under her tee shirt (no bra) and she had felt that he was hard.
At this point he excused himself and decided he was going home.
.... There is more of this story ...The source of this story is Storiesonline