[GillT]

Hi everyone,

I'm a long time reader but a first time poster. I'm after some advice.

I'm a 37 year old woman, married to a great guy (Graham) and have a couple of young kids (7 and 4). One of my good friends lives next door and has a 18 year old son who babysits for the kids. Last week when I was going out for my Christmas party and my husband was going to his separately. The babysitter came over just as my husband was leaving. My taxi was a little late so we got chatting about this and that. He said he liked my dress, and I made a joke about how it was a little loose and I was frightened it was going to drop down and leave me naked and embarrassed. Now I know I shouldn't have really made the joke, but it was from an innocent place.

However, his reaction really surprised me. He told me not to worry and that if it did happen I shouldn't be embarrassed. I told him I wasn't a spring chicken anymore! He then told me he'd made a list of 50 girls he knew that he'd like to see naked and I was in the top 5! Then to prove it he got out his iPad and showed me the list! And there I was, number 4! So he clearly fancies me! Just then my taxi arrived, and I got up and left.

I spent the whole night thinking about that list. Firstly I thought it was a bit sad that he had a list like that, I don't think he's an experienced guy and a bit of a geek which explains it a little. Just a fantasy thing. I won't lie, I was also flattered. Now let me set something straight, I am not going to sleep with the kid, I couldn't do that to my friend, and more importantly there is now way I could do that to Graham. However, I don't think it would hurt to give him something to help with those fantasies! Graham and I have taken a few sexual photos so perhaps I could allow him to tick off number 4 on his list! Although, I am worried that body won't really be what he's expecting (stretch marks, cellulite etc.) so I was thinking of giving him a little souvenir, perhaps a pair of my knickers?

Let me know if giving him either a photo or something is a good idea, and also if any of you have had similar admissions from friends children (or legal age)!

Gill x

[atskitty2]

I can understand that's very flattering.
I'll answer your question only, without elaborating, unless you ask for more info. I don't think it's a good idea to give this kid a pic or items or any more encouragement without talking to Graham.
Keep us posted and good luck!
Are you in England?

[GillT]

Thanks for replying atskitty2, Yes, I am in England. I would love some elaboration if you would care to give it.

I told Graham about the list, he laughed (I think at the list, not that I was on it). I knew he would be fine with it as we've had a couple of threesomes in the past, and whilst we're both a bit busy with the kids and what not for sex, we still talk fondly about the times we had the threesomes. I think I want to do something to not to encourage, but because if I was a 17/18 year old who had no confidence with women this might really give him a boost. I would make it clear that there would be nothing between us.

[atskitty2]

Well, I think it's a bad idea in general, but given your history and Graham's openness that does steer my opinions differently as well.
I think being honest and forthright with our partner is first, and you did that and if he is unoffended by your sort of flirtation with this kid, then that settles my first apprehension.
The age thing bothers me a little, but not that I think it's morally wrong, as he is old enough for dating and relationships. I think that immaturity may lead him to think more, even with your efforts to be clear that this is just a picture. I think it isn't really your place to see to his sexual/fantasy needs. He may interpret your actions very differently than you intend them, and even differently than you tell him.
I think there are probably better ways to boost a young man's confidence.
I think you should be cautious, as you simply don't know where those photos may end up, or who's hands they may fall to. Are you OK with all his friends seeing the pictures too?
Are you OK if/when his parents find out?

I just think the potential for this turning into a bad scenario is pretty high.
Please realize, I say this with our american culture in mind. I realize it's quite different there, but I wouldn't, if I were you.

I would be flattered but I think the boundaries are important to keep, especially since he's your children's caregiver.. What if your kids found the pic on his iPad while they were in his care?
I just keep thinking of more...

So, lest I sound harsh or judgemental, I will close by saying that I caution against it. But if you were my friend, and you do it, I will still love you and have a good laugh afterward with you...and I'd also let you vent to me without saying "I told you so", if it went badly.

[GillT]

I think you might be right. The biggest thing I worry about is the picture ending up somewhere else. Obviously, I trust him to look after my children for the occasional evening, but this is different and guys of that age can be immature. Which is why I wondered about giving him a pair of my knickers or something. I know it sounds mad that I'd want to do anything, but I think the flattery has turned me on a little, and maybe the idea of him getting off thinking of me also excites me. I guess I should act my age and just leave it though. Thanks for your advice Atskitty and also for not judging me. That certainly means a lot.

Out of interest are you a woman or a man?

[atskitty2]

I'm a 41 yr old divorced female. I can totally understand that it is flattering and would be arousing. I have been called lots of complimentary names and phrases by young men and teenagers, so I do understand that it can be very boosting to our sensibilities as busy women. These days it seems trendy for the boys to find older women attractive, and they are unashamed to make their lusts known, it seems. Enjoy the compliment, as I do and leave it at that, as I do. Some boundaries aren't worth crossing and some risks are simply not worth taking.
If I may offer an alternative?
You seemed to imply that things are a little lacking w graham because of how busy you both are. Maybe I mistook that comment...but if so, why not send HIM a suggestive pic instead, unexpectedly and spice up things with him? You surely can trust him much more...and it may be just what you both need.

[GillT]

Yeah it's something that we have been making an effort with over the holiday's. I handed him my thong that I'd removed at a party we were at the other night, which drove him crazy! Unfortunately once we got home our daughter was up unwell so nothing happened in the end. He's asked for another FMF threesome which I am happy with in theory, although we haven't done it for 10 years so I don't know where we'd find a woman up for it. Always scared to ask single friends. One thing I was going to suggest is anal. We've never done it,but I'm not sure if it's something that women get any pleasure out of. I know some hate it and others don't mind, but I've never heard anyone say they actually enjoy it.

Thanks for the suggestion - it's sweet that you care.

[atskitty2]

That's too bad about after the party
There are some threads here about anal sex experiences I'm sure, as well as info about hooking up with a willing third party-probably old threads, but nonetheless useful info.

Best of luck...keep us updated!

[DreamP346]

I also agree with atskitty. There is so much potential for something going wrong. If it was a random young man met during a vacation, I would say go for it. But since he is involved with your kids, I wouldn't risk it. If it turns you on so much, ask your hubby to do a teenage role play where you are the milf and he is a pool boy. Or maybe roll play an imaginary threesome (double penetration with toys) imagining that this younger man is there as well as your husband.

[jen1447]

I agree with kitty and sp346 about the risks, which does nothing to explain why I think you should do it.

The bottom line is that yes, all the risks are there. However, the kid is 18 so there is technically nothing wrong with what you want to do. Benefits include you getting a major shot to your libido (I suspect you're downplaying how much the thought turns you on - I mean you came here to post about it, you must have been pretty moved), and the kid as you describe him may never have something else so cool happen in his life and would likely have masturbatory fuel for years lol. Also, a bit more philosophically, I'm always kind of depressed at the thought of surrendering to life out of fear or apprehension or just common sense. Would it be potentially reckless? Yes. But do we really want to go through life being constantly safe about everything? I don't think so, personally.

If it were me, I'd make a point of being available to the kid afterwards if he needed any other consideration. I don't mean sex, I mean if he needed clarification of the boundaries or what your relationship consisted of, etc. To make a gesture like that (whether it be photos or panties) and then just turn a cold shoulder to him might be kind of confusing. Basically I'd always maintain a "have fun with that" attitude while never really teasing him further about the prospects for me, and if he inquired about them (which he very well might), I'd be very clear about it not happening. Then I'd encourage him you go look at his pictures again.

It might also be worth it in the big picture to get a different babysitter, which would remove some of the potential conflict of interest. (You could tell him you figured he'd be too busy now lol.)

Congratulations on your thirst for adventure btw - I always love hearing about this kind of stuff from courageous women. A good, healthy imaginative mind is always an asset. Also the panties-as-gift thing is awesome. I've given and received a few pairs and each instance has been very precious. There's actually few gestures as intimate and thoughtful as panty gifting, just because they're so symbolically weighty.

(Oh, also handing over the thong like that is just plain hot, lol. Good job. )