[rcoreyus]

Age isn't a big issue, maturity is. You know the 18 year old and may have a feel for this. If he is mature and sexually experienced, then this could be a great fantasy for him. If he is less mature, or less experienced, what would be a great adventure for you might be too important for him.

A lot of people (men and women) just aren't wired right for casual sex. I have a female friend who had serious problems when she had what both agreed was casual sex with a friend of her's, but he started to take it much to seriously.

Other than those possible objections though, enjoy!

[jen1447]

Missed the anal question - there are a lot of women that like it, even love it. I'm of mixed emotions (as a rare practitioner lol) - it can be intensely pleasurable but the pain is also unavoidable. (I don't know, maybe if you were extensively 'trained' or conditioned it wouldn't be.) An alternative would be to introduce him to analingus first (on you), and then go from there. There really can't be one without the other, meaning lol that no one goes straight to having something long and rigid up your bum. It's definitely a slow road.

As to FMF threesomes, my own approach to that is not to sneak around lol. Look at it like it is what it is and that you don't really care who knows and your options will grow. If you want to go down the hidden alternative lifestyle dungeon road that's fine too, but yeah you'll have a tougher time finding candidates, and they'll basically be strangers, which is riskier. That said, if you have your mojo about you it's not real hard for a woman to 'score' other women in the right places. Look for lesbian/bi friendly bars and clubs in your area.

Good luck, and let us know how this all turns out. We like to hear followups.

[GillT]

Ahhh Jen, you've confused me even more now! I'd pretty much decided NOT to do it, but then I read your reply and you're right about a lot of things. And yes, I think I did understate how turned on I was about this! Being number 4 on this kid's list is incredible, most of the girls on it are probably 18, flexible and have **** still pointing north (although being a smaller Lady has helped me there). So maybe I should do something. I was thinking if I did do anything I could test the water with a thong first, see how he re-acts. If he takes it well and doesn't get carried away then maybe I could send over a picture or two. One thing though Jen, and you might be able to steer me in the right direction as you have some experience, if I give him a thong should it be a worn one or a laundered one?

What do you all think? I think if I do anything it would be wise to get another sitter though. Makes things a lot easier!

In terms of anal, I was masterbating the other day and tried a little anal play with myself and I really didn't do that well with it so it's off the cards.

Thanks for your advice everyone, I do really appreciate it, just a little confusing too!

[jen1447]

Haha, this is so cool. You pretty much have to do it now, don't you? Not knowing would just drive you crazy.

As to thongs/underwear, yeah, IMO it has to be worn, otherwise it's kind of just clean laundry. The ones I've given and received have always been, anyway. Also I have another tip, in case you weren't aware: if they're um, dirty in more than just the way your underwear normally is at the end of the day lol (and I assume that's kind of the point too), he should have some specific instructions on what to do with them after a day or so for best results. They should be rinsed (not washed or scrubbed, just rinsed) in cold water only and left to air dry. What happens after that is magical - they retain their scent pretty much indefinitely (seriously, I mean like forever), and any ....substances that would have potentially turned unpleasant after a while are gone away. It's an amazing win for panty-gifting.

My natural question would be, how to you plan on giving them to him? Just walk up and plop them in his lap one day, or remove them in front of him and hand them over? Etc. There are lots of possibilities there.

Also, I think it's a foregone conclusion that he WILL get carried away when you do it lol. I mean, almost any 18 year old would probably flip out, let alone one who doesn't get much action normally. So be prepared for that. It'll moreso be a question of if he modifies his behavior toward you significantly as time goes on. Also, giving him stuff in stages might confuse him about the nature of this 'one-time-only' thing, but I understand the need to go kind of slow.

Oh, on anal, I understand - that's usually the initial result. You have to go about it very slowly and progressively if you want it to work, so I would suggest that you continue experimenting during masturbation and see if things become more comfortable over a longer period of time before you give up on it. I'd be content to let you let it go except that it really can be intensely pleasurable for some people, so I'd hate for you to miss the boat on that from giving up to soon.

[GillT]

Wow Jen, I really didn't know a rinse and a dry would do that! But then again I've never exchanged underwear before! Is it something you do often? And do you "use" it when you've been given it?

I'm really not sure how to give them to him, yes it would be incredibly sexy (for everyone) to take them down in front of him, but I'm not sure. I was thinking of wrapping them up in a little gift box (possibly post-rinse treatment - I can't imagine washing will be his strong point) or something. And I think you're right about lots of little gifts, so maybe I pop in a photo or a memory stick with some naked pictures on too, so he has the full experience in one go!

I might give anal another go, but not just yet. I'm far more excited about the babysitter and my knickers!

[jen1447]

Sure hon, go with the flow. Just please don't give up on your bum just yet.

Without getting too raunchy (we really should have an x-rated forum here for really frank talk lol), yeah I've gifted a lot of panties, and received quite a few pair. In my lifestyle, it's actually kind of customary. As to using, um yes sometimes. But honestly for me it's moreso a memento than anything else. But's it's SO meaningful! It actually makes me kinda emotional just thinking about it, hehe.

The gift box idea sounds oddly charming lol. Have you given any more thought as to how to protect your privacy/security with the photos?

[Claret]

Can I cut to the chase here? I've been reading this thread and it's clear to me that you have already made up your mind what you are going to do. There is no ambiguity. My big question is, so you were number 4 on his list, why would you consider that the most flattering position? Who were the previous 3? If he could have any of the previous 3 would he move on to #4? I don't want to shatter your dreams here but I don't really find that to be all too flattering. I'd have to be #1 or nothing.

At 18 given your conversations he doesn't need a boost in his ego or his confidence - he's got that already. It's your ego and your confidence that would get the boost.

He is there in your house in a position of trust for your children. Why would you jeopardize that?

I guess I just don't get it.

[jen1447]

Wow Claret, you've got pretty high standards!

Personally I think #4 out of 50 is pretty impressive. Of course the reality of the list is fundamentally juvenile, but I'm pretty sure the appeal for GillT is just the fact of knowing that this kid lusts for her. We all get a charge out of knowing we're hot in people's eyes.

I disagree about the confidence thing - you really think that being given a pair of panties by a woman you're hot for would add nothing to your existing confidence level from having the occasional conversation? I assume that to date, the hottest thing they discussed was this list and how her dress might fall off. More likely it's all been "have the kids in bed by nine." Not exactly hot confidence talk. The panties on the other hand could change his life.

I'm not really on the muscle about this, I just hate to see people's dreams scuttled. And the dream isn't really even all that ambitious - it's not like she's resolved to sleep with a thousand men in 2014 or anything. It's fairly limited really.

[Claret]

At any time during my son's teenage years I could look at him and any of his friends and pretty much tell that they probably had a list much like this 18 year olds. What the list really is, is a list of people they'd like to boink and probably nothing else. Walking down the street an attractive young woman or even a more mature woman for that matter, probably has some males looking at her and thinking to themselves "wow I'd like to ******** her". The list is nothing but an adolescent wish list that they all make at one time or another. Myself I simply wouldn't be flattered.

Re: giving the panties, it could just give him bragging rights to his friends as well. Trust me, they make bets all the time.

[Claret]

I don't mean to imply that ALL men do this, just that it's probably more prevalent than thought.