Nervous about having sex with a new man

[erasuregirl]

My divorce is finalized this week I was married for 11 years to my ex and have moved on. I met this guy while I was still married. We never really went past platonic friendship til now. Anyway, I planned a night out of town for us to "get together". Now, I am very much excited about this. We have kissed and grinded and I have seen his penis. But when we go to the hotel, we are definitely going to do the deed. I am nervous as hell. He has already started to talk about wanting me to wear 2 ponytails, Victoria's Secret, heels, etc.
I am a bit overwhelmed since my ex and I didnt really do much play "dress up" for sex. I am also not getting the whole "two ponytails" thing. What is up with that?
Does that mean I am to meet him wearing just lingerie? I am feeling very insecure...that I just may suck at this and he will never want to have sex with me again!

[sera300]

Wear what you are comfortable with then let the "fantasy" follow next time. Just do not wear "granny panties"!!! Put on a dress, with heels, nice lingerie (seductive types) or go commando under the skirt. I doubt he will have regrets.

[Brandye]

Sounds like he is into the "little girl slut" thing. I, too would be nervous. Sera gives the best advice and if he does not like it, so be it. There are many men out there.

I have done the lingerie under a raincoat across the lobby thing but that was with a rather long term involvement.

[EvilEvilKitten]

Yes he's into the "schoolgirl" thing BUT the real issue is: FOR A FIRST DATE?!?!? What is he THINKING??!?!?

It is FAR too early in this relationship for him to be asking you to play 'dress-up games'. Naturally you're nervous! The man is being PUSHY.

Wear something appropriate. His reaction will tell you all you need to know about him. Either he's into you as a person or he's just wanting into your pants.

[machine_rat]

If you have one, this may be his way of luring you out of your shell.

Does he mean pigtails when he says two pony tails? Think ditzy cheerleader.

[erasuregirl]

Well, he thinks pigtails are sexy. I never would wear it outside but I think i would be ok in the bedroom. by the way, we arent dating...he is more of a friend that i have an intense sexual attraction to. i am in my mid-30's, was the "good girl" for a LONG time. Now i want to play, but I have so much to learn!
He thinks doing stuff like pigtails and 4 inch heels will make this a memorable event. we are going to a hotel

[atomic]

I'd say don't give him the full show on the first date unless you don't want it to last long, and that is ok too
Unless you intentionally want to be dominated by him, it sounds like he is making the demands and you are just complying with them because you are finally free and just want to play - and that is also fine, if that is what you are wanting to do

I would keep him in suspense, and let myself get comfortable with things changing at my own pace. If you are not used to wilder things, start slow. If he is a considerate lover, he will let things gradually build up until you are ready to push your limits a little more.

But like I say, it sounds like you are both after a bit of fun, so enjoy it!

[cjb1981]

Pigtails make the most awesome handles plus they do a great job of keeping long hair out of the way...I do love pigtails

[EvilEvilKitten]

Sorry, but I have a problem with guys wanting grown women to masquerade as children.

The best thing any man can say is "Just show up."

[cjb1981]

Originally Posted by EvilEvilKitten

Sorry, but I have a problem with guys wanting grown women to masquerade as children.

The best thing any man can say is "Just show up."

Whoa, I didn't say anything about any kind of school girl outfit or anything, pigtails just rock, that's all