What to wear?

[Drinknumber11]

Hi all, hoping for some help with this and going to give some context which will explain why I’m so nervous.

horrible, abusive sexless marriage for 10 years - he destroyed my self confidence. Been on OLD 3 years and had all the horrific/funny experiences. Had a FWB he was hot but I never had an orgasm with him. That was over 2 years ago and not had sex since.

I have met someone lovely and we have been dating around 2 months. Really good chemistry. He’s taken things at my pace. He’s staying over this weekend and I’m sure we will sleep together.

I have underwear that is sexy but can be worn as everyday underwear. Do I need to go full on sexy with hold ups, corsets ?

when chilling out around the house do I need to wear stringy, lacy things or can I just be myself and wear my pyjamas (they are very nice but wouldn’t be classed as sexy!) 😂😂

Sorry for the stupid questions, haven’t had a relationship/dating for so many years so I have no idea what to do.

Id do whatever makes YOU feel most comfortable and sexy. I had my first sleepover of a new relationship recently and went lingerie under normal clothes for the daytime because it made me feel sexy and confident. I took boy short pants and a vest for nighttime as I didn’t want to share my Percy Pig pjs just yet!! However the dude in question is lovely and I’m pretty sure he’d not throw me out for bad pyjamas 😂

In all honesty I'd view it as a shopping opportunity and buy silk chemise/pj's with cashmere wrap cardigan to casually throw over the top to chill out in.
I'd wear a nice matching set for sexy time, but probably save suspenders etc for the next time... and the next.. getting sluttier ans sexier each time.

I’ve got a new bf of 2 months and we first slept together just after Christmas. I did buy some new lingerie, nothing too sexy, but nice. Not sure he even saw any of it properly as he pulled my tights off (no I didn’t go for hold ups, that would be for a dirty weekend away only for me) but he pulled my knickers off at the same time (he later said he didn’t mean to do that!), and it was pretty dark so he didn’t notice the bra very much either. I didn’t stay longer than 11/12 in the morning when I’ve stayed over so not sat around but I’d probably just wear normal PJ’s. I don’t think he’s expecting you to be wearing sexy stuff all the time.

Oh and enjoy! I’m enjoying having sex again but also with a very generous lover who doesn’t just think of his own pleasure!

As @XmasElf10 says being comfortable and warm is the most important they are ways to confidence.
I had a first meeting recently with a lady, I bought some new undies. Not exciting just a bit better quality than my everyday wear.
Also I took stockings so she saw me getting dressed slowly and carefully the next morning. That was more effective than stripping off.
Just an idea.

I would avoid going what might be seen as OTT the first time. You say you have underwear which is "everyday" but "sexy". I think that is your answer.

I like to think I have nice underwear, always aspire to match (sometimes fail!), I feel good and confident in it, but I would not dress up exclusively for the bedroom.

Whatever you feel most comfortable with, you can always spice it up after that. Good luck and hope it goes well x

Whatever floats your boat, perhaps a chance to buy something you hadn't tried before and definitely wear it under regular clothes.. unless you don't want to of course!!

You never know pushing your usual stuff might become the new norm!

Maison Close

Thank you everyone for all your helpful replies. Unfortunately the man in question cancelled our weekend (work commitments apparently), but at least I have the answer to my worries if I do decide to have a man over for a weekend in the future !

@Drinknumber11 his loss I suppose. Hope your chilling in your comfiest pj’s with a nice tray for yourself

Meant treat sorry

OP, l’m sorry it did not work out this time and wish you well with your next weekend adventure.

Looks like I'm a little late to this conversation as the big date didn't happen. But just to add that people are very different in terms of what appeals to them. I doubt whether there's a single style that appeals to all men. For example my own partner isn't terribly interested in the Victoria's Secret or Agent Provocateur kind of stuff but does get excited about more fetish-y outfits. Probably the best thing is to cultivate the kind of relationship where you can talk about what appeals to you. If you get to the first date, that is! Best of luck for the future.

I'm in my first serious relationship since I transitioned and we slept together for the first time recently. We'd been out and I'd worn leather jeans, cashmere sweater and heels which I knew had got him interested. Under I had grey satin bra and knickers with cream trim from Boux Avenue. Just normal undies tbh, he said they were really classy and very sexy. Turns out he's a big fan of smart looking lingerie. Big fan!