No worries
 

Just relax and don't overthink it!

My wife and I always enjoyed being naked when alone or with only strangers around (lake, beach, sauna, ...)
Up to about 2 years ago we never saw any of our friends naked. But as we get older (30 now) everybody get's more and more relaxed about nudity.
So we've recently been to saunas and nude beaches with a lot of our friends, sometimes only two couples, sometimes larger groups and it was always super chill and fun. Nobody was embarrased, nobody stared or made any comments.
It didn't change our firendship at all. Maybe it even strengtend them.

And don't worry about your size, I'm a "grower" too. Just enjoy your time. No worries.

If your wife is reluctant it’s for a reason. And if it doesn’t work out to her liking, it will be very awkward in more ways than one. Between you and your wife and between both of you and them.

You want to know how to make your wife more comfortable, but you don’t seem very comfortable about it either.

You are worried he might outsize you and embarrass you in front of both your wife and his. If he is, you are going to have a lot more questions. Somebody else can’t answer how long it will take you to get over it, and if you are already concerned, you might not get over it. And that might affect the two of you.

You aren’t ready for it.

We ran into someone from my fraternity at a nudist resort. He was a few years ahead of me, so we weren’t in college at the same time. We had dinner with him and his girlfriend with all of us nude. We saw him again that fall during homecoming. His daughter was with him deciding if she wanted to go to the same school. We talked while waiting for burgers during the homecoming parade and then back at the fraternity house party later. No issues, but we had already been nudists for a few years by this time. That resort is now closed, but we have a site at another nudist resort now. Now if we see him or any other friends at the resort we can invite them to come see our site and have a drink or two.

Most guys have the worries you describe before their first time going nude in public, not later. You don’t mention the name of the resort, but if it is affiliated with a true nudist group (AANR or TNS in the US, BN in the UK, or INF-FNI internationally) then I don’t see why you should be worried about size. It shouldn’t matter at all.

What I have told newbies to nudist resorts...the most difficult time is the last 500 yards to the gate of the resort, once in they are hooked.

Nude with friends
 

I may have written about this somewhere here, but when we were much younger we went on holiday to Belgium, there was a park with cottages and when we booked knew there was a spa complex. What we didn’t know was it was a nude, and no exceptions.

Of the other couple the girl was a colleague of mine, she had been to our wedding, but on her own. Her bf was fairly new and we didn’t know him at all really.

In the cottage we shared there were two bedrooms and we were pretty relaxed, both couples, us and them were young and horny. We disappeared to our rooms and fucked during the day and at night both beds were rattling, happy memories.

However the spa afternoon came round and we went in to discover it was nude and no exceptions - we were pretty brave, the other girl said would go topless and keep a towel on round her waist, my wife said similar so that was decision made. It was fantastic.

To saw her tits for the first time, her full bush and lips getting out the jacuzzi and in the sauna and steam room, the towels became quickly redundant!

The op mentions his size - I am a grower too but I just got on with it. I know she looked she made a comment about me being circumcised after the holiday so definitely looked but her bf was significantly bigger than me. I did feel a bit awkward but I was seeing things for the first time of her and didn’t really think about it.

My advice enjoy it, hopefully your wife will come round and go. We still get on great with the girl ( they split up) but now a married mum too. Hope that helps.

Make sure your wife understands that the worst part of going nude for the first time is just BEFORE you do it! Afterwards she'll be the same as everyone else, and after a few minutes of wandering around, talking to people, engaging in various activities etc, she'll forget she's even naked.

And remember that all conversations will be at eye level so nobody's checking out each others bits!

Acceptance
 

People in our nudist group of friends would occasionally bring an invited "textile" couple to our nudist camp. The men would usually get nude right away without further ado.

For some reason the women were usually reluctant to shed all of their clothing. Even though they were sitting and socializing with the other 4 completely nude women in our group. What were they shy about: All of the women there had tummies, breasts, butts, pussies and blemishes.

After a short while they would ease up and take it all off. However, some would continue to "hide" themselves by wrapping up in a towel or paraeo. They did not realize that being the only one covered up would bring more attention to themselves.

My wife thinks it was because of the perfect image promoted by beauty and clothing TV ads. On occasion she would hear one of them remark about being overweight, their butt or breast size, scars and wrinkles, and even their tampon string showing.

And as it turns out all of the women ( and men ) in our group had all of those "defects", too. We all just accepted our bodies as they were and got on with enjoying the nude life with friends and family.

Watch what you say afterward
 

If you do get to go, have a good time. But afterwards, like if you're at a non-nude social event and the other couple shows up, it will be OK to talk with that couple about your shared nude experience, but NOT in the presence of others. The couple you were nude with might not like others knowing about it, so respect that if they want to keep it under wraps.

Now go and enjoy yourselves.

I used to belong to a C/O non-landed club; and we'd have a fair amount of shy/reluctant newbie wives. They'd often start out in a T-shirt and shorts, or sarong. What would typically happen is they would interact with the nude women; and after a while would start getting self-conscious about hiding from women who weren't hiding from them - or being the only one covered. Some of the women in the club were really good at addressing these newbie's fears and encouraging them into joining in. It was pretty rare that a newbie didn't end up naked by the end of the day.

Sometimes all that's needed is a gentle nudge from a kind female nudist. That's exactly what happened with my ex. She was encouraged to loosen up her sarong; it fell off, and she was fine staying nude once that band-aid had been ripped off.

Being NUDE with anybody depends on the Person!
 

My wife and I have been a few places that we were with friends or neighbors, then had the chance to go on an Adult Cruise with my wife's cousin and her hubby! They have went a few times before and had asked Us, but we had always made excuses and never went but have later heard of their exciting adventures!
It seemed like my wife's cousin broke Us on more of the info about these Cruise and what to expect, then we were told it was for Adult's Only!
The more we heard from my wife's cousin, the more that made me wanna go since she is Busty in her clothing and I would just love seeing her showing those charms on the Tanning deck that they told Us about so you could get a nice all over Tan before stopping off at the Clothing optional Beaches!
While hearing more about what they had done before on these Adult adventures, I got the thought that they were just like Us with being open minded and wanted to add more Spice to their life by sharing some of the pleasures!
I never know what to expect from my wife talking after she had a few drinks and her cousin was the same way!
My wife had mentioned that I might get an erection if I seen some busty women ether on the Beach or on the tanning deck! My wife's cousin said that wasn't any problem at all and it happens lots of times and the people just ignore it or they can take some type of action?
After telling my wife if that's the only reason why we don't go, my wife's cousin said she'll take care of it as long as it was Ok with my wife? So then my wife agreed to it and made a deal that she'll do the same for her cousin's hubby in return!~
But for my 1st time going on they all went up to the tanning deck before me, I was a bit nervous!
On the deck I seen plenty of women either all Nude or Topless, then I spotted my wife and her cousin & hubby!
They were all Nude with the cousin's hubby sitting between the wife's, I took plenty of time to see and enjoy my wife's cousin showing her Busty beauty and trimmed Beaver off as well as my wife doing the same!
What amazed me was the cousin's hubby was looking at both wife's and he was as limp as normal~
Maybe it was just my mindset of being too over impressed by finally seeing my wife's cousin showing her tits and more then I Dreamed about? But I got a nice erection and told them I'll have to excuse myself, going back to our room. I had a knock on the door a short time later and it was my wife's cousin checking Up on me.
She took he robe off and did the same for me, asking if I wanted to enjoy some SEX on the bed? When I told her my wife might be back soon, she said my wife is with her hubby in their room and enjoying SEX too!
So all I can say is it might just depend on the individual person, cause you can be Shy or outgoing!
My wife told me that she been to Nudist Resorts in her early days because her GF's parents were Nudist along with most of their family members too! I heard plenty of stuff and seen pics from what that GF's mom had taken at their Cottage at the Lake!
At many of these places they might have a BAR and they also have people there that start up games to play and keep the action going! Having my wife get Up on the BAR counter all Nude and the BAR Tender pouring shots in her Private places, then asking others to come Up and enjoy a body shot was real exciting for her and Me too just watching!
I hope this helps some out with what to think about and if they have the same interest?
:)