[JW25]

Really enjoyed this thread, which evoked some brilliant memories of the first time my then girlfriend went topless on holiday.

It was actually our first trip abroad together and in the build-up I mentioned about whether she had been topless before and whether she would be doing so on this holiday. She said she hadn’t and that it wasn’t something she was comfortable with, and wondered why I would want her to. Like many others on here, the thought of her exposing herself to others - especially men - was a huge turn on. But I didn’t articulate it as such at the time and simply went down the route of saying nobody wants tan lines etc.

I was careful not to push it too much but was naturally hopeful it was something she would be willing to do once the sun and a few glasses of wine hit.

We spent the first couple of days around the pool and nobody else was topless so I knew there was zero chance she would in that setting. That said, she was quite comfortable sunbathing with her bikini straps loosened, often subtly exposing the tops of her nipples as a result, though I’m not sure she could really notice at the time.

A few days in, I booked an all-day session in one of the cabanas you often see dotted along small piers outside of beach-front hotels. I deliberately chose one right at the end - the most private - in the hope she would feel comfortable in exposing herself without many if any prying eyes. But it was definitely hope over expectation.

The morning arrived and as we were getting ready in our hotel room, out of nowhere she said ‘I think I’ll go topless today’. To this day, there’s something about the way she said this so nonchalantly and out of the blue that still gets me excited.

She applied sun cream to her 34DD tits, complete with the most perfectly round and pink nipples, before covering up for us to set off.

We arrived at our cabana and met our waiter for the day, a relatively young lad who I hoped would soon see my girlfriend’s tits close up.

After being served a round of drinks, we relaxed onto our sun loungers but there was an immediate snag - a lifeguard positioned on a high chair right at the end of the pier. I knew at this moment that my hopes would likely remain just that.

To my surprise, though, she asked ‘do you think I can go topless here?’. Naturally I encouraged it and she seemed willing, but said she would wait a little while.

What she did do was immediately untie her bikini straps and sunbathe on her front for a bit, eventually sitting up but quite casually holding her top to her chest. She actually got up and walked around like this for a while, all under the watchful eye of the lifeguard.

I thought this was probably going to be it but we found a slightly more private area nearby via some steps leading down to a decking area right on the sea. She asked if I could drag our beds down there and thinking what was possibly about to come, I jumped at the chance.

Once there, she asked me again - ‘do you think I’ll be alright going topless here?’. She wasn’t out of sight as there were other cabanas on different small piers scattered along the beach, but not close enough to get a really good eyeful. I said she could go for it as this was very private and then it happened, she undid her straps and pulled off her bikini top, exposing her tits in public for the first time.

It was an amazing moment made all the better when she started confidently applying sun cream to her chest and nipples, and thankfully she allowed me to take a few photos which I still regularly look at to this day.

She spent most of the time laying on her back but did occasionally sit up, even walking around a couple of times.

Throughout the day we took a few dips in the sea for which she put her top back on, but happily removed it when we were back on our beds.

Seeing her so confidently showing off her tits was an amazing feeling and I was hard for most of the day. One of the best moments was when our waiter reappeared to ask if we needed anything and while she attempted to cover herself with her arm as he was stood speaking to us, I’ve no doubt he caught a very good glimpse as he walked towards us and was still able to see plenty either side of her arm.

We booked another cabana later in the holiday and she did take her top off again but only briefly, though thankfully long enough for me to take some more photos.

That was really the one and only time she has been properly topless on holiday. It’s happened on a few other occasions, but mainly only as a dare and to flash quickly while I snapped a photo.

I did manage to convince her once to sunbathe naked on our balcony which was in full view of the hotel swimming pool by saying the glass covering it was opaque. That was another amazing experience, her facing dozens of people with her tits and perfectly hairy pussy on display, but later that day she realised the glass was in fact pretty much fully transparent and so that was that and I haven’t experienced similar since.

Naturally I wish for more in the future but even if not, I’ll always have the memories of that first time.