A couple of months ago, I went on vacation alone to a resort hotel in Phuket for a week. During my time there, I met three attractive, older ladies (or rather, MILFs) that I'll never forget for the rest of my life.
It was my second morning at the hotel. I was at the hotel café getting my breakfast when I realized that all the tables were taken.
That was when these three nice MILFs asked me to join them at their table. The three of them, in their mid 40s, were from England. Angela, Linda and Tara were long-time friends, and despite all of them having grown-up kids, they didn't have spouses - Angela was widowed, Linda was separated and Tara was divorced.
Now let me describe their physical appearances. Tara was thin - she had a slight (very slight) pouch but otherwise she was thin all over. She had small breasts and a pretty flat rear.
Angela and Linda were almost identical in body shape - they weren't exactly fat, but I suppose the politically correct term would be to call them 'full-figured.' They had broad shoulders, beautiful large breasts, they had a bit of a belly, nice butts and pretty toned legs. They were all brunettes. Angela and Linda had long hair while Tara's was short.
If you didn't know better, you'd think Angela and Linda were sisters! All of them were between 5'6' - 5'7'.
Anyway, they were a jolly bunch and quite fun to be with. They were quite open with their humor and didn't mind talking openly about things like sex. Anyway, after that first encounter at breakfast that morning, I bumped into them again later at the hotel swimming pool area.
All of them were wearing one-piece swimsuits. We got to talking again (I was always in T-shirt and shorts, as I'm pretty shy) and got to know each other better.
Over the next couple of days, we'd have breakfast and dinner together at the hotel. During the day, we'd chill-out together at the pool or go out to the nearby town together and have lunch outside.
Anyway, the real fun began when I started to hang out in their rooms.
On the fourth day, after breakfast, the three ladies told me that they didn't feel like sitting by the pool or going out and wanted to just relax in their rooms.
I was a bit disappointed as I found the three of them fun, and had no one else to hang out with. I think they saw the disappointment in my face, and asked me to join them in their room! Like I was going to say no!
I went to their room (they were all sharing) at 11am and was a little taken aback by their indoor behavior. They were mostly in their bra and underwear, or just wearing a towel with nothing under. In fact, Tara told me that if it weren't for a 'gentleman in the room,' they'd be topless or naked!
I told them to act as if I weren't there and that I didn't mind, and Linda jokingly said 'oh, he'd love that wouldn't he,' and we all laughed.
I told them if they wanted, I could strip down as well, and there was a weird silence for a short while. Then there was laughter, and we were all on the bed, talking about all sorts of things. Tara was in her bra and underwear, Angela was in a towel and Linda in bra and towel.
Nothing happened that day. They were all covered up. When I went back to my room that night, before sleeping, I jacked-off to the thoughts of being around those women. I had an amazing orgasm, especially thinking about Angela and Linda's huge breasts.
I later discovered they were both 38DDs, while Tara was a 36B.
The next day we hung out in their room again, and this time, all three women were topless! It was quite exhilarating! I just couldn't stop staring!
Tara casually asked 'do you like the view' and I said 'yes!'
It was weird, as I was just not used to it. We were again hanging out, talking about all kinds of stuff, except these women were topless.
I looked them straight in their faces when I conversed with them, but stole quick glances at their assets when they weren't looking. Again, Angela's and Linda's tits were almost identical. They were large, pear-shaped and saggy. Their nipples pointed down, towards the floor, and they were huge! Their nipples were as large as the tip of my index finger (I had never seen nipples that large in my life).
Tara's breasts were small and perky. Her nipples neither pointed forward nor down - they were in-between. Her nipples weren't that large either.
At one point, we started talking about sex. I told them that I was still a virgin (sad but true) and they asked me if I was offended by their attitude of not covering up.
Somehow, without thinking, I blurted out everything - I told them that I had been fantasizing about them the whole time, and that I thought they had beautiful bodies enough to make a hot-blooded male go wild.
They seemed pretty surprised by what I had said. Seeing the look on their faces, I apologized, and to my surprise, they all just burst out laughing!
Tara sat next to me on the bed, put her arm around my shoulder and told me 'it was ok.' I had never been this close to a naked woman before. I could smell her fresh skin, her hair, and loved the aroma.
They then told me, if I wanted, they could go fully nude, but said they would never do anything beyond that. I simply nodded.
For the next couple of days, I spent my entire day with three naked ladies. None of them were shaved, but they were trimmed.
I finally gathered the courage to strip too, but was so embarrassed. I'm not the most endowed male out there, and I actually apologized to them for that! But they were fine with me, and actually told me that they had seen 'much worse.'
They never made me feel uncomfortable - ever.
It was then that we talked about our sex lives, and all of them told me that they still touched themselves every now and then and occasionally urged for a 'good fuck.'
I jokingly told them that if they wanted, they could 'use me,' but they all just laughed, and just said that I'd be better off and happier with a younger woman my age. The discussion never quite went further than that.
On my last day with them (I was flying back home the next day), things really did get heated. I told them that since it was my last day with them, I wanted to go a little further then just looking at three naked women.
They asked me what I wanted to do, and they seemed quite firm about not having a romping session, and I asked them if I could feel their breasts.
They all seemed pretty nonchalant about it, and were more than happy to let me touch them! I was in heaven after that!
I first touched Tara. I cupped her tiny breasts in my hands, and they felt tender. I rubbed them, caressed them and touched her tiny nipples. They were soft and stayed soft. But I started getting hard.
Next was Linda. I had been fantasizing about Angela's and her tits for the past one week! Linda felt soft, yet powerful in my hands. They felt heavy too! When I got to her nipples it was bliss! I was more daring now, and started to squeeze and pinch her nipples. It was amazing, and I got really stiff.
All the ladies laughed.
'You're enjoying yourself, huh?' said Angela, while Linda said 'I think he's going to have his hands full tonight, girls!'
I then felt Angela, and they felt about the same as Linda's. I then told them that if they wanted, they could touch me in return. All three ladies took turns touching my chest, arms, belly, thighs, my butt (which they seemed to enjoy the most) and briefly, my penis.
They gently caressed it, but never going further than that - not even a tug or a brief stroke. I didn't want to tell them to do anything they didn't want, and was quite happy to continue touching them.
This went on for about half and hour. I was still playing with Angela's tits, when I asked her if I could touch her between her legs or her butt. She said 'fine' but don't get carried away.'
I don't know, but I took that as a warning, and caressed her butt briefly and then placed my hand between her legs. I was so hard now, and my head was practically spinning. I felt her fur, her warmth and her wetness.
It was very brief, when Angela pulled away.
'Alright hon, enough fun for one day.' I felt dejected, and smiled. All of them looked at my erection and laughed, and said that I 'needed to attend to it.'
I asked if anyone wanted to help me, and neither of them volunteered. They just laughed, and Tara said 'there's the bathroom, be my guest.'
It's so weird, why is it never like in the stories you read or in the movies you watch? Anyway, my erection subsided as we continued to chat for a while. Later, I dressed up and went back to my room. As soon as I got in, I stripped, went to the bathroom and started to jack-off like crazy!
I brought my right hand to my nose - and I could get Angela's strong scent in my fingers. That was enough to send me over the top, as I exploded and had the most amazing orgasm in a while. My legs nearly buckled under me!
Later in the day, I packed my things, then went to the three ladies' room and thanked them for the amazing experience. They each gave me a hug and a peck on the cheek, and I had tears in my eyes.
With that I said goodbye, and was off on my way. I wish I could've done more with the three of them, but I suppose it wasn't meant to be.
I still jack-off some nights to that fantastic holiday of mine - it truly was an unforgettable experience!