"The local paper prize – a naturist holiday for 2, but no one to go with her and so she invites me, her son in law to be"

To set the scene a little first. My name is Chris, I was a 24 year old man at the time who had been with my girlfriend (Leila) for almost 5 years. We had a good relationship and were on the verge of engagement to be married (although I hadn’t asked her at this point). In previous relationships I had always got on well with my gf’s parents, I was well spoken with a good job and so the dad’s were always happy, also I had a look that for some reason older women found very handsome. Not sure whether it was my big brown eyes , square jaw, designer stubble, short but thick and soft hair or full lips or the fact that I was very tall that did it for them or whether they were more honest about what they felt. To be honest it could have been that they were less fussy too!I had had a few flings with older women before I was with Leila, the whole milf/cougar thing really did it for me back then. Their confidence and lack of inhibition was very refreshing compared to the 16-18 year olds of my day. It was a great learning experience for me with them and they certainly enjoyed it too!

Back to my relationship at the time, Leila and I had slightly different attitudes to sex and nudity. I, due to my experience before her, was quite confident about my body and my sexual ability too. I would often walk around the house naked as I felt comfortable with it all hanging out, it felt like I was free. Now I don’t have anything to be shy about, if you know what I mean, my cock when hard is almost 10” long and very very thick, so much so I can barely fit my hand around it, and being 6’4 I have big hands. The other thing about my cock is that its what I believe they call ‘a show-er’ rather than ‘a grower’. This basically means that my cock doesn’t go that small, it is effectively 75% of its erect length and width when soft. So as you can imagine it hangs soft actually a bit bigger than the average erect penis. I loved the feeling of it swinging around as I wandered around the house.

Leila, however, was a bit of a prude sexually, she was very attractive with a good body but didnt have that inner confidence. She would prefer sex on her back so she didnt have to worry about her bits wobbling and was very rarely naked as she felt exposed and uncomfortable. Don’t get me wrong, she loved my experience and my size when she was in the mood, but she was a more a once a week girl and a little vanilla as opposed to my previous encounters with more adventurous milfs. Because of my penchant for nudity, I had always joked about taking her on a nudist break to try and get her over her insecurities, hoping that it would unleash the inner dirty girl inside her. However, she was still not convinced, thinking I was weird wanting to wander round naked with complete strangers.

Her parents had a bit of an age gap, her mum (Mrs P) was just about to turn 50 but her dad (Paul) was almost 65. I wouldn’t say her mum was a typical milf with long blonde hair and a tan etc but she wasn’t bad for 49. A similar height to Leila, Mrs P was about a size 12-14 in UK sizes (I think that’s 8-10 in the US). She had shoulder length brown hair, ample boobs and a fairly shapely butt. She also had a very cute grin and eyes. Paul was balding with a beer belly. They had got married very young but still were in love and it didn’t take much to see that. However, Mrs P and I seemed to get on very well, she would joke and flirt about stealing me from Leila, in that way that only middle aged women can get away with without being taken seriously. But she would always give me a peck on the lips rather than the cheek when we greeted each other which was something I hadn’t done with previous in laws and in private conversations with Leila she would always tell Leila how lucky she was to find a ‘spunk’ of a guy, was the way she put it . Leila and her mum had a very close relationship and discussed everything on a daily basis, I can remember over hearing them one time talking about sex and penises and Leila was saying how blessed I was and that it hurt some of the time. Now, they didn’t go into any gory detail, despite Mrs P’s best endeavours, as all I could hear from Leila was “Mum!, don’t be so rude, I’m not telling you that, I’ve told you he’s bigger than average and my biggest, you don’t need to know anymore than that!”. The conversation went on for a while but no real detail was discussed, in the end Leila finished with “Mum! TMI, I don’t want to know about dads small thingy, it worked didn’t it I’m here” she laughed.

I didn’t think about the conversations or the situation much to be honest, it was not really different to what I had encountered before. Then one evening Mrs P came round for dinner as Paul was working late, usually it was the other way round and she cooked for us but we helped out when we could. Anyway, we had finished dinner and we had had a few glasses of wine, I picked the plates from the table and said “I’ll wash up, you two go and catch up in the front room. Oh, and you can finish this wine while you’re at it” I instructed as I topped up their glasses.
They trotted off to the front room, which wasn’t too far from the kitchen so I could still hear the gossip while I washed up. I listened in on their discussions about the soaps and the next door neighbours and I was not paying attention as it was that boring when Leila shouted “oooh! Well done mum, what did you win?”

“you won’t believe me if I tell you darling” her mum replied

“Go on mum, I’m intrigued” she pleaded

“OK, OK” Mrs P caved in “I have won a week’s holiday in a luxury resort on a tropical island” she grinned.

“Wow mum, that’s great, that must be worth a fortune! Bet dads well pleased” she replied

“well, there is one catch” a more sombre voice replied “and your dad isn’t willing to agree, so I’m not sure we can go”

“Is it a time share thing or hard sell or something Mum? Why isn’t dad willing to go?” Leila enquired

“well, you see” her mum started to spit it out “the resort... well.. its errr a naturist resort” she finally admitted

“ah, I see” Leila replied “why doesn’t he want to go?” she asked

“He doesn’t see the attraction darling, he doesn’t like being exposed, I’ve tried talking him around but he wont even do it for a free holiday” she moaned

“calm down mum, I can see his point, I’m like that too, not too sure I’d be the first on the plane either” Leila stood up for her dad.

“I know babe, but its something I’ve always wanted to do, I want to see what it feels like to wander around free, and I’m not getting any younger, I don’t think I would want to go in a few more years as I don’t think I’ve got much more time before everything starts to droop” she joked

“Mum! That’s gross” Leila protested “well, cant any of your friends go? You must have seen them all naked before in the changing rooms at the pool so no issue there?” Leila seemed proud of her suggestion

“I’ve thought of that darling” she said “but its not that easy to take a weeks break at such late notice, plus they only have so much holiday that they can use to go away with their husbands” she started to get frustrated as if she had been through all the options before.

At this point Leila could see the disappointment in her mum’s eyes, she had mentioned this years ago about being something she wanted to do and here was her chance but didn’t want to go alone.

“well, there is one more option” Leila started to suggest. Her mum’s eyes started to brighten “yes darling, what? Who?” she was almost begging at this point.

Leila looked her mum in the eyes “Chris” she said bluntly. I stopped the washing up and started to listen more closely

“b..bb..but he’s your boyfriend Leila” her mum replied

“I know mum” Leila quickly answered “but hear me out. You really want to go, Chris has always said he wouldn’t mind trying one of these places and I really don’t want to go. So I’d rather he went with someone I could trust and so you both can enjoy it and then thats it then. Plus he’s got some holiday to use up and I haven’t so he would have only been sat around the house for a week” she continued to put the case.

I must admit the thought of my own gf sending me off on a naked week with someone else was weird, especially her mum, but weird in a way that was starting to make my cock twitch. I could feel it starting to grow when I heard “Chris!, come in here, we’ve got a proposition for you” Leila shouted.

I tucked my cock straight upwards in my jeans so my big jumper would cover any growing bulge and entered the room. “Yes Darling” I asked “what is it?”