Want my wife to cuckold me with my best friend.

For cuckoldresses and the men who serve them.
johnswan
Experienced
Posts: 174
Joined: Fri Aug 15, 2025 10:17 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Mon Dec 08, 2025 1:47 pm

scaryflyer wrote:
Mon Dec 08, 2025 8:48 am
Hey johnswan,
How about setting up a dual waxing with you and Greg together in the same room, the idea being Niki can instruct Lucy on waxing technique.
Lucy practices on Greg while Niki does the waxing on you to show Lucy the technique ;)
In this way Lucy might get a chance to see what Greg is packing :o
Greg will pay for his waxing so Niki should be happy :?:
Hi scaryflyer. On Nickie's first waxing visit, we watched each other being waxed by her. The idea was that I could then wax Lucy, and Lucy could wax me. But it's ended up that I'm waxing myself....well, pubes only, chest hair I've resorted to shaving with a razor. And Lucy has gone back to her trusted razor. Although I still sometimes do hers, for a more thorough smooth finish! 😛

But I'll try and get some combination worked out, on the day, where as much flesh as possible is exposed. 😁

Long Lurker 34
OHW Addict
Posts: 3200
Joined: Mon Dec 03, 2018 4:25 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by Long Lurker 34 » Mon Dec 08, 2025 4:00 pm

johnswan wrote:
Mon Dec 08, 2025 7:56 am
Long Lurker 34 wrote:
Mon Dec 08, 2025 4:36 am
JS
- As much as anything Lucy could always ask her friend for pointers and a demonstration to ensure she's doing it to best effect.
- If she's open to it perhaps her friend could also come and 'sit' you when she's on a date. Maybe combined with a supremely long ruined orgasm and milking session. :shock:
OMG. 😲😛 You mustn't suggest things like that at the moment. I've agreed to abstain from cumming for a few days, at least, before Lucy tries the prostate massage/milking again. And I've not even got to 24 hours yet!
With the scenario that you suggested, now in my mind, I might not last much longer! 😛😁
JS
- I can see you might break free from your restraints and require an even smaller cage for Christmas. Oh well an easy gift for Lucy. :lol: :lol:

johnswan
Experienced
Posts: 174
Joined: Fri Aug 15, 2025 10:17 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Mon Dec 08, 2025 10:58 pm

Bsod83 wrote:
Mon Dec 08, 2025 3:50 am
I just love getting pegged while stimulating my dick. I get crazy orgasms, moan like a little girl, and get a tingeling sensation afterwards. Its crazy good. I so understand why many gays like to bottom.

Not having sex / cumming for a few days increase the sensation a little more.

I really enjoy reading about your relationship, thank you for sharing
Hi Bsod83. I'm assuming that it is your wife or girlfriend doing the pegging to you.

And I'm assuming that there is a large domination element in that.

I don't think I'm quite ready for pegging. But I have to admit, thinking about it turns me on! 😊

johnswan
Experienced
Posts: 174
Joined: Fri Aug 15, 2025 10:17 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Mon Dec 08, 2025 11:27 pm

I have to tell you about something that happened over the weekend.

We went over to Lucy's parents on Sunday .They have an indoor sauna that we occasionally use. The idea was to go early enough so that we could use their sauna, have a break, have lunch, then watch the Formula 1 final race in the afternoon.

Before we left home Lucy asked me to wear the panties from the bra and pantie set we bought for me recently. The panties are bright pink, lacey etc, obviously feminine.
I only agreed on the basis that she went without a bra for the afternoon. I knew that we would be sharing the sauna with Lucy's sister, Jessica, and her boyfriend, James. I thought it would be fun for James to see Lucy braless! Under a top of some sort, of course.

Later, we were in the sauna, and Jessica almost immediately asked me what happened to my chest hair. In that I no longer had any (we've shared the sauna with her before, so she knew I had chest hair previously).
And before I could reply, Lucy said "I shaved it off". Her sister just sort of smirked, as did her boyfriend, them both exchanging looks with each other. Nothing more was said, fortunately.
Oh, and in the sauna I wore a pair of conventional male boxer shorts that I'd taken, Lucy wearing a fairly skimpy bikini. Her sister and boyfriend dressed similarly.

After the sauna I went with Lucy to her old bedroom, and waited while she showered. Then swapped with her when she'd finished. Lucy disappeared somewhere, leaving me to shower. After my shower I put the pink panties back on, and was sat on the bed, drying my hair with a towel. The bedroom door opened, and I assumed it was Lucy returning. But when I took the towel from my head, I saw that it was Lucy's mum!
She immediately apologised, saying that she thought we were still in the sauna.

She had obviously seen the pink panties.

She went to leave, then stopped at the open door, coming back into the bedroom.
She said "Can I ask you something personal? You don't have to answer if you don't want to".
I couldn't think what else to say, but replied, yes, she could ask me whatever she wanted.
She said "I know that Lucy can be a very.... determined lady, at times. And I know that you, John, are a bit of a softy with her. Which is nice. But....I hope that the underwear that you have on....is that your own choice? Or is Lucy pushing you to do things you don't want to?"

At first I didn't know what to say. Because, me wearing the panties wasn't my choice. But I hadn't really been forced to do it.
Ok, coerced a bit maybe.

So I tried to explain that, no I hadn't been pushed or forced into wearing the panties. And just, clumsily, tried to explain that it was something we occasionally did for fun.
I couldn't really tell her that the deal was that, if I wore the panties, Lucy would go braless under her top, to tease James.
And I certainly wasn't going to get into an explanation of Lucy domming me, to wear female underwear!

Anyway, she seemed happy that I wasn't being forced into doing things by her daughter. At which point Lucy returned, coming into the bedroom, and seeing me with just the pink panties on. And her mum there.

At which point her mum said, "ok, I'll leave you to it", and went to leave. But then stopped again.
She said "I've got an idea. Come with me, both of you". And she went out into the corridor. I looked at Lucy, who sort of shrugged, indicating she didn't know what her mum wanted. Lucy took my hand, to lead me out, to follow her mum. But I was hissing to Lucy that I couldn't leave the bedroom wearing only the panties!
Lucy checked outside, on the corridor and said there was no one about, pulling me to follow her mum.

Who led us to Lucy's parents bedroom.
Once in the bedroom, Lucy's mum told me to sit on the bed.

Just as a side note, I was familiar with Lucy's parents bedroom. When we were at university, and home for the holidays, I'd spend most of my time at Lucy's. I shared Lucy's bedroom, supposedly sleeping on a temporary bed, but obviously sleeping with Lucy. Which I'm sure her parents knew, but didn't seem bothered about. But if her parents were away for the weekend, or holiday, then Lucy would drag me to her parents bedroom, which had a large double bed. Which made me nervous, but was nicer than fucking Lucy on her single bed. Also, Lucy would rummage through her mum's extensive lingerie selection, modelling stuff for me, getting me very excited. I fucked Lucy a few times on that bed, with Lucy still wearing a pair of her mum's fancy silky, or satiny knickers. It's where I first discovered French Knickers, which I think are called 'tap pants' in the USA?

Anyway, Lucy's mum disappeared into their large walk in wardrobe and came back with a large carrier bag.

"This is some of my old lingerie, that I no longer wear. I have offered it to Lucy, as she is a similar size to these items. But she didn't want to wear her mum's cast off lingerie....understandably, I suppose. But they are too good to throw away, or give to a charity shop. So, I thought you might like them, to 'play' with. What do you think?"

She then proceeded to show me some of the contents of the bag. At which point Lucy excused herself, and left. Now I was alone with her mum, who was holding up various panties and other lingerie for me to see.
I didn't know what to say!

Then, she said "Do you want to try anything on, to check they fit you, before you take them..... assuming you'd like to take them?"

I wasn't sure if she was expecting me to try them on in her bedroom, there and then, or for me to take them back to Lucy's bedroom to try.
"No need to be shy" she said. "I don't suppose you've anything I haven't seen before".
Her mum is a medical consultant, so I'm sure she's seen plenty.

But I deferred on the offer to try anything on, and just said that, if she didn't mind, I'd take them and try them at home. She smiled, and said she understood.

Then she sat on the bed next to me, put her arm around me, and said "It's ok, you wanting to wear female things. Lucy's father.....well, we won't go into that.....".

Then she put a hand on my upper thigh, and squeezed it. And gave me a kiss on my forehead, pulling me to her.
"I'm glad my daughter married you" she said. "You are a very sweet boy".

At which point she got up and left to sort out lunch.

I quickly snuck the bag of lingerie back to Lucy's bedroom, and got fully dressed.

Later, when we'd got home, we tipped the bag of lingerie out, and spread it all out on the floor. There was lots of sexy stuff there.
But Lucy was a bit unsure about me wearing any of it. "But you'll be wearing my mum's underwear!"

Agreed, there is a strange element to this. But, most of the lingerie looked expensive. And would save us buying anything else specifically for me.

I'll see what Lucy thinks about it, after she's got used to the idea.

A surprising Sunday.

Gulfcpl
Player
Posts: 336
Joined: Thu Mar 02, 2023 9:16 am

Re: Want my wife to cuckold me with my best friend.

Unread post by Gulfcpl » Tue Dec 09, 2025 1:49 am

Wow, very hot in a strange way but still hot. Progress is being made in several different directions.

Paulypippa
Prepubescent
Posts: 8
Joined: Thu Oct 19, 2023 5:33 am

Re: Want my wife to cuckold me with my best friend.

Unread post by Paulypippa » Tue Dec 09, 2025 3:34 am

johnswan wrote:
Mon Dec 08, 2025 11:27 pm
I have to tell you about something that happened over the weekend.

We went over to Lucy's parents on Sunday .They have an indoor sauna that we occasionally use. The idea was to go early enough so that we could use their sauna, have a break, have lunch, then watch the Formula 1 final race in the afternoon.

Before we left home Lucy asked me to wear the panties from the bra and pantie set we bought for me recently. The panties are bright pink, lacey etc, obviously feminine.
I only agreed on the basis that she went without a bra for the afternoon. I knew that we would be sharing the sauna with Lucy's sister, Jessica, and her boyfriend, James. I thought it would be fun for James to see Lucy braless! Under a top of some sort, of course.

Later, we were in the sauna, and Jessica almost immediately asked me what happened to my chest hair. In that I no longer had any (we've shared the sauna with her before, so she knew I had chest hair previously).
And before I could reply, Lucy said "I shaved it off". Her sister just sort of smirked, as did her boyfriend, them both exchanging looks with each other. Nothing more was said, fortunately.
Oh, and in the sauna I wore a pair of conventional male boxer shorts that I'd taken, Lucy wearing a fairly skimpy bikini. Her sister and boyfriend dressed similarly.

After the sauna I went with Lucy to her old bedroom, and waited while she showered. Then swapped with her when she'd finished. Lucy disappeared somewhere, leaving me to shower. After my shower I put the pink panties back on, and was sat on the bed, drying my hair with a towel. The bedroom door opened, and I assumed it was Lucy returning. But when I took the towel from my head, I saw that it was Lucy's mum!
She immediately apologised, saying that she thought we were still in the sauna.

She had obviously seen the pink panties.

She went to leave, then stopped at the open door, coming back into the bedroom.
She said "Can I ask you something personal? You don't have to answer if you don't want to".
I couldn't think what else to say, but replied, yes, she could ask me whatever she wanted.
She said "I know that Lucy can be a very.... determined lady, at times. And I know that you, John, are a bit of a softy with her. Which is nice. But....I hope that the underwear that you have on....is that your own choice? Or is Lucy pushing you to do things you don't want to?"

At first I didn't know what to say. Because, me wearing the panties wasn't my choice. But I hadn't really been forced to do it.
Ok, coerced a bit maybe.

So I tried to explain that, no I hadn't been pushed or forced into wearing the panties. And just, clumsily, tried to explain that it was something we occasionally did for fun.
I couldn't really tell her that the deal was that, if I wore the panties, Lucy would go braless under her top, to tease James.
And I certainly wasn't going to get into an explanation of Lucy domming me, to wear female underwear!

Anyway, she seemed happy that I wasn't being forced into doing things by her daughter. At which point Lucy returned, coming into the bedroom, and seeing me with just the pink panties on. And her mum there.

At which point her mum said, "ok, I'll leave you to it", and went to leave. But then stopped again.
She said "I've got an idea. Come with me, both of you". And she went out into the corridor. I looked at Lucy, who sort of shrugged, indicating she didn't know what her mum wanted. Lucy took my hand, to lead me out, to follow her mum. But I was hissing to Lucy that I couldn't leave the bedroom wearing only the panties!
Lucy checked outside, on the corridor and said there was no one about, pulling me to follow her mum.

Who led us to Lucy's parents bedroom.
Once in the bedroom, Lucy's mum told me to sit on the bed.

Just as a side note, I was familiar with Lucy's parents bedroom. When we were at university, and home for the holidays, I'd spend most of my time at Lucy's. I shared Lucy's bedroom, supposedly sleeping on a temporary bed, but obviously sleeping with Lucy. Which I'm sure her parents knew, but didn't seem bothered about. But if her parents were away for the weekend, or holiday, then Lucy would drag me to her parents bedroom, which had a large double bed. Which made me nervous, but was nicer than fucking Lucy on her single bed. Also, Lucy would rummage through her mum's extensive lingerie selection, modelling stuff for me, getting me very excited. I fucked Lucy a few times on that bed, with Lucy still wearing a pair of her mum's fancy silky, or satiny knickers. It's where I first discovered French Knickers, which I think are called 'tap pants' in the USA?

Anyway, Lucy's mum disappeared into their large walk in wardrobe and came back with a large carrier bag.

"This is some of my old lingerie, that I no longer wear. I have offered it to Lucy, as she is a similar size to these items. But she didn't want to wear her mum's cast off lingerie....understandably, I suppose. But they are too good to throw away, or give to a charity shop. So, I thought you might like them, to 'play' with. What do you think?"

She then proceeded to show me some of the contents of the bag. At which point Lucy excused herself, and left. Now I was alone with her mum, who was holding up various panties and other lingerie for me to see.
I didn't know what to say!

Then, she said "Do you want to try anything on, to check they fit you, before you take them..... assuming you'd like to take them?"

I wasn't sure if she was expecting me to try them on in her bedroom, there and then, or for me to take them back to Lucy's bedroom to try.
"No need to be shy" she said. "I don't suppose you've anything I haven't seen before".
Her mum is a medical consultant, so I'm sure she's seen plenty.

But I deferred on the offer to try anything on, and just said that, if she didn't mind, I'd take them and try them at home. She smiled, and said she understood.

Then she sat on the bed next to me, put her arm around me, and said "It's ok, you wanting to wear female things. Lucy's father.....well, we won't go into that.....".

Then she put a hand on my upper thigh, and squeezed it. And gave me a kiss on my forehead, pulling me to her.
"I'm glad my daughter married you" she said. "You are a very sweet boy".

At which point she got up and left to sort out lunch.

I quickly snuck the bag of lingerie back to Lucy's bedroom, and got fully dressed.

Later, when we'd got home, we tipped the bag of lingerie out, and spread it all out on the floor. There was lots of sexy stuff there.
But Lucy was a bit unsure about me wearing any of it. "But you'll be wearing my mum's underwear!"

Agreed, there is a strange element to this. But, most of the lingerie looked expensive. And would save us buying anything else specifically for me.

I'll see what Lucy thinks about it, after she's got used to the idea.

A surprising Sunday.

Wow. Lots of spice there in
This situation. More than enough to suggest the Greg scenario can be a chance.

One question, does Lucy actually know how big Greg's cock is? If not would the waxing day be a good chance to unveil it to impress her?

Paulypippa
Prepubescent
Posts: 8
Joined: Thu Oct 19, 2023 5:33 am

Re: Want my wife to cuckold me with my best friend.

Unread post by Paulypippa » Tue Dec 09, 2025 3:35 am

johnswan wrote:
Mon Dec 08, 2025 11:27 pm
I have to tell you about something that happened over the weekend.

We went over to Lucy's parents on Sunday .They have an indoor sauna that we occasionally use. The idea was to go early enough so that we could use their sauna, have a break, have lunch, then watch the Formula 1 final race in the afternoon.

Before we left home Lucy asked me to wear the panties from the bra and pantie set we bought for me recently. The panties are bright pink, lacey etc, obviously feminine.
I only agreed on the basis that she went without a bra for the afternoon. I knew that we would be sharing the sauna with Lucy's sister, Jessica, and her boyfriend, James. I thought it would be fun for James to see Lucy braless! Under a top of some sort, of course.

Later, we were in the sauna, and Jessica almost immediately asked me what happened to my chest hair. In that I no longer had any (we've shared the sauna with her before, so she knew I had chest hair previously).
And before I could reply, Lucy said "I shaved it off". Her sister just sort of smirked, as did her boyfriend, them both exchanging looks with each other. Nothing more was said, fortunately.
Oh, and in the sauna I wore a pair of conventional male boxer shorts that I'd taken, Lucy wearing a fairly skimpy bikini. Her sister and boyfriend dressed similarly.

After the sauna I went with Lucy to her old bedroom, and waited while she showered. Then swapped with her when she'd finished. Lucy disappeared somewhere, leaving me to shower. After my shower I put the pink panties back on, and was sat on the bed, drying my hair with a towel. The bedroom door opened, and I assumed it was Lucy returning. But when I took the towel from my head, I saw that it was Lucy's mum!
She immediately apologised, saying that she thought we were still in the sauna.

She had obviously seen the pink panties.

She went to leave, then stopped at the open door, coming back into the bedroom.
She said "Can I ask you something personal? You don't have to answer if you don't want to".
I couldn't think what else to say, but replied, yes, she could ask me whatever she wanted.
She said "I know that Lucy can be a very.... determined lady, at times. And I know that you, John, are a bit of a softy with her. Which is nice. But....I hope that the underwear that you have on....is that your own choice? Or is Lucy pushing you to do things you don't want to?"

At first I didn't know what to say. Because, me wearing the panties wasn't my choice. But I hadn't really been forced to do it.
Ok, coerced a bit maybe.

So I tried to explain that, no I hadn't been pushed or forced into wearing the panties. And just, clumsily, tried to explain that it was something we occasionally did for fun.
I couldn't really tell her that the deal was that, if I wore the panties, Lucy would go braless under her top, to tease James.
And I certainly wasn't going to get into an explanation of Lucy domming me, to wear female underwear!

Anyway, she seemed happy that I wasn't being forced into doing things by her daughter. At which point Lucy returned, coming into the bedroom, and seeing me with just the pink panties on. And her mum there.

At which point her mum said, "ok, I'll leave you to it", and went to leave. But then stopped again.
She said "I've got an idea. Come with me, both of you". And she went out into the corridor. I looked at Lucy, who sort of shrugged, indicating she didn't know what her mum wanted. Lucy took my hand, to lead me out, to follow her mum. But I was hissing to Lucy that I couldn't leave the bedroom wearing only the panties!
Lucy checked outside, on the corridor and said there was no one about, pulling me to follow her mum.

Who led us to Lucy's parents bedroom.
Once in the bedroom, Lucy's mum told me to sit on the bed.

Just as a side note, I was familiar with Lucy's parents bedroom. When we were at university, and home for the holidays, I'd spend most of my time at Lucy's. I shared Lucy's bedroom, supposedly sleeping on a temporary bed, but obviously sleeping with Lucy. Which I'm sure her parents knew, but didn't seem bothered about. But if her parents were away for the weekend, or holiday, then Lucy would drag me to her parents bedroom, which had a large double bed. Which made me nervous, but was nicer than fucking Lucy on her single bed. Also, Lucy would rummage through her mum's extensive lingerie selection, modelling stuff for me, getting me very excited. I fucked Lucy a few times on that bed, with Lucy still wearing a pair of her mum's fancy silky, or satiny knickers. It's where I first discovered French Knickers, which I think are called 'tap pants' in the USA?

Anyway, Lucy's mum disappeared into their large walk in wardrobe and came back with a large carrier bag.

"This is some of my old lingerie, that I no longer wear. I have offered it to Lucy, as she is a similar size to these items. But she didn't want to wear her mum's cast off lingerie....understandably, I suppose. But they are too good to throw away, or give to a charity shop. So, I thought you might like them, to 'play' with. What do you think?"

She then proceeded to show me some of the contents of the bag. At which point Lucy excused herself, and left. Now I was alone with her mum, who was holding up various panties and other lingerie for me to see.
I didn't know what to say!

Then, she said "Do you want to try anything on, to check they fit you, before you take them..... assuming you'd like to take them?"

I wasn't sure if she was expecting me to try them on in her bedroom, there and then, or for me to take them back to Lucy's bedroom to try.
"No need to be shy" she said. "I don't suppose you've anything I haven't seen before".
Her mum is a medical consultant, so I'm sure she's seen plenty.

But I deferred on the offer to try anything on, and just said that, if she didn't mind, I'd take them and try them at home. She smiled, and said she understood.

Then she sat on the bed next to me, put her arm around me, and said "It's ok, you wanting to wear female things. Lucy's father.....well, we won't go into that.....".

Then she put a hand on my upper thigh, and squeezed it. And gave me a kiss on my forehead, pulling me to her.
"I'm glad my daughter married you" she said. "You are a very sweet boy".

At which point she got up and left to sort out lunch.

I quickly snuck the bag of lingerie back to Lucy's bedroom, and got fully dressed.

Later, when we'd got home, we tipped the bag of lingerie out, and spread it all out on the floor. There was lots of sexy stuff there.
But Lucy was a bit unsure about me wearing any of it. "But you'll be wearing my mum's underwear!"

Agreed, there is a strange element to this. But, most of the lingerie looked expensive. And would save us buying anything else specifically for me.

I'll see what Lucy thinks about it, after she's got used to the idea.

A surprising Sunday.

Wow. Lots of spice there in
This situation. More than enough to suggest the Greg scenario can be a chance.

One question, does Lucy actually know how big Greg's cock is? If not would the waxing day be a good chance to unveil it to impress her?

viking53
Trainable
Posts: 57
Joined: Fri Jan 05, 2024 1:24 am

Re: Want my wife to cuckold me with my best friend.

Unread post by viking53 » Tue Dec 09, 2025 4:26 am

johnswan wrote:
Mon Dec 08, 2025 11:27 pm

Later, when we'd got home, we tipped the bag of lingerie out, and spread it all out on the floor. There was lots of sexy stuff there.
But Lucy was a bit unsure about me wearing any of it. "But you'll be wearing my mum's underwear!"

Agreed, there is a strange element to this. But, most of the lingerie looked expensive. And would save us buying anything else specifically for me.

I'll see what Lucy thinks about it, after she's got used to the idea.

A surprising Sunday.
You wearing your MIL's underwear is incredibly hot, especially as she gave it to you specifically for you to wear. It definitely adds an extra dimension to Lucy's dominance so I'm sure that she will realise that and accept and actively support the idea.

Wantsomefunto
$2 Ho
Posts: 966
Joined: Tue Mar 14, 2023 1:17 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by Wantsomefunto » Tue Dec 09, 2025 7:10 am

Did you get hard as her mum showed you the lingerie? Did mum notice if you did

a2malways
Virgin
Posts: 25
Joined: Mon Apr 22, 2024 5:34 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by a2malways » Tue Dec 09, 2025 9:24 am

johnswan wrote:
Mon Dec 08, 2025 11:27 pm
I have to tell you about something that happened over the weekend.

We went over to Lucy's parents on Sunday .They have an indoor sauna that we occasionally use. The idea was to go early enough so that we could use their sauna, have a break, have lunch, then watch the Formula 1 final race in the afternoon.

Before we left home Lucy asked me to wear the panties from the bra and pantie set we bought for me recently. The panties are bright pink, lacey etc, obviously feminine.
I only agreed on the basis that she went without a bra for the afternoon. I knew that we would be sharing the sauna with Lucy's sister, Jessica, and her boyfriend, James. I thought it would be fun for James to see Lucy braless! Under a top of some sort, of course.

Later, we were in the sauna, and Jessica almost immediately asked me what happened to my chest hair. In that I no longer had any (we've shared the sauna with her before, so she knew I had chest hair previously).
And before I could reply, Lucy said "I shaved it off". Her sister just sort of smirked, as did her boyfriend, them both exchanging looks with each other. Nothing more was said, fortunately.
Oh, and in the sauna I wore a pair of conventional male boxer shorts that I'd taken, Lucy wearing a fairly skimpy bikini. Her sister and boyfriend dressed similarly.

After the sauna I went with Lucy to her old bedroom, and waited while she showered. Then swapped with her when she'd finished. Lucy disappeared somewhere, leaving me to shower. After my shower I put the pink panties back on, and was sat on the bed, drying my hair with a towel. The bedroom door opened, and I assumed it was Lucy returning. But when I took the towel from my head, I saw that it was Lucy's mum!
She immediately apologised, saying that she thought we were still in the sauna.

She had obviously seen the pink panties.

She went to leave, then stopped at the open door, coming back into the bedroom.
She said "Can I ask you something personal? You don't have to answer if you don't want to".
I couldn't think what else to say, but replied, yes, she could ask me whatever she wanted.
She said "I know that Lucy can be a very.... determined lady, at times. And I know that you, John, are a bit of a softy with her. Which is nice. But....I hope that the underwear that you have on....is that your own choice? Or is Lucy pushing you to do things you don't want to?"

At first I didn't know what to say. Because, me wearing the panties wasn't my choice. But I hadn't really been forced to do it.
Ok, coerced a bit maybe.

So I tried to explain that, no I hadn't been pushed or forced into wearing the panties. And just, clumsily, tried to explain that it was something we occasionally did for fun.
I couldn't really tell her that the deal was that, if I wore the panties, Lucy would go braless under her top, to tease James.
And I certainly wasn't going to get into an explanation of Lucy domming me, to wear female underwear!

Anyway, she seemed happy that I wasn't being forced into doing things by her daughter. At which point Lucy returned, coming into the bedroom, and seeing me with just the pink panties on. And her mum there.

At which point her mum said, "ok, I'll leave you to it", and went to leave. But then stopped again.
She said "I've got an idea. Come with me, both of you". And she went out into the corridor. I looked at Lucy, who sort of shrugged, indicating she didn't know what her mum wanted. Lucy took my hand, to lead me out, to follow her mum. But I was hissing to Lucy that I couldn't leave the bedroom wearing only the panties!
Lucy checked outside, on the corridor and said there was no one about, pulling me to follow her mum.

Who led us to Lucy's parents bedroom.
Once in the bedroom, Lucy's mum told me to sit on the bed.

Just as a side note, I was familiar with Lucy's parents bedroom. When we were at university, and home for the holidays, I'd spend most of my time at Lucy's. I shared Lucy's bedroom, supposedly sleeping on a temporary bed, but obviously sleeping with Lucy. Which I'm sure her parents knew, but didn't seem bothered about. But if her parents were away for the weekend, or holiday, then Lucy would drag me to her parents bedroom, which had a large double bed. Which made me nervous, but was nicer than fucking Lucy on her single bed. Also, Lucy would rummage through her mum's extensive lingerie selection, modelling stuff for me, getting me very excited. I fucked Lucy a few times on that bed, with Lucy still wearing a pair of her mum's fancy silky, or satiny knickers. It's where I first discovered French Knickers, which I think are called 'tap pants' in the USA?

Anyway, Lucy's mum disappeared into their large walk in wardrobe and came back with a large carrier bag.

"This is some of my old lingerie, that I no longer wear. I have offered it to Lucy, as she is a similar size to these items. But she didn't want to wear her mum's cast off lingerie....understandably, I suppose. But they are too good to throw away, or give to a charity shop. So, I thought you might like them, to 'play' with. What do you think?"

She then proceeded to show me some of the contents of the bag. At which point Lucy excused herself, and left. Now I was alone with her mum, who was holding up various panties and other lingerie for me to see.
I didn't know what to say!

Then, she said "Do you want to try anything on, to check they fit you, before you take them..... assuming you'd like to take them?"

I wasn't sure if she was expecting me to try them on in her bedroom, there and then, or for me to take them back to Lucy's bedroom to try.
"No need to be shy" she said. "I don't suppose you've anything I haven't seen before".
Her mum is a medical consultant, so I'm sure she's seen plenty.

But I deferred on the offer to try anything on, and just said that, if she didn't mind, I'd take them and try them at home. She smiled, and said she understood.

Then she sat on the bed next to me, put her arm around me, and said "It's ok, you wanting to wear female things. Lucy's father.....well, we won't go into that.....".

Then she put a hand on my upper thigh, and squeezed it. And gave me a kiss on my forehead, pulling me to her.
"I'm glad my daughter married you" she said. "You are a very sweet boy".

At which point she got up and left to sort out lunch.

I quickly snuck the bag of lingerie back to Lucy's bedroom, and got fully dressed.

Later, when we'd got home, we tipped the bag of lingerie out, and spread it all out on the floor. There was lots of sexy stuff there.
But Lucy was a bit unsure about me wearing any of it. "But you'll be wearing my mum's underwear!"

Agreed, there is a strange element to this. But, most of the lingerie looked expensive. And would save us buying anything else specifically for me.

I'll see what Lucy thinks about it, after she's got used to the idea.

A surprising Sunday.
johnswan

I have been reading your thread with interest and hope for you since the beginning, but for the first time I have a modest proposal

FUCK LUCY'S MUM!
FUCK LUCY'S MUM!
FUCK LUCY'S MUM!

Emmm, that is all.

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Re: Want my wife to cuckold me with my best friend.

Unread post by Long Lurker 34 » Tue Dec 09, 2025 4:02 pm

johnswan wrote:
Mon Dec 08, 2025 11:27 pm
I have to tell you about something that happened over the weekend.

We went over to Lucy's parents on Sunday .They have an indoor sauna that we occasionally use. The idea was to go early enough so that we could use their sauna, have a break, have lunch, then watch the Formula 1 final race in the afternoon.

Before we left home Lucy asked me to wear the panties from the bra and pantie set we bought for me recently. The panties are bright pink, lacey etc, obviously feminine.
I only agreed on the basis that she went without a bra for the afternoon. I knew that we would be sharing the sauna with Lucy's sister, Jessica, and her boyfriend, James. I thought it would be fun for James to see Lucy braless! Under a top of some sort, of course.

Later, we were in the sauna, and Jessica almost immediately asked me what happened to my chest hair. In that I no longer had any (we've shared the sauna with her before, so she knew I had chest hair previously).
And before I could reply, Lucy said "I shaved it off". Her sister just sort of smirked, as did her boyfriend, them both exchanging looks with each other. Nothing more was said, fortunately.
Oh, and in the sauna I wore a pair of conventional male boxer shorts that I'd taken, Lucy wearing a fairly skimpy bikini. Her sister and boyfriend dressed similarly.

After the sauna I went with Lucy to her old bedroom, and waited while she showered. Then swapped with her when she'd finished. Lucy disappeared somewhere, leaving me to shower. After my shower I put the pink panties back on, and was sat on the bed, drying my hair with a towel. The bedroom door opened, and I assumed it was Lucy returning. But when I took the towel from my head, I saw that it was Lucy's mum!
She immediately apologised, saying that she thought we were still in the sauna.

She had obviously seen the pink panties.

She went to leave, then stopped at the open door, coming back into the bedroom.
She said "Can I ask you something personal? You don't have to answer if you don't want to".
I couldn't think what else to say, but replied, yes, she could ask me whatever she wanted.
She said "I know that Lucy can be a very.... determined lady, at times. And I know that you, John, are a bit of a softy with her. Which is nice. But....I hope that the underwear that you have on....is that your own choice? Or is Lucy pushing you to do things you don't want to?"

At first I didn't know what to say. Because, me wearing the panties wasn't my choice. But I hadn't really been forced to do it.
Ok, coerced a bit maybe.

So I tried to explain that, no I hadn't been pushed or forced into wearing the panties. And just, clumsily, tried to explain that it was something we occasionally did for fun.
I couldn't really tell her that the deal was that, if I wore the panties, Lucy would go braless under her top, to tease James.
And I certainly wasn't going to get into an explanation of Lucy domming me, to wear female underwear!

Anyway, she seemed happy that I wasn't being forced into doing things by her daughter. At which point Lucy returned, coming into the bedroom, and seeing me with just the pink panties on. And her mum there.

At which point her mum said, "ok, I'll leave you to it", and went to leave. But then stopped again.
She said "I've got an idea. Come with me, both of you". And she went out into the corridor. I looked at Lucy, who sort of shrugged, indicating she didn't know what her mum wanted. Lucy took my hand, to lead me out, to follow her mum. But I was hissing to Lucy that I couldn't leave the bedroom wearing only the panties!
Lucy checked outside, on the corridor and said there was no one about, pulling me to follow her mum.

Who led us to Lucy's parents bedroom.
Once in the bedroom, Lucy's mum told me to sit on the bed.

Just as a side note, I was familiar with Lucy's parents bedroom. When we were at university, and home for the holidays, I'd spend most of my time at Lucy's. I shared Lucy's bedroom, supposedly sleeping on a temporary bed, but obviously sleeping with Lucy. Which I'm sure her parents knew, but didn't seem bothered about. But if her parents were away for the weekend, or holiday, then Lucy would drag me to her parents bedroom, which had a large double bed. Which made me nervous, but was nicer than fucking Lucy on her single bed. Also, Lucy would rummage through her mum's extensive lingerie selection, modelling stuff for me, getting me very excited. I fucked Lucy a few times on that bed, with Lucy still wearing a pair of her mum's fancy silky, or satiny knickers. It's where I first discovered French Knickers, which I think are called 'tap pants' in the USA?

Anyway, Lucy's mum disappeared into their large walk in wardrobe and came back with a large carrier bag.

"This is some of my old lingerie, that I no longer wear. I have offered it to Lucy, as she is a similar size to these items. But she didn't want to wear her mum's cast off lingerie....understandably, I suppose. But they are too good to throw away, or give to a charity shop. So, I thought you might like them, to 'play' with. What do you think?"

She then proceeded to show me some of the contents of the bag. At which point Lucy excused herself, and left. Now I was alone with her mum, who was holding up various panties and other lingerie for me to see.
I didn't know what to say!

Then, she said "Do you want to try anything on, to check they fit you, before you take them..... assuming you'd like to take them?"

I wasn't sure if she was expecting me to try them on in her bedroom, there and then, or for me to take them back to Lucy's bedroom to try.
"No need to be shy" she said. "I don't suppose you've anything I haven't seen before".
Her mum is a medical consultant, so I'm sure she's seen plenty.

But I deferred on the offer to try anything on, and just said that, if she didn't mind, I'd take them and try them at home. She smiled, and said she understood.

Then she sat on the bed next to me, put her arm around me, and said "It's ok, you wanting to wear female things. Lucy's father.....well, we won't go into that.....".

Then she put a hand on my upper thigh, and squeezed it. And gave me a kiss on my forehead, pulling me to her.
"I'm glad my daughter married you" she said. "You are a very sweet boy".

At which point she got up and left to sort out lunch.

I quickly snuck the bag of lingerie back to Lucy's bedroom, and got fully dressed.

Later, when we'd got home, we tipped the bag of lingerie out, and spread it all out on the floor. There was lots of sexy stuff there.
But Lucy was a bit unsure about me wearing any of it. "But you'll be wearing my mum's underwear!"

Agreed, there is a strange element to this. But, most of the lingerie looked expensive. And would save us buying anything else specifically for me.

I'll see what Lucy thinks about it, after she's got used to the idea.

A surprising Sunday.
JS
- There's got to be a story there some place. Perhaps over time you can tease it out of your MIL and, ah, pass it on.
- Is your FIL still in the picture?

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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Tue Dec 09, 2025 11:03 pm

Gulfcpl wrote:
Tue Dec 09, 2025 1:49 am
Wow, very hot in a strange way but still hot. Progress is being made in several different directions.
Yes, the 'progress in several different directions' thing, is a bit of a concern, actually. I feel that things are getting a little bit out of my control.

Ok, I know I can't possibly control everything, but, I'd like to try and keep the focus on a journey to my being cucked.

But, I can't complain. The other things we've started experiencing have been fun too.

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Re: Want my wife to cuckold me with my best friend.

Unread post by kaskap79 » Tue Dec 09, 2025 11:08 pm

I think that the more open you are to try things your wife wants you to, the more open she is to try the things you want her to do.

This game is not an one game, it is give and take.

But, we always have the rights to say no to something if it is too bad for us.
When you are lying of your death bed, you only regret the things you did not do.

The most beautiful woman in the world is the woman lying naked and sweaty next to me.

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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Tue Dec 09, 2025 11:09 pm

Paulypippa wrote:
Tue Dec 09, 2025 3:34 am
Wow. Lots of spice there in
This situation. More than enough to suggest the Greg scenario can be a chance.

One question, does Lucy actually know how big Greg's cock is? If not would the waxing day be a good chance to unveil it to impress her?
No, I've never told her about his cock size.
There is a story about that, that I'll try to post soon. But, suffice to say that, when we were at school, I think aged 17, he showed me his erect cock.

I think I'll tell her that story, if I can somehow blend it into a conversation.

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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Tue Dec 09, 2025 11:29 pm

viking53 wrote:
Tue Dec 09, 2025 4:26 am
You wearing your MIL's underwear is incredibly hot, especially as she gave it to you specifically for you to wear. It definitely adds an extra dimension to Lucy's dominance so I'm sure that she will realise that and accept and actively support the idea.
I'm certainly hoping so. Up till now I've always been the reluctant one when Lucy has asked me, more like told me, to put female underwear on. Especially when it came to putting on a bra. I was only able to do that because she absolutely insisted. It made me feel very ashamed and embarrassed. Which I suppose is partly the aim.

It started out being just Lucy's used panties, which did have an erotic element for me. But it escalated to the odd occasion where a bra was added, and sometimes stockings and suspenders. Which was difficult for me, because the feeling of submission I got was almost overwhelming.

Then we bought the pink bra and panty set specifically for me, just recently. And now, suddenly, my 'wardrobe' has just expanded considerably. The items that her mum gave me are all sexy lingerie. And, as far as I can tell, are expensive, from labels I've never heard of. They are clearly quality pieces. And as such, I do feel somewhat more attracted to wearing them.

We've just got to get over the thing about "but they're my mum's!". I'm going to suggest I try 'modelling' some of the items when we next get the chance.

And, as you point out, there is a strange dominance aspect to it being her mum's lingerie, that I can point out to Lucy, which might encourage her.

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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Tue Dec 09, 2025 11:46 pm

Wantsomefunto wrote:
Tue Dec 09, 2025 7:10 am
Did you get hard as her mum showed you the lingerie? Did mum notice if you did
No, not hard. But maybe slightly engorged. To be honest I was quite nervous about where her mum was going with the lingerie donation, so wasn't that aware of my cock size, at the time. But I was concerned about how much of my cock she'd be able to see underneath my pink panties. They have a mesh patch just around the crotch area, so I presume she could see quite a lot. I was concerned that she'd be able to see that I didn't have any pubic hair. And then tell me to show her!

The most nervous part, was when she put her hand on my upper thigh, and gave me a little squeeze. I thought she might just slip her hand under my panties! I think she knew that I'd feel nervous, and she was having some teasing fun at my expense.
Lucy, her sister and her mum are all 'teasers'. I've suffered from a few 'tricks' and 'teases' that they've played on me, over the years I've known them.

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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Tue Dec 09, 2025 11:56 pm

a2malways wrote:
Tue Dec 09, 2025 9:24 am
johnswan

I have been reading your thread with interest and hope for you since the beginning, but for the first time I have a modest proposal

FUCK LUCY'S MUM!
FUCK LUCY'S MUM!
FUCK LUCY'S MUM!

Emmm, that is all.
😊

I have to admit that, in the past, I have fantasised about her mum seducing me....fully!
She's got the same large bust as Lucy, is late 40's and has that 'mature woman, who knows what she wants' appeal.

But, it wouldn't be a case of 'me fucking her mum'.
More like 'her mum fucking me'.

But, no, getting back to reality, that's a complication I can do without!

One to keep as just fantasy. ☹️

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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Wed Dec 10, 2025 12:06 am

Long Lurker 34 wrote:
Tue Dec 09, 2025 4:02 pm
johnswan wrote:
Mon Dec 08, 2025 11:27 pm

Then she sat on the bed next to me, put her arm around me, and said "It's ok, you wanting to wear female things. Lucy's father.....well, we won't go into that.....".

JS
- There's got to be a story there some place. Perhaps over time you can tease it out of your MIL and, ah, pass it on.
- Is your FIL still in the picture?
I have already asked Lucy about that 'half' comment from her mum. But Lucy said she knew nothing about that. Her dad is a quiet man, with three females who are quite a handful for him to have had to deal with.
Could he have been into some cross dressing, or similar? You just never know, do you?

It's a bit like trying to imagine your own parents having sex. You know they've done it, are maybe still doing it. But you just don't want to know the details! 🫢😳

But, who knows, maybe her mum might divulge more, over time.

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Re: Want my wife to cuckold me with my best friend.

Unread post by kaskap79 » Wed Dec 10, 2025 12:10 am

Yes, who knows if Lucy's mother is a hotwife and Lucy just don't know it yet.
When you are lying of your death bed, you only regret the things you did not do.

The most beautiful woman in the world is the woman lying naked and sweaty next to me.

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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Wed Dec 10, 2025 12:19 am

kaskap79 wrote:
Tue Dec 09, 2025 11:08 pm
I think that the more open you are to try things your wife wants you to, the more open she is to try the things you want her to do.

This game is not an one game, it is give and take.

But, we always have the rights to say no to something if it is too bad for us.
Yes, you are absolutely correct.

We already do some 'horse trading' on things....the "ok, I'll agree to that, if you agree to this" type stuff.

My natural inclination is to try to retain control of things. I just feel 'safer' that way.

But, I also like it when Lucy takes control. Sometimes it's like handing over the reins of a horse, when you've been trotting along at a nice steady pace. And you know that she's going to make the horse gallop, as soon as she takes the reins.
And galloping can be fun too! 😲🙂

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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Wed Dec 10, 2025 12:30 am

kaskap79 wrote:
Wed Dec 10, 2025 12:10 am
Yes, who knows if Lucy's mother is a hotwife and Lucy just don't know it yet.
It's possible. People often use the phrase, "Like father, like son", but "like mother, like daughter" is equally valid.
I'm sure Lucy would have mentioned something to me before now, assuming that she'd have known anything about that possibility.

But, as you say, maybe her mum's been discrete, and Lucy has no idea.
Her mum wouldn't be short of admirers, that's for sure!
As I said, "like mother, like daughter". 😁

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Re: Want my wife to cuckold me with my best friend.

Unread post by kaskap79 » Wed Dec 10, 2025 12:33 am

It can be very fun, indeed.

But remember that Lucy having sex with another man is putting her in a place where she does not feel she is in control at all, and therefor it can be good that you are willing to try something where you also have no control at all. Just to show her that it can be done.

But you also have to make trust that this is something you only want if she also wants it. If she does not want it, I do it for you, it will destroy more than what you get.

When you start to discuss it, one thing I find useful is that set up a rule that both of you can stop the game at any time, including when they are just about to have sex or while having sex. No demand for explaining why one of you stopped the game. You can also discuss that later when times seems right.

Also if she agrees to have sex, then do not set up rules about what to do and not to do. Set guidelines instead. It is difficult to get over a rule being broken, but easier if it a guideline.
In the heat of the moment, it might be difficult to remember rules.

Anyway, good luck on your journey.
When you are lying of your death bed, you only regret the things you did not do.

The most beautiful woman in the world is the woman lying naked and sweaty next to me.

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Re: Want my wife to cuckold me with my best friend.

Unread post by Paulypippa » Wed Dec 10, 2025 2:35 am

johnswan wrote:
Tue Dec 09, 2025 11:09 pm
Paulypippa wrote:
Tue Dec 09, 2025 3:34 am
Wow. Lots of spice there in
This situation. More than enough to suggest the Greg scenario can be a chance.

One question, does Lucy actually know how big Greg's cock is? If not would the waxing day be a good chance to unveil it to impress her?
No, I've never told her about his cock size.
There is a story about that, that I'll try to post soon. But, suffice to say that, when we were at school, I think aged 17, he showed me his erect cock.

I think I'll tell her that story, if I can somehow blend it into a conversation.

Maybe you can jokingly say that there "will
Be a big surprise" if he's waxed all
Over on the day!

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Re: Want my wife to cuckold me with my best friend.

Unread post by Colliercuck » Wed Dec 10, 2025 3:29 am

If Lucy allows you to keep her mums panties, maybe then you should model some for her mum
She would probably enjoy that, and might even teach Lucy a few things
Could definitely be something that draws them closer and the two of them being in this position of power together could be an interesting dynamic

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Re: Want my wife to cuckold me with my best friend.

Unread post by Wantsomefunto » Wed Dec 10, 2025 4:41 am

I agree with the last post, pick something out her mum gave you and model for Lucy to take a pic and show her mom.

It’s very good her mom is open to you wearing ladies lingerie.

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