Want my wife to cuckold me with my best friend.

For cuckoldresses and the men who serve them.
Koolaide4fun
Prepubescent
Posts: 3
Joined: Wed Jan 06, 2021 12:18 am

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

Unread post by Koolaide4fun » Tue Nov 18, 2025 5:27 pm

Not that it would work for you but it's an idea to think about. I had a friend I grew up with that went in military immediately after graduation. He never was popular with girls he was the d&d rotc type nerd but he was good enough athlete to get scholarship as a defensive back he was free safety on high school team.
I had went to college forgot about him until I had graduated and was working for an advertising agency featured in commercials and using my marketing degree to get acting gigs. We had an account with huge military surplus warehouse who did these real funny commercials we needed an army n Air Force a marine and a navy solider for commerical they need to have there dress uniform it was the last day b4 moving on to different thing for the ad when a guy called and asked if we had a navy seaman for our casting I said no and I also need a Marine by 6 pm it was to film 2morrow I said it pays 250.00 only 2 speaking roles the army and Air Force guys will due it. The guy said he was friends with a marine he will call back in 5 mins an hour later he is meeting the others at the surplus store to rehearse the next day the director scheduled to comericals at same time so I went to help with the surplus ad it went off with out a hitch.
After I was telling everyone to pack up I had plans meeting a couple for lunch when The navy guy walked up and said big Phil as turning I said it's Mr. Phil now he was apologizing when I recognized him said he was fresh out of the navy and he was married and had 1 kid adding adopted. Asked did I ever settle down I told him why settle down when men will bring there wife to me to fuck. He laughed and asked about getting a beer I left my number with him and thought no more about it. A few days later he called asked where I worked out what gym I told him he said would I meet him there to workout we really pushed each other in high school I said sure told him the time and we had a great work out. While sitting in steam room he asked me if rumor in high school was true that I fucked that young female volleyball and softball coach who was still in college who was married to Mr. Kirkland the head of math department. I told him yes but to ensure he would not tell on me or her I had super 8 mm video no sound of him sucking my cock as he asked if a lot of the married women I fuck have husbands that suck my cock I pushed towel off and leaned back reaching down I grabbed my cock why would you ask would you suck my cock to see me fuck your wife. Looking at the floor he said yes Mr. Phil have you ever convinced a wife to bring her husband into being a cuckold instead of me asking her and introducing her to you. How about I tell her the director of commerical was friend from high school he wants to meet you and take us out to eat. I had only looked at floor in front of me 1 time b4 he was there watching my stroke my cock. I told him as I lifted my balls start licking here pointing under my balls not to far from my asshole I dropped my balls on his face and said stroke my cock I had a bottle of cold water and poured over his hand pulling by his ear so my heavy ball sac is now where he can kiss lick and suck my cock. I said you have worshiped a mans set of balls b4 you ever suck a cock like mine. He said no Sir in the navy he had female officer who would humiliate him and make him clean her lovers and her cum filled pussy. I ask does your wife work he said she does party planning but works from home 45 mins later I'm driving him home while he sucks my cock on his knees in passenger seat face in my lap. We pulled up at his house his wife was outside I had seen her thankfully for him I had very dark tinted windows she was maybe 8 feet from my car when I pulled him off my cock grabbing the sucker I had opened and licked a few times. I told him she can't see it pointing to his wife I told him catch that precum with your sucker put my cock away pointing out she's going to see my cock print in these nylon running shorts they were very lose around legs and had a pouch for avg 5 inch dick and balls not my 9 inch beer can thick cock and 2 handfuls of balls. I made sure he had the same color and size as I did white. I told him when you get out almost run around car and kiss your wife then tell her she has to me Mr. Phil from your high school class then open the door make sure she is where she sees me sitting in seat then step back while I get out of car I will introduce myself you be sure to stand beside me while I ask her if she and her little hubs would meet me for supper I will send a car. Then tell her how about I see if your little hub lied to me he said you would need to go shopping for a dress I take her hand and say keep up lil petey. 20 mins later I have picked out dress thigh highs and heals. I tell her she will be most beautiful lady at restaurant sexy3st also then say are we clear on what you are to wear she said yes I pointed that only that if it's not on that bed your not to wear it. I then asked lil petey do I need to choose your clothes also he said no Sir. I told him go get your jumper cables I will drive you back to your car. I walk up to Gina his wife and said I forgot the panties show me 3 of sexiest pair picking up the sheer neon pink g string they were stripper panties they fastened on top corners then only a string I grab them make him dress first in front of you if he don't put these on tell him call me. Phil. 3 mins later I walk out and with her looking out window I told her if she had any doubts what he wanted to walk down to park I will have window down. Sure enough 20 mins later I see her walking up I'm backed into treeline and can't be seen he is on his knees I'm leaning against my car legs spread and him hanging over and over choking Everytime I try to take my cock from him he begs please Mr. Phil. The thick saliva hangs from his chin and both cheeks his lip is busted and his eye is almost swollen shut from when I slap my cock across his face for dragging a tooth finally he is taken it all I hold him on it till he is frantic for air I'm out long enough to get 1/2 draw of air and I fuck his face balls slapping on his face then hold till he is frantic then not allow full breath saying you begged for me to cum on your mouth fuck your face try and hold my cock until you black out I will cum for you. I looking right at Gina your wife when I fuck your face then hold you tapping trying to pull back when for 1st 15 times I pulled you back only to slam cock back in your throat not allow a breath then when your given up hope of breathing I say stick your tongue out lick my balls I tilt his head and allow just faint airway to open then I push him to the ground I wipe up pee cum pouring out my cock and tell him crawl around car and get in knees in seat face in my seat wait eyes closed I lean in tell him open your cocksucker and shove the pink 5 backs in your wearing these tonight and dressing in front of your wife she turns walks away I sit in car my shorts in his wife's hand í say kiss and lick boy the next thing my cock will be in is your wife btw your getting my cum in all three holes I stop and tell him I'm waiting outside your to sit up walk up to door tell the guy Mr. Phill sent me said you know what I need I leave and after 15 minutes John walks back into room tell you why did you put shorts back on he quickly has wrapped rope around your hands and around ankles the stell bar in middle of back has your tiny clit and hips sticking out while hands and feet tied in like 1 min you felt cold steel ring around tiny clit and then your 2 inch boy clit is pushed that and another luck James hands you a mirro. The open hand slap across face with command did I say stop sucking it takes 2 of my load lil I mean no peter Mr. Phil will give your wife the keys to this with instructions on how to be a key holder he pulls rope and your untied James says Mr. Phil promised you a mouth full of cum he pushes you to knees it's not Mr Phil but your going to learn to love it as a substitute boy. Open up in about 3 mins cum is spurting right down throat in to belly then all over face then back in belly again then all over face again he said I got more for you 3 mins later he's covered in cum and told your cars out back go hime

Koolaide4fun
Prepubescent
Posts: 3
Joined: Wed Jan 06, 2021 12:18 am

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

Unread post by Koolaide4fun » Tue Nov 18, 2025 5:27 pm

Not that it would work for you but it's an idea to think about. I had a friend I grew up with that went in military immediately after graduation. He never was popular with girls he was the d&d rotc type nerd but he was good enough athlete to get scholarship as a defensive back he was free safety on high school team.
I had went to college forgot about him until I had graduated and was working for an advertising agency featured in commercials and using my marketing degree to get acting gigs. We had an account with huge military surplus warehouse who did these real funny commercials we needed an army n Air Force a marine and a navy solider for commerical they need to have there dress uniform it was the last day b4 moving on to different thing for the ad when a guy called and asked if we had a navy seaman for our casting I said no and I also need a Marine by 6 pm it was to film 2morrow I said it pays 250.00 only 2 speaking roles the army and Air Force guys will due it. The guy said he was friends with a marine he will call back in 5 mins an hour later he is meeting the others at the surplus store to rehearse the next day the director scheduled to comericals at same time so I went to help with the surplus ad it went off with out a hitch.
After I was telling everyone to pack up I had plans meeting a couple for lunch when The navy guy walked up and said big Phil as turning I said it's Mr. Phil now he was apologizing when I recognized him said he was fresh out of the navy and he was married and had 1 kid adding adopted. Asked did I ever settle down I told him why settle down when men will bring there wife to me to fuck. He laughed and asked about getting a beer I left my number with him and thought no more about it. A few days later he called asked where I worked out what gym I told him he said would I meet him there to workout we really pushed each other in high school I said sure told him the time and we had a great work out. While sitting in steam room he asked me if rumor in high school was true that I fucked that young female volleyball and softball coach who was still in college who was married to Mr. Kirkland the head of math department. I told him yes but to ensure he would not tell on me or her I had super 8 mm video no sound of him sucking my cock as he asked if a lot of the married women I fuck have husbands that suck my cock I pushed towel off and leaned back reaching down I grabbed my cock why would you ask would you suck my cock to see me fuck your wife. Looking at the floor he said yes Mr. Phil have you ever convinced a wife to bring her husband into being a cuckold instead of me asking her and introducing her to you. How about I tell her the director of commerical was friend from high school he wants to meet you and take us out to eat. I had only looked at floor in front of me 1 time b4 he was there watching my stroke my cock. I told him as I lifted my balls start licking here pointing under my balls not to far from my asshole I dropped my balls on his face and said stroke my cock I had a bottle of cold water and poured over his hand pulling by his ear so my heavy ball sac is now where he can kiss lick and suck my cock. I said you have worshiped a mans set of balls b4 you ever suck a cock like mine. He said no Sir in the navy he had female officer who would humiliate him and make him clean her lovers and her cum filled pussy. I ask does your wife work he said she does party planning but works from home 45 mins later I'm driving him home while he sucks my cock on his knees in passenger seat face in my lap. We pulled up at his house his wife was outside I had seen her thankfully for him I had very dark tinted windows she was maybe 8 feet from my car when I pulled him off my cock grabbing the sucker I had opened and licked a few times. I told him she can't see it pointing to his wife I told him catch that precum with your sucker put my cock away pointing out she's going to see my cock print in these nylon running shorts they were very lose around legs and had a pouch for avg 5 inch dick and balls not my 9 inch beer can thick cock and 2 handfuls of balls. I made sure he had the same color and size as I did white. I told him when you get out almost run around car and kiss your wife then tell her she has to me Mr. Phil from your high school class then open the door make sure she is where she sees me sitting in seat then step back while I get out of car I will introduce myself you be sure to stand beside me while I ask her if she and her little hubs would meet me for supper I will send a car. Then tell her how about I see if your little hub lied to me he said you would need to go shopping for a dress I take her hand and say keep up lil petey. 20 mins later I have picked out dress thigh highs and heals. I tell her she will be most beautiful lady at restaurant sexy3st also then say are we clear on what you are to wear she said yes I pointed that only that if it's not on that bed your not to wear it. I then asked lil petey do I need to choose your clothes also he said no Sir. I told him go get your jumper cables I will drive you back to your car. I walk up to Gina his wife and said I forgot the panties show me 3 of sexiest pair picking up the sheer neon pink g string they were stripper panties they fastened on top corners then only a string I grab them make him dress first in front of you if he don't put these on tell him call me. Phil. 3 mins later I walk out and with her looking out window I told her if she had any doubts what he wanted to walk down to park I will have window down. Sure enough 20 mins later I see her walking up I'm backed into treeline and can't be seen he is on his knees I'm leaning against my car legs spread and him hanging over and over choking Everytime I try to take my cock from him he begs please Mr. Phil. The thick saliva hangs from his chin and both cheeks his lip is busted and his eye is almost swollen shut from when I slap my cock across his face for dragging a tooth finally he is taken it all I hold him on it till he is frantic for air I'm out long enough to get 1/2 draw of air and I fuck his face balls slapping on his face then hold till he is frantic then not allow full breath saying you begged for me to cum on your mouth fuck your face try and hold my cock until you black out I will cum for you. I looking right at Gina your wife when I fuck your face then hold you tapping trying to pull back when for 1st 15 times I pulled you back only to slam cock back in your throat not allow a breath then when your given up hope of breathing I say stick your tongue out lick my balls I tilt his head and allow just faint airway to open then I push him to the ground I wipe up pee cum pouring out my cock and tell him crawl around car and get in knees in seat face in my seat wait eyes closed I lean in tell him open your cocksucker and shove the pink 5 backs in your wearing these tonight and dressing in front of your wife she turns walks away I sit in car my shorts in his wife's hand í say kiss and lick boy the next thing my cock will be in is your wife btw your getting my cum in all three holes I stop and tell him I'm waiting outside your to sit up walk up to door tell the guy Mr. Phill sent me said you know what I need I leave and after 15 minutes John walks back into room tell you why did you put shorts back on he quickly has wrapped rope around your hands and around ankles the stell bar in middle of back has your tiny clit and hips sticking out while hands and feet tied in like 1 min you felt cold steel ring around tiny clit and then your 2 inch boy clit is pushed that and another luck James hands you a mirro. The open hand slap across face with command did I say stop sucking it takes 2 of my load lil I mean no peter Mr. Phil will give your wife the keys to this with instructions on how to be a key holder he pulls rope and your untied James says Mr. Phil promised you a mouth full of cum he pushes you to knees it's not Mr Phil but your going to learn to love it as a substitute boy. Open up in about 3 mins cum is spurting right down throat in to belly then all over face then back in belly again then all over face again he said I got more for you 3 mins later he's covered in cum and told your cars out back go hime

johnswan
Experienced
Posts: 157
Joined: Fri Aug 15, 2025 10:17 pm

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

Unread post by johnswan » Tue Nov 18, 2025 11:36 pm

Koolaide4fun wrote:
Tue Nov 18, 2025 5:27 pm
Not that it would work for you but it's an idea to think about.
?

Or maybe I should say, "?", "?" and "?".

playwifeplease
Trainable
Posts: 58
Joined: Sat Nov 30, 2024 2:22 am

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

Unread post by playwifeplease » Wed Nov 19, 2025 12:28 am

johnswan wrote:
Tue Nov 18, 2025 11:36 pm
Koolaide4fun wrote:
Tue Nov 18, 2025 5:27 pm
Not that it would work for you but it's an idea to think about.
?

Or maybe I should say, "?", "?" and "?".
Yeah, that's a difficult read! :???:

MonaLisaOverdrive
Player
Posts: 275
Joined: Fri Jun 10, 2022 9:34 pm

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

Unread post by MonaLisaOverdrive » Wed Nov 19, 2025 10:14 am

playwifeplease wrote:
Wed Nov 19, 2025 12:28 am
johnswan wrote:
Tue Nov 18, 2025 11:36 pm
Koolaide4fun wrote:
Tue Nov 18, 2025 5:27 pm
Not that it would work for you but it's an idea to think about.
?

Or maybe I should say, "?", "?" and "?".
Yeah, that's a difficult read! :???:
Now thats what I call meth-posting :lol:

Cornoarg
Prepubescent
Posts: 7
Joined: Sat Nov 23, 2019 2:18 am

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

Unread post by Cornoarg » Wed Nov 19, 2025 11:03 am

My best friend is our main bull and we love it

User avatar
coastalkid
2 Bit Whore
Posts: 1200
Joined: Sun Jul 17, 2011 4:55 pm
Location: Central California Valley/Central Coast

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

Unread post by coastalkid » Wed Nov 19, 2025 11:58 am

Cornoarg wrote:
Wed Nov 19, 2025 11:03 am
My best friend is our main bull and we love it
I'm sure Johnswan would love to hear what is your best and worst thing about how it works with your best friend.
Hope is not a strategy but it's still good to have! Especially if you don't have a strategy!
I get my denial the old fashion way, I married vanilla!

johnswan
Experienced
Posts: 157
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 01, 2025 11:33 pm

Firstly, apologies for neglecting things here.

Since the weekend of 22nd/23rd November I was ill for a week with some sort of infection, followed by a week of catching up with various things.
So, until recently I've not really been in the mood for posting, or had the time.

But there are a couple of incidents that I'll share, that might be of some interest.

The first was on the Saturday before I got sick.

I went for a drink with Greg, my best friend, to catch up on various things. I wanted to tell him about Lucy shaving me, and me having my pubic hair waxed. It took a couple of pints before I plucked up courage to tell him.
He was quite surprised, and had lots of questions. Also, he was keen to see my shaved cock and balls. I think that was partly to embarrass me, and partly out of curiosity. Anyway, dropping my jeans and underwear, in our local town, on a Saturday night, wasn't the best idea, so I refused. Maybe another time.

He was interested in the waxing, and he decided that he will try having his chest hair waxed.
So Lucy has spoken to her friend Nikkie, and we will arrange a time, soon.

One reason I wanted to tell him about my shaving/waxing was to try to introduce him to the idea that me and Lucy don't have a solely vanilla sex life.

The second thing happened just before this weekend. Lucy and I had only just returned to having sex, and we'd only had time for a couple of quickie vanilla sessions.

But she was obviously in the mood for something more.
We had a session where she put my cock cage on me, then spanked me, much harder and longer than normal. This was something that I'd asked her to do, on my wishlist.
I did try not to give in, but she was quite relentless. No real super hard impacts, but just consistent regular spanks, that gradually build up the pain intensity. Eventually I had to ask her to stop.

But, mixed in with this, she had another idea in her head, that she'd read about (and I've subsequently learned, she spoke to a female friend of hers about). This was to give me prostate massage.
She did this after her first bout of spanking me. All this time I was on all fours on the bed, naked, her fully clothed.

Basically she lubed my bum, and gradually slid her finger into me, locating my prostate. Then started gently and slowly massaging it.
Then swapped back to spanking me again.
Followed by another prostate massage session.

The prostate massage was a completely new sensation for me. And I have to say, a very pleasurable one!

Anyway, we finished our session, Lucy getting me to lick her, while she masturbated.

I know that these two incidents don't contain any real cuckold content, but thought they were worth mentioning anyway.

For those that are interested, I've shared a long and detailed version of the above two sessions, with a couple of other members, via pm. If you are interested I can send the full versions. Just pm me.

Thanks.

Gulfcpl
Player
Posts: 333
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 02, 2025 12:46 am

Glad to hear you’re feeling better.

viking53
Trainable
Posts: 56
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 02, 2025 1:13 am

johnswan wrote:
Mon Dec 01, 2025 11:33 pm

For those that are interested, I've shared a long and detailed version of the above two sessions, with a couple of other members, via pm. If you are interested I can send the full versions. Just pm me.

Thanks.
Thanks for the update. Definitely interested in the detailed versions as I am sure many of your followers are. Please post them.

Long Lurker 34
OHW Addict
Posts: 3190
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 » Tue Dec 02, 2025 5:07 pm

johnswan wrote:
Mon Dec 01, 2025 11:33 pm
Firstly, apologies for neglecting things here.

Since the weekend of 22nd/23rd November I was ill for a week with some sort of infection, followed by a week of catching up with various things.
So, until recently I've not really been in the mood for posting, or had the time.

But there are a couple of incidents that I'll share, that might be of some interest.

The first was on the Saturday before I got sick.

I went for a drink with Greg, my best friend, to catch up on various things. I wanted to tell him about Lucy shaving me, and me having my pubic hair waxed. It took a couple of pints before I plucked up courage to tell him.
He was quite surprised, and had lots of questions. Also, he was keen to see my shaved cock and balls. I think that was partly to embarrass me, and partly out of curiosity. Anyway, dropping my jeans and underwear, in our local town, on a Saturday night, wasn't the best idea, so I refused. Maybe another time.

He was interested in the waxing, and he decided that he will try having his chest hair waxed.
So Lucy has spoken to her friend Nikkie, and we will arrange a time, soon.

One reason I wanted to tell him about my shaving/waxing was to try to introduce him to the idea that me and Lucy don't have a solely vanilla sex life.

The second thing happened just before this weekend. Lucy and I had only just returned to having sex, and we'd only had time for a couple of quickie vanilla sessions.

But she was obviously in the mood for something more.
We had a session where she put my cock cage on me, then spanked me, much harder and longer than normal. This was something that I'd asked her to do, on my wishlist.
I did try not to give in, but she was quite relentless. No real super hard impacts, but just consistent regular spanks, that gradually build up the pain intensity. Eventually I had to ask her to stop.

But, mixed in with this, she had another idea in her head, that she'd read about (and I've subsequently learned, she spoke to a female friend of hers about). This was to give me prostate massage.
She did this after her first bout of spanking me. All this time I was on all fours on the bed, naked, her fully clothed.

Basically she lubed my bum, and gradually slid her finger into me, locating my prostate. Then started gently and slowly massaging it.
Then swapped back to spanking me again.
Followed by another prostate massage session.

The prostate massage was a completely new sensation for me. And I have to say, a very pleasurable one!

Anyway, we finished our session, Lucy getting me to lick her, while she masturbated.

I know that these two incidents don't contain any real cuckold content, but thought they were worth mentioning anyway.

For those that are interested, I've shared a long and detailed version of the above two sessions, with a couple of other members, via pm. If you are interested I can send the full versions. Just pm me.

Thanks.
JS
- You should have her look into 'milking' you.

a2malways
Virgin
Posts: 24
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 02, 2025 6:17 pm

viking53 wrote:
Tue Dec 02, 2025 1:13 am
johnswan wrote:
Mon Dec 01, 2025 11:33 pm

For those that are interested, I've shared a long and detailed version of the above two sessions, with a couple of other members, via pm. If you are interested I can send the full versions. Just pm me.

Thanks.
Thanks for the update. Definitely interested in the detailed versions as I am sure many of your followers are. Please post them.

Agree. If there are things you feel you cannot disclose, it's understandable. But if it's cool I am sure many would love to see posted here.

And if not, can you send me a copy?

Post Reply