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How did it happen for the first time for you!??


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How did it all happen first time? 

Did you come up with the idea of cuckolding or was it your hubby?

what were your thoughts when it was first brought up?

And the actual experience of another man? 
my wife and I lost our virginity to each other so it is a difficult subject for her to have another man in bed. But I would like bigger better things for her and I.


I’d like to learn from your experiences

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Hi Brown. I don't really know how I got into this cuckolding lifestyle if I'm honest, but as a "usedtobe", rather than a "wannabe" perhaps my own experiences can help you . Debbie was my second wife, but I'd never had any cuckold tendencies with my first wife nor the woman I lived with before I met Debbie. My work involved me doing shifts of one week early, one week late, which led to Debbie gradually gaining a social life of her own  when I wasn't around. This could involve her drinking at my works' social club bar, going on girls's nights out with female friends or playing darts for a ladies team in a local pub and club league. This of course meant that she'd be in the company of men quite a lot and although she'd been quite promiscuous when she was younger and admitted she actually prefer male company to female, she seemed perfectly happy to be faithful to me.

Occasionally when we were out together I'd catch other men eyeing up my wife, which made me both quite proud and to a certain degree, aroused. Debbie had great legs which I encouraged her to show off in short dresses and mini-skirts, a far cry to the jeans she always wore when we first met. She didn't have big boobs, but with the aid of a Wonderbra and the wearing of my v-neck sweaters, Debbie was able to boost her cleavage and confessed to enjoying the extra attention she now attracted. I admitted that i liked it too.

From time to time she'd comment on TV or pop stars she fancied, quite often young guys in their early 20s and when a new club opened in town her and a friend visited on a few nights when acts were put on to encourage people to turn up. One band that appeared had a lead singer that Debbie took a definite shine to, telling her mate on the phone in bed with me later, how her pussy was twitching and getting wet when she spoke to him at the bar. Debbie told me he'd invited her to a club after their gig, even though his girlfriend was there. I told her she should have gone and if something had happened I'd be okay with that as long as she told me. "Oh yeah! As if!", was her first reaction, but that did at least broach the subject of her having sex with someone else.

Over the course of the next couple of years I would occasionally mention it again, but not so often that she got fed up hearing about it. She was working now in a 24 hour convenience store in a nearby town and would sometimes bring home a Playgirl magazine for us to look at in bed together and we'd enjoy admiring the naked men and their cocks. A couple we knew had brought her a novelty gift back from holiday, a plastic carrot which when you pulled on the green leaves at the top, reveal a fairly realistic dildo. We started using this in bed of course and it was this role-play that really got the ball rolling. I told Debbie how good it was watching another cock going in and out of her pussy and how naughty she was doing it with "him" right there in front of her husband. "You love it!", she'd murmur with a smile, as she climaxed more noisily than usual at the thought. "If you walked in on me actually having sex with someone, you wouldn't even try to stop me would you?", she said. "No, I wouldn't", I confessed, "I'd let you carry on." She liked that!

At work Debbie now told me she was being chatted up by Dave, one of their delivery lorry drivers. She was loving it and even changed her shifts to make sure she was there the days he came to her shop. He asked her out, suggesting she could stay at his overnight one weekend, but he lived quite a way away so she reluctantly declined. They did go to watch a football match together though, taking 2 of our kids with them. With them there they had to be discreet, but he did have his hand on her thigh and snatched a couple of sneaky kisses. 

Dave however was soon old news as a new name kept coming up in conversation when I asked Debbie how her day had been at work. A regular customer, a young guy called Chris, had started making a bee-line for Debbie and been chatting her up. Pretty sure that Chris was going to ask her out, Debbie ran the idea past me. She was very flattered by his attention and confessed that she'd like to go out for a drink with him. Would I be okay with that? And what if he wanted more than just a drink? "Yes babe. Of course. Go for it! I know you fancy having a toy-boy bit on the side. Do it."

Re-assured by my favorable reaction to her going on a date with a lad of 23 (she was just about to turn 35) she accepted his offer to meet her after work. He smiled at her saying she'd tell her husband she'd be late home due to "stock-taking" and they arranged it for the night after her birthday. Out for dinner together on her actual birthday our main topic of conversation all evening was forthcoming date with young Chris and what might happen once they leave the pub. To emphasise my approval, I even bought her a pack of 3 condoms for her to take with her.

Sure enough, the next evening Chris met Debbie from work in full view of her workmates and off they went to the nearby pub. After a few drinks Chris told my wife that his sister who he shared a flat with was out if she fancied going back to his place. Debbie readily agreed. This involved walking back past the shop though, so Chris and Debbie were seen on their way to his place not only by other staff, but also the little group of teenage boys that would hang around outside the shop in the evening. no doubt speculating that "that ginger married bird from the shop" is about to get a good seeing-to from their mate Chris. Indeed, he went down there and bragged about it to them all later.

No sooner were they in the front door, they were kissing passionately. Debbie's dark green uniform polo shirt was soon removed by Chris, followed by her white bra as he took in the sight of my wife's bare breasts before fondling and sucking on them. Having her tits sucked and her neck kissed made her putty in his hands and soon her black work trousers and panties were on the floor with her shirt and bra. In his bed they fucked feverishly. He'd had a condom ready, but Debbie said the packet looked a bit dog-eared, so made him use the ones I'd bought. She told him that she didn't want any more babies so he had to wear one and I think he was pleased to see a married woman come prepared. Perhaps he thought she did this all the time and he'd just found out what a slut she was. A very easy lay for the price of a few drinks.

Whilst Chris made coffee for them, Debbie quickly phoned me. For his benefit she told me how "busy" she'd been and that she didn't know what time she'd be home and she'd let me know what time to meet her train. I was at the supermarket doing our weekly shop with the kids in tow, but not surprisingly it was quite difficult to concentrate on shopping knowing my wife was currently in bed with a lad 12 years her junior. After that coffee, a cigarette and the stamina of youth, Chris was ready to go again. This time Debbie did all the work, putting the condom on his erect, young cock and straddling him so she could set the pace this time. Later, before he not only walked Debbie to the railway station but caught the train with her to make sure his "new girlfriend" got home safe, Chris fucked her again.

Chris stayed on the train and went home and I picked Debbie up outside the station. In bed she told me all about her evening and we made love - twice. We agreed that perhaps Chris could become her regular "bit in the side", but a day or two later I was struck by that "cuckold angst" and became very insecure. Asking her not to see him again, coupled to the fact that he hadn't even been in touch, upset Debbie. She felt dirty and used and we had a few quiet days where I just cuddled her to reassure her that everything was okay and no harm had been done. In hindsight, I should have held my nerve and let it carry on once he finally got back in touch. That set us back over 9 years, but Debbie was eventually persuaded to do it again, this time much more successfully and with a number of men.

We didn't live happily ever after though. We split up in 2012 and divorced 2 years later, but i have no regrets. I probably remember the good parts more than the bad though, so be careful what you wish for. All couples experiences will be different, but that's how we started. I'd do it all again too.



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  • 2 weeks later...

I'm surprised there haven't been more posts on this subject other than mine. Every couple that go into cuckolding are different so I expected to see all manner of other experiences here to help Brown. I think in my case I had a feeling that with my wife enjoying a social life without me it would only be a matter of time before she gave into temptation and had sex with another man. That prospect excited me though, whereas it hadn't with my previous partners. I decided therefore that if it were to happen, then I'd rather know about it than her have to do it in secret.

It was only a couple of years ago however that i discovered that just a couple of months before she went with young Chris she had cheated on me with an ex-work colleague of mine, basically lying to him by saying we'd split up to encourage him and offered him sex on a plate, almost refusing to take no for an answer. Naturally he was only too happy to oblige, but he finally confessed to me 20 years later that he'd fucked her just that once way back in 1999. I wasn't that shocked if I'm honest as they'd become friendlier than I'd liked some years before and we'd rowed several times about it. Once we'd got chatting and he realised that there'd been several occasions when I'd been happy to let Debbie do it with other men, he felt less guilty and was persuaded to tell me how she'd gone to his house whilst I was at work one afternoon and how she'd ridden him bareback in his bed. He admitted he was disappointed that it only happened that once, he'd have been up for making it a regular thing, but it was if he was a "trophy fuck" to her, just so she could say she'd had him and her curiosity had been satisfied.

In later years too she got very secretive and it was only after we divorced that I found out about other things, such as fucking her mate's step-dad on weekend visits to her mate's house and fucking another ex-workmate of mine for 2-3 years when I thought they'd only done it twice. It turned out that they'd even been away on holiday together when I thought she was with someone else entirely! He has been more than happy to enlighten me as to what my wife was like in bed with him and has even offered to provide the same service for my new girlfriend Becky if I can talk her into it. She wouldn't do it I know, but I'd be lying if I said the thought of him fucking another one of my women doesn't excite me, especially when he said that he'd report back to me on how Debbie and Becky compare between the sheets.

I'll probably never know now as Debbie won't talk about the old days, so I'm not sure if she grew feelings for him or any of the other guys she fucked or whether it was just more enjoyable doing it behind my back rather than having to come home and tell me all about it. 

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I was with my ex. I pretty much knew she was cheating but lacked any solid evidence. So, I called into work and didn't tell her. Drove a safe distance away, parked the car and walked back. Found a good hiding spot with a wide view. After a while, a guy shows up. I watch through windows. In short order she's sucking him, then they get undressed and find their way to bedroom. I thought about walking in an d all that, BUT, I'm rock hard. Well, I rub 1 out while watching them fuck. Didn't take long for me to cum. Only thing, I'm not getting soft. I'm still watching him fuck her bare. I start jacking off again. He breeds her and I cum even harder the second time. It took a while to go down. 

I didn't say anything to her. Instead watched many more times. 

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