My Story, My Dream, My Theorybycuckmeagain©
This is part confessional (my escapades so far) part aspirational (what I want from life in the future) and part explanational (why I think what I want works).
Part One – Confessional
I guess my first cuckolding experience came about when I was 17 or 18. I was out on a Saturday night and hooked up with a girl. Tall, thin, elegant, very well dressed. She genuinely could have been a model. I took her to a party that night that I knew of and ended up in the bathroom with her. All kinda normal stuff for a teenager back in the late 80's. What wasn't normal was that she was telling me all about her other boyfriends (plural) quite openly while I was sucking on her lovely nipples. I walked her home that night and found out a little more about her. She was 21, had various other guys on the go and didn't seem in the slightest bit ashamed about it. I had no idea why at the time, but it turned me on so much it almost hurt. I asked her then and there if I could be another one of her boyfriends (almost those exact words). She said yes, and we had a very sexy few months together. I never saw her with other guys, and it wasn't really talked about, but in the back of my mind, especially when we were in bed, I always thought about her with other men. We split up eventually because I had some kind of perverted male pride that tried to make her mine alone, despite how much her having other guys on the go turned me on. I've learnt a lot since then!
There were a couple of non cuckoldress types after that before my next exciting encounter, with just one 'almost'. A girl I knew from school, Sharon (and that's the only real name I'll be using here) was up town one Saturday night. A guy on each arm, and she introduced them to me as her "boyfriends". I was out with mates, and that same stupid macho pride stopped me asking if she wanted a third, and I've regretted that ever since.
My next interesting girlfriend was the first one I lived with. I must have been about 19 or 20; she was a couple of years younger, blonde, gorgeous, and an absolute exhibitionist. I found it a huge turn on to see her regularly showing herself off. She did the usual teenage girl things. She'd sometimes walk back from the pub after closing time bra-less and with her blouse unbuttoned all the way down to her waist. She'd go out with no underwear and a short skirt. What I didn't know was that she was cuckolding me behind my back for most of the relationship (a couple of years) and I didn't find out about it until after we'd split. Her friends told me about it, and then she confessed to me years later when we met and went for a drink one night. I so wish she'd have been honest with me while we were together. I still wonder to this day how many times I fucked her after another guy, and how many creampies I unknowingly ate. What it did show me, is how much of a turn-on it is if her friends know about it. More on that subject later.
When we split up I took on an evening job to give me something to do and to earn a little more money. I met some really interesting women through that, and learnt a lot more about myself. One was going through a divorce. She was in her 30's while I was still only in my mid 20's. Way back before the term Cougar had ever been invented. She was certainly making the most of her sexuality. We had a tacit understanding that I would always be there as a fuck buddy, and she quickly became aware of my kinks. Many times she'd turn up on my doorstep late at night after ending up in bed with one of the guys she'd met through work, and I'd always eat her out and then we'd fuck. That was an amazing time.
As I was getting fed up with working two jobs, I met someone else through the evening job. My cougar friend was moving away from the area so I started seeing the new girl. She eventually moved in with me as a lodger, and again, I learnt a lot about her very quickly. She was slightly younger than me and had just got divorced after a young marriage. She was quite open about the fact that her husband had divorced her because she couldn't stop cheating. Well I couldn't resist that now could I! Probably our most memorable time was when she had a guy downstairs, then came straight up after he'd left and sat on my face. That was the freshest creampie I'd ever tasted and confirmed for me how much I loved them. She met someone and moved out after a few months. We were nowhere near compatible for dating, but being cuckolded by a lodger is still exciting.
After that I had a very dry patch kink wise. I had a normal enough love life, but nothing cuckold related. Then I got married. I think subconsciously I must have thought that it was time to grow up and have a 'normal' life. Yes we were happy. Yes, the marriage got into double figures. When we split it was nothing to do with anything kinky or sexual in any way, but those years certainly showed me how hard it is to live without indulging your own particular kink, whatever that may be.
Right now I'm single again, having split up with my first partner since my divorce. I've been exploring the BDSM scene from both top and bottom roles, and I'd say I enjoy both equally. I've also been exploring (mild) bisexuality. One of my ex-girlfriends had a real thing for man on man sex. I never acted on that for her, more through fear of trying it than anything else, so I decided to give it a go. I now know that I'm certainly 90 something percent straight. I love women in every way and couldn't even imagine kissing a guy. I do know that I'm more than happy to be on my knees sucking a nice hard cock. I've been to a few gay saunas and tried this out, and enjoyed it. So next time I'm with a girl who likes gay porn I may just give her a treat!
Part Two – Aspirational
I'm looking for a cuckoldress. I guess that much is very obvious. What may not be so obvious is that I'm an absolute realist. Women are people, not kinks, not fetishes, not just a body. That may sound a perfectly sensible thing to say, but so many people who are into any one particular kink forget that.
I think my ideal scenario would be for us to both be subs. That way she can enjoy the attention of dominant bulls, and I can enjoy seeing/knowing about her being used and abused by them. The 'dominant daddy/alpha cuck' thing could work. I'm not averse to taking the dominant role, but it doesn't seem to sit as well within a cuckolding scenario. The Domme as a wife/partner with a submissive cuckold seems so much more 'realistic' and I'm not averse to that either. I'm not exactly what you'd typically think of as a sub though, so that would take one hell of a strong woman. Plus of course (and it's only my opinion) that a woman submitting to a guy sexually is visually one hell of a turn on. Hence my thoughts what a sub/sub couple would be the most potent version of a cuckold relationship.
And what about the other guy(s)? There's the whole BBC dynamic to start with. I have no issues with her seeing black guys. I have no issues with us both seeing black guys or couples. Again it's a very stimulating thing visually. It's just not the be all and end all of the cuckolding scene for me – and it has to be whatever she likes for this kind of thing to work anyway. I do kind of like the size queen scenario though. I'm not hugely endowed, but I'm certainly not the 'needle dick' of popular cuckold fiction, and have no interest in being belittled for being little (if you'll excuse the vague pun). There is once more a visual element though that a big cock is visually pleasing. And let's face it, if she's going to go with other guys, then it makes sense for her to get as much out of it as she possibly can. In much the same way, a woman who is a cougar is a big thrill for me. I dated my fair share of older women when I was younger. To have a partner who is in her sexual peak (as women are in their 30's and early 40's) who uses that sexual peak and see's younger guys is not only a turn-on, but infinitely sensible (more on that in section 3).
Single or multiple guy(s)? Once again, her choice. I think from an emotional point, I'd much prefer her to have a string of lovers, so that it's all about sex and there's less of a chance of a single lover getting romantically involved. We have to be realistic here though. There's always a health issue with multiple partners. It's something that needs thinking about seriously. Perhaps a single guy who's a married bull? I have no answers here, but it's just another part of the kink and a conversation a potential cuckold/ress couple need to have.
What involvement would I have? Well my ideal would be to be there when they fuck. Not always, but certainly as often as possible. I want to see her have amazing orgasms. I want to hold her hand, to look into her eyes, while she's being fucked. If we had a bull who was safe, then I'd love to clean her up and eat a lovely creampie afterwards. I'd like to prepare him for her if that's something she enjoys – sucking his cock to get it nice and hard for her. There are degrees less than this of course. I could just be told about what they get up to. I could be sent into the spare room while they take 'our' bed – just hearing but not being allowed to watch. The only thing that's completely out of bounds for me is bare faced cheating. I have no issue with my partner seeing other guys. I do have an issue with dishonesty – two completely different things.
Who knows? That's a big question. Ideally, she'd have some close friends who may be into something similar. I'd love people like that to know. What I'd hate is for my friends or work colleagues to know. That kind of thing ruins people's lives, and this is about fun, not ruining lives. Perhaps if we were a sub couple and were owned by a dominant couple there would be even more scope there?
Part Three – Explanational
I firmly believe that a cuckold relationship has to be the happiest and healthiest format of relationship – providing both partners are honest (and into cuckolding of course!)
Let's face it; if we're honest we all know that a woman's capacity for sex is way higher than a guy's in general. How many guys do you know who are capable of multiple orgasms? How many guys do you know who are ready to go again as soon as they've orgasmed?
Eventually, I think most women wonder if there's a guy out there who can make them cum harder (or at all in some cases). I think also that at some point most women wonder if they're still desirable. Being a cuckoldress will answer both of those questions.
I think guys generally tend to get lazy in a relationship too. Cuckolds never do. If you know your partner is seeing other guys, then you work damned hard to make sure it's you that she wants to come home too, no matter how much she enjoys sex with the other guys.
Cougars. It's becoming more and more common for the older woman to want to experience the younger man. And why not? It's been acceptable the other way round for generations. Being a cuckoldress allows women to experience this without all the tedium of trying to have a relationship with a younger guy – trust me, I've been that younger guy and it isn't always easy!
And that's it for now.
This has been my first submission to Literotica. Hopefully it's been of interest to some of you who've read it. I'll try to make future submissions more exciting and fictional.