Beginning Foray into Cuckolding

Hello everyone. Long-time lurker, first-time contributor. I'm 46, happily married for 20 years, but it's not my wife who's cuckolding me.

My wife and I are very much in love, but there's no sex, and no sexual attraction. We're polyamorous, and I don't cheat on her, and I do everything with her knowledge and consent. In fact, she actively ENCOURAGES my exploration with other women.

I'm submissive. (So is my wife, but that's another subject). I've been collared to two Mistress's in the past. I've recently begun a D/s relationship with a new Mistress. SHE is the one that this story is about.

My new Mistress is 24 (she'll be 25 in a couple of weeks, and she is LAMENTING that she's going to turn a "quarter of a century", LOL.) She's half-black, though I thought she was Hispanic when I first met her. Anyway - exotic features and brown skin, not really "African-American" in appearance. I think she's gorgeous!! She used to be a dancer. She has a 6-month old baby, but she doesn't look like she did. She's still got the body of a dancer!

So we met at a BDSM play party 2 months ago, and I spent the night serving her. Waiting on her. We hit it off well, and about a month ago, she made me her sub.

In the month after the party, we got to know each other, and be sure we were compatible before starting a relationship. One thing I made crystal clear from the start is that I was interested in a CUCKOLDING relationship.

Note: My wife and both former Mistress's TRIED to explore cuckolding with me, but found it emotionally very difficult, if not impossible. So I've gotten "glimpses" of what it would be like - but it was never the real deal.

The reason they found it emotionally difficult is - I also consider myself an emotional masochist. I LIKE to be hurt. Not physically, like many other people in the BDSM community I know. But emotionally. I LIKE to have things happen that make me cry, or feel afraid, or feel jealous or humiliated or - whatever!

And my former Mistress's couldn't "hurt" me in that way. The psychological was too much for them - it was hurting them more than it hurt me.

So before we started, I made sure my new Mistress was on board with Cuckolding being at least an ELEMENT in our relationship. (She has needs of her own, such as inflicting physical pain on me, so fair is fair - we're each going to get something we want!)

Well - she was not only "okay" with the idea - she was really ENTHUSIASTIC about it.

We've been an official D/s couple for about a month. Well, I saw her on Tuesday (9/2/2014) and she casually mentioned, in between bites of her burger, that she had gone on a date on Monday night (Labor Day, 9/1/2014).

This BLEW ME AWAY, and I tried to get her to tell me all the details. She only told me a few details, and she was clearly amused at my reaction. The guy she went out with is 6'1, 28 years old, a hockey player...

I'm only 5'3" tall, however, I've been training in Kung Fu for 28 years - and I work out very hard in my Kung Fu class twice a week, and I never miss. I'm a very skilled fighter, so for me, one element present in a lot of cuckolding relationships I read about is just NOT applicable - namely, feeling physically inferior or intimidated by the "other guy". Although - I'm KEENLY aware of being 46, and she's 24 and he was 28, so..... I do feel a bit inadequate in that regard. But I don't care too much about the age differences. I've dated much older women and much younger ones, and if THEY have an issue about the age difference - it usually doesn't work out anyway.

So - she tells me she had fun and she will definitely see him again! I, of course, enthusiastically encouraged it!

I should make sure it's clear - I don't live with her. So for her to go on a date - I wouldn't know unless she tells me. And I kind of LOVE the way she dropped the bombshell on me, in between bites of her burger. LOL - she's fun and playful, and she knew just how to make the right delivery!

I will keep you all updated. This relationship is in the absolute beginning stage, and so I don't have a very exciting story to tell "YET" - but I am very optimistic

This has all the elements to be a truly outstanding series of posts - I'm really looking forward to more.

Yes, I too look forward to your updates!


Cuck who loves a creampie.

Thank you both. Things will probably progress very slowly. But I promise to give updates whenever they do happen.

Thanks for that gf - if anything in life has any real value, it's worth waiting for. She's definitely got an excellent attitude towards cuckolding you, as and when it happens. Her just dropping the fact she'd dated some much younger guy out of the blue is a real killer punch! You can envisage her casually telling you eventually that she's just fucked some guy, with all the accompanying angst, jealousy, and excitement that brings.

Here's an update.

Sorry, but don't expect an extremely titillating story. Things are moving very slowly, on account of her being in school, and living in a house with 7 other people. (All related to her. Her m*ther and f*ther, sister and brother-in-law, 2 nieces, and of course her own 7-month old baby.)

She's kind of at her sister's mercy, when it comes to watching her baby, so my Mistress doesn't get to go out much. She doesn't have a car, and she is always dog-tired, from the baby and school.

But we've made an arrangement - I drive her to school every morning! So I see her for about 40 minutes a day.

So I've been keeping a slave journal. A nice notebook, where I write down my thoughts, feelings, fantasies, fears, concerns, etc. And she reads this journal about once a week.

Well, in my journal, I wrote how THRILLED I was that she went out with that hockey player on Labor Day. I also wrote a WHOLE LOT of other crazy sh*t - but she loves it. For example - I begged her (in the journal) to "LIE" to me. Cheat on me. I told her it would turn me on a great deal. (Of course the dilemma is - if I don't know I'm being lied to - how can I be turned on? Well, I always figured I might catch her in a lie, or, just always worrying about whether or not she's lying to me - that's hot too!)

And I wrote about a fantasy that I had - which is that, when she has a boyfriend, she'll let me get a "girlfriend"... a cheap vinyl blow-up doll. One of the very cheapest ones, that doesn't even have like hair or anything - it's just a painted-on face. And I would not be allowed to have any orgasm ever, unless it's fucking my "girlfriend".

She loved that fantasy!

Last night, I texted her, and she informed me that she was replying with her phone plugged into the charger. It died while she was skyping a certain hockey player! Then she said goodnight, and that was it.

Today, on the ride to school, she began talking about random stuff, and I said "so we're just going to completely ignore what you told me last night??

She laughed, and said "no, we can talk about that if you want." I said "HELL YES!"

So she allowed me to ask her 3 questions, and this is what has been unfolding...

(Oh! Before I forget - her birthday was last week, and at first, she told me she didn't want anything. But I wrote in my slave journal that I'd like to buy her lingerie for her birthday, that she would never wear for me, but would instead wear for another man. She laughed, and was delighted, and said ok, and allowed me to buy her the lingerie. She picked it all out herself. About $150 worth of stuff!)

So she DID go on at least one other date with the hockey player. She told him all about me, and he is fine with it. He's NOT her boyfriend - she's scared of the "B" word. And when I asked if they've fooled around, she said "not to that level". I don't know what level she meant, but my head was REELING!

Apparently, her and him skype a lot.

So I asked her if I may have an orgasm tonight. I don't wear a chastity device, but she has complete say over when I'm allowed to have an orgasm, and I have been 100% honorable. It's been about 2 weeks since my last orgasm, and I'm horny as hell. She said "yes, but text me before you do".

So I texted her a little while ago (she goes to bed at around 9. I go to bed around midnight.) I didn't want to masturbate until closer to my own bed time, but I wanted to obey her condition of texting her, and she told me:
Yes you may. Considering that may be the only form of pleasure you get until you get yourself a new "girlfriend". See you in the morning.

OMG, I am in 7th heaven! I have to confirm this tomorrow morning, but I believe this means she wants me to get a blow-up doll. And - that will be my only form of sexual release from now on. SOOOO freaking hot!! I'm excited as hell.

******************

I know my story is a little tame, compared to other cuckolding stories. It's still unfolding. And I do have other things to tell - that she and I have done together, that are NOT cuckolding related. For example, sometimes, she will allow me to do things that are humiliating, like sit around with my thumb up my ass, (literally!) Or she will allow me to kneel with my head in the toilet for an hour. To me, that's like being made to stand in the corner, but even MORE humiliating.

It was actually me who came up with both activities, but she readily agrees to my "perversions" or cravings, or whatever they are.

Well, I'm seeing her tomorrow morning

Goodnight everyone!

Please continue posting. Often times a really good story needs time to unfold, to develop. She certainly has all the qualities you would want in a domme/mistress situation. I hope that when the time comes, she seriously considers having you placed in chastity to help focus your attention on serving her and making sure she gets all she wants and needs.

kennyboy82
Not sure how well chastity would work for me. For so many reasons:
1. I do kung fu twice a week. I'm afraid of injury. Possible solutions - I take the cage off for just those sessions, and put it right back on again immediately after. OR - maybe tight-fitting underwear, like bicycling spandex or something would keep it all tight enough that I wouldn't get hurt.
2. I am a locksmith. For real. So a lock wouldn't be an obstacle. Solution: serial numbered tags. Nothing could stop me from taking the device off, but she'd know. OR - honor system. I would report to her any time I took the device off.
3. I've lost a nut to testicle cancer. And the remaining nut is very small. I'm not sure any cage type device would stay on. I'm reluctant to spend the money, just to "experiment". Solution: I DO have a PA piercing... but I'm afraid of the chastity device pulling on the piercing so much, it causes it to migrate...

Hmmmm

On the other hand - my Mistress has the final say in whether or not I have an orgasm, and even if I'm allowed to play with myself. I don't cheat - so that's working for us as well as a chastity device. I've gone as long as 28 days without an orgasm...

A lot has happened since I last wrote.

Last Saturday, I texted my Mistress and asked if I could go to a friend's birthday party. It was a BDSM/Kink/Play party, and a lot of my friends were going to be there. She wrote back "would you rather go to the party, or stay at home with your thumb in your ass, thinking about Scott going down on me?"

I really wanted to go to the party, but I of course opted for the latter.

But then it turned out she didn't get to hang out with Scott after all, so she let me go to the party.

I had a great time, and chatted with a lot of friends, but then a few of my female friends wanted to cuddle with me, and I went ahead and did it. (I'm stupid!)

There was no sex or petting or kissing or anything, just snuggling.

I don't hide anything from my Mistress, so I told her on Sunday what I had done. She was mad, but not terribly so. She told me I was going to be punished, but she had to think about what the punishment would be.

I drive her to school every morning, and on Monday morning she was in a very good mood. She wasn't interested in my punishment, as much as she was in reading to me her text log from Sunday night. Apparently, even though she & Scott couldn't get together over the weekend, they stayed up late texting to each other, and it was VERY hot and steamy. He told her he's going to tie her to the bed and blindfold her, and eat her pussy and then fuck her, and he was very graphic. She wrote back to him "I can't wait, SIR". She called him SIR!! and she was so bubbly and giggly, Monday morning as she was reading this to me, and she told me she would happily submit to him.

Well, I see her as Dominant, so seeing her act submissive towards another man was HOT! And of course I told her so!

She read a lot more of their texting (she calls it "sexting"). And it was all very hot and flirtatious, and she was getting horny all over again in my truck. But not for me! But she was making ME very horny too!

So she and Scott haven't fooled around yet. But they've been talking about it for a while, and it's probably going to happen tomorrow (i.e. Saturday). But I'll get to that.

So I dropped her at school, and then Monday night, she told me my punishment for cuddling with other women.
I'm cutting and pasting this directly from her text message (except Scott isn't his real name. I altered that.)

"You're going to write out what you're being punished for, why you're being punished for it and your reflection on Scott and I and our sexting. That's the first part of your punishment. Second, you're going to edge every morning and every night WITH a thumb in your ass for a week"

I thanked her, and joked that it wasn't really a punishment because I was going to LIKE it, but she laughed, and said that's okay. It seems she's much more absorbed in her own NEW relationship than in me or my transgression.

So if anyone's interested, I'll post what I wrote for the writing assignment.

As far as the thumb-in-ass assignment...
Well, today is Friday. By yesterday (day 4), my asshole was getting sore. I was using only my own saliva as lube. I went out and bought a bottle of real lube, and today was much more comfortable. Enjoyable, in fact!

Tuesday she read me more of their "sexting" and it was just as hot as Monday's. I can't really remember it too well, to reproduce it here, but it was all about what they were going to do to each other. He wants to make her beg for an orgasm, and all that.

Wednesday and Thursday she was not in the mood to tell me about Scott. (The f*ther of her baby has been giving her a lot of grief over visitation rights, and she needed to vent to me about that instead.)

Today, Friday, she told me she's seeing Scott tomorrow! And they're probably going to have sex!

I could not be more thrilled!! But at the same time - jealous and worried and sad and insecure. She knows I have ALL of those feelings, and she LIKES it! I'm an emotional masochist, she's an emotional sadist!

Well, here are a couple of other little points that didn't really fit into my story anywhere else, but I wanted to share:
1. Every Friday, while she's in school, I go over to her mom's house and help her m*ther take care of her baby. It gives me such a strong feeling of being connected to her when I am taking care of her baby!

2. Her BIGGEST obstacle to seeing Scott is finding a babysitter. I've told her many times that I will happily watch her s*n for a while, so she and Scott can be together. But she's still hesitant. She trusts me with her s*n, but I think the issue is - she'd be so worried, she wouldn't be able to let go and enjoy herself.

3. I've also offered to pay for dinner and a hotel room for her and Scott. And I told her I'd drive her to and from her date. But she hasn't accepted those offers either. She's told Scott about me, but I think the relationship is too new for her to start bringing me into it. If she EVER does.

All I can say is - I'm SOOOOOO excited and happy about tomorrow night!!

I'll write back here again as more develops!

By the way - this is all 100% true!!

Hopefully she sends you some text pic 's of her fucking him.

i122
DEFINITELY not going to happen.

Scott is not a bull, and may not even know what cuckolding is. He knows about me, but all he knows is that I am Jen's sub. She's probably told him that we don't have sex, so he probably doesn't view me as a threat, and he's okay with me being in the picture.

I'm hoping that he will eventually EVOLVE into being a bull.

But for now, I think the less he knows about me and my kink, the better. If she lets him think that part of this is about ME, then it might mess up what's beginning to develop between them.

Jen's 7-month old baby had a fever yesterday. She had to cancel her plans with Scott . I'm not even the least bit disappointed. This is not about me, it's about her. Her s*n comes first, of course! Having me as a sub, cuckolding me, and even her potential new sex partner are all for FUN. Fun is something you do after your real life needs are met. And I'm trying so hard to help her by making her real life needs easier. Driving her to school, helping to take care of her s*n, etc.

When the timing is right, she'll get her sexual experience, I'll get my cuckolding experience, and everybody will be happy. It didn't happen last night, but it would be obnoxiously selfish of me to feel disappointment. If anyone should be disappointed, it's HER. And I imagine she IS, but she hasn't said anything to me about it.

And it turns out today that both her and her s*n are sick.