Maybe it's not strictly cuckolding, as we are not in a relationship together, but there are aspects of both cuckoldry and chastity to what I've been having going on. I have a coworker (she is 31, I am 28) who has always described herself as a sex-positive feminist. Surprisingly, she never really seemed to come with the whole SJW package and seems conservative in other aspects. But with regards to sex, she has always been blatent that she believes women should be able to sleep with who they want, when they want and is always posting about women's rights. She is pretty dann attractive in a traditional way (no tattoos, died hair, only ear piercings), and I'm pretty sure the only thing that's kept her single is her outspoken feminism (not saying no one would date her, I don't know how interested she is in LTRs. We can call her Helen.)
Helen and I were always on good terms, and about 6 months ago she left the job that I met her at. We haven't really spoken much, and I was in a relationship with a little chastity play until about last October.
About a month ago, Helen made a Facebook post about cock cages. It was clearly a joke (kind of a #sorrynotsorry thing) and basically said this is the only way to stop husbands from cheating and expressed support. I was really shocked by it, and I wasn't the only one. I still had a cock cage from my previous relationship and honestly missed chastity. I found myself getting really turned on by her post for a few days and finally said fuck it, I'm going to message her. She is, after all someone I would definitely trust with a secret.
So I did it. I messaged her and essentially just said how are you doing and that I liked her post. I told her that I owned a cock cage and that my ex used to have me wear it. Helen was completely fascinated. She thought it was funny, sure, but not in a cruel way - it made me feel humiliated and hot, but she wasn't downright abusing me for it. She kept asking questions, and I said that my girlfriend had liked it because she thought I wouldn't cheat, but there was definitely a fetish aspect of it for me too.
We talked over the next several days, and the conversation advanced quite a bit. She asked for a picture of the cage (the cage itself, not me locked in it) and asked if I still wore it. I said I didn't have a keyholder but I would definitely be interested in doing again. Long story short, I finally worked up the courage to ask if she'd be my keyholder and she said yes.
There was almost no tact in how it went down. I went to her house with the cage. She offered me coffee. We sat and talked for a bit (had been talking quite a bit during the week), and she finally said, "alright, let's put it on." I said, "let's?" and she said yes. Right in her living room she had me pull out the cage, pull down my pants and put the cage on. She even teased me a bit, "Ahh, little dick's getting caged" and I don't think she even realized how much that turned me on.
I dressed again, and we started talking casually like it never happened - except she told me she was casually having sex with a couple guys.
Luckily, she lives super nearby. So I was first caged with her not long ago, and stuff progressed rapidly. I kind of took the lead at first in letting her know that I was willing to submit - I offered to buy her dinner and drinks. When I was over at her condo, she said she had to go get her laundry downstairs and I said I'd get it for her, and helped her fold it and put it away.
Within a couple weeks from the cage date, we were seeing each other nearly every day and its been really cool. For the most part we hung out as friends, although sex and chastity came up quite a bit. She asked me how I was feeling - I didn't ask her if and when she was going to let me out, and I told her I was raging with horniness. But of course didn't expect her to do anything about it.
Finally, she started teasing. I started staying the night over there. I started to watch movies with her and cuddle, and she walked around in her underwear. She even let me shower with her once and take pictures (see attached). I think she had honestly just become amazed that she owned a man, and that she could let me see her naked without me trying to fuck her. I'd touched her, sure, but it was mostly cuddling and she always initiated it.
Last weekend, her other guys came into it. I was at her condo and she said she was going to a bar with one (she had still been seeing them, but it had come up when I was there). I realized this was a big opportunity, and I offered to DD for her. I dropped her off at the bar and as a gesture gave her some money for drinks.
Then, when she called, I showed right up and drove her home as she and her guy (definitely an alpha) were all over each other in the backseat. I dropped her off and said goodnight, and she thanked me drunkenly like 5 times. I guess he asked later about me and she said I was a friend from work (basically true haha).
The dynamic shifted after that though. This is when she let me shower with her. She let me kiss her and eat her out. On Wednesday, she finally let me out of my cage for a few minutes and said I could go rub one out in the bathroom. Then, on both Friday and Saturday this weekend, I was able to DD for her again. I met her other fuckbuddy (also an alpha), and I guess he thought it was hilarious that I drove them home.
Helen and I have been talking about it today. I really, really want to watch or at least spend the night at her apartment when they fuck, but I'm not sure how she should ask her alpha since I'm not her boyfriend or husband. I also kind of want to ask her out- I don't want to ruin this, but we get along great and I would happily be a committed cuckold to this woman.
I know this is kind of the opposite of how things usually start (ie hubby asking wifey to fuck thick cock), but I really enjoy whats going on. I've only came once in the last month, and I'm not surprised at all that she's felt no remorse for this, but its super intense.
The longest my ex ever had me locked was 8 days. Anyways, I just wanted to share this with you guys here at the blog.
Hope you enjoy. I know I am.