Failure and temptation...

Warning: Depressing Content Ahead...


The Chastity experiment didn't go well.

Miss V allowed me to wear the device, then forgot about it. A week later, she unlocked it, we had sex (which was surprisingly unfulfilling to me) Then she allowed me to be locked again, but told me she didn't want me locked up, because she didn't enjoy it. There was no tease and denial, just ignoring, as in the presence of the CB was offensive, so I had to weigh my options, and decided to give it up.

There was absolutely no reaction from her part when I said that I didn't want to be in chastity any longer. I approached her a couple times for sex after that, and she consented, but was not an enthusiastic partner. The frequency of my approaches diminished to once a week. For a few weeks, we had sex every Saturday morning, until she started scheduling work for that morning too.

I was devastated. She insisted that she had to do the work, which is true, but I know she is the one that schedules it, so it doesn't have to be done that early. The people that work with her don't usually respond until the weekend it over anyway, so working later on Saturday or even Sunday does not affect her work in the slightest.

The truth came out recently, thought.

She told me that sex had not been pleasurable for her any longer and that it was actually beginning to hurt. She asked me for understanding and told me that I should just "take care"of my own needs by myself.

I explained that I don't want to become addicted to masturbation as I was during a previous relationship, where I ended up masturbating up to 5 times per day. She dismissed it and suggested that my hormones are less intense today than they were 20 year ago.

In the end, she agreed to participate in masturbating me, and offered, without any prompting of my part, to take me with the strapon on occasion.

Faced with the prospect of no sex, this seemed like a good idea, so I agreed.

She masturbated me once. I texted her that I needed her to give me a hand and she responded "I'll be there in 5 minutes". She came, gave me a blow job and finished with her hands (she doesn't swallow). then she said that this was to prepare me for the full day of work she had for me and gave me numerous tasks to complete, which I did happily, thinking that we could reach some form of stable relationship, even if it didn't meet all my expectations.

But that was it.

One day she told me that she would fuck me, but I was sick. She didn't offer again.

Now I'm in a bind, because on the one hand, I am in a no-sex relationship with my wife, and on the other, an ex-girlfriend who just got divorced moved back to town a few weeks back. I had seen her once or twice from afar, and discovered that my memories of her are still there...  to the point that she is now a recurring character on my masturbatory fantasies, but last Thursday I bumped into her when shopping and she told me that she would like to meet for coffee one of these days to catch up. This is probably an innocent proposal, as I don't think she will sexually assault me over coffee, but that has not precluded my horny, sex-deprived brain from creating all kind of scenarios where this woman, and not my wife, is the protagonist.

I'm feeling very confused right now. I know I love my wife and want to honor the vows I made with her, so I'll probably will not meet with my ex, but I'm being completely unfaithful to my wife in fantasy anyway, so I wonder if it would be best to just meet this woman over coffee, When nothing happens, maybe the fantasies will fade.

Now, to better understand why this woman tempts me so, let me explain a bit. She was one of my earliest serious girlfriends. She was still in high school when we started dating and was in college by the time we broke up. A lot of my "firsts" were with her. She gave me my first hand job, my first fully realized blow job and hers was the first pussy I tasted. She was always open to try new things, except vaginal sex. I never entered her love canal, because she had this strange concept of keeping her virginity until marriage I say strange, not because I disagree with keeping yourself a virgin, but because I think after all the stuff we did, calling herself a virgin was just a technicality.

Ever since I discovered my submissive desires, I have thought that had I slayed with my ex back then, she would have eventually become my mistress. Now, there is no way of knowing that to be true, but I FEEL that it is, and that's what makes the idea dangerous...

There is another angle to this:

A couple week ago, I was feeling guilty over having sexual fantasies of my ex (and her sister) and asked Miss V to spank me and spank me hard. She asked me if I self-spanked and I answered that over the years I have tried to do it (true) but it has never been fully satisfying (also true).

Miss V spanked me so hard that she felt the need to apply some lotion to the affected area afterwards and I agreed with it. I thanked her and told her that I would appreciate it if she would spank me regularly to "encourage me" as she used to do with denial before.

"I don't know about that," she responded and explained that I need to stop feeling guilty for taking care of my needs. (I had not told her what I was really feeling guilty for) and that I should just take care of myself... this has increased my fantasies to the point that for the last few days, they have flourished into outbursts of creativity. I even had a dream three nights ago, where my wife told my ex that she was grateful to her for being available to take care of a part of me she didn't like, and just sat there watching while my ex ravaged me with teeth and nails... Sadly I woke up before she swallowed my load.

This is sick... I know.

I know my ex. I KNOW I'm going to "bump into her" this week. I know I'll probably say yes if she ask me out for coffee again... I know she will ask... And she will ask with all the innocence and smiles of someone who doesn't know she's been my favorite demon for quite some time.

 And I feel miserable about it all.