My Confessions ⋅ 48 ⋅
Entries 79
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Success in Panties confessions
It’s been more than a week since I hit my 100 day goal and I’ve been hesitant to write about it. Originally when I came up with the idea, I had no real motivation other than just to see if I cou...
The lines in Ex wife confessions
As our relationship grew more serious, we started playing around a little more in the bedroom and quickly realized that I was the submissive partner. On the other hand, she considered herself a ...
The first step in Ex wife confessions
When I met my exwife, she had recently been in a long-term relationship with a woman. One of the things I noticed about her right away was that her bisexuality wasn’t just a random part of who sh...
Pink in Confessions
Sarah spent the night at my place last night. We sleep together regularly, but almost always at her place. She just prefers it that way, since her house is much better set up for her comfort. ...
Bulletin board in Confessions
Last week I went to Sarah’s place after work. She wasn’t home yet so I let myself in, with her permission. Then she texted me and said she probably wouldn’t be home for more than an hour, so it...
SSBBW in Confessions
It’s funny how being in a relationship with Sarah can change my perspective on things. I was flipping through channels this morning and not finding anything really interesting to watch, but I pa...
Flying in Confessions
Sarah and I discussed the idea of taking a weekend trip to Vegas in September. It would be our first real trip together since we started dating, and I’m excited about getting out of town with he...
Marsha P Johnson in Confessions
My ex is working with a group to develop a LGBT center in the city particularly focused on transgender people. A few months ago I agreed to make a $600 donation to the cause, which is a $50 paym...
New things in Sex confessions
It’s probably super judgmental of me to say this, but when I first started dating Sarah I made a few immediate sexual conclusions about her. The reason for my conclusions was completely because ...
75 days in Panties confessions
When I first started this, I was pretty sure that getting this far wouldn’t be too bad, but I wasn’t sure what the last 25 days would be like. Now that I’m at this point, I’m pretty confident t...
Yesterday in Confessions
Yesterday was kind of a test for me. Both in the sense that I was testing myself because I wasn’t sure what it would be like until I did it, and in the sense that Sarah was testing me because sh...
Official in Confessions
Sarah and I have gone on our fourth and fifth dates now, so I’d say this is really turning into a relationship. We had a conversation last night to clear up any doubt that we officially want to ...
The third in Confessions
Sarah texted me this morning and asked if I wanted to get coffee. I was literally doing nothing, so I quickly got dressed and met her at a coffee shop downtown. We both ordered and I paid. Whi...
It gets real in Confessions
I got a text last night from the friend I wrote about yesterday. She said that the local fat acceptance group meets up every Saturday morning and since I had expressed some curiosity about it, s...
Weight gain in Confessions
I met up with an old friend of mine this week. She was always heavy, but I hadn’t seen her in about two years and it seemed like she had gained over 100 pounds in that time. I was admittedly su...
Day 50 in Panties confessions
I am halfway to my goal now and figured it was time for another update. I think the changes to the panties are so gradual that I don’t really notice them, and I wonder if I could compare them to...
LGBT film festival in Confessions
My ex and I have been discussing going to the local LGBT film festival together later this month. I have mixed feelings about wanting to go to the festival, something we used to always enjoy whe...
The first 25 in Panties confessions
So I’m 25 days into my goal of 100, so I thought I’d write a little update about how everything is so far. This is without a doubt a TMI entry, so please be warned if you don’t want to read abou...
Gay porn in Sex confessions
When my wife and I first met, she was quick to let me know that she was bisexual and also expressed some disappointment that I was not. We lived in Boston, which is a surprisingly gay-friendly c...
100 days in Panties confessions
So I know this idea is going to be gross to most people, but it came to me a while back when I realized I had gone many days without changing my underwear. I decided I wanted to see if I could ...
Old ways in Sister confessions
For some strange reason when I was in my teens, something that sexually excited me was bad hygiene. And when my sister made rules for me that I had to shower and change my underwear daily, it al...
I like hairy women in Confessions
Not long after I started dating my ex wife, she commented about how much she hated having to shave her legs regularly. I responded that it didn’t really matter that much to me if she had smooth ...
Authority in Sister confessions
Once my mother seemed to give her approval, the amount of authority that my sister had over me started to really increase. When i got a little older, the internet was just starting to become a h...
Briefs in Panties confessions
One weekend when my wife and I had gone away on a little two day trip, after we arrived she realized she had forgotten to pack underwear. I had brought two pairs of panties and I told her she co...
Changing panties in Sister confessions
In my mid-to-late teens, I was openly cross dressing in front of my family and my sister was my primary disciplinarian. No one in the family treated it at all unusual that I wore girls clothes, a...
