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Friday, May 02, 2025

Outstanding in the field

Four years later and I'm back with a new post! Sometimes pictures write their own story, so I wanted to share this somewhere.

Not sure how often I'll post going forward, but will as the urge hits.

So without further ado...enjoy!


We live in a small town where everyone knows each other and gossip spreads like a weed. So one of my best friends was taken aback when I revealed I'd recently been thinking about gender identities and sexual preferences. And more specifically, how I'd been second-guessing my own.

I timidly asked him if I could give him head, just to see what it was like. He was rightfully reluctant, but I eventually made progress after repeatedly reminding him we could stop at any time, no one would ever know, and he'd be helping me out with my soul-searching.

So he agreed to drive separately to a remote field early one morning. I'd arrive first so I could change clothes and put on some makeup before he ever saw me. When he showed up, he met me out in the field, out of the sight of anyone driving by. 

Without talking, I helped him get his penis out and put it between my lips. He slowly grew as I worked him in and out of my mouth. We must've both enjoyed the sensations of what was happening, since we kept going at it. As an aside, I hadn't expected to make eye contact with him throughout, but yeah, that totally happened which was kinda sweet! 😉


After some time, I increased my pace and urgency, and he came in my mouth. I thought I was ready for this moment, but some spilled on the ground as I gagged a little. Oops! But I tasted everything he gave me, got a feel for his consistency and warmth on my tongue, and then swallowed it down.

I then waited for him to walk back to his car. Once he drove off, I cleaned myself up in my own car and changed back before heading home.

When I next saw him, I thanked him for our rendezvous, I know it took courage on his part. His face lit up and he admitted it wasn't as awkward as he first imagined. He asked me how my journey was going. I smiled and said, "It's going well, I'm definitely learning more by experience! Speaking of which, I really enjoyed our meet-up the other day. What would you say to a second secret date?" 

He said yes...I can barely wait! 

Tuesday, April 06, 2021

Hiatus

Thank you to anyone that has read my blog, and I hope you've enjoyed at least some of my posts.  

At this time I've decided to take a break from this blog.  

I've titled this post "Hiatus" since I know writing can ebb and flow, and may continue again sometime in the future.

Until then...

Friday, March 19, 2021

Subtle sissy hints

Talking to my wife about exploring my feminine side was one of the hardest things I've done in my life. 

How do you introduce the subject? 

How do you break the news? 

How will she react? 

What if she's repulsed? 

Luckily she listened and agreed to consider what I was saying, and over time was pretty accepting.

The second hardest thing I've done in my life was tell her I'd been thinking about cocks, wondering what it would be like to put one in my mouth. All of the same questions from before came screaming back into my head.

For whatever reason I started dropping hints instead of just sitting down with her and being honest.

For example I asked her, "Sweetie, why don't we take a day trip tomorrow? I was thinking we could take the ferry across the bay and find a hiking trail. It's almost peak foliage."

"Sure, Babe, that sounds like fun. Why don't you look up some trails before we go."

Then while I was preparing the backpack with supplies, I slipped a book into the bottom. Once we were settled on the ferry, I subtly took the book out and waited for her reaction.  She was busy watching the scenery out of our window and didn't take any notice.

That's when I dramatically lay down with a big sigh.  I put my head down by the window with the book covering my face.  

sissy reading i love dick book

That's when I heard my wife start giggling.

"Honey, is there something you want to talk about?" she asked.

Maybe my clue wasn't as subtle as I thought?  I peeked sheepishly over the book and took a deep breath. It was now or never.

"Actually, there is..."