So here's an intersting story of what initiated my crossdressing/sissy/gay-man/pegging fetish. 

 

Once upon a time, I used to always say, "I will never go near a man's bootyhole". Seriously. I NEVER thought I would ever be into pegging let alone crossdressing/sissy or even transwomen in general. We can all thank my lovely husband, whyamihere for that. 

 

One day, I left for work. Ten minutes in, I completely forgot my baby's diaper bag at home. So I had to turn around to go grab it. I didn't bother calling or texting whyamihere (some context, we just moved in with each other and have been dating for a whopping 4 months). I come up to the door with my kid in tow and opened the door. Sitting there was whyamihere, in my black/red dress and black heels jerking off on our couch. We made eye contact and the look on his face was pure horror. I stepped back and closed the door. I started snickering, picked up my daughter, and placed her head against my chest so she would not see anything. I walked right in and headed straight into our room. I closed the door behind me. Whyamihere came in, still in my dress, and shoes, and tried to explain himself. I just smiled sweetly and said, "Please just hang it up when you're done. If you gets anything on it, please wash it. I have to go. I am extremely late." I gathered everything up and left. 

 

A few weeks passed, and I started snooping. I went through his computer, and by "through his computer", I mean, I went through every single file possible and discovered he had an external harddrive. There I found EVERYTHING. His imagefap, his porn, pictures of ex's. EVERYTHING. Of course it consisted of tons of normal foot fetish (which I knew about already), but there was transwomen porn, sissy, crossdressing, etc. I had NO IDEA how to absorb what I found. At this point, we never addressed what happened and I just let it be. I ended up contacting one of my gay friends who happened to be a drag queen. I just needed SOME TYPE of insight. He ended up telling me that a lot of straight men crossdress, and are into transwomen. It's absolutely normal and I shouldn't worry. It was a relief. Now, I wanted to talk to him about it. I wanted to understand why, what, when, where, everything, about his fetish. I wanted to know what made him tick and why he was into it. It fascinated me. I just didn't know how to broach the conversation with him without him feeling cornered or scared that I was disgusted or disappointed in what I found.

 

A few weeks passed and basically the same situation happened. I came home unannounced and he was in the shower. I went to go in there to tell him I was home and there he was in the shower in my summer dress, flats, and bra. We just stared at each other... I slipped off my work clothes and jumped in the shower with him... this was the first time we fucked while he was dressed up. Afterwards, we sat in our living room naked and he opened up to me. He showed me all his porn, explained why he was into it, and I could not have been more happy.

 

From there on, we explored. I dressed him up, he dressed me up. We would go clothes shopping together. I would randomly buy him heels and dresses when I was out without him. I always just think of him when I pick out my clothes. Luckily, we're the same size in everything: dresses, leggings, heels, etc. So it makes shopping extremely easy. I found out his favorite heels are strappy, open toe, with rhinestones. His favorite dresses are short club style dresses. Basically I dress for him more so than myself.

 

Now, a year or so later. We moved, had his first/my second child. Kids were gone with their grandparents and we were alone. I was giving him a blow job and he asked me to stick my finger up his ass. At first I was hesitant. Buttholes are honestly gross. I had no idea the last time he showered, i don't know what's up there. But, I just went for it. I just licked and sucked on his balls, creating as much saliva as possible for lubricant and gently slid my finger in. The sound of his moaning made me suck, lick, deep throat even harder. I started fingering him harder and faster; making him arch his back and toes curl. Eventually he came in my mouth, and like a good girl, I swallowed it all.

 

We continue that, but it slowly evolved into me finger fucking his ass, one-three fingers at a time, while he was on all fours in my dresses/heels. For Valentines, I went to a sex shop and bought our first butt plug. It was a small one, probably slightly thicker than my ringer finger. We used that for a bit until he wanted to go up a size. I ended up purchasing my harness a few months later with a plug that was the size of his dick. The first time I assumed the dominant role, it was intense. We were drunk/stoned, and I dressed him up in one of my "innocent" dresses and I was in red velvet pumps and my black/red baby doll corset. He told me to take advatage of him, to imagine him as a women. Now, I'm bicurious and extremely picky when it comes to females. The more petite, blonde, the better. But seeing my husband bent over, ass cheeks spread, and him begging me to penetrate him... now that was a turn on. I come up behind and gently ease myself in and I swear I could feel him tighten around my pretend cock. I started out slow and worked my way up in speed and aggressiveness. Listening for his cues on what to do. After about ten minutes, I let my masculine/dominate side take over. I pinned him down by his neck, slightly choking him, and thrusted harder... faster. I grabbed his cock with my other hand and started stroking him. I pulled out and gaped his asshole, spit in it, then pinned him down once again. I pulled out and forced him to fuck me because I was wet and aching for his cock. To finish, I made him ride me and stroke himself. I wanted him to cum all over my face and to lick it up... and as demanded, he did just that...

 

Now, for the sentimental part of my post:

 

For all of you that are married/single/in relationship, what have you, and you're a closeted CD or you just have a fetish that you're ashamed of (be it a legal one, and we all know what im talking about), don't be. It's what makes you you. You can find someone who's accepting of it, someone that will love you no matter what. If you ever wondered what it would be like to open up to someone about it, test those waters. Bring it up in passing, gauge their reaction. If you feel comfortable that they will accept it, then tell them. If you feel like they won't, then by all means, don't. But think about it, would you really want to hide something that is a part of you from the person you're supposed to spend the rest of your life with forever? I believe that sex is one of the most important things in a marriage/relationship. If you have a stale sex life, mix it up. Do something different. Try something new. And if they oppose, just say this, "You can't say you don't like it until you try it".