Taking the plunge

My confession will be a little long and I appreciate anyone that sticks around to read it.

I first started dressing up in my teens and around the same time I'd also developed a full blown fetish for stiletto shoes & boots. I'd also discovered adult material by then and even though I experimented with crossdressing, I never thought of myself as anything other than being straight. The daft thing is, whenever I looked at any adult material I always imagined what it would be like to be the woman. I guess I was in some kind of denial.

I stopped cross dressing in my early 20's. Not because of one thing, but a factor of many which I won't bore you with. Anyway, the feeling of wanting to crossdress never really left me and it wasn't until my mid 30's before I got the opportunity to start dressing up again, albeit very, very occasionally.

Now, this is where everything changed because I'd discovered something new, something that really did awaken my inner girl. What I discovered was chastity cages and from the very first moment that I locked myself into one, I knew things would never be the same.

Every time that I was caged & dressed, all that I could think about was cock and for some reason, it was old men's cocks. I found myself searching for photos of them and I even registered on a gay hook up website. I started exchanging messages with old men on there, some would ask for a meet but they were always too far away or our circumstances meant a meet up wasnt possible.

But then, the stars aligned one day and I arranged a meet with an older man. He was in his early 60's, lived alone and he didn't mind me being locked in chastity. We arranged a time fir me to turn up at his place and I got myself ready.

I was absolutely terrified on the drive over to him. I was caged and I'd got my fem things in a bag. I parked up no too far from his house and as I got out of the car I felt so nervous. I couldn't believe what I was doing, I'd never been with another man before bet here I am, about to knock on his front door.

He opened the door and invited me in, I'm sure he sensed my nervousness but he just sent me upstairs to his bedroom and told me to get changed into my fem things. I did as he asked and as I fastened the last strap on my Mary Jane stilettos he walked into the bedroom, completely naked.

He was average height, quite a bit overweight & he had a musky smell about him. I felt myself swell inside my cage and my mind was racing with so many thoughts. How have I gone from lusting after hot women in my younger years to now being turned on so much by someone like him.

He didn't give me much time to ponder over it though. We ended up on the bed, kissing deeply & passionately as our hands explored each other's bodies. As I caressed his balls I felt myself leak a little from my cage. He must have sensed how much I was turned on as he told me to get on all fours. I did as I was told and he started to use a dildo on me. I knew he was loosening me up for his cock and with every push inside I'd let out a little moan.

After a while he told me to lay on my back. Again, I did as I was told. He then spread my legs apart before putting them over his shoulders, manoeuvring himself so the tip of his cock was pressed against my hole. Without saying a word he pushed his cock inside me and as he did, I stared up at my stillettos and it was one of the most intense erotic feelings that I have ever experienced. I knew in that moment that I never wanted straight sex again. Feeling him thrusting his cock in & out of me as I'm leaking even more pre-cum from my cage, staring at my Mary Jane's was a real Utopia moment for me. I wanted to stay in that moment for as long as possible.

After he'd finished with me, he told me to put my regular clothes on over the top of my fem outfit and leave. No small talk, no offer of a shower or to freshen myself up, nothing. I quickly put my regular clothes on, put my Mary Jane's in my bag and left.

Walking back to my car I was processing what just happened. I couldn't believe that I'd just gone through with it and that I'd just lost my anal virginity to him. He was an old man that simply wanted to use me for his own sexual pleasure. As I reached my car I felt myself leak a little more again, my hole still quivering from him being inside me.

I still think about that visit to him to this day. It was like an awakening to me and I am so glad that I took the plunge.