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During a game of “Truth or Dare”, my friends dared me to dress up in my girlfriend’s clothes and ride her dildo. Now, you would think that this would be a little too extreme, but not for our friend group. Every game we played had something that most people would never do, especially with their friends. Anyways, since I wasn’t a coward, I accepted the dare.
From my girlfriend’s closet, I took out a white blouse, blue skirt, and black pantyhose. I stripped off my regular clothes and put the new clothes on. I grabbed a dildo out of her drawers and suctioned it to the floor. I set up my phone so that I could film myself doing the dare, assuming my friends don’t believe that I did it. I lubed up the dildo a little, as I had seen my girlfriend do before. I sighed and began the dare.
I slid the dildo into my ass and began to ride it. I began to question why the hell I was doing this. I don’t know how my friends even talked me into it. Wearing women’s clothes is one thing, but riding a dildo? That’s a little much for a straight person.
As I rode the dildo, though, it didn’t feel too bad. There was a lingering feeling of pleasure. I guess I know why pegging exists; hell, even my girlfriend has suggested it a couple of times. Despite the pleasure, though, I figured that I could stop soon, since the dare didn’t require a specific amount of time to ride the dildo. I’ll give myself a minute at most.
Then I noticed that cum was starting to drip out of my penis. How’s this even happening? I wasn’t even hard! I’ve got to get it together. This was supposed to just be a simple dare, and now I seem to be getting pleasure by a simple piece of rubber. In my head, I want to stop, but I just can’t for some reason. What is wrong with me?
That’s when I began to experience a full-on orgasm. God, that feels so good. The orgasm caused me to leak an insane amount of cum, almost as if my penis were a fire hose. The pleasure is so intense that I practically zone out. I become lost in riding the dildo, with no chance of stopping. It’s almost as if something changed inside of me.
My girlfriend (having seen the video I took of me riding the dildo) kneeled on the bed behind me, prepping her strap-on. I laid there with a sexy red lingerie set on, matching nails/makeup, and hairless skin. I sighed, knowing that this is the only way I can orgasm now. My penis (now clitty) stopped working after that one night. I could no longer masterbate or have sex like a man, but luckily, my girlfriend was more than willing to help out. In no time, she slid the strap-on inside my asshole, solidifying me as a sissy. I guess this is my life now…
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