Corssdressing at Pride

I squirmed with pleasure as he rimmed me. The flicking of his tongue got me so aroused that I started to grind my ass against his face a little. I started to feel like trying to fit his monster cock in my ass. As if reading my mind, I felt his finger sneaking in on the fun. He lubed the finger up with his spit, then gently slid it inside me. I groaned approvingly, and started to rock back and forth against it. Encouraged, he followed with a second finger. He got to alternating between licking and finger banging, and I rocked harder every time the fingers came to let him know how which one I preferred.

Suddenly, he got up. "Give me a sec", he said, and he opened up a drawer. I saw him grab a white vibrator and a pink dildo, as well as a bottle of lube. Finally, I thought.

The vibrator felt good. This guy really knew how to find my spots. The dildo felt better. I was ready to try that cock. I pushed him on his back, grabbed the condom from my clutch (smiling inside that I'd remembered it) and gave him a little kiss on the dick before I covered him up.

Uh oh. The condom was regular size, and his snake barely fit. It didn't even come three quarters of the way down, and it seemed way too tight around the shaft. Oh well. I wasn't going to turn back now. I lubed him up, pulled off my dress and got in on top of him. After a last little kiss on the lips, I pointed it against my hole and slowly worked on sliding it in. This was the position I'd used when I lost my virginity, as it allowed the bottom to move completely at his own pace. In this case, it seemed like a good idea to do it again.

First the head. "Uhhhhhh... Your pussy is so tight," he groaned, as I carefully bobbed up and down a little to get comfortable. Just relax I thought, working through the initial pain. The weed helped a lot, and with every motion it got easier and easier to slide further down. Albert had now grabbed my cock too, and was gently masturbating me as I tried to wrap my body around his dick.

At last, I got comfortable with taking most of him inside me, and I got to fucking him. This felt good. So good. I had never been filled up like this before, and the weed got me horny as fuck. Albert's dirty talk really helped, too.

"Oh yeah... You sexy little whore... You like that big dick in your pussy, don't you?"

"Ohhh... Yeah... Yeah" was all I could moan in return. At one point, I went all the way down, his dick sticking into me all the way to what felt like chest height.

"Wait! WAIT!" Albert suddenly grabbed me, and I pulled off his cock.

"What? You can come if you want to"

"No, look!" He pointed at his cock. The condom was hanging around it like a burst balloon, ripped in half completely. Uh oh, I thought again. Oh well, I also thought again. The damage was already done.

"You're clean, aren't you?"

He nodded. "Got tested like a month ago. Can grab the results if you want."

"No, I trust you." I lay down next to him on my stomach. "Fuck me. Fuck me so hard in the ass, and then shoot your load deep into me."

"Ok... Can't refuse a lady." He got up behind me, and second later was hammering me doggie style. This was even better, hitting me right in the prostate with his huge python. This was becoming too much for me.

"Oh, that feels so good... I can't... I can't hold... Uhhh..." I came harder than I ever had. That seemed to trigger him, too because seconds later I felt his cock throb inside me, his load shooting deep into my ass. We fell asleep almost straight after.

The next morning was nice. He made me some eggs, and we joked around a little. Then, we took a shower together, and I got one more chance to take that delicious cock in my mouth.

I couldn't face doing the walk of shame in my dress, so he both lent me some of his clothes and a pair of flip flops (too big, but good enough for the trip) and called me a cab. He gave me a shopping bag for my other clothes, but he had a request before I went.

"Can I keep your panties? I'll buy you a new pair if you want, or I'll give you money to do so, but I'd really like to keep them as a memento."

"Sure. But you don't really need a memento. I feel like we'll be seeing plenty more of each other." I said, with a final wink. I kissed him, then walked outside to jump in the taxi.