All dressed up and got her first encounter

Hot Hook Up - A True Story - 24 Jan 2026

The story of Rochelle and her first hock-up

1 So he cancelled on Friday which pissed me off, but on Saturday he texted me, we had some general flirty exchangers and he asked me to pick him up. He was staying just down the road around the corner, which was really cool for me.
So anyway I picked him up and before I could ask he was rubbing leg. Asking me some stuff I wasn't listening to, feeling his hands wandering around my dress. My optimism quickly turned into how I could pleasure a man who obviously wants to release his frustration of his bisexuality into his desire of a feminine male.

Got back here where I had my sissy room set up and all lights down low
We sat on the couch and rubbed each other and kissed... He had a beard which I knew it wouldn't like and his taste was not the best. That was the only kiss. I like kissing, never forget when younger I kissed a girl who had pillows for lips.
Next thing he pulled off all of his clothes and his cock was in my mouth so fast.
I love the lips around my cock keep going, he said as I tried to negotiate the fatness of his cock in mind; His cock was fat and about 7". I wonder if I could get it in.

Wow, it felt so good that anyone wanted to do that with me. I sucked on it for a little while and got my tongue all the way to his balls making me gag a bit. Rochelle was apprehensive she was giving a blow job to someone who knew how a slut sucked cock. Her uneasiness was put to rest when the fatness of his cock hardened and he started to pull the dress up on my back
Next I took my dress off exposing the next layer of my sexuality for the first time in front of a total stranger hoping to get a reaction. Rochelle wanted to know so much about her hard work in becoming a crossdressing slut. Must of been alright because we play with each other for a while
Then he asked me about the sissy room ,so I grab his cock and lead to the room
He push me straight onto the bed and started to rip my panties off and rubbing my ass
I thought, he is going fuck me strait away and I stretched out as far as i could and just managed to get the lube and gave to him
Wham he was in and it hurt like hell. ‘get it out’ I said. Let's start was something smaller
passing a medium size dildo to him. Without a word he worked my asshole over.

2
So he was using the dildo in my ass, started off slow and it wasn't long before he had the whole thing in there. moving all around , in and out. I was waiting for the next thing, then he pulled it out. I moved to the middle of the bed on all fours and placed my head into the pillows exposing my gaping ass in the air. He rolled in behind and with ease he slipped his hot hard cock into the waiting hole. I felt the weight of his body slowly forcing down on my hips and I let out a moan of pleasure. Back and forward motions started to increase in pace. I was feeling no pain but instead my mind was floating into a world of heavenly lust of sissy slut. I just let it go and pushed my head further into the pillow to muffle the mix of moans and groans I was not sure how to release. Then he stopped... Looking up I knew he wanted a new position. Rolling onto my side sticking my leg into the air. We went for it again, but it wasn't going as well and he got off the bed to look down on me and I could see the amorous drips perspiration glistening on his chest in the dim light

3
I just wanted him in me, and immersed back into the pillows. Sure enough he was back in with a bit more vigour and my pleasure increased to a point of... Holy shit where the fuck am I, oh fuck what is happening with dry tears of joy rolling around in haze of confusion of man who was lost in his fantasy world of Rochelle's desires of becoming a crossdressing piss slut. It was only a few months earlier this lonely old man was pulling his pud to porn wishing to be the one on the film. Rochelle's rapture instantly became lust and started to push back on her knees to get the full length of the tower of power that was driving her into a foul mouth dirty slut that no mother should hear.
In hearing this he jumped to the other side of the bed and pulled her face straight onto his raging cock closing down any thoughts of being a pin cushion and faced fucked her to the appurtenant of lost of breath. Eyes rolling back in her head she wondered if she could take it anymore. Lucky the next thing Rochelle knew was her face was back in the pillows screaming harder not wanting it to stop. Then it happened, the climax. Those last few pumps that you know leaves a man emission of semen, and turns him into a guilty narcissist self-absorption of nasty copulation with the person you just fucked. Wow, I didn't think I would come up with that.
Getting off the bed and straight to the bathroom. Rochelle was left in a recovery mode that was more exhausted than she could ever know and with a huge smile on her face, like a giggling school girl fulfilling her character of a sissy slut. Getting up she put a new pair of panties on.

4
Going back into the lo wondering what’s going to happen next to see him putting his shirt back over his head saying “can you take me back now”. With that i grab the keys and open the garage door and get into the car still in a daze giddy disorganization of blissful bewilderment.
The drive back was not like the drive there and was quiet and fast. Pulling up to drop, Rochelle plucked up the courage to ask how he thought the night went for him. Opening the door Rochelle couldn't quite hear what he said, but heard the word wife and instantly knew she would not be seeing this guy again. Rochelle didn’t really care because she got what she wanted. Halfway home she could feel herself leaking into her panties and knowing when she's got home that she will be immersed in the thoughts of a sissy slut with a creampie to savour and enjoy to the full.

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