I had been on Grindr for a number of weeks making connections in my area and chatting to various guys hoping for a good meet. My profile on Grindr portrayed me as sissy girl Gigi, with various pictures of me in sexy panties and trashy outfits, which did seem to get a lot of attention.

One guy I had been chatting to for while was really keen to meet and the opportunity eventually arose when he had issues with a burst boiler and had to send his family to stay with with his wife’s parents for a few days.

We arranged a time one evening, after dark, for me to go around to his place. But there was an interesting twist. He wanted me to arrive dressed as Gigi and wanted to pay me for sex like you would an escort. He had never done that before and insisted he would pay me £100 for a 1 hour session, and offered an extra £50 so he could fuck me raw. He also insisted that I should be smooth all over, which I don’t mind of course. After some discussion we agreed on the deal.

On the night, I did my usual preparation, deep cleansing, full body hair removal, make-up, dress, wig, heels, the works.

I arrived at his place. It was dimly lit so I could just about see where I was, but no neighbours could see anything. Once inside, he turned up the music to further mute any noise we made.

He made me get on my knees to suck him first. He grabbed the back of my head and proceeded to fuck my mouth to the back of my throat. I felt his cock touch my tonsils. I also tasted his precum on my tongue, and I proceeded to lick off as much as I could. Since we had agreed an hour, he had time to cum twice, and proceeded to offload his first shot deep into my mouth forcing me to swallow it, and suck every last drop from his cock.

With my mouth still full of the taste of cum, he thrust his tongue into my mouth and aggressively French-kissed me.

After a while, he was ready again. It did help that I played with his lovely cock and sucked it some more. He lubed up, turned me around, bent me over, and worked his delightful cock into my sissy hole, bare as agreed. Because he had already cum once, the second load was going to take a lot longer. Fortunately we weren’t clock watching.

He pounded me for at least 20 minutes varying his pace while I sniffed that bottle of poppers to hit that mild high and I cease the intensity of that ongoing anal orgasm. And then there was that final thrust - he slammed it as deep as he could and I could feel it throbbing deep in me as he emptied his load deep in me. He then slowed down, pounding a few more times before withdrawing. I had brought a plug with me, which he duly grabbed and thrust into my sissy hole making sure his cum stayed in.

I straightened myself up, pulling my panties back up and making sure my hold-ups and skirt were in place. He duly paid me the agreed amount, thanking me for my time, and calling me a dirty whore at the same time. That was so hot.

I went off home, plug and cum still in, went to bed and woke the next morning, plug still in and feeling like I had the best fuck in a long time