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Tranny Phone Sex Taking Your Tranny V Card

I just love taking virginities as a tranny phone sex whore. It’s such a thrill to feel that tight ass clenching around my cock for the first time. Recently, I was at a party and spotted this young guy who looked like he could use some tutoring in anal pleasure. His name was Jack and he had no idea what he was getting himself into when he agreed to let me have my way with him.

I took him to the bathroom where we locked the door and turned off the lights. The anticipation must have been killing him because his breathing got heavier as soon as I started undressing myself. When I pulled out my huge tranny cock, Jack gasped in shock but also licked his lips nervously – it was clear that he wanted it even though he was scared shitless.

I knelt down in front of him and slowly pushed one of my fingers inside his tight little hole while rubbing his swollen dick through his pants. He moaned softly at first but then started begging me not to stop once I added another finger and began fucking him good and proper with both hands on either side of his head holding him still for my pleasure.

Finally, after teasing him mercilessly with every inch of my monster cock rubbing against sensitive spots outside of his body, I positioned myself behind him so that our hips were aligned perfectly before pushing forward hard enough to make sure everyone knew this wasn’t their first rodeo – including poor old Jack whose mouth fell open wide enough for me plunge two inches deep into his virgin ass! He screamed out in pain mixed with pleasure as I started pounding away at him, feeling every vein on my cock bulge against the walls of his tight passageway. His hole was so hot and wet around me that it felt like heaven itself; each thrust sent shockwaves through both our bodies while he tried desperately to keep up a steady rhythm despite how much it hurt (or maybe because).

As we fucked harder and faster together under cover darkness inside this public bathroom stall, sweat dripped down from our foreheads onto each other’s skin creating an intimate bond between us even though no one else knew what was happening behind closed doors. Eventually after about 20 minutes or so – during which time Jack had cum twice already just from being fisted by my massive tranny dick – I pulled out only slightly before shooting ropes upon ropes of thick creamy cum deep into his gasping throat as he sat there eagerly waiting for more punishment…and satisfaction too if truth be told!