Jim's Navy enlistment ended 7 months ago and lived alone with all of his friends out at sea for the next 5 months. He is a closet sissy, but is becoming less cautious now that he is on his own. He has been growing his hair out for the past 9 months, and recently shaved his entire body, getting weekly tans in a tiny thong bikini, leaving feminine tan lines. He is chatting with men on an alt dating app and finally agrees to meet one to give his first blowjob. The man tells him to show up en femme, so Jim wears a pair of tiny shorts with a pink g-string whaletail, crop top, heels and hair in pig tails. He is lightly made-up and put on a pair of slutty press-on nails. The man tells Jim a blowjob isn't enough, teasing Jim until Jim reluctantly agrees to anal sex. The man invites several friends and they all fuck and get sucked by Jim, taking lots of pics. Jim is easily manipulated and becomes a public sissy slut for their entertainment.
The click of the latch echoed through the empty apartment as Jim stepped out onto the small balcony, the city lights stretching out before him like a twinkling ocean. The night air was cool against his skin, and he could feel the warmth radiating from the penthouse below. He breathed in deeply, the scent of the city a familiar comfort.
He checked his reflection in the window, turning to admire the curve of his hips in the tight dress. It was a deep red, clinging to his body in all the right places. The fabric shimmered under the glow of the streetlights, and he couldn't help but smile at his own reflection. He looked good.