Sissy Erotica: Cruising Night

Erotic Stories, Sissies, sissy

Posted on August 29, 2018

Sissy Slut at the Alley

Miss Brat adjusted her sexy bra and gave the order. Her sissy knew what she was getting into when he first started having a relationship with Miss Brat. She was relentless, strict and domineering, a true mistress of his life and feelings. She would tell him what to do and where to go; whom to fuck and what to enjoy it. This time Miss Brat had special plans for him, for she ordered him to visit the local cruising alley. It was in the general downtown area, and everyone knew that all kinds of shady activities take place there: from local hustlers and people who just want to have sex to sissies and couples who were looking for adventures. She specifically ordered her to have as much fun and possible and to dress nicely. The sissy dressed in his best dress and put on make-up, and decided to have sex with strangers in the dark of the night.

It was past eleven when she first set out. He slowly adjusted his dress and walked confidently; attracting the eyes of the people he came across. The first guy who dared to approach her was a total stranger. After a few sentences, the sissy immediately understood the type. This was a powerful guy, probably an executive or a CEO, someone who was used to getting his way. The guy unzipped his pants and the sissy eagerly sucked his dick, feeling the salty pre-cum on his tongue. The slut swallowed the cock head and the entire thick rod until she started gulping, and then the guy started pulling his hair and rhythmically pushing his head up and down. She loved the fact that they could get caught any minute – after all, their only camouflage was a big bush – but nonetheless, they both enjoyed the experience. The big executive type came inside the sissy’s mouth and quickly cleaned himself, then walked away without even thanking him.

The Whore Wants More

After a few minutes to compose himself, the sissy slut continued his journey, as ordered by Miss Brat. Her influence was so strong in his mind; he could still hear her words clearly as she was standing in front of him. She spotted a middle-aged guy following him, and then the suddenly turned and showed him what he’d do to him. She could see the wedding ring on the guy’s finger; married guys were the best and most devoted fuckers because with a sissy they could do anything they ever wanted. The married dude fucked her in the ass, and the slut could feel his butt hole clenching and relax with each thrust. The guy was silent but after a dozen minutes or so started to moan. The sissy was grinding with his ass and directing his cock inside her hungry hole, imagining how pleased Miss Brat would be when she hears all the adventures that he had. The guy came inside his pussy/ass, giving him a shuddering orgasm, and the sissy slut quickly finished himself off with a few quick strokes. After the executive and the married guy, the sissy was ready to approach a random man who was eager to have his dick sucked. Sissy gladly sucked his dick off, enjoying in that hard cock inside his mouth. She finished the guy with a few strokes.

Then the whore decided to have a short break. Hours have passed since she set foot in the shady alley, and he was already a bit tired. He took a bite of chocolate and wanted to have some water before proceeding, but then he noticed a couple. They were both tall and slender, and the blonde wife was gesturing him to come along. The husband was athletic and good looking, and the sissy immediately knew what they were after. The wife asked her if he would be interested to share his time with them – and she said yes, of course. The wife wanted to participate with her, and they’ve decided to share dicks. The husband quickly unzipped his pants and revealed already hard dick, a big piece of meat that was oozing with pre-cum. The sissy eagerly swallowed the thick cock while the wife was licking his balls. Soon they were joined by another anonymous guy who was passing by. The Sissy swallowed a lot of cum that evening, but this one was the sweetest. They both wanted both cocks to be theirs but had only one month each. Sissy offered her cunt/ass to the other guy, and the guy pounded her while she was sharing the hubby’s dick with the wife. She loved being used and abused in such a way. After the husband came inside his wife, the sissy had the honor of cleaning the wife’s pussy and licking it clean! After all that the action she proceeded to call her Goddess Brat and tell her about her successful night.

(Brat Perversions)

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