Sissy Scare (Erotic Halloween Tale)

Written by the Therapist Samantha Summers™

Written on the 3rd of October the year 2014

First was published on October 5th, 2014

Originally titled “SissyStory” within

“Sissification (31 Days of Fetish)


Always going with a Goth style, Josh was always an outsider. Inside he was a Genius, just a month away from graduating from Berkeley despite only being 19. Being openly Gay, he got along with most of the girls on campus. But there was this one girl who was getting under his skin.

Tammy was the perfect example of someone with a silver spoon in hand, literally & figuratively. It was no secret that being the heir to American’s largest banking corporation was what got her into the prestigious school, not her C average grades. Shortly after getting in two years ago, she formed her fashionable click and made it a daily thing to tease & torment the Occult-loving Brain-boy. Tammy’s favorite term to use on Josh was “Sissy”; sissy this, and sissy that.

Well, today was the last straw. As Josh, minding his own matters, was being hounded by Tammy & her team, his neutrality was neutralized. Tammy’s direct attack of “Do you swallow like a sissy should?” was acknowledged by Josh for the first time. Josh looked up & said, “I hope that you become a sissy.”

After a tiny pause, Tammy started laughing, “I can’t become a sissy you stupid shit-packer.” As she pointed to her cosmetics, clothes & curves, she added, “I’m already super feminine.” Her & her clan continued their insulting laughter.

“So be it”, Josh said quietly. He then looked Tammy in the eyes, held out his open palm in front of her, and said in a loud & drawn-out manner, “By Ecanus, let the definitions drive your decisions!” and blew air across his hand towards Tammy.

Like some South-Beach Stereotype, Tammy placed her hand on her chest, smirked & said, “Oh… my… gosh… And when I thought you couldn’t get any lamer…” As Tammy & her roost broke out laughing, Josh turned face & walked off despite the continued verbal onslaught.

Her daily devilish devotional being done, Tammy went on about her day. So, after suffering through half of a lecture, she made her way off campus.

Instead of calling for her shofar as usually, Tammy oddly chose to walk instead, despite her place of residence being 5 miles from the university.

After around a mile of walking in platform shoes, Tammy was tired, and wisely chose to take a bus the rest of the way home. So, she took a seat at the closest bus stop, which she was the lone occupant of. Waiting on the next bus, she wanted to have the fee ready, so she pulled out the wallet from within her purse. In a futile attempt to find a single, she pulled out 8 or 9 one-hundred dollar bills; holding them in one hand as she riffled through the numerous sections of her wallet with the other hand.

Suddenly, the ear-splitting vocalization of “NAÏVE” sounded in her head. As she held her forehead from the stunning sounding, the bills were snatched from her hand in one swift swoop. She stood up, frantically screaming “Stop!” again & again as the hoodie-wearing figure fled down the empty street.

After several minutes of whining, foot stomping & muttering, Tammy slug her penniless purse over her shoulder and starting walking again.

After a few strenuous blocks, Tammy stopped to rest her sore feet. Looking around her surroundings, she spotted a homeless man near an alleyway. She stepped on over to him; as he laid there snoring, splayed out with spittle in his straggly beard, and surrounded by empty beer cans.

Leaning over him, “Are you alright sir? Can I do anything for you?” she asked. The moment she questioned his snoring body, like nails on a chalkboard, “NURTURING” announced in her mind.

As Tammy remained hunched over with her hands pressed against her ears, the man grunted, coughed & opened his eyes. Seeing the ‘T&A’ hovering over him, the grungy man raised himself on his elbows. Through a phlegmy throat he spoke, saying, “Well, hey there cutie…”

Startled, Tammy stepped back. In the back of her mind, she knew she shouldn’t be doing this, yet she couldn’t not do so. Repeating her question, Tammy again asked “Can I do anything for you?”

With a distorted smile that showcased a few decaying teeth, the man responded with “I normally take any spare change… but I’ll take anything you’ve got darling”, ending with a gurgling cough.

Tammy thrust out her chest and rolled her hands over her breasts. Then, in a matter-of-fact fashion, she said “I’ve got plenty to give” while gliding her hand along her backside. As she caressed her own ass, the skull-cracking reverberation of “FLIRTATIOUS” rang; her knees buckling from the sharp pain of it.

Unfazed by the abnormal sight, the grungy man fully sat up, knocking over one of the empty beer cans. After an almost snarling sound, he said in an aroused tone, “Well shit cutie… I’ll take some of that.” He then shakily rose to his feet, nearly tipping over.

Still crouched, Tammy let go of her own head. Looking up at the man clothed in almost literal rags, she simultaneously stepped over to the wall, her back facing him, and said “Take all you want.” Before her thoughts of shocked confusion could come to fruition, “RECEPTIVE” blared throughout every corner of her brain; the stunning verbal apparition tipping Tammy towards the wall, only stopped by her palms slapping against the brick.

Anxious & ambitious, for the first time in countless years, the man released his frayed belt and wobbled over to Tammy with his pants around his ankles. Behind her he said, “Letting you know… I don’t believe in rubbers.”

Partly disoriented, Tammy replied, “That’s alright.” Then her head knocked against the wall as “TOLERANT” hit her like a freight-train…

Needless to say, Tammy had quite a few negative consequences from her decisions; decisions defined by the stereotypical qualities of a Hyper-feminine “Sissy.”

The moral of the story is: Know what you say before you say it.

All rights are reserved by Therapist Samantha Summers™


The Samantha Summers Institute™

Sissy Scare (Erotic Halloween Tale) was last modified: March 16th, 2016 by Therapist Summers
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