Chapter 20
by CyntheDim
"Where!?"
Jennifer's bedroom.
Jennifer yanks Miguel out from the bathroom in nothing but his all white lingerie the cold wood panel floors sending shivers running up Miguel's back as he is pulled into a soft and comfortable room that he recognized as Jennifers room. She pulled Miguel forward towards a Vanity mirror and desk combo that had a large amount of makeup set out on it as Jennifer was finishing getting ready and sat him down in the spinning chair.
"Okay hun sit down and I'm gonna make sure you get your man!" Jennifer began snatching up different foundations and comparing them to Miguel's skin tone. "I dont know about this I dont think I ca-" Miguel was cut off as Jennifer pressed a finger to his pouty heart shaped lips. "Shh Maria its okay, see I had an interesting conversation with Robert the other day," Jennifer then began to apply make up to Miguel's face sharpening and softening just the right spots contouring his face until it looked like a beautiful girl ready to party. "And he told me that he met a girl that he really liked but was unsure because he isn't sure if he can see her after summer and doesnt think he can let go that easy!" Jennifer giggled as she grabbed eye shadow and lipstick applying them to Miguel's face touching up his features with eye liner and lip liner. "I bet now that you are that girl~" Jennifer said teasingly as she worked on Miguel's face.
Miguel's mind was racing as jennifer told him this his soft hazel eyes locked under closed eye lids. 'So he was scared to hurt me?' Miguel felt his heart flutter and his stomach turn as Jennifer drew across his face tickling and drawing small gasps out of his mouth. 'She is going to make me go try to get Robert what does that even mean!?' 'I've never even tried to hit on a girl how do i even flirt?' Miguel's mind began to be bombarded with doubt and shame the longer Jennifer worked on his look before he felt the chair shift and spin around.
"Okay hun go ahead and look!" Jennifer basically squealed with glee. Miguel opened his eyes slowly and scared of what he was going to see as he felt Jennifer toss his long hair across his shoulder and what he saw shocked him. Miguel saw a beautiful young Latina woman he had seen her a thousand times being slightly flirty in streams or dancing seductively across a mobile app, "Oh my God..." Miguel's voice trailed off as a shakey hand came up and touched his mouth that hung open in shock.
Jennifer giddily vibrated in place seeing Miguel's reaction before she sprinted over to her closest dragging out a large bag before unzipping it and throwing clothes away over her shoulder. "I have just the outfit to compliment that lovely lingerie set you have Maria!" She swiftly pulls out a set of dark black blue jean shorts and a tight almost sheer long sleeve black shirt with a low v-neck that will show off his small clevage before holding both and approaching Miguel hungrily a devious smile on her face. "Its time you stop hiding that wonderful body of yours Honey!" Jennifer giggles and throws the outfit onto Miguel's lap.
Miguel lifts the two articles of clothes causing his already blush covered cheeks to darken even further. "I can't wear these, they will make me look like..." Miguel's voice trails off as Jennifer walks over and lifts Miguel to his feet looking into a full length body mirror. "They'll make you look like a girl trying to impress a boy she has a crush on or they'll make you look like a girl trying to IMPRESS a boy." With a giggle jennifer makes a lewd blow job motion teasing Miguel as he lightly pushes her shoulder with a nervous chuckle. "I mean I do like Robert it would be nice to impress him." As Miguel stares at himself transformed the only idea of him being a boy is a tiny bulge that doesnt even slightly pop out of his tight panties.
Jennifer lets out another giddy squeal as she runs back over to the closet grabbing a pair of black and white heeled sneakers. "Then get dressed girl!" Jennifer tosses the shoes at Miguel's feet and with a nervous sigh and a shudder down his spine Miguel got to work slipping the tight shorts over his thick nylon covered thighs and up to his large bubbly ass the shorts parted his ass and lifted it making it stick out and appear far more prominent driving the lace thong further between his ass cheeks as the holes of it gripped and sunk into the flesh of his soft thighs making a small bulge of flesh and nylon where they meet. Miguel grabbed the shirt before slipping it over his head feeling the thin soft fabric run over his arms and grip onto his curves hugging each of them softly showing off his hourglass waist and pulling softly up on his chest giving him the illusion of small breast. Lastly he grabbed the wedge heeled sneakers slipping his small feet into them the nylon of his stockings slipping deliciously into the soft interior of the sneakers before lacing them up and standing proudly. "Damn Maria!!! I might just be jealous of Robert you look amazing!" Jennifer punctuated the comment by smacking Miguel's ass hard making it shake and jiggle.
With a yelp Miguel tried to cover his obvious nerves as Jennifer finished getting ready in a tiny tight red dress before grabbing Miguel's hand comforting him before she reached out and threw the door open a wave of bass and voices hit Miguel from the other side of the house as Jennifer yanks him down the hall closer and closer to the cacophony of voices.
How does the party begin?
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Creation of a sissy
Miguel's journey
Hey there I'm Cyn and I'm a bit dim this is my first story so please feel free to post criticism or praise and I'll be sure to read it all! So far it is only one path and its M/M! Holy hell 2,000 plus people viewed, 20 likes, and not to mention all the favorites and book marks. You people must really like my story ;) I hope y'all enjoy as i take it further and further for y'all! I am so sorry for being gone so long my lovely readers! Im back and im gonna try to be more consistent with the story until it reaches a good end cause UGH i hate a good story that just stops! <3 ;)
Updated on May 9, 2025
by CyntheDim
Created on Nov 5, 2024
by CyntheDim
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