Justin knew Shelly had a bad day at work. He could hear it in her voice when she called to say
she was going to be home late, something about deadlines and unrealistic expectations really
had her frustrated. As soon as he heard the frustration in her voice his mind started to wander
and he wasn’t really listening to details. In his mind, he already started planning a surprise for
the evening. He laid out Shelly’s favorite lingerie, a cute pink babydoll, white thigh high
stockings, and lacy pink satin and lace panties. As soon as he hung up he started to put his
plan into action. He knew he had a couple of hours to get ready, so he poured himself a drink
and took his time. Not only going to pamper Shelly tonight, but he would pamper himself too.
He sipped his drink while the shower warmed. He found himself thinking of the night ahead,
and his little penis started to get hard. He pulled out the trimmer and started to trim the most of
the length off his leg and body hair, this was going to be a special treat so he wanted to be
completely smooth. After lobbing off the bulk, he hopped in the shower. There, he took his
time, enjoying the warm water, occasionally reaching out for a sip of his drink. As he washed
his body he would think about how things would play out. Shelly would come home and see her
special treat, and would immediately feel comforted and special. He kept getting hard, but
wanted to save himself for the special evening. To keep his mind on task he focused on
shaving, making his body smooth.
It was harder and harder not to touch himself, he liked the feeling of being hairless too. The
warm water flowing over his newly exposed skin was so sensual. His chest, legs, his cute little
ass (Shelly called it that), and even his balls. His mind kept wandering…. If the water felt so
good, imagine how good it is going to feel when it’s her tongue. Shelly LOVED her mouth on his
body; anywhere, everywhere. He imagined her coming home to see her surprise, kissing his
lips, dropping to her knees and taking his little penis in her mouth, and licking his hairless balls
before working her way back up to his lips and leading him to the bedroom.
The water was starting to cool, far more time had passed in the shower than he realized, he
needed to get moving again. Justin pulled out a nice bottle of wine for Shelly, grabbed a glass
for her and prepped a quick snack for when she got home; she was going to need the energy.
It was very hard to keep his mind from wandering again, imaging the taste of wine and fruit on
her lips and where those lips would be later. His mind picked up where he left off daydreaming
in the shower, Shelly leading him to the bedroom, laying him face down on the bed and slowly
burying her face between his freshly shaven ass cheeks, her tongue eagerly licking his tight little
hole, he found himself audibly moaning while he was daydreaming.
His phone rang, Shelly was headed home and would be home soon. No more time for
daydreaming, he had to get in gear and finish putting his plan into action. He rushed back to the
bedroom and carefully donned the sheer pink babydoll. The thigh high stockings were a little
tricky, Shelly usually dressed him for ‘girl’s night’ and he should have paid more attention to how she put them on. He was trying to be careful but was rushing, as time was running low. In his
scramble to prepare for their girls night his thumb went through the stocking causing a hole that
ran the length from thigh to toe, he cursed under his breath; he wanted tonight to be perfect.
With no time to get another pair, he continued to prepare.
He caught a quick glimpse of himself in the full length mirror, Shelly would be pleased. She
loved how he looked and felt when he transformed into Justine. His mind started to wander
again about how she would call him her pretty girl and caress Justine’s body over the lingerie.
Shelly’s hand would softly brush Justine’s ass over the satin, and always over to his hardening
cock, she would always tell him that she loved how it looked and felt. The truth was, he did too.
I have no time for this, he thought to himself, he had to finish, Shelly was merely minutes away
and he wasn’t done yet. He headed to the vanity mirror and did his makeup. Again, Shelly
usually helped him with this, but tonight was a surprise. Fortunately, he paid attention enough
to look acceptably pretty; foundation, blush, eyeshadow, lipstick, and mascara. With each step
he felt and acted a little more feminine. Shelly always found the transformation incredible, going
from being a handsome, masculine man to a coy, pretty, feminine sissy. HER sissy, Justine.
Even Justine’s movements were feminine, from the way she stood, to the way she walked,
talked, and moved.
Justine was waiting patiently for Shelly, but too much time had passed. She started to worry,
then get frustrated. “Why hasn’t she called?” Justine paced the house in her white kitten
pumps when Shelly’s car pulled up. Finally!
Justine rushed to pour a glass of wine for Shelly and meet her at the door. Just as Justine was
getting ready to open the door, Shelly burst in, a couple of work friends in tow. Shelly didn’t
even look up before saying, “Sorry honey, I ended up gossiping with the girls…” She stopped
speaking when she heard the giggles, saw Justine and slowly finished her sentence, “and we
decided to come back here for a girl’s night.” Shelly slowly grinned and had an upward
inflection in her voice as she said girl’s night.
Justine was expecting to surprise Shelly, but she was the one who got a surprise. Justine was
shocked, humiliated, and embarrassed. She stood motionless, what should she do? There she
stood, at the door, head to toe sissy; full makeup, long curled hair, wearing pink lingerie,
stockings and heels in front of Shelly and her work friends.
Without hesitation, Shelly grabbed the glass of wine from Justine’s hand, gave her a quick kiss
on the lips and said, “Thanks, honey. Now be a doll and grab a few more glasses of wine for
Kate and Cindy.”
Shelly grinning from ear to ear as the trio walked by, Kate and Cindy holding back giggles. As
Cindy walked by she smacked Justine’s ass and said, “thanks, doll.”
Source: reddit.com/r/Erotica/comments/hfqr90/girls_night_sissy_crossdressing_humiliation