Patreon LogoYour support makes Blue Moon possible (Patreon)

Mommy's little shemale (SalesGirlAnna and samana44)

S

SalesGirlAnna

Star
Joined
Jun 14, 2011
40 year old Annabelle Stewart was a an executive vice president in charge of sales of a clothing company. and single mother. Her husband was killed when her son was just 3 years old. She got home early that night and headed up to her room.

She was wearing a blue blazer, a matching skirt that goes a bit past her knees, a white blouse, white stockings, 2" black Mary Jane pumps, pearl necklace and earrings. She had her long shoulder length red hair pulled back in a loose bun. She was 5' 7" 110lbs. 34B

She pulled her hair out of the bun and opened the door and was stunned to see her son, half naked in her room.

"WHAT ARE YOU DOING?!"
 
Her 21 son, Josh, suffered for a long time not having a father. This lack of male presence at home made him finding shelter in feminity, and he loved to sneak into his mother's room every night, looking into her clothes and underwear, putting on make up and strutting around like a model. Despite of being a man, his figure was quite feminine: he was very slim, a bit small and smooth figure.

This evening, after a hard day, he rushed into his mother's room nude and looked into her underwear drawer. He was appealed by a set he hadn't seen before, a purple satin bikini panties with a little bow at the front, with the matching bra. He slid it on his shaved body, put a blonde wig-shoudler length" and some 5"inch heels and was admiring himself, when he suddenly heard the sound of his mother's voice.

He looked back and felt utterly embarassed when he saw his mother's face by the door. He quickly put his hands over the bra and panties to hide, and coudl hardly speak "oh my... mom? you're'... why are you here? it's...it's not what you think"
 
"It looks like you are wearing my underwear!" Annabelle walked up to him and pulled the wig off his head. "Why are you wearing my underwear!" Annabelle crossed her arms crossed her chest and waited for an answer.
 
Josh's heart was racing. He could not believe what was happening: he was standing in front of his mother in women undergarment. This situation prevented him from thinking about a good lie, so he nervously said :"I... I was going to do some laundry and... I... I didin't want to go in the basement naked..."
 
"Bull!" said Annabelle, "Do you really expect me to believe that?! I want the truth young man and I want it now..." Annabelle was furious... She felt so violated... She wondered how long this had been going on. More importantly she had to figure out what she was going to do about it.
 
Her son began to burst in tear "Plea...Please forgive me mom... I... It's just that I was curious... I... I just wanted to feel how it is to wear women clothes... please, don't tell anyone this" he begged
 
Annabelle calmed down a bit when she saw her son crying, "Take my things off... Get dressed and go to your room... I need some time to think..." Once he was gone she sat down on her bed and started to think...
 
He ran into his room, locked the door and put on his mom pink evening gown and went to bed, afraid of what his mom could do after that... a moment later, he heard her knocking at the door "son, we have to talk"
 
Annabelle turned on her laptop. She did some searching for cross dressing and other related subjects. After about an hour and a half she walked over to her son's room and knocked on the door. "Josh... we have to talk" She came in and saw he was wearing one of her evening gowns she wondered what happened to it... She didn't say anything about it as she sat down on the bed. "How long have you been trying on my clothes?"
 
Josh sat on one side of the bed, avoiding his mom look: "well... I began 5 years ago... It began after a laundry day... I took a pair of black panties and tried it on, just for fun... and the truth is... I liked it... I felt happy, and it turned me on... so i tried on a bra too... then a skirt and stockings... And I felt very aroused...Oh excuse me mom, it was too much" he sobbed
 
Annabelle moved over to his side of the bed and wrapped her arm around him to comfort him then she said, "It's OK... see... So do you want to be a woman? or do you just like to wear women's clothing."
 
"I... i don't know... i mean.. I would really want feel how it is to be a woman but I really don't know how" he said
 
"I see..." Said Annabelle, She thought for a moment... "I have another question... It doesn't matter to me either way... Are you gay?"
 
"OK..." She said, "Josh, I love you very much. And I don't want to lose you. But, I know that I can't forbid you from cross dressing. That would be wrong. So, tell me what you want... Do you just want to dress around the house or do you want to live as a woman, full time?"
 
Relieved that her mother was not too angry after him, Josh began more comfident. He was lost in his reflexion during a few seconds, took a deep breath, and repleid "I... I would try to live as a woman but I am too shy to go outside crossdressed.. Even at home, I stay upstairs with all curtains down...that... that may sound awkward but... Would you help me to be more comfident?"
 
Annabelle nodded, "I will help you to be more confident. From now on you will live as a woman at home and out in public. Do you have a name for yourself when you are dressed or would you like me to rename you?"
 
"Well... for several months, at night, I have been thinking about being Jocelyn... Do you think that would suit well to me?"
 
Annabelle smiled, "Jocelyn is fine... OK, Jocelyn... Get a good nights sleep... we've got a big day tomorrow..." Annabelle kissed her new daughter on the forehead and left the room.
 
Josh-or Jocelyn- felt relieved and went to sleep, but could not do it. He thought about what happened, and what his mother would do to help him. Moreover, as he thought that he would soon become like a real woman, he surprisingly felt excited and decided to get some "unmentionable female activity" by softly rubbing his little "clit" through a pair of white panties he put in under the night gown
 
The next morning Annabelle was in the kitchen. She was drinking coffee and wearing a purple dress, with a black belt around her waist. She was also wearing white stockings and black pumps. She was waiting for Jocelyn to wake up so they could get started on the day.
 
She heard some noise in the stairs, and then saw Jocelyn entering in the kitchen. He was wearing the night gown but it was wide opened, revealing a pair of white bra and panties. The bra was quite basic, plain white, while the panties had a little pink bow at the front and a lace trim. Jocelyn kissed his mom and shivered as it was cold in the kitchen
 
Jocelyn blushed and replied "ye...yes... I'll have some tea and biscuits...Sorry, I didn't know you were already downstairs... Wow, you're beautiful in that dress! purple suits well to your skin colour"
 
Annabelle smiled, "Thank you dear..." She got Jocelyn some tea and biscuits, "Today is a big day... After you finish your breakfast... I want you to go upstairs and pack up all your old male clothes and any male things you don't want any more... We'll drop them off at the Salvation Army. Today, we are going to go to the salon and get your hair done then we are going to go shopping for some new clothes for you..."
 
You must log in or register to reply here.
Back
Top Bottom