Sissy and the Divorcee, Pt. 01

Dear Reader,

This story is told from the female's point of view. If you dream of being a woman, like I do, you may enjoy her perspective.

Sincerely,

Whippet

P. S. I've included a femboy fashion tip at the end.

--

Lois and I became acquainted at an evening yoga class. We enjoyed chatting after the sessions. She told me that she was a single mom with a teenage son, while I related that I was recently divorced.

One night after class Lois seemed distraught. She needed someone to talk with. So, we walked to a nearby coffee shop and sat in a quiet corner booth.

"It's my son, Aaron," she said with tears welling up in her eyes. "I don't know what to do with him."

"Tell me what's wrong, Dear," I replied handing Lois a tissue from my purse.

"I'll show you, Tracy," she said while searching through images on her phone. "Here, look."

I was seeing a picture of a pretty school girl in a plaid skirt and a white blouse. Her hair was in pigtails tied with pink ribbons and she was smiling coquettishly.

"This is your son, Lois?" I asked.

"Yes, that's Aaron but he likes me to call him April."

This revelation touched something deep inside me. I had always been fascinated by sissy boys and I'd even fantasized about having a pansy of my own. Life would be sweet with a submissive boy in skirts performing household chores during the day and attending to my personal needs at night.

Now Lois was sobbing. So, I slid around next to her in our booth and let her cry on my shoulder. I hugged my friend and ran my fingers gently through her wavey hair.

"He's 18 and he just graduated from high school but he doesn't have any plans. He just wants stay at home and live as a girl."

I sympathized with my friend and at the same time I reasoned that this could work out well for all three of us.

"Lois," I said encouragingly, "I may be able to help."

--

I drove to Lois's home the next Sunday afternoon. When she opened the door to me, April was hiding behind her. All that I could see was his flared skirt and the frothy petticoat peeking out from underneath. When Lois stepped aside to introduce us April ran away. A door slammed shut and I was left a bit dismayed.

"He's gone to hide in his room," sighed Lois. "Won't you please come in, Tracy?"

Lois led me to a cozy parlor where she invited me to sit on the sofa.

"May I offer you tea?" she asked pleasantly.

"I'd love a cup," I replied as brightly as I could.

Lois returned with a tea tray and served us. We sat side by side and chatted amiably for a while. Then she turned serious and apologized for April's rude behavior.

"I'm sorry that April ran away, Tracy," she said. "He isn't a bad boy but he's very insecure."

Lois began crying and I dabbed her moist eyes with my hanky.

"I understand, Lois," I replied sincerely. "I'd be frightened, too, if I were him."

Then I continued, "I think that April needs a woman in his life besides his mother."

"I know," she replied, "and I hoped that he'd accept you as a his friend."

"I still think I can be, Lois. What does April like to do besides dress in girlie clothing?"

Lois thought about that for a moment and replied, "He loves playing with his dolls."

"Well, let's try that gambit," I offered.

We walked down the hall to April's room. Then Lois spoke to her son through the closed door.

"April, Sweetie, Miss Tracy asked whether she could meet your dolls."

"Please, April," I affirmed in my sweetest voice. "I love dollies, too!"

"Do you really like dollies?" he replied suspiciously.

"Yes, Dear," I said, telling a white lie. "May I come in?"

"Only if Mommy comes with you," he said.

--

When the door opened, I had my first good look at April. He was absolutely adorable in his poodle skirt, back-button white blouse and Mary Jane shoes. Lustrous curly hair and pink lip gloss added to his appeal along with the innocent look on his angelic face. I wanted to take him in my arms and squeeze him.

Instead, I kept my cool and remarked on how much I liked his room. The centerpiece was his frilly canopy bed with a duvet featuring unicorns and rainbows. The wall paper was a cheerful floral design, and there was a lovely doll house in one corner.

"It was all April's idea," said Lois perhaps a little chagrined.

"May I see your dollies, April?" I asked in a honeyed voice.

"Yes, Miss Tracy," he said happily. Then April took my hand in his and led me to the doll house. His pretty polished nails and soft touch left me breathless. We sat side by side on the floor. A fruity aroma wafted from April's hair. I was barely able to keep my hands off of him.

"This is Katrina," said April excitedly. He was holding up a doll dressed in a poodle skirt and white blouse that were identical to his.

"She's very pretty, April," I cooed, "Just like you, Dear."

"Thank you, Miss Tracy," he replied happily. I sensed that April was warming to me.

"I see that you and Katrina are wearing the same skirt and blouse," I remarked.

"Yes, Miss Tracy," said April brightly. "We wear the same undies, too."

April lifted Katrina's skirt and petticoats to show me that she was wearing miniature bikini panties trimmed with lace. Then he lifted his own petticoats.

"See, I'm wearing the same ones," he said coyly.

April's panties were indeed like the doll's. There was one big difference though and it was poking out above the waistband. I hadn't seen a stiffy since my divorce and I was spellbound!

Lois finally interrupted my revery, "Perhaps that's enough for today, April. I sure that Miss Tracy has other things to do."

"Okay Lois," I said reluctantly, "but may I say goodbye to your charming daughter?"

"Alright," said Lois. "I'll be right outside the door."

I stood and helped April to his feet. Then I embraced him warmly and spoke softly to him.

"I like you very much April and I want to be your special friend."

"I like you, too, Miss Tracy," he replied. "Would we wear matching outfits?"

--

This story will be continued.

--

Whippet's Fashion Tip

Gurls, I recommend shortening the straps of your garter belt until your stockings are tautly stretched. I love how tight nylons tug on my garter straps, especially when I'm walking in public places. Tight stockings and a pretty garter belts are confidence builders.