Sissy and His Mom Pt. 13 Transgender & Crossdressers


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Dear Reader,

In the previous part of this , sissy Daisy’s mom urged him to have breast augmentation. Daisy was reluctant until his girlfriend, Caitlin, said that she wanted him to have a larger bosom. I hope you enjoy this installment.

Sincerely,

Whippet

Mom drove me to my appointment with the cosmetic surgeon. The receptionist showed us into Doctor Hughes’s office. She was standing behind her desk looking at an Xray. Doctor was a young woman with long raven hair and a statuesque build.

“Welcome, ladies. Won’t you please have a seat,” she said cordially. “I believe that the young lady is interested in breast augmentation. Is that right?”

“That’s correct,” answered Mother. “Just to be clear though Daisy is a transwoman.”

“I’ve done surgery for lots of transwomen, so that won’t be a problem at all,” answered Doctor reassuringly.

Then she looked at me and asked, “Daisy, have you decided what size and shape breasts you’d like to have?”

“My girlfriend Caitlin wants me to be a size C, so that’s what I want too. I didn’t know there were different styles though.”

“There are two common shapes, Daisy,” she said handing me a brochure. “The pictures show the rounded breast and teardrop shape.”

I showed the pictures to Mother and said, “I want my breasts to look just like yours, Mom. I think the tearshape is more like you. Right?”

“I think so, Daisy,” said Mother. “If you want to be sure, though, we can compare.”

“Can we please, Mom?”

Mother unrobed and we compared her marvelous bosom to the pictures. She was definitly teardrop shaped.

“Mom, how big are your breasts?” I asked naively.

“I’m size DD,” she answered.

“Do you think I should be a DD, too, Mom?”

“Maybe later, Daisy” she replied. “For now, you should be the size that Caitlin wants.”

I handed the brochure back to Doctor and said, “I’d like teardrop shaped breasts in size C, please, Doctor Hughes.”

“That’s an excellent choice, Daisy,” she said. “Tearshape is the more natural look and C is a good size to begin with.”

Then she said, “Would you please remove your blouse and your bra, Daisy. I want to examine you.”

I had worn a pink training bra with lacy cups for my appointment, so I was delighted to show it off. Doctor unfastened the front closure, looked at my chest and measured it. Then she felt my breast tissue and nipples, and declared me fit for surgery.

Next Doctor explained the procedure and advised me that there would be soreness afterward. She also warned that I must not let my girlfriend play with my new breasts until they were completely healed.

On the drive back home Mother said, “I’m excited for you Daisy. Pretty soon you’ll be a full figured young woman. How would you feel about dieting and waist training, Dear? Wouldn’t you like to have an hourglass figure?”

“Oh, yes, Mom!” I squealed happily. “I’ll start dieting right now! Can I have a corset too, Mom? Please?!”

Since Caitlin and I were getting more seriously involved, Mom decided to invite her and her mother, Margaret to tea. Mom bought me a lovely floral print dress for the occasion and a threelayer rainbowcolored petticoat to give it volume.

On the morning of our tea, she took me to her salon and had the stylist, Maureen, give me a cute 60s flip hairdo. After Maureen removed my curlers and brushed me out, she and Mom decided that I would look very comely with a wide ribbon in my hair. Mother let me choose the ribbon, and I decided on pink with lacy trim along the edges.

When we arrived back home, I put on my apron and helped Mom make a strawberry shortcake for the tea. While the cake cooled I set the dining room table. Just as I finished though I clumsily knocked a cup to the floor where it shattered. This was Mom’s best china!

I began sobbing and Mother rushed to comfort me. My heart was racing and all at once I felt dizzy.

“Mom, please call Caitlin’s mother and tell her the tea is off,” begged hysterically.

She took my trembling hands and led me to the living room sofa. We sat and she embraced me tenderly. Now I was crying even harder and I couldn’t stop shaking.

“Daisy, Sweetheart, I can’t cancel now. I just spoke with Margaret. She and Caitlin are so excited about visiting. I know you don’t want to take my Valium tablets, Honeybunch, but you’re having a panic attack. So, please, just this once.”

I swallowed Mother’s pill with the utmost reluctance but I must say that it worked wonders. I soon felt much calmer. Then I dressed and Mom helped me with my makeup. I was in a cheerful mood by the time that our guests arrived.

Margaret was wearing a lovely tea length dress, appropriately enough. The chartreuse frock had Chantilly lace accents and a ribbon belt that tied in back with a bow. Caitlin was dressed in a grey threepiece women’s suit. She had dark eye makeup and her lips were painted coral. Caitlin’s impressive appearance and her confident bearing made me weak in the knees.

Margaret complimented me on my dress and my hair, and Mom remarked on Caitlin’s handsome look. Then we sat at the dining room table where Mother poured tea for everyone. I served our strawberry shortcake and we chatted amiably.

During a pause in our conversation Mom said, “Daisy has some pretty big news. Would you like to tell Caitlin and Margaret, Sweetie?”

“Sure!” I said. “Mom took me to a plastic surgeon and I’m getting breast implants. I’m superexcited and the procedure is already scheduled!”

Margaret stared at me in surprise. After recovering her composure she said, “That’s wonderful, Daisy!”

Then Caitlin asked, “What size are you going to be, Daisy?”

Caitlin’s question provoked a strong reproach from her mother.

“That’s a very personal matter, Caitlin,” she said. “I think you should apologize.”

“It’s alright,” I said. “I’m going to be a size C and my breasts are going to be teardrop shaped, just like Mom’s. I can hardly wait!”

“I’m looking forward to when Daisy has breast, too,” said Mom. “Then we can shop for bras together.”

“I’m looking forward to Daisy’s boobies too,” said Caitlin with a wry grin on her face.

“Shame on you, Caitlin. That’s very rude!” scolded his mother again.

When Caitlin and I started giggling, our mothers joined in as well, and soon we were all laughing out loud.

After we finished our tea, Mom invited Margaret to see her flower garden. That left Caitlin and me alone.

“Would you like to go outside to the patio, Caitlin?” I asked.

“That sounds nice, Daisy,” she replied with a smile.

Caitlin pulled out a chair at the patio table for me. Just as I sat down a strong gust of wind billowed out my dress and exposed all three tiers of my petticoat. I was very embarrassed and I had to hold my skirt in place as the breeze kept blowing.

“I’m sorry, Caitlin,” I tittered. “You weren’t supposed to see that.”

“Don’t apologize, Daisy. You’re petticoats are lovely, just like you, Sweetheart.”

Her compliment made my heart flutter!

Caitlin remained standing in front of me as she said, “I have something for you, Daisy,” Then she drew a small box from her jacket pocket and presented it to me. Inside was a gorgeous sapphire ring with a white gold band!

“Oh my God!” I gasped. “I can’t accept this, Caitlin, it’s too much.”

“It is a lot, Daisy, but I love you a lot, Darling.”

Caitlin slipped the sparkling ring onto my finger. Then she bent toward me and kissed my waiting lips. I felt like a fairy tale princess!

When Caitlin finished kissing me, I excitedly asked her, “Can we show my Mom now?”

“Sure, Daisy. Our moms are still by the garden.”

Caitlin helped me walk across the lawn because my heels kept sinking into the soft ground.

“Mom, look!” I cried holding up my hand for her to see.

Mom’s jaw dropped. “Daisy, that’s a lovely ring!” Then she turned to Caitlin’s mom.

“Margaret, is this alright with you? It looks awfully expensive.”

“I have nothing to do with it, Janice. Caitlin bought it on credit. She can’t stop talking about your Daisy. You should hear her go on. ‘Daisy’s so pretty. Daisy’s such good company.’ Daisy this, Daisy that, all day long.”

Mom shook her head in wonderment and said, “I’m very happy for both of you, Caitlin and Daisy.”

When our guests were ready to leave, Caitlin took me in her arms, tipped me backward and kissed me passionately right in front of our moms.

Thanks for reading. More is on the way.

Whippet’s fashion tip: If you have difficulty putting on pantyhose while seated in a chair, try sitting on the floor instead. I find it much easier.

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