Sissy and His Mom Pt. 12

Dear Reader,

I received many encouraging comments about this series earlier in the year. Since I lack self-confidence, like most pantywaists, those remarks were very empowering. I am resuming this tale and hope that you like it.

Sincerely,

Whippet

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To recap, the story began with the sweet mother-daughter relationship which unfolded after sissy Daisy came out to his Mom. She supported her son's femininity and urged him to open up with other people. Then Daisy met a real girl, Caitlin, whom he fancied. She is an assertive young woman and she likes that Daisy is submissive. This installment begins with a very nervous Daisy getting ready for a date with Caitlin.

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"Mom!" I called out. "Which bra should I wear?"

"I'll be there in just a minute, Daisy," she replied. "Have you attached your breast forms?"

I had attached them and I was enjoying my topless reflection in the mirror. I love how my breasts jiggle when I shake my body.

"Yes, Mom," I answered. "Can you hurry please? I don't want to be late for Caitlin."

When Mother came to my bedroom she said, "Caitlin arrived early and she's in the living room, Dear."

"Mom!" I gasped. "Now she knows I have falsies!"

"Well, Daisy, do you expect her to think you have real boobs?"

"No, Mom, but I'm super-embarrassed," I whined as tears came to my eyes.

"You need to calm down, Daisy," she replied. "Can I give you one of my Valium tablets?"

"No, Mom, I don't want a pill," I said stubbornly.

"Alright, Sweetie. Then how about Mommy's breast?"

"Yes please, Mommy," I whimpered.

Mother sat with me on my bed and embraced me. Then she gently pulled my face to her soft bosom and stroked my hair. When she kissed me on the cheek I felt much better.

While I was still cradled in her arms, Mother whispered in my ear, "How sexy do you want to look for Caitlin tonight?"

"I want to be red hot, Mom," I giggled.

"And are you still planning to wear the white lace top?"

"Yes, Mom."

"Then you ought to pair that with your black pushup bra. It'll show through and you'll be quite the fetching little minx. Caitlin will definitely want to feel you up!"

"Oh, Mom, stop it," I tittered.

The bra and top looked marvelous together! I admired my reflection in the mirror while Mother zipped me into my black faux leather miniskirt. Then I put on my kitten heel slingbacks and I was ready.

--

Caitlin stood up when I entered the living room and she presented me a lovely wrist corsage.

"You're looking very pretty this evening, Daisy," she said with a smile. "I love what you've done to your hair."

"Mom took me for my first salon appointment, Caitlin," I replied excitedly.

"That's cool! How did you like it?"

"It was wonderful! The grooming and pampering made me feel so girly inside!"

"You're girly on the outside too, if you don't mind my saying."

I love being complimented like that and my toes curled with delight!

Then Mom said to Caitlin, "You're looking handsome tonight. I love the outfit."

Caitlin was wearing a jet black Ralph Lauren jumpsuit with wide legs and long sleeves. She looked stylish and in charge.

"Thank you, Janice," said Caitlin. "I was going to wear trousers and a blazer but Mom bought this specially for tonight."

"Margaret has good taste," replied Mother with a smile.

--

Caitlin and I chatted as she drove to the restaurant where she had made our dinner reservation.

"How is your job at the auto repair place going, Caitlin?" I enquired.

"Pretty good, Daisy. I get the routine jobs like oil changes because I'm new. The boss promised that I can start doing repair work soon though. How about you?"

"I really enjoy working at the fabric shop, Caitlin. I got the job because the owner, Karen, is friends with my Mom. Karen knows that I'm a guy but the customers haven't guessed that I'm a boy in girl's clothes."

"Don't you mean 'womens clothes', Daisy?" said Caitlin pointedly.

"Yes, sorry, Caitlin. I didn't intend any offense."

"It's alright, Sweetie, I know you didn't. Besides, which one of us is really the girl?" she teased.

As we approached the restaurant Caitlin said, "I hope you like this place, Daisy. The lights are dim and no one will recognize you here."

"How do you know about the lighting? I asked.

"A guy took me here. That was before I realized that I'm not really into men, at least not regular men."

"I'm glad that I'm not a regular man, Caitlin," I said sincerely.

"Me too, Daisy," she replied with a warm smile.

When she had parked the car, Caitlin opened my door, took my hand and led me inside the restaurant.

--

After the hostess seated us, our waitress appeared and asked whether we wanted drinks. We both ordered sodas because we're only nineteen. Then we went to the ladies restroom together.

I freshened my lip gloss and primped my hair.

Then Caitlin and I gazed affectionately at one another in the mirror.

"I can hardly tell that you're wearing makeup, Daisy, but your face is so beautiful," she said.

I blushed and said, "Thanks, Caitlin, Mom did it for me. It actually takes a lot of makeup to look like you're not wearing any."

"It works for you though, Sweetie. Your skin is so radiant!"

"Your makeup is amazing, Caitlin. I've never seen you look this way."

"The smoky eyes and coral lipstick were my mom's idea. I kind of like it though."

"It makes you look mature and assertive," I said with admiration.

"Thanks, Daisy. That's quite a nice compliment."

When we returned to the dining room Caitlin held my chair as I sat and smoothed my skirt.

Waiting for our entrees to arrive, Caitlin touched my knee and then started inching up my thigh. I took her hand into mine and removed it from under my skirt.

"Naughty, naughty," I teased.

We enjoyed our dinners while making small talk. Then Caitlin paid and we departed.

--

"I know a place where we can park the car and be alone for a while, Daisy," said Caitlin.

"Okay, Caitlin," I replied. "I think I'd like that."

After Caitlin parked we moved to the back seat, and she wasted no time in kissing me. Caitlin's lips were marvelously soft and moist. This was my first real kiss and it made me feel delightfully warm and fuzzy inside.

Then Caitlin put her hand under my skirt. I was already very aroused but I didn't want Caitlin to think that I was easy. So, I begged her to stop.

"Please don't, Caitlin!" I pleaded in a trembling voice. "I'm not quite ready for that."

"That's alright, Daisy," she said sympathetically while withdrawing her hand. "Can we make out some more though, or do you want me to drive you home?"

"Would you please kiss me again, Caitlin?" I asked.

This time Caitlin parted my lips with her tongue. The penetration made me feel wonderfully submissive and my sissy feelings grew strong. Then I put my tongue in Caitlin's mouth but that was a mistake.

"Daisy, I want you to act like a girl when I kiss you," she gently scolded. "Girls don't stick out their tongues, they suck tongues," she said. Then she slapped me lightly on the cheek for emphasis.

That precious little love tap made me leak cum into my panties.

"I'm sorry, Caitlin," I whimpered. "Will you please try me again?"

This time I put my lips around her tongue and sucked. I felt deliciously feminine sucking Caitlin's tongue.

Pausing for breath, Caitlin said, "That's lovely, Darling".

When Caitlin resumed kissing me she also felt up my breasts.

"Your tits are very nice, Daisy," she whispered warmly in my ear.

"Thank you, Caitlin, but they're just breast forms," I whispered back. Then I added, "Would you like me better if I had a boob job?"

"That would be amazing, Daisy. Are you thinking about it?"

"Mom says that I should but I'm not sure. If I do it, what cup size would you like me to be?"

"You'd be really stunning if you were a C, Daisy."

"Okay, Caitlin, I'll tell Mom that I'm ready."

"You're doing this for me, Sweetheart?"

"Yes, Caitlin. Just for you," I replied with a sweet smile.

Caitlin wrapped her arms tightly around my waist and squeezed me. Her firm embrace sent delectable girly feelings cascading throughout my being.

"I'd love to have you for my girlfriend, Daisy," said Caitlin, "and I'm going to buy you a friendship ring to prove it."

We kissed again as she continued holding me tight. It was like being in paradise!

--

Mom was still awake when Caitlin drove me home.

"Well, Daisy. How was your date?" she asked eagerly.

"It was divine, Mom! I'm Caitlin's girlfriend now and guess what," I said excitedly.

"Come sit with me and spill, Daisy!"

I sat next to Mom and she embraced me tenderly. We gazed into one another's eyes for a moment before I spoke.

"Mom, Caitlin's going to give me a friendship ring!"

"I'm thrilled for you, Daisy!"

"I'm so happy that I could burst, Mom! And there's more," I added.

"What is it Daisy? Don't keep me in suspense," she said with keenness.

I took a deep breath and said, "I'm ready to have my breasts done, Mom."

"That's wonderful, Sweetheart. I'm so proud of you!"

"I've never been this happy, Mom. I owe it all to you for helping with my feminization. I love you, Mom!"

"I love you too, Daisy," she said warmly.

We snuggled together for a while. Then I said, "I'm tired now, Mom, and I'm going to bed."

"Sweet dreams, Daisy," she replied.

Then we kissed good night.

--

I went upstairs to my bedroom. There I untied the ribbon from my hair and removed my makeup. Next came my white lace top and the black pushup bra. Then I peeled off my breast forms and put them in their satin-lined case.

In bed, I lay on my back with my legs spread apart and fantasized that Caitlin was ravishing me. A wonderful sense of feminine surrender radiated from my heart clear to my fingers and toes. I experienced sissy bliss like I had never known before. My happiness grew to euphoria and I joyously creamed my cotton panties!

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Thanks for reading. More is on the way.