Sissy is Successful!

A pantywaist like me has no chance of making love with a girl but I craved pussy anyway. So I entered the Cunnilingus Competition at the college that I attended in the nation's capital. I tanked my freshman year but improved each time after that. Then I won the Golden Tongue Award as a senior!

The campus newspaper ran a feature story on me. The article pictured me in my frilly yellow party dress holding up my skirt and petticoats to reveal my chastity cage. The caption read, "Sissy Josie is no threat, ladies. He just wants to make you squeal!"

I was immediately flooded with texts from co-eds wanting my services. Some offered me dinner dates, others promised gifts and a few proposed marriage.

The most surprising message came from the Dean of Students, Dr. Margaret Andrews. She asked to meet for lunch off campus. The restaurant had a 5-star rating!

I slept in curlers the night before and then spent all morning making myself pretty for the Dean. I wore my cutest pink lace minidress, a matching choker and 6-inch heels. Dean Andrews arrived wearing a pin-striped Armani jumpsuit with a deep V neckline. I almost creamed my panties when I saw the feminine power she exuded!

The Dean smiled as she shook my hand firmly. Then she held my chair while I sat and smoothed my skirt. I was completely enchanted by this mature and confident woman. I already wanted to lick her coochie!

Dr. Andrews asked about my college experience while we waited for our entrees. I told her that I was majoring in Women's Studies and that I hoped to be a woman myself some day.

"That's nice, Sissy Josie", she remarked. Then she asked, "Do you have any plans for after you graduate?"

"I'd like to be a secretary or a personal assistant to a woman," I replied.

"That's not very likely though, is it Dear?" she said skeptically.

"No. I guess not," I admitted.

"Have you considered using your tongue to earn a living, Josie?" she asked.

"I hadn't but it's a great idea, Dean!" I said excitedly. "How would I get started?"

---

Dean suggested that I perfect my cunnilingus skills with her help. I began meeting with Dr. Andrews at her office on campus every day. I took my place under her desk and she helped me to make her climax by giving feedback and directing my oral stimulation. We made a lot of progress and her orgasms increased from 1 per session to 5 over the weeks before classes ended.

As a graduation present, the Dean bought me a bikini swimsuit and took me to Bermuda. We stayed in our luxury hotel room most of the time and ordered room service. I gave her orgasms morning, noon and night. On the flight back home, she said I was ready to take on paying clients.

Dean Andrews was a socialite and I adored the sophisticated women that she solicited. Most were wealthy ladies who wore stylishly sexy clothing from famous makers. Dean introduced us over tea at her home and then showed us to the private room she had furnished with a lovely canopy bed and satin sheets.

I loved unzipping the ladies and seeing their luxurious lingerie. Lacy bras and panty girdles were my favorites. I couldn't wait to lick their professionally groomed pussies framed by elegant garter belts and Parisian stockings. Many of the women used fruit flavored douches that were an extra treat. I became an expert at sending my clients into rapture with my tongue. Their euphoria resulted in generous tips which I used to buy sensual intimates for myself!

My fame as a pussy licker and a giver of orgasms grew by word of mouth. Then one day, Dean Andrews dropped a bombshell on me at breakfast.

"The First Lady wants your services, Sissy Josie."

I was so stunned that I dropped the half grapefruit I was eating.

On the appointed day I was driven by limousine to the White House and taken in through a secluded entrance. A female Secret Service agent ushered me into the First Lady's private suite and ordered me to undress. I wasn't wearing much to begin with but I stripped naked. The agent put on nitrile gloves and inspected my mouth and my boy pussy. Then she allowed me to put on my lingerie and my dress again and told me to wait.

I was nervous about meeting such an important woman as I stood in her quarters. A short time later a woman I didn't recognize entered carrying a large black butt plug. She introduced herself as the First Lady's chamber maid.

"The First Lady wants you plugged and kneeling when you service her," she stated plainly.

I could hardly refuse such an order from on high, so I dropped my panties and bent over. The maid lubed the plug and pushed firmly against my bottom. It slid smoothly inside me when I relaxed my sphincter muscle. Then she had me kneel by the bed.

"Thank you for your cooperation. The First Lady will be here shortly. Keep your eyes on the floor and do not look at her."

The door opened and I heard the First Lady's high heels click-clack across the floor to the rug where I knelt. I smelled her lovely floral perfume as she sat on the bed in front of me. The First Lady was wearing an evening gown with two slits and a center panel. She pulled aside the panel and I feasted my eyes on the lacy merrywidow, embroidered garterbelt and sheer nylons she was wearing.

"You may unsnap the crotch and begin, Sissy Josie," she said.

She called me Sissy Josie! She knew who I was!

When I opened the garment's crotch the wonderful musky aroma of the First Lady's pussy overcame my senses. I fell in love with the august lady immediately and I wanted to give her the best orgasm of her life!

I began by licking her labia. She moaned and then pressed my face deeper into her glorious snatch. As I gently licked her clitoris the First Lady's breathing quickened. I continued licking and carefully inserted my middle finger into her pussy. She gasped when I located her G-spot and then climaxed in an explosion of female splendor.

I expected to be dismissed at that point but the First Lady pulled me up onto the bed. Then she got on top and fucked me!

---

The limousine returned me home to the Dean and I told her what had happened.

"Did she at least put a rubber on you, Sissie Josie?," she asked in disbelief.

"No. I went in bareback," I replied.

The First Lady requested more visits and I was happy to comply. She didn't even want foreplay after the first time, just my seed. Then she invited me one last time and told me that she was pregnant with my child. She kissed me on the lips and thanked me for my service. I fainted and her chamber maid had to revive me with smelling salts.

---

Nine months later the news media reported that the First Lady had given birth to her first child. The chamber maid came to our house and informed Dean Andrews that I would receive the Presidential Medal of Freedom for service to the country!

Dean was so impressed that she took me to the canopy bed and ravished me. She fucked me every day after that until I made her pregnant, too!