Miss Guided

I raved at his appearance and flattered him.

"Charles, you are a perfect sissy. A sexy, sultry, fabulous girl. Isn't this so much fun?"

He replied, "Dr. Em I love this. I just love it."

I replied,

"Yes, you a the prettiest sissy I ever saw...but those shoes...those kitten heels have got to go! They don't go at all with the rest of your outfit. You know, looking the way you, I can't continue calling you Charles. How about if I call you 'Charlene?'"

It has been about two hours and I heard Susan's car in the driveway. I met her at the door and prepared her to meet Charlene for the first time.

"Susan, don't act shocked. Just act normal. Charlene and I have been making a lot of progress while you were out.

Susan entered and saw Charlene and very non-chalantly said,

"Oh, Charlene, such a pleasure to finally meet you. I love your dress. What nice earrings. You look lovely. By the way, I picked up some nice pumps for you. I think they will go fine with you dress."

Charlene was beaming as he slipped into his new pumps with the 4 3/4 inch heels. Susan then said,

"You know, Charles, it's a very big day in a young girls life when she wears her first pair of high heels, so I know this must be a very big day for you!."

Charlene beamed with joy as she admired her legs in the mirror. And she said, "I love the way my legs look in these heels."

Dr. Em agreed saying, "They look fab, honey, and the heels also perk up your cute fanny in that tight dress."

Dr. Em then told Charlene to go upstairs and practice walking in his new spike heels.

During this time Dr. Em explained that the tests she had administered thus far gave her the impression that Charles could be a sissy.

Since seeing him as Charlene, a real knockout diva, I couldn't much disagree but I replied,

"It could also be merely an elaborate fantasy like a costume ball or Halloween party."

"I'm not through yet, Susan, I have a two or three more practical exams that will guide my final evaluation and diagnosis to Dr. Cooper. We'll have our answer tomorrow I should think." she replied.

We continued to chat and the doorbell rang.

Dr. Em said, "That must be the pharmacy delivery. Ask the delivery guy his name. If it's Jimmy, open the door."

It was a guy named Jimmy and he had "a prescription for a Mr. Charles Baker."

I told him that I would take it but he wouldn't give it to me and said that Charles had to sign for it. Something about notice and having been advised of contraindications I called out "Charles, could you please come down here."

Charlene appeared at the top of the stairs and descended the staircase like a Hollywood actress. She strode over to Dr. Em and me confidently in her new stiletto heels, not even noticing Jimmy standing, mouth agape, in the corner.

"Jimmy needs you to sign something."

Charlene sashayed over towards the young man and said in a very breathy voice, "Hi Jimmy."

Jimmy looked at Dr. Em and me and asked,

"This is Charles?"

I replied, "Yes, but in this dress he's Charlene."

Jimmy responded,

"You mean she's a man?

Dr. Em answered, Well, he's not a real man. He's a sissy."

"My God, she sure fooled me." he said.

"Do you find her attractive? Do you think guys would want to have sex with her?" she asked.

"Hell yeah, he responded enthusiastically, "I know I do."

At this point I interrupted with, " There will be no having sex with my husband."

Jimmy said, "You mean you're married to this fairy? Well, how about a blow job? Sissies are famous for that. That's what sissies are for."

Dr. Em interjected, "Sissies are known to be excellent at oral sex, you know, Susan."

I replied, "She wouldn't even know how to suck cock."

Dr. Em said, "Well, she has had pussyboy training and should have the right oral and lingual skill set. I could instruct him and would recommend this exercise, as the results will aid in my evaluation and report to Dr. Cooper."

I agreed.

Dr. Em said to Jimmy, "Jimmy, I don't have any cash on me to give you a tip but if you make yourself comfortable on the sofa Charlene will give you a blow job. Come here Charlene."

Dr. Em very sweetly said to Charlene,, "Now pay attention, Sugar, listen to my instructions and follow them.

"Kneel here in front of Jimmy. Be careful with your nylons as you kneel.

Now, pat his crotch gently as you look into his eyes and smile.

That's it. Do you feel where his cock is? Good.

Now, very quickly un-do his belt buckle, open the pants button, un-zip his fly and pull down his pants, underwear and all.

Do it quickly. This shows him how eager and hot you are to suck his cock.

Now what a nice cock he has. Take it in your hand and give it a slight squeeze and then fondle his balls with your other hand.

Very Good, Charlene. Now I want you to kiss it. Shower it with kisses up and down. Do you see your lipstick on his cock? That's your lipstick because you wear lipstick now. Sissies always wear lipstick. Now I want you to lick your man's cock. Yes, good girl, up and down. Do you feel it grow. Look how stiff it is now. That's the sign that it's ready to be sucked. Put it in your mouth and suck it. That's it. Swirl your tongue around it. Now bob your head up and down on it. You go girl. Suck that cock. Think about how you are wearing a dress and makeup and heels and nylons and have a real man's cock in your mouth. Do you feel it throbbing? Feel it pulsating on your tongue? Keep sucking, doll-face. He'll be coming real soon. You must catch all his cum in your mouth. If there's a lot you must swallow it quickly. Be ready..any moment."

Jimmy began to buck and moan and Charlene gagged.

Jimmy came all over Charlene's face.

Just then Jimmy's cell phone rang. It was the store informing him that he had to pick up another prescription right away.

He hurriedly pull up his trousers and said, "Good bye ladies. I have to run. Thanks for the blow job, Charlene,"

He left.

As Charlene knelt there with cum on her cheeks, cum on her mascara'd eye lashes and dripping down her chin, I said, "You know Charlene, it's a very big day in a young girl's life when she sucks her first cock. It must be just as big a day for a sissy."

Dr. Em then told Charlene, "Charlene, now you understand why I told you to swallow quickly. If you don't... you get your makeup all splashed

Also, men like to have you swallow. Some are insulted if you don't. Now, go wipe the cum off your face and re-apply your makeup. Your lipstick is all smeared."

While Charlene spent the next 20 minutes doing that, Dr. Em told me that she would prepare her evaluation and give it to Dr. Cooper in the morning.

She also said that Dr. Cooper's office would contact me to arrange the next appointment.