Frustration of Small Cock Pt. 03

Story Info
Continuation of Frustration Small Cock with a twist.
3.1k words
4.28
27.6k
11

Part 3 of the 7 part series

Updated 06/09/2023
Created 10/13/2018
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jamtby
jamtby
296 Followers

After 30 minutes under a warm blanket, I felt it being pulled away and I was once again laying naked in the room Liz smiled and said, "Ok Amiee, it's time to get you ready for a debut. Let me introduce you to Lisa."

A strikingly, attractive women approached my bed and smiled. "Hi Amiee, my name is Lisa and it is my responsibility to help form your persona as a female. Let's get started. Please move to the make-up chair."

I got to my feet and walked to the chair to the right of the massage table that had been the place of my erotic experience only a half hour earlier. Moving behind the chair Lisa started her work.

"Okay Amiee, I am going to show you some pictures and you tell me which ones are most pleasing to you and which one you would like to become, Ok?"

As I shook my head affirmatively, the flat screen TV lite up and images started to appear. The first was a woman in a French maid uniform.

Lisa asked, "Is this the image of your persona?" I said, "No that's not me."

Then the next picture of a slutty woman dressed very provokingly, then the high school cheerleader, a policewoman, a doctor, and college sorority girl. None captured who I wanted to be looked upon. Finally, a picture of Kate Middleton was shown.

"Lisa, that is the look I like and want to project." Smiling she said, "That is terrific. Most of our clients like the French maid or cheerleader. Only a few like the classic, professional look. That has some additional advantages you will come to appreciate."

"Liz we will need to perform the classic transformation for Amiee. I think she is best a Burnett with shoulder length hair. Work on those eye brows to make them more feminine. Be certain to shave her arms. I see you have gotten her nicely shaved and smooth."

"As for clothes, thigh highs, white thong, white bra, a coat dress like the one Kate Middleton wears, make-up, and 3-inch heels. Amiee will need to learn to walk in them."

"Guy is having a party at his place tonight and Amiee should make her debut. I am certain she will be warmly received, and Guy's guests will find her irresistible."

"Amiee, I will be at Guy's house and introduce you around and help you feel comfortable. You will have an amazing time."

With that Lisa left the room. Liz and a several women went to work as ordered.

"Liz, who is Guy?" Liz just smiled and said he is your benefactor and sponsor. You will like him, and he will make your life much different and better."

The transformation process took move than an hour as I sat naked in the chair and three women worked on me doing nails, eye brows, make-up and following every recommendation or were those orders that Lisa had given. I was starting to feel very vulnerable sitting there naked as others touched and worked on me. Finally, a Burnett wig was placed on me and brushed to look soft.

The chair was turned around facing the mirror. "Okay Amiee, look."

Reflection in mirror was someone I had never met. A very attractive woman sat looking back at me. All I could think was who was that person?

"Okay, Amiee, time to get you dressed. Although I prefer you naked, you can't go to a party like that at least not when you first arrive."

With that the clothes ordered by Lisa were brought out from a room in the back. Putting on nylons required some education from Liz, but she showed me how. Then the panties, bra, coat dress and matching blue shoes. "You may wonder how we have your size shoe? We have sizes 9 through 13 in every woman's shoe you can imagine." Liz said with a smile.

"I will need a size 12", with a bit of a smile on my face.

"Take a good look in the mirror you look amazing Amiee." Looking at myself in the mirror I was both pleased and a bit uneasy. Is this what I really wanted?

Liz said, "I need to help you learn to walk in heels. These are only 3- inch heels but eventually you will be able to wear sexier 5-inch ones. Now hold my hand and let's start to work."

The first wobbly steps proved to be challenging but with Liz's help I gained confidence and became reasonably comfortable walking in them.

"Okay Amiee, my work is done for today. During our next session you will learn how to perform the entire transition by yourself. That will happen tomorrow. In a few minutes a driver will pick you up and take you to Guy's home. You will enjoy the evening."

Within a few minutes a chauffeur arrived asking Liz if his passenger was ready.

"Yes, she is, and you make certain she gets to Guy's home in perfect condition." With that Liz gave me a hug and I was on my way out the door.

"By the way, don't worry about your car being here no one will bother it we have security to ensure that."

As chauffer opened the door to the back seat and let me get in. Within a minute we were heading west Gandy Blvd. I was very nervous not knowing what was ahead or if I was really Amiee, but the excitement of the moment was so strong I didn't really care.

In about 20 minutes we crossed the Bellaire Causeway. At Gulf Blvd the car made a right turn past some very large and beautiful beach homes. With a left turn we passed the open drive gates and arrived at the front on the mansion. Unaccustomed to having someone open my door the chauffer said, "Please wait miss, let me open it for you."

Stepping out of the car I entered the portico. Lisa was there to greet me.

"Welcome to Guy's home. Let me introduce you to our host."

Standing a few feet inside the door was a distinguished looking gentleman in his 60's. He had a dignified presence and a warm smile.

"Guy, I would like to introduce you to our newest client Amiee. She became a friend of Alex who has invited her to participate in your program."

"Amiee, I very pleased to meet you and glad you one of our new clients. I would like to chat with you for a few minutes but must greet the rest of my guests" "Lisa would you take Amiee to my office I will there in a few minutes."

Guy's office was beautiful with a great view of the Gulf of Mexico and the finest of furnishings. Lisa asked me to sit in a chair facing the Gulf and wait.

"Guy will be right in to visit with you. Would you like a drink while you are waiting? Perhaps a glass of wine?"

I replied, "That would be great a red Merlo would be great". Within a minute a person dressed as a French maid brought in a glass of Merlo. Guy followed very shortly after she left.

"Amiee, I have learned a great deal about you from Alex and my good friend Tim. We have been together for a long time. I know that most of our clients wonder why any would sponsor a program like this one. Over my life I have been cursed with a small penis. It has caused me much frustration and humiliation. Many men suffer from this problem but most only suffer in silence or engage in unhealthy activities.

Four years ago, I decided to help some who suffered and felt that perhaps they sexual identity was not what their anatomy dictated. So, each year I sponsor three candidates recommended to me by Tim and Alex. You have been selected to participate. I can see this was a good decision by Tim and Alex.

Ove the next 12 months you can experience a full range of feeling that a woman might feel and enjoy an alternate lifestyle that is based on a confidential understanding that no one will know your real identity. At the end of the 12 months you can decide if this is a way of life for you or whether you want to resume your old life. That decision is entirely yours. If you choose to continue, I can help pay whatever expenses you might have to fully make the transition. For example, laser hair removal has often been requested. I will pay for that. Some have gone as far to request reassignment surgery. I can arrange that as well through a quality medical organization. In the end the decision is yours.

We need to join my guests. Some of them are clients like your others are friends who enjoy "special times with special friends" there are no judgements here. So, let's go and meet our guests."

With that Guy took my arm and lead me into a very large living room. There were 12 people chatting and drinking wine. "Ladies and gentlemen, I would like to introduce Amiee my newest client. Please make her feel welcome."

As the evening progressed I met all the guests and Guy's clients. I recognized Lori from our meeting at Tim's place. It took her a minute, but she finally recognized me.

"Hi, Amiee, I am glad you decided to take Alex's invitation and join us. You will find this very rewarding. It won't be long before the guests will ask us to join them for personal time alone. There are many fine people here and I can guarantee you that you have a very exciting time." This was Lori's way of telling me there will be sexual activity.

She also warned me, "You see that tall woman with the pulled back hair, dark make-up, and leather outfit? If you can avoid being invited by her to her room, do so. She is a self-styled domminix and very demanding. Her name is just Ana and she could have worked for the SS."

Within a few minutes of Lori's advice, standing in front of me was a 6-foot woman in her early 50's with pulled back hair and dark make-up. "My name is Ana and Guy told me you were new to the group. I want to take you for some private time in my room come with me."

We walked up a flight of stairs, through a dimly lighted hall into a bedroom overlooking the Gulf.

Ana said, "This is my special room and what I say and want happens here. Girls like you don't object to my orders and I am in control. So only speak when I tell you to and do what I want."

I sloughed and shook my head in agreement. It was clear this woman had some issues and I hoped she wouldn't go crazy.

"Take off your dress now but leave you shoes on." That was the first somber order. My earlier conversation with Guy seemed to indicate everything would be okay so I obeyed. I slowly unzipped the dress and let it fall to the ground.

With a smirk she said, "You look pretty good, but I want to see your tits so take off the bra now and rub them for me."

Without hesitation I obeyed and started to rub them as she ordered. It was strange rubbing my breasts with a woman in the room.

"Very good now take off the panties and make it quick." I again did as tell and was standing there like so many women I seen in porn pictures wearing only nylons and heels.

"Come over here. Suck this butt plug for me." Why was I doing this perhaps I should run out of here, but I obeyed. Sucking the butt plug seemed to please her.

"Turn around and bend over." I knew what was coming within seconds the tip of the plug pushed against my anis and then it was pushed inside me.

"Keep that in you" was the next order. Ana was getting some sort of pleasure from the humiliation as I squirmed.

She then started the verbal humiliation. "I am rich; I am powerful; I control you; and I can do whatever I want."

At this point it appeared she had control, but things were about to change due to an unexpected accident. Lori, had shared with me that Ana always wore a leather bra that was cold. To anyone's knowledge no one had ever seen Ana's breasts. That seemed like a small, insignificant thing at the time. Then she ordered me to turn around and face her. Her cold hand reached for my cock and balls.

"You know you don't need these anymore." She started to squeeze then, and an intense pain almost overcame me. At that moment for entirely unknown reasons her bra clasp broke and the bra started to slip exposing her right breast. For reasons not clear at that moment, I reached out and started rubbing her breast.

It was like someone turn a switch and Ana became very increasing aroused and horny. Rather than being her submissive the tables were turned. It became clear I could control her by simply rubbing her breasts. Pulling the bra off her shoulders I continued to rub her right breast then she left, and she became very aroused and I could tell she wanted more.

"Ana, I am going to take control of this room so strip off your clothes and do it quickly." Not taking any chances I continued to rub her breasts and play with her nipples. The leather pants she was wearing slid down her long legs.

"Get your panties off and get rid of the shoes". That was my next command and to my surprise she obeyed with only slight hesitation. It seemed her breasts were so sensitive that simply touching them caused arousal.

I pulled the butt plug out of my ass. "Now turn around and bend over." She pleaded not be have a butt plug but that didn't stop me. I popped into her as she moaned.

"Now lay down of the bed." As she did I joined her and started to suck her nipples which only caused her to get more excited and moan. She suddenly started to shake and have a spontaneous orgasm. I had never seen that before. She continued to moan and cry like someone had released her from prison.

In a low soft voice, I asked, "Ana you are a beautiful woman and I have unlocked the chains that have held you. Now let me take you further."

"With a soft smile and pleading look she said, "Please help me."

Gently rubbing her breasts and belly the "bitch switch" had be turned off. Ana become a kitten wanting only to be loved.

"Ana, if you are willing to trust me and spend the weekend with me, I believe I can make you a very happy woman. Are you willing to see where we can go together?"

I had changed from girl back into a man even though I was still dressed (only partially) as a woman.

Ana could only say, "Yes, please give more of what you have just given me."

While Ana lay naked and exhausted on the bed, I pulled my cellphone from my purse to call a friend.

On the third ring a familiar voice pickup. "Dave this Jim do you have minute?"

Dave responded, "Sure, I am at the airport catching a flight to Michigan, but the flight was delayed due to bad weather around Detroit. So, what new right."

"I'm glad I caught you. I would like to borrow your place at Paradise Lake for the weekend."

He replied, "Sure you can I will be gone for two weeks anyway and it will be empty. I will call Jason, my neighbor who looks after the place and let him know you will be there for the weekend. You will need my gate code 3464 to get in. The key is under the flower pot on the porch, but I could leave the doors unlocked. Tomorrow I will call the Club manage and let him know you will be using my membership. "

"Great, thank you I plan to go there tonight if that's ok with you?"

"Sure, enjoy yourself. I finally am getting you to enjoy life a bit. You Buckeyes are a bunch of tough but worthless nuts. Go Blue!"

"Thanks and have a great trip. I look forward to seeing when you get back. As we say in Ohio "Go Blow. Talk with you when you get back."

I spent another 30 minutes rubbing Ana's breasts and stimulated her pussy. After a second orgasm I said, "In a few minutes I want you to get dressed except for that damn bra we are going to spend the weekend together, so we can learn more about each other."

Ana said, "Ok but where are we going and what do I need to take along?"

I replied, "It will be a surprise and you won't need to take anything. We will pick up what we need on the way."

Looking a bit confused Ana stood up. "Can I please take this butt plug out before I get dressed?"

"No, bend over I will take it out." This was an act of control. She bent over and after a moment of stroking her lovely ass, I pulled it out.

Ana started to get dress and still was unsure why or where she was going. I put my dress less the bra back on. Once we both were dressed I opened the bedroom door and we headed down to the living room.

Guy was standing there talking with several guests as we approached. He turned and smiled.

"I hope you have had a good evening and enjoyed each other's company. I replied, "Yes we did very much."

Ana just smiled. Guy looked at her and said, "Ana you seem a bit different and more relaxed. I am happy to see that because you are the hardest working employee in our company."

Again, smiling she said, "Thank you Guy for your confidence and support. Yes, this was a special evening. Amiee and I are going to take a trip together, so we can get to know each other better."

"Where are you both going?" Ana replied, "Amiee says it is a surprise and I will be very relaxed after the weekend."

Guy smiled, "Have a great time together. I will have Charles bring your car to the portico."

With one call on a house phone Charles was summoned and quickly pulled Ana's black 550 CL Mercedes up to the portico. Ana got in the driver's side while Charles held my door.

"Ana when you pull out on Gulf Blvd turn right then at the traffic light turn left onto the Bellaire Causeway.

To be continued

jamtby
jamtby
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UltimateHomeBodyUltimateHomeBodyabout 5 years ago
Need to proof read

The dtory is okay although seems to jump at times as you have trouble traversing ideas.

Silly mistakes make it hard to read, requiring going back over parts to find what word you meant. These chapters are so short you should be able to read ypthese yourself to find these errors. One sugfestion is to use text to speech software and let tbe computer read it to you. It does work as you follow the text as it reads.

jamtbyjamtbyover 5 years agoAuthor
Experienced Manager of Multiple Projects

I can not give you any real advice. You might try shaving to see if it provides you any erotic pleasure. I have found that it does for me but that is only a personal experience. Good luck.

There is more to come stay tuned. Thanks Jamty

betabradbetabradover 5 years ago
Interesting stories

I find your stories very interesting and relatable I also have a small cock ( actually , I feel ashamed calling what I have a "cock", I call it a "dicklette" or "sissy dick") , I have low testosterone and also can't achieve a full erection anymore. I know I can't satisfy a woman and I wonder if your story is what I am destined for. Is my destiny to become a sissy ? What role , if any , do I have in sex with a woman ? Should I also shave my dick ? Shave my legs ? Wear panties ?

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