Changing Attitudes About Sex Roles

Brandy was now becoming a bit more assertive. "Baby, I know it was a long time ago but we have got to figure this out for your sake. We will talk about it some more later."

Once inside the house Brandy pulled out the cards. She said, "Let's agree on the rules. Five card stud, three hands the winner must take two of the three wins. The winner decides what the loser must do tonight. If you win, you will be able to have me do whatever you want. Do you agree?"

I replied, "Yes, I agree and you should be ready for my demands."

Brandy just smiled, "You have to win first and I am lucky at cards. You deal the first hand."

The first hand I won with a pair of 10's while Brandy had nothing. Dealing the second hand I felt confident that I would soon be in charge. Unfortunately, Brandy held a pair of kings beating my pair of 6's. It was down to the third hand. I became a bit nervous.

"Ok baby, we are down to the moment of truth. One of us will win and the other will submit. To put some additional pressure on this last hand, what do you plan to do with me if you win?"

Smiling I said, "I am going to tie you to the bed and fuck you doggy style and then make you sleep naked."

Brandy replied, "You know that would make me scream because I don't like to be restrained. Sleeping in the nude I don't like either, but I would do as you wish."

She continued, "If I win you are going to become my lesbian lover for the night. You will property dressed, fondled, undressed and then fucked in the ass like a good girl would be."

I replied, "That sounds terrible. I am not a woman so how can I become your lesbian lover?"

Brandy said, "The difference between being a woman and man is not between your legs, it is the illusion that is created and the mental control your partner has over you. If I win you will become Jane and not Jim. You will want me like a woman wants another woman."

I responded, "That sounds pretty scary. But I am going to win so you can count on waking up nude in the morning."

I cut the cards and Brandy dealt. She held her 5 cards and I asked for 2. Then the moment of truth. I held a pair of jacks. Brandy held her cards for what seemed like an hour.

"Ok, Jim take off your clothes you are now Jane for the night." With that she put her cards on the table. There were 4 aces. She had won again.

"You heard me get those clothes off and follow me."

I started to protest but Brandy cut me off. "You agreed and you are now mine to use tonight. You are now Jane and will become a lesbian lover. No more complaining, do as you are told."

The assertiveness of her voice told me this was going to be a serious experience. I reluctantly stripped and followed her into the master bathroom.

"Stand in front of the shower. I am going to make certain your body is hair free like a woman's should be. I know you have been shaved, but this will make you smoother and free of all body hair."

She smeared this green stuff all over my body. My arms, arm pits, chest, legs, pubic region and finally my ass. This stuff smells a bit like pickles.

After standing there for 10 minutes Brandy ordered, "In the shower Jane and wash all that goo off of you. I want you hairless and smooth."

I obeyed and within about 3 minutes I stood there totally hairless. While the shaving had made me feel free, this was a total removal. I had not been this naked since I was born.

"Ok, Jane, get out dry yourself and sit on the side of the bathtub"

The cold tub on my bare ass felt somewhat erotic as I sat there waiting for what was next.

"Okay, Jane, I am going to put make-up on you and make you very pretty. Just sit still and let me do my magic."

It took almost 20 minutes but soon I had complete make-up including eye brow trim, lip stick, and a much different looking face, Then the wig came out from under the counter.

"Jane, you are going to be a brunette today. I think you look best that way. Besides it goes well with your hazel. eyes."

Looking in the mirror I didn't recognize myself. In fact I thought I looked pretty good.

"Let's get dressed. But before we do Jane has to restrain her male appendage. You need to cage it for tonight."

Before I could protest Brandy said, "This will only be worn for a little while tonight. I don't want an unexpected erection to give you away."

Within a few seconds the cage was slipped over my throbbing cock and locked. I felt the restraint and knew Brandy had something planned but would not tell me.

"Jane, don't worry, it won't hurt your little man and besides it will only make you more excited once I release you. Now its time to get dressed"

With that she handed me bra, panties, nylons, a garter belt, and a nice dress you would wear to a party.

I was told how to put each article of clothing on and in what order. Panties and bra first, Then the garter belt followed by the nylons which Brandy helped me put on and finally the dress she pulled over my head.

"Jane you look great. Go and look in the mirror"

Except for the restraint on my cock, I liked what I saw. I was a pretty attractive woman. That was definitely against what I have always held about the different sexes.

As I was admiring my new appearance, Brandy had changed into a more feminine dress.

Returning to the bedroom she handed me a pair of women's flats. "I know you wear size 12 so I found these for you to wear tonight. I wanted to have you wear heels but thought you would have trouble walking in them tonight. We can save them for another time. I think you would look absolutely beautiful wearing just a pair of heels and black nylons. A real turn on."

Now the imagine of me dressed like that flashed through my head. It seemed stupid but I had seen pictures of women dressed that way an it was a turn on. What about tonight?

"Jane are you ready to leave?"

My thoughts quickly went to leave? I asked, "What are you talking about I thought you wanted me as your lesbian lover for tonight and that you wanted to make love to me?"

Brandy replied, "I do and I will this is part of my evening. You and I are going to Baxter's, it is a bar where lesbians have fun and make connections. I want you to have the full experience, besides you look far to pretty to just sit in the house and let me ravish your body. So get in my car I am driving."

I did not want to go out in public dressed like this. Someone I know might see me and this could be a disaster.

"Don't worry no one will know who you are. My biggest concern is that some other woman will want to hit on you and take you home."

After a few more moments of hesitation, I agreed and got into the car. Why I did not know but I did.

It only took 20 minutes to drive to Baxter's. Before entering Brandy said, "Let me do most of the talking. If a woman hits on you or tries to feel you up, let me handle the situation. Ok?"

I quickly agreed.

This seemed like a friendly place. The only males were the bartender and waiter. The place was busy, but we found a table in the back. Brandy ordered two glasses of white wine and we sat there watching the crowd. Brandy was quick to point out a "bull dike" who was trying to pick someone up.

I asked, "How do you know some much about lesbians"

She smiled, "It was my master's thesis. The differences between dominant men and lesbians. You would be amazed that there are almost no differences in their mind sets, desires and the way they pursue more submissive types. The only real difference is their biological plumbing. Dikes have options to even eliminate that. It is very interesting."

"I didn't know you had a master's degree. Why are you working in insurance claims?"

Brandy replied, "It comes down to financials. As a psychologist I would earn around $60,000 a year. As a department head in claims I earn close to $100,000 and chances for future income growth. Besides, there really isn't too many real differences between dealing with people with psychological issues and insurance claims. Both people are upset, don't like what you tell them, and like to threaten you. At least in the claims business I usually can give them some money which helps reduce their anger."

The band started to play and women began to dance with one another. "Jane, do you want to dance?" Brandy asked softly.

I agreed and we moved onto the dance floor. It was different dancing in a dress. I did discover that my ass felt exposed in the dress. After a few minutes an older woman cut in asked if Brandy would dance with her. She agreed. "Jane, I will meet you back at the table."

After picking my way through the crowd I finally returned to our table. In a minute or so a tall, strong looking woman approached and sat down without an invitation.

"Hi, my name is Jean what is yours?"

I tried to be coy but whispered, my name is Jane.

"It is nice to meet you. I couldn't help but notice you on the dance floor you looked fabulous. Do you come here often?"

I responded, "No, this is my first time."

She continued, "This is a great place to meet new people who have similar likes and dislikes. How long has it been since you came out of the closet?"

Now I didn't know what to say. Where was Brandy when I needed her. I just smiled.

"Oh, I understand. Is the woman you are within a relationship with you?"

I shook my head in the affirmative.

Jean continued, "I know how nice it is to have a beautiful relationship. Sometimes it makes a relationship even better when you can get other experiences that will further cement the one you have. Ever thought about seeing another woman?"

I whispered, "No, I am quite happy with the one I have, thank you."

Jean continued, "I know you must be very happy together but if you ever need someone to talk with or get some advice, I am always available."

At that point Jean put her hand on my shoulder and began rubbing it gently.

Jean continued to talk in a low soothing voice. "I have helped many women who need to feel the love of another woman. I am able to relax them and make them release all of their inhibitions and freely express themselves. Some are like you who are relatively new to this way of life"

She continued to rub my shoulders and was ready to kiss me when Brandy returned.

Brandy said, "Hi, I am Brandy and who are you?"

Jean replied, "HI, I am Jean. I was just talking with your friend. She seems very nice."

Brandy replied, "Yes, she is. We are lovers and enjoy being together."

Jean replied, "I think that is wonderful. I enjoy meeting people who have a great relationship. Sometimes a third person can make it even more fun. Have you explored that experience?

Brandy replied, "No, it does sound erotically interesting but I don't think tonight would be a good time to explore a threesome."

Smiling, Jean said, "I know timing is everything but perhaps sometime in the future the three of us could get together at my house and have dinner and explore."

Brandy smiled, "That would be fun sometime. Where do you live?"

She replied, "I live in Westchase not far from the Publix."

Brandy laughed, "You know we live there too. It would be easy for us to get together."

Jean replied, "Perhaps you would consider stopping by tonight for a night cap. It would give us a chance to get to know one another better."

Brandy hesitated and looked at me. "I don't think that would be a very good idea. Jane needs to become more comfortable with her role. Besides you are so close."

With that Jean gave Brandy her address. It was very close to my house.

Jean was no more than a few steps away when Brandy said, "Jean, if your invitation is still open Jane and I would love to stop by for a few minutes tonight."

Turning around Jean smiled, "I will see you soon then at my place. We can have a drink and you will be on your way home."

Brandy shook her head acknowledging Jean's comment.

As we got ready to leave the bar, I said, "What in the hell are we doing. You know this woman wants more than a night cap"

Brandy replied, "Yes, I know but I will control what goes on. It will be a unique experience for you that you might otherwise never get. Remember, I won the bet tonight."

The 20-minute ride back to Weschase seemed like it only took a minute. I was very nervous and wanted to go home but Brandy was insistent and in control...

"You know most men never get the chance you are getting tonight. You can watch a real lesbian Dike try to control the night. The game I will play will make her frustrated because she won't get to first base. Just watch, you will enjoy the show."

Still not having a good feeling about the entire thing I said, "Brandy, I think this woman can get us to do things we never would have imagined. She is good and seems to have a very persuasive way of getting what she wants. Case in point; we are stopping by her house. That wasn't in our plans for the evening."

"Baby, don't worry. I have this under control and in fact I am certain she will do what I want rather than the other way around."

Within a few minutes we were standing at her front door, Brandy rang the doorbell and we waited. It seemed like a long time but only was a minute or two.

Brandy commented with a chuckle, "This house looks similar to yours. That should make you feel more comfortable knowing were all the doors are located."

The door swung open and Jean stood there smiling. "Welcome to my home. I am so happy you came to visit.

She ushered us into the family room which was beautifully decorated. AS with my house there is a fireplace on the back wall. Unlike my house about the fireplace was a painting of a nude woman. It added some strange erotic touch to the space.

Jean asked .What would you like to drink? I have wine, beer, and if you like rum I can make a mean rum punch."

Brandy chose the wine because no one can predict what a rum punch will do to your senses and inhibitions."

Soon a bottle of white wine was brought out and we all started to drink. At that moment I noticed Jean had changed out the clothes she wore to Baxter's and into something you would lounge around the house.

"Brandy, tell me about yourself."

" I grew up in Michigan near Ann Arbor. So naturally, I attended college at the University of Michigan. I continued and earned a Master's degree in psychology and started working at Henry Ford Hospital. It soon became clear that I could not make the type of money I wanted so I looked for some options. A former patient worked for a major insurance company and invited me to become a claims representative. I have since become the department head of that operation here in Tampa.

I was briefly married to a guy I met in college. We got along well but his interests were in drugs and their distribution. On a trip to Detroit he was shot by a rival drug dealer and died a week later. After that I just drifted through relationships. The right person never came along. Then while arguing with the sales manager from the Tampa office over a claim, I fell in love. He has been the love of my life ever since. We have fun together, he listens to me, and even does crazy things like becoming Jane for the evening. He put joy back into my life"

Jean replied, "You are a very lucky woman. You need to make certain you keep him happy. There aren't many guys like him."

Smiling and looking at me Brandy replied, "Yes, I know that to be a fact. Tell me about yourself."

Jean started, "Like you I was born in the Midwest, Indianapolis specifically. My childhood was rocky as my father and mother fought all the time. I won a scholarship to Purdue and like you I majored in psychology. While in school I fell in love with an engineering student who was very intelligent. His first job out of school paid him $75,000 a year. That was unheard of at that time. We have two children one lives in New England and the other California. At some point my husband decided he preferred men to me, and we were divorced. I discovered I preferred women and have developed a talent for helping them especially those who are repressed so they can release their inhibitions. Thanks to a very good divorce settlement, I only work when I want to on projects I like..

Brandy responded, "You sound like you're a living a happy life."

Jean responded, "For the most part. I do enjoy the freedom to make new friendships.."

She continued, "When I saw Jane at Baxter's I knew she was special. After spending a few minutes with her I know she was a "virgin" at all this and very nervous talking with me. When you returned to the table, I felt a giant sigh of relief come over her. You are her protector."

Brandy smiled, "You know there is something you need to know about Jane."

Without hesitation Jean responded, "Brandy, I already know that Jane is in fact your male lover. She is very attractive, but I have been around a long time and can sort these types of things out quickly. Why did you have him become your lesbian lover for the night?"

"We were playing cards with the winner doing what they want with the loser for the evening. Based upon my Master's thesis I had wondered if a male could really become a woman and vice versa. So, I thought tonight I would test this theory out. Jim, I mean Jane being a good sport and a wonderful lover agreed. She did not know that we were going to Baxter's and that we would end up meeting you."

I sat through this entire exchange not saying a word afraid that I might end up doing something I would regret.

Jean followed with a question, ""How curious are you about lesbians and their love making? It seems that by creating Jane you want to know and experience that for yourself. Am I on the right path?'

For the first time since I have known Brandy, she had no answer. Silence.

Jean continued, "Having worked with other women like you, I strongly believe you are really bi-sexual and would love to know what a naked woman would feel like against you. Am I right?"

Again only silence.

Jean continued as she got up and approached Brandy. "Let's see if I am right and also let's see if both of you would like to be part of an experiment. I will allow both of you to do whatever you want an no one outside this house will ever know about it. You both can decide what is a natural sex role and what has been mandated by society"

Still silence from Brandy. I didn't want to say anything because this was starting to get me excited. Would this completely destroy all my concepts of sexual roles and identity. It sounded frightening but something I wanted to find out. The only question was whether Brandy would decide to go for it.

Jean started to rub Brandy's shoulder like she did mine at the bar. Her voice almost became hypnotic as she spoke to Brandy.

"You are a beautiful and powerful woman who has accomplished so much in your life. You must be proud of all that you have accomplished. You also wonder about what makes you happy from a sexual standpoint. I hear it you voice you want to know what is the right sexual role for you in life?. Are you a woman, a lesbian, or a male stuck in a woman's body. I know you love how you look and are perfectly beautiful. But what do you feel deep inside?"

Watching Brandy I could tell something was going on in her mind but I was not certain what was she becoming excited or angry and ready for both of us to run out the door. At this point I was getting excited. My fantasy of an older woman taking charge was becoming reality.

Brandy started to become more docile than I had ever seen her. She seemed to be coming under Jean's influence. Whatever that was.

Jean continued, "Dear you can trust me with both you and Jane to make you safe and liberate you. If I asked you to show me some sign that you trust me would you?"

Brandy shook her head, "Certainly, I trust you whatever you want I will do as a sign of my trust and respect."