As Journey to Janet Pt. 02

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Jim is becoming Janet and reveals his inner self.
4.8k words
4.59
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8

Part 2 of the 3 part series

Updated 06/09/2023
Created 05/25/2019
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I didn't sleep very well. A combination of excitement; uncertainty about what I had just experienced; great sexual satisfaction; and a feeling of guilt all mixed together to make sleep difficult. Laying there naked I felt very vulnerable but also wanting to engage in another moment of passion. As I struggled with these emotions a hand reached across my body and started to stroke my relaxed cock. Within seconds and without any thought on my part it became very hard. I could not stop this new emotional surge.

A soft voice whispered, "It's okay Janet, you are doing well. Just let me take control and put you at ease."

I started to reach another level of passion like had a few hours before but Joeann just made me lay beside her as she stroked my cock and between my legs. Her soft touch gradually became firmer as I started to react.

"It's okay. Just lay here and let me take you. You don't have to do anything. It feels good doesn't it to have me take the pressure of you having to do anything but drift into a beautiful fantasy that is in fact your reality."

I started to softly moan as the tension built in my cock. I knew it was going to be impossible to prevent an eruption.

Her soft voice whispered further, "Go ahead release your white magic here now. You don't have to be afraid. Just let go and let me share this moment with you Honey. Go ahead please me and cum to me. Come on Janet release and please your Mistress."

Unable to restrain my body any further my cock released what seemed like a river of white onto the bed and Joeann.

"That's it Honey, release and let me feel your warm passion and become totally unafraid to enjoy this moment with me. Please let me hold you in my arms."

As I lay there totally spent Joeann pulled me to her breasts and held me like a mother would a baby. She stroked my back and kissed my head.

"Doesn't feel better? You were able to become very vulnerable by letting me take you. You were wonderful."

I lay in her arms unable to move and not wanting to. It was the most wonderful feeling I had in years if not in my life.

My next awareness was smelling freshly brewed coffee and the early morning light streaming into the bedroom through the skylight in the ceiling. A white terri cloth bathrobe wearing Joeann with coffee in hand.

"You probably need to get up and take a shower. After last night I am sure you feel a little sticky. You fell asleep in my arms and slept very soundly for the past 4 hours. You have time to take a quick shower and get home to get ready for work. This coffee will help."

Sitting up I took the coffee and then got out of bed to go to the bathroom for a shower. It was then Joeann commented.

"You are magnificent. Holding you last night was very special. I want to do this again sometime. Now hurry and take that shower before we are both back in bed and we'll both be late for work."

After a few minutes absorbing the hot shower water I started to feel awake. Within a few more minutes I was dressed and ready to leave.

"Will you give me your cell number? I have to go out of town on business later today and won't return until Friday. I would love to text and call you while I am gone. Would that be okay?"

I replied, "Not only okay I hope you will, and I would like to do the same. You are really special, and I have not felt this good for a long time." After a moment's hesitation, "I hope you felt the same."

Smiling Joeann said, "You have no idea how much our time together has meant to me. Yes, let's stay in contact and get together when I get back."

After exchanging cell numbers and giving each other a final kiss, I was out the door and on my way home. For the first time since joining my company I was late for work. This was not a big deal to anyone but me. As I got the day started working on problems for the company, I replayed the previous night over and over. It what been spectacular. I could not get the thought of being completely under her control and released from all worries and troubles for the night.

The day passed without hearing from Joeann. I started to worry that she was unhappy with me. Working late to make-up for my late arrival at the office (that only I, was concerned about) and trying to unravel a complex problem with one of our vendors, I received a ding from my cell alerting me of an incoming text.

"Hi gorgeous, this is Sexboss. Hope you had a great day. I am in Chicago on business and will be here until Friday. How are you doing."

That text was received with a mixture of happiness and sadness. Happy that Joeann had contacted me. Sad that she was in Chicago and would not be back for 3 days. I had hoped to see her this evening.

I sent a reply text. "I am happy you are doing well. I had a fantastic time with you last night and the memory stayed with me all day. I hope when you return from Chicago, we can get together for dinner."

What seemed like an eternity which was only about 10 minutes? I receive her reply.

"I would love to have dinner with you. Can you do me a favor and pick me up at Tampa International on Friday? It will save me catching an Uber and besides it would be great to have someone meet my flight. I will be on Southwest flight 1560 from Chicago Midway which is scheduled to arrive at 5:50 PM."

My response was immediate. "Yes. I will be at TIA to greet your flight. I will be waiting for you at Concourse C for your tram."

Within a minute she responded, "Thank you. I am looking forward to seeing you on Friday. I have to go to a dinner meeting with several clients who want to bid for our business. I am certain they will find our terms to be acceptable. Besides, they are paying for dinner at Morton's. Kisses Sexboss."

While Joeann was enjoying a steak at Morton's in Chicago, I was eating a warmed up frozen dinner and watching the evening news. But I was excited that I would see her on Friday. Between work and my daily activities, the next three days passed slowly.

Breaking this routine, I received a text from Joeann. "Hi there good looking. My negotiations are going well, and I landed a contract that will really save us money and improve the quality of our products. I still have another vendor to get a deal with, but I will make it happen. I got a text from a friend inviting me to a party on Friday night. I would like you to go with me. We can have dinner and then go the party. Is that okay with you?"

While I had hoped dinner and a trip back to her house would be the plan, going to a party would be good and give me a chance to spend time with her in a social setting. I responded:

"That sounds great. I would enjoy being with you at the party. Is there anything I should do in advance to get ready like buy some wine or something?"

I did not get a response for almost an hour and half then the ding on my phone.

"Hi, sorry I had to run. The person I was to meet arrived early and I had to talk with him. The meeting went well but still no deal. Yes, I am happy you will go with me. You don't need to do a thing in fact this is a non-alcohol party. Just bring yourself to the airport. If I don't attack you in baggage claim, I will later."

Smiling as I read her text, I sent a reply: "Glad your negotiations are going well. Hopefully, you get the deal today or tomorrow. I will see you at 5:50. I may not wait until the baggage claim. LOL"

Joeann sent me several more texts over the next day and a half. Most were just "I hope you are well. I am looking forward to being with you Friday." Type texts.

Friday afternoon finally came. I had spruced up to greet Joeann and meet her friends. While Friday was business casual, I took extra care to look sharp. My office is about 15 minutes from the airport. It was Friday and traffic seems to be heaviest on Friday as people leave early for the weekend. At 5:15 I left for the airport. Traffic was heavy and a minor accident slowed things down more. Frustrated with the slow-moving cars, I thought about potential alternate routes. Experience had demonstrated most "alternate routes" usually take more time than just going with the flow. The good news for me was that a service road at the back of the airport property had almost no traffic. I made the right hand turn off Spruce and instead of another 15 minutes of waiting, I drove almost unhindered by stops and red lights. I arrived at the terminal at 5:35. I thought, "That was close."

Flights on Southwest always seem to be early when flying from western destinations to Tampa. Today was no different. The flight arrived 10 minutes early. I had made to Concourse C just before the first passengers were getting off the tram from the Airside C. Joeann was not in that group. Within a minute the second tram pulled in and there she was. Smartly dressed in a business suit, she looked very professional and very sexy. Pulling her carry-on, she saw me and moved quickly. We hugged and kissed like to lovers.

"Welcome home. I hope you had a good flight."

Smiling she said, "It was a productive trip, good flight, and the best part you were here to greet me. I usually pack lite so just my carry-on, briefcase, and purse. I am ready to go."

"That's great we don't have to wait for baggage so let's go to my car. I made a 6:30 reservations at Coopers Hawk for dinner."

When we arrived at the restaurant our table was ready, and we had dinner. Joeann shared with me about her trip to the "Windy City" and all that she accomplished. I shared about my week and a couple of really "thorny" problems I had to work through. Between dinner and a couple glasses of wine it was almost 8:00 before we finished.

Joeann said, "We need to leave because it will take almost 45 minutes to get to where the party is being held. There is a special woman I want you to meet. Let's go. If you don't mind, I will drive because I know the way."

After paying the check, I handed her the keys and jokingly said, "I am at your command."

Smiling Joeann said, "Yes you are and will enjoy this evening."

As we drove Joeann started to talk about our time together and ask me a few questions.

"How did you feel when I shaved you and made you smooth?"

My initial hesitation prompted her to ask, "Please share with me I want to know how you felt?"

"I have never had anyone do that to me. At first I was embarrassed have you do that but after looking at myself in the mirror... uhm"

"Go ahead tell me."

"It made me feel horny. I thought I looked pretty good. I wasn't sure what would happen next, but I was having fun at that point."

Smiling she said, "At that moment I sensed you were really wanting to go further and see what might happen. Did you feel threatened when I started rubbing your back on the bed."

"No, to the contrary it was a wonderful feeling. I was enjoying it and really becoming aroused. I could not hide it when you had me rollover. My cock told the story."

"Yes, I saw you were excited and wanted me to go further. When I started calling you Janet, how did that make you feel?"

Again, I could only say, "Uhm."

"It okay. You seemed to become very compliant and wanted me to do whatever I was going to do to you. Am I right?"

After another minute of silence, "Well yes, I felt like you have become my mentor and could lead me. When you pulled me to the side of the bed all I wanted was to have an orgasm."

"I see, I knew you were very aroused. Let me ask you did you feel uneasy when I started calling you Janet and fucking you?"

"I shouldn't admit this but that was the best part. I had never felt so free and excited. You brought something deep within me that begged to be released. That was strange and I have some guilt feelings about that because that's not normal, but I loved it. Did you loose respect for me because reaction?"

Without hesitation she said, "No, Honey, if anything I grew in love and respect for you allowing yourself to submit your deep desires to me. I suspect no one has ever allowed you to do that."

"It was a special moment. I cannot get out of my head. I kept me awake several nights this week just reliving that special feeling."

"Very good. That means you really could release your inhibitions and become who you want to be. Tell me how you felt laying naked next to me trying to sleep and I reached across and stroked your cock?"

I responded, "I just wanted to lay there and let you take me. I only stroked my cock once in my life in front of another person and that was when I was in college. It was not a pleasant time. You made it much better and when you cuddled me after I orgasmed, it was the best feeling."

"Tell me about your experience in college."

I slowly started to share my story. "I have never shared this story with anyone. It was a private thing that I am ashamed to admit."

Joeann's soft voice simply said, "Go on you are safe with me."

"During the summer I was working as a general maintenance person for a company that managed several apartment complexes. The usual routine of work such as cleaning a vacant unit before the new tenants move in, mowing lawns, and fixing minor items such as replacing filters on heating/cooling units. One afternoon I had to replace a broken ceiling fan in a unit. The male tenant was home at the time. I went about repairing what was in fact a very minor problem and was ready to leave. The man asked me if I wanted a drink before leaving."

Listening and driving Joeann said, "Continue and tell me more."

"He asked if I wanted a beer or iced tea. I was on the clock, so I said iced tea. He brought me a glass and we sat and talked for a few minutes. About 5 minutes into my tea, I began to feel dizzy and faint. I tried to stand up but had to sit back down. At that point the man came over to sit beside me. He started to stroke my thighs. The next thing I knew he was pulling my clothes off and I was naked."

Joeann responded, "That sounds like you were being seduced. What happened?"

"I was told I could not leave until either I masturbated for him or he fucked me. The choice was mine. He was a Voyeur and wanted to watch me. I refused at first but when he said I had a virgin ass that needed to be broken in or I could just masturbate for him, I decided that was the best course. So, I pleased that pervert and jerked off for him. He took pictures of me while I was doing it."

"When I finished, he told me that if I tried to say anything to the cops or my boss, he would simply show them the pictures and tell them he caught me jerking off when he came home. I got dressed and staggered out of his place. I got a coffee and tried to shake off the dizziness."

Listening intently Joeann asked, "How did you feel about doing that for that guy?"

"Uhm...well it aroused some sort of strange feeling. I felt aroused and a sense of total release being totally under his command. It made me feel like I could do that again."

Joeann asked, "Did you?"

"No, I also was ashamed to admit I liked being naked with another person, especially a man, in the room and performing for them. When you stroked me the other night the desire to submit to whatever you wanted just reinforced the feeling I had after my day in that apartment. Then you made me feel secure by holding me against your breasts. I truly wanted more."

Joeann softy said, "You will have more Honey. You are safe and secure. Thank you for sharing that very personal story with me."

Within a few minutes we turned into a dark, old, subdivision in Lutz. The houses were from the 50's and 60's. In another half a mile we pulled onto a gravel driveway. A man at the gate asked, "Are you expected?"

Joeann replied, "Yes, my number is 9442." With that the gate was raised and she pulled the car to the back of the building.

"We are attending this party primarily so you can meet a very special friend of mine. Most people know her as Madam LaBotshi. Some of her very special friends know her as Beth."

"We are going into to a very private club. Only a select group are members. There are very specific rules that must be obeyed. People only know each other by a screen name so I am Sexboss to all the members. Beth is "Truechange". The owner and person in charge is Sir Thomas. His wife is "Sisterdaisy". We are here because Beth only is in town for a week before leaving for a month's trip to Europe. She only meets people here because it is a safe place."

Puzzled I followed Joeann into the building. A small sign over a counter clearly states, "This is AN ALOCHOL, DRUG FEE CLUB" . There was an area just inside where people could leave their possessions. I later learned that meant their clothes.

Joeann started to show me around. "The large meeting room is where all the exhibitions are conducted." There are all sorts of equipment and harnesses in the center and chairs along the walls.

"The club has a couple of rules that cannot be broken. An offender will be warned and if a second warning is needed the person is out. The big guy standing on the far side of the room is the enforcer. He is a former Canadian league football player and form wrestler for the WWE. He has a master's degree, in psychology and working on his PHD at the University of Florida. He is writing a book on sexual interests and obsessions of men and women. If he is required to act, he is not gentle. "

She continued, "The rules are simple. No drugs or alcohol period. No means no. If a person is told that their participation or requests are not wanted, then they stop and leave that person alone. The private rooms in the back are meant to be used for those who want some privacy, and nothing is off limits as long as everyone agrees and there is no intentional harm. The rules a simple but strictly enforced."

Walking by one space with heavy black drapes Joeann said, "This is the "grope room". All bets are off once you go in there. It is assumed everyone entering is saying yes. There are no limits. For those who first visit this club, I do not recommend they go into that room."

Moving further into the building we passed a hot tub with several men and women talking. It was immediately clear that clothing was optional. Another group of men and women were standing around several tables drinking soft drinks and eating snacks. Most of them were wearing some very skimpy clothes. As we passed by, one of the women gave me a wink.

Finally, we reached a group of rooms in the back. The one on the extreme right was where we were headed. Entering the room, I saw an older, heavier woman wearing what looked like a "cover up" women wear to the beach or swimming pool.

Joeann immediately rushed over to hugged her.

"Hi, Truechange, it has been a long time since we have seen each other."

With a smile, "Sexboss, you are beautiful. How have you been?"

After a few minutes of chit chat Joeann said, "Truechange, this is my friend I talked with you about on the telephone." With that the woman grabbed my hand and pulled me to her breast.

"It is so nice to meet you. I want to learn more about you. Please sit in that comfortable chair and let's talk."

There was a very comfortable brown leather chair which felt great.

"Truechange, I need to change out of these clothes and into something more comfortable. While you and my friend, Seeker123 get to know one another."

"Sexboss, yes please change and we will get acquainted."

Looking at me "Truechange" started to speak in a soft, hypnotic voice. I quickly started to relax.

"Sexboss tells me she had a wonderful time with you and that you are a very special person. That is wonderful. Now relax and don't worry about a thing. You are safe here and there is no judgements or rules when someone is with me. I have known and worked with many men and women over the years. Sexboss told me that you were very happy in her bed. That you responded so beautifully especially when you became Janet. How did that make you feel?"

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