Vickie's New Girl Jennifer

He was now the only person I could trust to help me in my current situation and decided to turn to him for help. I explained how much I loved my husband and that were going through a rough patch and needed his help. I explained the sensitivity of the situation, and I needed him to be understanding and he assured me that our friendship was important to him and he would never betray my trust.

When we were in Tampa after we settled the lawsuit, we had a late dinner. It was then that he told me how valuable I was to the firm, and that I was their best litigator. He offered me a position as a Partner at the firm. Of course, I was ecstatic but before I accepted the promotion, I explained my current personal issues and wanted him to know what I was going through. I told him it would not impact my work and I'd be happy to accept the position but being a friend, I felt he should know. I explained how I caught Rick dressed up in female clothes and my plans. I explained that I did some research and needed to know how far he's willing to go given an opportunity. I told Peter about my plans for dinner on Friday and how I needed his help. Of course, he said he'd be happy to be my date. He agreed to pick up Blake and play along with the story I developed. The story was that Blake worked at the firm and was celebrating the lawsuit.

"I owe you big time for this Peter, you're a good friend. I'll set up the reservations and text you all the information for Friday night. Just follow my lead and hopefully, I'll know much more about the situation. Thank you again for the promotion, I promise I won't let you down," I said touching his hand. We shared a moment, but it passed when the waiter came by with our coffee.

Friday night after getting ready, I took a limo to the restaurant and knew exactly where to look for Jennifer. At first, I didn't recognize the woman at the table but as I approached, I realized it was Rick, or now Jennifer.

"Oh my God! You're beautiful!" I said as we shared an air kiss like any girlfriends saying hello and not wanting to mess up our makeup.

"Thank you, Vickie. I'm very nervous out here like this," Jennifer said in a voice she hadn't heard before.

"Oh, don't be nervous, nobody would guess you are a man, and where in the world did you get that voice? It's so sweet, and very feminine. Please use that voice when you're Jennifer from now on, it completes the illusion."

I was happy that I had Jean put that pill in her purse and that I made her swallow it because, when the men arrived, she would need it for sure. After the guys arrived, I took her to the lady's room and explained our plans, and how the night would go. I advised her to be on her best behavior and not to embarrass me with my boss and the pretend co-worker.

My intention for all of this was to see how she looked and acted when in female mode. I knew that in his male mode, Rick would never tell me all of his secret feelings, so I planned to get him out as Jennifer, relaxed with some drinks, and in a safe environment and watch his behavior and learn the extent of his desires. I didn't expect to see a beautiful woman waiting for me but so far, he, or should I say, she's, a natural. He even seems comfortable with feminine movements and walking in his heels. Yes, I already can tell that he has had much more experience in dresses than I realized. Tonight, I hope to accelerate the learning curve and find out exactly who I've been married to.

She was shocked when I made her sit in the back seat with Blake. I saw the look of panic on her face and mouthed the word, relax. It was interesting to be out on a double date with my husband, who was now much more female than any of my friends.

I could hear Blake talking and asking questions, but Jennifer was frightened, and wasn't saying much as we arrived at the restaurant.

Seeing my husband as a woman and now being helped out of the car by her date, was odd, to say the least. Watching him hold Blake's hand and walk alongside him was interesting to watch but Jennifer kept up with him and stayed by his side. I kept giving her smiles of encouragement and trying to keep her calm. She didn't object to anything so far and accepted the female role faster than I had wished. But this was the reason for the dinner, and I wanted it to play out until the end. I truly loved my husband and if there was any way to keep us together, I would help make it happen.

Jennifer did great at dinner, was a delicate flower as she sipped her wine and ate her dinner as Blake chatted her up. I intentionally spoke with Peter about our client and we toasted to our win several times to keep up the illusion of a celebration.

I could tell Jennifer was very relaxed from the pill and the drinks. The real action was going to be at the club, and that's where things got interesting. Would she let Blake touch her, kiss her, dance with her, and go home with him? All things I arranged and watched with great interest.

When she cornered me in the lady's room and questioned me about where I was with Peter for the missing time, I couldn't help myself and tease her with a little fib. I made it seem as if Peter and I were getting it on, and that I took care of his needs. It wasn't fair but it was fun, and I would tell her later we just were at the bar talking.

What I did find interesting is that she was completely in the role of a girl as she danced with Blake. Several slow songs, holding him tightly and watching Blake grab her ass and pull her tight. I took some photos and videos that I would share with her later. My heart was heavy when I saw them kiss. Not once but several times, but what troubled me is that Jennifer didn't resist, but accepted his kisses, which I also filmed.

Peter could tell I was disappointed. I explained that I was hoping that my husband would not put up with my request, definitely not accept a dance with another man, and the kissing drove home the point that my husband accepted his role as a female, without hesitation.

"Well Peter, thanks for doing this tonight. You've helped me and I won't forget that. It's obvious now that I have to decide how to handle things with my marriage. I do love him and want him to be happy and I don't want to leave him over this. I guess I'll see how this ends up later on after you and I duck out and leave her alone with Blake. That's when I will see if our relationship can last," I said as Peter rubbed her arm trying to comfort me.

It was now 1 o'clock and I was exhausted from the long week. When Blake took her out on the dance floor, I decided it was time to leave and put the final part of my plan into action. Blake was aware of my plans and played along perfectly. Peter and I waved to them from our table as they danced. When they started kissing in the middle of the dance floor, I told Peter it was time to leave. We did, and Peter walked me out to his car and drove me to his place for a nightcap.

Blake had a note that I had prepared, and he was instructed to give Jennifer when I was gone and that's exactly what he did, I learned afterward. Blake said she was scared and nervous about being all alone until she read the note.

The note said, "Jennifer, tonight you're a woman and I want you to live your dreams. As you probably know by now, Blake knows about your little secret, so you don't have to be nervous any longer. Blake will take you home and I want you to experience anything you desire. Peter will bring me back home, not sure when but not until very late. Enjoy this opportunity and live your dream, wherever it takes you. I love you."

Blake said she stood there in shock until he took her in his arms and said, "Jennifer, it's OK. You're safe and I'll take you home, relax." He explained that Jennifer didn't say much after that as the Uber drove them back home.

When they arrived, Blake said he asked Jennifer to let him come in for a nightcap, but she refused.

"Come on, Jen. Let's have one drink and I'll make sure you get safely into bed," he said.

"No thank you. It was a fun night, but I should go in," she said.

Blake took her in his arms, and they kissed for several minutes as the car waited. "Can I call you for another date?" he asked.

Well, it turns out that the little princess did give Blake her cell phone number. I only found this out from Blake a few days later. Jen never mentioned that little piece of information. Blake told me that after they kissed, she left him there and walked into the house. All the information would be useful, as I figure out his true desires. In the meantime, he was alone for 4 hours as I stayed out with Peter until late

We stayed up and talked on his couch until 5 o'clock when I finally said I should get home. He was kind enough to drive me home and pulled into our driveway offering me anything I needed. I thanked him as he held my hand. We again shared a moment as we looked into each other's eyes. If I stayed there any longer, we probably would have ended up kissing in the driveway. I believe that sharing intimate things like this can create an unexpected closeness. I got out quickly before I lost control and headed into our house.

The poor thing had a very stressful evening and had no idea what Peter and I were up to. I'm sure it was painful to think I was having an affair with Peter, but somehow, I didn't feel too guilty as I remembered how we got here.

Jennifer was waiting up for me when I returned and entered the bedroom. She was still dressed in her clothes laying on top of the comforter and sat up as soon as I came into the bedroom and said, "Oh my God, Vickie. Where have you been, and what is going on?"

I took my time and got undressed then laid next to him in the bed. I touched his fake breast and smiled.

"You do realize that you make a lovely girl, and I'm so happy I got to meet the real Jennifer tonight. You're prettier than most of my girlfriends and much more feminine. And the way you handled yourself with the guys was impressive. It sure looked like you had fun with Blake, I mean all that dancing and kissing. Oh my, you made quite a scene."

"Vickie, answer my question, where were you? I've been worried sick for the last 4 hours," he said.

"Well relax, nothing happened. I spent a few hours with Peter at his place just talking, that's all. After being with Jennifer all night and realizing just how feminine you are and how easily you go on with another man, I was a little surprised and just needed a friend to talk with. Peter was there for me and helped me tonight. Nothing happened between us, I promise," I explained.

"What about what you told me in the lady's room, when I asked where you and Peter were, and what you were doing? You told me you spent time with him and took care of his needs. What were you doing?" he said showing his jealousy.

"Well, to be honest, you were acting like a little bitch, and I needed to teach you a little lesson. By not trusting me I made up that story to give you something to worry about. We just sat at the bar and watched you acting like a girl with Blake.

After I decided to give Jennifer a chance to stay in the relationship, I had to find out what makes her tick, which is why tonight happened. Many of the other wives I spoke with suggested this, and I agreed that it made sense. I assumed you would maybe go through with the makeover and spend some time as Jennifer. I anticipated you putting your foot down and just say no to dinner with two men, but you didn't. I was shocked when you went along with this, without much of an argument. Once you agreed to dinner, I assumed you would adamantly say no to going to a dance club with the men and demand we go home. Again, you shocked me with a weak objection but quickly gave in and went along, like a submissive little girl.

Yes, there were many surprises, like when you accepted Blake's hand as he led you out to the dance floor. The way you danced to those slow songs, the way you handled yourself in those heels, how you let him hold you, how you let him kiss you. Yes, I learned a great deal about Jennifer, and we will have to sort things out but now, I'm exhausted and need some rest.

We can pick this up later today. Now go get undressed, grab one of my nightgowns, and lay with me and get some sleep.

Revelations

We slept late into early afternoon and woke up in each other's arms. We made love and held each other and shared our feelings and expressed our love. Vickie was naked but I was still wearing her nightgown, which gave me some extra excitement and an exciting love making session.

"Wow, you were amazing and very hard. I guess you really enjoyed the last 24 hours," Vickie said kissing and fondling Jennifer before they got up.

"I needed that, and yes I did have fun. Thank you for everything" Vickie, he said hugging her before they got out of bed.

"You're welcome. I think we should go out for a late lunch since you are still in your Jennifer mode. Let's clean up, get rid of any facial hair and then I'll help you with your makeup. I'll take out some cute outfits for us and then we can get dressed together and spend the rest of the day as girlfriends. Doesn't that sound fun?" she said.

It sounded fun and I told her so, "Yes, it does. I can't believe I'm so lucky to have you as my wife. I've always dreamed of getting dress with you like that, it sounds fun."

"Well, then it's settled. We will spend the rest of the day as girlfriends. Now let's get ready, I'm starving," Vickie said.

I sat at her makeup table as she fixed my hair and helped with my makeup and I loved the image she created. We both got dressed together and I was in ecstasy. She had our lingerie on the bed, Pink Pantie and Bra's for both of us. On top of my pile I noticed the silicone pads that she placed and a new package of pantyhose on my side of pile and instructed me to get dressed. I slipped on the bra and panties and enjoyed opening the new package of pantyhose in front of Vickie, it was a dream come true. I slid the pantyhose up my smooth legs and adjusted them as Vickie watched how I handled the garments.

"Very nice, you did that perfectly. You seem very adroit in handling those delicates, just lovely! Now, let's get finished," she said as she pointed to my outfit on the door. It was a yellow sun dress, which fell a few inches above my knee, along with a pair of her floral print wedge sandals. I expertly put on the outfit and shoes as I watched Vickie slip into the denim miniskirt and sheer blouse and heels. We made a cute couple, albeit my outfit was much dressier and more noticeable, but I loved how it looked on me as we stood side by side in the mirror.

An hour later we were sipping a glass of white wine as we sat close to each other at her favorite outside café. I was starving and wanted a big dinner, but Vickie had other ideas and ordered avocado salads, as she smiled and said that us girls need to watch our figure.

"We need to talk Jen. Last night was fun, but also revealing and I think we need to understand where we go from here. You can't tell me anymore that your dressing up was just a hobby or something you enjoyed from time to time. No, the way you handled yourself, your voice, mannerisms, and willingness to be out in public tells a different story.

Now you know I love you and don't want to lose you, but I demand the truth, no more lies or secrets. I need you to tell me you won't keep anything from me again. If you do that, then I think we can get past this and find a way to make this work. I won't accept lies or secrets. Are you OK with that?" Vickie said.

I was surprised by her question after a few seconds, answered her question, "I'm sorry for not telling you everything. I thought it was something I could control, and I know now I was delusional to think it wasn't a bigger part of my life. I'll never keep anything from you again, I swear. You are the most important thing in my life and I'd never intentionally do anything to hurt you. I promise, full transparency from now on. Thank you for giving me a chance and letting Jennifer out of her prison," I said with tears welling up in my eyes.

Vickie saw my pain and placed her small feminine hand over mine and smiled. "We'll get through this baby. Now, I do have lots of questions and I expect you to be honest with me, OK?"

Nervously Jennifer said, "Yes, ok."

"Please understand that I'm not trying to make you feel uncomfortable but the only way I'll understand is by asking questions. That's probably because I've been attorney for all these years, but I promise I'm not trying to hurt you or make you feel bad," Vickie said.

Vickie: "When did you start crossdressing?

Jennifer: "Very young, maybe 4 or 5 years old. I remember putting on some of my mom's panties and things when we lived in our first home. We moved when I was 5 so it was around that age."

Vickie: "Wow, that is young. What happened as you got older, did you continue dressing? Tell me about it honey."

Jennifer: Taking another sip of wine Jennifer continued, "It never stopped. I remember sneaking things out of the laundry basket all the time. I also would go through her drawers after school, while she was at work. At first, I just enjoyed the feeling of the silky things but later it became something I thought about all the time. I remember putting on one of her girdles and stockings under my school clothes when I was in second grade, and then wearing them to school. I can still remember the excitement I had wearing them.

Vickie: "That's amazing and kind of cute. Wearing mommy's lingerie to school. Did you get caught?"

Jennifer: "Not then but when I was older, Mom found my sisters pantyhose, bra, and sweater in my closet when I was in 9th grade. I was about 15, I guess. She never mentioned it, but I remember hearing her and my dad talking about it and then heard my mom blaming my dad for my dressing up. To this day, I'm unhappy she blamed him because he had nothing to do with it and I'm sure it hurt him. From that moment on I swore I would never get caught again. I would stop forever, and nobody would ever know about it again. It was hard for me at that age to understand since I had nobody to talk to. There was no internet and crossdressing was not mainstream. I blamed myself and carried a great deal of guilt, as you can imagine. They never said a word about it to me and it became a dark secret."

Vickie: "Oh my! Being so young and not having anyone to help you, how terrible. It must have been hard for you back then. So, you've carried this secret and desires for all these years?"

Jennifer: "Yes. Every time I think I had it conquered some desire would overtake me and I would find myself dressing again. My desires and fantasies have grown over the years as this developed.

Vickie: "How did it change, what were some of you fantasies?

Jennifer: "This is hard. There were many, many, nights I would go to bed praying to god to make me a girl when I woke up. I begged god to tell me why he did this to me, many times. I had so much anger and hope but nothing changed. I wanted to wear those items and become a girl, not knowing why. There were many times I would take my mother and sisters things, dress up and go out of the house, just to be outside. I made sure it was safe, but I always had the need to be out as the girl I wanted to be."

Vickie: "How were you dressed, were you completely dressed as a girl?"

Jennifer: "Completely. Makeup, wigs, heels, lingerie, dress, everything. I remember watching mom and my sister do their makeup and I knew where everything was. The moment they left the house I carefully put on their things and practiced. Because of my desire to look like them, I got very good at my makeup and hair. There were times I had the full day to dress and I would practice my movements and voice as I pretended to be a girl. They were some of the happiest times of my life."