Vickie's New Girl Jennifer

"Well, I'm not convinced just yet but perhaps after tonight, I'll be convinced. Now, open your purse and the side zipper," she instructed. I did as instructed and saw something wrapped in a tissue. I opened it and saw that it was the other half of the pill that Jean had given me earlier this afternoon. I looked at her puzzled.

"Jean told me how the pill he gave you helped you relax and go along with things today so I asked him to put the other half in your purse. I have a feeling you're going to need it to get through the rest of the evening so go ahead, take the other half, and swallow it now," she said in a commanding voice. I washed it down with some wine and sat there quietly.

"While that takes effect, I'll tell you about my day, OK? Thanks to my strategy, we settled that Corporate Lawsuit in favor of our client. I've been in such a good mood all day and I have been looking to celebrate all weekend and we're starting tonight.

I never realized how nice a shape you have, and now I understand why you kept yourself so slim. Jean did an amazing job on your hair and those extensions look so natural; they will last for months before you need to have Jean fix you up again. Now, I've been rambling on and haven't given you a chance to speak yet. That was so rude of me, Jennifer. Is that pill working yet?"

"Yes, between the pill and the wine I'm definitely starting to feel more relaxed," I said in my Jennifer's voice. Obviously, she wasn't prepared for that and looked shocked.

"Oh my god, what a lovely voice. I want you using that from now on, Jen. What other surprises do you have for me, I wonder. Well, I've done a great deal of research on you over the last week and learned a great deal which is why we're here today. The truth is I was not OK with learning about your feminine needs and extremely hurt on how I found out. Betrayal and cheating are things I cannot tolerate but to be fair I needed to see Jennifer and try to be understanding. By the way, you speak and move so gracefully I'm convinced that there's a lot more to Jennifer than I originally contemplated. You are obviously experienced and submissive, which is good to know and will determine where our relationship leads us. By now, I'm sure that pill has done its trick and you're probably feeling no pain, am I right?" I smiled and nodded.

"Good, because I don't want you all nervous and anxious before the evening even starts," she said as a car pulled up in front of the restaurant. I saw Vickie wave to the two guys that got out and watched them come over to our table.

She looked at me before they made it to the table, smiled and said, "You wanted to be a girl, well I am making your dream come true! You better be convincing and not embarrass me or I promise you will regret it, and that's a promise, not a threat. Do you understand?"

I was speechless and just nodded as the two men came over to our table. Vickie did the introductions, "Hi guys, right on time as usual. I'd like you to meet my best friend, Jennifer Clark. Jennifer, this is Peter the senior partner at the firm, and Blake is one of his good friends," she said accepting a friendly kiss from Peter as if it was an everyday occurrence. I immediately got concerned because whenever Vickie goes out of town, she has always traveled with Peter, who she said was always integral to client negotiations. Now I wondered if there was more to the story.

Blake took my hand and said, "Nice to meet you, Jennifer." I smiled shyly and said hello.

"You girls ready to go? We have reservations in thirty minutes and there seems to be a little traffic," Peter asked firmly.

"Yes, just let us visit the girls' room and we will meet you in the car. Peter, be a dear and close out the tab for us please," Vickie said as she controlled the situation and told me to come with her to the ladies' room. I didn't argue because I really had to pee and was happy to get her alone and find out what was going on. The problem was when I stood up I almost lost my balance and fell all because of the two glasses of wine and the pill that now had fully kicked in. Vickie grabbed my arm as we walked arm in arm to the ladies' room.

"Vickie, the drinks and the pill really hit me and I almost fell. Why do those guys think we are going to dinner," I asked as we entered the ladies room. Vickie told me to be quiet and pointed to the stall and whispered, "Remember to sit girl," and led me to the stall. I realized I was in a public ladies' room and had to stay in Jennifer mode. I carefully rolled down my panties and pantyhose enough to pee. I was holding my pee back for hours and it felt so good to relieve myself that I just smiled after a few seconds.

Quickly, I got dressed and met Vickie out by the mirror. We were alone for the moment, looked at me, and said, "Take your lipstick and fix your lips, honey."

I opened the purse and saw some makeup and other things that she had placed in there and took out the lipstick. I followed her movement and applied my lipstick and touched up my face as I looked over at her and said, "You know I'm not going anywhere with those guys. Let's just go home, Vickie."

She laughed, "Now that's funny! No, we're going out to dinner and celebrate my win and you're coming out as Jennifer. I'm not giving you a choice here, or maybe I am. For what you did to me by betraying my trust, this is your payback. You wanted to dress up and be Jennifer, then that's what you will be, and either you love me enough to share her with me or you can go home by yourself. And if you decide to go home by yourself and not follow all my instructions tonight, you can just pack up your things and move out tomorrow. So, I guess you do have a choice, Jen. You can go out tonight and enjoy your time as Jennifer or betray me again and move out. What's it going to be, baby?"

"OK, I get it. I'm Jennifer tonight and I'll prove my love for you and do what you want," I said.

"Oh goodie, we're going to have so much fun together. Remember to keep using that sexy voice and whatever happens tonight, you and I have been friends since college. That's what they believe, so just keep up and follow my lead, girlfriend. Now hurry, the boys are waiting for us," she said as another girl came into the ladies' room. She held my hand and led me through the lounge out to the waiting car parked in front.

Vickie quickly slid into the front seat, leaving me to sit in the back with Blake. Peter gunned the Tesla and we quietly flew out into traffic as he drove towards the restaurant. Peter and Vickie started talking about the settlement as Blake tried to chat. Not knowing how to act, I tried to relax and gave short answers the entire way to the restaurant.

Peter pulled up to the Valet and without hesitation, the guys jumped out and helped us exit the car. As the valet drove away, Peter took Vickies' hand and Blake took mine at the same time and led us into the restaurant.

Allow me to take a second and describe the scene as I remember it. Even with my head spinning and trying to comprehend what was happening, I can now recall things more clearly. I remember sitting in the back of the car with Blake and answering his questions as I kept my legs crossed and my hands on my lap, trying to act as demure as possible. I remember trying to listen to Vickies' conversation but Blake kept me too busy in the back seat.

All the feelings came back to me and I can remember how wonderful it felt wearing that dress and feeling the silky material slide over my pantyhose and very tight pantie. Seeing my pink long nails on my fingers and the taste of my lipstick along with the sweet smell of my perfume, are fond memories of my first time out in public.

Blake and Peter were large men compared to Vickie and me and both towered over us by at least 3 inches, even in our four-inch heels. I remember feeling small next to him and the grip of his large hand as he held mine still gives me chills. Trying to keep up to him in my heels and short dress, as he led me into the restaurant, made me realize I was now the weaker sex, and in a submissive position. I later admitted to Vickie that enjoyed that feeling and that I would love to feel that way again.

Having to watch my movements, speak in my Jennifer voice, and follow along in conversations was tricky after Vickie poured several glasses of wine. All of my inhibitions left my body and I was left with a very relaxed, and content feminine persona, Jennifer. Apparently, up until this point, I fooled the boys, and nobody realized that I was actually Vickie's husband, a man with something to hide.

When they took us to a club after dinner, I was concerned that my secret might come out if Blake got any more handsy under my skirt. I stopped him several times, but I wondered how long I could hold him off. In the meantime, Peter and Vickie were out on the dance floor for a very long time, and at one point I hadn't seen them for over an hour. I saw them emerge from a hallway and return to our table.

"Welcome back Vickie, you two having fun?" I asked sarcastically.

She gave me one of her award-winning smiles and said, "Oh Yes! We're having a great time, but I really need to use the ladies' room. Join me, and I'll tell you all about it."

We left the men and I followed her to the ladies' room where I peppered her with questions. As soon as we were inside the empty ladies' room I started asking her questions.

"Where were you all that time? You left me all alone with Blake and I had to dance with him and put up with all his advances. And you sure seem very cozy with Peter," I said with some obvious anger.

She was smiling, "Settle down, Jen. Peter is one of the Partners at the firm and he's one of the reasons we're celebrating tonight. After my win today, Peter convinced the other partners to make me the first woman Partner at the firm. That means much more money and a partnership in the firm. Tonight is for us, baby. You won't have to work anymore which will be helpful because I'll be working a lot more hours and I'll need you at home to help out more. I've worked toward this for years, isn't it exciting?"

"Well yes, I'm happy for you but where were you all that time?" I asked.

"I was so excited about the news I just had to thank Peter in a special way, if you know what I mean," she said touching up her face. I looked at her shocked with my mouth open.

"Oh Jennifer, she said with an emphasis on Jennifer, stop acting like that and stop being so naive. Peter is a powerful man and it's the least a girl can do for what he did for my career. Besides, I enjoyed it and I'll be doing it again," she said turning to me and pointing at my lips.

"Jen, your lips are a mess. I guess you and Blake are getting along nicely but fix you lipstick sweetie and let's get back to the boys. Oh, and by the way, Blake and Peter know all about your little secret but don't worry, Blake is an old friend of Peter that happens to like special girls, and this has all been arranged, so just let yourself go and enjoy the evening," she said as two women entered.

She again took my hand and led me back to the table. I was upset but still very confused and high from the drugs and drinks, but I knew things weren't right. When we got back, she sat close to Peter and was leaning into him as he placed his arm around her. He gave her a warm kiss when she sat, and it was clear that she and Peter were closer than I wanted. I felt jealousy rage and my stomach turned as I watched her kiss him back in front of me. She smiled over at me and gave me a wink as Blake had just put his arm around me at the exact same moment.

"Let's dance Jennifer," Blake said as he stood and led me out as a slow song was playing. As we danced, he held me close and whispered in my ear, "Jennifer, I think you are beautiful and I want to be with you and yes, I know all about you. Vickie told us everything."

I was in shock and leaned back to look up at him, but that only ended up with him planting a strong kiss on my lips. In an effort to avoid being smothered, I tilted my head and leaned back. He took that a sign of submissiveness and proceeded to kiss me right there on the dance floor, in front of everyone, including Vickie and Peter.

When he finally released me, I tried to recover and placed my head on his shoulder, trying to comprehend what was happening. As we danced, I noticed that Peter and Vickie were no longer at the table and I didn't see them on the dance floor. I panicked and started to look around. Blake knew what I was doing and whispered in my ear again.

"Jennifer, Peter has taken Vickie back to his place for the night. Don't worry, I'll take care of you tonight and get you home safely. Vickie instructed me to tell you to enjoy yourself and not to worry about her tonight and that she's in good hands. She asked me to give you this note when we were alone......

Vickie's Recollection

I couldn't believe my husband has kept this secret from me for all these years. From what I've seen this is much more than a hobby. His makeup and hair were perfect, and the way he looked in that dress was all female. No, this was much more than a hobby or an infrequent escapade.

Spending the weekend on-line and talking with the wives of other crossdressers, helped a great deal. I was actually amazed at how easy it as to find chat rooms with other wives that had husbands that crossdress. They were kind and understanding as they answered most of my questions. My friend Jean, who has also been my hairstylist for many years, is gay and helped me through this. He calmed me down and explained that crossdressers are not all gay and just enjoy wearing women's clothes. He gave me some good ideas to experiment with and find out.

The wives I chatted with, also helped me understand why Rick kept this part of his life secret to avoid humiliation and the loss of respect. Unfortunately, the way it was discovered was impactful to both of us. I'm not sure where we go from here, but I'll know more after next week.

I told Jean about my plans for a complete makeover on Friday and he was happy to help us through this. He also suggested a way to find out about my sexual proclivity and explained that he has a good friend that likes to date crossdressers. A very good-looking, alpha type male that would be willing to help us and owed him a favor.

Jean went on to explain, "Let's see how he acts during the make-over and if I think he's passable and ready for this I'll tell my friend Blake to be available. Do you have anyone you can double date with on Friday night? We can make some last-minute plans if you do."

"Jean, you are incredulous, but I love the idea. It would give Rick, or should I say Jennifer a chance to live out his fantasy, and it would let me know the truth about his sexual desires. I can come up with a friend for dinner. If you don't think Jennifer is ready, I can just make it a business dinner with a friend and send her back home. From what I saw, I think Rick will be passable, but I'll let you tell me if you think Jennifer is ready for a double date with your friend Blake. It would be fun to watch, in an evil kind of way," Vickie replied.

"Yes, I think we can set this up. I'll get Rick to loosen up and confide in me and find out if he can handle it and let you know on Friday afternoon. I'll see if I can get Blake on standby and in the meantime, you need to get a dinner date set up for Friday night. I'll handle Jennifer and Blake, you handle the reservations, logistics, and a date for yourself which I know won't be difficult. As pretty as you are, I'm sure any guy you ask will jump at the chance of taking you out for dinner. I'm off this Friday but for you, I'll come in and help both of you. Send him in at noon and I'll have Jennifer ready by 5 o'clock. I'll let you know if she's ready by 2 o'clock and then I'll call Blake and tell him the details you will have arranged. After that, you will have to direct things that night. Promise me you'll tell me everything because I can't wait to hear all about it," Jean said.

"You know Jean, the more I think about it, the more I like the idea. It will allow him to live out a fantasy and it will give me an idea of where we go from here. I do love him, and I want this to work. You're a good friend and I really appreciate you coming in on your day off to help us, and I'll pay you generously for this. I'll want the works, whatever you think is needed. I'll send him over with a list of things to do but feel free to add whatever you think will make him as feminine as possible and I mean anything! "Don't mention anything about dinner or a double date. I will need to put him, or I should say her, in a situation where she can't back out, so leave all that to me."

The planning was easy, but I did avoid any contact with Rick until this played out. I didn't want to let up on him just yet and being out of town made it easy to avoid any conversations. I arranged for my good friend and employer, Peter from work to meet me for dinner and he agreed.

I was hoping that Jean would call me and tell me that my husband was not ready to go out in public or that he wasn't passable, but when Jean called it was not what I was hoping for. Jean explained how Rick had been dressing for years and loved pretending to be feminine. He was amazed by how feminine he transformed and how natural he was as a female. "Vickie, Jennifer is very convincing and enjoying this transformation, more than even I anticipated. Jennifer is definitely ready for a debut and I think you will be absolutely amazed, I know I am. So, what would you like me to do Vickie?"

"That wasn't what I was hoping for Jean, but it is what it is, and I thank you for your help. Is Blake still amenable to play the role of her date tonight?" I asked.

Jean answered, "Yes, we just spoke a few minutes ago, right after I sent over a few of her photos. He said that he's happy to help and in fact, he said he's looking forward to it."

Thanks for taking care of that Jean, but I will admit, I'm disappointed. I was hoping for a different outcome, but things seem to be falling into place. Perhaps it's a good thing for all of us. I'll have Peter pick up Blake as I want them to arrive together. I've instructed Peter on things and he will explain the plans when they drive over to pick us up. I just need you to text me Blake's address and Peter will pick him up at 5 o'clock. Do you think Blake will be OK with that? Be sure to tell Blake I don't expect him to pay for anything and we will take care of any expenses he has, please."

"No worries, he's a cool guy and you will like him, and oh my, he's also very handsome. It will definitely be an interesting night," Jean said.

"In the envelope, there is a note that I would like you to give to Jennifer when she is done. I need her out of there at 5 o'clock to be at the restaurant on time. Can you please make sure she's out the door at 5 o'clock, with the note?"

"No problem, I'll be sure to follow all of your instructions and get her on her way at 5 o'clock sharp," Jean said.

I remember hanging up the phone and letting out a sigh. It was at that moment I realized there would be some decisions to be made in our relationship. Friday night would tell me what direction or marriage will be headed. I felt sorry for Rick in a way and was trying to be an understanding wife. I love him so much and I just want him to be happy, wherever that may lead.

Now I had to make all the plans, including dinner reservations, and find myself a date for Friday. The only person I felt safe telling was Peter, my boss, and my closest male friend.

Peter has owned the firm for the last 15 years and we've become good friends over the years as we have spent so much time working on projects. A year ago, he and his wife were going through a divorce and I became his support person, and the only person he could openly speak with. He told me things he knew I'd never repeat, and I helped him through a very rough time.