Jackie Pt. 03


Monday was a very depressing day. I knew I wouldn't be spending the night with Angie till the following weekend if we had it free. We had agreed it was just too time consuming for me to come over and still have to work the next morning. That morning I almost cried while I removed my press on nails. Angie consoled me by telling me the weekend was only five days away.

Over the next few weeks we had developed a game plan. During the week we would go out to dinner each night and after the first week Angie gave me a credit card with my name on it so I could pay for our meals. She told me she didn't want anyone thinking I was a kept man.

On the weekend I was always her girlfriend. We would shop together, go out to dinner and the movies together and often we would go out dancing together. The weekends were great and I basically survived the work week till I could put on a dress for Angie.

Thanksgiving was wonderful as we had off from five o'clock the Tuesday before till nine o'clock on the following Monday. I spent the entire week end as Jackie. We fixed Thanksgiving dinner together and celebrated the holiday like we were family. When Monday came I was totally depressed and I think Angie was too but she never said anything.

Seeing the office would be closed for almost two weeks over the Christmas and New Year holidays Angie had decided to go away for that time. She had made her plans the previous June and of course her plans didn't include me seeing we weren't working together at the time.

Angie told me she wasn't going with out me, but she had problems getting me on a flight. It wasn't until two days before her flight was to leave before she finally got me a seat. We had to scrabble to get packed in time, as we really didn't think we were going.

For ten days I was Angie's boyfriend on a tropical island in the Caribbean. She wanted me as her girlfriend a few days but that wasn't possible as we couldn't explain where I came from. We were sure some one would have noticed the resemblance.

Our last day on the island we were sitting having dinner on our patio when Angie took my hand and said. "Jack honey I think its time we start telling people at work we're dating. When we get back I'm going to tell my managing partner that we are a couple."

We had talked about this a few times over the last two months. I for one wasn't sure how it would be received. There was usually an unwritten rule that couples couldn't work together, but I never heard of it at our firm. I really thought Angie was taking a chance with her career.

"I know I am sweetheart," She told me after I voiced my concerns. "But I want them to know about it before I ask you to move in with me. I don't want any surprises. Besides if they don't like it I'm more than willing to strike out on my own."

I was completely stunned by her statement. Not so much about her striking out on her own, but that was surprising in and of it self. I was even more stunned by her statement about asking me to move in with her. I had hoped we would but I also thought that was wishful thinking. I never knew she entertained the thought too.

I was so stunned I didn't say anything for a few seconds so Angie asked, "What's the matter sweetheart don't you think I could make it on my own?"

"Of course I do. You would be a success in no time." I told her before I asked, "Were you really going to ask me to move in with you?"

"I've thought about it quite a bit these last couple of weeks." She told me as she squeezed my hand tighter. "I know you're very depressed when we have to go back to work on Mondays and I'll tell you I hate Mondays as much as you do. I think its time we live together. It really makes sense don't you think?"

"Of course I think it makes sense but I'm pretty partial." I told her in jest.

Angie laughed and said. "I am too my love. I'm partial to having you and Jackie around me all the time. I think you should move in next weekend though I want you to take the money you were paying for rent and put it toward your school loans. I can't see you paying all that interest when you don't have too." I couldn't have agreed with her more.

The first day back in the office Angie went to her managing partner and told him we were seeing each other. Angie told me the partner couldn't have been happier and there was no reason to break us up. Word spread quickly through the firm that I had tamed the queen bitch, but of course it was she that tamed me.

The following weekend I moved into Angie's house. I really didn't have all that much to move. Of course I had my clothes most of which Angie bought for me. Except for a few personal belongings everything else I either gave to some one else in my apartment building or just threw away. Angie hired a service to clean the apartment so I could get my deposit back.

Two weeks after I moved in I found myself at home alone. It was a Saturday afternoon and Angie had a very important meeting with the partner from the firm. Every one at the firm knew it was the day they divided the spoils from the previous year and handed out bonuses to all the partners, junior partners included.

Seeing I was home alone and would be most of the day I decided it was a good day to clean. The house wasn't that dirty but it needed a good dusting and vacuuming. I finished the down stairs in no time so I went upstairs to clean the bedrooms.

As I was vacuuming the floor I found a pair of Angie's heels under the bed so I went to put them in her closet. As I walked it I realized it was the first time I had ever been in her closet. It was a large walk in closet with room to hang things on both sides of the door. In the back of the closet there were shelves for putting folded articles on.

After putting the shoes where they belonged, my eyes drifted to the shelves. On one of the shelves I saw Angie's strap on harness and her cock. There were three other dildos on the shelf that I hadn't seen before. There was also a pair of fur lined handcuffs and several magazines.

I picked up one of the magazines and noticed it dealt with cross dressing. I saw on the cover there were articles about make up tips for men. I figured this was where Angie had gotten all her information. I grabbed a few of the magazines and went back to the bedroom to look them over. I figured I might learn a thing or too.

The first two magazines were very informative though I already knew most of what was written. The third magazine was informative as well though not in the same sense as the first two. The third magazine was called Sissy World and it told how to turn a man in to a sniveling sissy.

The magazine had more pictures in it than actual words. In the pictures I saw men dressed in girls cloths some of which were very sluty looking. These men were being forced to do things with other men and their own women or mistresses as the called them in the magazine. These mistresses would fuck their sissies and make them have sex with other men. The mistress even had sex with other men while they berated their sissies, telling them they were worthless men.

It was all pretty demeaning toward the sissy and I could see myself in their shoes or should I say heels. After all wasn't Angie doing much the same to me? Wasn't she turning me into a sissy?

What was really odd was the fact that while I was disgusted with the pictures I was also turned on by them. From the moment I opened the magazine and saw the bound up sissy my cock became hard. My hands were also shaking each time I turned the page to a new set of pictures. That was how Angie found me.

I hadn't heard her come in to the house as I was on the second floor. She told me she tip toed up the stairs in case I had lain down for a nap. She found me lying on the bed still dressed in my short A-line skirt and crop top cashmere sweater.

Before I even knew she was in the room she said. "Hi love, what do you have there?"

She was standing next to the bed looking down at me. I closed the cover of the magazine and said with as much distaste as I could muster in my voice. "I guess it's your training manual." I saw recognition in her eyes the moment she saw the front cover.

Most people would have denied knowing what the magazine contained. Others would have accused me of snooping into their personal belongings. Angie wasn't like most people she simply sat on the bed and picked the magazine.

I watched as Angie went over her answer in her head. After a minute she said. "I'm sorry you found this. I really should have tossed it out the day I bought it." She pointed to the other magazines on the bed and said, "I thought it was like those, you know something to help with your girly side. I didn't know it was a sex magazine."

Her reason sounded plausible and to tell the truth I wanted to believe her. I couldn't imagine the woman I love doing something like that to me. "You mean you don't want to do those things to me?" I asked hoping she would say no.

"Oh no baby I would never do these kind of things to you." She told me. She then flipped open the book and pointed to a picture. The picture showed a sissy bound and gagged on his knees. The mistress was standing over him with a riding crop posed to strike his ass. You could see he had been hit several times already by the red streaks crisscrossing his ass.

"Look baby," She said pointing to the sissy on the page. "Have I ever done anything like that to you?" Of course I had to shake my head no. "Don't you think I would have done it sometime in the last three months? Have I ever made you feel bad about wearing clothes I bought you and picked out for you?" Again I had to shake my head no. "Of course I haven't, I am so lucky you do this for me. I know you like it too but really you would never have started it if I didn't want you too."

When I thought about it I could see she was right so I said, "I'm sorry Angie I guess I let my imagination run a way with me. You've never done any of those things to me and I'm sure you would have by now. I'm sorry I doubted you."

"I'm sorry I kept this thing, tonight after we get back we'll burn it in the fire place together." She told me as she gave me a hug.

"Where are we going?" I asked.

"I'm taking you out to dinner tonight. I have some really good news and I want to celebrate"

When I asked what the news was she wouldn't answer so I asked, "Where are we going and how should I dress?"

By this time I was picking out my own cloths but I still had to ask how I should dress. Angie knew I was asking if I was going as Jack or Jackie. Even though she would always say it was my decision she would make her preference known.

"As you know love I am as happy to be in Jack's company as I am in Jackie's but tonight I would like Jack to accompany me. This news concerns him as well." She told me with a kiss to my cheek.

It took me a while to get ready. First I had to remove all my makeup and the nail polish I had put on the day before. My own nails had grown out and now I didn't have a need for the press on type unless I wanted really long nails. I also had to use the solvent to remove my breast forms. Of course I had to take a shower.

The clothes I wore now were so different from the ones I wore when I met Angie. The suit I was wearing cost three times what I would have paid for a suit. Angie insisted my suits be of high quality. I also wore high quality shirts but that was to hide the lingerie I wore underneath. My ties were made from silk instead of the polyester ties I wore before. In my ears instead of the gold start posts I wore before I now wore diamond studs that Angie gave me for a Christmas present.

The pant legs of my suite were two inches too long but that was so they would hide the fact my shoes had a three-inch heel. That was so I was the same height Angie was when she wore heels. Angie wasn't bothered by my slightly shorter height but she said it would look better if we were the same height to others around us.

Angie had also showered and changed for dinner. She wore a burgundy knit dress that stopped five inches sort of her knees. It had a plunging neck line and left the insides of her breast exposed for the entire world to see and it was tight enough to show off her figure to perfection. Around her neck she wore a gold heart shape locket that held my picture. The locket was a Christmas present from me. For shoes she wore a pair of burgundy pumps that had a three inch heel that was so thin you had to wonder how it could possible support her.

As always Angie drove her car to the restaurant, she loved driving and she would never give up the driver seat to anyone. I for one didn't mind as it gave me the chance to look at her while she drove. I know most guys would bristle at this but they weren't looking at what I was.

The restaurant we went to was one of Angie's favorites. We were well known as we went to the restaurant once or twice a week for the last three months. Jackie had never been to the restaurant as I always showed up as Jack.

After checking our coats at the door Angie took my arm and we followed the mater'd to our table. A long the way she whispered, "Jack honey, order a bottle of Dom Perignon once we're seated."

This surprised me. Normally Angie didn't drink champagne. She said it was for special occasions. Also she didn't order a Dom Perignon at the drop of the hat. This must have been a very special occasion. When I told the mater'd I wanted the bottle of champagne even he seemed surprised as it was the first time we ever ordered it.

Once the wine was poured and our dinner orders were taken Angie picked up her glass and said. "Congratulations Jack you have been promoted to Senior Research Assistant."

For a second I was taken aback. I had been promoted with out even knowing it. Then I realized by taking the position I would be going to work for one of the full partners instead of Angie who was a junior partner.

Angie saw my reluctance to pick up my glass so she asked. "What's the matter love don't you want the promotion?"

"Not really, if it means I won't be working for you any longer." I told her.

Angie smiled her warn dazzling smile and said. "I told them you wouldn't take the promotion and leave me so they told me I had to take my promotion too. I am now a full partner at Allen, Allen and Rogers."

I was stunned by this news and said. "That's great Angie I so happy for you."

"I'm happy for the both of us sweet heart and apparently I owe my promotion to you." She told me as she took a sip of the wine before continuing. "Apparently they were ready to have their first woman partner but not a lesbian. Once I told them we were seeing each other and we were living together they figure I really wasn't a lesbian and it was okay to promote me. As you can see if you hadn't come to work for me I wouldn't have made partner." I was sure that wasn't completely true but I really couldn't argue with her. We merely toasted to our mutual success.

After a very enjoyable dinner we went dancing for an hour or two. After dancing we went home and made love like two teenagers who just figured out what sex was. We were still going at it when the sun started to rise in the east. By then we were so exhausted neither one of us had the energy to shower so we passed out as we were, covered with sweat and cum.

Two weeks later was Valentines Day. Seeing it was on a Saturday I thought I would do something special for Angie. I had an idea to dress up as a French maid and be her servant all day. Actually I got the idea from the Sissy world magazine. I remember seeing a picture of a sissy dress as a maid in the book.

I really didn't know where I could find a maid's uniform but I had thought I could go to the store where Angie bought the gaff from. She had gone back a few times to buy more gaffs and she told me they had a large selection of clothing including costumes.

I had procrastinated for so long, as I was nervous about buying a maid's uniform that I didn't get to the store till the day before Valentines Day. I can't tell you how nervous I was entering the store. In fact I sat in my car for about a half hour to work up the nerve to go in. After all, the store was supposed to cater to men that dressed up like women. I mean, what would I do if they realized the uniform was for me. I was planning on telling them it was for my girlfriend.

After finally getting up the nerve to go in I walked into the store. The first thing to hit me was the smell. There was the pungent aroma of leather and the tangy scent of latex. Under those two scents was the smell of lavender and cinnamon.

The part of the store I walked into was the back of the store where the sexual paraphernalia was on display. There were several strap-on harnesses on display each with a large dildo fully engaged. There were also a variety of dildoes and vibrators on display.

As I walked further into the store I could see Angie was right the store was filled with all kinds of clothing. There also shoes that looked too big and too wide for women's feet but they did look like women's shoes.

As I looked around for where the costumes could be I felt a tap on my shoulder which caused me to jump. When I turned around a very tall middle age woman was standing in front of me. She was well over six feet tall, with the heels she was wearing I say she was six three or four. She had beautiful long blond hair, pale skin, blue eyes and cherry red lips. Her smile was quite warm.

I'm sure she saw the surprised look on my face as she said. "I'm sorry to startle you honey. There is nothing to be scare of in here, we don't bite I promises. My name is Anna is there something I could show you," She asked as she held out her hand for me to shake.

"I was looking for um... a maid's uniform for um... my girlfriend." I told her haltingly.

Anna's smile lit up her face as she said. "Mm you would look wonderful in a maid's uniform, French no"

"No, I mean yes a French maid's uniform, but it's for my girlfriend not me." I told her nervously.

Anna's right hand came up and she touched my left earring and said. "Of course it's for you girlfriend sweetie. Please follow me and I'll show you what I have."

Anna walked past me and I step in behind her. She had an exaggerated wiggle to her walk that seemed to really get her hips moving. From the view I had she had a really nice bottom and with her long legs, it was an excellent view to follow.

After we passed the leather section we walked into a section that had a wide selection of maid's uniforms. Anna stopped turned toward me and said, "As you can see we have an extensive selection of maid's uniforms. Now do you happen to know what size you, I mean your girlfriend wears?"

"Yes she wears a size five in most things." I told her, which was the size I wore.

Anna smiled and said, "Are you the same height." I nodded my head. "Was there any special style you were looking for or is this for Valentines Day."

"It's for Valentine's Day. I doubt she'll ever wear it again." I told her.

"That's sweet honey, I just happen to have a pretty little thing that was just perfect for Valentines Day." Anna looked through the rack of uniforms and finally pulled one out before saying. "Here it is and a size five just like you wanted."

The uniform was made of cherry red satin. There was a heart shaped apron made from white lace. There was also lace around the collar and the cuff on the short sleeves. The skirt was positively micro in length and there was an underskirt made of several layer of stiff crinoline. It looked quite sexy and I quickly said I'd take it.

Anna smiled again and said. "I knew you would love it. Now would you like to try it on, Oh that's right it's for your girlfriend? You have to pardon me I am so use to men coming in and buying pretty things for themselves. You do know we cater to cross dressers don't you?"

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