Shopping for the Date, Breasts Included

I still can't believe I am going on a date this friday. With. A. Man.

I have so many conflicting emotions and thoughts. Fear. Excitement. Nervousness. Will he like me? Will he think I'm pretty? Why do I care. I mean, I've never meant him. I don't really know much about him.

I know he's older, in his 40s. Miss Emily only told me he's the kind of man lots of women would want to date. She says I should be proud he wants to take me out. Proud? I don't know. My head swims when I think about it.

Of course, Miss Emily wants to make sure she has me looking the way she wants for the big night on Friday. That involved shopping. Lots of shopping.

Last week, I spent trying on dresses, buying new shoes and a purse to go with the lacy pink dress she chose and even new lingerie. I wasn't surprised a new corset was chosen. I am usually in one. This one is stiffer despite how girly it is. It's all pink and white with lace trim and even little roses at the top of each garter strap.

The biggest surprise is that Miss Emily had realistic breasts glued to my chest. They aren't very big but I am constantly aware of their weight. They meant I had to get new bras to fit my new figure. I wonder why a man would want a sissy with fake breasts? Did I really think that?

Friday afternoon I have an appointment at the salon. I go regularly but this seems different. It almost feels like the first time I went to the salon. I wonder how my hair will be done and my makeup.

Part of me wishes it was Friday night already and part of hopes it never comes.

But I know it will.

<curtsy>

Catching Up

It's been a couple weeks since I posed and a lot has happened. It's hard to know where to start. I think I'll just do a post now about things and then maybe others if I think of what I want to say.

First, I had a wonderful week away with Miss Emily to a vacation home her family owns. Her sister was there for a couple of the days, but otherwise I was just her wife. We went hiking. Keeping up with her tough. But she said I looked "cute" in the L.L. Bean outfits she bought me.

I spent a lot of time kneeling between her thighs and she used her strap-on every day. I was so sore. But content too. I was even allowed to cum twice. I doubt that will happen soon.

The big bombshell was that Miss Emily told me she wants me to go on a date with her man's friend. To say this scare same is an understatement. She says every girl needs to experience it.

When Miss Emily makes up her mind she moves quickly. The date will be this coming Friday night. I am thankful that she and Jack will be along. My stomach is churning thinking about it.

Miss Emily tool me shopping last week for a dress to wear. I'll write more about that lately.

After serving at a party on Saturday things are back to normal this week as a think about going on a date. With a man. Yikes!

<curtsy>

Treated Like a Wife

Jack left after I served breakfast to him and Miss Emily on Sunday morning. I was in a daze. I was tired and I really didn't have many thoughts in my head. Once in a while I'd remember how his cock felt in my mouth when he came.

Since it was Father's Day we went to Miss Emily's parents house for dinner. It was a relaxing day and I was dressed in pink short shorts and a white tank top with pink trim. It was nice to be a wife more than a maid, although I did help with serving dinner and doing the dishes.

When we got home I received a treat when Mss Emily said she wanted me to stay up while she did some work in her home office. She finished up and called me to come to the den. She wanted to watch basketball (I'll never get the sports thing lol!). She had me on the couch next to her.

Usually I would be at her feet and if I'm luck I'd be allowed to worship them. This time she had her arm around me. I was so tired form the long weekend that soon I had my head in her lap as she cradled it.

I could feel her fingers in my hair. It was so peaceful and I felt so peaceful. I guess she got bored with the game because she turned the TV off and led me to her bedroom. She kissed me hard and I felt week. I could feel the strength in her.

I knew was going to get her strap-on and that she would use me. I was excited. It was like my sleepiness was gone.

She did fuck me and hard. She had me begging for more. She doesn't ask me to beg for that it just seems to happen. I was still locked in my chastity device but i could feel the dripping.

Finally she was finished. She allowed me to sleep with her in her bed. And when I awoke she had left for work. That is rare.

Somehow she knew exactly what I needed.

How does she do that?

<curtsy>

Nagging Questions?

One of my readers offered his (or is it hers? hard to day since the comment was anonymous) thoughts about my relationship with Miss Emily.

I admit I was shocked. Maybe I have not been clear enough about I fell about her. I adore her.  love her. She is the best thing that ever happened to me. Serving her needs comes naturally.

Despite that I do question myself. I always have. I don't know if that will ever change. Add to that the fact that I am coming to terms with the fact that I am better off as a wife and servant and I just can't help feeling what I am doing is against the way I was brought up.

For most of my life I imagined having a wife and a job and a family. But from the first time I met Miss Emily I wanted something else. She understood me better than I understood myself. It was so easy to be with her and to let her lead.

We have talked many times about our relationship. My place is clear as is hers. I tell her when I am upset or concerned or confused. I know she loves me by the way she cares for my feelings. That doesn't mean she does what I want her to do but she is aware of my safety and emotional well-being.

Having read about female-led relationships on the internet, I know what I have found is rare and beautiful. But I also know that is a long process for a sissy like me to accept the truth about herself.

I adore Miss Emily for showing me the way.

<curtsy>

Serving Others

Last night Miss Emily was home and that meant I was back to being a maid. This time, we weren't alone. She invited her sister over for dinner and to watch the hockey game. Her sister is every bit the dominant that Miss Emily is. She finds it amusing to out me on the spot.

Last night was no exception. Miss Emily had ordered me to dress in my French maid's uniform. That isn't unusual when company is over. When I answered the door i curtsied as I have been taught. I have spent hours practicing the correct way to show respect. But my curtsy wasn't good enough for Miss Amanda.

"is it the best you can do?" were her first words to me. She made me do it over ten times until she said "I suppose that will have to do." I can't explain how humiliating this was and how near to tears to I was. I was sure Miss Emily would be disappointed in me. But Miss Amanda didn't say anything, at least that I heard.

I served them dinner. I had prepared steak, asparagus and baked potatoes (which must be cooked in the oven not the microwave). Other than pouring wine and clearing dishes I was ignored as they talked the way sisters who are close do.

As always, my dinner, a salad and small slice of steak, waited until after they had finished. While they watched the game they continued to drink wine. Miss Amanda enjoys making me uncomfortable. At one point, she asked me how I felt about being a cuckold.

That was the first I knew that Miss Emily had shared that with her. I was kind of in shock I think. I couldn't think what to say. I looked to Miss Emily hoping she'd rescue me from having to answer. All I saw was the look she can give me that I know means I'd better obey.

I told her I was happy for Miss Emily and her desires were all that mattered. Miss Amanda said "You are fucking sissy." They both laughed.

I wanted to crawl in a hole. Yet I could fell a wet spot on my panties. I felt so pathetic.

The rest of the night they watched the game and I filled their wine glasses. Miss Amanda was a little drunk and Miss Emily insisted she stay in the guest room.

This morning I washed her clothes before she awoke and served her breakfast before she left for work. Miss Emily had left earlier.

I'll never understand why being treated like a servant excites me, but it does. sigh.

<curtsy>

The Cuckold Path

I actually don't want to write about this but Miss Emily has ordered me to.

I was afraid Miss Emily had something big in mind when she texted me yesterday and told me she needed to have a talk with me when she got home. That doesn't happen much and neither does her telling me she wanted to see her wife. I am almost always in a maid's uniform at home.

Deciding what to wear is always hard for me. I have a few outfits but I always worry she won't approve. I had trouble but Misty helped me choose a pink linen dress while we chatted. It's sleeveless and comes just above the knee. It shows off the necklace Miss Emily gave me.

I have to wear a corset to fit into it. It's uncomfortable but it makes feel pretty and more feminine. I added a little more makeup than usual and put my hair up. I usually wear studs but for some reason I decided to wear the drop earrings. They felt heavy.

Then I waited for Miss Emily to come home. I was fidgeting and tired. I had tried to take a nap but I was too nervous to sleep.

When she got home I she had a big smile on her face. She kissed me and told me I was pretty. I felt so good hearing that. She whispered in my ear and I could feel her hand rubbing my butt through the dress. She told me we needed to talk and that if I was a good little sissy wife she might fuck me with her strap-on later.

I moaned. I wished I hadn't. It makes me feel silly. She laughed a little and gave me her coat. She told me to get us each a glass of wine and meet her in the den. She rarely allows me to drink and this made my stomach churn more. I was truly worried.

I could barely carry the wine into the den. My hands were shaking. She actually told me to sit next to her on the couch. That doesn't happen much. I usually am sitting at her feet.

I was surprised that she seemed nervous. She is always so confident. I wondered if she wanted me to leave or something. I felt sick. She stroked my cheek. That felt good. But I thought I might cry.

She told me she loved me but that she has needs a sissy could never fulfill. I knew what was coming and the tears started to flow. She stroked my cheek again and held my hands in hers. I felt awful thinking about what she was saying.

She said she was going on a date tonight. I think I closed my eyes and tried not to think. I felt so bad. She told she was going with her partner at work. I'd met him a long time ago when I worked at the office. I didn't remember much but I know he was tall and looked athletic. Not a sissy.

After she told me Miss Emily put her arms around me. I started sobbing. I felt like a child. She tried to comfort me. Had me blow my nose and drink some more wine.

The rest of the evening is hard to remember. She talked about how she wanted me to help her get ready for her date. I know she told me she expected me to be an obedient sissy.

We ate dinner. I was allowed to eat pizza and have more wine. After that Miss Emily took me to her bedroom and kissed me softly.

Then she used her cock on me. She was gentle and fucked me slowly. I was locked up but I could feel my clit dripping.

And then she allowed me to stay in her bed all night. I didn't sleep much. My mind was racing.

Now Miss Emily is getting her hair done.

I know I don't have a choice but this is a scary day.

<curtsy>

Romance and Humiliation

I am back from California and it was quite a trip. Miss Emily treated me like her bride. We had some candlelight dinners and she even allowed me to drink wine, which I am usually not allowed to do. The first glass was on the plane. I had never flown before and I was pretty nervous.

I had six orgasms while we were gone. Each time I licked up my sissy cream. Miss Emily loves to see me do that. She used her strap-on on every day we were gone and also had me lick her till she had two or three orgasms.

Being in San Francisco was different. Stores we went into didn't have any problem waiting on me. Miss Emily purchased several outfits for me. My favorite I think is a pink linen suit. It has pants and a skirt.

Besides the romance, which included a trip to Carmel for two days, Miss Emily found ways to humiliate me. One afternoon she took me to a store that sells fetish clothing. The women there dressed me in different outfits. One was a plaid schoolgirl dress with knee socks and mary jane shoes. Hearing them tell Miss Emily how men would just love a sissy dressed like that had me nearly in tears.

I also got a new chastity cage. It's pink. One of the women at the store suggested it. She laughed when she saw me unlocked and that I needed an extra small cage.

The most humiliating thing that happened was in a bar one evening. I don't know if Miss Emily planned it or not. A man came over and told Miss Emily what a cute sissy I was. They started talking and he bought us drinks. He was older. I think maybe 60 or so. He started asking me questions. I was so embarrassed when he asked me if I had ever sucked a man's cock. I told him I had never touched one.

He told me how special I was and took my hand placed it on his crotch. He rubbed my hand across it and I could feel his cock jump. It felt so big. A lot bigger than mine. I didn't realize it even but he took his hand off mine. Then he said to Miss Emily that I must like touching his cock because I kept rubbing it. They both laughed. I felt so ashamed.

 I was glad it didn't go any farther.

One other thing that happened is I got my first tattoo. It's a chain of pink daisies around my left ankle.

I think I am still thinking about everything that happened on the honeymoon. I will write more later.

Today it's back to housework and lots of laundry.

<curtsy>

The Wedding Night

Miss Emily has asked me to post about the first time she used her strap-on on me. It was our wedding night. And yes I was a virgin. I had never penetrated a woman or been penetrated other than by Miss Emily's fingers.

At our hotel she had me go in the bathroom to get ready. She told me to wear what I found there. What I found was a white box tied with a big pink bow. Inside was a white lace nightie. It was short. It had a matching garter belt, panties and white stockings.

I was shaking as I put the clothes on. My penis was hard inside the lace panties, although there was only a small bump there. I decided to slip on the white shoes I had been wearing. They had a two inch heel. There was a tube of pink lip gloss on the counter. I used it. Looking in the mirror I felt embarrassed and excited.

When I walked out to the bedroom I saw Miss Emily with her back to me. As I approached her she turned. I looked from her face down toward her feet. I was shocked by the lifelike dildo she was wearing. It was long and thick. She later told me it 8 inches.

She stepped toward me and pulled me to here in her arms. She kissed me hard on the mouth. I felt so weak. I could feel her dildo against my stomach as her hands squeezed my butt. She broke the kiss and told me how pretty I was. How perfect my mouth would look on "her cock."

Her hands pushed on my shoulders and I found myself on my knees. She told me to kiss the head of her cock. I did. I was so scared and nervous. Then she told me to worship it. As I did she told me what a good little bitch I was and that I was made to suck a cock.

I knew she was going to fuck me but I tried not to think about that. At one point she grabbed my hair and rammed the cock in an out of my mouth. I could her moaning. I felt violated. But I wanted her to keep doing it. Strange to feel that way.

Finally she pulled away and said it's time to consummate our marriage. She took my hand and led me to the bed. She slipped my panties off and had me get on my back. She used pillows to prop up my hips and lubed me. I could feel the coldness of the lube as her fingers worked inside me.

Finally I watched as she lubed her cock. I was shaking and ready to cry. She stroked my face and told me I was going to love being fucked.

She bent my knees and pushed my legs back. I felt the head of her cock at my hole. I begged her not to to do this. She said "hush." She locked her eyes on mine. I wanted to look away but I couldn't. Without warning she shoved her cock inside me. I cried out and the tears flowed down my cheeks.

That made her smile even more as she started to push deeper in side me. Then she started fucking me. She was rough and relentless. She stroked my little cock (my clit, now) and told me not to dare cum till she gave permission.

Despite my tears I started to meet her thrusts. She pulled mostly out and stopped. I wanted to feel her penetrate me again. She just waited. Staring at me. Daring me in a way. Finally, I begged her to fuck me.

I kept begging until she started again. Finally, she told me to cum. She moved her hand off my clit and then I came all over my stomach. She fed me my cum. And then she pulled out of me.

I was sobbing. I was scared, humiliated and excited all at once. I fell asleep as she held me. She fucked me in the middle of the night and I came again.

In the morning I received my wedding present from her. A cb-6000 chastity belt. That was a shock.

But i was different now. I was more broken by her in a way that I hadn't been before. I felt humiliated and yet I adored her even more.

<curtsy>