A Little Character Building

"One more and then I'm out of here forever, out of your life forever. It was annoying, but there is this one guy that you have apparently been seeing for years, but there are no pictures of him at all. I couldn't find any. There are pictures of his dick of course, cause you are a slut I have discovered, but nothing else."

"Well," I looked up at the ceiling and held onto the chair, "He, is my favorite." He was the one I WANTED to talk about with her. Without him, this would all be so fruitless.

***

We met at a wedding three years ago. He was wearing a gray suit and gray shoes to match his slightly gray hair. He had a crisp white shirt and an off-white tie. He was so tall and handsome, I couldn't keep my eyes off of him.

"Wait," Lita stopped me, "You went to a wedding three years ago? Did I go with you?"

"You didn't but my mother introduced me to you that night. I didn't want to go to the wedding and I didn't want to meet anyone. My mother sort of forced you down my throat, ha." I sat back down and poured some of the whisky I finished the bottle of wine. "My mother came over to my apartment the day before that wedding, she wanted to convince me to go. I was cleaning, I had the vacuum running. She walked in on me, I didn't hear her. She shut off the vacuum."

"I'm sorry," She said, "Have you seen my son? This is his apartment."

I was in a sleeveless white flowered dress, full E cup underneath. I had on off-white stockings and white pumps. My hair was flowing over my shoulders, I didn't know what to do. Years I have hidden my crossdressing and here was my mother looking at me. I'm sure ten years were shed from my life at that moment.

"Mom, don't get mad, it's me." She looked at me, she got mad. She picked up the vacuum and threw it toward me. It was pretty heavy. She yelled for twenty minutes, I stopped listening after three.

She then gave me an ultimatum, "Tomorrow you are going with me to Mickey and Angela's wedding and you are meeting a woman, whether you want to or not." She stormed out. She called me the next day and said she would be over in fifteen minutes. I was ready. I put on my only suit, I had a terrible time, I met a horrible woman. But... I met a wonderful man.

***

I knew I had to introduce him to my female self. He was divorced and older than me, and I couldn't take my eyes off of him. I didn't even know I was attracted to older men and usually, I didn't find men exciting unless I was dressed like a woman. He was totally different.

It was easy finding out where he lived, my mother knew him. I started hanging out with him a little bit, getting to know what he likes, what he liked to do. We actually had very similar tastes. I came up with all types of excuses to visit.

It was now almost a year since that wedding. He told me he was going to a cocktail party at some bar called Claire's, not too far from either of us. I decided Wendy was going to make an appearance.

I went to a salon to have my hair, nails, and makeup done. The girls made my hair long and straight, no wig, I wanted him to meet me with my real hair. I had my D cup breast forms on and nude pantyhose. My dress was sleeveless, long, and of course pink. It came down to my darker pink heels. The dress had a slit up the front, starting at the top of my thigh. I was sexy and sophisticated, exactly his type. The girls gave me dark pink nails and lips and my makeup was a little more dramatic than I was used to. I put on a new perfume and headed to Claire's.

It was a big bar and half of it was sectioned off for the cocktail party. It was for a law firm he worked with. I found a seat at the bar and waited until my courage came or I got drunk enough to go over, whatever happened first. I saw him enjoying himself, talking to everyone, he seemed very popular. When he was alone I went over and introduced myself. He seemed quite taken with me. he kept on glancing at my breasts and I was finding reasons to touch him. We left together.

He took me home and he kissed me at the door, he told me he knew someone who lived in the same development. I gave him my number and waited patiently.

He wanted me to come to a family party with him but unfortunately, I had my own family party to attend. I was upset, already I was letting him down. He called me a couple of days later and we went out for dinner. It was wonderful, he laughed at my little jokes and he complimented me the whole night. This was my life starting, then my mother got involved again.

She was waiting for me at the apartment. "I sent flowers to your lonely girlfriend, don't you even call her. She was going out with someone else when I ran into her. Somebody named Tyler or something."

I hated that she was so involved. She made me call and set up a date, my heart was not in it. My mother came with me and made sure that we had a good time, Neither of us did. I decided it was time for me to move and I wouldn't tell my mother I was leaving.

I called my new older boyfriend, we talked all the time, but I wanted advice on buying a house. Two months later I was all moved in and we started seeing even more of each other. We went to tennis games, out to dinner, museums, everything, I was falling in love. He wanted to sleep with me. I had to tell him. We had been going out for seven, eight months, though the times we had together were few and oh so far between. His family and ex-wife kept him busy. He was in the process of divorcing her, for years, but she wasn't having it.

One day he showed up at my apartment, he didn't call. He was knocking on the door. He called me by my boy's name and I started to cry. I figured he was going to beat me up, but I didn't care I have been lying to him.

"Why didn't you tell me?" He asked.

I didn't even know what to say. I asked him if I could get dressed up I didn't want to talk to him dressed the way I was. He said alright and sat down and had a drink.

When I emerged I was in the sexy red dress. I had on my long wig and big earrings. I took my time, I wanted to look perfect. I felt bad because I didn't want him to wait for me, I wanted to be a good girlfriend. I made him try some of the Japanese whisky to keep him busy. It would be nice if he had some alcohol in him. I didn't really know what I was thinking. I didn't even know what he was going to say to me.

When he saw me he smiled. "Here she is." And he held out his hands, I was nervous. "Please come here." I grabbed his hand and he pulled me to him. His hands were all over me. He was rubbing my ass through the dress, I felt him pull up the back and rub me through the pantyhose. he was so hard and he was horny, I really wasn't expecting that.

"You're not mad at me?" I whispered as he rubbed his body against me.

"Well, I had known for a while. I had a feeling that we met before meeting at Claire's. And, I'm never mad, actually, I think knowing this about you is better. It gives you a little edge." He looked at me and smiled.

I looked at him. "You are kidding me right?"

"Maybe. Does it matter?" He said and then he picked me up, I grabbed him around the neck. He brought me outside. I was standing on the steps, he wanted to take pictures of me. He took around a hundred, I was having so much fun, the people around the new house were watching us. He kept telling them I was his girlfriend, it made me feel so good.

"Hey, doesn't my girlfriend look great in that dress?" He yelled at a guy walking his dog. I started blushing.

We went back into the house and he pulled me to him, I felt him lift my tight dress exposing my pantyhose. My bottom was rubbing against his now hard cock.

"What are we doing?"

"Well first we are making love, and then we will come up with some sort of plan for our future." He laughed and kissed me. I grabbed him around the neck and he brought me to my bed. I took off his clothes and he took off my dress.

His mouth started exploring my body. "I'm sorry I didn't tell you I knew, we could have been making love for months." I smiled and pulled him on top of me.

His hands explored my body. "I knew these weren't real," He said while holding my fake boobs. "But I have to admit they feel incredible. My ex had the smallest boobs, these would put her to shame." He started sucking on the silicone nipple, he was making me so excited. I never would have imagined that would happen. He laid me down on the bed and started to bring down my pantyhose. He pulled off my heels with the stockings. He started to kiss my panties. He turned me over and started to kiss my backside.

"I'm so ready to fuck you, baby," He told me. I gave him some lube and he greased us both up. As he started to push into me I got nervous all over again. He had such a busy life, an awful lot of people depended on him. Did he really want to be involved with a slutty crossdresser? After a while, it didn't matter his cock entered me slowly and soon he was all inside. I forgot everything else. We fucked for so long, he rubbed my legs, my back and played gingerly with my hair. He made love to me the rest of the night. I had my first prostate orgasm, I was very proud of myself, it was a goal of mine. I let him come inside me the first time but the second time he came inside my mouth. He had very good aim, better than Hudson.

We laid together for...

***

Just then there was a commotion and someone was knocking at the front door of the house.

I got up and Lita yelled at me. "Where are you going?"

"To get the door this is my house." I opened and Lita's father was there holding a garment bag and some daisies, my favorite.

"Wow, look at you." And he kissed me on the cheek and then handed me the flowers. I let him in.

He went in and kissed Lita, "Here's that bag, I thought you were taking it with you. You left it on the porch."

She got up and looked at me and then at her father. "Don't you notice something is a little off?"

"All I notice is that Wendy is wearing my favorite dress of hers." He then grabbed me around the waist, kissing me and squishing the daisies between us.

I put them in a vase as Lita watched.

Her father shook her out of her trance. "So I guess you two finally had that little talk? Took you long enough."

Lita was still speechless, it was quite nice.

He chuckled, "Did you find anything incriminating on her computer dear?"

"What," I walked over and leaned into him, my hands still wet from the flowers. "You made her go through my pictures? I am officially cutting you off." He grabbed me by the waist again and kissed me in front of Lita.

"I had to give her the password." He laughed, and kissed my neck.

Lita finally spoke, "What... how long..."

Her father interrupted, "What's goin' on outside, there are a bunch of people in front of the house." her father then went to look out the window, through the blinds. "I had to squeeze my way in."

"Daniel, who's out there," I asked.

"I don't know."

Lita then yelled towards me, "Holy fuck! Dad's got a picture of you in his room, you're wearing that fucking peach dress. Shit, shit, I knew you looked familiar."

"Of course I looked familiar you have known me for three years."

"What the fuck is going on." She stood with her hands on her hips again. I just shrugged.

"Well honey," Daniel walked up to his daughter, "You are exactly like your mother, I just wanted Wendy to see what I had to deal with all of these years. It was a shared experience, haha. It was just a little character building, well... for the two of you." Her mouth was wide open. "Wendy hasn't been visiting you, she has been coming to see me." He smiled at me again, "And now we can finally pick out a ring."

'Ring'

The doorbell started to ring.

"Wait what time is it?" Lita asked.

"It's midnight." We told her.

"Shit, I didn't think anyone..." She walked to the window. "I sent an email from your girlie email account saying you were ready to get married, I even have the fucking dress. I sent it to all the men in your contacts. I told them at midnight you turn into a pumpkin."

"What?" I was way confused. Then the doorbell rang again. I answered it. Hudson and his girlfriend, Jane were at the front of the line with a bottle in their hands. Tom and Laura were behind them, looking down at my feet and then handing me some more flowers. There were over a dozen people, and I knew them all. I saw Mike, Ian, Hal, Roman, and a couple of other stragglers circulating in the back.

"Come in, welcome to me and Daniel's new home." Everybody walked in and I went and opened up another bunch of wine bottles and poured some Japanese whisky neat. "Welcome to our first party together, sorry it's so late." I was so happy to see everyone, and I was ecstatic to finally introduce them all to Daniel.

Hudson came over to congratulate me, of course checking out my lip color, "I'm glad you invited us I couldn't wait to meet your fiance. You talk about him all the time." I smiled over to Daniel he was giving Roman some legal advice.

Lita still had her hands on her hips. Too bad she didn't drink alcohol, she could forget about how mean she was to me, her new stepmother.

Jane unzipped the garment bag to see Lita's wedding dress, "Um, Wendy I think there's been a mistake. This dress is horrible."

"Ha," Me and Daniel laughed, I went into my new office, unlocked my walk-in closet, and threw away the key. I brought out my new wedding dress to show everyone. "Here it is." It was beautiful, I spent months with Sonya from the salon looking for the perfect dress. I showed it to Laura from the Shoe Warehouse, to see if she can find me heels to go with it.

She looked approvingly and shook her head. "I have so many size eights, feel like taking a ride?"

I did. We all did.

***

The End

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