Hit the Button Pt. 01

This story is about Cross-Dressing and a Loving Relationship. If you're not interested in these topics, I encourage you not to read any further. I'm still trying to become a better writer, so please be understanding with any of my errors or mistakes. (The Title will make sense in later chapters)

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Lisa and I have been together since pre-school. You see, our moms became friends since our first day at school, and we've been as close as twins since we met. Our moms became best friends, and Lisa and I had weekly play-dates at her house, which had a pool and was where the women liked to chat. Because we spent most of the time at her house, I learned to play her games, which included dolls, playing with her Barbie collection, and tea parties. I never gave it a second thought and enjoyed being her friend.

The two of us even looked similar, with the same blond hair and blue eyes. Even our height and weight were similar and were often mistaken for twins. We became inseparable, and throughout our school years, did everything together. There was never a fight or a time we can remember being upset with each other. It was uncanny how well we knew each other, and often completed each other's sentences. Everyone always assumed we would be together forever, but of course life can throw a curve ball and change your world.

One weekend in our junior year of high school, Lisa came over excited when she told me they accepted her to go to Stamford on an academic scholarship. They accepted me at Ohio State for engineering after being turned down at Stamford. She was sad because she knew they did not accept me to her school and that it would be difficult for us to be apart, and tried to ease the pain.

"It will only be for a few years and we can see each other on holidays. We can FaceTime every night and be there for each other. Besides, it will be good for you to make some new friends and meet some new people."

After we cried and held each other, we both knew we would not be together and that it was time for us to grow up and spread our wings. My four years away went quickly, and I graduated with top honors and was offered a job in California as an engineer for a government contractor. Lisa applied to Law School and remained at Stamford after I started my job. We remained close but we both dated other people and actually had no intimacy since high school, which never included actual intercourse but lots of oral activity.

Life went on and I learned that Lisa was engaged to one of her classmates. I was happy for her and sad that my closest friend was going to be out of my life. After several years at my job, I became successful by coming up with some patents that made my company a great deal of money and recognition. Lisa was now an attorney at one of the large firms in LA, married to her college sweetheart going on 4 years. I dated and had lots of friends but nothing serious as I dedicated my time to work and my career.

One year later:

It was mid-July, and I was celebrating my 25th birthday with some friends in San Diego one evening when I ran into Lisa, who was in town and heard about my celebration from my mom. It was the best birthday present I could wish for, and we spent a few hours after the party catching up.

She had just signed her divorce papers after catching her husband having an affair with one of her friends and was devastated. I consoled her and got her laughing about old times. It was like we were never apart. To make a long story short, we became a couple again after that night. She put in a transfer to work out of the San Diego office, and we moved in together three months later.

We picked up where we left off and we both knew at that moment that we were destined to be together. After a short time, we decided to get married and spend our lives as one. A month after our wedding, she asked me something that shocked me to my core, and revealed a secret that only my sister and mother knew about.

My sister came to town a few days before the wedding, and Lisa and some friends went to her bachelorette party a couple of days before our planned wedding. Apparently, after many drinks, my big mouth sister asked Lisa if I still liked to cross dress. She said it as she laughed and thought that Lisa would have known, since we had been so close.

"You really didn't know? Oh my god, you two have been so close, I can't believe he never told you. I feel bad now, don't hold it against him. I'm sure it was just an adolescence thing."

"Nope, I had no idea. He never told me about that, which is odd because we knew everything about each other. It's probably my fault because I made him play all my girly games and with my dolls when we were little. We're almost the same size so my clothes will probably fit him, I think it might be fun to dress him up sometime. I'll let you know."

The girls enjoyed the party; we married a few days later and enjoyed a week in Hawaii for our honeymoon. It was romantic, and we both knew we had found our soulmates and would be together forever. It was our destiny.

Our sex was great, not wild rodeo sex, but loving sex. As I wasn't exactly large down there, I learned to please Lisa with my tongue and always brought her off with amazing orgasms. She always said she never came as hard as when my tongue made love to her sexy, smooth pussy. Lisa had the most beautiful pussy I had ever seen, and she kept it shaved and smooth, which I enjoyed when I pleased her with my mouth. When she was excited and about to come, her clit would enlarge and pop out of her tight pussy lips, and I knew exactly how to suck and tease it until she was screaming and pushed me away.

A month after we were back from our honeymoon, she brought up the cross-dressing question after another great night of sex. We were cuddled together after another wonderful love making session when she asked me about it.

"Jason, why didn't you tell me you used to dress up like a girl when you were younger? I thought I knew all of your secrets, so you can understand why I was surprised when Sally asked me if you were still cross-dressing."

My entire body tensed up, and I felt my stomach do a flip as I realized that my big mouth sister told Lisa my deepest secret, which only she and my mom knew about. I tried to act cool and nonchalant but it was obvious she reached deep into my soul with that question.

"Well, it was so long ago I didn't think it was important. I was embarrassed when mom caught me and didn't think it was something I wanted to share with anyone. I'm sorry I didn't bring it up, but since it was so long ago, I didn't think it was important."

"You're right, it's not important. I was just surprised I didn't know about that part of you. I mean, we've always been so close I really thought we knew everything about each other. Is there anything else I didn't know about?"

"No baby, that's my darkest secret. I always tell you everything and I know you do the same, which is the most important thing in our relationship. Our total honesty and openness are something I've never had with anyone else except you, and I love that we trust each other completely. I'd never lie to you, and I know you would never lie to me."

We kissed and hugged and eventually fell asleep after several minutes in each other's arms. Life continued, and our marriage was perfect. We spent every minute together, making sure the other person was happy and satisfied. We were again as close as any couple would be and we loved each other unconditionally.

One Saturday after Lisa came home from the cleaners, she was putting her dresses away and came out of the closet with a dress in a plastic bag. She held it up to my body as I stood there wondering what she was doing.

"Sweetheart, I just saw this old dress in my closet, which I never wear anymore, and thought that it probably would fit you. Would you let me play dress up with you today? You remember how we always played dress up with my dolls, well today I'd like you to be my real-life doll, and let me dress you up. What do you say, would you let me do that?"

I felt my face turn red from embarrassment at her request, but at the same time, I felt my excitement stir at her question. Trying to remain calm and not give myself away, I told her I'd be happy to be her doll for the day and it would be like old times.

"Goody, I can't believe you'll let me do this, I love you so much! It will be so much fun, and I promise you'll make you very happy in bed tonight, as a repayment for being so kind and letting me do this."

"I like the sound of that, and I'll take you up on your repayment in bed tonight. I hope you're ready for a fun night."

"You will be smiling all night, baby, I promise. Now, I want you in the shower and I want your legs shaved and smooth. Use my lotions and razor and then come back in the bedroom and I'll get things ready."

I probably should have protested and acted like I didn't want to, but the truth was that I did want to play dress up with her. In fact, it had been a fantasy I kept hidden, and never in a million years thought I would ever have this opportunity. With this in mind, I was going to do whatever she wanted and just enjoy everything about it. The best part is that it was her idea, which left me guilt free. After all, I was doing this for her.

True to her word, there were piles of lingerie on the bed and several pairs of shoes next to the makeup table. She had a big smile on her face, and was clearly going to have fun with me as her real-life Barbie Doll for the day. She had me stand in front of the bed and picked up several pairs of panties and bras until she selected the matching set she wanted me to wear.

She was happily surprised with my familiarity with the garments, and commented on how nicely I put on the pantyhose without getting a run in them. She placed some padding in the bra, adjusted my pantyhose, and then took a step back to admire her work.

"That looks perfect, and it looks like most of my things will fit you. You're only a couple of inches taller but we have similar body shapes, except for your bust, which we can easily fix. Oh, this is so much fun. I can't believe you never told me about this, we could have played dress-up all those years when we were younger!"

She sat me at her makeup table and expertly used all of her products to create a perfectly feminine outcome to my face. She smiled as kissed me when she was done and then started working on my shoulder length hair, using clips and hairspray. The image in the mirror made me smile when I realized I could pass for her sister. With the same color hair and eyes, and being similar height, we could actually pass as twins with a little more effort.

"Oh my goodness, you're beautiful. I mean, you really are pretty, and this is just the first time we've tried this. You have to promise me we will do this again, I just love dressing you up like this. What do you think, how do you think you look?" she said as we stood next to each other in the full-length mirror.

"To be honest, I can't believe I look this good. I mean, you really did a number on me, and if we wore the same outfits we could pass as twins. I definitely will let you do this again, as long as you're OK with your husband looking like your sister," I said with a grin.

She laughed, "Oh honey, I don't care about that. You're my soulmate, and I love everything about you. We are one, and I could never think badly of you. I'll love you forever, no matter if you're in a dress or my macho hubby. Right now, I like you in a dress, and it's making me wet. I need your tongue inside my pussy, right now, baby."

For the next hour I brought her to three screaming orgasms with my mouth and another one when I came inside her to finish the evening. We collapsed, and I fell asleep still dressed in her lingerie and makeup. It was one of the most exciting sexual times we've ever had together, and she commented, 'we will need to do this more often.'

All of the dressing brought back so many memories. They were memories that I had suppressed but were now coming to life. Wearing that cute dress with the lingerie and high heels felt electric and exciting. And being able to share this with Lisa was indescribable. It was a dream come true, and I knew we would do this more often.

We repeated the same game every Saturday until Jason returned Sunday morning. There were now seven outfits that Lisa didn't wear that became part of Amanda's wardrobe. Amanda became my name when dressed, which was always a one of Lisa's favorite girls' names.

She made space for a section of her walk-in closet for Amanda, and soon I had a nice selection of clothes to wear each week.

Lisa's sister was a makeup artist in LA and over the years had taught Lisa some of her makeup skills. After several dress up sessions, Lisa started teaching me the same skills, and after a few weeks we were putting on our makeup in front of the mirror side by side. Two girlfriends getting dressed for a day of shopping, dining, and dancing. Yes, dancing. Living in California is a cross-dresser's dream. Others always accept us, and going to dance clubs is a normal part of life for our age group, and we enjoyed ourselves. There were several clubs we went to after our Saturday night dinner, and enjoyed the evenings together as girlfriends.

We often danced together and enjoyed listening to the music with a glass of wine. Guys were constantly asking Lisa and I to dance, and we both agreed to limit ourselves to 2 dances per night with any guys that hit on us, in order to be cordial, and to enjoy the experience as girlfriends without having to worry about each other. We never danced unless the other was dancing at the same time, and we always kept an eye out for each other. I even admitted to Lisa that dancing in a dress and heels was fun and that I liked it. After a few weeks and several dances with men, I became comfortable enough to just enjoy the feelings and being Amanda. Other than a hand on our ass or a quick kiss, nothing happened, and we always shared notes back at our table after we told the boys we weren't looking for company.

Giggling and laughing at our exploits was something I had never anticipated but enjoyed. We would tell each other how the boys tried to flirt or touch us and if we made them hard, or how big they were. In fact, we both enjoyed our nights out as girlfriends more than I ever dreamed, and were now closer than ever before.

As I mentioned, the area of the country we lived in was accepting of our lifestyle and we had no issues when we went out together. However, the lack of feminine movements gave away my gender, which continued to inhibit my openness and willingness to try new things. Even though my appearance was clearly female, my hand movements and the way I walked gave away the fact that I was not a true female. Every Saturday we would get Amanda dressed up, and we went out to trans friendly places, had dinner and went to movies, and even some festivals on the beach.

Over the many weeks, Lisa continued to coach me on my movements and wanted her Barbie Doll to become her real-life girlfriend. I was an eager student and learned many of the feminine secrets she grew up with, and practiced them every Saturday afternoon until we went out that night.

Our Saturdays became a ritual play date and started as soon as we got out of bed that morning.

Lisa had made friends with Mark, one of the senior partners at work, who had a boyfriend that we met and went out with. Several Saturdays, we ended up double dating with the boys. We were two girls out with the two guys, and nobody gave us a second look. It was an interesting dynamic, which made me comfortable as Amanda, while out with men.

Since there was no threat, we even split up and danced together. Mark would dance with Lisa, and I would dance with Steve. In fact, we did this so often that I became comfortable dancing as a girl, being held, and following during slow dances, and falling into the female role. Several times Lisa commented about how proud she was of my progress, and how natural I was becoming in my movements and confidence.

Lisa and I were out alone one night when two of the local military servicemen came to our table and asked us to dance. It turned out that the man interested in Lisa was Dawson Dakota, the commander at the naval base and a well-known ladies' man. He was a big guy, and Lisa looked tiny while she danced in his arms. I danced with Joey, one of his friends, but I was clearly not his type. But he kept me company, as he was Dawson's wing man. We sat together, and they bought us drinks all night, and for the first time, I saw Lisa enjoying herself with another man other than me. It was obvious that she was infatuated with this big tough guy and his status as a Naval officer. She was giddy and flirting like a schoolgirl, which made me a little uneasy and jealous.

Seeing her with another man confused me, and brought up new emotions I couldn't explain. That night in bed while in each other's arms, I asked her about Dawson and how she acted.

"That was a fun night, and you really seemed to enjoy being with Dawson. It kind of made me jealous to see you flirt with him like that," I said with a shaky voice.

"Oh, sweetheart, I love you. Don't be jealous, I was just having fun, and you were right there the entire time. It was just different with him, I mean, he was so big and strong and he made me feel, well, different. I love you and don't want anyone else, but it's hard to explain, I just had fun. I love you and would never want anyone else, honey," she said as she kissed me gently and stroked me to another orgasm. She cleaned me up, and we fell asleep in each other's arms.

The following days I noticed she was answering more text than usual and asked her about it.

"Who have you been texting to, baby?"

"Just Dawson, he's been telling me about his upcoming hiking trip."

"How did he get your cell number?"

She saw the sad look on my face and quickly reassured me, "I guess I gave it to him at the club. I'm sorry. Should I not have given it to him? I can stop if it bothers you honey, he's just a friend."

Not wanting to appear jealous, I just smiled and said, "It's OK to have a friend, but remember, I'm your husband. I can't compete with a guy like that, and I hope I'm not losing you, honey. You know I can't live without you."

"Never, baby. It was fun being out with Amanda and kind of being on a double date with Dawson and his friend. I mean, you seemed to enjoy dancing with him and spending time that way. It's just fun, let's not make it anything else, baby. Besides, he knows I'm happily married, that I love you, and that I'm dedicated to our marriage."

The texts continued, and they became good friends, but Lisa was great at keeping him out of our relationship. I knew nothing was going on, and she was happier than ever, so I just observed and allowed life to continue.

My Job had an upcoming closure. Every year we closed for a month in coordination with our government contracts. I would usually spend the time lying around or going to the beach. This year, however, Lisa had an idea that eventually changed things forever.

A week before my time off, we were out on Saturday night. Lisa had made reservations at the C-Level Lounge on the harbor. We wore the new outfits we purchased the previous week, along with our sexiest lingerie and high heels. She wanted us to look extra cute and have a dress-up date night, and by that time, I was happy to go along with her plans. She had me dressed in a pink silky sheath dress that fell to mid-thigh. I wore a pair of thongs under my suntan pantyhose while it tucked away my small penis, which remained unseen under the flowing skirt.

Lisa wore a black silk dress that also fell to mid-thigh, but under that, she wore stockings attached to black lace garters. I loved how the top of her stockings peaked out when she crossed her shapely legs. I also loved the attention we both received by the other guest. Having two sexy dressed girls eating alone attracted a lot of views from the other patrons.