Pandora's Box

Pandora's Box

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Please note: This story contains male/male sexual activities and cross dressing. If that is not to your interest or liking, do not continue with this story. Condoms are used even when not stated. Not all terms used are politically or socially correct, but they fit the characters and storyline.

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My wife and I were sharing one of the last days of our vacation on LBI before we had to return to the city and our real life. Vacation time was over and I had to get back and start looking for another job. Something I was definitely not looking forward to.

We drove north on Long Beach Blvd. and through the small beach towns, each with its own charm. As we drove up the island, we entered the section called Loveladies on our way to see the Barnegat Lighthouse. We passed a few massive beach houses and I slowed down to take a look at one in particular. I was about to pass the big grey and white beach house with the seagull sculpture in the front drive.

This was the house, where a few nights ago, I'd had my first girly boy fling in a very long time.

As I slowed the car, looked up at the balcony deck, and flashed back to Alan standing there that night. It was hard not to smile to myself as I recalled how I felt as I walked up the stairs to meet him.

Fuck! My first impression of him was that he was so damn good looking.

Actually, he wasn't good looking, he was handsome. He had dark, curly hair, that he wore longer on top. His eyes were a dark brown and he had a killer smile. He was taller than me. I'd guess about 6 feet, four inches tall. He weighed about 240 and my first thought was that he was built like a linebacker, wide shoulders, strong torso, hard, flat stomach, and a narrowed waist.

When I got up close, he looked familiar. But I was sure I would have remembered this guy if we'd met before. He shook my hand and turned to lead me onto the patio deck. His ass was amazing. Even with his pants on, I could tell he had a tight, firm ass, and muscular thighs.

As soon as he walked me in and toured me around the house, I recognized him from his pictures. To my surprise, it turned out, he was a linebacker. He played for one of the local professional teams and decided to come to the beach for a few days before the official start of the season.

"Do you know who I am?" he asked as I picked up one of his photos and stared at it.

"I do now."

"Can I trust you?"

"Yes, you can," I nodded and meant what I said.

"This can't get out. It would ruin my career and devastate my family. My parents don't know."

"I would never out you. You can trust me."

I knew a lot of men who led two lives and I knew how difficult it was for them. I was one of the lucky ones.

"What do you do for a living?'

I smiled. I knew exactly why he was asking. He wanted to see if I had an important career that I would want to protect too.

"I was working in the administration and finance division for a major pharmaceutical company. Unfortunately, I was recently downsized out of my position as V.P. of Finance."

"Damn. That sucks. Married?" He asked as he looked at my ring finger and saw the tan line from where I removed my wedding band.

I laughed and nodded, looking at the indention and white skin that was located where my wedding band usually sat.

"Yeah."

"What would she say if she found out?"

He looked me directly in the eye as he asked. There was a touch of sadness in his eyes as he asked. It was like he was apologizing for what he was doing, but felt he had to do it anyway. I understood what and why he was doing what he was. He was looking for something to even out the risk scale.

Nothing he asked or said was done in a threatening manner, but I understood his reason for asking and his meaning. He figured it would be as devastating for me as it would be for him if our date was to be made public.

"She knows. She knows everything about me."

"You're kidding?" He said with a shocked look on his face and disbelief in his voice.

"No, not kidding. We've been together since college. She found out back then and stuck with me anyway. She's aware of my...predilections, shall we say. As long as I don't do anything without talking to her first and as long as I'm safe, she's okay with my meeting my outside needs on occasion."

"She knows you're here? With me? She knows what you want from tonight?"

"No. She doesn't want the specific details. Well, not usually. She just wants to know when and where. It's a safety and trust thing more than it is a curiosity thing or distrust. You know what I mean?"

"Yeah. Fuck. Do you know what a special lady you have? Not many women would be okay with that."

"I know. I'm very lucky."

"Fuck, man. That's not luck. That's winning the lottery. You have something...I don't know what it is but it's rare. I can tell you that."

"We're uniquely different. She's uniquely different."

He moved closer and as soon as he stood next to me, I felt it. I'm an athletic guy, but he was huge compared to me, and he was solid muscle. His dominant size alone made me feel subby. My submissive nature came to life and I couldn't wait for him to take me in his arms. I couldn't wait for a lot of things that I was hoping were going to happen that night.

As I thought about my meeting that night, I took a deep breath and sighed.

Alisa saw me look at the house and knew immediately why it had my attention.

"Is that the place?"

"Yes."

"It's huge. Does he own it?"

"I think so."

"What's he do for a living? Own a bank?"

I looked across the seat at her and gave her my 'do you really want to know' look.

"Never mind. Forget I asked. Sorry."

"You never have to be sorry for anything. Never. If you really want to know, we can talk about it later. For now, let's enjoy our day together."

"Sounds like a plan. Ice cream?"

"Like that's even a question."

We laughed as I pulled up to the ice cream place we love to go to when we're on this end of the island.

************

I don't know exactly what made me feel like I needed to dive into those waters again, but I did.

An overwhelming emotional, psychological, and physical need to be topped and controlled took hold of me and there was no way I was going to suppress it. Not that I wanted to. I had mixed emotions, but none of them led me to want to stop in my tracks. If anything, it was those emotions being brought back to the surface that made me realize I'd missed this part of me. It had been some time since I'd felt the need this strongly, to express this part of who I am.

I can't say for sure, but I think it was ignited by my recent life change and the state of flux it had put everything in for me.

Losing my job weeks earlier when the major pharmaceutical company that I'd worked for completed a year long merger process was painful. When our west coast based sister company, primarily focused on agriscience, merged with us, a lot of positions became redundant. We were downsizing administrative positions on both coasts as we merged the two corporate offices.

I thought my position was safe. I thought that I was safe. I soon found out that I was wrong.

I was the only Vice President of Finance the company ever had that increased annual profits in our northeastern division by over 20%, three years running. In addition to that, my team and I had developed and presented a strategic portfolio for the division that would grow profits over the next five years a minimum of ten percent annually. Both of which helped to ensure the company's profitability and sustainability well into the future.

Those things alone should have secured my position within the company.

The one thing I didn't take into account was the fact that the merge would place me in direct competition with a senior board member's son in law. Guess who lost that competition.

I was devastated, but Alisa was wonderful and fully supportive as always. We had saved enough money that we didn't have to worry about the loss of my salary for some time. Plus, I had a nice severance package coming my way. But that didn't make me feel better. On top of that, having my wife tell me in a very supportive and caring way, that she made enough money to carry us as long as needed didn't help my ego either.

Basically, my psyche had taken a bit of a beating and I was feeling a little in need of comfort. A type of comfort that my wife couldn't provide for me given the situation. My submissive needs were flooding my mind and my body. And, those needs were presenting themselves in old and familiar ways.

My history, since I was eighteen, was that when I was feeling needy or wanting comfort and caring, I opted to dress in women's clothing. When my mom died, my dad did his best to be there for my brother and me, but he was busy with work. My brother was already away at college and, more or less, on his own. That left me alone to cope without any real support.

I was left to grieve alone that summer. I had just graduated and was going to start at university in the Fall. I didn't have a summer job because my parents had told me, It's your last taste of freedom before you start college and then work the rest of your life. Take it off and explore.

Little did any of us know what I would begin to explore that summer.

At first, I liked having a sweater or a piece of my mom's clothing with me and found it helped in bringing me some sense of peace and comfort. Her scent, the softness of the material, all made me feel safe and comforted. But then, I noticed that things were slowly progressing and taking on a life of their own.

Initially, I was only sleeping with her clothing. Then I began carrying a scarf or something small with me. With time, it developed to where I was wearing something of hers to bed at night. When I found that that made me feel good and gave me some solace, I didn't stop there.

Later that Summer, I asked my dad if he wanted me to start packing up some of my mom's things. He looked relieved not to have to ask me or to do it himself.

"Think you could do that?" he asked. "I don't want to leave it all to you, so if you can't, I'll do it. I just can't do it now."

"I'll take care of it. I'll separate things I think you might want to keep and box up the things we might want to give away or donate."

"Thanks, David. I don't think I could have gotten through this without you being here. I'm sorry I haven't been here for you as much." He reached out, pulled me to him, and gave me a big hug. "I love you, buddy. You know that, right?"

"Yeah, dad. I know. I love you too."

When my dad left for work, I went up and started going through my mom's things. I pulled out one of her silk blouses. I rubbed the soft, cool material against my face. It felt so good. I couldn't resist putting it on. I loved the feel of it against my skin.

The next day, while searching through her drawers, I found her under things and lingerie. I couldn't help myself. Initially, I ran the intimates over my arms. Then I found the need to be naked and rub the silky material all over my body. The more I did it, the more I wanted it.

It was arousing in so many ways. I didn't know how to describe it then, and even now, when I think back to those days, it's difficult to find the right words to express what I felt.

One day, when my dad said he would be working late, I laid out an entire outfit. For almost an hour, I stood there and stared at it. I was dying to see how it felt to put it on, but I couldn't do it. At least not that time. Two weeks later, when my dad was away on business for a few days, I did it. I picked an entire outfit to wear.

I looked through her undies and bras and picked out a satin, cream colored bra and pantie set. My mom was a stylish dresser and she had a lot of extremely nice and some very sexy clothing. There was a matching camisole to the bra and pantie set, so I took that too. I walked to her closet and opened the door wide, looking through everything, I finally decided what I wanted to wear. I chose a soft jersey cotton, summer dress. It was sky blue and I loved the feel of it. Soft cotton on the outside, sexy, soft satin next to me. Who knew it would become a thing for me in the years to come?

That was the first time I ever dressed femme. I recall I was standing there naked, looking at my body in the mirror as I slid the soft satin panties up my legs and then tucked my cock into the front of them. I watched my reflection as I pulled the straps of the matching bra up my arms and reached back to fasten it. For a few minutes, I didn't move. I stood there looking at my body. I was excited by how everything made me feel.

When I pulled the dress over my head, I slid my hands over the front and sides to smooth it to my body. It was like being caressed by someone else's hands. My cock immediately came to life and the tight fit of the panties made my full erection feel even better. It was a little uncomfortable, but so much more exciting.

Simply the thought of my hard cock being constrained by silky women's panties made me leak pre-cum.

As I looked at my reflection, I realized something was missing. I went back to her closet and found a pair of her wedges. I tried to shove my foot into one, but there was no way it was ever going to fit. These shoes were a size nine and I wore an eleven. I placed them back in the shoe rack and made a note to get a pair that would fit me.

That thought alone should have shocked me, but it didn't.

I wore the outfit all day. Later that evening, when I took off the dress, I didn't want to remove the panties and bra. I laid on my bed and fantasized about all sorts of things I'd never thought about before. My hands were all over my body. Before I knew it, I was stroking my cock with one hand and pinching my nipples with the other. The last thing I remember was that I was moaning out loud and cumming in my silk panties.

I went the entire week my dad was away, dressed in women's clothing. It did something for me. I couldn't explain it at the time, but I felt more alive, more whole than I had been in a long time. I also had a feeling of freedom. I wasn't limited to any one thing. I was able to be, to do, to act anyway I wanted to. I was brushing off the rules of society and being whoever I wanted to be. It felt amazing.

I became so emboldened, that one day, I went to the mall dressed as a woman and found myself shopping in the ladies department. I actually bought an entire outfit that was for a younger woman and more my style. It didn't take much longer or more exploration for me to find that I really enjoyed the feeling it gave me to wear ladies undies and bras.

It wasn't simply an appreciation for the softness or the feel of the material against my skin. It was deeper than that. It was soulful in a way. An awakening of something in me that until then I wasn't aware it existed.

By the time I left for college, it had become something I simply had to do. When I met Alisa, I tried to change. I tried to deny myself, but I found I couldn't leave it behind. It was months before she found me out and I had to explain.

I was never so nervous in all of my life. I loved her and I was pretty sure she loved me, though neither of us had said the words. But in that moment, I thought I'd lost her forever.

It was our junior year and we'd been dating the previous semester and over break. We'd just started the Winter semester when it happened. One night she came over to study. She was in my room and I ran down to pay for the pizza we ordered.

I wouldn't say she was snooping or anything sinister, but she was looking around and opened one of my drawers. She found my stash of lingerie.

When I came back into the room, she was sitting on my bed and holding a pair of black lace panties. There were tears in her eyes.

"Are you cheating on me?" She asked and threw the panties at me, they hit me right in the face, only to fall onto the pizza box and hang there.

I looked down at the black lace and then over to her. Tears were starting to stream down her face.

"No."

I was at a complete loss of words. What could I say? I wasn't cheating. I loved her. But, I couldn't tell her the truth either. I didn't know what to do.

"Then how do you explain those? How do you explain the drawer full of women's things in your dresser?"

I don't know how long I stood there, but it felt like forever before I could move or form a complete sentence.

"I don't know what to say."

My voice was barely audible. I felt like I was going to cry. I never wanted to hurt her. I never wanted my secret to come out. Now, I wasn't sure what was going to happen.

"Try the truth," she said through her crying. "It can't be worse than what I'm thinking."

I placed the pizza box on my desk, took the panties, and walked over to the bed. She quickly moved away as I tried to sit next to her. I didn't blame her. I lied to her. She was hurt, and now I was about to get what was coming to me. No matter what I said, I was sure she'd leave me.

My head fell and I was staring at the black material in my hands wishing there was some other way to explain the drawer full of girly undies and other things.

If I let her believe I was cheating on her, we were over. If I told her the truth, she would leave me. There was no way for me to win. I was sure either way I chose was going to cause her pain, but I'd rather she hated me for the truth than for a lie.

We'd always promised to listen to each other when we had something to say, or argued, or had a little fight. I was hoping she was still willing to listen.

"No matter what I say, I think you're going to hate me." I could barely hold back my own tears as I continued. "I'm not cheating on you. I promise. Please believe me."

She looked at me with a tear streaked face and wet eyes. All I wanted to do was take her in my arms and hold her.

"It's hard to believe that when you're holding those." She nodded her head to the panties in my hands. I was nervously playing with them and had them wrapped around my fingers. "Whose are they?"

I looked up and turned to face her. I offered her my hand and prayed she'd take it. It took her a moment, but she did. As I held her hand, I began to cry as I told her the whole story of what happened the summer before I started university. Surprisingly, she sat there the entire time I spoke and she quietly listened.

When I looked up at her again, she again had tears running down her cheeks. I was holding her hand so tightly, both of our hands were white from lack of blood flow.

"Why didn't you tell me?"

"I was afraid. I didn't want to lose you. I love you."

At first she was quiet. Then she said, "That's exactly why you should have told me. You should have loved me enough to trust me."

"I'm sorry. I'm so sorry."

I couldn't hold back any longer. I started sobbing. As much as it hurt, I also felt a sense of relief and I couldn't stop myself.

To my surprise, Alisa moved closer and took me in her arms. She held me and stroked my head and back as she quietly talked to me.

"I love you too. I only wish you would have told me."

"I'm sorry. I'm so very sorry. I didn't want to hurt you. I'm sorry."

"You hurt me by lying to me. Not by telling me your truth."

We fell asleep in each other's arms that night. For the next week or so, we talked about it over and over again until I answered all of her questions and she was satisfied that she knew all there was to know.

Several weeks passed before the topic came up again. We were in my room and playing around. I was caressing her body and kissing her breasts when she placed her hand on mine and asked the big question she must have been saving for just this type of moment.