Dan and Brenda Pt. 01

I was really nervous as I drove down the highway. I was going to see this guy that I met online. I had never done something like this before, and never would have thought I would do it, ever. I am a transgender woman, I live my life as a woman, but can't afford to get the hormone therapy started yet. But that is my intention. I hate the way I look, but do the best I can with makeup. I have long hair, but it's thinning so I often wear a wig when I can.

I met Dan on a web forum and we immediately hit it off. So many things sounded so close for us, I was worried I was just being lied to. But the way he talked, and the things he said, made my heart flutter in a way I hadn't felt in years. I love restraints and being restrained, but only in a kind and loving environment. That might sound contradictory, but to surrender yourself to someone else's control, and put yourself in a vulnerable situation where they could really do anything, you must be very sure you are safe, and hopefully genuinely loved and cared about. When that happens, the feeling of being in someone else's control, where they may push boundaries just a little for you, the one's you want pushed, is exquisite. I was going to meet Dan, and see if our chemistry was real, and frankly I was so excited and worked up about surrendering to him, I was making a wet spot in my panties.

Before leaving the house, I had dressed hoping for something magical to happen. I started by showering and shaving my body completely smooth as I always did. I put a very light spritzing of perfume on, then I put on this wonderful black body shaper. It's basically a body suit with a snap crotch, but the rear side has an opening for access to my ass while it is still snapped closed, thus keeping my male member tucked, which is my preference.

My penis still works, but I don't like to see it. When I do, it kind of tweaks my brain a little. I also don't like it visible if I am being intimate with someone, and of course I was hoping things would go well and I would be getting intimate.

I slid the body shaper over my head and it snuggly slid down my body. After getting it positioned right, I pull my remnant of manhood back in it's tucked position, and snap the crotch closed. I then slide my large breast forms in place and look in the mirror. I don't like looking at myself, but my body looked pretty good there. I sat down on the bed, and slid on some new black stay up stockings I had bought for the occasion. I would wait for the shoes until I was dressed.

I had sewed a new black sleeveless dress for the occasion. Very basic and simple, and was cut to show off my shape to look better. It's specialty however was that I had made the shoulder straps with snaps in place. So, undo the two snaps, the dress falls to the floor.

I slipped the dress over my head and let it fall into place. Next, I sat down and carefully applied my makeup. By far, my biggest challenge. The long brown wig was next, which had bangs just the way I like, and the hair hung part way down my back. I slipped on my black pumps with 3-inch heels and was ready to go. I had already painted my finger and toe nails earlier so they looked fine.

I grabbed my purse, keys and a long black coat and was out the door.

Now, two hours later, almost to his house, I was thinking about what I had gotten myself into. And wondered if I had forgotten anything. I had a gym bag with me, where I had already packed some of my favorite toys. Things like dildos, butt plugs, vibrators, leather cuffs, a leather collar, blindfold and a few gags.

I was hoping to explore some of these things with Dan, but only time would tell. I was still so nervous as I drove down the highway, my heart fluttering and when I thought about things he had said, my body would quiver. And my bodysuit was developing a wet spot from my boy part.

At last, I see his house. The porch light is on, and the old car he described is in the driveway. I pulled past the old car, and parked way down the driveway as he had instructed me to. I grabbed my purse and my toy bag and headed for the door.

My heart was pounding as I walked. What am I doing here? I'm like a bitch in heat, I want to feel this man inside me so bad. My heels were making their distinct sounds on the concrete driveway as I walked to the porch. Dan was already there, at the door waiting for me as I stepped onto the porch.

"Hello Brenda, I'm so glad to finally meet you." He said holding the screen door open so I could step inside.

I'm sure my voice was shaky; I was as nervous as a long-tailed cat in a rocking chair factory.

"Hi Dan, it's so nice to meet you in person." I managed to blurt out.

He laughed and gave me a kiss on the cheek. "Come on in, Brenda. Relax. I really am delighted we could meet." He put an arm around me and guided me into the kitchen where he had some candles set on the table and a bottle of wine.

We had a wonderful conversation over a delicious steak and bake potato dinner. I was delighted because I don't eat many foods, but a good steak is happily on the list.

All through dinner, we connected like we had known each other for years. We talked about intimate details about things that turn us on, and what turn us off. I shared my background of being transgender and what led to that. He even got out of me that years before, when I was always submissive, that I went by the name Jennifer or Jenny. I hadn't used that name in years because I made a conscious decision to choose a new name (Brenda) for myself to remember I am a strong (trans) woman and I can be dominant or submissive and enjoy both roles immensely. Around Dan however, I was enjoying him being in control.

After dinner, I helped him clear the table and we went into the living room with glasses of wine to talk some more. I found myself falling under his trance. He just seemed so genuine and kind that I felt I could trust him. This coming from someone with trust issues. But he made me feel cared about, and appreciated. Eventually, I couldn't stand it any longer. I asked him if he could show me the shop area he had described to me.

"Sure Brenda, let me show you, my shed." He said, offering his hand to me. I stood up, and instinctively grabbed my gym bag with the toys in it and followed him back outside and behind the house to a shipping container. He opened the door and turned on the bright lights. There at the far end, was what I had been fantasizing about experiencing every since he described it. There were two chains hanging from the ceiling on either side of the container, and about three feet from the back wall. I immediately walked straight for it. There was other stuff in there, but I have no idea what. I didn't look or care. My heart already told me I wanted him to chain me up and tease me, and hopefully let me please him. I stood in the middle, between the two chains and grabbed one and was looking at it. They were not too heavy, but not too light either. They were clean, shiny and clearly not used for anything else.

Dan walked around behind me, wrapping an arm around my waist. "Jennifer, would you like to try them on?" He softly said in my ear. He may have said more, I don't know. My heart was fluttering and my body felt weak. Calling me Jennifer immediately put me in submissive mindset, and I badly wanted to be. And I thought it was so sweet that he had listened to what I had said. I pointed over to my gym bag, which was sitting on a chair, where I dropped it. Dan walked over, picked it up, and opened it.

"Well, look what we have here? Jennifer came prepared. Would you like me to use this on you tonight?" He purred.

I was very quiet, and I'm sure my voice was shaky and almost whispering as I replied. "Yes. I want you to chain me up... please."

He was very sweet, and as he pulled out two leather cuffs from my bag and said "It's okay, Jennifer. I'm going to take care of you tonight." I held out my wrists to him, and he buckled the two cuffs on. He then stepped to my side, and raised my arm up over my head, and connected my cuff to the chain hanging there. He then stepped to the other side and did the same with my other arm.

I looked up at my arms, connected to the chains, and pulled on them, and they were secure. I was no longer able to get away, whether I wanted to or not. It wasn't too late to pull out... unless of course I misread who Dan is, in which case he owns me now and there isn't anything I could do to stop him.

"Are you okay Jennifer? How do you feel?" He asked with a tender sound to his voice.

"I'm a bit scared... I haven't done this with a man before, and it's been years since I did this with a woman..." I wasn't done trying to describe my feelings, but Dan just held me close to him and gave me gentle kisses. First on my mouth, then my cheeks, then my neck... he stepped closer to me, pulling my body against his. I could feel his growing hardness as he pressed against me.

I whispered again, with labored breathing "are you my master, Dan?" I asked.

"I am tonight, Jennifer. And as long as you want me to be. But don't worry about that now, you are safe, and you are surrendering to me, tonight. I will only do things we already talked about, and only if you want me to. And now that you are mine, how I am I supposed to get this dress off? Do I need to grab my scissors?" he asked.

"No, master, on each shoulder is a snap. Just unsnap those" I said quietly.

"Master? Okay, Jennifer." He replied while he unsnapped the shoulder straps for my dress, and as expected it fell down. Dan carefully picked it up, as I stepped out of it and set it aside. He looked me over and licked his lips. I was watching him carefully, scared he may not like what he sees.

Dan reached back into my bag and pulled out two more leather cuffs, then kneeled down and buckled one on each of my ankles. He then wrapped a hand around my nylon covered leg and gently moved it to the side and attached a chain laying on the floor to my ankle cuff. He then did the same with the other. My legs were just on the verge of really uncomfortable, but also extremely exciting to me. My pulse rate was racing, as I thought about how vulnerable I was now.

He then pulled one of my gags out of my bag. This one is a penis gag, that is almost as long as I can take in my mouth without coughing and gagging. He held it up to my mouth. "You want this, don't you." He asked, but it was more of a statement.

"Yes" I whispered back, and he stuck the penis into my mouth and slid the wide elastic band around my head, securing it in place. He then grabbed a bright scarf from somewhere and put it into one of my hands.

"If you drop this, I will stop everything and immediately release you. But we will be done. Do you understand?" He asked.

I nodded my head yes. He then reached back into my bag and pulled out a blindfold and put it on me.

My world went dark. My heart rate racing, my body completely at his disposal. I heard a click, and some music started softly wafting in. I immediately recognized Pink Floyd's "Wish You Were Here" album. One of my favorites. He really was listening when we talked. That made my desire to please him go up. I could hear things going on in the room, but with the music softly playing, I couldn't determine what I was hearing. And every so often, I would feel his hands on my body, or he would stroke my trapped member. At one point he was rubbing my nylon covered legs. I softly whimpered every time, enjoying the sweet sensations of what he was doing to me.

I heard the soft whizzing sound of one of my vibrators, then felt it between my legs, pushing against my trapped member. I moaned into my gag and started gyrating my hips against it. Then as I was getting too worked up, the sound stopped and he wasn't touching me anymore.

I then felt his body pressing against my back, pulling me against him. I could clearly feel his manhood, fully pushed into the crack of my ass, pressing hard against me. He pulled away from me, and if felt like he had crouched down. Then I felt his finger against my bare skin. I realized that he had noticed the opening in my body shaper giving him access to my ass.

"Oh my, Jennifer! Look what we have here!" He said in a mock innocent tone.

"You are a bit naughty, aren't you! Was there something specific you wanted done here?" He asked, knowing full well I was gagged and can't answer.

"Well, since you won't tell me, I'll see what I can find." He announced again, teasing me.

I felt his well lubricated fingers around my hole. Just enough to make sure there was plenty of lube there. He already knew from previous conversations, I don't want someone's fingers inside me, I've got toys for that. The idea of an infection scares me, so I am very careful there.

A moment later, I felt the familiar feel of one of my penis shaped dildos being slid slowly inside me. I moan as it slides deep inside. He slowly pulls it back out, and then pushed it back inside me, slowly at first, then faster and a little deeper with each thrust. My legs were getting weak. I had never felt something stroking inside me while I tried to stand. I was trying to hold myself up with my hands gripping the chains locked on my wrists. My body was gyrating back and forth as he continued his attention. And as before, as my excitement was growing, he stopped and pulled the toy out. A moment later, I felt him replace it with one of my butt plugs which can stay in on their own. It was quite big, and he seemed to be making sure that he pushed it all the way in. I moaned my approval at his choice.

Afterwards, he again stopped touching me. I could hear stuff happening, but no idea what it was. I suddenly felt him holding one of my arms, which he released from the chain. A moment later, he released my other arm, and took the scarf from my hand that I was still holding. My legs were still immobilized, but I could rub my arms which were beginning to ache a little from being chained up. But I happily admit, I was enjoying every second. It was like so many of my fantasies were being played out, and Dan made me feel safe and loved.

He rubbed my arms a little bit as well, to help with the circulation, then pulled my wrists behind my back and locked them together. He did it so suddenly, I was actually surprised. I thought he was getting ready to release me, but Dan had other ideas.

He disappeared again for a moment, then I felt something push against my hips in front, and his body pressed against me from behind. Then his hand was pushing against my back, forcing me to bend over and thankfully I could feel pillows on whatever table or cart he had stuck in front of me. He was still standing behind me, and I could clearly feel his hard dick flat against my ass again. I realized, he wasn't wearing pants anymore, because the only thing between us was the thin fabric of my body shaper.

He leaned over, his body weight pressing against me, holding me down, and making me feel like I was owned, and his property. To do with as he desired. My mind was swirling with all kinds of thoughts when I realized I could feel straps being pulled around my body. He raised himself off my back, then I heard the familiar sound of a ratchets... he was ratchet strapping me down to the cart or table! I could feel two straps going over my arms that were already locked behind my back, and tightly securing my body to the table.

He must have sensed my momentary freaking out because he gently said "don't worry Jennifer, I just don't want this cart to roll away from you. I won't let you get hurt, Jennifer. I take good care of my women."

I felt him move away again. My heart was jumping inside me at the idea of being his woman. Or, at least being one of his women. I had never felt so much lust for a man before. Given my current position, I knew he certainly would be taking me in my ass. And frankly, I wanted it. I really wanted it. I hadn't felt a real dick inside me, and this man made me want to feel his. I found myself whimpering, involuntarily. I was so turned on being held like this, I thought I might orgasm just lying there.

I felt his gentle hands on my head. He carefully removed my gag from my mouth and slipped it off my head. I moved my jaw around to get it to feel normal again. A moment later, he removed my blindfold too.

It took a moment for my eyes to adjust, and I was shocked by what I saw. The room was not brightly lit with shop lights like before, but by candles lit around the room. The toolboxes and tools, whatever, were covered with dark tarps or something giving the room a romantic, comfortable feel. Much nicer to me than feeling like I was getting raped in a garage. Although, I wanted Dan so bad, I would have been fine with that too.

I then saw him, standing across from me. Dan had removed all his clothes, but was now wearing beautiful black, patterned crotchless hose and high heels. His manhood standing at attention sticking out in front.

I said "Oh, baby. You look wonderful. Let me suck on you."

Not very romantic. I immediately felt like a slut instead of a princess being wooed by her captor.

Dan slowly walked towards me, looking sultry and a bit teasing.

"I kind of had that in mind." He said gently.

I took the moment to step out of character, because I felt I wanted him to know how much I was truly loving what he had done.

"This is beautiful..." my voice just trailed off because, it suddenly wasn't important to me anymore. I opened my mouth as he approached, anxious to taste him inside me.

I closed my eyes to savor the moment, as I tasted a man's dick for the first time. I quickly wrapped my lips around his shaft, and sucked him into my mouth. My tongue working on him as I held him in my mouth. It was so much better than I imagined. My love of restraints had me even more excited because of my position. I tried to rub a little against the cart I was strapped to, but instead it just moved with my body. Being on wheels, and with my body tightly held down, and my legs chained wide, arms behind my back, and a plug in my ass, it all just made me even more turned on. All those things are super sexy to me, and now I have a dick in my mouth too. My turned-on meter was pegged.

He placed his hands on my head, as I sucked on him. He was very kind and didn't try to shove in deeper than what I could handle. I eagerly licked and sucked on him, trying to do whatever I could think of that I thought would feel good. And after a few minutes, he pulled away from me.

Happily, I didn't have to wait long for him to give it to me again, this time in my ass. I felt him pull the plug out, and apply liberal amounts of lube to himself, and my waiting ass, then I felt him push against my hole.

I'm expecting to feel him press inside, but instead he asks me "do you want me to do this Jennifer?"

I'm breathing hard, and really worked up. Even though my own member is trapped, I have orgasmed that way before, and I am so worked up, I figured I was pretty close anyway. I tried to answer with a reasonable voice, but I'm sure I sounded like a love sick slut "yes, I want it. Take me! Take me now!" I answer.

And happily, he does. I feel him slide deep inside me. I feel my body rocking back and forth, with the wheeled cart I am strapped to. His hands, gripping my hips and he drives inside me. I find myself wishing I had my gag in, as I loudly squeal and moan, enjoying the myriad of sensations I am experiencing. And as I suspected, I very quickly have a massive, explosive orgasm. My whole body shuddered with an overload of sensations. My trapped member made a mess inside my body shaper, not that I cared. Dan might have known, or maybe not. Either way, he doesn't stop. He keeps riding me, sliding in as deep as he can inside my bound and captive body. It didn't take him long before he fills me with his cum. I can feel him flexing his member deep inside me. We both lay there a moment, catching our collective breath.