Almost Damsel Almost in Distress Ch. 02

"Ohhhh, like what?" I purred.

"Oh no," he said, wagging a finger at me, "I'm not ruining the surprise." I turned my lip down in an exaggerated pout. He came over and kissed me, just making me melt again, why did him kissing me have such an affect? It was weird, I never really thought of myself as gay, maybe bi since I was very attracted to guys when I dressed. I never really thought about the other parts of a relationship with a guy, hell I'd never really thought about anything besides sex with a guy! So, the idea of falling for a guy was a bit strange to me. One thing at a time though, we'd really only just met, but there was something magical here...

We broke the kiss and I was smiling softly. He smiled back at me, "So, looking through this stuff reminds me, I think you owe me a fashion show."

I looked puzzled for a moment, then remembered, "Oh, right! Do you really want to see all the clothes? Like even the non-fetishy stuff?"

He nodded, "Yeah, sure. Any chance to watch you show-off."

"I do like to show off! What should I do first?" I asked opening my closet and looking through my femme stuff.

"Go ahead and surprise me," he laughed as he settled one the bed, watching me intently.

I frowned, "Well, then you need to... close your eyes or turn around or something." He looked puzzled, so I explained, "It won't be a surprise if you see the outfit before I put it on."

He laughed, "Fine, that makes sense. How about I go make us some coffee?"

"Sounds good to me," I replied already digging around in the closet. "I can put on some make-up, too."

"Well, if you're going to do that, then I'm going to run back to my place for a moment," he called from outside the door.

"Sounds good," I replied, pulling out a dress I'd been dying to wear for a while, trying to figure out how to do some quick make-up, since I didn't want to take all day with it, but still wanted it to look good!

Several minutes later, I opened the bedroom door to the smell of fresh brewed coffee. I saw Alex sitting on the couch, reading something. There were two mugs of coffee on the table in front of him.

He turned as I came out, "I wasn't sure how you... wow! You look fantastic!"

"This old thing?" I replied casually, striking a pose to show off the slinky red dress I had on. It was just long enough to be modest, but short enough to be sexy, slightly above knee length, it was a figure hugging red dress with a modest neckline. Just enough to show some cleavage, but still cover the fact that I'm using falsies. Cap it with red fuck-me pumps, and it made a pretty sexy look. At least that's what I thought anyway.

Alex made a twirling motion with his finger, so I took a few steps forward and did a slow turn, making sure to wiggle my ass a few times as I did it.

"That is sexy, babe. You would slay at a club or anything... wow," he shook his head, grinning from ear to ear. I blushed a bit, but smiled happily. I knew he was exaggerating a bit, but still it was really nice to hear him gushing about how great I looked. So, I strutted over in my red pumps and leaned over to give him a long, slow kiss.

"So, you still want to see everything?" I asked hesitantly.

"Absolutely," he nodded back.

So, we spent the next couple hours with me showing off the variety of different outfits I had. I went from simple, fun outfits like a polka dot sun dress, to a very practical shorts and t-shirt, to a sexy but stylish business suit, to a super prim and proper taffeta gown. I enjoyed showing off my leather pants and the white shirt I paired with it, and the variety of shoes and heels I had. I was impressed, Alex was attentive and had different things to say. Some he liked, some he thought were interesting, and others he simply asked, "Where were you planning on wearing a taffeta gown?"

Of course, I saved the really good, fetish stuff for last, but gave him a few teases of leather mini-skirt, and pleather bustiers and some sexy boots and heels. Once I came out in my PVC catsuit, Alex got the hint that the fashion show was shifting to new territory! I showed him my few latex pieces, like my latex skirt and gloves, with my patent leather corset. My vinyl mini skirt and tube top showed a lot of skin, but was still a super fun outfit. I even showed off my leather crop top, thigh high boots and my backless leather skirt! That got his attention! And got us talking, too.

"A backless skirt, eh? I guess you'd get some attention wearing that one out?" Alex quipped.

"Well, I guess, but not sure I'd have the guts to wear it out," I admitted.

Alex looked at quickly, "What's the point of having them, if you're not going to show them off?"

I shrugged, "I don't know. I guess its like having bondage gear you can't use. It just seemed like something you wanted to get and made sense at the time."

"So, would you ever wear something like that out?" he asked, a wry smile on his face.

I shrugged again, "I don't know, maybe. I mean, I get turned on by the idea, but not sure, I'd ever have the guts to go through with it."

"So," he grinned, "You like the idea of teasing guys with your ass hanging out?"

I blushed and looked down at my thigh-high boots, "Well, yes, I love the idea."

"So, if your Master ordered you to wear that and took you out, you'd be pretty excited?" he was smiling slyly. I could almost see the wheels turning. I was both scared and excited about where this was going.

I shuffled my spiked feet back and forth nervously, nodding nervously, then finding my voice, it was raspy with my arousal, "Yes, Sir. I'd be very excited about that."

"And a bit nervous, too?" he smiled at me.

I nodded, "Yes, Sir. But if I was on your arm, then I'd feel pretty good about wearing out anything."

"Anything?" he asked seriously. I nodded, biting my lip. "Even this? A backless skirt."

I blushed, but nodded, the arousal winning out on the embarrassment. He stood and came over to kiss me and hold me. Leaning in close, he raised my chin so I had to look him in the eye, "Don't ever be embarrassed by what turns you on." He smiled softly, "I love that you're so sexy, and slutty, and it turns me on to no end. I assure you, I've had some wild fantasies and there are all kinds of crazy things I want to do with you... and too you," he smiled mischievously.

"Oooh, like what?" I purred.

He shook his head, "Oh no, that's the advantage to being the Dom," he smirked at me. "You have to tell me yours first and I get to decide how much of a freak you really are."

I looked up at him, frowning one corner of my mouth, unsure if he was teasing or being serious. He smacked me on my bare ass and added, "Now, girl." It was funny how a smack on the ass redirected me to sub mode! So, I thought about some of my wild fantasies of being the only girl at a gangbang, or being bound and used over and over at a bondage party, or being tied down and whipped, or being dressed as a pony girl and pranced about, or being led into a place with a bunch of horny guys on a leash, or being dressed like a slut and pimped out on a street corner, I had so many that were a bit wild, and they just went up from there! So, I decided to go for a wild one that didn't seem too out there.

"Well," I looked up into his eyes, "one of my favorites is being at a bondage party or dungeon type situation, and being spanked and shown off and fucked in front of the whole group."

He raised an eyebrow up like he was looking at me funny, "Really?" was all he said.

I smacked him on the arm, "Don't be an ass."

He smiled, "Actually that's pretty damn hot, I like it. I wonder how you'd look all tied up and being taken over and over by a group of guys..."

"Or girls," I added.

He looked at me sideways again, "Oh, really?"

My face flushed and I started getting hot again, "Sure, if they have strap-ons, or depending on how I'm bound if my mouth is available." I was getting worked up again!

"Nice, anything else?" he asked.

"A girl's gotta have some secrets," I replied with a faux haughty accent.

Alex grabbed me by the hips and pulled me in close, kissing me on the cheeks and whispering in my ear, "Well, if a girl wants to make her fantasies come true, she also needs to learn to share." He then began kissing my neck and nibbling on my ear, which just drives me crazy.

After a few minutes, I was clawing his shoulder and started biting him without realizing it. "Owww, damn! Are you okay?"

I was looking at him, panting, "You keep doing that and I'm going to have to jump you right now."

He grinned down at me, knowing exactly the effect he was having on me, "Well, I'll tell you what, why don't you get changed again, this time into something cute and good for a lunch date."

That pulled me back, "Are we going out?" I asked, both excited and a little nervous.

"That's up to me, so you better pick something good," he kissed me on the forehead and turned to sit back on the couch. I scurried off to get changed!

What seemed like a very long fifteen minutes later, I had gussied myself up in my sundress, a nice pair of wedge heels and even some nude stockings. Of course, I went for subtle on the make-up. I'd been trying to practice with subtle looks in addition to wild and outlandish looks. With my fairly pale skin, I liked to go for a more autumn look with lots or brown, but that would let me mix in some red or yellow for a splash of color. So, I did my eyes with a very light brown, mixing in a soft pink for a nice reddish-brown blend. Of course, I went very light on mascara and decided to skip the eye liner since I was trying to be quick! I did some blush, but again a light brown, mostly for some soft color. I then did a light pink on my lips, since I wanted them to be kissable, but more cute than sexy.

My hair was a slightly different story, I tried to go for the most natural looking wig I had. I only had a few, but there was a shoulder length reddish-brown that I thought would be the perfect complement to my make-up! I brushed it out, and tried to style it, but again, I was trying to be quick. So, I just went with it brushed out and down loose.

When I came out of the bedroom, Alex looked at me, and seemed surprised. "Wow, you look great!"

I beamed, and even did a little twirl to let the dress flair up a bit! "Not too much?" I asked hesitantly.

"No," he replied coming over to look me up and down, then wrapping me in an embrace and kissing me. "You look great, sexy but in a cute fun, going on a date way."

"Not in a vinyl fetish sex whore kind of way?" I joked back.

He answered by kissing me again, "You make both styles look good, babe."

Awww, I was bubbling and smily! This was amazing! "Are we... going out?" I asked hesitantly.

He nodded emphatically, "With you looking like this, hell yes!"

He took me on his arm and led me out to the parking lot, he even opened the car door for me. I could get used to this!

A few minutes later, we were at a local place I'd never been to before called Dante's Pub. As we were about to get out of the car, I took a few deep breaths to try and calm down. My hands were shaking I was so nervous!

"Are you okay?" Alex quietly asked, sounding a bit worried.

I nodded, afraid my voice was going to quiver, "Yeah, I always get... nervous? Scared? Something... when I go out."

"Okay, we don't have to go, we can go back..." he started.

"Oh no!" I blurted out, "I want to go, I just need to get my nerves tamped down."

He grinned, "Okay, well we can wait a few minutes. You want to talk about it?"

I nodded, "Yeah, maybe that will help me rationalize it."

"So, why are you so nervous? You really look great, if that's it," he stated, smiling.

"Thanks," I smiled nervously. "I don't know why. It happens every time I go out. I get really scared and nervous. Almost to the point of shaking. " I held up my hands to demonstrate. "It eventually goes away, I just have to kind of calm down that irrational part of my brain that is screaming 'Run! Everyone knows and they're all judging you!' I guess it's a survival thing, I don't know. See, better already." I held my hands up again, and they weren't shaking at all.

Alex smiled, then kissed me softly, "Well, one thing is different this time. " I raised my eyebrows quizzically. "I'm with you, so you have someone there that's definitely not judging you."

So, we headed in. Alex opened the door and I held onto his arm as we went in. Partly from nerves, partly to keep in contact, but also partly to help with the heels! They weren't the highest I had, but even four inch heels in a parking lot can be an adventure! By the time we got to the front door, I was feeling really good and was even comfortable on the heels. In fact, I was feeling fierce!

The restaurant was a quiet little place done in an English pub kind of style. It was also fairly dark, which I appreciated since it would help me blend in more. The waitress saw us to our seat. As I sat, I almost yelped as my sore ass made contact with the wooden seat! Jan, the waitress, introduced herself and went to get us some drinks.

We sat and just talked for the longest time. It was a wonderful date, and probably a good idea as a "get to know you" type thing. Alex was the youngest of four kids. His parents had recently passed away. I offered my condolences, which he was very sweet about. His brother and two sisters were both much older, so it was assumed he was an 'oops' baby. His parents never treated him any different for it, but they were older, in their late forties when they had him and they'd been in their sixties when they passed. Alex was the only one still around home, since his siblings all had gotten married and had their own families. Only his oldest sister was still in the area, but still several hours away.

So, he'd been working in a transportation company and had taken over managing the third shift when both his folks got sick. Apparently his mom had been sick for some time fighting lung cancer. She had gone into remission several years before, but it came back with a vengeance last year. While she was fighting that, his dad got sick and died of lymphatic cancer within a very short time. His mom was terminal, so it was just a matter of making her comfortable while this was going on.

He talked about all of this with the quiet confidence of someone who's told this story a number of times. Working the late shift, let him be able to make a fair amount of money, but still take his folks to appointments and things like that. He'd gone to a trade school and was qualified as a vehicle mechanic, but he only did that for a couple years, before his intelligence, confidence and way with people had him moving up.

I explained that I was an only child. My mom left when I was little, so I never really knew her. It was mostly my dad and I growing up, but he was kind of an odd person, so I was mostly on my own. He did remarry when I was a bit older and Terri, my stepmom, was okay, but both of them worked, and had their own stuff. That was probably part of the reason I had a very vivid imagination!

I also explained about going to school and getting my degree, then getting my programming job which paid pretty well, and let me be able to live on my own and also let me do a lot of shopping!

After talking all of that, we got our food and Alex asked the key question, "When did you start crossdressing?"

"Well, I was interested for years. I always remember seeing girls at school and such in cute little dresses. The big thing was when I was seven or eight, I was the ring bearer in my uncle's wedding. I had to wear this itchy, uncomfortable suit and tie, but the flower girl... she got to wear this really pretty, cute, fun dress. Everyone gushed over both of us, but I hated my suit and she was having a blast. She even got to wear make-up, had her hair done and all that. I was so jealous!

"I also remember playing with my cousin Allie growing up. Whenever we played at her house, we'd always play Barbie and I loved all the variety and types of clothes she had for all of them! It was so much fun, I wanted to get my own Barbies, but how do you ask for something like that as a boy? I never felt like I could do that. Especially with just my dad around. The turning point really came because of Allie actually. We'd been swimming at the local community pool near my house most of the day, and you have to understand, when Allie left, she would always forget something. Well, this time, she left her one-piece bathing suit hanging to dry in my bathroom!

"I couldn't pass up an opportunity like that, so I locked the bathroom door and tried it on! Oh my, I knew the moment I pulled it on that I was going to be dressing in girl's clothes again! I still remember the exact thought I had was, "I'm doing THIS again!" I was so excited that of course, I played with myself. I managed to not make a mess in the suit thankfully, but that was the start of years of sneaking into my stepmom's stuff and trying things on. I don't think she ever knew, but over the years Allie managed to leave a bunch of her clothes at my house, so I managed to get a pretty good set of my own girls clothes, that I didn't need to sneak into my stepmom's for."

"Do you still have some of those?" Alex asked.

I shook my head, "No, I purged all of that out when I left for college."

"Purged?" he asked, a bit confused.

"It's a trans thing. A lot of us do it. The idea mentally is if I get rid of all my femme stuff, I won't be tempted to wear it any more. The problem is that its not the stuff, dressing is in your head. So, the urge always comes back, and you wind up getting more clothes. I guess sometimes, especially when you're young, you think it's a phase, so maybe you'll grow out of it." I shrugged, "either way, its something most of us do over time, and its one of the dumbest things we can do. Yet we do anyways. I lost a lot of nice stuff over the years."

"Was that the only time?" Alex asked.

"No, I also purged again when I finished college. While I was at school, I had roommates and such, so I rarely got much time to dress, but thankfully in the laundry, college girls are just as bad guys and they forget and lose stuff all the time. So, I got a ton of girls clothes that I almost never got to wear! When I moved to my own place, I again purged figuring I'd never have to worry about wearing girl's clothes again. I figured I'd meet a nice girl and have her wear all the fun clothes. Then the urge started again and I started building the wardrobe you've seen. I've also vowed, I am never purging again!"

Alex nodded, "Good, I'd hate to see all those great clothes, go to waste."

"So, how about you?" I asked him. "When did you get interested in trans girls?"

"Last night," he deadpanned. I frowned and looked at him sideways. "What? No?" He laughed. "I think I've always been interested, I just never had a description for it. Through school, I dated girls, and even was... intimate with a few, and I enjoyed it, but it just wasn't what I was looking for. So, then I wondered if I was gay. I dabbled with a few guys, and I enjoyed that as well, but again, it wasn't quite what I was looking for. I still remember discovering trans porn and suddenly I had a name for what I was looking for!"

"Did you meet or date a lot of trans girls?" I asked, curious.

"No, not for lack of trying. I did meet one girl who was a lot of fun, but she was married, so she was just looking for dates and sex. She wasn't interested in a relationship. She moved away last year and then with my folks being sick, I really hadn't had much time to look. I'd only just started looking again a few months ago," Alex summed up. "So, what about bondage? When did you discover that?"

I blushed momentarily, I don't even know why, I just did! "Well, I tried tying myself up a few times, but it was never quite the same. I think you can understand, but last night was... well, a fantasy come true."