I couldn’t deny that when we shared a dorm room I envied Trudy a bit. I wished I was more spontaneous, a little naughty like her sometimes. Hell, who was I kidding? I envied her more than a bit. I was confident enough in many areas of my life but I still worried how people might think of me. I was worried about how I might appear to other lawyers, to my parents and friends. Hell, I worried about how complete strangers might judge me. I wasn’t sure why, though. I guess I just wanted to fit in for some reason, for people to accept me. I guess I was afraid of being singled out. But as I considered that, I discovered it didn’t bring me a lot of joy. It just made things easier.
“You want to go out tonight?” I asked.
“I’d love to but I’ve got a date,” Trudy told me. Damn. I suddenly wanted a taste of Hogs and Heifers, a taste of my night with Jack. I sighed, disappointed but Trudy saved me. “It’s not really a date. I was going to meet Sarah, the crossdresser, for dinner and drinks,” Trudy said.
“What do you mean it’s not a date? I thought you were dating him...her,” I asked not sure what to call a man dressed up like woman.
“No, we only went out a few times, but we’re friends now. She’s cool. You want to go with us?” Trudy asked.
“Where?” I wondered but I don’t think I cared. Going out with Trudy and Sarah sounded fun. Suddenly, I wondered how many times I’d heard of something fun but didn’t do it. How many times had someone invited me to do something interesting or daring and I turned them down because I thought it wasn’t something people would agree with or I was sure it wasn’t for me. That was kind of sad.
“We we’re talking about just going out to a bar we like. Not really a gay bar but a bar that caters to all kinds, you know. It’ll be fun. You’re welcome to come along,” Trudy assured me. It sounded fun and a bit scary. It wasn’t me but suddenly I didn’t want to be me, or at least not the me I thought other people thought I should be.
“What should I wear?” I wondered, sure I was going now.
“Something hot. Wait till you see Sarah,” Trudy said excitedly.
“I want to go,” I told Trudy. She smiled.
“Cool!” she replied. We finished our water and off we went. I had butterflies but it was excitement as much as nerves. I wondered what was going to happen and discovered I hoped that whatever it was, it would be something nobody would ever expect me to do. Kind of like my night with Jack, I guess.
>>O<<
I got back home at around four that afternoon. Trudy took me to get my car after we finished our hike. I hopped into the shower as soon as I got home, excited about the upcoming night out with Trudy and her crossdressing friend. I meant to relax a bit after getting out of the shower before getting dressed as we weren’t going out until seven but I ended up dripping wet on my bed with my fingers buried between my creamy thighs. It felt so good but it wasn’t the physical sensations that made it special.
Talking with Trudy helped me see the previous evening in a different light, but it didn’t solve the Jack problem. I still couldn’t forget what we did and how he made me feel. Imagining Jack was with me and I was being his bad girl again drove me wild. I was doing things for him I’d only read about in those dirty books on my Kindle and immediately deleted so no one would know what I’d been reading. I felt a bit guilty for fantasizing about Jack like that, but I forced myself to ignore those feelings.
After a particularly wild orgasm, I stopped pleasuring myself and lay on my bed, still wet from the shower and breathing hard. Why wouldn’t I want another night with Jack? Who was I kidding? I loved the way he fucked me. I needed more of that. I wondered if he’d forgive me, assuming he was angry in the first place. I bet if I looked the part of the bad girl he brought out in me, he couldn’t resist. I got up and went to my closet and found something to wear that he might like. I wasn’t seeing him, but I wanted to dress up like I was. Once I found what I wanted, I finished getting ready.
“Girl, you look hot!” I said as I looked myself over in my mirror. Leather boots with spiked heels, fishnet stockings and a black lace garter belt, a way too short black skirt left over from a Halloween costume and to top it all off I found an old baby doll t-shirt that had “Princess” emblazoned across my boobs in rhinestones. I guess I wore my clothes tighter in college because that thing left little to the imagination. I also began to wonder if I didn’t have some kind of stocking fetish. I had like fifty pairs. Maybe that was the bad girl expressing herself.
For a moment, I almost took it all off. But something about this felt...I don’t know...right, I guess. I felt sexy and hot and excited. I felt alive. Then I had an idea. I left my dark hair down and I’d applied my makeup fairly heavy but I needed something else. I rummaged through my dresser and finally found what I was looking for. A black satin choker that had come with some outfit or another and I thought looked stupid. But now, it tied this whole outfit together and looked perfect. It made me look a bit naughty and a whole lot submissive.
I was having fun. I felt a bit wicked and I liked it. I’d seen girls dressed like this and wished I could too but I always told myself that it wasn’t me. That was always my excuse. It wasn’t me. I wasn’t that type of girl or whatever. But it was me and I was just afraid to admit it. I was afraid of what others might think if I strayed from the straight and narrow course. But deviating from the norm was sort of liberating. I grabbed my hand bag and left to meet Trudy and Sarah, excited to see where this might lead.
We met for dinner at a little Thai place in a strip mall. I was stunned when I met Sarah. She, as both women informed me was the proper way to refer to a crossdresser, was stunning. A bit tall and broad in the shoulders but Sarah wasn’t the man in a dress I’d imagined. I couldn’t help wondering what was under her slinky dress after Trudy told me they had slept together. The idea blew my mind, especially seeing how incredibly sexy she looked. Did that make them lesbians or what? I wasn’t sure.
Sarah had a on a tight red dress and pantyhose with matching heels. She had no issue explaining to Trudy and I all the tricks she used to look as good as she did while we ate. Her long, straight honey-blonde hair wasn’t hers and neither were those lush eyelashes or the round breasts, but you couldn’t really tell. Her voice was husky but feminine enough and kind of sexy too. She had a Kathleen Turner sound to her. Her long red nails gave her hands a feminine look as well. I wondered how many men checked out the tall crossdresser and had no idea they were really looking at a man. The idea was sort of amusing.
Trudy, on the other hand, was in black lace leggings and a cute green tunic that showed of her ample cleavage and matched her eyes. She wore black platform pumps but she still barely stood five-foot seven and Sarah dwarfed Trudy in her own heels. Once again, I couldn’t help but imagine Trudy and Sarah having sex. I forced myself to stop because it was kind of erotic. Sarah, however, didn’t seem ashamed of her crossdressing in the least.
“Damn, I’ve got to go to the ladies room. My dick is all bent and twisted in these pantyhose. The things I do to look this good,” Sarah joked and excused herself. I had to go to the restroom too and joined her. Trudy stayed behind at the table to watch our stuff. “So, you don’t seem too shocked,” Sarah said as we entered the ladies room.
“Trudy told me about you. Honestly, you look great. I’d never have known you were a...,” I said and stopped unsure of what I should say. Sarah looked at me and smiled.
“Don’t worry about it, Brandy. I’m a guy most of the time. I have a dick. You won’t offend me,” she said and then as an afterthought looked under the stalls to make sure we were alone. We were. If we weren’t some poor woman would be getting an earful.
“Sorry, I’ve never met a girl like you,” I said and Sarah hiked up her dress and shoved her hand into her pantyhose and bent her legs awkwardly a she adjusted herself. I looked away and found a stall to do my business. She kept talking as I did.
“I’m glad I don’t scare you. A lot of people just don’t get it, you know. They think I�
��m a weirdo, and I guess I am. But I’m just being true to me. This makes me happy. I’ve got a girl inside of me and she needs to get out and have some fun too. I was miserable before I embraced Sarah. Trudy is my savoir,” Sarah told me.
“Trudy?” I wondered from my stall.
“Yeah, she was the first person I told my secret too. We were dating and she dragged it out of me. She really helped me be OK with Sarah. In fact, she helped me pick out my name,” Sarah explained. I got it now. Sarah was the miserable person Trudy spoke of on our hike. I wondered how she knew. She said she was an empath. I assumed she wasn’t reading minds but Trudy did seem to have a knack for guessing how people felt and helping them work through it. She had done so for Sarah and she’d done it for me too on numerous occasions.
“I didn’t know that. Trudy’s a good friend that way,” I replied.
“Yeah, she is,” Sarah agreed. I emerged and washed my hands before checking my outfit in the mirror as Sarah did the same. She turned towards me and asked, “Can you see a bulge?” I giggled and looked her over.
“Nope, you look good,” I replied finding the whole scene a bit surreal.
“I don’t know about you, but I’m ready to party,” Sarah said. I nodded.
“Me too,” I told her and I meant it. I wanted to go out with Sarah, the sexy crossdresser, and Trudy, the cute empath, apparently, and get into some trouble. We left the restroom and settled up with Trudy who had paid the bill. We left in a cab for The Kurtain Kall, a trendy club just off the Vegas Strip. We’d all taken cabs to the restaurant because it was likely we’d all be taking them back home later. That was the plan anyway.
As advertised, The Kurtain Kall catered to all kinds. There were rockers, gays, lesbians, hipsters, clubbers, ravers, you name it. Sarah wasn’t the only crossdresser either. Some were far more flamboyant, however, and I’m pretty sure some weren’t simply transvestites. Everyone fit in and at the same time, nobody did. It was an eclectic mix of people, a melting pot of lifestyles and cliques. We ordered drinks but we didn’t bother trying to find a seat. There weren’t any open tables or stools at the bar. There was room, though not much, on the dance floor and that’s where we ended up.
Trudy, Sarah and I danced together to the pounding dance music. We made quite the strange trio but who cared? We weren’t the strangest group of partiers in the place. Next to us a guy danced with two women, his hands all over both of them and all three of them wore wedding rings. There were couples of all types beyond that threesome, gay men, lesbians, straight people and more. You couldn’t help but wonder what went on behind closed doors as you looked around the crowd and I wondered which of the women in the threesome was stepping out on her husband and if he knew it or not.
We danced and drank and soon I was feeling a bit tipsy. I was having the time of my life, however. This was so much fun, just dancing, drinking and people watching. Then out of the blue, Trudy and Sarah began dancing together. Their hands roamed one another’s body and then Sarah bent and kissed Trudy deeply. I couldn’t help but stare at the display. Sarah caught me looking and broke the kiss and let Trudy go. “You’re turn, sexy,” she said and came my way.
I giggled despite myself as Sarah danced her way towards me, her hips swaying and a prominent bulge now showing in her dress. She slipped her hands around my waist and pulled me close staring into my eyes. Her bulge rubbed against me as we danced and then she kissed me. I was shocked and went stiff but I relaxed after a moment. “Go, Brandy!” Trudy shouted and I laughed breaking the kiss with Sarah. Sarah laughed too and I could tell she was just having a bit of fun, playing around.
“Your dick is showing,” I teased. Sarah looked down.
“Little fucker escaped,” she exclaimed at then we all had a good laugh but Sarah didn’t make any attempt to rectify the situation. Sarah and I danced a while longer and then Trudy joined us. As surprising as Sarah’s kiss was, it was fun. It was sexual but in a casual, friendly way. No pressure, no expectations, just playing around for the sake of playing around. I found I liked letting go and just doing what felt good. Yeah, I wondered what people might think if they knew I was kissing a man in a dress but I also discovered not caring made me feel good. Hell, it felt awesome! The song changed and this one was even faster and the three of us joined the crowd, jumping up and down and getting a bit crazy.
Then the DJ spoke over the music, “Don’t forget the wet t-shirt contest at ten. Ladies can win $500. Come see me to sign up.” Trudy and Sarah immediately looked at me.
“Oh no! I’m not getting up there,” I said wagging my finger at them but I already knew I’d do it if they pressed the issue.
“You danced half-naked on the bar at Hogs and Heifers,” Trudy reminded me. Sarah looked from Trudy to me and back again. I could tell that surprised her a bit.
“I’m sorry I ever told you that,” I said and scowled playfully at Trudy.
“Really? C’mon do it, Brandy. Show us your tits,” Sarah said. I rolled my eyes and tried to think of a reason not to do it.
“Brandy, you’ve got to do it. Come on. You’re boobs are fantastic. Not like my floppy tits,” Trudy said and I laughed as she grabbed herself. I had to admit, my boobs were rather perky for being so big and full.
“And these I bought at Amazon,” Sarah said and grabbed her own. All of us laughed at that.
“I hate you both,” I said but Trudy and Sarah were already leading me to the DJ to sign up.
“OK, hang out here and we’ll call you up in a minute,” he told us. Again, I had butterflies but they were a mix of nervousness and excitement. A minute later, a woman grabbed me, took me aside and handed me a white t-shirt. It was cheap, thin and two sizes too small.
“You can change back there,” she told me and pointed to a door behind the DJ booth. I went back there and several other girls went with me as well. Some of them seemed to have done this before. They immediately began removing shirts, tops and even dresses and pulling the thin, gauzy white t-shirts over their mostly thin torsos. Two other girls, obviously first-timers too, and I followed suit. I could barely pull my t-shirt over my breasts and when I did, it was nearly see-thru stretch over my big breasts.
Before I had the chance to reconsider my decision, the woman that handed me the t-shirt called us out onto the makeshift stage near the DJ booth. We followed her and lined up before the crowd. Trudy and Sarah were right in front cheering me on. I glared at them but they seemed to be enjoying my discomfort. I was second to last in a line of seven women. Some were thin and athletic with perky, natural boobs. Others were like human Barbie dolls with tits as fake as the dolls they looked like. The balance of the victims...I mean competitors, were pretty women with average boobs just having a good time.
But I, and a by quite a wide margin, had the largest breasts of the group. If big was the point, I would probably win but I suspected one of those Barbie dolls or the fit, workout queen with the perky B cups and the pencil eraser nipples would be more popular with the crowd. I was also the biggest girl on stage but I tried not to let that bother me.
“All right, Ginger. Let’s get these ladies wet,” the DJ called out and the woman that led us on stage began dousing cheap t-shirt-covered breasts in water and by the sound of the squeals and screams, it was ice water. She finally got to me but had barely two inches of water in her pitcher. She looked at me and then the pitcher. She gave the crowd and exaggerated frown, shrugged her shoulders and signaled to someone else to bring more. The crowd laughed and cheered. Lovely. Two perky girls walked over to help her out, each with a pitcher in hand.
The girls took up positions on each side and poured one pitcher of ice water over each of my boobs. I shrieked as the girls, obviously following a carefully crafted script rendered my already nearly see-through shirt all but invisible. My nipples immediately shrank and became painfully hard and I was left shivering as the girls bounded off stage. Bitches!
The DJ began the show, giving each girl a chance to introduce herself and
then show off her assets to the crowd. I watched when I wasn’t glaring at Trudy and Sarah but they seemed to take delight in my dilemma. Each girl shouted out her name and then felt herself up or shook her breasts for the crowd who in turn cheered wildly. Then the woman who had led us on stage, Ginger apparently, put the microphone in front of me and winked. She‘d done this a thousand times before and was lending me a bit of courage. I sighed and did my duty.
“I’m Brandy,” I told the crowd and they cheered encouraging me to show off my boobs. Trudy and Sarah joined them.
“C’mon, Brandy. Shake those tits!” Trudy shouted. I couldn’t help but laugh but instead of shaking them, I lifted one breast to my mouth and sucked my nipple through the thin cotton fabric and then squeezed them both and licked my lips. That got a reaction from the crowd and my companions laughed and high-fived each other, proud of their work.
“I hate you!” I mouthed at them bringing even more laughter from my companions. The show moved along and soon we were being judged for the finals. The crowd cheered for each of us in turn as the DJ judged the relative volume of the cheers for each girl. When it was over, he called my name along with the workout queen and one of the Barbie dolls. I was in the finals. I moved over next to the other girls, each perfect in her own way and tried hard not to judge myself in their presence.
“OK, girls. This is winner takes all. Five hundred dollars is on the line. Show us what you’ve got!” The DJ announced and Ginger doused us all again with water that felt even colder than the first time if that was possible. The Barbie doll was sure she had it in the bag and simply felt herself up almost as if she was bored by the proceedings and just wanted her money. The workout queen was in nothing but panties and the t-shirt and she danced seductively for the crowd and boy could that girl move. I tried to figure out a way to top them but I ended up just shaking my hips and rubbing my nipples.
Fearless Curves Page 5