Rochelle's

"Oh my gosh, Alex, is that YOU?!"

A sickeningly familiar voice called from close by as I sat at the bar. My eyes stayed down under my freshly curled eyelashes. Part of me hoped that if I just didn't move, the owner of the voice might doubt herself (or that I might become invisible, which would be even better). But when I felt a hand start to graze the top of my own as it was resting on the bar, I knew that plan wasn't working.

"It IS you! Alex, what are you doing here?! And dressed like...THIS?" The woman's voice was clearly shocked, but friendly, now demanding my attention as she grabbed my hand.

My head turned and my eyes raised to look up at Marisa. Her dark brown hair was slightly longer since I'd last seen her, now draping down over the tops of her shoulders. She had on a shimmery red dress with short sleeves that I was certain I'd seen once before. With her fair skin and hazel eyes, any guy would normally be perfectly content to have a cutie like this come up to them at the bar. But normally the guy wouldn't be dressed as a woman, and it wouldn't be his ex-girlfriend.

Marisa's timing was unfortunate, although I knew that I had been rolling the dice with this routine I'd started. For the past month, a couple times a week I had been dolling myself up and coming this bar, "Rochelle's". I don't know that it's exactly a gay bar, but it's gay enough that whenever one might see a woman drinking alone on a quiet evening, there was always a chance that things were not as they seemed.

Most nights I'd get approached by at least one or two men who would always offer to buy me a drink. Sometimes they were surprised to find out I was a man, and sometimes it was clear I was exactly what they were hoping to find. In every instance though, I would politely decline the drink, because that's not why I was there. I wasn't after free drinks or a one-night stand; I just wanted to be myself out in public every once in a while. If the guys wanted to talk, they were welcome to stay, but things would always end right there at the bar.

My relationship with Marisa had concluded a few months ago under amicable terms. She was starting a grad school program that would take her out of the country and since we'd only been dating a short while, we agreed it would make the most sense to call it quits before she left.

The relationship, while short, had been a wild ride. Despite Marisa's unassuming outward demeanor, her behavior in the bedroom was anything but vanilla. Following our second date, she insisted that I allow her to swallow my cum after a very enthusiastic blowjob. A couple dates later she wanted me to provide the same experience to her asshole. She was always experimenting with lingerie, roleplay, and even a sprinkle of bondage. We packed as much as we could into the time we had.

During our affair, I flirted with the idea of opening up to Marisa about my zest for crossdressing. She was the first girl I'd ever been with who made me believe that she might mean it when she said nothing was off the table. I wasn't sure if Marisa was the "marrying" type, but there was a certain appeal in getting to be with someone who made you to feel like you could be your complete self.

As we neared the end of our time together, Marisa hinted at a proposition that caused me to shelve any plans to disclose my crossdressing habit. One afternoon while we were laying on the couch together following an hour of her bouncing on my cock, she turned to me and said, "I think it would be really hot to get to watch you fuck some other girl. Something about getting to see my man make some girl squirm the way you make me do...it gives me goosebumps!"

I had never given thought to the possibility of being in a 3-way. While I believed I was a good-enough-looking guy who was maybe slightly above average at having sex, I didn't have the sort of alpha-presence you would normally associate with guys who take on two girls at once. But if Marisa was going to facilitate a 3-way, then I didn't want to do anything that might dampen her perception of "Her man". I figured that if I was going to ride this train of sexual endeavors with Marisa, I might as well ride until the final stop.

So I never came clean with her about the crossdressing. And the 3-way never happened.

When it was time to say "Goodbye", I was sad to see Marisa go, but part of me recognized that the whole thing was probably more of a "fling" than it was love. I was ready to move onto the next stage of my life, whatever that might be.

But as time progressed, I found myself pining for the relationship more than I expected I would. Yes, I missed Marisa, and the sex was great, but I missed how comfortable she made me feel. I felt like I had blown an opportunity to be myself with her, and I spent a lot of time wondering if I was ever going to have that chance again.

Part of the problem was I wasn't even certain what it would mean to "be myself with her", or any other person for that matter. There would undoubtedly be questions asked by Marisa that I wasn't sure I had the answers to for myself. Was I trans? I didn't think so. Was I bisexual? Maybe. How did I feel about anything of those things? Clearly not great if I couldn't bring myself to discuss them.

Shunning all of those questions had me lost in a loop, so I decided the only way I was going to get answers was if I allowed myself to embrace whatever feelings I had that came along. So with Marisa out of the picture, I began to dress more often. I learned more about the clothing and make-up. I gradually tailored my looks to be more conforming to my body and face shape. I even began to incorporate some exercises into my gym routine that I thought might contribute to a more feminine appearance. With each passing day, I began to grow more confident in the feminine appearance that I wanted to display.

Despite the improvement in my "look", my relationship with the situation only seemed to worsen. I grew anxious over the disparities between my day-to-day male appearance and my occasional feminine look. I felt as if the time I spent in my stereotypically male lifestyle was just a holding pattern until I could feel like a woman again. All the while, I hated myself for feeling that way. Whatever pleasure I felt in the moments of getting to be myself was always discounted by the contrasting feelings of self-loathing.

I turned to the internet to see if there were any other crossdressers out there who shared a similar experience, only to discover this was apparently a core aspect of the lifestyle. Moments of pure bliss, followed by agonizing shame, and a determination to refrain from such behavior. Apparently hating myself was part of the process. Great!

I came across on one Reddit user with the name "SarahslittleSecret21", who recounted their own experience of occasionally visiting local "safe" bars while dressed up. She said that visiting places where she knew she wouldn't receive any grief gradually helped her feel more comfortable being dressed up. She said that it's even given her the confidence to come out to a couple of her close friends.

"So maybe there is some hope", I had thought to myself. I was getting desperate to feel better about the situation. The whole point of this journey had been to become surer of myself. If I was ever going to open up to Marisa, or anyone else for that matter, I knew I was going to need to acquire some level of acceptance of myself.

The first time at Rochelle's was more stressful than anything else (I barely lasted 20 minutes). But the second time was better. The third time I felt like I'd actually had fun, and after the fourth, I couldn't wait to be back at the bar (even if I mostly kept quietly to myself).

In fact, with Marisa's hand now there resting on mine, I realized that this was the first time in about a month that I'd felt stressed out in public. Suddenly it felt like I was there at Rochelle's for the very first time all over again.

I was in far too deep to try to make a run for the door, so I opted to play it as coyly as I could.

"I'm having a drink", I replied coolly, the tremor in my voice hardly noticeable, "what are you doing here? Is your program finished?"

"I can see that, and uh...", she was somewhat flustered herself, "yeah, it finished a few weeks ago. I just got back into town last week."

I took a sip of my drink, my eyes looking forward into the bar before I turned back to her. As I pulled the drink away from my lips, I noticed only the slightest stain on my glass from my dark red lips. I knew that matte-finish lipstick was worth the money.

"That's cool", I answered her, "did you enjoy it?"

Her eyes were as wide as could be, her mind only partially processing the question. I could tell that there was some part of her that felt like she'd entered into an alternate universe where her ex-lover was now some sort of strange feminine character in a bar.

"Yeah, it was good-but okay, hang on-", Marisa had gathered herself and her voice was growing stern, "What the fuck is this though?" she barked at me as she gestured up and down at my appearance.

I was grateful for the change in her tone because I wasn't sure how much longer I could act aloof. That said, I wasn't really sure how to describe what it was either, so I decided to play dumb.

With a sheepish smile I looked back at her and said, "What do you mean?"

She about lost her mind.

"What do I MEAN? You know damn well what I mean! I leave my boyfriend to go to Peru for 4 months, and I come back to find him looking like some sort of inconspicuous Taylor Swift wannabe?"

Despite her tone, I had kind of felt like it was a compliment. She kept going.

"Were you doing this while we were dating? I'm going to be so pissed if you tell me that you were."

People hovering nearby had started to notice the conversation, and while most patrons kept to themselves at Rochelle's, it was hard to ignore what was going down. The last thing I wanted with any of this was more attention than it had already garnered, and I felt like I was one wrong answer from a full-blown fight.

Trying to figure out what to say, I asked timidly:

"Why do you care if I was doing this back then?"

"Because we could have had so much fun, dumbass!" She chirped back.

She hopped into the chair next to me and we started to talk. Initially, she had a dozen questions about why I was dressed that way, and right away it was clear to me I couldn't give her a wrong answer. In fact, the only thing I said that disappointed her was when I told her the truth about how I'd never kissed a guy in the bar, much less gone home with one.

About 15 minutes into our chat, a guy who I would guess was a couple years younger than us approached the two of us.

"Hello ladies," the guy said confidently and politely, "I don't mean to interrupt, but would you mind if I bought each of you a drink?" the man smiled at me before offering a wink to Marisa.

She rolled her eyes, but not for the reason I thought she was.

"Oh Joe, could you not be such a dork for once?" Marisa quipped at the man before backhanding his arm, "Joe, this is my ex-BOYFRIEND Alex. Alex, this is my friend Joe."

Joe's head snapped back to me as if to do a double-take, his eyes going wide.

"Oh SHIT! YOU are Alex? Bro, I thought you were really a chick! I've heard about you; Marisa told me you guys had some good times. I think she even said she was thinking she might call you up when she got back. She didn't tell me about this though, damn!"

He took a step back to take a second look at me.

Joe seemed like he was being genuine, but I could feel my face burning up. Among the mixture of emotions, at the very top was a sense of shame of being exposed to this man, a few inches taller and many pounds stronger than myself, who seemingly had some sort of close connection to Marisa. The whole thing felt extremely emasculating.

"Joe, again, could you not", Marisa butted in as her palm met her face in empathetic embarrassment.

Joe turned back to her.

"How are you about to tell me about half the stuff you guys would do, and not mention he can also pass as a chick?" He questioned intently.

"Because I didn't know about it until tonight!" She snapped back, "I'm just as surprised as you are!"

"Ohhhhh...." Joe hummed to himself, now having his own moment of discomfort. But it didn't last long.

"Well shoot. Alex, I'm sorry if any of this was rude, bro. I just thought you looked good. Well, you still do, ha!" He winked at me before ducking under Marisa's attempt to smack him in the back of the head and scampering away.

After he was out of earshot, Marisa turned back to me,

"I'm so sorry about him. He's harmless. Decent cock now and then. I always thought he'd make a good friend with benefits, but he just does so much stupid stuff that I can't even go anywhere with him."

"No, it's all good," I reassured her, feeling relieved to hear this wasn't a new boyfriend, "so you guys aren't a thing?"

Marisa looked at me confused,

"Me and Joey? Oh no. I mean, sure, we've fucked a few times over the years. But it's not serious. This is the first time I've seen him since I've been back in town. I wasn't even certain we'd go home together tonight, I just felt like going out."

"Oh okay," I replied quietly, suddenly feeling excited that perhaps this night might go in a direction I never anticipated. Feeling a bit more secure in the situation, I decided I'd give Joe his flowers, "I mean I would understand. He's a good-looking guy. Seems like he has a good sense of humor."

"Yeah, he is, for sure", Marisa agreed nonchalantly before pausing. A wry smile started to creep at the edge of her lips, "wait a second: You just said he's a good-looking guy-"

"Nooooo, no, no, no-", I tried to stop her but I was too late.

"Are you interested in him?!" She poked at me, suddenly the wry smile becoming a big smile as it swept over her face.

Now I was blushing again for an entirely different reason.

"OH MY GOSH, you ARE! You little freak!" Marisa cried out before I had a chance to defend myself.

"I am NOT," I insisted, laughing and a little embarrassed, "I just was flattered that he thought I could pass."

Marisa was not convinced, but she dropped it for the moment.

"Well," she started, "you can definitely pass. In fact, if you hadn't ordered your stupid Jack and Diet, I wouldn't have even taken a second look at you at this bar. But when I saw that, it made me think of you, and I wondered what kind of a woman would order my ex-boyfriend's drink of choice."

Suddenly she leaned in close to me, her hand slowly sliding up my thigh, her fingers tracing over the top of my green velvet dress.

"You know," she whispered into my ear, "you really should think about these things if you don't want us to know THIS is here..."

Her hand moved from my thigh to my rock-hard cock that was pinned across the top of my leg.

She pulled back to just far enough for us to see each other face to face. Her eyes scanned my make-up laden face before they came to rest on my lips while she bit her own. I had seen this woman in some sort of sex-crazed state many times before, but never like this.

Marisa took a deep breath and said, "You know. We never had that threesome."