Crossed Lines Pt. 12: Flirt w/ Tom

// Author's Note: I'm so sorry for the delay in getting this next part out. I've been experiencing quite a bit of major depressive disorder these last several months so please bear with me. //

Recap:

Part 1: This part takes place after Part 2 through Part 10. It details a breaking point in Aiden and Lacey's relationship that results in infidelity.

Part 2: The chronological start of the series. Given Lacey's promotion and long work hours, Aiden uses porn for sexual release. This made it difficult to maintain an erection. Insecure about his erectile dysfunction, Lacey avoids sex. To spice things up and stop him from masturbating, they use a male-chastity that he wears when Lacey working. Sexually unsatisfied, Aiden starts crossdressing. Due to the chastity, he can't find relief via orgasm, causing his crossdressing to amplify.

Part 3: The sexism and misogyny Lacey faces at work left her feeling a lack of control and security. When she catches Aiden crossdressing she takes out her frustrations on him by making him wear the chastity and her clothes much longer than planned. Despite the lack of sex, Aiden likes the punishment. He becomes the best "housewife" by fulfilling all household chores. But going to the community laundry room required him to pass as a real woman. This motivated him to improve his makeup, feminize his voice, and exercise his glutes.

Part 4: His female persona 'Bri', became a frequent fixture, with Lacey encouraging it. This created a sense of control for her, and she no longer felt obligated to have sex with him. Lacey treats Bri to a shopping spree at a thrift store, buying her first set of female outfits. She then takes them for a drink at a gay bar.

Part 5: Aiden is crossdressing at least 3 times a week now, and is better at passing. He surprises Lacey with facials at a day spa. Aiden's esthetician recommends he try temporary lip fillers. Lacey encourages him to follow through with it.

Part 6: Aiden believes 'passing' at a straight bar is most validating. He convinces Lacey to go out to a bar called The Nebraska. Over drinks, they discuss fantasies, like their attraction to men. The conversation escalates to Aiden/Bri disclosing she finds a man at the bar to be cute. Bri turns to go to the bathroom and bumps into him, causing his drink to spill.

Part 7: Bri meets the man's girlfriend Jess, and they exchange numbers. The evening ends with Lacey and Bri fantasizing about Bri having sex with men and discussing the use of a strap-on. Lacey instructs Bri to book her first laser hair removal appointment.

Part 8: Feeling insecure about having a square-shaped waist, Bri purchases tight-fitting shape-wear to give her an hourglass figure. Jess texts Bri and encourages her to create an Instagram which she does. Lacey tests Bri's obedience by making her get her ears pierced. Aiden/Bri misses an important work meeting in order to satisfy her commands. Lacey then orders Bri to purchase a strap-on dildo.

Part 9: Lacey makes Aiden wear the strap-on while he is still wearing the chastity. She orgasms and then fucks him with the strap-on while he's dress as a woman. They fantasize about him getting a boob-job. This part ends while Lacey is fucking Bri with the strap-on.

Part 10: Bri follows through on her laser hair removal appointment, encouraged by Lacey. They discuss how expensive it is, and begin researching insurance workarounds to afford future sessions. Lacey becomes more comfortable with Bri's feminine persona in public settings. Bri gets a surprise text from Jess inviting them out again.

Part 11: Bri books a Planned Parenthood appointment to get a gender dysphoria diagnosis so insurance will cover laser hair removal. Though she plans to fake it, the experience becomes real, and she's surprised when the doctor offers her hormones. Bri agrees, thinking it will help justify the diagnosis. Bri and Lacey plan another night out, with Lacey teasing Bri about flirting with Tom again.

Part 12

As Tom walked away to buy me a drink I gasped for breath, fighting against the tight fitting shapewear around my waistline.

I wore the smallest sized shapewear I had, wanting to look as feminine as possible. I loved how it gave me a nice figure, making my hips and fake breasts more pronounced.

The constant pressure was a reminder of my feminine presentation.

The loud music felt like a good distraction in the crowded nightclub as I struggled to get my variance after that intensely flirtatious banter with Tom.

I shocked myself with how well I could flirt. Flirting with women as Aiden had always been a disaster, yet here I was, effortlessly teasing and enticing a man like it was coded into my DNA. I guess I assumed I would be way more nervous and awkward around Tom, especially knowing that he might have a thing for my female persona.

Although I still felt a little nervous about him returning to talk to me, there was a lot less fear associated with that. I now felt nervously excited about talking to him again.

What was so wild was the positive feedback I was getting from him. Within minutes he offered to buy me a drink!

Why am I way more confident and comfortable being a woman at a nightclub than being a man?

It didn't really matter because I was starting to have a lot of fun. I turned around, carefully balancing on my heels, looking for Lacey; I couldn't wait to tell her that I was getting a drink bought for me!

Spotting her with Jess, I slipped between bodies to join them, the fabric of my dress sliding against my thighs with each step. Jess turned to me with a grin and said while pointing, "Oh hey, I saw that you finally made an Instagram. Did you see I added you?"

Fuck. My heart dropped for a little bit and I glanced at Lacey quickly to see her reaction. I really wished Jess hadn't said that. Mainly because I should have spoken to Lacey first about making an Instagram account for my female persona.

"Oh... yea," I responded cheerfully, attempting to mask my fear.

"Instagram?" Lacey said, looking more confused than annoyed.

"Yea, I peer-pressured Bri to make one," Jess replied, alcohol mingling on her breath. "She didn't tell you?"

Jess came across as a little harsh and competitive. Like one of the characters from that Mean Girls movie.

Lacey glared at me. I could tell it upset her.

"No, he didn't-- she didn't, I mean," Lacey answered, taking the opportunity to take a jab at me.

"It's nothing really, I'm not following anyone or anything like that," I said, trying to pass my Instagram account as no big deal.

I was worried that Lacey might think I was keeping it a secret. I was sort of keeping it a secret but I didn't really think it was a big deal even tho I figured she might think it was.

Jess could pick up on the growing tension and awkwardness between Lacey and I. Not knowing we were a married straight couple she said, "Bri, Insta is a single girl's resume. That's the first thing a guy's going to look at after meeting you."

I exchanged a short awkward glance with Lacey before saying to Jess, "I'm not really looking for anyone right now. Just working on myself."

"Ok, hold on," Lacey said a bit forcefully as she stuck her finger out to make a point. "You did call dibs on Tom, remember?"

What the fuck?! Why would she say that out loud? Oh my god... what if Jess says something to Tom?

I mean technically she's right, I did call dibs on Tom, but it was during our dirty talk in the bedroom. I'm surprised she even remembered me saying that.

I must have looked like a deer in headlights, before turning to look at Jess to observe her reaction.

She looked surprised and intrigued as she heard the tea Lacey just spilled.

"I can sense some competition going on here," Jess said loudly over the music and noise of the club as she took another drink from her cocktail glass. "You should definitely jump on it before he gets on the dating apps."

"Is he not on Tinder or bumble?" Lacey asked.

"No, but he's been thinking about starting one," Jess replied.

Lacey then looked at me and asked half joking, "Do you have a Tinder or a bumble you're not telling anyone about?"

"No," I replied quickly. "I've never had one."

"Bri, what?" Jess asked with a surprised look on her face. "How have you never used a dating app?"

I cocked my head at an angle and lied, "I just don't want to be judged. It makes me nervous and what if nobody likes me?"

"Bri, you're a babe," Jess said as she motioned with her hand, pointing to my body. "You'd get so many guys to swipe on you. Are you on the dating apps, Lacey?"

"No," Lacey said, shaking her head, before saying something that surprised me, "But now I'm thinking about it."

I couldn't tell if she was being serious or taking a jab at me with that statement.

"What if you both make Tinder accounts and see how many swipes you can get," Jess spoke, clearly more intrigued by the conversation than Lacey and I.

My cock started throbbing in my groin as I imagined Lacey swiping right on other men. Would they touch her like Tom had touched me? Would they do more?

I could feel my breaths getting shorter and faster as the shapewear continued to compress my waist. The conversation wasn't helping.

To my relief I felt a hand at the small of my back, lingering just above the curve of my ass. It was Tom.

His fingers pressed into my waist slightly, possessively. It wasn't just flirtatious--it was claiming territory, and my body liked it.

He was holding two cocktails in his other hand, gesturing for me to take one.

I reached with both hands and took the cocktail from him, my painted nails briefly brushed against his masculine hands.

Normally, I wouldn't notice a casual brush of my fingers against someone else's, but this was different. It was the first time my 'female hands' ever interacted with a man's.

I didn't hate it. It didn't feel "gay" either. In fact, I wanted our hands to touch again. Would our hands touch again?

Tom didn't put himself into the conversation between the three of us 'girls' and instead stood to my side implying that I turn to talk to him.

I felt a little guilty but I didn't feel like Lacey was happy with me at that moment so I didn't want to talk with her. Instead I delicately turned to face Tom.

At the corner of my eye I could see Jess and Lacey shooting glances at me as they spoke amongst themselves. I could tell that Jess was talking about whatever chemistry there could be between Tom and I, and I'm sure Lacey was playing along.

I shot another glance back at Lacey and she did not look pleased. I felt like I was on her shit list but I really didn't want to deal with that right now. I figure I'll ask for forgiveness rather than permission and keep chatting with Tom.

"You gotta let me know what you think," Tom said, motioning to the cocktail I was holding.

"Oh, thank you," I said in my girliest voice as I shot him a sweet smile. Our eyes met for a moment longer than necessary.

My thoughts returned to how he got my attention by placing his hand on my lower back. It really enforced the femininity I was feeling all night in this outfit. It was so validating to have another man touch me gently as if I were a woman.

I must be getting tipsy because I felt so confident. It was this weird feeling like everything was going right and nothing could be wrong in that moment.

I guess it's odd that I would describe it as weird but the more I think about it the more I realize that confidence was a foreign feeling to me. It wasn't something that I ever really felt in my life.

In girl-mode, confidence is something I've found myself feeling a lot more often. I guess that's one of the reasons why I continue to explore my feminine side.

It doesn't hurt that Tom is boosting my ego. He's so charming, witty, and flirty. I love the validation he's giving me and I don't really want to stop. But now I'm worried because I don't want him to get any ideas. How do I keep a guy like Tom in the friend zone while still being really flirty with him?

At what point do I hit the brakes and end this seemingly natural escalation between us?

I held the straw of my cocktail between my painted finger nails and took a sip. My eyes traveled upwards to meet Tom's. He was making direct eye contact with me and smiling.

I looked away, shy and brimming.

"What do you think?" he asked.

"I like it," I lied, then twirling the straw with one finger I added with a playful smirk, "But I'm more curious about what you're drinking."

His smile widened.

"Well, why don't you try it," he said, before handing his drink to me.

I instinctively took his cocktail in my hand and thought about how sharing drinks with someone is quite an intimate thing to do. I felt a little guilty and wondered what Lacey might think if she saw me. I brought up the glass to my lips and took a sip while simultaneously turning slightly around to see if Lacey was watching.

But she was no longer standing there. I was a bit relieved at that but also a tiny bit concerned about where she could have gone.

"It's really good," I said to Tom before handing the drink back to him. Then feeling a little brave because Lacey wasn't there, I said with prolonged eye contact, "I like your taste."

Tom paused, setting his eyes on my lips, and replied, "I have good taste in lots of things."

My heart was racing as we stood there incredibly close. I also got extremely nervous because as he looked at my lips I instinctively looked at his and realized we were within kissing range.

That pause lasted way longer than I wanted. What was I thinking?! Not just that but the feelings I was going through were wild. Why did I pause? Was I expecting him to kiss me?

I awkwardly looked down at my drink and brought the straw to my lips and took quite the large sip. Since the cocktail was mostly full of ice I was going through it pretty fast.

We continued chatting for quite a bit before Tom noticed how quickly I drank my cocktail and said, "I should have got you a double. Let me get you another one."

Before I could say no and tell him that I had to find Lacey he turned slightly to begin walking through the crowd then he reached out with his hand motioning me to grab it.

My body moved before my mind could catch up.

When our hands met it felt so thrilling, and sexual even. It also felt like I was cheating on Lacey. It felt so wrong to feel our hands grasping each other.

All of this flirty build-up was no longer just harmless banter. It felt more real now.

He was so gentle with me, holding my manicured hand so softly. What if Lacey saw us?! I would feel so awful.

I was surprised at how much it turned me on too!

I'm not gay, and although it didn't feel gay to hold his hand, I couldn't help but be shocked at how much I enjoyed holding onto a man's hand.

It felt safe, like I was being taken care of, as he guided me through all those people. Some were dancing, huddled closely together.

It was such a validating thrill to know what it feels like to be a girl in a nightclub.

If you saw us you'd think we were 'together', and that thought sent a warm tingly sensation down between my legs where my dick was locked in chastity.

Tom continued to guide me through the moving bodies. My padded chest brushing up against random strangers as my heels clicked against the sticky floor. I was hyper-aware of everything: how warm his hand was, how confident his steps were, how I was letting myself be pulled further and further.

He gripped my hand with more firmness as we pushed through the more crowded areas. I reciprocated his grip and squeezed onto his fingers more tightly. Holding on to another man's hands in a way that wasn't a handshake was very new to me. In fact I was holding it with a sense of desire. It felt so strange and wrong but I still liked it and I couldn't resist him.

I couldn't believe that all this work I'd put together to look like a woman and now I was finally feeling like I was being accepted and treated as one. The way he held my hand with our fingers almost entwined felt like this entire fantasy was actually real. It was such a simple gesture but it was a completely new and validating thing to experience.

Tom was giving me a sort of validation I've never felt for anyone before.

All these feelings started to terrify me because I had this random thought that I want to do this again. I want to recreate this night over and over. I want to go clubbing on a regular basis and I want to see Tom more.

Why couldn't I be this confident as Aiden? Why was it so much more fun and comfortable and safe when I'm dressed as a woman?

When we finally escaped the crowd he continued holding on to my hand and I continued holding on to his, not wanting to let go.

It wasn't until we finally reached the bar itself that he let go to flag the bartender down.

"Another for the lady," Tom said smoothly, "Make it a double."

He then turned to me, his eyes glancing over me in a way that wasn't crude--but intentional.

I bit my lip, shifting slightly on my heels. My heart was beating faster than it should've been. I loved that he kept looking at me with hungry eyes. It was so validating and it really made me feel like I was an attractive woman. I couldn't get enough of his validation.

"You okay?" he asked, leaning in, his voice just loud enough to cut through the music.

I nodded, though my brain was screaming. You need to find Lacey.

But God, it felt so nice to be looked at this way.

The bartender set the drink on the bar, and Tom handed it to me like he'd done it a hundred times before. I wrapped my fingers around the glass, brushing his in the process.

"Thank you," I said, looking up at him sheepishly like a helpless and thankful girl.

I then reached for the straw, noticing Tom's eyes following it as I brought it to my lips and took a sip.

"There's something compelling about you," he said, his voice dropping slightly. "You've got this energy, something about you. I'm not sure what it is."

My throat tightened a little, because there is something about me. I'm not a woman and I don't think he has a clue about it.

"Maybe you don't want to know," I replied, trying to sound playful, but it came out a little too honest.

Tom smiled, "I think you do."

I didn't respond. I couldn't.

I looked away, scanning the room again for any sign of Lacey--but the sea of bodies all blurred together. I couldn't see her. Couldn't feel her presence. And the guilt, the panic, it started to creep up my spine again.

Tom must've noticed because he stepped in just slightly. "Everything alright?"

"Yeah," I said, a little too quickly. "I just... I need to check on my friend."

He nodded, but didn't step back. "You think she might be back in the crowd where we were standing earlier?"

"Um, maybe," I replied with a feminine shrug of my shoulders.

I should have just gone on my own to look for her but Tom didn't make a good point. We should at least go back to that spot to make sure she's not there before I go out looking for her again.

Tom held his hand out like a gentleman and I set my hand in it. This time it felt a little more sensual as he held onto my hand more securely while guiding me through the crowd again.

When we got to the spot, Lacey wasn't there.

"If we stay here she'll know where we are if she comes looking for us," Tom said, making another good point.

Hopefully, Lacey won't be upset with me.

I nervously took another long sip of my cocktail, careful not to smudge my lipstick.

"I should at least try to text her," I said to Tom as I reached for my purse to pull out my phone.

I could see Tom pulling something out of his pocket. It was his phone.

"Since you have your phone out," Tom said, "Why don't you give me your number so I can text you if we lose each other in the crowd tonight."