Night Out Ch. 03: Talk to Me

I wonder if it's too late? I mean...it has been three days.

"Jamie, we have a meeting coming up around 2:15 pm. Did you get the email?"

He looked up ungluing his zoned eyes that were unfocused on the screen of his work computer. Again, he was lost in his thoughts as he feigned being busy due to the inability to focus. Evy was heavily on his mind; invading his workday. He almost didn't recognize his name, which highlighted another obstacle of hesitance with reaching out to her.

"Uh yeah. It was sent out hours ago Lisa." His response was flat unlike what he planned, but he did not want her to linger. "I'm a bit preoccupied with this new client's records, I need to focus..."

What's the point of sending email hours ahead if you go around asking each time.

He didn't wait for an answer and sighed when he felt her presence leave for the next victim. June stared at the spreadsheet ahead of him and groaned before running a hand through his hair. He was thankful for his job by not having to deal with many people in person, leaving some of his more personal choices like hair length, a non-issue.

His work itself wasn't too bad despite him working as a financial analyst for a small company. It helped that they had an established clientele and he mostly updated the new information. June pulled out his phone and looked at the time, 1:45 pm reflected back at him. He then found his finger scrolling his contacts and landing on Evy.

"Hey, remember me?"

No.

"It's me June? Actually Jamie, but you can call me June."

No.

"Fuck why am I making this hard."

June looked up to see coworkers leaving their areas, fifteen minutes had passed. He decided to head to the conference room to make sure he picked a decent seat; not too close to need to pay attention and not too far to get lost thinking about Evy.

He snagged a seat midway to the conference table and wondered how long it would last. The meeting would most likely cover their stats as a company; how to improve, new guidelines, regulations, and possibly new tools. Stuff that would most likely not affect how he did his job. But a welcome reprieve from being stuck at his desk.

He looked at the time again, it was almost meeting time and the room had filled with most of his co-workers. June thought of leading a text with the promise of returning the clothing Evy provided but that wouldn't do.

"Hey, it's me J-" His boss came into the room popping streamers and celebratory items announcing a new partnership with a highly desired client. The suddenness made June jump; finger hit send along with an audible "fuck" that left his lips, silenced by the merriment of the room.

--

"Hello, my name is Evy. How can I assist you?"

She rolled her eyes and made the shoot me handgun to imaginarily blow her brains out. Call center work was wearing her down, the only thing that kept her going was some co-workers and not having a new offer accepted. Also, not winning the lottery.

She nudged the headset, it was beginning to hurt her ears, and did her best to get the customer off the phone. They were simple to assist and a decent human being unlike many of her interactions most days.

Despite the pace of the days, her thoughts would slip to June. She almost dared him to message or call her, it's been three days. She was almost mad at herself, so worked up over some beautiful and handsome androgynous-looking crossdresser with a nice and thick dick who...

She shook her head and squeezed her thighs, "I'm supposed to be mad at him. He is a stranger anyway I shouldn't care. It was bound to happen. He probably did things like that all the time." The nerves in her stomach rejected that idea.

Evy turned her attention back to her computer as the headset signaled an incoming call, "Hello welcome to June, my name is.."

Shit.

She stuttered and corrected herself while the caller on the phone laughed and told her it was May. She could feel the heat rising in her face embarrassed that thoughts of him were that strong. The phone call had lasted for a while, as she had to look up a bit of information and reach out to other departments. Long calls were usually her favorite but she had felt her phone vibrate.

The pang of excitement ran through her chest, she had been like this all week when it came to text only to be disappointed when it wasn't June.

I doubt it's him, it's the middle of the day anyway.

Once the phone call was finally over, she cleaned up to prepare for lunch. She debated eating or deciding if she wanted to go outside and pretend there was some freedom to her madness.

On a whim Evy gave in to check her phone, her face lit up despite her trying to pout.

"Is that all he's going to say after three days? Really?!"

She texted back, "J who?" out of spite and grinned when she saw he had already received it.

She was upset with how happy she was but glad he decided to reach out.

"I'm sorry, it's me June...I was startled and sent the message too soon. I hope you have been well Evy."

She felt a tingle between her legs as she could hear him in her head saying her name, he said her name many times and in different ways last time they were together.

Her fingers began to furiously type, she was excited and it was showing.

"You know I had this whole thing in my head, I was going to chew you out for not saying anything for this long. But do you want to meet again? And you have my stuff, I'll fight you for those shoes."

--

June smiled as they text back and forth, he couldn't hide the enjoyment. And eventually felt curious eyes on him after the celebrations calmed down.

He ended up texting Evy to let her know he was supposed to be paying attention but would love to meet again. He invited her to his place since he went to hers the last time. She accepted and they planned to meet the upcoming weekend.

--

Friday rolled around and Evy couldn't wait, she didn't know what to expect but her stomach did somersaults thinking of June. They had planned to meet after she got off work, her workplace was surprisingly close to his apartment and she left work later than he did. Thus he had time to clean up or prepare before she came over while giving them the fastest time to meet after work.

"Look sir if you'd stop interrupting me and allow me to finish maybe you wouldn't have any questions." She groaned having a difficult customer for her last call who was working her patience. She was sure she'd get reprimanded for that response but she had plans. And a customer not listening to the last fifteen minutes wasn't helping.

"Wow, I'm so sorry I'm having a hard time hearing you, I think we're losing connection." She quickly dialed to transfer the customer and dropped him into that line. Her office buddy looked at her before giving a sly smile as she clocked out and began waving bye.

She was quickly on her phone and texting away, "I'm on my way, see you soon."

--

June had received her text letting him know she was outside. Mark watched curiously poking at June about having company over.

"You hardly ever bring chicks here and when you do you sneak them out so fast. This one must at least be a 5-6? I swear the last one I heard had claws when she was creeping out, I thought you had a raptor in the kitchen."

June grimaced at Mark before he responded, "I'm sorry you get so fuck up that you get your dates mixed up with mine. I mean, they gave you a chance at all, you should be honored."

Mark mouthed a "fuck you" before he went to look out the window as June stood by the door.

"Damn, I wish she was coming here. But I know she is not here for you, dude you could never."

Evy was walking by closing in on their apartment door unaware of the comments and eyes following her movement. June gave a smug look before he opened the door moving out of the way to let her in.

Mark stood by astonished, wondering how they met. Neither he nor June brought back women they would actually be interested in.

"Hello Evy, don't mind him, that's Mark my roommate. I'd advise you to ignore him completely, it saves your sanity. Trust me."

June smoothly led her down the hall into his room and closed the door, Mark was left dumbfounded and a little proud.

"My boy..."

--

Evy looked around admiring June's room, it appeared to be decorated with artwork of various forms and styles. Everything was neat, and clean, unlike her bedroom that had been a mess with clean clothes piled in a basket in the corner.

He had also cleaned her clothes that were placed neatly folded at the end of his bed. Insecurities whispered in her ear and she debated if he had everything nice and tidy so she could get everything and leave quickly. But he sat with an innocent look when she read his features, giving off a sense of ease and welcome.

Finally, she broke the silence, "Have you been avoiding me because of how we met? I mean...maybe that's not how to ask."

He offered his bed for her to sit on as he sat into his office chair and turned on some light music.

"I...I told you that was my first time right? Until that point, I had only played with the idea and my sister did make up on me a few times. But me doing it myself, wearing that dress and all was a spur of the moment. And then I met you."

She sat in silence absorbing his words and trying to follow his train of thought, "Did you wonder why?"

She invited him closer to her by holding out her hands, he took them enveloping them in his warmth as he sunk the bed down sitting with her.

"I want to say it was the same with me, it was my first time going out alone. If I had gone with friends I doubt I would have ended up in VIP to meet you or anything. But I guess that is part of it."

"Right place and time." He whispered while debating another question. "But you had a certain expectation and...you still went along."

Evy smiled thinking back to his reveal in the bathroom stall. "I won't lie, it caught me off guard, but I don't know it doesn't bother me. When we met we weren't exactly thinking we'd go home for sex or did you?"

She asked while giving him accusing eyes that held a glimmer of playfulness.

June held his hands up in surrender, "No way, no expectations. I almost didn't leave the apartment."

"I think that helped, I'll admit I was thinking about it a little but blame it on the alcohol. But we kind of became friends first and we vibed. There weren't any people around to give input or influence. So...I just went for it."

June laid back on his bed and felt Evy follow suit and snuggle up against him.

"You happening to be a man was just a reverse uno to me but...I don't know I felt like if you were showing as much interest in me then why not?"

He looked down at her as she trailed off trying to formulate words to say what she was thinking.

"It's really complicated, we as a society have expectations of how things are or should be. So when we are met with something we don't understand it either upsets you or you accept it..."

She then ran a hand over his chest in a comforting motion, "And it was hot."

"The things you do to me." June groaned as she gave a cheeky smile before presenting a question of her own.

"Do you want to continue, what do you want this to be?"

Silence permeated the room again, but Evy stayed where she was pressed into the comforting warmth of June as he seemed deep in thought.

"I don't know what this is. It feels odd to me because you are basically a stranger to me yet the first and only to know what I consider the most intimate thing about me. I don't know much about you, compared to that."

"So then no more sex or anything?" She quipped.

"Let's not get ahead of ourselves."

She laughed and sat up, "We don't have to decide anything yet. Maybe we can be friends who happen to do kinky things together."

"I think I like the sound of that, I'm not exactly sure what that's supposed to be but I hear kink and we."

Evy whispered, "I consent to this as long as I have the power to fully terminate if you tell me terrible jokes."

He hesitated and sat up to look her in the eyes, "Termination requires a fee of 6 more sexual encounters and offer to reissue after said encounters."

"All jokes aside Evy, I was afraid of having this so tightly attached to you as an actual person. I don't want to mess it up. Also, my real name is Jamie but you can still call me June..."

--

They continued to talk through the night joking and getting to know each other. Evy had loosened up a little and walked around his room admiring what she found out to be his personal artwork. He even showed her his closet that had his sister's clothes. From what she could tell his sister was smaller in both height and size, it gave her an idea.

"June do you have any measuring tape? Not for construction but for clothes?"

He looked at her curiously wondering if she was secretly some master seamstress but she turned to him with lust-filled eyes.

" I have to take your measurements June, stay still for me."

His skin bristled with excitement, she trailed a hand along his happy trail into the front of his pants. Then she followed descending onto her knees in front of his clothed body. With quick haste, she undid his pants and slipped down his boxers shortly after.

Evy took care to give him daring eyes as she told him she needed to measure him.

June gave her an incredulous sound knowing the effect she had on him, he was already halfway hard before she dropped to her knees. She took the tape and wrapped it around whispering about maybe getting measurements later.

She then playfully wrapped it to completely cover his skin, "Wow June, someone's excited. and look, here's a chance to learn about me."

She gently tugged the measuring tape off his dick and licked the tip. June hissed in pleasure and wavered in her hot mouth as it crept further along his length. He looked down in shock to see her nose pressed firmly against his pubic mound. She even wiggled her tongue and tickled at his balls as a trail of saliva followed her lip while she slid him out.

"No gag reflex...so if I ever end up choking you have to know what to do or write my obituary."

She gave him no time to respond because she sucked June back down her throat. His thickness almost disallowed her to do so but she was getting turned on hearing his voice and moans. She saw the way he looked at her, she knew they had both been on each other's minds.

Sucking and licking she left his dick glistening in the light. Whatever her mouth wasn't touching her hands were. She could feel him twitching between her fingers and releasing a pearl of precum that she lapped up languidly. She made sure to lick and suck on his balls making him moan and sway.

Evy then looked up at June with a shiny wet face from her efforts, "Do you trust me?"

The question surprised him, was it a trick? "Fuck...I-In what way?"

She popped his cock out her mouth so loud he wouldn't have blamed it if Mark heard it, "As your kink buddy I make it my duty to try things with you. Is that alright with you? And...if you say stop for anything I will."

June's eyes could barely stay open, Evy was threatening to suck his soul from his body. "Yes, I trust you-Ah shit."

Suddenly she stood up asking June where the bathroom was. He watched her bewildered as she removed her touch and wiped her face.

"I need to wash up, you don't mind do you? Don't do anything without me...you better not cum while I'm gone." Evy quickly excused herself with a wicked smile, she took her phone with her and the clothes June had washed. He told her where the bathroom was and where to get a towel.

June managed to sit on the edge of his bed looking distraught at his hard angry cock as it bobbed against him. He wondered if this was a good idea but her words commanding him sent a tingle down his spine. He groaned in frustration but he was also excited to follow her orders.

This arrangement might make him find out more than he thought he would about himself.

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