Our Story

By Lindsey S.

Published on Feb 17, 2018

Transgender

I wrote this story for Jeff. Thank you for your inspiration, this continues to be so much fun.

Readers, feel free to write me, Jeff did and I loved it. Lindseycd4rp @ G M A I L. com.

Nifty is a wonderful place. Think of all the money you save on therapy because you come here and find out that there are other people just as kinky and messed up as you. They deserve a donation.


Will was surprised to get invited for a drink after work. It wasn't normal for there to be happy hours on Wednesday afternoons like this, and he wasn't a regular, but he figured there was no rush to get home. He had worked out already that morning and his evenings were usually pretty boring, living alone had lost it's excitement.

When it turned out that it was just Jeff and him, Will felt unusually comfortable. An introvert, he didn't usually do well in situations where he had to talk a lot, especially with somebody he didn't know. Jeff made it easy, his charisma and genuine curiousity made things seem natural. He kept the conversation going, talking about work at first, then moving to sports, with occasional personal questions mixed in.

By the time they were ordering their second drinks, Jeff gauged it as the right time to make a joke, "Maybe you should order something pink like your panties", which illicited a nervous laugh from Will. Jeff smiled back, "I'm just joking, but I do like the color."

Nervously Will tried to change the subject, "Is anybody else coming, or did you just invite me?" But he couldn't stop reaching back to make sure his lace thing was hidden. His mind raced trying to figure out how Jeff knew, when he could have seen.

"No, just us." Jeff cooly responded.

"Oh, OK," Will said, now seeming nervous. He tried to recover, "Well, thanks for inviting me, I didn't expect it I guess." He looked Jeff directly in the eye, for the first time, knowing Jeff was in on his secret.

Despite the conversation moving forward, Will could not stop thinking about how suddenly his world had just changed. He had kept this secret for years, and in one small casual joke, he felt totally exposed.

The bartender walked up with their drinks, and both Will and Jeff reached For their wallets. Jeff shook his head, `No, it's on me."

"You don't have to..." Will began.

"I always pay on the first date, unless you insist."

"Oh, ummm, OK." Will stammered, just wanting the moment to pass as quickly as possible. The word date stuck in his head. "I'm not gay." Will suddenly blurted out, but then stopped, having realized how stupid he sounded. "Not that there is anything wrong with that or, I mean, I have just never been with a guy, or I haven't wanted to, I mean....". He realized he had made his hole even deeper so he just shut up and looks at Jeff. "Thanks for the drinks. You didn't have to."

"Sorry about the first date comment, I didn't mean to be so forward," Jeff said with a sincere look. His genuine apology made Will relax which Jeff picked up on, bringing a smile to his face. Jeff smoothly changed the subject to work as they kept drinking.

Will found himself watching Jeff's face or hands more. his mind started to drift to sex as he watched him and finished his last drink. Will hadn't really looked or noticed before, but Jeff had some handsome features. He had an average build and they were roughly the same height. If he had to guess Jeff must be active but most likely was not as religious about his workouts as Will was. As Jeff moved his hands Will couldn't help but wonder what they would feel like against his skin. Once he started thinking about what Jeff might look like under his clothes, he knew he had to leave.

"I need to get going, it is a work night you know." His eyes watched Jeff's to gauge his reaction.

"I can give you a ride if you need," Jeff offered.

"No, I am good, but thank you. I had a lovely time." As soon as the words left his lips he realized how it sounded, and he wished he could take them back. He wanted to exchange them for something that didn't sound like they were on a date.

Before Will could react, Jeff said sweetly, "We should do it again sometime, let me know if that's something you want when you are ready."

"Ok, again thank you for the drinks." Will said as he stood up. Jeff followed suit but allowed Will to walk ahead of him, his eyes watching Will's ass, trying to picture the thong between his cheeks. They walked out of the bar together and went their separate ways.

Will spent the entire walk to the car wrestling with himself about what happened. Jeff just smiled, happy and content at the seed he had planted.


Once he got home, Will followed his evening ritual, which was a little more fun with the happy hour buzz. He stripped off his work clothes, so he was just wearing the pink thong he had put on that morning.

It was a little earlier than usual, but he couldn't help himself. Will closed his eyes and pictured himself as Lindsey on a date with Jeff. She was dressed in a cute little skirt and a bright pink top. She crossed her legs on the bar stool and played with her pink martini that Jeff had ordered for her.

Lindsey's thoughts moved to Jeff's hands and how he might touch her thigh. She would smile when he called her "Lindsey," and she would put her hand on his as it worked it's way up her leg, just under her skirt.

She felt her panties tightening, and her fingers reached down inside them as the scene progressed in her head. Her skin was already hot and she wasn't sure how she was going to be able to control herself tonight. Normally she liked to edge herself, but she already felt an urgency to climax.

She pictured herself on her knees sucking Jeff's hard cock as he encouraged her. "I love your panties," he said. "You were born to suck like this and look cute for me." She wondered what that would be like, to feel him getting hard, and what he smelled like, what he tasted like.

She couldn't help it, the picture in her head and the fact that Jeff actually knew about her panties was too much. She slowed down her jerking but it was too late, cream shot into her panties and onto her hand as her hips moved back and forth. She let out a soft whimper and closed her eyes tighter as her body released its sexual energy. The thought of Jeff cumming in her mouth came after she had cum, sending one last shiver up her spine. Embarrassingly she slid her hand out of her panties.

Normally she would have wiped it off, but something came over her that she had thought about before but had never done. She closed her eyes and brought her cum covered hand up to her lips. "I wonder if he would taste different than me" she thought as she sucked a little off her hand. "I want all of his," she thought before taking a bigger glob and letting it coat her tongue. Slowly she cleaned her hand and swallowed all of it.


Will felt like the next day at work was just like any other, except the constant distraction of Jeff. He made a point to come by Will's desk in the morning to say hi, and quickly began talking about the project they were working on. Will would see Jeff watching from across the office and Will would try to act like he didn't notice.

Every time Will felt his panties glide against his skin, he hoped that Jeff somehow sensed they were there. The thought of Jeff complimenting his panties again was beginning to take over every thought he had. It became so persistent that he decided he needed to do something about it.

After lunch Will worked up some courage to act, which was a first. Not only had he never fantasized about a real guy, he actually knew Jeff, and it was about more than just a disembodied penis. This was about Jeff. Will followed him into the bathroom, and was happy to find they were the only two in there.

"Hi," will said as Jeff stepped up to the urinal.

Jeff smiled back, "hey, how was your lunch?"

"It was fine, I am just getting ready for that meeting in ten minutes."

Will walked into the stall next to Jeff and pulled down his baby blue silk bikini briefs. He sat down and watched Jeff's feet under the stall, hoping Jeff noticed them.

After hearing Jeff flush, Will pulled up his panties and washed his hands. Jeff was done washing his hands and handed Will a paper towel making sure their hands touched. That shot a bolt of heat straight through Will, and he instinctively started to pull away, but regretted it as soon as he did.

They chatted for another minute, and Will could not help but look down at the ground when Jeff looked him in the eye. They were quickly interrupted by a coworker rushing in before the meeting. A little embarrassed, Will managed to look up one last time to smile at Jeff as they both walked out together.

During the meeting Will had to try hard to focus, but struggled to not sneak glances at Jeff. Whenever he would talk Will would watch intently focused on his lips, and occasionally Jeff would make eye contact with him. Every time he did Will's panties got a little tighter.

On the way out Jeff made a quiet comment to Will, "maybe for the color they should try pink or baby blue, either would look great."

Will smiled to himself, wishing he hadn't pulled away from his hand in the bathroom.

Before leaving Jeff stopped by and ask if Will had plans for the evening, and Will felt more excited than He thought he would. Deep down he wanted to cancel them, but his plans meet an old friend had been postponed twice already. "Rain check?" He asked.

"Sure just come and let me know when, I'm sure we can work something out." Jeff said, smiling at Will's reaction.

"I'm free Friday." Will blurted out before realizing how desperate or excited it sounded.

"Great. I can pick you up around seven." Jeff's response is casual and welcoming. "Dinner good, maybe a bar afterward?"

Will hadn't thought about a real date, he had just suspected they would meet after work again. Nervously he agrees, "Sure, that sounds good."

Jeff watched Will's eyes as he respond, "Are you sure? No pressure."

Will looked down at the ground for a second, then back up at Jeff, "Yeah, that sounds fun."


Jeff went home satisfied. After dinner and some TV, he couldnt help but reflect on the day, specifically how excited he was that Will had agreed to see him again. His thoughts started innocent enough, but quickly he felt his cock hardening thinking about what could come next. He pictured Will in his panties, crawling across the bed and sliding his hands up, grasping his hardening cock.

"You like my panties?" Will asked as he engulfed Jeff's cock. The images raced through his head. What it would look like from behind, that pink thong barely covering his hole, and a smooth little set of balls hanging down. How Will would probably play with himself while he did it.

As Jeff stroked his own cock, he let his mind wander, "she would make a sweet little girlfriend," he though as he pictured his hands running under a bra. "Mmm that's my girl he thought as he imagined sucking her nipples. He felt himself close to orgasm as she moved up, kissed him hungrily and slid his rock hard cock against her ass. Bent over in front of him, she looked like she was ready for whatever he wanted.

He couldn't take it, and let out a soft grunt as he erupted all over his stomach. Laying there for a Minute he couldn't help but think that if she made the mess she should have to clean it up.

Next: Chapter 2


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