The next two days went by with hints of familiarity, but Will couldn't forget that he said yes to a real date with a guy. His questions and anxiety ranged from "what will other people think about two guys out for dinner?" To "should I shave my legs and what will I wear?"
Jeff was so sweet at work. He sensed not to come by too often, but his smile kept reassuring Will that they would have fun. Will followed Jack with his eyes whenever he could, and by the time they left work on Friday Will's crush on Jeff had solidified.
When seven finally rolled around Jeff arrived right on time, which Will was prepared for but did not fully expect. Slipping out the door, Will felt strange getting picked up at his door, it was something he hadn't thought about. He just assumed Jeff would text him when he arrived, and he would head to the car unescorted. But here they were walking to the car together. As Will sat in the passenger seat he listened to Jeff make small talk and anxiously waited for it to get awkward. He was not disappointed that it never did and by the time they sat in their booth at the sports bar, Will felt a little more comfortable. Jeff had done everything in a way that felt familiar, after all he had gone to a sports bar like this with guys plenty of times.
After handing us then heir drinks the waitress walked away. "To pink and blue, and whatever color you chose tonight," Jeff said, clinking his beer against Will's.
Will couldn't help but smile at that. After talking a sip, he responded "I went with black." He intended it to be funny, but it was a little flirty. It felt natural and Jeff's smile immediately diffused any embarrassment Will might have felt.
"Uh oh, expectations?" He joked, "They say you only wear black when you want somebody to see them."
Will shrugged his shoulders, "Maybe..." he felt a little nervous again, all the sudden. What if he wasn't up for it, he wasn't sure about kissing. What if Jeff decided halfway through the date he didn't want anything to do with him...
Jeff sensed his tension and backed off a little but made sure to stay on the subject, "Why do you wear them?"
Will looked at the table, "I don't really know," unsure if he was even being honest with himself, he looked up at Jeff's face, "I like the way they feel, I guess."
"Hmmm," Jeff grunted softly while listening. "When did you start wearing them?"
Will paused to think and was a little more comfortable because he had concrete and honest answers to these types of questions. "I was curious in middle school, and then just for fun on college. Only in the last couple weeks did I start wearing them to work or other places." A weight lifted off his shoulders. "It feels good to say that out loud." He smiled and took another sip. "You are the only other person that knows about it," he added.
"Well, when I saw them the other day, I have to say I was pleasantly surprised at how aroused it made me." Jeff was peeling the label on his beer as he spoke. "I liked that I knew and nobody else did." He leaned in closed, "but why did you show me the pair in the bathroom?" Jeff asked.
"If you aren't gay, Why did you want to show me?"
Will nodded his head, "I'm sorry about that gay comment, I was defensive and shocked, and it was a dumb ignorant thing...". The smile on Jeff's face made Will stop mid sentence. "What?"
"Don't worry about it, it's not a big deal." Jeff said, "You are out on a date now with a guy, I don't care what you call it, I just want you to have fun. And I am more interested in an answer to my question."
Will smiled at Jeff as the waitress walked up, which allowed him a chance to think. After ordering Will tried to leverage his position.
"I will tell you, if you tell me why you asked me out afterward," He said.
Jeff smiled, "Sure, that's fine. Why did you show me?" He asked again.
"Because it turned me on that you knew," Will said. "I liked that in the morning I put them on knowing you would see them." Will's skin began to flush and his panties got tight as his cock started to swell. The honesty was making their conversation feel intimate. He was already aroused and they hadn't done anything physical.
Jeff nodded, his attention focused on Will. After a couple seconds, letting it sink in, he realized what Will was waiting for. "Oh, my turn I guess," Jeff said. His voice wasn't nervous, but it was obvious he didn't think he would have to explain this to anybody. "I had planned the happy hour before I saw your pink surprise," he started, and then paused. "I guess I kind of know you from work, but not that well. Then I got curious about what I saw and just didn't invite anybody else. There was no plan or anything like that," Jeff looked at his beer, then at Will. "I just figured that I was curious and liked what I saw so drinks alone would be more fun." He thought he was done, but the pause lingered and the question still felt unanswered. "I'm not hung up on gay or bi or anything, I just want to get to know you better I guess, and I really like that you wore those black panties tonight."
Will listened intently, and smiled at Jeff's last sentence. Even though he hadn't been in a situation like this before it felt like a normal date. "I have really enjoyed the last two days." he said. His eyes locked on Jeff's. The alcohol was starting to kick in and he felt lighter. "So if you are not into labels, I don't know, I guess we just see what happens?" Will awkwardly asked.
"I am interested in kissing you, and getting to know you. If you aren't gay then I want to be whatever allows me to do that." Jeff's answer landed perfectly, making Will's cheeks warm.
Will tried to hold back his nervousness. "Ummmm, I've never kissed a guy."
He couldn't ignore the strain in his panties anymore. He shifted around in his seat and swallowed hard, unable to stop thinking about it.
Jeff reached under the table and took Will's hand, "how about this to start."
Will grasped his hand, it felt comfortable, "I don't know, feels a little gay," he joked.
Jeff smiled. Holding hands till the meal came they chatted about their past a little. Once the food arrived the conversation turned to the sports that were on the TV's. As they finished up the waitress dropped off the check.
"So I pay on the second date?" Will asked reaching for his wallet.
"We can split it if that makes you more comfortable."
"Sure, we can do that." Will said placing his card down. He left his hand on the table and fidgeted with his beer. "Do you want to go out? Or are we done for the evening?" Will's eyes were fixed on the bottle, trying not to look like he had a preference. "I would go out, do a movie or something?"
"There is a pool hall down the block, do you play?" Jeff asked.
"Ummm, not really, but I would go if you wanted."
"How about we go see a movie." Jeff said, reaching out to Will's hand. "I will check to see if there is anything playing soon."
Will glanced down at their hands, "All right, I would like that," he said.
Jeff let go, which disappointed Will more than he thought it would. Within a minute, Jeff was listing off movies and their times. It was last minute and they didn't have many options, so the choice was pretty obvious. Neither of them had seen it even though it had been out for awhile, but it hadn't gotten very good reviews.
"Well, if it's not good we can always just leave, come back and play with our sticks and balls at the pool hall," Jeff said.
Will laughed out loud. The theme of the evening seemed to be how easily he was amused by Jeff. He smiled and then bit his lower lip for a second before shuffling out of the booth. As he got up, Jeff put his hand on Will's lower back guiding him forward. Jeff's touch sent lightning through Will's body, and he applied the right amount of pressure so Will never felt forced. Will felt disappointed as soon as the moment passed.
At the movie theater they made their way up to the ticket booth, and Will decided he was not going to let another moment slip away so easily. As soon as he felt Jeff's hand touch his back again he tried to respond to let him know it was welcome. Will looked him in the eye and smiled, reached out and touched Jeff's hip, "thank you," Will said as he walked through the door.
They made their way through the empty theater and chose a pair of seats close to the middle but more toward the back. Jeff put up the arm rest between them, which brought a smile to Will's face. Jeff began chatting about the last movie he saw before grabbing Will's hand and placing it on his own lap. Will could not help but notice how close his hand was to Jeff's cock, the closest it had ever been to one other than his own.
He noticed both of them take a glance at a girl in a short black skirt that barely covered her ass as she walked up to the row in front of them with her date. Her and the guy she was with clashed in every way possible. She was very fair skinned, and he was very dark. She was dressed like she was going to a club, he was wearing a button down shirt and dress pants. He was probably six foot five, she was barely five feet tall. But for each contrasting feature, they seemed very comfortable with each other. She was hanging onto his arm, and he would occasionally look down at her and smile. Eventually, she leaned in and kissed him on the cheek. After a couple glances Will thought he might as well share his thought.
"I like her skirt." Will always looked at what women were wearing, but this was the first time he had ever told or shown anybody.
"Ha, yeah, they are really opposites," Jeff said. "I wonder how long they have been dating."
"I would say it's relatively new, they are both pretty dressed up, but they are obviously comfortable with each other."
Jeff smiled, "What date number do we have to be on before I get to see you in a skirt like that?" He squeezed Will's hand and looked him in the eye.
Will blushed, and returned the gaze, "I would need to go shopping because I don't own anything like that," Will began, but then worried he was blowing it. He paused for a second, he tried to collect himself. "Maybe the third," he said, not sure what to expect.
Jeff leaned in, "It's a date then, you need to go shopping." He let go of Wills hand and reached to his neck, snaking his hand to the back of Will's head and pulled his lips close. Will closed his eyes instinctively at Jeff's tender touch, every muscle in his body frozen. After a couple seconds, Will licked his lips, eyes still closed, waiting as his heart pumped hard in his chest. He felt Jeff lean in the last inch and kiss him softly on the lips, making every muscle in Will's body instantly relax.
"Ohhhh," Will let out a soft moan. He felt Jeff's lips turn into a grin against his.
"That good?" Jeff asked as he pulled away a little.
The lights began to dim as Will opened his eyes. He smiled and licked his lips again. "Yeah, I liked it," he said.
Jeff leaned in again, but this time did not hesitate. He pressed his lips against Will's and stayed there for a second before opening his lips and letting his tongue slide out. Will closed his eyes again, and reached for Jeff's thigh. He squeezed it as he felt Jeff's tongue probing his lips. He slowly opened them and let Jeff's tongue in. Will squeezed Jeff's thigh a little tighter before letting out a loud exhale. Will didn't realize he had been holding his breathe that long. As the pre-views played Jeff continued to lean into Will, his hand on the back of his head moving down to Will's stomach.
Slowly their kiss settled down, leaving both of them more comfortable holding hands and touching. As they turned their attention to the start of the movie it became clear why nobody was in the theater. The movie was awful. Jokes fell flat, the acting was bad, and the plot seemed completely random. Jeff's hand held Will's, and after about 15 minutes their attention was more on the couple in front of them than the movie.
As they watched the other couple make out, Will's panties grew tight, and he felt himself growing curious about Jeff's cock as they watched the couple's hands roam. Flashes of light from the screen allowed them to see random details, like his hand up her skirt and that her tongue was inside his mouth. Will kept wanting to see if she had gotten him in her hands yet, but could not see well enough to know.
Jeff broke their silence as if he was reading Will's mind, "Can you imagine being her?" He whispered in Will's ear.
Will responded with a squeeze of Jeff's thigh. "I think I would like to know." Will responded.
"I bet it makes those panties you wear pretty wet thinking about it." Jeff said. His hand rested on top of Will's and squeezed his thigh. His other hand went to Will's thigh, just inches from his panties. It slowly began making its way up, making Will unconsciously spread his legs further apart. Will's hand mirrored Jeff's and inched in closer to his groin. He could almost feel its heat.
Jeff lifted his hand up and slid it under Will's shirt, then ran his fingers against the lace on the elastic of his panties. Will let out a soft gasp as he felt Jeff's fingers against his skin. "Do you wear something like that to be seen or to play in?" Jeff asked.
"Both," Will responded, sliding his own hand onto Jeff's buldge and rubbing it. He turned his face toward Jeff. "And to be called Lindsey," he said.
"Nice to meet you Lindsey," Jeff said sweetly. He turned his face to hers and leaned in, kissing her softly on the lips. She closed her eyes and slipped her tongue out, inviting his to play. She felt his hand unbuttoning her jeans and sliding between the lace and her skin, his finger brushing the wet head of her cock.
"Ohhhh," she cooed, grabbing his bulge and squeezing. She could feel him pushing his hips up against her hand, so she used her palm to rub up and down against it. He responded by sliding his tongue hard against hers, pushing back into her mouth. His hand reached around to her bare ass cheek, making her sit up on her hip as he fondled it.
She could broke the kiss coming up for a little and, and letting Jeff kiss her neck. His hands traced down the back of her thong, and she continued to rub his crotch. Jeff stopped kissing her neck, and she looked at him. His eyes were focused on her panties, making her smile. As he looked up at her face, she leaned in and kissed him softly in the lips. "I'm glad you like them." She said.
His hands moved to her stomach as the house lights slowly came up, the movie and credits now over. Lindsey quickly reached to button her pants and glanced around checking to see if anybody had seen. The couple below them was also, fidgeting around. As they walked out Jeff couldn't help himself, "what a great movie," he said, loud enough for the other couple to hear, making Lindsey grab his hand as she shook her head.
The entire walk to the car and ride home, Jeff and Lindsey held hands. Their finger interlaced and on Jeff's lap as he drove, Lindsey could not help but think about how she was going to say goodnight.
"I had a lovely night." Lindsey said as she opened the car door. Both walked slowly to the front door, unsure what to expect. This time Lindsey reached for Jeff's hand, her chest tight as Theh walked up the last step, and she reached for her keys. She open led the door, not really sure what would happen next. "I hope you don't regret asking me out again." I said.
"Not at all, I would like to do it again." Taking their clasped hands he wrapped them around her back so their hips touched. He leaned in, holding her hand behind her back and moving the other to her hip. As he kissed her, she used her free hand and out it over her shoulder. As their tongues found each other again, she let go of his hand, and wrapped it around is neck.
She felt a mild laugh come on, "this is pretty fun," she said.
"It is, isn't it?" Jeff said. his hand sliding down the back of her jeans under her panties. It makes her tilt her hips, grinding against him. She watched his eyes as she humped him, and has to closed hers once she felt his hard cock against her. She tried to hold back but couldnt, and gave another quick dry hump. Sne felt his tongue prying her lips open, so she opened her jaw wide, expecting what came next. The force of his tongue and his lips drove her wild. INstinctively she reached down and grabbed his ass, squeezing it with both hands. She lifted her knee up, standing on one leg and felt his hand reach down to her thong and start grabbing. They could feel each other breath, sharp inhales, as she tilted her head to the side, offering her neck.
"God that feels good," She moaned, as they ground against each other. "I just don't know..." She started.
Jeff slowed down, pulling his hand up a little, but not out of her pants. Her hand slid to his stomach and she put her foot back on the ground, her chest heaving.
"Yeah, you might be right," he said.
She closed her eyes and pulled on the waist of his pants. "I think I need to figure out what I'm doing, and what I want."
"Yeah, it's tough to know what you want," he responded with a smile and a squeeze of her ass.
"I know I like that, and if we are being honest I have more I want to do right now, but I can't kiss a guy for the first time and... Well, do some of the other things I just realized I might want to do." Her eyes studied his face.
"Ok," he said, "all right." He took his hand out of her pants.
"Do this again?" She asked. Reaching down she felt his cock through his pants. "This is my first time touching anybody else's."
Jeff smiled, "and hopefully not the last time touching mine."
With one last kiss, she walked inside and closed the door. She watched as Jeff drive away. Within minutes Her mind was racing, trying to comprehend what had just happened. She ranged from thinking this was ridiculous, to wanting to call him and tell him to come back. Finally she settled on a simple text that said, "thank you. I know I'm not supposed to send this so quickly, but I had a lot of fun."
She got ready for bed, and as she was laying down she got a response, "no worries, I am mostly disappointed I never actually saw those panties, you have my mind racing."
She smiled, and started to feel a little flirty. "I didn't mean to tease," she texted. After thinking about it for a second, she got up, turned her back to the mirror and snapped a picture of her thonged ass. "How about this?" She asked, and attached the picture.
Jeff could not believe his eyes. He was not expecting that, and with a new set of expectations, he texted a picture of his bulging boxer briefs.
"Love that pic. Waiting for your hand, of whatever else you want to use."
Lindsey licked her lips, "was thinking about that actually. With my hand in my panties."
Jeff texted back, "will only believe if I can see it."
She took a deep breathe, and tried to stay calm. Turning over onto all fours, she propped up her phone to take a picture. Covering her self with her hand, she let the timer run down and snap a shot from under her. She looked at it and was immediately critical. As she was about to delete it, Jeff texted again. Opening it she saw his fully erect cock being held up by his hand, pre-cum clearly visible on the tip. "Waiting," is all he said.
"I need to shave, and the lighting isn't good..." she responded, but knew what she had to do. She attached the picture. She laid in her back and began stroking, staring at the picture he had sent.
"You look great babe," texted back, "are you close to Cumming?"
She smiled, "I can be if you want me to be. Your pic has me pretty fired up."
Jeff couldn't help himself, "next time you can see it in person."
"I want to feel the it too, all over my body," she was losing control. She closed her eyes and started rubbing herself.
"Take it baby," was all he texted, and it was all took. She erupted in her panties.
"That's twice you've mad me cum," she said.
"Show me, I want to see your soaked panties."
She snapped a picture of her black lace with her white cream oozing out of it. She brought some to her lips, and snapped another picture. "Wondering what you taste like."
Jeff bit his lower lip as he rubbed rubbed his cock. He couldn't stop looking at her pictures. In his mind he could picture her bent over on all fours, waiting for him to come over. Waiting to let him climb on top of her. "I'm close myself baby," He replied, "I would love to feed it to you."
She couldn't believe this was happening, and how bad she wanted him to be there next to her, or in her mouth, or kissing her. "You are turning me into a dirty minded girl."
That was all he could take, letting himself pump harder till he let out a grunt. Cum shot up onto his stomach and began driping down his hands. Snapping one last picture he texted her, "you want to clean up?"
"I'd be happy to!" She replied.