Our Story

By Lindsey S.

Published on Feb 23, 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.

The next morning was Saturday, which is the day Will usually did his long workout. He woke up in his dummy panties, And flipped through his text exchange from the night before. A smile crept up onto his face as he thought about Jeff getting off chatting with Lindsey. Stretching one last time, he rolled out of bed and got his cycling gear on.

As he rummaged through his drawer, he got an idea. Pulling up an old sports bra that an ex girlfriend had left, he hesitated for a second before trying it on. She had been a B cup, and the fit was pretty snug around his chest, but he liked the way it felt. Grabbing a jersey, he zipped it up and checked himself. Only people that were staring at him would be able to tell.

He glanced down at his panties before slipping them off. Naked from the waste down he bent over and pulled his cycling shorts up his thighs, pausing before getting them all the way up. He took one hand and covered himself, turning side to side. "I think I need to make sure I keep my pubic hair groomed," he though to himself before pulling them up the rest of the way.

Will walked out the door with his bike on his shoulder, set it down and hopped on. As he glided forward and clipped his shoes into the pedals, he had one last thought about Lindsey needing heels or boots before he locked in on his two hour bike ride.

The weekend went by and Will tried not to worry too much about going to work and seeing Jeff. Even though he had gotten two texts from Jeff over the weekend, Will worried he might have regrets, or that somehow he might have ruined things. Jeff, however, quelled those fears in the first five minutes at the office.

"How was your weekend?" Jeff asked. Will smiled back, worried he might actually be blushing. Two co-workers listened as they Will and Jeff chatted before the morning meeting. "Didn't you have a date Friday?" Jeff asked.

Will shook his head, "I did, it went well."

"Think you will go out again?" Jeff's face was confident, his eyes locked on Will's.

"I hope so," Will said. "We made some open ended plans, and we seemed to have some things in common that we might enjoy doing together." Will met Jeff's gaze briefly before their moment was interrupted by another group of people headed into the board room.

Will pulled out his phone to send one last text before the meeting began, "I would like to go out again."

He watched Jeff read it from across the table and text back, "Sure Lindsey, I would enjoy that. Let's hold off on plans for now though."

The meeting began and Will tried hard to focus, but could not get off the text to Lindsey. His mind wandered, as he tried to figure out when he was Lindsey and his Jefff would know. After several minutes his focus became glued on details for their next date.

At lunch Jeff stopped by Will's desk, where Will was stuck trying to make a one o'clock deadline. Jeff began by making small talk about work, and after three minutes Will couldn't figure out what Jeff wanted. The conversation fizzled out, and Jeff just stood there for a couple seconds, before pretending to drop his keys on the floor. Will instinctively reached down to grab them before realizing what Jeff was up to. He let the back of my shirt come up, showing the purple top of my panties.

"You..." Will began to say as he sat up.

"Just curious," Jeff said sweetly, interrupting Will.

Will bit his lower lip and looked around, "I have work to do," He said, pulling up the bottom of his shirt, still keeping a watch out. He pull up the waist of my panties just enough so Jeff could see they were purple with white accent bows and stitching. Jeff could also make out the sheer fabric that most encased Will's cock.

For the rest of the week at work it was hard for Will to ignore why he was wearing panties. It wasn't just about the feeling of the material anymore, it was about Jeff's reaction. Every morning he would slide them on and think about how Jeff would be aroused even before he got to see them. When they were alone at work it was like the rest of the world faded away, and Jeff made sure to talk to Lindsey when they could. Getting back to work after those escapes came too fast everytime.

Wednesday came and Will was anxious to get some plans made. After a brief back and forth, they struggled to be able to find a time when they were both free. So, Will took a chance that he was a little uncomfortable with, and asked Jeff if he would want to come to a super bowl party.

"I want to spend that time with you, and it's my only real open time that fits this weekend. I'm not nervous about my friends meeting you, I just didn't see it happening for awhile," he explained to Jeff. "I'm not ready for others to know, but I had a great time last weekend."

Jeff thought for a second, not because he didn't want to go, but he wanted to make sure Will was really OK with it. "That will work," he said, "but I am going to call you Lindsey when we are alone."

Will smiled, "I can handle that."

Sunday, Will was still sore from his long run the day before. His main issue was his tight his hamstrings were, and he found himself periodically stretching throughout the day. When Jeff showed up at the party, Will was already in the kitchen, taking a break from helping get food and drinks out, by stretching. Erin, Sill's friend had invited a girl she wanted to set him up with, and they were chatting by the counter as Will stretched.

"Hey Jeff," Will tried to not sound excited he was there or be rude to the girl he was talking too. "This is Jeff, I work with him...". Will went through and introduced him to everybody in the kitchen. He bit his tongue trying to contain himself as he listened to Jeff field all the normal questions. To will it felt like it wasn't real, this cool and handsome guy who had already captivated some of his friends interest.

People started making their way around the house, and were in and out of the kitchen. It occurred to Will that he didn't even really know everybody there which was usually intimidating for him, but Jeff made it easy. Eventually, they found a chance to be alone, still in the kitchen, and began what looked like a casual conversation. "Have any predictions about the game?" Will asked.

"Lindsey, Are you trying to start some bets?" A smile curled the corners of Jeff's mouth.

"Maybe," She said, flirting. "Any predictions?"

"Hmmmm, Let's start with the coin flip. If it's heads you have to get down on your knees and suck my cock by the end of the first half. If it's tails I need to lick your ass."

Lindsey's heart raced, she had never done either of those two things before. Jeff looked around before grabing her hand. With nobody watching he calmed her down, "It will be fun." He whispered in my ear. "Remember the movie..."

"I do want to," She said, "I'm just nervous."

Jeff smiled. "Follow me." They Walked out the backdoor where the cooler was, alone for the first time that evening. "We won't get caught," he assured her. "See," he said as he reached for her hand and put it over his shoulder. Losing her eyes she tried to relax. Grabbing her by the ass and pulling her in tight to him, she instinctively ground her my hips against his. "There's my girl." He said.

She opened her eyes and smiled as they slowly ground against each other. She leaned in to kiss him, "it's a bet," she said softly before putting her lips to his.

Their make out session was abruptly interrupted by the sound of the sliding screen door opening. Lindsey pretended that they were just talking, but the two people who she barely knew did not even notice or acknowledge them. Casually they talked holding hands behind her back.

The other people on the deck lit their cigarettes, turning Lindsey and Jeff's private spot into a cloud of smoke, so they headed back in the house. As soon as they were in the door, Erin called Will back over to A conversation she was having with the girl she had invited just to meet Will. Begrudgingly Will went over and joined the conversation. His mind was on Jeff, and whenever he could he would glance around and try to find him. He must have gone to the living room because Will couldn't see him from the kitchen. As their conversation wound down, Will made his way to find Jeff, when he was stopped by two of his friends. They convinced him to put twenty dollars into the big pool for halftime and end scores.

"Yeah, your buddy from work Jeff did," they told him. Will listened intently about what else they had to say about Jeff. They obviously liked him, and Will couldn't hide the smile from his face as he listened.

Finally able to get to the living room he found Jeff sitting behind the couch on a bar stool, sipping his beer and Watching the pre-game. The teams were heading out of their locker rooms when Will sat down on the stool next to his. He subtly insert himself into the conversation Jeff was having, and all three of then stopped to watch the coin flip. Nobody was watching as Jeff feached behind Will's back and gently rubbed as they waited for the outcome.

"Heads," is all Will heard before feeling Jeffs hand start to rub lower on his back. Other people that made prop bets cheered or groaned, but somehow for a second it felt like they were the only two in the room. `Before half time," Jeff said quiet enough so only Will heard him, making his panties a little bit tighter. Within seconds Jeff removed his hand is off Will, And he had restarted the conversation they had interrupted.

Will jumped in as soon as he could, trying to act casual, "I am glad it's not a team I care about. When the Cubs won the World Series, that was too stressful. I mean, I was really happy they won, but I was nervous that whole series."

As Will finished his sentace, the other guy got up to get another drink, offering to get one for everybody.

"No," Will said, "I'm good." He watched Jeff's face as he also declined. Will gathered a little courage, "If this were the Cubs or the Bears I wouldn't be leaving this seat for more than two or three minutes at a time." He licked his lower lip and put his hand on Jeff's thigh.

Jeff chuckled, "hmmmm, Yeah, that wouldn't be good for me then would it?"

His hand slipped down the back of Will's panties and slid under the lace.

"Even if I had lost our bet I would want longer than that," he said, sending goose bumps up Will's spine.

People came in and out of the room, and everybody began talking about the game and commercials as the first quarter came to a close. Twice Will tried to put his hand anywhere on Jeff but couldn't get himself to do it.

"I think we both need another drink," Jeff said and together they walked out of the living room, and found themselves alone in the hallway. Jeff took a slow step so he was behind Will and grabbed his hips. He steered him away from the kitchen, and toward the stairs. Once they turned around the corner, Will felt Jeff twist him around and push him against the wall. Before Will had his barrings Jeff's body was against his. Will could feel keff's semi hard cock poking against him.

"Mmmmm," Will moaned as He felt Jeff's body. He tilted his head and offered him his neck to kiss, which Jeff gladly accepted. "Who won the bet?" Will asked. "Because I wanted your cock in my mouth since I got home the other night." He wrapped his leg around the back of Jeff's, standing on one leg.

Jeff reached for hjs hand, which was on Jeff's hip, and put it on his crotch. "Fine," Jeff said, his lips right next to Will's ear. "Claim your prize Lindsey."

Lindsey gently rubbed against Jeff's jeans with her hand. "I think we should go upstairs." She said, hearing noise coming down the hallway. Sne tried to move but Jeff kept her pinned against the wall. After an additional couple seconds of Jeff kissing on her neck he let her lead the way to an upstairs bedroom.

Lindsey felt Jeff's hands reach up for her hips as they climbed the stairs. She helped him pull down the back of her jeans exposing the T of her thong, just before Jeff gave a playful smack on her ass. She turned her head to look back at him and his eyes were locked onto the red and black disapearimg between my cheeks.

When they got to the first room at the top of the stairs they walked just inside the door. She turned around to face Jeff, "Ok, I'm a little nervous I won't be good at this," She said.. She reached for his belt and begin to pull open the buckle.

"Nothing we have done suggests that could be true," Jeff assured her as she slid his pants over his hips, leaving him in his underwear. "If you are half as good at this as you are at kissing you will leave me very satisfied."

She smiled, still a little nervous, reached down and felt the weight of his half hard cock. He pulled her in close and kissed her softly as his cock gree in her hand. Lindsey opened her mouth expecting Jeff's tongue to meet hers, but it wasn't there. She reaced it out further, touching her tongue to his lips. "See, you can do this," he chuckled. She forced her tongue through his lips hungrily searching for his tongue, letting out a soft sigh when they finally touched.

Jeff tilted his head back and Lindsey worked down his neck. Jeff's hands grabbed at her chest, forcefully massaging a. "Ohhh," Sne moaned as she felt his strong grasp.

"Girls don't wear panties like that unless they want somebody see them," he said, encouraging her.

"Mmmmm," She slid her hands around his back and squeezed his ass, still kissing his neck. "That is true," She said. Sliding down to her knees. She unbuttoned her pants and pulled them down to her mid thigh, exposing her thong. His cock was hidden behind his boxer briefs, but she could see it's size bulging out of the fabric, and a little wet spot at the tip. She peeled down her underwear, letting it pop out.

He grabbed it with one hand and put the other on the top of her head. She looked up at him before wrappkng her hand over his. Opening her mouth she stuck out out her tongue. "I've wanted this for awhile now," he said.

"How about you?"

She nodded her head as she teased her, waving it in front of her. "Tell me," he said.

"Yes, I want to suck your cock," the words felt so dirty coming out of her mouth. He let go of his shaft, leaving her hand alone. Instinctively she pulled it up to the head and slid it back down to the base as she brought it up to her lips. Jeff let her jerk him into her mouth, his hand still on her head. He smiled as he watched her panties, her ass resting on ner heels. She leaned forward as she wrapped her lips around it. Swirling her tongue around the head she had to open her jaw wider to keep her teeth away from it. Jeff heard her breathing through her nose, it was the only sound upstairs. Sne swallowed and pulled back, taking it out of her mouth she looked up.

"Lindsey, you look so good on your knees," Jeff said.

Jerking him slowly she lifted it up and slid her tongue along the underside of the shaft while her other hand ran up his shirt to his stomach. Her panties were getting tight and wet as she sat up higher onto her knees so she could get back to sucking. Before she took it back into her mouth she whispered, "it's so big."

The taste of his pre cum on her tongue, she opened her jaw again, feeling exposed as her ass hung out. It's hard to move her legs with her pants pulled halfway down, so she shuffled awkwardly forward, trying to get closer.

"That feels good Lindsey," He said, watching her as she tried to get as much of him into her mouth as she could. Lindsey began sucking which made a loud sound before she tightened her lips all the way. Jeff smiled down at her, watching her spit start to run down to his balls. Lindsey looked straight ahead at his shaved pubic area and had to touch it.

She pushed his cock against his stomach and rubbed it down, her hand stayed at his balls. Using the other hand to hold the head she licked down the underside of the shaft. She looked up and saw him watching and realized she was totally uninhibited. She couldn't help but smile as she licked down to his balls, making Jeff softly exhale. She used her tongue to flick the bottom of his sack before pulling the head down and kissing it again.

Closing her eyes she lost herself in his smell that came with every inhale through my nose. "Ohhh, like that baby," She heard him say as she jerked him into her mouth. She took the ncoursgemenf and tried to get as much into my mouth as she could, pushing his cock to the back of her throat. The hand on the back of her head held her there for a second. Jeff let her come off a little, but then push her right back on. She swallowed, pretty sure of what was coming. His hips pushed forward and she gave a startled, "mmmmmm" that was almost a squeal from the surprise pressure. Jeff did it again, which made Lindsey feel Jeff liked it.'mmmmmmm' She moaned, and she felt him start to tense.

Lindsey was not sure what to do, so she started to pull off to get just the head in my mouth. Before she like the first shot hit the back of my throat, making her gag and pull off. The second hit her cheek, And she managed to get him back in her mouth to catch the third, finally getting the taste she had wondered about.

She felt it cost her tongue, and she moved it around her mouth before swallowing. The hot sticky glob on her cheek dripped down. She wiped it off with the back of her hand, then wiped it on Jeff's cock so she could lick it up. She closed her eyes and continued to gently suck as she felt some blood leave, softening him and making it easier to keep in her mouth. She could feel his pulse through her lips.

Jeff's breathing slowed down as he relaxed, and she felt him getting softer in her as she drained as much of it as she could. Her mouth kissed the head one last time before she stood up. "That was perfect," Jeff said before pulling her against him. "How wet did it make those panties of?"

He reached down and touched them.

"Pretty wet," She said, trying not to sound too ridiculous. Jeff continued to play with her through the lace, teasing her.

They heard a voice coming up the stairs and she froze. Jeff's hand continues to tease her as they hear them open the bathroom door down the hall. "Want to get caught, or hurry up?" Jeff asked.

"I want to come," I whisper. " I want you to help me cum."

You turn me around so my back is against your chest, and put your right hand up to my lips. I instinctively suck them in and swirl my tongue around them. Your left hand reaches down and ease my cock. I feel your breathe on my ear. Your right hand reaches between us and presses against my asshole, making me squirm. You stop teasing my cock to hold me around my stomach. "Help with the front or back?" You ask, teasing my holoe with my own saliva.

"Both" I say grabbing your hand with mine and trying to bring it back to my panties.

"I do one, you do the other." You say, stilnteasing my hole.

I reach up and lock my fjngers before wrapping them around my cock, jerking myself. I hear the toilet flush and the sink run in the other room but it doesn't register, your finger is too distracting. "Cum baby," you whisper, "are you close?"

The door opens. "Yes, I'm going to cum," I say tilting my hips against your finger. The extra pressure makes it slide inside me. "Oh fuck, I'm cumming." I mutter loud enough that the footsteps in the hall stop. Cum coating my own hand as you finger me. I'm just opening my eyes when I see my friend standing in the door.

"Will," he says confused. I know he saw me, pants around my thighs and in panties, being held up by you. I'm pretty sure he heard what I said seconds before. Once it sinks in he just turns and walks out.

Lindsey stood shocked and emabarrassed. "Your OK," jeff assured her as he reached down and grabbing her cummy hand. Kissing her my neck he tried to distract her. "We should head back disnstairs," He said. She nodded, reached down to pull up her pants after he helped her lick her own mess off her hand.

Next: Chapter 4


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