Our Story

By Lindsey S.

Published on May 12, 2018

Transgender

Sorry this took so long. Editing sucks and you might find some mistakes below. This has been sitting half done in my drafts folder for a month.

Going into the conference room wasn't the same after they had begun their affair. Lindsey couldn't help but think about their weekend make out session at the mall or their fun viewing at the sex shop. She could not feel like anybody but Lindsey around Jeff, so sitting across from him in the board room made it pretty hard to focus on the meeting. He was sitting so close to her and she could not stop thinking about getting his fly down.

She had dropped a couple hints over a couple days that she would like to host him and he could stay over on Valentine's Day. Politely, Jeff suggested dinner at home, something simple.

"Sure," Lindsey smiled, "I would really like that."

"So it's a date," he replied. "What should I bring?"

Lindsey almost forget they were in the break room where anybody could walk in at any second. She took the chance and leaned in, kissed his cheek and whispered, "a bottle of wine and your big cock." She watched his reaction and was not disappointed. With a small smile he showed he was a little surprised, just enough to show it wasn't unexpected.

"I will make sure I hydrate," he said before smacking her ass playfully.

The moment had passed, and just in time because the office assistant that gossips about anything and everything came in. But that didn't stop Jeff from grabbing at Lindsey's panties as she walked away. He grabbed the bag of her khakis, pulling out the back of her shirt and quickly exposing the `T' of her thong. Lindsey grabbed at her shirt quickly and sat down, hoping the assistant didn't see anything, and Jeff just smiled, watching her tuck in the back of her shirt.


At work on Valentine's Day, Lindsey tried to get done early so she could get home and prepare for their evening. A couple deliveries of flowers had come to the office, and she found herself watching each woman try to maintain their work composure while they were clearly excited by the gift. All of them smiled as they opened and read their card. Each delivery she watched for too long and had to conciously tell herself to get back to work.

By three o'clock she was ready to head out, when another delivery came to the front desk. It only took a couple seconds for her to clear her desk, and in the background she heard the assistant saying `there is nobody by that name here,' To the delivery man. Just like all the other flowers that day, she watched as she walked to the exit, hoping not to draw attention to the fact she was leaving two hours early. As she got closer, she heard the delivery person say, "well can you make an announcement or something to see if somebody meant them to delivered to Lindsey, but got the addresses mixed up? That happens all the time."

She slowed down when she heard her name. The roses were pink, and there were six of them with a small card attached. Blood rushed to her face.

"He didn't," was her first thought. As the assistant picked up her phone to make the announcement she stepped forward quickly.

"Wait, that's me, I mean those are mine, I mean, I made that mistake." The truth was in Will's flushed cheeks, but deep down Lindsey hoped that she fooled them. "I ordered them for my friend, I must have put the wrong address, Lindsey with an `e', right?"

"Yeah, you're right." The delivery guy handed her the clipboard to sign.

"This is ridiculous," She said under her breath, but smiling ear to ear. She glanced in the direction of Jeff's desk, but didn't see him. Accepting the flowers she apologized, to both the delivery person and the front desk assistant. "It was a stupid mistake."

Lindsey took one last glance toward Jeff's desk, and then walked out. At the elevator she saw him walking by, clearly proud of hisf. The door opened and Lindsey called his name, letting the delivery man go down by himself. As the door closed she hit the button to call another elevator as Jeff walked up. "I am headed out but wanted to talk to you, can you walk out with me?"

"Sure," he salad, "is this about,"

"Yeah, you know," She cut him off. The nexf elevator arrived and they walked in alone. The door closed and Sne playfully hit him on the shoulder.

Grabbing her wrist he pulled her in and kissed her, immediately pushing his tongue to her lips. Moving To her ear he asked, "like your flowers?"

"Yes, I haven't read the card though." She gasped, letting him nibble on her ear lobe.

Jeff stopped as the elevator got to the first floor. "See you tonight," he said before kissing her softly on the lips just before the door opened.

In the car she read the card and couldn't help but giggle. "The color that got you noticed and the number of successful dates we have been on, to my Valentine, Lindsey." The entire ride home she could not help but be happy.

At home she first got dinner prepared. Chopping the vegetables and getting as much done as Sje could before the time table became too tight. She wanted to make sure she had enough time to get ready and cook while looking like a hot date.

Preparing the bath she dropped in some bath salts, and took her time. Lindsey used a loofa to scrub herself, and when she got out she felt feminine. Her skin smellled and felt like She wanted it to, soft and flowery. Putting on some lotion before gettong dressed, she rubbed her hands up and down her legs, anticipating the lace trap she was about to set.

Lindsey put on her lingerie first. It's the most fun to slide into and It felt wrong to be walking around naked. She watched herself in the mirrors and made some small adjustments to the black lace thong and matching push up bra. What little she had on her chest was pushed up over the shelves, and she gave them a quick squeeze. Roling each stocking up her legs, she felt like she was getting ready for one of her triathlons. She wanted everything to be laid out and perfect and she had spent so much time thinking about what was going to happen tonight, she didn't want a missed detail to ruin it. The lace on the top of her stockings held them in place, and she felt them as she walked to get her little red silk robe.

There was not much she could do with her hair, so she went for a little spiked dykey look. Putting on her mascara and eye liner, she finished up with some lip gloss.

She headed downstairs and checked the clock, Jeff would be there in fourty five minutes. Lindsey began putting things in the frying pan and preheating the oven. The time went quickly as she cooked, and she made sure to clean as she went. "Dirty dishes are a turn off" she thought. Right on cue the timer went off, she pulled out the roast from the oven, and headed upstairs to finish getting ready.

Finally she stepped into a black dress that came to mid thigh and hung off one shoulder, exposing the strap of her bra. The top was looser, making her feel a little less masculine and less insecure about her cup size. She looked in the mirror and made a note that she should buy a necklace at some point.

Walking back to the kitchen She finished getting the atmosphere ready by setting the table, lighting two candles and putting her roses into a vase in the middle. She took the last five minutes to put some finishing touches around the living room, when she heard the doorbell ring. She gave herself one last look in the mirror before opening the door.

She felt strangely comfortable as she smiled to herself, especially considering this was the first time she had dressed like this for somebody and they both knew she was going to lose her virginity tonight. Any nervousness before she dealt with by getting and now his smile disarmed her.

"Happy Valentine's Day," She said, holding the door open. His hands were full, holding a bottle of wine, a pair of roses and a small silver box.

He held out one rose, "another date," and then handed over the other, "and one for tomorrow morning."

She laughed, "presumptuous, especially considering your little trick today. I was so embarrassed."

"You deserve to be treated like every other lady today, and flowers at work was a thing," Jeff's voice is half joking but half serious.

"Well, thank you." She closed the door behind him as he walked in. His blue button down shirt and black pants are striking as he waited to hand over the present. After Lindsey put the roses in the vase with the rest she, Jeff offered her the wrapped gift and stepped in, putting his arm around her wait.

"Now or later?" She asked.

"Depends," he said with a smile, "can you wait?" He leaned in to kiss her, "I like this dress by the way," he ran his hand down her bare shoulder and slid his finger under the bra strap. His motion looked as if he was inspecting her, his eyes focused on small details of her outfit and make up. She closed her eyes and opened her mouth expecting a kiss on on the lips, but She fort his tongue on her shoulder, then her neck. She let out a soft moan as she felt his body and lips on her. She felt irresistible, and she was waiting anxiously to get her hands on him.

"Mmmmmmm, I usually hate Valentine's Day," She said.

"Why is that?" He asked, his lips still working her neck.

"Expectations, and a rough history I guess." She felt him kissing her ear, "maybe you are the one that can't wait?" She asked with a sigh, her panties already feeling tight and warm.

"You should open it," he sayid, standing up and letting his arm wrap around her waist. "First, can we open this bottle of wine?"

"Oh, sure." She lead him to the kitchen and went to the drawer to find the wine key. After pouring two glasses, she lead him into the living room and sat down next to him on the couch. They both took a sip before She began to open the box.

From the shape of it, She would have assumed it was a small box of chocolates, but Was surprised to find a white gold necklace inside with a tiny heart pendant. There was no hiding the pleasant surprise from her face. "I was just thinking that I needed to look for something like this, it's perfect, Thank you." She turned her back to him as he helped her fasten it. Holding her hand up to feel the charm, he slid his hand up her stockings.

"I like these," he said, letting his fingers glide along the lace tops.

"Are we even going to make it to dinner?" She asked, spreading her legs a little inviting his attention.

He sipped his wine with the other hand, "I just assumed Inwas going to unwrap my present too," He jokes.

"This isn't your present," She said. "Yours is up in the bedroom."

"Hmmmmm, well, let's have some dinner and then go take a look."

They got up and headed to the table where Lindsey began bringing out the food. Jeff was polite and flirty, and Lindsey tried to balance between hostessing and enjoying Jeff's company. By the time they were done, Most of the kitchen and dining room were clean, so there was only a little time where Jeff was left alone on the couch. By that time they were just finishing the last of the bottle. This was the first time she had been this tipsy around Jeff, she was not drunk, but She was not inhibited by any means.

Straddling him on the couch, her dress could not spread far enough so it rode up her thighs. Her stockings were plain view, inviting his hands to play with them. She put her hands on his shoulders and rubbed them gently as she hovered over him. He put his hands on her hips and looked her in the eye, "dinner was wonderful, thank you for cooking," he said.

"My necklace and flowers and the wine were wonderful, thanks for coming."

She leaned in and opened her mouth, letting her tongue touch his just before pushing through his lips. "MmmmmmmmM" She Let out before lowering myself onto hislap, her dress now up around her waist. Jeff too his hands and ran them from her knees up her inner thighs, to the front of her panties. He teased the head of her cock with his thumb.

Exhaling She broke the kiss and watched himy while She unbutton his shirt. Kissing his bare shoulder first She worked her way down to his chest where She began licking his nipple, occasionally suckling it. Her other hand reached up to his lips, and he kissed it before she slid two fingers into his mouth, and letting him suck them. His tongue and hers both made circles as they played. After a couple swirls around, She brought her wet fingers down and pinched and pulled on his other nipple. She could feel his body relax under her as he let out a soft grunt.

Lindsey looked up at him while she played, his eyes were closed, like an animal relaxing in the sun. His hands have been roving up and down her body, from her thighs to her shoulders. Once she started moving her mouth back up to his, he grabbed her ass and pulled her up so they were chest to chest. Her panties rubbed against his stomach as he squeezed and spread her thonged ass. "Mmmmmmmm , I love when you do that," She said between kisses.

He gave it a quick smack, making herflinch. "How about that?" He asked. She nodded, illiciting another quick smack.

"Just not too hard, remember that's your ass tonight so don't break it." She giggled.

He gave another smack, just a smidge harder than the others. "You dirty girl," he whispered softly.

They continued to make out and she oukd feel his cock growing hard under her.

"We should go upstairs," She said.

"Hmmmm, sounds like a waste of time to me," he responded.

"I promise it will be worth it," she said.

"Fine, but I want to see what's under here while we go," He pulled her dress down, exposing her push up bra. Then he slid it down exposing her thong and stockings. Taking one good look he helped her up off his lap, and he move forward so he was sitting on the edge of the couch. He kissed her stomach as she stood there. Putting her hands on his head She played with his hair for a second before backing up. "Lead the way," he stood up, put his hands on her hips, and followed her up the stairs.

They walked into the bedroom and she crawled onto the bed next to a fairly large box. Sne got on her knees and hand it over to him. "Some for you, some for me, all for us," she said.

He pulled open the ribbon and lifted the top. She watched his reaction, and was not disappointed. "Read the card," she said. He placed the box down and ripped open the envelope. The message read, "happy Valentine's Day, I cant wait till you make me your girl tonight. Use these any way you want because tonight is all about your desires and me fulfilling them. Xoxo xoxo, Lindsey"

"Hmmmm, where to start?" He asked. He pulled out the blindfold, "this seems logical, but I like looking at those pretty eyes."

He slipped it on over her head, leaving her in the dark. She could hear him moving and felt him lift her knee and push it toward her chest. That force made her lay on her side and she could feel he was leaning over her. His warm tongue slid from her hip down the elastic of her thong till he got to her taint. "Oh baby," Sne moaned as she felt his tongue slip along her rim. She coukd feel the heat from his breathe and pulled her knee up against her chest allowing him to use his finger to tease her. "Your tongue feels so good on my pussy," She moaned as he slid a finger inside. His lips wrapped around her cock as she felt herself losing control. He must have sensed it because he backed off with his mouth, just teasing her balls now.

"Your so soft and smooth, I want you like this all the time," he said as he moved back to the box.

She felt a cold hard rubber hit her lips and instinctively she began sucking. She knew exactly what it was, and the soft end swaying against her thighs confirmed it was the fox tail.

Suddenly the blindfold was lifted off her head, and she found Jeff watching her. She smiled as she kissed the toy. She knew he wanted a show, and she was happy to oblige. After a minute of showing off her tongue, he pulled her so she was sitting up, almost on his lap. His pants were still on and she could see his raging hard on sticking out.

She slid hand down his chest, over his stomach and started rubbing it. Jeff wasted not time pulling the plug down to her hole, where she promptly helped by pulling her cheek to the side, giving him access. "Foxy lady," he chided before pressing it firmly against her. He watched as she tried to let it in. A little More pressure and she could feel it stretching.

"Maybe my cock would help you relax," he said. No sooner was the sentence over than we're her hands working to get it out. He chuckled to himself, "you really do love sucking cock don't you?"

She was so focused on setting her appetite she didn't realize she was bent over his lap, until the plug settled in with a pop. "Ohhhhhb," she let out involuntary, making Jeff laugh again.

"That's my girl," he said, holding his cock with one hand and pressing the plug with the other. This time she felt the tail swinging between her legs as she moved her hips from side to side. It went back and forth like a pendulum as Jeff playfully smacked her ass.

Lindsey couldn't contain her hunger, and the rhythmic slaps did little to distract her from trying to suck all the cum out of Jeff. Her lips wrapped tightly around as she took him deep inside her mouth, pushing back against her throat. Each breathe through her nksenshe could smell him, all his masculinity coming through her nostrils making her drunk. After several minutes of head bobbing she noticed the thin film of sweat on her chest, and the soft grunge coming from Jeff. Cock still in her mouth she looked up and saw his eyes on hers. He immediately grabbed her and pulled her up to kiss him. She wasted no time climbing up on top of him, making out like they were a high school couple in the back seat in some abandoned parking lot. She could taste his pre cum mixing with their saliva, and it dripped down her chin. Her ass still stretched from the plug.

She felt him pulling it by the tail and with a pop it slid out. She let out a gasp feeling empty, and her legs started to squirm, wanting something back inside her. Rolling on top of her she reached down and grabbed his cock, "please," she begged. Jeff lifted his chest off her, and cool air brushed against her sweaty skin.

"I want you inside me." She said a little less urgently. Jeff slid the straps of her bra off her shoulders and pushed down the cups of her bra, exposing her stiff nipples. He began rocking his hips back and forth as she guided his cock to her waiting entrance. Pinching her nippples, he pushed so the head of his cock teased her. She closed her eyes and waited. She was sure she made a ridiculous face as she felt him push inside but she didn't care. She let go of his cock and ran her hands up his back, then down to his ass, trying to pull him deeper. He leaned back down and kissed her, but she was too distracted to kiss him back with much attention. All she could focus on was trying to get all of him inside as he stretched her.

"Holy fuck," she exhaled as he started to pull out, but she tightened her grasp and squirmed to keep him halfway in. "No, deeper baby."

"Your so tight, I don't want to hurt you," He replied.

"Mmmmmmm, no it feels so fucking good," she whispered in his ear as she tried to grind her hips.

He gave a little push to go half an inche deeper, making her gasp and then smile. "Yes, like that," she moaned.

He puumped deeper quickly again, then pulled back slowly. "God you are so tight baby," he said letting out a soft grunt as he pushed again. Her cum began to leak between them and a warmth filled her body. She knew what was coming but had never had it happen with anybody inside her before, just her toys. The sensation was coming from right where his cock pressed against her insides. She lost her breathe and began to pant. Two more quick thrUsts were all she could take, small steaks of cum pumped out of her, leaving her dizzy. Cum covering his stomach, the smell filled the room.

"I came baby, all over your stomach." As soon as she spoke she realized how dumb it sounded. "Don't sorry I can clean it up." She was so distracted by Jeff's new rythm she couldn't think straight.

Jeff's focus was on getting as long of strokes as he could. He barely heard her as he tried his best to hold himself back, as he was also on the edge of orgasm.

"Do it then," he said, happy she offered so he could take a break. He pulled out of her, and let her slink down to his stomach where she kissed her own cum off him. She could smell the difference of his cock after he had been inside her, and it turned her on more. Under him, she felt him rubbing it against her chest as he stayed hard as a rock. The taste of her own cum was salty, and left a thin layer on her tongue as she tried to get every last drop.

Jeff rolled over and sat up. Lindsey took the cue and straddled him. He guided his cock back to her hole and she pressed herself against it. "I think I like this just as much as sucking your cock," she said as she pressed deeper. "I love being your girl and getting your cum." She began sliding up and down as his hands grabbed at her ass.

Her bra still on, he fumbled to get it off, and ended up with it around her waist like a garter belt. Her abs flexing with each motion. She could feel him losing control. He was grunting so hard she could feel it in her own chest. "Yes baby, give it to me, I want your cum. Make me your girl, take my tight little ass for your own."

He erupted deep inside her and held her hips so she couldn't go up and down, cumming the deepest he could and holdingnit there. Swear ran in drops down his chest as he grunted, burying his head in her chest. As he came down she could feel him relax, and she slid off him. With a soft smooth exit, her ass home slowly tightened and closed back up. Small leak is came out on her sheets as they laid together in silence.

"We didn't use all the toys," she whispered in his ear.

"We will have plenty of time for that," he replied. "Right now I just want to lay here, and maybe shower before we try that again."

She smiled. "Promise?"

"Mmmmhmmm," He said, giving her a kiss on her forehead. "You won't be able to go a day without me wanting to get back in there."

Next: Chapter 7


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