tagTransgender & CrossdressersLove with a Twist Ch. 01

Love with a Twist Ch. 01


Hello Readers!

This is my first try at this type of story. I have two other chapters I will be posting in the coming days so I hope you enjoy this one enough to see what happens next.

I want to give a special thank you to my amazing editor Cristal Bell. She was very helpful with this story and one of the best editors I have ever run into thank you.


The plane lurched slowly causing Robert's stomach to turn slightly. Robert was never a fan of flying and could feel his tension rising as he slowly reached for the cup of water in front of him. His nervousness was not only the result of flying but also because of the impending meeting he was about to have.

Robert sighed as he shifted in his seat thinking back to the last conversation he had with Partygirl05. Partygirl05's real name was Sarah and they had been speaking almost daily since finding each other online a year ago.

Sarah was everything he wanted in a women, she was funny and had a quick wit, but was very compassionate and serious when it was called for. They met in an online chat room called Open Minded, and after several days of regularly meeting in the chat they exchanged instant messenger names and spoke at length about everything. They had a lot in common, liking the same taste in music, a passion for movies and even enjoying the same type of video games.

Robert was only 32 but was still a very avid gamer, owning all of the latest gaming consoles and also a homemade PC he built himself. Sarah was 30 but still very much a teenager at heart, and a hopeless romantic like him.

After several months of chatting online, things naturally progressed to phone conversations and text messages. Robert loved the sound of her voice; it was very soft and delicate and very much fit her personality. They talked for hours at a time, even late into the evening. Sex had come up naturally, in most of their conversations but it was only a month ago that they attempted phone sex. It was one of the most erotic events Robert had ever had on a phone and they both came quickly, after which they both knew that their relationship had changed.

Which makes what happened several days ago exciting. Robert felt the plane lurch violently to the left as he heard the familiar ding of the seat belt sign come on.

"This is your Captain speaking it seems we have run into a bit of weather up here. No worries we are on our final approach and should be starting our landing shortly. Please make sure your seat belt is on and fastened, as I have turned on the seat belt indicators. Thank you." The muffled voice came through the small speakers above Robert's head.

Robert closed his eyes and leaned back holding onto the folded piece of paper in his left hand. It was the e-mail he had sent Sarah which explained that he would be flying to Florida, where she lived, on business and asking if they wanted to meet.

Robert worked for a small computer company that made financial software for other companies. His boss asked him to fly to Miami, Florida to take a look at a problem one of the companies was having with the software. Knowing that Sarah lived in Miami, Florida he jumped at the offer. He was only supposed to be down there for a couple of days but after speaking with Sarah, who was excited to finally meet him, Robert put in for a week of vacation, and planned on staying down there longer.

Robert carefully unfolded the e-mail which had her response, she wrote about how excited she was that he was coming to visit and included a picture of herself. Robert looked down at the picture of her smiling face. She had shoulder length brown hair that curled slightly at the ends. Her face was very round with soft deep blue eyes and full red lips. She was holding up a peace sign with her right hand and Robert could tell that her breasts where about a B cup but seemed tight and perky. She wore a tight white t-shirt that read "Party Slut" across her breasts. The photo stopped at her waist but Robert was awed at how sexy she looked in the simple attire.

Robert himself was no body builder. He stood about six feet tall with short cut brown hair, with a neatly trimmed mustache and goatee. He had some muscle on his arms and chest but nothing like six-pack abs. He walked nightly and also tried to eat right. He was never into sports but loved to go swimming and being in the water.

In a years time, the topic of exchanging pictures never really came up, they were both enjoyed the small fantasy and descriptions that they provided to each other. They were both drawn to each other's personalities and feelings, which seemed to weight much more then looks alone. That is why Robert was a bit shocked when she sent him the picture he now clutched in his hand; Robert had sent her one of him as well, just before leaving on this trip. He gave her his flight information and she told him that she would meet him at the gate.

Robert felt the plane slowly descend as the captain came on the speaker explaining that they would be landing soon. Robert felt his stomach twist again as he quickly folded up the e-mail and stuffed it into the pocket of his jeans. Leaning his head back he closed his eyes and tried to recall the sound of Sarah's voice as he felt the plane turn into its final descent.


Robert was relieved to be off the plane as he stepped from the door leading to the plane into the waiting area. Robert quickly scanned through the crowd trying to find Sarah's face, the mass of moving people made it difficult and he gathered up his bag, which he had carried on with him, and slowly started to walk to the main aisle way in front of the gate, which lead to the baggage claim. Robert's stomach dropped as he watched the crowd thin in front of the gate, with no sign of Sarah. Sighing to himself he slowly turned in the direction of the baggage claim. He had only taken two steps when he heard someone say his name, and felt a tap on his shoulder. Turning around he saw her standing before him with a beaming smile on her face.

She was just a head shorter than him and was wearing a yellow t-shirt that followed the curve of her body nicely and a pair of jean shorts that were slightly loose around her hips but showed off her slightly muscular and tanned legs.

"Hey how are you?!" Robert said as he smiled broadly back at her. Sarah quickly stepped forward and wrapped her arms around his neck as she hugged him tightly. Surprised, Robert gently reached around and held her tightly to him. His stomach stopped twisting and he felt lighter as he held her warm soft body close to his. He heard her sniff quietly as she buried her head in his chest. "Hey you ok?" Robert whispered into her ear.

"I am sorry, I have been wanting to do that for months now." She whispered back as she lifted her head and looked into his eyes. He could see the small tears streaking away from her eyes, but it was not sadness he saw but something else. A passion, or love maybe. She quickly pulled away from him wiping her eyes with her hands and giggling softly.

"Don't be sorry." Robert said as he reached out and pulled her back to him. "I wanted to do the same thing."

"Do you have some other bags to get?" Sarah asked as she welcomed his embrace letting him guide her body back to him.

"Yeah. I think the baggage claim is over that way." Robert said as he pointed towards a sign.

"Ok lets go, and then maybe grab some lunch?" She said as her hand drifted down to rest against his. Robert felt her hand, and slowly slipped his fingers between hers, loosely embracing her hand.

It was tough to fight through the crowd of the airport to get his bag, but they made it through quickly and found themselves walking through the parking lot to her tan colored Jeep. Robert found himself sweating just in the short walk to her Jeep. He cursed himself for wearing his jeans and dress shirt, but felt the jeans and t-shirt would have made a horrible first impression. He could feel beads of sweat running down his cheeks as the heat of the day rose in the July weather.

"You ok?" Sarah asked as she tossed his other suitcase in the back of the Jeep.

"Yeah, just should have worn my shorts instead of these jeans." Robert chuckled as he whipped his forehead with his shirt sleeve.

"Do you want to go back and change?" Sarah asked as she leaned back against the Jeep crossing her arms under her breasts pushing them up slightly. Robert felt his manhood stir as he looked over her tanned well defined body in the sun.

"No, I really don't want to push back through the crowd." Robert said with a frown as he pulled out his sunglasses and put them on.

"Why not just change in my Jeep? I promise I won't peek." She said with wicked grin.

"I don't know..." Robert replied as he glanced around the parking lot.

"Come on its fine, tinted windows, nobody will see a thing." She said as she rapped her knuckles against the rear window of the Jeep. Robert debated quickly in his head what he was going to do, but a bead of sweat ran down his back causing him to shudder and make up his mind, he needed to get out of these heavy clothes.

"Ok...but no peeking!" Robert said with a chuckle as opened his suitcase and dug through the contents locating a pair of shorts and a t-shirt.

"I promise!" Sarah said as she placed her hand over her heart. Robert climbed into the back seat and slowly pulled his clothes off and changed. Thoughts of her secretly peeking in on him as he changed caused his manhood to swell. By the time he had his pants off he was semi erect and very noticeable. Digging around for his shorts he glanced out the front window and caught some movement in the passenger side mirror. Looking at the mirror he saw her face and realized that the mirror was adjusted in such a way that she could watch him change without having to move from her spot next to the door.

Feeling cocky he decided to give her something to see and planted his feet on the floor and lifted his hips quickly pulling at the front of his boxers he made sure that the head of his cock slipped through the hole in the front letting his semi-erect penis bounce into view. Sitting back down in the seat he glanced to the mirror again to see that her eyes were wide with shock and then quickly she turned away from the mirror. Robert finished dressing and climbed out of the Jeep to stand next to her.

"Cheater..." Robert said with a smirk on his face. Sarah glanced down at the ground as her cheeks turned a bright shade of red.

"I have no idea what your talking about." She said with a grin as she put on a pair of sunglasses and slowly walked away from him. Robert watched her hips sway as she walked away from him and felt his penis getting harder as he watched her tight ass shift inside the loose fitting jean shorts.


The drive down the coast was pleasant, Robert listened intently to Sarah as she pointed out some landmarks and other things along the freeway as they drove into downtown Miami. Robert examined her body more closely; he loved how tan and smooth her skin was. Her body seemed to flow so nicely from the gentle curve of her neck down into the soft curve of her breasts. Robert followed the line of her stomach to her waist and then something caught his attention. It wasn't very noticeable, but it appeared to be a bulge in her shorts along her left inner thigh. He watched her shift her legs and it appeared that the bulge became smaller... Robert shook the image from his mind as he convince himself it was just the way her shorts were bunched up.

"So what do you think?" Sarah asked as she glanced over at him.

"About What?" Robert asked as he pulled his gaze from her crotch and to her face, noticing right away that she had an inquisitive look in her eyes. Realizing that she had asked him a question that he had not heard, he glanced about quickly hoping something would give him a clue as to what her question was. "Ummmm" Robert said as he blushed and glanced around the vehicle.

"What do you want for lunch silly?" She laughed as she pulled the vehicle to a stop at a red light.

"Oh! Uh whatever I'm easy." Robert replied as he shifted in his seat looking out the window.

"Yeah, I heard that about you." Sarah replied with a laugh as she pulled into a driveway of the Golden Omelet Restaurant.

Robert chuckled as he replied "Yeah, well I was told easy was your middle name!"

"Maybe later you can find out?" She said with a grin as she released her seat belt and opened the door. Robert's head whipped around and a look of shock crossed his face as he watched her slowly climb out of the vehicle. An image of her naked sweaty body rocking softly under him with his cock buried deep in her pussy, flashed through his mind, making his manhood stiffen painfully.

"You coming?" She said with a heavy emphasis on the word coming.

"Um yeah..." Robert replied as he slowly unlocked his seat belt and opened the door. Robert held the door open for her to the restaurant and even pulled her chair out when they reached the table. Sarah had sat down to his right and was quietly flipping through the menu trying to decide what to order.

"So where are you staying?" Sarah asked as she flipped the menu over to look at the pictures of the many omelets offered on the back.

"Um the Motel Blu on Biscayne Blvd." Robert replied as his stomach growled quietly. He had not eaten all morning feeling too nervous with the flight and meeting Sarah. Now that his nerves had quieted his body was telling him its next need.

"Oh you're kidding! That place is such a dump!" Sarah said as she placed the menu down in front of her. Folding her arms across her chest. She looked like she was in deep thought as she stared at the menu in front of her.

"Yeah well..that would be my company for yeah." Robert said as he flipped to the back of menu.

"Hey come stay with me!" Sarah said excitedly as she leaned forward, placing her folded arms on the table.

"I don't want to put you out or anything, and what about your roommate?" Robert said as he mentally choose to order the Farmer's breakfast.

"Bah! She is gone for the next week on vacation and I have plenty of room, you won't be putting me out!" She said as she waved her hands in a dismissive gesture.

"Well..." Robert said as he fingered the napkin in front of him.

"Settled then! You can crash with me, it will be fun, trust me!" Sarah replied with a grin as she sipped on her glass of water.

"Well, you know I have to work tomorrow right?" Robert replied as he watched her sip the water, the way she pursed her lips and licked them slightly after taking a drink was so arousing.

"Yeah, no worries I can drop you off in the morning on my way to the gym, and you can call me when you get done." She said with a smile as she felt his knee brush against hers, sending a warm rush through her body.

"Ok well cool then." Robert said as he nodded his head and felt her knee against his. He slowly bounced his knee making it rub against her soft flesh. Small jolts of electricity shot up his leg to his now swelling cock at the touch of her soft skin. They chatted over their meals, and played catch up since the last time they spoke. After they had finished eating they ordered some coffee and sat for a bit enjoying the quiet moment and conversation.

"So! What do you want to do?" Sarah asked as she drank the last bit of coffee from her cup.

"I don't know, its your town, what did you feel like doing?" Robert asked as he leaned back in his chair putting his empty coffee cup on the table.

"Hmmmm... Well we could go back to my place and freshen up a bit then I will take you out around the town show you the sights, then grab some dinner and maybe a movie or something for later." Sarah replied as she set her cup down as she rubbed her shin against the back of his bare leg.

"Sure sounds good. I could use a hot shower, I hate flying I always feel so tense afterwards." Robert said as he slipped his hand under the table, and placing it on her knee.

"Good! I will be right back, need to powder my nose." Sarah said as she untangled her leg from his and headed off in the direction of the bathroom. Robert sighed contently as he watched her leave, trying hard to imagine her naked, but was cut short of his daydreaming when he felt his phone vibrating in his pocket. Reaching down he pulled the phone out to see he had gotten a text message from his boss.

It read: "System has crashed, need you there ASAP!" "Fuck!" Robert cursed quietly as he flipped the phone shut and jammed it back into his pocket. Robert pulled the phone back out and flipped it open scrolling through his list of numbers to find the one for his contact at the Florida Company. Dialing it he got a gentlemen on the phone who was frantic over losing the last two month's payroll. Robert calmed the man down and got his address and some directions. He promised the man that he would be there in the next hour to fix the problem. Just as Robert closed the phone he saw Sarah walking back to the table. She had a worried look on her face as she could see the anger on his own.

"What's wrong?" Sarah asked as she sat down next to him.

"I have to go in to work today, I just called the company and they lost two month's worth of payroll and need me to fix it." Robert replied sadly.

"Ok...well...I can take you over there, how long are you gonna be?" Sarah asked as she looked at the directions Robert had written down on a napkin.

"I don't know, it depends on how much damage was done." Robert stated as he put the phone back in his pocket and reached back to pull his wallet from his shorts. Pulling out a 20 dollar bill he placed it on top of the check.

"Well then lets do this. You call me when you are done, and I will grab some dinner and some movies while you are out and we can do the tour thing tomorrow." Sarah said as she picked up a small wrapped mint off the check tray and slowly unwrapped it.

"Look I am really sorry." Robert said as he watched her place the hard candy mint into her mouth. He watched her skillfully roll the candy over in her mouth using her tongue, making a small sucking noise.

"No, don't worry about it, we have all week to hang out." She said with a smile as she stood up and gathered up her small purse. The ride over to the business was quick and uneventful, as they quietly chatted. Pulling into the parking lot they saw a large gray building with thousands of windows covering its exterior.

"Ok I will call you when I get done." Robert said as he climbed out of the Jeep.

"Ok. Hey Robert?" Sarah asked as she looked at him with a worried look on her face.

"Yeah what's up?" Robert asked as he gathered up a small black bag containing his laptop and several different programing books.

"I...I am really happy you came down.." Sarah said as she watched him pack his bag. Robert smiled and climbed back into the Jeep, kneeling on the seat and placing his hands on the arm rest.

"Me too." he whispered as he leaned in and kissed her softly on cheek. He watched her eyes close and a red blush cross her cheeks. She turned her head and leaned close to him, he could feel her warm minty breath on his lips as she opened her eyes slightly, which had a dreamy look in them.

"I...I" she whispered as a loud vibrating sound cut through the silence in the truck.

"Damn!" Robert sighed as he fished his phone from the front pocket of his shorts. Flipping it open he saw that it was his boss again, this time he was calling as the phone kept vibrating. Robert looked to Sarah who was silently watching him with a slight frown on her face.

"Get going, call me when you done." She whispered, as she gently placed her hand on his. Robert slowly climbed back out of the Jeep, grabbing his bag he made his way up to the building, and placing the phone to his ear.

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byLostinmich© 3 comments/ 69510 views/ 74 favorites

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