Tgirl Blind Date Surprise

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This is a transgender story. If you don’t like that, then stop reading now. If you’ve read BBW Blind Date Surprise, you’ll find that this story is a riff on that one. Consider this an experiment. It’s almost identical in plot, and dialogue with a few obvious differences. Hope you enjoy it. Special Thanks to EmmaTG and Holly and Salina for their input. But let me repeat this is a TRANSGENDER story. If you don’t like this genre or subject hit the back button now.

2019 Sethp


It wasn’t meant to be a blind date or a surprise. It was just a simple mistake that came about from multitasking, not focusing and doing things too fast. That was one of Robert’s problems though, and he’d soon find himself in an entirely new situation, and enjoying it in spite of himself.

Robert had decided to try online dating, on a whim. He’d been dating for a long time, but none of the girls he’d been with had seemed to pan out. Either their interests and life goals didn’t match his, or their personalities were terrible. He was beginning to see his life as a sham. Was he really this shallow? He really didn’t care about anything his friends did anymore. His last girlfriend, although a beautiful, petite blonde, was also shallow and self-centered. Robert had always found himself drawn to the stereotypical blonde all-American college girls, but finding one that wanted to sit down and binge watch the new sci-fi series or latest zombie movie on Netflix with him was near impossible. Was that really so much to ask for?

Robert worked out a lot and was proud of his body. He spent five days a week in the gym and watched what he ate. He worked at a brokerage firm and everyone there seemed to be a carbon copy of Robert. They all worked out. They all dated the same type of shallow women. They were all obsessed with image and reputation. Robert was starting to get sick of this life though, and was seriously considering a new job and trying to find dates that had a lot more in common with him. He really wasn’t sure how to do that, though.

It was after working out one Wednesday, that Robert created an online dating profile. He had taken his time with it and uploaded some great pictures. He’d already had a couple of messages and things were looking good. Maybe this was the change he needed in his life. He knew that he couldn’t keep doing the same things over and over again.

He was browsing through his matches when he came across a picture that took his breath away. She was just his type with thick blonde hair, deep blue eyes, and a smile that could melt a glacier. He clicked into her profile, seeing more of her. He admired a couple of her other pictures. She seemed like a country girl; a little bit different than what he normally dated. She was the one. He was sure of it.

His doorbell rang, and expecting his nosy sister, he memorized this country girl’s username and closed the tab in his browser. He was slightly embarrassed at using an online dating site and didn’t want his sister asking him a million questions about why he needed to use one.

It turned out to be his neighbor upstairs asking about a notice he had received from the homeowners association. Robert came back to his computer and opened back to the website annoyed that he had to log back in. Just then his cell phone rang. This time it really was his sister.

“Hey Robert.”

“Hey sis.”

“Whatcha doing?”

“Finishing up some emails and getting ready to make a salad.”

“God Robert,” she snorted, “order a pizza and live a little bit.”

“I care about my fitness and health, Jane,” he said a little annoyed and forgetting his password already.

“So do the rest of us. We just don’t obsess over every little calorie. You look great. Hey what happened to Gretchen?”

“Oh… we broke up.”

“Good, she was a bitch.”

“Jane!” He snapped, finally logging in and accidentally clicking on ‘heatherTS’ instead of ‘heather34C’. Distracted by his sister he didn’t even notice the pictures or profile that he was on, and went straight to send message. He wasn’t going to let this little hottie get away. He had to message her fast.

“Are you even listening to me?”

“Sorry… What?” He replied. typing madly away, putting his real email address in the form. It was way faster than the in app message system. He pressed send.

“… and then I said hell no,” he heard his sister finish.

“Wow, that sounds crazy,” he replied having no idea what his sister was going on about.

“Yep, that’s your typical, ‘I haven’t heard a word she was saying’ response. Eat some damn carbs and learn to live and I’ll talk to you later. I still love you little bro. Oh and try not dating any more bitches. Ha!” And with that last barb, Robert’s sister hung up.

Robert shut down his computer and went to make a salad and then sat down to watch a couple of episodes of Black Mirror. God, he loved that show. Gretchen only wanted to watch the Big Bang Theory or Friends. He hated shows like that. He knew his new hottie, Heather would be different. 1080 porno He just didn’t know how different she would end up being.

The next morning before work, Robert checked his email. BING! He had an email from Heather.

“Hi Robert! Thanks for messaging me. I checked out your profile and you are super cute too! I’d love to go out with you. Your profile didn’t mention that you liked girls like me, so I’m really glad you contacted me. I would have passed right over you! Let me know when you’d like to go out. I’m free most of this weekend. Thanks! Heather.”

“Hell yeah,” Robert said out loud to himself. “I’ve still got it. Wait till the guys at the office get a load of you at the office pool party!” He wasn’t sure what she had meant by “girls like me” but he assumed he had messed up something in his profile, or maybe he’d clicked a wrong age bracket by accident. He made a mental note to double check his profile later. He sent Heather an email asking if she was free Saturday night and they could meet anywhere she liked.

When Robert got home from work he was pleasantly surprised to find a couple of emails from Heather.

“Hi Robert! Well I love to eat, but you already knew that! Hehehe…let’s do Italian at Primo Optimanis! It’s my new favorite place. Meet you at five?”

Then the next one.

“Gosh, I just re looked at your profile again, and I’m so glad you messaged me, or I would have passed over you, for sure. I’m super excited though!”

He liked her already. He replied that he loved Italian and that he was excited too. He made another mental note to check his profile. Why would she have passed over him? Maybe he needed better pictures and better summary.

Saturday arrived and Robert was determined to impress his Blonde, petite cutie. He thought he was dressed well, but not too formal, and he had even picked up a rose for Heather. He arrived early, got a really good table and sent Heather a text saying what he was wearing and that he’d be looking for her when she came in the door.

People came and went, but no Heather. He decided to walk to the lobby to double check. There was an extremely tall, muscular, statuesque, busty brunette waving in his direction. Robert looked behind him, didn’t see anyone and kept walking towards the door looking for his blonde hottie. When he reached the front foyer, he couldn’t ignore the tall lady any longer. She came right up to him and gave him a big rib cracking hug.

“Uh…” he muttered smothered in her strong arms. Before he had a chance to ask if they knew each other, she backed up and took the rose from his hand. “That’s…” he started to protest.

“…Adorable,” she said smiling warmly at him. “Thank you!” Then she give him another hug, kissing him on the cheek. “You’re even cuter in person,” she said, “and just as funny… pretending you couldn’t see me! I know I’m not hard to miss! Do you already have a table?”

Robert wasn’t a completely stupid man, and in a couple of seconds he had ran through all of the possible scenarios in his mind, coming to the realization that he had messaged the wrong Heather on the dating app. “Heather,” he said, and then when she glanced over at him. “Right this way!” He continued, warmly. Inwardly berating himself, knowing that someone was going to swoop right in on his online hottie. He had missed a prime chance with his stupidity and carelessness by clearly messing up profiles.

“Wow,” he muttered, stealing a glance at her massive chest.

“Wow?” Heather asked, eyebrows raised.

“Yeah!” Robert responded quickly. “You’re even cuter in person too. I’m so lucky!” he lied.

“Thank you!” She beamed at him sitting down.

Robert had to admit that she was beautiful, just not his normal definition of cute. She was probably several inches taller than him, with a really warm smile. She had thinner lips than he normally liked on a woman and long, jet black hair hanging down past her shoulders. She was wearing a tight black dress that accentuated her muscular arms and legs, and large firm breasts. They jutted out proudly from her chest, seemingly defying gravity. Amazonian, was the word that popped into Roberts’s brain.

“So do you date a lot of ‘girls’ like me or only girls like me,” she asked, almost immediately.

Robert wasn’t sure what she meant. Did she mean muscular, athletic women that were taller than him? “Most of my dates are shorter than me,” he responded, taking a sip of his wine.

“Oh okay. You’re profile wasn’t clear. It wasn’t clear on a lot of things.”

“I’m sorry, I put it together a little too fast and I think I messed it up,” he laughed. “Sorry.”

“It’s okay,” Heather said, smiling at him.

Damn that profile, Robert thought again, vowing to see what he had put in it, when he got home.

After ordering their dinners, the conversation became more a lot more casual and Robert had to admit that he was starting to relax and actually having a good time. He just hoped none of his friends walked in 2 k porno on him. He felt a little bit uncomfortable, because Heather was more muscular and taller than him, and probably a few years older as well. She had a deeper husky voice that he really liked though. This was definitely different. During the course of dinner, Robert found out that they both liked the same shows, music, movies and books. It was really astounding how much they actually had in common.

As they sat there finishing their chocolate mousse dessert, Heather asked. “So, I was really nervous about meeting you. I’m a little bit older and taller. I don’t date much because of, well you know, but I really had a great time tonight.”

“You know, I did too.” Robert said truthfully. “I had a really great time. Thanks for going out with me.”

“What do you like about girls like me?” She asked suddenly, looking into his eyes. She didn’t mess around with the hard questions.

“I don’t know,” he said truthfully.

“Well, I think we have a lot in common, don’t you?”

“Yeah,” he smiled, “We do.”

“And I know you like these,” she said subtly cupping her large breasts. “You’ve been steeling glances at them all night.”

“Uh… sorry,” he muttered, feeling embarrassed. He never felt embarrassed or off balance on dates. This was a first for him. He had to admit that he was fascinated by her. There was something about Heather that he couldn’t place. Maybe it was everything together. She had a wonderfully, husky voice, she was muscular and strong, she was tall. He wondered what those big breasts looked like unclothed.

“Don’t be sorry,” she smiled. “I like the attention, and you aren’t a jerk about it.”

“Thanks… I,” he sighed. “I don’t even know what to say.”

“Then don’t say anything,” Heather said, reaching across the table and taking his hands in hers. “You have nice hands.”

The bill came and Robert paid it and walked Heather out the door. “Did you drive here? I mean do you need a ride home?”

“I took an Uber, actually, and yes I’d love ride home please,”

“You bet, come with me,” Robert said walking ahead of Heather. He led her to his BMW.

“Wow! That’s a really nice car. I’ve never been in one. Oh, these seats are so small,” Heather said squeezing herself into the passenger side seat. “You already know this, but my profile said I like guys with big trucks,” she laughed. She had a great laugh.

Robert drove Heather to her apartment complex. The seatbelt accentuated her cleavage. Well that was wrong, Robert thought. The seat belt got lost in that cleavage. He had to fight himself to keep from looking over at her. They pulled in to her complex, and it was probably the shadiest place he had ever been to in his life. “You live here?”

“Yeah,” Heather said, defensively. “It’s not as bad as it looks. I’ve never had a problem here, the neighbors all know each other. We all look after each other.”

“Well, let me walk you up to your door, at least,”

“I was hoping you would,” Heather smiled at him.

Robert opened the passenger side door, taking her hand. She had a hard time getting out of the car, but Robert managed to pull her to her feet. It was kind of nice holding hands with heather as he walked her up to her apartment. Gretchen never wanted to hold hands. When they got to her door, Heather paused for a moment and then wrapped her arms around Robert and kissed him. It was a great kiss and her large firm, breasts felt heavenly against his chest.

“That was really nice. Will you come in for a minute?” She asked.

He wanted to say no, but he couldn’t. “Yes.”

Once inside, Heather pushed Robert against the door, grinding against him, kissing him deeply and sliding her hand down to the front of his pants. Despite himself, Robert was hard as a rock. Heather moaned against Roberts mouth as they kissed, urgently rubbing her hand against his cock. Then she pulled back. “I need a drink.”

“Me too,” Robert croaked.

Heather poured them both a glass of red wine. Robert downed his in one swig. Heather laughed at him as she joined him on the couch.

“Sorry, I don’t usually do that,”

“It’s okay,” Heather said, peeling down the top of her dress, revealing two perfect, gravity defying breasts.

“Wow!” Robert said, kneading them and kissing Heather again.

“They’re not too big?” Heather asked, pulling back for a moment. “I wasn’t sure what size to get and everyone always says bigger is better.”

“They’re perfect,” Robert said looking up at Heather, palming them and kissing her again. He’d never been with a girl with fake boobs before. He didn’t mind them in the least.

“Stand up,” she ordered.

Robert obeyed, taking off his shirt as he did.

“My god you’ve got a great body. I’ve dreamed of someone like you,” Heather said, unfastening Robert’s pants and pulling them to the floor. His cock was straining against his boxer briefs. Heather pulled those down as well, letting Roberts cock spring 3 k porno free. “It’s so big,” she cooed, and took him into her mouth. She slid her lips all the way down to the base of his cock, letting the tip touch the back of her throat.

“Unggng,” Heather slurped noisily, as she bobbed her head up and down Robert’s cock, drooling.

“Oh fuck!” Robert croaked. This was already one of the best blow jobs he had ever had. He looked down, locking eyes with Heather as she worked her mouth up and down his cock. Embarrassingly, he was already about to cum. “I’m so close… I can’t… I’m going to… I’m sorry…”

Heather grabbed his cock and pumped her fist on it as she sucked him. She didn’t give him a chance to pull away; she wanted him to cum in her mouth.

Robert grunted as he shot his load onto her tongue. She moaned as she received his sperm, swallowing every last drop of it.

She pulled her mouth away when he was spent. “That was delicious. No mess either.” she giggled, sitting back on the couch and pulling her dress all the way off. Robert marveled at her six pack and muscular body. “My turn,” she hissed at him, breathing hard, breasts heaving and sitting there in only her panties.

“God that was good,” Robert managed. He’d never had a girlfriend that had let him cum in her mouth before. It was an amazing first. He’d only seen that happen in porn. “Of course,” he said, kneeling down in front of Heather. He’d gone down on plenty of girls but never one as athletic as Heather. He paused suddenly. She had an obscene bulge in her panties. It looked like she was hiding a cock in there that was bigger than his.

“I…I…” he stammered, shocked.

“Please…” Her eyes were pleading. She looked like she was about to cry.

Robert placed a hand on her leg and Heather grabbed it moving it up to the bulge in her panties; moving his hand over it. Robert, despite his shock, grabbed it, hard, squeezing it.

“Oh God yes!”

Was she really a trans girl? Did it make him gay if he wanted to see Heather’s cock? Did he care about any of that? She looked so vulnerable there, grinding her pelvis up against his hand, needing the release that she had just given him.

Heather lifted her hips off the couch, letting Robert pull her panties down. Her magnificent cock waved free. It was definitely bigger than his. She took Robert’s hand again, placing it on her cock and he started to slowly stroke it for her.

“God Robert,” she hissed. “You hand feels so amazing. It’s been so long since anyone’s touched me. Suck me…please,”

She lifted her legs up onto Robert’s shoulders as he moved in. It was then that he realized that she smelled amazing. He gave her cock a nervous lick and she almost shrieked. Then he engulfed as much of her as he could into his mouth, trying to imitate what she had done to him.

“Yes! Oh, Yes Robert!” she had her hands in his hair, urging him on.

She was driving her hips up off the couch, pushing her cock deeper into his mouth, causing him to gag a little bit. He had to pull off of her a little bit, grabbing her cock again to control it.

“Oh… oh fuck! It’s been so long… you feel so good… don’t stop,” she pleaded.

Robert didn’t stop. He pleasured her as well as he could. He pleasured her because she deserved to feel good. He was savoring her moans of pleasure, thrilling in the fact that he was going to make her cum. It didn’t take very long.

“I’m cumming!” she screamed at Robert. He kept his mouth clamped around her shaft. Heather’s whole body shook in orgasm and she squeezed her muscular legs against his head. “Oh my god!” she screamed, erupting into his mouth.

Robert had never tasted sperm before. It was a new experience; salty. He tried to swallow it like she had for him but there was so much and the sensation was so new. It started to spurt out the corners of his mouth. He had to pull his mouth off and was rewarded with a final rope of sperm across his face.

When Heather was finished with her orgasm, they just sat there breathing heavily and staring into each other’s eyes. She grabbed her panties, using them to wipe her ejaculate off of Robert’s face, giggling. “I’m sorry. I should have warned you that I’m a heavy squirter.”

“Come on,” Heather insisted, getting up and pulling Robert with her. She dragged him down the hallway to her bedroom. She had a huge King sized bed that Robert admired for a moment, before gazing at his new lover.

Robert was hard again at this point. Heather opened a drawer beside her bed and pulled out a condom. “I need you inside me,” she said handing it to Robert and getting on the bed. She had a tube of KY open and applied some as Robert slid the protection on his painfully hard erection. Heather moved over, motioning Robert to lay down on his back and then she climbed on top of him, grabbing his cock and guiding it into her.

She felt so wonderfully tight. Robert had never felt anything like it. She leaned forward kissing him pressing her hard body on top of his. She sat back then, getting into a rhythm, slamming up and down on his cock. Robert was in heaven, grabbing on to her hips as he thrust up into her. Heather came again as she rode him. Her cum squirted onto Robert’s stomach as she screamed his name. “Robert!”

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