First Time for a Trans Babysitter

I am a transgender woman who writes erotica about and for transgender women. My stories feature trans women being treated like women and having the diverse sexual experiences that they deserve. Enjoy and let me know what you think! More stories to come.

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The Palmer kids had been too peaceful. Normally, Isabella would've been grateful. Tonight, though, she needed a distraction. She just graduated from high school and wondered what the future would hold for her as a transgender woman. Now that the kids were in bed, her mind had nowhere else to turn apart from rumination about what lay ahead for her.

She hopped onto the plush living room couch and sat back, alone with her thoughts. Anxiety tightened her chest. She needed to get a summer job. Babysitting for Mr. Palmer was great, but she needed to save up more money for college. And she needed to get her driver's license changed. It had her old name and photo and said she was a guy. The last time she got pulled over, the cop thought she was trying to drive using her brother's license.

She didn't know what her college experience would be like as a transgender woman. Hell, she didn't know what the rest of her life would look like. She wanted a career and a husband. Someone like Mr. Palmer. He was charming and had deep blue eyes. He had raised the kids alone after his wife died in a tragic accident, managing the stress of children and work effortlessly. Isabella was happy that she was babysitting for such an upstanding man.

Though he wasn't just upstanding. He was stunning. He had salt and pepper hair and was as tall as a basketball player. Sometimes Isabella couldn't help but notice the thick biceps that she could see ripple under the starched shirts he wore for work. And those eyes -- she found it hard to make eye contact with him when they spoke. Once or twice, she got lost staring into them and forgot her train of thought. He would smile while she stammered awkwardly under his gaze.

Sometimes she fantasized about him.

But he didn't know her secret. He didn't know that she was transgender. Would he still like her if he knew? Would a man like him even give her the time of day if he knew?

Just then, her train of thought was interrupted by the roar of the garage door opening. She sat up. "Mr. Palmer is home earlier than usual," she thought. "I hope everything is alright."

The door to the house slammed shut. Usually, Mr. Palmer had a gentle touch. Something must be wrong. Then, Isabella heard a shout.

"You had someone over in my house?" Mr. Palmer yelled from the kitchen, a few rooms over. It wasn't a question, though. It was an accusation.

Isabella darted from the couch to the kitchen. She didn't know what he was talking about. The tile was cool under her bare toes, but Mr. Palmer's face was hot with anger.

He was holding her ID.

"I trusted you, Isabella," he said. "I thought you were a good girl. But I find a guy's driver's license dropped on my floor? What's going on here? I can't believe you would use my house to have sex!"

"It's not what it looks like, Mr. Palmer!" Isabella shouted.

"I don't want to hear any excuses," he said, stern. His eyes flashed at her. Even when he was angry, he was attractive.

"I... I... that's..." Isabella was flustered. Looking up at him, pleading with her expression, she could hardly form any words.

"Spit it out," Mr. Palmer said to her.

"That's me!" She said finally. "That's my old ID."

He took a step back. "I don't see what you mean," he said.

"I'm transgender."

Mr. Palmer stopped for a beat. Isabella thought she saw his eyes flicker down to look at her breasts. She shivered.

"That's ridiculous," said Mr. Palmer. "You're beautiful. You don't look male at all. Just confess."

This was her deepest secret, and he didn't believe her. She couldn't believe she had been outed like this. It was all too much. Before she knew it, tears were streaming down her cheeks. Her legs felt weak. She couldn't stand under the whirlwind of feelings. She sat on the floor and laid back. The tile drew the warmth from her cheek.

Mr. Palmer was still. What did he think of her? Would he kick her out? She kept her transness a secret because of how she feared people would react. She had already lost friends, stressed her relationship with her parents, spent innumerable hours in doctors offices, even foregone sex. Was this going to be just another humiliation in the life of a trans girl?

She looked at his legs. Even in her current state, she couldn't help but notice how they were almost bursting with muscle. If he rejected her because of her trans identity, she would miss the money, she would miss helping out such a responsible dad. But god, she would also miss looking at him.

He crouched down to her. The anger was gone from his face. He tried to speak but struggled. This was the first time she had seen him lost for words. He sat down next to her.

"I understand," he said after a while. "Well, I don't understand, I don't think I can understand. I can't imagine what it's like."

He rested his hand on hers. She trembled underneath his touch. His skin felt like warm leather against her soft hand. His grip was firm and gentle at the same time.

"I support you, though," he said. "It's courageous. Living as the real you. I'm sorry I didn't listen to you. I shouldn't have been so stubborn. I just had such a frustrating date."

He wiped the tears from her face, making long swoops with his hands. He dried them on his shirt over his chest.

"She just kept going on about politics. She was such a bigot." He took a beat. "I don't know why I'm telling you about this, though. I'm just sorry. That's all."

"It's okay, Mr. Palmer," Isabella said. "I understand. I'm just emotional, tonight. I just graduated and I feel like I have such little experience with the world."

"It gets better, Isabella."

"I don't even know what I'm doing. What life will be like. How being trans will affect me. I've never even been on a date."

"I'm surprised," he said. "I meant what I said. You are beautiful. I would think all the guys would want a girl like you."

He smiled down at her as he spoke. Isabella was ready to discount his comment, but from the look in his eyes she realized it might be more than just an attempt to brush away the awkwardness of the situation. "Is he flirting with me?" she thought to herself.

"I don't believe you," she said.

"You don't believe me?" he asked, chuckling.

"No," she said. She smiled and met his eyes. Usually, she had trouble sitting under his gaze but there was a hunger inside her now. She pushed further. "I don't believe you. You're just saying words."

Mr. Palmer brought his face close to hers. She could see his broad cheekbones and sharp chin. "You are stunningly gorgeous," he said.

"Prove it," she said.

He brought his lips to hers. Before she knew it, they were kissing. He kissed long and deep, holding her neck with his firm hand. It felt like her neck was made for his grip. It all just felt natural.

He started to stroke the nape of her neck but it tickled. She couldn't help but giggle through the kiss.

He rushed away and looked down at her with gentle eyes. "Are you okay?" he asked. "We don't need to do this if you don't want to."

"Sorry," she said, blushing. "You just tickled me."

"Oh," he said, laughing and taking the back of her head into his palm. "I was worried you were nervous."

"Well, I've just never done something like this before," she said. "I am nervous." She looked up at him. "But I'm also excited,"

"It's okay," he said, stroking her cheek. "We can take this slowly."

But maybe she didn't want him to take it slowly. She dove into him, kissing him on the lips and grabbing his shoulders. He grabbed her back and tilted her onto the tile, which was cold under her head. Any discomfort from lying on the floor, though, was far from her mind. She felt like she had just swam in the warm ocean for the first time. She felt the warmth of his body against hers, the hardness of his muscle through his ironed shirt, how tender her lips felt against his.

She felt his tongue start to explore her mouth. In this moment, she realized why french kissing was so popular. His tongue felt so nice. As it retreated, she stuck her tongue into his mouth a bit too quick.

"Woah, there," he said, taking his head back, looking down at her and smiling. "You're very eager."

She blushed. She felt embarrassed.

"You're so experienced, though," she said. "And I'm so new to this."

"Don't worry," he said, "I'll help you."

She smiled and looked up at him. But then her smile vanished and she turned white. She pushed him back and scooted away.

"Wait," she said. "You know what me being transgender means, right?"

"Yes," he said, laughing. "I'm not ignorant."

Isabella was still nervous.

"I support you," Mr. Palmer said.

"I know," she said and took a pause. "I just... I haven't... I haven't had any surgery, yet."

"I see," he said, and looked down between her thighs. Her womanhood had been swelling against her jeans. She looked down and noticed her wetness was also seeping through the denim. When she looked back up, he was smiling his bright, wide smile. "Maybe this is a bit new for me, too, then," he laughed. "I think I'll be able to make do."

"Okay," she said, feeling better. He anxiety eased with his smile and all that was left was the nervous excitement of being with him.

"I don't know if exploring is best done here, though," he said.

"Sorry?" she asked, not quite getting what he meant, such was the state of her thoughts, all jumbled and melting under the anticipation of what they were about to do.

He gestured around to the kitchen.

"Ohh," she said.

"Let me take you to the bedroom," he said and swooped her up in his arms. He held her like a bride, one hand under her shoulders and another under her knees. It was effortless for him. It felt magical, like she was floating on air. He ran across the house to the stairwell and up the stairs. When he threw her onto the bed, he wasn't even breathing hard.

"Oh my god," she said. The bed enveloped her. It was a king -sized mattress and she felt like she was lying on top of a cloud. There was so much space! She couldn't believe she was lying where Mr. Palmer slept every night, where he sweated in his dreams, and that he was standing over her, looking down at her and stretching, getting ready to take her virginity. Her heart beat through her chest. She soaked him in as his strong hands took off his shirt button by button.

"Is this alright?" he asked. "I don't want to get my shirt too dirty," he said with a wink.

"Yeah, it's fine," she said, shy.

He glanced at her.

"I mean yes," she said, bashful and blushing. "Yes, please."

"There's no need to be embarrassed," he said. "I need to know you want it. I want you to feel safe. You're only 19 years old, so you need to be sure of what you want to do." He leaned down and put a hand on her knee. "I only want to do what you want to do."

She sat up. "I want this," she said.

"I'm glad," he said, and she could tell that he meant it. His eyes were soft and his expression showed that he cared for her.

He kissed her and pushed her against the mattress. He leaned over her and pushed his tongue into her mouth. Her anxiety started to melt away along with the rest of her body. She only felt his lips and how badly she wanted to continue kissing them.

When he pulled away, it was like she was coming to after surgery. The world was new. She wanted him again. She tried to lean up from the mattress and grab him but he playfully pushed her back down.

"You're distracting me," he said with a smile. With this, he stood up, stretched again. and continued taking off his shirt. First, his chest was exposed, two hard slabs of muscle. Then, she saw his abs, which looked like they could stop a bullet. She always knew he was in shape, but she never knew that he was *this* in shape. He pulled it off and there Mr. Palmer was, standing half-naked in front of her. She bit her lip. She wanted desperately to touch herself but didn't want to offend him. She wanted to wait for him to give her instructions. He just had that aura, that he should be in charge, and she was glad. She wanted Mr. Palmer to be in charge of her.

He sat down on the bed and drew her into his arms. Her head was in his lap. She felt his growing manhood through his jeans under her cheek. He held up her head and placed a kiss on her forehead. He was about to kiss her on the lips again when he stopped.

"I need to know that you're okay with this," he said.

"I'm okay with this," she answered, not missing a beat.

"I need to know for sure. I need you to beg for it."

"You want me to do what?" she asked.

"I need you to beg for it."

She was happy to.

"I want you so bad," she said. "Please."

"What do you want me to do?" he asked. He started to stroke her long, soft hair.

"Anything you want," she said. Her eyes were pleading, searching.

"You're going to have to be more specific than that," he said. "Should I touch your breasts?"

"Yes," she said.

"Yes, what?"

"Yes please."

"I'm not convinced that you want it," he said, even though she was biting her lip so hard it almost bled.

"Please. Please, can you touch my breasts?"

"Hmm," he said. "I can't tell how badly you want it." She could tell he was enjoying this. He was enjoying watching a beautiful and young transgender woman beg for him to touch her. And she enjoyed his enjoyment. She enjoyed it so much that she had to use all of her willpower to not fling herself at him.

"I want you so bad," she said. "I want you. Please. Please. I need you. I need you to touch me."

He smiled and reached into her shirt to grasp her breast with his right hand, using the other to continue stroking her hair. It was ecstasy. Her breast fit so well in his hand that she thought for a minute that maybe it had been molded for his grasp. After holding her breast for a bit, enjoying her soft flesh, he took her nipple between his fingers and rolled it around. Waves of pleasure emanated through her mind. It felt like previously unconnected wires had been activated for the first time.

She moaned.

"I'm going to take your shirt off, okay?" he said.

"Yes please."

"Good girl," he said and sat her up so she was sitting with her back to him between his strong legs. He kissed her neck as he found the bottom of her shirt and pulled it off of her. She felt the air against her breasts. She felt exposed. Nobody had ever seen her naked chest apart from her since she started transitioning. She was insecure about her breasts, worrying that they were too small or shaped incorrectly. But it was like Mr. Palmer read her mind, because as he took both of them in his arms, he whispered in her ear: "You are *so* beautiful." He continued to feel them, tracing his fingers up and down across her nipples as she shivered with his touch. The feeling went down her spine and her whole body was set alight with the warmth of his touch.

He continued to kiss her all over her neck as he touched her bust. Involuntarily, she squeezed her legs together and moaned, overcome with arousal. She could feel her wetness dripping now and pooling between her thighs where she was tucked. She realized how good it felt to squeeze her thighs together and rock back and forth, stimulating her womanhood and pleasuring herself.

She was getting excited, moaning louder and louder with the intensity of his kissing.

"Woah, there," he said, suddenly stopping. "I think you're getting a little ahead of yourself."

"Sorry," she said.

"You can't come yet," he said. "I have so much more to show you."

"I'm sorry, Mr. Palmer," she said. She felt his hardness against her back.

"It's okay," he said. "You can make it up to me."

"Yes, please," she said. "I'll do anything you want me to do."

He stood up. He was so tall that, even though she was sitting up on the bed, his groin was almost level with her eyes.

"Do you want to take me in your mouth?" he asked.

"I do," she said.

"I need you to be sure," he said, smiling and ruffling her hair.

"I'm sure," she said. "Please let me take you in my mouth."

He unbuttoned the top button of his jeans and she was overcome with anticipation. He unzipped the zipper, pulled his jeans down, and there lying against his boxers was the outline of his manhood. He was huge. Isabella's eyes grew wide. She was looking forward to the challenge.

Mr. Palmer pulled his manhood out of his boxers. The tip gleamed. She put her face next to it and noticed that it smelled nice, like musk.

"Go ahead," he told her.

She opened her mouth and licked his shaft, which tasted slightly salty. She took him in her mouth. She knew what to do from instinct, taking him further and further, feeling his warmth inside her mouth, tasting his juices, going up and down on it. She felt like she could keep going forever. Mr. Palmer stroked her hair as she took his manhood.

She kept going, feeling like her mouth was perfect for his shaft, until he placed his hand on her shoulder and pulled himself out of her mouth.

"That's enough for now," he said. "You did a good job." He leaned down and kissed her on the mouth, then gently pushed her back onto the bed.

"Do you want me inside you now?" he asked, his hand on her hip.

"Yes," she said. "Yes, please, I want you so bad." It was true. It was the only thing on her mind. The only thing better than having him in her mouth, she thought, would be having him inside of her opening.

He unbuttoned her jeans and pulled them off of her legs. She felt exposed. The cool air of the bedroom played against her skin, raising gooseflesh on her legs. Now, she was in front of Mr. Palmer, wearing only her panties. They were now almost completely soaked where she was tucked. Looking down, she saw her womanhood, hungry for him, pushing against the gusset of her underwear. She crossed her legs, suddenly self-conscious, again.

"It's okay," said Mr. Palmer. "I want all of you, Isabella."

She uncrossed her legs and Mr. Palmer pulled them up to his shoulders, bringing her closer. He peeled off her underwear.

She was completely naked for Mr. Palmer.

"I want to give you head, first," he told her.

She was a little nervous but gave him a clear yes. He brought her even closer, grabbed her thighs, and put his head between them. He ate her out almost like he would a cis woman, licking her all over. She had never imagined that a guy would go down on her like this, so enthusiastically, with such attention to detail. More than this, she never expected that it would feel *so* good. In that moment, it was almost like she had a vagina. She didn't feel her physical anatomy, just the pleasure coursing from the movements of his tongue and his wet spit. She felt herself getting close to orgasm.

"Oh my god," she moaned. "Oh my god."

"Are you close?" he asked.

"Oh my god," she moaned again. She could hardly think of words. "Yes, I am. I'm close."

She felt the pleasure collect at the bottom of her spine.

"I'm going to come," she said.

"Come for me," he told her, and she did. She felt herself spasm under the wetness of his tongue. It was like she was a bird sailing on a current of air. Time seemed to slow down. She heard the hum of the air conditioning, felt the soft embrace of the mattress, smelled the musk of Mr. Palmer, enjoyed his tongue still working over her. He stopped and lay next to her. She was still for a moment.

"I'm ready," she said exhilarated. "I'm ready for you to go inside me."

"Are you sure?" he asked.

"Yes," she said. "Very sure. Perfectly sure."

And she was.

He climbed on top of her and kissed her neck, bringing a moan from her lips, which he then kissed, for good measure. He continued kissing her as he held his manhood against her opening.

She gasped.

"Are you alright?" he asked.

"Yes," she said. "It's just a lot."

"We can wait, if you want," he said. "I'm perfectly fine--"

"No," she cut in and grasped the back of his neck, pulling him close to her. "I don't want to wait."

He nodded and kissed her lips again. He rubbed himself up and down against her opening, eliciting moans.

"Please," she said.

He pushed inside of her and the world stopped. All that mattered was that he was inside of her. It was unlike anything else she had ever experienced or imagined.

She felt full. She felt like some part of her that she had anticipated for so long had been fulfilled; she felt complete.

"Does this feel okay?" he asked.

"Yes," she said. "Yes, yes, yes, yes, yes."

He started to slowly thrust in and out. She moaned with each thrust. In this moment, she knew that she had made the right decision. So many decisions, so much worrying, had led to this night, this beautiful, wondrous night, with Mr. Palmer. Together, they made a unity. For all her insecurity about her transition, she knew now that she was where she belonged. She knew this was what was natural. This was what was right.

He moved faster and faster in and out of her. She felt like she was floating on air but at the same time she felt like she was grounded in that moment, that she was part of the mattress, part of Mr. Palmer, part of the world. She wrapped her legs around him and moved her hips up and down to match him, wanting him to go deeper and deeper into her.

She had just orgasmed a few minutes ago, but felt like she was now on the cusp of another, greater orgasm.

"Oh, Mr. Palmer!" she moaned. "I might come again."

"You better come again, Isabella," he responded.

She let herself escape into the flow of their rocking, feeling the pleasure build and build, until she came again. She felt her wetness, the result of her orgasm drip down her stomach and her side, but she didn't stop bringing her hips up and down against him.

"Good job, Isabella," Mr. Palmer said. "That's my girl."

He kept thrusting, and the pleasure continued to build inside her, until she felt close again. She had never experienced anything like this, before. There was something there that was beyond human arrangements, something that felt deep and ancient and animalistic. She knew that she needed him and he needed her.

"Isabella!" he yelled as they both finished. He collapsed on the bed next to her. They both stared at the ceiling. She could have sworn that in its beige she saw something holy.