Jessie Raiye: The First Date

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#7 of Jessie Raiye


Derrick grinned up from his position on the couch in the Raiye family living room. Jessie had just walked into the room, dressed up and expecting company, but she was caught completely off guard by Derrick being there. It was a complete surprise, albeit a very pleasant one.

"Is there something wrong with the way I'm dressed? Do I have something on my face?" Derrick chuckled as he questioned Jessie.

"No, why?"

"Well, you're staring at me like there is something wrong with me. Though I take it you're just happy to see me."

Jessie blushed softly, before nodding. "Yeah, I was really upset that I couldn't make it to school today. I really wanted to see you."

"Why weren't you at school anyway?"

"Ummm," Jessie blushed, unable to think of a lie on the spot.

"Jessie was having ... feminine problems," Vivian giggled from the kitchen.

"Oh, well I don't want to know about that," Derrick laughed, standing up. Both Derrick and Jessie were acutely aware of their difference in size, as Jessie only came up to Derrick's mid-chest. But Jessie found that comforting, knowing that Derrick would protect her if anything came up.

"Umm, Jessie. I know this is sudden, but would you be interested in going out to dinner with me? Like, right now?"

Jessie blushed brightly, before reaching forward and wrapping her paw around his stronger claw. "I'd love to. Where would we go?"

Derrick smiled as he held her paw. "I'm not really sure. I don't know much about this area. And we're young, so it'd probably have to be in walking distance. Unless your sister would drive us."

"Too busy making dinner," Vivian called from the kitchen. "But you could always go to that nice restaurant a couple of blocks west of here. It's a nice place."

"Sound good?" Derrick questioned, looking down at his petite vixen companion.

"Yeah," Jessie blushed. Just holding Derrick's hand was arousing her, but she had to keep herself under control.

Blushing and smiling, the young couple stepped out of the house into the brisk, spring night. From the kitchen, Vivian grinned widely.

"It's so nice to see young love blossoming. But I'd better not let them distract me, or I'll burn the roast again."

***

"So, do you have any siblings other than Vivian?" Derrick asked as they walked along towards the restaurant.

"Yeah. My sister Lexi, who's a year older than you."

"Wow, three girls. Your dad must feel outnumbered."

Jessie stopped in her tracks, surprising Derrick. "Actually, my dad left when I was younger. Though he wasn't even my real dad. I've never met my real dad."

"Sorry to bring that up," Derrick replied sheepishly. "I didn't mean to upset you."

"It's fine, you didn't know. What about you?"

"It's just me, my dad and my younger brother. My mother died not long after my younger brother was born. Jace, my brother, is only 8." Derrick smiled softly, taking a hold of Jessie's paw, before giving her a little tug. "Come on, we'd better get going. We want to be able to get a table."

"Oh, uh, right," Jessie blushed as she walked along beside her hunky man.

***

Once seated in the restaurant, Derrick was quite shocked at Jessie's order. Every other girl he knew, especially the attractive ones, would have ordered a salad or pasta. But Jessie ordered herself a nice fancy meat dish.

As the waiter left, Derrick cast Jessie a confused glance. "I've never heard of a girl like you who doesn't order salad or pasta."

"Oh ... well," Jessie blushed, never thinking that most females try to watch what they eat. Sudden inspiration gave her a perfect rebuttal. "Do you think I need to watch my figure?"

"Uh, no," Derrick stammered, "you look perfect. I was just meaning ... uh, never mind."

Jessie giggled, before blushing brightly. "I just realized this is our first date."

Derrick reddened slightly at the thought. "I kinda thought this was just a friendly dinner."

"We're more than friends, aren't we?" Jessie asked softly, placing her paw on Derrick's claw.

"But we barely know each other."

"It doesn't matter to me. I knew we were meant to be more than friends when I first met you," Jessie lowered her eyes slowly. "But if you don't feel the same, I guess I can understand."

"I do Jessie. I was just meaning that we should probably learn a little bit more about each other. I never thought I could feel this way about anybody."

Jessie blinked back tears of happiness and love as their meals arrived. Looking down at her delicious meal, Jessie got an idea. "Okay Derrick. How about this: we eat our meals, head back to my place and learn more about each other? Anything that we think might be important for each other to know. Sound good?"

"Sure thing Jessie," Derrick grinned.

"Oh, and I hope you don't mind paying for the meal, hunk. I left my purse at home."

Derrick laughed, shaking his head. "I should have guessed. Good thing I thought to bring my wallet."

***

Grabbing up the ringing phone, Amanda sat down on her bed as she answered it. "Hello?"

"Um, hi. Is Amanda there?" Kayden lay on his bed, really nervous about making this call. It had been fourteen years since he had last talked to her.

"Kayden ... I'd recognize your voice anywhere, even after all of this time. So I guess you got my message?"

"Yeah. Amanda, you should have told me from the start. I mean, I knew you were married and I didn't care. I always wanted a daughter. And now I suddenly find out I have one."

Amanda gulped softly. "About that. Technically, she's not your daughter."

"What do you mean? You said she was my kid and -"

"I mean she's not your daughter. Technically, she's your son."

Kayden blinked in confusion, staying quiet for three whole minutes before gasping out loud, "What the hell does that mean?"

"Your daughter, Jessie ... she was born Jake. A boy. But that's not who she is on the inside. She never really was a boy. So, for her thirteenth birthday, she admitted that to us. And we helped her become a girl. It's only been two weeks, but the whole family has embraced her as a girl."

Kayden laughed softly. "As long as she doesn't looks like a guy in drag, I don't care. She is my daughter after all."

Amanda grinned widely. "She really wants to meet you. And I wouldn't mind seeing you again either."

"Set the time and the date babe, and I'll pack up house and home if you want me to."

***

"Come on!" Jessie pleaded, kicking her stocking-clad foot-paws as she and Derrick sat on her bed. After they had finished their meal, they had walked back to Jessie's place. Now sitting on her bed, the two were getting to know each other better.

"No way Jessie. I'm not telling you."

"Please?" Jessie pleaded, pouting and leaning into his chest. She could feel his strong muscles under her as she pressed herself against his chest.

Derrick blushed softly. Feeling Jessie against his chest like this was so wonderful. "Well, I guess I could tell you ..."

"If you tell me your most embarrassing moment, I'll tell you mine."

"Fine. It was at the regional qualifiers last year. We started the last race, which would determine who would move on. Halfway down the track, I lost my shorts and my underwear. They just ... fell off," Derrick blushed brightly.

"No way!" Jessie squealed. "What did you do? Did you stop to pull them up?"

"Well, I couldn't risk losing the race and not going on to the nationals. So, I just stepped out of them and kept running, half-naked. I ended up winning in the end, but it was pretty awkward. Mainly cuz like everyone saw my groin and ass. As soon as I had finished I ran back, grabbed my clothes and threw them on real quick."

"Wow, that is really embarrassing," Jessie giggled, poking him in the chest.

"Yeah, I know. Now, I believe it is your turn to tell me your most embarrassing moment. So, what is it?"

Jessie blushed brightly. "Actually, I don't really have a most embarrassing moment. At least, not yet. I'm pretty sure I will in a few minutes."

Derrick blinked, looking down at Jessie. "What do you mean?"

Jessie sighed softly, snuggling into Derrick's chest. "My mom told me not to tell you this until I was sure you wouldn't care but ... I need to tell you. I can't keep this a secret from you any longer."

Derrick held her close, sensing that she was on the verge of tears. "Tell me Jessie. I promise it won't bother me."

Taking a deep breath, Jessie blurted out, "I'm a boy." Giving Derrick a second to let it sink in, she continued. "I was born a boy, and I've actually only been a girl for two weeks. I hope you won't hate me."

Derrick softly stroked Jessie's hair. "Jessie, I have to admit something. I found out about this earlier today. My friend Leif told me. He told me that the youngest of your family was Jake. So, I kinda guessed that you really were a boy."

"Wait ... you knew before we went out for dinner? And you still wanted to go out with me?"

"I still want to be your boyfriend, no matter what. I like you for you, for your personality and your beauty. I don't care what you used to be. It's who you are now that matters the most."

Jessie blushed brightly, staring up in surprise at her draconic companion. "Boyfriend?"

"You don't want me to be your boyfriend?"

"Well, sure. I guess we could -"

Jessie's sentence was suddenly cut off by Derrick as he gave her a soft kiss. Slowly, the young couple's soft kisses began to grow in passion, until they were rolling around on Jessie's bed, tongues entwined. They kept their paws and claws to themselves, wanting to take the sexual part of the relationship to a minimum at the moment.

Slowly breaking their passionate kisses, the young couple held each other close as they lay on the bed together. Getting up slowly, Derrick smiled down at Jessie.

"Sorry Jessie, but I'd better get going. Will I see you at school tomorrow?"

"No, not til next week or so. But that doesn't mean that you can't come by tomorrow after school. I can't wait to see you again," Jessie giggled, blowing her boyfriend a kiss.

"Me neither. I'll hopefully see you tomorrow." Derrick chuckled as he left Jessie's room.

Once she was alone, Jessie couldn't help but release the sexual tension that had been building inside of her all night. Once it had been released in an explosive orgasm, Jessie fell asleep quickly, without even getting dressed for bed.