Sylvester's Family Tales 36

Story by Ragemend on SoFurry

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#35 of Sylvester's Family Tales

Sylvester and Jamie go to visit Sylvester's parents, but Jamie agreed to cross dress for the trip.


"I can't believe I let you convince me to do this." Lamented Jamie.

Sylvester and Jamie waited Friday afternoon on the same curb that Sylvester always met his parents for a ride home. However, instead of a quiet weekend at home supplemented with intimacy from his brother or father, it was going to be a busy weekend home with Jamie. And, as a special perk with a promise of no one noticing it, Jamie agreed to dress as a girl for the entire trip.

"Are you sure no one will recognize me?" Asked Jamie, starting off the weekend in skinny jeans that showed off his butt, a women's hoodie to hide his lack of a chest, and a floral headband.

"I can almost guarantee it." Smiled Sylvester, waving at his mother as she pulled up.

The pair got into the back seat of Sylvester's mother's car after loading their bags into the trunk. Jamie blushed, whether or not they convinced Sylvester's mother was the first test to see if he could pass for feminine.

"Hi, mom. This is Jamie." Said Sylvester.

"Well aren't you a cute little thing." Responded Sylvester's mom, sweetly.

"Nice to meet you, Mrs. Pussycat." Said Jamie, uneasily.

"She's polite too, you've finally found yourself a nice girlfriend, son." Giggled Mrs. Pussycat.

Jamie was too relieved that he passed as female to worry about Mrs. Pussycat's "girlfriend" comment. This left Sylvester to hastily correct his mother on the subject.

"She's not my girlfriend. She's just a friend, mom." Assured Sylvester.

"Well, friend or not you're sleeping on the couch and she can have your bed. You're at that age where you're too old to be sharing a room with a girl." Smirked Mrs. Pussycat.

"Mom..." Blushed Sylvester.

However, Jamie wasn't paying attention, and missed that comment from Sylvester's mom. He was too busy watching the world go by as they drove, far away from anyone who could catch him in such an embarrassing outfit. When Sylvester told him people would be too busy with class to catch him in skinny jeans, a hoodie, and a floral headband he almost didn't believe the cat. But, he was right, no one saw.

"We should find a way to thank Blaire for letting us borrow her clothes." Whispered Jamie to Sylvester.

"We'll buy her some salt water taffy while we're home. Denise said Blaire loves the stuff." Whispered Sylvester.

"Whispering to each other in the back? You're not doing to well at convincing me you're not a couple, son." Grinned Mrs. Pussycat, looking at them from the rearview mirror.

"We're just talking about some friends from volleyball, mom." Groaned Sylvester.

Jamie blushed again, and didn't whisper to Sylvester anymore. He stayed quiet for the rest of the trip to avoid Sylvester's mom thinking that they were a couple. He watched the trees go by from his back seat window. Their small college town gave way to a nice city skyline as they drove around Lillidale to get to the decently sized town that the Pussycats resided in.

"Have you ever been to Lillidale?" Asked Jamie to Sylvester, breaking the silence that had overtaken the car.

"A few times, my older brother goes to school there." Responded Sylvester.

"Oh, right. His name is Tom, right?" Asked Jamie, hoping to keep away from topics that Mrs. Pussycat could turn into ribbing about them being a couple.

"Yeah, I guess I forgot to introduce you when he visited before." Replied Sylvester.

That was it for car talk. Sylvester seemed afraid to look at Jamie, lest he encourage more embarrassing comments from his mother. That was fine with Jamie, less talk meant less of a chance his voice would give away his true gender. After they got to the Pussycat household Sylvester quickly dropped off their bags in his and Tom's room. Jamie went into their bags and pulled out a miniskirt.

"Do I really have to wear this?" Asked Jamie to Sylvester.

"Well, no. You just do what you're comfortable with, but I think that you might enjoy it." Responded Sylvester.

"I'll go change in the bathroom and we can go out and grab dinner." Said Jamie.

Sylvester nodded and went to find his father. After checking his parents' bedroom and the computer room he found his chubby father watching TV. The jovial man got up and hugged his son.

"Your mother says you brought your girlfriend back with you." Grinned Pops.

"She's not my girlfriend, dad. She's just a friend." Groaned Sylvester.

"Well, I hope she likes your mother's pot roast." Chuckled Pops.

"We're actually going out to eat... I was hoping we could borrow your car." Replied Sylvester.

Pops dug into his pocket and pulled out his keys, placing them in Sylvester's paws. Sylvester hugged his father again and went to find Jamie. When he did he was left speechless. Jamie looked amazing in the camisole and skirt that Blaire had lent him. Before he managed to speak Jamie hurried over to him and whispered in his ear.

"Are you sure this looks okay?" Asked Jamie.

"A-amazing." Blushed Sylvester.

"Okay, let's go get something to eat, then. I'm starving." Smiled Jamie, the weight of his appearance off his shoulders.

Jamie and Sylvester quickly left the Pussycat household, avoiding the kitchen to keep away from Mrs. Pussycat trying to get them to stay or making more girlfriend comments. Once they got into Pops' car they drove off, going to a fast food place for a quick stop. After parking, they went inside and got on line, the restaurant smelled like french fries, not that either of them minded. When it was Jamie's turn in line the teenage cashier took notice.

"Well hey there, cutie. What can I get you?" Said the cashier.

"I-I'll have a veggie burger, a large fries, and a soda." Stammered Jamie, not used to being called "cutie."

"And I'll have a hamburger, a medium fries, and a sweet tea. It's all to go" Said Sylvester, walking up behind Jamie.

"Okay, that will be $11.26. If you'll please take a seat your food will be right out." Said the cashier, losing his flirty attitude after assuming that Sylvester was the cute mouse girl's boyfriend.

"He called me cutie..." Blushed Jamie, sitting down with Sylvester.

"You are cute." Smiled Sylvester

They waited for a few minutes and the same cashier brought them their food, winking at Jamie as they got up and left. They got back into the car and drove out of town, up to an overlook that showed Lillidale in the distance, the city lights piercing the evening sky. They quietly ate, enjoying their food and each other's company. Once they were done eating Jamie broke the silence.

"Sylvester, I have a confession to make..." Started Jamie.

"Dressing like that really turns you on?" Guessed Sylvester.

"How did you know that!?" Gasped Jamie.

"I can smell you getting turned on, I've smelled it since we got in the car." Chuckled Sylvester.

"Care to do anything about it?" Asked Jamie.

Sylvester grinned at Jamie and climbed into the back seat of the car, motioning for Jamie to follow him. He laid back on the seats while Jamie straddled him. Sylvester quickly pulled down his pants and underwear while Jamie pushed his damp panties to one side. He let his dripping pussy rest against Sylvester's hard length, rubbing himself against the cat's uncut cock. After a minute of teasing Jamie couldn't take anymore and shifted his weight, letting Sylvester's cock stand at attention before sliding down on it. Jamie let out a contented sigh as Sylvester's cock penetrated him. Sylvester put his paws on Jamie's hips and started to thrust into him.

"It's amazing how wet a little crossdressing can make you." Marveled Sylvester.

"It's amazing how well you can push my buttons when we fuck." Grinned Jamie, starting to bounce on Sylvester's lap.

"Like this one?" Asked Sylvester, shifting one paw from Jamie's hips to his clit.

"Fffffuck." Whined Jamie when Sylvester's paw rubbed against his clit.

Sylvester fucked into Jamie and teased him, the mouse knew he wouldn't last much longer at this rate. Just as he was reaching the precipice of his orgasm Sylvester let out a loud grunt and shoved himself deep inside of Jamie's cunt. Jamie felt Sylvester's load surge out into his depths and reached his peak, clenching around Sylvester's throbbing cock as he came. They both moaned loudly as they came, with Jamie soaking Sylvester's lap and the car seats and Sylvester spurting a thick load deep inside of his lover. They kept their position until they both were done cumming, but after Jamie slid off Sylvester's length and put his panties back in place to catch the incoming feline seed.

"I think I'm going to have to do laundry at your place, Sylvester." Panted Jamie.

"I think those panties are mine now, and I don't think you should wash them." Replied Sylvester.

"Why not?" Asked Jamie as he climbed back into the front seat.

"Because I want them, mess and all." Smirked Sylvester, getting dressed and climbing back to the driver seat.

"Well, they're yours then." Giggled Jamie.

They drove back to Sylvester's house with all the windows open to air out the smell of sex and got home around 11 pm. Sylvester and Jamie trudged back inside. Sylvester walked Jamie to his room but remembered what his mother said and bid him goodnight at the door, walking back to the living room to crash on the couch. However, Pops was waiting for him.

"Have a nice night, son?" Asked Pops, a goofy grin on his face.

"Yeah, dad. Thanks for letting us borrow your cat." Replied Sylvester.

"Did you clean up after yourselves?" Asked Pops.

"Yeah, we aired the car out too." Responded Sylvester, wanting nothing more than to crash on the couch.

"Good boy, I'll see you in the morning." Said Pops, getting up to go to bed.

"Night, dad." Said Sylvester, waving goodnight to his dad.

Sylvester didn't bother undressing, he just flopped on the couch and fell fast asleep. He was thankful to have understanding parents, even if they did make a few too many girlfriend jokes at his expense.