Sydney’s Pajamas Pt. 01

Last weekend was my brother's birthday. He lives an hour away from me with his little family of three, so I decided to spend the weekend at his house. Their only daughter's name is Sydney, and she's almost nineteen. I drove down friday with plans to head home Sunday. The party was on Saturday, so the plan was to have dinner and watch a movie Friday. They always did movie nights on Friday and I was happy to join their crew.

My sister-in-law, Jade, made a delicious Italian dinner, and after eating far too much lasagna and tiramisu I was ready to lounge. I plopped down on a recliner, but my niece stopped me before I got settled.

"That's dad's spot, uncle Jack!"

I sighed dramatically and cracked a smile before slowly standing up.

"My apologies, Syd. Are there any open seats left or is it standing room only?"

"Well, there's one available seat, but it's in the V.I.P. area so it'll cost you extra this close to showtime!"

"Oh yeah? How much? And where is this expensive seat located?"

Her light green eyes sparkled as she held back her laughter.

"The seat is on the chaise lounge next to your favorite person in the world. And it costs, umm, after fees and everything...200 dollars!"

"Wow," I said to her, pretending to actually consider her silly proposal.

"I spent 200 bucks on a V.I.P. seat a couple months ago in Vegas at Robby's bachelor party, but that included drinks and a lap dance! Can I at least expect a back massage if I pay for the spot?"

"Oh my gosh, uncle Jack! I suppose I could give you a back rub if that's what you want. The show starts in 30 minutes! I'm going to put my pajamas on. Don't be late!"

She turned and walked out of the den. I thought back to that night. Robby is my best friend. We were at the Palomino Club. I stretched the truth when telling my niece how much I spent. It actually cost $800 just to get a bottle of Don Julio 1942 and our own V.I.P. booth near the stage.

I walked to the bedroom I was staying in to get my stuff organized and put on some comfortable clothes. I'd packed my favorite pajamas. They are soft cotton tapered pants with red and white stripes. They look ridiculous, but they are the most comfortable item of clothing I own. The whole family got matching sets two years ago for Christmas from my parents. I changed into the pants, put an old t-shirt on, and put my other clothes away in the dresser.

There were some random clothing items already in there, including a set of pajamas that match mine. There was a matching top for them too. I looked at the tag and saw size XS. The top was definitely too small to belong to my sister-in-law, so I determined they were Sydney's. I thought it would be fun to wear matching pajamas, so I walked across the basement to Syd's room and knocked.

She opened the door wearing just her leggings and a black and white Calvin Klein bra. I held the red and white pajamas out to her.

"Wanna be twins?"

She laughed and took them from me.

"I grew out of these two years ago!"

I pretended to think hard about something.

"Jeez, I guess I'll just keep my $200 then. This doesn't seem very V.I.P."

"If you actually give me $200, you are more than welcome to pick my outfit for me. But I know you won't."

I pulled out my phone and sent her $200 on Venmo. She got the notification and her jaw dropped.

"Looks like we will be matching!"

"I guess we will, uncle Jack!"

When she emerged from her bedroom five minutes later I was in awe. Sydney's pajamas were practically painted on. I could see the outline of her mound and her distinct camel toe. Her breasts barely fit inside the top, either. I followed her over to the small couch and got under the covers with her.

"Do you like the pajamas?" she asked me quietly.

I just put my hand right on her plump mound and began rubbing her. I slid my hand inside her pajamas and my fingers felt her soaking wet pussy for the first time. She just stared at me as I traced up and down her slit and slowly dipped my middle finger inside her. The rest of the family was still upstairs and I made a bold decision. I picked Sydney up and carried her to the bedroom I was staying in. I laid her down on the bed and immediately pulled her pants off. Her puffy hairless pussy was wide open as I spread her legs apart. I buried my face in between her legs and sucked on her clit as I fingered her aggressively. I didn't have much time to waste, so I stood up and dropped my pants. My rock hard cock was pointing straight out as we made eye contact.

"Are you going to fuck me?"

I just nodded my head and lined myself up. She gasped as I entered her and I put my hand over her mouth and shoved my cock deep inside her. She closed her eyes as i fucked her tight little cunt. I lifted her up and turned her around on all fours. Her inner labia protruded out like flower petals. I once again ate her out, giving some extra attention to her ass hole. She twitched as my tongue first licked her there, but soon she was moaning as I went back to licking her pussy. I dipped my thumb in her ass hole as I got on my knees. With just a little bit of resistance, I was a knuckle deep in her ass as I put my cock back inside her soaking pussy.

I bucked her aggressively while fingering her butt. She was so wet that my fingers easily slid inside her ass. Her face was buried in the pillow when I pulled out and put my tip against her bum. She gasped again as I slowly drove my cock inside. We slowly got into a rhythm and I was balls deep in her 18 year old ass. I couldn't control myself any longer. I don't know why I did it, but I pulled out and stuck my dick back inside her perfect little pussy. I felt my cock spasm inside her. My moment of pure ecstasy lasted barely a second, though.

There were three knocks on the bedroom door. I came ropes inside her as I heard my brother outside the door.

"Are you almost ready?"

"I'm coming!" I replied.

And I still was. I drained myself inside Sydney's pussy. She let out a sigh of satisfaction as she looked back at me.

"Oh my god!" she said in almost a whisper.

I was still inside her as I heard my brother again.

"Is Sydney in there with you?"

"I'll be out in a minute, daddy!" she said.

We both fumbled around to get our clothes back on. When we finally walked back out to the den the family was all ready to go in their seats by the tv. I saw my brothers eyes glance down to Sydney's cameltoe and I was thankful the room was mostly dark. We sat down on the love seat and she draped a leg over my lap and covered us with the blanket.

"Those PJs are pretty small for you, Syd."

My brother looked over at us. Sydney replied matter-of-fairly.

"Uncle Jack picked them out for me."

I chimed in right away.

"We wanted to match!" I chuckled to hide my fear and discomfort.

"Show your mom what you're wearing."

"Ok, daddy."

Syd stood up and my sister-in-law flicked on the lamp. As she stood in the light it was easy to see the entire outline of her labia and gash. I felt myself getting hard again. She stood in front of her dad and I watched as my brother reached out and pulled her towards him and told her to bend over. My cock was rock hard as she laid her butt up on his lap. He spanked her three times before pulling the waistband down revealing her bare ass.

"You need to go out some panties on and wear clothes that fit you."

He spanked her one more time before letting her go. She didn't make an effort to cover herself right away, and as she stood up everyone got a clear look at her naked butt and bare pussy. Her inner labia poked out and her engorged clit was poking out and glistening with moisture. As she walked towards her room, my brother stopped her.

"Just sit down and watch the movie. Good thing it's just family here. Next time dress decently or we will have problems."

"Yes, daddy."

She sat down beside me again. My dad flicked the light off and started the movie.

I finally was beginning to relax when Sydney spoke up.

"Uncle Jack likes these pants, daddy."

I was in shock. My brother looked at me and Syd. He was trying to figure out what she was talking about. I slowly removed my hand from her cunt as she blurted it out.

"Right, uncle Jack?"

Before I could come up with any reasonable reply to her question, she found my cock with her hand and gripped my shaft over my pants.

"Uncle Jack fucked me, daddy."

My brother and I stared at each other. At first I was terrified, until he just sighed.

"Isn't she fucking irresistible?" My brother asked. Before I could answer Jade asked Sydney, "Does he have a nice dick babe?"

In a flash the covers were off, my pants were at my ankles, and Jade was fingering herself as my niece tried to take my cock in her mouth. I looked at my brother and he just shrugged.

"Out of the way, baby. Mommy's turn. Jade stripped naked and walked over to straddle me, taking my entire 8 inches inside of her trimmed but hairy cunt. She was bouncing up and down so much it began to hurt. My brother once again spoke up.

"Fuck my wife in her ass!"

As Jade adjusted herself and I felt her warm hole take my cock inside, I glanced at Sydney. She was vigorously fingering her pussy. I looked at my brother. Nothing but stares from him.

"Aren't you going to fuck her?," I asked him almost nonchalantly given the circumstances.

To be continued...