Paulina is heard Masturbating
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This is a work of fiction. The characters exist solely in my head. And, well, here too.
If you haven't read the other stories about Paulina's adventures, please do so, as they will offer some background and context. The collection can be found here:
https://www.nifty.org/nifty/transgender/teen/paulina/
I suggest reading "Paulina -- An Introduction" first of course. More stories will be added as they are ready.
Please let me know what you think. I have received wonderful feedback on my other stories. Email me at deviantigusti@yahoo.com. If you have criticism, please be constructive.
Here are the main characters: Paulina: 15, crossdressing boy. Pretty, Italian looks. Dawn, Shawn: Early 30's. Parent's friends Paulina is closest to. Joe (Pervert): Early 30's. Another long time family friend. Marie: Paulina's mother Hank: Paulina's stepdad
The anticipation of the trip to see my parent's friends Mary Sue and Big Jim for some fun in the country the coming Saturday was very exciting, to the point that I knew I wouldn't be able to sleep without some help. It was about 11 pm on Thursday night and I didn't want to be awake all night because I had school in the morning. I knew that both my mother and stepdad would have a drink or two before going to bed sometimes. I guess it calmed them down. I would have to be very stealthy to be able to make one unseen on a week night, so I dismissed that idea. Something else might work better. I decided to go out and see who was in the living room. I was already wearing my favorite baby blue tank top, so I put on the tight blue nylon gym shorts that my girl Delaware had picked out for me a few weeks before...
My stepdad, Shawn, Dawn and Pervert were sitting on the sofa watching TV. They all looked a little high. Thankfully, my mother was nowhere to be seen.
"Hi y'all" I said cheerfully.
"Hey, how's it going?" my stepdad replied.
"Good, I guess. I have a question. I'm gonna try to go to sleep later, but I'm wide awake and that's probably not gonna change by itself. I really want to get some rest. Um, do y'all know anything that'll help?"
"Sure man, take a `lude (Quaalude)" Pervert answered matter-of-factly.
"Don't tell her that! She's fifteen, so she can't. Paulina, pretend you didn't hear that!" Dawn replied before anyone else.
My stepdad threw him a disapproving look. "Not cool, man."
"If you were older, I'd say share a joint with us, but you're not, so you can't" Shawn added.
"No, y'all, I definitely don't want to do THAT! Smoking that sounds yuck!" I made a face, at which everyone chuckled.
"I guess we don't have to worry about you becoming a pothead, huh?" my stepdad laughed.
"No, I don't think I will. But I heard you can put that in brownies? Does it taste good?"
"Maybe when you're older, I'll make you some." Dawn patted my shoulder.
"So, any other ideas? I don't wanna stay up all night. When I can't sleep, it lasts for hours. The other night I didn't fall asleep till three o'clock!"
"Kiddo, you can't be staying up that late. It's not good for you."
"Well I don't do it on purpose" I said with a little pout.
"I know, but still. Maybe there's something that'll help."
"Don't drink any Coke, man. Caffeine and sugar won't help." Pervert raised his bottle to me.
"Hey, I might know. You remember when I was having allergy problems?" Shawn asked Dawn. "You gave me some Benadryl. A little while after I took it I was knocked out. Maybe try that?"
"Yeah, that's right. Nyquil might work, too." She replied.
"Cool. I'll see if we have any."
.
I stretched my arms above my head and arched my back a little, which caused a few pops and cracks that everyone heard.
"You alright? That didn't sound good" My stepdad asked with a little concern.
I twisted my neck, causing another pop.
"I'm just stiff and sore. Sorry."
"Come see. You need your neck and back rubbed." Dawn patted the ground in front of her.
"Okay." I sat down in front of her. I wasn't going to pass up an adult touching me.
She started kneading my neck and shoulders. It felt good immediately.
"Oh, that's nice" I said sweetly.
"You have some knots in here. That's probably why you're sore. I'll try to work them out."
I leaned back a little closer to her as she worked on my shoulders. It felt like her hands were not quite strong enough to smooth them out though.
"These are too much for me. Shawn, rub these out for her."
"K. Come here and sit."
I got up and moved in front of him. I sat cross-legged in front of him scooting my butt against his legs.
His strong hands began working on my neck and shoulders, attacking the knots as he felt them.
"Damn girl, you're all knotted up."
"I know. I've been really sore."
As he rubbed, he kept pushing the straps of my baby blue tank top out of the way. It was aggravating, so I pulled it off.
He stopped rubbing me for a moment. I looked to see everyone looking at me.
"What? It was getting in the way."
"Um..." Shawn sounded very unsure.
I turned around so that everyone could see me. My nipples were hard since Shawn had been touching me.
"Look y'all" I pointed at my chest, "Nothing y'all haven't seen before." I gave them both a little pinch, surprising everyone.
"But Paulina, when you look cute like you do, you shouldn't be taking your top off in front of guys." Dawn said sweetly.
"But I know y'all. I don't mind if y'all see me. I don't take my clothes off in public. I know not to do that."
"Good. I don't want you doing that in front of strangers" my stepdad added protectively.
"I won't. Rub please?" I gave Shawn a sweet look as I tapped a shoulder.
"Okay." He resumed his rubbing. Working out each knot, it felt better as he went.
"Mmm, that feels so good, Shawn!" I leaned back into him a little.
"Glad it's helping."
His hands were slowly moving lower down my back until he realized what he was doing, and quickly brought them back up to my shoulders. He wasn't massaging Dawn.
I let out a quiet `uwhh' of disappointment when he moved back up to my neck and upper back, which I'm sure he heard.
"Alright, you're done. How does that feel?" He asked.
"That was wonderful. You're the best, Shawn. Thanks!" I turned around and gave him a big, close hug, making sure he could feel my hard nipples against his chest before putting my tank top back on.
"Anytime, P." he ruffled my hair before I got up.
I couldn't help but notice Pervert eyeing my hard nipples. I caught his eye and gave him a big wink as I pinched one of them. He subtly stroked the Coke bottle between his legs.
"Alright y'all, I'm gonna try the cold medicine and see if it helps me go to sleep." I got up and blew everyone a kiss goodnight. They all gave me a little wave back.
Shawn gave Pervert a little punch in the leg after I was gone.
"Dude, you can't tell a kid to take `ludes! Not cool, man."
"I was just jokin'" he replied with a straight face, but no one was buying it.
"Save that for some chicks whose pants you're actually tryin' to get into" my stepdad told him with a chuckle.
"Now that's not cool!" Dawn playfully scolded as she hit him in the knee.
They all laughed a little before rolling another joint.
I looked in the medicine cabinet and found both Benadryl and Nyquil. Since I really wanted to sleep later, I took both. But I knew what else would help. I wet a washcloth and brought it back to my room with me.
Locking my door behind me, I stripped out of my clothes. Laying a towel on the bed, I set the washcloth on the nightstand and took out my toy and a tube of KY I took from my parent's bathroom. The toy used to be the end of a wooden pole like one that would be in a closet to hang clothes on. It was nine inches long and about six inches around, which made it about two inches wide. One end was flat where it had been cut off the pole, but the other end was rounded to the tip. It looked like a hard, uncut dick but without the foreskin pulled back.
Lying on the towel, I spread my legs and lubed my fingers with the KY, making sure to get a big dollop on my fingertips. I then pushed the lube inside my tight hole. Satisfied that I inserted enough, I started to finger myself with one hand while I stroked my big clit with the other. Once I was able to take three fingers comfortably, I grabbed my toy to really fuck myself.
The toy was big, but I played with it often and knew I had to work it in slowly. Starting with the tip, I pushed it in about a half inch at a time. As it always did, the first push hurt. It felt like my ass was on fire just inside the rim. It was painful but felt good. I waited a minute for the pain to subside and then pushed it in again. The more I did it, the less it hurt and the more it felt good. Going deeper with every stroke, I slowly pumped it in and out. I could feel the hard tip push against my prostate, that sweet spot inside. As I fucked myself, I replayed in my mind Bernard's big cock stretching my little ass open. I was trying to be quiet but could not totally hold the sounds of my pleasure in. I sounded like a woman who was getting fucked well. I was hitting that sweet spot on every thrust now and couldn't hold back any longer. I sped up the thrusts and stroked my big clit at the same time until I came. It was like an explosion inside, making me shake with pleasure. I cried out, not able to hold it in. "Ohh...ohh...unh...unh...ahh...unh...ahh...uhn...ahh...omygod! omygod! omygod!...AHHH...AIIIEEEAHHH! UNNNNHHHHHH! AHHHHHH! OHHHHHH!"
As the wave of pleasure inside crested, I squeezed my ass hard around the wooden cock up my ass. My big clit and balls clinched up at the same time, then released a burst of cum, which shot to the end of the bed. Each time I clinched, a small shot of cum came out. The feelings were so intense that I thought I was going to pass out.
As my orgasm subsided, my ass began to relax, releasing the vise-like grip on the toy inside. I clinched my muscles a few times more to get all I could out of my orgasm. As I slowly pulled the rod out of my ass, the last bit of cum dribbled out of the head of my big clit. I brought it to my nose and inhaled the scent. It was strong and musky and familiar; the smell of my sex. The rod was now covered with the creamy film of my boy pussy juice. I licked it clean, tasting the savory film.
Having had such an intense release, my tension and energy seemed to evaporate with each breath as my heart rate and breathing slowed down back to normal. Without getting up, I wiped myself and the toy clean with the washcloth. I put the rod back in the drawer as I felt my eyes slowly closing. Pulling the sheet over me, I closed them and fell fast asleep.
In the living room, everyone was relaxing around the coffee table when their ears perked up.
"Hey, quiet. Y'all hear that?" Shawn asked.
"Yeah. Sounds like a chick gettin' fucked good and hard" Pervert added with a sly tone.
"Is...is that...Paulina?!? No one else is here, right?"
"No, so that's gotta be her" my stepdad replied in a low voice.
"Oh...she's loud" Dawn said as she cocked her head to listen.
"Ohh...ohh...unh...unh...ahh...unh...ahh...uhn...ahh...omygod! omygod! omygod!...ahhh...aiieeeahhh! Uunnnnhhhhhh! Ahhhhhh! Ohhhhhh!" could be heard coming from my room.
"Wow...that sounded intense. Um, that sounds like she's getting fucked. That's not just jerking off."
They all sat silent for a few moments as they each imagined how I would look, picturing me on my back, or bent over on my knees with my ass up as I got fucked. The guys tried not to be obvious as they adjusted themselves while Dawn discreetly slid a hand between her legs and gave her crotch a couple of rubs.
"Sounds like she might have gotten Marie's sex drive" Pervert said with a little smirk. Everyone gave him a dirty look.
He kept a straight face. "What? All I'm sayin' is that she's hot blooded like her mom."
"If she was a real girl, I'd say get her on some birth control. The sooner the better. I guess it's good that we don't need to worry about that." Dawn tried to sound positive.
"Yeah..." My stepdad never expected to be faced with me being physically sexual so soon. He hoped I would just stay cute and sweet and flirty for as long as possible. Of course he knew that it was just a parent's dream. After hearing me fuck myself to such an intense orgasm, his image of me changed, and he knew it couldn't go back.
"Well, cumming like that'll definitely put her to sleep" Pervert added.