Her First Halloween Ch. 02

"Oh my god, wtf is happening," I think to myself as I'm now on my knees in his bedroom next to Karla, staring at Andrew's crotch right in my face.

"Okay, David, I'm going to show you how it's done. Don't be nervous."

I'm open mouthed staring in surprise as Karla pulls down Andrew's pants and his dick pops out fully erect. It was big. Much bigger than mine. Easily over 7 inches and inches away from my open mouth.

I'm frozen. I don't know what to do. I've never thought about being with another man before but dressed like this, especially in the pink thong still moist from Karla's use, I couldn't help but feel horny.

"Go ahead, Jenny, just give it a little kiss like this," she says as she leans over and gives it a juicy kiss right on the tip. I feel a sense of relief as she calls me by a different name. Andrew seemed really drunk and I'm hopeful he doesn't think it's his best friend down on his knees dressed like a slut.

Still, I'm frozen but Karla eases my face towards his dick and my lips are pressed against his head. I don't fight it and just accept it as I give his head a light peck.

"Oh come on kiss it like you mean it!" Karla says. I gulp and give his dick the same juicy kiss Karla gave it.

"Good now I'll show you how to really get him going."

Karla then takes his dick in her mouth and goes to town. Sucking vehemently and I start dripping pre cum into my thong as i watch this happen literally in front of my eyes. After a minute or so she says "Okay, now you know how it's done, so you try."

This time she doesn't give me a chance to think about it as she shoves my open mouthed face toward his dick. I try to take it all the way in, but I start to gag. This was a lot harder than it looked, and I could only fit about half of it in my mouth before needing air. Karla tells me to relax my throat and I do. Eventually I'm getting the hang of it and I try my best to deep throat it like she did. Her advice helped and after a few minutes, with some assistance from Andrew pushing down on the back of my head, I was able to take all of it in. The taste was musky but not nearly as bad as I thought. I never thought of myself as gay but I was really starting to enjoy this. I was rock hard in my panties, as I started to go at it with the same tenacity Karla did beforehand. A nervousness was starting to overcome me, though. Andrew was really getting worked up and I was afraid he may cum.

Andrew confirms my suspicions as he says, "Karla I can't hold on any longer we gotta do this now."

"Go ahead, baby."

I've watched enough porn to know where this is going and I brace myself for a mouth full. He suddenly pulls out of my mouth. I'm expecting a facial but he grabs me by my arm and drags me toward his bed. He sets me up on all fours, lifts up my short dress, and grabs my dick through my panties.

"Oh yeah, David, I always knew you were a little weird. Thank Karla here for helping you let your inner girl out. It was all her idea. She's been saying for a long time now you were a sissy on the inside and that you would love this. I was very hesitant to agree with her at first. We've known each other for years and you've never tried to pull a move on me before. I mean I always knew you were a bit different and shy around girls, but I never thought you actually wanted to be one. I guess it takes a girl to know a girl."

I can't believe my ears and I'm filled with embarrassment and shock. Andrew knows and he isn't nearly as drunk as I thought he was. They planned the whole thing and there's no way I would ever be able to live this down. How would I go back to normal life? The heels and silicone breasts are all starting to make sense. This was premeditated. I stare at Karla with tears in my eyes as she smiles. How could she do this to me? And more importantly, how did she know? Andrew then pulls the thong out of my ass and to the side as he starts lining up his dick.

"No, Karla, Andrew, I can't do this. I didn't want to dress up like this, Karla just convinced me and I was so drunk I couldn't say no. Please, Andrew, stop this. I've never done something like this before. I really don't want to."

Karla puts her finger to my lip and says, "Hush, now, little Jenny." Tears start to well up in my eyes. I guess Jenny was my name for tonight, and this was really about to happen. "You are going to love this believe me. Andrew will go slow and make sure your enjoy your first time."

My first time. I'm now realizing this is my first time ever having sex. And instead of me fucking a girl, I was getting fucked like a girl. I start sweating and practically hyperventilating, but before I can get my thoughts together he works the head of his dick into my hole.

"Ohhhhh!" I scream.

It hurts but my dick is rock hard. I try to pull away but Karla ensures me it's fine and to relax. I do as she says and Andrew continues inserting his member into me. He eventually works it all the way in and I scream again in both pleasure and pain.

"You love it don't you David?" Karla says. I can't answer as the pressure in my ass is making it hard for me to think, but I am. I'm loving this. The fullness, is making me super hard and I scream out again in euphoric ecstasy as I feel his tip reach my prostate.

Andrew starts really going to town on me now. Going in and out at a steady pace and I can't help but moan out in pleasure.

"Oh I knew, it! You are loving this! Come on let the screams out. Let ur inner girl inside you yell out in pleasure as your best friend fills you up with his giant cock," Karla says. Those words send me over the edge as I start rocking back into him meeting his movements.

"Yes, Andrew! Fill me up! Make me feel like a woman!"

"Don't call him, Andrew, call him Daddy."

He's still laying into me with everything he's got. I feel his balls smacking against my balls each time his member goes fully inside me. I'm practically drooling and I can barely say anything.

"Say it, David! Say fill me up with your seed, Daddy!"

"FILL ME UP WITH YOUR SEED, DADDY!"

"Make me the sissy I am, Daddy!"

"MAKE ME THE SISSY I AM, DADDY!"

This was all becoming way too much to handle. My asshole was literally quivering and both my legs were shaking. I couldn't hold back anymore as I scream, "YES, YES, YESSSSSSSS!" as I start cumming into the thong Karla gave me. As I cum Andrew rumbles and groans as he unloads his seed inside me. I collapse on the bed, trying to catch my breath. Andrew releases his cock from my ass. The cum starts to drip out as Karla fixes my thong back into place, stands me up, and straightens out my dress.

Andrew is passed out on his bed and Karla leads me out of the room as I'm still struggling to get my mind over what just happened. I had fucked my best friend. Actually, no. My best friend fucked me. My legs were weak but I managed to get my bearings and walk out of the room with Karla.

"Wait, Karla, where are we going? What just happened? What about Andrew?" I say as I look at the clock. It's nearly 9:00! The Uber was for sure gone and now there was no way we'd make it to the club. I feel slightly relieved as I was having second thoughts about every thing after I had my release.

She looks out the window and says, "Uber's gone but that makes sense. We were in there for quite a while. No worries though, we can just call another one. Slight change of plans though, we're going to Cherry's house to meet up with the girls, first."

I freeze. Cherry's house? She was our friend from high school and I hadn't seen her in years, but we were pretty close back in the day.

"Who's gonna be there?"

"You know, all the girlies!"

Thoughts are running in my head wildly. All of them? I hadn't seen any of them in a while but we all hung out fairly often in the past.

"I don't know Karla I really don't want to go out in public like this. I'm a mess right now and I feel like I may be leaking," I say as I feel cum dripping out of my ass into the skinny fabric of the thong between my ass.

I feel a strong hand on my shoulder and turn around to see Andrew's dad. His huge hand gripping my shoulder tight. I'm frozen again and I stare into his eyes.

"Karla, you and your friend here aren't going anywhere till I'm done with this little thing."

I gulp. Oh my god, his parents were home? How much did he hear? I wasn't exactly quiet in there.

Andrew's dad sits down on the couch, bends me over his leg, and lifts up my dress up. He pulls my thong to the side in disgust. "Really you slut, you couldn't clean up after yourself? You like the way it feels in there don't you? Filthy little whore. That's fine I guess but I can't have you leaking all over my floor. Karla, do you have anything for this?"

Karla happily says yes and pulls a butt plug out of her purse. I look and I can just barely see how big it is. I want to say it's about 5 inches with a decent width, he takes it from Karla and shoves it into my ass.

"There you go. It's a nice fit." He then smacks my ass real hard. My ass stung as he leaves his hand there and starts rubbing it. "Okay let's go over some rules. In the future, whenever you're in my house you will be plugged up at all times. Got it?"

I don't know how to answer. I was trying to convince myself this was a one night thing, but now I'm not so sure anymore. Before I could answer he smacks my ass real hard for a second time. "I said got it?!"

"Yes!" I say, but that wasn't good enough as he smacks my ass again which makes me moan. Am I really enjoying this?

"That's yes, SIR, to you!"

"YES, SIR!"

I tell him what he wants to hear, but I don't plan on going through with it. He doesn't realize it's me. He never saw me arrive. He probably thinks I'm just one of Karla's slutty friends.

"Good girl. Secondly, you are to dress this way from now on whenever you visit, Andrew. You got that... David?"

I froze. He knows it's me. I'm in full on panic mode. Not only is Andrew's dad aware of me dressing up but is demanding I keep it up past Halloween. Another hard slap on the ass wakes me up and I can't do anything but say, "Yes, sir."

"Good girl." He massages my ass for a bit, then reaches around my thighs to the front of my panties and places his hand on my cock.

"Oh my god, did the fucking my son put on you really make you cum into your sissy panties?!" He reaches inside and scoops up all the cum he could get and forces it into my mouth.

"A sissy like you should always clean up her messes. Isn't that right, Karla?"

"Absolutely, sir!" Karlas exclaims. "How is it, Jenny? Good, right?"

"Yes," I say with a mouthful of my own cum. Surprisingly, the taste wasn't bad at all. The consistency was a little weird, but I actually enjoyed the taste. Andrew's dad seemed to notice I didn't put up much a fight with that one.

"I knew a sissy like you would like that." He pulls my thong back over my dick and up my ass giving me an even bigger wedgie. "And keep wearing the thongs. They suit you."

One more smack on the ass and he lets me go. "Okay, you girls have fun now."

I slowly get up. Getting used to walking with the plug in me. It's a foreign feeling, but one that is keeping me in a constant state of arousal if I'm being honest.

Deep down, I was loving everything that was happening to me, but I couldn't admit it. There was this part of my brain telling me I shouldn't like dressing up and that hooking up with Andrew was wrong. I can't hook up with guys. I'm not gay! Plus, I hang out with Andrew all the time! Now every time I'm over his house I have to dress like a slut? Where would I even change into the clothes? I couldn't leave my house dressed in an outfit like this for my parents to see. I try to put my foot down.

"Karla, there's no way I can wear this stuff in the future. I'm a straight man for crying out loud!"

"Don't talk like that! When your dressed like this you're no longer, David, you're Jenny, and it's not gay. In fact, your not even a man. In that outfit you're all woman! And a very pretty woman at that! So quit whining and worrying about being gay!"

What she was saying sort of made sense. "But, Karla, how can I dress like this all the time? You heard what his father said. I have to enter the house dressed like this and I don't have any other clothes!"

"Oh stop it with those excuses. Don't worry, I'll let you borrow some of mine until we can go get you some more." Her phone dings with a notification. "Awesome, the Uber's here! And, Jenny, don't worry, practically all I own are thongs so you'll be good in that department," she says as she smacks my ass and before I know it we're out the door.