Her First Halloween Ch. 03

The Uber drops us off and we arrive at Cherry's house. The outside air creeps up my super short dress and it feels heavenly. Walking towards the door, the bottom of my dress flows in the wind, revealing my panties to any passerby in the area. Luckily there are none, but the breeze on my bare legs and ass has a magical effect on me. I was really enjoying dressing up like this but the events at Andrew's house were constantly on my mind. My ass was aching from the fucking he put on me, and his father demanding me to be plugged and dressed like a slut from here on out! Karla calmed me down a bit before we left but I was still freaking out. I don't know what I got myself into or how I'll get myself out of it.

I walk inside and I'm greeted by Annie, one of my old friends. She was beautiful. About my height, but with the legs of a model and a gorgeous physique. She hugs me and says I look absolutely beautiful. She could hardly tell I was a guy. Great. So everyone here is aware of my true identity. I walk inside and see a number of people, several girls, all of whom I knew from high school. None of them are dressed up yet but all complimented me on my outfit. Flushed with embarrassment, I thank them all. I ask where Cherry was and they reply that she was just getting ready.

All the girls greet me with hugs, giving me a warm welcome. Some go under my short skirt and pinch my ass. Annie, the boldest of the bunch, lifts my skirt, revealing my thong for the whole room to see. "Oh my god," Annie says, "Isn't this the cutest little thong you girls have ever seen?!"

They all agree as Karla says, "It sure is. I had a pair of plain cotton panties for him but he insisted on wearing a thong. So I literally had to give him the one I was wearing to shut him up. It was the only one I had at Andrew's house!" Laughter ensues. I couldn't believe Karla blatantly lied like that, but what was I supposed to say? It would be impossible to prove her lie, and honestly, pointless. I was still standing in the room, with my frilly pink thong on full display, as Annie gave my ass a few slaps before letting me go.

Annie and Karla take the last available seats, leaving me standing in the middle of the room. I look around and realize there's one person here I don't recognize. Sitting on the couch I see a black man, about 6'2', and well built. Karla, noticing my dilemma, says, "Jenny, don't just stand there like an idiot, go ahead and sit on Richie's lap! I'm sure he won't mind."

Sitting on his lap is the absolute last thing I want to do. But all the girls egg me on and Richie pats his lap, so I guess I have no choice.

I take a seat, as far away from his lap as possible towards his knee, but he pulls me closer. The dress was so short that it rode up and only the thin line of the thong separate me from the growing bulge I could feel in his pants. He holds me here with his arms around my waist as I uncomfortably listen in on the conversation everyone's having. I can't pay much attention, though, as he starts rubbing my sides. I feel his dick hardening against my backside.

Karla, sees my predicament and says, "Now, Jenny, I know you didn't just sit on his lap without giving him a thank you."

I swallow a lump in my throat. Nerves rise, but I quickly let out a quiet thank you.

"Oh no, you can do better than that. Say thank you like you mean it. He didn't have to offer you his lap to sit in."

I say it loud enough for everyone to hear, but this still wasn't good enough.

"Cmon, Jenny. If you're really thankful, maybe give him a kiss."

A kiss?! Now that was way too far. As dumb as it sounds, it almost felt more gay to kiss a guy than it was to take one up my ass. Sex was sex. Kissing seemed almost... too romantic. Plus, I was sort of forced into the sex. This would be voluntary.

"Umm, Karla, I don't know. I already said thank..."

Karla doesn't let me finish my sentence. She leaps to her feet, infuriated, and gets right up in my face.

"I'm sick of this disrespect! I treated you so nice today and had you experience pleasures you've never dreamed of. And you have the nerve to say no to me?"

I'm dumbfounded. I can't believe she just snapped at me like that. I've never seen her this angry. Plus, I was still a man, right? A week ago, I would've said something back to her. A woman demanding me to do things? Yeah, right. Now, though, I was embarrassed and very aware of the situation I was in. Dressed in a slutty angel costume, sat on top of a muscular black man, with what feels like a massive dick. Feeling very submissive, I whimper out a response.

"I'm sorry, Karla. I just don't know how I feel about all this right now."

Karla, surprisingly, changes her demeanor. Going from demanding to understanding.

"Well, you can trust me, Jenny. Have I steered you wrong yet today?" She says rubbing my cheek, now, talking in a much softer tone. I realize she has a point. Sucking Andrew's dick, getting railed from behind, having a butt plug shoved up my ass. I hated to admit it, but it all did feel really good. "Go ahead and give Richie a big juicy kiss just like you gave Andrew's cock back at his place."

The girls chuckle and I'm again flushed red with embarrassment. Still sitting on Richie's lap, I turn my head and give him the same juicy kiss I gave Andrew's cock the second time, afraid of Karla's wrath if I do anything else. Emotions flood through me and I feel a tingling inside. We are entwined for what feels like hours and I can't help but moan as we share this moment. Finally our lips disconnect and I see some of my pink lip gloss on his lips.

"Wow..." I say in a breathy voice as I look down and notice my dick is sticking rock hard through my skirt and panties on full display for the whole room to see.

"See, Jenny, I told you I wouldn't do you wrong. By the way, from now on, refer to me as Mistress, like a true sub. I will not be putting up with anymore back talk from you missy."

"Yes, Mistress," I reply, starry eyed, as Richie lifts me up off his lap and places me back on, this time facing him. We engage in another kiss. This one is sloppier, but he is the aggressor and I let him dictate the pace. I start rocking back and forth on his lap, feeling his long, hard dick through his pants, as I'm touching his face with my hands. Karla was right, I was loving this. I couldn't help but rub my member that was sticking through my thong onto his stomach. His hands wrap around my waist, squeezing my ass. His finger starts to hover near my plugged up hole. He gives it a few taps, when all of a sudden, I feel it. Vibrations so intense I have no choice but to hump into him harder. Moans escaping my lips as our tongues danced. The sensation continues as he rubs the outer edge of my plug in circular motions and I lose control. I cum right there. The kissing combined with the plug sent me overboard, causing me to explode.

The kiss stops and I stay on his lap, panting like I had just run a marathon. Karla starts rubbing my shoulders and gives me a hug from behind.

"Awwwe, Jenny, you just came from a kiss. That was soooooo hot. You are such a sissy. Of course I might have helped a little with this thing," she says, holding what must have been the control of the plug.

She helps me up off of his lap. I see most of the cum was caught in the panties, but his shirt caught some as well. Karla licks the cum off his shirt.

"I'm sorry, I just couldn't help myself, little one. That made me sooooo horny, I had no choice. Don't worry though, you can clean your panties yourself. I'm sure you remember what Andrew's father said."

She lowers my thong down from under my dress and has me lick the remains straight from it. I do it with no question. After licking it clean, Karla takes the panties from my mouth and works them back up under my legs, into place between my cheeks, tucking my penis in the process. I'm so lost in bliss I forget the entire room is full of old friends. David, the seemingly normal guy, was no more. Sissy Jenny took his place. I focus my eyes for the first time in forever to see some of them with mouths agape and others with an evil looking smirk, especially Annie.

Before I can even gather my thoughts. Cherry comes bursting out of the bathroom, with a towel over her head and a bathrobe.

"Omg, Davey, it's so good to see you! Karla bring him, or should I say her, up here. Her makeup is a wreck!"

In the bathroom, the sink was filled with makeup clutter. Cherry leads me in holding my hand with Karla close behind. They close the door and Cherry immediately gushes over my outfit.

"I've missed you so much, David! I'm so happy you decided to dress up. And omg you look so sexy in this angel costume. Karla didn't you wear this last year?"

"Yes I did, but she's taken sexy to the next level," Karla says as she lifts my dress, revealing my thong. Cherry is giddy with excitement upon seeing my underwear choice.

"That thong is so tiny! How did he even fit into this. I know he's a small guy but I would think his man bits would be slipping out."

"Well, she may be bigger than the average sissy down there, but it's still not enough to spill out of these cute panties. Do you know he insisted on wearing a thong? He wouldn't accept anything else!" They both laugh and I just stay silent. There she goes with the lies again, making it seem like I willingly wanted to dress this slutty, but I knew better than to talk back to her. "Isn't that right, Jenny?"

"Yes, Mistress," I reply, leaving a shocked look on Cherry's face.

"Mistress?" she asks.

"Yes, Cherry, she was being a bit difficult before and I decided to lay the law down and demand her to refer to me as such. She knows now to never disobey me. Isn't that right, Jenny?"

"Yes, mistress."

"Also, Cherry, please refer to Jenny as a she from now on. This is her preference."

"Oh no problem. I'm sorry I'm just so used to calling him, David, I didn't know what else to call him, I mean her. Jenny suits him."

"It does, doesn't it?"

With my dress back in place, Cherry continues with the compliments. "And wow look at how short this is. You're feeling a little daring tonight. I'm glad, tonight's going to be so fun." She turns me around revealing how short my dress actually is, shrieking in excitement. "You are such a little slut! I can see the bottom of your cute little bubble butt. Omg we aren't going to be able to keep the guys off you."

"You got that right, Cherry. In fact, we may have a hard time keeping her off the guys, as well. She had quite a good time downstairs before you hopped out of the shower."

"No way, did she hook up with, Richie?"

"Not only that, she came from just kissing him!"

"You little whore!" Cherry shrieks in excitement slapping me in the arm. It feels weird just standing here, listening to them talk about me like this. But they are right. I am whore. How did I cum from just a kiss? Granted, the kiss was amazing. Wait, amazing? How could I think something like that?

"I know she looks great in this outfit," Karla says, "but she's kind of ruined it with the night she's had already. It's all sweaty and gross. I'm thinking we make her the main attraction tonight." Main atttraction? What the hell was she talking about?

"I completely agree with you, but first let's clean her up."

Cherry and Karla lift the dress over my head, leaving me there in my bra and thong. Cherry goes into the closet and pulls out a tube. She pulls down my panties to see a butt plug staring her dead in the face.

"Did Jenny insist on the butt plug too?" Cherry asks.

"No, that was all Andrew's fathers idea. He said he should be plugged up and slutty at all times when in his household."

Wow, I can't believe she just told Cherry that! Why couldn't she lie about the plug like she did the underwear? I'd rather that than Cherry knowing Andrew's father saw me in this state.

"Omg, his father saw him like this?"

"Oh, honey, you have no idea. I'll tell you all about it in a second. First lets get this enema going. We need to make sure her pussy is nice and fresh for later tonight." I guess my night was just beginning. I ignore her referring to my ass as my pussy and shudder to think of what else they have planned for me.

Cherry removes the plug to cum dripping out of my rectum. "What is this?!" She exclaims. "Now who is this from?"

"Andrew, of course, but hurry up with the nozzle. Valerie just texted me saying she's on her way with the others right now." Great, more girls I used to chill with are going to see me in this state. Karla wipes the cum leaking out of my ass with her finger and sticks it in my mouth, which I obediently sucked on. Cherry can't believe her eyes.

"Oh, she's such a little freak! I love it!" Cherry then removes the butt plug. I was getting used to the feeling of being filled up and was secretly hoping it would be put back in before the night was over. "Now what should we do with this?"

Karla grabs it but struggles to find an open spot on the sink. Her eyes light up. She walks over to me, now on all fours getting ready for the enema, and places the butt plug inside my mouth. I can taste the disgusting residue on it but obediently suck on it as Cherry and Karla work the tube into my ass. At this point, Cherry doesn't even question it. What's happened to me?

"Now, you're going to feel very full, Jenny, but that is totally normal. Just relax and we'll make sure your nice and squeaky clean down there."

Karla starts telling Cherry all about the night I had. By the end of it, Cherry is left aghast.

"No, freaking way, so his first time with another guy was with his best friend?"

"HER first time, and yes, but not just her first time with another guy, her first time with anybody," she says giving me a wicked smile. How did she know? She must've just taken a guess, but it was true. The realization of it all came flooding back to me and I couldn't hold back anymore. I started crying. I was bawling my eyes out while on all fours, with a tube in my butt, and a plug in my mouth. Cherry comforts me by rubbing my back.

"Oh no baby, don't cry. It's alright that you lost it to Andrew. Everyone's first time is supposed to be special, and yours was. You had you're best friend of years take it. And there's nothing to be ashamed about."

I continue sniffling and Karla removes my plug, so I could talk.

"But it was with a dude! I'm not gay! I like women, but I've never even gotten close to a girls pussy, and Andrew took mine like it was nothing." I continue sobbing, ignoring the fact that I referred to my asshole as a pussy. Now even Karla comforts me.

"Hey, Jenny, that doesn't matter at all. Remember what I told you. You're not gay, you're all women today, and losing it to Andrew was the best thing that could have happened to you. Like Cherry said, your best friend took your virginity, and made you understand how good it felt to be a woman. It's gonna be a moment you remember and cherish forever."

I sniffle some more, but ultimately see her point. I did lose it to my best friend.

She continued, "Most girls lose it to someone that they think care about them, when in reality they don't. They're just there for the deed. You know Andrew cares about you, so cheer up a little girly!"

"I think you're right, Mistress," I say still sniffling.

"Atta girl," she says, lightly tapping on my back, "But I am going to have to punish you for your language." Language? What was she talking about?

"Girls pussy? Really, Jenny? That's no way a pretty young lady such as yourself should be talking about other women. It's inappropriate, and you're going to learn how to talk like a lady. The only time you should be saying pussy is when you're referring to your own. For now, though, you'll be punished for your foul tongue." She stands up and walks in front of me with her back toward me. Her ass is directly in my face. She lifts up her dress to reveal her pantyless bum. "Now eat my ass, Jenny."

I don't know how to react. I don't want to hesitate for too long and I wasn't allowed to, as Cherry shoved my face directly into Karla's ass.

"Eat it, bitch!" Karla yells.

So I start licking away. Lapping up her hole like a hungry little slut. The taste wasn't as strong as my plug, but maybe I had just gotten used to it. It tasted almost salty in a way, and to be honest, I enjoyed it. I went to town on her, when all of a sudden I hear her stomach rumble. Then she farts. I instantly recoil, trying to get as far away from her hole as possible, but Karla shoves my head back in.

"Oh no you don't slut. Keep at it. I'll tell you when to finish. That foul tongue of yours deserves the foul taste of my ass."

The taste went from enjoyable to disgusting, fast. I don't know if it was because of the humiliation, or the fact that I was this close to a women, but I couldn't help but get hard. I continue licking for who knows how long before she finally lets me go.

"That was actually quite enjoyable, slut. That won't be the last time I use that mouth of yours for my pleasure. Now open up. Lets get this plug back in you and that tube out of you."

I obediently do as told and am soon led to the toilet to empty my bowels. This is done a few more times before they plug me back up (my butt that is) and sit me down in a chair to begin my makeup.

Cherry gets to work on me, and much like earlier with Karla. I had no idea what was going on, as there was no mirror.

"Okay, now that she's looking pretty again, what should we do about her underwear? The bra seems fine but her thong is soiled!"

"Ah don't worry about that. She's a bit of a freak, she likes feeling filthy. Isn't that right, Jenny?" Karla asks.

"Yes, mistress," I say defeated. Karla didn't like this response.

"Yes, mistress what?" Karla says as she rubs my dick through my panties. "Say you love it."

"Umm, yes mistress, I LOVE feeling filthy. Please let me keep this pretty pink thong on."

"Okay if you insist," she says as she stops rubbing my penis. "And I'm sorry honey, I know you love your little angel costume but we have something even better for you." A new costume? What on earth did Karla have in mind.

Cherry re-enters the bathroom with some sort of small pink polyester like material, with what looks like a fuzzy white cotton ball inside of it. She opens it up and I can't even make out what it's supposed to be. She tucks my dick between my legs and has me step into it and works it up my body, working the straps over my shoulder. It was a tight one piece that was probably a size too small for me. The back went straight up my ass giving me an intense wedgie. They then worked light pink thigh high nylons up my legs. They finish it off with a pair of pink bunny ears on my head and I realize exactly how they dressed me. They lead me towards the mirror and I see I went from a slutty angel to a slutty bunny.

This costume made the other one look conservative. Makeup wise, I looked much like I did earlier when I was first done up, except this time Cherry took the time to pluck my eyebrows into a feminine arch, as well as giving me whiskers on my cheeks with eyeliner. In glittery letters on the front of the tight pink one piece said the words "SLUT" in cursive. The back of the costume left my ass on full display and was so high cut my hips and part of my stomach were revealed as well. I stared into the mirror stunned. Where else was this night going to take me? There's no way I could go out dressed like this.

"Oh yay, Valerie's here! Jenny, why don't you go downstairs to greet her?"

I reluctantly agree as I walk down the stairs to all the cat calls in the living room from the ladies. I open the front door to see Valerie, also dressed like a bunny, but hers was more traditional, being black instead of pink, and not nearly as tight. I guess she didn't have on a size too small like I did.