Something New Ch. 15

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A day of firsts.
3.1k words
4.77
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Part 15 of the 27 part series

Updated 06/16/2023
Created 08/11/2022
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The next morning I got up early, having set my alarm much earlier these days to make sure I gave myself enough privacy to go downstairs and give Jared his daily blowjob. I got downstairs and could hear moaning coming from their bedroom and I knocked and my SIL bade me enter. opening the door and sticking my head around I saw my SIL bent over doggystyle while Jared fucked her.

"There's our little slut. Early whore gets the dick right?" She said between moans and gasps. "I pulled out a new outfit for you. Figured we needed to make an impression on your first day as a sissy hooker."

Turning to her in surprise she chuckled "Jared told me when he came back in from fucking you in the shed yesterday. Heard he made you scream like a whore."

Turning away I opened her closet and saw on display a pink schoolgirl outfit just like the one I have worn for my wife.

"That's one of my favorites and it's silk and thin so it'll fit under your suit just fine. Put it on."

I got undressed and put the outfit on. Sliding on the knee high socks and the frilly pink short skirt and the deep v neck blouse with wide collar. I looked like an anime schoolgirl.

Jared bucked into his girlfriend a few more times before pushing her down on the bed and he got off, his glistening hard Nubian cock swinging in the air like a club. As he got closer I immediately dropped to my knees.

"Oh look at that, she already knows her place. On her knees worshiping black cock. Are you a black cock slut?"

I looked up at Jared as he slapped my face with his big heavy wet cock.

"I'm a slut for big black cocks." I chanted as I took Jared's dick in my mouth, not wasting any time deepthroating him. I bobbed my head in such deep long strokes I was fucking my own face on his rock hard dick.

"Oh yeah, such a filthy little cocksucker. I bet the guys at the office are just going to love having a white sissy slut like you to play with. Are you going to suck off every black man in your office, you sissy slut?"

Humming my agreement I stroked Jared while I sucked him. I could taste the familiar juices of pussy on his cock.

"Can you taste her pussy on my cock bitch? Imagine if that was your wife's pussy you were tasting."

"Oh, my sister is a black cock whore just like her husband. Did you see how she played with herself watching that porno. She wants it."

I pulled back to disagree but Jared grabbed my head and stuffed it full again.

"I didn't say you could talk bitch. Keep sucking. Unless you want me to take this cock upstairs. I bet I could make her scream just like you bitch."

"Oh my sister is definitely a screamer babe."

Feeling jared tense like he was about to cum I doubled my efforts.

"That's it, you sissy whore, make me cum. Take my cock bitch."

As he came I was aware of my growling stomach. I've been on an almost exclusively cum diet, eating precious little else. It must be affecting my cognitive reasoning. Finishing Jared off I was commanded to leave and so I did.

I got my suit on top of my schoolgirl uniform with little issue before my wife woke up. I tried to leave as quickly as I could, trying not to linger and risk my wife looking at me too closely. When my wife finally started down the stairs I gawked at what she was wearing. She was in a tight string tank top with no bra, her hard nipples poking through and short skimpy silk shorts. It was a normal pajama set she wore but given Jared's attitude toward her it made me panic. I looked to my SIL and she was holding back her obvious amusement

"Good morning," my chipper wife greeted us all.

I was standing behind the counter next to Jared and my SIL was across from us and turned to face my wife.

"How did you sleep sis?"

As my wife started chatting with her sister Jared's hand lifted to my butt and gave it a squeeze. Without being able to stop myself I jolted by the forbidden touch and my wife looked at me when I squeaked.

"Sorry hot coffee.'' I said bringing the cup up to my face trying to hide my face as it turned obviously red. Not trying to look suspicious, I didn't look at Jared as he continued to grope my backside.

"Oh honey." my wife caught my attention. "I was thinking, what if you took the day off and we all went to the water park today?"

Before I could respond, Jared answered for me, "Oh big dawg wouldn't want to join us, he was just telling me what big things he's got planned with Lawrence."

"Lawrence?" my wife asked.

"Oh yeah he didn't tell you? Lawrence is a buddy of mine and works with your husband at the office."

"Is that so? That's so cool. Are you sure you can't come with us?"

"I would love to sweetie but Jared's right there's a lot to do at the office."

"Okay I just thought you could use a break. You work too much."

"I know dear I'll find a balance here soon....a lot of new developments."

"Well I for one, am excited. It's going to be so much fun. I haven't worn my bikini in weeks."

"Oh I don't wear bikinis in public."

"Nonsense, I got just the suit for you. You will look absolutely fuckable."

I couldn't miss the obvious subtext my SIL was spilling.

"I don't know. I'm really not comfortable showing so much skin like you are. What do you think babe?"

Jared squeezed my ass hard making his message clear.

"Uh you should do it babe. You are beautiful, you would turn a lot of heads and go have fun."

"Okay I'll try it on and see, I don't know but we will send you pictures so you can see what you'll be missing" my wife said as she and my SIL escaped to the guest room.

I was left alone with Jared. Meekly I looked up at him.

"You better get to work. Don't worry, I'll look out for your wife." she told me, winking as he gave my ass another squeeze.

"Wait...'' I reached out to him. He looked at my hand and I removed it. "Are...are you...what do I have to do so you don't try to fuck my wife?"

"Don't you think that's up to her?" Jared answered smiling.

"I just....I don't....'' I stammered.

"You're so cute when you stutter. Okay I will promise you I will not fuck your wife..." he told me hand on his heart.

Sighing with relief as a great burden was lifted from me, until he continued.

"...until you beg me too."

Stunned, I looked at his devilish smile and he walked to the living room turning on the TV.

Looking at the clock I realized I had to leave so I shouted my goodbyes and heard my wife shout her goodbyes in reply.

When I got to work I buried myself in my work. Losing track of time. My phone buzzed and I got a message from my SIL. It was a picture of the three of them at the water park all smiling. The more I stared at it the more I got concerned. My wife was sandwiched between the two of them and she was in a bright pink polka dot bikini and obviously my SIL is much less endowed than my wife because my wife's breasts were spilling out. Jared's arm was around both of them and the other hand was resting on my wife's bare stomach.

I got several selfies and group pictures and one of my wife under a water spout with her head back and her tongue sticking out and at the top of the water spout was Jared so it looked like the water was coming out of his crotch.

I was startled by a sharp knock at my door and it opened as I was putting my phone down and Lawrence popped his head around the door.

"Hey, is this a good time?"

"Um yeah what's up..." forgetting that it was the same time as yesterday.

"Well it's..." he motioned to the clock. "and i figured it was safer in your office than in the bathroom you know what i mean?"

"oh OH right right yeah um yes definitely" I flustered

"Jared told me you accepted my offer."

"He did? Uh yes I did. He kind of persuaded me last night."

"Is that so? Physically?"

Biting my lip while my face turned red in response

"Well either way that's great to hear and I got your first client."

Wait, client? I thought I was going to suck him off today, not another guy. Not already.

"Um, really? who?"

Reaching out the door he motioned someone in and another tall black man entered. I saw Lawrence close the door and set the lock.

"Have you met terry? He works in HR."

"Um, no I haven't. Hi, Terry."

I stood up and reached my hand out and he took my hand and he had such a firm grip.

"When I heard we had a sissy in the building I never thought it'd be you. Aren't you married?"

"Yes he is. The reason for the need for discretion." Lawrence spoke for me.

"No problem here. So how do you wanna start?"

"Um, how about I take off my clothes." I suggested.

I started taking off my suit and the slow reveal of my pink sissy schoolgirl costume got both of them grinning ear to ear.

"Excellent choice. Innocent schoolgirl uniform."

"Do you have a sissy name by the way?" Lawrence asked me.

"Um no I don't...."

"No matter what about Jennifer? It'll help protect your identity."

"Um sure yeah sounds good."

"Alright Jennifer, get on your knees." Terry said, rubbing his bulge.

Sinking to my knees I reached up and undid his zipper and fished out his dick. He was so thick but shorter than Lawrence and Jared. I didn't hesitate to take it into my mouth. Wrapping my arms around the back of his legs and bobbing my head. His thick cock was really stretching my jaw.

"Oh fuck this bitch doesn't waste time does she?"

"I told you she was good."

I made sure to make eye contact with Terry as he held back his tie down.

"Fuck yeah this bitch is worth every penny. She's such a good cocksucker."

I moaned a hum in thank you. I lost myself in the rhythm of bobbing my head on this black cock when I felt something land on my shoulder from behind me. I looked down and saw Lawrence's cock was out and hard and in my face.

"Have you ever served two black guys before?"

"Um no. I told you I was new to this."

"Well, no time like the present Jenn."

Taking Terry's cock in one hand I took Lawrence into my mouth and bounced between the both of them. Lawrence pulled out his phone and pointed it at me as I sucked two big black cocks while on my knees dressed like a sexy schoolgirl.

"Don't worry babe you'll get all the copies. Can you believe she doesn't have an onlyfans?"

"Oh fuck baby you would make so much bank. Everyone wants to watch a sissy white slut servicing black guys."

Resting my mouth I jerked both of the cocks at the same time as I looked up to the camera.

"Do you like my white sissy mouth wrapped around your big black cocks?"

"Oh fuck. How much to fuck this bitch."

"$100."

"Fucking worth it. Come on bitch bend over the desk."

Terry dragged me to the desk and flung everything onto the floor and pushed me down, bending me over my own desk.

"You ready to get fucked bitch? Sissy schoolgirl slut."

Looking back over my shoulder I must've looked nervous. I have only been fucked by Jared's massive horse cock and now I was about to take two big black cocks at once. Both Terry and Lawrence were getting naked while I remained dressed like a schoolgirl though my front blouse was wet from my drooling sucking both cocks.

"Yes sir fuck my white schoolgirl pussy with your big black cock."

"That's a good slut beg for our cocks."

Terry stepped up behind me rolling on a condom and Lawrence was walking around the desk to my front side. While I felt Terry's thick cock pressing into my ass I pushed back into him. Once his cock opened my hole I exhaled deeply. Terry's cock was nearly as thick as Jared's. When I exhaled Lawrence took the opportunity to shove it in my open mouth, surprising me.

Terry's hands grabbed my hips tightly and he pushed me forward until the head of his cock was all that remained and in one hard thrust shoved his cock violently into me. I used my hands to brace myself on the desk but Terry put one hand on my back and pushed me down hard. My head hung over the desk and Lawrence reentered my mouth. Lawrence didn't even have to move with as hard as Terry was fucking me it was consequently forcing my head on and off his cock. I looked up at the sound of Lawrence's voice to see he was pointing his phone in my face as I moaned getting fucked dressed like a schoolgirl.

"Are you a bad little schoolgirl Jennifer?"

Looking into the camera between my moans I said, "Yes, ah, yes I'm a naughty schoolgirl slut. Oh fuck."

"Do you like getting fucked up the ass?"

"Oh yes I love getting fucked up my tight white ass by big black cocks. I'm a black cock anal whore. Please fuck my ass. Teach me a lesson."

"Oh fuck girl you're gonna make me cum. I'm going to cover your sissy face with my cum bitch."

Terry pulled out his cock from my ass and as he walked around the desk to change places with Lawrence. He removed the condom and shoved his dick in my mouth. While he was pumping into my mouth Lawrence spread my cheeks open and pushed his cock into my ass.

"Oh fuck you are one tight white boi. Does Jared not fuck you regularly?"

"He fucks me every day."

"Oh fuck you've had three cocks in your ass today? How does that make you feel?"

I looked back at Lawrence still holding his phone up.

"I feel like a sissy whore. Please fuck me sir."

"Mmm that's a good slut. Now beg for my cum on your face." Terry grunted at me.

"Please cum on my face. Mark me a black cock cumslut. I've been such a bad schoolgirl."

Terry came on my face with a violent explosion. My mouth opened as I gasped and some strings of cum hit my tongue so I stuck it out to catch more. Terry finished and moaned loudly.

"Oh fuck. You are such a good slut."

Still bouncing from Lawrence fucking my ass I thanked him and hoped I'd see him again. Terry nodded and smiled and got dressed and heard him leave.

"The bastard left the door unlocked." Lawrence stopped to go lock the door and I just hung there on the table feeling my legs shake.

"Do you want to try another position?" Lawrence asked.

Caught off guard I stuttered, "Um I don't know any other position. I've only ever been fucked bent over..."

"Yeah that sounds like Jared." he laughed.

"Here lay down on the carpet."

Raising myself off the desk I crawled to the floor and rolled onto my back. Lawrence knelt down between my legs and he gently opened my legs. I grabbed my thighs and presented my fuck hole. He leaned over me and got the head of his cock lodged in my ass before leaning closer to me, his face inches from mine and he slowly almost lovingly pushed his dick deeper. I felt pressure behind my balls. He was hitting my prostate. I rolled my eyes back and moaned.

"Does that feel good, baby?"

"Yes, that feels so good, oh my god."

Smiling he nestled his head in my neck and kissed as he slowly pumped into me. My penis was sandwiched between the two of us and I could feel it getting hard.

"Oh my god how are you doing that?"

"What do you mean?" Lawrence asked, raising himself up.

"I haven't been able to get hard for hours after Jared fucks me."

"Oh poor girl, Jared likes to dominate his sissies completely. Not me, you're safe with me."

He grabbed my wrists and raised them above my head. Pinning me down as he thrust harder into me.

"Oh fuck that feels so good. Oh fuck yes cum in me."

"That's it, Jennifer begged for it."

"Cum in me Lawrence, fill my ass up with your seed. Oh fuck yes that's it right there. Oh fuck don't make me cum. Don't make me cum."

"Trust me baby. Dum for me. It'll be okay."

I stopped holding myself back and let loose. I came up with my stomach spurting hard. As I came my ass spasmed on his cock and I could feel him cumming inside me. He collapsed on top of me and we just laid there panting.

When he finally got off of me I just laid there in my schoolgirl uniform, the skirt up to my waist and my cum splattered up my stomach.

"You did good today, here you go." Lawrence, grabbing his clothes, handed me cash. "You should get dressed before I open that door."

I got dressed and wiped my face on my already ruined blouse and Lawrence went to leave but before he did I stopped him and thanked him. He just smiled as he left.

I looked at my phone and there were more suggestive pictures. One of which was my wife in Jared's arms, her legs wrapped around his waist and his hands on her ass holding her up in the air.

I got a ding on my phone. It was a message from Lawrence. It was the video he shot of me getting double teamed by him and Terry. Then a message.

"You did great, sweetheart. I might have something for you tomorrow too. See if you can get your hands on some cuffs. P.S. I'm serious about that Onlyfans."

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