Careless Whispers (part four) [Anal: wife] [Anal Play: sister-in-law] [Fingering] [Blowjob]

Katherine didn’t seem to notice anything amiss and the day came to an end without a fuss. I managed to sneak a couple of gifts into Gia’s room without anyone noticing, though I wondered if she would find it or not. I was restless all day, wanting a reason to be in my study late so I could check to see if Gia did a show or not, but I never came up with one and had to curb my wants by begging my wife to let me have her ass. Katherine had a nice and tight cunt, but I was trying to mimic what Gia’s body would feel like and my wife’s ass was her tightest hole.

I pulled out last minute and pushed Katherine onto her back, cumming on her clit and mound as she glared at me, “Now I have to actually shower,” she whined.

I smiled, “I can come clean you up,” I offered.

She shook her head and pushed me away, “No, you have to go to bed so you can make sure Gia gets up in the morning after I take the kids to school so you two aren’t late to the office. Are you sure it’s a good idea to just bring her in without talking to the boss first?” she asked.

I nodded, “I’m almost certain he’s going to be all for it. As you mentioned before, he’s a lecherous old man and having her there is more likely to give him the encouragement needed to secure the internship for her. Currently the intern is lined up to be Vince’s nephew, but I’m hoping the two of them can work together instead of having it go to one or the other.”

Katherine laughed, “And you think the guys seeing her in the office will make that more likely.”

I nodded, “I think I will have to stay with her constantly to make sure they don’t try anything,” I said.

She sighed and went to shower and I went down to the kids’ bathroom to clean myself up. Gia was just across the hall…I could peek in without Katherine noticing…maybe?

I opened Gia’s door and saw her sleeping on her side, no blankets on her. Her pajama top was lifted slightly and her shorts clung to every curve of her body. The thought of waking her up with my dick on her lips filtered into my head, but I just shut the door then checked in on my kids, ensuring everyone was safe and sleeping in case Katherine saw me checking on Gia.

Katherine woke me up when she left with the kids. I let Gia sleep a little longer then came into her room and stroked her cheek, “Gia? Did you get your presents last night?” I asked softly.

She half smiled and opened one eye, “Were they presents for me or you?” she asked in a still sleepy voice.

I smiled, “Use them before we leave for work and it’ll be for both of us.”

She stretched and I slid my hands under her top, pulling her up to me by her back, her eyebrow arched as she looked at me, “Will Katie be back before she goes into work?”

“She doesn’t normally, but she might stop in to see you off for your first day,” I said.

She pouted and nodded, “Fine, how business versus casual do I dress?”

I looked over at the closet, “Did you unpack?” I asked.

She nodded, “Closet has business-y stuff, drawers have more casual stuff, are you going to pick out my outfit for my first day?” She teased me with a curt little smile.

I smirked at her, “Would you trust what I picked out?”

She nodded.

I looked her over, “Go hop in the shower and I’ll have an outfit laid out on your bed for you when you get out.”

She lazily crawled out of bed and headed to the door but stopped and looked back at me, “Did you set up a towel and washcloth for me?”

I shook my head, “Not this time,” I said with a smile.

She pouted and I pointed to the bathroom, “If we have time we can have breakfast together,” I teased.

I searched her closet and drawers and found the outfit that felt right for my office. I pulled out a candy-red lace bra and panty set, an eggplant colored leather mini skirt and moto-style jacket and a white sleeveless silk blouse that looked to be tailored to fit her body, allowing for coverage but a definite draw to her chest and cleavage. I pulled some jewelry from the bureau where she had it laid out, a copper wire wrapped necklace and earring set with striped flourite accents, and a wrapped leather watch. I left her room to head back to mine, I needed to shower and get ready myself. My office wasn’t super stringent on dress code, but interns and new hires were expected to be a little more on the business side than the casual side. I wore dark blue jeans, a white button up dress shirt, undone just at the neck, and a black suit jacket with a platinum watch.

Gia’s jewel-toned hair was in a sleek braided crown and bun style when I next saw her. I came up behind her and let her hair down from the bun, but secured the braid for her with a red leather hair clasp, “Your hair down will make a bigger impact on the boss,” I whispered as I inhaled the scent of her delicate perfume and shampoo.

I slid my hand up the back of her skirt and rubbed my finger under her panties, working my finger to her asshole. She held her breath as I grazed the jewel of the small plug I’d left her. I smiled and she closed her eyes as I played with it just a little. “Did you use your other present, too?” I whispered as I pulled my hand away from her.

She blushed and looked at my reflection in the mirror as I ran my fingertips over her collar bone and cleavage. She pulled away a little and turned to look at me, “I like the outfit you picked out, but isn’t this going to be hot?” She asked as she tugged on the jacket.

“You don’t have to wear it until we get to the office, we keep it cold in there and if you want to make some friends you’ll bring a jacket instead of asking to adjust the temperature,” I offered as I crossed the hall to wash my hands before we left.

She pulled the jacket off and we headed downstairs. Katherine was just coming in, closing the door behind her as she looked up and saw us, “Ohh! Good I didn’t miss you two! I want a picture. I promised mom and dad I’d send one of your first day,” she said to her little sister.

I stood back and Gia put the jacket back on and stood up tall, trying to reach the same height as her older sister, but falling about half a foot too short. They stood side by side and I took a picture of them. Katherine ushered me over and I stood slightly behind Gia, my hand on her shoulder as my wife took a picture of us as well.

“If this doesn’t work out, will Gia still be able to intern with you?” I asked her as Gia and I got our shoes on and got ready to head out the door.

Katherine nodded, “Yeah, I worked it out so I can give her a separate orientation if need be. I told them this would work out better for her degree but it’s not set in stone and we’ll find out today if it works out. So call me when you know, okay?”

I kissed her on the cheek, “Okay. Do you want us to come get you for lunch?” I asked.

She shook her head, “No, she should mingle with your office, take her out with the guys but please keep her safe,” Katherine said as she hugged Gia tightly.

Gia groaned, “I’m twenty, stop treating me like I’m two!”

Katherine grabbed her sister’s jaw and lifted her face to look at her, “Not my fault you never got taller…,” she teased.

Gia pouted, “I’m almost five feet tall! Mom must’ve smoked when she was pregnant with me or something…,” she complained.

Katherine laughed and I did too. Gia was sensitive about her height. She was the shortest in the family. Even though none of the women were exceptionally tall, Gia was on the exceptionally short side of things, barely standing four foot eleven. Our twelve-year-old son just crossed the five foot mark and Gia was quite mad about it when she saw him on Saturday.

We headed out to my car and waved to her sister, as we pulled away. Once we were on the road I glanced over at her, “So, *did* you use your other present?” I asked.

She said nothing, just pulled her skirt up to her hips and spread her legs in the passenger seat. I reached over and put my hand inside of her panties and felt her, she was slippery all over and her panties were soaked. I smiled and started gathering her fluids up on my fingers as I rubbed her clit in little circles. I’ve no doubt that at least a couple of cars could tell what was going on by the look on Gia’s face. I rubbed her gently and slowly, just taunting her and teasing her pussy.

I glanced to her as I pulled my hand from her panties and started cleaning her stretchy fluids from my fingers, “We’re going to be a little early, there’s a little cafe on the street level, we can have breakfast there before I take you up to the lion’s den,” I said with a chuckle.

She fixed her skirt and squirmed a little, she was sensitive and wanting. I planned on keeping her that way all fucking day, little teases to keep her dripping for me. Her laptop was in her bag in the back seat and I was honestly trying to figure out a way to break her in tonight. Not having my dick in her was killing me, but I had to make sure Katherine couldn’t find out. Which meant I had to be careful and plan this out so I didn’t have to rush anything.

When we pulled into the parking garage I pulled my seat back and unfastened my pants, Gia’s mouth happily descended on my rod and she easily got me off as I restrained myself from grabbing her hair and messing it up before she met my boss. I wiped her lipstick from my cock and she reapplied it in the visor like it was something she’d done a million times, and I wouldn’t be surprised if she had.

I wanted to eat her out before we went in, but I knew that would be harder to pull off without someone noticing as they walked past the car, so instead I decided on something else. “Give me your panties,” I said as I looked her over.

“What?” she asked.

“Your panties, I want them. I’ll give them back at the end of the day.”

She lifted her hips in the passenger seat of the car and slid them down her thighs and off her legs. I neatly folded them and put them in my pocket.

Heads were turning as soon as we went into the cafe. She had a lemon poppyseed muffin and orange juice and I had a ham, egg, and cheese biscuit and a coffee. I mostly just watched her eat. She picked at her food, tearing off dainty bird bites, picking around the muffin to leave the best looking bits for last. Then she asked if she could try my sandwich and I handed it to her. She took a big bite and handed it back to me, making me laugh as she clearly bit off more than she could chew, almost literally. I finished my sandwich, she finished her muffin, and we went up to the office.

Presenting her to my boss was easy enough. He got one look at her and he was on board with whatever I wanted to keep her in the office but insisted on her going through the same tests he normally puts interns through. I think he expected her to just sit around and be eye candy for the guys in the office, but she wasn’t into being idle.

She worked her ass off for the first part of the morning. She jumped in feet first and had the guys leaning on her for support as she helped them with various tasks and paperwork as if she’d been doing this kind of thing for years, even showing me how to better format a form I’d used for nearly a decade. It was humbling to see that she wasn’t just aiming for a career in a high paying field typically laden with guys because she knew she was pretty and could coast by. No, she was putting in the effort and using the things she was being taught in school to make us more efficient and our jobs a little easier.

When lunchtime came around the boss took me, Gia, Vince, his nephew, and a few of the higher up bosses to a tavern across the street. Gia was not old enough to drink yet and I knew exactly what the boss was doing. He set up every new intern with this test. Very few of our interns have ever been old enough to drink and he wanted to see if they would try to order alcohol with the rest of us or stick to the law. It was one of the few things that mattered to that man, skirting the rules for personal gain meant a lack of integrity in his eyes.

Vince’s nephew failed, trying to order a beer right off the bat. Gia ordered a cranberry soda. The boss nodded to me, a slight look of approval on his face. She passed. She got the internship and Vince’s nephew wouldn’t be back after today because he tried to pull a fast one on the waitress. I leaned over and whispered to Gia, “I think you’re in.”

She smiled and looked from me to my boss, he licked his lips as she blushed lightly and sipped her drink. When our food came out she leaned over and whispered, “What are the odds on your boss making a play for me?”

I coughed, stifling a laugh that wanted to bellow forth, “High,” I said softly.

Every guy at the table shifted uncomfortably watching me interact with my sister-in-law. We were comfortable with each other. As much as I wanted to lift her up onto the table and bang her in front of all of them, I refrained and carried on through the rest of the day as if it was absolutely normal. No one caught me fingering my sister-in-law or whispering lustful thoughts into her ear to make her squirm, no one caught me playing with the plug in her ass or the way she looked at me when I smiled at her. Most importantly, though, no one noticed me jerking off with Gia’s panties after lunch, nor heading to the bathroom just before we clocked out to put a fresh load of cum in the crotch of her panties.

When we got back to the car I handed her panties back to her, “Put them back on, baby girl,” I said with a smile.

She unfolded them and found an ample amount of wet cum on the crotch of her panties and a dried, stiff coating on the rest of the fabric, “This is just from you, right?” She asked as she carefully got them on her feet and up her legs. She moaned as the thick wetness of my cum rubbed against her pussy.

I nodded as I reached over and rubbed the fabric against her a little more, “Traffic is pretty bad heading home…We could stay here until it lets up a little,” I offered.

She nodded and bit her lower lip.

“Gia, you know I can’t take your virginity at home, right?” I asked.

“Why not?” She asked.

“Because you’re going to bleed and if your sister sees blood on a towel or on the bed or bedding and no tampons in the trash it’s going to be a little obvious what the blood is from,” I said.

“So how are we doing to do it?” She asked me.

“Does your sister know about the cam show?”

She shook her head, “If she does she’s never mentioned it to me. I haven’t gotten lectured, so no, I don’t think she knows about it.”

“Good. There’s a convention I have to go to with my boss on Friday, we’ll be back Sunday night. I want you on that trip. I know I can get the boss on board but Katherine might take some convincing. You’re going to convince her to let you go, but I have to act mad about it.”

She smiled at me, “So you’ll have me at the convention?” she asked.

I nodded, “Repeatedly. Now, when is your next show?” I asked.

“Tuesday,” she said, “I do them every Saturday, Tuesday and Friday. You don’t have to send money with the requests, you know?”

“I know. Is that what gave me away?”

“That combined with ‘baby girl’ made me question it,” she said with a smile.

“I’m gonna stop by the hardware store to get a lock for your door, do you need anything else to make things more comfortable for you to do your show from your room?” I asked her.

“Soundproofing,” she said, a smirk lingering on the corners of her lips.

I picked her up some soundproofing while I was there. I know she’d meant it as a joke, but it seemed fair that she be allowed some privacy and she records songs and puts them up on YouTube from time to time, so her wanting to record music in her down time after work seemed a good enough reason to soundproof her room. I took the time to set it up while she helped Katherine make dinner. While i don’t think she could freely scream in pleasure without someone noticing, it was enough of a dampening to allow her to get off if she wanted to.

Dinner was filled with laughter and smiles as Gia raved about her first day in the office and how everyone took to her almost immediately once they realized she actually knew what she was studying and was pretty passionate about it.

I complained about a few spreadsheets that I never quite got to finish in the office as we were cleaning up after dinner. Katherine looked to me, “Do you think it’ll take long to finish?”

“I don’t know. Depends on if the formulas cooperate or not. It’s two spreadsheets that just aren’t adding up right, so I have to have a mistake in the numbers somewhere. I need to go through the file and double check all of my entries for the entire month,” I said with a sigh, “I should be able to get to bed by two if it goes smoothly.”

“Gia, why don’t you help out? Sometimes a fresh set of eyes can catch a mistake you’ve been staring at but just don’t see,” Katherine said with a smile.

I shook my head, “Nah, I don’t want to keep Gia up to help me fix my mistake. I’ll be fine.”

“I don’t mind,” she offered, “Katie’s right. Sometimes you go number blind when you’ve been staring at the same problem too long and you need the eyes of someone who hasn’t been looking at them to catch it.”

I looked to Katherine, “You sure you don’t want to spend time with your sister instead of relegating her to unpaid after hours work?” I asked with a chuckle.

“I have my own work to catch up on and the kids need a shower before bed. I’ll catch up with Gia tomorrow night, no work is to be brought home the rest of the week though, yeah?” She said.

I nodded, “Swear, this one’s just been driving me batty and I need it done by the time I get in the office in the morning or I’d put it off indefinitely,” I said.

Gia and I went into my study while Katherine got to work dealing with the kids’ bedtime routines. I couldn’t do much with the risk of Katherine walking in at any minute, but I had Gia sit next to me while I filled out a meaningless spreadsheet. Listening to her little gasps as she fingered herself next to me was thrilling. I took the time to stroke my own cock a few times, carefully watching for Katherine to come in.

She did, eventually, and I put my head in my hands as Gia stared at the screen and pointed something out before Katherine even got the door open. “I’m going to bed guys, don’t get carried away and stay up too late, work can be finished at work too, ya know?”

I laughed, “You’re the queen of bringing work home, love. I won’t let Gia stay up past eleven and I won’t stay up past midnight, I promise,” I said.

Katherine smiled and turned around, closing the door behind her as we listened to her go up the stairs. The bedroom door closed and I picked Gia up and put her on my desk, “Pull your panties down,” I instructed.

She slid them down her thighs and I stopped her just above her knees. A quick tug on her thigh brought her ass right to the edge of the desk and I looked her in the eye, “Don’t move…”

She watched intently as I rubbed the head of my dick along her slit, gathering her fluids on me as I stroked my dick against her pussy. I could easily have pushed forward and stained my desk with her virginity, but I restrained myself and just came on her clit and hole before I pulled her panties back up her legs and lifted her from my desk so I could pull them up over her ass. Squeezing her cheeks gently in my hand as I pulled her against me, “Was that plug the first time your ass has been stretched?” I asked.

Gia shook her head.

“Have you had anal sex before?” I asked.

“No, I’ve used a dildo there on cam before, just a little though,” she said softly.

“Did it hurt?” I asked.

She shook her head.

“Good,” I said, “Tomorrow morning we’re going to use a bigger plug to stretch you more. Your ass is going to be the first thing I take at the conference on Friday, baby girl. We’re going to want to keep going up in size each day, maybe even again before bed, so I can open you up with my dick without hurting you.”

Her breath caught and I kissed her lips hard, holding her to me as I rubbed my fingers over her asshole, just barely dipping into her. We’d only used a small starter plug today, but I could get my thickest finger into her with ease, it took more effort to get that finger into her cunt when I tried. She kept her eyes locked on mine as she opened her mouth, trying to moan while she was afraid of being too loud.

I fingered her ass and kissed her jaw and neck. Her hands curled on my sides and I pulled my fingers from her ass and resumed rubbing her puckered hole with my fingertips. My lips lingered at her ear as I held her tightly against my body, “I still want to know why you’re doing this for me,” I said softly.

She smiled and looked at me, “What makes you think this is for you and not for me?” she asked as she tilted her head.

I furrowed my brow and let go of her to shut down my computer, “Go on to bed, Gia. I’ll give you the new plug in the morning after Katherine leaves for work.”

She turned and left and I sat in the study for a little while before I went into the half bath and scrubbed my hands of Gia’s scent. When I crawled into bed with my wife I half expected her to just know and start yelling at me for fucking around with her baby sister. But she just turned over and pressed her knee between my legs and pulled herself against me and whispered, “Love you, Billy.”

Well, that just erased the inkling of guilt lingering in my head.

Source: reddit.com/r/Erotica/comments/i2rtr4/careless_whispers_part_four_anal_wife_anal_play

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