Cheryl, Mom and I Hook Up

2019 was an eventful year for our family. Mom and Dad's divorce was final in November, ending a long and contentious settlement battle. A couple of months earlier my sister Cheryl and I filed for divorce from our spouses after discovering that her husband and my wife were having an affair. The picture of the two of them naked in our shower was certainly unsettling but did lead to uncontested divorces.

At midnight, New Year's Eve the three of us, Cheryl, Mom, and I toasted good riddance to 2019. While our lives had changed significantly, we welcomed the new year with optimism.

As I hoisted my glass I remember saying "Here's to a great 2020 and fresh starts for all of us."

The year started off alright. Our divorces were granted in January. Then I got a promotion and big raise, Cheryl also got a promotion, Mom got a huge advance on her new book. After the good start, things began falling apart. Covid reared its ugly head early on.

A major fire in Cheryl's apartment building displaced her. She put what she could salvage into storage and temporarily moved in with me. Shortly thereafter, Mom was diagnosed with Covid, apparently transmitted by her housekeeper. Her case was severe but thankfully didn't require hospitalization. So, Cheryl moved again, this time to care for Mom.

Fortunately, we all work from home. I create web pages for a multinational clothing retailer. Cheryl is a forensic accountant for a big three accounting firm and Mom writes mystery novels. We lived within a few miles of each other in the city in which we all grew up. The lockdowns, masks and social distancing didn't really impact us too much as we already spent our workdays at home and none of us had a very active social life as the pain from our divorces hadn't worn off.

I visited Mom and Sis regularly, helped with housework and maintained the yard. Mom's health improved but she was always tired and slept a lot. Often during her naps Cheryl would hang out at my house for a change of scenery. On one of her visits, she walked into my office and observed me viewing a page of scantily clad women.

Sarcastically she exclaimed, "Oh, into porn now I see."

"Not exactly smarty pants. I'm looking at talent for a lingerie shoot. I'm on a deadline and the files I received were corrupted. Rather than wait for replacements, the company asked me to take new shots."

"Shots of what?"

"A new line of bras. I'm looking for a model."

"Hey, let me be your model."

Laughing I said, "Be serious."

"What, you don't think I look good enough?"

"It's not that. I have to use an agency model with all the proper releases and such."

"So, I'll sign releases. You just don't think I'm pretty enough."

"Sis, I think you're gorgeous. Wait a minute. What size bra cup do you wear? I need a b."

"That's what I wear."

"Are you wearing a bra now?"

"Yeah."

"OK, take your shirt off. Let me take some shots to see how you look on film."

She pulled her top off.

She put her hands on the bra snaps and asked, "What about this?"

In college, I began having a wild and crazy friend in my head I call Willy. Willy's comments, "Go ahead jump", "Just do it", "You can make it", has led me to a lot of fun but also to some broken bones, trips to the ER and numerous traffic tickets. Lately he has been joined by a more conventional voice, "Look before you leap", "Is it really worth it", "Stop and think", etc. I call him William.

The two of them usually appear whenever I'm presented with an adventure opportunity like this.

Willy, "Have her take it off."

William, "Stay cool it's your sister."

Staying cool, I said, "Just leave it on."

I asked her to slowly turn around. Seeing no scars or skin imperfections, I grabbed my camera and snapped a few shots. We reviewed them on my monitor. I had seen her in bikinis but looking at her close up in a skimpy bra was arousing. I kept reminding myself, this is my sister.

Finally, I said, "Cheryl if you really want to do this, I'll try to get the agency to sign you. You'll probably have to be interviewed and maybe create a portfolio. And it's got to happen quickly. The good news is that if they sign you, you'll get paid."

"That would just be a plus, I want to do it because it'll be fun."

"Ok, I'll call them and get the ball rolling."

Of course, the agency signed her. It was like free money for them.

Within a couple of days, she was back in my office/studio for her shoot. I had told her not to wear a bra or any tight clothing to avoid skin marks that would show. The lights and backdrop were ready. I had laid 4 bras on the desk in different colors.

When she came in, I pointed to them and said, "Just pick one and put it on in the bathroom."

She was wearing the black one when she came out and looked great. I had her do a little straightening then started shooting.

Finished I said, "Good job, pick another one."

She walked to the desk and removed the black. Turned to face me, naked from waist up.

Willy says, "Grab a tittie."

William, "Don't, she's your sister."

Willie, "At least get a shot of those babies."

William, "Don't do it."

She picked up the pink and slowly put it on.

With her arms out to the side, asked, "What do you think?"

After a pause to catch my breath, I said, "Very nice."

She repeated the process of baring her tits as she put on the next two.

After the last one she removed the bra and walked to the bathroom. Coming out she had her shirt in her hand and moving in front of me slowly put it on.

She stepped up to me, grinned, gave me a hug, and said, "I like this modeling stuff, it's fun, and I'm getting paid. Thanks bro."

With her braless tits mashed against my chest, I kissed her on the forehead, and said, "It was fun for me too."

The next morning Mom had a doctor's appointment and Cheryl had a zoom meeting, so I picked up Mom and drove her to her appointment. As usual there was a long wait. Finally, back at the house Mom laid down for a nap and I went to say goodbye to sis.

She was still on the call. I waved goodbye, she held up a finger and mouthed "Almost done."

I sat down as she was wrapping things up. After a couple of minutes, she signed off, leaned back in the chair and asked how Mom's appointment went. I filled her in then stood to go. She also stood. She was wearing a nice silk blouse with nothing on below that. I'm sure I stared at her bare pussy.

She giggled, said, "Whoops" and sat back down.

"Do you always dress like that for your meetings?"

"I got up a little late, so I just threw on a blouse. They couldn't see anything but that anyway."

"You didn't have time to put on panties?"

"I never wear panties anyway. I don't like how they feel."

She stood up again.

With her naked pussy staring at me, she started walking and said, "I'll put on some shorts, you can close your eyes if you want."

I didn't want. I stared as she crossed the room, bent and grabbed a pair of shorts off the floor.

Willy, "Grab that ass."

William, "Don't do it she's your sister."

I wanted to grab but just stared and trembled.

In less than 24 hours I had seen my sister's bare tits, bare pussy and bare ass. The images were burned into my brain. I would later use those images to release some tension in my dick.

A few days later she showed up at my house. I took a break and we chatted on the deck. She was wearing baggy shorts. Knowing her naked pussy was inside them drove me nuts. It was somewhat hard to focus as those images kept flashing through my brain.

I was able to ask, "What have you been up to."

She replied, "You wouldn't believe me if I told you."

"Well tell me and I'll decide whether to believe you."

"Ok, you asked for it. An hour ago, I was jacking off our mother."

"What???"

"I was giving her an orgasm."

"Now I know you're shitting me."

"I knew you wouldn't believe me. Let me tell you how it started. She's been feeling better but was always fidgety and cranky. One day I told her she needed to unwind. Go have an orgasm and loosen up. She told me she'd never had an orgasm."

"Not even when she masturbates?"

"She said that she doesn't masturbate."

"Bless her heart. She's in her forties and never had an orgasm. That's sad but how did that lead to you...uh...getting her off?"

"Well, I kept bringing up the subject trying to get her to try. I even offered to masturbate in front of her, but she wouldn't look. One day she was lying down for a nap, I convinced her to let me rub her clit so she could see how good it feels. She couldn't watch so I covered her eyes with a towel and got her off with my fingers."

"Did she like it."

"Oh yes, said it was wonderful but still couldn't bear to touch herself. So, a few times a week we have our little sessions. I cover her eyes with a blind fold and have at it."

"So, she lets you give her a hand job but won't touch herself."

"Yeah. Crazy, isn't it?"

I laughed, "You're what I'd call a loyal daughter."

"Actually, playing with her pussy turns me on. I like to use my tongue. I like the way she tastes."

"You really eat her pussy?"

"She really likes that and sometimes I use a dildo though she doesn't like vibrators."

"Boy, I'd like to watch sometime."

"Come on over she'll never know."

"Let me know when, I'll be there."

The next afternoon she texted, if you want to watch, now's a good time. Be quiet, take your shoes off and tip toe to her room.

I tip toed quietly. As I entered the bedroom there was my mother naked on her back with her legs tucked behind her arms. Obviously, I had never seen my mother naked. I was surprised by how flexible and small she was and what a great body she had. Cheryl's face was buried in her crotch. I tapped her on the shoulder, she raised up and like a game show model, waved her hand presenting moms pussy. It was a full bush somewhat matted down by Cheryl's saliva.

Mr. dick began tenting my shorts. Cheryl grinned and pointed to it. I tried to turn away to hide it. Cheryl hooked her fingers in my shorts and pulled me closer. Then she reached in and pulled my dick out. With her hand firmly holding it she stood and walked us to the side of mom's bed.

"Hey mom, I got you a new toy. Here, feel it."

I couldn't breathe, just stood there.

Mom's hand squeezed me and said, "It doesn't vibrate does it.

"No, I think you'll like it."

With her hand on my shaft, she pulled/walked me back and rubbed the head up and down moms slit.

Willy, "Stick it to her."

William, "Stop. Don't, it's your mother

Cheryl grabbed my butt and pushed me inside. Nature took over from there. I hadn't been in a pussy in forever. Moms was warm and tight. I was slowly pumping her when Cheryl began tonguing her clit. With me pumping and Cher licking, soon mom began to tremble and breath hard. I couldn't hold back, just pushed in hard and shot my load. As I was pulling out Cher used her hand to wipe off the cum.

She asked," So, Mom what did you think of that toy?"

"It was nice, warm and the squirting thing was a surprise."

Grinning, Cher pushed me towards the door. I left quietly.

On the way home Willy and William had a lively discussion.

A couple hours later Cher texted, Have U 8 yet?

No

Don't cook I'm bringing carryout, chill some wine.

I was on the deck when she came out and started pulling boxes from a huge sack from our favorite Thai restaurant.

She said "Pour the wine I'm starved. Driving with this stuff in the car is worse than with bring home pizza."

I filled our glasses

She raised hers and said, "Here's to your first family fuck."

I nodded and said, "First and last. I can't believe you did that."

Munching on a stuffed shrimp she said, "So you didn't like it?

"No that's part of the problem I enjoyed it too much."

"Well, you have to do it again, Mom loved her new toy."

I almost choked on my pad Thai, washed it down with chardonnay then said, "Oh my god, what have you done?"

She said, "We'll talk later now I'm starved."

We ate in silence. She was wearing a peasant blouse, skirt and mid-calf strappy sandals. She looked great but I kept thinking about what was under her skirt. We both ate too much but it was so good. As we finished it was getting windy, so we cleaned up and went inside. I refilled our glasses, when I brought them in, she was sitting on the sofa. She patted the seat next to her.

I sat down at the other end. She turned and put her feet on my lap. I enjoyed looking at her feet and calves but my mind kept peeking under that skirt.

I started to say something, she said, "Before you say anything I want to say I know I should have talked to you before uh, you know. It just popped in my head after I saw your hard-on. Now admit it you liked it."

"Well after you put my dick in her, I just went with the flow. And I admit she's really nice looking and I was so horny, and it felt so good. It's just so... you know."

"Well, we did it and we're sort of committed."

I said, "Maybe."

She wiggled her toes and said, "My feet are tired will you take off those sandals?"

I undid the straps and slipped them off. Her skin felt so soft. I massaged her calves where the straps had left marks then rubbed her feet. After a few minutes I raised a foot and kissed her toes.

Willy, "Lift up that skirt."

William, "Don't you dare, she's your sister."

OK I admit I was hoping by raising her leg I could get a glimpse of her crotch. She raised her other leg and rubbed her foot on my face.

She said, "Oh that feels good."

"You have such pretty feet."

I started sucking her toes.

She said," Now that I'm a professional lingerie model and all do you think I could be a foot model too?"

I took her foot out of my mouth, held it close to my face and said, "I think you'd be perfect for it.

She lifted up her skirt exposing her cute pussy, "How about a pussy model?"

I couldn't take anymore. Didn't wait for voices, just dove under her skirt and buried my face in her pussy. She dropped the skirt over my head. I licked her sweet juices and sucked her clit until she had a small orgasm.

She pulled the skirt up and her blouse down, no bra just those perky tits and said, "Now do me like you did mom."

I yanked my pants down and drove my dick in as far as I could. Just stayed pressed into her for a while before slowly pumping her.

As I was coming, she said, "Kiss me."

With our lips locked and our tongues entwined I shot my second load of the day into a family member, this time without regrets.

We laid like that until she said, "Bro, can I spend the night?"

"Hell, you can move in if you want."

"I need to use the lady's room. Why don't you refill our glasses?"

I was pouring wine when she walked back in bare assed naked.

She said, "The wind died down, take off your clothes and let's drink these on the deck naked."

"The neighbors will see."

"We'll leave the lights off silly."

She sat on my lap. I loved feeling her skin against mine and enjoyed playing with her hard nipples."

I said, "What a day, I never saw this coming."

"Are you sorry."

"About fucking mom, maybe. About us fucking, no. I know it's not normal to fuck your sister, but I think you were wanting it too. After seeing your tits and ass I certainly wanted to. I didn't know how to suggest it."

"Oh, I did. I've been horny since the divorce. Since I've been doing mom, I've been masturbating several times a day. I may fuck you to death."

"What a way to go."

We made out in between drinks for a while.

Finally, she said, "I feel something hard sticking me in the butt. Let's get a shower and play some more."

We washed each other, not missing any vital areas then dried off quickly and jumped on my bed. She immediately sucked me into her mouth. I twisted her around so that I could lick her pussy. She had a nice orgasm just before I came. She swallowed my cum. We rolled on our side, she continued to lick me and play with my balls as I fingered her.

She was rubbing my dick on her cheek, said, "If you were serious about me moving in, I'll take you up on that. Mom is doing much better. I can still help her with the house and of course her needs."

"Good plan. I think we can have some fun and I've got plenty of room."

She scooted up and we enjoyed wet kisses before she pulled the covers back and stretched out on her side. I spooned her and we drifted off to sleep.

I woke up early, my morning wood pressed against her warm naked body. I spent some time just enjoying her presence and reflecting on the events of yesterday. I carefully pulled back the covers baring her cute butt with my stiffy nestled in her crack. She stirred, pressed back against me.

She softly asked, "Are you awake?"

"Yes."

"What are you doing? I feel something warm and hard?"

"Admiring your nice ass."

"You think it's nice?"

I scooted down and started kissing a cheek.

She said, "I'll take that as a yes."

She rolled onto her stomach. I gave her a couple of cheek hickeys then spread them and ran my tongue across her little puckered hole. Soon she was well lubricated.

She raised up on her knees. I took that as an invitation and rubbed my dick head along her crack, she pushed back and I entered her tight warm ass.

As I slowly pumped her, she started flexing her sphincter. It felt like her butt was jacking me off. Watching my dick easing in and out and feeling her squeezing me, I came way too soon. I kept it inside as long as I could. Finally, it popped out. Spent, I fell on the bed.

She moved over me, said, "That was so good."

We kissed then she moved up with her tits over my mouth. I sucked and licked them for a long time.

She scooted back down gave me a big kiss and said, "I've got to go, I have an early conference call. Come over this afternoon and we'll tell mom our plans."

I laid there for a while amazed at how I went from constant horniness to a satisfying sex life all in one day.

Just before lunch, Cheryl called.

"You won't believe this one. Mom and I were having lunch she asked if we could do it this afternoon. I said sure mom if you want. Then she said I want the new brother...ah I mean the new toy."

"So, she knows I fucked her."

"Yes, she admitted she can see through the blind fold."

"What should we do?"

"Why don't you come over this afternoon and we'll have a family meeting about this and tell her about my move at the same time."

"OK, see you later."

When I got to the house Cheryl was just finishing a zoom meeting. She signed off and stood up. A nice blouse up top and bare pussy below. She came over gave me a wet kiss while I fingered her pussy.

She put on some shorts and said, "Let's meet in the kitchen. I'll get Mom."

The three of us sitting at the table, Cher started, "Mother, you're feeling much better. I don't think I need to be here all day everyday so I'm moving in with Gene. I'll still check on you and help with the chores. Are you OK with that?"

"You're right I am much better but why are you moving in with??? OH, I get it you two are fucking, aren't you?"

"Yes Mom, we are. And we love it. As for you, he knows that you know he fucked you. So, no pretending. We do need to discuss where we go from here."

I said, "Mom it was wrong to fuck you when I thought you didn't know it was me. Now that I know you knew all along, I feel better. I hope you understand."

Mom said, "It's all right. I know it was your sisters doing."

Sheepishly she added. "And I enjoyed it."

Cheryl spoke up, "So the question is what about you? I've been getting you off quite regularly and now he's fucked you. Where do we go from here?"

After a long pause mom answered, "Cher, I want you to know you've really helped me get in touch with my body. I've even started masturbating. I'm so much more relaxed now. I sleep better than I have in years. I never thought I'd ever enjoy sex, but thanks to you I really do. Can we just go on? I mean with your brother also. I can even come to his house."