Simon Says Ch. 01

She laughed and smacked my chest gently. "Don't be mean to your mother. Go sit down, I'll get you something to drink." I sat at the table and she brought me a glass of juice. With her standing next to me while I'm sitting, her breasts hang at face height.

"Here you go," she said, placing the glass in front of me. She hesitated before continuing. "If you wanted to see if I have any milk left you could. It used to help you feel better," she ended, her tone clear that she knew that it was a lame excuse.

Before she even finished, my mouth was already attached to one of her breasts, sucking on her nipples. I wrapped my hands around her back while I teased her nipple. A part of me wished that she actually had milk for me to suck on. As I switched my attention to the other side, I realized that there was no reason why she couldn't. I knew that the process wouldn't be instantaneous, but unlike my sisters, I had planned the entire summer at home, so I had time.

Start producing milk, I thought at my mother as she held my head to her breast. The feeling of expressing milk is going to be a turn on for you, but someone drinking your milk straight from your tits is even more erotic for you.

My mother suddenly held my head even tighter and I could smell her arousal. I made no pretense of hiding it as my hands dropped to her ass. It was a glorious mix between soft and firm, and perfectly rounded as well. I lavished some more attention back on the first side, groping her behind as I did, before pulling away. By this point, she was panting, in the verge of cumming.

"Why don't you sit down next to me, Mom? You look like you are about to fall over." She sat down and I could see her squeezing her legs together. "You know, I've heard that it's easier for women to get off with their legs spread and playing with their clit than it is by clenching their thighs tight," I said in a dry voice.

"You don't think it's weird? You won't be embarrassed or disgusted?" "Of course not. You are beautiful and sexy. I would be honored if you felt comfortable enough with me to masterbate while I'm here."

I watched as she slowly spread her legs, exposing her trimmed pussy. She started out slowly and timidly, the embarrassment having dulled the edge, but it didn't take long for her head to be thrown back and her finger to be rubbing her clit furiously. I sipped my juice and watched as she brought herself to orgasm, her hips thrusting out of her chair as she moaned loudly. She settled back into her chair and looked at me, face flushed, and started to apologise. She rushed off to wash her hands, and I just watched her beautiful ass swaying as she went.

I finished my drink and headed to find my sisters. I found them already working on the lights in Andrea's room. I dropped down onto her bed and watched them work naked. I decided to play with them while they worked.

Every time Andy passes you something, you are going to squeeze one of your tits, I thought at Tiffany.

You can only bend at the waist to pick things up, I thought at Andrea.

I watched as they each began following my orders, seemingly unaware that they were doing it. Andy was the first to notice Tiff but just smirked at her. I could tell that she was sure that Tiffany was still worked up from the morning. When Tiff noticed Andy bending at the waist to pick something up, she smacked her upturned ass, causing Andy to jump. Tiffany and I both laughed, and I cancelled the commands.

"Andy, just how flexible are you?" I asked.

"And why would you like to know? Got something in mind?"

"I guess after this morning's display and then seeing you bend in half, I'm just curious," I responded while thinking at her that she should show us.

"Why don't I give you a demonstration?" She took a step back to make sure she had space and then began. She started with bending forwards, placing her hands flat on the ground, giving us the same perfect view of her ass. She then lifted her legs into the air and spread them until they were straight out in a split. I marveled at how strong she must be and wondered just how deep I could get in her with her spread like that. She then shifted again, bringing her legs down on the other side of her, bending her body in the other direction, with her back bent almost in half.

Tiffany and I whistled and clapped as she slowly stood up. Encouraged by our responses, she then proceeded to show how she could get both legs up behind her head and her hands forward, turning herself into a human pretzel. Her ass and cunt were both opened wide and her tits were on perfect display. "Do you want to see the craziest part?" She asked, seemingly unaffected by the position she was in. We nodded and she pushed even further back on her legs until she was just short of being able to lick her own pussy.

"I'm so close," she said, the strain now evident in her voice, "but I just can't do it."

I got up from where I was sitting and crouched behind her. "Have you ever tried getting help?"

"No, I was always too embarrassed."

"Tell me if it hurts too much," I said.

Thinking at her that she could do it and that she could bend more, I straddled her legs, effectively trapping her in her current position. I gently pushed her shoulders forward and put more weight on her legs, pushing them back. I watched as her mouth slowly approached her slit, her tongue out and eager.

As her tongue finally touched, she said, "ok, that's enough." I stopped pushing, but didn't get up any further than to release her a drop. "You can get off now," she said, her voice stained.

"You finally made your goal. I'm not getting up until I see you enjoy it."

"Fine, but if I end up with a strained muscle, I'm going to kill you." I watched as she began licking her own clit. I kept her at it for thirty seconds before slowly getting off her. She started to complain, but unfolded herself and did some stretches to relax her strained muscles.

"That was incredibly hot," Tiffany said, "but looked like way too much work for it to be worth it."

I spent the rest of the morning with them while they finished the room. I warned them that both of our parents had joined the trend they set, so neither was surprised when we got called to lunch. I watched my sisters give my father an unabashed detailed visual examination, and they both seemed satisfied with what they saw. I knew my father worked out regularly and from earlier I knew that I got my slightly larger than average size from him, so I wasn't surprised. It was the looks he gave them when he thought that they weren't looking that shocked me. I was wondering how long it was going to be before he fucked one of them. For a second I debated stopping it before I realised how much of a hypocrite that made me.

Our first naked family meal started out awkward, but after a bit, settled down to the normal banter. My father promised that the AC would be fixed by the end of the week, but I doubted that any of us were going to go back to wearing clothes inside on a regular basis. After cleaning up from dinner I called my mother into my room to talk. As she settled into the chair across from me, I sent a command to be open and honest with me.

"How are you feeling?" I asked curious what she was thinking at this point. She sighed.

"Honestly, Simon, I'm confused. On one hand, I'm your mother, and the fact that we are naked together, and especially what happened earlier, should bother me, and the fact that it doesn't, is weird. On the hand, I really liked having you suck on my breasts and touch my bare skin, even when you grabbed my ass which I don't usually like, and I'm still feeling kind of horny. Which is also weird, because I got off already twice today, once with your father and once with you."

"I get what you are saying about it being weird, but I've decided to accept it as the evolution of our love for one another," I responded, echoing the statement with my thoughts. "And if you would like me to touch you or suck on your breasts at any point, I'm happy to help out."

"You are so sweet. Tell me, have you had sex with your sisters yet?"

The question came out of the blue, but I went with it, since it headed in the direction I wanted. "Tiffany gave me a blowjob and Andrea and I had sex. Is that an issue?"

"No. If you are all happy with it, then I'm happy for you. It's not like you would want to do anything with your old Mom anyways."

"Come here, Mom," I said, holding open my arms to her. "Not only are you not old," I continued once I was holding her, "but you are sexy as hell. If I hadn't just cum twice right before, I would have exploded watching you this morning. As it was I had to exercise a lot of control not to play with myself." I held her tight with one hand and gently caressed her with the other, running my hand down her back, across her ass, down her legs, and back up.

"Do you really mean that?" She asked in a soft voice.

I took her hand and placed it in my crotch. "What do you think?" She grasped my erection and slowly started playing with it. "What did you mean earlier about me playing with your ass?" I asked while reenforcing my earlier suggestions about liking my playing with it.

"In general I don't like butts. Especially not my ass. And don't like it when anyone touches it, but for some reason, when you touched it earlier, it set off a spark of pleasure."

"You have an amazing ass, Mom," I said, gently caressing her ass. "You should be proud of it. I'm happy that you like me touching it."

"And why is that?"

"Well, firstly, it's an amazing ass and I would be sad if I couldn't play with it. Second, since I've had Tiff's mouth and Andy's pussy, that means that as the remaining family member...." I trailed off running a finger down her crack and sending thoughts at her about how hot it would be if her son fucked her ass.

"What about your father," she asked softly, sighing into my chest as I swiped her asshole again.

"What do you mean," I asked, not sure where she was going with this, but assuming that she felt like she was cheating.

"You haven't fucked him either."

"That's a conversation for later," I said, pushing the thought out of my mind. "For now, I think that we are going to focus right here," I said, resting my finger on her rosebud.

"And since I'm old and last, I get stuck with the butt. Is that how it is? The rest of me isn't good enough?"

I sent a flurry of thoughts before responding. You are beautiful and sexy. You are loved and adored. You want to get fucked in the ass, especially by your son. You will give him your body completely if he asks. You love how dirty it is that your son is going to fuck your ass.

"You are not old. We covered this already. And while yes, you are last this round, I plan on fucking your mouth and the pussy I came out of. I'll even let you go first next round and pick."

"I'm scared. I've never had anything up there before."

I realized that not only was I going to be fucking my mother in the ass, but that I was going to be taking her anal cherry. I should have realized earlier from what she was saying, but I was too distracted. You love how dirty it is that your son is going to be the first person to fuck your ass, I thought at her, wanting her to enjoy this as much as I was. "I promise to be gentle, and that you will enjoy it," I said, lifting her face and kissing her on the lips.

A dam seemed to break and she kissed me back hungrily. I let myself enjoy dueling tongues with my mother for a few minutes while my hands explored her body, but I didn't let her distract me for too long. I rolled her onto the bed and onto all fours with her ass in the air facing me. I tried to hold myself back, but I couldn't resist.

SMACK! SMACK! I landed two quick slaps across her ass. I was ready to adjust her response if needed, but I was shocked by her response.

"Ohh," she gasped, "that's right. Spank your dirty mommy. Spank her harder."

Never one to disappoint, I applied myself to the task at hand.

SMACK!

"Ahh."

SMACK!

"Yes!"

SMACK!

"Harder!"

SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK!

By the time I was done, her ass was red and she was mumbling that I should use her like a dirty bitch, her face was flushed, and she was panting. I was ready to move onto the main event. I stared by pouring a liberal amount of lube around her ass, and pressing my finger against her heretofore untouched anus. I slowly pressed in to the sound of her groaning. Her ass was so tight as it clamped down on my finger.

Relax your ass, I thought at her, and I could feel the immediate loosening as she complied. I pulled my finger out, re-coated it, and slipped out back inside, going deeper than I had the first time. I repeated the process a couple of times until I was knuckle deep in my mother's ass. Each time I pressed in, she let out a combination of a groan and a moan. Still with a single finger, I began to fuck her ass, slowly at first, but building up speed when I was sure there was no resistance.

"Oh, god!" She cried out. "I don't know why I was so scared of this. Fuck my ass harder!" I laughed and slipped another finger inside her, causing her to yelp. Not letting up, I continued stretching her open, adding another finger once she adjusted to the thrusting.

When she was panting from three, I decided she was ready for me. I pulled out my fingers and chuckled as she protested the emptiness. After pouring more lube onto my cock, I lined it up at her now eager hole.

"Are you ready to lose your anal virginity?" I asked.

"Yes!"

"Are you ready to be a real dirty slut mommy and get fucked in the ass by your son?"

"Oh, god, yes!"

"Are you going to beg me to take your ass hard?"

"Please fuck my ass. Fuck it hard. Make your dirty mommy into your little anal bitch!"

As she yelled out the last sentence, I noticed the door crack open and Tiffany peeked in. I winked at her as I pressed my cockhead against our mother's virgin asshole. My mother moaned loudly as the rim of my head pushed past her sphincter, stretching her even more than my fingers had. I slapped her ass again before starting to press in. As the first inch spread her open, she started fingering her clit and begging for more. I pulled back and pushed forwards a bit deeper, making her groan again. I thrust gently in and out, working my way into my mother's no longer virgin rectum, to the symphony of her fingering herself and urging me to fuck my dirty mommy deeper.

The next surprise was that as I finally bottomed out in her ass, with my balls pressed against her cunt, she started cumming. I looked over at Tiffany who until now had been playing with herself, stopped and stared in awe as our mother shook and moaned a litany of oh god's with my dick buried inside of her. I gave my mother a minute to adjust before slowly pulling all the way back out until just the tip was still inside, and then pushing back in slowly. As I did I could feel her ass still pulsing as she continued orgasming. I went slowly a few times before starting to speed up. I slapped her ass a few more times as I picked up speed, but after a few sharp strikes, I instead reached for her hair. I pulled her head up as I slammed back into her. She yelped in response and I could hear her eyes bulge out.

As I began fucking my mother's ass as hard as I could, I motioned to Tiff with my free hand, still holding my mother's hair tight. My sister quickly understood what I wanted and scrambled into bed and into position before our mother could react. I thrust in hard and leaned forward, dropping my grip on her hair so that my mother's face buried itself in her daughter's pussy.

Tiffany grabbed our mother's head and said, "that's right Mom, lick your daughters cunt. Get deep in there you slut."

I pounded her hard from behind while Tiffany held her head in place. Tiffany threw her head back in pleasure and I felt our mother start cumming again between us. I knew that I wasn't going to last much longer, so I started spanking her again as I slammed my cock into her a few more times. Burying my cock inside her ass one last time as deep as I could, I let out a growl of pleasure as I emptied burst after burst of hot seed deep into my mother's bowels. I could hear her yelling out in pleasure even muffled by her daughter's pussy. I held there a while as Tiffany keep our mother in place, but eventually I pulled out with a loud popping noise. I watched as my mother's now defiled anus contracted slightly, but did not close all of the way. I gave her another slap on her already very red behind, and climbed onto the bed.

I was going to lay down and enjoy the show, but then I had a better idea. "You are still on cleanup duty," I said to Tiffany, standing up on the bed. She started to protest when I grabbed her head and shoved my dirty cock into her mouth. Clean it, I thought at her, and felt the command take hold.

"Tiffany told me earlier just how much she likes butts. I'm sure that after the taste she is getting now, she will be happy to clean yours in the same way," I said, looking down at Mom, who was still licking Tiff's clit.

Once I was sure that my now deflated cock was clean, I dropped down into my bed. I watched as my mother got my sister off again. Tiffany let her go and slumped back. I pulled Mom, who by now was wrung out as well, to me for a kiss and sent a command back to my older sister. Tasting pussy on my mother, I watched as Tiffany crouched behind Mom and stared licking her ass, cleaning the cum that had started leaking out. When she finished cleaning, I pulled her up and we cuddled for a bit, recovering from our exertions.

After a while, I was rested enough to get up and I shook both the women who were resting on me. "You both need to go brush your teeth," I told them, sitting up. "And while I don't mind the taste when it's fresh, stale pussy is not my favorite, and no offense, Tiff, but neither is ass."

They both laughed, and we got up. Walking down the hall, we heard the sounds of sex coming from Andy's room. We stopped by the open door to see Andrea with her legs once more behind her head and Dad pounding deep into her.

"I. Was. Showing. Dad. Just. How. Flexible. I've. Become." Andy said when she saw us at the door, panting between each word. I noticed that Dad refused to look at us. I guessed that he was either embarrassed, ashamed, or angry. I pushed Mom into the room.

"Go join them," I said quietly. "I'm sure Andrea would be more than happy for you to ride her face." Tiffany and I watched as our mother approached our father and sister. They didn't stop fucking until my mother gently laid a hand on my father's back. He stopped and turned his head to look at her, but we couldn't see his face from our angle. All we could see from our position was her take his face in her hands and kiss him.

After a moment, she pulled back, looked him in the eyes, and swung a leg over their contorted daughter and settled on her face. "Fuck her good," Mom said encouraging, and ground her pussy against Andy's face.

Tiffany and I watched as our parents rode our younger sister for a minute before I dragged Tiffany away. Mom and Dad were kissing while we headed to the bathroom.

"On your knees," I told my older sister, "I need to piss really badly." I expected her to protest, but she obliged without comment. Placing the tip of my dick in her mouth, I relaxed and started peeing. I saw her desperately trying to swallow, and tried to slow down so she could catch up. At the end, all of my piss except for a few drops ended up in her stomach. Like a good slut, she licked my tip to get the last drops and then washed her face and brushed her teeth.

We finished up and went to watch some TV before bed. I wrapped my arm around my older sister and gently played with her large breast while we watched cuddled up. Halfway through the show, the rest of the family stumbled in. Our parents sat together and Andy took my other side. We watched for a bit before everyone decided to go to bed.