Mom's Family Villa Pt. 02

By Charlie Flemming

Copyright 2022 Charlie Flemming

Author's Note: ALL Characters are over the age of 18

Other Books and Series By Charlie Flemming

The Family Mansion

A Halloween Story: Sister Tricks Brother for Mom's Treats

Blackmailing My Moms

A Mother's Duty to Her Son

Caught Watching Mom's Porno

Donnie Dates His Family

Dr. Mom

DTF RPG

Eating Out (with) Mom

Family Massage Therapist

Final Family

Helping My Mother Pay Rent

Incestuous Medicine

Long Family Road Trip

Mom Punishes Son

Mom's New Addiction

Mom's Protein

Mom, Son, And Daughter Body Painted for the Labor Day Parade

New Thanksgiving Traditions

One Hung Stud

Porn-Watching Family

Robbing My Mom

Sex-Addicted Mom (and Daughter) Molest Sleeping Son During Quarantine

The Monster

The Quinn Family Halloween Costume Party

What Mothers Are For

A Complicated Family History

Family Facials

Mom's Family Villa

Buddy-MC

Bella-Mom

Sally-Sister

Cybil-Sister

Lexi-Aunt

Kori-Aunt

Amy-Aunt

Riley-Cousin, Aunt Lexi's daughter

Mary-Cousin, Aunt Amy's daughter

Mom really confused me when, after a full day of her ignoring me and acting too awkward to talk to me, we were pretty busy in different sections of the villa, but still. When I got in bed later, that's when Mom entered my room again.

"You don't mind if I sleep with you tonight, do you Buddy?" She asked. She was only wearing a very long t-shirt that hugged her front and I could see she wasn't wearing underwear.

"Um, I'm naked," I told her.

"Haha," she giggled like a schoolgirl but then caught herself, "Uh, I knew that. You always sleep naked. But I don't mind, just so long as you behave yourself." She gave me a wink. I had no idea what she was planning but I allowed Mom into my bed.

She snuggled up against me and buried her head in my chest. She seemed to be breathing in my scent. Needless to say, my cock was rock hard in seconds. I was already wondering if she'd give me another handjob or blowjob...

"Thank you for letting me share your bed tonight," she said as she ran her hand down my chest, almost to the point I thought Mom was about to grab my cock but then traced it back up my chest again, "I hope you don't mind if I do this every once in a while. I just like having a partner when I sleep...sometimes."

"Of course Mom," I said as I smiled down to look at her, she looked back up, her blue eyes reflecting the dim moonlight coming in through the window, "I'd do anything for you," I said, trying not to sound too corny while saying it.

But Mom didn't seem to mind the corniness. She smiled at me, a big toothy grin showing me just how sexy one woman could look as she rest her head on my chest. "Thank you, Buddy, I really appreciate it."

I kissed her then, just quickly on the forehead, and said, "I love you, Mom."

"Mmm, I love you too, son." She moaned softly and didn't say anything for a while but kept running her hand up and down my chest. Until she let it go all the way down and her hand grabbed my cock.

"Mom?" I asked in the dark, wondering if she was really ready to go through all this again. But she didn't answer. Instead, she just started jerking off my long and thick cock with one hand.

I enjoyed the feeling for a moment and then had a thought that maybe Mom had fallen asleep and was doing this in her dreams. It didn't matter, either way, my Mom was jerking my hard cock in her soft hands and I was going to take pleasure in the feeling, at the very least.

"Cum for me, son, cum for mommy baby!" She moaned softly, and I knew she wasn't asleep.

She was jerking me very fast by that point and I had been holding back as I wasn't sure if cumming on my sleeping mom would be seen in a positive light when she woke up, but upon hearing my mom's words I could no longer hold back. I started spraying her face with my cum, since her head was still laying on my chest and directly where my cock was pointing when I started to shoot.

"Oh fuck!" Mom moaned, no longer able to whisper, "This is a lot of cum!" She wasn't wrong, along with a huge cock I also have humongous balls that produce a copious amount of cum. Mom probably didn't notice before because she was swallowing it all but now, with her face getting the brunt of my jismic force, she couldn't get away from my barrage of jizz.

She also couldn't get enough, "Oh shit son! Cover me in cum! Give me a bukkake! Cover your mother like the cumslut she is!" She said, turning me on even more as I covered her face in my jizz.

My orgasm was so strong that I just fell asleep right after that. Mom was not in my room so I assumed she got up to clean my cum off her face and went back to her own bed after that.

***

After my morning shower, I decided to talk to Mom about what kept happening between us. I found her in her room.

"Mom?" I said as I came in.

She turned to look at me and glanced at my crotch right away, "You don't look hard, do you need some inspiration?" She asked.

"What?" I said, "Do you mean-"

"To show you my breasts again?" Mom said as she stood and took her top off, she wasn't wearing a bra underneath her sweatshirt today either, which was kinda weird considering how large her breasts were but now she was half naked in front of me.

And yes, my cock was rock hard in a heartbeat after that. I had completely forgotten why I came into the room.

Mom licked her lips and gets on her knees. I do nothing to stop her as she takes my pants by the waistband and pulls them to the ground. My cock popped out and she grabbed it with both hands, "Okay, we can't have you getting erections around all the women who will be staying here, so if you need more help be sure to tell Mommy about it and we'll take care of it." She said in a sexy baby girl voice as she jerked me. God damn, my Mom was turning into a really horny lady lately.

I tried to hold back and enjoy the moment but Mom kept saying naughty things like, "I love feeling your cum on my face. I want to wear it all day. Walk around with your cum dripping down my face. Lexi would ask me about it and I'd just tell her that my son just blasted a load of jizz all over his mother's face and- OH!" She moaned as I started to cum on her face as she wanted.

I shot one rope along the left side of her face and the second rope on the right but then mom opened her mouth and took my cock past her lips once again. She swallowed like an expert porn star taking the rest of my gigantic load of cum down her throat.

"Mmmm-mmm," Mom moaned as she swallowed the last of it, "I think I could probably learn to love the taste of your cum, Buddy. You're turning your mother into a real cumslut, you know." She gave me a wink as she took the cum off her face and licked it from her hands.

I pulled my pants up and felt I had to talk to her still, "Mom, don't you feel weird doing this stuff with me?" I just blurted out before I lost my nerve about it.

Mom shrugged as she ate the rest of my cum off her face and put her shirt back on, "Well, it's weird, but I'm having fun and I think you are too. If you want we can stop, but," she added, "I do mean it when I say that you can't have an erection all the time, especially once your other aunts move in and your cousins. I think, for now, this is a good enough solution." Mom explained this as I had just gotten a bump on my head and holding ice on it was a "good enough solution" to the problem "for now."

I do have to say, starting the day with a handjob from Mom did make the work that day a whole lot easier than the day before.

***

After our work was done, I got a text message from Mom that said "come to my room."

I wondered what she wanted and if maybe it was something sexual. My answer was given as soon as I went into her room. Mom was completely naked. When she saw me she got down and kissed me, "I just wanted to give you a very special thank you for all the help you've been doing for me lately." She explained as she got on her knees in front of me, a position I was really getting used to Mom being in lately, and she took my cock out again.

Once my pants were off she looked up at me and ordered, "Lie down on the bed."

I did not have to be told twice, I wasn't sure what was about to happen but I was ready, no matter what it was.

Mom got on top of me, and grabbed my cock but not so we could have sex, just the opposite. She pushed my cock on my chest and then sat so her pussy was grinding directly against the shaft of my cock, "I really want to make you feel good. I want to make us both feel good." She explained as she started grinding her pussy the full length of my shaft and then back down again.

This was the next best thing to sex, it almost felt like we were fucking as she did that, the hotness of her pussy and her cunt juices leaking down all over my cock and balls, it was practically like simulated sex with my mother. I reached up and grabbed her tits. I was loving this.

Mom surprised me by leaning down and kissing me, using her tongue and we Frenched on her bed while she continued to grind her pussy against my cock. I wished we were really fucking instead, but I supposed that beggars couldn't be choosers.

Soon, I was ready to cum, and I told Mom that I was and she got off me and took my cockhead in her mouth again so that she could swallow it all. This time, before she did, she opened her mouth and showed me that she had an entire mouthful of my jizz, before swallowing it all down in one mighty gulp and then showing me her empty mouth. She reiterated what she said that morning, "You're going to turn me into a cumslut, you know that?" Then she went to brush her teeth.

***

In the afternoon I came to Mom's room again, but this time just to ask her a quick question, "Mom when are you going back to work?"

"Um, well," Mom said looking a bit sheepish, she looked sexy when she was trying to hide something, but she always looked sexy so I guess there's no getting around that, "Well, I actually quit my job when I moved to the villa."

"Oh?" I asked, feeling a bit confused, "Then what about money? Should I get a job?"

"No, you don't!" Mom practically shouted before calming down, "No, your aunts will be paying their fair share of the villa and I'll be the landlady, so to speak." She smiled then, looking much less embarrassed, "And I was going to talk to you about that, well, maybe you coming on board and being my permanent assistant once the cleaning is all done."

I was taken aback. I mean, I was really looking forward to getting out of there, but that was before Mom started helping me with my orgasms...still, I knew Mom wasn't going to do much more than handjobs with an occasional grind session or sucking out my cum at the end for a partial blowjob, I didn't think it would get much further than that. I mean this was my mother, there's no way at all she'd want to fuck me. That'd be even less likely than my sisters or aunts fucking me and they hadn't even given me a handjob yet, unlike mom...

Being that we had grown so close lately, I decided to just voice my concerns, "Well, I want to find a girlfriend, and-"

"And you'll be surrounded by your family members and getting blowjobs from your mom, got it." Mom said looking a bit forlorn. I noticed she said "blowjobs" instead of handjobs or grinding so maybe she was already thinking about going a bit further. That gave me some hope but I still didn't want to fuck my mom, not really, even if she was the hottest person in the world and I was jerking off to her constantly... I don't know, I guess I was as confused about this as Mom was...

Still, I wanted to comfort her, "Mom, I love you. You know that right?"

"Yes, of course." Mom said, looking a bit angry at my attempt to coddle her, "I'm not looking for pity. I'm just upset you don't want to work for me."

"Ugh," I groaned, this is one of those Mom moments where you know if you agree and do what you want to, she'll be upset and hold it above your head forever, "Of course, I want to work for you Mom, I just want to find a girlfriend too." I conceded.

"Yay!" Mom said as she stood up and hugged me. When I put my arms around her, I put my hands on her ass without a second thought and squeezed her perfect buttcheeks with both hands. She didn't complain, instead, she said: "I'm so glad you're going to work for me, Buddy. You really made my day!" She then put her hand on my crotch, of course, my cock was rock hard with mom pressing her body into mine as I was openly fondling her ass, "Maybe I could thank you with a blowjo-"

Before Mom finished that sentence the door opened. Mom was just as suddenly five feet away from me and looking through her clean laundry as if that's what she was doing the whole time.

Standing at the door was Sally, my younger sister who was 18, "What's going on?" She asked as she looked at the two of us suspiciously. She saw my very obvious erection as well, "Why does Buddy have a boner?" She asked, surprising me profusely.

Mom didn't miss a beat and said, "Oh? Does he? I didn't notice." Then she looked at Sally like an angry mother would, "Don't look at your brother's erections, young lady. That's not a very sisterly thing to do."

Sally's eyes went wide with both shock and anger, but then she just shouted, "I HATE YOU!" And stormed off, slamming the door behind her.

I glared at Mom, very angry at her, "What the hell, Mom!?"

"What? She, uh, we, erm-" Mom started to stammer.

But I wasn't listening as I was already going down the hall and after Sally. I couldn't believe Mom would blame her daughter for the very thing she was guilty of! I mean, I knew that she was just covering for the both of us, but I was too angry to care at that moment. I just pushed my way in through her bedroom door. It was unlocked.

What I didn't expect to walk in on was Sally's ass, covered only by a pair of red, thong panties, so I could see both her ass cheeks fully. The rest of her body was under her bed. When she came out from under there, she was wearing a matching red bra and nothing else. She was also holding a dildo in the other hand. My erection had begun to go flaccid but it was now rock hard again as I thought about the perfect, half-Asian beauty fucking her beautiful body with that dildo.

I wondered if she was about to think about me...

I then realized she hadn't seen me yet because her back was turned. I used this opportunity to slowly close the door and walk away from her room and down the hall to my own.

***

I found Cybil right before she went on one of her walks. She was my blonde sister who was a year older than me and we got along most of the time, but lately since she saw my humongous erection (even though it was in my pants) she keeps having these moments when her eyes seem to just glaze over as she's staring at me.

"Hey Buddy," She said, then immediately looked down at my crotch even though I made sure my cock was completely flaccid before coming to talk to her. When it wasn't it was like nothing got through to her at all and she just spent the entire time I was talking to her looking down at my dick.

"Hey Cyb," I said back, "Do you mind if I join you on your walk?" I asked.

"Oh, sure, of course, Bud," Cybil said, breaking out of her trance. I walked beside her. I wished I could trust her enough to tell her about Mom and ask her if she thought I should keep working there when the cleaning was done but it was hard because I was having a difficult time with explaining that part of the reason I wanted to stay was that Mom was jerking me off topless when I wanted her to.

I almost opened up to her about it anyway, just not telling her the whole truth, but that's when Cybil tripped on a very obvious rock in the path through the back woods we were taking, probably because she had her eyes on my cock as I walked right next to her. And as she tripped I turned and grabbed her.

"Are you okay?" I said as I cradled Cybil in my arms.

"I, um, I-" My sister stammered before jumping out of my arms, "I think that's enough walking for now." She explained before walking back to the house. I never got to talk to Cybil on that walk as she ran ahead of me the rest of the way back to the villa.

***

Sally came at me next. She confronted me after Cybil went through the door leading into the resident's house in the villa and Sally came out of the door before I could go in.

"Ugh, what?!" I moaned in frustration as she came up to me.

"I know something happened between you and Mom and I want to know what it is!" She said as she came up to me and stood practically up to my chest and looked up into my face looking as threatening as she could when I was over a head taller than she was.

"Nothing happened, you're being ridiculous." I said with a scowl, "I've never seen you like this before. You're usually very shy around me."

That made her scowl too, "Oh, well it's not every day that your brother is fucking your mother!"

I did my best not to react in any way. I'm pretty sure I did okay, "What?" I asked, legitimately confused.

Sally stared at my face, probably waiting for me to give her a tell. But I didn't. It probably helped that she thought we were fucking and we hadn't done more than handjobs basically. But it was still kind of scary being put on the spot like that.

"Well, I may not be able to prove anything, but I think you're full of shit, Buddy." Sally said, "And I'm going to get to the bottom of this if it's the last thing I do." Then she walked away.

I think I may have peed my pants a little...

***

Though we didn't discuss it, Mom and I stopped fooling around for the time being. It was just too close with Sally before. And for the next couple of days, I spent it working and not really talking to anyone. I was still texting my cousin Riley as the only sane person left in the family, it seemed (myself included) but she was too busy finishing up school to come out yet.

But then it came time to move some more of my Aunt Amy's furniture. Unfortunately, Aunt Amy was a total fucking bully to me all the time basically. I was not looking forward to going over there.

What I didn't expect was to find Aunt Amy gone and my cousin Mary there instead. Mary was very much like her mother in that she was very mean most of the time. She was about average height but then a totally perfect female human specimen after that. Mary was strong, and she was beautiful. She liked to lift weights at the gym, she was one of those types of women.

"What the fuck are you doing here?" Mary said as she gave me a look like she smelled something awful.

"I'm here to pick up furniture, this was planned over a week ago," I said looking back at her annoyed.

Then her face softened and she was actually very cute when she wasn't angry, "Oh, yeah, I forgot that was today." And she helped me move some benches onto the truck I brought. She was a lot stronger than she looked, and Mary looked quite strong.

Mary and her mother weren't moving in yet though, and for that, I was grateful.