Are You Up?

"Are you up?" Ashley texted to her son.

Three simple words that would lead to a change in their relationship.

Landon had moved off to college a few months before, and Ashley and he texted often. Actually, they were texting now more than they did when he was at home. Landon had moved into an apartment he shared with a couple of other guys, though he had his own bedroom.

In the two-plus months that Landon had been at college, their texts had been non-sexual other than Ashley inquiring about his social life, if he was dating, if he had met any girls, that type of thing.

But on this Friday night, the dynamics changed with three little words.

"Are you up?" Ashley was having her second glass of wine as her husband had gone to bed early. She couldn't get into the book she was reading. Nothing good on TV. So, she decided to see what her 18-year-old son was up to.

Landon: Yes, I'm "up"

Ashley: Ok, I didn't know if you were still up

L: I'm very "up"

A: Ok... not sure why you keep putting "up" in quotes

L: Because I'm "up" mom

A: I know, we are texting

L: Mom, really I am "up" as in standing tall, erect, aroused

A: OMG

Ashley looked at that last text. Why would he be telling her this? She looked back at the top of the text chain to make sure it was her son. It was.

L: Sorry but I'm a little drunk and you texted at a time when I was browsing some porn. Just having a little fun with you

A: first of all, why are you drinking and second of all why are you watching porn?

L: Mom, it's no big deal. I had a few beers at home. I'm not driving. I'm not out making a fool of myself. I'm just drinking and got a little horny

L: And, I watch porn because I need some relief!

A: I understand guys your age need that release

L: Yeah, so it's no big deal. You always say you want to know what I'm doing, so....

A: Well with that, I will let you go back to your business

L: You don't have to do that. I can type one handed

A: OMG seriously?

L: What are you doing?

A: Well certainly not what you're doing! I'm just having my second glass of wine. Dad has gone to bed

L: Do you ever watch porn when he's asleep?

A: Landon, that's not any of your business

L: So, that means you do. What do you like?

A: I'm not answering that

L: I'm watching a vid of an older hot blonde woman with huge tits banging a college guy

A: If that's what you like, but I really don't need to know that

L: It is what I like. Hot, blonde, stacked

Landon wondered if his mom was putting together the likeness. Ashley, at 39 years old, was the definition of a MILF. She was a trophy wife, married to her second husband Bill, who was now 52, when Landon was just 2 years old. She worked out daily, keeping her ass tight and her stomach flat. That toned stomach made her 36DD tits look even more magnificent.

L: For some reason, that's what I go for. What do you go for?

A: I'm married, so I go for your dad

L: C'mon mom, I'm talking fantasy. Surely you have fantasies. Like right now I'm fantasizing that I'm the guy in the porn vid, driving hard and deep into that hot mature MILF

A: I can't believe you're telling me this. You do remember that I'm your mother!

L: What are you wearing mom?

A: What are you wearing? Wait, forget I asked

L: I'm totally naked

A: Why did I ask?

Ashley now couldn't help but picture her son lying on his bed, stark naked. She had seen him enough in swim trunks to know he had amazing abs, broad shoulders and strong, buff arms and a solid chest. She wiggled in her chair and took another sip of wine.

A: Are you about finished? I can't believe you're texting one-handed lol

L: Almost but I need something to get me over the top. Tell me something that will help

A: Like what?

L: What are you wearing?

Ashley again looked at her phone. Was her son really wanting to picture her in the dark living room... She sipped her wine. Her big tits sagged just a little, but were firm and sexy. Her butt was the creation of hours of squats at the gym. She looked good... but to her son? She hesitated, then typed.

A: A cami top and silky shorts

L: Wowwwww... bra?

A: No bra. I'm in my pjs

L: Are your nipples hard?

A: Landon!

L: Almost there mom! Please!

A: Use your imagination

A short pause.

L: omgggggggg

L: Fuck!

A: I guess you finished?

L: I did! Wow mom! That was incredible!

A: Well glad you can use two hands to text now! Go to bed! Good night

L: Love you mom

A: Love you too honey

Ashley finished her wine and noticed that her pussy was sticky. She absentmindedly rubbed it with her free hand, thinking it had been about a week since she had gotten laid. Her husband Bill wasn't the best fuck she had ever had but some dick was better than no dick, she reasoned.

Ashley slumped down in the chair and reached her fingers below her shorts. She slid her fingers up and down her slit, finding her clit. She dreamily started moving her finger in circles. Damn, she needed some release too. It wasn't her son that got her so worked up, she told herself. It's just been too long without an orgasm.

Her fingers kept circling her clit. With her eyes closed, she saw an image of her son, laying naked on his bed with his fingers wrapped around his bloated young cock. Damn, it just hit her. Landon was jacking off thinking about her... what she was wearing. Or more specifically, what was underneath her clothes. She moaned thinking about it. What is wrong with her? Nothing, Ashley thought, I just need to get off and get it out of my system.

She tried to muffle herself as she started cumming. She groaned, moaned and kept frigging her clit, having a quick but intense orgasm.

Ashley cleaned up a little bit and then went to bed and heard Bill snoring. She smirked as she thought that he has no idea what transpired here just a few minutes ago. She crawled into bed and drifted off to slumber.

The next day, Saturday, Ashley didn't hear from Landon all day. Was last night too awkward, she thought? Has this ruined our relationship? She fretted about what they had done. They had both been tipsy and a little lonely, but they shouldn't have pushed the envelope that far.

She texted him twice, once in the early afternoon and again right before dark. Just a simple "Hey!" and again "Just checking on you." No reply.

Ashley was really starting to worry about what happened the night before. They had gone too far, she worried. Gone to a place that a mother and son should not have gone.

Then, about 8 p.m., her phone dinged.

Landon: Hey you!

Ashley: Everything OK? I was worried

L: Yes, everything is great. I went hiking with some friends and we didn't have service where we were. Sorry, didn't mean to worry you

A: No problem. Just wasn't sure if last night had messed up our relationship

L: Not at all! Last night was fantastic! I've been thinking about it all day.

A: Whew, glad to hear that

L: I'm about to take a shower (naked again...) and then grab some dinner. Will you be around again tonight?

A: I can be, if you want to chat

L: Definitely. 11ish?

L: Oh, btw, what are you wearing?

A: What are you wearing? Dammit don't answer

L: About to get in the shower so I think you know. Swinging in all its glory

A: GO! We'll talk later

While Landon lathered up his hard cock in the shower and stroked himself thinking about how easily it was to flirt with his mother, Ashley could feel her own skin flushed and warm. What were they going to chat about tonight? She could only guess.

Ashley's phone dinged at almost exactly 11. Once again, hubby had been in bed for at least an hour. She was just starting her third glass of wine, which was one more than she normally had. She felt a little giddy, a little drunk maybe.

Landon: Hey hot stuff

Ashley: Who do you think you're texting? One of your college sluts?

L: No, I'm texting the hottest woman I know

A: Pffffft. Whatever

L: Seriously, I even changed your name in my phone a few weeks ago

A: What is my name now?

L: Hotmom

A: Ha! Ok if you say so

L: What is my name in your phone?

A: Landon

L: Change it

A: To what? Momsboy?

L: How about MomsBigBoy

A: Oh, big are you?

L: That's what I've been told

A: Well, you are about 6-2, so I guess that's accurate

L: Yeah, that's what I measure standing up. Laying down is a different story

A: OMG are you going there again?

L: I've had a couple of beers and feeling good. How about you?

A: Sipping my wine, as usual

L: What are you wearing?

A: What are you wearing?

L: Nothing at all

A: Do you always lay around naked?

L: I've started doing that when I'm chatting with you?

A: What is this obsession with me all of a sudden?

L: It's not all of a sudden. Mom you're smoking fucking hot. I've known that for a while!

A: Well thanks, I guess. So are you... doing it again?

L: Jacking off?

A: Yes

L: I am. Want to see?

A: NOOO

L: OK, just asking. Have you ever gotten dick pics? I'm sure you have

A: Every woman with a phone has gotten dick pics, I'm sure. Yeah, guys have sent me dick pics, probably dozens

L: And?

A: And, what?

L: Do you like them? Be honest! Don't be all mom-ish

Ashley looked at her phone twice. Mom-ish? He thinks I'm a prude? She took a drink of wine. I am NOT a prude and I'm not mom-ish, she thought.

A: Ok, honestly, some have been quite impressive. Not all men are created equal. Some have been pathetic and some have been like, that's just gross! Try manscaping, you hairy beast!

L: Any that you have replied to?

A: Maybe

L: Mom, give me a little something here

A: Yes, I have replied to a few of them

L: To the big, impressive ones?

A: Yes

L: How many times?

A: Probably only two or three

L: Which is it? 2 or 3?

A: Four

L: I just got harder

A: Glad my confessions can help

L: How far did the conversations go? More pics? Sexting?

Ashley took another drink of wine. Does she dare share those secrets with her only son? She loved the excitement their texts brought. She loved how she could get an 18-year-old so horny, even if it was her son.

A: Yes, some sexting. With one guy in particular

L: With who???

A: I won't tell you that. It's not fair to the guy, but he is a pastor in town

L: Holy fuck!!

A: Very well endowed. Like huge

L: I'm jerking it so hard mom. Tell me more

A: One handed again?

L: Yessssss

A: We were on a school committee together, so he had my phone number. He texted a few times about school stuff, then things got a little more personal. I remember your dad was away for about two weeks and I kinda got a little sidetracked

L: How personal did it get?

A: He told me his dick was too big for his wife. That it hurt her. I told him that he must be huge because that's never been a problem with my husband lol

L: Is dad little?

A: Average, let's say

L: So this pastor sent you a pic?

A: Yes, a lot of them. From all angles

L: What did you say?

A: I told him it was huge! It was! He took a pic with a ruler beside it and it measured 9 inches long. And very thick

L: Did it get you wet?

A: Blush

L: Did you finger yourself?

A: Blush again

L: Tell me mom! Did you masturbate with him?

A: Yes, we did phone sex and both got off!

L: Phone sex? Really? Damn that's hot

A: Yes, we did it twice but both felt so guilty that we ended it before it got more complicated

Ashley then felt her phone buzz and she looked down to see Landon was calling. She had to answer it.

A: Hey you

L: Mom, I'm almost there. Tell me what you told him on the phone

A: We just talked about what we would do to each other, but it was just a fantasy

L: Tell me

A: I told him I'd... suck it

L: Fuckkkkk

Ashley, hearing her son's lust-filled voice, became more bold. She wanted to make him cum, she wanted to be the reason her son shot his big load out of cum out of his teenage balls. She envisioned him with his long fat cock in his hand, stroking up and down.

A: I told him his dick was so big that I wasn't sure it would fit in my mouth but that I'd love to try. I wanted to stroke his huge dick and bring it to my mouth so I could run my tongue up and down the shaft and take it in my mouth.

L: Oh my gawd

A: I wanted to suck his bloated balls and taste his precum while I sucked his big mushroom head between my red lips. Then, I would wrap my big DD tits around his shaft and titty fuck him up and down. My firm tits riding up and down his shaft while I licked his cock head.

L: Ohhhhhh fuckkkkkk. Fuckkkkkkkk. (Landon panted into the phone, groaning and breathing hard) OMG mom I just blew all over the place

A: I'm so glad that I can help you! Did you like what I was saying?

L: Fuck mom! I came so much

A: Hehe, yeah, the pastor liked that too. He came pretty hard. He loved how naughty I could be.

L: Damn mom, I love how nasty you are too! Are you going to play with yourself mom?

A: Not right now, maybe later

L: Will you tell me about it?

A: Maybe, now get cleaned up!

L: Love you mom

A: Love you too honey

Sunday afternoon and Ashley's phone dinged. It was from MomsBigBoy.

Landon: Is dad taking his usual Sunday afternoon nap?

Ashley: Hey, MomsBigBoy. Yes, he is

L: So you did change my name

A: Sure, you asked me to... and it seems a little more fun

L: Will you do anything I ask you?

A: Lol, it depends.

L: I'm coming home for a couple of days. School is closing for the virus and will be online for at least a week

A: Oh baby I will be so happy to see you

L: Me too! I am so into our texting lately

A: LOL, I wonder why

L: What are you wearing?

A: Just a comfy sweatshirt and leggings. What are you wearing?

L: You know...

A: Again? My gosh, how often do you masturbate?

L: Lately, it's been every time we text

A: I've noticed

L: What kind of panties are you wearing?

A: None

L: Fuckkkkkkk

A: Like that?

L: OMG mom

A: No bra either

L: You're fucking killing me

A: Sorry, I'll stop

L: Don't you dare!

A: So, no bra and no panties

L: What kind do you usually wear?

A: Thong usually and as far as bras go, something that will hold these 36DDs

L: Damn mom

A: Don't you mean Hotmom?

L: Yesssss

L: When I get home, I want to take you shopping for underwear

A: Really? Thong shopping with mom? Hmmmmm

L: Yes mom

A: Ok BigBoy, we can do that. When will you be home?

L: Soon, right after I cum

A: Do it then baby, so you can come home. Do it

L: I want to send you a pic of it

A: Blush ok baby

Ding. Ashley's phone lit up with one of the biggest, sexiest cocks she had ever seen. It towered above Landon's waist, protruding out at least 10 inches. It was thick and long and powerful and sexy. Ashley mouth dropped open. She had no idea that Landon was working with such a huge tool.

A big blue vein ran up the side and there were red veins criss crossing it. Ashley couldn't help but admire her handiwork.

L: Do you like it?

A: Baby it is magnificent! I mean really! Wowwwww

L: Bigger than that pastor's?

A: Longer. Thicker. Sexier.

L: Really?

A: Longer. Thicker. SEXIER!!!!

L: Is it the biggest you've ever seen?

A: It's right there at the top.

L: So if it's bigger than pastor's, whose have you seen that as big as mine?

Ashley felt her pussy moisten. She loved big cocks and she loved looking at them and talking about them. Her mind raced to the biggest she had seen, which was very comparable to her son's cock.

L: Was it my real dad?

A: His was big but nothing compared to yours baby

L: Then who? Tell me

A: Do you remember your Uncle Wes?

L: Omggggggggg

A: I know you've only seen him once, when you were about 7 or 8, because he lives in Australia. But, yeah

L: When? How?

A: I was about your age and had been drinking at a party Wes was at. He took me home and I ended up laying down in his lap as he was driving.

L: Did he pull it out?

A: No... I did lol

L: Fuckkkk mom

A: I could feel it against my cheek and I was so drunk. I grabbed it through his pants and before I knew it, I had it out. Let's just say, your size comes from my side of the family.

L: Did you suck it?

A: Maybe

L: Fuck, I'm so horny. Did you fuck it?

A: Maybe

What Ashley didn't tell Landon was yes, she and her older brother fucked like rabbits for several years, until he graduated college and moved off to Australia for work. He came back once, about 10 years ago and stayed for two weeks, when they fucked ever day, usually all day long. She even took him back to the airport a day early and they rented a hotel room so they could fuck and suck for a day and half before he went back. His cock made her cum like no other. Now, her son has a look alike cock.

L: Ohhhhhhh fuckkkkkkkkkk

Her phone dinged and brought her back to reality.

L: Dammmmmmm fuck

A: Did you bust your load, MomsBigBoy?

L: I did, Hotmom. OMG you're sexy, I want to hear more about you and Uncle Wes!

A: LOL silly. See you soon!

Landon pulled up to the house about 9 pm, just enough time to get there to see his dad before he padded off to bed. Ashley was waiting up in the same outfit she had on earlier -- leggings and a sweatshirt with nothing on underneath.

Ashley wondered if their first meeting after their sexting would be awkward, but Landon ran up and hugged her like he normally would, though he did hold her tight against him a few seconds longer than normal. She felt him grind just a little against her. A peck on the cheek, with his lips lingering a bit long. Her massive tits pressed against his chest. But, that was it.

Ashley felt relief. She wasn't sure how she would navigate having him home for a week, but she was relieved that things seemed relatively normal in the meantime.

"Do you want something to eat, baby?" Ashley asked after Landon came back into the living room after dropping off his clothes in his own bedroom.

"No, mom, I ate on the way," he said. "I think I will take a shower before hitting the bed, though."

Then, Bill spoke up. "OK, Landon, glad you're home. I'm going to say my goodbyes because I'm heading up to bed soon."

Then there was that look. Landon glanced over at his mother and their eyes locked. They both knew what was coming.

"Ok, dad, see you tomorrow."

Landon retreated to his room and then Ashley saw him heading to the bathroom for his shower.

A few minutes later, her phone buzzed.

Landon: Is dad still there?

Ashley: Yes

L: Then don't let him see this

A: See what?

Next flashed up a pic of Landon's big cock, not quite hard but definitely not fully flaccid. It was larger soft than Bill's was hard. The glorious cock was something Ashley didn't think she would ever tire of. It was magnificent, even when not hard. Ashley kind of gasped, which made Bill look over.

"What's wrong, honey?"

"Oh nothing," Ashley lied. "I was just yawning."

"Well let's go to bed."

"Ok honey, I will be there in a few minutes."

Ashley: Take care of yourself tonight. I need to go to bed with dad or he will stay up with me

Landon: Ok, this will be waiting for you tomorrow

A: I have no doubt that as soon as one hard on leaves, another one arrives

L: You'll find out tomorrow

A: LOL damn that thing's incredible

L: I want a pic of you

A: What kind?

L: Your incredible sexy tits!

A: Ok, when I change, I will send it

Ashley went to her bathroom and slipped her top off. She had enormous, fantastic tits. Just a slight sag in the 36DDs but just enough to know they are real. Her big pink nipples were always hard, it seemed, and were especially now. She clicked off several pics at various angles and set them all.

L: Holy fuckkkkk! Your tits are even more incredible than I imagined! Mom, please stay up and chat with me. I'm dying here