There are defining moments in life that make you look at things or people differently.
For me, that moment came a couple of years ago with respect to my mother.
My mom and dad got divorced when I was 10. My dad really wasn’t in the picture much and my mom did her best at raising me.
The internet is a wonderful tool. It allows people to connect and act in ways that they normally wouldn’t. It also allows us to be someone we aren’t if the mood strikes us.
The internet is the means that changed the way I would look at my mom forever.
Shortly after school let out for the summer, I arranged to stay over at my friend Tim’s house for the weekend.
Tim’s parents were going to be gone that week, but his older brother Chris was going to be around.
Chris is a pretty cool guy over all. The only difference between him and his younger brother is the fact he is gay.
That never really bothered me, since he’s been ‘out’ since I’ve known Tim and he’s never shown any of ‘that’ kind of interest in me.
I arrived over at Tim’s house around 5. We didn’t have much planned, just thought we would play some Xbox, order pizza and soda and goof around.
Things were pretty normal until about 9, when Chris said he was going out for a while.
We knew that meant he might be home by 7am.
“OK, Cool”, was all we replied and he was out the door.
We finished up the game we were playing and Tim asked, “You want surf for chicks?”
“Sure, sounds like fun”.
We went over to the computer and Tim signed in under Chris’s account.
“What gives?” I asked.
“Chris doesn’t have any restrictions on his account, so we can browse anywhere we want”
“Awesome!”
For the next couple of hours we floated in and out of chat rooms trying with some success to chat with girls or find any nearby.
We talked with a few for a bit and arranged to chat more later.
We finally found one that wanted to chat, so Tim and I took turns talking with her.
All was going alright until she typed ” gotta pic?”
I looked at Tim, as if to say “Now what?”
I have pics on my computer at home but I’m not there.
Tim opened a file manager and went in to one of his folders and sent out a picture.
“Wanna see something gross?” Tim asked.
“Sure!”
Tim opened up one of the folders under Chris’s name. He clicked open a folder and opened one of the pictures stored inside.
The next thing I knew there was a picture of some 50 year old guy naked with an erection plastered across the screen.
“Yuck, dude, make it go away!”
Tim explained how each folder contains pictures of the guys that Chris talks with or meets up with online. He’s looked through some of them and found some really nasty looking guys in there.
“There are even pics of guys our ages in there too.”
I tried hard to get the image of the old dude out of my mind and focused on the conversation at hand.
That sweet “Mail has arrived” melody played and we promptly opened it.
Well, the girl we were talking with said she was cute, but that really is a matter of opinion.
She wasn’t ugly, but she’s not a model either.
We slowly separated ourselves from the conversation and moved on to search the web for porn.
About 2am, Tim said he was heading to bed. They had the spare mattress on the floor in his room for me.
I told him I would be in a little bit, just wanted to check out a couple more sites.
Looking at naked ladies is always a fun way to kill time and it was getting to me.
I decided I would go and browse around in the adult area chats for a bit and see what was going on there.
I went in and out of a couple of rooms before I came across one named “Moms and Sons”.
I entered the room and looked up a couple of profiles at the top of the room list.
Mostly bots for phone service or websites.
I watched a little bit of the conversation scroll and realized quickly what mom and son were doing.
There were a couple of “boys” looking for “mommies”. There was a lady looking for a guy to play her step-son.
I was getting ready to leave when I saw a message pop in the room.
All it said was “Hi Room”. But that wasn’t what caught my eye.
I looked at the screen name. It was MY mom!
I thought I was just tired or seeing something. Maybe it was a similar name.
I pulled up her profile and sure enough, it was my own mother.
“OK” I said to myself. “What is my mom doing in THIS room?”
I was about to go wake up Tim to show him when a different thought came over me.
Why not see why my mom came in here. Maybe I could find out some dirt that I could use next time I got grounded.
I decided to message her and see what I could find out.
I couldn’t decide what to type, so I did the lame “Hey, what’s up?”
I don’t believe I wrote that. Hardly anyone responded to that kind of a lame start to a message.
Surprisingly I got a response “Not much, just checking things out… you?”
“Thought the room looked interesting” I typed.
“It can be ;)” she replied.
OK, this isn’t my mother. She’s a nice enough lady, but flirting like this, with a total stranger?
“How old are you” she asked?
Now came the hard part. I needed to think of a lie I could keep.
Before I knew it I typed in my real age and sent it.
Oops!
I figured that would be the end of things, but again I was surprised.
“Kind of late for you to be up, isn’t it?”
“Parents aren’t home, so I figured I’d stay up a little late”.
“Oh, so you’re a naughty boy?” she replied.
OK, who is this mother I am chatting with?
Luckily Chris’s profile didn’t say a lot in it. It only said he was male, lived in this state, enjoyed biking, swimming and going to the gym.
“I have a son about your age” she added.
“Is that a problem” I asked?
“No, I like younger guys”.
My head was swimming after that comment. It’s hard to believe that my mother would be saying anything like this.
She’s always been pretty strict with me.
But, I was getting some good dirt for next time I got busted.
“Have you been with any?”
“A couple” she responded.
Oh? Now this was getting interesting. I was going to find out some good dirt on my mom.
Then she asked “What’s your name sweetie? Do you have a Pic?”
Oh no! Now what do I do?
I remembered back to the ugly dude’s pic and the other folders Chris kept.
I quickly looked through a couple and found a guy about my age that looked a little like me. The name on the folder said Dan.
“Dan, what’s yours?”
“Martha, nice to meet you” she replied.
That confirmed it, it was my mom.
“U 2. Yes I have a pic, do you?”
What am I doing? Asking to exchange picture with my mom? Hell, I know what my mom looks like.
“Yes, s2r” she answered.
“OK, here I go”, I thought. How much stranger could this night get?
I sent one of the Dan pictures that showed him from the shoulders up. No biggie.. Just something to through her off a little.
“Very nice”. And with that. “Message has arrived” chimed in.
I opened the email and to my surprise was a picture I have never seen of my mother.
I never really thought about my mom as being pretty or sexy before, but this picture sure changed that.
She was sitting on her bed with a blue, short, silk nightie on. She was sitting with her legs under her, and her hands on the bed. It looked like she was leaning forward a little and she had a very seductive look on her face.
The nightie was a little loose and showing some very nice cleavage.
I was stunned!
“Wow!” was all I could type back.
“I take it you like then?” she asked.
I tried to remember that this was my mother, but the picture didn’t do anything to remind me of her other then it looked like her.
“Very much” I replied.
“Good!”
“Did you have your son that that picture” I posed. Since I knew the answer I figured I’d go fishing a little.
“No, I took these with the help of his best friend”.
Huh? My best friend? Tim had taken that picture?
OK, that was not what I was expecting. Time to go wake him up and beat the crap out of him!
But first I wanted to find out how it happened. After all, I can kick his ass in the morning.
“Really? Does your son know?”
“Not that I know of, he wasn’t home when we took them”.
“Is that the only one he took?” I decided to see how far this all went.
“No, he took several pictures of me. We can trade more if you like?”
I opened up the folder again and sent off another picture. This time it showed the guy from head down to his abs.
“Mmm, very nice.”
I couldn’t believe my mom was writing these things to me. But I had to remind myself that she didn’t know it was me.
The picture that arrived from her was even sweeter then before. This time she was raised up on her knees and the straps of the nightie had dropped down.
She was looking down toward the bed and the top of the nightie was being held up by her hands just above her nipples.
It almost looked as though she was groping her breasts.
“How did you persuade him to take these pictures?” I had to know. I couldn’t believe my best friend took pics of my mom.
“Offered to give him a blowjob if he helped me”.
I felt dizzy. My mom? A blowjob?
OK, most of us try not to imagine our parents having sex. Let alone giving your best friend a blowjob. I didn’t even think my mom knew about those!
This was almost too much to take. I thought about signing off and running around screaming, but something else wouldn’t let me.
I kept looking at that picture of my mom and thinking, “God, how sexy!”
I wanted to see more.
My mind ran in circles. I was actually thinking of seeing more pics of my mom. Finding out more about her sucking off my best friend.
I guess you could call it the “Internet Syndrome”. I wasn’t myself tonight.
I opened and sent another picture. This time the guy had his pants open and you could just see the top of his pubic hair.
“So he accepted?” I asked.
“More than once”.
Huh? She’s done it more than once? Too crazy to be true.
“Is that all you did for him?”
“No” was all that returned.
I had to know more.
“What else has happened?”
“Message has arrived”.
I opened the email as I awaited the answer.
I almost didn’t hear the IM arrive.
My mother was leaning forward again with her hands on the bed. Only this time the nightie was bunched at her hips and her breasts were fully exposed, framed on both sides by her arms.
I swallowed hard. She had a great “Come heather” look on her face and her nipples were erect.
I too was erect. I had to think for a minute.
This is wrong! I’m getting an erection while looking at my own mother.
I clicked back to the IM and really got dizzy.
“I was his first”.
Tim had told me his first time was with an older lady he met at the mall. Though he never would tell me much about it.
I always figured he was bullshitting or something about it.
And here it is, the lady he met at the mall. My own mother.
“Is he the only one our age you’ve been with?” I asked.
I wanted to know how many other guys she’s been meeting online like this.
“I’ve met a couple and giving a few bjs, but he’s the only one I’ve slept with so far”.
So far? A couple?
I slowly asked more questions about the others.
She met a couple of them on “business” trips. I remember the trips being just one night.
Little did I know she took the day off to go meet guys.
She told me how she wanted pictures taken and she had noticed Tim checking her out.
He came over to get some of his games while I was at work and she persuaded him to help with the pictures.
She told me how she sucked him until he came, and then arranged to meet again to have sex.
I sent another picture. Trying to get one racier without showing it all.
The picture that returned was almost as intense.
My mother was lying sideways on the bed, naked. She was propped up on her elbow in one side and her other arm extended down her body with her arm and leg bent to hide her crotch.
I never really looked at my mom much before. I knew she went to the gym, but her body was kickin! She was toned, her breasts weren’t super firm, but they didn’t sag much.
“Lucky guys” I added.
“Do they call you mommy too?”
OK, I am just full of corny lines tonight I thought.
“Mom or Mother mainly”.
“I like it when they call me Mom”.
This is still crazy! I have a mother I never knew.
I attached one of the last 2 pictures I had in the file I was using. This was the one that showed the guy and his erection.
I could only imagine what would be returned.
The IM that returned caught me off guard first.
“Mmm, very yummy! Almost like my own son”
I had picked that folder because the guy looked similar to me, but I didn’t think he looked that much like me.
I wasn’t nearly as cut and not quite as big. Though I do hold my own at 7″.
“You’ve seen your son?”
“I’ve seen him coming out of the shower and I’ve seen him when he’s masturbated before”.
I felt myself turning red with embarrassment. My mom had caught me jacking off? And she didn’t say anything?
“Does he know you’ve seen him?”
“I do now”, I thought.
“Not that I know of. He doesn’t always close his door all the way”.
Note to self.. Close door.
“What did you do when you saw him jackin?”
“Watched”
“For how long?”
“Until he finished”.
“Then what did you do?”
Was this conversation getting weird to anyone else? I had just found out my mom watched me jack off and wanted to know what she did.
Part of me wanted to hear that she went away and felt embarrassed for watching and how she repented for doing such a thing.
But the other part of me was hoping for what came next.
“I went to my room and played with myself”.
“Message has arrived”
I nearly jumped out of my chair when the alert sounded.
Would this be my mom, in all her glory?
I was aching to find out. Aching so much I had to undo my pants and release my erection.
What I saw almost made me cum on the computer.
My mom was reclined at the head of the bed on her pillows. She was lying on her back with her legs spread slightly apart.
Her hands were up pulling her hair in a bun and had a big smile on her face.
As I followed the picture down, over her breasts, (38C I found out) down over her stomach and then…
My mom was almost completely shaven. She had a small brown strip that started at her bikini line and ended right above her slit.
I had always figured my mom did a regular bikini trim, with the big patch of hair all the way down.
I instinctively reached down and started to stroke myself.
All I could think of is my mom had watched me play with myself and then went to her room,
Laid back on her bed like in her picture and fingered her pussy.
And she did it while thinking of ME!
“I think your son would love to see you like that” I responded.
“I know I would!”
She sent back a wink first then replied, “I don’t know if he would be willing”.
“Oh, I’m sure he would!”
What was I saying? Was I really trying to hook up with my own mom?
Was she actually saying she wanted to?
“Do you want to be my son?” she asked.
“I am your son!” I wanted to send her. But that might backfire.
“Sure” I typed.
“Are you touching yourself?”
“I have been since your 3rd picture” I told her.
“Good, Me 2”.
I don’t think I could last much longer. The thought of my mom playing with herself was causing my balls to boil.
“Would you like me to suck on your son?”
The words danced in my head. I tried to fight the idea that my mom didn’t know it was me. She was talking to a stranger.
But I let myself in to the fantasy.
“Oh God mom, YES!”
She started telling me how she would start to lick my shaft. How she would use her tongue to slide up and down and her hand to stroke me.
She told me how she loves having me in her mouth.
It didn’t take me long before I had to type, “I’m going to CUM mom!”
All I got back was, “Mmm, cum in mommy’s mouth”.
With that I shot my load all over my chest and shirt. I don’t know if I had ever came so much playing by myself.
I felt completely exhausted.
“Thanks mom” I typed back.
“Anytime son”
With that she signed off.
I quickly copied the contents of our IM in to an email and sent it to myself.
Then I signed off and headed to bed.
It was 4:30am. I was tired but had a hard time falling asleep.
All I could think about was how to make that come true when I got home.
But that’s another story.