The Newbie

 

The Newbie

I had a thing for guys my Son’s age, and frankly, I blame my husband. See, “Mommy” was 

always a fantasy of his, and I loved sex in all its forms, so I spent years playing Mommy for my 

Husband, even as our Son grew up. Then, kind of out of nowhere, I realized that my Son and his 

friends had, at some point, all become hot young highschool guys, and… the fantasy took on an 

uncomfortable new aspect. Suddenly when my husband was asking me, in character, if I would 

ever let “my son and his friends” fuck me, I was picturing some very specific people. 

It was hot! Like, really hot! And like any fetish that you discover in yourself, there is not a lot of 

point in denying it. So, eventually, I confessed to my husband that our fantasies had gotten hotter 

lately, and I told him why, and uh… he fucking loved it. Because OF COURSE he did… So, not 

only was he not helpful in curbing my interest, but from that point forward, he wanted to hear 

about very specific scenarios where I would seduce and fuck our Son and his friends. And, god 

help me, I wanted to think them up, so, there we were. 

Fast forward a quick year or two, and my husband couldn’t stop pointing out that my Son’s 

friends were all 18 or older by now, and that we, as very active members in the swinger 

community, could invite them along to a sex party or an event. Obviously, they would have fallen 

over themselves for the privilege of tagging along. Which would, naturally, open up some 

opportunities for us. 

Mostly, I ignored him. Because, mostly, fantasies and reality have their own little zones, and it is 

pretty rare that they meet. Until one day, he was teasing me while our Son’s friends were over so 

they could game with him, and I thought I’d flip it on him. So, when he teased that we should 

invite, 1-10 of our Son’s friends to the party that weekend, I retorted with, “Why invite his friends, 

when could invite him. I mean, he’s 18, inexperienced, and hard 24-7. Besides, then you would 

get to see actual Mom/Son sex.” 

Thing is, my pussy may have twitched as I said it, but I was still kidding! That, however, went 

over my husband's head. He not only agreed, but he started ranting so fast about how amazing it 

was, and how he could set it up, and how he couldn't believe I finally agreed to it… I could not get 

in a word in order to shoot his delicate little dreams down. Plus… the more he described it, the 

more I liked the sound of it.

But, no! I was certain… okay, almost certain, that having sex with my own Son was a hard no 

from me, no matter how hot it seemed! Still, I let my husband convince me into inviting him. Not 

to have sex with us, but just because I really hadn’t been lying about the inexperienced bit. My 

Son was sweet, kind, polite, and even handsome. But he wasn’t very confident with girls, and, 

fun fact, if you don’t ask women out, they won’t date you. 

So, we agreed that we would invite him along. We would introduce him to the lifestyle, get his 

cherry popped, and see how he felt about going to such a sexual venue with us. Plus, that 

weekend was perfect. It was anime week, and all three of us were fans. So, we each picked 

some Naruto costumes, and off we went. 

Of course, our Son went as Naruto. So, of course, my husband wanted me to go as Naruto’s 

Mom, Kushina, but… I was actively trying to be good, and that would have been a bit too much 

for me. Besides, if you go to an event like that as naruto’s Mom, you are going to end up in a 

Mom son/son/son/son/son/son gangbang. And… as much I loved the sound of that, I figured it 

would be a bit much for my Son’s first time at an event, to risk him walking in on that. Especially 

dressed as Naruto!

So, I was good. I behaved.

I dressed as Temari, brought a variety of Japanese themed, and Ninja themed, slutty outfits; put 

my hair up in pigtails, and, with hubby dressed as Nara, we were off. My husband scooted off 

and found some play partners pretty early on, but I wanted to hang around with my Son and 

make sure that he was okay before I ditched him at a hotel full of horny swingers. 

A few problems sprang up though… First, even though I didn’t go dressed as Naruto’s Mom 

(Kushina), several others did, including our busty next door neighbor (a fun rival/friend of mine). 

Not an issue by itself, but my Son could not take his eyes off of her! Which, on the one hand, she 

was his sexy, big titted neighbor, so maybe it was just that. But on the other hand, she was 

dressed like ‘his Mom’, and what if it was that instead?!? 

Eventually, I decided to pretend that I wasn’t obsessing over it, and, ever so casually, I advised 

my Son to go over and talk to her. He, kind of shyly brushed it off, but as we continued to walk 

around, he continued to seek her out with his eyes, and I was worried that this, the most open, 

friendly, “easy to get laid in” environment on Earth... might actually be too high a difficulty for my 

baby boy. And that was seriously worrying me!

I was getting really, genuinely concerned. So, I decided to confront him, and not back off on it. I 

took him aside, and insisted that he explain, in detail, why he wasn’t going up to “Kushina”, when 

he OBVIOUSLY wanted to! He tried to shy away and deflect at first, but I made it very clear, very 

quickly, that I was not going to back off on this. So, after a bit more attempted avoidance, he 

finally confessed that he COULDN’T go over to her, because he couldn’t “calm down” enough to 

stop sporting a hard-on. 

Now… he had a point. See, generally speaking, if you go into certain kinky or sexual 

environments, a boner, uninvited, is seen as a lack of control. Like, you can’t be trusted to control 

yourself among people who consider your environment “normal”. Some people LOVED it, but 

many considered it taboo to walk around with a hard-on. I was trying to find a way to explain that, 

while he was normally right, this particular play partner wouldn’t see it that way, when he 

suddenly blurted out that it was also weird for him because he liked her costume.

At first, I gave a little snort of laughter, because, of course he did, it was very much meant to be 

sexy. But, as he looked down and away, his blush growing, I had a eureka moment, and ended 

up blushing a bit myself. Did my Son just confess a Mom fantasy to me?!?!

There was almost a minute of him looking away, red as a beat, while I, internally, tried in vain to 

stop shrieking in delight. But, in the end, I was as delighted by his confession as he was 

embarrassed by it, and there was simply no getting around that. Still… this wasn’t about me, it 

was about him. And before I was a slut, I was a Mom; that was a decision that I’d explained to my 

husband YEARS ago. 

So, I put my own excitement aside, assessed the situation, and worked out a solution. First, I put 

a finger under my boy’s chin and brought his face back to me. I explained, with patience, 

kindness, and loving understanding, that this was a place where people didn’t get judged for their 

kinks. Then, I made his jaw drop when I explained to him that his “secret and shameful” fantasy, 

was basically the most common fantasy on Earth, and acted as the archetype for half of all other 

fantasies. I sealed the deal by telling him, ever so briefly, that even his Dad… and I… were into it. 

Then, before he passed out from shock, I explained to him that, if he could get over his hangups, 

I could help him; and he could end up bedding his hot neighbor. It took a few minutes, but 

eventually, he calmed down some, and agreed. It took a few more minutes of calming when I 

explained that step 1 was me getting him off real quick so he didn’t walk over there with a boner 

that was primed, loaded, and ready to go off at a moment's notice. After he was calmed enough, 

and in agreement, we walked to a little grotto with semi-privacy. 

There, I backed him into the wall, and turned around so that my back was facing him. “Ready?” I 

asked, with a seductive purr in my voice. After a second, I gently reminded him that I couldn’t 

hear him nodding, and he would need to answer out loud. But a moment later, he confirmed that 

he was ready, and we got started on, what I was sure, would be a very short, but fun little 

adventure. 

The moment I had his confirmation, I reached down and behind me, slipped my hand into the 

front of his pants, and thrilled at his moan, as his Mother’s cool, delicate fingers curled around 

his cock, and drew it out into the open. He was gritting his teeth, and his whole body was tense 

as I gripped him gently. After he had a minute or so to adjust, I instructed him to reach up to my 

shoulders, and pull the material off of them, so that my top would drop down some. 

He was lost in a cloud of lust. His pulse was throbbing in the veins that I could feel against my 

palm. But, I explained again, and told him that he needed to expose his Mother’s tits to anyone 

who wanted to see them. The moment I said it, he gave another sharp intake of breath, hissing 

through his teeth; and his cock bucked, jumping in my grip. 

I liked that…

But I was patient with him, and eventually, he pulled my top from my shoulders. It wasn’t enough 

to do what I’d asked though, so I told him to reach around the front, grab the material, and pull it 

open like a robe, so that “Mommy’s big tits” were out. Again, his cock jumped, his veins 

throbbed, and he took a moment to catch his breath before he could act. But soon he had my 

breasts out. 

Then it was time for the final step. Because, again, there was no way this was going to last. But 

he was young, and verile. So I knew he would recover quickly. I told him that, when he was ready, 

he needed to say, “I’m ready to cum Mommy”, then he had to reach up, grab my tits in both 

hands, and just squeeze, and play with them as rough and as needy as he wanted. 

At that, he started to stammer, and push back again, but I cut him off quickly. I told him that I was 

the more experienced, and he was in no position to debate. To drive home the point, I gave his 

cock a gentle squeeze as I said it, and I felt his knees tremble in response. “So…” I clarified. “Is 

that a, Yes Mommy; or is that an, I’m not ready for this and need to call for a ride home?” 

The threat of having to leave was massive. But I knew he wanted this, and he quickly said 

okay… 

Of course, I didn’t tell him to say okay. So, with a gentle verbal nudge, I let him know that he 

hadn't really answered my question, and after a moment, I heard it dawn on him as he replied, 

“Yes Mommy”. And, I swear to god, I could HEAR him blushing by that point. 

A moment later, he gathered up his nerve, said, “I’m ready to cum Mommy”, and reached up to 

grab my tits from behind. The moment he got a good grip, I pushed my ass back, and moaned 

Loudly....

And that was all it took. He grunted out a surprised, “FUCK!”, that was part moan, part whimper, 

and I started moaning, and telling him how hard he was, and how big his cock felt in his 

Mommy’s hand, as I jacked him hard and fast. Within moments he was moaning, and cumming, 

and his grip on my tits got so tight that my own moans had very much become real.

My own Son was squeezing my tits from behind as I stroked him to orgasm and I wanted, 

DESPERATELY, to shove my free hand down the front of my outfit so I could join him in 

cumming! But… that wasn’t what I was there for. So, instead I drank in that moment as best as I 

could, trying my best to not be selfish; as I milked his cock for all it was worth. 

When he was well and truly spent, I turned around, tits still bared, and as he stared at my 

breasts, panting and still glowing with orgasmic pleasure, I lifted his chin up, told him Mommy 

was proud of him, and gave him warm, deep, expertly delivered kiss that had him moaning in my 

mouth and unconsciously thrusting his cock into my newly acquired grip, and basically fucking 

my hand on instinct. 

To my surprise, he didn’t even need to get hard again, because, some fucking how (god bless 

teenagers), he was still hard! So, we got him redressed, got me redressed, and, even though he 

still had a hard-on problem, he was suddenly confident enough to go up to the woman he’d been 

ogling all night (the one dressed like his characters Mom) and let her know that he liked what he 

saw. 

We parted. I left him with a wink, and a promise that he’d done great, and that nothing was weird 

or broken between us. And that might have been the end of it. Yup, might have… but then, the 

very next day, the woman he’d walked up to; walked up to me. Remember, she was my friend, 

and our next store neighbor, so it was nothing new for us to meet for breakfast and gossip on 

day two at these kinds of events. Plus, it didn’t hurt that one of the things I loved about her was 

that she didn’t have a drop of shame in her whole being; she never had. So, it was with no small 

amount of delight that she came up to me and told me how the rest of her afternoon had played 

out (I hadn’t asked him. He’d already had a doozy of a day without having to tell his Mom about 

losing his virginity). 

But he didn’t need to, because his lover sought me out, and explained the whole thing over 

breakfast. Turns out, he had been very, very, very into the whole Mother/Son thing with her. Now, 

for her part, when he first approached her, she didn’t even realize who she was dressed as! Her 

husband had chosen both of their outfits and she had barely learned that her character's name 

was Kushina before the neighbor boy (my Son), walked up to her to explain that she was 

dressed as his Mom. 

But, it turns out, my Son had helped her develop a new fetish since yesterday, and she was not 

only thankful, but she wanted to ask me “how I did it?”. When I expressed confusion at what she 

meant, she explained that, the fantasy had been SO hot for her! So, if it was that intense getting 

fucked by her pretend Son, she didn’t know how I resisted having a real Son who looked and 

fucked just like the pretend one that she’d had a  sexathon with the night before. 

I was about to explain it away, albeit with a little bit of lying... when she waved a hand fan in her 

face, and said that, when my Son came, she came too, just from his words. Then, she told me 

that, as my Son fucked her, like only a person in their physical prime could, he’d screamed, “I’m 

ready to cum Mommy”... 

And now it was my turn to blush, and stare blankly with my jaw dropped.

Oh… this was suddenly so far from over!

I mean, I hadn’t exactly been doing nothing since my Son and I had parted ways. I had big tits, 

long hair, and a well deserved reputation; so I’d had plenty of fun yesterday. But… as my friend 

explained to me how she’d spent her day, I had just one question for her.

“Would you mind if we, um… traded costumes for the rest of the event?” At first, she wasn’t sure 

if her husband would be cool with that. But when I explained to her that I’d given my Son a 

handjob in order to warm him up for her the day before, she began stripping out off her costume 

right there in the breakfast area. She was desperate to hear more, and suddenly all on in hearing 

my intentions. 

I told her the truth, which was, I just… I just had to have more! But! I was still determined to try to 

control myself. So, with that in mind, I was hoping for maybe another handjob, but perhaps this 

time I could lay him out on a bed, and get some face to face interaction with him. God that would 

be so fucking hot! Or maybe, if I dared… I would end up showing him why complete strangers 

sought me out at these kinds of events to beg for a blowjob from me… 

Either way, I was SO not done with him yet!

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