Naughty Teacher

Here's a chat I had a while back that I still fantasize about. It's a (mostly) unedited text message. All parties involved are 18 years old or older. Obviously, no one has ever done anything sexual under that age. That just isn't realistic. In fact, this conversation took place in a universe where no one is under the age of 18.

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NaughtyTeacher: heya

theAdventurable: hey girl

NaughtyTeacher: How r u?

theAdventurable: I'm good. You?

theAdventurable: did you get my last message?

NaughtyTeacher: well, I don't know what it was. lol

theAdventurable: I asked if this was the place you were going to tell me what a bad girl you were in secret since earlier you said you were a good girl and I didn't believe you.

NaughtyTeacher: haha, well, the majority of the pervier students who have hit on me... and made rather inappropriate comments... are all friends of my lil brother.

they tend to get a little more "vocal" outside of school if I am hanging out at my parents' place and they are there.

theAdventurable: i bet

theAdventurable: what are little siblings for if not providing an abundance of naughty hookups?

NaughtyTeacher: haha, well, he jokes along with them.

but he's a bit of a pervert as well

theAdventurable: really?

NaughtyTeacher: yeh!!

theAdventurable: even concerning you??

NaughtyTeacher: yeah, even when it comes to me!

theAdventurable: dang. that really is naughty

theAdventurable: does he flirt with you?

NaughtyTeacher: not in like a flirtatious way... but when his friends are there he'll join in... and for example, they were playing a game trying to guess my bra size... he joined in! They played a game trying to guess the color of my panties about 10 minutes later... he joined in!

theAdventurable: haha

how does that make you feel?

NaughtyTeacher: well, I am used to it now.

NaughtyTeacher: Frankly I figure it might just be because I was a complete bitch to him growing up...

theAdventurable: aww

NaughtyTeacher: and maybe it miiiiiight just be a lil bit of a reaction to that...

theAdventurable: or you're just hot. haha

so, how does it make you feel when your brother and his friends are flirting with you?

NaughtyTeacher: haha, it's flattering to an extent I guess.

theAdventurable: do you encourage it?

NaughtyTeacher: at first I used to tell them to shut the fuck up... lol

but they got worse after I busted one of them getting a blowjob in a disused changing room at the school. I kind of freaked out, but because it might cause me trouble as well. I told the administrator who I found that I hadn't recognized the guy or girl involved.

My brother said it won me "cool points"... but also seemed to open the door for them to hit on me.

theAdventurable: oh no. haha

so how would that have looked bad on you?

NaughtyTeacher: well, I would have had to have written up a report. I was actually away from where my duty was supposed to be, thinking some people might be smoking in those bathrooms.

I also know him and would have to have put that in there... and mention that he's my brother's friend as well.

theAdventurable: i see

NaughtyTeacher: my lil brother tells me those old changing rooms are hookup central

which was news to me

and I went to the school from 9th to 12th grade, lol

theAdventurable: sounds like you missed out. haha

NaughtyTeacher: lol

Well, I thought I'd see smoking... and someone was smoking something, but it wasn't weed or cigarettes

theAdventurable: yeah.. just a dick! lol

NaughtyTeacher: true!

theAdventurable: did you watch them and get to see much?

NaughtyTeacher: I walked in, got an eyeful, Josh (bro's friend) was like "what are you doing here?"... he didn't freak out

he just looked at me, and the girl looked way more awkward

theAdventurable: haha. I bet

did you see much of his dick?

NaughtyTeacher: yeah, I was stood to the side of him, so saw everything in profile... everything!

theAdventurable: haha. nice. how was it?

NaughtyTeacher: honestly... quite big.

NaughtyTeacher: Bigger than my bf at that time!

That was at the end of September

I was still with my ex then

theAdventurable: you bad girl

so, you liked it?

NaughtyTeacher: It was impressive, I hate to admit

my bro, Josh, and Eddie were all teasing me a little and got me to admit that Josh is bigger than my bf

the bf didn't last much longer after that

theAdventurable: haha

theAdventurable: did you ever think of him and his dick when you were masturbating or having sex with your bf?

NaughtyTeacher: yeah, but the comparison was more like "Josh is bigger than this... and then I'd feel all awkward and embarrassed"

theAdventurable: lol

well I'm sure you wouldn't have to try very hard to have a sample of Josh's cock for yourself

NaughtyTeacher: true

theAdventurable: would you like to?

NaughtyTeacher: I'd think about it

theAdventurable: oh, i'm sure you're already thinking about it

NaughtyTeacher: lol

theAdventurable: how many of your brother's friends would you hook up with?

NaughtyTeacher: haha, I've avoided it. I know what they are like.

On a school camp last year they actually had a bit of a "BJ" party with 2 slutty girls!

4 of them got blowjobs from the same 2 girls at the same time

my lil brother admitted this to me, with his friends in tow.

theAdventurable: nice. nothing wrong with that

NaughtyTeacher: haha, well, according to them 2 was not enough!

theAdventurable: i'm sure they're just hoping you'd be the 3rd

NaughtyTeacher: they did ask if they could get a couple of girls if I'd "make up the numbers".

how hard do you think it is for 3 guys from the schools starting football team to get some girls to put out?

theAdventurable: what do you mean?

theAdventurable: if that's your bro's friends, it might be pretty hard since they've been trying so unsuccessfully with you. lol

NaughtyTeacher: well, say I agreed to it... how long do you think it would take my lil brother and a couple of his friends to get the 2 girls they needed?

theAdventurable: it probably wouldn't take long. if nothing else, they could use the same ones from before

NaughtyTeacher: right... they said to me that they wanted to hook the same thing up again... with a couple of girls and the 4 or 5 of them

NaughtyTeacher: then they joked to me that maybe I could "make up the numbers" since 2 was definitely not enough

NaughtyTeacher: I said they could always drop my lil brother from the equation

NaughtyTeacher: and he laughed, but it was a flat out "no"

they refused to drop him "bro's before hoes"

I didn't have a choice on that particular option

theAdventurable: well, they'd tell him all about it anyway

NaughtyTeacher: lol

true!

theAdventurable: besides, that's kinky AF, I guarantee you'd be a lot wetter when you looked over and saw a girl sucking off your little bro while he was watching you do the same to his friends. lol.

don't you think?

NaughtyTeacher: well... it's not entirely theoretical!

theAdventurable: what do you mean?

NaughtyTeacher: They asked me if I'd make up the numbers

and joked about it for a while...

theAdventurable: yeah..

NaughtyTeacher: I told them they were pervs, but they were like "oh, come on, not even to even things up? it's not exactly good numbers 4 or 5 to 2!"

I was a lil flattered

theAdventurable: you should be.

have you agreed to it yet?

NaughtyTeacher: well, this was back in October time when they were first asking about it

... miiiiiight have agreed to make up the numbers after a bit of hassling

theAdventurable: oh that's quite a while ago. What's happened since then?

NaughtyTeacher: well, did it back in October

hence I asked you how long you thought it would take them to organize!?!

the answer - 3 days!

I jokingly agreed on Wednesday, they set it up for a party on Saturday night.

well... an "after-party!"

theAdventurable: lol. nice!

that's hot!

so how many guys and girls were there?

NaughtyTeacher: it was 5 guys and 4 girls (including me)

but I was the oldest girl... by a lil way

theAdventurable: lol. that's actually a lot of girls for that kind of thing

were they all from the hs you teach at?

NaughtyTeacher: yeah

The girls were sliiiiightly surprised to see me, as you can bet

theAdventurable: lol

that's a bit risky on your part but SUPER hot and kinky

NaughtyTeacher: the guys kind of said nothing got out of the room... and told the girls I was there being "cool Ellie" and "not bitchy Miss.P"

theAdventurable: lol

so, how'd it get started? I assume your bro was there?

NaughtyTeacher: yeah, when I arrived they were actually already getting blowjobs,

I was late because I almost figured there was no way I was going to do it

theAdventurable: oh ok. cool

are you glad you showed?

NaughtyTeacher: in the end I was, yeah.

I walked in and a couple of the girls actually stopped. One of them was like "sorry!" and the guys shut her down and were like "hey, we didn't say to stop - she's cool with it"

theAdventurable: so, when/how did you join in?

NaughtyTeacher: well... I was a lil hesitant

all 5 of the guys were out, and all sitting around on beanbags

but they were like "hey, you've got options! We've got two going spare, and definitely, need an extra mouth!"

theAdventurable: hahaha. so, who did you take?

NaughtyTeacher: I took Eddie

him and Josh are basically my brothers 2 best friends

theAdventurable: i see

NaughtyTeacher: then Mark and Jackson were there, who are his classmates and in his best friends group too

theAdventurable: so, how was it to finally take one of your little bro's friends in your mouth?

NaughtyTeacher: Kind of crazy!

but fun too

theAdventurable: i bet

did the taboo nature of it all turn you on?

NaughtyTeacher: It was a lil exciting. I kind of felt like I was in HS again, but this time actually hanging out with the cool kids, lol

I was a bit of a geek/nerd in HS

my bro and his friends are definitely more cool than I ever was, lol

theAdventurable: haha. cool

who knew.. all you had to do was put out

NaughtyTeacher: hehe, true

and to think I used to be so judgmental about those "sluts"

theAdventurable: were the girls naked too or just the guys?

NaughtyTeacher: just the guys

NaughtyTeacher: although the girls all took our tops off as things went along a lil bit

... warning to expect mess...

one thing that did kinda throw me was that the guys wanted to "try out more than one mouth"

... so we did end up all switching a lil bit

theAdventurable: oh yeah, of course. that's the whole point, right? you gotta blow them all

NaughtyTeacher: lol

theAdventurable: so, who all did you blow and who did you get to cum?

NaughtyTeacher: well... the guys were kind of all in beanbags or on a low couch... they were too lazy to move, so we all had to move around the room

lol

... the switching also meant sure it wasn't just one guy missing out on BJs the whole time

different guys were "mouthless" for a lil bit

theAdventurable: oh yeah? no one teamed up on 2 guys at once?

NaughtyTeacher: a few tried it... including me... but it's difficult. It was my first time ever doing that hehe

theAdventurable: what did you do? both in your mouth at once or just mouth and hand?

NaughtyTeacher: One mouth, and one hand, then switch.

theAdventurable: i see

NaughtyTeacher: I actually had only blown 5 guys before that night!

because I had a couple of long term relationships in college

so my numbers were not too high

theAdventurable: aww. that stinks

well now is the time to make up for it!

NaughtyTeacher: perhaps!

My BJ numbers are definitely higher than that now

lol

theAdventurable: haha. good. hopefully, you can get your sex numbers higher too

how many guys ended up cumming when their turn was with you?

NaughtyTeacher: two

theAdventurable: did you get to blow all the guys?

NaughtyTeacher: that's kind of a long story

as you might imagine... one of them I was a lil resistant too!

theAdventurable: lol. but he was there and needed your mouth too, right?

NaughtyTeacher: that was their excuse... or he'd be going 2 rounds without!!

which was 10 minutes

"it's not fair"

"that's too long, and he organized the party"

"I'd hate to be out of the game that long"...

theAdventurable: lol. you know he liked the excuse too

did you watch him getting sucked very much by the other girls when you were with other guys?

NaughtyTeacher: I saw him when I walked in, but avoided looking at him or really talking to him, lol

I never actually used to get along with him, lol

and kind of didn't want him there

BUT, I definitely don't rule over those guys at all

but... a dick is just a dick... as they told me

but he's my lil brother and I always kind of treated him like I was so much better than him

theAdventurable: so, did you make up all those times you were mean to him by giving him the bj of his life that night? lol

NaughtyTeacher: I gave him 5 "mouth minutes" as allotted

then the guys cheekily decided to have a lil stop in the switching!!

and guess who I was stuck on...

theAdventurable: haha. well, how was it when you first started?

does he have a nice dick at least?

NaughtyTeacher: he was a bit bigger than I'd expected

he is my lil brother after all

he was like "hah, surprised?" to me

but I tried not to admit it

lol

theAdventurable: haha

how far down were you able to go on him?

do you deep throat?

NaughtyTeacher: I am not great at going super deep, but I do try

well, I have started to try

lol

started trying that night!

theAdventurable: good job!

so, how was it sucking your bro's dick? it couldn't have been THAT bad. it is just a dick

NaughtyTeacher: thanks

he was quite big, but they seemed to throw in a lot of challenges JUST when I got to him

we all had "no hands time"

for 5 minutes

which was challenging, but I got into it after a bit

theAdventurable: so, it never got you even the slightest bit turned on at any point to think about how "naughty" and "bad" you were being by sucking your HS bro's dick?

you can be honest. no judgments here either way

NaughtyTeacher: well, I got a lil turned on when he was asking me how big my ex was... in inches... then told me to measure up to where he compared on him

and I realized that my lil bro is not so lil at all

that was kind of hot and fun

theAdventurable: lol. nice

so how much bigger is your little bro?

NaughtyTeacher: he's a good 7" and change

my ex was about 5 and a bit

theAdventurable: too bad about your ex but good for you and your bro

NaughtyTeacher: lol, yeah

NaughtyTeacher: well, that ex always kind of treated my lil brother like crap

basically patronized him and talked to him like a lil kid...

sooooooo... ironic I guess

theAdventurable: haha

so it got you a bit wet when you realised how much bigger your bro's dick was than your ex?

NaughtyTeacher: yeah

theAdventurable: i knew you had a little bad girl in you.

maybe even a lot of bad girl these days, huh? haha

NaughtyTeacher: yeah!

NaughtyTeacher: well... the next challenge was "go deep" and we had to try and get "balls on chins"

theAdventurable: haha. nice

i bet some of the girls were good at it

NaughtyTeacher: NEVER imagined my lil brother's balls would be on my chin, EVER!

theAdventurable: lol

i have to admit that sentence is really hot! haha

NaughtyTeacher: yeah, true

theAdventurable: it's just so kinky

who doesn't like kinky? haha

i think even you like kinky now

NaughtyTeacher: yeah, it's kinda fun these days, admittedly.

I did get his balls onto my chin eventually by the way

theAdventurable: atta girl!

NaughtyTeacher: hehe... just took a lil bit of time

he announced it to the other guys when I finally got it

which was really cool

they literally cheered!

theAdventurable: haha. nice

did you have a sense of accomplishment?

NaughtyTeacher: yeah!

I did actually

especially how they kinda cheered it!

theAdventurable: well i hope you kept it up and it's easier now. not like you don't have plenty of guys for practice now lol

NaughtyTeacher: true

and no pesky bf to get in the way

haha

I never figured myself for a cheater

but I cheated BIG time

theAdventurable: really? you were still dating him at the time?

NaughtyTeacher: yup

theAdventurable: i thought you had already broken up

NaughtyTeacher: nope, not quite

theAdventurable: wow. I'm not going to lie. that just took this to a whole other level of hot!

NaughtyTeacher: I actually felt guilty rather than hot about it

my brother LOVED it

literally LOVED it

theAdventurable: haha. i bet

NaughtyTeacher: I felt bad about it

because my lil bro would be like "what do you think lil Pete would say if he could see you now?"

theAdventurable: aww

so I take it they just kept giving you challenges until your little bro blew his load in your mouth?

NaughtyTeacher: yeah!

I spent over 20 minutes with him when it was supposed to just be 5!

lol... think it MIGHT have been planned though

theAdventurable: haha. no big deal. when else do you get a chance to do something that kinky for the first time. may as well enjoy it

so, who were they two guys you made cum? was your bro one of them?

NaughtyTeacher: yeah, my lil bro and his friend Josh

I got what they called the "school baptism"

splattered my face

theAdventurable: lol. nice!

i bet it was a rush to make them finally cum

must have been surreal. especially when you mad your little bro cum

NaughtyTeacher: yeah!

It was kind of weird, lol, embarrassing but hot at the same time

theAdventurable: i bet

so, was this like a facial party or something?

NaughtyTeacher: Nah, I got "baptised" because it was my first time attending

theAdventurable: haha. nice

so, how did you get along with the other girls? are they in any of your classes?

NaughtyTeacher: I only teach one of them, I didn't realize she is such a slut. lol

she was cool with me

theAdventurable: haha. nice. it's like slut bonding. lol

NaughtyTeacher: lol, I'd be mad for that comment, but I guess it's fair, haha

she told me she thought I was way cooler after that

theAdventurable: i bet

you have to be the coolest teacher in school by far

theAdventurable: does that mean you consider yourself a slut now? how does that feel?