Chat Confession

Story Info
A true confession in a chat room.
1.8k words
3.48
30.8k
2
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
danielx3
danielx3
110 Followers

MrSmith:- Hello Bonnie

MrSmith:- m 39 boston

BonnieBlue:- hello

MrSmith:- how old?

BonnieBlue:- 50/f/co

MrSmith:- ok

BonnieBlue:- people tell me i look younger though

MrSmith:- up late as well, eh?

MrSmith:- or early lol

BonnieBlue:- actually..up early...can't sleep

MrSmith:- much the same

BonnieBlue:- k

MrSmith:- does that mean you're single too?

BonnieBlue:- no

BonnieBlue:- married

MrSmith:- hubby still asleep?

BonnieBlue:- yes

MrSmith:- do you come into chat often?

BonnieBlue:- not that often..u?

MrSmith:- sometimes

MrSmith:- it depends how the mood takes me

BonnieBlue:- sounds familiar

MrSmith:- and I like the anonymity of it

BonnieBlue:- :)

BonnieBlue:- can i ask a question?

MrSmith:- yes

BonnieBlue:- do you masturbate here?

MrSmith:- yes, I do

BonnieBlue:- cool

MrSmith:- do you?

BonnieBlue:- yes

BonnieBlue:- my husband doesnt have much interest in sex anymore

MrSmith:- mmm ... sad

BonnieBlue:- yes

BonnieBlue:- can i ask what u look like?

MrSmith:- 5'8 fair hair blue eyes, average build, I guess

MrSmith:- I used to do roleplay, but I've kinda grown out of that

BonnieBlue:- what do u like now?

MrSmith:- chatting, some confessional stuff

BonnieBlue:- ok

MrSmith:- I can talk opernly here without fear of being recognised

BonnieBlue:- yes

MrSmith:- and share my exploits, that can excite me

BonnieBlue:- really?

MrSmith:- mmm, yes

BonnieBlue:- i can share my fantasies...i know what u mean

MrSmith:- its fun testing the reactions of others

BonnieBlue:- ok..so test me

MrSmith:- and, in some cases, reliving events

MrSmith:- ok

MrSmith:- last week I made my 58 yr old secretary suck me off

BonnieBlue:- oh wow

BonnieBlue:- how did u do that?

MrSmith:- I told her that the company were laying people off

MrSmith:- which was true

MrSmith:- her job was kind of at risk

MrSmith:- also true

MrSmith:- of course, that worried her

BonnieBlue:- yes

MrSmith:- she's unmarried, lives with her elderly mother

BonnieBlue:- k

MrSmith:- a bit of an old spinster, I guess

BonnieBlue:- is she attractive?

MrSmith:- in an old schoolmistress sort of way. She could be attractive if she tried but I don't think that she wants any male attention

BonnieBlue:- k

MrSmith:- slim, nice figure for her age

MrSmith:- but a bit prim and proper

MrSmith:- that was a bit of a turn on for me

MrSmith:- just imagining her sucking on a cock was so unthinkable it was exciting

BonnieBlue:- hot

MrSmith:- I asked her how important her job was to her

BonnieBlue:- go on

MrSmith:- I could see she was getting even more worried, nervous

MrSmith:- she said she really couldn't manage without it

MrSmith:- I nodded, kinda sympathetic like

MrSmith:- I said that she'd find it difficult getting another job at her age

MrSmith:- especially one so well paid

MrSmith:- she looked at me, I could almost see tears in her eyes

BonnieBlue:- keep going

MrSmith:- then I sprung my nasty trap

MrSmith:- I said:

MrSmith:- do you want to suck my cock, Jean?

MrSmith:- he he he

MrSmith:- I loved the shock effect

BonnieBlue:- that's really pretty bad

MrSmith:- she colored slightly

MrSmith:- I beg your pardon, she said

MrSmith:- she'd heard, I know, but she didn't really believe

MrSmith:- she was sitting down, I got up from behind my desk and walked round

MrSmith:- let me put it this way, Jean, I said

MrSmith:- I was unzipping my trousers as I spoke, she was looking at me kinda shocked

BonnieBlue:- wow

MrSmith:- you dont have to suck my cock, that is entirely up to you

MrSmith:- but it is entirely up to me whether or not you will have a job tomorrow

MrSmith:- I had my cock out in front of her, it was semi-hard because I was turned on by the situation

MrSmith:- I stroked it in front of her

MrSmith>:- the colour had suddenly gone from her face, I was afraid she'd faint

BonnieBlue:- is it big?

MrSmith:- 7 inches and broad, the head is big and bulbous :)

MrSmith:- but I don't think she'd seen a cock up close like that for a long time

BonnieBlue:- did she stare at it?

MrSmith:- fascinated, I let her stare at it for a while, probably thinking about having it in her mouth

MrSmith:- I wanted to shock her a bit more

MrSmith:- I watched her expression

MrSmith:- I said that it excited me to think of filling her mouth with my spunk

MrSmith:- I could see that disgusted her

MrSmith:- but some color came back into her cheeks

MrSmith:- she was starting to get angry, I think

MrSmith:- think of your position, I said

MrSmith:- then she found her voice

MrSmith:- she told me that it was disgusting, that I was a nasty pervert, that she had never been so insulted, etc etc etc

BonnieBlue:- wow

MrSmith:- but she didn't storm out

BonnieBlue:- was she still looking at it?

MrSmith:- not while she was shouting at me, but after she had lost steam, she was still sitting in her chair, still with her eyes fixed on the end of my cock

BonnieBlue:- she probably hadn't seen one in years

MrSmith:- actually shouting is sort of the wrong word, but you know what I mean

MrSmith:- more of a tirade

BonnieBlue:- k

MrSmith:- and, no, I don't think that she had seen a man's cock in years, especially a fully erect one. I loved having her looking at it. it was quivering about a foot in front of her face. I wondered if she was thinkkng of it inside her mouth.

BonnieBlue:- omg

MrSmith:- I knew that I had almost won, if she wasn't going to do it, she would have left

MrSmith:- and maybe reported me

BonnieBlue:- true

MrSmith:- but the risk is all part of the excitement

MrSmith:- I told her that she was lucky that I was a pervert, because I was giving her a chance she wouldn't have otherwise got

MrSmith:- and she should think of it as just a few moments unpleasantness

MrSmith:- and wasn't her job worth that?

MrSmith:- I was still stroking my cock in front of her face

MrSmith:- I like to think how nasty it must have looked to her with precum leaking from the tip

MrSmith:- she had calmed down a lot

BonnieBlue:- oh wow

MrSmith:- still looking at the tip of my cock she asked in a quiet voice, almost a whisper

MrSmith:- I will keep my job, Sir?

MrSmith:- I almost laughed at the 'Sir'

BonnieBlue:- wow

MrSmith:- I promise, I said

MrSmith:- you'll never tell anyone?

MrSmith:- our little secret, I said

MrSmith:- she opened her mouth, but didn't move any closer to my cock

MrSmith:- so I moved towards her, took hold of the back of her head by the hair and pushed my cock inside her mouth

BonnieBlue:- wow

BonnieBlue:- did she suck it right away?

BonnieBlue:- please don't stop

MrSmith:- once my fat cockhead was inside her mouth shje settled down to sucking on it

BonnieBlue:- wow

MrSmith:- I kept hold of her head, but with my free hand I was able to reach down and grope her tits

BonnieBlue:- did she like that?

MrSmith:- no, she tried to squirm away, but I had her head held fast and like that she couldn't stop my hand going under her blouse and inside her bra. with her left tit in my hand I trapped the nipple between my thumb and forefinger - that made her squirm too and the buttons of her blouse became undone.

MrSmith:- my cock felt so hard ;)

BonnieBlue:- yeah i bet it did

MrSmith:- I knew it wouldn't be long before I came

MrSmith:- I started fucking her face

MrSmith:- when I felt my juice building up inside me

MrSmith:- I forced my cock hard into the back of her mouth and released my jizz down her throat

MrSmith:- then I pulled back to fill her mouth with the rest.

MrSmith:- I wanted her to get the full taste of my semen

MrSmith:- she was struggling to get her mouth free at that point

BonnieBlue:- lol

MrSmith:- when I let go she pulled away coughing and retching on my cum

MrSmith:- I took advantage of the moment to finish by jerking off over her

BonnieBlue:- wow

BonnieBlue:- hard to believe

MrSmith:- she looked a real sight

MrSmith:- my cum dribbling down her face

BonnieBlue:- mmm

MrSmith:- one tit out where I had groped her, with more of my spunk on her blouse

MrSmith:- when she had cleared her mouth and throat she looked up at me

BonnieBlue:- what was she doing

MrSmith:- you filthy dirty bastard, she said

MrSmith:- that made me laugh

BonnieBlue:- omg

MrSmith:- I wiped my cock on her blouse

BonnieBlue:- amazing

MrSmith:- she pulled it away trying to cover herself up

MrSmith:- I felt kinda mean

BonnieBlue:- i would think so

MrSmith:- but I also kind of liked abusing her like that

BonnieBlue:- mmhmm

BonnieBlue:- i think it is hot

MrSmith:- she was trembling a little, I had the feeling that the whole experience was exciting her, but she wanted to continue playing the victim.

BonnieBlue:- i bet

MrSmith;- I wasn't sure what to do next, I hadn't really thought it all through

MrSmith:- so I told her to take off her clothes

MrSmith:- she refused

MrSmith:- she said she'd sucked my thing and I should let her go now

BonnieBlue:- ok...

MrSmith:- I looked at her, I wasn't sure what to do

BonnieBlue:- ok...

MrSmith:- but I wanted to do something more, humiliate her just a bit more

BonnieBlue:- mmm

MrSmith:- I told her I wasn't going to let her go until I'd had a feel of her cunt

MrSmith:- I used the word 'cunt' because I liked how nasty it sounded

BonnieBlue:- yes...it does sound nasty

MrSmith:- she obviously wasn't going to help me, so I pulled up her skirt that she was trying to hold down

MrSmith:- and pushed a hand up between her thighs

BonnieBlue:- omg

MrSmith:- she let out a little cry, bUt I got her legs apart and pulling her knickers aside ran my fingers along her slit

MrSmith:- then I slipped a finger up inside her fuckhole, deep into her cunt

BonnieBlue:- wow

MrSmith:- her eyes opened wide and she gasped loudly

BonnieBlue:- u r daring

MrSmith:- she was slick and wet

BonnieBlue:- i can imagine

MrSmith:- then I pulled my finger out, wiped it on her skirt and told her she could go

BonnieBlue:- nice

MrSmith:- she took a while to sort herself out

BonnieBlue:- that's mean but so vrry hot!

MrSmith:- I think she was going as quickly as she could though. I continued stroking my cock. She was probably afraid that I w

as going to fuck her.

BonnieBlue:- I'm fingering myself imagining that you did.

MrSmith;- She went straight home, pretending to be sick. The following week, feeling that I had got away with it, I fucked her, but that is another story and another confession.

BonnieBlue:- you raped her?

MrSmith:- You'll have to be the judge of that, next time.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AnonymousAnonymousover 15 years ago
Cool Story!!

I had my secretary suck my stiff dick too but didn't have to force her...lol She went for it like a duck to water. She was married but couldn't wait to take that drive...YAHOO!!

The format of your story is VERY original!!

*

*

malapulga@yahoo.com

RhymeFairyRhymeFairyalmost 18 years ago
Oh My !!!

Good Lord I about had a heart attack!!

What a *confession. *fans self*. Naughty, pure

naughty !!

Share this Story

Similar Stories

The MILF Mentor Rocky the MILF teaches Billy about sex.in Mature
Dude, You Slept With My Mom?! Ch. 01 Most people have a bucket list; I have a Fuck It list.in Mature
Community College Slow burn hate for StepMother and family that abandoned him.in Mature
Masseur and the MILF A new career derails when a masseuse's ex's stepmum show up.in Mature
Our First MFM Mature MFM first time.in Mature
More Stories