So, this is kind of two parts. There is a real part, and then my fantasy of where it went.
(this part is real) I had a connection one time with a school principal. I was helping kids at the high school, and needed to connect with her to relate how they were doing, and I needed to get attendance reports from her. I was 30, she was 50.
She left a voice mail on my machine one day that started with “hey gorgeous!” which was completely inappropriate. Another time, she asked me if I wanted to go with her to a poetry reading that one of the students from her school was doing. It sounded a bit like she was asking me out. She was married, and had a daughter. Another time, she pressed her breast into my arm…for a while. It was obvious
After a couple of years, I moved, but stayed in touch via email. One day, I was scheming how to send her some naked pictures of myself, I told her I had lost some weight and asked her if she had a personal email address I could send some pictures. She asked why I couldn’t send them to her work email, and I said, well I took my shirt off for some progress pictures, and they’re not really safe for work. She said, “you know what, why don’t you send them anyway, I’m going away for work, and I’ll check it while I’m away so you won’t have to worry.
So I sent her the pictures. 3 pictures, me in shorts and a shirt, me in just shorts, no shirt, and me in compression underwear and no shirt with a hard on bulging as big as mine goes.
She told me she liked the pictures. I hinted at sending her more, and naughtier ones. I wanted her to ask me to send her nudes. She hinted at wanting them over and over but she never asked. I wanted her to ask…..
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(So….Anyway, my fantasy.)
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She was a little bit of an over-mothering mother. Her daughter was leaving for college when I was her working with her….
Mom (Debbie) calls me up one day, and she’s nervous, you can tell on the phone….
She asks me, “would you mind coming over to our place for a bit today, I need to …..um….ask you a pretty big favor.”
“what’s up?”
“I need some help from a man that I trust, and you’re the only one in town that I trust for this…”
I say I guess, it sounds a little fishy, but I don’t want to let her down. So I head over, and I get there about 10 minutes later.
Debbie answers the door and asks me to come in. Her daughter Shelly is there, and Debbie introduces us. Debbie sounds really nervous, and we struggle to make small talk. Finally I ask her what’s going on?
“Um…I need to ask you a favor, and it’s going to sound really weird (nervous laughter)…I just don’t know what else to do or who else to ask, and I need help.”
“What can I help you with?”
Debbie is really nervous, and she’s trying to laugh it off…”Shelly is going away to college next month, and she doesn’t know how to put on a condom, and I am NOT having her come home pregnant at Christmas, so I was hoping we could show her how to put one on…….I KNOW, it’s crazy, but I really don’t want her going to school without knowing how to do this. Would you please just show her?”
“I don’t know, this is going to be really awkward won’t it?” I am protesting, but I really want to do this, I’m getting hard already.
“It won’t be weird, please…”
“I don’t know….I guess, I can help if you really need it…but I don’t have any condoms on me.”
“don’t worry, I do!” And Debbie pulls out a roll of condoms from the drawer on the end table.
Shelly is now getting very embarrassed and her face is getting red. I start to unbuckle my belt and undo my pants. I open up the fly and pull the pants apart so my underwear is visible. I’m really getting hard at this point, and there’s an obvious bulge coming out through the opening in my pants. Shelly and Debbie are both looking while obviously trying to not stare, their eyes aren’t away long before they come back to the opening in my pants.
I slide my pants down, and step out of them. I take off my shirt, and now I’m in just my underwear. I start to play with the waist band a bit. I’m trying to pretend like I don’t want to do this, because I’m trying to hide how much I want to do this.
I am playing with the waist band, pulling it out and sliding it down and then pulling it back up again. The women are no longer trying not to stare, their eyes are locked on my bulge. I ask one more time, “are you really sure you want to do this?”
“Yes, Steve, it’s really important.”
“Ok then…” and with that, I slide my underwear down over my dick, and down my legs. I’m trying to cover my dick with my arm, embarrassed that I’m hard already. I pick my underwear up with my hand and use it to cover my dick when I stand back up.
“ok, Shelly, now watch as Steve puts this on” Debbie says to her daughter as she hands me condom….
I slowly let my underwear drop, finally exposing my cock to the women. It’s hard to tell who is enjoying more, the married mother, or the inexperienced daughter. They’re both staring openly while occasionally looking up and laughing nervously.
I grab the condom package, open it, pinch the end, and roll it down my shaft.
“see how he left a little at the end Shelly? And just rolled it down?”
“yes, mom, I saw it….duh..”
Then suddenly Debbie reaches out to take the condom off. Her right hand grabs the base of my cock below the condom, and her left hand grabs the condom at the end, and she pulls it straight off. The feeling of this married woman’s hand on my cock sends a shiver up my back! The daughter watches the whole thing, but seems so engaged in what’s happening, she doesn’t say anything.
“Ok, now it’s your turn.”
I get a little confused, “now it’s whose turn?”
“Shelly! I want to know that she can do it….relax it will only take a second”
With that Debbie throws Shelly a condom. Shelly struggles to open the wrapper but finally gets it.
Debbie gives her some instructions “just pinch the end, put the middle of the circle on his penis, and roll down the outside.”
Shelly takes the condom, pinches the end, but is so nervous, she struggles to manage getting it on. She’s trying to do it without really touching my cock. “Come on Shelly, it’s not going to bite you, and with that Mom grabs the condom, pinches the end sets the condom on my tip, and rolls it down, getting another good feel of my cock.
After it’s on, she again grabs the base of my cock, grabs the tip of the condom and slides it off. Only this time, she doesn’t let go of my cock when the condom is off. She leaves her hand wrapped around the base of my shaft. She finally lets go to grab another condom package and gives it to Shelly.
This time Shelly is able to get pinch the tip of the condom, get it on the tip of my cock, and roll it down.
YAY! Mom yells, see, it’s that simple. Mom again reaches up, grabs the base of my cock, and takes the condom off. This time, she leaves her hand on again, and I can feel her squeezing and releasing, and ever so slightly moving her hand up and down my shaft just a little.
“Mom, can I try one more?” Shelly asks, grabbing another condom.
“Good idea” and mom finally lets go of my dick. Shelly pinches the end, sets the condom on my tip and slowly rolls the condom down.
“that’s great” Mom says, reaching up again and grabbing my cock. This time, not even trying to hide the fact that she’s jerking me a little. She grabs the condom and pulls it off.
I think this is about to end, and my fun is over when Shelly looks at her mom, her face as red as a tomato, she says …….
“Uh…..Mom……can I ……..would you…..I just…….”
“Jesus honey, spit it out, what are you asking?”
“mom, how do you …do you think Steve would mind…..how do you….um….do a blow job?”
“OH MY GOD” Debbie says, “How do you NOT KNOW THAT?? ……….Just get Steve to sit down on the couch.” And with that she gave me a little shove and I sat back down in the middle of the couch.
“Now just kneel down in front of him….” and with that Mom kneels down by my left knee while the daughter is kneeling down on my right knee.
“okay, so just get in between his knees a bit…there you go. Now just grab his penis, and you ….you …. you just suck on it…”
Shelly grabs my penis, which her mom is staring at and she kind of looks at me as if to ask, is this ok? I nod slightly and she starts trying to suck it. Except, she’s got her tongue pursed and she’s licking the shaft like she’s trying to lick a lemon without getting too much on her tongue.
“You can’t be shy about it honey…..why don’t you start by licking the shaft of his penis a little….no no no, not like that…get out of the way…”
And with that mom spins around my knee and scooches her daughter over, and all of a sudden she’s got my cock in her hands. This is a married woman, who’s daughter is watching her, and she’s wrapping her hands around my dick…
“Like this, just start licking” and with that mom puts her tongue at the bottom of my shaft and slowly starts licking up the entire length of my shaft before stopping before my head. I’m looking down at her, and her daughter is staring at it intently, and it’s getting difficult for me not to cum..
Then she goes back to the base and does it again. Soon after getting close to my head and stopping again, she looks at her daughter and says “ok, now you try.”
Shelly grabs my dick, and this time does a much better job, she keeps her tongue soft, starts licking at the base and goes all the way to the same spot her mom did before stopping. Then she goes back again.
“okay, now, once you’ve done that a couple of times, go ahead and wrap your mouth around the top…”
As instructed the daughter licks up from the base of my shaft, all the way up to the head, and she pauses, and looks at me, not really knowing what to do. I look at her with my eyes begging her to put it in her mouth..
She opens her mouth, wraps it around my head and closes her mouth. Her mom is looking at me, and looking back at her daughter. She reaches down and pulls the daughter’s hair back over her ear so she can see what’s happening. Then, as her daughter has her mouth around my cock head, mom reaches out and starts stroking my shaft. I reach down with my right hand and slip my hand inside the daughter’s shirt and start playing with her nipple. Then the mom says
“okay, one more thing, while you’ve got him in your mouth, use your hands to jerk him off a little” and the mom slides back to the middle grabs my cock and looks me in the eye, winks, and slides my cock in her mouth. Here’s a married woman, with her daughter watching and she’s putting my cock in her mouth and taking the whole thing.
My hand hand came out of Shelly’s shirt when she moved, and I hurried to put it back in. I start playing with her tits again, while mom is sucking my cock, and she’s stroking and all of a sudden I can’t hold it.
“Debbie, I’m going to cum” thinking she’d use the warning to get out of the way. But instead she starts going harder….I blow my load and she keeps sucking, but I think the velocity of the shot shocked her a bit. She sat up, and kept stroking. She had some cum coming down her chin. She went back and licked up what was left on my cock.
I still had my hand in the daughter’s shirt. I collapsed back on the couch completely spent, unable to move.
Source: reddit.com/r/sexystories/comments/ir5zql/m30_f50_f18_mom_needs_to_teach_daughter