Chastity Keyholding Play Becoming Reality, Mistress F, Part 1

Mistress F, Keyholding Play Becoming Reality, Part 1

Preface: This is a real story, unfolding in real time, with personal details withheld, we are currently on Day 8, and this story will be updated to eventually reach the present day. User feedback, especially ideas both for pleasure and discipline, are strongly encouraged. We need ideas for enforcing staying locked and not breaking free, as no cage is full proof, and I’m pretty crafty to get a cage off if I wanted. Both the chaste and Mistress will be reading the comments. Mistress F notes that methods of punishment for if the chaste breaks free to pleasure himself are especially wanted.

Day 1.

Seducing other mom’s online [FF]

While my husband is at work, I log onto Reddit with my SFW account and try to strike up friendships with conservative mothers in mom groups.

We begin by talking about recipes, children, clothing, and life… but my goal is always the same, have them talking about sex.

Most of these women have never done anything naughty online before, but I’m shocked to discover how quickly they start going into intimidate detail about their sex lives and husband’s dick sizes, and fantasies, etc.

After a few weeks of chatting, I’ll send them a few pics of my body and they’ll compliment me then respond in kind.

The sexiest thing is when we have moved past the “Billy’s tee ball game” stage and 100% of our talk is about sex… their pussies, masturbation habits, and hidden lesbian desires.

On a few occasions, we’ve cyber sexed, with them rubbing their clits at my command! This gets me sooooo soaking wet!

The older I get, the more I love milfs!

Steam Room Mishap [MF] [CFNM]

I [36M] had recently joined a fancy new gym near the office and I was excited to test out all of the facilities. Everything seemed to be state of the art and very modern. After a tough workout I decided I would treat myself to some relaxation in the steam room that was attached to the men’s locker room.

A quick stop at my locker, where I stripped off my clothes and secured my phone and wallet, and I was off to the steam room. The gym did have any full-size towels, just these space-age shammy things about the size of a hand towel. I grabbed one of those to sit on but I was otherwise completely nude, which is generally customary for single-sex locker room facilities.

Despite my working out, I was still a bit overweight, but very muscular. I would describe my penis as a “grower” not a “show-er” as the saying goes. It’s about 2″ soft and grows to a nice, thick 7″ when hard. I’ve always enjoyed being naked and sometimes I need to focus my thinking in order to not sprout an erection when roaming the locker room. This is an important point for reasons that will become clear.

Pat My Frog

The evening is winding down and the fireworks are just about to start. Pat is lounging just slightly off the bed staring out the window. I can see that there’s an excitement about him as he prepares for the show. I have seen them a million times, but through his eyes, it just sparks something in me.

It’s so strange, Kermit thinks to himself, that there’s a childish wonderment inside this hard muscular hunk of a man. There’s a kindness about him that could even make a man like Mr. Rogers jealous.

Kermit utters a whisper to himself under his breath, “Oh, Kermit, let this night never end.”

Bang! The first fireworks start going off. Pat starts relaxing and letting loose, a slight smile on his lips. More fireworks go off – Bang-Bang. Schwee – each firework is like one more of Kermit’s balloons of self control popping away or flying off in the distance.

Kermit touches Mahomes on the back slightly, and then starts giving a floppy shoulder massage. As well as any puppet muppet could do.

“But the finale, we will miss it”, Mahomes says with a mischievous twinkle in his eyes.

[MFF] The story of how my [M46] gf [F33] lost her virginity and her early sex-life is way more exciting than mine.

>!TL;DR (Spoiler) – my gf lost her virginity in a threesome with her best friend, and her friend’s boyfriend.!<

We’ve been together for 7 years now and the start we both agreed not to bring up details of our past (beyond the basics like number of serious relationships, how long etc…). I’ve been in relationships in the past where I have found out more than I had bargained for and it ended up bringing out some insecurities, so I was quite happy to leave it at that. As time has gone on I’ve matured a lot and now feel really secure with my gf but up until the last year or so still never knew that much about her past and never really had the inclination to bring it up.

Denying myself for Daddy – Part 1 of Delayed Gratification [D/s] [Denial] [Fsolo]

My Apple Watch buzzes to wake me. I blearily lift it to turn off my alarm, only to find that it’s ten minutes before the alarm is set to go off. What woke me up was a message from Daddy. *Edge yourself three times,* the message says.

I grunt, only halfway awake, but reach my hand down obediently. There’s a bit of stubble on my pussy, I’ve been waiting to shave it for our date tonight. Our first date in a week. My first chance to orgasm in nearly two. After thirteen days of denial, my pussy is wet before my fingers find it, sliding between my lips to find the clit. I breathe a satisfied sigh as my fingers find it.

The watch buzzes again. *Where I can see it,* he texted me. I obediently kick the covers off and rotate in the bed, laying in it sideways so the webcam on the nightstand can see between my smooth legs to the little pink slit. I reach for the lightswitch by the headboard and turn on the overhead light, blinking in the sudden brightness before I get back to my task. Daddy doesn’t text again as I spread my labia and start rubbing my clit in full view of the webcam.

The time I woke my husband to fuck because of pregnancy hormones [FM]

While being pregnant for the first time is an exciting time, I was not expecting to be as horny all the time. I realize it’s not something every pregnancy delivers, but I’m pretty sure it wasn’t covered in the, “What to expect…” books. My body craved the attention. Soaked panties were the norm. Sex was frequent and solo sessions even more so. I was so open for attention, we even started writing with dirty pen pals just to get different stimulation.

Likely due to the lack of comfortable sleeping positions further into the pregnancy I would wake up and not be able to fall right back asleep. Most of the time it requires using the age old technique of getting an orgasm to help me drift again, even if my husband and I had just fucked earlier that evening.

The unsexy side effect of my pregnancies was my snoring, so most nights meant we cuddled together until I fell asleep and then my husband would move to the guest room to sleep. So most evenings my late night sessions were solo affairs.

Enslaved And Educated Pt. 2 [Femdom] [Masturbation] [MF]

*I advice you to read Episode I first.* [*It is over here*](https://www.reddit.com/r/dirty_boy69/comments/vf095c/enslaved_and_educated/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

I was living a peeping toms dream. I was jerking off like maniac. Whenever my roommate was around. She always smiled at me when I was looking at her, with my rock hard boner in one hand and my balls in the other one. It went that way for about a month.

Then it happened. It got out of control. I accidentally nutted my load onto the Persian carpet in the living room. The fun was over within seconds. She gave me a view that immediately made me regret my failure. I was fucked. She stood there, arms crossed, tipping with one of her feet, I knew that something terrible was going to happen.

No she didn’t lost it. She stayed calm. Very calm. She took a very deep breath: “Look what you have done. I told you to not spit your filthy juices anywhere. Now, there is a stain on the carpet. Well done.”

A Sexual Chronicle chapter 3 [MF] (Exhibitionist/Voyeur)

[Chapter 1](https://www.reddit.com/user/CaptainPervlord/comments/vbugjd/a_sexual_chronicle_chapter_1/)

[Chapter 2](https://www.reddit.com/user/CaptainPervlord/comments/ve20v0/a_sexual_chronicle_chapter_2/)

I don’t think I flagged for a minute in the time we were waiting for Sarah to arrive. Katie went to the toilet at one point and I could help noticing that when she came back, the pubic wedge that had overlapped the ropes before was now perfectly lined up inside them. My girlfriend had evidently decided that if there was to be a show, it needed to be a good one.

As the minutes wore on, the confidence that had made Katie tidy her bush waned, and I felt myself growing nervous as well. Sure, I’d set this afternoon in motion, but it had gone so much further than I had ever expected. I thought about sensible, adult stuff like if my relationship with Katie and if both of our relationships with Sarah would be different after we displayed ourselves to her naked and post-coital. I also worried about childish stuff, like if she’d like the look of my dick, if it would compare to other men she’d been with, even if she’d laugh at me. A naked woman, especially one with Katie’s body, had a kind of universal appeal, even to people not into girls. A naked man – a surprise penis – suddenly appearing in front of you tended to have more of a shock factor, even a funniness to it. Unless you’re super ripped (and while I take care of myself, I certainly am not), men just don’t get appreciated the same way.

Second Time I Watched My Parents Having Sex [MF] [Voyeur]

[In my last post](https://www.reddit.com/r/eroticliterature/comments/vfif9x/first_time_i_saw_my_parents_having_sex_mf_voyeur/) I talked about the first time it happened, and lucky for me I had another chance of witnessing them, but much closer this time around!

It was a couple of years later, in the story from the last post I was in university and the second time happened shortly after I graduated. I went straight back home since I didn’t have anything lined up and my parents were more than happy to have me back. My younger brother, who was 19 at the time, was also happy to not have all the chores to himself, and glad that I could cover for him when he wanted to get high.