Incredibly, today Mistress and I had our seventh Femdom session of this chastity year… which means we’ve only missed two (August and October) so far and if (as we plan to) we have another session just after Christmas we will be on track to equal our record of eleven sessions (2013-2014) assuming we have one each in Jan-Feb-Mar. But even if the worst happens and we don’t have a single session before the end of March 2022, this will still have been our best year since 2015-2016 (nine sessions) which is a fantastic result (we had six for the last two years).
Mistress and I slept in again today, though I don’t think either of us benefitted greatly from this – I was constantly dreaming last night (unpleasant some of them) which meant I didn’t wake up exactly feeling ‘refreshed’ despite nine hours in bed, and Mistress was also feeling very stiff when she woke up.
But instead of feeling sorry for ourselves and ‘putting it off til next week when we’re bound to be feeling better’ we elected to go ahead, cos if there’s one universal truth about a Femdom session is you never feel worse for doing it. In fact, there’s nothing better to make you feel absolutely amazing!
I was told to ‘Surprise’ Mistress at the start of the session, which meant I got to choose which things to start the session with. While I was getting the kit out of the bedside drawers I came across a couple of things, firstly the ‘prostate’ massager we bought…. ooh, I don’t know when. Ten-fifteen years ago maybe? Can’t honestly remember, but we’ve never actually used it. And secondly, a vibrating butt plug with dead batteries in it that I’d completely forgotten about.
I remember we tried that and it wasn’t particularly amazing, it was too small, not strong enough and it fell out too easily as I remember, but I thought it would certainly ‘surprise’ Mistress. But then I thought that if I put it in my ass then there was every chance that Mistress would whip me, catch the thin, delicate cord from the control box and break it… so instead I decided to insert the ring ended dildo; being glass this goes in with the barest minimum of lube (to prevent fall out, although it still tried to of course…).
In addition I pegged my nipples, slipped on my red rubber blindfold, the Oxballs Cocksling (and the usual wrist and ankle cuffs) and waited for Mistress to enter the room.
Mistress was amused to see the pegs on my nipples and remarked that she wondered if I would be thinking that was such a good idea in half an hour’s time. Regular readers may remember the last time I chose to peg my own nipples at the start of a session; they were tingling for days as they rubbed against my shirt!
As expected Mistress decided to give me some whipping and paddling to start the session. I didn’t have any illegal touching to confess to, but Mistress still made me wince, especially the last five or so strokes. Once that was out of the way she had me worship her beautiful feet while she started to play with her glass dildo.
As I was worshipping her beautiful feet she mused over whether she would let me cum today and suddenly asked me if I was allowed to cum, where would I want to be allowed to shoot. She didn’t give me any time to think about it and demanded an answer straight away, and of course I answered that I would want to cum on Mistress’s gorgeous feet.
Mistress found it interesting that my immediate snap reaction was to choose her feet, but she reminded me that even if she did let me cum there was no guarantee that she would take my wishes into consideration. She said she might just make me cum all over her glass dildo and lick it clean instead, which was very hot for me to hear.
Once satisfied that her feet had properly worshipped, Mistress had me get up on the bed and kneel upright. She knelt in front of me and said ‘I’m not convinced that these pegs are doing the job they are supposed to’ and opened the one on my left nipple. I winced loudly as the blood rushed back into my nipple and she replaced it, then did the same with the other one. Then she told me to lie down and she secured me to the bed.
Mistress stood over me and told me she would permit me to see her now and allowed me to beg her to remove the blindfold. Mistress looked gorgeous in her leather skirt and PVC bra. In her hand she held her dildo. I watched as she lifted her skirt and started to slide it in and out of her pussy, listening as she taunted me about how much I wanted to replace the dildo with my tongue, or my cock.
The dildo was pushed into my mouth and I sucked the juices off of it, tasting her delicious pussy from the hard, smooth surface. Surprisingly my cock wasn’t responding much yet, but as soon as Mistress straddled my face and ordered me to lick her wet slit I felt it getting VERY hard VERY quickly.
Despite being rock hard Mistress pretty much ignored my cock to start with and I wondered if she was intending to follow through on her previous comments that she could disregard my cock for the whole session if she wanted to… as it turned out this was only a temporary situation and she eventually started to slap and whip my cock (and my balls to now and then), which only made my cock even harder.
Mistress knelt down beside me and bent forward to take my very hard, very red cock into her mouth. It felt amazing, but she was teasing more than she was sucking, her tongue flicking against the underside and even my tightly bound balls. She sat upright and made me beg to see her gorgeous breasts, which she offered in turn to my eager mouth.
Then she straddled my head again and my cock got even harder as I tasted how wet she was becoming. Then she turned around and started teasing me with her amazing ass… meanwhile the slapping and whipping continued and then she decided to use the cock whip on my chest. She flicked the small whip against the peg on my left nipple and it flew clean off.
Fuck that hurt! But Mistress didn’t miss a beat, she picked up the peg and asked me if I wanted it back on or not. I told her she should do whatever pleased her and she placed it back on my nipple. I love that Mistress did not slip out of character when this happened. In the past I’m sure she would have been worried about ‘hurting’ me, and obviously that is a sensitive topic, but this is just momentary pain… and as much as I did not like the pain in that moment, the truth is I would put the pegs on my nipples again without a second thought because I love the idea of suffering for my Mistress’s amusement and pleasure.
Mistress continued teasing my cock and then reached back and pulled the peg off my nipple again without warning. It didn’t hurt as much as when she flicked it off with the whip but it still hurt and while I was still thanking her she plucked the other one off too (though that one wasn’t as painful).
Mistress stood by the bed and put one foot up on the mattress. She picked up her glass dildo again and told me she would be leaving me for a few moments and that she wanted me to be thinking about what she was going to want me to do, or was going to make me do when she came back. She slid the glass cock inside her pussy again and then had me lick it clean.
When she came back she stood on the bed and unfastened her leather skirt, slipped it off and then straddled my head again. Her pussy was still soaking wet and I couldn’t wait to get between her beautiful thighs and make her cum. Mistress untied me and told me to remove the Oxballs Cocksling, and then get up on my hands and knees.
I felt what I thought was the paddle striking my ass, it turned out later that it was the crop (another toy we’ve had for at least ten years and barely used). It felt okay actually, I was a trying to figure out which side of the paddle Mistress was using on me, so I think it’s fair to say it feels somewhere in between the harsh leather side and the softer red side.
She took hold of the ring end of the dildo and started fucking me with it, reaching beneath me to stroke my cock – though having just taken the Cocksling off it was pretty soft. Mistress asked me if this was as good as when she fucked me with her strap-on last time. I said it wasn’t, it doesn’t create quite the same ‘submissive’ feeling as being ‘fucked’ properly, although it’s still fairly challenging mentally.
Mistress started using more of the length of the glass dildo, which (probably because I only used a tiny amount of lube to get it in) suddenly felt quite intense… and indeed I noticed it started to rub against my prostate and I felt… it’s hard to describe really, it’s not like edging through stimulation to your cock, it’s much more intense and ‘deep’… more like a feeling of losing control, I’ve read that it feels like you need to urinate and that’s quite accurate actually.
I can imagine if Mistress did make me cum that way it would be pretty powerful and I’ve read that it feels very intense even with zero stimulation to your cock. Now that I’ve found the ‘Eros’ prostate massager, maybe we can try it out properly…
Then finally it was time to worship Mistress’s gorgeous pussy and make her cum. She was still really wet and she tasted delicious as she always does. As much as I love everything we do in these sessions this is still the best part for me, nothing gives me as much pleasure as feeling Mistress tensing up and cumming under my tongue.
Once Mistress had finished cumming she stood up on the bed facing away from me and ordered me to lick her clean. She was really soaked and one particular rivulet of juice made it past her knee. I greedily licked up everything I could reach and then Mistress turned around to allow me to clean her pussy too.
Then she told me to lick the sheet clean and lie down on my back. She stood over me again, but left my arms free and allowed me to rub my hands up and down her legs and to pull her cheeks apart to expose her gorgeous, pink asshole. She slapped my cock and stroked it until it was hard again as she continued to tease me with her ass. She eventually told me that she wasn’t going to allow me to cum today, but that she was going to let me worship her asshole, as long as I begged her convincingly.
After some heartfelt begging Mistress lowered her ass down onto my face and allowed me to taste her. As I lapped at her ass I felt her take my cock into her mouth again, which I might tell you is a pretty fucking awesome feeling! :) Mistress lifted off and pumped my cock hard, trying to get me to the edge no doubt, before she made me beg for a second taste.
Mistress sank down onto my face a second time, pumping my cock as hard as she could. It felt so good, but too soon Mistress lifted off and knelt beside me, continuing to stoke my rock hard cock, teasing me with her gorgeous breasts until finally I got to the edge and Mistress let go…
Well that was pretty awesome, roll on Christmas!
FEMDOM SESSION: 5th December 2021
The Ultimate Male Chastity Key Holding Experience
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