As you will have seen from the previous post, Mistress and I managed 8 out of the 12 planned Femdom Sessions in the last Chastity Year (Apr 1 - Mar 31), which was our best since 2015/2016! However, we faltered at the last and actually missed out both February and March... which meant that this session was the first one since the 30th of January.
Maybe we should aim for every three weeks instead of every month, then we would maybe manage 12 out of 17? It's certainly worth considering...
Before I recount this session, I just noticed that someone left a comment on our Novermber session post...
"I hope Mitsress starts fucking your ass regularly and makes all your orgasms anal-only. Then you will know what frustration really feels like, when your cock is twitching and leaking as she pounds your ass with her strap on."
Thanks anonymous, I'm certainly hoping for more frustrating orgasms (more ruins and less full ones) so this is certainly something to aspire to in the future... ;)
Okay, so... for this session Mistress instructed me to wear my wrist and ankle cuffs, a blindfold and either the Oxballs Cocksling or the Oxballs Ball Stretcher. (Seriously, when is Oxballs going to start sponsoring me, I mention them every god-damn time!) I chose the ball stretcher, cos I really like how tight it makes my balls, but it's harder to get on than the cocksling. I had to put it on twice this time because the first time it didn't feel quite right. I've had this before with the cocksling, if you get it on right it is great, but if you get it on wrong it can actually hinder you getting hard. It's very odd and difficult to explain, but take it from me you need to get it in the right place.
I waited on my knees for Mistress to come into the room, knowing full well that the first thing she was going to ask me was had I touched my cock without permission... and I knew that I had. I think the last two sessions I hadn't, but obviously the longer the gap between sessions the more likely it is. But first Mistress stood in front of me and asked me if I could guess what she was wearing. I had hinted that I would love to see her wearing the PVC all in one outfit she got last year. She has only worn it once (May 2021) and I've been hoping to see it again because quite frankly it looks fucking amazing.
So I was definitely hoping for that, but then I felt Mistress brush her leather skirt against my face and that made me think she was probably wearing the open cup basque type top that you see at the top of the blog. She didn't tell me either way, in fact she told me not to guess right then... I was just hopeful that whatever it was her beautiful breasts would be on display when she decided to take the blindfold off me.
So then came the question I was dreading, and of course I admitted my illegal touching. I think Mistress was actually quite pleased, because it meant she was totally justified in dishing out a longer and harsher punishment. She ordered me onto my hands and knees and whipped my ass several times before switching to the paddle.
The red felt side of the paddle is actually not too bad, but every stroke that lands I'm not really thinking how it is actually not too bad... because I know that sooner or later she will switch it over to the leather side and then it really stings. And so it came to pass.... and sure enough it really fucking stung! It's at times like this when I wonder why I get myself into these situations, because I don't actually enjoy pain. I do however like the effect it has on Mistress...
Well the last few strokes with the paddle stung like a bastard, but I took heart from the knowledge that Mistress would be getting wet already with the sound of each painful stroke echoing around the bedroom. It amazes me how it can sting so much but within a few minutes the pain is pretty much gone, I shudder to think how much pain you would have to take to be unable to sit 'for days'!
Thankfully, once the spanking (or this spanking, there was more to come) was over, Mistress turned me towards the bed and offered her dildo to my mouth. She told me to suck on it and get it wet for her and soon she was reclined above me with said dildo working between her legs while I worshipped her beautiful feet in turn.
I was still not sure the Ballstretcher was on exactly right and I hadn't had the slightest inkling of an erection as yet (early session nerves and the stinging in my cheeks weren't helping!) but kissing Mistress's gorgeous feet always makes me feel very calm and submissive and I wasn't really concerned at all, I just tried to relax and forget about the paddle and concentrate on making Mistress feel worshipped.
I needn't have worried, while Mistress played with her favourite dildo she first described what she was doing and then branched off into fantasy, breaking off to double check that even though I had admitted to touching my cock without permission I hadn't accidentally (or deliberately) made myself cum. Satisfied that I hadn't, Mistress resumed her dirty talk and suddenly my cock was getting very hard... in particular when she talked about making me kneel and worship her feet while another cock fucked her pussy... then how she would make me suck it clean before licking the cum out of her. Hearing those words coming from her lips rather than me just imagining her saying something like that (like I often do when she's teasing me) was extremely hot and when Mistress eventually climbed off the bed and stood next to me she commented on how hard my cock was without even being touched. Umm, well, yes!
Then she told me to get up on the bed.
As soon as I was on the bed, Mistress ordered me to stay on my hands and knees and we had round two of the paddle, not so hard this time (thankfully), before she tied me down on my back. Mistress decided that now would be a good time to take my blindfold off, but first she made me beg for it (only too happy to) and finally I was able to see exactly what Mistress was wearing. I was a little unsure at first because from my position all I could see to start with was Mistress's gorgeous breasts and some PVC below and her leather skirt... but then Mistress lifted up the front of her skirt and I realised that she was wearing exactly what I'd hoped for.
Mistress slid her glass dildo into her pussy again and then had me suck it clean before she straddled my face and I got to taste her properly for the first time. She tasted amazing, and already very wet.
Then she turned her attention to my extremely hard cock and immediately started antagonising the head with the cock whip. I flinched a bit as it was quite painful, but when Mistress asked if it was too much I said no and she continued, her pussy no doubt getting wetter with each stroke.
Then she picked up a vibrating butt plug that I found in our drawer of toys a couple of sessions ago, you may remember I was thinking about fitting it at the start of a session but was worried that Mistress might break the wire with the paddle or whip. The controller has a rocker switch, down to turn it on and then seven possible settings scrolled through by pressing upwards.
I don't know which setting Mistress used it on, but she started using it to stimulate my already extremely hard cock (which felt amazing) and after a minute or so she turned it off and straddled my face again. Then she turned around and started to tease me with her gorgeous ass. As she did so she wrapped her fingers around my cock and I could feel how ridiculously hard it was, she literally couldn't even move it because the skin was so tight.
She went back to teasing me with the vibrating plug and I arched my back up with frustration, it felt absolutely incredible and I can't believe we hadn't done this before. Well, actually I say that, but I have a feeling we did try using a very small vibrator a long time ago but it was obviously very weak as I could barely feel it and it did next to nothing. This was so much better, I can't wait to try it again and Mistress was clearly very impressed with the effect it was having on me too...
At some point Mistress straddled me and slid my cock inside her wet pussy, but only briefly, and then she was straddling my face again, before more whipping and vibrating... which was fantastic!
The vibrations were driving me nuts, but Mistress shut it off again and announced that it was time to leave me alone to calm down. She plucked the pegs from the nightstand and attached them to my nipples before standing over me, gently rubbing her beautiful breasts.
"I was thinking about leaving you with the vibrator pressed against your cock.... but I don't think that's a very good idea because I don't want to come back and find you've had an accident..."
She sank down until her pussy was right over my face, her pussy was visibly dripping her juices (so-fucking-hot) and she sank down further onto my face (thankfully avoiding the pegs this time!). Then she lifted off me, climbed off the bed and left me alone to get my breath.
It's funny, I remember years ago where I read in a story that a guy was in a chastity cage and his Mistress made him cum just by using a vibrator on his cage (and possibly his balls). At first I thought this was artistic license, but of course now there are many, many videos on the internet of exactly this happening - so clearly it is perfectly possible. In stories this often leads to the realisation for the Mistress that if the slave can cum in this most frustrating of ways, there is really no 'need' to unlock his cock ever again - truly a hot fantasy, even if like me you aren't actually locked up (but love the erotic cruelty of the idea).
The sensation was best under the head, but there were actually several places it felt really good and once Mistress was gone and my cock started to soften a little, I looked down and saw a single drop of pre cum escape from my cock and rest on the tip. I was clearly a lot closer to cumming than I actually thought and I really hope Mistress will adopt this as one method to ruin my orgasms in future. :)
I was going to tell Mistress about this when she came back into the room, but was distracted by the fact that she had shed her skirt and now I got the full impact of her magnificent outfit. Then before I could speak, Mistress walked up to the bed and gave my balls a firm slap sending the drop of pre-cum who knows where... ah well.
Mistress delighted in making me beg her to remove the pegs and then smirked as I winced in pain when she did. Then she released me and told me to remove the ballstretcher (I was more than ready to get it off by now as it was starting to sting), then she got on the bed and stood in front of me, pulling my head between her legs as I lapped at her delicious pussy.
Soon she pushed me back and then settled down on the bed. She looked absolutely incredible with her beautiful pussy peeking out from the PVC around it and her wonderful breasts showing through the cupless outfit as she played with them.
I sank down between Mistress's silky smooth thighs and gently started to lick around her pussy before moving towards her clit. Mistress was clearly turned on (she later said she knew it wasn't going to take long) but I didn't want to rush it. I took it very slow, determined to give Mistress time to enjoy it as much as possible, but eventually of course things fall into a rhythm and Mistress came relatively quickly and pretty hard.
Mistress allowed me to gently clean her with my tongue before ordering me back down onto the bed on my back. She didn't tie me down this time though and my hands were free to caress her awesome legs and sexy ass as she stood over me (facing away), which she didn't seem to object too.
I felt Mistress grab hold of my cock and start to stroke it as she teased me with her ass again. This time I kissed all over her cheeks (which I really loved doing) and then I felt the vibrating plug being used on my cock and I was soon rock hard once again.
Mistress had me beg to lick her ass and when she finally lowered herself down onto my face I reached up and slid the thong part of her PVC outfit out of the way and lapped at her delicious asshole.
Mistress allowed me to do this four times, and I loved it soo much... my throbbing as I pushed my tongue into Mistress's hole, desperate to taste her and make the most of this incredible moment. I really didn't want it to stop, but finally Mistress climbed off and I thought it was the end of the session, but instead she knelt next to me...
I reached up and caressed her left breast as she grasped my cock and stroked me hard and fast until I had to warn her I was getting close. To my great surprise she looked at me and told me that I was allowed to cum. The sensation continued to build and build and just as I was about to explode Mistress loosened her grip until only her fingernails were touching my cock and I slowly tipped over the edge into an agonisingly intense and extremely frustrating ruin. Struggling for breath I watched as my cum dripped painfully slowly down my shaft; my second ruined orgasm in a week after months without one.
As the cum continued to creep down my shaft I said 'Thank you Mistress.'
"Thank you for what slave?"
"Thank you for ruining my orgasm Mistress."
She smiled contentedly and scooped up some of the cum and spread it on her breasts, then she bent over me and allowed me to suck and lick them clean. Then she fed the rest of it to me with her fingers.
Wow, this session was absolutely AMAZING; I loved Mistress's outift (she looked even more incredible than she usually does, I really hope this outfit is put into regular use now!). I loved how wet she was and how hard she came too... it's totally worth the pain in my ass knowing that it turns Mistress on to punish me like that.
I absolutely adored being allowed to worship her divine asshole while she vibrated and stroked my cock, and that vibrating plug felt absolutely incredible pressed against my cock. I kinda hope Mistress does leave it tied to my cock next time.... :)
Finally I loved that she ruined my orgasm and fed my cum to me from her gorgeous breasts and fingers. I love to feel so submissive to my beautiful Mistress and it really made me appreciate how lucky I am to have such a wonderful wife and Mistress.
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