The Sex Lives of KinkyMira and Friends

Kinky and filthy things that have happened to us, all explicitly told

Tag: Feminisation

Pegtember: Taking The Tentacle (Update 2)

12 September 2026 / / 0 Comments

My husband was, so far, taking his daily peggings well, and he was enjoying our gentle foray into feminisation, proper women’s panties, tiny skirts, stocking and suspenders were all adding to the appeal of the peggings for him, and I have to say, us women were loving the feminisation, and the degradation of the spitting and drooling was playing well with him and us too.

Sunday (6th) was no day of rest for my husband’s poor abused asshole. By now, his asshole was complaining, sore, stretched, but we had to be so careful. If we injured his asshole, it would be game over. But it is hard when we are so excited, and his asshole so accepting. At the rate we were going, he would be pegged for well over forty hours by the end of this, and his asshole had to last.

Stacey came back to do the rimming and spitting, and was joined by Ella, as we decided to do two twenty minute rimming sessions to soothe him, and the girls checked in with him to ensure he was happy to carry on. Saturday was intense, and Sunday would be no walkover, as Sara was on a flying visit, and stayed overnight to peg my husband along with me and Ella, and on that day, I gave Sara the honour of the massive dildo at the end, and she fucked his poor asshole hard and mercilessly. On her arrival, she was wearing her own baby blue tie-sided bikini style panties, which it turns out she had worn for three straight days to prepare them for this evening, masturbating into them three times a day, cumming into them three times a day and pulling them over her messy cunt each day after her husband fucked her whilst pulling them aside. She held them to my husband’s nose whilst Ella drooled on his asshole and then started his pegging, and then Sara re-tied them to fit my husband, and put them on him, pulling them aside for us to further peg him, just like her husband pulled them aside to fuck her. All the while she was pegging my husband, she was talking about her panties full of girl cum, and how only sissies would cum hard from wearing her dirty panties and from being ass fucked by a number of wonderful voluptuous women. Her language was vicious, her pegging even more so, and my poor husband came and came. She was particularly nasty with the large dildo, and you should have seen her eyes when she saw the tentacle dildo he had ordered. She had no plans to come to peg him again, but that changed her mind.

Monday (7th) arrived, and Sara did the first twenty minute aftercare soothing sloppy anilingus, before she set off for the rest of her day. I did the other twenty minutes. I was hopeful the tentacle would arrive, but there was no joy, and it fell to Anna and Helen, with a little bit of me, to punish his asshole that evening with what we already had. At one point, Helen told him to stop whimpering, as this wasn’t even a quarter over, and his asshole wasn’t going to survive this. He came. Helen picked out the panties and stockings and suspenders, lacy black bikini panties, that they moved aside to peg him, over matching black stockings and suspenders. He also had the cock cage. Anna wanted that. As his second wife, she could see long term use of that. She particularly enjoyed sliding the steel into his urethra, an act that, on his part, demonstrates the utmost trust. And they both spanked him, in between the peggings, in between playing with his caged cock. As we were all called to be with our second husbands overnight, I left them to it part way through, and Helen and Anna both shared the warm-ups and the brute, before Anna stayed with him overnight, spooning him and loving him, whilst keeping him caged well beyond the pegging, and Helen went off to be ass fucked by Tanya’s husband.

Tuesday (8th) and Rose’s husband gave me my Submissive Sodomy whilst my husband gave Anna hers, and at her request, he still had the panties on. Anna then did the twenty minute analingus session (with the panties pulled aside) before going off to work, and Ella did the other one. I arrived home to find the tentacle dildo, unwrapped and on display. And I’d use it on his asshole that night. I sent a picture of it to Nikki, and she vowed to come up and use it on his asshole. But that night, the pleasure was all mine, with him warmed up by Ella and Laura. I’ve never lubed an asshole so much as I did that night. The tentacle was, quite simple, huge, a highly textured brute. I teased my husband all day about it, and in the moment, he was scared. But he knows I know how to manage his asshole. I’m eight days in. I have twenty two to go, so I’m not going to injure him. Yes, I’m going to push him and I’m absolutely going to train him. And that started at the end of a long and hard warm-up pegging from the girls. Its shape kind of pushed and stretched his asshole naturally as it started to go in. It stretched, it twinged a little, and his eyes moistened as I slowly pushed in. Ella nudged at his face, kissed and snuggled him telling him how well he was doing and repeating the “take it like a girl” line, perfectly mentally stretching him. I got over half way in, more than I was expecting, and then I fucked that little bit pushing it a little extra in each time, before finally admitting his asshole had taken enough for a first try. Ella still kissed him telling him he was a perfect girl, with sexy pink girly panties and a dildo up his ass, not just any dildo, a massive tentacle one.

Wednesday (9th) saw Ella back for sloppy analingus (she was rather enjoying it, especially the demeaning spitting and drooling), and Carla on the second leg, and Carla and Anna for the evening, with each of them doing a bit of tentacle work as well as me. They both got so excited about it and I know they’ll be on for full steam fucks when he can take it. The end of the dildo is huge though, so I didn’t know when he would be able to take it all the way. They put him in the cock cage, his urethra again being invaded by a stick of steel, and whichever one of them wasn’t fucking his asshole was playing with the cage, pinching and squeezing his balls and teasing his metal caged cock. You think his asshole was suffering, but his cock was too, caged, stopped from cumming and tortured by two women with an evil streak. He barely survived the evening, and clearly needed some cock sucking aftercare, Carla doing the honours, as well as the twenty minute sloppy rimmings the following morning. Anna spooned him for a bit immediately after his pegging, as I was required to be bred by the farm hand. Fitting all this pegging in with our free-use commitments takes some work!

Thursday (10th) saw me sucking so much cum out of his poor cock, and Stacey and Anna providing the rimming sessions, and Stacey was back for the evening, with Poppy, another new pegger, but Stacey had picked it up quickly and I was able to help out with teaching Poppy too. That session was long, but was calmer than some in recent days. Don’t get me wrong, he was pegged hard, but there was less frenzy, and that was quite fun. His cock was caged again, with whoever wasn’t pegging him gently playing with it, the teasing was just as bad for him though, the pain of not being able to cum was forefront as the pegging hit hard. But I had the tentacle, and wanted to make progress on getting it further in his ass. I was pressing into his ass hard, smooth, but not slamming, and I think Poppy realised what I was doing and kissed him and played with his balls in her hands, distracting him from the stretching his asshole was feeling.

He moaned a little at the pressure on his asshole, but Stacey dropped to her knees and said calmly in his ear (whilst Poppy was still kissing him) that “he was such a Good Girl, and if he took that tentacle all the way in, she’d piss for him, sexily, confidently, openly, whenever he wanted, however he wanted, she’d let him hold her cunt lips open to view, to taste, to enjoy. She’d become his own little piss slut any time he wanted if he just gets that little old tentacle all the way in.” God, she knows how to give him an incentive. As I pushed further in, she carried on sexily speaking to him, whilst stroking his hair, telling him “to make his asshole a big slut, like her pisshole would be for him. Imagine watching her bright yellow stream streak across the air, imagine drinking her warm sweet yellow piss directly from her pisshole.” I don’t know about him, I was still nearly cumming at what she was saying. She looked at me and saw me push it a little further in. She carried on, telling him he was almost there, calling him a Good Girl once again, a Good Sexy Girl. As I pushed in again, making his body shudder with the stretching, Poppy broke off kissing him and offered to piss for him too. “Not just once”, she said, and looking at Stacey, she added, “neither of us are just once”. She then looked at me, applying constant pressure to his asshole, willing the last bit in, and she added “Just like Mira pisses for you. Think how much you love that. And you’ll have two more.” She guessed I pissed for him. She was right. Mind you, Anna does too, and some of the other women. Still, it was a good incentive.

As I pushed it in, he rasped, amongst hard breathing, “Get it in, piss queens.” Instead of constant pressure, I started slow strokes, him yelping at each one, a yelp I wouldn’t normally ignore, but he’s made his wishes clear. Each stroke crept a millimetre further in, until suddenly it slid all the way in. He cried out, and I held the dildo as deep in him as I could. Stacey stroked his hair, and told him she was proud of his panty clad ass. Poppy told him he was such a good ass slut, and I, well, I was fighting to keep the tentacle buried deep in his asshole.

Once I got my breath back, I told him I was going to do a dozen slow strokes, ending all the way in, before I pulled out for tonight, and handed over to his new piss queens for a dozen each from them, and so I began, slowly, rhythmically, pushing all the way in, then pulling all the way out. As we passed a dozen, the pushing in got easier, and we hit twenty, the slams got harder, and the poor man, cock still caged and plugged, took all 36 deep strokes with the monster tentacle in his stride. Stacey pulled out of him, leaving his asshole quite sore, and Poppy removed the cock cage and gave him a blow job until he came, until he was finally able to unload the contents of his big heavy balls. I spooned him that night as well, big spoon to cuddle him. He deserved it. I think he needed it. And that night wasn’t the night to make these women piss for him either, no matter how much he wanted to.

It is clear that he is needing more aftercare on the night after a pegging, not his asshole directly, but loving, caring, cuddling. He’ll definitely get what he needs. It is also clear the morning after spitting and lickings are absolutely needed, to both soothe and moisten his abused hole. Maybe even three will be needed by the end. This is a marathon, not a sprint.

Pegtember: Tiny Skirts, Women’s Panties and Massive Dildos (Update 1)

6 September 2026 / / 4 Comments

We interrupt the normal posting schedule for our first Pegtember update. Five days in, and my husband’s ass has already been pegged for nearly eight hours in total. The general consensus of the girls is they want to average over an hour a day, with more than two hours on a Saturday, or Party Night as were calling it. That’s a really harsh amount for his asshole to take, I mean each pegging hour is harder on the asshole than an hour of anal by cock just because the materials involved are not natural and are more rigid, but he’s done it so far. It’s my birthday present and he always does his best to give me what I want. Which is why I asked him for another (late) Birthday Present, a fantasy tentacle dildo. To use on his asshole. He bought it immediately, obviously. Should arrive any day now.

Tuesday (1st) started with him finding the Pegtember box in his office and coming downstairs wearing delightful women’s pink satin crotchless panties, completely failing to contain his cock, and waving some stockings around. Quite simply, if I wanted him to wear stockings, he’d have to have his legs being waxed. Fabulous idea, and it felt like a real step forward. I asked on the group chat if anyone had waxing strips, but Stacey suggested I call the village mobile beauty therapist Tasha, who does a lot of emergency work. Initially, she said no, but when I mentioned it was the next step in my husband’s feminisation, she said she’d be round in minutes.

When she arrived, he was wearing only a standard man’s t-shirt and the women’s pink satin crotchless panties, and nothing more. She had him stand and removed the panties, so she could inspect what she had to do. He was, of course, cleared of hair in the “boy shorts” area by electrolysis some years ago, so her waxing task was straight forward. Something Tasha always does to make customers calmer is to slip her skirt and panties off to match their nakedness with hers. So, naked from the waist down, she cracked on immediately, and was about halfway done when Laura and Victoria arrived. Given Tasha knew what was going on, and was half naked, Laura and Vicki took their tops off and changed into their teeny skirts and strap-on harnesses, loaded with the first dildos, appearing just as Tasha was finishing his legs off and checking to make sure she hadn’t missed anything. Her checking included his cock and balls (a few times), and over his ass cheeks and down his ass crack, none of which she actually waxed. I took this as a cue to ask her if she wanted to stay for the pegging, and she said she could only stay a bit.

Laura, Vicki and Tasha quickly got him dressed for the pegging. Laura put on his white stockings and suspenders, taking great joy in how they slipped so easily up his perfectly smooth legs, Tasha put back on to him the pink satin crotchless panties she removed earlier (thus ensuring his panties were over his suspenders, as they should be for any Good Girl), and Vicki put on to him his obscenely short tartan skirt and thin white girly blouse. This was a schoolgirl outfit, that would only be improved if he had tits.

He was bent over the arm of the sofa, into the position we were going to peg him in, and Laura parted his ass cheeks, displaying his pucker for the first time, whilst I lubed his asshole, lavish amounts, including pushing it deep with my fingers. Then, in a degrading piece of symbolism I know he loves, I drooled onto his asshole, rubbing it in. Laura and Vicki each spat on his pucker and rubbed it in, and even Tasha drooled on his asshole and rubbed it in. She looked so cute, being bottomless and rubbing her drool into his pucker. She had a beautiful cunt and ass, and was totally hairless from the waist down, as you might expect from someone who waxes for a living.

Well, Laura and Vicki were insatiable. They fucked his asshole so hard, all while a bottomless Tasha was watching, and when I let her out, I invited her to come back another day and take part. She started to say no, and then instead went for maybe. Laura and Vicki carried on until his asshole was well stretched, well ready for me and the largest dildo he can take all of at full speed, a 9 inch long 7½ inch circumference realistic looking cock with big weighty balls that slam into his body on each stroke. I am training his asshole to take a larger one, and I’m not far off getting there. I’d use that larger one the next day, but I wanted his first pegging to be all full speed, full power and full length. I think what made Laura and Vicki fuck him that hard, apart from the excitement, was that schoolgirl outfit, and in particular the women’s pink satin crotchless panties. He looked so sexy with his cock escaping from panties not made for it, and with the tiny skirt flipped up to show his ass, our usual position. Laura and in particular Vicki had wanted him to wear a skirt and panties for pegging for so long, and each and every dildo was inserted through the gap and he was fucked very very hard.

Wednesday (2nd) started with me licking his asshole, a simple piece of aftercare that we agreed beforehand, twenty minutes of sloppy analingus to soothe his misused asshole, including quite a lot of spitting and drooling on his asshole, something he finds invigorating, but quite degrading. I don’t want to overdo the spitting and drooling, but it will be a part of every pegging and every rimming, he loves it that much, he loves the degradation, and his asshole does need to be soothed. I checked he was OK with what happened, every element, and that he enjoyed himself. He thoroughly did. Only 29 more peggings to go.

The evenings peggers were Carla and late replacement Paula, who came in as Anna had to be away for the night. Paula had never pegged anyone before, so she had some lessons from Carla and me, and she soon got in the swing of it. And this day was his first wearing the Gates of Hell cock cage with built-in Penis Plug. I have to admit I nearly came helping Carla to put it on him, lubing his urethra and inserting the long stainless steel cumstopper. He is used to sounding, but normally him doing it, not someone else. The rod was snug, as it was meant to be, and he was struggling before even one peg occurred. We put an obscenely short skirt and a teeny virginal white thong on him, cotton but so small his cage would never be contained, and then Carla spanked and paddled him a few dozen times, before Paula moved the thong aside to lube his asshole. Much lubing and finger penetration later, and we all three spat on his asshole before Paula pushed in the dildo. It was her first ever pegging session, and she really got in the hang of a hard pegging quite quickly, really fucking his asshole vigorously and mercilessly. Carla went next, Paula had another go, and then Carla ended up with the huge dildo I ended the session with the previous day. That is because I was deploying his latest nemesis, one he couldn’t take all the way, one I was training him for, and one I was determined he’d be able to take soon, well before the end of Pegtember. This is a 10 inch long 8 ¾ inch diameter brute, again realistic, but this time, the balls are large, heavy and move independently of the dildo like real balls do. Like all the other dildos, I made him suck it first, and lubed it in front of him, as Paula relubed his asshole. I normally ask him during training how far he wanted me to go, but not today. I told him he was going to this take more and further in than he ever had before. Saying the size really emphasised what was about to invade his asshole, and his cock did move, although was severely restricted by the cage.

I was very gentle, pushing it in, all the time talking to him about what a Good Girl he was, and how much he had taken. I reached the point where he yelped last time, and he hadn’t, so I pulled back out and pushed in again a little further, until he yelped. I stopped, stroked his hair and told him how proud I was, and how he only needed to take a little more, and then I withdrew and pushed in again, again pushing a little further than before. He yelped again, and Carla said he was so close, and a good cock caged girly like him could take the last half inch of length, and I pulled out and pushed back in again, this time ignoring his yelp mere millimetres from being all the way in. He felt the balls touch his ass and he knew. I held it all the way in as Paula praised and kissed him and Carla played with his cock cage, and then I pulled out and pushed all the way in again. He didn’t yelp. Again, Paula kissed him and Carla played with his balls as I did stroke after stroke, all gentle, but pushing all the way in, with a brief pause before pulling out again. This wasn’t yet a hard slamming ass fuck, but it would be soon.

I was doing stroke after stroke until Carla stopped me, with the dildo buried all the way, and she kissed him and told him he’d had fifty full penetrations with this monster, and did he want to end with a couple of dozen slightly faster ones. He was sweating, and just nodded. So I started, slightly faster, a slight slam at the end, and his grunting was showing the effect. And he managed all 24, and I felt that was enough for the day. Carla removed the cock cage and then gave him a blow job until he came in her mouth, something she shared with Paula and me.

The next day, Thursday (3rd), I did the twenty minute aftercare rimming and drooling session right after he gave me my morning Submissive Sodomy, and the evening peggers were Laura and Ella, Ella too not being experienced at pegging. We made him wear the cock cage and a tiny mesh florescent pink thong, which again didn’t handle the cage, and the blouse, but no skirt. Laura gets up some speed with pegging, and Ella, being young and energetic, wasn’t far behind. There was lots of slamming before, inevitably, I donned the 10 inch long 8 ¾ inch diameter again, starting slowly, but fully in after only four strokes, a few more slower ones, and then the bulk of the strokes at the fastest pace from yesterday. Ella and Laura were alternating between encouraging him and watching the brute impale him. When I thought I was well past 50 strokes, I stopped, pressing the dildo into his asshole, and asked him if he wanted faster. As if he was going to say no, I told Ella to count the 24, and I set about slamming the dildo into his asshole harder. If I’m honest, I wasn’t far off full speed, and his asshole took it. Sometimes, I’m amazed what his asshole can take. Clearly his cock suffered in the cage, and his asshole was really stretched, so after his asshole was emptied, I cuddled him and said how amazing he was whilst Ella sucked his cock clear of cum, again her sharing it with Laura and me.

Friday (4th) saw Ella pop in to do the rimming, with us both doing the spitting and drooling, and I did a quick check-in with him after that. The evening was a cage free one with him cumming a load all over the place whilst being pegged. The white cotton virginal thong was back, as were Carla and Victoria, and it was a first outing for the French Maid’s outfit. I was fairly broken, from a whole day of free-use as the only woman available all day, so I just watched as Vicki and Carla swapped, until Carla ended up with the brute, and she only did a couple of warm up strokes before slamming in hard. He yelped and, she slapped his ass, telling him to not be a wimp and to take this monster like a girl. He was almost in tears, but he took every stroke, every slam and his cock in such a mess. Vicki had to clean him up, whilst Carla told him how much she enjoyed doing that to him, but I’d slam even harder tomorrow. I wasn’t sure I could manage that, but I’d give it a try.

Saturday (5th) saw Carla do the sloppy analingus, and the evening we decided was Pegging Party Night, his asshole being the centre of attention. The twist here was that as someone stopped pegging him, he had to lick her asshole whilst his asshole was lubed for the next dildo, and with every change of pegger, that person would degrade him a little by spitting or drooling on his asshole and rubbing it in before pushing the dildo in. On duty were Laura, Victoria, Paula, Stacey and me. It was Stacey’s first experience pegging a man, and she had been wrecked by him earlier in the day, a four hour fucking session where she came so so much. He had the bright pink crotchless women’s bikini panties on, and his cock poked out of the waistband, meaning his cum sprayed all over his belly as we pegged him. I did my best at full speed slamming with the monster, and Stacey had a go too. What have we unleashed in this girl? He took the hard slams with the monster easier than the day before, meaning he was getting used to it. He needed to because the tentacle is even bigger. His asshole was being fucked for over 2½ hours, and as soon as everyone left, I got to be big spoon, giving him some love after his ordeal. It’s only day 5. 25 to go. His asshole simply had to manage.

I’ll do another update in a good few days. The first five days were hard on his asshole, and there was much degradation, but it will get harder as his asshole is used up more. I do have to say though he has thoroughly enjoyed it so far, he’s cum so much, he’s loved wearing the panties and women’s clothes, he’s loved the demeaning spitting, drooling and language and he loves the cock cage, particularly the rod down his urethra. And remember, this is MY birthday present. My mind is working on what his birthday present might be……

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