The Sex Lives of KinkyMira and Friends

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

Tag: Challenges (Page 1 of 2)

Pegtember: Tanya, School Uniforms, Harshness and Kindness (Update 3)

19 September 2026 / / 0 Comments

We are getting into the harder middle section of the thirty day Pegtember challenge, where his asshole had received ten peggings, but there were still twenty to go, and by halfway, I would have left on a business trip and left him being pegged by a crowd of big-titted vixens, all eager to fuck his asshole that little bit harder, that little bit longer, that little bit meaner.

Friday (11th) saw both Stacey and Poppy return to each give his asshole a twenty minute spitting and licking, him definitely needing the soothing effects of their tongues on his tender, abused asshole, his wonderful asshole that is learning to take the monster that is the tentacle. He’s fine for length and girth, from now it’s all about taking it faster and harder, full speed hopefully before I go away.

On this night, it was Helen and Tasha, who turned her maybe into a yes. It is a first for him to be pegged by a woman before he’s had any sexual contact with her at all, and I think she enjoyed the power in that. Like all us women when we are pegging him, she is topless, so her 30H tits are swinging away. She brought a tiny black leather micro-skirt, merely four inches deep, making her body very exposed and making her look rather dominant.

With the harness on and dildo in place, she asked Helen to take a picture of her for her to send to her husband. He’s at home, cock in a cage, very much like my husband’s, waiting to hear from her, waiting to hear about his wife fucking someone else. He’s a proper little cuck, who really wants to watch his wife get fucked, but she virtually never lets him, instead teasing him with pictures. Occasionally, she’ll let him hear, but obviously not today. His cock is caged because she doesn’t want him wanking whilst he’s waiting for her. Seriously, Tasha seemed so sweet, but she’s totally a hotwife, with a number of bulls. I suggested my husband would enjoy being a bull to her, and with a mischievous smirk, she said she hoped he would, and she leant in and kissed me, properly, hard, with tongues, whilst Helen took a picture for her husband. My husband could hear the kissing too, and his moving cock showed it was getting to him. But his cock was caged, so it was suffering as he listened.

We taught Tasha how to peg and she slammed hard, totally going for it with every stroke. Helen took a number of pictures of Tasha in action, and when Helen took her turn pegging my husband, Tasha was sending the evidence of her pegging him to her cuck husband. She then crouched at my husband’s face and whilst his asshole was being slammed, she stroked his caged cock and asked him if starting next month, he’d be one of her bulls. He asked for the panties from their first session for his collection, and lightly twisting his metal clad cock, she told him he’s a bull, so what he says goes. If he wants to keep her panties, then he keeps them. He nodded, whilst all the time moving from the dildo slams, and then he told her he’d have her ass first, and she told him how they fucked would always be his choice.

But she also told him she doesn’t do that much anal, and so asked him to be gentle. As if to emphasise what was happening to him, Helen slammed hard, and he told Tasha he would, at first, but he’ll end up slamming her asshole as hard as she slammed his. Oops. She delicately kissed him and said “You’re the bull”, and with a final play with his balls, she left him to be ass fucked by Helen. As she turned and saw me, she came over and said how wonderful I was for sharing my husband with so many women, and I pointed out what he shared me with loads of men too, and women, and she asked, almost scared it seems, if I wanted to fuck her? I put my arms round her neck, kissed her, with tongues, and after responded so eagerly, so passionately, I said yes. She thought his hotwife fucking a woman would really get to her husband. Helen was expecting to hand over again, but she saw Tasha and I kissing, so she carried on. She had plenty left in her legs.

And as if to up the ante, as if to make my husband be harsher on her asshole when he finally gets to fuck it, Tasha slammed him hard with the tentacle, him taking all, but from her delivered brutally. She was unrelenting. He screamed. But he loved it. Not sure his asshole did, but he did.

Tasha tongues kissed Helen too, as I cuddled and soothed my husband. He needed the aftercare, but he was so excited at getting to be a bull for Tasha, and at getting her asshole first and her panties for his collection. It was a great day for him. His asshole not so much.

Saturday (12th) and Helen and Ella were on duty for his sloppy analingus session, but Tasha turned up to arrange a talk with me (more of that discussion in later post), and took a turn sloppy rimming as well. The evening was another party night with Anna, Ella, Laura, Poppy and me. Tasha wanted to join in, but she’d got another bull lined up for a hotwifing session, and this bull normally fucks her four times in eight hours, texting her caged husband between with how satisfied his hotwife is and how much he made her scream. And he really does make her scream. She loves it, and so does her husband. He’s the one that started all this. Carla had to work, so she couldn’t join in, but I was going round to hers at whatever time it finished for some sexy barmaid time.

And for the Saturday Party, we had the French maid’s outfit, with black open-backed frilly women’s panties, and white stockings and suspenders. What made this one fun was combining prolonged spanking of the maid for poor performance, with the pegging, meaning the panties kept being pulled down and put back up again (as once again, he was wearing stockings and suspenders correctly, under panties). He was always spanked bare-assed, but sometimes was pegged with his panties round his knees and sometimes through the open-backed panties.

And at the end, whilst I was pushing to again get the tentacle all the way in, Anna and Ella were trash-talking him about how the maid couldn’t even take a dildo properly, despite all the spanking, and how a Good Girl would do it, no matter what. He wasn’t wearing the cock cage, so he came and came, despite his cock not being touched, strings of cum kept coming out of his cock. They then told him the maid would have to lick that up, as they weren’t wasting good cleaning materials on cum. After I had got the tentacle all the way in and slamming it harder than before, Ella rode his asshole with the next biggest dildo down, before Laura fucked his asshole some more with the tentacle and Poppy had him sucking his ass taste off her dildo.

Ella was so kind to him, in helping him to lick up his cum that was sprayed all over the sofa, and she not only swallowed the cum she licked up, she kiss swapped and then swallowed the cum that he licked up, all the while, Poppy played with his caged balls and licked his glans so softly and gently, whilst Laura licked down his ass crack and gave aftercare to his ass pucker.

Anna stayed to cuddle him overnight and gave him that loving snuggling aftercare, whilst I went to fuck Carla, and Carla took it out on my asshole, to give me a taste of what I was subjecting my poor husband too. I loved it!

Sunday (13th) saw Anna and Stacey give him the sloppy rimming, and Stacey was back in the evening with Ella, the young dream team, who had him in the Schoolgirl outfit and the crotchless bright pink women’s bikini panties, over white lacy stockings and suspenders. And he was in for a treat, because Ella and Stacey were each wearing a modified version of their actual school uniform, Stacey’s from last year, Ella’s from a couple of years ago. I had been modifying them for this exact event, as I knew he would love it.

Whilst they went to different schools, their outfits were similar. I cut their knee-length skirts horizontally to create two, a mini-skirt that just about covered their ass and a micro-skirt that ended half way down their ass cheeks. They each wore their micro-skirts and each bought a white see-through blouse with a knot at the belly to keep braless tits in place, and tight across them to make them bulge out of the blouse. Their respective school ties and white stockings and suspenders completed their schoolgirl outfits. Oh, and massive dildos attached to strap-on harnesses.

And then they started fucking his asshole in those uniforms. It was so fucking sexy and after each pegging (and while the next pegging was being carried out), each of them made him lick their ass cracks (to clean out sweat) and their cunts (so he could taste their excitement). All this was so intense for him, that he needed an awful lot of loving aftercare after this session. He was doing well, but both on the day aftercare and that the following day was key to finishing this. And I wanted to be pegged by these two in their schoolgirl uniforms, they were so very very sexy.

Monday (14th) and Ella and Stacey did the sloppy rimming, and then Anna and I had a chat with him, to make sure he was OK, and he was. He was experiencing mini-sub drops after each session, so the cuddles were needed, and the sloppy analingus did soothe his asshole and soothe his mind.

But I was worried now. Within an hour of this check-in, I was leaving until Friday, a well-paid work assignment where I was expecting some serious fucking as well. And I felt I was leaving him at the worst possible time. He reassured me I was good to go, and he had a plethora of big-titted vixens to look after him, all of them aware of his aftercare needs, and also how vicious and prolonged the peggings would be. He’d be in good hands, or really bad hands, depending on your viewpoint. The peggings would be recorded for me to watch if I had the chance, and the girls would keep the chat updated with what had happened.

And with that, I was bundled in the car for the trip, Passenger Princess blow jobs on the way before my husband left me in the hands of my ex-boss and his business partner. He got home and had a chance to rest before Laura, Paula and Victoria were back for the evening pegging, where he was in baby blue stockings, suspenders and open-backed panties. This was a much more loving session, trash-talking was all more positive, the ass-pounding was still as hard, and after Laura got the tentacle all the way in, but slowly and gently at first, harder by the end of her thirty, Paula and Vicki each did thirty hard slams with the brutish tentacle, with Vicki giving him a load of aftercare cuddles, praise and love, whilst Laura and Paula fucked each other in another room. I think he was seriously emotionally flagging at this point, and we are not even half way just yet.

Tuesday (15th) saw a second consecutive day of Ella and Stacey on the sloppy rimming, and it was Anna, Carla and Helen on pegging duty, his schoolgirl outfit deployed, a tiny pink thong to move aside to be pegged, the cock cage in play to stop him cumming, and spanking again because of her poor school performance. They were a little harsher with the tentacle than the day before, but it was going all the way in, and there were lots of slams. His asshole is so accommodating and so receptive, it is amazing. With three fully fit big-titted vixens, this pegging was longer than most. They were just about to call it a day, when he started begging to have the cage taken off and to be allowed to cum, so obviously, the evil streak meant that they said no and fucked his asshole some more. Eventually, when they were all exhausted, Anna removed the cage and sucked every drop of cum out of his cock, sharing it with Carla, Helen and the schoolgirl “as any Good Girl should”.

That fuck marked half way in the challenge, fifteen consecutive ass pegging sessions, fifteen consecutive feminisation sessions with panties, skirts and stockings and suspenders, and calling him a Good Girl and having degrading spitting and drooling on his asshole. Watching it from afar later that evening (between fucks), I realised how far he had come, and wondered what the second half would bring, and wondering whether his poor abused asshole would survive.

Pegtember: Taking The Tentacle (Update 2)

12 September 2026 / / 4 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 / / 7 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……

Pegtember: Power Shift

1 September 2026 / / 4 Comments

Oh, my husband’s asshole is so going to massively regret this.

A couple of months ago, he asked what I wanted for my birthday. I think he was thinking something nice to wear, perhaps something to show my body off, or a new sex toy or piece of kit for our sex room. What I replied was that I wanted him to complete Pegtember. He gave it a little consideration, and then said OK, if that is what I wanted. It was, and then, in a flash of inspiration and without massively thinking about it, I told him I wanted him in Girl Mode every time we pegged him, panties, skirts, costumes, that sort of thing. He looked a little wide eyed, but told me it was my birthday present, and if I wanted to peg him with him in a skirt or panties, so be it. I don’t think he really thought it through.

For those who don’t know, Pegtember is an event where someone is pegged every single day of September. Thirty consecutive peggings. Now, he’s normally pegged once a week, sometimes twice, normally Laura, Victoria and me, sometimes Carla and me, sometimes Anna and me. As you may remember, my body isn’t up to giving his ass the seeing to I think it deserves, so I get support. They get to do the long hard warm up, and I normally get to finish with the monster, the big dildo, the one that really stretches his asshole. Long satisfying pegging for him, building up through dildo sizes until I arrive with the huge one. Win-win for me, getting to watch him get near, then getting to use the huge one on him as a finale.

But a whole month. Thirty days, not missing a single session, will be hard for his ass. Mind you, I get sodomised every day, so he owes me, right?

I told the girls. I told them I needed at least one of them every single night to support me in his pegging, ideally two. I know some people do shorter peggings for Pegtember, to help the poor peggee’s asshole get through it, but I’m not. I want long, full, brutal peggings just like normal. Just more of them, just every day for a month. He’s always pushing me to take longer, harder, bigger. Now it’s his turn.

We started putting names in the calendar, and I realised I’m away working (well, fucking in the name of work) for a few days in September, so the girls agreed to peg him in my absence, live on video for me to watch and masturbate to in the comfort of my hotel room. There were lots of volunteers for pegging him, and the girls insisted on a 45 minute minimum pegging each and every day, whether I was there or not. I happily and eagerly agreed, after all it wasn’t my asshole, although I suspect my asshole will pay over the long term. It’s used to it. He’d have no choice but to agree, he’d have no choice other than to take whatever pegging we wanted to mete out.

We made up a Pegtember box for him. All the strap-on harnesses and dildos. Lube, lots and lots of lube. And women’s panties to fit him, panties I’d bought specifically for Pegtember. Proper girly panties. Tiny thongs, crotchless panties, open-backed panties, ones that wouldn’t hold his cock, thongs we would move aside to penetrate him, crotchless and open-backed ones we’d fuck through.

Also in there is a French Maid’s outfit and a Schoolgirl outfit I made for him, complete with stockings and suspenders I bought for him. I’ve been meaning to sort these outfits out for so long, and this was the excuse to get my sewing machine out. Paula and Laura wanted to peg him in a French Maid’s outfit, Anna and Victoria is a Schoolgirl one. All four will have their way. There were tiny skirts like he has me wearing, including some of the indecent variety I often wear at home, and a blouse, one for someone with tiny tits.

This Girl Mode shouldn’t be a surprise if you read my post about buying him panties and short skirts earlier in the year. He’s worn the panties a lot, and the skirts quite a bit at home, and out to the event he wanted, but I really wanted to move this on, wanted to get him into Girl Mode, which he has yet to do. This is a good chance to cement Girl Mode for him.

And also in there is a Gates of Hell cock cage with built-in Penis Plug, a stainless-steel torture device to use sometimes. Rings down the shaft, a ring round the base of his cock, a ring round the base of his balls, a ring under the edge of his Glans, and a Penis Plug, long enough so that even when he is as erect as he can be in that thing, his urethra will be full of metal. It will stop him cumming. Laura and Victoria wanted to stop him cumming. Apparently it makes the man focus on the pegging even more. And I’ve wanted one of these for him for the longest time too.

I won’t post updates every day, just occasionally. We want it to be tough for him, a struggle for him. He likes pushing us to extremes in the hunt for sexual gratification, now it’s our turn. We are going to enjoy the pegging, the costumes, the skirts, the panties, but above all, we want him to enjoy it, as well as endure it, and I want him to get really into Girl Mode and to want to do it more.

The Pegtember box is on his home office chair, waiting for him to come home from work. Laura and Victoria are due about 8pm. Let the pegging fun begin!

Cake And Cunnilingus Day – April 14th

14 April 2019 /

Ever since I first heard about this day a couple of months ago, I’ve been really looking forward to it. After all, I love cake and I love having my cunt licked. To combine the two sounds divine, all on the same decadent day.

Cake and Cunnilingus Day is a response to the male-centric Steak and a BJ Day (March 14th). My husband and I have observed that in recent years (even though I don’t like steak and I can think of much better things to do with his cock than a blow job, but Steak and a BJ Day is not about me, it is about my husband and his pleasure).

Steak and a BJ Day is in itself a response to Valentine’s Day (February 14th), and all the corporate bullshit and sales opportunities that surround it. We’ve never observed Valentine’s Day, but I decided it would be nice to observe Steak and a BJ Day, as he’s a wonderful man who deserves all the pleasures I can throw at him.

He did express a desire for an equivalent for me, and we were both pleasantly surprised by the existence of Cake and Cunnilingus Day. I know his tongue is up for the challenge, as in our version of Cake and Cunnilingus Day. there is lots of cake, and lots of cunt licking.

On the day before, I made three cakes, a Country Farmhouse cake with sultanas and crunchy sugar on the top, a gooey Chocolate cake with chocolate ganache on the top and cherry jam in the middle, and a traditional Victoria Sponge. That’s a lot of cake to get through (and I decided to be kind and let my husband have some too!)

In our version of Cake and Cunnilingus Day, each time I eat cake, he needs to eat out my cunt. He’s not allowed to stop before I finish my cake, but he can go on afterwards if he wants. I’m not allowed to stop him licking me out once he starts, so he can make me cum if he wants, and he can continue to lick my cunt regardless of how sensitive it becomes (which is sometimes does with a lot of licking). (Remember, this is about me and my pleasure, in the same way that Steak and a BJ Day is about him).

I didn’t get far beyond midnight when I asked him to bring the chocolate cake. He placed a slice on a plate in front of me, then parted my legs and buried his face in between them. As I picked up the cake, he started licking, and had a nice rhythmic stroke up and down my lips with his tongue, occasionally burrowing deeper. I felt my cunt start to tingle in a way that meant I was about to cum, so I slowed down the cake eating. Now realising that I was about to cum, his tongue flick speeded up, and as I came, he buried his tongue deep into my cunt and sucked away at my juices. He saw I had finished off the cake, so he left my cunt and moved up to kiss me. He knows I love the taste of my cunt on his face, so I licked all my juices off his face, before kissing him passionately.

I drifted off to sleep thinking about how much he’d lick my cunt, how many orgasms I’d have, how much cake I’d have, and what a fabulous day this would end up being.

I awoke to him gently licking at my cunt. It is a lovely way to wake up. I looked down at him and smiled as he meticulously explored my lips with his tongue. I looked left to my bedside table, and there was a slice of the farmhouse cake, which I picked up and took a bite. I was in no mood to cut short the licking, as it felt really good. It was about 15 minutes before I finished the cake and he finished licking me. He then lay next to me and I snuggled in his armpit. I was feeling quite soppy and very loved.

My next cunnilingus was about an hour later. I needed a piss, so I had him lying on the floor, I crouched over him with his tongue flicking over my pisshole, and I drained my bladder into his mouth (as we often do, he swallows of course), then he carried on flicking his tongue over my lips and clit, whilst I had a slice of the Victoria sponge. In this position, it feels like he can get his tongue deep inside my cunt, and soon, I began to realise he was going to make me to cum again. I finished the cake just before he did and he got me to the edge of cumming, then held me there, only flicking his tongue across my cunt occasionally, having it buried deep but stationary the rest of the time. He held me on the verge for about 10 minutes before finally allowing me to cum. At least I didn’t have to beg this time!

A further hour on, and I was again squatting over him, this time the other way round, so his eyes were by my ass rather than my cunt, and he was again licking me out. I almost forgot the cake I was so zoned in on the licking, but he reminded me, and I had another slice of the Farmhouse cake.

My next cunt licking was at lunch. We had a light lunch, and for dessert, I slid forward on the chair, so my ass was precariously perched on the edge of the seat. He was under the table on his knees and licking at my cunt, whilst I had some Chocolate cake.

After lunch, he had me dress in a skirt and blouse, and we went for a walk in a secluded spot we know. We usually fuck when we are here, but today, he handed me a piece of Victoria sponge, he leant me backwards against a tree, flicked the front of my skirt up past my waist and he started licking me right there. Being outside and possibly being caught always adds to the arousal, and it was very clear that he was going to make me cum again, due to his unrelenting focus on my clit, with only occasional flicks across the rest of my lips. I take occasional bites of the cake, as I know when he does this, he builds me up for a massive orgasm, and that takes time. As he finally allowed me to cum, he held on to my ass, as he quite rightly guessed that my legs would give way and he’d have to hold me up. I think I yelled to as I came, but I could quickly flick down my skirt as we innocently went back to the car.

His tongue had a couple of hours break after that. It was pretty tired, but I didn’t want to wear it out. Our next cunnilingus was at dinner, like before with him under the table. After another hour, I was on the sofa, and he arrived with my mains-powered wand. He plugged it in, and he told me to get my cunt nice and tasty, and he settled down to watch me make myself cum with my wand. Today was a good day, as I was so aroused, I managed to get a rolling orgasm with it. I know that type of orgasm means my cunt and legs are very messy, and soon after I finished, he handed me more cake, and started licking me out. My poor clit was very sensitive, so his licking had me on the edge between pleasure and pain, but he persisted, and despite us having to slightly shift positions regularly, he licked me out for over an hour.

In no time at all, it was about 10:30, and time for my final cake and cunnilingus of the day. He again gave me the wand, and despite my poor sensitive clit, he told me to make my cunt yummy again. I’ve never managed two rolling orgasm events in one day before, but I did that day, what with his relentless focus on my abused clit, my general level of arousal, and my need for a final piece of that chocolate cake. When my rolling orgasm naturally died down, he took his place between my legs and started with a very gently licking, slowly getting firmer, faster and more probing with his tongue. He was certainly cleaning every drop of my juice from my cunt and was making me generate more to replace it. I reached the point where I’d normally tell him I’d had enough, but not today. I had more cake as he powered through my sensitivity and brought me to one last big orgasm, which he cleaned up with his tongue. Finally, his tongue had enough, and he left contact with my cunt. I sat there with my quivering cunt still on display, as he slumped in a chair and watched me.

We were both exhausted, I’d eaten far too much cake, and his tongue was barely able to function. What a brilliant day. We decided to book next April 14th off work, as we wouldn’t want to waste part of the day not being together. We are definitely doing a full-on cunt and cunnilingus day again next year!

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