The Sex Lives of KinkyMira and Friends

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

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Pegtember: “Schoolgirls”, Listening and Tentacle-Filled Aftercare (Update 4)

24 September 2026 / / 0 Comments

It is half way in our Pegtember challenge, and I was away for work, getting myself copiously fucked in the process. But he was at home, being pegged nightly by a rotating cast of big-titted vixens, who were filming the events and keeping me fully informed.

Wednesday (16th) saw Ella giving him his first sloppy spitting rimming session of the day, but she ended up taking a Submissive Sodomy session first. Poppy gave him his other rimming and then I spoke to him, did a welfare check from afar. He was looking forward to the evening, when Nikki would be there for her first night of pegging, with Ella and Stacey. Nikki wanted the schoolgirl outfit, and she’d brought hers too, as she was enjoying schoolgirl fucks herself at the moment, and she hoped the following day, my husband would fuck her in hers. Ella and Stacey were wearing theirs again, their micro-skirts being as short as Nikki’s. She picked some backless tiny white frilly panties for him, and after Stacey lubed his asshole and Nikki’s dildo, she pushed the dildo in through the panties, pushing at his pucker until it took it. For a warm-up dildo, it was fairly large, and she fucked with enthusiasm and with power. It’s been too long since she’d pegged a man. She went hard.

In between peggings, the “schoolgirls” made out, kissing, masturbating, all within his vision, but without him being able to touch. Sometimes, whilst two of them made out, the other played with his uncaged cock, milking little drops of cum and pre-cum out of him, squeezing and stretching his balls, as he was admonished for reacting to “schoolgirls” fucking, and being spanked for it, before the next pegging began. His cock swollen, his ass red, his asshole sore, but still he carried on, still he loved what he was watching, still he took the punishment his ass and cock was receiving.

But since she arrived, Nikki had been adoring the tentacle, stroking it, playing with this monster, wondering just how his asshole would take that all in, teasing him for his upcoming pegging with it, and he knew Nikki was in awe of it, he knew she’d fuck him ridiculously hard with it, he knew his ass would know she’d used it. And she did, hard for a long time, all the time Ella and Stacey took turns with one kissing him and twisting his nipples whilst the other squeezed his balls and masturbated his cock, somehow managing to extract more little drops of cum and pre-cum.

His cock made a mess, his ass was a mess with all the lube, and after she ran out of steam, Nikki snuggled behind him, arms around his body pulling him tight, his ass still fully impaled by the tentacle, a kind of loving aftercare whilst still having his asshole fully impaled, whilst still being reminded of his filling and her possession. He went to sleep almost immediately, contented.

Thursday (17th) saw him awake still in Nikki’s arms, still impaled by the tentacle. She carefully removed it from his asshole, before removing the harness and giving him a long loving sloppy blow job, preparing his cock, making it hard, making it ready to invade her own asshole, to give her a hard dose of Submissive Sodomy. That he did, driving hard and for a long time, taking his asshole’s discomfort out on hers, all the while denying her an orgasm she so desperately wanted.

Submissive Sodomy certainly worked on her, making her feel so submissive, and yet so loved, and all three “schoolgirls” came back for his aftercare spitting and rimming sessions, they felt he needed three.

And Nikki was still feeling submissive when he ordered her onto her knees, her head on the floor, her tiny schoolgirl skirt flipped up, him holding on to her hips as he drove his cock into her accepting cunt, and he kept her there for ages, not rubbing so she would cum, but filling and emptying, keeping her on edge, until her head started going swimmy from being lower than her body, and still he fucked her, not allowing her head up, not allowing her tits to stop hanging in her face, the swimmy feeling and her submissive feelings keeping her there, keeping her on the end of his cock. She felt her body starting to wobble, but his hands were keeping her cunt where it needed to be. Her body tried to give way, but his hands were holding it firm, and with her cunt being rhythmically fucked, out of nowhere, an orgasm came, a swimmy, woozy orgasm, the woozy feeling completely taking over her emotions and her body, his cock completely taking charge of her orgasms.

Her brain was swimming, her cunt was dripping, filled and another orgasm was on its way, and when it broke, it was dreamy, and she felt another coming. Wave after wave or woozy swimmy orgasm gripped her for some time, him determined to milk her orgasms the way she was cruelly milking his cock the previous night.

She lost all track of reality, her entire world was just cumming in a hazy reality, until she was ripped back to her fuck by his cock throbbing, by him spurting cum deep into her cunt, over and over, hard spurt after hard spurt, and when he was done, he just laid her down and left her, sending Paula in to give her some loving aftercare. Nikki had to recover, as she was due to peg him again that night.

And as well as Nikki and Paula, Anna pegged him, his cock cage in place, his French maid uniform, black and white frilly backless panties, white stockings and suspenders under the panties, repeating the panties up and down dance, as he alternately gets spanked and pegged, them settling on panties down for a spanking, panties up for a pegging through the backless panties. His cock cage was mercilessly played with, his balls squeezed and stretched, his cock twisted a bit, spat on and wanked over the cage, and unsatisfactory wanking that frustrated him more than anything, all the time his asshole taking hard slams from bigger dildo after bigger dildo, and they each gave him more raw, hard tentacle than anyone else before, whilst telling him they were out to destroy his asshole completely. He was crying at the need to cum, but that made the three women just do more tentacle fucking on his asshole, and deployed my cat-o-nine-tails to his ass cheeks, a lot. This was the harshest punishment his cheeks had taken, the longest tentacle session his asshole had taken, and the most distress his cage had caused him.

And at the end of it, when the three women were exhausted, Nikki repeated the tentacle in the asshole hugging aftercare she did the night before. He didn’t drop straight to sleep this time, so she held him tight, keeping the tentacle in, and told him lovely things about how impressive he was and what a good little pegging girl he was. Soothing, loving, whilst Anna and Paula used the cat on each other, then fucking with a double-ended dildo, then the cat again, before splitting, Anna off to be bred by the farm hand, Paula heading for a fucking machine session with Carla.

Friday (18th) and after another Submissive Sodomy session for Nikki, all three women gave him his ass licking spitting aftercare, and as a treat for him, they asked him to use the cat on their ass cheeks again, him repaying them for what they did to his ass the previous night. Then he dropped Nikki off at the station (paid by a Passenger Princess blow job in a lay-by half way there), and then he came to my hotel to pick me up, making me take my skirt off for the journey home, so I was bottomless all the way home, and he collected another Passenger Princess blow job from me when we were nearly home.

And it being a Friday, as soon as I was in the village, I had a constant stream of free-use fucks, hard fucking from men that missed my cunt and asshole, all the while my husband watched, his cock in Ella’s mouth, not a blow job, just a comforting enclosed warmth, just an emotional attachment caused by his cock’s presence in her mouth.

I wanted him to reclaim me, but I knew that wouldn’t happen tonight, so instead, I put him in a black leather micro skirt, black frilly crotchless panties over black stockings and suspenders, and I realised Tasha would need to come back and wax his legs again, hopefully the next day. I also put his cock cage on way too early, playing with his cage cock, telling him how much I needed to be reclaimed, but how out of action his cock was, and how I’d have to deal with that later. I must have played with his caged cock for nearly an hour, interrupted by Tanya’s husband and Rose’s husband fucking me.

His pegging was long, brutal and over half of it was with the tentacle, so much so that I began wondering if we needed something bigger, and quickly too. That was, perhaps, a job for tomorrow, after my reclaim fucks and after Victoria, who was coming to give me a prolonged cunt licking session in my queening chair.

But after that night’s prolonged pegging, I thought I’d try Nikki’s aftercare with the tentacle on my strap-on buried in his asshole. As I snuggled him inside and out, Ella used bondage straps to keep the dildo in him, one strap round my and his left thighs, one around our right and one around our waist. Then, with his inside and out snuggles continuing, Ella drained his uncaged cock and balls, and then wanked his cock until it was a little sore and uncomfortable, all the while saying sweet things to him, until he, and I, drifted off.

Saturday (19th) and he sodomised me, reclaiming my first hole whilst not allowing me to orgasm. That was resolved with Vicki licking me out, making me cum and cum, and when her tongue needed a break, he sodomised her too, and then, me, her and Ella gave him his sloppy rimming aftercare session, with the other two staying to watch him reclaim my second hole, my cunt, with his dirty cock from two assholes, and then Vicki had some lovely mixed cum to lick from my cunt when I was back in my queening chair.

Tasha returned to wax his legs, and she and I fucked, double ended dildos, snogging, playing with tits and clits until we came and came and came, with her caged husband listening on the phone. We ignored him and just let him hear us fucking, and Tasha was part of the Saturday night team, so she trash talked him when we took a break fucking to say how he wouldn’t be able to listen to my husband’s pegging, how my husband would take a far bigger dildo than he could, for far longer than he could and how my husband was a much better girl, a much better wife than he would ever be, and she told him she would empty his balls when she got back, not into her, but straight into the bin, where his pathetic cum belonged. And then, with no niceties, she just hung up. She said he would love it, and be obsessed for the whole night with that she and the rest of us would be doing to my husband’s asshole, and it would take over his mind that I’d be wanking him into the bin. She smiled as she said if he was a good boy tonight, she might let him watch a bull fuck her tomorrow. Might.

And Tasha produced a tiny neon pink thong she had bought with her husband’s credit card for my husband to wear, and she wanted a longer skirt on him, as she wanted the fabric to be collected round his waist, a feeling she loves and wanted him to enjoy. Luckily, I had a longer one for him, and black stockings and suspenders, oh and the cock cage. Tonight was to be another night of discomfort for his wonderful cock, and on this night, he had over 2½ hours of pegging, over 1½ with the tentacle at full speed. There was no spanking, so it was merely a matter of endurance for his asshole, five women switching over and over to keep the pace up with his pegging, five women who ended up using the tentacle as hard and for as long as they could, five women taking every hard ass fuck they’d ever had out on his asshole.

And then, on camera, she uncaged my husband’s cock and gave him a loving, long, lingering blow job, visibly milking every drop of his cum in to her mouth, showing the camera and swallowing. When she got home, she showed it to her husband, before uncaging him, kneeling him in front of the kitchen pedal bin, having him kneel on the foot pedal to open it, slapped his cock round a bit and then just wanked him, not loving, dismissive, uncaring, annoyed even at having to do it, and after every drop of his cum did spray into the bin, she got him up and told him she was having a bull round tomorrow, and if he was a good boy, he could watch. So, wanting to be good, wanting to worship her, he worshipped her tits for a while, and then, after he did a good job there, she let him lick her out, lick her to orgasm after orgasm, until his tongue could do no more. And he went to sleep as little spoon with her gripping his flaccid cock.

As for my husband, Stacey was strapped to him, repeating the penetrating aftercare position I was in yesterday, and Ella stayed in front, milked his cock and gave him more praise. They both stayed with him, they both slept with him. I went to fuck Carla.

Nineteen pegging sessions are completed, there are eleven still to go, and my husband has been pegged for over 29 hours already. He seems to have hit his stride now, being able to take more and more, and he’s wearing the panties and tiny skirts much longer than for the peggings. I think he really likes it. I think he’s enjoying the feminisation.

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……

Free Use 2.0 (Part One)

15 July 2026 / / 3 Comments

I don’t think any of the five women had come down from our weekend of sex, of submission, of our first ownership by our second husbands and of our collective taking of Helen. To be honest, the men hadn’t either. They were rampant all week, they used us way more than usual, and we were all so up for it. And Helen, she’d been fucked so much that week, she’d barely got anything else done. Welcome to the future Helen!

But from this night, the new Free-Use arrangements would be complete. The whole new free-use community were gathered in our lounge. Eight men, seven women. The men were still fully clothed. Ella had her slutty waitress outfit on, in her full tits out, short skirted, pantyless, fishnet stockinged glory, and she was already busy giving drinks out. The rest of the women were in our Roman Togas, our left tits on display, our right covered up. There was no ceremony in removing our coats, revealing our first tit each, although Poppy’s tit was obviously exciting and was the centre of visual attention, but left untouched for the moment. That would change soon enough.

It was the party to celebrate two years of free-use, and now the extension with the new rules. Free-Use 2.0

There wasn’t an unexcited person in the house. The air was full of anticipation, of hype, and of promise. My husband was Master of Ceremonies, and explained that each woman would be strapped into our gyne chair for an intimate examination from the free-use community, male and female. The new women would be examined by every member, male and female, including measurements of their cunts, asses and tits as the four original free-use women had at the beginning of our free-use adventure. The new men would also get to examine the four original free-use women. Each inspection could only be for a few minutes, as there were a lot of inspections to do, but it was the perfect way to start the future, as it was so very revealing and enormously exposing.

We drew lots to work out the order of our examinations, and Ella went first. Probably sensible, as our husbands could set the pace with her examination and the new men could follow at the end.

The rest of the women would have our togas removed by one of the men, Ella (as her tits were both out already) would merely have her tiny skirt flipped up to reveal her cunt. Then all of us would have our tits worked by the same man, our tits would be groped, squeezed, pulled, twisted, stretched and generally manhandled. My husband did a sterling job on Ella’s magnificent tits. The postman did similar with mine. After our tits were sufficiently abused, the examinations would begin.

The examination was invasive, clinical. Inspections, insertions, stretchings, all to prepare us for a measurement. Ruler inserted into the cunt to measure depth, cunt lips measured as they are and then stretched to the point of pain to get further measurements. The diameter of nipples and areolae measured in a natural state, then worked by a monster mains-powered wand to peak arousal for more measuring. Clit diameter and length measured in its natural state, and then the same brutal wand making it as big and hard as possible for more measurements. Inflatable butt plug, inflated until she could take no more, used to measure her asshole. And many more measurements of her tits, cunt and ass.

As part of each measurement, photos are taken and each man will have them on a secret app, an app that syncs all their photos of us to all the men. For pure photo purposes, a speculum with wide outside flaps was used to display her pisshole and a metal sound used to push just inside, and then a different sort of speculum, longer, deeper was used to display her cervix and the same metal sound used to push just inside that too. So invasive, so demeaning.

They have hundreds of pictures of each of us original four, spanked asses, penetrated asses, penetrated cunts, sloppy blow jobs, gagging blow jobs, make-up ruined, you name it. That app holds our shame, those photos are our shame, and these new ones would be added. I’ll be honest, I don’t much like the photos, but the men want them, so they get them.

And when all the measurements were completed, when all the men had inspected her, Ella was masturbated until she came. Clinical. Unfeeling. Unemotional.

Rose and I went next, Helen followed, and then Anna and Tanya. Helen was inspected like Ella, the other four just had the new people inspect and a clinical orgasm.

That left Poppy. In some ways, that was pleasing, and her inspection was also like Ella and Helen, although she was forced to have two clinical orgasms one after the other. I have no idea why.

Despite being such an old friend, Rose had never seen Poppy fuck before, not even seen her cum before. She was probably the one friend Rose had never masturbated with. To be honest, she had little idea about her sex life at all, and yet here she was, offering to fuck Rose’s husband while she was away, and now about to take cock after cock like a fuck weary slut. Sometimes, even old friends surprise each other.

Next, as he had with Helen and her husband, my husband made all the new members verbally consent to free-use now and for the future, a consent given with witnesses. All did so willingly. One could tell from the tenting trousers on the men that they were ready to go.

Men would be chosen at random to fuck, until all eight women had fucked, then they’d start again. The women were already placed in sequence, Ella, Helen, one of the original four, Poppy, and then round again. No man could fuck his wife, or his second wife, so if they were drawn, they’d go back in the pot. I know my husband wanted Poppy, and I know he really wanted her asshole first, as he always does with new women.

I was on the second cycle, and of course, I drew my husband, so he went back and I ended up with the farm hand. I just looked at him and told him to breed me. He had a glint in his eye as he spun me round, bent me over the arm of the settee and masturbated me for a couple of minutes. He was rough, unfeeling, business-like. He then lent in past me, grabbed a hanging tit in each hand and started milking them, squeezing and elongating the nipple whilst squeezing the flesh to get milk out. Of course, there was no milk to get out (much to my sadness), but he milked my flabby hanging tits for all they were worth. Once he felt I’d been milked enough (and by that, I meant he ignored my comments about tender nipples and carried on until he was good and ready), he lined up behind me and just pushed his hard chubby cock in through my cunt lips and then slammed in hard. He was young. He had energy, stamina and power, and he just slammed me like an animal, pulling me into the right position, slapping my ass if I was even a millimetre away from where he wanted me, hauling my body to be in the perfect place for a deep penetration, pounding over and over with hard rhythmic slams. There was no finesse, no love. This was breeding, at its cold, harsh, business-like best. What made it even more electric for me, what made me even more kinky for me was the way he was talking the crowd through the breeding process like I wasn’t capable of understanding, like I was Buttercup a prized cow, the indignity of the discussion, the clinicalness of the breeding and his offhand demeanour just made the breeding so much more intense, so perfectly orgasmic. And of course, I came and he carried on breeding me, explaining how one orgasm was necessary before he planted his seed, before he impregnated me. Oh my god, the language, turning a decent fuck into an amazing fuck. And as soon as he came, he pulled out and explained how the prize cow needs to be left there for his cum to work it’s magic, and so I was left, bent over the sofa arm, legs spread, cunt gaping slightly, my breeding all but complete.

And there I stayed until my husband was drawn again, this time he was drawn last, this time he got Poppy. And as Tanya’s husband had used Poppy’s cunt the first time round, my husband took advantage of that situation to pull out the lube and announce to Poppy that her asshole would be his, would be filled by his hard cock, would be filled by his thick creamy cum. She looked very slightly scared as he bent her over the kitchen work surface and started lubing her asshole, but she knew that if she wanted to replace Rose properly, she’d have to take all their cocks in her asshole, and soon, and she was excited about that overuse prospect, so now was as good a time as ever.

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