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.