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.
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