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……
Recent Comments