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Introduction:

An optional part 2 to the first story for those into pegging
Hypnotising My Brother to Cure His Shyness optional part two

*Be warned this part is optional for a reason, it involves pegging which for the uninitiated is when a girl uses a strapon on a guy, it's not for everyone.*

I then when I recovered got Adam to clean up and dress. One of the nicest things about hypnosis was ordering someone to clean up things. She couldn't wait for tomorrow but she had to set things up. ‘Ok Adam in your room in the top drawer I have placed a butt plug and a tube of lube you are to insert the plug and wear it for the rest of the day only taking it out for the toilet’ ‘ok’ Only you are to know about it so you must not mention it’ sometimes patients do silly things like talk about what they are doing like it's the most normal thing in the world. ‘I want you to spend time with me and your mother tonight, not going to bed until we do.’

By the time their mother came home Adam had been wearing the plug for a few hours and it was humorous to see him walking awkwardly with it around the house. We cooked together and I suggested we watch a movie, my mother agreed and I think we watched Back to the Future 3. ‘It's good that we are here together. It's been a long time since we sat and watched a movie just the 3 of us’ Said mother after the movie. ‘Oh I think we should watch another one if you're not too tired?’ I said ‘Oh I can, What do you want to watch?’ ‘I think Adam should decide… Adam’ ‘uh what about Grease? I haven't seen it in years’ ‘Grease it is’ Ma looked surprised it was really unusual for Adam to speak never mind express an opinion or to choose anything. ‘I’ll get the drinks’ I said as I left for the kitchen ‘I'll get us some popcorn’ said ma as she left for the kitchen. ‘I don’t know how you are doing this but its working Fiona, he still looks uncomfortable but he really is trying his best to be more sociable’ I froze and tried not to laugh at the uncomfortable comment ‘Its true its working, He has had some big breakthroughs at work and that helps his confidence. He has been able to talk to a woman at work’ I said as I grabbed the cokes from the fridge ‘Maybe one day he will find a good woman and she shall take him to bed, that would sort him out’ I almost died inside the fridge, my mother was wiser than she knew.

Back in the living room and Adam had got the movie ***********ed and paused at the start. ‘Heya little bro you’re doing so well.’ ‘Thanks sis’ Ma was still in the kitchen and I had a naughty thought. I put the cokes down and sat on his lap and put my arm around his neck. ‘It's so nice having you here with us’ He was trying desperately not to look uncomfortable not just because of the social anxiety of the proximity to me but because of the added pressure to his plug. I kissed his cheek and cheekily wiggled my butt on his crotch. I felt him stiffen. ‘Love you but I best get off before Ma comes in and thinks I'm seducing you’ I got off and he looked relieved but I could see the bulge in his shorts.

Ma came back and we watched the movie even joining in with the songs where we remembered the lines, even Adam joined in he actually had a decent voice. After the movie ma hit the hay first which was great as I could give Adam his last instructions. I put him back under with a few phrases and actions and asked him some things ‘How does your Buttplug feel Adam’ ‘It feels good but.. Uncomfortable’ ‘Ok when you get in your bed you may take it off for sleep’ ‘Ok’ ‘I want you to wake up at 10am and shower and toilet before putting the plug back in, come wake me at 12 if I am not up yet Adam’ ‘yes’ ‘No masturbation tonight Adam’ ‘Ok’

I had looked up this pegging fiasco and it was an interesting phenomenon which involves role reversals between a man and a woman. At first I thought Adam might be hiding homo-erotic thoughts but when i quizzed him on this he surprised me by saying it was important it was a female and he had no desire for a real cock. I had researched it more then and athough bisexual involvment were not unknown, the overwhelming majority of participant in the fetish said the same. This was interesting to me in a professional capacity and I must admit I was slightly turned on at the idea myself. I loved watching girls pose as they penetrated their partner, clearly an enjoyable experience for both participants. So I bought a strap on and tried it on. It was so strange to suddenly have a penis and I'm not gonna lie I loved touching it and even walking around with it on. I had stressed a bit on size and I went with a modest 7inch cock, I still had no idea if it would even go in. I was going to find out tomorrow.

The next day Adam showed up at noon as instructed I put him under. ‘Is mother away?’ ‘Yes’ ‘Ok lets go to the bathroom.’ This time I woke him within his box and restored his memories of the day before, I asked him to wash me, eagerly he agreed. It was nice having his hands all over myself rubbing me and rinsing me. This job had its perks. ‘Ok Adam we are going to my bedroom. I expect you to carry me there. No clothes’ He did as he was told and placed me on the bed looking hopeful. ‘Ok Adam, what's pegging?’ He looked shocked ‘Uh its about a girl fucking a guy in the ass with a strapon’ ‘You told me when I hypnotised you, you wanted to do this well I think it would help you to live out that fantasy..’ I pulled out the strapon and Adams' eyes went to it focusing on it ‘uhmmm..’ ‘Listen this might be the only chance you have of actually doing this, it's up to you Adam.’ ‘I want to try it! I just want you to tell anyone’ he confessed ‘You have my word, your my patient after all’

‘How would you like this’ I said, slipping the cock on as Adam watched with big eyes… I teased him by applying lube and stroking it on my girlcock seductivley. ‘I always liked the idea of being on my back first…’ With that he slowly sat down on the edge of the bed and as I approached he raised his legs. I ignored his ass at first. I began giving him a slow sloppy blowjob as he watched me looking up at his face. His cock felt bigger than yesterday. I then put a cock ring around him and one around his balls. This moved his balls up and stopped it deflating, in my research most men struggled to maintain an erection with pegging. That done I sucked the even more swollen tip of his cock and swirled my tongue around his head making him moan. I then moved down to his balls gently licking them both giggling as he flinched at the sensation.

Without looking and still suckling on his balls I found the pullring for the butplug and slowly began to remove it holding it at several points to hold his anus open. I then removed it entirley ‘You ready for my girlcock?’ ‘Yeah, i'm ready’ he said, sounding eager for it ‘Now remember you need to relax it for it to go in’ He looked at me as I stood up and pushed his legs back further. I lined it up with his anus and loved the reaction as he flinched involuntarily. My eyes met his as I began to put pressure down on his anus. It took a couple of attempts but then the tip popped in. ‘That ok Adam’ ‘Yeah it feels good’ ‘God Adam you're such a little slut.’ I slowly inched it forward until it was all the way inside loving the moan as I finally bottomed out. I let him get used to the sensation then asked him ‘Well Adam are you ready to get fucked by your big sister?’ His brow furrowed but I wasn't going anywhere till he answered’ ‘Yeah… Fuck me sis’ ‘Fuck you where?’ ‘Fuck my ass… please’ God this was a turn on I could feel myself gushing underneath the strapon. I began to move slowly I began moving a little and I adjusted the strapon a little then a bit more out then in, Adam was lost in the feeling as I began clashing my thighs against him then I grabbed his cock and began stroking to the rythm I was fucking him. He was looking at me in the eyes and I could tell he was loving the sensations. ‘You love being fucked by my girlcock huh Adam’ ‘God yes… this feels great’ Then I stopped and pulled out he looked kinda sad at that ‘Ok slut I want you to turn over and get on all fours’ Clearly I was enjoying this Adam Did as he was told and I slid back into him without any issue. I was able to pound him harder from this angle and the noise of me fucking him filled the room along with his moans ‘You like this, being fucked like the bitch you are?’ I pulled him up till he was straddling my girlcock and reached around and stroked his cock as fast as I could… he quickly erupted ‘Oh god… Fuuuuuck’

Ok Adam I want you to make me cum now. Adam responded by helping me take off the strap and placing it aside. He kissed me from the kneck all the way to my pussy where he ate my sopping wet hole with gusto it really didnt take long I was thinking of the fun of fucking his ass I really think I found a new kink for myself. Then Adam did something unexpected. He moved slowly down to my asshole and licked it just once. I flinched and he looked up to me, his eyes asking an unexpected question ‘uh… ok.. Just take it slow ok.’ He did as he was told, this was unplanned. I had never tried any buttstuff but this was important to him and Having just done what I had I kinda wasn't entirely against the idea. I felt him lick around my anus then slowly he began to lick it and it felt great… tickly but great. His tongue went inside and I squirmed but I can't deny I enjoyed it. After a while he looked up and surprised me again ‘Sis, would it be ok… if I put it in?’ I looked at his cock erect again already.. I was dubious it was pretty big. ‘Uh we can try but if its too big take it out ok… and use a lot of lube.’ He did as he was told and even applied lube with his finger to my ass. The tip went in easy enough and slowly very slowly he eased more of it in. My ass burned slightly as it stretched to accommodate this monster. But slowly it made it all the way inside. ‘Ok… stop… for a second… its sore’ ‘You ok sis’ He bent down to my breasts and began sucking on my nipple. This helped more than I expected and when he touched my clit it began to feel actually quite nice. I hadn't noticed him begin to move but it felt kinda nice. He moved my hand to my pussy nodding at me as I began to play with it quickly finding my clit. He leaned back keeping my legs in the air and started to penetrate me at an angle that rubbed my pussy walls though my ass. It felt extraordinary and in no time I felt a strange build up. I thought at first he had ejeculated but he was still going.. Strong. I was screaming with pleasure at this point loving every time he pushed into me and my ass clinged to him as if not wanting to let go. Then he kicked it into high gear and I was on the verge of something massive as I came then I felt myself clamp down on his cock and this in turn made him ejaculate with a loud moan of effort. I wondered as he lay there beside me kissing me holding me who had discovered more about themselves here me or him?

This had to end like all good things, I made him clean up the room after putting it back under. Then we showered together for the last time and he fucked me in the shower one last time and No lie I wanted nothing more than to keep this all going but it was wrong on many levels. I hoped this had worked as I then removed the box from his mind and he would remember nothing of our encounters or even the movie the night before sadly. It worked though as he went on to be fully cured of his shyness and within a few years settled down with a nice girl and had a family. I found myself seeking out partners who loved the idea of being pegged.. It was my fetish now. I even enjoy buttstuff almost as much as they do.

-fin-
1 comments

Cloudblower719Report 

2021-10-18 04:47:50
I also enjoy a nice pegging.

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