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Chapter 21 by WBD
Whose messages does Jack check and who does he respond to?
Kelly , let's get some matchmaking started
(Work in progress)
Jack clicked the message from Kelly, he figured it would be the best one to answer anyways, the message thread opened and the newest set of messages were not that old. Jack read threw a few of them Kelly had sent within the early morning.
'Morning Jackie, I didn't want to wake you but I'm off to work now, let me know how your feeling when you wake up.'
'Hey sleepy head are you even awake yet or did you sleep in, if you awake tell me your ok.'
'Hey Jack, tell me about your period, like do you think you are higher or lower on the oestrogen producing scale, is it a lot of blood? Also do you want me to start looking for you know some female attention for you for you or are you gunna have a guys day or night or something?'
'Your starting to worry me it's already like 10am, did you leave your phone to do chores, I said I don't mind if you don't do anything I can do stuff myself when I get back home. Also I know you didn't say yet but I already started thinking about who to set you up with. Just let me know if you want me to bring someone or some people back home tonight and I'll scout out all the potential candidates so you can have the pick of the menu.'
Ah geeez Kelly was already asking people, Jack thought. Well better message her back before she told the whole female world Jack was on his period and wanted, craved, needed sex even though at this point he might have wanted any and all women to just bed him. Jack quickly messaged her back.
'Hey Kelly, sorry I slept in, then went to the bathroom before checking my phone my bad sorry. I'm ok or well I have my man period now I guess so yeah I guess we were correct about the place I was in the cycle and all. I don't really know how to tell for sure but from what the Internet says I'm probably somewhere on the higher end, it comes and goes but I feel it's tingling inside and I feel warm and horny too, I've got a need it's like I want physical touch I assume from a woman oh and just now I started to feel like I want something more you know, I'll probably play with some toys but I guess if your already asking people if there interested in me then sure. We can find a date for me, but I want someone super nice to lose my virginity to I guess and hopefully someone who wants to claim me as their partner, you know someone loyal and wife like and come live with us maybe too that would be nice. I guess hopefully there is someone like that but if you have good ideas of partners otherwise then send me a full roster by all means. It's hard to tell because I'm not used to it but I think inside me really wants what's inside a woman to be inside me so I guess make it someone who wants to cum a lot also.'
Jack clicked send
Immediately there was a flurry of excited replies from Kelly
'Omg thank god your ok, and omg yes Jackie of course I'll find you some of the cutest and sexiest lady's and send you profiles of the ones I find, I already know a few I'd want to set you up with, you know my friends and some work colleagues but I'll search around everywhere, online, at work, in cafes or bars, the gym, the hospital, the old peoples home haha oh and for sure there is got to be lots of interested young women in the various university's and collages in the city, I bet most young women especially those who just turned legal and most will be looking for guys to lose it to also. Oh I bet the science technical collage has loads of shy young nerdy girls who just want to find and sit on their first and probably only penis in life, plus I bet those in medical schools they would be super interested in your period too. I bet you'd love some poor introverted thing, one with tones of cum saved up just for you. Or perhaps you would prefer a lady with a bit more experience, maybe someone dominant or mature who is already set in life and wants to settle down and have a bunch of kids. Oh this is all so exciting Jackie I'm going to see if I can clock out early after lunch to go gather potentials for you, I promise your womb is gunna get its first taste of womanly semen tonight even if it all just leaks out by the morning with your period.'
Jack relived in the knowledge that he'd get to have a try at real sex, his body feeling more and more needy by the second in this reality and Kelly was kind and willing to search out potentially amazing women for him to chose from, even if the idea of potentially getting pregnant in this reality scared him a little. In the mean time he was feeling horny, and hungry and also a strange feeling like he should have been making himself useful doing chores but at the same time his period was making him feel all awkwardly too he almost re-texted to beg for someone quick but he figured he'd try stay a big independent man and hold off as long as possible. Every now and then his belly would cramp and he would feel like a stronger gush kind of like an almost peeing sensation more than just a leak. In fact the regular slow leaking sensation in general was almost constant but the tampon was doing the goddesses work absorbing it inside him, he'd have to change it in a bit its absorption would only go so far but first he decided he'd find something for at this point brunch and he would also do a chore of some kind to make himself feel less bad for staying at home all day, after that he'd definitely go back to trying new sex toys and porn or something to distract himself and help out his body's cravings whilst he waited for Kelly's sex selection.
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currently re working the story have to up to here so far but i have ideas i dont know how to fit in yet. past this i have not reworked yet.
What's next?
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Jack and Kelly's excellent adventure
A spinoff of "changing the rules" by street0
(Changing the rules by street0) story line but just from one route, story follows Jack who downloads a app onto his phone that claims it can rewrite rules of the world. He is shocked to learn that it is real and it can. In this story Jack is a closet straight submissive with ideas of being in a more female lead world, various fetishes may occur depending on story branch. Idk I kinda just have ideas sometimes and write random rubbish.
Updated on Apr 26, 2026
by WBD
Created on Mar 27, 2025
by WBD
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