Welcome my lovelies to your Sissy Tasks and Challenges. Here you will find a selection of tasks to undertake ranging from the very easy to a series of expert dares!
Please note. These sissy tasks are for entertainment purposes only. https://sissysite.co.uk/disclaimer
When meeting new people or going out alone dressed up, please stay safe. Do be aware of your environment and don’t put yourself in to any dangerous predicaments or situations that make you feel uncomfortable.
So are you ready for some fun? Then Let’s go.
1. Here’s a simple task to start your sissy journey. Apply some clear lip gloss and pretend that it’s lip balm.
2. Apply some clear nail enamel or very pale pink. If anyone asks, say it’s special stuff to stop you biting your nails. Or for those who are more adventurous, wear some darker shades.
3. Wear a vanilla flavour ladies perfume or body spray. You can say that you’ve just eaten a vanilla doughnut.
4. Start using hand cream as this will keep your hands soft and smooth, ready for when you dress in your fragile clothing.
5. Start moisturing your face with some quality, fragrance free face cream as this will keep you looking younger and will help later when you play about with make up. You don’t have to spend a fortune on a tub or tube of cream, just as long as you don’t get an allergic reaction from it.
6. Create some online sissy accounts on meet up / chat apps and social media platforms so that dominate and alpha men can contact you for some fun. You can add pictures on them at a later date when you feel more comfortable.
7. Start watching sissy hypno videos to transform your way of thinking.
8. Store your cash in a pretty girly purse and use it whilst out shopping or going for your daily coffee.
9. To feel even sexier when you purchase your stockings, start to shave or wax your legs. Then use a body moisturiser to smooth and calm your skin.
10. Again, start preparing your body by shaving your armpits and cock area as men like their sissies nice, smooth and girly.
11. Go to the shops and buy a pair of tights or stockings and say they’re for yourself!
12. Take a trip to the shops and go and try on (and preferably buy) some ladies shoes and say that they are for you.
13. Wear a pair of lacy knickers underneath your work clothes. If you don’t own any, now is the time to stock up on several pairs as you’ll be posing in them soon.
14. Wear a pair of stockings or tights under your clothes, but no socks and see if anyone notices your nylon clad ankles.
15. Invest in some Sissy jewellery. Anklets are ideal as you can wear them discreetly under your trousers, or a bracelet can be hidden underneath your shirt sleeve. And if you’re feeling a bit braver, attach a sissy themed keyring to your keys or bag.
16. To open up your eyes and to make your lashes look longer, black, brown or clear mascara should be applied. This product is easily available and comes in many shapes and sizes. Don’t forget to buy the eye makeup remover and cotton pads too or otherwise you’ll end up looking like a panda.
17. By now you should have a small collection of panties. So to match them, you’ll need to go and buy some sexy lingerie such as suspender belts, bras and possible a basque. If you’re still nervous about going to the shops for yourself (you shouldn’t by now) then click that mouse and shop online.
18. Now that you have your outfits and are looking after yourself, its time to prepare yourself for playtimes and being used. So go to an adult store / sex shop and treat yourself to a dildo. And don’t forget to buy the lube as well. https://sissysite.co.uk/dildos-whats-your-size/
19. To get use to drinking all of those man juices, have a go and taste your own cum.
20. To be a true sissy and succumb to those sexy alphas, get used to wearing a chastity device. https://sissysite.co.uk/are-you-ready-for-locktober/
21. Be a good toy for those alpha’s and wear a butt plug all day. This will stretch you nicely for all those hard cocks thats going to enter you soon.
22. Including your face, take a full length picture of yourself dressed in your slutty or sissy gear then post them online to your sissy social media sites and chat apps.
23. With your new online profile, become a Sissy Cash Pig by serving a Master or Mistress online and donate some money to them. And don’t forget you can click on our Donations link below too. https://sissysite.co.uk/donations
24. Join some online Sissy groups and send some pics of you dressed. If you’re feeling brave and want to be shared, then send pics with your face showing.
25. Find an online chat room, dress up in your sexy outfit and parade about on cam.
26. With your confidence growing, answer your front door wearing some sexy lingerie or a naughty outfit.
27. Log on to an online dating / meet up app at work and see if there is anyone near you. If so, then send them a message and start a chat. Remember to put in your bio / description that you’re a sissy who wants to play!
28. Drive to a truck stop, open your car door and take some selfies of you wearing some sexy lingerie.
29. Wear something naughty and slutty and go for a walk up your street. Or if you wish, drive out somewhere further that’s more private and take a walk. Stay safe.
30. Find someone or a group of people who are organising a naughty party and ask if you can dress up and be their sissy servant for the evening. Say you are willing to do anything for them.
31. Go to a gay pub or club and wear something really revealing.
32. When meeting playmate, start taking action pictures so that you and others can share them online to expose you as a sissy.
Do remember that these are some ideas for you if you wish to take up the challenges. Good luck my lovelies and enjoy your discoveries.
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