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1. Tanning booth in a itsy bitsy bikini, so that the sissy can experience tan lines.
2. Make him put nail polish on both his hands and feet.
3. Make him sit on the toilet like he has a vagina to relieve himself.
4. Clip on extensions to his hair and leave the house like that.
5. Tell him to wear a full glam face of makeup, including lashes.
6. Send him to get his eyebrows waxed or threaded thinly at the beauty salon.
7. He should talk in a high pitched “feminine” voice in public.
8. He needs to wear a thong and bra inside all of his clothes for the day.
9. He should go for a bra fitting in a shop where they specialise in bra fittings.
10. Should remove all of the hair on his body, so he is nice and smooth apart from his eyebrows and lashes.
11. He could buy and wear some high heels, and if you want to take it a step further he could buy some stripper heels.

13. Follow a “How to twerk” or “How to lapdance” tutorial
14. Lock himself in chastity
15. Go swimming in a bikini or a bright pink one piece with a pink swimming cap on.
16. Masturbate with a dildo or butt plug.
17. Cum to shemale or monster cock porn.
18. Get both of his ears pierced.
19. Practise his fierce runway walk for 1hr per day, to pop music.

20. Drop a pencil and bend it over suggestively at work.
21. Swallow someone elses cum.
22. Get a wig professionally fitted and styled.
23. Get nipples pierced.
24. Pretend to have a menstrual cycle by buying tampons and pads, wearing them. Then use a tens machine or something like that to experience period pains.
25. He should finger his ass and moan out loud how much he loves fingering his pussy.
26. He needs to put a vibrator on his cock, and pretend he has a clit.
27. Respond to a booty call.
28. He should have anal whilst in chastity.
29. Service a gloryhole
30. He needs to create an alter ego, his sissy alter ego and give her a pretty name.
31. Keep a pink, girly diary and write lines in it every day about how much he loves being a sissy.
32. He should go out on a date with a man, whilst wearing a dress, heels with his wig all done up.
33. Get his lips enhanced.
34. Subscribe to women's gossip and fashion magazines
35. Practise his deep throat skills with a large pink or purple dildo.
36. Invest in a sweet smelling womens perfume and wear it daily.
37. Watch makeup and hair tutorials on YouTube daily.
38. Go to yoga and pilates class wearing a tight womens workout outfit preferably in a bright pink, purple or yellow colour.
39. Audition to become a stripper at a local strip club - go dressed in the part.

40. Wear a pink diamante collar at all times.
41. He should always flirt with other men, whenever he goes out in public as blatantly as possible.
42. Listen to sissy hypnosis.
43. When it is hot weather, wear some booty shorts, a crop top and some roller skates and skate around seductively.
44. Cum in a cup, add water and drink it.
45. Make a phone call in a sexy and seductive high pitched voice.
46. He should order some food, then answer the door dressed up like a slut.
47. He should make an only fans as a woman.
48. Redecorate his home in pink.
49. Hump a pillow for an orgasm whilst spanking himself.
50. Show up to a pole dancing class dressed up like a stripper.



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