Your wife has become extremely jealous of your much younger, hot roommate and she suspects that you fantasize about her. She decided to kick her out and the roommate comes to you for help. Is your wife serious? How is she supposed to find another place to stay? She has noticed you checking out her big boobs and knows that you like big boob JOI porn. Maybe you and her can help each other? She can oil her big boobs, tease you and encourage you to stroke your cock and in return you will let you stay! What? Your wife was right and she is bad news after all? Maybe that's the case, but you will enjoy it ;)

You are in an open marriage with a very hot girl who is also a sex worker. She has many clients with huge cocks, yours just can't compared and a few months ago got pregnant by one of them. Now she can't continue working, but she loves her clients and doesn't want to disappoint them, so she promised to find a replacement for them. The real problem is that she doesn't know any woman that she can trust and she was getting stressed until she thought of you! She decided to feminize you and teach you everything you need to know, so you can be the perfect sissy sex worker! Don't worry, you will be sucking 20 cocks per day and will soon love the taste of cum and learn to deepthroat! You will make a fine sissy! Besides, as a full time cuck, you were already going to take financial responsibility for the pregnancy anyway, why not use your ass and mouth to make a lot more money? Opening your marriage was the best decision for you, your cock isn't big enough, you are not very masculine and you will look amazing in bra and panties! Your sissy training begins!

Your hot step-sister has started to attend nursing school and she just found out what the minimum medically normal penis size is. Wow, your pathetic cock isn't even close to that size! She bets that when you went to the hospital for a check up, your sad small cock was the joke of the day between the nurses. If anyone asks, she doesn't know you, she doesn't want to be known as the step-sister of the small dick guy. Do you remember when you showed her all that hot taboo porn where the step-brother fucks his step-sister? Yeah, that will never happen, although she has a very tight pussy, your cock is too small to satisfy her. Just give up already, buy a porn subscription and jerk off with 2 fingers, that's all your sex life from now on!

You come home and see your hot step-mom doing housework as usual. You seem very upset and she asks you what's wrong. You confess to her that you have a foot fetish and when your gf found out about it, she freaked out and dump you. Your step-mom reassures you that there is nothing wrong with liking feet and that in fact she also has great feet too! For the first time you pay attention to your mom' s thin pale feet and become very hard. She notices and offers to help you by giving you an oily foot job. Will you end up cumming on her feet or her big tits? ;)

Ever since your step-mom got divorced, she has been going on dates without success, the last guy told her that her lingerie are too fancy for just a second date! What a loser, right? At least she will have you forever! What? Why is she acting like a whore and undressing so soon? Well, your step-mom has sexual needs too! Now that she thinks about it, maybe the lingerie was indeed too much, she should have worn panties without a bra, do you want to help her choose which panties are the best? She will start a very special panty try on show just for you! You are already hard? She can play with herself and watch you stroke your cock and before you know it you are fucking like crazy and she is begging you to cum inside her! Enjoy ;)

You have been wanting to move out and your step-mom is devastated, how can you do that to her? Not only that, but you need her to co-sign the lease for your new apartment! There is only one way to convince her to do it: You have to get her pregnant, so she can have another step-son to keep her company and she isn't lonely! In fact, she decides that you should try to impregnate her right now and before you know it she is sucking and riding your hard cock! She is begging you to cum inside and impregnate her and you can't resist her tight pussy and blow your load inside!

Your step-sister caught you stealing her dirty panties from the laundry basket! Wow, so it has been you the entire time? No wonder she has no panties to wear! Why are you doing this? You can't stop smelling her dirty asshole and jerking off your cock? Wow she didn't know that her step-brother is such a terminal pervert? But since you love the smell of her ass so much, why not get it directly from the source? She will let you smell her butthole and give you detailed jerk off instructions and in exchange you will pay for everything and do all the house chores! Now that she realized that her ass has so much power over you, you have no choice but do anything she wants you to! Are you ready to stroke?

It's time for your sissy training! CEI at the end!