Girlfriend’s Mom Dominating Young Boy 5 – A Gurly Sissy

Girlfriend’s Mom Dominating Young Boy 5 – A Gurly Sissy is the fifth episode of the virgin cuckold boy “Angel” who explored his bisexual side. His GF’s mother will force him to become a Sissy.

Read the previous episodes:

Girlfriend’s Mom Dominating Young Boy 1 – Force jerk-off

Girlfriend’s Mom Dominating Young Boy 2 – Chastity for Safety

Girlfriend’s Mom Dominating Young Boy 3 – The Virgin Cuckold

Girlfriend’s Mom Dominating Young Boy 4 – Anal Ejaculation

Do your work as boi

Angel got used to the idea of his orgasms not being up to him thanks to the chastity that Ms. Anderson made him wear. Then, before even having sex for the first time he got used to watching as Mike, the black Bull, fucks his Girlfriend Emily in front of him.

After that Ms. Anderson made him drink cum and suck cock and even tricked Angel to get anal fucked by Mike’s gay friend Tom. Angel learned how to cum in his chastity with anal stimulation and this became his routine. Either Ms. Anderson herself with a dildo or Tom with his cock fucked Angel’s ass as he watched Mike fuck his girlfriend.

One afternoon Ms. Anderson called Angel to their house so she can talk to him privately. Emily was not around. After everything that happened, Angel was kind of sure that Ms. Anderson will take things further as she always does. He was just obeying and not questioning anymore. However, he wasn’t sure what is going to come next.

Ms. Anderson was asking if he liked Tom so far or not. Angel was kind of shy about it.

Angel: well, I am still kind of confused what does he do with all of this. Your dildo or his cock feels good in my ass but I am not gay and I have a girlfriend.

Ms. Anderson: I know. You might not be gay or you might just have some bisexual feeling which is ok. But you liked how he puts his cock in your ass, don’t you?

Angel (became red and with a lower voice as his head was down): yes, however, I felt good because I was watching Emily with Mike. And that was hot.

Ms. Anderson: Yes I know. In all of this, you make each other feel good. Mike has sex with Emily because he is the best at doing that and making her cum. And, Tom puts his cock in your ass so you can feel good and cum. Don’t you think you should do your part too?

Angel: What is my part?

Ms. Anderson: Tom enjoys fucking your little as but you should put some effort that he enjoys this better. For example, we can get rid of all of the hair on your legs and body so he can feel it all smooth.

Angel: really? Do you think he will like it?

Ms. Anderson: sure, now let’s go. I made a reservation for hair removal.

Again Angel had some questions but he just did as she said. They went to a special saloon and made all of his body completely hairless.


The next day Angel came to Ms. Anderson’s house again. This time she was waiting with her daughter Emily. They had lots of girl clothes on the sofa next to Emily.

Ms. Anderson asked him to take off his clothes. With a little hesitation, he obeyed. Angel’s Chastity Cage (Cock-Cage) was jiggling as he took off his boxers.

Ms. Anderson: first of all let’s get rid of this chastity.

She took off the chastity with her key around her neck. Angel noticed that she had a few other keys there. For a moment Angel was happy and thought that he is finally free of chastity. But soon enough Ms. Anderson brought even smaller chastity which was the tightest that he could think of.

Ms. Anderson: This chastity is now feet for you. As you were unable to have an erection, now you fit perfectly in this sissy chastity… Ok, now we should choose some panties and bras for you.

Angel: What? But I am not a girl. You told me to get rid of my body hair and we did.

Ms. Anderson: Are you disobeying me? (Angel became silent) I thought you were a good Boi. Now you will become a good sissy gurl because this is how Tom likes it. He doesn’t know yet but we are going to surprise him. If he is going to fuck your ass let him enjoy it as much as possible. Besides, you said that you are not gay. So you should become girly so entering a penis into your ass will become acceptable ok?

Angel didn’t say anything further. Ms. Anderson and Emily continued dressing him up with cute and colorful girly clothes with a short skirt and little tight top and some sexy socks and high heels. Finally, they made beautiful make-up on him and put on a nice blond wig.

In the beginning, Angel felt weird and had difficulty walking in high heels. But then, they took him in front of a body mirror so he can see how he looks. He couldn’t believe it. He looked exactly like a teen girl. Angel was actually beautiful, a beautiful girl.

Girlfriend’s Mom Dominating Young Boy 5 - A Gurly Sissy
Girlfriend’s Mom Dominating Young Boy 5 – A Gurly Sissy

Ms. Anderson: I think she looks gorgeous. What do you think Emily?

Angel: She?

Ms. Anderson: Of course, you are not a good boy anymore. You are a good sissy gurl.

Emily: Yes, We can hang out like girlfriends. And I will introduce you to my friends.

Angel: But, but … I can’t wear these all the time. What my family will say?

Ms. Anderson: Don’t worry about them. I will talk to them.

The doorbell rang. Emily went and opened the door. Mike and Tom arrived. Both of them were wowed as they saw Angel. Especially Tom was amazed.

Tom (came close and with a low voice): you look really, pretty Angel.

Angel (shy and with a low voice): Thank you… (she looked how Tom looks) you look handsome too

This was the first time Angel was looking at Tom like that. It was like the clothes changed how she perceives. Does she like men now?

Ms. Anderson: Look how cute they look together… Now let’s go to the bedroom. Tom and Emily, you can go first.

Emily and Mike went first. They started kissing each other there. Ms. Anderson said that she is going to take wine with some glasses.

Tom and Angel were alone. Angel felt a bit shy. Tom came clothes and started caressing Angel’s wig.

Tom: you look really beautiful…. Um, I know this is just sex for you, and you want to watch them… but can I ask something first?

Angel: Sure

Tom: Can I kiss you?

Angel was stunned. She didn’t know what to do. So she didn’t answer. Tom felt that probably it means yes. So he started coming closer and closer. Angel was seeing that her comforting black face was coming to her face and she was able to smell his scent. It was too late so she closed her eyes.

Tom’s lips started touching hers. Angel felt great. She wasn’t sure if this was better than the kiss with Emily or not but she felt she was in the air. When Tom finished and took a step back. It took like 30 seconds before Angel was able to open her eyes.

Ms. Anderson arrived and took them to the bedroom. Emily and Mike were naked and Emily was already sucking Mike’s big black cock. Ms. Anderson gave a glass of wine to Angel and Tom and put the glasses of Emily and Mike next to them.

Angel looked reddish and just took a sip from her wine. Tom took Angel’s hands and brought her in front of him. Then, he pushed him down and took his black cock out. Angel was used to the idea and just put the cock in her mouth like a good girl she became. This time Angel was kind of happy. Maybe Ms. Anderson was right. The clothes helped Angel felt like a true girl and she was sucking Tom’s cock not because Ms. Anderson said so but because she was actually enjoying it. Especially now that she was looking into Tom’s eyes and see how much he was enjoying it.

Finally, Tom took Angel to the sofa and put her in a doggy position so she can watch as Emily was getting fucked by Mike’s BBC. Tom took Angel’s little skirt up and took down her thin panties. He used some oil to massage Angel’s asshole and fingered it a little.

Angel started moaning like a little girl and he was a bit surprised about it. Ms. Anderson was smiling and sipping her wine as she saw Angel was moaning.

Tom put his cock in front of Angel’s ass and started pushing it little by little. Angel was getting fucked in the ass again. But this time she was getting fucked like a sissy girl she became.

Black Bull fucking cuckold Boy in Chastity While watching Girlfriend

To be continued…

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