1. Rock and Roll Sissy Cruise Pt. 03


    Date: 3/30/2024, Categories: Transgender & Crossdressers, Author: byxyz775 

    I didn't get much sleep after sucking Big Joe's cock last night. He said he was looking for a sissy boy to be his slave for the rest of the cruise, but I needed to improve some of my feminine skills. First thing I apparently need to do is shave all my body hair. It seems that guys don't like hairy chests or legs on women or sissies.

My wife has me get naked and starts rubbing something on me. She takes out a razor and shaves my leg and chest hairs. Fortunately I am not that hairy of a guy. With a bare chest and legs my wife smiles and says. "Time to shave your pussy."

Two days ago that would have upset me, but after meeting Big Joe and the thought of being his slave has me excited.

With everything shaved my wife starts takes a picture and sends it to Big Joe. Then she starts dressing me. She was so, so right, the panties and stockings feel amazing now that I am shaved. She dresses me in a conservative outfit. "You shouldn't be that slutty in the morning." She helps me with my makeup and tells me. "Pretty soon you will have to do this by yourself." Today she adds some jewelry and matching pink nail polish to complete the look then tells me to smile. She sends another picture to Big Joe who texts her back. "Very nice. Remember while you and Brianna go to breakfast she needs to pick up a guy, suck his cock while you take a picture and send it to me. You can not help her pick up a guy, but you can give her tips."

My wife relays the message.

"I don't know how to ...
    ... pick up guys. I've never done it by myself."

"You will do fine. You look extra hot the morning, I guess it's the glow from sucking a big cock last night."

We go down for breakfast. It's not very crowded, people get a late start after the previous night's concerts. We find a table, and a few minutes later two couples join us. After about 10 minutes of conversation my wife excuses herself. She whispers in my ear. "Freshen your lipstick and you will be fine, hopefully you will meet me in our room with a hot guy in a little while."

I am now sitting with two couples that I 've never met wondering how am I supposed to pick up a guy. Finally I see a young man that looks like he works for the cruise ship. I excuse myself and go talk with him. He looks like he is about 19 years old. I ask him some dumb questions about what concerts he has seen. He tells me he has been too busy. The way he is looking at me I can tell he wants to fuck me. I tell him that I need something fixed in my room. When he tells me he can call maintenance for me I tell him he's cute and I start kissing him. I rub his cock thru his pants and he is already hard. I take his hand and I walk him back to our room. When I get there my wife is waiting, cell phone in hand, waiting to take pictures. I am about to introduce her as my sister when I realize I don't know this boys name.

My wife says." You don't need to know his name. I bet Big Joe will think it's hot to suck a total stranger's cock."

The young man ...
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