Thebreezy1 - A Sissy's Diary

Slowly start doing more and more with a different guy and less and less with me. Until I have to live on the memories of your hands, mouth, and pussy while another man gets to experience all of you whenever he wants.

Both when I jerk off and when we have sex. This thought is how I get hard

Normal sex for us is me pumping my half hard penis into my gf 3 to 5 times as it quickly cums and goes completely limp, insuring she almost never orgasms from PIV. So I’m sure she would want to be fucked extremely hard and rough if she ever cheated.

The dream

You had fantasized about getting with your crush for months, and now was finally the time to show her what kind of man you are.  She was in your arms and you were making out, feeling each other up.  Her hands probed down to your crotch, searching for hard cock.  She felt around, unable to find it. She laughed a bit, and reach into your pants.  She started to rub your flacid member, talking dirty into your ear. Nothing happened.

Eventually she pushed you away and started to console you.  But don’t worry, this isn’t the end of the evening. As a consolation prize you get use a nice big dildo on her. You can watch her orgasm in pleasure and imagine what it would be like if she was writhing around on your cock instead of the dildo.