Jamie is so excited about her new much younger boyfriend, Matt. Jamie is quite the cougar and preys on younger men but due to the age difference they tend to be step-momma's boys. She waits for Matt in the car but he is taking forever. He is so sexy she watches his every move but when she goes in her room she doesn't like what she sees. Matt has his big dick out and is rubbing it into her purple lace panties. He went in her drawer and got her drawers! What a sissy, just like all the boys she dates. Well this one is worth working on Jamie takes out some special clothes for the occasion, a sl...

Jamie is so excited about her new much younger boyfriend, Matt. Jamie is quite the cougar and preys on younger men but due to the age difference they tend to be step-momma's boys. She waits for Matt in the car but he is taking forever. He is so sexy she watches his every move but when she goes in her room she doesn't like what she sees. Matt has his big dick out and is rubbing it into her purple lace panties. He went in her drawer and got her drawers! What a sissy, just like all the boys she dates. Well this one is worth working on Jamie takes out some special clothes for the occasion, a slip, some lacey panties and a bra. Matt has a great physique he actually looks super hot in women's clothes but he is so ashamed to be caught and now made to look like a major sissy boy. Jamie makes him pose and says that this is their special sissy time. Maybe if they get it out of the way once a month he can go back to being her "real man." There does have to be a punishment though and Matt is taken over her lap and submits to a spanking over his slip, his tight panties and then bare bottom and his cheeks (with legs spread)get as red as his face. When naught Matt's sissy buns are burning his is allowed to stand up and sit on Jamie's lap while she explains he will be MILKED and his sissy cream taken out of him once a month as part of an attempt to get this girly part of out her man! He stands in front of her while she strokes him and after he asks he strokes to a good cum in her panties while she caresses his balls. The sissy has been spanked and milked and now Jamie has her new boyfriend back! This clip features ORGASM and JOI elements as well. Plays on Iphone and Android.