Mrs Loving has had a wonderful time enjoying and feminizing her many sissies. On rare occasion she’s able to bring two sissies together for an enhanced training. Here’s some photos from her latest training session with one of her favorite sissies, Monika and an up and coming sissy trainee, Allyson.
Posts Tagged ‘sissy humiliation’
Sissy Allyson is rewarded by suckling at Mistresses breast then milked, masturbated until his sissy cream erupts when he comes. You’ll enjoy seeing the sissy as she cuddles up to Ms Simone as she hold out her breast and rests it in his open mouth. This is very touching ans sweet clip but also very, very hot. What sissy wouldn’t want to nurse while being milked
Mistress pulls up his sissy panties to cover the dildo in his ass. Then she takes his cock out of the leg opening of the panties. Now it’s time for the sissy milking to begin. She teases his cock until it’s nice hard like a good sissy cock. Mistress plunges the dildo in and out of his sissy ass pussy stroking his hard cock at the same time.
Sissy gets fucked in the ass by Ms Simone as part of his feminization session. Sissy is humiliated and teased and still his cock gets hard and erect. She pulls the pink nylon girlie panties down lubes up his sissy pussy asshole and begin to insert the large black cock into him. She pushes it deeper and deeper until the sissy moans with pleasure
Standing in the pink satin sissy dress, Mrs want to see him in, he was red with embarrassment and still his cock was hard and throbbing. Mrs Loving teased him about how hard he was and that really made him a sissy. She teased him about how his panties were going to fit over his big cock. She told him to go to the sissy panty drawer and bring her three pairs. She looked at all three and chose the light pink full cut nylon ones with the rosebud embroidery and little pink satin bows. These were very much like little girl panties and she knew that’s what her sissy needed.
She told him how she wanted to see him put them on so she would get as much pleasure she could from his humiliation. He slipped his feet into the panty and pulled it up his legs slowly until he got just below his hard cock when Mrs Loving took his cock into one hand and the panties with the other and pulled them up and over his erection. He was getting harder and wetter by the minute and was afraid he was going to be naughty and spurt his sissy cream right into her hand and the panties.
Sissy Lauren is humiliated, teased and paddled before the feminization session continues. With a bright red bottom and hard cock Mrs Loving begins the most exciting part of the training for sissies. First she puts Lauren in a black bra. She slips his arms through the strap and fastens the hooks in back. Once tugged into place she insert silicone breast forms to fill out the cup of his bra and give him realistic titties for her to play with. His sissy clitty cock is hard and excited even though he’s embarrassed being almost naked in front of Mrs Loving. Next, she picks out on of the most sissy of dresses. A pink tight fitting satin dress with thin feminine strap. The bottom flare out like a ruffly pink tutu. You can see Sissy Lauren turn bright red at the tough for putting it on but you could also see his cock throb and leak with his excitement.
Sissy Lauren is caught wearing and masturbating in his Auntie’s Panties. She found him in front of her bedroom mirror wearing her favorite pair of pink satin panties. His was rubbing his cock through the panties while looking at himself in her mirror. Auntie told her sister who told her to do what she wanted with him. Auntie thought that he could benefit from feminization training so she sends him to Mrs Loving for serious training. This clip starts off with Sissy Lauren being punished and spanked as Mrs Loving embarrasses him by making him tell her what he had done.