Sissy Stepson Part 6 Caroline s Sissification
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Sissy Stepson 8 - Caroline's Milking free porn video
Part 8 - Milking Caroline
"Our sissy is going to get ready for milking, I have enough knee highs
for everyone to participate" said Mrs. Monet excitedly. She gave
everyone three knee high's, sissy Caroline was going to get the milking
of her life!
Caroline came back to the group with here outfit on and was instructed
to sit next to Regina for milking. Regina encased the Caroline's sissy
stick with the nylon and instead of using her hand. She took off her
high heel and stuck the toe of the shoe over the head of her sissy
stick. Regina then proceeded to pound the toe end of the shoe on to the
sissy stick head.
Caroline thrusted her hips to meet the toe end of the high heel and
Regina laughed, "Look he enjoys humping my high heel, you have really
messed this sissy up good Rita!" Regina said in a very excited voice.
"Tell your stepmother Rita, how would like to hump her shoes,
Pantywaist!" Caroline stammered, "Stepmother Rita please let me hump
your stiletto shoes and shot sissy cream into them!" Caroline lost her
cookies at that point and Regina made here clean the inside of her heel
and as well as the knee high.
Caroline, begged Regina to milk her with a shoe again and she obliged
the pathetic sissy. Regina continued humiliating and castigating her
sissy step grandson while letting him hump the toe end of her shoe. She
had the sissy trained and held the shoe still and laughed as the
pathetic pansy thrust his sissy hips. Caroline was thrusting his hips
wildly so that the nylon encased sissy stick would make contact with
the inside of the pointed toe of her stiletto. "Look he follows
wherever I move the shoe." Regina said. "Oh, mother I can't believe how
effective shoe milking can be." Mrs. Monet commented.
Regina kept pulling the shoe away as Caroline begged her step
grandmother for relief. "Please, grandmother Regina I just want to bury
my sissy stick into your shoe and shoot my sissy cream!"
Regina took her high heel and began furiously jamming the toe end of
the shoe on top of Caroline's sissy stick. Caroline fell back on the
couch in a prissy sissy daze and she could feel her self control give
way as she shot another load into her step grandmother's shoe.
Caroline collapsed on the couch with the end of Regina's shoe buried
onto her swollen purple head of her nylon covered sissy stick. Regina
gently pumped the top of the shoe down and squeezed Caroline's aching
sissy sack to finish the milking. Caroline gazed out into space with
his head swimming with thoughts of being milked again by his evil
dominant step grandmother. Regina feed her effeminate step grandson the
sissy cream out of the knee high and forced the pathetic pansy to lick
the inside toe of her shoe clean.
"Well dear do you want to try it again?" asked Regina. "Yes, please I
need more high heel milking." said Caroline in an excited voice.
Caroline's step grandmother again put her third and final knee high on
his sissy clits and sack. She then asked for a pair of old stockings
from her daughter who brought a pair that the sissy had put runs in
during the week. "Hear use these, that pantywaist ruined these" her
Daughter Rita commented.
Regina took her high heel and again put the toe end on top of the
swollen head of the sissy stick. This time she used the stockings to
tie the shoe around the waist of the pansy. "There you go dear, my arm
is tired from milking you and now you can do it yourself!"
"But, How?" Caroline asked, as she walked around with a high heel
secured to his pathetic hard little sissy clit. "Oh, my god, mother he
looks so hilarious!" laughed his stepmother as she pointed at the
humiliated sissy stepson. "You've got hand, now use it SLUT!" yelled
Regina and the sissy began masturbating by pumping the shoe down on to
his harden sissy boy cock and thrusting his hips to meet the downward
thrust of the shoe. Caroline became very excited and everyone could see
his eyes glaze over in a sissified trance as he rhythmically moved the
shoe up and down.
"Lay on the floor and start humping that shoe hard" screamed Regina.
Caroline fell to the floor and laid on top of the high heel and began
humping. Everyone laughed at the site of a sissy shoe humping, but
Caroline was too enthralled to stop or care about his humiliation.
"Look at the shoe humping sissy whore you made of your stepson" Regina
laughed loudly. "I had some help, what a pussy, other boys play sports
and he humps woman's shoes!" chimed back Rita.
Caroline's head was dizzy and swimming with thoughts of nylons, panties
and stiletto's. She humped her step grandmothers shoe hard and furious
screaming out "Oh, I love to being a sissy shoe humper, I want to hump
all my step mommy's beautiful high heels!" His stepmother shouted
"don't worry about that my sissy stepson, you're going get your chance
soon enough."
Caroline finally explode his sissy cream into Regina's high heel.
Reginah made the pathetic pansy get up and she pumped her shoe up and
down to release the rest of the pearly girl cream. She then untied the
shoe and made Caroline lick the inside clean while her limp sissy clit
remained drench in a cocoon of nylon and sissy cream. Maryann remarked,
"I hope the sissy isn't finished, I've got three milking nylons for her
to fill."
Regina yelled "get that bag of girl cream off your limp pathetic dick
and it's dripping all over your stockings and high heels! What a
simpleton slut! In deed, by now the sissy cream had seeped down
Caroline's legs and was merely a translucent glaze on his red limp
sissy dick.
Fawn
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