Sade Olutola
DEAR READER
he wasn't even looking at me and he found me

Andulka

blake kathryn

Product Placement
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2025 on Tumblr: Trends That Defined the Year
art blog(derogatory)
trying on a metaphor
Cosmic Funnies

titsay
i don't do bad sauce passes
Misplaced Lens Cap
Not today Justin

shark vs the universe
Keni
AnasAbdin
No title available
$LAYYYTER
seen from United States

seen from Saudi Arabia
seen from United States
seen from Estonia

seen from Saudi Arabia
seen from Taiwan
seen from United States
seen from Denmark
seen from United States

seen from Germany
seen from United States
seen from United States

seen from United States

seen from Italy
seen from Malaysia
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seen from United States
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seen from United States
@tightsslutm
Reblog if you want your asshole destroyed.
Obey and call me mommy
If only I wish
Mummy Issues
Aunt Bridget was on her travels again, this time to see a more distant part of the family. Her cousin, Margaret was unwell and Bridget volunteered to help out with the running of the house.
Margaret was a little older and very much mirrored Bridget in her approach to matriarchal domination. But it was clear that the lady’s powers were diminishing somewhat……a situation typified by the behaviour of the elder son in the house. Aunty and Margaret fondly spoke of old times, and the need to whip everything back into shape. Bridget especially knew how to deal with troublesome boys, and she headed out for a productive day’s shopping.
As she descended the stairs in her soft leather skirt, heels and blazer, she saw the boy skulking in the kitchen….barely acknowledging her. Bridget smiled and said nothing….her plan for the coming days had now started to form in her mind.
Admittedly, it didn’t take long for the boy to trip himself up. Margaret was a larger lady, with a very generous bosom and an austere dress sense. The two ladies had a mutual appreciation of vintage lingerie and when appropriate, practical underwear. Bridget suspected that this misbehaviour was a sign of something else and when she carefully laid out the old fashioned undergarments on her bed, she waited…..
Sure enough, the feckless son furtively began to rifle through the attire….taking a long sniff of the worn bloomers and fondling the oversized bra. His shameful little bulge was straining in his own underwear and Bridget stepped into the room as he was about to start his dirty wanking.
With a strong arm, Aunt Bridget had the boy bent over the bed, his face now fully in one of the mammoth bra cups. His mother’s stern treatment had indeed encouraged his sissy side to blossom and within moments, he was clad in the worn underwear, pleading with Bridget for mercy.
Unfortunately, the little pervert was unfamiliar with Aunty’s methods and as he was made up like a pretty girl, other items for today’s lessons had been revealed. The wide leather collar and the armbinder were introduced to the wretched boy, and he was swiftly restrained. With the pairs of massive granny pants now also laid out, his eyes widened as Bridget took at least 2 pairs and shoved them deep in his mouth.
Layers of clear tape sealed the impossible gag in and the scarf over the head completed the look…..or did it?
Of course, Mummy Margaret’s huge bra was the final humiliation…..along with the ludicrous fake breasts that Aunty had procured from her shopping trip in the darker side of town. Our unruly sissy boy was now stood in front of the bedroom mirror, with the monster gag forcing his mouth open and cheeks bulging. The huge false breasts were filling Mummy’s bra most comfortably and his feet were wedged into his Mother’s high heels.
Aunt Bridget roughly grabbed the boy and she marched him down the hallway to Margaret’s room. He was grunting and pleading into the stuffed gag. He didn’t want to be seen like this, but Aunty was firm and pushed him into the room. The boy’s Mother nodded in approval, and Bridget bent him over the bed. The stiff hairbrush was raining blows down upon his backside and Margaret landed a few herself as he squealed like a piggy.
A check of the boy’s crotch showed some foul leakage and Bridget opted for the last treatment of the day. A snug steel cage and fat, vibrating butt plug.
Now cock locked and ass loaded, sissy boy would be tied to his bed for a few hours while Aunt Bridget continued her work in the house. Occasionally, his agonised groans could be heard as the plug hummed into life.
Tomorrow would undoubtedly bring a new lesson.
@dinabound
If you need set of panties,mommy got some for you,don’t be shy if you a sissy 😌🤤
Pink is my go to color.
Yes, every Sissy wants pink panties too
Mummy Issues
Aunt Bridget was on her travels again, this time to see a more distant part of the family. Her cousin, Margaret was unwell and Bridget volunteered to help out with the running of the house.
Margaret was a little older and very much mirrored Bridget in her approach to matriarchal domination. But it was clear that the lady’s powers were diminishing somewhat……a situation typified by the behaviour of the elder son in the house. Aunty and Margaret fondly spoke of old times, and the need to whip everything back into shape. Bridget especially knew how to deal with troublesome boys, and she headed out for a productive day’s shopping.
As she descended the stairs in her soft leather skirt, heels and blazer, she saw the boy skulking in the kitchen….barely acknowledging her. Bridget smiled and said nothing….her plan for the coming days had now started to form in her mind.
Admittedly, it didn’t take long for the boy to trip himself up. Margaret was a larger lady, with a very generous bosom and an austere dress sense. The two ladies had a mutual appreciation of vintage lingerie and when appropriate, practical underwear. Bridget suspected that this misbehaviour was a sign of something else and when she carefully laid out the old fashioned undergarments on her bed, she waited…..
Sure enough, the feckless son furtively began to rifle through the attire….taking a long sniff of the worn bloomers and fondling the oversized bra. His shameful little bulge was straining in his own underwear and Bridget stepped into the room as he was about to start his dirty wanking.
With a strong arm, Aunt Bridget had the boy bent over the bed, his face now fully in one of the mammoth bra cups. His mother’s stern treatment had indeed encouraged his sissy side to blossom and within moments, he was clad in the worn underwear, pleading with Bridget for mercy.
Unfortunately, the little pervert was unfamiliar with Aunty’s methods and as he was made up like a pretty girl, other items for today’s lessons had been revealed. The wide leather collar and the armbinder were introduced to the wretched boy, and he was swiftly restrained. With the pairs of massive granny pants now also laid out, his eyes widened as Bridget took at least 2 pairs and shoved them deep in his mouth.
Layers of clear tape sealed the impossible gag in and the scarf over the head completed the look…..or did it?
Of course, Mummy Margaret’s huge bra was the final humiliation…..along with the ludicrous fake breasts that Aunty had procured from her shopping trip in the darker side of town. Our unruly sissy boy was now stood in front of the bedroom mirror, with the monster gag forcing his mouth open and cheeks bulging. The huge false breasts were filling Mummy’s bra most comfortably and his feet were wedged into his Mother’s high heels.
Aunt Bridget roughly grabbed the boy and she marched him down the hallway to Margaret’s room. He was grunting and pleading into the stuffed gag. He didn’t want to be seen like this, but Aunty was firm and pushed him into the room. The boy’s Mother nodded in approval, and Bridget bent him over the bed. The stiff hairbrush was raining blows down upon his backside and Margaret landed a few herself as he squealed like a piggy.
A check of the boy’s crotch showed some foul leakage and Bridget opted for the last treatment of the day. A snug steel cage and fat, vibrating butt plug.
Now cock locked and ass loaded, sissy boy would be tied to his bed for a few hours while Aunt Bridget continued her work in the house. Occasionally, his agonised groans could be heard as the plug hummed into life.
Tomorrow would undoubtedly bring a new lesson.
@dinabound
Erm is it not obvious yet 🤦🏼♀️💖
Yes please mommy
@losingmy5hit
If i do, do you promise not to post the photos on Tumblr?
My favourite place to worship a pantyhose arsehole 💯
That’s how I got started. She had such pretty things.
Yes this was my start
This is how it all started for me.
Yep. Didn't we all?
All about sissy slave lifestyle
How submissive are you willing to be?
Swipe in my inbox now!