More Fun Boston Crybaby Stories

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Kry-baby

by maxdname on Sep 1, 2017
Group Sex

Nina and I arrived on an AEROFLOT Tu-214 Friday at 6:38 PM Pacific Daylight Savings Time. After almost 12 hours on a plane it was wonderful to park my ass on a cushion that wasn't careening through the skies at 600 miles per hour and bouncing with every pocket of turbulence. When I unlocked the door to our room at the St. Max Hotel, one of San Francisco's fi...

The Rose Diaries Ch. 19

by RoseB on Jun 5, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. * I suppose I should start from the beginning. Like, the very start... I was born on February 10th, 1988 in Austin, Texas. I was a healthy little boy who was born to a semi-loving couple and had my entire life ahead of me. Except that wasn't exactly it. My mother Racheal Collins...

Amy vs Matt cry baby match

by Littleprincespanties1 on Apr 22, 2025

Amy is 41 years old and Matt is 38 they have been talking and Matt turned to Amy. You know something Amy I would love to see you get humiliated and brought down a peg or two,”Really Matt and how would that happen. Matt starts to think “Well I think you in a crybaby match would be great. A what Amy asked “A crybaby match where to win you must strip the other...

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Joel's Stressful Afternoon

by justincbenedict on Jul 18, 2018
BDSM

"You are, too a crybaby." Yvette smiled as she said this to the perspiring Joel, her ever devoted older boyfriend. They'd just come in from walking home with ice cream cones. "You complain, and whine and wimp out. You're a big sissy." Joel, not yet scenting the danger, protested good naturedly. "I don't think that's true. I do give you your own way a lot,...

Letter from Vancouver

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: Having enjoyed so many of your letters from BDSM enthusiasts in the States, I thought I would tell you about my husband, Conrad, the Canadian Cuckold. (Catchy?) My husband Conrad and I are at the Levinger's party, socializing, but of course he is almost ignoring all the other women there, he just gazes earnestly, plucking my arm...he is i...

Blind Squirrel Finds Nut

by komrad1156 on Sep 25, 2017
Mature

In spite of the warning bells going off inside his head, Josh decided to stop. He knew a woman, even one with a young girl with her, who was hitchhiking, could have a man somewhere near her; a man with a gun or ill intent. Still, it was cold and getting dark, and there was no way he wasn't going to at least offer them a ride. He pulled the F-250 that was to...

Letter from Acapulco

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom, This should be a "Letter from Scottsdale" as we are settling in Arizona, but I did tape this little convo I had with my new husband...hope it doesn't bore! Joslyn Handelman "Oh, stop moaning, Grady." "But..I'm tied to this uncomfortable wicker chair and you're rubbing my dick with, what is it, dental floss?" "Yup.Dipped in bacon grease...

Property Ch. 03

by GvilleWriterGuy on Sep 12, 2017
BDSM

"Please can I cum?" she begged, kissing the top of my shoe. She was on her hands and knees, her big ass in the air, whimpering at my feet. "You are so adorable when you beg, pig," I chuckled, ruffling her hair with my free hand. I had a cigarette in the other hand, and the ash was getting long. "Open wide." She tilted her head up to look at me, and with a...

Throne of Panties Ch. 02

by scur on Sep 16, 2017
Fetish

This story continues where "Throne of Panties" left off. A man made the mistake of allowing a stewardess to see him in panties and stockings and instead of getting a blowjob he was pushed to the ground and now another passenger becomes involved. I think both stories would benefit from being read in order. ***** "Oh really." the other passenger said. "Does...

OZone 11 : Child Proof

by SZENSEI on Sep 17, 2017
BDSM

12:20 PM the Smokey Mountains of Tennessee The "BRIGHT EYE SWALLOW" bus had made its trek from Louisville, Kentucky in record time. Carrying a wide range of interesting passengers on it's journey to the Gulf. Two riders in particular stood out among the hicks from the sticks. Lovely, "Renee Cherish" was given the task of not only being a Counselor but...