Caught by his Sister
A cross-dressing sissy gets caught by his sister and her boyfriend
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Jimmy was in deep trouble.

What had started out as a harmless, fun-filled afternoon of prancing around in his older sister's clothes had turned into a disaster. He'd returned to her bedroom to grab one of her lacey bras when he suddenly heard footsteps coming down the hallway. For some reason, he'd failed to hear either a car pull up or the front door open as he normally did. Now, he was stuck in his sister's room about to be caught dressed in all her clothes!

Jimmy was so terrified, he nearly wet himself. He'd always known he was a sissy and he was used to being pushed around at school on a regular basis. One of the worst bullies was Chad, his sister's boyfriend who played on the school's football team. Chad was constantly pointing out Jimmy's feminine aspects, including his long red hair, and mocking him for his nerdy ways. And Jimmy's sister Brooke never did anything to discourage him. While she was unaware of Jimmy's secret fetish for dressing up in her clothing, she nonetheless agreed with Chad's general opinion of him.

That was all about to change as Jimmy stood there, cringing in one of Brooke's dresses, pantyhose and high heeled sandals. The look of shock on Chad and Brooke's faces was considerable but brief. Chad began laughing uproariously although Brooke was incensed at her sissy younger brother.
She immediately began shrieking at him while Jimmy tried to stammer out some sort of coherent excuse. In his distress and angst, he tried to run out of the room and past Chad but the bulky linebacker wasn't going to allow it.

"Oh no you don't," he said, gripping the fragile sissy's shoulder with his meaty paw, "You want to act like a girl, I'm going to see you get what you came for."

Chad pushed Jimmy down on his knees as unzipped his pants in one swift motion.
"I always knew you were nothing but a big, prissy sissy," he said as he fumbled for his cock, "Now we're going to take it to the next level."
Jimmy began pleading with Chad but he'd never had much in the courage department and everyone knew how much of a pushover he was.

"Open up, it's time you sucked your first cock," Chad said in a husky voice.
"" Jimmy squealed in his small, high pitched voice. He made a half-hearted attempt to get up but Chad easily held him in place.
Jimmy shook his head and tried to pinch his lips shut but Chad slapped him on the side of his face which caused him to cry out. Chad responded by jamming his swelling cock deep into Jimmy's mouth which made the sissy gag reflexively.

"I see you're learning to put on make-up," Chad said as Jimmy's warm mouth closed over his hardening cock, "With your sissy features, you could almost pass for a chick."

Jimmy could do little except struggle to accommodate the massive erection expanding and filling his mouth. He found his head bobbing up and down as Chad's slick pole was driven deep into his throat.

"I want you to look up at me when I blow my load into your mouth, sissy boy," Chad said as he guided Jimmy's auburn head into a steady rhythm that could only lead to one result.
It had been almost a week since Chad had last came and he knew he would be giving Jimmy a load that would fill his mouth to overflowing.
Being too terrified to stop the raping of his mouth, Jimmy sucked dutifully, hoping the jock who's pole he was sucking would make his humiliation short and quick.

"Look up at me Jimmy," Chad said as his breathing grew heavy and labored, "Because this is only the first load of many that you'll be getting."

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This one is really good, although I would prefer that there were diapers somewhere involved, I still would like to be in Jimmy's place right now :)
Lots of tight and long hugs!
I really liked the story leading up to the pic. I would encourage you to do some more, this one is really good.
Baby Bobby__
Chad exploded in Jimmy's mouth with a deafening moan of pleasure. Holding Jimmy's soft face firmly in his hands, he forced the poor overwhelmed sissy to swallow what seemed like gallons of his hot, creamy semen. Jimmy gagged and squealed but it was like drinking from a firehose. The only hope he had to prevent from drowning was to swallow the salty spunk as best and fast as he could. The only problem was--no sooner did he gulp down a load when it was replaced with another. From his own pathetic experiences cumming, Jimmy was used to the small, ineffectual wet spots he made in Brooke's panties but this was like gulping from a barrel.

At last, the big cock in his mouth began to soften and Chad's grip on his head weakened. Just when Jimmy thought his humiliation was at an end, he saw his big sister cinching up what had to be the world's biggest strap-on dildo.

"Now I know why I've been losing all my panties," she said angrily, "This little pansy's been masturbating in them every afternoon."

"No--no--" Jimmy pleaded as he unconsciously licked the semen dribbling from the side of his mouth.

One look at the fat phallus buckled around his blonde sister's hips had him quivering in panic.

"Hold his wrists for me, Chad," she said tersely, "I'm going to teach my sissy brother a lesson he won't soon forget."

Her boyfriend chuckled and roughly bent Jimmy over the bed, exposing his virgin bottom for Brooke's intentions.
"First things first," she said as she tore off the dress he was still wearing, "I'm not going to have you cum on my clothes while you're taking it in the ass."

Jimmy pleaded with his sister as she lubed up the massive rubber dildo hanging from her harness but his pleas fell on deaf ears.

"If I was you--I'd relax--this will hurt a lot more if you resist me," she warned the whimpering sissy.
Jimmy wasn't sure if she was right or not but he did his best to obey as she began pressing the fat, blunt end of her strap-on against his puckering hole. As he whined and squealed, desperately squirming over the bed, there seemed no way the gigantic intruder would fit.

"No!--No!--No!" he cried but his sister only responded by pushing harder.

Gripping the thick, slippery shaft in her hand, Brooke stubbornly pushed harder and harder, trying to force the leviathan into Jimmy's reluctant back passage. As her boyfriend held his wrists securely, Jimmy looked up into his grinning. leering face.

"Here you go Sissy--just what you've always wanted," he snickered.

At last, the titanic dildo pushed past Jimmy's defeated sphincter, and he let out a cry of anguish and pain. His sister stopped only long enough to allow his overstretched hole to get used to the fat, rubbery girth before sliding it all the way until it bottomed out.

"OOOHHH!!" he moaned helplessly.

"Let that be a lesson to you--next time you decide to play dress-up in my clothes," she barked as she held Jimmy by his long hair and plunged the dildo in deeply.
charlee shultz
@ Baby Bobby__
  he is no longer a virgin 
Girls rule  
I love this story. My older sisters name is Brooke and I used to fantasize about her catching me dressed in her clothes. I always wondered what would happen if she caught me, now I know. You are a great writer, and I love the way you use the pictures at the end of each section of your story. I really hope there is more...
This story keeps getting better and better. I really like the way that you are doing these caps, with the storyline up above followed by a clean pic. It lets you get into the story before seeing the pic, whic to me at least, is much more sensual and exciting. Your storytelling is excellent!
I like your work, although I'm not into forced homosexual. Would you consider tagging future works as such?
Joe jones
Hi I want to become a sissy sex slave 24/7 
charlee shultz
He got his first lesson and learned it fast he had no choice  
Girls rule  
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