Punishment For The Sissy Lipstick Thief

 

Punishment For The Sissy Lipstick Thief

James was fighting a battle he could not win.  The urge to dress up as Jamie, the woman he just knew he was meant to be, had become overpowering.  He fought this with everything he could, but it was no use.  He'd gone beyond dressing up in his room when he could get away with it to going out in public when he thought he could get away with it.

He knew this was wrong, so he fought it.  He was so scared about getting caught that he constantly cleaned the cookies on his computer and stored files on a flash drive that he hid in a safe place with his clothing and makeup stash.  His friend Rebecca had told him about a support group he could go to, but he hadn't quite gotten the nerve to go yet.

His trips in public were anonymous.  He'd go to other neighborhoods and walk around, sometimes taking trips through the mall. He would browse clothing stores when he got up the nerve and actually did shop, but when a lady asked if she could help him find something, he'd still get spooked and leave.  How could he stop this?

He made a trip to Wal Mart to pick up some things for home that his mother asked him to get when he saw the red Color Stay lipstick and lip gloss.  He wanted that particular shade, but he didn't have the cash.   He could have put it on his debit card, but he was scared of having it appear on a bill with his name on it.  He put it in his pocket along with a couple of pairs of pink panties.

He went to self-check out to avoid the line and was on his way out.  The checker at the door looked in his bag and checked his receipt.  It was all going well until he got outside and heard a female voice.  "Excuse me.  Where do you think you're going?"

He froze and turned a shade of white.  The lady approached him from behind and reached into his right front pocket to retrieve the lip stick and gloss.  She looked at it and smiled.  "Oh, that's a good color honey.  I bet it would look good on those lips too."

He turned around to stare face to face with a short-haired brunette lady with the red lipstick in a security uniform.  "I can explain."

She gently grabbed his arm and led him back into the store.  "Uh huh.  They're for your sick mother?  Or maybe you're girlfriend?"

"I didn't mean to, " he pleaded, "but I can't..."

She chuckled.  "Girlfriend?  Who am I kidding?  A dainty little thing like you?  They're for you, aren't they?"

"Please ma'am, " he begged.  "I can pay for them.  I just didn't want anybody to know they were, um."

She stopped and looked at him.  "You didn't what, " she asked with an arched eyebrow?

"I didn't want anybody to know they were for me, " he explained as he started to cry.

"Uh huh, " she said as she reached into his other pocket and pulled out two pairs of panties.  "What about these?  I like the lace, by the way."

He started crying.  "They're for me.  I'm sorry.  I can't help it.  I'm sick."

She led him to the back.  "Well, I'm gonna have to file a report."

"Please, don't tell my mother.  I'll do anything."

She approached a door with the word Holding on it and unlocked a couple of locks as she looked at her watch.  "Shoot.  It's lunch time.  You're gonna have to wait, but don't worry.  We have somebody here to keep you company."

She opened the door to reveal a plain room with a couch, two chairs and a small table.  A black man stood up.  Did you find my receipt?"

She let James go and looked at the other man.  "Not that I know of."

"Well, look in the shopping carts.  It's probably out in the damn parking lot.  I ain't lying.  I bought that stuff."

"Yeah, okay Antoine, " she replied.  "If that's what you say."

"Just look, " he insisted.

"I have people looking.  Nobody's found anything yet."  She looked at James and Antoine.  "You two behave yourselves.  I'm on my lunch break.  I'll be back in a bit."

She left and locked the door behind her.

Antione looked at James as if he was sizing up the slender framed white guy.  "What are you in here for?"

"Shoplifting, " James replied as he wiped a tear.

He looked at the blonde pony tailed white boy, who was still in his teens.  "Anybody ever tell you that you look like a girl?"  James said nothing.  He touched James' arm.  "That's a compliment, baby.  You pretty for a guy.  You could be a girl."

James looked away.  "Please.  I don't want any trouble."

Antoine grinned as he grabbed his crotch.  "I ain't giving you no trouble, baby.  But, you getting me hard."

"So, " he replied, not even looking at him.

"So, I think you need to do something about it."

"I'm not doing anything, " James replied as he walked away.  "Leave me alone."

Antoine followed him.  "The way I see it, you have two choices baby.  You can get down on your knees and suck my cock.  Nobody gets hurt and you might even like it.  I bet you would."

"Please don't."

Antoine grabbed the white boy's head and turned it to make sure he was looking at him.  "Or you can resist and call for help.  They might come, but not before I whoop your ass good and make you wish you had sucked my cock."

James started crying.  "Please don't."

"I don't want to baby, " the big black man replied.  He looked like he could hurt him pretty badly if he wanted to.  "All you have to do is suck my cock."  He pulled down his pants and revealed a rather thick and uncut eight-inch cock.  "Here, look.  I bet you want to suck it."

James looked at it.  It's not like he hadn't imagined sucking a cock before.  "Come on baby.  Suck it.  You're a little sissy boy anyway.  I bet you want to suck it."

James felt a couple of tears run down his cheeks as he reluctantly got on his knees.  He resolved to suck the cock in front of him to end this peacefully.  He opened his mouth and started sucking.  "Use your tongue baby."  James started to lick underneath the cock and pulled back to the tip.  He licked all around the tip as he sucked it.  "Yeah, like that baby.  Lick my balls."

James held up the massive cock as he licked his hairy balls.  "Suck them, baby."  James did as he was told.  "See, I knew you was a sissy cock sucker."

James went back to sucking the cock.  This was his first experience, and he could taste him.  "Slow down baby.  Take your time."

James started thinking about what would happen if somebody entered the room and saw him sucking cock.  They could save him.  Did he want to be seen that way?  Antoine pulled his cock out of the sissy's mouth.  "No, baby.  I need some of that tight white ass."

James looked up and pleaded with him.  "No, please don't."

Antoine shook his head.  "Pull down your pants, baby.  Let me have a look at that ass."

James felt the tears as he pulled down his pants to reveal a pink pair of lace panties with the words Girlie Girl written on the back in glitter.  Antoine laughed.  "Shit, I knew you was a little sissy faggot.  Here, bend over the table.  I gotta get some of that."

"Please don't, " James begged as he bent over the table.  Antoine wet a finger and inserted it in James' ass.  "Damn, you are tight baby.  No problem."  He reached into his pocket for a packet of something.  James felt wetness on his ass.  "Astroglide, baby.  I always come prepared."

Was this really happening?  James was in disbelief.  The hardness pushing against his tight rear opening let him know it was real.  "Relax baby, " Antoine said.  "It will go easier if you relax."

James whimpered as the tightness gave way and Antoine's massive invader started penetrating him further.  "Damn, baby.  Are you a virgin?"

James was sobbing.  "Yes."

"I'll try to be gentle, but I got to have some of this."

James felt the pain as about half of Antoine's hard eight-inch cock was inside his ass.  "Oh God.  It hurts."

"That's what they all say at first, " Antoine chuckled.  "But they get used to it."

Antoine started thrusting in and out slowly.  "Oh fuck, baby.  I wish I had you at home in my bed where we'd have more time.  I don't think we have a lot of time here."

James pretty much just lay on the table, resolved to the fact that Antoine was going to have his way with him.  The grunts and moans of the big black man let him know what was about to happen.  About five minutes later, he shot his seed inside James’s ass, and he felt the warm wetness lubricating his insides.

When Antoine was finished, he pulled out. James put his panties and pants back on and sat on the couch.  He began to cry.  Antoine stuck his cock in his face.  "Clean me up, baby."

James did as asked, and Antoine soon pulled his pants up.  Moments later, the security guard returned.  "Good news, Antoine.  We found your receipt.  It matches what was in your bag.  You can go.  Sorry for the inconvenience."

He smiled as the woman handed him the bag and he walked past her.  "That's what I told you.  I didn't steal nothing.  People always messing with a bother."

The woman looked at James, who was sobbing on the couch.  "Aw, what's wrong?  Are you scared?"

He looked at her with tears in his eyes.  "He raped me."

She walked over and looked at him.  "You don't look like you're hurt.  Are you sure he raped you?"

"I didn't want to get beat up, " he yelled.  "This is your fault.  I didn't deserve this."

The lady sat down and started laughing.  James was furious.  "This isn't funny.  He raped me."

"Was he big, " she asked as he stared at her in disbelief.  "I'm sorry.  I never introduced myself, " she smiled.  "I'm Destiny."

"What the hell do I care, " he replied incredulously?  "I was just raped!"

She put her hand on his leg.  "Look, sweetie.  I was going to make an offer to you anyway.  I think I may be able to help you out, but you need to tone down the attitude a little bit.  I'm gonna let you off here, but I can help you if you show me some respect."

James didn't know quite what to make of this woman.  "Offer?   What sort of offer?"

She stood in front of him and looked down at him.  "I suppose you've heard of a Dominatrix?"

He nodded as he felt some of Antoine's cum leaking out of his ass.

Destiny smiled.  "I thought you might have.  Well, I'm a Dominatrix.  My brother manages this store, and my cousin manages the one across the freeway on the other side of town.  I'm head of security at both places, and they are both my sissies."

James gulped.  "What do you want from me?"

Destiny grinned.  "Isn't it obvious James?  I mean, Jamie?  I think you'd make a pretty girl, and I can help you if you serve me.  How does that sound?"

James looked at the door.  "What if I refuse?"

She laughed.  "Oh, you can refuse if you want. Maybe I'll tell your mother about your thieving activities and how I caught you in our bathroom entertaining Antoine."

James stood up and protested.  "But I didn't entertain him!  He raped me!"

"Oh, my dear sweet sissy, " she said seductively as she put her hand on his face.  "You and I may know that, but your mommy doesn't.  Who do you suppose she will believe, you or store security with camera footage of your thieving activities?  We have a camera in this room too."

The sissy's mouth was wide open in shock.  "You wouldn't."

Destiny smiled and nodded.  "I would."

James looked down.  "Okay, what do you want from me?"

"Your obedience, my dear."  She pointed to the floor.  "I want you on your knees.  Kiss my boots and pledge your obedience to me."

James got on his knees and looked up at her.  "I will serve you Mistress.  I will do as you say."  He kissed both of her boots.

Mistress Destiny laughed.  "There now, that wasn't so hard, was it?"  She reached into her back pocket and handed him a card.  "There's an e-mail address on there.  You are to send me an e-mail the moment you get home and wait for your first instructions, is that clear?"

"Yes Mistress, " he replied.

"Okay my dear, " she reached out her hand to pull him up, and he noticed her beautifully manicured red fingernails.  "To show you what a caring Mistress I am, you may keep the lipstick and panties."

"Thank you, Mistress, " he replied, still in shock from what had happened.

She pointed to the door.  "Now go home and do as I've asked."  Jamie walked to the door as he heard laughter behind him.  "Oh, and try to stay out of trouble.   I do punish my sissies when they have it coming to them.  Your stuff is in the cart right outside the door."