A Sissy's Encounter With The TSA

 A Sissy's Encounter With The TSA

Sissy Jillian finally got a look at the lower back tattoo Mistress had her get and was starting to cry. It had the words Insert Sperm Here on it with an arrow pointing down to her pussy hole. "How could you do this to me, Mistress?"

Mistress Abigail shook her head. "I did it for you, my pet. You've been doing so well in your training and have accepted your new role here. I thought that this was better than some boring butterfly tattoo. We can get one of those for your arm maybe."

"But, I'm not gay. " The sissy protested. "Now, if somebody sees this, they're gonna think I want to be fucked."

Mistress laughed. "First of all, if somebody sees it, chances are that you are about to get fucked. Secondly, whose pussy are you gonna get? Not mine, unless you're eating it. Furthermore, your locked up clitty won't be fucking anybody, not that it was ever good enough to begin with."

The sissy put her head in her hands and cried. "How could you?"

Abigail finally had enough. She reached for her paddle. "You know what? That's it. Assume the position, right now."

"But..."

"I said right now, " Mistress knew she had to be assertive. "You heed to learn your place."

The sissy reluctantly got on her hands and knees after lifting up her skirt. She felt the sting of the paddle five times and started crying. "I'm sorry Mistress."

"Damn right you're sorry, you ungrateful little bitch." She swatted her three more times. "I decide to give you the gift of a pretty tattoo in pink and black like you wanted, and you act so ungrateful."

"I'm sorry Mistress, " the sissy sobbed.

"That tattoo is gonna make the guys so horny when I have you serving them drinks at my party next month, and I thought you'd love it. But do I hear any gratitude?"

She paddled her ass hard another five times. "I'm sorry. Thank you, Mistress. I don't deserve you."

"That's right, you don't, " she replied, and she dropped the paddle on the bed. "Sometimes I don't know why I even bother with you. So ungrateful after all I do for you."


Jillian wept on the floor. "I'm sorry Mistress. I'll do better, I promise. I love you."

Abigail laughed. "Of course, you do. You'd better love me, you bitch!"

Abigail did love her sissy sub, but she got a big thrill out of the punishment aspect of their relationship. She knew her sissy craved all of it, but she didn't know how much she would enjoy it. She had invested a lot of money in stuff to put her sissy in her place.

Jillian actually made pretty good money as a free-lance writer and had written a successful romance novel with two more on the way. All of that money went to Abigail. It was agreed that all financial decisions would be made by Abigail.

The sissy was getting used to dressing full time, but she was very nervous about the flight she had booked for a special romance novelist convention that her publisher expected her to attend. He knew about her dressing, but she had never dressed in his presence. This would be the first time.

Mistress took her sissy by the hand. "Come here. I think it's time you went to bed."

"Yes Mistress."

She led her sissy to her bedroom, which was almost like a little girl's room with lots of pink and pictures of princesses on the walls. She made sure her sissy dressed in her pink nightie and panties. Then, she proceeded to restrain her to the bed and blindfold her.

She smiled and kissed her sissy on the cheek. "There. All safe and secure. I'll check on you in about six hours to make sure you're not in pain from the tattoo. You may need more meds."

She walked to the door and turned around. "Oh, I've decided you will remain in chastity for your flight. You need to be taught another lesson."

Jillian panicked. "But I can't. What about the TSA?"

Mistress laughed. "The TSA will be okay with you. You just need to explain things. You may need to go to the private screening room, but that's okay."

"But..."

Abigail took the ball gag from the stand and placed in on her sissy. "That's about enough out of you, Missy. Now go to sleep."

Jillian was nervous. Mistress not only forced her to remain in chastity, but she also ordered her to wear a pink butt plug on the flight. She could have just broken out of the chastity and removed the plug, but she didn't want to risk it. Mistress would punish her good for her disobedience.

She wore a short sleeve baby blue dress over a smooth figure shaping corset. The dress came down to her knees, and the black boots she wore came just up to her knee. Fully made up with her medium length black hair in a page boy style, she walked through the airport.

She had checked in her one bag, while dragging a pink carry-on bag behind her. She knew everything about her screamed sissy, and she dreaded trying to go through security.

The female agent looked at her ticket and laughed. "Jack Johnson?"

The sissy blushed. "I'm Jillian, " she replied in her best female voice. "Jack is my male name. I'm transgender."

She didn't look all passable to the agent, but she had been given sensitivity training on the matter. "Okay, go on through."

Another hurdle cleared, but now came the scanners. This was the part she dreaded. She removed all of her jewelry and opened her purse up before setting it in a container. Her boots were next. Then, she removed the laptop from her bag and placed it in a container with her smart phone.

She nervously entered the x-ray scanner with her arms over her head. As anticipated, a warning sound went off. A female African American TSA agent spoke to her her. "I'm gonna have to ask you to come to the security room."

Jillian blushed. "It's a chastity device. My Mistress made me wear it, and... um... a plug too."

The agent stifled a laugh. "Plug?"

Jillian couldn't remove the red from her face, even with the best makeup. "Butt... Butt plug ma'am."

"Oh, " she said with a grin. "In any case, I'm gonna have you ask you to follow me."

There was a little room not far from there, and the agent led the sissy in before turning around. "Joe, could you get those three containers and bring them here sweetie? Thanks."

She shut the door behind her. "Am I in trouble, ma'am, " Jillian asked nervously.

"Maybe, " she said with a grin. In reality, the agent had experience in the BDSM lifestyle. "What's your name?"

"I'm Jillian ma'am, " she replied, extending her hand to shake hers.

The agent shook her head in amusement. "Cute name. I'm Renee. You may call me Miss Bailey."

Joe entered the room with the containers. "This one has a smart phone and a laptop. Let me take a look at that laptop."

Miss Bailey grabbed the smart phone. "You do that. We can't be too careful in this day and age." She turned to the sissy. "I'm gonna have to ask you to strip down to your panties and bra..."

She paused for a moment. "You are wearing a bra and panties, right? What am I saying, I bet you're in a sexy pink lace bra and panties. You know, on second thought, strip naked."

"Miss Bailey, I don't think I have to do all of that. It's just a chastity..."

The female agent was starting to feel her dominant side coming to the forefront. "I didn't ask you what you thought, Missy. I said strip down now, or you will be in bigger trouble."

Jillian slipped out of her dress to reveal the pink bra and panties and corset. "What did I tell you? She's in cute sissy lingerie."

Joe laughed along with her at the revelation. "Um, Renee, take a look at these pictures."

Renee glanced over at the computer to see photos of sissies being put through their paces by a Mistress. "Oh my. What have we here?"

"It's just porn, " Jillian explained as she removed her corset. "It's all legal stuff."

Renee laughed. "Yeah, I'm sure. Who is Abigail?"

The sissy couldn't hide her embarrassment, but her chastity device kept her excitement from showing too much. "She's my wife.... I mean Mistress."

Joe was laughing. "Oh, I gotta tell Darnell about this."

Miss Bailey shook her head. "Only Darnell Joe, let's not create a scene here. Well, a bigger scene than we already have."

She typed a text to Mistress Abigail. "This is Miss Bailey. You have a pretty sissy here Miss Abigail, but she triggered our alarms with her chastity device and butt plug. What do you suggest we do about her?"

Jillian stood naked in front of Miss Bailey. "What do you want now?"

Renee walked around the sissy and touched the steel chastity device with her white latex glove. "All snug and secure I see."

The smart phone buzzed with a message from Abigail. "This is Miss Abigail. Do whatever you think needs to be done to my naughty little sissy, you have my permission."

Renee laughed. "Oh my God. You are in trouble now sissy."

Jillian started to get frightened. "What? What happened? What did I do?"

The female agent walked to the sissy's carry-on bag. "If I open this, I'm not gonna find any naughty toys, am I?"

Jillian blushed, and Abigail had her answer. Joe returned to the room. "Darnell will be here in a minute."

Jillian pulled out a six-inch blue dildo. "Perfect. Lock the door. He'll knock when he's here."

Joe locked the door and Miss Bailey stuck the dildo in the sissy's face. "Wanna explain this to me?"

"I... Um.... My Mistress made me bring it so I could practice, ma'am."

She grinned. "I told you, you may call me Miss Bailey. It seems your Mistress has given me permission to do whatever I need to do, and I think you need to show me what you do with this toy."

"But, ma'am, I..."

She slapped the sissy in the face and sat down in her chair, holding the dildo between her legs. "Show me what you do with this toy, sissy."

Jillian stood there and Miss Bailey ordered her again. "Show me what you do with this toy, or you will be punished."

Jillian knelt between her legs and started sucking on the dildo. "That's what I thought, " said Renee. "We have a sissy cock sucker on our hands."

Joe noticed the bandages on Jillian's back. "Hey, what's that? Did you get hurt?"

"It’s probably nothing Joe, " said Renee. "Just relax. Maybe I'll have the sissy give a demonstration on you next."

Jillian was relieved that the tattoo was not revealed to anybody. Then, she heard the phone buzz again.

"Be careful with the bandages on my sissy's lower back. I just got her a tattoo, and I don't want it getting infected, " read the text from Abigail.

Renee laughed as the sissy kept sucking her dildo. "What kind of tattoo did you get sissy?"

Jillian blushed, but her head being impaled on the dildo hid her expression. "Oh, it's nothing."

Joe stood up. "I want to see."

Renee grinned. "Go ahead and look, just be careful with the bandages."

Joe slowly peeled it off to reveal its slutty message. "Oh my God."

Jillian stopped and was admonished by Miss Bailey. "Did I tell you to stop sucking, Missy? Keep going before I spank that ass good."

Joe laughed. "From the looks of it, she's been spanked pretty good already."

"So, what's it say, Joe?"

He was still chuckling. "Get this, it says insert sperm here and points to her ass."

Renee grinned. "I like a sissy that cones with instructions."

She stood up and motioned to Joe. "Take your pants down Joe and give this sissy a nice cock to suck on."

"But, " Jillian tried to protest, only to get spanked on her still sensitive butt cheeks by Renee's hand.

"I didn't say you had a choice sissy, " Miss Bailey asserted. "Suck his cock now. You're about ready to show me what else you do with your toy."

Joe willingly sat on the chair. "Okay sissy, suck my dick."

Jillian reluctantly began sucking his cock. She had never sucked a cock before, only her Mistress's strap on. However, she understood what needed to be done."

Renee pulled the pink plug from the sissy's pussy hole and then inserted the vibrating dildo at medium pulse. "This is the advantage of plugging a sissy right here."

Joe laughed. "You've done this before, Renee?"

"Damn right I have, " she proudly proclaimed. "In fact, this little sissy right here is making me want to get a sissy of my own again. From the looks of things, Joe, you're not well endowed. I could train you if you want."

He was enjoying the way Jillian took his cock deep down her throat, gagging a little. "Fuck no." Jillian continued sucking.

"Come on, what's not to love? Plugged all the time, locked in chastity so you can't cum unless I milk you."

Joe said nothing. Renee worked the dildo inside Jillian's pussy, being careful to hit her in just the right spot. She was quite efficient at giving sissies orgasms this way in the past, and she used to make pretty good money as a Pro Domme doing this sort of thing. "How does that feel sissy?"

There was a knock on the door, and Renee shoved the dildo in deep before going to unlock it. It was Darnell. She opened the door and let him in before locking it. "Hey baby, I found us a sissy."

The bulge in his pants told the story. "I know, I had to shut off the camera in the other room and delete the recording. Girl, you got to be more careful."

"She's loosened up for you and she comes with instructions."

Darnell looked at the tattoo. "Oh fuck. I can do that, " he looked at Joe. "She any good at sucking cock?"

Joe grinned. "Oh yeah."

He looked over at the table. "Lay that bitch on the edge of the table. I have an idea."

Joe helped Jillian up and led her to the corner of the table with her back on the table. Her ass was at one end and her head hung over the other. "Perfect, " said Darnell as he stuck his hardening eight-inch black cock in her mouth. "Suck it baby."

Joe stood on the other end. "Mind if I have a go at her ass?"

"Fuck the sissy's pussy and lube her up for me, She gon' get stretched in a minute, " Darnell laughed.

Renee looked at the plane ticket. "You're gonna miss your flight, but we can put you on a later one. Will that hurt your plans at all sissy?"

"Nuh uh, " was all Jillian managed with a mouth full of Renee's boyfriend's cock.

"Good, " I'll set that up from here. "I think you need to learn a valuable lesson about trying to be sneaky with airport security."

Joe shoved his cock into Jillian's virgin pussy and began steadily fucking her. She was lost in a wave of emotion. How could Mistress let this happen to her? This was so cruel, even for her, but why did she like being in this vulnerable position so much?

Mistress had always talked about pimping her out to guys, but it was bedroom talk, or so the sissy thought. When she had that tattoo put on her, she began to realize that Mistress had other plans for her. This moment, lying on the table taking cocks at both ends, drove the point home.

Joe was fucking her steadily, and she found herself squeezing ever so gently when he pushed in. It wasn't long before he released his seed inside her formerly virgin pussy. "Oh, fuck yeah, " Joe proudly proclaimed.

Jillian was starting to taste hints of Darnell's cum when he pulled his rock-hard cock out of her mouth. "My turn, sissy."

His cock slid right in, though it was a tight fit for his girth and a good two inches longer than Joe's as well. "Yah see, Joe, this is why I like seconds. Gets a sissy's pussy ready for my big cock. Then I can pound that pussy good.”

Renee brought the dildo back to Jillian's face. "Suck it, sissy. Taste your pussy on it."

Jillian sucked as instructed. She knew this might not be right, but she had surrendered to the moment. She was now a full-fledged sissy slut, and her life would never be the same.

Miss Bailey looked at the sissy's face. "You like that big cock inside you, don't you?"
"Uh huh, " she moaned.

"Gonna let you in on a little secret. Darnell knows how to make a sissy like you cum, even if they're locked up."

"Oh God, " was all she managed as she was lost in a wave of pleasure."

Renee shoved the dildo back in her mouth. "I didn't tell you to stop sucking, bitch. Damn, I wish I had my strap on."

"Damn, baby, we need you go back to storage and get your stuff out. I think we need another sissy for our own. This bitch is tight, " Darnell was fucking her hard and deep, and she was talking it like a pro.

She smiled "I think your right."

As Jillian felt an orgasm build up, she was encouraged by Miss Bailey, "Let go, sissy. Cum for us. You know you want to."

"I can't, " Jillian replied.

"Yes, you can, " the female agent in insisted. "Stop thinking like a man and think like the sissy you are. A big cock in your pussy makes you cum. Don't fight it."

This talk drove the sissy over the edge. She started feeling her orgasm build and cum started leaking from her caged clitty. The feelings went on for a while as she enjoyed her first anal orgasm from being fucked by a guy. Mistress had given this to her with a strap on before.

"Here come the waves sissy, take it, " Darnell proclaimed as he erupted inside Jillian's pussy. When he was done, he moved back to her mouth. "Clean me off slut."

Renee put the plug back inside the sissy's hole. "Don't want to let any of Darnell's cum leak out of you now, do we?"

Jillian felt like she was in another world, "No ma'am."

"I gotta go back to my station. Get this bitch dressed and get her out of here, " Darnell said as he kissed Renee. He and Joe excited the room with the door still locked behind them.

"Get dressed. " Miss Bailey instructed as she texted Mistress Abigail once more. They exchanged texts the whole time the sissy got dressed.

"Okay, here's the deal sissy. You are on flight 108, which will leave in a couple hours. Your Mistress said you already have a motel room and the convention isn't starting until tomorrow morning."

Jillian looked down, still ashamed of herself. "Thank you, Miss Bailey."

Renee smiled. "No need to be ashamed of what you just did, honey. Lots of sissies are proud of doing this, and you were great. In fact, your Mistress says you will be flying quite a bit and locked up like the sissy you are. I told her to send you to us and we'll take care of you."

Jillian blushed. "Thank you, Miss Bailey."

"Fix your lipstick, Missy"

Jillian grabbed her lipstick and compact mirror and reapplied the shade of red she wore. She felt so dirty, but still turned on.

Renee handed the sissy her smart phone. "You now have contact information. Darnell and I would love to have you over some time, and your Mistress has invited us for a visit in a few weeks. I think we may just take her up in it."

Jillian left the room feeling violated, used and abused, but still turned on. She would make it to her destination on time, but this encounter had changed her. If she didn't understand where she stood with her Mistress before, she did now. She was her Mistress's sissy slut.

"I'm a sissy slut for Miss Abigail, " she thought to herself. "I can never be her man again. I am just a little sissy in chastity." She realized she was smiling at that thought. "I am so lucky."