More Than He Bargained For (R-18) (UPDATED)

(warning: this chapter is mostly smut, but there is the story. But if you don't like sex scenes, you can skip or wait till my next chapter comes out.)

"Well, well, well, look who's back." My face was crimson, but my resolve stayed. I looked at her with a really shy look on my face. She let out a giggle. "I am really surprised you came back. Most naughty little boys never go to the same store twice." She let out another laugh as I felt her eyes going up and down my body. She puts on a more professional face and says. "So, what brings a naughty little boy to my humble place of work."

I stutter, trying to say, "I'm looking for some underwear." While my face was burning hot.

She looks unamused. "Well, of course, a naughty boy like you wants underwear, but what exactly are you looking for."

Still stuttering, "I'm looking for a set of bras to match the panties from last time."

Her smile grows wicked again. "So the naughty boy wants some pretty bars to match his pretty little panties, But before we get you anything, I must ask." She says, stepping closer while her smile is splitting her face. "Are you wearing your pretty little panties like a naughty little boy should?"

Despite all the embarrassment, I slowly shake my head up and down, hating every second of it. She quickly steps back, clapping her hands and looking like she won the lottery. "Well, let's begin first. Let's get your measurements." She says as she walks behind me, places her hands on my shoulder, and pushes me further into the store. Guiding me to the changing rooms, she grabs a tape measure and pushes me into a changing room. "Ok now Strip."

My stutter reaches an all-time high. "What do you mean strip? Why do I need to take my clothes off?"

"Well, of course, you need to strip. How else am I gonna get your exact measurements for your bars? Bars are not just a one-size-fits-all set like small, medium, and large. They are based more upon the endowment of the person wearing it and their overall torso size, like size A for young developing women all the way to size J for the most well-endowed. But you won't need to worry about that. We just need to find the right size for you. NOW STRIP!" she says with a more forceful tone.

#########R-18#########

(Femdom, Humiliation, Feminization, Sissification, Pegging)

I slowly do as she says and start to remove my top. I try to stop there, but she gets annoyed. Instead of voicing it, she takes action by placing her hands on my hips, and with one Swift tug, my shorts are around my ankles. Making me squeak and surprised.

"My my, what perky Little Titties you have," She says as her hands come up and start to massage my chest. She avoids my nipples and focuses on the area around them, making me slightly aroused. Finally, one of her hands makes a quick pinch and twist of one of my nipples, making me moan. Her other hand isn't far behind getting a double attack makes me keep moaning, and It makes my penis hard. "Ho Ho, so my naughty Little boy likes his nipple played with, and look at your Little dick. No more like your Little Clit has gotten so hard just from playing with your nipples. I bet if I keep going, you will cum hands-free like a Good Little Girl should."

Suddenly, she stopped making me moan with displeasure. She says, "Don't worry, my Little Sissy, I'll get back to the pleasurable part soon, but first, we have a business to settle" She then takes the tape measure and starts taking my chest measurements, and while doing so, purposely rubs against my nipples, making me moan once again. Getting what she needs, she begins to head out the curtains to get the bras that match the panties I'm currently wearing. But stops and says," Don't you dare touch yourself while I'm gone, especially your Little Clitty." Giving me a very stern glance before going to get the merchandise.

Left alone in front of a mirror and nothing but my underwear with my Clitty rock hard. Wait What? What did I just say? I just call my penis a Cilt. Why are her words influencing me so much anytime she would call me Naughty or call me Little or refer to my underwear as Pretty, or call me a Sissy or a Girl. My Clitty would jump and spasm uncontrollably. It would make me overly aroused for no reason. Something was wrong, but I just couldn't put the pieces together. While I was in mid-thought, she returned carrying a medium-sized bag.

"I see you were a Good Little Sissy. Let's put your bra on, and we can return to the fun part." She says, pulling out a matching set of bras and underwear, seven bras that match the underwear I bought before, and another 7 sets of pink with black trim bars and panties. She hands me a set of pink and tells me to put them on, and unable to refuse, I slowly slip out of my panties while she helps me put on the bra and teaches me how to do it myself. Then, when I bend over to put on the pink panties. She sees the bright red crimson diamond of my butt plug. She places a hand on my back, preventing me from standing up. "My My, I knew you were Sissy the first time I saw you, but to think you were such a Slut to already be wearing a plug to prepare your Boy Pussy for A Real Man's Cock."

I try to think of something to refute her words, but nothing seems to come to mind. It seems after her words, my Clitty hasn't stopped leaking as if proving her point.

She told me to stay in place and don't move, so I stayed there leaning over in front of the mirror with my ass in the air. She pulls my panties up just below my ass and then pulls out my butt plug with one sharp pull Causing me to let out a very slutty sounding moan. "Well, someone's a little more trained than I thought it might fit." Not understanding what she meant. She turns and walks back to the bag she walked in with. She pulls out something and then steps into it like she's putting on underwear, but I can't quite see what it is from the reflection in front of me. Then she turns around and presents what she just put on. She's wearing a medium-sized dildo in a bright pink color, sitting about 8 inches long, twice my size, for sure. For some reason, the site of it makes my Clitty leak even stronger. She stepped up behind me, resting her cock on my ass cheeks, and slowly started to grind back and forth. She asks, "Do you feel that Big Hard Girl Cock? That's right, this is what a Real Cock looks like. You don't even compare, and it's about to make you a Real Girl, a Little Sissy Girl. It will take every last piece of your masculinity like it should be." she says, slowly pushing the head of her Big Cock into my Little Bussy. I moan just like a Girl, and I can feel her excitement from the hands on my hip at hearing it. She slowly sheaths it all the way to the base, then slowly pulls it all the way back out to the tip. Then starts rocking back and forth with each push and pull. I let out more and more Girly moans. I'm far too gone in the fog of lust to care anymore. She hits my prostate, causing me to cum on the ground and putting out the loudest and Girlyest moan of them all.

But she doesn't stop there. She doesn't care that I came. She keeps getting faster and faster, constantly hitting my prostate and making me cum over and over and over again. I lost track of how many times I came in a row, but eventually the cum stops flowing. She had completely milked me, but I hadn't stopped climaxing. All the while, she's fucking me; all she is saying are degrading and humiliating things. "Kami, you're a Little butt Slut. It's like you were born to take Cock. to think a perfect Little Sissy would walk into my store just so I can take his virginity. Kami, I'm blessed! Do you understand you were born to take! Not give it! Take it! Your Little Clitty will never know the inside of a woman. You will die a Virgin, for no woman will ever let something so small even near them. Do you understand, Sissy, you are not a man, you are not a boy, you're nothing but A Little Sissy Born To Take Cock.

After what felt like an hour, she finally pulled out and replaced my butt plug and gave my ass one good final slap. At the slap, I realized she had been holding me up the whole time, for my knees had given out early into the session. Causing me to fall face-first into my own pool of cum again for the second time today. She tells me to clean up my cum like a Good Little Sissy. Unable to control myself, I started to lap up all the cum on the floor. It took me a while for my balls to be fully drained of cum. But when I finish, she grabs me by the back of my head and forces her Cock down my throat, and makes me clean her cock until I have another dry orgasm. She pulls free and lets go of my head, and I fall to the floor, exhausted. She looks down at me with a look of pride and lust, she then says. "What do you say to someone who helped you?" I look up and say thank you, but she says, "No, properly thank me. Get on your knees, bow your head, and say exactly what you are and what you are thankful for, and end it with Mistress. Unable to fight back, I fight to get into the kneeling position, lower my head to the ground, and say, "Thank you for teaching me my proper place in life, Mistress, that I'm Not A Real Man and never will be. That I was born A Little Sissy Bitch meant to take Cock for life and stay a Loser Virgin for the rest of my life, so thank you, Mistress, for putting this Sissy Bitch in Her place."

She looked down please herself before ordering me to get dressed and head home and that she was done spending her time with a Little Sissy like me. I slowly got dressed, which was hard because I was physically exhausted, but I eventually managed it slowly and then made it to the front of the store. I see her holding the same brown paper bag by the front door. She said she's giving it to me for free, and she even threw in a little extra gift for her favorite Little Sissy. I grabbed the bag and headed out the door, but the moment I passed her, she gave me one last slap on the ass, striking my butt plug really hard before closing the door behind me and locking it.

#########End Of R-18#########

I suddenly feel the butt plug vibrate like when I first activated it. Causing me to let out another moan in the middle of the street. I feel it gets slightly bigger than before and a little bit longer, but suddenly, the weight increases all over my body. I hear the cracking Of glass, and suddenly, I also see space in front of me cracking apart; as if a fog was parting, everything made sense. From the moment she clapped her hands, she placed a Genjutsu and me. Allowing her words to have more influence over me and making all her words like gospel, implying that there was no other truth, that her word was law. She made me her Sissy, and I think if it weren't for the butt plug and its special effects. I would've gone on living believing I was her Sissy for life. This realization sends a shiver down my spine. Knowing how terrifying Genjutsu really is. Too afraid to confront her, I rush home, hoping to get as far away from her as possible. Once in my bedroom, I throw everything in the closet, put on my pajamas, not even caring that it's basically négligée, and pass out on my bed, hoping to forget everything that just happened.