"I'll see you then," said Emily, "you'll be paying."
"Okay," I replied.
"Now take care of yourself and go to bed, and no masturbating," Emily added.
I promptly said goodnight and signed off then went to bed. I felt like I didn't have a choice. I usually would have stayed up a bit later. I actually also didn't masturbate, which I did almost every night, I had a roommate, but my bed was strategically positioned in a sort of alcove, so he couldn't observe me unless he really wanted to crane his neck, and he would be far creepier than me masturbating if he pulled that kind of stunt.
After my classes on Thursday were over, I went back to my room, I showered, shaved, and wore some of the few nice clothes I had. I was extremely nervous and headed to Starbucks to ensure I got there early.
I sat down in the corner and ordered an Earl Grey Tea, I took it black. I got a text from an unknown number for a Venti order than went on for two paragraphs. It ended with, "have it on the table before I get there." So I placed the order and upon its completion I brought it over to a table in the corner.
Emily entered the Starbucks about five minutes after the order was done, and she looked remarkable. Her curvy frame was accented by tight shirt showing ample cleavage and a short pleated skirt, showing off what I could tell were athletic thighs and she wore some short, fashionable boots and had her light brown hair tied back in a ponytail. She seemed to glide more than walk as she entered the room. She sat down and looked at the coffee she got took a sip and said, "Good boy! Hi Holden, I'm not really sure what else to say, this is my first time with this in truth. The other guys seemed to just want sex and didn't care how they got it."
"That's okay, I have no experience in this kind of thing either. This is experimental and I've never had sex," I told her.
"Well, for starters, we might want to talk about no-gos and expectations. First, in public we're just any other two friends, I will be bossy and tease a bit, but in general, we'll seem within what is normal. Of course, I'll still be in charge whenever we're together, but everything will seem reasonable. Now, when it's just us and we're safe, that's when the dynamic changes. I want to be perfectly in charge. I'll be giving you a safe word for now, but I want to eventually take those training wheels off. In private, you call me Mistress, and whatever I say has the power of law. You'll be serving me not only by cleaning my dorm, doing my laundry, and driving me places, but also you'll be able to have your fun, if you do a good job, cleaning my dorm might get you sexy perks, of course a bad job and I might give you a spanking or even finding me kicking your balls," Emily smiled in a predatory way. You'll become obedient in time. Now, of course in public you can wear whatever you normally wear, but in private....well maybe you'll be naked, or in panties, or in a cute maid uniform I bought. You might also be wearing makeup. If you're really good I might take your virginity, but for now, if you get sex it's with my strap-on. Of course, I'll be having sex when it strikes my fancy, so be sure to keep my room stocked with condoms and keep it spotless. What do you think?"
"Uh...that's a lot to process, Emily..." I began.
"Shut up!" said Emily sternly, "see how this works? I'm the boss." She smiled sweetly and said in a stern voice, "Your answer? This is my fantasy; it sounds like it's your fantasy too. Your dick seems to agree." I looked down and had tent in my pants. I was terrified, but this was something I desperately wanted and never thought I could get it with a girl as cute as Emily.
"Yes, I agree to that, Emily," I said.
"Good boy," said Emily in a sweet tone, switching back to firm, "now as it is a weekend, we're going to go back to my dorm for an orientation session. You will be allowed to ask questions for the duration of the day. My roomie, Chrissy, is going home for the weekend, but if you stay on as my slave after this weekend, you will serve her too. I'm sure you won't object," she showed me a picture on her phone of a girl with messy reddish hair, "right?" Chrissy looked cute in the picture, with a trim figure and large breasts, and was definitely someone I wouldn't mind being my Mistress.
"Focus on me, boy," said Emily, "I'm your actual Mistress, Chrissy you will simply call 'Miss,' do you understand?"
"Yes, Emily," I said.
"Good boy," Emily said, then she continued, "I'm almost done with my drink, I think we should walk back to my room to give you an idea of where to go and what to do."
"Certainly," I said.
Emily took a big swig and said, "throw this out."
We walked back to her dorm. Emily walked in a very upright and confident way, and I followed behind her, looking more cautious and nervous. She said hi to a few girls before swiping in and beckoning me to follow. As we went through the halls a few other girls were smiling and giggling, mostly just gossipy types, but was it possible they knew about my special arrangement with Emily?
As soon as Emily unlocked her door and directed me in, she shut it and locked it and said, "so to start, no more Emily. It's Mistress Emily, understood?"
"Yes, Mistress Emily," I said.
"Good boy," she replied, "Now get on your knees."
I fell to my knees.
I surveyed the room, it was tidier than the room I had, it wasn't extremely meticulous, but neat enough. The beds were made, Emily's bedspread was dark blue, but her roommate's was pink, which matched the rug they had put in. The desks had two closed laptops on the desks, Emily's was black, the other was silver. Emily's had a logo of the track and field team at our college and a sticker that said "Girl's Rule!" on it. I had a feeling that would prove to me more than just a cute teenage slogan very soon. There we a couple of posters with different singers and music groups that girls' liked, One Direction, Katy Perry, Taylor Swift, whomever. Chrissy had a rally sign that read "Biden Harris, 2020." This wasn't going to be my choice, not that I had any love for the alternative. Emily had a poster that said "The Future is Female." That was yet to be decided, but within the four walls of this dorm room, that was going to be very true.
The clothes in the open closet were ordinary and the window showed a nice view across campus. A gentle and early autumn breeze rolled in. I was taking it in before Mistress Emily spoke again, "okay boy, clothes off."
I got my shoes, socks, shirt and ultimately pants off and she said, "Undies too, let's see what you're working with. I slowly peeled them down; Emily gathered my clothes and tossed them to the side. I instinctively covered my genitals with my hands.
"Hands at your sides!" said Emily with a harshness and loudness. She began pacing back and forth in front of me before standing directly in front of me. "Not a lot of muscle definition, definitely a weakling." Emily flexed a bit, she was right, she was definitely stronger than me.
Emily held my penis in her and then put her hand on my balls, she was gentle, but examined them. Needless to say, the instant she touched it I was erect. "A little on the small side," said Emily finally, "but not too small, but most beta boys like you are hung the same way. I will certainly be getting my pleasure from more adequate men, if you're lucky, or I'm having a rough night maybe your tongue is more adequate. Now get on your knees, bitch." I dropped to my knees quickly.
"Tell me, slave, how does it feel to be on your knees?" asked Emily.
"Mistress Emily, I feel beneath you," I said.
"That's because you are, being on your knees just makes it clearer. Now kiss my boots and let me explain the rules," she said.
I kissed her boots as a gesture of submission. Then came back to my knees to listen.
"You're going to be here all weekend. If I remember you at all from high school, I trust you were a good little geek and got your homework done in advance. If not, I recommend it going forward. Friday and Saturday night, unless otherwise noted, you will sleep on the floor underneath my bed. You will be permitted a blanket and pillows, if it's particularly cold that may increase, but for now it will do. Clothing is a privilege to be earned, my roommate and I will determine what should be allowed. Every Saturday morning you are to awake at 7 AM, and 8 AM on Sundays. You are to go to the kitchen near the lobby of my dormitory and make me breakfast. I will leave instructions. Any guests who stay here will be entitled to the same benefits. If no orders are submitted, you may prepare scrambled eggs and toast. The breakfast ingredients needed will be in my fridge. You may have breakfast, but will eat it from a plate on the floor, where you will have all meals, unless otherwise noted. Good behavior can be rewarded with eating over a table, if you're really good maybe my roomie and I can let you eat it off our feet or bums." Emily smirked at my erection and said, "you like that, huh bitch? Just know if you're bad, I may take your utensils away or limit your breakfast to cold gruel. So you better behave. Clearly, you'll need to go in public to make our breakfasts or do other tasks so, you can wear you regular clothes, just with this underneath." Emily showed me hot pink pair of panties and smiled.
"After breakfast we usually go to the gym, this will make us stronger, which will make any punishments we inflict more severe. It also makes us hot and athletic, say thank you," said Emily.