Teach Me Ch. 01

I threw my hair up in a messy pony, slipped my sneakers on, and hit the trail. I ran hard, my legs pumping faster and faster until my legs ached, but I pushed through the pain.

Pain. I needed the pain like I needed air. As a child I hated pain, falling off my bike, scraping my knee on the playground. As I grew into my teens and now early adulthood, I learned to need the pain. I exercised daily, pushing myself to higher limits every day.

But there was always something lacking. Some kind of shortage that needed replenishment but had never even been full in the first place. So I kept running, most days. Some days I went to the gym, but that was only when it was raining too hard to run outside.

I ran to my best friend's house a few blocks away from my apartment and entered unannounced. "Hey girl, it's me!" I hollered down the hall from the doorway. I took my sneakers off and fixed my wild hair, smoothing it back as best I could. She didn't answer right away, so I thought maybe she had company. I walked down the hall and rounded the corner to see her sitting in her lavish living room. Cross-legged on her plush white couch, completely absorbed in her laptop.

"Hey Jenni, what are you doing?" I asked and plopped down next to her. She looked at me sheepishly, her smile slowly spreading wider until all her brilliant pearly white teeth flashed. She was beautiful. Blonde hair, blue eyes, and a trust fund that would make a celeb envious.

"Haven't you wondered what I've been up to lately?" She asked with the same sheepish grin.

"I've been blowing your phone up all week, duh I want to know. Why do you think I ran so fast here?"

"You run fast no matter where you're going." She booped my nose and I swatted her hand away. She was oddly cheery. "I've been with a man Cassy. Like a real man." She was waving her hands now in excitement. My look must have prompted her to give more details. "So, this girl from work told me about this website and I had to check it out for myself. Everything is so legit and safe, with notarized contracts and tons of tests to pass and whatever but it was so worth it. I've had two sessions already and it is literally life-changing." She gushed, still smiling.

"What in the actual fuck are you talking about Jenni?" I questioned, eyebrow raised. "You bought a hooker?" Her smile dissipated and she stood up, slamming her laptop on the coffee table.

"No Cass, it's not like that at all. I hired a teacher. And we didn't even have sex the first session. It was all about getting comfortable with each other and talking. Everyone is clean. No STDs, no pregnancy, or anything like that. They teach you how to be a better version of yourself, like sexually." She tried to make me understand. I understood what she was saying, but I didn't really understand. I had never heard of anything like this before and was it even legal?

"How much did it cost? And they? How many people did you sleep with?" I asked trying to conceal the judgment in my tone.

"Just one, I just meant they as in not everyone gets the same person. We're not allowed to share names or any other really personal information. It's strictly business and it works." She was pacing around the living room. "I'm not sure how many there are, but I know there's both guys and girls and after the initial screening with the top guy, he chooses who your teacher is. And holy shit I wish I got him, don't get me wrong I love my teacher but he is so gorgeous, I've never seen anyone like him. Tan and dark, and mysterious. Just the perfect tall glass of water I'd gulp right down." She giggled and my eyebrow raised again. She could not stop gushing and I started to realize she was absolutely dead serious about this all. What was worse, it was slightly sparking my curiosity and that disturbed me.

"This is all just way too much information at once, why didn't you tell me earlier this week?" I prodded her.

Oh hmm, maybe because I knew you'd act like this? You're twenty-three and you still act like sex is some touchy subject." She laughed sarcastically and plopped back down in an armchair across from the couch I was still sitting on.

"Well can you blame me? You hired a sex teacher. I thought your sex life was perfectly fine. Why do this? And no I don't, it's just not my favorite topic." I prompted.

"Well, it should be. Anyways, my sex life has always been good, since I was a teen. But it's just gotten so, I don't know, boring. I needed something different, but I had no idea what. You ever heard of BDSM?" She asked nonchalantly.

"Yeah duh. So that's what this guy is supposedly teaching you? Whips and chains and all that?" I interrogated. I was disgusted, but then again that slight curiosity crept its way into my thoughts.

"It's not just whips and chains Cassy, it's so much deeper than that. There's an entire kink community out there doing things you could never dream of, but would probably love. I used to be weirded out by it all too, trust me. But I expanded my horizons a bit, so to speak." She looked down and picked at her fingernails. "And I don't call him teacher, I call him daddy." She looked up quickly as to judge my reaction to this bit of information, a smile playing at the corner of her lips.

"Jenni! You do not." I had to laugh this time, it was just too much at that point.

Her face turned red and I knew I'd hurt her feelings. I couldn't believe how serious she was about this shit.

"You'd like it too. I know it and don't deny it. Don't judge shit before trying it." She gritted between clenched teeth and stood up as if to leave the room. I stood up too and grabbed her wrist.

"Look I'm sorry, I didn't mean to upset you. I'm just new to all this and it's a bit shocking, you know?" I looked into her crystal blue eyes, but they weren't the same eyes I'd looked into nearly my whole life. They were different. Not in a bad way, but not in a good way either. Just different.

Her bristles went down a bit and she sat back down, taking a deep breath and then another.

"I booked you a screening, and you can't back out because I already paid." Her words all rushed out at once. I blanched, mouth slightly agape.

"You fucking did what?" I growled.

"You need this Cass, trust me. I'm nowhere near as bad as you and I needed it. Just trust me okay? And maybe say thank you because that shit is pretty expensive." She crossed her legs and pulled her phone out. "I'm sending you all the info now."

I literally had no words. I was genuinely and thoroughly pissed the fuck off. Why would she do this and what did she mean she's not as bad as me? It took me a minute to collect my thoughts. My phone chiming broke me out of my reverie.

"What do you mean I'm not as bad as you? What the fuck is that supposed to mean?" I demanded.

"You act like you hide it so well like I haven't known you my whole life. Your whole weird pain thing, all the running and the self-harm when we were kids. You still have the scars. Not to mention your horrid sex life." She said matter-of-factly. My face burned with heat.

"Why are you being such a bitch? It's not my fault I have no clue what I'm doing in bed, I'm not a slut ok? And the pain thing is my own and I don't like talking about it, you know that."

"Being with people doesn't make you a slut, you're just nervous you won't be good and you've chosen really shitty partners. And I do know you don't like talking about it, which is why I'm helping you do something about it." She chimed.

"Jenni, this is nuts and there's no way I'm doing this." I blurted. I stood up and looked out the window, chewing my bottom lip. There was no way I would do something like this, was there? My thoughts drifted to the pain, I needed to run. I turned toward the hall and started walking towards the door. Surprisingly, Jenni let me go.

"Just sleep on it alright? For me?" She pleaded as I headed out the door and ran home as fast as I could. I needed a long hot shower. It was as if there was an internal battle within my mind, one side telling me to do this and the other telling me to stay far the fuck away. I was once again disturbed at my own train of thoughts. But the pain beckoned me with its taloned finger.

I sat on the shower floor and curled into a ball, my chin resting on my knees, rocking back and forth gently under the scalding water. My skin prickled and tingled under the water, keeping my frayed thoughts at bay for the time being.

Eventually, I finished and got out to get dressed. I glanced at my phone on the counter, it chimed with unread texts. I swept it off the counter, pushing my reprieve aside, and opened the messages. All from Jenni.

I sighed and plopped down on my bed, reading the text she sent regarding my screening. I was expected to be at a building downtown at 9 am sharp on Monday. It was Friday. There was a suite number along with the address and that was it. I gnawed at my lower lip, lost in thought when my phone chimed again.

Jenni: I'm sorry I sprung all this on you so suddenly. I'm sorry it seemed like I was being a bitch, but I'm honestly trying to help you, Cassy. I love you and you've suffered for so long now. Just give it a try and I promise I won't be mad if you don't like it. But just try it for me, ok?

I bounced my foot hanging off the bed, and nearly chewed my lip right off. I had nothing going on in my life, nothing substantial anyhow. Work, run, home, rinse, and repeat. My love life was all but nonexistent and the last guy I dated was so short-lived I'm not sure if it even counted. I'd slept with only three guys. The first I had lost my virginity to and we only had sex the one time because it was so uncomfortable. I hated sex for years. Then the second guy introduced me to oral, and I started to like it a bit more. It turned me on so much that sex actually felt okay. We dated for a few months before I broke his heart. There just wasn't a strong enough connection. The third guy was just all together awful in bed. He wasn't well endowed and lacked the necessary skill to make up for it. We dated a couple of weeks at most, ending mutually.

No one had ever truly and deeply sexually pleasured me, and I craved it from time to time. But I didn't exactly know what I was missing, so it didn't drive me crazy or anything.

All the sex talk and thinking about it all and I realized I was soaking wet. My panties were sticking to my throbbing pussy, and it was uncomfortable. I needed to do something about it. So, I went to the bathroom and pulled out my vibrating dildo. It could suction to the wall and floor and was the only sex toy I liked and that got me off.

I went to my bedroom and shut the door. I dimmed the lights and laid on my bed. I took my panties off and started to finger myself and rub my clit in little circles, getting wetter and wetter. When I was wet enough and starting to make small little sounds of pleasure, I slipped in my vibrator. I moved it in and out slowly at first, and then harder and faster until I was covered in a sheen on sweat and was panting.

I clicked the button for the vibrator, and I could feel myself getting close. I arched my back upwards and went faster until I was slamming the dildo in and out, but it wasn't hard enough.

I moved off the bed and suctioned the dildo to the floor so I could ride it. I got on my hands and knees and arched my back as if someone were watching. I roughly sat down on the dildo and rode it hard, until I was moaning and squeezing my breasts in my hands. I twisted and pulled my nipples and rode it harder until I started to cum. I thought of a tanned, muscled, tall man that would make me call him daddy and I started to shake uncontrollably and screamed out. My body rippled with waves of pleasure, and I rolled onto my back on the hard cold wood floor. I rubbed my clit in little circles again to draw out the last bit of my climax and my legs shook.

I sat up and rubbed my face. I had thought about the man Jenni had described and I didn't know if that was a good thing or a bad thing. I was scared, going out of my comfort zone but I realized that I was going to do this. I needed to.