Well, I did it. I did what he told me to. Admittedly, I didn’t want to do it at first. After all, I hardly know this man. Aside from a few friendly emails, some intimate photos exchanged and a couple hot chats, I can’t really say that I know this guy from jack. And along with not knowing my instructor, I don’t know how I feel about being told what to do. I’m new to sexual exploration, new to being with men that aren’t my husband. But for reasons I can’t explain, I wanted to comply with his demands more than I wanted to question them.
His instructions, which he called “homework”, were simple but at the same time complicated. I was to take a bath so that I was nice and relaxed. Then, with my towel underneath me to catch my juices, I was to lay in my bed naked. With my fingers, I was told to make myself wet, then fuck myself with thick markers, one in my pussy and one in my ass. “Double penetration,” were his exact words. “I want you fucking them. Not just putting them inside you.” I was to take my bullet vibe and press it on my clit. I was to make myself cum multiple times leaving both markers inside me. Then I was told to write this essay about my experience, and after all was said and done, I’d be rewarded.
I was reluctant at first. Sitting on the edge of the tub, filling my soaking tub with water, I stared at the markers and the small, silver bullet. I wondered how I was going to manhandle such items all at once while still being able to feel pleasure. After enjoying the warm water for a nice relaxing soak, I moved to the bed. I laid a clean towel down and crawled into my white sheets. I shivered for a moment, but quickly warmed under the bedding and decided that it was time to see if I could accomplish my assignment.
I rubbed my soft skin, my breasts, tummy, thighs. Lingering in the warm, quiet of my bed, I put off touching myself and considered taking a nap. But the cold, metal bullet lying next to me in the bed rolled into my leg, reminding me of the assignment that needed completion.
I touched myself, tenderly rubbing my lips, circling my clit lightly, and dipping the tip of my finger just inside my pussy. It didn’t take long before I was wet, very wet. In my mind was the photo my teacher had sent me of his shoulders, and with that vision in my mind and my fingers in my crotch, arousal was consuming me.
With my free hand, I found one of the thick markers. I touched it to my clit and shuttered. I ran it down my slit to my wet pussy and slowly slid it inside. I moved it in and out while I orbited my stiffening clit with my pointer finger. The tip of the marker grazed my g-spot and I gasped. I reminded myself not to touch my overly sensitive g-spot until I was ready to cum, so I decided to focus on my ass.
Penetrating my ass with the other marker proved to be a much harder task for me. With the dripping wet marker from my pussy, I poked and prodded my tight pink star until it was tender. I consciously worked to relax–counting, breathing–but nothing seemed to work. I was growing with frustration so from my nightstand, I grabbed a small container of Vaseline I use to take my makeup off and I smear the rounded end of the marker with it. I took a deep breath, closed my eyes, and slipped the end of the marker just inside my throbbing anus.
I had to catch my breath. After a few minutes, and a comfortable grasp on both markers, I was slowly starting to fuck the props inside me. The fullness, having something in my ass and pussy at the same time, was like nothing I had ever felt before. The marker in my ass burned. Each time I moved against it, the burn intensified and only after it was two inches inside me did the burn turn into a pleasurable heat.
I arched my back causing the stretch in between my pussy and ass to tighten. It felt wonderful. I arched it again, and rolled my hips into my hands holding the markers close to me. I knew I wouldn’t last long once the motions became rhythmic, so I grabbed the bullet and pressed it against my clit.
I held the markers steadily in one hand and the bullet in the other and hesitantly turned the little vibe on. The friction, that hot buzzing against my clit, was intoxicating. Not a full minute passed before I had my first orgasm, and I hadn’t moved at all.
I removed the bullet and took a moment to bask in the post-orgasm quivers moving throughout my body. I knew I couldn’t enjoy the pause too long or my courage to keep going would fade with each second. I touched the bullet to my sensitive clit and grabbed a hold the markers again. I turned the bullet on, and after moving against the two markers just four times, I came again. The second orgasm I had was quick and strong, stemming from a space within me that I had only felt one other time. Resting for a moment, I thought back to the time that my lover had fingered me so deep; it felt like the orgasm started in my soul.
I opened my eyes for a moment and inspected myself. My nipples were stiff and puckered–a tell-tale sign that I was enjoying myself physically. My legs were bent and open and there was wetness all over both my hands and the bullet. I noticed the tip of the marker sticking out of my ass and pinched my ass muscles around it, the zing of stinging heat intense. Like a switch had been flipped, I suddenly wanted to cum again and again.
I replaced the bullet on my clit and got a good grasp on the markers. I was ready. I turned on the small vibe and immediately went to work fucking my homemade dildos. I bounced on the bed, rocking my hips to meet my hands thrusting the markers into my two wet holes. The bullet purred against me, just below my clit, and not long before I was fucking myself fast and hard, did my third orgasm, from deep inside my pussy, erupt. I screamed out. I couldn’t help it. It was all consuming, and the sounds I was making matched the pleasure I was feeling.
I pulled the markers out at the peak of my climax and a gush from my pussy hit the towel underneath my ass. I wiggled back and forth, moaning, shaking, out of breath, lost in the orgasm that felt like an eternity in calming. But I knew I wasn’t done. There was one more orgasm within me from a spot I hadn’t yet touched. I didn’t feel relief, I wouldn’t feel relief, until I had experienced it.
My clit was tender to the touch. I inspected the small bullet in my hand and wondered if I was about to do permanent damage to my sensitive organ. I decided to concentrate on the marker in my ass. I pulled it out and slowly pushed it back in, repeating the motion for a lingering amount of time. It felt amazing and I couldn’t help but to add the second marker in my pussy. I plunged and pulled the plastic objects from my holes, my hips rising and meeting the rhythm in lustful sync. The burn in my backside was strong. Each time I pushed the marker in to my ass, I was one step closer to that final, freeing orgasm. I pushed the marker into my pussy and left it there and grabbed the bullet. I pressed it against my clit hard, the tenderness very real but almost welcomed. My mind went to an image of passion; me lying flat on my front, my ass in the air, and my teacher’s cock pounding me hard from behind. In harmony with the visual porn in my head, I fucked the marker. I jerked and bounced as the vibe trembled against my clit. Without warning, the orgasm started and was unstoppable. It started in my ass and I screamed out as it ravaged me, mind and body. It was the strongest, most intense orgasm I’ve ever had through masturbation.
I didn’t move for almost an hour after completing my homework. I savored the quiet, the spent feeling of having satisfied myself multiple times, the pride I felt from not giving up on penetrating my own ass, and the gratification in knowing that I had not only survived the assignment but that I enjoyed it.
Today, I’m still sore. My clit is tender to the touch, as is my ass. But as I write this and prepare to enjoy my reward, I know with all my heart that my homework definitely taught me something … my fingers aren’t always going to be enough.