Popping My Own Cherry
Ever since I had learned "The Art of Masturbation," (which I don't think is an actual book; I just figured I'd capitalize it as though it were a decent topic, which I believe it is and maybe I should write about it and publish it) when I was about eighteen and a half, I was hooked. And yes, the age is true. My parents were very strict, and scarcely let me out of their sight until they finally trusted me to go off to college, realizing they would eventually have to let their daughter out into that big, bad world. For various reasons I didn't start college until I was nearly 21, but that's kind of beside the point.
Back to the masturbation and orgasm topic. I found it, big time: The thrill of orgasm surging through my senses, through my muscles, through my body, through my mind, managed to hook me, and deep. Soon after that, I fantasized about taking a cock deep into my pussy, bumping and grinding away, him splashing his load of semen deep into my vagina. How would it feel? I wondered: How would a great huge throbbing cock feel in my puss? How deep would it go? What would it feel like when he came? I had to know these things!
Strangely enough, I felt pity for the guy who would introduce his cock to me. I mean, there it is, so stiff and straight and upright, and now he has to bend it to get it into my waiting pussy? It sounded a little painful and cruel. And so I practiced. I rolled my hips back while I masturbated, imagining my first-time lover intent on entering me. I didn't want to cause him any pain. Turns out I had it wrong, but that'll come later.
But pain...
I knew that with the first penetration would come pain, for me. I didn't want to stop that precious act of sexual intercourse involuntarily, because of some hurt. Even though I longed to give my cherry to a man, I wanted to do it without pain and drama on my part. I wanted to be ready to take it all, and fully experience the whole act.
So I determined to take my own cherry. To bust my virginity, so to speak. To pop it on my own.
Shortly after my third semester started, and on the advice of some good friends, I was downtown at an "Adult Book Store." I'd talked this over with my friends, and they described what I should look for. Without them there with me, I felt exposed, naked, dirty. On the other hand, I don't think I could have gone through with it had I had company with me. I smiled at that.
I imagined Shiela (yes, I spelled that right: "Shy-la", not "She-la"), her tawny locks braided up over her neck, laying back and opening her legs for her lover. What advice would she offer me, in the here and now? We all knew that she'd gone all the way, but I think we all wondered how it was for her. Did she get off on it? Did she put out for Burt all the time? How was the foreplay, and what did they do? Andrea was another one. Get her alone, and she'd give you the goods: "Here's what you do, this is how it'll feel," that sort of thing. Dang... I get hot even today just thinking about her descriptions. She had a way with words, and you could tell she was speaking the truth.
But neither Shiela nor Andrea nor any of my other friends were there with me. So, back to the pain, or the avoidance thereof.
Standing in this adult bookstore, I wondered where to turn. It seemed like any other bookstore, respectable video store, that sort of thing. A woman came up behind me. I hadn't seen her. The first I knew she was there was her voice: "Can I help you with anything?" she said.
I must have jumped out of my skin. My heart seemed to be in my throat. I turned to look at her, and my pulse skipped a beat. Here it was: I was about to talk with an employee of an Adult Book Store! After a considerable effort to calm myself, I managed to answer "Yes, that would be great." I couldn't help but stare at her. Her piercings really caught my eye: two rings in her earlobe, three studs through the top part of her ear, both eyebrows pierced and adorned with pins that looked like golden, teeny-tiny dumbbells. The hair on the right side of her head was close-cut to her scalp, and the rest brushed over to the left and dyed a shocking shade of green.
"OK. What is it you're looking for?"
"Um, toys," I answered lamely. Isn't that what Shiela and Andrea called them?
"OK. They're back here."
I followed her back to the end of the video section, still fixated on her hair, and now, the tattoos on her shoulder and the back of her neck. One that I distinctly remember is a snake holding a bouquet of roses in its mouth, and from the middle of the flowers rose a skull, with yet another snake, but smaller, slithering out of one of the empty eye sockets. Creepy.
Anyway, there on multiple pegs and hooks was a huge collection of dildos, vibrators, and what all else I couldn't tell. "Is there anything in particular that interests you?"
I had no idea! "Well, um, this is my first time..." I was about to say "here," (at the bookstore, I meant) but she interrupted me.
"I see," she said. "And you want to get ready for that special friend in your life?"
Damn, the woman was perceptive! "Um, yeah," I answered. I fought the urge to look down at my feet and not shuffle. I felt hot color come to my cheeks and I couldn't stop it.
"I'm Electra, by the way," she said. "And you are?"
"Meesha," I answered. "Short for Michelle."
"What a pretty name! But Meesha, I have to ask, are you 18 or older? This is an adult establishment, and we do need to know - "
"Yes, I understand." I fumbled for my wallet, took out my driver's license, and handed it over to Electra.
"Very good, Meesha." She handed it back. "The assortment of toys can be overwhelming for a first time shopper. May I make a guess why you are shopping?"
"Um, sure," I said.
"I think you're ready for that certain someone, and you, well, you know..."
"Yes! That's it exactly!" I exclaimed, and immediately wished I hadn't. I was so embarrassed. I felt my cheeks flush for the second time.
She seemed not to notice my embarrassment or my trembling hands. "Then you'll want something life-size and life-like, I think." She reached up to a peg and took down an enormous rubber pecker. "I've had a number of young women come in with exactly your intentions. This is what I've recommended to all of them, and I've had a more than a few of them come back as repeat customers. Many have told me it was just the right thing."
"OK, I'll take it!" I wanted to be out of there so bad, but this time not because of embarrassment: I wanted to see what this was going to feel like!
I paid for it and was out the door and into my car in a whirlwind. I thought of what I'd just done, and of the package sitting on the passenger seat (in the proverbial "plain brown wrapper"!), and I couldn't wait for the privacy of my room. I was so, so hot and bothered.
Finally I was in my room, alone. I was still living at my parents' house, but they wouldn't be back for hours.
My hands shook with anticipation. "Come here, you," I spoke to the bag. I took it out and gave the thing a closer look. I had no idea a cock could be that huge! As I was to learn later, though, it was larger than the real thing, but that was all right. I found a pair of scissors and cut the package open. Soon I had the Rubber Monster in my hands. I couldn't help it and I put it to my mouth and opened my lips around it. With a rush of heat I took it deeper, and soon felt an urge to get myself off. But I had to wait, I told myself.
I knew it was likely going to hurt at first, going in. I knew from Andrea's description that there would very likely be blood. I went to the closet and got myself a towel. I tossed it on my bed, smoothed it out, and then shed all my clothes. I reached down and touched my pussy. I was so wet I was nearly dripping. I put a finger up inside me and whispered to myself, "It's almost time." I got on the bed, spread my legs over the towel, and picked up the rubber penis.
No foreplay. Uh uh. None. Zero. This is it. The Main Event. This is not a drill.
I placed the head at the entrance to my vagina and pressed it in. It wouldn't go deeper. "Here we go," I said in a whisper. I pressed deeper, and there it was: the pain.
Is this what Shiela and Andrea experienced? How did they do it? With a rubber cock first, or with the real thing first? In the heat of the moment, I couldn't remember what either one of them had said about their first time.
I, on the other hand, was vacillating. Shove it in, or wait and relax? I so, so wanted to feel it deep inside me. I took a couple of deep breaths and waited. Tentatively I pressed it deeper. Deeper still.
All of a sudden I felt a horrible sensation, like a tear or a cut. It was in. I sucked my breath in through clenched teeth.
That was it!
