Meesha's Firsts Ch. 01

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!

I waited for the waves of pain to ebb.

I pressed the rubber phallus in as deep as I could and began rubbing my clit like crazy.

I came and came again in endless waves of orgasmic bliss as I thrust it in and out of my pussy.

When I finally relaxed, eased out the dildo and rolled off the towel, I was surprised at how little blood there was. No matter, I thought to myself. Every woman is different. I made a mental note to ask Andrea about it.

But that was it! I was no longer a virgin. At least, not in the anatomical or physical sense. The sad thing, of course, if there was a sad thing, was that I'd just lost my virginity to a blob of latex rubber. Oh well. I wondered how many of Electra's customers felt the way I did.

But I was certainly ready for my first real Fuck, and yes, I mean that with a capital "F"!

Conversations with Andrea

Now that I had the virginity and pain issue resolved, the next step was the real thing. Actually, this story is unfolding a little too fast, so let me back up to before I talk about "The Main Event." Several smaller events happened on the path to my lost virginity, so let's not get ahead of ourselves and miss all the delicious foreplay.

I had some interesting conversations with Andrea, who was genuinely interested in my recent adventure.

"I didn't know you were going to go toy shopping," she said.

"Well, that was kind of the point of our earlier conversations about virginity, wasn't it?"

"Yeah, I suppose so. But tell me: did you really, honestly do it? On a rubber prong?"

I nearly shot beer out my nose, I was laughing so hard. Finally I calmed down enough to answer. "I did. And I named him."

"You named him? I mean, you named your rubber friend?"

"Yeah. Mr. Cox," I felt myself blush. "Maybe a little obvious, but I thought that after such an intense and intimate encounter, he should have a name."

Now it was Andrea's turn to choke off a gut-wrenching laugh. "Mr. Cox. How original! You'll have to introduce me to him sometime."

"I might. But I have a question, kind of a personal question, if that's all right."

"Sure. Shoot."

I wanted to know the answer, but I didn't want to ask the question. I stalled out, saying nothing.

"The question, Meesha?" she prompted. "It's all right, really. Now ask it, will you?"

"OK. Well, um..." I still didn't know how to go on, so I just blurted it out. "Did a guy take your cherry, or did you do what I did?"

"Both," she answered.

"Both?" I answered, confused.

"Yeah. I was worried we wouldn't be able to screw because I'd be in so much pain, so we went and bought a dildo. That thing was absolutely huge! I doubted I'd even be able to get the thing inside me, but my boyfriend assured me we would.

"We were at it as soon as we got alone together. We were both super turned on after making the trip to the sex shop. We started with just some soft, gentle kissing that got pretty hot, pretty quick. He was feeling me up, and I was struggling with his jeans, working to get his cock out. All through this, we were lip-locked, tongue to tongue."

"Yeah?" I was getting into this and starting to get turned on while I imagined the scene unfolding.

"Oh yeah," Andrea answered. "It seemed like we couldn't get our clothes off fast enough. I bent over the bed for him, and he slowly started working the dildo into me from behind. It seemed like the most comfortable way to get it in. But before it got very deep it started to hurt. It felt really good bending over the bed like that, waiting for something, you're-not-sure-what, and being totally horned out, but I decided I wanted to see it happen, so we stopped and re-arranged ourselves. I got on my back with my legs spread wide and a pillow under my ass. Pretty soon he had it in as deep as before; it seemed impossibly big and I kept thinking it couldn't go any further. He backed off then, letting it slip out and started licking my pussy. He went at it for a while and I lost all sense of time. He sucked softly on my clit while he worked his fingers in and out of my pussy. I got so fucking wet! I just remember grinding my pussy against his tongue until he stopped suddenly. He got the dildo and pressed it to my pussy once again. By now I was soaking and I had no idea what to expect, but that it might hurt in some way, but I was too fucking horny to give a crap."

"And?"

"He did it. Nice and slow and gentle. There was a stinging sort of sensation, but that was it. Suddenly he was pushing the whole thing into me! There was a lot of pressure as it slid in, deep into my pussy. Filling me and spreading me in a whole new way. I imagine it was like you with Mr. Cox." She smiled and chuckled. "Mr. Cox. I love it, Meesha!"

I wanted to say something rude, but I couldn't interrupt her.

"Do you want to hear the rest, when we went all the way?"

Oh boy, did I! "You know I do," I answered.

"Ok. Anyway, it was only the next night we were in bed together. Me, a virgin to intercourse, and Jack, the same , or so he said. I learned later from someone else that I wasn't his first. It pissed me off that he'd lie about that, that I was his first, but I guess that's a guy for you.

"Jack? Not Mark?"

"Yep. Jack turned out to be a first-class asshole, so I dumped him. Hooked up with Mark not too long after.

"But you wanted to know how this all went... I'll give you the play-by-play.

"We started full-on, hands groping, hair pulling, makeout. In fact, one of my favorite things when we're making out is when he grabs a handful of my hair, pulls my head back, and goes at my neck, especially when he's up inside me. Total submission. Pretty soon we were totally naked and up against each other. I could feel the heat and hardness of his cock, and I had to have it in me.

"He sucked on my breasts as he worked a finger up inside me. I couldn't believe how wet I was! I'll bet you're going to find the same thing.

"He moved up from my breasts and we started kissing. He was still fingering me like crazy. I think I climaxed at some point there. Anyway, he worked his thigh up between my legs, and I knew exactly what was going to happen. I lifted my upper leg over his hip to give him better access, and the next thing I felt was his cock pressing against my pussy."

This was as good as reading a sex story! Actually, it was way better: I was hearing it straight from the source, from one of my very best friends, and I could ask all the questions I wanted. I was totally entranced!

"Shall I go on, Meesha?"

I nodded, mesmerized by her tale. I had to know how it all went, how they both came together!

"Ok. Well, the feeling of his hard, hot cock was like nothing I'd ever felt. It was way, way better than the dildo. It was hot. I was hot. He moved against me with a will not my own. Intercourse (to me, anyway) is a feeling of complete surrender. I lifted my tits to offer him to suck on, and he did. I was beside myself with lust. He started fucking me deeper. Each thrust felt deeper and stronger than the last.

"I threw my head back, and he brought his lips to my neck, his tongue gliding over my skin. I went over the edge before I even realized it was about to happen. The fullness and motion in my pussy took over my whole body as wave after wave hit me. My newly de-flowered pussy squeezed around his cock in convulsions while I had my first cock-fueled orgasm.

"He moaned he was coming. I scarcely heard him. I think I told him to come inside me... that I had to have his hot rush inside me." She stopped talking, a blissful, far-away look in her eyes.

"And...?" I asked, trying to urge her on.

"And that was the end of my virginity, my friend." She smiled wickedly. "If you want more, you'll have to experience it yourself."

"But did he come inside you?"

"He did."

"And what did it feel -"

"Like? You'll have to find out for yourself! Hot and slippery are good words to keep in mind, Meesha."

"Aw, come on, you can't just leave me hanging like this!" I protested. "What did it feel like exactly?! Did he-"

"Whoa whoa whoa there, Cowgirl! One thing at a time! You have to learn these things on your own. It'll come naturally, so to speak, on its own. And then, we can compare notes. Meesha, seriously, I'm so excited for you!"

"So I'm sort of back to square one."

"How do you mean?"

"Mr. Cox doesn't exactly fit the bill. I mean I still don't have a boyfriend. And I want to experience the whole thing, from kissing to coming. I want that feeling of a hot, hard cock inside me, Andrea!"

"Jumping the gun there again, aren't you, Cowgirl?"

"I'm not!" I answered defensively. "But I'd like a little help learning how to pick up guys."

Andrea suddenly laughed so hard it came out as a snort. "Girls don't worry about that. We've got it covered. It's the guys, with their friends, who want to know how to pick up girls. I think you've led too sheltered a life."

Don't I know it, I thought. I ignored the remark. "So, what's the best... uh..."

"Way? Well, it depends. I'm not you. You're not me. How about this. Let's go out Friday evening if you can get out of the house."

"I think I can. I mean it's about time I do. In fact I think I need to move out." I said with growing determination.

"There's no 'I think' about it, Meesha. You do. Much more freedom. No Dad waiting up for you to ask how your evening was. No Mom watching your every move. Ugh. Girl, we have got to get you straightened out."

We talked some more, and came to the idea that I'd accompany Andrea on a "Lady's Night Out." Shiela was going to come too, which secretly pleased me. I knew I couldn't hold a candle to her Scandinavian good looks: blue eyes, deep yellow hair, tight butt, firm full breasts, all that sort of stuff, but I had my own particular charms. Tall, at five eleven, 130, and 36C. Deep red hair, light green eyes. Shiela had told me once that I was "eminently fuckable." I loved her assessment.

Learning to Kiss

A day or so later Andrea and I were sitting on the sofa in her & Shiela's dorm room, talking about not much of anything, and sort of watching a movie, which was pretty stupid. Neither of us were really watching it, each in our own world of day dreams. I know what mine were, but Andrea's, of course not.

"Hey, tell me something," Andrea said, completely out of the blue.

"Yeah?" I looked over at her; her eyes were still on the screen, the characters engrossed in a hot kissing scene, which was probably the only good part of the movie

"Ever kissed a guy?"

Wow. That one caught me way out in left field. "Um, why do you ask?"

"Wondering. Wondering if you'd thought about. Wondering if you've done it. I mean, given everything else, one has to wonder..."

For some reason that kind of irritated me. "Well, I suppose you're right, and yes, I have kissed a guy, on prom night actually."

"Just a peck, or full on?"

Now I really was irritated. What business was it of hers? I decided to answer, hotly and brusquely. "What the hell has this got to do with anything?"