Ally Explores Ch. 01

This is chapter one of a three part story. Each chapter sort of stands on its own, but they will make more sense read as a set.

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This is the story of how I changed from an innocent, although sexually curious girl, to a woman who is constantly in pursuit of new ways of achieving physical pleasure. Looking back on it with the benefit of the passage time, I guess things happen for a reason. If you can overcome the disappointments and roadblocks that are put in your life path, you can really find happiness. At least, that has been my experience. My name is Allison, but I go by Ally. I'm in my thirties now, but this story is about the relationship twists and turns that I navigated when I first got out of college. That uncertain time when you feel like, just maybe, you've finally become an adult.

I'm a Midwestern girl from downstate Illinois. My family tree is Scandinavian and German, so I'm blessed with blonde hair and brown eyes. I think I'm fairly attractive, more on the cute side of the scale than gorgeous. I'm five foot five and take pride in my figure. My boobs aren't massive - 34B, but neither is my butt.

Sexually speaking, I was pretty inexperienced when I went to college. I'm an only child, so there weren't older siblings to clue me in. My mom gave me a very sterile birds and bees talk when I was about twelve, and sex ed in school filled in some blanks, but I really didn't understand the pleasurable nature of sex. That all changed shortly after I turned eighteen and I discovered masturbation.

Kate was a close girlfriend of mine who had older sisters, so she was light years ahead of me regarding sex. Her eyes were opened early on when she had stolen a trashy romance novel from one of them. Reading it she figured out that what had been clinical words in class, like erection, nipple, semen and vagina took on a whole new meaning, and she made sure to keep me up to speed. And there were new words like cunt, fuck and cum that we whispered about when we were alone.

Early in my senior year, I was at Kate's house after school one day she pulled out her laptop. She told me she had figured out how to get around her parents internet filters to access porn sites, and she showed my how to do it. She told me the on-line porn showed so much more than what they had told us about sex in school. I was admittedly interested, but before we could delve into any of them, Kate's mother came home. I quickly wrote down the filter bypass instructions and one of Kate's favorite free porn websites on a post-it note and slipped it into my backpack under all my schoolbooks, and snuck it into my room when I got home.

I was eager to hit the web, so shortly after dinner I told my parents that I had a lot of homework, and that I'd just go to bed when I got done. This wasn't new behavior for me. I was a good student and took school seriously, so my parents didn't even raise their eyebrows. After I finished what homework I had, I stripped down to my panties, put on a loose night shirt, grabbed my laptop and got into bed.

It only took a few minutes to start an anonymous internet session that got through all the tracking software my parents had installed to keep me "safe." I went to Kate's favorite site. She wasn't kidding that there was more to sex than we'd been told. I had visions that intercourse was a mechanical thing. But the moaning and the fluids and the athleticism and energy involved in the various acts was mind blowing. The more I watched, the more I began to get flushed. I felt a moisture between my legs that was a new sensation to me. My hand wandered down to my panties as I continued to read, and eventually my fingers slipped inside the waistband and travelled to my pubis mons. When my fingertips brushed my clit, I sat up like I had been shocked. I immediately put the laptop down and checked to make sure my bedroom door was closed completely.

Satisfied that my parents couldn't see or hear me, I laid back on my pillow, raised my hips, and pulled off my panties. Cautiously, I returned my fingers to my clit. Once again, the electric shock surprised me, but it felt soooo good that I started to gently probe the contours of what was now a very hard nub. After a few minutes of exploration, I began to gently rub two fingers back and forth across it. God, it was an intense and exciting feeling. In no time, I was frigging myself so fast my hand was a blur.

After a few minutes, I could feel a wonderful charge building in my crotch. It was kind of a cross between an itch and a tensing muscle. When our sex ed teacher explained the word orgasm in class, she described it as a "climax after stimulation," and several of the kids had giggled. Ignorant of what she was talking about, I had laughed along and tried to appear like I was "in the know." As I continued the assault on my clit, I realized that I was going to find out very soon exactly what a climax after stimulation entailed.

By this time, I had kicked off the bed covers and drawn my knees up to spread my legs. The nerves in my clit and vagina were firing rapidly, and I could feel moisture leaking from my opening. I also discovered that as my nipples rubbed against the inside of my night shirt that they had become very sensitive and VERY hard. Harder even then when I got out of shower in a cold winter bathroom. I guided my free hand under my bunched-up night shirt to touch one of my nipples. When I made contact, it felt like a circuit was completed between the nipple and my clit. I whimpered softly and then bit my lip in an effort to stay quiet. I began to roll the nipple in my fingers, all the while strumming my clit insistently.

All of a sudden, what had been an "itch" feeling crossed over to an amazing burning pleasure spreading outward from my clitoris. I felt contractions begin in my vagina, and then before I knew it, the contractions became quaking spasms. My legs went straight and stiff. I raised my head and shoulders off the bed. My nipples were on fire. I could hardly breath. "Unnnnnnghh," I grunted deeply as my very first orgasm ever overtook me. My vagina was powerfully clenching and unclenching as I tried to continue to rub my clit, which seemed to be the epicenter of all the pleasure. I was pinching my nipple so hard it hurt, but that just seemed to amplify the orgasmic wave I was riding. I remember thinking, "Ally girl, you're cumming!," as my whole body twitched. "Ohhhhhhh," I moaned quietly as my orgasm started to subside. I released my nipple, let my strumming hand come to rest, and collapsed back into my pillow.

I lay there exhausted in bed, breathing raggedly. I smelled an aroma that I recognized could only be coming from my female sex. My hand was really tired from constantly rubbing myself, but I managed to move it down to the opening of my vagina and I found that my pubic hair was matted with moisture, and there was a fairly sizeable damp spot on the sheets. I was responsible for doing my own laundry, so I wasn't worried about it, but I made a mental note to plan for this outcome next time. Because I knew there would most certainly be a next time.

As much as I wanted to fit in with my friends and date in high school, I never found a boy that appealed to me as a boyfriend. The guys at school all seemed either immature or insecure, so for the rest of high school, masturbation in bed at night was my only sexual release. And I did enjoy and look forward to masturbating. It wasn't like I was playing with myself every free minute. On average, I probably went to bed three nights a week without underwear, but with a small towel that was guaranteed to end up being soaked with my juices. After I had exhausted most of the videos on Kate's original site, I moved on to look at other porn sites that friends at school talked about in the locker room or at parties.

The visual pornography excited me more than web sites with sex stories, but there were some aspects that I found to be a complete turnoff. I had always been raised in a home where gender equality was very important. So highly produced porn with women obviously faking their pleasure disgusted me. So did things I thought debased women. In that category were blowjobs, especially when the guy finished on the woman's face or body. I also couldn't imagine swallowing a man's sperm. Bondage was certainly out. I thought women shaving their pubic hair was catering to a male view of sex. Vibrators didn't appeal to me. Nor did some intercourse positions I thought were degrading, like doggy style. I wouldn't every let myself be dominated like that. I wanted sex to be an intimate, mutual experience. Most of what I watched were home videos of amateurs just energetically fucking. Once in a while, because I had never seen it in person, I watched videos of well hung amateur men jacking themselves off until their sperm shot out.

After high school, I went to a highly regarded university in a neighboring state. The boys there were much more my type. Serious about their education and excited about their future and place in the world. Eventually, through mutual friends and common classes, I met Victor. I'm not going to spend much time writing about Victor, because it brings back feelings of hurt, but to understand me now, one must understand the relationship Victor and I had.

Victor and I started out as friends of friends. As we got to know each other, we discovered we liked to be in each other's company. We sat together when our group got together, saw each other daily in a couple of classes, and eventually just kind of evolved into dating. At first it was innocent things like meeting up to study for an exam, but soon it was much more social and increasingly flirty.

I was still a virgin, and I was a bit self-conscious about not having checked off the intercourse box. Not only was I still a virgin, I'd never even made out with a guy. Sex wasn't a mystery to me of course (see masturbation, porn above!), but I was worried I wouldn't be good at it my first time. Kate laughs at me now about the whole thing. Her belief is that for college guys, any sex is likely good sex, and that's probably true.

With that in mind, I decided the first time Victor made a move, I was going to let it go all the way. We had talked about my lack of boyfriends in high school, so he knew I wasn't a slut, and I suspect he knew I might be a virgin. I was in love with him, and I wanted to show it. I got ready by taking a red-faced trip to the drug store to buy condoms. Long story short, one weekend when my roommate went home to visit her family, I invited Victor over to the apartment. We had some wine, listened to music, played a couple of games of Scrabble and then ended up in my bedroom. I guess you could say I seduced him.

Soon our clothes were strewn on the floor, and I was spreading my legs for him. Victor was gentle and attentive, but it turns out he wasn't very experienced either. It was kind of awkward, especially the fumbling with the condom. He eventually got himself sheathed, entered me and thrust until he came. Not much happened for me. By then I'd been masturbating myself to orgasm for a couple of years and he never got me close, but it was intimate and sweet, and I felt attached to him.

Our relationship went on until just before we graduated from college. Our sex skills got better of course, and I got a prescription for the pill from campus health services. Victor learned to finger me and make me cum. I learned to enjoy giving Victor a hand job where he would reward me with ropes of jism arcing onto his chest. And we screwed often, alternating who was on top. I even got so that I could orgasm once in a while when I rode him, grinding my clit against his cock while I pistoned up and down.

Still, periodically Victor would ask me to do things that I just didn't want to do. Oral sex was a big one for him. He also wanted me to masturbate to orgasm while he watched. I explained how I wanted to have an equal and mutual physical relationship, and I thought he understood.

We were interviewing for jobs our senior year and both had several offers. I thought it was obvious that we would have to discuss making decisions that were good for both of us and would allow us to continue as a couple. One night at my apartment I raised the topic. Victor stunned me by saying that he wanted to break up and that we should each go our own way. I was devastated. I thought we were in love and headed toward marriage. We'd even joked about baby names. With tears streaming down my face I asked him why. "It's the sex Ally," he said. "We just aren't compatible in bed."

"How can that be?" I sobbed. "I gave you my virginity. We have sex all the time. You've never once complained."

"You just won't try things. You won't expand your horizons. You always say you want mutual intimacy, but you won't do oral sex even though you know I'd love to go down on you. You won't shave, or masturbate for me. I can't even take you from behind for crying out loud."

"RIGHT! You can't TAKE ME. I won't PERFORM FOR YOU," I screamed. "Get away from me you asshole. Get out of here!" And he did. Turned on his heels. Grabbed his jacket. Slammed the door. And he was gone. I curled up into a little ball on the couch and cried for hours.

I was in a funk for several months. I graduated and took a job in Chicago. I threw myself into my new career. I put on a brave face, but inside I was a wreck. I was mad and hurt and strangely, I also felt guilty. That somehow, I deserved some of the blame for Victor leaving. Kate knew of the breakup, but not the details. She checked in with me regularly to try to elevate my mood. She was working in Detroit, and had fallen for a guy she had met. His name was Brett and it sounded from our talks like he was good for her.

Kate's opinion was basically that I needed to get back on the horse and find a new man. I wasn't anywhere near being ready, and I told her that. Kate said if that was the case, she was going to come to Chicago for a girls' weekend and cheer me up. I reluctantly agreed, and we found a weekend that worked for both of us and put it on our calendars. Two weeks later, Kate drove down from Detroit.

She rolled into town at about nine o'clock Friday night. I have to admit, seeing her smiling face at my apartment door was like a breath of fresh air. Kate is a spunky, pixie of a girl. She was a gymnast in high school. She claims to be five foot one, but that's generous. She has shoulder length brown hair that she has worn in a high ponytail for as long as I can remember.

"Ally," she said, "we are going to have a great weekend. But tonight, you are going to pour us each a humongous glass of wine and we are going to have a heart-to-heart talk."

"I am, am I? What if I don't want to talk? I'm still in a pretty dark place."

"That's what I aim to change. Just get us some wine."

I opened a bottle of red and generously filled two glasses. Kate and I sat at opposite ends of the couch. Kate took a big sip of wine. "First off Ally, I need to understand what happened with you and Victor. I was thinking there were going to be wedding bells and all of a sudden, it's all over. What gives? Why the split?"

I paused for a moment collecting my thoughts. How much should I share? The issues were all intensely personal. They involved sex, and what kind of sex I enjoyed. I wasn't sure I was comfortable opening up to Kate. But in the back of my mind, I still had that little nagging feeling of guilt that somehow Victor wasn't totally in the wrong and that some of the blame for the relationship failing belonged with me.

"And?" Kate said, looking at me expectantly. I knew I had to hear her opinion.

"Well," I said, "I guess you could say we weren't on the same page sexually."

"Not on the same page how?" Kate asked.

At that point, the dam that was holding me back burst and I told her everything. What I was willing to do and enjoy, and what Victor wanted me to do or try. I was blunt and graphic, and I tried to explain why I was so keen to have sex be mutual and intimate. I told her about the guilt I was feeling that maybe I was partially at fault. "What do you think Kate?" I asked. "Honestly, tell me. Am I crazy? What could I have done differently? I'm never going back with Victor. That's over. But I can't bear to go through anything close to this ever again."

"Honestly Ally, I get where you are coming from," said Kate.

"That sure sounds like there is a "but" coming," I replied.

"Yep, you're right. BUT I think you are really missing out on what can be intimate and mutual by drawing the lines where you have. Let me give you a couple of examples. Masturbating for your man can be intensely erotic. Knowing you are the cause of his arousal. And let me tell you, they don't just sit there watching. They play with themselves too. So it's mutual, just like you said you wanted. And I can't think of anything much more intimate, especially if you take your sweet time getting yourself off, and then sit back and watch him spurt."

"You've done that?" I gasped, a little surprised. I knew Kate was comfortable with sex, but I had just assumed she was conservative in that regard.

"Ha. Many times, with more than a few guys. I've done most of the stuff that's on your prohibited list. Oral sex - both giving and getting. Because I'm short, getting into a 69 position is easier for me than most, and there isn't much better than a guy's tongue on your clit while you suck his cock. Again, I think that's the definition of mutual and you can't get more intimate. I've fucked in a bunch of positions, and have enjoyed most of them. I'm also shaved bald as a baby."

I sat there stunned, and for the first time in a couple of months, feeling a bit turned on. We had opened another bottle and were on our third glass of wine by then, and I was getting a little tipsy. I knew my face was a little flushed, and I could feel a familiar tingle starting in my cunt. My nipples were beginning to harden too. Embarrassed, I wrapped my arms around myself to try to hide my growing excitement.

"Kate, you're kidding me!"

"Not at all," she replied. "I enjoy sex a lot. Always have. Experimentation is good. And you could say I haven't been afraid to experiment. Here's a suggestion Ally, instead of saying sex should be mutual and intimate, why not go with trusting and enjoyable? I get that you want to be on equal footing with your guy, but you can't make that judgement based on each individual sex act. You have to look at the entire sexual relationship."

"Here's another way I think of it," Kate continued. "There's a difference between having sex and making love. Making love is about the emotional connection and the sharing. Having sex is about the physical pleasure and cumming hard. I don't have any problem letting Brett take me from behind for a quicky, if the next time he spends extended time with his tongue in my pussy for example. It all evens out."

I could feel myself starting to lubricate. Visions of a faceless Brett pounding Kate doggy style were flashing through my brain. "Uh, I guess that makes sense," I mumbled. "I'll think about it if I ever find someone."

"You'll find someone Ally, sooner rather than later. You're cute, successful and intelligent." Kate glanced at the clock. "Wow, it's getting late, and I'm pretty worked up after all this smut talk," she said chuckling. "If you don't mind, I think I'll retire with a little motorized friend I brought and take the edge off."

"Motorized friend?" I asked without thinking. Then my hand flew to my mouth as I realized Kate was talking about a vibrator of some sort. "Oh, I'm sorry Kate, how stupid of me."

"That's okay," she said laughing. "That was the wine talking. But I am horny. You must be too. It's been, what, four months since you've slept with someone? No one night stands? And all you have are your fingers, right?"