An Unvarnished Tale of Seduction

Author's Note: This short piece is a real, nonfiction story from my youth. It is the unedited, very uncouth, story of me losing my virginity at the age of twenty. This story contains what I call the 'good, bad and ugly' of my real-life experience so I'm not promising it will be to everyone's taste. It is absolutely accurate in every detail if that counts for much.

I considered dressing it up like so many other virgin stories, but I thought it would be fun to just put out the unsophisticated version for a good laugh. If you interested in lots of dynamite sex scenes, you might consider one of my longer, fictional works.

The 'first time' topic is a new area for me. This piece is also the first time I've ever written about myself in the 'first person' perspective so it feels a little strange to me. Please vote and leave a comment letting me know if it works.

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I was twenty years old and still a virgin. I know it sounds kinda unbelievable but it's true as shit. Not only was I a virgin, but I'd also never had a girlfriend, never kissed a girl and never even held a chick's hand. And it wasn't that I didn't want any of this. Quite the opposite! I longed for it daily. I knew from the time I could walk that girls were special. By the time puberty came along, I thought about them every waking second.

I just never developed the skill at connecting with them in a romantic way. I've always been reserved, quiet and even shy at times, but nobody could say I wasn't trying. In those early years, I lost count of the number of rejections I was dealt. Hell, maybe I was trying too hard!

Now I had scores of super hot, female friends and they adored me, particularly in good conversations. I have a gift for listening and offering thoughtful responses. I've always been decent looking, in good shape and I'm very nice, polite and respectful. Making friends was easy for me. Still is. Attracting girlfriends back then was impossible. Every time I tried to get past the friend zone, the barriers came up fast. Even the ones that didn't currently have boyfriends suddenly did when they rejected my advances.

I thought I did a reasonably good job at hiding my failure from the world but that was the perspective of a young, nerdy kid with no game. I'm sure now the reality was I stood out like a loser and not worth a young lady's efforts. I think by the age of twenty, I'd all but given up trying. Oddly enough, for years, I'd been noticing older women taking hard looks at me, some even openly flirted. In those years of my youth, I had a hard time allowing myself to feel attracted to older women. I'm not really sure why. I suppose it just seemed taboo to me, and I grew up a rule follower. The things I'd do differently if I could!

I grew up with a good friend, Brenden, and we were practically inseparable in those early years. Even now, at the age of fifty-five, he and I are still best friends.

Brenden was a very interesting, colorful character and you'd never guess that a guy like him could be friends with a guy like me. In fact, when I later became a cop, he was still hanging out with his Hells Angels buddies, experimenting with LSD and any other psychotropic substance he could find. Didn't affect our friendship one bit and we quickly learned to not discuss certain things out of respect for one another.

But I'm getting too far ahead of myself. In our teenage years and up until I was nearly twenty-one, we used to hang out and drink regularly. Generally, with friends from his side of the tracks. They were every bit as colorful and lots of fun to be around. For some odd reason, I could go to a biker party with Brenden and despite being a nerdy, 'do gooder' from the nice side of town, these people were totally cool with letting me hang out, drink their booze and stare at their scantily clad women.

One of the homes we regularly partied at belonged to Brenden's female friend, Candice, though everyone knew her as Candy. Technically, it belonged to Candy's mother, Roxy, who I absolutely craved. She was the only older woman I would have been happy to step out of my comfort zone for. When there was a chance to go to Candy's place, I was fucking down because I always knew Roxy would be there.

Roxy was pure trailer trash, and I loved every inch of her. She was somewhere in her late thirties, but her rough lifestyle made her look like she was in her forties. Her slender, tattooed body told me early on that she was a 'long in the tooth' stripper. It was Simi Valley and in 1989, that place wasn't attracting the highest quality women to work the poles. Nevertheless, she was perfection in my eyes. Seeing her in a tank top with no bra and a minidress with her legs spread all unladylike just made my prick ache! And the unfiltered cigarette that was usually hanging out of the corner of her mouth was simply 'yum yum' for reasons I still can't explain.

Roxy was always home and in retrospect, that should have been a clue to how she paid the bills considering the volume of seedy guys that visited her on a daily basis. We often hung out in Candy's room which was adjacent to Roxy's. I knew Roxy liked to fuck because most times I was there, we could hear her getting railed in her bedroom. Weird as it may sound, it became background noise after a while. I knew she was getting pounded, I wanted to be the guy doing it, but I accepted the hot, trashy slut was way out of my league.

So, one Friday night, we were hanging out at Candy's, in her bedroom. The room was small, so we typically sprawled out on her bed as we got drunk and bullshitted into the night. This time, Brenden leaned against the headboard while a buddy of theirs, John, sat at the other end. Candy and I crashed in the middle and drank Jack Daniels from the bottle while we listened to Brenden and John debate whether anarchy could actually work in America. Candy kept egging me on to drink more and I recall thinking it odd she would pay me so much attention since she didn't normally.

Candy was not in her mother's league, by my estimation, but she certainly wasn't unattractive. She was around five and a half feet tall and had an average build, weighing perhaps a hundred and twenty-five pounds. A natural redhead, she had fair skin and green eyes with very curvy, very succulent lips. If her lips were her sexiest feature, her breasts were definitely the most noticeable. I never have been into large breasts, but these babies were enormous! Like DD size, easy.

While I never felt great sexual chemistry with Candy, I always recognized that I'd do her in a heartbeat if I had the opportunity. But in the years, I'd hung out with her, she never showed much interest, so I never gave her much thought after a while. Tonight, just felt different so I let it play out, trying to impress her by going toe to toe with her on the bottle swigs.

For a girl with fifty pounds less body mass, she could put the drinks away. It wasn't long before I was feeling completely shitfaced, leaning back into her and sitting between her legs as she rested against the bedroom wall. Brenden and John were still jabbering on, but I don't believe they had a fraction of the booze Candy and I had. And while we were smack in between them, they just talked around us as if we weren't even there.

As I tried to sober my thoughts just a little, I noticed Candy had been running her fingers through my hair. I couldn't even be sure how long she'd been doing it. It felt wonderful, so I gave her a little, 'mmmm,' and put my hand on her leg.

Minutes went by and I thought I detected hot breaths on my neck. Moments later, she was kissing and sucking my neck and ear. I heard a faint moan from her and all I could think was 'Fuck, yeah! This is amazing!' She must have read my mind because her hands came around my chest, roaming and groping before making their way to the growing bulge in my pants.

Turning my head as far as I could, she grabbed my face and smothered me in wet kisses. I quickly turned my body to face her, and we made out like maniacs for what felt like days. There was a point where I no longer heard Brenden and John's voices and where I couldn't hear anything in the house, despite the loud music. Whether it was a trick of the mind from the alcohol, or I was just so into her, all I could hear was the wet, sloshy sounds of our passionate kissing.

After a while, she stripped off her shirt and I was absolutely stunned by the sight of her enormous tits. She hadn't been wearing a bra, and being the clueless dipshit I was, I never noticed somehow. But I noticed now! And as if that wasn't enough, she had ridiculously long, meaty, hard nipples. Of all the women I've known since, I still haven't met their equal!

She rolled me onto my back and fed them to me one at a time, periodically switching them out as I learned a new skill. She particularly enjoyed me chewing on them lightly so, I was all too happy to please. From this point on, I didn't care what we did exactly as long as it was with her!

I lost all track of time and soon, she unbuttoned me and whipped out my rock-hard prick. Teasing my knob and swirling precum all around it, I groaned in satisfaction. Smiling, she went down on me, and I finally knew what head felt like. She sucked on me for the longest time but in my drunken state, I had no compulsion to ejaculate. I wanted it to last forever, anyway.

As she bobbed up and down feverishly on me, I threw my head back and just rejoiced in her gift. For the briefest of moments, it became clear that Brenden and John were still talking, and it pulled me into a moment of pure clarity.

These two guys were still talking around us as though we were invisible! And they were talking about Dungeons and Dragons of all things. 'What the fuck', I thought. My aching prick is getting sucked on like a popsicle and these guys are talking about a role playing game? Totally oblivious to what's happening only a couple feet away?

Just then, Candy told me she was going to the bathroom for a minute and not to go anywhere. 'Where would I have gone', I thought. And more importantly, why would I consider leaving now? A couple minutes later, she retrieved me and dragged me out of the room by the hand.

The house was only a tiny two-bedroom, ramshackle place, so when we went into the other room, I knew it could only be Roxy's. Damn! How many times had I imagined fucking Roxy senseless in that room and in a bizarre twist of circumstances, I'd be doing her daughter in Roxy's bed instead. Since I had such a huge crush on Roxy, it seemed like a hell of a step in the right direction!

As we crossed the hall to the other room, I noticed Roxy drinking with a couple dudes in the living room. Our eyes met and she smiled. She knew exactly what her daughter was up to! No doubt if Brenden and John left, we would have remained in Candy's room but the ease with which Candy adjusted to the situation left no doubt that she and her mother had some sort of strange agreement.

She turned off the lights prior to entering the room but there was a nightlight nearby which provided enough illumination for us to get to work. She dragged me to the bed, stripped off my clothes, then dropped to her knees to suck on me more. I was really getting into things now and felt comfortable making loud grunting and groaning noises which only had her slurping and sucking more aggressively. I was hoping Roxy could he me through the thin walls!

Had I been able to cum, I gladly would have, but the whisky was messing everything up. I had never tried to get off while drunk so it simply didn't occur to me that it could have such a drastic effect. Strangely enough, I didn't feel dull in any way. My dick was hard as stone and I could feel every tongue stroke, but I just couldn't crest the hill.

After a while, she stripped down and got onto her back for me with legs spread invitingly wide. While she clearly expected me to mount her, I wanted to show her what a big man I was by treating her to some of the same oral pleasure she gave me. Sure, I'd never done it before but there was a time when she never sucked dick before too.

I dove into her box and licked her everywhere, beaming with pride. Seconds later, I was asking myself if pussy normally tasted so horrible. Sure, it was my first one, but I kept thinking, 'why would guys enjoy doing this? It's terrible!' Days later, I learned Candy used some sort of contraceptive gel down there to avoid getting pregnant, so, uh, yeah, lesson learned! Despite the awful taste, and not knowing better at the time, I continued like a trooper, determined to get her off.

Mercifully, she eventually beckoned me to climb up and mount her. I needed no instruction here! I climbed on and fucked her with reckless abandon. She seemed less interested in kissing me for some reason, but I was in my groove now. I wanted to fuck! At one point, I noticed the bed had been knocking the wall the entire time but that was fine by me! That wall faced the living room, and I wanted Roxy to hear it all!

I tried so hard to will myself to cum, but it just wasn't happening. I must have fucked her hard for a solid ten or fifteen minutes when she started shuddering and suddenly screamed out in rapture.

Candy probably had no idea I was having trouble getting off and must have thought I was a real stud! That's what I tell myself anyway. Soon, she suggested another position and I was totally game. She got on all fours next, and I easily found my way back inside. Grabbing her by the hips, I plowed her wet box hard, immensely satisfied when the bed started hitting the wall again.

Anyone standing out in the hall or using the bathroom would no doubt have heard my loud, primal grunts every time I hit bottom, and they certainly would have heard the loud, smacking noises our bodies made!

After another twenty minutes, Candy started moaning louder and I knew now she was getting close. Tired as I was getting, I drilled her even harder and told her to scream out loudly. When she did, I took great pleasure from it. Twice now, I made her cum and both times, her slutty mommy overheard it!

At this point, I was wiped out and started to worry there was something wrong with me. We continued to try different positions and while I was having the time of my life, I really wanted to finally orgasm.

Flipping her back onto all fours, I tried something different. I pretended I was fucking Roxy instead of Candy and within minutes, I could feel it was about to happen. I kept my mind on Roxy, knowing she could hear me through the wall and as I erupted, I roared like a fucking lion in triumph. Fuck, that felt good! I never imagined cumming inside a pussy could be so amazing.

We both collapsed on the bed and Candy held me for a while. When she complimented me for giving her a good fuck on my first time, it became obvious that somehow, she knew I was a virgin. Didn't matter anymore, I told myself, since I no longer was one. She asked me why I didn't have a girlfriend, and it felt very much like she was feeling out my interest in dating her. I told her I didn't know but the truth, of course, was that I didn't yet have the skills to land one. Thankfully, she let it go at that.

Around this time, my head was spinning bad, and I felt like I would soon puke if I didn't stand up and move around. Not wanting to ruin a great night with something like that, I quickly got dressed and got out of there while Candy ran off to the bathroom to clean up.

When I made my way out to the living room, I could see everyone had already split. I found Roxy standing alone in the living room with a knowing smirk on her face and her hands on her hips in this sexy, little 'come fuck me' pose. It might have been a 'Good God, took you long enough' pose but I like the thought of it being the former!

It seemed fairly obvious she had been waiting to get her bed back but the look she gave me kinda suggested she wanted some of what I just gave her daughter. The perspective of a drunk kid, no doubt!

With a heavy heart, I said goodnight to my big crush, for fear of vomiting everywhere if I stayed, and started walking home, replaying the nights fabulous events. The best thought being that sexy, slutty Roxy would soon be lying in the wet spot I created. Even more appropriate, I felt, since I was thinking of Roxy when I made it! The cold air on the four mile walk home did me a world of good and helped me think again.

By the time I made it home, I realized I missed out on a wondrous opportunity with Roxy. If I hadn't been on the verge of getting sick, I might have even tried. I like to think I would have. Something changed in me that night. Like a light switch. I recognized that I had a powerful attraction to older women. And I certainly found new confidence! Seeing how Roxy looked at me was something I'd seen before with older women yet foolishly, I never attempted to act on those opportunities. A mistake I'd never make again.

Because I enjoyed myself so much with Candy, I attempted to get a regular thing going with her in the days that followed, but she didn't appear all that interested. A part of me was actually glad. We never had sizzling chemistry, and she was probably not my type anyway but all these years later, I see she was exactly what I needed, when I needed it. I can't honestly say she'll hold a special place in my heart or something corny like that, but I can honestly say I'll never forget her or what she did for me.

On a humorous note, Brenden admitted to me more than thirty years after the fact that he put Candy up to it and she agreed ONLY because she wanted to do a virgin. You gotta admit...that's a good friend looking out!

Three months after losing my virginity to Candy, I met a woman eleven years older than me who was hot and very flirty. I came on to her in a clumsy, immature manner but she looked past that and had me in her bed on the second date, teaching me how to eat her out in the way she preferred it. And this time, I really enjoyed it. It's become one of my favorite things, in fact.

I was with this older woman for a few years, and she often called me her 'boy toy,' even to her friends, but I didn't give a shit. She was turning me inside out on a nearly nightly basis, and I learned volumes from her on all matters sex. My sex life just kept getting better after that!

So, besides having a pretty fun 'first time' experience, I took something very valuable away from it. No, I'm not talking about 'don't go down on women who use contraceptive gels' or 'don't drink too much or you'll never get off,' no, the thing I took from it was that I had been going about my problem all wrong.

Something about my personality works very well with women thirty and over. Once I redefined my target, I had no problem finding sensational women to be with anytime I wanted. All I was doing in my early years was spinning my wheels with young, immature girls when I should have been focusing on older hotties all along!

Oh, and I still fantasize about Roxy. I tried catching her alone many times but couldn't. But I have to credit her for this; To this day, I adore trashy women. Especially the ones who smoke. I attribute that entirely to sexy Roxy!

The End