A First Timer’s Tale

Erotic stories,first time, A First Timer’s Tale.. I’ll be honest. After all, isn’t that sort of the whole point of this place? To be a place where we can finally be honest? And in all honesty, I just don’t get the appeal of wanting to read about somebody’s first time. To me, it’s a hell of a lot more fun to read about when at least one or more has a clue beyond a general idea of what goes where.

But, maybe that’s just me. I don’t know. It seems like a lot of people want to hear about those stumbling fumbling bumbling real “no shit, true story” first times any road, so here goes.

Oh, yeah. Almost forgot. All people engaging in coitus in what follows are over eighteen. The following is pretty much what happened to my recollection although it’s only my side of things and about as true as any eyewitness account, with one small proviso. Names and places and a few identifying marks have been switched up to blah blah blah.

Fuck it. That’s enough of that shit. Let’s get on with it.

I guess maybe I might have had chances to see what all the fuss was about earlier than I did. God knows I was interested, but that should hardly be a surprise. A teenage boy interested in sex. Go figure. And I found out years later that some of the girls I stayed in contact with were interested back then.


But, I never got further than some kissing and touching the odd tit over at least two layers of clothes. Odd as it may sound, I was the one who stopped it and didn’t allow it to go any further than that.

And it didn’t actually have more than just passing to do with being a good Baptist boy. Sure, I was a holy rollin’ Bible thumper in the buckle of the Bible Belt and was a mite more serious about it than the ones who brought their hangover to church on Sunday because that’s what we were supposed to do.

But, sex went beyond just a mere temptation for me. Hell, might as well say I was “tempted” to take a deep breath when I surfaced from swimming the length of the pool scrapping my belly along the bottom. Before I discovered nightly controlled masturbation would fix the mess, I had “wet dreams” every night.

Just about the only thing that held me back from crossing that Rubicon at an earlier age I think was being adopted.

“What the hell does your sorry ass being adopted have to do with anything, Dumbshit? Get to the good part!”

Well, frankly, I was the result of a pair of fifteen year old kids getting frisky and doing some exploring and “whoops! Working as the factory intended.” I guess they could have aborted me. While rarer back then, abortion wasn’t unknown. Instead, they gave me up for adoption.

And don’t get me wrong. I love my family. They are my real parents in every way that matters, God keep their souls. And I never once doubted that I was loved and treasured by them so long as they lived.

But, I also know that my sperm and egg donor tossed me aside like a used condom or tampon.

And I would not, could not possibly, risk passing that along to another possible child. Nope. Nope. Nope. I could wait to have sex until I got together with someone whom we were both willing to stick by each other and raise a kid together for the next eighteen years, if one happened.

Frankly, Wendy wouldn’t have been my first choice. In fact, if it had been left up to me, I doubt I would have ever gone on a date with her. Or even spoken to her.

But, then, if it’d been left to me, I might not have had a single date through college and grown old alone.

Wendy was not the prettiest girl working at Sam’s Wholesale Club running the registers while I brought in carts. That, if I could only choose one, probably would have been Deanna, although Lori and Kayla were so damn close tied for second as to make it a matter of how they were wearing their blonde, red, and brunette manes that day. Not to mention Luna who appeared in Playboy’s “Girls of the Southwest Conference” that year. Although Luna wasn’t really “pretty” so much as she had big tits and a wasp waist.

But, no. Wendy wasn’t the prettiest by a long shot. But, neither was she ugly. I could easily to this day, decades later, name ten cashiers that were uglier without even mentioning the two hairy legged guys.

Wendy was, however, the strangest.

It was the 80s, the age of “big hair”. Wendy wore her “dirty-dishwater” mane cut at shoulder length, which I guess wasn’t really all that strange even then. Or wouldn’t have been if she’d just left it alone. But, she swept it up into a topknot sticking straight up on top of her head right in the big middle like Alfalfa from the Little Rascals. Only instead of slicked or pointed, it was held in a rubber band and bushed out like paint brush.

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An unfortunate choice since with her heart shaped face, narrow shoulders and modest breasts, from the waist up “paint brush” was exactly what leapt to mind the first time I saw her.

And then there were her clothing choices. Her boots were too clunky. Her jeans were…not firm like denim should be and her ass wiggled around like two pigs wrestling under a blanket when she walked away. Most of the time she wore men’s crew neck basic white t-shirts up top.

Wendy never really smiled, either. Oh, she was almost always sort of smiling, most of the time anyway. But, it looked like only the left side of her mouth worked when she smiled. The left corner would twitch up by itself, and no teeth showed. It gave her a sardonic twist and I always felt subtly ridiculed whenever she turned it on me.

Not that I was any great catch.

Yeah, okay. I had played football in high school and was a little bit of a fanatic about working out. I was pretty solid with broad shoulders and a lot of muscle and little enough fat that the team Doc had called me out to put some fat on if I wanted to stay healthy.

But, I was only five and a half feet tall, so all that bulky muscle made me look more like a fireplug than an Adonis. Useful for pushing a string of twenty-five carts at a time back in, not so much for impressing the girls.

And, lest we forget, it was fucking July or August in West-by-God-Texas when we first laid eyes on each other. And I was running around on an asphalt parking lot for six and eight hour stints right through the hottest part of the day. I was always drenched in sweat, covered in salt from previous sweat not to mention dirt, and my face was usually peeling away in chunks from sun and wind burn.

I usually wore shorts and tank tops, which might have showed off my musculature to advantage to any that were into bulk. But, I was also cursed with enough body hair that my team nickname in high school was “Link” for Missing Link. And thick body hair hadn’t been a thing since the mid-70s so most guys peeled the glued toupees off their chests.

I don’t wonder why Playgirl never called.

So, perhaps it wasn’t really all that odd that Wendy and I, neither of us the prime specimens of our respective genders, managed to find each other. But, I doubt we would have even so, if she hadn’t grasped the bull by the horns and asked me out.

It was either late August or early September by then. I don’t remember which. I only know it was because the sun was touching the horizon when we both got off at closing time rather than a finger high in sky.

I was hot, sweaty, and tired. I was covered in parking lot grime and I’m pretty sure I wouldn’t have smelled too good even if I hadn’t stepped in the dirty diaper someone had thrown out after changing their baby. I really just wanted to drive home, which I still lived with my Mom thirty miles away in one of the smaller surrounding towns, shower and maybe veg in front of the television before getting some sleep. I had a dollar in my car glove box. And I wasn’t really interested in Wendy per se.

But, I’d also been without a girlfriend since early July and had lost touch with my high school buddies already as we’d scattered after graduation like dandelion fuzz on the West Texas winds. Maybe I was lonely. I don’t know. I’d never been all that popular, but I had kept busy.

And I was intrigued both by Wendy’s strangeness and her sheer chutzpah to walk up to me and ask me if I would go grab a bite to eat with her and offer to pay for it when I said I didn’t have any money. At least as long as I didn’t order the whole left side of the menu or anything crazy.

I don’t think I would have classified that first outing to McDonalds as a raving success by any scale as we limped around in conversational circles without really finding any common ground.

I was a Baptist who still went to church when I didn’t have to work. She thought her family might have been catholic, but she’d never been in a church in her life.

I’d played football and worked out incessantly in the off season hoping to overcome my lack of height to make a college team, which I hadn’t. Wendy had worked at a local music store when school was over for the day and had skated out of any extra-curricular through work/study.

Wendy liked to go to dance clubs, which I still think qualify as bars since they serve alcohol, and dance. Did I mention I was Baptist and actually pretty serious about it? Dancing was a no go. As was drinking. And such places were obviously dens of iniquity.

Yeah, all in all I think Adolph Hitler and Mahatma Gandhi would have had better luck finding something to talk about. Just don’t ask me which of us was which in that comparison.

Thinking about it now, I really could not say what in the hell she might have been thinking to ask me out again a few days later. Or what was running through my mind that I actually went.

But, we did. And then again. And then again.

She dragged me to the dance club. I dragged her to football games to retaliate each time. We tried miniature golf and bowling, which I don’t think either of us liked much since we only did each once.

And, oh God, the movies. I liked starships, sword and sorcery, or action films with a quota of bullets and explosions. I swear Wendy liked anything but those. I had more class than to heckle when it was her turn to pick like she did with mine. I just dozed.

And the food choices were ridiculous. About the only thing we could agree on was McDonalds so I could get a couple of Big Macs and she could get a salad. Other than that, I was a chicken fried steak kind of guy with a little spicy Tex-Mex when I was in the mood for something exotic. Wendy wanted to eat Chinese, or Thai, or Indian, or some other crap from some other continent with weird names and even stranger appearance. I drew the line in the sand at that creepy joint where the so-called food was still wriggling on the plate.

But, somehow, some way, we kept ending up spending time together two or three or more times a week until one day I looked up and realized she’d passed from that weird slightly annoying acquaintance you can’t quite seem to shake to a bona-fide girlfriend.

Maybe it was when we met each other’s parents. I’m not sure. I don’t really remember exactly what point we first held hands or kissed. I’m sure they would have been big deals to me, whether or not they were to her, but I just don’t remember. Mostly because of what overshadowed them later.

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I said at the beginning I’d never done more than some kissing and some petting. Nothing below the waist.

Wendy had. Only with one guy, granted. But, she had.

Maybe the smartest thing for me to have done would have been to back away from the relationship quietly and easily when she told me. Maybe then I would have remained the four cornered guy I was and gone on to lead a much quieter, if dull and boring, life.

I might have graduated with a different degree which would have led down a different career path. Maybe I would have stuck with engineering or maybe I still would have changed but to something else.

Maybe that’s too heavy a load to place on Wendy’s slender shoulders and our, rather questionable, relationship. But, I calls ’em like I sees ’em. I’m too damn old to do different at this late date.

At any rate, Wendy admitted to me that she’d had sex with her former manager at that record shop. It was really a rather sad story. In a way if it had been to keep her job, some sort of quasi-rape where he used their positions to force her like we hear about in the news, or drugged her or got her drunk, it might not have been quite so sad as what actually happened.

Seems he was the first guy to really pay attention to Wendy. They worked together and eventually got to spending even more time together outside of work. For the first time in her life, Wendy had something like a boyfriend and she liked it. They did the kissing and petting like what I’d done, but she stopped him from going further because back then everybody knew that good girls didn’t do that.

And he seemed to accept the “nothing below the belt” unspoken policy for awhile.

Then he seemed to start drifting away. Nothing big at first. Just spending a little more time with customers wearing low cut tops or high cut skirts. But, then he started being too tired for company after they closed.

I don’t know if “panic” would fit. But, Wendy felt something about losing him strong enough that she decided to go ahead and just do it if she ever had another chance.

And the next time they got together at his place to listen to music and got to kissing and petting, she went further.

And did not enjoy it at all. I don’t know the details. She didn’t offer them and I didn’t think it appropriate to ask. But, at least it seemed to work. For a little while. They stayed together and had sex a few more times.

Wendy broke it off, going so far to quit her job and come to work at Sam’s, after one night when he commented that he would never marry a woman who’d slept around.

I knew what he meant, or thought I did. And I didn’t think it was meant to include Wendy sleeping with him and only him. But, that was how she took it and so she ended it before he could.

Dumb asses all of us. Him for popping off at the mouth without thinking it through first. Her for misunderstanding and not giving him a chance to pull his foot out. Me for, for whatever reason, not heeding the warnings and strolling away, slowly so as not to draw attention.

Bigger dumb ass me, I didn’t have the first idea that the female of the species could actually get horny.

Sure, sure. It’s funny now, how naïve I was. But, I seriously didn’t know. In my indoctrinated world view, women gave sex to get love and men gave love to get sex. Men got horny and women put up with it for relationships and kids and whatever.

I damn sure never figured that women, some women anyway, could get horny enough that it ached.

After so long, I’ve learned enough to know that thinking of women as a collective is just as big a mistake as thinking of men as a collective. Both genders can run the gamut from never feeling the slightest sexual drive at all to it being only slightly less important than breathing but more important than food.

Wendy was the first I’d met that experienced an ache, a deep abiding ache she hadn’t felt before she’d had sex, although I didn’t have the slightest clue.

We’d been going out for a couple of months, maybe three, and hadn’t done more than hold hands, kiss, and a little light petting (and very little of the last), when we reached that fateful evening in late October.

We’d grabbed some McDonalds, the only compromise we could find, and after eating had gone to a park she liked to take me to when she wanted to talk about something she wanted privacy to discuss.

We hadn’t worked that day and I had driven in, fresh from a shower, to spend time with her. I doubt things would have fallen out as they did if we’d been sweaty and stinky from a long day at work.

We’d left my car at her parent’s house as we usually did. In her words, “if you burn your gas driving for a half-hour each way to spend time with me, we can burn my gas in town”. Again, I don’t think things would have worked out as they did if I’d had a steering wheel protecting my lap.

Most of it, I remember as if it were earlier this evening. Parts I guess just didn’t make a lasting impression.

I sort of remember her shutting off the engine and looking out the windshield at the playa lake in the middle before turning to look at me, although that may be a composite of the many, many times she took me there before that night to talk about something “important” in relative privacy.

I don’t remember what it was she said, although I know we were there for several minutes with me listening and trying to pretend to care.

Then, Wendy leaned over and kissed me.

I know I said we’d kissed before that, and we had. But, it was really more of a junior high or high school kind of “adults might see us” kiss. Somewhat longer and gentler than quick perfunctory pecks, but not quite up to playing on the big screen in Hollywood.

The kiss Wendy laid on me reached down through my throat and pulled out my soul with her tongue.

Time out.

I should probably explain here that I’d sort of overheard our favorite uncle teasing my younger sister several years before about kissing. He claimed the couple kissing on the television, the guy was spitting in her mouth. My little sister was maybe eight at the time and of course busted out with “Ewwwww!”

And I wholeheartedly agreed with her. I ran for the bathroom as fast as my twelve year old legs would carry me and threw up a little.

I mean, seriously now. That was just nasty.

As a result, almost all of the kissing I’d done up to that point had been mostly of the “dry” variety. A couple of girls had gotten a little sloppy, but I’d pretty much managed to keep their slobber out of my mouth. And I’d darn sure kept my saliva locked away behind my lips. I mean, it was only polite to do so since I wasn’t really wild about the idea of hocking loogies at each other.

Yeah, yeah. Pretty damn funny. Heap big jock getting grossed out by slobber like some little grade school girl chanting about “cooties”.

But, when Wendy laid that kiss on me, damn. My brain turned off and I forgot all about worrying about such things as saliva being a bodily fluid and thus capable of spreading some diseases albeit not the worst like that new HIV shit they were talking about in high school health classes and the news.

Her soft lips were pressing and sucking and mashing and tugging on mine. Then her strong tongue pressed against my slightly parted lips and I didn’t even think of trying to keep the invader out, but flicked my own tongue out to fence with hers.

Suddenly, she paused and pulled away.

“God, Kevin.” She panted. “You have no idea how long I’ve wanted to do this. Or how much.”

I knew there was a reason we hadn’t, but I couldn’t think what it was in my dazed lip drunk state. Nor was I given a chance to track down the thought as she leaned into me again.

It couldn’t, could not possibly, have been comfortable for her. The steering wheel was pressing against her on the left, the seat she was twisted in didn’t give her much room to pull away from it on the right. And she drove a Volkswagen Rabbit with a manual gear shift she was leaning across to reach me where I was sitting comfortably, not even turned, in the passenger seat.

Maybe that’s why she paused again long enough pop the steering column up and slide her seat back and then clamber over the hump to straddle me in the passenger seat where her hand found the handle on the side to cause my seat to fall back.


“Shh.” She said. “Please. Just let me kiss you, Kevin. Really kiss you. It feels so good to finally just do it.”

Having her straddling me and the words she said, particularly the final sentence, sent alarm bells jangling, but they were muted as her lips found mine once more.

Almost of their own accord, my arms wrapped around Wendy as she leaned into me, our lips and tongues dancing like flames. There was no way she could put her arms, slender as they were, between my back and the seat, and her hands clutched at my shoulders instead.

Stopping her never entered my mind. I could have blissfully sat there and basked in my first “real” kiss as it stoked the fires of passion between us with absolutely no complaint.

Wendy’s hands slid from my shoulders to my pecs.

That was new.

My previous “girlfriends” had either kept their arms around my neck or their hands on my shoulders when we exchanged much more chaste kisses. No one had ever touched my chest before and it sent a totally unexpected thrill shivering through me. Who knew that guys could enjoy getting their chest felt up too? Not me!

Wendy’s lips left mine and drifted across my cheek and over my jaw to my neck. I was so distracted by this incredible new sensation I didn’t notice her fingers working the buttons of my shirt until it was open to my belt and her cool hands slipped beneath it.

I was a little startled and figured she would pull away.

Time out.

I know I mentioned earlier that I am hirsute. But, I think I should probably flesh out just how that affected me.

In the seventies, it wasn’t unusual to see guys with their shirts unbuttoned to the waist displaying a hairy chest behind gold chains. Hollywood showed us a bunch of guys like that. Tom Selleck comes to mind. Or Ron Jeremy. I had more hair than them when I was fourteen. About the only guy I saw that came close by the time I was eighteen was Robin Williams.

You could still see skin through it. I wasn’t like dog furry or anything. But, it was pretty thick.

And apparently gross.

From the time I was eleven and it started sprouting until I was fourteen, I absolutely loved chasing my little sister around without a shirt on trying to give her a hug.

But, think it through. My sister was grossed out. My mother was constantly telling me to put a shirt on. The only females who ever saw me shirtless were obviously put off by it. I never saw Dad without a freaking tie knotted right next to his Adam’s apple, much less shirtless.

And billboards and magazine ads in the 80s transitioned away from hairy chested males of the 70s to Calvin Klein smooth chested androgynous male models.

Okay, maybe that’s not completely fair. They weren’t really androgynous, I don’t guess. But, they weren’t layered with slabs of working muscle like me. And if they had any hair other than what was on their heads and faces, you couldn’t prove it to me using those pictures.

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The understanding I drew was that hairy, especially as hairy as I was, was chick repellent.

To have Wendy’s cool fingers threading through my chest hair as she ran her hands over my all but naked pecs and her lips danced across my sensitive neck was beyond a turn on. It was redemptive. I was not so disgusting as I’d been led to believe. At least not to everybody.

Even more so when her lips left my neck and she sat up to let her eyes rove over my bare chest by the halogen street light streaming through the fogged windows as her hands pressed the panels of my shirt yet wider. She didn’t say a word. Not with her mouth anyway. Her eyes told me that she liked what she saw.

Although perhaps she was just so far gone in her own haze she just didn’t mind.

Whatever may have been the reason, to have her looking at me like that flipped another switch in my brain to “off”. So much so that I didn’t so much as blink when she tried yanking my shirt tail out and, when it didn’t come, started fumbling with my belt.

“Please.” She moaned then. “I want it off. I want to see you.”

Assuming she meant the shirt, I untied the, largely decorative, knot off to the side of the buckle of my woven leather belt, unbuckled it, and undid the top button of my Levi 501s to untuck my shirt. Her fingers quickly found the last two buttons of my shirt and undid them.

I sat up, pressing close to her, as her hands went to my shoulders to shove my shirt down my arms. On a whim, I nuzzled her neck and let my lips graze the delicate skin there.

I guess that must feel even better for a girl than it does for a guy because Wendy responded by shoving me back and peeling her cable knit sweater over her head.

“Come here.” She said as it fell behind her.

I wasn’t so sure though. But, not because for the first time I was looking at a girl in nothing but a delicate bra from the waist up, not counting ones with staples on either side of their navels.

“Uh, Wendy?” I glanced around. “Should you be shirtless here? What if someone comes?”

“The windows are fogged.” She all but panted. “We’ll see the headlights and I’ll have plenty of time get behind the wheel and either pull my sweater on or drive away before they get close enough to see through them. Besides, I don’t really seem to care right now. Now, please. Kiss me some more.”

There was a flaw in her logic, but I couldn’t put my finger on it.

Kissing some more sounded good. It sounded real good. Kissing was my new favorite contact sport.

But, when I leaned up and went for her lips, she tilted her head, moving them away. I might have chased after them with all the drive I’d chased down nimble quarterbacks for three and five yard losses, but she offered up her neck to my mouth instead as her own teeth found my earlobe. Her nails raked my back, drawing upwards against the lay of the hair there, easing an itch I’d never known I had.

God, that felt amazing!

And I don’t think it’s just because I’m particularly hairy either. Over the years, I’ve used that particular trick on no few women, not one of which had a hairy back. And they all rather enjoyed the attention of a good back scratch once I learned to control my strength.

I don’t know if Wendy would have enjoyed having her back scratched or not as it didn’t dawn on me to try. My thick fingered hands roaming over her skin was welcome though, I dare say.

As was my lips and tongue kissing and pressing the delicate skin down her neck, across her collar bone and to the mound of her modest bra encased breast.

The bra in question was a delicate thing. Wendy wasn’t full breasted enough to need much support and I think it was more for modesty than any actual need. The thin strap on her right shoulder easily slipped down her arm ahead of my questing mouth. The thin material of the cup bent easily ahead of my chin.

I’d stopped caring if she was kissing me back or not, which was just as well since she had her head thrown back, her forehead pressed against the roof of the car, her hands alternately caressing and raking my broad back.

“Feels good.” Wendy whispered. “Feels really, really good. Wait. Lean back.”

Puzzled and afraid I’d done too much since the bent cup exposed the top arc of the areola, and feeling a twinge of guilt that I’d gone so much further than I’d ever dreamed I would allow myself short of my honeymoon bed, I leaned back and took my arms away, fully expecting her to climb off and reach for her sweater somewhere in the floorboard behind her.

I was wrong.

Wendy didn’t reach behind her. Not for her sweater, nor to unlatch her bra. She didn’t have to for the latter since it was held with a plastic clip in the front. A deft twist of her fingers between her modest breasts and she was even more exposed above the waist than I was with my shirt waded somewhere behind my ass.

Her arms swung behind her for a brief moment, letting the thin straps slide down her arms to join her sweater between my feet in the floorboard.

“Now.” She said with that familiar sardonic lift on the left side of her mouth. “Where were we?”

I couldn’t have answered, staring at my first real life nipple tipped scoops of flesh, which was just as well since I wasn’t given a chance.

Wendy half fell, half leaned over me, pressing her bared breasts in my face. I didn’t mind at all. Kissing nude breasts was my new all time favorite contact sport. And I went at it with much more enthusiasm than skill.

“Ow!” Wendy said. “Not so rough. They’re attached and really sensitive. Gently, please. Gently!”

I paused mauling her tits with my right hand completely covering the scoop of flesh on her left and about half of her right in my mouth. I don’t mean the nipple. I mean I’d started at the nipple, worked my way past the puffy areola, and sucked half her right tit inside my mouth and had been working on seeing if I could get the rest in there.

“Sorry.” I said once my mouth was clear of breast meat. “Got a little excited.”

“It’s okay.” Wendy said. “I like that I can excite you like this. But,… Well, don’t forget you are incredibly strong. You could easily hurt me by accident. Maybe badly.”

Chastened, I caressed her with my hands and admired her nude flesh from every angle I could manage pressed back in the passenger seat with her kneeling above me.

“I didn’t mean you had to stop with your mouth.” Wendy panted. “Just, more like what you were doing before I took my bra off. Kiss them. Lick them. Tease me like you were.”

I wasn’t quite sure what to make of that last since I hadn’t been teasing. But, I figured she wanted me to be more gentle and I could manage that. I could be so gentle she thought a butterfly was flapping it’s wings against her skin. And I set out to prove it.

“Yes.” Wendy hissed. “Just like that.”

She wasn’t cooperating with my attempts to caress her with nothing more than the heat wave in the air over my skin of my right hand or my tongue around her left nipple and leaned more firmly into my touch, pressing her nipple against my lips.

I discovered goose bumps on her skin and wondered if she was getting cold. It was late October and brisk enough she’d chosen to wear a thick sweater after all. Although her knee length Navy surplus pea coat had been left folded in the back seat.

“Do we need to stop?” I managed to get out as she shifted to replace nipples brushing my lips.

“No. Please.” Wendy groaned but pulled away far enough to look down at me. “Do you want to?”

I knew I should, but I didn’t. I really, really didn’t want to stop.

“No.” I said. “I don’t want to.”

“I’m so glad you said that.” Wendy smirked and leaned in to plant her mouth on mine.

I was wrong. Or rather I was right the first time. Kissing was actually my favorite contact sport. Kissing with bared breasts pressing and rubbing against my bared chest, that is.

Wendy’s hands couldn’t reach my back. At first, she cupped my face as I rested my hands on the bare flesh of her back between her prominent shoulder blades and just above the waist of her jeans. Then her fingers fell away to caress my shoulders and down my biceps, squeezing and kneading.

My hands were forced lower on her back as her caresses of me pressed them down. With my attention wholly focused on the dual sensations of her lips against mine and her taut nipples burrowing through my hair on my chest to touch skin, I didn’t notice at first that I had been shifted down to touch the beginning curve of her full ass. Once I did, I decided if she didn’t mind, I didn’t. It wasn’t as if I was grabbing or cupping the bottom of it after all.

“You feel even better than I thought you would.” Wendy broke off kissing me to whisper into my mouth.

“Yes.” I said. “Yes I do. I never dreamed anyone could make me feel this good.”

Wendy chuckled with her lips pressed against mine once more and her hands drifted to touch my pecs. I didn’t mind at first because not only did having my chest felt up feel really good, but the motions were pressing her breasts, mounding them and pressing her nipples, dragging them inwards.

Then her hands squeezed between her nipples and my flesh and I missed my new favorite things in the world for about a second until her fingers found my nipples.

Holy God and sweet suffering Christ!

I’d always thought nipples on guys were just sort of ridiculous. I mean, God is perfect and he has a reason for his designs. Or so I was taught. But, I also suspected him of having a sense of humor considering the duckbilled platypus and male nipples. I mean what possible purpose could be served by those little skin tags? I never, ever would have thought touching them might feel so damn good!

“I take it you like that?” Wendy grinned.

“Unh huh.” I managed, swimming in the sensation overload. “Maybe too much.”

I’d been dimly aware of my cock lengthening down the leg of my jeans, trapped between our bodies, and tried to ignore it. In my indoctrination, that was what you were supposed to do when that happened and you couldn’t escape. Like, for instance, in class.

But, when my nipples were tweaked, a zing sang through my body on a direct route to my crotch and my cock tried to finish the salute. Which was more than a little painful the way it was folded and pinned.

“Sorry.” I winced, pushing my hand between our bodies and try to adjust myself.

“Let me.” Wendy said, clambering back into the driver’s seat on her knees and reaching for the remaining buttons on my 501s.

As the buttons parted, my cock sprang to it’s full upright position. The relief was so great, I didn’t think about the fact that only my cotton briefs were keeping me from being indecent.

Until her cool fingers slipped inside the elastic waistband to pull my dick into the October night air.

“Is that better?” Wendy asked.

“Uh.” I said brilliantly.

I knew there was something I was forgetting, some reason that I shouldn’t allow her to touch that part of my body, much less expose it. But, it felt so good with her cool fingers wrapped around my hot skin.

Sex stories:   My Step by Step Transformation

“It’s so big,” she breathed as she leaned closer, her fingers stroking my shaft.

Time out.

Oh, shut up. I told you I played football and we get three. And I’m taking my final one to set up the two minute drill.

I knew I wasn’t “big”. I didn’t just think it, I knew it.

First, I’d been in locker rooms with other guys my age. Granted, at the time I didn’t know diddly about “grower” versus “shower”. But, I knew a lot of the other guys… well, they dangled. I didn’t. When I wasn’t erect, I looked like a turtle peeking out of tall grass to see if the pond was safe.

And since I didn’t know about the grow/show dichotomy, I assumed the rest of those guys expanded comparatively just like I did. If they had, one or two could have lined up three cheerleaders and reached the third.

Then, also, I’d gotten my hands on some stories that made it abundantly clear that nine inches was the absolute minimum acceptable length. And yeah, I measured and got depressed as hell when I came up an inch and a half short.

Since then, I’ve learned more, enough to know I’m actually a bit over the average. But, at the time Wendy said it, I “knew” what she said wasn’t true. Which just made the fact that she said it as her fingers squeezed my hardness impact me even more.

“Big and hard too.” Wendy said.

“We, uh, we shouldn’t… shouldn’t…” I stammered.

“Shouldn’t what, Kevin?” Wendy asked. “Doesn’t it feel good for me to touch your hot, hard, big cock? For me to wrap my small hands around it?”

“I…” I moaned. “Yes, it does. But, we should… Oh.”

My eyes fluttered shut and I forgot all about what we should or shouldn’t be doing as her hand began to slide up and down my shaft.

I’d taken up masturbation, but for me it was a nightly chore so I didn’t make a mess in my sheets. Brush the teeth. Take a piss. Dump some cum. Night night. I didn’t really enjoy it all that much and often took a half hour or more just to finish.

The feel of Wendy doing it for me while I knew she was doing it was so very much better than my own calloused hands abrading the skin there while I tried not to allow myself to think of anyone I actually knew.

As good as her hand felt, the next sensation very nearly took the top of my head off.

My eyes shot open to see the back of her head as she’d bent double until her mouth could touch my madly pulsating cock. Later, I learned enough to know she was touching the head with her lips in soft kisses and reaching out with her tongue to lick the ridge of the mushrooming helmet. All I knew at the time was something even softer than her hands, something wet and not so cold had gotten involved.

And I had a new favorite contact sport!

Then her lips closed tightly and she began to draw me inside her mouth. She didn’t take very much, maybe half my length, as her hand trapped my thick bushy pubic hair.

Wendy wasn’t actually very good at fellatio, but I had no way of knowing that, nothing to compare it to, and I was certain I’d died without knowing it and gone to my reward in heaven. The only reason I didn’t immediately coat her tonsils with cum was some last shred, a miniscule vestige of the thought we shouldn’t, that I shouldn’t, be doing what we were.

After only three hesitant bobs of her head, I caught that silly topknot and pulled her up.

“It hurts.” Wendy hissed, her face in a grimace.

Thinking she meant my hand in her hair, I quickly let go. But, her expression didn’t change.

“It aches so bad.” Wendy said. “It feels like three months of cramps rolled into one.”

I didn’t know what she meant. And I hadn’t had a clue the hand she wasn’t using to hold the forest undergrowth back from my trunk had been so busy with something else. Wendy had loosed the laces on her left boot and slipped it off while I was enthralled and couldn’t notice.

At least I guess that is what must have happened since she unfastened her pants and somehow slipped the left leg completely off even as she clambered back over the gear shift to straddle me with just a sock on her left foot and her pants only on her right leg.

“Wait.” I managed to choke out. “Stop.”

It wasn’t supposed to be like this. Not only were we not in our nuptial bed, we weren’t in a bed at all but fumbling in a car. Not only were we not married, but I wasn’t so sure we even liked each other. We had absolutely nothing in common. If what I had been taught was right, this was so wrong on so many levels I wasn’t sure where to even begin counting.

My body was so far gone right and wrong just didn’t matter to it. I was hanging by a thread between what my body wanted and what my mind had been taught was wrong to want.

Wendy snipped that thread.

“Please.” A tear rolled down her cheek, catching the light from the street lamp coming through windows so fogged I couldn’t see out them. “Please. It hurts so bad. Help me.”

“What hurts?”

“Here.” Wendy took my hand and pressed it against her somewhere between her navel and her own thick curly bush. “Deep inside where I can’t reach. But, you can. You can make it not hurt so bad.”

Whatever reservations I had melted. Along with everything else, I’d had hammered into my thick skull that I was given what I had been so I could help people when they needed it. Wendy’s plea for help was exactly the right tactic to flank my rapidly crumbling walls.

I didn’t say it was okay. I didn’t tell her to go ahead. I just withdrew my hand from between us and stopped trying to stop her. She decided to take that for assent.

Wendy’s nether lips were so swollen and I was so hard, neither of us had to guide. I felt something slick and hot press against my tip and then part to engulf me. A tight sleeve slipped over my shaft and down, down, down.

“Ah.” Wendy sighed when I was almost fully ensconced. “That helps. It’s helping. A little. It’s not quite so bad, now.”

The warm moist sleeve sheathing my shaft felt incredible. The pinch of my underwear and jeans on my scrotum just behind my balls, not so much. My eyes were opened to just how tempting actual sex could be, but I wished like hell if we were going to do this I could get my pants lower.

Then, Wendy began to move.

If she’d bounced up and down, sliding that slippery molten heat along my length, I wouldn’t have lasted more than maybe two or three trips. But, she didn’t. Instead, her hips worked back and forth pulling my cock away from my belly and causing me more discomfort on top of the pinch behind my balls.

But, the little shifts her motion allowed, letting me slide just a tiny amount inside her was enough I would have let her break my dick right off.

On one last hard thrust of her hips I thought she had. Pain shot through me, overwhelming my enjoyment, and I felt wetness coating me down where I couldn’t see.

“Aaargh!” Wendy groaned to the car roof. “Yes. Oh, that’s better. So much better. Thank you, Kevin. You have no idea how much I needed that.”

Wendy slipped off me, back into the driver’s seat. She pulled her pants back up her left leg while I was still checking to make sure the wetness I felt coating my still erect cock wasn’t blood.

“Could I have my clothes, please?” Wendy asked, her cheek pressed against the steering wheel as she laced her boot back up.

“Uh, yeah.” I tucked myself back in, still hard, and leaned forward to retrieve her bra and sweater from between my feet. “Here.”

“Thanks.” Wendy said and set about slipping her bra back on and pulling her sweater over her head while I wrestled my shirt back over my shoulders and buttoned back up.

“Seriously, Kevin.” Wendy leaned across and turned me to face her. “Thank you. I can’t tell you how much you helped me. How much better I feel.”

Then she gave me a gentle kiss.

“I’m glad I could help.” I said. “So, uh, what else did you want to do? Dancing, I guess? I think that’s about all that’s still open.”

“Actually, I have an early class.” Wendy said, cranking the ignition. “I should probably take you back to your car and think about getting some sleep.”

“Oh.” I said. “Why didn’t you tell me?”

“Because I wanted to see you, silly.” Wendy laughed, swinging out onto the street. “I wanted to spend some time with my boyfriend. Didn’t you like what we did, too?”

“Well, yeah.” I said. “Of course.”

I did and I didn’t. It had felt better than anything else I’d ever experienced, but I also felt like I’d taken a helmet to my balls. I was still wanting more, but I felt guilty for what we’d done.

“I am really, really lucky to have found a guy like you.” Wendy said, lacing her fingers with mine.

We kissed goodbye on her parent’s porch, a much more chaste version for the evening if not so perfunctory as what had come before that night. Then I drove away.

During the thirty minute drive home, all I could think about was what we’d done. I’d been taught it was wrong, but parts of it had felt so right. There had been some that was so good I couldn’t believe that much pleasure existed on this plane. And other parts that were such discomfort that I couldn’t believe any children were ever born.

Worst of all, may God forgive me, I was still so incredibly worked up it felt like the skin of my cock was going to split.

Safely home, I laid in bed awake until Mom and my sister were safely asleep, just replaying the evening in my mind.

Well, I guess I could go on. I guess I could tell about how I masturbated using lubricant for the first time that night, and used seven different kinds trying to find the right one, jacking myself to seven climaxes until I finally fell asleep about an hour before dawn with empty aching balls, a sore shaft, and a newfound fascination with sex.

But, then I’d have to go on and tell some more about Wendy and how she turned me into a satyr over the next two years before dumping me when I bought a ring and offered it to her. We had a lot of firsts over those two years, just about everything two people, one male and one female could do to or with each other. First time I licked pussy. First time for anal.

But, if I did that, it wouldn’t be about my first time having sex. And that was what started all this mess in the first place. People saying they wanted to hear true stories of people’s first times.

Well, there ya go. It wasn’t pretty. In fact it was downright awkward. But, that’s about as close as what happened as I can recollect these decades later.

Maybe I’ll share some of the other sexual shenanigans I got drug into over the years, with Wendy and others, sometime if I feel like it. But, I’m done for now.

And if it wasn’t what you wanted from a first time, then I’m sorry. Give me your hands and let’s part as friends while you go back and look for some people that are actually good lookin’ and studied the Kama Sutra before they ever saw anybody other than the mirror naked.

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