Herman: Tomboys Grow Up

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[This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies and perhaps some female fantasies as well. It is a fantasy and as such, the story may or may not conform entirely with reality. But isn’t that the whole point of fantasies? With historical exceptions, all other locations, events, and characters are entirely fictitious and any resemblance to actual persons, living or dead, is purely coincidental.]

I do not practice nor do I condone any of the sexual acts about which I write, other than straight, heterosexual relationships. Beside the fact that most other forms of sexual behavior are illegal, I still don’t judge consenting adults for their sexual preferences except where such behavior is hurtful/harmful to others, such as pedophilia.

None-the-less, many people have FANTASIES of such taboo laden behavior to achieve sexual gratification or whatever, but have no intentions whatsoever of carrying out such behavior in actual practice. That said, if I have struck a particular fantasy of yours, read and enjoy.



Roxie Creegan………………….19–Girl next door, bosom buddy of H.R.

Herman R. Saxon………………18–Next door neighbor and bosom buddy of Roxie


I remember that spring fifteen years ago like it was yesterday. Spring came early that year. Warm, short sleeve weather came in mid-March and never really left. My eighteenth birthday occurred back on February fifteenth, I was in the last half of my senior year at Cherry High School, I would be leadoff batter for the baseball team for the second year in a row, and I was the high school yearbook photographer.

Girls liked me well enough but I dated infrequently since my sophomore year. I didn’t have a really significant other, at least not in a romantic sense. There was a girl, but I thought of her more as a boy. She was also eighteen and a senior at Cherry High School.

Roxie was a tomboy. She lived in a house across our driveway and hers or about thirty feet. We grew up together since before the first grade. She was a year older than I, but in the same grade with me due to her late in the year birthday. None-the-less, she always willingly followed my lead.

Neither of us had any siblings. Roxie liked all boy things and activities and got sorely vexed at anyone who hinted that she might be a girl. We were inseparable from preschool all the way through the end of our sophomore year in high school. That was possible because she was a really late bloomer.

The dear girl didn’t develop all the female attributes that normally begin at puberty until our junior year. Oh, she got her first period about the usual time, but that was about all, puberty just seemed to come to a standstill for her. I know because there wasn’t anything we couldn’t discuss and sex was one of our frequent topics. She was very happy with her slow development and our relationship.

Not only could we discuss sex or anything else, but we were free and open with our bodies. We’d go skinny dipping together with no false modesty or feelings of shame about our bodies. We explored each other’s bodies frankly but were never intimate. Roxie was just my best buddy. With any other girl, my hormones would have been out of control. But that wasn’t the case with Roxie and I never new why.

All that would change starting about July or August before and through all our junior year when she suddenly, to my thinking anyway, became a woman–a very gorgeous and extremely sexy woman at that. She acquired a hefty rack, the hourglass figure, the tight bubble butt–all of it.Seemingly overnight, or almost, she transformed and we drifted apart, slowly at first, but then faster and faster. Roxie was all wrapped up in her new role and I, Herman R. Saxon, better known to my friends as H.R., well I sorta faded into the background. The male of the species suddenly flocked to her like bees to honey and she had more guys trying to date her than she could keep track of. Once she started dating, she was well and truly hooked.

I was just too shy to press my case for her in the face of all that competition. Besides, I didn’t think she’d think much of me anymore with her new social standing. All I could do was despair and admire her from afar. What had happened to my Roxie? What had happened to US?

As I said in the beginning, it was spring, mid April to be exact, and senior prom was just three weeks away. Back at the time of our junior prom, Roxie and I had already drifted apart. She went with someone else and I went stag. I had a miserable time and went home well before the dance ended. No after prom for me.

For my senior prom, I was determined to have a date–even if it had to be only a platonic, one of a kind type of date. Only in my wildest fantasies did I ever think I’d get to take Roxie. It just wasn’t going to happen.

I ran into Roxie, literally, at the end of that school day. She had turned from her locker and stepped in front illegal bahis of me and–BAM, I plowed into her before either of us knew what happened,. She banged back into her locker pretty hard, spilling books all around her.

“Oh God, Roxie, I’m sorry. I didn’t meant to, ah I didn’t see…’

In a sort of daze, she said, “Oh, H.R., where have you been?”

I dropped to my knees to pick up her spilled books. She dropped beside me to help.

“H.R., I just suddenly remembered that I haven’t seen much of you for a while.”

“Yeah, Roxie, for over a year.”

“OH GOD, H.R. It’s not been that long–has it?”

I didn’t reply to that.

“Can I come over to your house, now? I want to talk to you.”

“I’ve got baseball practice right now, Roxie.”

“Oh. Well, can I come over after supper?”

“It’s Friday night, Roxie, don’t you have a date?”

“Yes, I do, but I’ll break it. I want to see you.”

“Ok, come about seven. My folks will be going on their Friday night ‘date.’ I’ll tell them you’re coming over. Since they know you, they’ll be fine with it.”

“Great.! See you at seven, H.R.”

I went on to baseball practice. I was so damned flustered, I couldn’t do anything right throughout the whole time. Coach yelled at me every time I flubbed up after the first two times.

“Jesus Christ, Saxon, can’t you do anything right today?”

“Guess not, coach,” I’d mumble under my breath in reply.

Practice seemed interminably long. I was about done in when coach finally told us to hit the showers. I couldn’t get outta there fast enough. Practice had run from four thirty to almost six. I was in for a late supper, if any. Hopefully, Mom left something for me. That wouldn’t give me much time before Roxie came.

In fact, I was eating heated leftovers when Roxie arrived. My folks had left thirty minutes before that. I almost choked on a mouthful as she came in through the back door and into the kitchen–her usual route of long standing as it was mine when I used to go over to her place.

Roxie was drop dead gorgeous in her halter top, shorts, and sandals sans socks. Her brilliant red hair hung over her shoulders and looked on fire in the sunlight streaming through the window. Her emerald green eyes were ablaze and alert. Her tits and the cleavage she exposed were just unbelievable. Her long legs were tanned and supple. She glowed with health.

“Something go down the wrong hatch, H.R.?”

I took a big gulp of milk as answer to her question and sighed in relief.

“Take a chair, Rox, I’ll be finished in a minute. Got to keep up my strength.

“H.R., it suddenly occurred to me today there at my locker that I’ve been sadly neglecting you. I’ve not been terribly happy this last few months and now I realize why. I’ve just missed you something terrible. It’s just taken me too long to realize that.”

“Missed me? How could you? You’ve had all those guys sniffing around you all year, giving you all the attention you could handle.”

“Yes, but not the kind of attention we gave each other. All they ever wanted was to get into my pants.”

“Did they? Oops, that’s none of my business. That just came out. Sorry.”

“Funny, but I think it is your business, H.R. To answer your question, NO, none of them ever got into my pants. A few came close in some heavy petting, but that was all. I-I’m still a vir-uh, a virgin.”

As I said before, we could always talk to each other about anything, even it seemed, after the space of a year not seeing each other.

“How ’bout you, H.R.?”

“Me? Yeah, I’m still a virgin as well.”

“How come, H.R.?”

“Truthfully? Because I always thought you’d be my first. Why you?”

“Would you believe, I’m still a virgin for the same reason? I always thought you’d be my first too. Maybe that’s why nobody has gotten into my pants yet, subconscious restraint waiting for you.”

“Did you enjoy your dating around?”

I finished eating and cleaning up my mess and Roxie answered my last question on our way into the living room. We sat on the couch together our backs to the arms and our feet intertwined , looking at each other.

“Yes, I did enjoy that. But when you bumped into me today, something clicked in my head to make me realize, no one measured up to you as a companion.”

“So, where does that leave us now, Rox?”

The only thing you and I never did, except for a little doctor/nurse kind of thing a long time ago, was explore mutual sex. I wish we had. Uh, I, uh, I want to now. There, I’ve said it.”

She quit talking and stared directly into my eyes, waiting.

The moment dragged on as we continued to make silent eye contact. The frozen silence continued, neither of us breaking eye contact. A seemingly interminable amount of time passed.

“God, H.R., say something, do something.”

A moment more and a tear ran down her face beside her nose.

I slowly opened by arms in her direction. She fairly leaped across the distance between us and crashed into me in an embrace illegal bahis siteleri that knocked the wind out of me. Then her tears did run freely and dripped onto the back of my neck and shoulder.

“Oh GOD, H.R., I’m so sorry I left you out of my life for over a year.”

“Sh, it’s ok now. I’ve got you.”

My one hand was on her butt cheek and the other rubbed up and down her back in slow, sensuous strokes. Her hands were stroking the back of my neck and down my spine.

Rox was on her knees while I was still sitting with m legs stuck out in front of me. One of her naked knees was between my legs. That knee suddenly moved forward to press against my cock and balls. The knee proceeded to massage up and down my growing erection. Both my hands had dropped to her ass and were finding contentment on those firm cheeks through her shorts.

“Take me to your room, H.R., now please.”

We untangled and as I stood up, I picked her up in my arms. One arm went under her knees, the other went around her back with that hand resting firmly on her tit. No bra under that halter top. The nipple hardened immediately to my touch.

Though puffing some, I made it up the stairs and into my room. I sat Rox down on the bed.

“Oh, God, H.R., make love to me. Mad love. Don’t hold back. I want you so damned bad.

I slowly removed her sandals.

“Stand up, Rox.”

Slowly again, I pulled her shorts down her legs, exposing a tiny black thong. I pushed her to sit again, spread her knees and gazed at the sight before me. My mouth and tongue began at her left knee and slowly worked up her inner thigh to her pubis. I mouthed her mons and then went down her right leg, totally ignoring her pussy lips. Rox was shaking with anticipation.

“H.R., PLEASE, don’t keep me waiting.”

I grabbed a mouthful of black thong. She quivered into a mild climax. With my teeth, I ripped the thong away. She was already wet. Really wet. Pushing her open wider, my mouth went to the crease between her vulva and left leg, kissing and tonguing. Then I went to the other one. There was another mild climax. When I dropped my mouth to her outer pussy lips, there was yet another mild orgasm.

Without warning, I suddenly gave a wide, wet tongue lap from her anus to her clit, going deep as i moved up her dripping slit. I gobbled up her erect clit, gently used my teeth to pull and let it snap back. I engulfed her clit again and laved my tongue on it. Rox burst into one gigantic orgasm that shook her whole frame.

“Oh, oh, oh,” was all I could hear from Roxie.

I stood up and mouthed her nipples through her halter top.

She got rid of the halter in a blink. Then I blinked. My God, her tits were magnificent–not gigantic, not small, just perfect on her frame.

“I love your big aureola and nipples, Rox. God, your tits are just too much.”

My mouth went to the naked flesh of those tits, trying to swallow one whole. I couldn’t, of course. I hummed and slurped in the valley between those beautiful mounds of flesh. Another minor climax for her was my reward.

I started to stand but only got part way up before Roxie grabbed my head and pulled it to hers. Our lips locked in a long, passionate kiss that turned sloppy as our mouths opened and our tongues fought a duel. Her hands dropped to my belt and the next thing I knew, my slacks and boxers were around my ankles.

I felt Roxie grab my cock and stoke furiously. Our kiss broke. She stood, forced me to sit, and then dropped her mouth over my cock to give it a real work out. She was a damned good cock sucker too. I was sure that was one thing she had done before.

“On the bed,” she gasped, “on your back. NOW.”

I complied. Roxie immediately straddled me on her knees and positioned her pussy over my erection. I felt her soft, wet folds envelop my helmet in warm softness. She inched down as her maidenhead met my cock. All motion stopped as she stared into my eyes. A moment or two passed. Without warning, she dropped, hard, until her pubis met mine.

“God Damn that hurt,” she screeched.

“I’m sorry, Rox, but you need to go a bit slow the first time to let the lubrication ease the way.”

“Now you tell me,” she gasped. But she smiled when she said it.

“You’re on top, Rox, you run the show.”

And run it she did. She went into motion, moving slowly at first, but picking up the pace ’til she was really pumping on me, her knees and thighs pistoning her up and down. My hands found her tits and went to work with a vengeance. Her nipples were rock hard. Her eyes and face had a look of wild lust I’d never seen before.

One of my hands dropped to the point of our connection. My thumb rubbed her clit in circles. When she leaned forward a bit to swing her tits back and forth above my head, I shoved a finger into her ass. That tipped the scale for her.

Roxie went off into a wild, shivering orgasm that just kept going. I peaked and sprayed my load into her depths in a bone rattling orgasm of my own. Jesus, the old right hand could never canlı bahis siteleri compete with that kind of action.

“Oh my God, H.R., I wish we’d done this a long time ago–a very long time ago.”

“You aren’t the only one, Rox.”

“Let’s do it again!”

“Fine, but you have to give me some time to recover. A guy just can’t go back to back without some recovery time.”

“Maybe I can help.”

Roxie immediately began to gyrate her hips in circles along with a bit of up and down. Damn, if I didn’t start rising to the occasion. I flipped her over, got her legs on my shoulders and fucked her like there’d be no tomorrow. I got a loud, “Oomph,” out of her each time I hit bottom in her pussy. I paused for just a moment and got an immediate, “More, God damn it, MORE.”

We fucked off and on ’til near midnight. Both of us were getting a bit sore by that time.

“Rox, you’ve got to get dressed and go home. My folks are due back any time now.”

I’m not going home;”


“You heard me, I’m not going home. I intend to spend the night righty here in this bed with you so we can fuck our brains out all night.”

“If you’re not too sore before sunrise. What about my folks? What do we tell them?”

“The truth. Anyway, I’m simply not leaving. Now fuck me again.”

We finally managed to grab a couple of hours of sleep starting just before dawn. I woke to the yells of my mother from the foot of the stairs.

“H.R., get up. It’s ten o’clock and time you got your sorry backside out of bed and got something done around here. Get up, now.”

Roxie heard most of that dialogue.

“Well, H.R. shall we go shower together?”

“Boy, you don’t give up, do you.”

“Believe it, H.R., believe it.”

While the warm water sprayed us and I was soaping Roxie’s tits, she asked, “Have you got a date for the prom, H.R.?”

“Let’s see, I’ve got to decide which three lovelies that threw themselves at me that I want to take. Maybe all three?”

That got me an elbow in the chest, albeit, a gentle one, mostly.

“Quit fucking with me and…”

“Literally? Quit fucking you?”

That got me another elbow, harder that time.

“Just answer the question.”

“No, Rox, I don’t have a date for the prom.”

That got me a passionate kiss and her pussy shoved into my dick.

“Good, then you won’t have any trouble taking me, would you.”

It wasn’t a question. But I had one for her.

“Don’t you already have a date, Rox?”

“As a matter of fact, no, I don’t.”

“Why not? I’d of thought you’d have a date sewed up a long time ago.”

“I kept putting off all the requests. I kept telling them I hadn’t decided who just yet. I didn’t know the real reason until last night.’

“And just what did you find out last night” I grinned.

“As if you didn’t know, dummy. I guess I just really wanted you to take me. So, you still haven’t answered my question. Will you be my date, H.R.?”

“Your wish is my command, Madame. Yes, I’ll escort you to our senior prom, with great delight, I might add.”

That got me another passionate kiss as she took my erection and placed it between her legs, saying, “Fuck me again.”

We’d both just reached a mutual climax when Mother yelled up the stairs again, “Are you two going to take all day getting down here? I’ve got an early lunch about ready.”

With total surprise, Roxie and I looked into each other’s eyes and chorused together, “You two?”

“So that is what she said,” I gasped. How the hell’d she know?”

“H.R., I don’t think we were as quiet as we tried to be with our fucking after your parents got home.”

“Oh, shit. I wonder if she kno…”

“Roxie, kick his butt and get him down here.”

“She knows, H.R.”

As we sheepishly walked into the kitchen, Mother said, “Next time you need to be a bit more quiet, especially if you’re going to leave your door open at all. I looked in on you this morning when I got up to see if you had more than one girl in there with you. You made enough noise to make one think so.”

“Oh,” chorused Roxie and I.

“You’re not mad at me, Mom, at us? About us sleeping together?”

“Not with Roxie. Anyone else and you’d be in deep doo doo boy.”

“Does dad know?”

“No, he doesn’t. He can sleep through anything and I mean anything. He left for the golf course while you two were still asleep.”

“But why aren’t you mad about our behavior, Mom?”

“Oh, don’t get me wrong, I’m not entirely happy with you two. But, I figured it was a forgone conclusion and I don’t think either of you could’ve picked a better partner. I’m only surprised it hadn’t happened a long time ago.”

“So were we, Mrs. Saxon. So were we. As a matter of fact, it was the first time for both of us old virgins.”

That tickled Mother.

“So, may I assume you two have clinched a prom date?”

“Yeah, Mother, you might say that.”

We all giggled at that.

Overnight, Roxie changed. We became an instant couple and no one at school could or did fail to miss that fact. More than one friend told us we looked as if we were walking on clouds as we strolled down the long main hall at school. There were a lot of broken hearts left behind us and none were female hearts.

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