The Girl with the Freckles

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He gets his freckled fantasy girl.
4.4k words
4.62
34.5k
57

Part 1 of the 5 part series

Updated 06/08/2023
Created 06/02/2017
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(to Janet, forever unrequited; and Sarah, forever unattainable)

*

I can never explain the how, or why of this, but for as far back as I can remember, I've been captivated by girls inundated with freckles. Not merely a thin scattering across the bridge of the nose, but a dizzying display from head to toe; the more, the better. To this day, when confronted with that singular archetype of my libidinous desire, the physiological response remains unchanged: heart palpitations, shortness of breath, dry mouth, increased perspiration and tingling nerves. Can't talk or think straight; I'm completely overwhelmed.

That's the way it was the first time I saw Janet. There she was, first day in 7th grade home room; a willowy 14 year old girl with a page boy haircut and milky white complexion blanketed with a vast array of beguiling freckles. The sun left it's imprimatur anywhere it touched her; a teeming infinity of tiny flecks echoing the light brown color of her silken hair. I found myself staring at Janet and her freckles every chance I got. She was the prettiest girl I'd ever seen.

But, as a shy, awkward 14 year old with no idea how to act on this overwhelming attraction, I did nothing. My reticence was deepened by fact that Janet was constantly teased about her freckles. Given all my adolescent insecurities, I couldn't endure the peer ridicule that would occur if Janet and I became - well - boyfriend/girlfriend. So I did nothing. We would exchange pleasantries, occasionally superficial conversation, and I would steal glimpses of her at every opportunity; but that was as far as it went.

Then I was accelerated a grade, and advanced one year ahead of Janet. We'd still cross paths in the hallway occasionally, but were no longer in the same classes.

By my senior year in high school, I had begun dating and made the initial forays in sexual exploration with several willing girls. Yet I could never get Janet out of my mind. I fantasized about her heavily freckled naked body, showering it with kisses, sucking on milky white breasts, and making the kind of mad passionate love that elicits cries of ecstasy; but I still did nothing.

After graduating and starting college, I took a part time job stocking shelves at a local supermarket. Janet lived a few blocks away, and worked in the drug store across the street. I'd see her through the store window manning the cash register when I'd walk by on my way to work. Occasionally, we'd make eye contact. I would wave hello, and she would smile back at me. Then one day she stopped by my supermarket and finally, I decided to do something.

"Hey Janet, how's it going? You're graduating this year, are you staying in the city for college?"

"Hi. Yeah, I'm pretty sure I'm going to Hunter. You go to Queens, right? do you like it?"

"It's good; l mean, it would be even better if you went." That brought a smile to her face, so I decided to go for broke.

"So, umm, we should get together one of these days. Give me your number and I'll call you."

"Ok, I'd like that." She took a pen from her bag, as I handed her a discarded register receipt to write on. "Here" she said, as she returned the paper with a smile.

"Great. I'll call you when I get off work, maybe we can set something up for this weekend"

"Tomorrow's Friday, I'm free, I'm up for getting together." She paused, and added somewhat tentatively, "You know, I always kinda liked you"

"Really? I always liked you too. I'll call you as soon as I get home. Promise"

"Great. Talk to you later." As she walked toward the exit, my eyes stayed glued to her. Twice, she glanced over her shoulder and smiled back at me.

Finally, I was going out with my freckled obsession, and my heart was pounding with the realization. Moreover, she freely admitted she liked me; my imagination raced with possibilities.

I practically sprinted home after work and went straight for the phone. As I finished dialing the number, I felt a choking rush of nerves that nearly made me hang up the receiver. But, the line began to ring, so there was no turning back. She answered.

"Hello?"

"Hey Janet, it's me. So, umm, how about tomorrow night? I get off work around 6:30, I'll go home and clean up, we can hook up around 7?"

"Great, what do you feel like doing?"

"Umm, can I buy you dinner? I'd like to take you someplace nice, anywhere you really wanna go?"

"That's so sweet, nothing fancy, how's the Blue Bay Diner? It's close and we can meet there."

"Great, looking forward to it, see you at 7."

"Me too, see you there."

Friday night couldn't come soon enough. All I thought about was getting together with Janet. Would we kiss? Maybe more?

I didn't want to overdress, so I put on my coolest understated jeans and a plain black gap tee shirt, the basic uniform I wore when playing guitar with my band. I arrived at the Diner a few minutes early, and to my delight she was already waiting. She wore skin tight brown Capris that complimented her long legs, and a silky gold short short sleeve open neck blouse. Naturally, I studied her freckles. They were like cascading raindrops, sprinkled over her pretty face and running down to her chest, across her shoulders to the backs of her willowy arms, down to her fingers, even reappearing on her bare calves, and I thought to myself....god, how stunningly beautiful. If I hadn't masturbated before I left home as a precautionary measure, I would have had an instantaneous - and embarrassingly obvious - erection.

She saw me and smiled. I tried to sound charming.

"Hey Janet, you look really nice."

"Thanks, you do too."

As we sat down to eat, I was nervous that I'd flub the conversation, seeing as my thoughts were utterly consumed by the desire to ravage her freckled body. But we chatted comfortably, reminiscing about school and friends, joking about parents, discussing music and life in general. She was so easy to talk to, and shared my sense of humor. By the time we finished our burgers and fries, I found myself genuinely liking - in addition to lusting after her.

"Walk you home, it's a nice night?" I offered.

"Sure, let's go"

I paid the check and we left. As we crossed the street I took her hand. Her fingers intertwined around mine as she looked into my eyes and smiled.

I took a chance: "you're so pretty, I - I really want to kiss you."

She closed her eyes and leaned into me. Our lips met and lingered, and I felt a jolt of electricity surge through my entire body.

When we finally separated, she smiled and said "that was nice"

"Yeah, it was" I replied. I took her in my arms and we kissed again. This time, her lips parted as our tongues twirled in a playful dance. For that instant, it felt as if the world around us melted away, and she and I - connected by a kiss - were all that existed.

We continued walking to her place, hand in hand, comfortable in the silence. When we got to her front door, she turned towards me and I pulled her close. We kissed again; it was intense and lingering. When we separated, she looked up with a hopeful expression on her flushed freckled face.

"Do you want to come in and hang out for a while? My parents are away for the weekend, we'd have the place to ourselves?"

"Sounds like a plan." I replied.

As soon as we entered the hallway, we practically leaped into each other's arms and started necking like the sex crazed teenagers we were. As my kisses trailed down her slender freckled neck, she just managed to gasp "let's go to my bedroom"

Without missing a beat, I swept her off her feet and carried her down the hall until she said "here." She kicked open the door and we tumbled onto her bed, laughing and giggling between kisses. I straddled her heaving body and began to unbutton her blouse.

"Wait!" She pleaded.

"What's wrong?" I asked, surprised by her sudden reticence.

"Can we turn off the lights, I'd feel more comfortable"

"Why, I really want to see you"

She turned away from me.

"It's just.... it's just that I have so many freckles, I'm afraid you'll hate them"

I had to stop myself from laughing at the irony.

"Oh my god! From the first time I saw you in 7th grade, I adored your freckles. Ever since then I've had this huge crush on you, your freckles are my biggest turn on. Please? lights on?"

"Your serious? You actually like my freckles"

"I don't just like them; I LOVE them. They're really beautiful; I think you are really beautiful."

Her eyes began to well up with tears, and she threw her arms around me in a passionate embrace. She sobbed; "no one ever told me I was beautiful before."

I gently stoked her hair.

"I'm an idiot. I should have told you how I felt years ago. Don't be upset, I'm such an idiot."

She lay back down on the bed. The tears subsided, replaced by a smile, and she slowly began unbuttoning her blouse. At the same time, I quickly pulled off my tee shirt and watched as she removed the garment, revealing her bra-clad milky white bust line. She was covered with a galaxy of freckles; densely packed and almost cloud-like on her shoulders and upper arms, gradually thinning out as they approached her pale breasts. I pulled the bra straps off her shoulders, she deftly undid the clasps, and it fell away, revealing luxurious mounds capped with light pink nipples.

"I kinda small," she said with in an apologetic tone. "Hope you're not too disappointed."

My eyes feasted on her beauty.

"You're perfect. So perfect. More beautiful than I ever imagined."

I lowered my mouth to an engorged nipple, grasping it with my lips as I flicked my tongue across the tip, while gently teasing the other nipple, kneading it between my fingers.

"Mmmm, that feels soooo nice," She purred.

My hand trailed across her taut, freckled waist, drifting down to the top button of her capris. I undid the button and and unzipped the fly. I looked up into her eyes. "I want to make you cum."

She nodded her consent.

As she quickly shimmied free of her slacks, I looked hungrily at those shapely freckled legs. Her pink panties were stained with a distinct wet spot, and she gasped, as I ran my hand over her pussy.

"Oh, God that feels good"

Reaching under the elastic band, I navigated the sparse, delicate tangle of pubic hair and caressed her moistened labia; she was ready. My middle and ring finger easily penetrated her opening, as the outer digits anchored my hand in position. One of my band mates taught me this technique, which allows for simultaneous contact and stimulation of the G-spot and clit. I played her pussy like an instrument; increasing the speed and pressure of my thrusting fingers to match the changing rhythms of her respiration and moans of pleasure.

"Oh God, that feels sooo gooood. Oh yes, that's it, right there. Oh God, go faster, pleease don't stop. Oh my GOD, you're gonna make me cuuuumm. Uhhh, uhhh, I'm cumming, I'M CUMMING!!!"

Her hips bucked controllably. My fingers were drenched in a warm flood of vaginal fluid. She orgasmed; once; and again; and then again...

When it was over, her body slumped into the bed, a look of sublime ecstasy etched on that enchantingly freckled face.

After a few moments, she regained her composure.

"That was...that was so..I mean, I don't have a word to describe how amazing that was. I've made myself cum before, but never like that."

"Well after all," I responded rather cavalierly, "a guy should know how to get his girlfriend off, don't ya think?"

A huge smile crossed her freckled face. "So, I'm your girlfriend now?"

"Uh huh"

She glanced at me slyly, and in a mock babydoll voice, said "Well, then I guess a girl should know how to get her boyfriend off, too."

"Seems logical," I replied as she unzipped my jeans. In record time, my pants, sneakers and socks were tossed aside, and she began running her hand over my BVDs, tracing the outline of my swollen member. At the same time, she began licking and sucking my nipples.

"Do you like that?" she asked with a wicked grin.

"God yes" I nodded.

"I don't have much experience, so your gonna have to tell me what feels good, ok?"

"Well, you can start by squeezing your hand around my cock and stroking up and down." I suggested.

"Like this?" She asked innocently, as she pulled down my underwear and followed my instructions to the tee.

"Oh yeah," I moaned.

"Maybe there's something else I can do to please my boyfriend." she offered.

"I think I'd like to suck your cock."

So there I was; a girl I had fantasized about for years, with her naked, hot freckled body hovering over me, volunteering to give me a blow job. For a minute, I thought, am I dreaming?

She began by running her tongue around the head, then slowly up and down the shaft.

"Am I doing ok?"

"Oh my god, Janet, great"

As my erection pulsed with excitement, she engulfed the head and began taking me deep in her warm, wet mouth. Her tongue flicked across the surface of my cock, as she increased the suction from her cheeks. She even covered her teeth with her lips. My girl is a prodigy, I though.

"Baby, if you keep that up I'm gonna cum in your mouth"

She paused momentarily.

"I want you to, if it makes you feel good, I'll swallow my boyfriend's cum."

With that, she quickened her pace, and I felt my orgasm building as I watched that beautiful freckled face rapidly bobbing up and down on my cock.

"Oh my GOD, here it cooomes..."

I exploded in her mouth, shooting jet after jet of hot jism. She swallowed every drop, licking her lips as she withdrew from my spent phallus. I lay there, nearly paralyzed by the waves of pleasure.

"Did I do ok?" she asked with mock innocence.

When I could finally respond, I choked out "not bad, not bad. Of course, there's always room for improvement."

"I'll get better, I promise," she replied. "I'm just gonna need a lot more practice, I hope you won't mind."

I suddenly pulled her down to me, and began raining wild kisses all around her body as she giggled uncontrollably.

"Stop, that tickles!" She protested.

"No way, I'm hunting for hidden freckles, and I won't stop till I've kissed every one."

We wrestled around in bed, laughing, kissing and caressing, when suddenly, the phone rang.

"Oh shit, it's my mom, I forgot to call her. Please don't make a sound, I'll be quick, I promise."

With that, she picked up the phone.

"Hi mom, sorry, I was about to call. C'mon, it's not that late..after 11? I...I lost track of time, I was......watching a movie."

Then I decided, time to play dirty. Without warning, I dropped down between her legs, pinning back her thighs with my arms and began an unrelenting assault on her pussy with my tongue, as she struggled to retain her composure.

"The date? It was gr..great, he's re..really nice." She tried in vain to push my head away from it's succulent target. "We.....ate out...". I winked at her as she soundlessly mouthed the words "please stop!" I did not comply.

"blue bay diner....he wo...wouldn't let me, I off..offered. Yes, you'll get to me..meet him, look mom, can we pick this up tomorrow.? I...I really... have... to.. pee bad!!

Ok, say hi to dad, love you, bye!"

She slammed down the receiver and glared. "That wasn't fair!!!" She protested.

"Want me to stop?"

"Oh god, no I'm so close, yes babeeee, Oh GOD, I'M GONNA CUMMMMM!

Her mouth open in a silent scream of pleasure as I drove her to yet another climax.

When she caught her breath, she looked at me with a cute little pout and whined, "you are sooo evil, you know that? I'm gonna get you back somehow."

Then I realized how late it was getting. "Shit, I really should get home, my parents will freak. But I just don't want this night to end."

"Please don't go. Stay with me, I want to wake up in your arms."

I knew that nothing could make me leave. "Let me make a call"

I picked up the phone and dialed home.

"Hey dad, it's me. Umm, listen, I'm at Steve's house, we're working on some new material." Just then, Janet dropped to her knees, swallowed my cock, and began going down on me.

"I...we...umm, I'm gonna stay over, ummm, we're not finished..umm, yeah, Okay, bye..."

I hung up and she started laughing as my resurrected hard-on dropped from her mouth.

"Damn, you got me back. Hope you're not gonna leave me like this?" I protested.

Suddenly her expression turned serious.

"No. But I...I want you to do something special for me. It would mean so much...everything to me."

"What is it? I'll do anything for you."

"Umm, don't freak out, but...I'm still a virgin. I want you to make love to me. I want you to be my first."

"Janet, I want to be with you more than anything. I'm just scared, I don't want to hurt you, you'll bleed and..I never want to hurt you."

"Don't worry, I promise it won't get bloody. Last year I slipped when I was practicing a routine on the beam. Landed hard right here," as she pointed right at her groin. "I bled like crazy. Gynecologist told me the balance beam ruptured my hymen. So the painful part has been taken care of by some gymnastics apparatus."

"Wow; never thought I'd be jealous of a piece of athletic equipment. I mean, I'm nowhere near as large as a balance beam. But, I promise to be much more gentle; no splinters, either."

We laughed together, as I drew her in for a kiss.

"There is one other thing" she said. "Protection"

"Well" I replied tentatively, "I hope you don't get the wrong idea, but I happen to have a condom in my wallet, not that I was planning anything."

Much to my relief, she replied "Oh thank god! I was ready to break into the drug store where I work and steal a box! I actually have a spare key."

"Glad I kept you from embarking on a life of crime" I said.

"Worth the risk to be with you. I....I just...I want you inside me so much" I sensed she was holding back and wanted to say something else. So did I.

I retrieved my jeans and pulled the wallet out of the back pocket. Tucked in one of the folds I found that little foil packet. I anxiously tugged on the edge, which stubbornly refused to yield. Janet smiled at my frustration and snatched it from my hands. She bit down on a corner, tore it open and pulled out the latex circle.

"How do I put it on?" She asked.

"Just place it over the head of my cock, grab the tip, make a circle with your fingers and kinda unroll it like a sock." I instructed.

She leaned over and positioned the prophylactic.

"Wait, let me get you wet, I think it'll be easier." She engulfed me in her mouth once again, providing her own generous coat of lubrication. I smiled at her resourcefulness.

"Mmmm, your cock tastes yummy " she cooed, as the condom slid on easily. Then she laid on her back next to me, spreading her legs in a seductive invitation.

"I'm ready," she said.

"Let me get you wet, first."

I went down on her, ringing my salivating tongue around the perimeter of her opening, and thrusting it as far inside her as I could. She moaned.

"I could spend hours eating your pussy, it's delicious.. oh my god, it even has freckles! Sooo hot."

"You really do love my freckles, don't you. I've spent most of my life hating them, but now I'm glad I have so many."

"Mmmm, me to. Are you ready?" I asked as I positioned my rock hard manhood over her slick vulva.

"Soooo ready" she replied.

As I pushed the head into her tight opening, it slowly yielded, and I began making short, slow thrusts, each penetrating a little deeper.

"Let me know if I'm hurting you"

"No, no it feels sooo good, keep going"

And then, my shaft was fully sheathed inside her. I felt a flood of her vaginal juices as I continued the rhythmic piston-like motion. My full consciousness was consumed by the sensations of that pole of flesh moving inside her.

"feel good?" She asked.

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