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Confession Of A Tomboy

While the story takes place in the mid-1970s, today, the mentioned Inn in Vermont is still open for business, but sadly the dorm building is no more.

She was hot, the girl of my dreams, and all she was thinking about was using her talented oral skills to please me, to drive me crazy and make me cum. She knows taking me deep into her throat while squeezing my balls will bring me to the edge, to that point of no return.  I’m lost in sensations threatening to overwhelm me.  

Beep, Beep, Beep!

I stretch and hit the alarm off button as I awaken with a morning hard-on. I remember dreaming, something erotic, but I can’t remember much about it. However, my “stiffness meter” indicates it might have been pretty good. Rolling out of bed, I awkwardly pull on my underwear and stumble to the shared bathroom to pee and shower. I’ll be at work in forty minutes prepping to prepare breakfast for sixty-plus overnight guests. 

Even if the pay isn’t great and the early hours suck, at twenty-two, I’m lucky to have this job as number three line chef at one of northern Vermont’s premier historic Inns. Twenty-one other people also work at the restaurant, the majority of which are seasonal hires, with over half of those being female.

If we want it, seasonal employees can have a room on the top two floors of an Inn-owned dorm located nearby.  It’s that, or else you must find other accommodations on your own.  While the dorm rooms are small, sparsely furnished, and share a bathroom on each floor, they are free. It wasn’t a hard choice to live in the dorm.

Restaurant work can be hard with long hours, and most of us are also living in close quarters of the dorm, so friendships develop quickly in this intimate environment.  And sex, either as a topic for discussion or as an activity, is never far from anyone’s mind.

On that matter, my interests have focused on two female coworkers. There’s a connection with one girl, but I’m also confused by her, and the other girl, if I’m honest, is certainly more about my state of perpetual horniness than any romantic interest.

For a while, I’ve chatted up Linda, a blondish twenty-year-old. She’s friendly, talkative, and has a quick smile. Her looks and body make her a cheerleader fantasy for most guys. We’ve spent a considerable amount of time together talking but, it’s become clear she’s still in love with an on-and-off-again ex-boyfriend that is at the moment off again. It is also evident all other guys are in her friends-only group until she finds closure.

One evening, when I’m fed up hearing all about Mr. X, I tell her he is a stupid fuck, and she’s a fool if she doesn’t recognize that. 

We’ve hardly spoken since I made that keen observation known to her.  Honesty sometimes has a price.

The other girl, the confusing one, is Cindy. She’s twenty-one, has short dark hair, green eyes, flawless skin, and on occasion, a wonderful smile. Sadly, she seldom seems to smile. She stands five feet four inches tall with a lean, athletic body, narrow hips, flat waist and petite breast. But, In a thin cotton t-shirt on a cold day, her nipples are pretty damn outstanding!  Yes, I’ve noticed!  

Cindy is not shy in speaking her mind but is somewhat in your face, even angry at times for no apparent reason. That’s what confuses me. I don’t know why or who she’s mad at, and if asked, she replies, “It’s nothing!”

I’m attracted to Cindy, but I’m uncertain of what to make of her personality’s edgy and angry side. So, I’ve remained a little cool and distant when we talk or are together.  

But I have to admit I find her adorable, and I always notice her when she’s around.

One evening, after a hard workday, we “dorm rats” are hanging out on the stairway, doing our best to kill a case of cold beer. There’s music playing, pizza to share and lots of talking and laughter. At times some are dancing to their favorite tunes on the landing. It’s a relaxing evening for everyone.

Before the event winds down, I noticed Cindy on the landing swaying to the music and starting to dance. Surprisingly, she begins a slow expressive modern free dance, beautifully performed with flowing, hypnotic moves. 

I can’t look away as Cindy’s lithe body contorts to the musical rhythm. Her motion expresses the mood of the music perfectly as her bare feet float across the floor. There’s a small smile as she pauses for a moment to gather and tie her loose shirt under her small breasts, exposing a flat and toned mid-drift. A small white gold ring is in her pierced belly button above tight light-weight dark grey leggings riding low on narrow hips. She again dances as my eyes follow her every move, and I memorize every detail. 

I’ve not seen this side of Cindy before, and I find myself reevaluating every previous thought I’ve had of her.

The music fades to silence, and I manage to turn away long enough to wish good-night to the last of our group retiring to their rooms. As they depart, I see in their eyes and knowing smiles they understand and approve of whatever is happening between Cindy and me.

Cindy moves to a spot just in front of where I’m seated on the bottom steps as the music begins again. It is just the two of us now. Cindy gracefully sways to the music, then pivots with her back to me as she slowly begins to bend at the waist. Her hands move to her ankles, stretching her leggings tightly across her firm ass. While continuing to sway slightly, she slowly brings both hands up the insides of her thighs before meeting to caress between her legs.

Only inches from my face, the thin legging material leaves little to my imagination. There’s no trace of underwear beneath, and I catch an enticing scent of sexual arousal from a noticeable small damp spot where her hands are playing. I take a deep intoxicating breath as my cock begins to harden.

Hearing Cindy’s giggle, I flush as I realize she has me exactly where she wants me, totally flustered and aroused. She stands slowly and turns, facing me, inching forward until only the thin material of her leggings separates her mound from my face. Directing my eyes upwards to look into her own, she whispers, “Can we go somewhere more private?”

I am beyond my earlier uncertainties and reservations about Cindy. Hell, I’m beyond caring or even thinking clearly as I rearranged my hard cock and stand, taking her hand.

Our desires spill over into deep passionate kisses as my room door closes behind us.  We cling to each other momentarily until Cindy, with some effort, breaks our kiss and pushes me to a sitting position on the edge of my bed.

“Now, where were we,” she grins while unbuttoning and dropping her shirt, revealing petite breasts with lovely pointed nipples as she turns her back to me. With her feet slightly apart, she again doubles over but doesn’t reach for her ankles this time. Instead, she hooks her thumbs in the waist of her leggings and slips them down, ever so slowly, revealing a lovely ass and bare pouting pussy.  

“You’re quite the tease aren’t you?” I ask while trying to keep my voice steady as my heartbeat pounds in my head.

“Not often, but you can take it beyond being just a tease anytime you want,” Cindy responds nervously.

Taking that as permission, I swiftly help finish removing her leggings and gently run my hands up the outside of silky legs to caress and knead beautiful smooth ass checks.

“So lovely,” I whisper to myself while leaning forward until my lips and tongue gently kiss her exposed glistening pussy.  I hear a slight gasp and the release of a held breath from Cindy as the sweet nectar gathered by my tongue inflames my needful lust to continue exploring the wet secrets of her delightful sex. 

“Now who’s teasing?” Cindy moans as she shifts her weight ever so slightly from side to side.

“Not teasing, I fully intend to follow through. But I’m taking my time to relish you,” I respond.

I use my hands to gently expose Cindy’s anal rosebud as my tongue traces a wet path from her pussy to lick and probe said rosebud.

A deeper moan escapes Cindy’s throat as she pushes back to intensify the probing sensations. I ease a finger into the smooth tunnel of her wet pussy and begin a slow fucking motion, softly rubbing across her clit with my thumb on each stroke. I match the intensity of my efforts to her body’s corresponding responses.

“Yes, I’m almost there. My legs feel weak, but don’t you dare stop,” Cindy’s near breathless voice exclaims.

Sliding silently off the edge of the bed, I brace myself in a kneeling position behind Cindy, wrapping a supporting arm loosely around the top of her thighs.

A moment later, I feel Cindy’s knees go soft as her body tenses. “Ohhhh fuccckkk yessssssssss. I’m cumming!” She loudly gasps as a climax overtakes her.

I hug Cindy tightly, and as I feel her weight shifting to me, I lift her across my bed, where she lays upon her stomach, my hand gently stroking her back until her spasms fade.

Cindy raises her head when awareness returns and says in a breaking voice, “I need you to fuck me.”  She then lifts her hips to a kneeling position while arching her back with her face down and ass up, out and over the bed’s edge. 

I quickly stand and strip, my cock springing out unbearably, almost painfully, hard. Inching forward, the head of my cock parts the glistening wet lips of Cindy’s waiting pussy. She clenches as I move my cock sightly up and down just within her lips, randomly brushing against her clit. Reaching back through her legs, Cindy grasps and aligns my cock with her entrance.

“Fuck me now, hard!” she demands.

I wait only seconds before sinking my cock slowly and entirely into her tight hot channel. I feel her pussy resisting and then molding itself around my member ever so tightly, causing me to utter, “Oh, damn, you feel so good.”

Only, “Yessssss,” accompanied by a soft whimper, escapes her lips.

Adjusting to her tight heat, I begin to fuck her in earnest. In and out slowly, then building speed. She tenses at first but soon relaxes as she starts moving in time with me. Driving forward, Cindy pushes firmly back, absorbing our impact before slipping away, eager to repeat.

I felt like an animal in heat, with my mind lost in a zone where fucking her is the only essence of my existence. My arms and hands tightly gripping her hips, my cock pistoning in and out, as the naughty sound, “flap, flap, flap, flap,” of our bodies echo in my ears in time to our steady rhythm.

My balls slap against Cindy’s clit with each hard impact as she mutters muffled sounds, cries, and perhaps partial words. Her hands repeatedly shift between tightly gripping sheets, pinching harden nipples and reaching back to rub herself or touch my balls. In that very moment, we’re both slaves to our pleasure and pain, with little difference between the two.

I feel my release nearing as Cindy’s velvety tightness propels me past a point of no return. In preparation, my pace slows slightly but becomes even more deliberate, desperate, and intense.

Cindy discerns that change as the approaching finale, telling me, “Cum in me!”  We’d briefly spoken earlier about protection and birth control, so there is no hesitation in fulfilling her request.

“Yessss,” I tightly but loudly cry, and with a needful groan and one last desperate stroke, my hot cum erupts deeply within her. My body tenses and jerks repeatedly as my eyes squeeze tightly shut; time seems to stand still while my orgasm jolts me.

In those exact moments, a cry escapes Cindy’s lips as she rides her own orgasmic waves. I feel them rippling through her marvelous pussy, adding to my pleasure.  

Some minutes later, when our climaxes have ceased, my fingertips trail gently down Cindy’s lower back as I slowly extract my softening cock from her. Thick rivulets of translucent cum follow and begin trickling down her inner thighs as she shivers from the sensations.   

Cindy collapses forward across the bed, and I carefully move to lay beside and along her back. Our skin glistens from our efforts, and there is a pleasing salty taste as I kiss her shoulder, back and neck. Pulling her close, I feel a need to express my awe, “That was incredible. You were incredible.”

“Yes, it was beyond incredible,” she responds, pushing back into me.

We lay for some time, silent and satisfied.  

“I’ve been wanting that to happen since we first met but it is far better than I ever imagined,” Cindy softly says as she turns and rolls into my arms. 

My face betrays some uncertainty as I respond, “But you were often angry and confrontational when we spoke. I didn’t know what that meant or how to handle it and you wouldn’t tell me, so I’ve kept my distance.”

There’s a glimmer of tears in Cindy’s eyes, and I know whatever she is dealing with is painful for her, so I wait.  

Finally, speaking so softly, I strain to hear, she says, “I know I’m not beautiful like some girls, and I don’t have breasts and curves. I don’t dress like them, act like them, or enjoy a lot of girly things. So, often guys treat me like a buddy, not a woman. It can hurt, and sometimes I’m sad and angry at nothing because of it. I guess I act out because I don’t know what else to do.

“I liked you a lot and I didn’t want you to think of me as a buddy, even as one with benefits. But I didn’t know how to keep that from happening. You can’t imagine how difficult it was for me to do what I did on the stairs tonight – to put myself out there hoping you wouldn’t reject me.”

Stunned, it takes a few moments to corral my swirling emotions and thoughts before I can respond. “Cindy, no, you’re not other girls. You’re unique and amazing in your own right. As you should realize now, I don’t think of you as a buddy, I never have, and I never could. I think you’re a beautiful woman, and I feel lucky to be with you. I want us to spend more time together and I hope you feel the same way.”

“Yes, I’d like that,” Cindy says, giving me a soft kiss before continuing, “I know you have work in a few hours so I guess I should go back to my room so you can rest.”

My breath catches as I see her delightful nude body starting to crawl off my bed. Reaching to her, I grab her arm and pull her firmly back to me.

With a kiss and a devilish grin, I say, “Stay with me until we have to get ready. I don’t care if I’m tired at work as long as it’s for a good reason and you’re the best reason I can think of.”


Beep, Beep!

I quickly hit the alarm off button before quietly turning to confirm Cindy’s still asleep. It will be a wonderful day, and I look forward to springing the surprises I’ve arranged for her. I don’t think she’s expecting anything special, but I always enjoy exceeding her expectations, especially since it’s our fortieth wedding anniversary.  It’s hard to believe it’s been almost forty-five wonderful years since we first met in Vermont, and she became the love of my life.  I often think back to that day and still marvel at how lucky I am.

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