There was a young woman that I met while working my first job, at age 16. We’ll call her 'H'. She was beautiful with long dark hair, brown eyes, glowing white skin. 'H' was 21 years old, 4’11” with cantaloupe sized breasts and a mother’s soft stomach. 'H' had an independent personality and a laugh that was to die for. When she smiled at me it was like standing in the sun on a summer's afternoon, all warmth and comfort. Like the shadows of night could never have existed. 

'H' works the opening shift in the Safeway deli. I work the opening Courtesy Clerk and Bottling boy shift. My tasks were fairly simple and short most days. So I end up with a lot of time to help 'H' with things like reaching the top shelves and heavy lifting.

She and I would laugh and joke around in the confining space behind counters and in the cooler, where other employees wouldn’t see if she brushed against me. After a few days of gentlemanly behavior and 'H'’s dirty humor I start to develop a crush on my deli lady.

It was after about three or four weeks that I notice my break schedule is flexible for my first 15 minute and my lunch. I decide that 'H' and I should magically start our breaks at the same time. This gave us time to sit side by side and really get to know one another.

We found out that we truly had quite a few things in common. We both like action and drama movies, enjoy rock music, and a sexually deviant sense of humor. It took me a few months to recognize that 'H' was actually flirting back with me, and not just being friendly (with women I can’t always tell for sure).

I find my-self gravitating towards her. As if I can hardly stand to put distance between us.

'H' realized this the third time that I accidently brushed against her butt one day.

“Are clumsy today, or just trying to feel my ass?” 'H' asks me.

When I can do little more than blush and stammer, she leans her breasts against my arm, whispering, “Hey we should go see a movie together on our day of this week.”

I do the only thing I can think of, I say, “I’d love to.”

Remember I am only 16 years old. I am working my first job and am on the high swim team. Seeing as how I don’t always recognize when I am being flirted with…… ok, ok, and hit on by a female. It should make perfect sense that I had never asked a girl out before.

Oh, I had been wingman on many a blind date to double with my friends (both of them) but not alone. I never even dated anyone older than me. My strategy with women was more of a sit/stand looking mysterious, handsome and only talking when spoken to.

They make the moves, not me. They asked me to the dances, not me asking them. If they wanted to make out, great, but they had to start kissing me first.

The most I have ever done sexually with a girl or woman in my life was French kiss and fondle while fully clothed. How I ended up with girlfriends and dates was truly beyond my understanding. So it comes as little surprise when I say that I felt out of my league and scared as all hell. 

The day started like any other. The sun rose in the east and I woke up. It’s the big day. I cover all by bases, shower, brush teeth, gel-spike my hair, eat breakfast, and brush teeth again. I decide to take it casually in my best black T-shirt and blue denim shorts. I wear my black belt with the silver buckle.

One hour before my date is to show, I spritz one small squirt of my Really Ripped Abs Bod body spray on my bare stomach and chest. Give it time to set in the pores as well as to dissipate so that I don’t choke any one, with scent less is more. I begin the ritual of drinking two cans of coke-a-cola classic. This lessens the strength of toothpaste flavoring my mouth deliciously.

This was about the time that I realized how much older than me 'H' really is. She is 21, shouts my ego in delight. The rest of me starts feeling a little anxious about what 'H' will expect from me. I’ve been told many times that I’m great kisser, but 'H' would probably want to do more than just kiss, though that implies that she will make a move on me. There is no way I am going to try and make the first move. Too embarrassing, though the opportunity to feel her wonderfully endowed chest has me sporting an erection already.

This is when I hear 'H'’s Volkswagen Passat pull into the driveway. I head to the door, trying to adjust my erection when my mind stalls. I see my date walking up to my porch in a flowing short black skirt, and spaghetti -strap tank top on. I can do nothing but watch the sun shine on her bouncing cleavage, and try not to drool. As I open the door she notices me watching her. 'H' looks me up and down. With a sly grin she twirls in place. I get a chance to see quite a bit of tan thigh and shaking boobs as my erection grows to full length in my shorts.

'H' takes pity on me by asking, “Shouldn’t we get to the movies now?”

I laugh nervously as I get into the passenger seat, finally having a semi-private moment to adjust my pants. In-between shifting gears and steering 'H' starts to place her hand on top of mine. I rotate my wrist to hold her hand in turn. My heart is pounding again. My stomach feels like it may have dropped a few feet. I’m so anxious. My body feels hyperaware of ever little move that 'H' makes.

As we get into the theater parking lot I feel H’s soft smooth fingers massaging little circles on my wrist and palm. 'H' parks in the back of the lot near a small park filled with trees. I turn to look her in the eye.

That is when she asks, “May I kiss you?”

I say, “Of course you may.”

She places my hand on her skirted thigh as she leans over. I put my free hand around her shoulders, lowering my lips to hers. 'H'’s lips are even softer than I imagined. Her lips taste like strawberries, tongue almost tasteless as it make a cautious exploration of my mouth. Her hands encircle the back of my neck and shoulders hold me to her feeding kiss.

We break apart. Breathing hard, I look down to see that I inadvertently slid 'H'’s skirt over half way up her thighs. I can’t seem to regain my composer.

Placing one of her hands on my cheek and jaw 'H' asks “Are you a virgin?”

I can do no more than look slightly down blushing in embarrassment, whispering shyly, “Yes.”

With a wicked gleam in her eyes, 'H' starts to breathe a little faster in excitement. Using two hands, 'H' guides one of my hands to the front of her breast.

“Have you felt this before?” she whispers to me.

I let my hand slide softly over the fabric of her top. My palm holds the weight of her breast as my middle and index finger straddle her nipple. Bringing my middle and index fingers together I let them squeeze her nipple as the rest of my hand plays with the surrounding flesh.

Eyes closed, 'H' breathily whispers, “Yes, you have.”

I kiss her to let her know that she is correct. We start making out all over again, only now I am fondling 'H'’s wonderful breasts. I run my hand over the shirt fabric, up to the soft smooth skin of her cleavage. I let my fingers flirt with the top material and the idea of sliding inside.

'H' has pulled my shirt up so she can touch the (then) flawless skin of my hairless stomach and chest. My young muscles quiver and flex under her smooth fingers. I break our kiss off, panting as I remove my shirt fully.

I hear 'H' whisper, “Have you felt this before?”

As I put my shirt on the dash, I feel 'H' pulling my left hand toward her again.
 
'H' puts my hand flush against the smooth skin of her soft stomach, under her tank top. I let her guide my hand up ribs. I notice that she took off the bra of when my hand meets my first naked breasts. All my movement pauses in wonderful excitement at the feel of a voluptuous breast and erect nipple, on the skin my hand. I don’t know what my face looked like, but 'H' seemed encouraged by it.

Pulling up her top she says, “It can help to be able to see what you are doing.”

Stunned I do nothing more than stare and let 'H' move my hands around her tits. After about 15 heart beats I finally start holding and massaging on my own only to be shocked again.

Taking hold of my face 'H' lowers my mouth to her waiting nipples.

“You kiss these the same way you kiss my mouth. Only suck the areola a little way into your mouth, as well as nibbling at my nipple. Remember like with your hands you want to create pressure, not pain. It helps to roll your lips over your teeth. That way you learn how sharp your teeth bite, and create a wonderful pinch.”

I lean forward tentatively with my eye glued to the breast not in my hand. I hesitate three quarters of the way to look a question at 'H'’s eyes. She grins wickedly, a look in her eyes like nothing I have ever seen. That look is almost predatory, as she nods and breaths the words, “It’s O.K.”

I seal my lips around her areola like she taught me.

I pull the base of my tongue back to create suction and to place the tip at the base of her stiff nipple. Scared I won’t do it right, I decide to slowly circle with my tongue. 'H' gasps hard letting a loud moan escape with her exhaled breath. Feeling more confident I flick my tongue up and down, finding that this changes the intensity of suction while also stimulating the whole nipple and areola.

I brace her breasts, one in each hand, so I can move my mouth from one to the other. I use all my senses to gauge the girl's enjoyment. I feel her quiver and brake out in goose bumps. I hear her breathy moans and keening. I smell the scent of 'H'’s sex filling the car, making me light headed, like a drug. 'H' slowly reclines her seat. The arms around my shoulders, her breasts in my mouth and hands lead me on halfway out of my seat and onto her.

'H' starts running her hands over my back, chest and stomach. Her fingers play in my waistband, teasing me in brand new ways. I feel so turned on that I want to return the favor. So I start kissing and licking 'H'’s front torso and neck in the places her hand had touched me, without releasing her breasts from my hands. I kiss my way down to belly button, and then wash each stomach muscle clean of sweat with my lapping tongue. I move further down to wash the waistband of her skirt and panties before making my way back up to drink her kiss again and again.

I can tell that 'H' really enjoys my efforts to please her, but I am really scared about where things seem to be going. 'H' is holding me tightly to her chest and kissing me with a reckless passion that speaks of experience I don’t have.

“Oh god,” 'H' moans in my ear as I graze my teeth over her earlobe. “Let’s get in the back.”

I learned the neatest thing about Volkswagens; the backrest of the back seat folds forward so you can access the trunk. If you keep your trunk empty there is space for people to lie down with feet in the trunk and heads on the back rest. The only thing in 'H'’s trunk was the blanket she spread out for us.

She looks at me aggressively saying, “Don’t worry, it’s clean. I put it here with a plan to seduce you.”

I take off my shoes and socks leaving then up front as I lie down on my side.

H takes her shirt back off after sliding in facing me. Putting her arm around my chest 'H' guides my body over her, kissing me deeply all the while. I brace my torso on my forearms, positioned on either side of her head. I let the weight of my lower body fall completely on her hips and between her thighs to the floor. With both arms wrapped around my back 'H' squeezes her moist breasts into my chest.

Running one hand down to grope my now available ass, she starts to grind into me. 'H' kisses my shoulders and chest as she removes my belt.

“The buckle hurts when it presses against me,” she says, to the worried look on my face.

I attack her neck with enthusiasm I have not yet shown to hide my worry. Responding with keening delight 'H' starts to grind against my erection with wanton need. She clutches my butt with both hands in order to gain more force and precision. I react with an involuntary shudder through my whole body.

I can’t begin to describe how much I enjoy my ass being grasped and held. I swear my penis gained a never before felt size at how aroused I was in that moment. Seeing the effect this had on me 'H' began to massage my ass. She gripped and released in time with her thrusting hips and sucking mouth. I can’t think strait any more. Now 'H' slides her hands up to my chest, holding me back.

Looking me in the eye she says, “I want to be your first. To be the person that you compare every other sexual partner to. I care sooo much for you and you’ve gotten my pussy dripping wet. Please, will you have sex with me?”

I stall with the only words that come to mind, “I don’t have any condoms.”

'H' has already pulled her panties to her knees; I had moved automatically to accommodate her. She gets one leg out as whispering back, “It’s O.K. I’m on the pill. Besides I’m allergic to latex.”

I can’t stop staring at the first pussy I have ever seen in my life. Taking this for permission 'H' undoes the button and zipper on my shorts. She pushes her hands into my pants. One hand goes straight to my virgin penis, the other runs behind me pulling my pants down below my ass. I feel her skin sweep the flesh of my ass and can’t help but to thrust into 'H'’s grip.

Pressing my ass down 'H' lowers me to her body. She leaves room to let me get my shorts off, but not letting go of me either. 'H' never lets go of my throbbing boyhood as she presses up on my ass, pulling me between her spread thighs and into her warm, wet womanly embrace. I feel the slick, heated flesh part as I am sliding in. Fear spills through me mixing with the pleasure of being made a man. I lean my body down and kiss at 'H'’s earlobes, inadvertently pushing myself all the way in. I meant to hide my fear. I crave 'H'’s respect and comfort.

Once I regained some composure, I started to mirror 'H'’s grinding movements. I find that she can’t help but to moan and gasp in pleasure, though this barely stimulates me. Thus I will last a longer than if I were to slide all the way, like sex-ed described.

“Oh….. My clit. Your pelvis rubs against my clit. You fit my pussy like we were made to go together.”

Encouraged by these word I start to use my ankles and calve muscles, pushing of my toe to rock my body and stretch 'H' a little deeper. Finding that I will be able to stand this without cumming too soon, I pace myself to her.

When 'H' increased her speed I would increase my force, never letting my pelvis leave her clitoris alone. I listen and watch in order to learn what to do. I listen to the moans, breathing, and holding of breath. I watch her start to tremble and shake. I feel her body clenching my enveloped man hood, 'H'’s hands pulling my chest in a tight embrace. Her hands clench as I feel liquid run down from her sex. I don’t stop.

I kiss deeply into 'H'’s mouth to smother the sounds. 'H'’s screams and enthusiasm fill me with the urge to make sure she has an orgasm. I slow my pace with her. We’re riding the waves of 'H'’s rhythm and passion. I don’t take time to listen to my own body; it is secondary to hers.

'H' moves her hand down to my butt and grabs tight. She is holding her hips to mine as I lower my knees to bring us even tighter together. I can now use slightly different muscles to keep my cramped calves from hurting too much.

This shift causes 'H' to start writhing beneath me with a full body quake. She can hardly breathe.

'H' is using all her air to utter, “Fucking god, fucking god. YOU are my FUCKING GOD.”

I can feel a sudden increase in wetness that was shaken loose. She starts to slow again and I follow. I’m scared now, really anxious that I will wear out before I can bring her to climax. I let her shoulders touch the floor again and bring my knees up under me. With 'H'’s thighs spread over mine, I start to move up and down, back and forth. I look into her eyes for her approval. 'H' grants it by taking my hands in hers.

She lifts them to her breasts, where I start to pinch and roll her nipples. I spread my hand wide and take large grasps of flesh. I start to increase my breathe rate. I follow 'H' into a gasping pant; I find it’s too much to take. I have to stop soon. My stomach is cramping. My calves have gone to shit. My shoulders are shaking from holding my position so long.

I feel really embarrassed as I ask the question, “Are you going to cum?”

'H' whimpers, “Hold out a little longer. Please... I am almost there.”

I hold out, moving with renewed energy now that my goal is in sight.

My trembling shoulders start to fully spasm. My stomach is one big cramp, so I let it stay flexed with my prick buried as deep as it will go.

My legs begin to give out as 'H' cries in my ear, “I’m cumming. Fucking god, you make me cum so hard.”

I fall on her thrashing body as my arms and legs give out. 'H' is gripping my ass to keep me inside of her. I feel more wetness run around my dick during her keening praise of my prowess. It’s only now that I realize she had reached orgasm before now. My body burns from exertion while I lay on my side to catch my breath.

I was too anxious and intimidated to relax enough to reach my own orgasm. I did what I needed to do for 'H', and that is what matters. I can always get one the next time.

After we calm down and get cleaned up, 'H' looks at her phone.

Looking at me she informs me, “You just fuck me for three hours straight, there is no way you’re a virgin.”

I reply, “I swear I am. I just followed your lead and paid attention to your reactions.”

In the end she believed me.

I have never nor will I ever clue her in to the fact I didn’t orgasm the first time we had sex.