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My Very First Time

"The surprising night I lost my virginity to a close friend."

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Famous Story

It was Amy’s big occasion, the day she was to be recognised for her photography and she’d chosen me as her date. At only sixteen, I wasn’t really prepared for a fancy gala at the Royal Photographic Society in Bristol, but it meant the world to her. 

She’d worked hard and today she was going to accept the Young Photographer of the Year  Award - the first step on a glittering career.

I’d known Amy for a couple of years and we’d grown close but never gone out. She had dated a friend of mine and my first real girlfriend had also been a classmate of Amy’s. But now we were both young and single - hell, we were only kids.

Tonight she looked magnificent, her hair pulled back and an amateur attempt at makeup paired perfectly with her with her blue and white flared dress - all a teenage boy could ever want. I felt inadequate but well dressed in a grey suit, tie and my favourite Church’s Oxfords.

Too young to drive, we had been driven to the event by Amy’s overtly-proud parents. Together we wandered around the exhibit, grabbing canapés and glasses of champagne from the silver trays as they glided by.

Finally, we reached the section dedicated to her. It was the first time she had seen her work blown up so large and on public display. Even to my non-expert eye, I could see the beauty in her pictures, a study of the seasons over Chepstow Castle. Everything from sunrises and sets to a meteor shower during the height of summer.

Her parents simply gushed at how proud they were of her and the hard work she’d put in.

Then the speeches began. The crowd gathered together looking at the podium. Amy being six inches shorter than me, stood in front with her parents to my right. As the speaker began talking about Amy and her work I felt an overwhelming sense of joy and emotion towards Amy.

Reaching forward I put my hands around her waist and hugged her.

“Well done,” I whispered, “you’ve done an amazing job - I’m so proud of you.”

She didn’t say a word and just pulled me tighter, stirring a growing stiffness in my trousers. Feeling my excitement, and out of sight of her parents, she reached her left hand behind her and squeezed my cock and balls. I didn’t know what to think but nearly came on the spot.

By 10 pm the ceremony was over. Amy had her award and a newly-won camera, now we were making our way home in her parents’ car. The journey was interminable, we sat in the back seat unable to talk about what had happened given the company we were in.

Arriving home Amy announced we were going to her room to watch a movie she had rented earlier in the day (yes an actual VHS from a rental store - those were the days). Her parents didn’t object, just saying not to stay up too late.

“I’m just going to get changed,” she said as we climbed the stairs. “See you in a couple of minutes.”

I dashed to my room and changed from my suit to my usual teenage uniform of jeans and a T-shirt.

Entering her room, where I’d been many times before, I saw she had put on a long T-shirt and shorts. We then did exactly as she had said and settled down on a pile of cushions on the floor to watch the movie. 

We still hadn’t mentioned what happened at the gala and I was too shy to bring it up.

As we sat watching the newly-released Reservoir Dogs Amy leant on my shoulder, her head nestled gently next to mine. Reactively I put my arm around her and pulled her close. 

I didn’t even notice as she placed her hand on my chest and rolled her leg over mine - suddenly that’s just where we were. 

She looked up drawing my gaze and before I knew it we were kissing. Tentative at first, her lips barely brushed mine as she sought unspoken permission. As our lips parted I stared into her eyes and for the first time in my life saw longing - a sheer desire for me.

Bringing my hand to her cheek I drew her mouth to mine and kissed her deeply. Our tongues meeting for the first time, dancing around each other in a silent tango of lust. 

Within seconds Amy twisted her body and climbed on my lap grabbing my face with both hands as her tongue probed the deepest recesses of my mouth. 

“I want you,” she said in between passionate kisses, “I want you now.”

With a new sense of purpose, my hands slid down her back to her firm ass squeezing her well-defined cheeks as much as possible. I could feel her years of dressage and showjumping had certainly paid off.

Without hesitation she grabbed her top and pulled it clear, releasing her gorgeous breasts - the first I’d ever seen in the flesh.

“You like?” she asked coyly. 

The expression on my face didn’t need translating and she was sure that I did.

Hardly believing my luck, I leant forward taking a tit in my mouth, all the time running my hands up and down her naked back as I pulled her to me. As I teased her nipples and fondled her boobs she moved away slightly lifting my T-shirt over my head. 

For the first time, I was skin to skin with a semi-naked girl!

Amy could feel my desire growing and rubbed herself across my swollen cock as her tits pressed firmly into my chest.

Sitting topless on my lap she looked at me and whispered: “We need to be quiet, my parents are in the next room.” 

Grabbing the top of my jeans she began unbuttoning them without a word. Instinctively I lifted my butt to make things easier for her.  

There she was between my legs with just my boxers between her and my throbbing dick. A thousand thoughts raced through my mind. 'What do I do? Will she like my cock? Will I do it right? My god, I’m about to see a pussy!, What the fuck do I do with a pussy?' and many more.

But before I had a chance to process anything she whipped my boxers down and was staring at my package - at least she didn’t look disappointed!.

Taking it in her hand she bent down and guided it towards her mouth. It’s impossible to describe that initial sensation. The wet warmth of her mouth engulfing my swollen head, the feel of her breath against my balls, and the incredible sensation of her hand on my shaft. Each one a new and almost unbearable experience.

Within moments I could feel my balls grow tight and knew I was going to cum. Still too shy to say anything I simply grunted: “Ugh, ugh, ugh!” as I came in Amy’s mouth.

It clearly wasn’t her first time and despite no warning, she took every drop of my first ever load with someone else without flinching. Catching my breath I looked down and caught her eye as she sucked the last drop from my tip.

“That was incredi…” I started

“Was that your first time?” she asked with a smile.

I’m sure she already knew the answer but I stammered: “Yes… and it was…”

Before I finished she winked at me and stood up. Wearing just a pair of loose shorts and despite her diminutive stature, she towered over me.

“W-w-what now?” I mumbled.

Amy reached down and took my hand pulling me up and into a deep embrace, her heaving breasts pressed into my chest as her tongue darted into my mouth. Still (naively) unsure of what to do, my palms pawed across her naked back dragging her tighter and tighter to me.

Grabbing my hands Amy slammed them onto her ass, saying: “You really can’t take a hint can you?”

With our bodies locked together and my hands gripping her ass cheeks, we fell onto her bed. Our tongues battled as I explored her body. 

Nervously, I slid my hand down her stomach towards her shorts, she didn’t resist for a second as my fingers dived beneath her waistband and into her underwear. Further down they went, through a mound of pubic hair and between her thighs.

I felt her warmth long before I reached it but her wetness was totally unexpected. As a virgin, the sheer excitement of reaching for her pussy was out of this world, regardless of whether I could see it or not.

The moment my fingers touched her soaking slit, Amy grabbed my face and kissed me deeply, her tongue diving into my mouth once more.

“Mmm,” she moaned as I slid my fingers down my very first cunt.

Eager to see what I was playing with, I pulled down her shorts and panties. The first thing that hit me was the intoxicating aroma, nothing like a boys’ changing room or my balls. A unique scent that begged me to get closer; a strong yet delicate fragrance, a mix of musk and passion, femininity and desire - totally unique and desirable.

Looking down I caught my first glimpse of a woman. She had a full mound of light brown pubes speckled with her own juices and then her pussy! I’d never seen anything like it outside of magazines and didn't really know what to do with it.

Sensing my panic, and confident beyond her years Amy looked at me and said: “Lick it.”

With a new-found confidence, I parted her legs further and moved between them, my face now inches from her hairy pussy. To this day, the scent of an aroused cunt is the most intoxicating smell I can imagine and I credit Amy for that.

Inhaling her aroma I dived in - still not knowing what I was doing - I ran my tongue her entire length before the taste hit me. The sweet tang of her juices was like nothing before. Imagine you’d taken the finest wine, some soft, sweet fruit and added desire. It was a taste I could enjoy every day for the rest of my life.

Feeling more like a gynaecologist than a lover I stared dumbstruck between her thighs. As they fell open her lips began to part revealing the delicate pink folds of her interior. Without thinking I simply opened her further and stuck my tongue deep inside and wiggled it around.

“Mmm, oh yes, mmm,” she moaned  - clearly I was doing something right.

“Mmm, don’t stop, mmm,” she muttered as I slid first one, then another finger inside her - my god how wonderful that felt as her young passage clasped onto my exploring digits.

Now I was getting into my stride. She liked my tongue, and my fingers seemed to be working so I just kept going. Before I knew it she was moaning loudly (nearly too loudly), bucking her hips against my face as her pussy clamped on my fingers and her hot cum shot over my hand.

As I looked up I proudly, I saw Amy biting her lip and gripping her pillow tightly to avoid screaming out.

By now my cock was raging once again thanks to my youth. Amy reached to her bedside table and grabbed a condom. Ripping it open with her teeth she sat up and eased it onto my erection.

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Despite what had gone before I still couldn’t actually believe I was about to have sex - this was not how I had envisaged this evening going.

As soon as she had my cock covered she told me to lie down, so we switched positions. I gasped as she straddled me and watched in awe as she slid onto my engorged dick. Those puffy pink lips opening to welcome me inside.

At first, there was an initial resistance as my bulbous head nudged its way in, swiftly followed by the warming embrace of her tight tunnel. 

Without a pause, Amy slid down until she was sat firmly on my lap, my cock stuck deep within her. Leaning forward she grabbed my face and devoured it - stabbing her tongue into me and grinding her hips against my shaft.

I’m not proud of it, but mere moments afterwards with Amy’s hot, tight pussy clamped onto me and her riding me vigorously I was bursting to cum.

“Ugh, ugh, I’m going to…” I started.

Before I could finish my sentence Amy put her finger on my lips and bucked her hips even harder. As my orgasm ripped through me, I buried my face in her shoulder as I fired shot after shot of cum into her.

Totally spent and heaving for breath our eyes locked on each other and she lunged in to kiss me once more. As we parted, Amy climbed off me and sauntered to her walk-in closet, my eyes following her every step of the way. 

After she pulled a fresh nightshirt on she came over to me and whispered: “We need to get you back to your room and my parents need to hear you leave.”

I quickly pulled off the condom, threw it away and dressed. As I headed out, Amy and I made sure to talk loudly about the movie which had finished without us paying any attention and made fake plans for tomorrow.

Back in my room, I collapsed into bed with a mixture of elation, passion and exhaustion mixed with an underlying fear of failure and dread that I had not lived up to expectations. Despite my reservations, I fell sound asleep.

Dreaming deeply I was roused with a hand firmly grasping my cock - instantly I was awake. Looking over my shoulder I saw Amy smiling at me: “Morning sleepy. My parents are at work already.”

Not wanting to miss the opportunity I pulled her towards me as I rolled onto my back. To my surprise she resisted. Then to my delight, she grabbed her nightshirt and pulled it off - leaving her standing naked in front of me once more.

Climbing on top of me I could feel her pussy against my bare stomach and within seconds my dick was fully erect behind her as she draped her tits over my face. 

Keen to please I grabbed them and kneaded their beautifully soft flesh before taking the nipples into my mouth.

But what I was most interested in was rubbing against my stomach. As we kissed I could smell the sweet aroma of her cunt as it grew wetter and wetter.

“I want to fuck you again,” Amy said.

Desperate to taste her again I replied: “I want to lick you again!”

Almost instantly I felt her naked vagina drag up my chest and over my mouth.

“Are you going to make me cum again?” she asked.

As much as I wanted to, I couldn’t reply as my face was swamped by her delicious cunt.

I didn’t need encouragement now and grabbed her hips, pulling her closer to me as my tongue delved deep inside. I was licking from the back to the front lapping as hard and fast as I could. 

That was when I spotted it, just inches from my nose and literally begging for attention.

I’d discovered the clitoris.

Carefully I pulled Amy lower so my tongue could touch her clit. Softly I licked, at first a single, light pass to ensure I was doing the right thing.

“Ohh, yes, do that again,” she said.

With the green light to continue, I felt emboldened and started teasing her firm jewel, taking my time to ensure maximum pleasure. My focus clearly paid off and soon Amy was grinding her pussy against my face with urgency.

“Mmm, ahh, ahh, that’s it, right there, right there,” she moaned as I felt her orgasm building. Within seconds she clamped her thighs against my head and bore down even harder, screaming out loud as a powerful orgasm coursed through her body.

If the taste and scent of a pussy is near to heaven then the sensation of a woman cumming on your face actually is heaven and I savoured every second of my first experience.

Her body, damp with sweat, lay on top of me as her waves of pleasure subsided. We rested there in a loving embrace for what seemed like an eternity, my cock throbbing so hard it threatened to burst.

Once recovered Amy slid off my chest and reached for my dick, delving into my boxers. She gently started tugging it up and down as she snuggled next to me. 

“So are you going to fuck me?” she whispered seductively into my ear.

Without hesitation, I ripped my boxer shorts off and looked around for a condom. Now I sincerely regretted not bringing my own protection.

“Do you have a condom?” I asked pathetically.

Amy told me to go and grab one from her bedside table and I leapt from the bed and rushed naked to her room, tearing the packet open as I returned.

Greeting me as I entered my room was a perfect picture that is etched into my mind for all time. Amy on all fours, her ass and pussy pointed right at me.

“I always like it from behind,” she smiled.

Carefully approaching her, I rolled the condom on and tried to casually slide my engorged member into her. But being so inexperienced I failed miserably. Reaching behind her, Amy grabbed my cock and expertly guided it to her soaking opening.

Today it felt even tighter than the previous night. As I eased inside I could feel every inch of her pussy firmly clasping onto me as if she was trying to juice an orange. 

However, now I felt more in control, plus I couldn’t see the look of passion on her face or (more importantly) her gorgeous tits and was determined that this time I would last longer.

Taking my time I thrust in and out holding her hips the whole time. Each time I felt my balls contract, I slowed my pace and tried to think of anything else. Relishing every move, my confidence rose and my pace along with it.

Soon I was properly fucking Amy, my thighs slapping against her ass cheeks and I could hear her excitement.

“Oh yes, that’s it. Don’t stop, please,” she begged as I slid in and out of her.

As her screams got louder, I knew she was going to cum once again and allowed my own orgasm to build. Pushing harder and faster than ever, our bodies moved in unison towards a combined finish. Hearing her moaning crescendo was enough to push me over the edge.

“Ugh, ugh, ugh,” I grunted as I came deep inside Amy and collapsed on top of her, my dick popping out of her as we fell.

There we lay panting hard trying to catch out breath our sweat-drenched bodies drained.

“You’re a fast learner,” she gasped.

“Well I have a great teacher,” I cheesily replied as Amy turned to hug me.

Gradually our breathing slowed as we held each other close.

“We should clean up. Want to join me for a shower?” she asked hoping out of bed.

Like a dutiful puppy, I followed her to the bathroom and into the shower. 

Basking in the afterglow of sex she looked beautiful to me as the hot water sprayed all over her. I remember thinking she looked like a commercial for some shampoo advert as she pulled her wet hair from her face.

I couldn’t take my eyes from Amy as the water cascaded down her chest, across her breasts and over her body.

“Wash my back?” she asked flirtatiously while turning around. 

The glass door steamed up as the temperature rose and I stared as the torrent from the shower ran down the arch of her back across her firm butt.

Grabbing the shower gel, I keenly began soaping her back anticipating the moment the lather would reach those pert cheeks. The moment they did I took my opportunity to wash, caress and squeeze her behind. Boy, was I appreciative of all the toning those years of horse riding had provided her cute derrière.

“That feels nice,” she said pulling me close, my cock sliding between her cheeks.

It wasn’t until years later that I discovered anal sex, otherwise I might have taken different actions. But the feeling of my dick pointing skywards slipping back and forth in soapy heaven was immense. 

Despite having orgasmed just ten minutes or so earlier my erection was as firm as ever (oh, the joys of being young). Reaching around I took her tits in my hands using them to create leverage for my thrusting.

“Mmm, that’s wonderful,” she moaned.

My pace and intensity quickened and the tightening began in my scrotum signalling another climax was on its way.

“Amy?” suddenly another voice pierced the thick air. “Amy, are you here?”

“Fuck, that’s my mother!” she exclaimed. Now panic filled the room and she pushed me away, quickly washing the bubbles from her lithe body.

“I have to go. You stay here for a while then get dressed and come downstairs,” she stated, urgently grabbing a towel for her hair and a bathrobe. 

With that, she was gone. Despite the fear of being discovered my hardness remained and I couldn’t get the image of her wet, naked body out of my mind. It only took a stroke or two for me to fire another load of semen straight down the plughole.

Now I’d had my release, I quickly shampooed and washed to ensure I’d be clean and free of the scent of sex. I got out, dried off, returned to my room and got dressed.

Nervously, I tiptoed down the stairs to find Amy and her mother sat at the kitchen table casually having coffee.

“Morning,” she said, “Do you want a coffee? Amy told me she had to wake you up - you must have slept well.”

“That would be lovely,” I replied.

 “I thought I’d pop home to make you both lunch,” she said, handing me a steaming mug of coffee.

My panic slowly subsided as it dawned on me that she had no idea what we’d been up to.

“That’s very kind of you,” I said, glancing over to see the smirk on Amy’s face as she excused herself to get dressed.

After that pivotal day, Amy and I dated for a little under two years until she went to university in Bristol and I headed to Philadelphia. 

We did see each other occasionally after that but only socially. However, last summer when I went home to visit my parents we met for coffee. Together we proudly reminisced about the night she took my virginity.

Published 
Written by LondonLimey
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