I was ready to take my prize. Milla had been worth all the effort to get her to the edge.
It started with a bet, a simple wager and progressed from there.
Only five weeks earlier I had bet my best friend Brad $250 that I could nail Milla before he could nail Trina. The rules of our game were simple. We had a code we needed to keep, meaning we couldn't lie about our successes and our failures and we needed to keep each other posted on progress. Rules agreed upon included nothing forceful and the prey had to be fully conscious to win the bet.
We had until Labor Day, as of that date no nailing meant a tie. We started in June knowing that ten weeks would be enough to succeed or we would give up if it became hopeless before the end of the summer.
Milla was different in looks from her long time friend Trina in that she was a gorgeous blond just eighteen, tall and slender with legs you couldn't believe and a shy smile that would kill. The almost nineteen brunette Trina was of average height with a set of perky knockers to drool about on her hourglass figure. Both amateur teens were dream boats who had kept their virtue for marriage. There wasn't a normal stiff in town that would pass up the chance with these ladies, so our bet was a long shot with these two keeping their legs tightly closed.
Finally we agreed it was a kind double dipping if could pop the cherry without protection. The bet was $500 for that victory.
We both clearly understood that we would have to start slowly by double dating. This was the easy as we both had taken the amateur teens out in previous summers numerous times but harmlessly.
The Best Laid Plans.
I knew this was going to be a slow and painful process that would require great planning and full attention to detail. Knowing this, I put together a plan that I hoped would work.
Week One
Friday: We met casually at the beach with friends, where we all seamed to hang out in the warm summer months. Late that afternoon Brad and I asked our dream boats if the movies the next night were something we could double on. Friends like the idea of dates in pairs and the amateur teens were no different both agreeing to go out with us.
Saturday, Date one was to the movies. This was simple no kissing, no moves, no nothing.
Tuesday, Date two was the same as date one, Milla and Trina were both home by ten.
Thursday, Date three same thing except we went for some shakes afterwards.
Week Two
Date four was at the beach on Saturday, just lying the whole day in the sun. We were four friends enjoying sand between our toes, beach balls, swimming and chat. We met again that evening walking the waterfront and having a good time. I made the first move and took Milla casually by surprise by taking her hand into mine. We held hands cautiously for 45 seconds before I broke it off. An hour later I had my fingers entwined with hers again. small did Milla know this was the first step towards victory.
Brad had also gotten so far with Trina and in fact they walked arm in arm. But my plan was devious, I wanted Milla to be unsure of our relationship the whole time. I planned to use her insecurities to my fullest advantage. She never needed to know what was next, surprise was to be my weapon.
Week Three
And so it went, small calculated steps.
I kissed her good night after going to the movies, smiled into those puppies eyes and then didn't call or see her for five hard days.
Week Four
After five long days Milla saw me walking and laughing with Beth at the beach at dusk. I knew she was looking so I gave Beth a long hug and a kiss. Beth was clueless to my plans or what was going on. But she didn't who care, she was a nice amateur teen who had an undeserved reputation as a slut. In reality she wasn't, she was just different.
I called Milla later in the week. She reluctantly agreed to go out for pizza. I had to make my move.
Saturday night we kissed in the car. I brushed her breasts while kissing but never made real contact. We talked and agreed to meet on Wednesday for movies. I pushed a small further throwing attention to her shapely legs placing my hand on her leg at the movies. We kissed good night when I drove her home and agreed to meet again at the party on Friday night.
My strategy was clearly on course. I knew there was three basic ways to bring a amateur teen to give it up. Some amateur teens, the "bad ones" chose outright to get laid that day, but this was not how it would be. Some get caught in lust and emotions and it somehow happens, I doubted this was the way either. Then some lose a struggle with their boyfriends advances and their own emotions, they rarely see it coming before it is in them.
Every female reaches a point where she knows and accepts the fact that she is about to be royally fucked. At that point in time she willingly gives in to the inevitable, a good amateur teen pounding.
Milla was a challenge. I needed to use her insecurities, emotions and naivety. She was jealous of my relationship with Beth, and believed Beth put out for me even though she didn't. I planned to use this to my advantage. She struggled with our relationship as well as her blossoming sexuality. Above all she struggled with the challenge of being caught off guard. I would use all of these weaknesses to get into her pants.
So as the Friday night developed I took baby steps designed towards breaking this philly until she would collapse for my pleasure.
Milla was nothing short of delicious "eye candy" that night. Her flowing strawberry blond hair and creamy complexion was to die for. She wore a simple tight baby blue tee just barely exposing her midriff and a dangerously short jeans skirt revealing her stunning legs and curvy ass. Looking at her, I knew there wasn't a man alive who wouldn't turn his head to get a second look at this marvel of nature. And any man alive would dream of the pleasures of getting into her skirt, including me.
The party at Marks house began slowly, some music and lots of chat. To my advantage Milla became visibly annoyed with Beth's arrival. Arriving without a date and worried Beth might try to snatch me away from her was a tool to be used. Milla was smart, very smart but naïve. Uncharacteristically Milla started to loosen up. Someone brought a bottle of Southern Comfort and she threw back a couple of shots, and soon afterwards a third shot to show off her maturity. Wow, Milla wanted to show she was grown up, to party hardy to gather my attention. No way could this have been planned better; alcohol weakens the intellectual senses but raises basic instincts. Breathing, heartbeat and of course reproduction are all basic.
I intended, drooling mentally, about fulfilling Milla's basic needs. I wanted to get her amateur teen steaming hot and then ram my penis into her. But I would need to message her emotions. Intentionally chatting with Beth, I occasionally naughtily glanced over at Milla. I was placing our relationship on the line trying to arouse a response from Milla. No way would I have done this without the Southern Comfort. It worked. Another unwise hit of Southern Comfort moved things along for my advantage.
Milla wanted me alone for herself and asked me to dance. The trap was set, she set it.
We went outside to cool off after two hot dances and continued to dance, tease and laugh in the cooler air. A slow song gave me the opportunity I needed to get close, very close. I pulled Milla as close and tight as I could. With my knee wedged in between her legs, skin to skin, I could feel what I want from her. Pulling her tight with my hand against the small of her back I am not going to let her go until her juices started to flow.
It was perfect, her skirt rose up slightly as my leg pushed between her hot legs. That warm luscious body tightly against me on a cool summer night was electric.
After a half dozen more songs Milla and I found our way to the boathouse. With her back against the wall I planted a deep kiss slowly spreading her innocent full lips apart and teasing her tongue with unexpected in and out motions. Our tongues danced for what seamed like all to long before I led her by the hand to the far side of the boat house towards the dock.
Milla asked "where are we going"?
"Exploring" I replied, but Milla was innocently unaware that my exploring intentions were to be of her body.
Milla was totally loosened up and the taste of the Southern Comfort was undeniable when kissing.
I took her to my spot where we could barely hear the music from the party, alone together under the stars. Milla leaned, her ass against the docks edge supporting her tipsy weight, our toes in the sand as I put my arms around her lower back and wedged my knee, once again in between her stunning warm legs. Her skirt rode up as felt the warmth of her amateur teen against my leg.
It was time to move forward; affectionately kissing my hand took a slow journey up her bare back under her tee shirt and unclasped her brassiere. With her shocked puppy eyes Milla asked "how far do you get with Beth"? Perfect opportunity I thought to myself, small resistance, I will fuck her before the night is done.
"How far do you suppose?" I teased.
Sliding a hand under her loosened bra, I cupped her left tit and then began gently tweaking her nipple. We kissed again as she allowed access to her tender pearly globes.
Breaking off the kiss she asked "this far?"
Preying on her insecurities and weakened state of mind I teased again with my answer "Maybe, maybe not".
Oh? She answered unsatisfied.
"Milla, do you really want to know?" I asked.
"Yes" She replied firmly.
"Really?"
"Yes", she giggled.
"O.K. Sometimes she lets me touch her." I lied.
"What, you mean?" was her stunned answer.
"I shouldn't tell you, but she lets me rub myself against her until I sometimes come." I answered.
"That sounds weird." She asked.
"Not really, Its like sex without going all the way." I replied to her curiosity.
"Forget about it Milla, were here right now just you and me."
We kissed for a small longer. I continued fondling her breasts gently noticing her nipples growing and becoming incredibly hard. The idea was turning her on, I thought. I need to take advantage of her curiosity and move in for more.
Milla I ask. Are you jealous of me seeing Beth?
"Yes", she answered.
"But you know I have urges, us guys need relief every now and then".
"I know", she again giggled.
Kissing her deeply I took her hand and moved it on the bulge in my shorts. She struggled but slowly her curiosity gave in to her aroused state and curiosity.
"Stroke it gently" I asked quietly. She slowly started tracing my penis with her gently fingers.
This is her first experience with cock. She will learn a lot tonight.
"Milla", I whisper.
"Do you want to be my amateur teen?"
"Yes."
"Then you need to help me through my urges." I ask as my hand moves down to her cunt.
"How?" She asks as I slowly begin tracing her full lips gently with my fingers.
"I already told you, I want you to try to make me come, can we try?"
Not sure and confused with her feelings she says nothing. She wants me for herself. But how far is she willing to compromise?
"OK its easy, I rub my penis along your amateur teen until I come." I tell her softly.
I kiss her deeply and pull her into a standing position. Grinding slowly I hold her tight against my body with my hands behind her luscious soft cheeks.
Trembling and uncertain she asks. "Will this be it?"
"No, are you kidding? It isn't that fast." I laugh.
"Will you stay away from Beth?" Milla demands.
"Yes, I think so." Is my answer.
Taking the lead I pause unzipping my shorts and asking her "Touch me".
She laughs nervously.
"OK."
Within moments Milla is exploring my penis as I am deep throating her with passionate kisses and feeling her wetness build between her legs as I trace the folds of her steaming amateur teen with my index finger.
"Are you OK", I ask?
"I guess." She answers.
"Don't be worried this will be fun." I whisper.
I go back to kissing her deeply with her ass pinned against the dock.
Pulling her an inch away from the dock I slowly lift her skirt above her waste exposing her panties.
I'm at work now arousing her from every angle. Deeply kissing her I fondle her breasts gently and push my throbbing penis along the thin cloth of her underwear between her dripping virtue and my manhood. The finger tracing of her amateur teen left a nice crease for my penis to trace along.
Time is on my side, especially with the assistance of my friend Southern Comfort.
With each minute passing Milla's breathing grows harder and harder and tattered.
She is so near.
I continue my pursuit. I enjoy the dripping wetness from her cunt, I know she is far beyond her protected virgin state. She is so close to losing it and letting me fuck her. But she has no clue.
"You're so wet Milla, I need, I want to come." I ask her deliberately.
"I want to use your wetness to help me come. If I rub against your amateur teen I know your wetness will help."
"You're serious, I've never messed around like this before?" She asks not sure.
"Yes. Let me do this, like I do with Beth"
"No one has ever touched me there before , and your penis is so hard."
"I'll be careful Milla, ok?"
Knowing I need time to heat her up some more I kiss Milla and resume the assault on her resolve. Gently fondling her tits, I slowly begin rubbing my penis along her dripping wet panties. Milla's breathing again becomes tattered. Before she knows it I slip my penis into her panties and begin rubbing penis against bare virgin cunt. Back and forth motions work as her full lips begin to spread apart.
"Oh that feels so good" I whisper.
"Yes" confused she fights to answer.
Milla is trapped, her back pinned against the edge of the dock I trace back and forth along her dripping wet amateur teen lips. The stimulation has her ready for fucking.
Feebly she asks me "Will you come soon?"
"Yes, I think so" I answer smiling inwardly, knowing that soon I will be deep inside of her, planting my seed for my excitement.
To increase the game I slide both hands into her panties cupping her firm cheeks. Milla is unaware of my intentions, I am removing the piece of cloth covering her virginity. I step back from the docks edge and go to my knees. Slowly I finish removing my souvenir from her body dragging her cotton panties down to her knees, and then to the ground.
Effortlessly Millas' panties have taken their journey to the ground disappearing from play.
Skirt lifted and panty less I admire her last moments of virginity seeing her nakedness from the waste down.
Innocently I laugh, "Oops." And return to my attention to her steaming cunt.
I know I am close, very close.
Placing my hands firmly under her cheeks I have to position her for my entry. I slowly lift Milla's weight until she is barely on her tiptoes between me and the dock. She is trapped between sitting and leaning against the dock, her legs spread wide apart I stand perfectly ready with my hardened shaft along her slit. Her drenched amateur teen begins to slurp in acknowledgement of the shaft running along her lips.
The time has come, to fuck this amateur teen silly.
Arching my back muscles I reposition and nestle the swollen head of my manhood pointing upwards between her full lips as she stands on her outstretched toes. The tip of my penis waits for what will follow, now just barely buried between her amateur teen full lips as they begin to open in acceptance. Milla knowing her position, holds me tightly around my back as we continue to kiss, only it is her who is now passionately kissing me. She has only one way to go from her raised position and that is down.
Milla knows and accepts the gravity of her situation; she can not stay on her toes all night. She is slowly slipping onto me. If she lowers her weight any more, she will be fucked.
Do you love me? She asks.
Milla, I'd love to fuck you. Is all I can think.
So I reply, "You feel so hot."
After a long deep minute of kissing Milla, she struggles to support the weight on her toes and begins so slowly to slip onto my cock. She is losing her grip. She drops slowly, maybe an inch, but not yet to her heals. My loaded gun continues its journey as she lowers her weight. The head is now passing between her amateur teen full lips that are opening in acceptance. She is so tight I am not yet screwing her. I need and want to get deep into her love tunnel; she will very soon take me into her.
Milla knows if she drops any more she is fucked, but she has supported her weight far too long.
Her decision is complete.
"Milla I wasn't planning on screwing you." I lie.
"But I can't stop now, you know Beth never would go this far, she's saving herself."
No longer just at her lips, the amateur teen channel becomes my possession, I break though her hymen. her amateur teen now begins to enveloped my cock.
I pause in victory, pull back and plunge violently forward, tearing deep into her reproductive channel as she removes the remaining weight from her toes. Milla shrieks in pain.
Three more hard penetrating thrusts and I am all the way reaching her cervix wall. Sweet victory.
Fully focused on completing my fuck, I begin a slow in and out penetrating motion and begin to pick up the pace. Milla is now my toy.
Milla holds me closely around my back as I spread her legs wide open bringing her feet back off the ground with her knees above my waste. She takes my penis willingly and deeply.
"Pull out before you come." She whispers.
"I don't want a baby."
"Ok." I whisper.
But how can I pull out of the most stunning screwing amateur teen in the world.
No way, I planned to knock her up, which was my plan from the beginning. I pound as deep and hard as she can take. Milla feels me drive deeper and deeper. I pound into her cervix and push beyond finding her uteris. I stop pounding as I explode inside her planting potent streams of warm goo deep up her uteris.
Oh God she screams as she realizes and senses that my seed is jettisoning rapidly for her egg.
Afterwards, stuffing her virgin panties into my pocket I ask "when was your period?"
"Thirteen days ago, I think, is her answer."
"Perfect!" I reply.
By Labor Day Milla is visibly carrying.
More proof that I had won.
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