First Time By The Bay

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He recounts their first experience together.
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I write these stories for my long distance lover to help her along in life and she often reads them to me on the phone as we pleasure ourselves. She is not very experienced, but is willing to let me have my way with her, so my letters also serve to give her some idea of what she will be subjected to upon our next in-person tryst.

I should also mention that I like being romantic as my depraved fantasies unfold because it makes her feel even dirtier, and I love making her feel like a bad little girl. Love romancing her until she is so relaxed she can't put up much of a fight when I start treating her like a whore.

This one in particular recounts my memories of our first sexual experience with one another. Though it is indeed a recurring theme in my letters to her, I make it a point never to embellish - instead with each new reminiscence different aspects are focused on and the night becomes increasingly more precious to us both.

Hope you enjoy!

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Dearest Julie,

I admit it – I am a little ashamed how much time I spend whenever we talk on the phone hoping and praying you will suddenly confide to me that somehow, something I said has sent a chill down your back and up between your thighs.

Sounds sappy or even desperate, but whenever you reveal to me that without the slightest manipulation from anything other than my voice, a tingle runs over your clit and your sweet little hole becomes moist it makes me feel very special.

Very wanted... very happy... and without fail, very hard.

We share a lot of things with each other and all of them are precious, even the sad things cause we often feel better after letting them out and that is no doubt a precious thing. Might be a day or 12 late from time to time, but I will never turn a cold shoulder on you - our thing runs way too deep for any thing like that. Not to mention I owe you so much in return for help you have given me or my sincere and ongoing interest in your happiness!

I know that you would prefer to speak of our friendship as a separate, entirely different thing than our admittedly odd, but intensely fulfilling relationship as lovers - but indulge me as I attempt to clarify why I cannot, by recounting yet again some of my favorite moments as these two sides of Us, at least for me, were fast becoming blurred beyond any hope of repair.

First an admission of something naughty I did while skateboarding downtown recently. Didn't have any money to spend, but I thought it would be nice to cruise by the old smoke break spots and after work hangouts we used to haunt. It was fun, but it got an unexpected result that would not be ignored, so without money to spend I had to seek privacy in the form of Casey's bar even though I would have preferred that other more fancy place we loved to drink at.

Anyhow, the lingering ghost of memories we made downtown got me very excited and I wanted to do something I hope makes you happy and snuck into Casey's bathroom where I spent 15 minutes slowly stroking my rock hard cock. I thought of how good it felt when you first slid your tongue into my mouth, and mine deep into yours. About how nervous I was when, after hoping for so long that you would someday let me, I toyed with your clit and gently pushed a finger up inside you for the first time. I can still feel the heat of your hands working their magic until the pre-come so deftly teased from my balls coated your fingers and see the wonder in your face as you played with me like some sloppy new toy.

I remember how silky your hair felt as I giggled and tried to bend down to kiss you, winding it in circles around my fingers, pulling back and down ever so slightly until like some cheap back alley slut your mouth opened wide and your tongue gently swirled over the head of my stiff cock, dipping into the hole. Makes me weak to think how you slurped on the tip like some perverted pacifier as I ran my fingers down your back, down into your pants and began to massage your clit through panties which slowly disappeared between the velvet lips of the cunt my fingers began slowly spreading open.

Every nuance of how after you teased me with that first, solitary attempt to eat as much of my hard on as you could your eyes smiled up into mine, my dick slid out from between your lips and you ask so innocently "Am I doing OK so far?" is etched upon my mind in crystal clear detail.

You gazed up at me like a little girl who honestly needed approval, pumping my rigid shaft with her fist until I answered "Please, don't stop..." and began pushing my dick back up into the mouth gingerly closing around it. Your trembling lips and tongue felt even better as I slowly increased the pressure on the back of your head and inch by inch began to force my cock deeper into their wet embrace.

Kneeling like you were across the front seats of your new car, I can still see myself disappear between your lips a few times just before you try spreading your legs a tiny bit more, even though I hadn't been able to get your pants pulled down past the middle of your soft, thick thighs.

Struggling against the tight fabric biting into your flesh you nearly slide off the seat and I can still feel the self conscious laugh melt down over my dick give way to the moan you made as I started to finger fuck your warm, inviting hole. Forcing a finger past sticky lips and down into the wet hole of your cunt I suddenly remember a drunken conversation not weeks before that explained why you felt like a High School Freshman.

Complaining and feeling sorry for ourselves again you lamented it had been more than 4 years since you last had anything more than a single finger or a tampon up your cunt and were scared it would hurt if you ever got a boyfriend again.

I relish the feel of a tiny choke as I push down on your head harder and force a second finger into the other end of your body. Releasing my grip I whisper for you to keep sucking, I reach down to pull one cunt lip to the side, then the other until I feel your cervix between the two fingers of my other hand as I roughly jab them up you.

Playing with it for a moment, pushing the tip of a finger into that hole too before pushing your face down onto me once again as I spread them as far apart as I can. Enjoying the feel of your now dripping lips, jelly like to my touch, the process is repeated, driving the 2 fingers down the tight throat of your pussy slightly harder each time as it gets wetter and wetter around them.

The sensation of wetness drooling out around my fingers and down over my balls at the same time is totally unique to that night and its something I will forever love you for.

Your cunt was so wet and so tight around my thrusting fingers, it almost makes me kind of sad that we never pushed my cock up it instead that night - but the feeling of you clenching down around my fingers and trying so hard to get my whole dick in your mouth almost makes up for it I suppose...

Of course there is the tiny squeal of surprise you made around it as I pushed the tip of my dick to the back of your throat for the very first time and ripped down into your cunt using 3 fingers at the same instant. If you recall, feeling your hole tense up around them only made me drill them harder into the rubbery ring of muscle, causing you to pull your head off my dick trying to catch your breath.

Even though you kept jacking me and tried like hell to relax during your breather, I relentlessly kept trying fuck all 3 fingers past the vice like opening of your vagina. But you never stopped licking the head as you jerked me off so I kept at it and even though I have no doubt it hurt, I loved doing it to you all the same.

Nor I will ever even consider an apology for what I did to you next - it was simply too fucking good. Besides, you honestly seemed to be enjoying yourself as you bobbed up and down on my dick and I started to fuck your beautiful drooling mouth in time with the fingers that were probing deeper and deeper into your fiery hot cunt.

Remember how it felt when I finally drove all 3 fingers all the way inside? I do, and it was so good Julie – it almost felt like I popped your cherry, and judging by the noise you made it probably felt that way to you too.

Bet that's why I felt you clenching your cunt as I spread my fingers open inside you and began to pull them out. You pushed them back together just as one slipped past the mouth of your hole that closed tightly around the other two as they left.

Sitting the way I was with you half kneeling, half crouching down onto me provided a killer view straight down your ass when I looked and I was just in time to see a string of wetness glistening in the glow the street light, stretching from my fingers back into your cunt. I slowly massaged it into your clit, worked my way up to rub your asshole in gentle circles before spreading your lips open like a butterfly and once again drove 3 fingers into the exposed hole between them.

I could feel your sweet pussy still clenched around my fingers tight as it would go and the way you whimpered in pain like a little girl as I forced my way back inside was awesome!

Once I had pleaded with you to relax, massaged your G-spot a few times while whispering what a good girl you were, how good it felt to have you sucking my dick I was able to get 3 fingers deep enough to twist them in half circles around your cervix. Drilling you like this I asked you to try and suck me deeper than you had ever sucked any other boys dick then promised I would be nicer soon, but that you had to let me do one more thing to you first.

You started to play with my balls with one hand as I told you how sexy you looked when I spread my fingers open inside you and lifted my hand at the same time because I could see your cunt hole stretched open underneath it. You must have believed me because you relaxed a little and the open hole between my fingers got a little wider and made a slurping noise to match the ones coming from your face.

In fact when I try hard enough I can still feel the heat from your face between my legs as it drew ever closer to them, and have no problem recalling the feel of your tongue rolling down my cock as you swallowed, trying not to gag when I started pushing harder on the back of your head. Still remember how it felt to rub my thumb in circles over your asshole too, lubricated almost as much as the wet hole I had my fingers in.

(I'm not sure if you remember or not, but as I spread your cunt open from deep inside with my fingers I pushed my thumb half way into your ass. I recall wondering if you would like it or not – the short squeal and clenching around my thumb told me 'no' but I kept it up you anyway.

Later that night, after we moved to the back seat and I had convinced you to take your pants all the way off so I could eat you, I did more than just lick and tongue fuck your cute behind. Kneeling beside you in a semi-69 so you could suck and play with my dick at the same time, I sucked the sweet honey of your pussy from above. Once enough wetness had drooled out of your cunt down over the tight little hole below, I violated it with the entire length of my right my index finger.

Before long I wasn't even eating you out - I just crouched there, coaching you as you played with my dick and cautiously started fucking you up the ass with my finger. Tried to be as gentle as I could and I guess it worked because you kept your legs spread for me like a good girl for at least five minutes. Whispering for you to stay just like you were, I turned to kiss you and pushed my finger all the way up your ass.

As it slid gently out of your tight little hole you didn't think twice when I asked you to open your mouth. Playfully holding your tongue out and those bright, happy eyes gazing into mine I felt bad for a second - there's no way you would want to do this, but how could you not know why I asked you to open wide?

Then as my hand reached your face you smiled a little, the eyes fluttered shut, and I began to tremble, my moment of doubt passed. Still warm with the heat of your asshole, I laid my finger onto your outstretched tongue and you curled it around me. Twisting into you as you began sucking like it was my dick; I was struck by how similar the delicate pucker of your butt hole was to the puckered lips on your face. I wanted so badly to stick it back up your ass and make you lick it clean again - instead my own tongue joined the party in your mouth.... But I digress...)

As you may recall, before I got sidetracked there, I was testing the limits of your cunt with one hand and beginning to force your slurping face down onto my dick with the other. As I teetered on the edge of shooting my load down your throat I almost wanted to pinch myself to make sure it wasn't just another dream. I could hardly believe this beautiful, sexy woman making deliciously sloppy noises as I fingered her from behind and even better ones as she struggled to get the last inch of my dick past her lips was my friend Julie – the very woman I had longed to find in this exact position some day.

But it was, and as we acted out our innermost fantasy and forbidden desires with each other, I swear it felt like you utterly surrendered control of your body for a few moments just to make me happy... and I was. Even now as I relive the experience for the millionth time I am overcome by how amazing you were, how amazing you are, and ache to taste your soul again.

Waking from my instant of timeless bliss, you must have figured out what was coming next cause as my cock swelled deep inside your mouth the deep breath you tried to take through your nose was cut short. With a sudden, fluid movement I using your finger filled cunt as leverage to push your body forward, thrust upwards with my hips and shoved your head down until your lips wrapped tight around the base of my cock.

I could have stayed frozen in that instant and not cared – cock half down your throat, 3 fingers ripping into a drooling hole on the other end and a hand firmly holding your beautiful face tightly down around my manhood as every muscle in my body tensely tried to hold back just one more second before exploding.

The way your mouth and throat rippled over my dick as you forced yourself to swallow hard in a desperate attempt to keep from gagging during those few priceless moments is something I had never felt before or again and is something I will never forget. As your tongue rolled down your neck your throat would convulse in an incredible deep kiss around the aching head of my dick and I could feel of your heart pounding on it the same way I felt it on my 3 fingers stretching your sweetness open from the inside is something I treasure as well.

But nothing tops the way it felt when you let a tiny cough escape around the tip of my throbbing cock. The kiss of your swallows turned to instantly into the fluttering reflex of your chokes and it rolled up from deep inside your pussy out over my fingers at the same time. Close on its heels came more of the urgent, deep swallowing that, much to my delight only sucked me deeper down your throat but I felt everything inside of you go tight, teetering on the verge of panic.

I couldn't help myself – I forced your face down onto my cock even harder and pumped myself deep down your throat 3 or 4 times, just enough to feel you start to really choke and let loose my first blast, flooding your throat and mouth with thick, hot come. You struggled and fought against me as I pushed one final time into your throat, choking you with a second stream.

Jerking up hard with your head you fought to keep it down and I instantly took my hand away as you gulped around me for air as I shot another blast into your incredible mouth. Then to my amazement I felt your pussy ripple along my fingers that were still up inside it and you threw your face back down onto my throbbing dick and started tossing your head up and down on it, swirling your tongue as you swallowed stream after stream of my come.

It is a treasured memory of pure happiness to be sure, but the icing on the cake is more than just remembering how you brought me to one of the hardest orgasms of my life and not only let me come in your mouth (which is a rare thing in and of itself) but then hungrily swallowed the huge amount of come I shot into you (not to mention 2 more that night) but you kept sucking my cock like no one ever has until I was soft , even though you hadn't been able to take a real breath after I choked you with it!

The truth be told, that's all prelude to the really treasured memory of that night though:

After taking so much abuse to your tender vagina, being forced to choke on my cock as you gagged on a huge load of come in the front seat of your new Volkswagen - you continue to work come coated fingers over it as my cock slips out of your mouth and you shyly look up into my face with an embarrassed smile.

I can see one small rivulet of semen on your chin as your tongue runs over the dark red of your lips and you once again speak with the voice of a young girl who is deathly afraid she has not done well enough to hear the praise she so desperately needs.

"Well..? Did I do OK? I mean did you like it? If you want, I can try and do it better in a few minutes..."

I caressed your cheeks, dipped a finger between your lips to pull your face slightly down and guided my half hard penis in along side it. Rubbing come that was still oozing out onto your lips like lipstick I started to giggle and you looked so confused.

Face streaked with tears shed as you struggled to breathe only moments before, a dewy sheen welled up in your eyes once more, and through a very nervous smile you shyly whispered "...I mean it, it's ok - really... if you want me to... I mean if I didn't do it good enough and you want me to suck it for you again I can... I will, just ask me ok?"

Picturing you in that moment always makes me come like a volcano.

Just like I did that night in the car that night and just like I did in Casey's bathroom as I sat pleasuring myself, hoping in vain that you might find me there, thinking of you... praying you'd find me and with that 12 year olds voice, those bright, shining eyes smiling out from a tear streaked innocent face as you swallow the last of my load, ask if I want you to suck it some more...

You are an awesome lover there is no doubt, but you are an even more incredible friend and that is why I so badly want to make you feel even half as good as you made me feel, at least twice, over and over again until we are old and sick of each other.

Yours,

Chris

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