Friends Discover Benefits


My name is Jason and I first met Gabby in eleventh grade religion class in my catholic high school.   I wanted her from the first moment I saw her, but restrained my libido because I knew she had a boyfriend.   We quickly became close friends, and the more I saw her the more I wanted her, but because she was already taken I didnt make a move, especially since I didnt know how she would react.   But seeing Gabby every day in class and many weekend nights drove me crazy.   I spent most of the time trying to sneak glances at her slim figure, with her incredibly tight ass and phenomenal tits (32C, I checked one of her bras one day), especially for a girl who barely weighed 100 pounds.   I think she caught me on more than one occasion stealing a glance down her shirt, but if she did her piercing green eyes betrayed no annoyance at all.    

Gabby and I both went to the local community college and remained close friends.   Though by this time I think she knew I had a thing for her, she never said anything to me about it.   At least it didnt seem to effect our friendship.   She was still with her boyfriend and I did my own thing, so it didnt seem to matter.   I still wanted her badly though.   Our community college was one of the few that actually had dorms for students, and Gabby and I lived in the same one.   We spent lots of time together, including many late nights, when I would enjoy watching her walk around in her modest yet tight-fitting pajamas with no underwear.   More than once I stared at her erect nipples protruding proudly from beneath her t-shirt; she definitely witnessed my involuntary reaction on several occasions, as my hard cock made a rather obvious tent in my basketball shorts that i did little to hide.  

And so it went for most of freshman and sophomore year.   Gabby and I remained close, spending many days together and more than a few nights either together in person or on the phone.

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    One night, during a phone conversation that continued late into the night, Gabby and I were discussing Star Wars, which we had seen together with a group of friends several days before.   Gabby had gotten dragged into going by her boyfriend and had little interest in the flick.   I wanted to see the movie, so I tagged along.   Anyway, Gabby told me on the phone that she barely paid attention to the movie at all and actually had her eyes closed for most of the time.  

"Were you sleeping?" I asked.   "No, just focused on other things," she replied.  

This piqued my interest, mostly because it wasnt like her to hide the ball.   "What other things?"  Silence, though I could hear her breathing softly into the phone.   "What other things were you thinking about?" I repeated.   "Noth-, uhh, nothing," she sputtered.  

I normally would have let it go at that, but something seemed strange.   I could hear through the phone that Gabby's breathing was getting heavy, almost as if she were sleeping, but she clearly was not.   And now she seemed to struggle to get out even a few words.   "It doesnt sound like nothing.   Why were you so distracted?"  Silence.

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    I waited, and then she finally answered, "Because I had my eyes closed and was playing with myself in the dark. "

My mind started racing.   I could tell that she was getting herself off on the phone right then and there.   I wanted to hear more, but I thought she might be nervous and I did NOT want to fuck this up by pushing too hard.   "What were you thinking about?"  "You," she confessed, and as I reached down to rub my stiffening cock I pressed further, "What about me?"  "Isn't it obvious?" she replied.  

It was, but I couldn't let it go at that.   I had to make a decision.   I could let this go and see where she would take this conversation or I could try to push it myself.   My rock hard cock, which I was now fully but slowly stroking, made the decision for me.        

"I think so, but I want to hear you say it. "  With that, I started breathing a little bit heavier to let her know that two can play the poorly hidden phone sex game.   "Why?" she coquettishly asked.   I let out a soft moan into the phone and stated the obvious, "Because I want to hear you say it. "

And then she began.   "I was thinking about a couple of nights ago, when you left my room and gave me a hug goodbye.

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    I was thinking about how hard you were and how good it felt when you pressed it right up against me.   Did you notice that I held your hug for a little bit?  I wanted to feel you for a little longer. "  

"Yeah, I noticed, but didnt know what to make of it," I lied.   I hadnt noticed anything, but wasnt about to say so.   "Is that all you were thinking about?" I asked as I slowly exhaled into the phone, "A hug?"

"Well, I was thinking about what could have come after," Gabby purred.   By this point, we both had clearly decided to take our time and enjoy every minute of this moment, knowing that it might change everything, but just not caring at all.   "What could have come after?"

"Well,. . . . I was thinking about how I should have kept holding on to you and pulled you back into my room.   I should have reached down and started to fondle you through your pants, stroking you slowly, making sure to play with the head, as I looked up into your eyes. "

"And then what?"

"Well. . .

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  " she had a tendency to start every sentence this way, and each time there was a longer pause before she would continue the story.   I could tell she was thinking about it, then rubbing her clit, and then filling me in on her thoughts.   "We would kiss slowly, tentatively at first, but then you would take control and start passionately kissing me.   Your hands would start exploring, softly and gently like the way you give massages, my neck, then my back, and finally reaching down under my pajamas to cup my ass and bring it in towards you. "

"Mmm. . . . I know you know how much I love your tight ass and how hard it makes my cock.   What happens next?"

"Well. . . . . you keep your hands under my pajamas and slowly pull them down towards the floor, bending down in the process, until your eyes are level with my waist.

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    I spread my legs just a little bit to give you a better look and you see that I am already starting to get wet. "

"How much hair do you have on your pussy?"

"Almost none.   I trim it regularly. "

"And are you wet right now?"

"Um. . . . yeah.   Very. "

"What are you doing?"

"Well. . . . I am doing the same thing I was in the theater. "  Thankfully, without my prodding, she went on.

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    "I am laying in bed rubbing my clit and thinking about you. "

"Good.   And I am laying in bed rubbing the length of my cock thinking about you.   This isnt the first time that I have jerked off while thinking of you, by the way," I confessed, taking a big risk.   "You dont know how hard I cum when I think of you. "

"Mmm. . . . good.   And now you are going to hear me cum soon.   I cant stop thinking about you and how I would have gently pushed your head into my pussy.   And how you would have started to taste me slowly and gently, lightly blowing on my clit at first, then softly licking it with your tongue as I begged you to move faster.   Finally you do and when you insert your tongue all the way into me I cum for the first time. "

Hearing the girl I have dreamt about for years getting herself off at the thought of me tasting her pussy is incredibly erotic and now I have to work hard not to slip over the edge.

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    I dont want to cum too quickly.   I want to cum with her, so hopefully we do this and more next time.

"What are you wearing right now?" I ask.   I want to get both scenes in my head.

"One of my red silk Victoria's Secret nighties and I just pulled down one of the shoulder straps so that I can play with my nipples with one hand and my clit with the other. "  I think she's lying about what she's wearing--though she had a ton of sexy lingerie from Victoria's Secret, she rarely wore it for no reason--but she's doing it for my benefit, so I roll with it.

"Oh Gabby, Im picturing you laying in bed right now and I want to go to your room so badly. "  I figured it was worth a shot, but when I got no affirmative response I quickly moved on.   "What happens next?"

"I pull you up from your knees and sit you down on my bed.   I kneel down in front of the bed and start to run my hands up your legs, under your shorts, until I finally reach you.   You throb in my hands.   You're so warm and hard, and I wrap one hand around you while I try to pull your shorts down with the other.   It takes a while to get the elastic over you, but I am finally rewarded when it springs out in front of me, pointed right at me.   I look up into your eyes while I bring my head down below your waist and slowly lick your smooth underside while using my other hand to stimulate you. "

She refused to use the word "cock" or "dick" or "balls" and I really wanted her to.

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    "What are you licking?"

She pauses, but I'm not worried.   Her breathing is so heavy by now I know she wont turn back.   "I'm slowly licking the underside of your dick from top to bottom and then running my tongue around the head.   I do this a couple of times very very slowly, teasing you, until you beg me to take it all in my mouth.   Finally, I do.   I start sucking your dick, taking as much in as I can, while I caress your balls. "

"Oh my god Gabby, I want to fuck you so bad.   Please keep going.   I want to cum.   And I want to hear you cum too. "

"I keep sucking your dick.   Changing speeds and motions, until I feel like you might cum.   I dont want you to.   I want to save that for later.   So I slowly stand up and lay you flat on your back as I climb onto the bed and on top of you.

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    I mount you, place the head of your dick at my entrance and then slowly descend until you fill me completely. "

"And how does it feel?"

"I have dreamt of this for such a long time and I start cumming again as soon as you enter me and my clit makes contact with your body.   My walls clench against your cock and I can see you straining not to cum.   Thankfully, you succeed and I lean down to give you a kiss and then stay low to your body so that you can lift up my shirt and play with my breasts. "   

"Are you playing with your tits now?"

"Yeah.   My nipples are really hard and I'm imagining you slowly licking them and then nibbling on them just enough to hurt a little.   I am sweating right now and I am soaking wet. "

"Put two fingers inside your pussy and pretend its my cock. "

"Oh Jason, that feels so good.   Im thinking about the rhythm we start building up, and the sounds our bodies make coming together, and how good our sex smells.   I turn myself around into a reverse cowgirl so you can see my ass bounce up and down on your dick.   And I use my hands to stroke your balls, bringing you closer. "

"Gabby, are you close to cumming?  I want to cum with you.   I want to hear your pussy explode. "


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  . . I'm almost there.   I am hurling myself up and down your cock.   I want you to cum inside me so bad.   Suddenly you turn me around again and sit up so that we are eye to eye with each other, with me on top of your legs.   I lean one arm back and start thrusting myself up and down on your cock.   My breasts are bouncing up and down.   I see your eyes start to flutter and you tell me your about to cum.   I beg you to cum inside me and then you take my hips and force me up and down two more times and then plant me down hard on your dick.   I feel you start twitching and you pull me close to your chest.   My pussy clenches hard again and I start to cum, just as you start to shoot deep inside me.   You start screaming my name and. . .



I cant take it any more.   "Gabby I'm going to cum!  I want you so bad!!"

"Jason, please fuck me!  Oh my god, Im so sweaty and wet.   Please fuck me!  FUCK ME!! FUCK ME!!!"

My cock twitches, I close my eyes tight, and my cum starts shooting everywhere.   I can tell by Gabby's screams that she just came too.

I lay there for a while, exhausted, slowly catching my breath.   She does the same, repeatedly commenting on sweaty she is.   I keep imagining her laying in her bed, partially under the covers, naked, and covered in sweat and smelling of her own cum.  

Slowly it dawns on us both that, for better or worse, everything just changed.
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