tagFirst TimeA Friend In Need

A Friend In Need

byRemy_James©

Let me first explain that I'm an alright looking guy, I've gone on a few dates and I know my way around a pussy, I just don't prefer to get attached to people because, let's face it, high school doesn't last as long as we'd like and ideally, graduation is the last time you see your friends before departing to bigger and better things. Well, we had finally embarked on our last week of full-classes which was humbly known notoriously as Senior Prank week. Now, unlike most conventional prank weeks that high schools have adopted, these pranks weren't limited to teachers and faculty- or even the vicinity of the campus- no, these pranks are meant for the seniors themselves, meant to be waged against one another in a war-like commitment.

In my group I had some good friends but there were a couple douches there as well- it's complicated but we were sort of the 'leftovers' from other groups that had dissipated over the years due to the public school systems' effective regiment of there being "no child left behind" which bastardized us away from our former cliques in with one another. Sounds great and it was at times, but there was more of a rivalry there than anything else.

You see, I was more of the writer/journalist of the group while on the opposite end of the spectrum was this loudmouth ass. A self-proclaimed Jock, though no longer since he flunked out last year and this is his second go-around. He was always challenging people to fights and overall just raising hell whenever he could out of spite. As you can probably guess, we were definitely in each others' crosshairs in senior prank week.

Now, obviously we do get along now and again and in fact, one common ground we do share is an intense trust and friendship with his little sister- we'll call her Robin. I had known her since Freshman year and me and the Jock immediately butted heads because he assumed I was hitting on her during a research paper in which we were paired up to write a paper outside of class- which meant hanging around in the library, each others' houses, at public places, etc. And we just happened to click and get along so we've been talking ever since which turned me from "random lit geek to pick on" to "liability to waking up with evil glare of little sister". Now because it's the PC thing to do I can't continue until I let you know that when I say "little" I don't mean that she's a Sophomore or anything- I mean that she's 18 like me and he's almost 20 in high school.

That being said, I know what you're thinking "So what does she look like?"

Well she's blonde, about 5'8", washboard chest- some guys have an issue with that, I'm more of an ass man myself and yes, just as her brother she is quite athletic and reprised the mantle of her flunky brother as "senior athlete" which he was devoutly proud of. She's quite popular with the guys most of the time- but getting past her brother is something that just doesn't happen too often and I felt bad for her since she was obviously not the slutty type that seemed to be the status quo at this point.

Speaking of which, I had a girlfriend at the time, a beautiful Puerto Rican chica we'll call Soledad. She was quite curvy and a bit heavy but carried it extremely well, especially in her generous breasts. The only problem is that although we both knew this was just a casual fling, she never put out and rarely returned my advances. I would often share my frustrations with Robin over the whole thing and she would begrudgingly listen to my woes while also criticizing Soledad's lack of self-respect, though I suspected envy as Soledad was quite well endowed and often had her breasts on display most of the time.

The week prior to Senior Pranks Robin expressed her deepest worries regarding the potential bloodshed and epic war campaign me and her brother would wage against one another and I refused to disclose any details to her at all for fear that she'd ruin my plans by narcing to her brother. Not that she was the type to do that, but I didn't want to take any chances with the idea I had.

I started off with a preemptive strike which included making him believe that I had filled a balloon full of urine (it was actually full of mildly heated vinegar-) and hit him over the head with it as he left class in the empty parking lot in front of mutual friends and passersby. This prompted him to freak out and begin heaving as though he was going to puke. Gagging and convulsing aside, there was no real harm done, no one was hurt and it was a good laugh after I showed him that it was indeed vinegar and not urine. Besides, a longstanding rule in the school was that if anyone went to the teachers and narc'd then not only would that hurt the whole spirit of the week- but due to anti-prank regulations on campus we may not be able to walk at graduation and the tattle would be shunned.

So it was on, the war had begun.

I thought I was ready for anything.

So that Thursday I'm at lunch, sitting with my buddies and they're all talking about graduation night events and what we'll do to celebrate- suddenly Soledad sits next to me in this very revealing crop-top that gave me a great view of her deep cleavage. She then insists on me trying some of her cookies she brought from her parents function the prior night and hands me a cookie while rubbing her breasts against me adoringly. Thinking nothing out of the ordinary (she was quite a good baker) I had a few cookies as she continued to urge me to keep eating as much as I wanted. I had about three of the chips-ahoy sized pastries until I realized everyone was choking their laughter back and looking at me.

My first thought was that someone had replaced the cookies and somehow put laxatives in them. I looked to Soledad in fear but she also had the same look on her face. "What's going on?" I asked slowly.

The Jock suddenly rushed me and laughed triumphantly, after a brief back and forth which took far longer than the setup for this story that I'm going to have you endure, he finally said,

"You have about an hour before lift off-"

Suddenly my head was spinning. Did he lace the cookies with speed? LSD? Marijuana? Luckily for me I had only one class left that day but there was still the ride home to think about- before I could ask further he took out a box and set it in front of me so that everyone could see.

"Viagra???" I exclaimed.

Everyone burst out laughing.

My first instinct kicked in and I looked at Soledad, she too was laughing hysterically and hadn't the single hint of sympathy. She knew the cookies were drugged! After 10 minutes of trying to ascertain if this was some payback for making him believe I cruelly pranked him the day before and maybe he was trying to psyche me out, I realized that this was all too serious. When I pulled Soledad aside behind the bleachers of the gym so that we could talk about this in private without anyone else having to know of my disposition- she simply announced that "it's just time to go our separate ways".

I protested, completely befallen with fear.

Suddenly, yanking the tie from the crop-top- the hammock falls freely along with her tan breasts, her dark nipples starring at me angrily as she uses both hands to jiggle them. I go silent and in horror, before I can even get my breath back- I'm hard as a rock.

Without saying a word she smirks and ties her top back, tucking away her brown spheres and saying, "We knew this was going to happen, you go your way and I go mine."

"You can't leave me like this-" I protest but she won't hear of it. She leaves, swaying her ass as she walks away and out of my life for good, leaving me and my disposition for the entire world to see.

There I emerged, exposed and vulnerable.

And it hurt, my cock felt like thousands of pins were sticking into every single nerve and I felt buzzed. Without a single idea as to what to do- or reason to remain in class- I ran to my car and pulled out as the Jock ran up to the window and banged on the door hooting and hollering while my- his- friends began making jerking motions in the air and I realized that that's probably what it was going to take to get this hard-on to go away.

But this was Viagra, it wasn't a matter of tossing one off and turning on the TV, this was probably the long-lasting, elephant hormone crap meant for hundred-year-old men with ED.

"FUCK-" I screamed, driving home and weaving wildly.

I'm about average size a little under 7 inches, but my cock felt at least slightly longer and I mean that in the sense that it was uncomfortable- it was so humiliating I didn't know what to do, who to call. As the guys put it, I'd probably spend the evening jerking until my arm fell off.

Finally it wasn't until I got home that it occurred to me the old warning about Viagra- any erection lasting longer than 4 hours would be hazardous and may even lead to impotency. As in, if I didn't cum soon and relieve that tension I may never had an erection again.

Running into my empty house and clumsily locking the door behind me, I darted to my room, dropping my pants and horrified at the sight of my swollen cock- and no that's not me complimenting myself- my cock looked like it was suffering from anaphylaxis. I looked like a dildo about to explode. The engorged cock was indeed uncomfortably longer than usual and it was at full-tilt upward, revealed to the rest of the world as though it had a grudge and purple as ever.

I wrapped my hand around the firm shaft and began jerking, careful to look over my shoulder and make sure that they hadn't planted cameras anywhere or that this was only the first phase of something much more pervasive.

"Okay get a hold of yourself-" I muttered, walking to my computer as my cock bopped agonizingly in the open air. "I'll be okay-" I reassured myself. I logged into my computer, there was an email from my mom explaining that she wouldn't be home until late tonight- wonderful. So I ditched the email, went to my preferred porn site and I found a 30 minute clip from a site that had the most beautiful natural women on the net (in my opinion) and began jerking away.

The video consisted of a white woman with pale nipples, she had EE cup breasts and a big round ass with long dark hair that went all the day down the small of her back. The video began with an interview and subsequently lead to an all-out hardcore fuck with a well-endowed man. Try as I might, maybe it was the embarrassment, maybe it was the pain/pleasure ratio, maybe I was just overworked and freaking out, but I was about 25 minutes through the clip and nothing- my heart was racing, I was sweating bullets and at any time I stopped to take a rest, my cock simply buzzed and throbbed as though it was the ultimate case of blue balls.

Suddenly there was a knock at the door, but the door bell what made me jump.

I ignored it once and continued trying to cum until the bell came again.

"It's me, Robin!" the female voice chirped, "I know you're here, your car is upfront, please answer the door-"

I stopped, winced at the excruciating agony and stood, pulling my boxers from the ground, slipping them over my sensitive member and waddled to the door. I cracked it open to see Robin standing there, she looked worried and I guess my strained expression only made her even worse.

"I came over her as soon as I heard- I am so fucking sorry-"

"It's okay," I grunted, "So I guess words spread already-"

"The doesn't matter, we need to get you to a hospital-" She insisted.

"NO-" I told her, "I've been humiliated enough-" I hyperventilated. This was too much, I didn't want to be humiliated like this anymore and I was in very bad pain at this point but felt as though at any given moment I'd cum buckets. The frustration and indignity was too much to handle and I found myself beginning to break down.

"Let me in at least," Robin told me, slipping through, I still hid behind the door and tried to regain my composure and also felt completely perverted if I were to display my erection before someone I considered family. She looked at me sympathetically and told me, "It's okay, you can close the door- I'm not here to hurt you anymore like those idiots-"

I closed the door, locking it and subsequently revealing my tent.

Robin's eyes were immediately glued to it as I made no attempt to hide anything. I simply lowered my head. Yet she made no smile, nor interest in my cock, rather evaluated my state of embarrassment and pain.

"We're both adults here," She told me in a calm manner, "This isn't the first one I've seen and I think it would be best if we air it out a bit and get comfortable, that's a lot of blood coursing through it and we don't need anything getting cut off."

What else could I do?

I dropped trow and revealed my swollen cock, stepping out of the puddle which my boxers produced. She simply looked at it and asked, "Does it hurt?"

I nodded, unable to speak in front of her.

She paced around for a moment, as though contemplating what to do next, "When did you first get hard?"

"Almost an hour ago." I replied.

She took a deep breath, "This isn't good-"

"It hurts, Robin." I whispered. "But I don't want people to know about..." I trailed off.

"My brother is an idiot for this-" She growled, " I can't believe he would be this STUPID- And Soledad- I'm going to kick her ass-"

"I started it-" I replied dismally-

"But this is taking it too far." She clarified, looking at my member.

Another moment passed and my hand gesture to it as though my cock was controlling my body and urging me to finish the job somehow. I let out a frustrated grunt, I wasn't going to jerk it in front of her and I was hoping that the overall embarrassment of being on display would scare the hard out of it. Robin then put her hands to her face and announced-

"I'll help you."

I looked to her in disbelief.

She withdrew her hands from her face and looked at me as seriously as she possibly could. "You're in pain, You obviously are too worked up to be doing this alone, and my brother is the reason why all of this is happening- it's the only way we can make things right and maybe since I'm a chick it'll be easier to get off.."

"But-"

"I lost my virginity awhile back," She admitted, "I've had vibrator since I first got into high school and someone told me penetration was the best way to get an orgasm- long story short I had to go to the hospital because I shoved it in too far and popped my cheery and I freaked out..." She looked away, breaking eye contact with me, "I know it's very humiliating to go to the hospital in such a manner and I wanted to be there for you if you had to go- but I can also do this for you too-"

"But Robin-" I tried to protest.

She then began stripping down in the most elaborate and unromantic way a woman can strip, taking off her shirt, jeans, kicking off her shoes until she was only in a modest sports bra and lace panties, "We don't have much time and if we don't resolve this then you could be really hurt."

Robin stood before me, the blonde young woman was very lean and tan, which led me to wonder if she sunbathed nude because I didn't seen a hint of tan-lines anywhere. "You're my best friend and you've been there for me so I want to be there for you." She said in a half-genuine/half-embarrassed tone, "Even if that means giving myself to you." I hesitated, she then chuckled nervously, "I love you, man. Let's just... Do what comes natural..."

She then turned around and peeled her panties off revealing a very toned ass to me, bending all the way over and exposing her beautiful flower to me before kicking the garment aside and bracing herself against the sofa, "I'm on the pill to regulate my period and I've been on it since I was a Junior- and I'm a relative virgin so don't be shy, just please let's do this okay?"

I achingly stepped over to the girl as she looked ahead, I could tell she was nervous and I was frantic at this point. Just then, this voice emanated from her that was womanly and not what I was used to hearing- but also motivated me, "Take what you need."

This was insane, "Please don't..." I told her.

"Sorry, I'm not sure how to-"

"I'm already hard I think we've covered that." I clarified.

"Maybe I just want-" She then yelped.

"What?!" I asked, looking at her in fear my cockhead was pressing against her lips and threatening entry but I hadn't done anything just yet, "I'm not even in-"

"I know, I know-"She replied, "It's just... Really warm and I'm sorry-" She said, sounding more embarrassed, "Go on, put it in, I'm just not used to someone else touching me there is all." I slowly inserted my cock into her velvet purse, delicately and respectively not trying to hurt her..

"Robin?" I groaned as she shook,

"What's up?" She asked colloquially.

"This is my first time." I replied, "I've never had sex before..."

She paused as I slowly fed her my entire cock, never stopping until my stomach was flat against her round ass. She then moaned, "I'm honored..."

"Are you alright?" I asked.

"Fuck me." She simply replied.

I pulled back and thrust into her slowly- the sensation was unlike anything that can be described. It was like a wave starting at the tip that cascaded down, into my groin and somehow cascaded out from my pelvis to every single nerve in my body. I groaned loudly and I felt as though my orgasm would come at any moment- though this was nothing new compared to the blue balls I've been enduring for almost an hour since Soledad flashed me.

"Are you-"

"NO-" I replied.

We both laughed.

Adjusting her stance, raising her ass she muttered, "Now after all that whining about Soledad, the least you can do is use some of that pent-up aggression on little old me, or are you worried that you're gonna break me in half?"

"Maybe." I replied.

She purred, "You can split me in half, I want you to leave a couple marks on me- it'll be funny a fuck to explain them to my brother-" I thrust deep into her as she buckled, "Yeah, that's the shit, baby-" She urged as I rammed her again, using the back of her sports bra like reigns on a horse as she tilted her head back, "Fuck me good babe-"

I withdrew and thrust once more- this time it caused the sofa to move up a tad and she shivered, "You know, you can do this faster right?"

It put both hands on her hips and began thrusting inside of her, plunging into her like a drill and fucking her pussy as though my life depended on it. She gripped the pillows on the sofa which she could reach and howled in pleasure.

"I thought you said this was your first time-" She asked, panting and tossing her head back as I plowed her.

"It is-" I groaned, the orgasm building but nothing came, I then said in futility- "I can't cum-"

She moaned in response, "Keep trying..." She breathed, "Oh GOD- keep trying-"

I pulled out- she looked to me in protest as I shoved her onto the sofa back-first, achingly making my way around it and mounting her in a missionary style, she looked at me surprised.

"I need to see your face." I explained, "It'll help."

She smiled, putting a hand on my cheek lovingly as I inserted myself into her.

I looked at her black sports bra and decided it was time for it to go- I lifted it up and peeled it off of her body much to her chagrin. "Why not?" I asked.

"I have nothing there-" She muttered, but I managed to get the bra off revealing a flat chest with two, very pert, pink nipples.

"Oh I see a couple things-" I replied taking the left nipple into my mouth. I had heard a rumor that the smaller the breast the more sensitive the nipple, and Robin was living proof of that. Soledad was always lukewarm when I pleasured her- but Robin was more responsive to the nipple-play than my cock in her pussy.

"OH YES-" She screamed as I quickened my pace and she wrapped her long beautiful legs around me, "DON'T STOP-" She screamed again forcing me in deeper.

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byRemy_James© 3 comments/ 96141 views/ 22 favorites

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