My Friend Jack

craigjeffers

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"So it has simply been to long, Louise, you have to help me get laid," I said.

My friend Louise laughed as she said, "Ha, well, that's one way to get past the small talk, just blurt out the good stuff." She went on, "I don't think that should be a problem, there are lots of guys in the city and with the assets you are sporting it won't be a problem getting them interested."

She was referring to my rather large chest. 36Cs perky and firm. I feared that might be part of the problem despite having an attractive face and big green eyes to go with my shoulder length straight brown hair, I was a bit overweight. It wasn't that bad, it certainly helped my breasts reach their full potential but I had begun to doubt myself during my dry spell of 8 months.

"Well thanks for the compliment, but I don't think it's as simple as just meeting a guy in a bar," I said.

"Well why not? Just go up to a guy flirt a little bit, buy him a drink, whatever, and after an hour or two ask him to take you home."

"I've done the one night stand thing before. It's not so much for me."

I explained I had had two one night stands neither were memorable. The guys had seemed cute, interesting, but when it got intimate it was awkward. One time it wasn't bad exactly, but didn't really do it for me. I guess I need to know a person a bit, which poses a bit of a problem for me now as it has been eight month since I've gotten any, and its hard for me to think straight once I think sex might be on the agenda when I'm talking to a guy. Also, the first time I did the one nighter was a disaster. The guy lasted maybe three minutes, and we just lay there next to each other for a bit before he left. I didn't want to go down that road again.

Louise was not to be deterred however, "Fine, then, no pickups tonight, but what about exes, or former flings that can get the job done?"

"Come on now, I'm not a complete novice here, I've tried; they are all out of town or dating people."

"OK friends then? That's why you keep guy friends around right?"

"Well there is this one friend Doug who seems interested but I am worried it would be weird, and"

Louise cut me off "Wait, seriously, I can't believe we are still talking about this - Jack, just trust me, your friend Jack."

"Jack... really... Jack? Oh wait you guys fooled around that time at my lake house right?

"Why are so surprised," Louise said. "No worries about Jay being a two pump chump, like you are worried about picking up tonight.

I was stunned. "Wait you and Jack didn't just fool around? You had sex? With Jack?"

A bit of background at the moment I'm 25, Jack and I had know each other been good friends since we were kids. Sweet guy, lots of fun, funny, but I had never really seen him dating anyone. Seemed sort of asexual. When he got back from college I heard some stories from him about girls, but he more or less seemed like the same old Jack. We had seen less of each other of late, were still friends, but not quite as good friends - I was a bit intrigued and needed more info.

"Yeah Kim," Louise said, "he and I had sex, and quite a bit of it actually, on the beach in front of the lake that night at your place. You, I guess saw us fooling around on the balcony, but we quietly excused ourselves and snuck off down to the beach."

"Wow, OK, cool, I had no idea, neither of you ever mentioned anything. And it seems so out of character for Jack to have sex with someone he just met."

"Well, I had just broken up with Matt a few weeks before if you remember and was looking forward to finding someone that weekend and getting him out of my system. Jack did that and then some."

"Really? I can barely picture him with a girl, let alone getting someone else out of your system. He was... good?"

"Good, yeah, that's one way to put it. My memory is a bit hazy - we were both pretty drunk, but he was great! Great oral, we did it for a while out on the sand and then snuck into the pool and did it in there. It was wild, he could go on forever, and was very well endowed. Like huge, like my forearm sized. No complaints from me. Actually thinking about it now, I wouldn't mind seeing him again. But you seem to need him more!"

We talked about it some more but my mind was made up.

Couple of weeks later Jack and I are standing in the parking lot of the multiplex having just finished seeing some very forgettable movie. I realized when we met up earlier that night that while Jack and I were still friends, we didn't laugh quite as easily or seem quite as close as we had before. This made my mind up for me completely that I would try and get him into bed tonight. I got increasingly more and more turned on as I half paid attention to the movie and half paid attention to the sex I would hopefully be having in short order. I figured being blunt was my best bet and once we are out in the parking lot saying goodbye and getting ready to head to ours homes, it was now or never.

"So Jack you know who I had dinner with the other night?"

"Who?"

"Louise, you remember her from that weekend at my folks lakehouse?"

"Yeah, what's she up to," he said giving nothing away.

"Doesn't matter," I answered, "Your name came up though."

"Oh did it," he said with a mischievous grin.

"It did, and I think you know why," I said with a smirk.

"Oh shit, is she pissed at me. I was thinking about asking you for her number, but then I knew she just broke up with someone and I was happy to be the rebound guy for the night and let her be. Did I play that wrong? I feel bad."

"First of all, no, she is anything but pissed at you, said some very nice things about you I might add," I smirked. "I had no clue you guys slept together though." I said hoping that talking about sex would get him in the right mood for when I sprung the idea that it would us tonight having some fun.

"Ok, glad she's not pissed, but now I have to know what these very nice things were!" he sarcastically demanded.

"Well," I gulped, "we were talking about how long it had been since I last got laid - its been quite a while by the way. And the idea of sleeping with friends to get out of a dry spell came up and she very quickly said, I should sleep with you. I was kind of surprised, but she said you guys had quite a bit of sex and that it was really very good and that you are... kind of.. well ... you know," gulped again "large."

"Oh did she now?!?" he cockily laughed.

"She did, and I have to say I have been mighty curious about what it'd be like since she said it. You're a guy, in all the year's you've know me you must have been curious too?"

"Well, of course, I have to say I have always been curious, what with those full lips of yours, what kind of blow jobs you would give," he said looking right at me.

"So what are we waiting for then, let's go to your place," I excitedly said.

"Well, let's do it tomorrow, I'm staying with my father and sister tonight and it would be weird if I weren't home in the morning."

"We could do motel or something?" There was probably more than a hint of desperation in voice at this point, but my embarrassment at that was more than offset by my desire to get laid.

"A motel, come on how cheesy can you get? If you've waited a while what's another day?" He said also this very non-nonchalantly and matter-of-factly, and I couldn't tell if he was teasing me or not.

"Well, fine, no motel, and this may be a bit too cliche for you too, but what about my car? Its an SUV the back seats fold out... the trunk is nice and roomy..."

"Alright, you're on. But not here, there seems to be a security car that patrols."

He explained that this park behind our old high school would be secluded. We agreed on the spot and he hopped in his car and headed there. I walked over to mine, got in, and was the easily the horniest I had been in my whole life.
 
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craigjeffers

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About ten minutes later shut my headlights off, and the field by the park was pitch black. I got out of the car and waited for him. It was a warm night for February but still a chill in the air. I was a bit worried that he bailed but then I saw his car pull up and I got really excited all over again.

He got out of his car, said nothing, walked up to me, lightly grabbed my face with his hands and leaned down to kiss me. Tentative, kisses on my lips for a couple of minutes began to heat me up. I was ready for more something deeper, but he was taking his time. Finally, a little tongue, he knew what he was doing. Our kissing grew more passionate and he pinned me against the side of my car. Slowly he lowered the zipper on my jacket and threw it on the car's roof. I know my big breasts are my best feature and he wasted no time demonstrating that he agreed. Through my pink silk blouse he expertly massaged and kneaded my breast sending tiny sparks of pleasure to my brain.

I was ready to find out what my friend Louise had meant by well endowed and slowly reach my hand down between his legs. I could feel the outline of his very large, still flaccid penis, before he grabbed my hands and pinned them against the car, above my head with one of his hands. The other began massaging my right inner thigh and working its way up while he kissed me neck. He made very light contact with his hand over my clit through my pants and panties and I let out a soft moan. He squeezed my left inner thigh and again begin working his way up that side.

He whispered in my ear, "So how long has it been?"

As he groped me in earnest now through my pants and panties I tried to moan out an answer, "Oh, oh... 8 months... ahh."

"Damn shame..." he said. He was totally calm and relaxed while I was beginning to get really into it, trying to grind myself against my hand.

He pulled his hand back not letting me get the contact I desperately desired. He moved his hand back up to my breasts and slowly began to unbutton my shirt.

"oooh, not sure.. ah... losing the shirt is... ahhh.... is such a great idea....ooooh, its pretty cold."

"Don't worry I'll heat you up," he said, his voice restrained but finally showing some hints of passion.

And with that my shirt fell away and he buried his head between my bra clad breasts. I took my right leg off the ground wrap it around him best I could and tried to dry hump him while pinned against my car. I could feel his cock begin to stiffen slightly through his jeans, and had to do a double take, it seemed to large to be a penis, I looked down trying to catch a glimpse of a bulge.

He chuckled, knew what I was trying to catch a glimpse of, "Louise wasn't lying, you're going to get it and you are going to love it, every inch."

His head still between my bra covered breasts, his hand slip down to the front of my pants and undid the clasp. Any protests about it being too cold were now the furthest thing from my mind. He quickly lowered my pants a bit and slipped a finger under my panty waist. His middle finger quickly entered me and his thumb began to work my clit. I was in ecstasy, it was so long since I had been with anyone, and here I was beyond aroused, about to get fucked by an apparently very well endowed guy who clearly knew what he was doing. Just as soon as his middle finger found a really sensitive spot, his thumb began drawing light circles around my clit, I leaned my head back against the car and began to quickly approach orgasm. He just as quickly removed his hand.

"OK, why don't you get in the car and get it ready for us, I'll start losing some of these clothes and I will meet you in the back seat to collect that blow job you owe me." I was annoyed that he had cut me off as i started getting close to orgasm, but one look at what appeared to be a monster bulge in his jeans had me completely willing to do whatever he said. I turned the car battery on and put on a bit of music and got in the back seat as he was climbing in with only his boxers on.

He sat down next to the door and watched me stare at the magnificent bulge he was sporting. It was eye popping. The sheer force of it lifted the waist band of his boxer a couple of inches away from his stomach. I was amazed it didn't bust right through the cotton. He kind of chuckled at my being so transfixed and it brought me back to the delicious task at hand. I reached in and removed his huge erection from the fly of his boxers. My God! I just stared at it for god know how long. It was huge, my fingers didn't meet as they wrapped around. Its impressive length reached well above his belly button. I have no idea how long I stared, I was transfixed. I could feel my juices really begin to flow. In the back of my mind I was also getting quite nervous as well; how exactly was this thing going to fit inside me? Would it hurt? Would it ruin me for normal sized men? He cleared his throat and brought me back to earth. I lied along the back seat with my head positioned above his lap and got ready to take him in my mouth.

"Shit," I said, "I know you thought I would give good head, and usually you are right, I do, but I'm not even sure I can fit your monster in mouth, let alone do anything with it once its there."

He laughed, "well only one way to find out."

I began by kissing his giant mushroom head and then started to slowly kiss it with more and more tongue. Finally I had his giant head in my mouth with both hands attempting, yes with the head in my mouth there was still room for both hands on his massive shaft, to suck it deeply. After a couple minutes I got a couple more inches in and began to work my tongue on the slit in his cockhead and he began to squirm in pleasure. I deepthroated as much as i could, until I gagged. Determined I tried again, but I couldn't get more than half of it down. My jaw was beginning to hurt a bit so I took it out of my mouth and began stroking it.

"Holy shit Jack, your cock is huge! I've never seen anything like it!"

Using his hands he flicked the base of his cock and it lunged forward lightly tapping my face. I ran my cheek up and down against the impressive shaft. He continued lightly hitting my face with his huge manhood I continued, "Damn, its just so fucking big! Just staring at it makes me wet. I'm half worried you are going to kill me by putting it in me and half worried I will die if you don't fuck me with it right this instant!" I had no idea where this was coming from, I engaged in some tepid dirty talk from time to time with exes, but nothing like this.

The combination of my blowjob/handjob and cock worshiping soliliquy had him panting and thrusting into my hand. I wrapped my mouth back around it, stroked what I couldn't swallow and sucked for all I was worth. A few minutes later he bellowed and came in prodigious amounts. I swallowed what I could and the rest landed on the back seat.

He lied back sated and exhausted and I cleaned up a little drank some water and spit it out to clean the cum out of mouth, downed a couple mints and excitedly got in the backseat with him. Together we lowered the backseats to expand the size of the trunk and he moved me into the trunk in a sitting position with my back against the sidewall.

No teasing this time. Deep passionate kisses while his hands removed my bra, allowing those perky, firm 36C beauties of mine to spring free in the their full splendor. He dove down toward them. Tongue on my left breast, fingers on my right. Slowly making ever smaller and tighter circles around my nipples. Right before the circles got so small they would encompass my nipples he switched. Tongue on right, hand on left. As the circles got smaller and closer to my stiff nipples I was desperate for some contact and thrust my chest out at him. He pulled away.

Began kissing a trail down to my panties which were more or less soaked through. He began lightly tonguing my lips through my panties, getting more insistent as he went. Also growing closer to my clit at the top of each stroke of his tongue. A couple of light clit tonguings from him and I was crying out.

"Oh god, Oh god, oh god."

Right as I attempted to grind my pussy in his face, he again pulled back and move his head back up to my breasts. Tongue on left breast, fingers on right. Again tighter and tighter circles, right before he reached my taut nipples he switched. This time, thank god, when he reached my nipples he let his fingers pinch one and his mouth suck on the other. It sent intense electric pleasure sparks throughout my whole body.

"Oh god Jack, oh, god. please....Please....PLEASE!" not sure exactly what I was asking him for.
 

craigjeffers

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He moved his head down began licking my lips and labia again through my wet panties. This time less teasing. Pushing his tongue slightly into my opening, the rough wet lace of my panties moving ever so slightly inside of me felt great. A couple quick licks of my clit and I again felt myself approaching orgasm. He pulled his head away.

This time no disappointed as his hands began pulling down my panties. I lifted my ass to help them along and he moved his head closer to my now exposed pussy. He breathed lightly against me, making me quiver, then much to my chagrin moved his head up, attacked my breasts. Kneading them firmly, sucking and biting and pinching my nipples. It felt incredible!

"PLEASE... PLEASE.... my god Jack!"

He took his head away and moved back down to my pussy. Licking my labia and inner folds first gently then with increasing force. He pulled back a bit and began very slowly licking his way up to my clit. No teasing this time thank god, he finally, began tonguing circles around and across my clit. I wrapped my legs around his neck to make sure his teasing ended. It did, he pulled back a little to create room to insert a couple of fingers inside me. He didn't fuck me with his fingers but moved them up and down inside me and in tight circles finding some of my most sensitive spots. My hips started bucking wildly and he moved one hand onto my stomach to keep me in place. As I neared orgasm he stopped licking my clit and concentrated on the motions his fingers made inside me. He added a third. As I neared an orgasm from his fingers began licking my clit again.

Finally he had his timing down and he triggered an orgasm with his fingers followed immediately by one with is tongue on my clit.

"oh..Oh... OH OH OH FUCK, GOD, OH GOD FUCK... AAAAHHH!"

I came with a force I didn't think possible, months of sexual frustration released, finally. As I regained my senses Jack lied down and instructed me to mount him. I did as told. Eager to get his monster cock inside me, knowing if he was half as good using it as he was with his tongue it would be amazing, but hoping it was going to be even better. I spread my legs with my pussy hovering above his torso and lowered myself on to him. I rubbed giant mushroom head of his cock along my dripping lips to lubricate and help him to go in easier. When his head made contact with my clit my whole body froze up.

"Unnn...oooh. Fuck."

I needed him in me and I began to sink down on him, very slowly.

He lied still below and let me take as much of him as I was comfortable with. It was a bit painful at first as his giant head opened me more than I thought possible. Once I got it in he told me to take it slowly and get used to his size for a bit. He took the opportunity to get his head in between my breast. The slight pain I felt began to be overtaken by a deep intense pleasure. I wanted more. I needed more. I wiggle around and began to slowly slide down his thick rock hard shaft. It took what for a second I thought to be all of it. I reached down and felt there was amazingly still a few inches to go. I kind of rocked back and forth on him. I wasn't yet in a position to ride him and was to intimidated to try. But the sheer size of what I had taken inside of me felt incredible. The pain began to subside and was replaced by an intense building pleasure and need. I needed to take it all. I rocked my way down completely into his lap. His legs behind me, mine behind him. His face in my breasts rose up and asked if I liked it/ I was moaning. He wasn't moving but the ten minutes or so I imagined it took me to take all of his huge cock had me close to another orgasm before he even thrusted once.

"Yes, YES, Ummmmmmmm. AHH, so good!!"

"Ugh, yea you like it deep that like?!" he said

Again I have never really been a dirty talker, but it in my pleasure it seemed like the right thing to do.

"Oh god yes Jack. So deep. So goddam fucking deep. Oh god OH GOD YES AAAAAAAHHHHHHHH."

I nearly passed out, he hadn't thrusted, just brushing up against a intensely sensitive spot at the very back of me that I didn't know existed, because no one else had ever reached.

We shifted positions a little so I could really ride. It was incredible. Him thrusting his giant cock up into me while I writhed around and tried to slam down onto him.

"Yea, Kim, you can really take a big cock," he said.

"Oh yea, fuck, I love this big cock of yours, sooooo GOD. DAMN. BIG. Soooooo gooooood."

I rode out another big intense orgasm. And rolled off him out of breath and spent. I looked over and his giant cock hard as ever and still pointing straight up. He asked:

"Can you handle more or need a break."

"Oh yes, more please!"

We awkwardly rolled around until he was on top of me and has incredible cock was about to re-enter me.

"OK, you ready to really get fucked now?"

"Oh god yes, please give it me!" I wanted it very badly indeed. Wanted really anything he wanted to give me.

He started slowly and built up a rhythm over time until he was really pounding me hard and deep. Not a thing I ever wanted or enjoyed before, but now, my god. I just gave myself over to him and his cock and was thrusting back into him and begging him. "Oh yes, harder! Deeper! Fuck you fucking stud! Playing to his ego a bit to be sure, but not a word I said wasn't true. I came once, he kept going. Finally his rhythm got a bit irregular and his grunting intensified and he started to come to deep inside of me. It triggered my biggest orgasm yet and I a blacked out. Came to a few seconds later exhausted and grateful for the fucking of my life