Summer Vacation Ch. 01

It all started, as these things normally do, with a couple of drinks.

Well, maybe it was more than a few. And maybe it was more than just drinks.

I guess I should start at the beginning, as if there were any place else to start. The beginning of the wildest, most surprising summer of my life.

I'm 24, just out of college and single. I've never had a ton of luck with women but that's not to say I don't get laid at least semi-regularly. You know how these things go, when I'm hot I'm Joe DiMaggio when I'm cold I'm loading the bats and gloves into a bus headed to Tuscaloosa.

I've had a few girlfriends, really only one serious relationship, and, of course, she broke my heart. We were just out of high school and when she got tired of the long-distance thing she told me she found someone else and his cock was huge.

This really fucked me up, like, inferiority complex fucked up, but as I got out onto the dating scene I found out I was well above average, myself. Needless to say this restored my confidence.

I still wasn't the smoothest with the ladies, I have a bad habit of saying things that offend people and making bad first impressions, and my proclivity for drinking as much as I possibly can often gets in the way of my "game."

But college was college and there was, at least as many times as there wasn't, a drunk enough co-ed looking to end her night in a stranger's bed.

After college, though, the fun slowed down.

So it was on a bit of a cold streak my friends and I took our annual trip to the Jersey Shore for Memorial Week.

My friends are my family. We all grew up in the same neighborhood and have basically all known each other since birth.

People change, pursue interests that aren't best for the family or outright do things that are unforgivable, and a few friends have been lost along the way. But, for the most part, I am a part of a group of friends who care about each other than most families.

There's seven of us now- Frank, Mike, Drew, Steve, Brian, Austin and myself. The group that takes the trip every year has grown based on who's got a girlfriend worthy of taking a family trip but it never subtracts, even if someone has a occupational obligation, everyone finds a way to make it down to the house, even if only for a day or two.

It was Saturday, check-in day. Most of the group couldn't make it down until Sunday.

There were only three of us in the house for the first night. Mike, my best friend, his girlfriend Delia and me.

Delia, Dee we call her, was the newest addition to the group. Her and Mike had been dating for about a year and this was the first time she'd been in the house.

I'd spent a lot of time with the two of them recently, and Dee was easily the coolest girl Mike ever dated. Easy going, fun-loving, yoga type.

Dee was short, maybe 5'5", with long, brown hair, a tight little yoga body, small, perky breasts and an ass that was asking to be slapped, despite her skinny frame.

The three of us were sitting at the table playing the card/drinking game "Asshole". If you know anything about the game then you know playing with only three people is a recipe to a pretty quick drunk.

Dee had an Xanax prescription and she was very generous with her "mind-erasers," as we called them, probably one of the reasons she was so quickly accepted into our family.

So the three of us are pounding Miller Lite, passing around joints and gobbling up anxiety medicine and just bullshitting the time away. As our inhibitions dwindled the conversation started to take on a sexual vibe, and as that happened the card game slowed but the drinking did not.

Being the single-asshole-character I can sometimes play, I started busting my friend's balls, in a playful manner.

"Honestly Mike, you got lucky as hell. Dee is about ten times cooler than the girls you usually bring around. Remember Brit? Yeesh!"

Mike rolled his eyes and started to reply but Dee butted in a retort. "And when exactly are you going to bring a girl around? You know, it's been a year and I haven't seen you with anybody. All this third-wheeling you've been doing is..."

"Sad." Mike interrupted.

I ignored my best friend's verbal jab and looked at Dee. Really looked at her. She was looking damn sexy, sexier than I'd ever cared to notice before.

She was one of those girls who looked good dressed down. Tonight all she was wearing was a pair of tiny black shorts and a two-sizes-too-big black tank top with no bra. Her hair was still a little wet from the outdoor shower she and Mike shared after leaving the beach earlier that day.

I'd tried to catch a glimpse of them earlier that day, just out of bored, lonely, sexual curiosity. But there's a towel rack in front of the window that overlooks the outdoor shower and they'd thrown their towels over it, blocking my view.

I answered her. "What can I say? Most of the girls I meet aren't the 'bring around the family' type."

"Not like me?" She asked in a funny, high-pitched voice, then posed with her hands folded and a big innocent smile on her thin, sunburnt face.

"Nothing like you," I answered far more seriously, "nothing like you at all." I gave her another long look, as the don't-give-a-fuck-at-all effects of the prescription meds fully kicked in.

Dee must have been feeling the same. "You know, Mike and I were talking the other day..."

"Babe..." Mike interrupted, but only half-heartedly and he kind of trailed off and just shrugged his shoulders.

"What's with him?" I asked Dee.

"Oh, he took a bunch of Xanax. He's kind of built up an immunity to it recently so he took a lot more than usual. He's been using it to last longer in bed."

"Aw I didn't need to hear that," I said. "What's the matter, Michael? Quick trigger?"

"Dude," he said again in a burnt out lazy tone, "look how little she is. You can't imagine how tight that shit is."

"Mike!" She scolded.

"What? It's a compliment." He answered hazily.

"I told him his, well, lack of endurance wouldn't be an issue if he weren't so small, too."

Mike and I had been friends for two decades and we'd managed to avoid each others' genitalia in that time. Mike's considerably taller than I am, maybe 6'4" to my 6' and I guess I just always assumed he was well endowed.

"That's just a bummer." I answered, kind of unable to reply.

Dee kept going, "Anyway, like I was saying, Mike and I were just talking in bed the other day and he asked me if I could sleep with one of his friends who would I choose."

"Would you ever cheat on Mike?"

"well..." She started to answer.

"We have a deal," Mike threw out nonchalantly, "if one of us is going to fuck someone else the other has to be there."

"That sounds like the opposite of any deal I would ever make." I said, a little confused and a little excited about where this was all going.

"Don't you wanna know who I said I'd fuck." The way she held the "F" in fuck and annunciated it slowly made my dick jump out of its drug coma.

"He obviously knows you picked him, you've been eye-fucking each other all night." Mike said, but not accusingly or aggravatingly, just matter-of-factly, like it was no big deal.

"Oh yeah?" I asked, now both intrigued and a little weirded out that my best friend seemed to be asking me to fuck his girlfriend.

"Well, under one condition, really. I'm not going to fuck around on my boyfriend unless it's an upgrade."

"What do you mean 'upgrade'?" I asked.

"I want something I'm not getting. If I'm going to fuck another guy I want a BIG guy. Someone who can fill me up and finish me off."

That was it. I wasn't fully hard yet, because of the booze, weed and Xanax, but I was getting there. I just stared. First at Dee, then at Mike then back at Dee.

"So? What are you staring for? Let's see it," she demanded.

Dee was staring at the bulge in my shorts now and was now asking me to pull my cock out. She was sitting next to me, between Mike and I, at the table. She grabbed my belt and pulled, urging me to stand. I looked back at Mike, he offered another shoulder shrug.

I stood, unhooked my belt, unbuttoned and unzippered my cargo shorts and dropped them to my ankles. My dick was bulging in my boxer shorts and I looked at Mike one last time and he offered no objection so I pulled my cock, which was hardening by the second, through the fly of my boxers.

Dee's mouth and eyes widened. She was now staring longingly at my now totally erect long, thick cock. It's not especially long, really, about seven-inches, maybe a little more, but I've been told the girth is, "a lot to handle," on more than one occasion.

I gave Mike a quick glance and he seemed impressed as well, just sort of staring back and forth between my cock and his girlfriend's face.

After what seemed like an eternity Dee turned to Mike and said, "we're doing this."

Dee got up from her seat, took off her shirt, grabbed three shot glasses and a bottle of tequila off the counter behind us and poured three shots.

Her small, perky tits were beautiful. Her nipples were small and pink, hard as rocks. She handed us each a shot and we all drank them down.

Dee dropped to her knees and grabbed my cock, with both hands. Her fingers didn't wrap all the way around.

"Let's go to the bedroom," Mike said.

Dee, who had slowly begun to stroke the underside of my shaft with one hand and rub my balls with the other, said, exasperatedly, "okay, fine. Let's get this going."

Dee lead me without letting go of my cock into her and Mike's room. As she walked in the door I took her wrist and separated he hand from my throbbing cock. "Just a minute," I told her and closed the door behind her.

I turned around to Mike who had followed behind us. "Listen man, are you sure about this?"

"It's what she wants."

"Okay, dude, but I don't want this to fuck things up with us, you're my best friend."

"We're on vacation," he answered, and pushed open the door for me to walk in.

Dee had taken off the shorts and was on her knees in the middle of the room when we walked in. She looked at both of us and beckoned us over with her index finger.

We met her in the center of the room and she pulled off my boxers. I took off my shirt and she and I were both now totally naked. She then turned to Mike and pulled off his shorts and boxers, dropping them to the floor.

I was said to see what she'd said earlier was true. Mike, fully erect, had to be less than five inches long, and thin.

He and I were standing across from each other with Dee on her knees between us. She took each of our cocks in one of her hands and played with them, like she was a scale, weighing them. She turned to Mike and said, "I love my little Tic-Tac," then took the small, pasty white head of his dick in her mouth for just a second, then took it out and kissed the tip.

"Now go sit in the chair," she told Mike.

Obediently he stepped out of his shorts and walked over to the chair in the corner behind me and sat down.

Dee turned us so Mike had a full side profile from his seat and started going to work.

She slowly started stroking me again and playing with my balls, tugging them lightly and rubbing them.

"Put it in your mouth, baby." Mike said from the corner, stroking himself.

Dee looked up at me and I nodded. She stopped jacking me off, held my cock straight up to my bellybutton and licked the length of it, from my balls to the tip, wrapping her lips around the thick head and slowly bobbing, trying to get more and more of it in her mouth.

The size was already getting to her, and as she took more than the head in her mouth her eyes began to water.

She took my cock out of her mouth and licked all around the head, up and down the underside and then moved down to the balls. She tried and failed to get both in her mouth at once so she went back and forth sucking one then the other while stroking me rapidly, my cock still wet from her mouth.

She took a second to breathe and I took her hand and pulled her up. "You're amazing," I told her. "Let's take it to the bed."

She obeyed and laid on the bed. I laid next to her and she asked, "How do you want me?"

"Like this," I said, then rolled on my back and picked her up and spun her around into a 69-position. Her face and my dick were facing Mike in the corner as I gazed into her tight, gorgeous pussy at the head on the bed.

Her slit was already parted and soaking wet. She was shaved clean and so very pink. I so badly wanted to push her down to the end of the bed and bury my dick deep inside her juicy pussy but I held off.

I stuck my index finger in her slippery vagina and slowly fingered her. I moved my head closer and started flicking her swollen clit with my tongue.

She was moaning with my cock in her mouth, an outstanding sensation that put me on the verge of cumming. As if she felt it and wanted to prolong our fun she pulled my cock out of her mouth as I was now fully chowing down on her sweet, tight pussy.

In between gasps of ecstasy she began taunting Mike in the corner.

Rubbing the base of my dick and slapping the shaft and head against her face she said, "You see how much bigger it is than yours? Keep stroking that little tic-tac of yours, watch me take a real man."

With that she swallowed as much of my cock down as she could, at least two-thirds of it, and held it.

This must have been the tipping point for Mike as I heard him let out a moan.

Dee took my cock out of the back of her throat again to make fun of her boyfriend while I continued to work vigorously on her pretty little box.

"That's all you've got? You couldn't jerk off as long as your best friend's lasted throat-fucking me? You're gonna miss the bessst, aw fuck, ooohh, FUUUCK, uhhh, ohh FUUUUUCK!"

Just like that she came. Hard. I'd been using every trick I'd had eating her out while she sucked me off and berated her boyfriend and it paid off. Her body quivered and she continued to moan as she used all that sexual energy to take my cock deeper and deeper in her out-stretched lips.

I could feel the corners of her mouth struggle to open widely enough to accept the whole thing.

I looked around her upward pointing ass in my face at Mike. Apparently watching Dee cum so hard and only want more of my cock made him hard again. He was stroking himself again, with a horny, drunken smirk on his face.

Finally I had to fuck her.

I grabbed her hips and lifted her up so my cock flopped out of her mouth. I pushed her ass down towards my throbbing cock and pulled her body up towards me. She was now laying flat on top of me, her hair in my face, her pussy and my dick inches apart.

I took a handful of hair in my grasp and bent her head so her ear was on my lips.

I bit her ear lobe. Twice. Sucked it in my mouth, swirled my tongue around it and gnashed my teeth on it. She let out a high-pitched "Ahh," the first time and a lower moan of pleasure the second.

I held her hair and told her, "now fuck me."

Laying on top of me still, on her back, Dee reached down and grabbed my cock. She brought it up to her crotch and started rubbing the head against her clit then up and down her slit. She was teasing herself with my big cock like a sextoy while her boyfriend longingly jerked off in the corner.

She was teasing me, too, and I was dying to be inside her.

Finally I rolled her over by her hip, sat up behind her and positioned her doggy-style.

My desire got the best of me and I jammed my cock in her tiny pussy and thrusted.

Dee let out a pained, "Oww!" But when I started to pull out she reached back and grabbed my ass, pushing me back inside her.

I got back to thrusting until I realized Mike was behind us, only really able to see my ass and my balls thwapping against his girlfriend's small but shapely ass.

With one hand on her stomach and the other squeezing and pinching her perky little tit I lifted her up slightly and shifted us around without pulling out so Mike could see his girlfriend's face as I fucked her. She caught the drift and went back to taunting Mike as I worked her over from behind.

"You see that, baby? Why can't you manhandle me that way? Oh fuck your best friend's cock FEELS SOOO GOOD! SO FUCKING GREAT!"

I couldn't help myself. Making Dee writhe under me while she emasculated her boyfriend made me thrust harder and faster.

"OOOH fuck baby my pussy's never going to be the same again. This will always be YOUR PUSSY now, Mike needs your permission to fuck me now, AHH FUCK!"

She was close to cumming again, and I was on the verge, as well. She could feel my breathing getting faster and reached around again, this time grabbing my balls in her hands and tugging them, bringing a stop to any thoughts of blasting right then and there.

"Oh no, not fucking yet!" She said, "I don't go to yoga six days a week not to use it."

She crawled forward and my dick flopped out of her pussy. She was still so tight pulling out was a near-orgasmic sensation.

She crawled to the end of the bed rolled onto her back and put her legs in the air. She looked over at me catching my breath and asked, "what are you waiting for?"

I stood up off the bed and met her at the end of it, pulled myself in close to her and slowly entered her soaked, eager pussy.

Her legs were up around my shoulders, her ass slightly raised off the mattress.

I pushed the head of my cock in and out slowly until the both of us were staring into each other's eyes, silently begging each other for it.

I pushed all the way in and she instantly came. "AHA FUCK! MY FUCKING CHRIST THAT'S AMAZING!"

She was quivering under me again, gasping for breath between moans.

I leaned forward and pushed her legs so her feet were near her ears.

"Fucking yoga," I said, amazed how easily I could bend her.

I had her by the ankles now, fucking her rapidly at the foot of the bed. Id been delaying orgasm the best I could but I knew now I was close. She read it in my face again and squirmed out from under me.

She saw the exasperation in my face and said, "Don't worry, you can cum now, you just have to fuck my throat."

She rolled over on her back with her head hanging off the bed. She took me by the cock and pulled me into her. She opened her mouth as wide as she could and I dropped as much of my dick in as I could.

I started pumping my cock in and out of her mouth slowly. I got about halfway in when she started to gag, but instead of pulling out I went deeper. My whole dick was in her mouth and I held it there.

Her eyes were watering, running her makeup all over her face and I could feel her throat muscles trying to adjust to the about to explode cock in her mouth. I held it deep in her esophagus as long as I could then it was time.

I pulled out and laid my dick on her face. She stuck out her tongue and started lapping around my head and shaft. She kissed the underside of my cock, sucking it and licking it and then I finally popped.

I sprayed stream after stream of pearly white hot cum glazing her face, her neck, her tits and her stomach while she played with herself, rubbing her clit and fingering herself deeply.

I collapsed on the bed next to her and laid next to my best friend's girlfriend who was soaked in my semen.

Dee had still been playing with herself and finally finished herself off then looked up at Mike, who still had a hard-on, and said, "get over here and clean me up."

Mike grabbed a towel and wiped Dee off. She was absolutely covered in my cum.

I laid on the bed on my back as my dick shrunk back to its flaccid state. While Mike cleaned her Dee noted his penis hard was about the size of mine soft. Mike just grinned and finished toweling the pools of sticky, warm cum off his girlfriend.

"I hope you were taking notes, tic-tac. I'd hate to have to leave you for your best friend." Dee rested her head in my still naked lap and continued. "He just owned my pussy; Wore it the fuck out. It'll never be the same again for you again."