Siblings with Benefits Ch. 11bylovecraft68©
Road Trip pt1; the night before.
Shit! I thought as I glanced at my watch and saw that it was ten fifteen. I was supposed to be home by Ten and at the pace I was driving I was still a good fifteen minutes from home. Well I would just have to be late then, the roads were icy but more importantly I was driving with a bit of a buzz and the last thing I needed would be to be pulled over and hauled in the day after Christmas and the night before we left for our Christmas visit to Dad's brother; my uncle Ray in North Carolina.
Because my father was a psycho and insisted on not only driving but doing the 16 hour drive in one day we had to be on the road by 4:30,am, he had told Mark and I to be home by ten. I held my breath as I took the corner onto Cranston Street and drove past a cop sitting in a parking lot. I glanced in the rear view and let the breath out as I saw he was still just sitting there. I was driving fine I told myself just a little nervous. I sighed it would be one thing if I could say getting in trouble for being late was worth it, but that wasn't the case. The night with Jack had started out perfectly but couldn't have ended much worse.
Jack was the bartender at Vinnie's; he was tall, blonde, blue eyed, and damn hot! all the girls that worked there and most women in general seemed to have a thing for him. On any given night there would be three or four girls hanging around at the bar all but throwing themselves at him. Jack was also thirty years old and from some of the stories I had heard had been in a bit of trouble in the past so as flattering as it was when he started hitting on me a couple of months ago I didn't exactly jump on in.
There was also my issues with men in general. Jack was a bit too aggressive for me and I could not see myself getting comfortable with him. Besides all I would need is for dad to find out and he'd be down there making a scene. Finally though after a couple of weeks, curiosity and the nasty girl inside got the best of me and I agreed to let him take me out. Jack was good our first date we had gone out right after work on a Saturday afternoon and he had brought me back to my car at Vinnie's we kissed but that was about it. Although I will admit that the long, lingering, tongue filled kiss that he had given me had left me driving home wet.
On the third date we went back to his place and had sex. As usual I left frustrated. Surprisingly for his reputation Jack had gone pretty slowly, and when he went down on me he took his time and I came pretty goddamn hard. I returned the favor not getting him off, but impressing him with my ability to deep throat him. He had made a remark about it, saying no other girl had done it that easily and I recalled thinking "whatever" I mean he was hung fairly well but my brother had to have a good three inches on him.
Of course once we got to the actual sex the old Megan kicked in. I started off okay but when he wanted me to rollover I hedged then felt stupid the rest of the time as we stayed in missionary. I tried to spend the night, but woke up a couple of hours later on edge and had to leave. An hour later I was curled up with my brother. We hadn't had sex, I wouldn't if I had been with someone else, but I had needed to feel close to someone to feel the way I should after having had sex.
After that I was surprised that Jack asked me out again. We had a couple of more so- so nights and I finally just told him I was nervous, that I had hang ups and left it at that. Jack had said it was a shame because I was pretty damn hot and he could tell I wanted to. Then flashing that lady killer smile he had said that all I really needed was to just relax, and he knew just what could help. I knew what he was talking about and told him it didn't seem right. Jack had rolled his eyes and said if drinking was that bad for you he wouldn't have a job, and besides isn't that why everyone drank; to relax?
The next Friday night I got off at eleven and sat at the bar to wait for Jack to get off a t Midnight, while sitting there I drank three "sodas" that Jack had added some Captain Morgan to. He hadn't made them strong but I have to say I felt pretty damn mellow by the last one. I had worked at Vinnie's for awhile so leaving my car overnight was no problem. We went back to Jack's and the sex was indeed better as it had been the several times since. I had also been spending the night as well. Whenever I felt that old anxiety lying there I would have a glass of wine while I was there and be able to sleep.
We weren't really a couple, I was pretty sure he was seeing other people and at this point we didn't go out, just back to his place. I was okay with that I really wasn't looking for a boyfriend just some company, and some sex that didn't come from my brother. At this point Mark and I were probably fucking a couple of times a week but always made it around Krissy or Jack we would never with each other on the same night. Although we did sleep in the same bed sometimes afterwards but that was just so we could sleep. I have to say that although the relaxed Megan was a much more fun Megan I still wasn't half the nasty girl I was with my brother.
Normally Jack and I only got together on the weekends but seeing I was going away for a few days he had arranged to get off at 8. I had the week off from RISD so I had worked earlier in the day and come back to hang out at the bar and "relax" for an hour or so before he got off. I was wearing a tight black dress with the knee high black leather boots Mark had bought me for Christmas-that of course I had modeled for him last night- and had curled my normally straight hair. When Jack came over to give me a "coke" he leaned over, gave me a kiss, and told me how fucking hot I looked. It wasn't exactly smooth but it still sounded good.
I have to say I was pretty flattered however, as even though the bar had quite a bit of business that last hour, Jack really did seem to have a hard time keeping his eyes off of me. I noticed the drinks were definitely stronger that they used to be, but I was also getting more used to the effects. As I sat there I certainly didn't mind watching him. Jack really was hot with a nice body and pretty decent cock to go with it. Oh tonight was going to be a good night I thought as I finished my third drink, I was not only feeling damn relaxed but I was even feeling a bit... nasty.
We went back to his place where with a smile he reached into his jacket pocket and pulled out a small bottle of ginger brandy he had lifted from Vinnie's. He took a couple of swallows and handed it to me. I'd already had a few but why not? I'd be okay to drive in a couple of hours I took a long swallow then another enjoying the way the liquor burned down my throat and the warm feeling it gave me.
Speaking of warm feelings Jack didn't waste any time, within minutes he was kissing me while unzipping the back of my dress. I stepped back from him and gave him a playful push so he would sit back in the chair and standing in front of him slowly let the dress drop to the floor. I was wearing a matching black see thru bra and panty set I had bought a couple of days ago and decided to leave the boots on.
"Goddamn you look sexy tonight." Jack said his eyes wandering up and down my body.
"Yeah you like?" I asked, putting my head down and batting my eyes at him.
"I love it."
"What about my sexy new boots Jack; you like those?" He nodded smiling, and I added;
"You want me to keep them on?"
"Oh yeah." Jack said all but licking his lips.
I walked over to stand directly in front of him and turning slowly bent over shoving my ass in his face, but pulling away before he could grab it.
"I love that bad ass tattoo of yours." He told me referring to my Baphomet tramp stamp.
"Oh is that all you love?"
Turning back to him I put one knee up on the arm of the chair and reaching back removed my bra and let it fall.
"You don't love these?" I asked holding my tits up for him.
"Oh Megan I love those pretty little tits of yours."
Jack was smiling broadly sensing how playful I was and probably thinking "about time". Well we'll see if he thought that in a few minutes because this nasty girl had a bit of a game in mind for good old Jack.
"That's not nice," I pouted. "Calling them little."
I leaned onto the chair and shoved my left tit in his face.
"I think you should say you're sorry Jack."
"Aw come here." Jack said and eagerly sucked my nipple into his mouth.
As he did his right hand dropped between my legs and he expertly slid his fingers into my panties and right into my wet pussy.
"MMM I'll let it slide I guess." I told him pumping my hips into his fingers. Jack switched to my right nipple, his fingers still working my pussy as he did I reached down and unbuttoned his shirt taking a minute to rub my hands across his strong chest and flat hard stomach. As I did I waited for him to add his thumb to my clit but he didn't. I pulled away a bit reluctantly after all his fingers did feel pretty good, but they were just a tease as Jack himself had been lately. Jack made a sound of protest as I moved away but that quickly changed as I dropped to my knees between his legs and unsnapped his jeans.
"Ohhh you are feeling good tonight aren't you baby?"
"Oh trust me you'll know how good I feel soon enough honey." I answered with a wink.
I smiled up at him as I reached in and pulled his hard thick cock from his underwear and squeezing it tight gave it a couple of long slow pumps. I flicked my tongue across the tip getting him to moan and twitch his hips. Jack really did have a nice cock probably the biggest I'd seen next to my almost freakishly endowed brother. I licked his shaft up and down a couple of times then paused with my mouth right at the tip.
"Oh come on Megan don't tease me."
Not yet I won't I thought. With no further hesitation I opened my mouth and in one quick motion took him down all the way until I could feel my lower lip touching his balls. For someone so super cool Jack moaned as loud as a teenager. The moaning kept up as I went to work on his cock with a purpose bobbing my head up and down in a quick steady rhythm all the while pumping my hand along his shaft. Oh this nasty girl had a purpose all right. After being very attentive the first few nights the last couple of times Jack had not even gotten me off. He teased and played for awhile then fucked me and that was it. Last time I had asked him to keep playing with me and he claimed he was too tired and I should get going.
This time would be different. I hadn't really been thinking of it earlier but after the second drink it occurred to me that if my own brother had to follow the rule that I always cum first then why shouldn't Jack? After only another minute of me sucking on him with a vengeance I felt Jack's thighs start to tremble and he moaned out;
"Oh yeah baby, damn you can suck cock."
A romantic Jack was not but I would be lying if hearing him say that didn't get me going. Jack would certainly know that I could suck as I had given him an eye rolling blow job each of the last couple of times we'd played and gotten nothing for it. Well not nothing Jack was a decent fuck, but without cumming it was like a sundae without whipped cream. Jack let out another loud moan and started gasping out;
"Oh yeah baby! Just like that just like.... Hey!" He exclaimed as stopping suddenly I removed his cock from my mouth.
"Hey babe I was close."
I smiled up at him and said;
"I think tonight I get to cum first Jack."
"What?" He asked looking at me as if I were nuts.
"That's right Jack you haven't been very good to me the last couple of times after I was very good to you so I think tonight I get mine in advance."
With that I stood up and turning started to walk away.
"Hey where are you going?"
"To lie on your bed so you can come be good to me."
I stopped at the coffee table and picking up the bottle took another swallow then turning walked into his bedroom. I was still wearing the lace panties and I was giving my hips a little extra swing not to mention I'm sure the high heeled boots were doing great things for my legs. Without turning to see if he was following I went into his bedroom and after putting the bottle down on the nightstand lied down on my back. Jack was in the room before my head had settled on the pillow. I slipped my panties off and slowly spread my legs open.
"Come on Jack, come take care of my pretty little pussy with that nice soft tongue of yours."
I pouted and even though he was bit put off Jack had to smile at that. Pausing to strip Jack crawled up the bed and lying between my legs spread my pussy open and started flicking his tongue across my clit.
"Ohhhh yeah that is sooo nice." I told him.
My plan worked pretty damn well as Jack proceeded to do a hell of a job on my pussy. I really thought he would have rushed through but maybe he was trying to prove a point as he really was taking his time getting me close then backing off. After the third time he had me right there he stopped and started to slide up as if he were going to start fucking me, even leaning over to grab a condom from the nightstand. I put my foot up on his chest and held him there.
"Where you going baby? " I asked. "I didn't cum yet."
Jack all but rolled his eyes answering;
"I'll go back I just really want to fuck you right now."
I pushed with my foot.
"You can fuck my hot little pussy after I cum baby. That way it'll be even hotter and wetter for that nice big cock."
That got him. I had never talked like that before. Jack smiled;
"Well when you put it like that I..."
"And you know what else Jack? Forget that damn rubber I just want to feel you."
Screw it. I mean it's not like I could get pregnant, and those things were such a mood killer. Not needing to be told twice Jack went back to my pussy and this time it was him going to town like it was a race. Sliding a finger inside he rapidly swirled his tongue in tight little circles over my swollen clit. As he did I started playing with my nipples. Jack looked up and his eyes widened as he watched me.
"Yeah you like that show Jack?"
"Oh yeah." Jack breathed into my pussy.
After another minute of his furious licking, I felt myself getting ready. In the past I had held back a little not feeling completely at ease tonight however I was feeling damn fine and when I came squeezed my thighs around his head letting out a long loud squeal that I'm sure his neighbors heard.
"Oh that was nice!" I breathed out.
"Now let's see how wet that got you."
At that Jack slid up between my legs and plunged his cock deep inside of my now sopping wet pussy.
"Oh damn!" I moaned out as he began giving it to me with nice long hard thrusts.
I wrapped my legs around his waist and reaching up grabbed him around the neck pulling him down into a long deep kiss. I couldn't believe how good this felt! I was totally relaxed and enjoying every minute of it! I had even played him and gotten exactly what I wanted, no not gotten, taken what I wanted. Jack broke the kiss and smiled down at me as he continued to pound my tight little pussy
"That's it baby," He told me in between panting. "Now we're having fun no?"
"Lean back on your knees and we'll have more." I told him.
Oh yeah, this was the night the nasty girl came out with someone other than her little brother. Jack leaned back as I asked and taking my legs from around his waist I placed one on each shoulder, seeing the leather boots up behind his head was a hell of a turn on, but nothing compared to how fucking good it felt when I angled my hips up and he drove his hard cock even deeper into my pussy than he had before.
"Oh damn Jack!" I exclaimed as he wrapped his hands around my thighs and pulled me up even higher.
"Yeah Megan you like that?"
"Oh fuck yeah!"
I was lying there getting it hard and fast and loving every minute of it! Just as it should be and then Jack uttered those words that never failed to set me off;
"If you think this is good baby then you need to roll over."
With that Jack slipped his cock out and sat back on his knees waiting expectantly. As soon as he had said it my euphoric high slipped away and I felt that all too familiar tightening in my stomach. I gave him what I hoped was a sexy smile and rubbing the heel of my boot along his chest said;
"Come on baby that felt really fucking good just keep giving it to me like that."
"It'll feel even better the other way, come on Megan get on your knees for me."
I closed my eyes and took a deep breath, my rush suddenly turning into a headache. Jack reached down and grabbing my thigh gave a little push to try to guide me over. As he spoke I swore I could hear an older harsher voice in my head
"Let's go baby, roll over for me." Jack implored me. I said roll over you little bitch!
"No." I said opening my eyes and shaking my head.
This time Jack did roll his eyes;
"Oh for Christ sakes Megan I thought you wanted to have fun tonight!"
I sat up pulling away from him.
"I sucked your cock and I'm naked except for a pair of boots sorry if I'm not enough fun for you Jack."
Here we go I thought another night shot. Jack looked at me for a moment, surprisingly his cock was still hard, and he gave me a little smile.
"Hey Megan you're a hell of a lay really I just want to try it that way that's all."
"Well I don't really feel too good about it." I told him and started to get off the bed ready to concede the night, another casualty of my fucked up past.
Jack reached out and put his hand on my shoulder, and when I stopped slid over and putting his arm around me kissed my cheek, his face smelled like my pussy.
"Hey Megan look we been together a few times, you know I'm not going to hurt you I just want to have a good time with you."
"Yeah?" I asked relieved that he didn't seem angry.
Jack moved my hair and kissed my neck as he did he slid his hand up and started playing with my left nipple causing my breath to catch. Everything had felt so good I didn't want it to stop.
"Yeah baby, just relax and let me try, it'll feel damn good and you know it."
I wanted to I really did. Taking a deep breath and feeling like a pathetic little kid I looked at him and whispered;
"You'll go easy? You promise?"
Jack's answer his- perfectly smooth answer- I would realize later was to gently turn my face up to his and give me a soft sweet kiss.
"As easy as you want me to be." He then flashed that killer smile. "I mean hell Megan I just want to see that fantastic ass of yours up in the air, I mean it's perfect and you know it."
I laughed a little nervously;
"Yeah you like my ass?"
"I do I...hold on"
Jack paused then leaning over grabbed the bottle of brandy and handed it to me. I took it and after hesitating briefly thought fuck it I needed to get past this somehow. I took several long swallows and would have kept going but Jack took the bottle from me.
"Whoa their baby I want you to actually remember this, besides you need to get home tonight."
I nodded closing my eyes for a moment as my head spun. When I opened them I felt calmer, where that uptight feeling had been was now just a warm one. Looking down I saw Jack wasn't fully hard anymore. Which gave me an idea;
"Awww," I cooed. "Somebody's not happy to see me anymore I should fix that."
I bent my head to Jack's lap and sucking his semi hard cock into my mouth started blowing him as hard and fast as I had earlier.
"Ohhh goddamn," Jack moaned as he began running his hands through my hair.
"hmmm mmm" I encouraged sucking faster trying to get him close. The closer he got the less he would be able to fuck me, maybe I could even get him off...