Jack Ch. 01

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Jack and Shelly come home to visit Lindsey.
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jackh.
jackh.
1 Followers

Shelly walked to the front door of Lindsey Collin's door. Her brown curly hair and blue pea coat were getting covered in snow. I sat in the car putting the two bottles of Sky vodka we had bought on the way in my black overnight bag. She turned to look at me and smiled as she rang the doorbell. I climbed out of the car and shut the door looking out as the final rays of sun ducked behind the horizon.

Shelly is about 5`5, she stood about three inches taller with her high black boots that came up to just below her knees. Her legs were athletic, toned from four years of swimming and track. She was wearing her pleated school skirt that did not quite cover her smooth thighs and were wrapped in nylons that gave her legs a white glow in the light of dusk. Under her open coat she still had her V neck green school sweater on. The green and gold School patch with its large globe resting atop a table covered in books heaved out from the pressure of her large breasts against the thin fabric. Her white blouse was opened at the first three buttons further revealing the size and shape of her bust.

Shelly's tits were great. They were large, at least a 36D. She loved showing them off. She was constantly getting looks from guys at school because of them. Even in the conservative school uniform the girls in school had to wear Shelly was always coming slightly unbuttoned and revealing too much leg. Her skirt was hiked up and the shape of her ass was clearly visible. It was large and round, the product of the end of a long swim season. Shelly was by no means a big girl, but she had amazing curves.

It was starting to snow hard and I jogged up to Shelly at the doorstep just as Lindsey opened. Loud music was blasting inside, and Lindsey was wearing a pair of flannel blue pajamas. She screamed with joy and jumped into Shelly's arms. I could tell she was already a little drunk.

Her red with highlighted orange hair was pulled back in a pony tail, her eyes were a sparkling emerald green and she had a great smile. The bottom button of the pajama top was open, every time she moved her arms away from her body her toned stomach was revealed. Her medium sized breasts pushed away against the flannel, and it appeared she wasn't wearing a bra.

We walked in the open door and into the foyer of the large house. Lindsey grabbed Shelly's hand and dragged her into the high-ceilinged kitchen, I followed them and dropped my bag on the counter. A wine cooler was open on the counter.

"Oh my god I'm so excited you guys are here" Lindsey said excitedly "it sucks I have to stay here alone all week, I've been so bored."

"We are gonna have a great time honey, I'm sure of it" Shelly said, turning to me "you should put those bottles in the freezer jack."

I reached into my bag and pulled out the two illicit bottles of vodka and a pint of watermelon puckers. Lindsey ran over and grabbed a bottle.

"Oh my god you guys are the coolest, I only had a couple of beers that I stole from my dad" Lindsey stated with a smile. "We are going to get blasted tonight"

"That's the idea Babe" Shelly smiled, giving me a sideways glance.

Shelly had met Lindsey on the swim team, when we were seniors she was pretty high up on the ladder on the team. Lindsey was her "baby sophomore" that she had taken under her wing. She took her to parties and to the mall, she got her drunk for the first time and had introduced her to boys. Now little Lindsey was a senior, and Shelly got a random email from her saying that her next trip home she should visit.

My relationship with shelly started around the same time, on her 18th birthday Shelly's friends threw her a party. Shelly got incredibly drunk and started ordering guys to do things to her, stupid things like demanding, "Its my birthday so you have to get me another beer." and "Its my birthday so all the guys have to take their shirts off for my entertainment." We all played along for a little while, and Shelly corners me in the bathroom and demands I make out with her. I reached in and kissed her, the next thing we know we are in the unheated pool house changing room in the dead of a New Hampshire winter and I'm banging the birthday girl.

Three and a half years later, we were still fucking whenever we got the chance, never actually dating, but at least once a week (leaving out times when we were dating other people...well, most of the time) we would be somewhere fucking. We clicked because we always kept the sex interesting, we would let each other explore any sexual fantasy we had. When I wanted to fuck her ass, she let me. When she wanted to dominate me, and tie me up, I let her. We kept this discreet, no one knew we were anything more than friends.

So one day when Shelly came up to me in the hall outside apartment and asked me how I would feel about a threesome I was game. She wanted to fuck another girl and had for a long time. For a while last summer she had gotten wasted and been hooking up with a girl who lives in Philadelphia, but had not wanted anyone in her family or school to find out about her lesbian tendencies so she broke it off quick.

I agreed that the thought of fucking her and another girl was a great idea. She suggested that we keep it away from school and, but had no idea how. Luckily this conversation occurred one hour before innocent 18 year old Lindsey Collins would e-mail Shelly and tell her that her parents would be away for a week and a half, and that Shelly should come stay over one weekend. Shelly quickly hatched a plan to seduce her. The first Friday night Lindsey's parents went away Shelly and I would stay over her house. This would provide a chance for the plan to actually happen. Shelly told me to leave everything to her, if anyone could pull this off it was Shelly.

I walked into the living room with my bag, Shelly followed and asked Lindsey to come in. I pulled out my little pouch and opened it, taking out a glass pipe and a canister of pot. Shelly had said that Lindsey had just started smoking pot, and to get some of the best in school so we could get stoned. Lindsey skipped into the room with a screwdriver in one hand and a remote control to the houses central sound system.

"So what do you guys want to listen to, I have like thousands of songs on the computer.." she stopped and looked over at me. "Awesome jack you have pot. Can we smoke?"

"Anything you want Lindsey, I'm your guest. I got this the other day its really good stuff." I smiled then looked at Shelly, "Shelly said you guys haven't been able to party at all because of

the swim season. I'm sure its going to be a crazy night."

"Yeah totally I'm already sort of drunk! would you guys like to have a cigarette outside?"

"You should show Jack the way the way Lindsey, ill get my cigarettes" Shelly purred, the got up and walked into the kitchen.

Lindsey walked swiftly through the house and out the sliding door onto her deck, in one corner under a balcony was a table and chairs, on the other side was a large hot tub.

"Is that on?" I suggestively asked, pointing at the tub.

"Yeah, its great to go in when its snowing like this, its so quite and no one can see inside." she whispered back, then covered her face and exploded in a burst of giggles.

"Hmm... maybe we will have to try that some time." I said with a grin, and turned toward her and handed her my lighter

"Anytime you want Jack."

I was impressed by Lindsey already, before I had known her as Shelly's little friend who was always calling when I was trying to get laid. Now she seemed to have a personality, she really seemed to want to impress me and Shelly too. I wondered what Shelly's plan was for tonight, she said not to worry about her plan, just to go with the flow, she would handle everything.

Shelly opened up the sliding door and walked out onto the deck, She lit a cigarette and pulled her coat tightly around her. "guys, I'm wicked stressed."

"What's wrong Shell?" Lindsey asked her voice full of concern.

"Well I just realized I don't have a bathing suit to go in the hot tub."

"Well we could all just go in naked." I stated sarcastically, "its only fair."

"Good idea" Lindsey joked.

"Yeah Honey" Shelly smiled back "that would be your dream, in the hot tub with two hot girls from the swim team, ill keep that in mind..."

We finished and went into the house, settling in the living room on the large wrap around couch. Shelly placed the vodka bottle in the middle of the table and broke out three shot glasses. Lindsey was getting loud, she definitely was feeling the vodka. She crashed down on the couch next to me, and sank in close to me.

"So you guys wanna play a drinking game? Its really fun." Shelly said, looking me in the eye. "Your gonna love it, its like truth or dare."

"Ill play" Lindsey blurted "I'm no chicken"

I looked at Shelly raising a eyebrow, she grinned at me. I asked "what are the rules?"

"Well you guys wanted to really party right? if you pick truth you have to answer a question, if you don't answer you have to drink, same with a dare."

"Sounds like a good time Shell, I'm in." I said, winking at her. I reached onto the table and poured three shots. I looked at Shelly "if I can ask the first round."

"Ok" she said smiling.

"Shelly, truth or dare?" I asked, looking her dead in the eyes.

"Truth, I have nothing to hide?"

"Ok" I sat back and scratched my chin. "Who did you loose your virginity to?" I knew she would lie, or take the shot. We both knew that I was the first guy she slept with, and would never admit it for fear of blowing our cover.

"Well, that depends. The first person I had sex with didn't take my virginity." she looked at me with a smile. "I lost my virginity to Catherine Kass the summer before I had sex with Bill Palmer."

She was lying of corse, she had sex with Catherine Kass the summer after I had sex with her, but I was surprised she would tell Lindsey this.

"What, you had sex with a girl?" Lindsey asked excitedly. "Are you a lesbian?"

"No way, I just like to have sex with girls sometimes. Believe me its awesome" she giggled, her cheeks were turning red. She looked at me and smiled. "Ok its Lindsey turn."

"Ok Lindsey, truth or dare?" I looked at her and asked, smiling. She kept making eye contact with me and then breaking away. Her smile was soft and she was obviously drunk.

"Ok...da...no...truth."

I thought for a second. "Lindsey, you have lovely red hair, are you a natural red head?"

"yes of corse" she responded happily.

"Well, prove it." I said

She stopped for a second, looking me in the eyes, then turning to Shelly who was lounging on the couch next to her.

"I think he is asking what color your pubic hair is Lindsey?' Shelly laughed, Lindsey face instantly became bright red, contrasting to her ivory skin.

"Umm...I don't think so." Lindsey stammered then giggled. "Ill show Shelly if you leave the room."

"No way, she could lie, looks like you gotta take the shot." I said flatly. I reached down and lifted a full shot to Lindsey.

"Oh come on honey" Shelly assured her "the whole point of the game is to do something outrageous, think of how you can get him back If you do this one little thing."

"Ha your right, ok ill do it. Your going down Jack" she stood up, and opened the bottom of her shirt. I looked at Shelly, her eyes had lit up when she saw the little Redhead looping her thumbs under the waistband of her pants.

"Ok, here goes..." Shelly leaned in, her eyes fixed on Lindsey. She pushed her waist band down, past her hips, and bent down, her round toned ass moving up as she did it. She rose up glancing at the two of us, our eyes fixed on her, he red pubic hair was trimmed in a small vertical stripe. I licked my lips and looked and shelly. "Ok I think you guys got enough" she said as she bent down and pulled them up. "Ok Jack your turn. Truth or dare, What will it be?"

"I'm no chicken, ill take a dare." I stared Lindsey in they eyes, taking on a serious tone. Shelly reached over to the table and took a shot, raised it to her lips and drank it.

"This should be interesting." she said as she placed the glass back down on the table.

"Ok Jack" Lindsey looked at me with a sly grin. "I showed you mine, now you show me yours, pull down your pants."

"Ok Lindsey, you got it." I stood up and untucked my shirt, I turned around as I unbuckled my belt and unzipped the fly on my jeans. I turned and asked if she was ready, then I jumped around, and dramatically dropped my pants. My eight inch dick was starting to get full and slightly hard from the excitement of the game.

I lingered with my pants around my ankles, letting the girls appreciate my cock. Shelly looked approvingly as I stood their in all my glory, she always complemented me on my dick, she loved it when I fucked her deep, and she said it was the prefect width.

Lindsey stared open mouthed, I wondered if she had ever seen such a big dick before. She gulped then looked up and made eye contact with me. I smiled back and she blushed and looked away embarrassed. She turned back to look at me again, her gaze lingering. Her eyes widened as she too me in.

"Its ok to look, remember I saw you already"

She stared back and smiled, then looked back down. I knew she was turned on a little, and this in turn got me even harder. I pulled up my pants when Lindsey noticed the fact that I was getting aroused.

Shelly sat up and looked at me. "Its my turn" she started taking off her school sweater, her sheer short sleeve white shit was unbuttoned showing her ample tits, and her black bra was showing thought the sheer fabric. "Ok Jack, truth or dare?"

"Ill take dare, for the second time I might add." I responded, laughing slightly.

"Ok...I dare you, to make out with Lindsey for two minutes, Ill keep time." she looked at Lindsey and asked "that's alright with you honey?"

"Umm, I don't know, I mean, if he wants to..I guess.." she stammered.

"Ill do it" I interrupted her, then turned and faced Lindsey on the couch. I lent in and brought my face level with her "just relax baby" I said moving in to kiss her.

Our lips met, she awkwardly turned her head then came into me, I kissed her softly at first then her mouth opened and she started kissing me passionately. I moved myself on top of her reclining body, pressing myself onto her, my arms wrapped behind her neck and back and I pulled her close, my now full erection pressing into her leg.

She gasped when she realized what it was, and then pressed her head into my neck and wrapped her arms around me. She nibbled my neck and kissed under my chin. My arms softly brushed her sides and began trailing up to her breast, just sliding below the left one under her pajama top.

"Ok lovebirds time to stop." Shelly yelled. "You guys looked like you were enjoying that a little too much." she laughed and smiled.

I lingered my hands just barely touching the bottom of the swell of her breast. I glanced up at Lindsey who hadn't lifted her lips from my neck, I lifted myself up, breaking the embrace.

I smiled and swallowed hard, looking deep into her eyes I said "wow Lindsey that was great...""

"Its ok Jack, it was...really nice." she stared at me, her hand still griping mine. She shifted on the couch, still lying on her back, leaning her body away from me, but still lying her legs across mine.

"Ok, I believe its my turn" I looked over at Shelly, her smile beaming. She knew I really enjoyed that, and I felt I should reciprocate a little. "Shelly, truth or dare?"

"Hmm... I pick...dare." she looked at me and smiled, her face flushed with anticipation.

I turned to Lindsey and smiled,"Well, I would just like to say, how nice it was to kiss Lindsey, and I think that my friend Shelly should experience that. That is if Lindsey would let her." I turned toward Shelly, "Lindsey is really beautiful, I cant believe I didn't notice before."

I was laying it on pretty thick, not that I didn't think Lindsey was beautiful, but that I wanted this plan to work. The thought of fucking the two of them silly was just too much to deal with. I looked at Shelly who sat up and looked over at me.

"I accept the dare, if Lindsey would let me." She looked at Lindsey, who was lying on the couch. I rubbed her leg, almost encouraging her. She looked me in the eye, then glanced at Shelly, then back at me.

"Yeah, ok, I will." she smiled and giggled, I passed her a shot and she gulped it down.

Lindsey sat up and moved closer to Shelly. Her hand slowly moved next to Shelly's thigh. Sensing her hesitation Shelly grabbed her hand and placed it on her thigh, then slowly moved her body. Lindsey turned her back against the couch and Shelly moved over her, Lindsey sat back as Shelly's mouth started softly kissing her neck while holding her hands at her sides.

Shelly was taking control of Lindsey, she loved to dominate over her partners. She lifted her head and looked down. The redhead turned her head into Shelly's, intimidated slightly by the force Shelly was using. Lindsey then wrapped her hands around Shelly's waist, sliding them under her untucked shirt. Shelly slowly moved her head closer, and gave Lindsey a soft kiss on her cheek.

Lindsey looked up at Shelly, their eyes met and Shelly dropped her lips so they were touching slightly, then pressed her body into Lindsey. Shelly's hair was pushed off to one side. Her cleavage heaved against the black bra that was nearly revealed through the blouse that was unbuttoned at the top. Lindsey pulled Shelly down onto her harder, her hands moving across Shelly's back.

They kissed, softly at first then gaining intensity, Shelly's arm was moving up across Lindsey's belly as Lindsey rubbed her lower back. I could hear a light moan of pleasure come from Shelly move closer to her on the couch. She wrapped her other arm around Lindsey neck and I could see them kissing each other with open mouths.

Lindsey leg was still draped over my lap, I could feel her rubbing her foot back and forth over my thigh. She stretched out farther bringing the foot in contact with my hard dick. Through my jeans she started rubbing her foot against it. I reached out and rubbed her upper thigh, feeling the soft flannel of her pajama bottoms.

Shelly's hand had moved under Lindsey's top, I could see that she was ribbing her breast, tweaking the nipple. Shelly broke the kiss and started kissing her neck, looking at me slightly and smiling with lust when she saw me rubbing Lindsey. I smiled back realizing that our plan was working perfectly.

Shelly intensified her kissing and a loud moan escaped Lindsey as she focused on her neck. I rubbed her thigh faster, placing my open palm flat against the back and moved up, until I was just slightly rubbing the bottom of her ass. I dropped my other hand to her foot that was

rubbing my dick, I wrapped my large hand around her little foot and started massaging it, still letting her rub my dick through the fabric. I moved slightly closer to the two girls, looking them over, watching Shelly as she turned this little redhead on.

"Ok that was more like five minutes guys, the rule was two." I said, interrupting them before I was left out of the fun.

Shelly broke the embrace and sat up smiling, her hair was all over the place and another button was undone from her shirt, "Jack your ruining our fun!" she moaned.

I looked at Lindsey, "and how are you Lindsey?"

"Mmm that was great..." she trailed off, the pleasure dripping off the words.

"I'm glad you enjoyed it, I certainly did" I glanced back at Shelly, who was biting her lip and smiling.

"Lindsey, its your turn to ask." Shelly said, pouring another shot.

"Ok, Jack, truth or dare?"

"Ok, truth" I say glancing at Lindsey who was shifting herself up and staring at Shelly, giggling a little.

jackh.
jackh.
1 Followers
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