First Time Cumslut

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Jennifer entertains two men in a hotel room
3.3k words
4.27
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Twenty-one year old Jennifer arrived at the Hamilton Hotel, already dressed in her little schoolgirl outfit. She got some curious looks from people in the lobby, but she really didn't care. After ducking into the restroom briefly to fix up her hair, she quickly made her way to Room 107. She knocked on the door, and a man was quick to answer it. "Hi, I'm Jennifer," she said shyly, and the door opened with a smile.

"Hi, Jennifer. Wow! I'm Bill... Come on in!" Jennifer walked into the room as Bill closed the door and bolted it. "Hey, Scott!" he called into the bathroom. "You've got to see this girl!" She blushed as Scott walked into the room.

"Holy shit..." Scott muttered. The two men gawked over sweet young Jennifer, dressed in her little schoolgirl outfit.

Jennifer wore a crisp, long-sleeved white blouse, with a red/black/yellow plaid necktie. Her torso was caressed by a matching buttoned-down red/black/yellow plaid vest which fit snugly, accentuating her firm breasts and flat tummy. Jennifer's skirt was made from the same plaid fabric, layered in tiny knife-pleats, riding high on her lovely slim thighs. Her white cable-knit knee socks and black-and-white saddle shoes completed her sweet outfit nicely. Jennifer's lips shined with her red lipstick, and her hair was swept to the sides in two ponytails, with bangs draping across her forehead.

She enjoyed playing the part of an innocent little girl, and she swayed from side to side slightly, like a nervous youngster. "Do you like my outfit?" she asked, spinning around for the guys. Her flimsy, lightweight skirt flared out its pleats and gave the horny men a fleeting glimpse of sweet white cotton panties. "Shit, yes!" Bill blurted.

"What did you guys want me here for, anyway?" she asked, teasingly. Scott smiled at her, and then stepped up to her. He patted her ass lightly through her little pleated skirt.

"It all depends," answered Scott. Are you a good little girl, or a naughty girl?"

"Well, most of the time, I'm good, but when I'm naughty, I'm even better..." Jennifer replied, with the wink of an eye.

"Well, now, my little sweetheart," Scott answered, "let's see just what a naughty little schoolgirl you are..."

The stereo in the room was playing a very sensuous song, and Jennifer decided to use it to enhance her charms. She sat in a wide chair across from the bed. The men sat on the bed, watching her intently. Jennifer put a saddle shoe up on an armrest, and cocked the other leg wide to the other side. Her little school skirt draped down across the gap between her legs.

Scott and Bill were mesmerized. Jennifer was simply delightful in her little uniform. As they watched, Jennifer slowly slid her plaid pleated skirt up over her tight white panties, showing them her lovely panty-covered crotch. Jennifer loved every minute of this. She slowly slid a finger in through the leg band of her panties, probing her wetness, moaning softly to add to the effect. She could see their jeans begin to bulge ominously.

Jennifer continued to finger herself, her fingers moving in and out of her cunt under the panties, her knuckles stretching out the fabric. Her other hand slowly unbuttoned her vest and began massaging her breasts through her soft white blouse. "Would you guys like to see my little pussy?" she asked.

"Oh, yeah..." they both muttered, horny as hell.

Jennifer hooked a finger around a leg band and pulled the fabric to the side, exposing her almost-hairless treasure. The soft curls of pussy hair were glistening with her moisture, and the sight of it, coupled with the school uniform and her provocative pose, were enough to almost make the guys come in their pants right then and there.

"God, I could cum right now!" gasped Bill. "

"Oh, no, don't do that right now," said Jennifer. "You've got to fuck me, first! Let's see those cocks..."

The men quickly stripped before her. In seconds, their clothes were thrown aside, with both men standing before her, their pricks hard and lewdly wobbling in worship to the young princess. The men pulled her up from the chair and brought her to the bed.

"Hey, Bill, why don't you let her suck you while I eat her pussy?" Scott suggested.

"Great idea!" Bill quickly agreed. He lay on the bed, his head propped up on a pillow.

Scott reached up under Jennifer's flimsy little skirt and thumbed her panties down, tugging them over her precious ass cheeks, till they fell to the floor. Jennifer tossed her vest to the floor. She crawled onto the bed, slowly moving her way up between Bill's legs to his waiting prick.

As she gripped Bill's warm, hard cock in one hand, she felt her little skirt pulled up high on the back of her ass, high in the air as she knelt on the bed, and the wonderful sensation of a man's tongue on her pussy lips.

She knew she was going to really enjoy this night. Scott lay beneath her, holding her ass with both hands so that her scent and essence was close to his face. He licked up the length of her labia, from the perineum between her pussy and anus all the way past the clit to her curls. She shuddered with pleasure and ground down on his chin, all the while stroking and licking Bill's cock. Scott slipped two fingers inside her pussy, his ring finger into her tight asshole, and used his thumb to press and circle around her clit while he licked and sucked the juices that flowed freely from her hot hole. She pressed down and thought she'd never felt so full, but she was to be proven wrong before the end of the evening.

Meanwhile, Bill was savoring the attention she paid to his cock. He knew he'd have to pace himself if he wanted to last the night, and he hoped he could go two or three times. He wanted so badly to see his cum spurt over her lips, tongue, teeth, nose, and chin, but he also wanted to feel her young, tight, hot box gripping his cock while he came.

She began stroking him faster and faster, and sucking the head of his cock like sucking the shine off a doorknob, and before he knew it, he got his fist wish. She arched up a bit to let his cum jump over two or three inches of space to hit her face over and over as he convulsed and released spurt after spurt on her face. She smiled all the while, knowing she was putting on a good show, and enjoying Scott's skillful tongue and fingers as they continued to probe her.

He got up and found a towel, dampened it and offered it to her to wipe her face. "What a gentleman..." she murmured, gratefully accepting as she continued to ride Scott's face to another of several orgasms. She arched her back and turned a bit to see Scott's cock bobbing, its angry purple head looking like the doorknob mentioned earlier. "Can I sit on that, and ride your big prick for a while, darling?" she asked.

As his response he took her by the hips and slid her down, settling the head of his cock easily between he soaking pussy lips, and threw his arms out to the side as if to say, "Go for it babe, it's all yours..." She slipped down, down, down his pole, taking it centimeter by centimeter, excruciatingly slow, until he filled her completely.

She sat up to unbutton her blouse, but left it on. She caressed her tits and rolled her nipples between her thumbs and fingers as she ground her pelvis left and right a bit, then slipped herself back so that his cock would caress the front wall of her pussy with each stroke. She threw her head back and started to ride him, eyes closed and hair whipping around her shoulders as her thighs clenched and she pushed herself up and down on his member.

The sight of that gorgeous young thing fucking his friend with such complete abandon made Bill's cock wake up and take notice. He was thrilled to be back in the game so soon. Scott's eyes were closed, an effort to keep from cumming too soon, but Bill could see Jennifer's small perky breasts bounce as she thrust up and down on Scott's long cock.

After watching her have an obvious orgasm and slow her pace, Bill came up behind her, between Scott's knees and reached around to tweak her nipples. She arched her back, pressing her lovely breasts into his hands and covering his hands with her own as she showed him how she wanted, how she needed, to be touched. He leaned her back onto his chest and held her while Scott thrust up into her. She could feel Bill's cock pressing against the small of her back and she opened her eyes to give him a look that said, "I've got an idea...follow my lead."

She leaned forward across Scott's chest and stretched to reach a bottle of lubricant she saw on the nightstand. Handing it back to Bill, she asked, "Have you ever been in someone's ass while they were being fucked before? Let's try it now...it'll be my first time, too." He was so surprised (and excited) by this he wanted to cry. A girl who asks for anal? He could just imagine that tight canal clenching around his cock, which leaped in his hand at the thought.

Bill lifted her short skirt up over her ass again, and opened the little bottle. He drizzled some of the silky, oily, berry-scented substance down her crack, and onto his cock too, for good measure. He moved closer, kneeling behind her and between Scott's legs, which she straddled, thus opening her ass cheeks wide. She looked back over her shoulder at him and smiled, and Scott lay still waiting for everyone to be in place. Then she looked back at Scott and kissed him passionately, stroking his mouth with her tongue as she felt Bill's cock ease into the entrance of her tight asshole. He pushed a little, then waited to let her muscles relax around him, then pushed a little more. He kept looking at her to gauge her reaction, but she gave no indication that she wanted him to stop. Little by little he slid the entire length of his cock into the slippery, tight puckered hole, feeling Scott's cock bulging like a long pipe through her interior wall on the underside.

"Okay, we're set," he said, and Jennifer began to move forward and back, forward and back.

Then she said, "It might work better if you two just do the movement...I don't want to lose contact with either of you. My god, I've never felt so filled before--it's fucking fantastic!"

So Bill and Scott began the thrusting motions, the same rhythm and the same pace, so that they were stroking each other's cock at the same time as they slid in and out of both of Jennifer's tight, hot, throbbing holes. The pace was somewhat slow and deliberate, but constant, and when she started to moan very quietly in the back of her throat, they knew she was going to cum like never before. They kept it up, steadily stroking, stroking, and Scott was the first to lose it. She was laying on him, supporting herself with her arms, but with her head next to his shoulder, he heard her soft moans and mewling cries first.

She was incoherent when she came, and all he knew was that his well-ridden cock was ready to explode, and her soft voice and audible pleasure was just the thing to push him over the edge. With a loud grunt and a load of cum that shot deep into her pussy, he came, thrusting and rocking again and again. Bill held off a little longer, but soon felt the tingling deep in his balls that meant he'd be showering her with his cum juices soon, too, so he pulled out and watched white cum fly out of the end of his cock onto her sweet, upturned ass.

Sighing with utter satisfaction, they flopped onto the king sized bed and Scott reached for the damp towel to clean her off, above and below. Jennifer excused herself to the restroom and Bill used the towel to clean off his cock that had just been buried, balls deep, in her ass. When Jennifer emerged from the bathroom she was wearing only an oversized white t-shirt. With everyone clean and dry, they curled up, triple spoon style with Jennifer in the middle, and slept for the rest of the evening.

Later, Scott was the first to awaken, and as he was cuddled behind Jennifer, he slid his hands up under her t-shirt and gently, but firmly, massaged her breasts. She sighed and stretched and rolled around to face him and snuggle her face into the warm cave of his shoulder. Bill still snored soundly. Scott whispered to Jennifer, "I want some of what Bill got earlier...will you let me...?"

As her response she smiled mischievously and reached down to stroke him.

They moved to the other king-size bed in the hotel room and Scott sat on the edge of the bed while Jennifer got to her knees in front of him. "You have an absolutely gorgeous cock," she said, stroking him with two fingers from the head of his tool down to his balls. "I'd love to feel you fuck my face, and slide your prick all the way deep down my throat...I can lay back and you can 'feed' me your hot dog...would you like that?"

He groaned and asked, "Where have you been all my life?" She smiled and began to lick and suck his member. She ran her teeth gently up and down the length of it. She closed her teeth tightly and ran her pearly whites up and down along the veined ridge on the underside of his cock. She took him down lower and lower and lower until he felt the head of his cock pop past the tighter barrier that was the depths of her throat, until she said, "Okay, hon, it's time..." and stood him up while she herself lay back on the bed with her face looking up at his member, her neck partway off the mattress. "You are the perfect height for this...just stay standing and fuck my face," she said.

She leaned back her head and opened wide her mouth, and he slid himself straight down to the back of her throat with one long, slow plunge. She took a deep breath in on his outstroke and grabbed his ass with both her hands, inviting him to stroke again and again, deeper and deeper, staying down for longer and longer periods. She held his ass hard against her face, nose buried against his balls, lips stretched wide at the base of his cock, throat muscles totally relaxed and open, and to all observers appeared to savor and enjoy the sensation.

When she was able to, you could hear her moan and purr, the vibrations of her throat carrying to his prick and massaging him...had she not been taking it deliberately slow, he'd have blown his wad long before, but he could tell she wanted, no craved the sensation of being stuffed to the gills with cock. She took her right hand off of his ass and reached down between her own legs to stroke her own swollen sex.

Suddenly she realized there was another pair of hands assisting with her exploration, so she let Bill (who had awakened and joined the twosome) stroke her clit and lips, finger fuck her and lick her. She opened wide as he put both hands on each of her inner thighs and spread her, burying his face in her tasty treat, sticking his tongue as far deep as it would go and nibbling her petal-like lips and the core of her pussy, her erect and pulsing clit. Jennifer continued to be face-fucked by Scott, and she put her hands once again to her erect and hard nipples, to roll them between her fingers and pull and pinch them roughly. She was in the mood for some harsher play tactics.

After munching her hot box awhile, Bill slid his hard cock into Jennifer's pussy and, holding onto her hips, slammed her hard and fast, making her head bounce hard against Scott's thighs. Scott withdrew his cock and leaned over her chest, licking and biting her nipples as she offered them to him on by one. As Bill's movements were getting faster and harder, her tits bounced around her chest and Scott had to hold them still so he could nuzzle them.

By now his five o'clock shadow was growing in, and his whiskers left a red angry rash on her chest. Bill pulled out and shot his load onto a towel nearby, then went back to eat her swollen, throbbing cunt. Scott joined Bill between her legs and they took turns licking and sucking her clit while she writhed and moaned and squealed, holding hard to the pillows and blankets.

Jennifer pulled away for a moment, turned herself over and kneeled ass-up holding on firmly to the headboard. Bill slid underneath her and continued to pummel her cunt with his tongue and fingers. She looked over at Scott and said, "Come on, sweetheart, take my ass!"

Scott needed only one invitation. Her asshole was already slippery and wet from her cum-juices, which had poured from Jennifer during her multiple orgasms. She wiggled her tail a little as a tease just as he was getting his head near her pucker, and he said, "Well, hold still for me!"

Giggling, she said, "Alright, but make it fast--I can't wait to feel your cock riding high inside me." Her breath caught in her throat as she finished speaking, for Bill had her clit firmly trapped between his fingers and was sucking it for all he was worth at the very instant Scott slid his cock, none too gently, up her ass.

Sucking her breath in quickly she exclaimed, "Oh, shit! You're too big! Give me a second to get used to you..." and she tried to climb forward away from his tool.

Bill held her firmly by the hips and Scott grabbed her shoulders and said, "Not so fast, sweetie, you asked for this--you're getting it all."

Squeezing her eyes shut and focusing on the lips that were still pleasuring her button so intensely, Jennifer relaxed her ass and realized soon that she was enjoying the hell out of being so filled. Bill stuck two fingers up her cunt like Scott had done earlier in the evening, only this time his lips held firmly to her clit and her ass was full of Scott's cock, not his ring finger. Even getting fucked there earlier by Bill hadn't quite prepared her, since Scott was somewhat longer and wider, and they had used more lubricant before.

Quivering wildly, squealing and slamming the headboard with each thrust, Jennifer came and came, and finally felt Scott's hot jism course through her ass, stinging a little from where he'd been so rough. He slid out and leaned across her back, hugging and stroking her, while Bill continued to slowly lick the cunt that quivered and shook in front of his face.

Exhausted for the second time, they lay spent, as finally they realized how starving hungry they all were. Bill ordered room service while Scott and Jennifer showered, gently and lovingly caressing each other's body, and sliding soapy hands everywhere, then Bill came in and they all got covered with suds and warm water. They were truly spent though, and their hands slipped innocently across each other's bellies, backs and legs, just letting the cum wash away down the drain.

Jennifer knew right then that she loved how she felt, and that she wanted lots of cock, all of the time. She was going to become a permanent cum-slut for these two, and for any friends they might choose to invite next time.

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3 Comments
Will6969doWill6969doabout 9 years ago
Well written!

And it is obvious that you love to dance. And I love just how well you switch partners. It also seems that you learn new steps very quickly!

Loves_music_loves_to_danceLoves_music_loves_to_dancealmost 10 years agoAuthor
Response to Yesss Assss

Sounds like you're a gay man, so I'm super flattered that you read my story! Or are you bi-sexual? Either way, it's hot stuff to think about!

AnonymousAnonymousalmost 10 years ago
Yesss Assss

Nothing like a hard cock shooting a big load of cum up your ass is there? I try to get it as often as I can, after all, it's not just the ladies that like to get fucked there, and I don't mind having a big cock down my throat at the same time. Juicy and tasty and sure as hell sexy. oldvintner@msn.com

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