tagAnalShy Girl

Shy Girl

byJamesSD©

Have you seen her? You probably know, or perhaps can remember, a girl like her. She's the cute girl who sits in the back of the classroom and never says anything to anyone. She quietly takes her notes and leaves when class is over. Sometimes those kind of girls have secrets. Wonderful, naughty secrets.

She's quite the riddle. She's pretty, but not stunningly beautiful. The sort of young woman that men notice, but don't trip over themselves to talk to. She puts on glasses during class to take notes, which only adds to her charm and mystique. She dresses casually and comfortably. This girl doesn't feel a need to wear heavy make-up or high just to go to class, unlike many of her peers.

What's her name? Does she have a boyfriend? A fuck-buddy? Does she live with her parents, or in the dorms? God, what's her name? A glimpse at the top of her test page reveals her name is Lisa.

The best way to meet a shy girl like Lisa is to be brave, bold and somewhat direct. Introduce myself, smile, be friendly but not overbearing. She smiles back shyly, and answers questions with one word responses. Luckily the answer to "Want to grab a cup of coffee?" is "Yes."

Lisa isn't much of a talker, but she smiles a lot. She seems really happy just to actively listen, nodding and occasionally asking for clarification. She seems more impressed by sweetness and honesty than bravado. The conversation flows fairly easily. She's eighteen, almost nineteen, and a freshman. She used to dance all the time but her knees started giving her problems, and school is keeping her busy now anyways.

"What do you do for fun on Friday and Saturday night? Go out and party it up?" I ask her.

She looks a little embarrassed. "I usually stay in. Sometimes I watch a movie with my friend Katie, but not so much anymore now that she has a boyfriend. I read a lot, and I know this makes me sound like a huge nerd, but I like to study at the library on Friday night. It's much quieter there than on Sunday and then I can go out and enjoy the day on the weekends."

"So I guess you don't have a boyfriend?" I ask.

She quickly shakes her head no. "I have an ex. We went to high school together. He now goes to college 1,000 miles away," she replies, somewhat sadly.

"Are you seeing anyone now?" I ask, trying to sound casual.

"You're awfully interested in that, aren't you?" she replies with a teasing grin. "No, I'm currently free. I'm not ready for another relationship right now though. I'm just focusing on my classes."

I think she can see the disappointment in my face. I start to think about saying my goodbyes, that it was nice to meet her. She stops me with "Want to go back to my dorm room?"

I study her, wondering if it's the invitation I think it is. Now, an invitation to a girl's dorm room isn't the same as being invited into an adult woman's apartment. It can mean an invitation for sexual activity, or it can just be to hang out and talk. Of course, I accept Lisa's invitation, eager to find out where this is heading.

On the walk over she's still very friendly, but hardly flirtatious. No soft touches, no brushing against me. The conversation slowly dies after I resort to bringing up the weather.

Her room is tidy, with two small beds on opposite sides. "My roommate works late tonight," she tells me. I have to imagine that's a hint. She sits down on one of the beds, crossing her legs and looking nervous. I sit down next to her, a couple feet away.

"So, you aren't looking to date right now?" I ask her, breaking the silence.

"No, not seriously," she responds.

"How long has it been since you kissed a guy?" I ask.

"That's rather personal!" she responds, then adds defensively "It's been months."

I look at her, studying her body language. I can't read her. Her posture is defensive, yet she's obviously watching me, waiting for me to do something. I lean in slowly, moving my head towards hers, waiting for her to move away. When my lips are only inches from hers, she finally moves, closing the gap between us and kissing me.

Her lips are super soft, almost like silk. She kisses very delicately. Somehow I can detect her pent up passion that is aching to be set free.

After a minute or two I break the kiss and whisper, "We can do as much or as little as you want to. We can stop whenever, ok?"

"Frankly, I don't think that's going to happen. But that's still sweet," she tells me with a smug grin.

With that she turns and straddles me, grinding against me through our clothes as we resume kissing passionately. I slide my hands down to cup and squeeze her firm little ass, eliciting a load moan from her.

I nibble on her neck and tease her earlobe. I really want to get her out of her clothes, but don't want to rush anything. I break our kissing to remove my shirt. She takes the hint, and lifts her own shirt up over her head, first exposing her tummy and then her brightly colored bra.

She's small on top, like most slender women are. I kiss her shoulder, her collar bone, sliding my hands up and down her sides and across her bare back.

"You really know how to get a girl worked up!" she exclaims. "And I can feel something in your pants that tells me you're just as excited as I am."

"That's very true," I reply, grinning stupidly.

"That can't be very comfortable. Let me help," she said, sinking to her knees on the floor and unbuttoning my pants. I lift my hips to help her slide them off, my erection now contained only by my boxer-briefs.

"Oh my, yes, you are looking very excited," she coos, sliding her hand across my inner thigh. "I wonder, should we do something about this?" she teases, looking up at me with her gorgeous blue eyes.

"Like I said before, we can do as much as you want to," I reply.

"I plan to hold you to that," she says, then slides her hand up to caress my package through my underwear. She teases me like that for a while, taking her time before hooking her delicate fingers at the waistband of my boxers and tugging them down.

The head of my cock catches on the waistband, so it angles down before springing up to full attention once it's free. "Oh my!" Lisa exclaims. She reaches her hand out tentatively to stroke my erection. "Yes, I think I know exactly what to do with this."

We both watch in wonder as her hand slides up and down my cock gently. I don't want to even blink, I want to remember everything and burn these images in my memory forever. She smiles at me, a naughty, mischievous grin, then moves her head forward, tongue extended.

I actually jump when her slippery pink tongue makes contact with my cock for the first time. She lets go of my cock with her hand, so the only contact between us is the tip of her tongue and my erection. She slides it up and down my entire length, then swirls it around the head of my swollen member.

"God..." I moan.

"Would you like something?" Lisa asks, once again grinning impishly.

"Would you... god, could you suck on me?" I ask, more desperate than I'd like to.

Lisa smiles sweetly, then opens her mouth and swallows half of me.

Her mouth is as heavenly as her nubile body. She sucks up and down me slowly, maintaining tight contact yet avoiding even the slightest scrape of teeth. She bobs up and down on me with practiced ease. I admire her confidence; she knows she's making me feel good, she doesn't have to ask.

Now I'm in a minor dilemma. I don't want it to ever end, yet I know I'm going to need release at some point if she keeps this up. I'm not sure if I can come in her mouth. I'm also not sure if she wants me to fuck her. "I'm close..." I moan softly.

Lisa immediately releases my cock and stands up. She unbuttons her jeans as I watch with rapt attention. Almost painfully slowly, she slides them down off her hips and legs and steps out of them gracefully. Her panties are a pink, tiny low-rise thong. She quickly hops back onto my lap and kisses me, my erection pressed against her miniscule undies and squeezed between our stomachs. I squeeze her bare ass cheeks, savoring their soft yet firm texture.

My hands roam all across her body, up and down her smooth back, catching on the back of her bra. I seize the clasp and open it, with surprisingly rapid success. She leans back just enough to toss her bra aside before pressing her bare chest against mine and kissing me once more. Still, I caught a wonderful glimpse of her small, bright pink nipples adorning the tops of her adorable little breasts.

We kiss and grope for a long time before she whispers, "I'd love to have you fuck me. Would you like that?"

I groan and nod enthusiastically. "I don't have protection," I inform her.

Lisa springs up and bends over to open a drawer, giving me a chance to admire her tight little butt. She glances over her shoulder and sees me looking, then wiggles her ass for my enjoyment. I see her pull a condom package out from the back of the drawer and inspect it closely before smiling.

"Hasn't expired yet," she informs me. "What can I say, it has been a while," she adds with a sheepish grin.

I reach out for the rubber, but she shakes her head no. "Let me." Once again she sinks to her knees, ripping open the package and slowly rolling it down the length of my cock. She slides back up my body and kisses me again.

"How do you want to do this?" I ask her, acutely aware of the latex around my shaft and the tiny layer of fabric still covering her pussy.

"You're the man," she replies huskily. "Take me any way you want me. ANY way."

"You sure?"

"Yes. I love it when a man takes charge. It makes me so horny."

"Well," I tell her between kisses, "first I want to fuck you with me on top."

She nods. "And then?"

"And then I want to fuck you from behind."

"Oooh, I'd love that. That's my favorite position," she replies excitedly.

"Let's get you naked," I tell her, trying to extract her thong from between our entwined bodies.

"Just to warn you, I'm a little fuzzy down there. I haven't exactly had reason to shave lately," she tells me. When I nod, she stands and slips off her thong.

Her pussy is hardly what I'd call hairy, but there is a dusting of soft pubic hair. I smile at her reassuringly and say "You look so sexy naked. Now lie down."

She follows my instruction, lying on her back. I use my hand to spread her legs slightly and move my hips between them. I slide my hand across her pussy, feeling her wetness. "You're very swollen," I tell her.

"Yes, I'm very ready for you. Please, fuck me," she replies.

I rub the head of my cock against her pussy, teasing her, and getting her ready to be penetrated. "Enough teasing, I need you now!" she pleads. I slide forward gently, pushing the head of my cock past her slippery outer lips and into her hot wetness.

"Mmmmm," we moan in unison as I work more of my cock inside her pussy. "You feel so good," she gasps. "I love how you feel inside me."

I kiss her lips tenderly as I rock back and forth, finally burying my whole length within her tightness. It feels wonderful to have my body pressed against her small, soft, feminine shape. I'm sure she enjoys having me on top of her.

"Oooh, yes, that's it. Faster, please," she encourages as I start thrusting into her. I support my weight on my forearms to get more leverage. "God, I love it," she continues. "Please, don't stop."

I look down and watch my erection penetrate her, sliding deeply into her slippery folds before emerging back out of her. My gaze runs up her body, to her nipples, then back to looking into her eyes. I thrust into her again and again, savoring the sensations of her warm young body pressed against me, kissing her lips hungrily. I penetrate her for several minutes, driving my erection deep within her, causing her to moan almost continuously.

When I pause momentarily to catch my breath, she caresses my face and states, "I'd love to get fucked from behind now."

I nod, and we quickly rearrange ourselves. I admire her firm, wiggling little ass for a moment before grabbing her hips and plunging my cock back into her with one powerful thrust, hitting her deeply.

"Yes, like that, you're hitting my g-spot!" she cries. She slips a hand between her thighs to rub her clit. I grip her hips and watch my cock slide into her, enjoying the feelings of her tight, warm pussy and the feeling of her buttocks against my hips.

"Don't stop. Oh God, don't stop," she instructs, frantically rubbing her clit. I pick up my pace a little. I'm very close, but I can tell she is too. Her pussy grips me, clinging to me tightly. "Yes! Yes, I'm coming!" she cries out. I can feel it, and it's exactly what I was waiting for. With a loud grunt I slam forward, thrusting my cock deep into her as I climax, feeling the rush of pleasure course through me.

We collapse into a panting heap, slippery, sweaty bodies entwined together. "God, that was so nice," she says, kissing the tip of my nose. "I've really missed getting fucked," she giggles. She glances down at my cock and asks, "Still hard, huh?"

"Yeah, I am. You're very sexy," I tell her.

"Well, I'm no expert, but my ex got soft almost instantly. I suppose every guy is different," she tells me, watching me take off the condom and wipe myself clean with a tissue. I settle back down and we sit in silence for several minutes, with me tracing my fingers gently across her back.

"Still hard," she observes. "Does someone want to go again?" she asks, hopefully.

"I'd love to," I reply. "But ladies choice this time."

Lisa nods, sliding her body down mine. She licks the head of my cock gently. "I love cock," she tells me. "I really enjoy just playing with one. It's so hard and yet soft at the same time. I get really turned on giving head."

"Your boyfriend was lucky to have you and stupid to break up with you," I observe as she takes me in her mouth.

"I broke up with him," she replies, releasing me momentarily. "Like I said, I knew that it was just too far to make it work. We both have needs, although I guess I haven't exactly been taking care of mine lately. Thanks for the help on that, by the way," she says with a wink.

Lisa sucks on me gently, much more relaxed and tender than the first time. I just close my eyes and enjoy it, letting my mind wander. When I open my eyes Lisa releases my cock and studies me for a moment. "Could you... would you please..." she stammers shyly.

"You know, at this point I would do almost anything you ask," I reply. It's true, considering how much I was enjoying the head she was giving me. "What would you like me to do for you, Lisa?"

She looks like she wants to say something. "I... you probably wouldn't be into it. You'd think I was dirty, that I was really slutty. Well, sluttier than I already am for brining you back here with me."

"If you've acted like a slut today then I definitely don't think it's a bad thing!" I reply. "What do you want us to do together?" I ask, curious.

After thinking silently for a moment longer, she slides up my body and presses her mouth against my ear. There's a moment's hesitation, and I can feel her warm breath in my inner ear. Finally, she whispers hesitantly, "Could you fuck my ass?"

"Seriously?" I ask, surprised.

She nods silently, staring into my eyes. "My ex used to do me that way. He was kinda small; definitely smaller than you. You guys love hearing that, don't you?" she asks, grinning and patting my rock hard dick. I can only nod in agreement. "So yeah, it was his idea at first, but I started to really like it. Ok, I love it. Like, I masturbate thinking about it. That's pretty bad, huh?"

I'm amazed by her confession. I've fantasized about anal sex, but my previous lover would have none of that. She thought anything involving the butt was gross. "I don't think that's bad. But, are you sure I won't be too big?" I ask her.

She blushes. "I have a toy, it's about your size. I've used it on myself there."

My eyes grow wide at the idea of this cute young thing getting herself off with a dildo in her ass.

"What can I say, I really miss it. It's just so... naughty. Plus, and I know this will sound a little weird, it's just freeing for me."

"How so?" I ask.

"Well," she continues, "again, I don't want to sound crazy, but a lot of the time my brain just won't ever shut off. I swear, I think too much. But when I have a cock in my ass, I just feel totally connected to my body. It's impossible to think about anything else. It just makes me feel so... so alive!"

"That sounds hot. I'd love to fuck your ass, Lisa." It feels good to say it, especially because it makes her eyes glow with excitement. "What's the best way to do it? Doggy style?"

"Hmmm, no, it's hot that way but it's actually easier if I'm on my back. It's a lot easier for you to go in slow that way. Plus, I want to be able to see your face when you're in my butt," she answers. She opens a drawer by her bed and pulls out a bottle of lube.

"Give me your hand," she instructs, pouring a good amount of the viscous clear liquid in her palm. She takes my wrist and coats my index and middle fingers. "Just slide your fingers into my ass for a bit and lick my clit, ok?" she instructs. "I need lubrication, and it helps if you warm me up with something smaller than your dick."

I can hardly believe that I just spoke to this girl for the first time less than 6 hours ago and now she's instructing me on how to get her ready to fuck her ass. Needless to say, I quickly moved between her legs and rubbed my fingers against the entrance to her ass.

"Mmmm, that feels nice," she moans as I slowly slip the tip of my finger into her tight bum. "That's right, slow and gentle."

I lick her swollen clit as I slide my finger in and out of her ass. "Slip another finger in," she whispers, sooner than I expect her to. I comply, and she starts moaning.

"That's nice. God, it's been a while since I've had someone else do this," she says. Her ass clings to my fingers as I slip them inside her, sliding in with greater ease thanks to the lubrication.

"I think I'm ready, stud," she informs me. "Just please, please, please, go slow."

"I will. Just tell me what you want and I'll do it," I tell her, slipping my fingers out of her and sliding my body up hers. She has to roll her hips upward more than for conventional fucking, but she doesn't look too uncomfortable. I rub the tip of my cock against her now slippery asshole.

"Rub lube all over your cock too," she instructs. I coat the condom liberally with lube.

"Ready?" I ask her.

"Oh yes. Fuck me in the ass with that big cock, stud," she tells me with a wink.

It takes all the willpower I have not to ram myself deep within her tight bum. Still, the fear of hurting her holds me back. Between the lube and her experience it actually isn't that difficult getting the head of my cock into her ass. She gasps loudly as I feel myself slip past the tight outer opening.

"You ok?" I ask, concerned.

"Yes. Don't stop. Just go really slow," she replies, eyes tightly closed.

I take her advice, rocking back and forth and slipping deeper into her, millimeters at a time. I marvel at the novel sensation of her ass compared to her pussy. It's tight, possibly tighter. Yet once my cock slips past the entrance it isn't so snug, except when she tightens her muscles around me, pushing me outwards and causing me to groan with pleasure.

"You like it when I squeeze you with my ass?" she asks. "I'm glad you do, because I love how it feels. Just hold still for a moment. I'm going to squeeze you, but don't let me push you out."

I nod, looking down at my cock, half of which is now buried in her ass. Lisa closes her eyes and clenches tight around me. I hold myself in place within her. It feels amazing. As she releases I slip deeper into her, no longer hindered by her resistance.

"Oh fuck," she moans, followed by something unintelligible.

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byJamesSD© 7 comments/ 149439 views/ 33 favorites

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