Freshman Girl Second Night

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I have anal sex with a girl for the second night in a row.
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This story was inspired by Damonx's story Freshman Girl.

*****

I decided to stop by Blondie's room for breakfast. That way I figured I could assuage any grudges she might have. A half hour spent now could prevent difficulties later. The look on her face when she opened the door told me I had made the correct decision: she was definitely not happy to see me. She held the door like a shield, her pale blue eyes a mixture of fear and doubt.

"Hey babe, how you doing?" I smiled pleasantly. "You wanna get some breakfast?"

"Uh, no, thanks...," she resisted.

"Come on," I cooed "most important meal of the day!"

She was very reluctant, but she was just a little freshman and unable to stick up for herself. A few more minutes of cajoling and she caved, emerging minutes later dressed but unhappy. I led our conversation, light, friendly banter, getting her to give simple responses. A smile finally cracked her face as we arrived at the dining hall. I complimented her hair and she thanked me. Soon I was getting answers out of her and we started to talk. Last night never came up, like it was no big deal. By the end of breakfast I was her friend again. She smiled and laughed with me. Crisis averted. You never know what foolish thoughts a little freshman girl might get in her head from all the sexual assault awareness the Uni shoves down their throats.

Late that night, my studying was interrupted by a timid knock. Lo and behold, it was my little Karen. She looked totally adorable, in plaid baggies and a loose red Coke tee. Her blond hair was pulled back in a ponytail. Her bare toes curled into balls and she didn't look me in the eye. I invited her in and closed the door behind her.

"So what's up?" I asked.

She couldn't even bear to face me, looking aimlessly around my room. "Um...,about last night."

"Yeah?"

"I'm...like...it hurts," she finally whispered, risking a glance at me.

I suppressed a snicker and put on a concerned face. Last night I had taken her anal cherry; the reality was that her ass was going to be sore. I hadn't gone easy on her. The phrase "She won't shit straight for a week" came to mind.

I said nothing.

"I think you hurt it."

"I think I wrecked it," I thought. "Well, I am pretty...big," I admitted. "And you are pretty...small."

She nodded in vigorous agreement, scared eyes flashing to mine.

"Have you been able to go?"

She nodded. "It hurt."

"Okay, well, maybe you tore something." Her eyes almost popped out of her head. "Let's get some shoes on and I'll walk you over to the clinic," I offered.

"Oh God, no," she answered, wrapping her arms around her with a horrified look on her face.

It was precious! She was so innocent she was terrified of telling a nurse she'd had anal sex! Once again I had to force myself not to laugh.

"Well, then what?" I asked, knowing exactly where this conversation was going. Having her say it would be much more fun, however.

"I was wondering if..." she started. I nodded to encourage her. "You could look at it," she whispered.

I frowned and raised a quizzical eyebrow. "I'm sorry?" I asked as if I hadn't heard her.

"Could you look at it and make sure it isn't...torn or something?"

I put on my best doctor look. "Karen, I am pre-med, but I am not a licensed health care provider. The clinic is just across campus, I'll walk you over and they can have a look."

"No, I...I'd rather not," she pleaded. "Could you...?"

I sat quietly, as if in indecision.

"Please?" she asked. "It hurts."

I stood and took her cute little chin in my hand, turn her face up to mine. "You sure you don't want to go to the clinic?" She nodded. "Okay," I finally agreed.

She flinched a smile at me and I sat back down, my dick starting to harden. I decided to take charge and move this along.

"Pull down your pants," I ordered.

The look on her face as she realized what would have to happen in order for me to take a look was priceless. I wondered how dense she really was. How else was I going to take a look? She swallowed and looked around the room again. She turned slowly and , bless her little dingbat head, little by little pushed her pants down. Sadly, her tee fell to obscure the view. I beamed inwardly and gave my crotch a squeeze, savoring the sight of this coed in my room with her pants at mid-thigh.

"You're going to have to lift your tee up," I pointed out.

She nodded, still facing the wall, and lifted her tee, She was blushing so hard, her butt was pink. And what a cute little butt it was, young and firm and ready to pounded. She was tensing her cheeks together. I let her stand like that for a few moments as I admired the view.

"Okay, this isn't going to work like this. Take off your pants."

"Take them off?" she begged in protest.

"Yes."

"Do I have to?"

"Yes," I answered in exasperation. "Do you want to go to the clinic? It will be the same drill there." Well, maybe not to same drill...

She seemed to gather herself for a minute before she allowed her pants to fall to the ground. God, she had great legs. After stepping of them, she looked over her shoulder at me for direction.

"Fold them," I asked a bit too harshly. "Don't want them to get messed up." I finished with a smile.

She nodded and quickly obeyed, folding them neatly. I took them from her and placed them on the shelf above my desk.

"Now, get on your hands and knees on the bed."

"What?" she asked with startled eyes as her head snapped around.

"You want me to take a look, right?"

"Yes but..."

"Hands and knees." I pointed firmly to the bed.

Like a good little patient she minced over, a hand demurely covering her sex. The wall jags in around my bed, such that the bed is surrounded on three sides by wall. She delicately mounted the bed across the foot, head to the wall and a shoulder against the other wall. Once in position, I pushed the tee up, leaving her glorious ass exposed to the room. I placed a pillow beneath her head and sat on the bed beside her.

"You okay?" I asked quietly, stroking her bare calf. She nodded, her face flushed in embarrassment. "Put your head on the pillow."

She lowered her head, still facing me. In a burst of inspiration, I had her turn to face the corner of the walls. Now, I could operate without her seeing what I was doing. She complied without argument. I positioned my chair behind her rump and couldn't help but smile. Her thighs were clamped tightly together. I quickly took a few pictures with my phone producing an anatomy book, as if I needed a reference. With her head facing the corner she was completely oblivious.

"Now Karen," I said, "I need you to spread you knees apart a little." She shuffled a little, but I encouraged her until her thighs were shoulder length apart, opening her crotch to me. "Now reach back with both hands. Both hands, Karen. And spread your cheeks for me, just like last night."

Her hands slowly took hold of her fleshy globes and parted the great divide. I adjusted my desk light to shine directly on the wonderful sight: her hairless pussy and pink asshole displayed for my inspection. I snapped a few more pictures. Much to my joy I discovered that in her position, her tee hung far enough from her body to show she was braless, her small boobs hanging deliciously. Her rectum was slightly inflamed, but nothing serious. Her pussy, perfectly shaved, was also on full display. I was going to have to make a decision soon. I allowed her to hold her position like that for a few minutes while I stared and planned my next move.

"Does it look okay?" she finally asked timidly.

"Well, from the outside it does. I'll have to probe you to determine if there is any damage under the surface."

She didn't respond, but didn't move either. I casually got my lube. Seating myself inches from her, I made her clench her asshole several times, catching her winking pucker hole on video this time. Next, I placed a dollop of lube on her and gently rubbed it around with my finger. She twitched as I worked but held her position. I went and got a nozzle for the lube, and inserted just the tip through her sphincter and injected more lube.

"Is that okay?" I asked as I settled my hand on her thighs, stroking lightly. She nodded. "We'll let it sit for a few minutes to take effect."

And sit we did, her bent over holding her ass open for me, me chuckling at my luck of finding such a good girl. I leaned close to inhale her precious feminine smell, all the while tenderly stroking her thighs. I allowed my hot breath to wash over her and had her clench a few more times.

"Okay, I'm going to insert a finger. Let me know if it hurts."

She nodded and tensed even more. I lubed up my pointer finger, paused, and rammed it in to the knuckle. She bucked and yelped from the unexpected ferocity of the intrusion.

I immediately pulled it out. "I'm sorry, did that hurt?" I asked, watching her ass clamp reflexively.

"Kinda," she whispered.

"Okay, I have to do this, are you ready?"

She nodded again. This time I slowly inserted my finger, allowing myself to feel every millimeter of her backdoor. Once fully inserted, I slowly wriggled it around. Twisting my hand, my eyes fell to her pussy, and much to my joy I could see the increased pinkness of her sex.

"Karen, does this hurt?" I asked, transfixed on her cunt.

"Not really."

"Good. I need you to clamp down as hard as you can." Her anal ring immediately tensed around my finger. "Good girl. Now, keep squeezing," I encouraged, then slowly pulled my finger out. She tried desperately to hold me in, but the lube did its job and my finger slid free, eliciting a small whimper from her.

"You doing okay?" I asked. She nodded. "Did that hurt?"

"No," she answered quietly

"Okay, I'm going to do that again. I need you to clamp down as hard as you can. I'm going to work around your rectum, making sure everything is in order, okay?"

"Yeah."

I smiled and slowly pushed my finger back in. Like a good girl, she squeezed down as hard a she could. This time I pushed to her left, giving her the impression that I was testing that section. I slowly removed my finger again, finally popping free from her pressure. Again I was rewarded with a small moan.

"Did that hurt?"

"No."

I slowly inserted my finger. She clenched again. This time, I pushed left and a little up. She squeaked with each insertion and removal, her hips wriggling in concert with my finger. I repeated my line of questioning each time. She repositioned her hands on her ass to get a better grip. She was holding on so tight she was leaving hand prints. I smiled as I noted the moisture on her slit. I patiently finger fucked her ass, working meticulously around her rosebud. By the halfway point, she was moaning and practically fucking herself on my finger. All I had to do was place my finger on her and she rocked back to impale herself, squeeze, and then pull forward until I popped free. I paused between insertions, watching as she pushed back against air, searching fruitlessly for contact. When I finally touched her again, she lunged back with a groan and repeated her routine. I added a second finger and grinned as she pushed back again, accommodating both fingers. This time I left my fingers in her, letting her fuck herself on my digits. I decide to add one more twist.

"Karen," I started. "Karen," I repeated sharply. She froze, shocked out of her stupor. "I need to check one more thing, your inner walls. Is that okay?"

"Yeah," she panted, not bothering to ask what I meant.

With one last squeeze of my boner, I reached up and inserted a finger into her wet pussy.

"Oh my God!" She jumped, her hands leaving her ass and grabbing the sheets. I pressed my inserted fingers together across her vaginal wall and slowly began sawing them in and out of her. She gave a long moan as her hips started to work in rhythm with my fingers. I was rock hard. She was voicing perverted obscenities as I finger fucked both her holes, incoherently begging me to fuck her ass. Once again I was amazed to hear how filthy her mouth got. Knowing how worked up she was turned me on even more. Finally good and ready, I pulled my hands away, dropped my shorts and lubed my cock. She twisted around to look at me, lust burning her eyes.

"Oh God!" she begged, staring at my manhood. "It's going to hurt!"

"It will be fine, you'll all warmed up this time. We'll go slow, just relax. Does your ass hurt?"

"No."

"Let me know if it hurts too much, I'll stop." I positioned myself at her back door. "Push back on me."

She did, cautiously skewering herself on my dick with a moan. After allowing her to work a good few inches in at her pace, I took hold of her ponytail and slammed myself home.

"Oh God!" she screamed.

I paused for a moment. "Karen, does it hurt?"

"Yeah, a little."

"Do you want to keep going?"

"Yes," she whimpered.

"Clamp down on me," I instructed.

I pulled out slowly, savoring the tightness as she tried to hold me in. With only the tip left in her, I pushed myself home again. After just a few thrusts, I used her ponytail to reposition her so we were aligned with the bed. With both hands on her back, I pressed her into the mattress as I quickened my pace and started to ream her ass.

"Where's my cock?" I asked.

"In...my...ass," she gasped.

"Louder! Where's my cock?"

"In my ass!" she practically screamed.

I grabbed a hold of her ponytail again and fucked her ass with long, full strokes, my balls slapping her pussy with each thrust. I noticed her hand was beneath her, fingers working quickly while we fucked. I wanted tits, so I pulled her arm away and pushed her tee over her head. Her arms were entangled as I reached under and filled my hands with her boobs, mashing them against her body. My fingers found her hardened nipples and squeezed them, eliciting yet another enthusiastic response from her. I could feel my balls start to boil, so I grabbed hold of her ponytail again and pulled her head back.

"Baby, you're going to make me cum!" I growled into her ear.

"Cum in my ass!" she shouted.

I obliged, pumping her ass full of my cum for the second straight night. My orgasm was even more intense this time, ripping through my mind as I deposited my seed in her ass. I came so hard it felt like I pulled a nut. I collapsed on top of her in a post orgasmic daze.

"Jesus, you're good," I panted as I lay cheek to cheek with her.

Finally my senses returned and I thought to ask if she was okay. She nodded shyly into my cheek.

"Does your ass hurt?" I asked as I softened in her.

"Yeah," she giggled.

I rolled off. I watched contentedly as she slowly slid from my bed. She craned her head back to take a look at her butt before getting her pants and gingerly put them on.

"Well, let me know if you want me to take a look at it tomorrow."

She grinned sheepishly. "Maybe I will." She let herself out of my room.

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6 Comments
roveroneroveronealmost 3 years ago

Agree w/6 yrs anonymous-very rapey, sick...one star

got agree with one tag on your story-clueless

AnonymousAnonymousover 5 years ago
she is cured

No more pain means more visits. Very nice and good short story.

AnonymousAnonymousalmost 9 years ago
A THRILLS A THRILL, YOU KNOW A THRILLS A THRILL, EVEN IN PARADISE...

Long John Baldry sang those words over 30 years ago. So who am I to whine.. oh it hurts. Or as Frankie Goes To Hollywood sang- Relax...

AnonymousAnonymousalmost 9 years ago
Damonx, you are missed!

Nicely done.. Not only do you pick up the thread nicely but I like how you keep to the tone.

AnonymousAnonymousalmost 9 years ago
It's OK to like it dirty.

Helping a freshman co-ed is a fond memory for me. She liked the attention and would do anything I asked of her. She learned to obey and I learned to dominate.

Sure wish I knew then what I know now.... Third Night is the charm.?

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