16 comments/ 349423 views/ 75 favorites Freshman Girl By: damonX (Based on a true story.) "No. No. No. Maybe if I was drunk. No. No." Reaching my hands up and placing them lazily behind my head, I reclined against the large oak tree at my back and continued to check out the steady stream of girls walking past me. "No. Yes. No." I said to myself, as a trio of eighteen year olds made their way past, casting a few flirtatious glances my way. I loved the beginning of the College year. No studying, the weather's nice, and best of all, the place is filled with new impressionable freshman girls. I think deep down inside, that's what made me decide to come back to complete my Master's degree. Not a thirst for knowledge or a desire to make more money (although that was a nice bonus), but to get one last chance to de-virginize a few young coeds. I was however, a little disappointed at the new crop so far. I had been sitting by that oak tree for almost an hour and I had only picked out a handful of decent girls. "Oh well," I muttered to myself, standing up from the soft grass. "Let's see how the dorms are." It was getting late in the day and I still had a lot of unpacking to do so I decided to head back to my room. As I neared my building I noticed a cute little blonde girl holding a large box and struggling with the door. I quickened my pace to make it in time to play the part of the gentleman. "Here," I said, sliding my key into the door. "Let me get that for you." "Thanks," the girl said quietly, still struggling with the load in her arms. I held the door open as she walked through, stumbling forward as the box began to slip from her hands. "Whoa," I said, grabbing the box and preventing her from falling flat on her face. "Why don't you let me help you with that." "Oh it's okay," she said meekly, regaining her footing and pulling the box out of my arms. "Are you sure?" "Yeah, I'll be okay." "Don't be silly," I said snatching the box back. "You look like you're about to die. What floor are you on?" "Three." "Perfect. Me too." With that, I took off up the stairs. "So what's your name?" I asked as the girl followed close behind me. "Nicole." "Hi Nicole, I'm Damon." "Nice to meet you," she replied softly. I could tell she was quite shy. "First year?" "Yeah," she said. "How can you tell?" "You freshmen stick out like a sore thumb around here," I returned, flashing her a smile. Nicole smiled a little herself, and turned away slightly as her face began to turn a light shade of red. She was cute. Not hot, but definitely cute. She was short, about 5'2, with shoulder length blonde hair and a round, cherubic, innocent looking face. "Okay, I said as we reached the top of the stairs. "Lead the way." Nicole walked past me and made her way down the hallway towards her room. As she walked, I continued to check her out. She was a little bit round, but definitely not enough to be considered chubby. Her breasts were fair size and her ass looked great in the pants she was wearing. Round and plump, it still looked firm as it fought against the tight material hugging her curves. "Well, this is me," she said stopping in front of one of the doors. I walked in and set the box on the bed. "There you go," I said, taking a quick glance around. "If you need any more help I'm just down the hall in room 325." "Thank you," she said smiling coyly. "No problem. Maybe I'll see you tonight. There should be some good parties." "Okay," she said. "I'll see you later." I smiled to myself as I left Nicole's room and headed towards my own. This was going to be easy! * * * * After I got back to my room, I unpacked the rest of my stuff before calling some friends. As it turns out they were going to a party off campus, and after a few minutes of persuasion they convinced me to go. I quickly got dressed and headed out to meet them, stopping briefly to knock on Nicole's door. I gave the door a few raps with my fist but there was no answer. "Oh well," I thought to myself. "I have all year." The party turned out to be a bust. The house was tiny and too packed to even move. There were hardly any girls there and the one that were there, all seemed to have boyfriends. Nevertheless I was still quite intoxicated when I decided to leave early. After saying goodbye to my friends I took off, embarking on the 30 minute walk back to campus. By the time I reached my building I was still feeling the effects of the alcohol, but had sobered up considerably. All around, I could hear the sounds of people partying, making me feel a little lame for packing it in so early. When I reached my room I had barely put the key in the hole when a voice yelled out to me from down the hall. "Damon!" I turned to see Nicole making her way towards me, with one hand on the wall for support. It looked as though she had had maybe a bit too much to drink, but I could tell she wasn't in pass-out mode yet. "Hey cutie," I said as she approached me. "How was your night?" "Good," she said. "I'm a little drunk though!" "Yeah I can tell," I said with a laugh. Nicole had changed her clothes from earlier and was now wearing a little pink skirt with a white tank top. She had also put make-up on and was looking even better than before. "So what are you doing now?" I asked, opening my door. "Nothing. Just looking for something to do." "Want to come hang out for a while?" "Sure!" she said enthusiastically, skipping into my room and sitting down on my bed. Closing the door, I walked over and put on some music. "So did you have fun?" I asked, sliding onto my bed beside Nicole. "Yeah it was ok," she answered. "I did something bad though." "Really? What?" "I kissed a guy." I let out a laugh and slumped back on the bed. Nicole turned and glared at me with a fake scowl. "What's so funny?" she demanded trying not to crack a smile herself. "Nothing. It's just that I wouldn't describe a kiss as something "doing something bad." "I think my boyfriend would though," she said reverting back to the shy girl I had met earlier that day. "Oh you have a boyfriend?" I asked, trying to hide my disappointment. "Yeah. We've been going out since like grade 9." "Wow. That's a long time." "It is. That's why I feel kind of bad for kissing that guy tonight." The was a bit of an awkward silence before I spoke. "Don't worry about it," I said nudging her playfully with my foot. "You're in college now. You have to see what's out there." "Yeah, I guess," she said quietly turning to look at me with her adorable blue eyes. "Thanks for helping me earlier by the way. That was really nice." "No problem," I stated nonchalantly. "You can pay me later." Nicole smiled at the joke but still gave my leg a light slap. "Jerk," she said blushing. "How about I owe you one?" "How about you give me a kiss instead." Nicole's eyes widened and her face turned a deeper shade of red. "I..I can't." "Come on," I coaxed. "Just one little kiss. It won't hurt." Nicole sat there staring at the wall for a moment before turning to face me. "Okay," she said finally. "Just one." I smiled and sat up, taking her hand in mine. She licked her lips nervously as I leaned in pressing my mouth to hers. Nicole closed her eyes and I could make out a faint moan as our lips touched. After a few seconds she opened her mouth up a little more allowing my tongue to slip inside. Gently I placed my hand behind her head and kissed her deeper, our tongues dancing together in a wet embrace. She tasted sweet. Almost like candy. I decide to go a little farther. Nicole shivered as I placed a hand on the bare skin of her leg. At first she did nothing, but as I began to slide it a little further up her leg, she dropped her hand onto mine, stopping my exploration. "We shouldn't be doing this." she said, pulling her mouth away from mine. "I'll stop whenever you say," I said quietly, leaning back in to kiss the soft flesh of her neck. "Do you want me to stop?" Nicole closed her eyes and moaned softly as I continued kissing her neck. "N..No," she murmured. I smiled to myself. "Here," I offered. "Why don't you lay down. It will be more comfortable." Nicole nodded and laid down on the bed, resting her head on one of my pillows. I crawled up beside her, propping myself up with one arm. "Damn, you're cute,"I said, looking down into her eyes. Nicole blushed again, turing her head to the side in mild embarrassment. I reached down and placed my hand on her chin, gently turning her face back towards me. She bit her lip nervously as she gazed back up at me. I smiled at her once more and began to kiss her again. She was a little more receptive this time, kissing me back and reaching a small hand up to gently grasp at my shirt. I ran my hand up the side of her body, lightly touching her. Slowly, I slid my hand over her breast. I was expecting her to stop me again, but Nicole remained laying there passively as I continued to explore her body. She even let out a sexy little moan into my mouth as my fingers brushed over her nipple. Gently I squeezed, causing her to squirm under my touch. "Are you okay," I asked looking down at her with concern. "I don't want you to do anything you don't want to do." "I'm ok," she answered shyly. "This is fine." We resumed kissing as I placed my hand back on her leg, gliding my fingers over her smooth skin. When I reached the hemline of her skirt, however, her body tensed up again. "Relax," I whispered, kissing her ear as I slowly moved my hand up under her skirt. I could feel her body loosen up a little, but she was still laying there like a board. To coax her along, I took one of her hands and placed it between my legs, letting her feel the hardness contained within my pants. "Do you feel that?" I asked, pressing her hand against my dick. "Do you feel how hard it is?" "Uh huh," Nicole whimpered as I continued to lick and suck at her ear. "You did that. You're turning me on so much." Nicole moaned and began to grasp at my cock, massaging it with her fingers through my pants. I then slid my hand farther under her skirt grazing the outside of her thigh until my fingers came in contact with the soft material of her panties. I let my fingers linger there for a few minutes as we kissed, before moving my hand between her legs. Nicole gasped as I touched her, but made no move to stop me. Her breathing quickened and her grip on my dick increased, as she slowly moved her hand up and down, stroking my shaft. I pressed my fingers up between her legs, feeling the moisture of her panties and the warmth radiating from her pussy. Through the thin material I could make out her engorged lips and thin, wet slit. Using two fingers, I pressed them into the crevasse and stroked her through her underwear. Nicole was still pawing at my cock through my pants, so I reached down and unzipped my zipper, coaxing her hand inside. I closed my eyes in pleasure when I felt the warmth of her hand encircle my bare flesh. Slowly she stroked me in unison as she began to rotate her pelvis, grinding her soft mound against my hand. Subtly, I slipped a couple fingers under the elastic clinging to her inner thigh, and pulled her panties to the side. Nicole suddenly stopped kissing me and looked into my eyes with an expression of seriousness and contemplation. I looked back at her, waiting for her to speak. "Go ahead," she said quietly. I smiled, leaning back in to kiss her as I gingerly rubbed my thumb along the top of her pussy searching for her clit. When her hand began to move faster on my dick I knew I had found it. Slowly, and deliberately, I pressed my thumb into her little fleshy button as two of my fingers found their way between the soft folds of her pussy. "Ohhh," Nicole moaned as I pushed my fingers in up to the knuckles. It felt as if her whole body was shaking as she lay there passively allowing me to explore her tight little eighteen year old pussy. With every thrust of my fingers she became more and more wet, with her juices running down my hand and dripping onto my bed sheets. Leaning down I planted a soft kiss on her thigh. Nicole released her grip on my cock and brought her hand to her face, gently biting her pinky finger as she closed her eyes. I continued my way up Nicole's leg, encouraged by her quiet sensual moaning. Reaching up under her little pink skirt. I curled my fingers into the waistband of her panties and began to pull them down. At first Nicole resisted, but after a few more kisses on her inner thigh, she lifted her hips, allowing me to slide the white underwear down her legs. As I began to lift her skirt, however, she did stop me. "Can we turn the lights off?" she asked looking at me, pleading with her innocent blue eyes. "Don't worry," I said assuring her. "You have nothing to be ashamed of. You're beautiful. I want to see you. I want to see all of you." Gradually she relented, allowing me to push her skirt up bunching it around her waist and completely exposing her entire lower body to my hungry eyes. Obviously embarrassed, and a little self conscious, Nicole turned her head to the side, averting her eyes. Her pussy lips were pink and engorged, with a light tuft of blonde hair situated atop her juicy little mound. "Mmmmm," Nicole purred, as my tongue flickered over her lips. Enjoying her taste, I surrounded her little wet hole with my lips, sucking her sweet nectar into my mouth. I then buried my tongue in her pussy, forcing her legs out wide with my arms. "Fuuuuuckk," she droned, running her hands through my hair. Hearing such a nasty word coming from Nicole's innocent little mouth turned me on even more and I continued eating her tight young pussy with renewed passion, sliding a couple fingers inside her. As I licked her, I tested the waters by running my finger down to her asshole. Nicole immediately squirmed and shifted her hips, showing her discomfort with that particular part of her body. I decided not to press my luck, and returned my finger to her grateful pussy. When I had had my fill, I kissed my way back up to Nicole's mouth, pressing my body into hers. She wrapped her legs around my waist, grinding her naked pelvis into mine. My cock was aching and straining to break free and get inside that tight little cunt. "I want you so bad," I hissed into her ear, thrusting my hips into hers. I then grabbed her arms, pinning them over her head as I locked my mouth onto hers. Nicole just moaned as she let me have my way with her body. Placing my hands at her waist, I began peeling off her little white shirt, pulling it over her head, up her outstretched arms and off. Her bra was quick to follow leaving Nicole completely naked under me, with the exception of the little pink skirt that was still bunched up around her waist. My hands and mouth quickly found Nicole's breasts, as I sucked one nipple into my mouth as my hands caressed both of her round, succulent tits. Her moaning became louder, as I gently pulled her nipple with my teeth. I could feel her pussy pulsing as she writhed underneath me. Rising to my knees, between her legs, I opened the button on my pants and began sliding them down. "Damon," Nicole said, with a concerned look crossing her face. "I'm sorry but I can't have sex with you." I froze. I was about to say something, when she spoke again. "I'm not on birth control and I don't want to risk it." I silently cursed myself for not buying condoms. "That's okay," I said, running my hands along the outside of her legs. "We don't have to have sex." "Really? You're not mad?" "Not at all. But just because we can't have sex, that doesn't mean we can't still do other stuff. Right?" "I..I guess so." Fuck she was cute. Leaning back down, I kissed her for a few more minutes before making my next move. I finally reached down, and freed my dick from the constraints of my pants, sliding them down my legs and kicking them onto the floor. Moving up the bed, I positioned myself near Nicole's head. Her eyes were glued to my throbbing cock as I brought it closer to her face. "Open up baby," I said, coaxing her to part her lips. Nicole looked up me with those child like eyes and obediently opened her mouth. As I touched the head of my dick against her lips, she gave it a kiss and began sucking and licking it in much the same way one would suck a lollipop. Im my current position, Nicole could barely get her mouth over the crown of my dick so I swung a leg over her chest, resting my foot on the bed. I was now pretty much straddling the sexy young coed, with my cock resting comfortably across her pouty little lips. Again she parted her lips, this time allowing much more of my cock into her mouth. I could tell she was quite inexperienced, so I decided to take over. Reaching down, I held her head in place and began slowly thrusting my hips, sliding my dick in and out of Nicole's mouth. The underside of my shaft was gliding over her tongue as she rested her hands passively on my thighs. Slowly I started to build up speed, being careful not to choke the poor girl as I fucked her mouth. "Oh yeah," I moaned reaching forward to grab the headboard of the bed. "Good girl. Suck that cock." Nicole was accepting everything I was giving, staring up me with those beautiful blue eyes as my balls repeatedly slapped her in the chin. I could have easily fired a load down her throat, but I wanted to save myself. I had other plans for Nicole. With great reluctance, I withdrew my aching cock from her mouth, dribbling saliva down her chin and neck. "Thanks baby," I said leaning down to kiss her. "That was great. But I want to do something else now." "What?" she asked, wiping her spit from her chin. "I want to lick you again. But this time from behind." Nicole seemed unsure, but soon relented to my persuasion. After denying another request to turn the lights off, I coaxed her onto her hands and knees. Trembling with anticipation, I pushed her skirt up around her waist again, revealing her beautiful, full, round ass. "Damon," Nicole whined softly. "I feel kind of weird. Can we just do it the other way again?" "Just relax," I said, running my hands over her ass. "It'll feel good. I promise." With that, I leaned down and kissed her soft ass cheek, feeling her shiver with anxiousness. I then gently spread her cheeks slightly, getting a good view of her little pink ring. "What are you doing?" Nicole asked meekly. "Shhh," I said kissing her tender flesh again. "I told you I was going to lick you. Now lower your head and stick your ass up in the air." I made my words as gently as possible as not to scare Nicole off. And they must have worked, since she did as she was told, dropping her head down to the bed. "Good girl," I said, giving her a light slap on the ass. Nicole giggled a bit and looked back at me smiling. I then lowered my head and ran my tongue along her little wet slit, eliciting more of those sexy moans which I had become so accustomed to hearing. Stabbing my tongue into her, I could feel the heat from her hot little hole on my lips. I began giving her long, wet licks up the entire length of her pussy, gradually getting closer and closer to her butt hole. Nicole started to shift uncomfortably as I began to zero in on her ass. "Oh!" she yelped as I startled her by running my wet tongue across her asshole. "Don't lick me there," she begged, reaching back to cover herself up with her hand. "Don't worry about it," I said softly, pulling away her hand. "Just relax and you'll like it." Again, Nicole relented, giving me free reign over her backside. Lewdly, I jammed my tongue into her hole, wiggling it around her tight little star. She shifted her body forward trying tin vain to escape my nimble tongue, but I grabbed a hold of her calves, fixing her in place as I continued to lick her puckered little rosebud. Freshman Girl Second Night 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. Freshman Girl "Spread your ass for me baby," I suggested, slipping a finger into her pussy. Reluctantly, she reached back, and pulled her ass cheeks apart, exposing her most private area. I took a moment to take in the site of the young woman in that nasty position. Her asshole was picture perfect. A tight pink ring, glistening with my saliva, framed by a beautiful round ass. I slipped another finger in her pussy to help take her mind off the tongue bath I was giving her asshole, and it seemed to work. Her tiny pucker relaxed enough for me to force the tip of my tongue inside her. Nicole squealed at the feeling of my tongue in her ass, but was soon moaning as I began tongue fucking her tight little butt hole. Pulling my fingers from Nicole's pussy, I started running one of my slippery digits over her asshole. "Damon?" she asked, in a cautious tone. "You're not going to put that in there are you?" "Just one. Then you can see how it feels. If you don't like it, I'll take it out. Okay?" "Okay," she agreed, inhaling deeply as I pressed the tip of my finger past her tight muscular ring. "Relax," I reminded, pushing it in up to the second knuckle. I began to wiggle it around inside her ass, marveling at the site of her tight little butt hole hugging my finger. "How is it?" I asked, moving the digit in and out, slowly finger fucking her virgin asshole. "Do you want me to stop?" "It's okay," she panted. "You can keep going." I smiled and kissed her all over her tender ass cheeks, even rimming her hole, licking around my own finger as it slid in and out. Nicole gasped when I inserted another finger, burying her face in my bed sheets. Soon I had two fingers sawing into her ass as Nicole moaned into my blankets. "How about I put something else in there?" I asked optimistically, twisting my fingers around inside her. Nicole raise her head from the bed. "You mean...?" "Yes, baby. I want to fuck your ass." "Okay," she said after a long pause, surprising me with her response. "Just go nice and slow." Hopping off the bed, I dug a bottle of lubricant out of one of the boxes sitting on the floor, as Nicole remained patiently on her hands and knees. "What's that," she asked. "It's lube," I answered. "It'll make it a little easier. I climbed back onto the bed and uncapped the lube, squirting a liberal amount into the palm of my hand. I then applied the slippery substance to my throbbing cock as I leaned over and gave Nicole's ass some more lube of my own by giving her a long wet lick over her tight little hole. "Damon," she said as I was getting into position. "Maybe we shouldn't be doing this. I have a boyfriend remember." "Don't worry baby, you'll like it." "Yeah, but....Oooooh!" Nicole squealed with pleasure as the tip of my lubed-up dick touched her asshole. "I..just...d..don't think..it's..right." "Are you sure?" I asked, rubbing my cock up and down her ass. "Well...." "Come on," I prompted. "Okay, she said quietly. She sound unsure but it was good enough for me. "Good, now try and relax again." It took a few tries, but soon I was able to force my way into Nicole's virgin asshole, slipping the head of my dick inside her. "ughhhh..ughhh," she groaned as a few inches of my cock disappeared inside her. "Fuck baby, your ass is so tight!" I gritted my teeth and pulled Nicole's hips back towards me, forcing her ass to eat up more of my cock. "Oh fuuucckkk," she squealed as I slowly began to move my hips back and forth, moving my dick in and out. My cock was barely even moving but it was enough to cause Nicole's body to shake and squirm as she repeatedly gasped for breath. My hands dug into her fleshy ass as I began to move faster. "Oh yeah! I'm fucking your ass! I'm fucking your tight little asshole!" Profanity began to spew forth from my mouth as I watched Nicole's eighteen year old butt hole swallow up more and more of my dick with each thrust. I was losing control. "Where's my dick Nicole?" I asked, fucking her harder and harder. "Where's my dick?" "In my ass," she replied meekly, her face still buried in the sheets. "Louder," I demanded, reaching forward and grabbing a fistful of her honey blonde hair. "In my ass!" she howled, as pushed my cock up to the hilt in her tight little hole. It was then that I felt a tingling feeling surge through my cock. I knew I was going to cum. "uhhhh, ughhhhhh!" Nicole groaned louder with every thrust. With one hand I gripped her thigh and with the other I pulled her head back by her hair, driving my dick as far as it could go into her ravaged asshole. My balls tightened and my cock exploded, dousing the inside of Nicole's anus with creamy hot cum. Her tight little ring spasmed around my dick at the feeling of being internally assaulted by streams and streams of the hot slimy liquid. "Fuck," I muttered, as the intensity drifted away leaving me with feelings of tiredness and fatigue. Carefully, I pulled my cock out of Nicole's abused, cream filled butt hole. "Thanks babe," I said giving her a light slap on the ass. "That was amazing." Nicole quietly got up and began collecting her clothes. A closer look revealed tears welling up in the corners of her eyes. "What's wrong?" I asked, laying back on my bed. "I shouldn't have done that," she stated, fighting back the tears. "I feel so dirty!" "It's no big deal," I offered, although I wasn't the one with an asshole full of cum. "But I'm going to have to tell my boyfriend! He's going to think I'm such a whore!" "Hey, hey, hey," I said, grabbing the frantic girl and pulling her close. "You don't have to tell him. Everyone makes mistakes. It's not the end of the world." "Yeah, I guess," she replied meekly. I embraced her for a few more minutes before she was composed enough to gather up the rest of her clothes and head back to her own room. I said goodnight and gave her a goodbye kiss before she headed out the door. I had a feeling I'd be seeing more of Nicole. "Ahhhh," I said to myself slumping down on my bed exhausted. "Freshman girls."