Ashtons First Time

Ashton was the pure vision of beauty and womanhood. It was hard to imagine that such a lovely creature could be only 19 years old and even harder to come to terms with the fact that the object of my desire was my roommate's sister. I had lived with Michael for two years in college and had become close friends when he strolled into our room one day with his sister in tow. She had just started at our small private college and was coming to meet the roommate her big brother had told her so much about.

Ashton was relatively tall at 5'9", and though she was not the stick figure that is so popular these days, she carried virtually no extra pounds on her lithe frame. Because of her height, the first thing I noticed after her long blond hair and bright blue eyes were her long and shapely legs. She had a wonderful set of breasts, full and perky, and her beautiful behind was encased in a tight pair of jeans. She smiled shyly up at me behind her brother, and we shook hands like we were new business partners, but the slight shaking of my hand almost betrayed the fact that I was looking at the girl of my dreams.

It was her beautiful face I was imagining one fatal day while stroking my hard, thick cock. It had been several months, and I had not managed to work up the courage to tell Ashton how I felt about her (not to mention her brother). So, I sat in the dark in my room, stroking my throbbing dick, remembering the low cut top and tight skirt she had worn to a party in our room the night before. I squeezed my dick imagining her beautiful lips wrapped around the tip of my cock and moaned aloud.

I heard a gasp nearby and turned to my bedroom door. It was slightly ajar, and my first thought was that Mike had walked in on me jerking off. I pulled up my boxers and dashed into our small dorm living room. As I threw open the door to my room, ready with an apology, I was stunned to discover Ashton standing just outside of my bedroom. My breath caught in my throat and I choked. There before me was the object of my desire, and I was standing in front of her wearing nothing but a pair of boxer shorts which did nothing to cover my obvious erection.

"I'm sorry" was all I managed to say at first before the thought process of my brain managed to catch up to the current situation. "I was just... er... how long were you standing there?"

Ashton's full body flush told me all I needed to know. Even the swell of her full breasts visible above the top of her tight shirt turned a deep red. "I'm sorry too, I was just looking for Mike and the door was unlocked and um..."

Her eyes dropped to my stiff cock, rudely pointing straight out at her. I made a feeble attempt to cover myself and she half laughed. "No, it's okay," she said, "I'm sorry, I shouldn't have just walked in."

"I'm sorry too, it's not your fault," I replied weakly.

"What were you, um, thinking of..." her voice trailed off.

"What?!" I replied in shocked surprise. Her hands quickly covered her mouth as if she had said too much, and she looked for a second back towards the door.

My head swam for a second with indecision before I finally replied. "Um, I was thinking about you." Her eyes quickly turned back to face me, wide with her own surprise. "The way you dressed last night," I managed to continue, "it was so sexy I just um..."

There was an awkward pause. I thought for several terrible seconds that she was about to run out of the room before she responded quietly, "I did that?" Her eyes returned to my cock, still tenting in my shorts.

"I'm sorry, but you have to understand, you were so sexy and your body is just..." I stopped as Ashton blushed even deeper.

"You can't be serious, I mean, I'm not all that good looking," she said. I couldn't believe my ears.

"Ashton," I replied, "you are by far the sexiest girl on this campus."

She looked up weakly in my eyes, and I couldn't believe it when she stepped closer. "I just can't believe that you think I'm sexy."

I tentatively put one of my hands on her shoulder, and she cringed a little but allowed me to draw her closer.

"You are so sexy," was all I managed before I couldn't resist leaning into her. Her beautiful face gazed up at me so innocently and her soft lips and bright eyes were just inches from my face. I was so horny, I almost didn't realize what I was doing until my lips brushed hers. We kissed very softly at first, our lips gently touching and rubbing so slightly that at first I couldn't tell if she was returning my affection. But soon enough I felt her wet tongue run across the surface of my mouth, and my lips parted to allow it entry. Our tongues danced and we began to kiss deeply and insistently. I brought my hand

up and caressed her face.

She pulled away. I knew it. I had crossed the line and now she was going to walk out and her brother would kill me. She turned away from me and hid her face from my eyes.

"I'm sorry..." I managed.

She wheeled on me and pressed one of her fingers against my lips. "Don't," she said, "just listen."

"I've always found you attractive," she continued, "but Mike and I agreed before I came here that I was off limits to you. I don't know what I'm doing, but... seeing you there on the bed... doing that with your... I can't help it."

She stepped into me and suddenly my semi-erect shaft brushed against her stomach. The stimulation was enough to send it back to full mast, and as she ran her hand down my arm, my rapidly growing cock rubbed against her belly.

"I really want to," she continued. "You're so nice and if I'm going to, I want it to be with you."

I thought I was starting to understand, and I asked "if you don't mind me asking, what have you done with a boy before."

She looked at her feet and replied, "I gave a boy a blowjob once. He kind of told me he wanted it, it was after prom." Our hands locked and our fingers mingled. "We were in the back of his car and he kind of took my head and guided me to his thing and I put it in my mouth. I licked it for a long time, and finally he spurt he cum at me. Most of it went in my mouth, but some of it didn't. Anyway, afterwards he told me I wasn't very good and I heard he told his friends that I blew him and I didn't do a very good job."

Ashton looked straight into my eyes. "I want to be better. This is college and I'm supposed to be learning this stuff," she said almost half-heartedly. "I don't even know why I'm telling you this, but I think you're a good guy."

"I would love to be the one who teaches you," I said, and she actually smiled at me. I couldn't believe the turn of events! I had never imagined this happening, and I brought her into a soft hug.

"What have guys done with you?" I asked.

"Well," she replied, "one time I was camping with some guys and one of them pulled my shirt up and he sucked on my breast. That's about it."

I couldn't believe how innocent this young freshman still was. She was so beautiful and so inexperienced.

"Did you like it?" I asked.

"Uh huh." She replied.

I bent down and planted another soft kiss on her wonderful lips. Her tongue came out, expecting to dance again, but I kissed my way softly over her cheek, down her chin, and down her neck. My hand came up and dove under her shirt, finding her full breast. I had imagined feeling her weighty tits in my hand, and couldn't believe that I was actually squeezing her wonderful breast. I continued kissing my way down her neck, licking her lightly as my fingers found her nipple under her sheer bra and began to squeeze it. She actually moaned aloud, and I could feel the vibrations in her chest.

I lifted her tight shirt up and freed her breast from her bra. Her soft, pink nipple popped free and I eagerly sucked it into my mouth. She began to shiver lightly and grind her crotch against my leg as I flicked my rough tongue over her hardening nipple and then ran my hard teeth over the tip of the breast.

She pulled back slightly, and I looked up somewhat alarmed. "We don't have to do anything you don't want to," I tried to reassure her.

"No," she said, and flashed me another one of her heart stopping smiles, "that's not it." She reached behind her back, unhooked her bra, and stepped back toward me.

I began alternating, sucking on one nipple and running my tongue sloppily over her nipple, while rolling her other nipple between my fingers. Then I'd switch, and kiss my way across to her other breast while my fingers roamed across to gently pinch her other nipples. She was moaning in earnest now, and I could feel the heat of her pussy on my leg.

I lifted her in my arms, kissing her again on the lips. As our tongues danced, I carried her into my bedroom and closed the door behind us. Her tongue ran across my teeth as I laid her back on the bed and began to pull on her shorts.

She lifted her ass to accommodate me and I removed her shorts, but she looked up at me very pleadingly. "Please be gentle, Kevin."

"Don't worry, it'll be fine," I replied.

I ran my hands across her thighs and down her legs, up and back down repeatedly. Eventually, my hand brushed her hot mound and she moaned. My fingers found her hot, weld folds, and I traced her swelling lips with my finger. I bent over her mound as my finger found her hard clit and rubbed a teasingly slow circle over her hard nub. Ashton moaned loudly and her hips bucked slightly as I began to rub hard into her clit. I couldn't resist any longer, and licked the lips of her pussy with my outstretched tongue.

"Oh God!" Ashton cried out, looking up at me in alarm. "No one has ever licked me down there... Ohhhhh." Her voice trailed away as my tongue began to slather all over her clit and ran circles with my rough tongue all around her sensitive spot. As I lapped at her juices and sucked her clit into my mouth, I began to push aside the folds of her pussy with my finger. It was a great surprise when Ashton suddenly clamped her thighs over her head and came hard on my tongue. I could barely hear with her legs pressed tightly over my ear, but I felt her body shudder with a lustful cry, watched her chest heave up and down shaking her creamy breasts, and looked deep into her sparkling blue eyes as she orgasmed.

I sat back once she released me from her grip and watched her absently rub her stomach as she came down from her hard orgasm.

"I'm sorry I didn't last very long," she said, "but no one has done anything like that to me before." She smiled weakly.

"Don't worry, I'm just glad that I could help," I said coyly.

Ashton slid down to face me on the bed and I couldn't help but gaze into her playful eyes and smile at her beautiful face. She reached out with her hand and grabbed my cock. I was startled both by her fowardness and the fact that I hadn't even noticed I had stayed hard the whole time I had gone down on her.

"It's only fair that you get a chance now," Ashton whispered with an evil grin. Obligingly, I stood and dropped my boxers. My stiff dick sprung free and pointed straight at Ashton's face. She looked it over curiously before once again grasping it with her hand and slowly pumping my engorged seven inches. I don't think I've ever been as hard or as long as the moment her soft hands first gently caressed my member. I could have cum just from looking at her with my dick in her hands, but she drew my cock towards her face and softly kissed the engorged head. I twitched in her fingers as she smiled playfully up at me.

Then, while looking straight into my eyes, she sucked my throbbing cock into her mouth. Her soft lips felt incredible wrapped around my dick, and her tongue tickled and teased the underside of my shaft. She kept a tight seal around my member as she began working her head slowly back and forth, milking me with her mouth. The velvety soft feeling of her cheeks rubbing against my cock was bringing me rapidly towards orgasm. I knew that between my early self stimulation and the very sight of Ashton naked, I couldn't hold out long.

"Ashton, you're incredible. I'm not going to last much longer," was all I managed to say. With that, she began bobbing faster, milking my dick. Her hands reached up and carefully cradled my balls as she moaned onto my dick. Those vibrations were more than I could handle and I erupted into her mouth. She drank down my cum hungrily, sucking every last drop from my cock as I rolled into a ground shaking orgasm. My knees actually buckled and I slipped out of her mouth as I finally fell, still crashing through one of the most intensely pleasurable experience of my life.

Ashton laughed at me as I lay on the floor with my eyes closed, legs splayed, shrinking dick hanging limply on my leg.

"I don't know what that guy was talking about because you were fantastic," was all I managed to say.

She actually climbed out of bed and lay down on the floor beside me. We kissed very sweetly and tenderly as I wrapped my arms around her, feeling the soft skin of her ass and the wet touch of her tongue. Before long I had wandered to her beautiful breasts again and my hands floated gingerly over her pink nipples. She bit her lip and smiled at me as I began to lightly twist her nipples between her fingers. I pulled tentatively on one nipple and she moaned, thrusting her wet pussy against me. My cock was beginning to regain steam as one of my hands wandered down to her pussy and gently rubbed into her folds. She kissed me on the neck and moaned into my ear as I resumed my finger assault on her clit, rubbing hard and slow circles around her sensitive spot. I scooted down and sucked one hard nipple into my mouth as I rubbed insistently at her clit.

She slid a had down and grasped my cock. I expected her to start up another hand job, but she carefully placed the head of my dick at the warm entrance to her pussy and slid it around, coating it with my juices.

"Have you ever had sex before?" I asked.

"No," she replied, looking down at my hard rod in her hands, "but I want to with you."

I picked her up, cradling her in my arms, and laid her back on the bed. She spread her legs widely for me as I perched over her and coated my cock with more of her pussy juice. I took one last look at her pink virgin pussy before I worked the head of my dick between her folds. She was unbelievably tight, and I knew instantly that she hadn't lied about being a virgin. I had barely managed to work my head into her pussy when I felt the barrier of her resistance. Ashton cringed slightly, but moaned in pleasure as I worked just the head of my cock in and out of her pussy. Finally, I waited just outside her lips before driving deeply into her soft mound.

She cried out briefly, grabbing hard onto my shoulder, as I thrust through her virginity. I paused for several seconds, buried in her tight folds while she became accustomed to the dick in her pussy. I began slowly working my cock in and out of her tight folds. It was like fucking a vise, the grip of her tender pussy walls squeezed against my dick. If not for her earlier blowjob, I may have come from just a few thrusts in her soft and tender pussy.

Ashton whimpered slightly at first, worrying me, but after several minutes of slow, deep fucking I had managed to work most of my cock into her and she started to moan again.

"Oh Kevin," she said, "you're so thick and... Uhhhh... it feels so good you... Oh God... filling me."

A gentle sheen of sweat now coated her soft breasts. I reached down to play with a nipple while I continued to work my cock in and out of her. Before long she was thrusting back up and me, the tight grip of her pussy taking more and more of my dick until I was buried to the hilt.

"It's feeling GOOD," she said. "I think I might be close to another... ooohhhhh."

I reached down and ran the rough surface of my palm over her nipple while I began to fuck her harder and faster. I withdrew almost to the tip before shoving the full length of my thick me back into her wet folds. I rammed her faster and deeper, staring down at the unbelievable sight of her angelic face. Her firm breasts swayed up and down with our fucking, her lovely body coated in a soft sweat, and her beautiful blue eyes always staring back at me.

I slammed into her over and over again, feeling her pussy grip me tightly. Her eyes went wide and she began to buck hard against me.

"OHHHHH GAAAAAWWD!!! I'm CUUUUUUUUUUMMMMMMMMING!!!" she screamed. I felt her puss muscles contract and milk my dick inside her as the wetness of her orgasm washed over my buried penis.

I worked my dick into her slowly a few more times before I paused. She looked up at me concerned.

"You didn't cum," she said puzzled.

"I don't want to get your pregnant," I replied.

"I'm on the pill, it's okay," she said, but she sat up and my still erect dick slid from her folds.

"It's a little tender now" she said in explanation, slipping up against me. She wrapped a hand around my penis again, this time coated in her own juices. She began to pump me again slowly, squeezing my dick in her hands and working my shaft from base to tip.

"I've never cum so hard before," Ashton continued, "or more than once in one night." She kissed me lightly on the cheek. "I'll let you decide what position I'm going to finish you off in."

I couldn't believe my ears. If this was a dream, I never wanted to wake up. I couldn't take my eyes of Ashton's incredible body, and staring at her beautiful face while she gave me a tender hand job was almost enough to set me off again. Only my previous orgasm had kept me from cumming already.

"You ready again?" I asked.

"Sure," she replied with a smile.

I pulled her up and then pushed her over onto her hands and knees. As I positioned myself behind her, she giggled. "So you like it doggy, huh?" was all she said.

I carefully found her warm folds with the tip of my cock and slowly worked the head back into her tight pussy. She gasped as I bottomed out, withdrew, and then slowly bottomed out again.

"You're even deeper and ... oooohhhh... it feels so... ohhhh... good."

I once again marveled in the velvety soft fold of her tender young pussy. I began to work her faster, using my hips to jackhammer harder and deeper into her. She attempted to push back and meet my thrusts, but I began withdrawing almost to my tip again and then shoving the full length of my thick cock back into her wetness. I reached around with one hand and began kneading one her swinging breasts, while my other hand worked down and began rubbing her swollen clit. The effect was immediate. She began moaning loudly and continuously as I pumped hard into her, her blond hair whipping side to side with her head as I assaulted her breast and clit. With my weight resting on her hips I was able to thrust hard and deep into her tight channel. Her soft folds against my prick were bringing me rapidly to the point of no return, but she was clearly losing it.

As I deep circles around her hard clit, she began screaming a constant stream of obscenities. "Oh Kevin FUUUUUUUCCCKK MMMEEEE, " she cried out, her head whipping side to side. "OOOHHHHHHHH GAAAAAWWWD your cock is SOOOOOOO HAAAARRD. I'm going to CUUUMMMMMMM. FUUUUUUUCK MEEEEEE."

I could feel the heat rising from my feet and the cum bubbling in my balls as I pounded my cock into her over and over again. Suddenly, she arched her back and screamed, "FUUUUUUUUUCCKK. CUUUUUUMMMMMMINNNNNGGG."

Ashton's body shook violently with her orgasm, and I could feel her pussy spasm around my cock. The wetness from her eruption spilled over my swollen member and began to leak down her thighs. She stopped moving but I was soooooo close that I kept fucking her.

Suddenly she crawled forward and pulled away. She turned over immediately and saw the disappointment on my face. I collapsed on the bed next to her with my legs dangling over the side, my cock still at full mast and covered with her pussy juices.