Being Katie's First

My friends all call me Creepy David. I've always been a writer, but had never tried my hand at erotic writing until now. I figure the best way to start is to write what you know, so this is a real experience I've had. I'd appreciate any feedback on writing, but please keep any criticism on myself or Katie to yourself. Thanks.

It all started this past August. Class had started and Ann had made a new best friend in school. We'd been together for 3 years now, and had both moved here for college. I normally don't take much notice of her friends, and Katie was no different. In the beginning I'd pretty much ignored her. She was cute, but tiny and mousy and not very talkative. I later learned that this was because she had grown up in a small town a few miles away with a very poor and equally conservative family. Her dad had left when she was little, and her mom was so germaphobic that Katie was never allowed to have anyone over, and therefore grew up without any real friends. Ann was her first. She had also just recently discovered dressing like a girl. She had always worn her older brother's hand-me-downs, but now that she was on her own and living decently on her student loans she had her own clothes; skirts, tight pants and tank tops mostly. Her new clothes were actually why I had first taken notice of her. She had a pair of black pants that were so tight that they perfectly outlined her pussy at all times. I'm really not sure that she even knew they did, until I was caught staring one day. She just blushed with the smallest hint of a smile, until Ann realized I was looking. Then they both yelled at me. She didn't wear the pants out anymore.

Anyway, last Halloween she wore a Sailor Mars costume. It was incredibly slutty, and I made a comment to Ann about it looking like Katie was trying to get laid. Then, Ann told me something that made perfect sense to me, but I had never realized it until then. Katie was a virgin. After that I really couldn't look at her without a very significant part of me wanting to fuck her.

Then, a few days later, we were all three hanging out in her dorm room together before going to get food. I was talking about hating the dorm beds, because if my head were touching the wall my feet still hung off the bottom to my ankles. Katie said they were the perfect height for her, and stretched out her arms and legs. Her hands and feet each barely touched the four posts. Something about seeing her spread out in that position was the final straw in my mind. I was going to have Katie, but I knew she'd be too nervous to let me, because it was her first time and Ann was her best friend.

I decided to wait for Thanksgiving weekend. I had run it over several times in my head before then, and had gone and bought four sets of handcuffs and a scarf. I'm sure you can assume by now that I wasn't going to take no for an answer, but no part of me wanted to hurt Katie. I also found a guy online who would sell me GHB. He called it "Bedtime Scoop" or some crap like that, but it works the same. I wanted Katie out so she couldn't fight or get hurt, but I also wanted her to be lucid when she woke up. It wasn't my intention at all for her to not know what was going on. I know someone who can't remember her first time, and I didn't want Katie to have to go through that.

Ann had left for the whole week of Thanksgiving, which is part of why I'd picked it. Katie was going home the day of, but I knew she'd be eating in the caf that week. We always do, and the three of us usually do together. So I made sure that I happened to be there at the same time as her and we sat together to eat. After lunch everyday, Katie went back to her dorm to study before Journalism. She always had a water bottle with her wherever she went, which I'd always found odd because she brought it to the cafeteria and then drank soda from the fountain. We talked for a while, then Katie got up to get dessert. I looked at my phone to see the time and noticed that we usually leave within the next 15 minutes. She had left her water bottle sitting on the table, so I decided it was now or never. I pulled the vile out of my pocket, opened her bottle, and poured it in making sure that no one saw me.

Katie returned with her dessert and we continued our conversation. After finishing her slice of cake, she stretched and said that she'd better be going. "I'll walk you." I offered. She didn't object, so we set off toward her dorm. Halfway through the walk I began to worry that she wouldn't drink it in time, when she finally twisted the cap and took a drink from her water. I put a lot of effort into hiding my relief at that point. The walk is about 15 minutes on its own, so I knew I'd have to buy a little time. When we reached the honors dorm she turned and said, "Bye Dave." leaning in for a brief hug.

"Now what kind of guy would I be if I walked you home, but only the entrance? Besides, Ann's jacket is upstairs and I was hoping to grab it while I was down here." I hoped this worked.

"Alternative motive to walking me, huh? I thought so. Come on up."

Why wouldn't it have worked? I was a pretty trustworthy guy until today. We climbed the 2 flights of stairs together when I noticed her first start to seem a little drowsy. She leaned on the wall a little as we entered her hallway.

"You alright?" I asked and placed my hand on her shoulder.

"Yeah, it's just been a long day. I'm pretty tired." she replied.

We arrived at her door and she unlocked it, looking sleepier every second. We stepped inside and I began pretending to look for the jacket, making small talk as I did. She did her best to talk back, but had already curled up on the bed. A few seconds later some part of her must have realized what was going on. She rolled onto her back to look up at me and very quietly said, "Please don't." Then her head fell to the side and her eyes closed. She was out.

I opened her dresser and found the black pants I had been missing for some time now. I slowly pulled her jeans off, admiring the beautiful skin on her legs. Her thighs were pale and smooth and perfect. I couldn't help but kiss them as I finished removing her jeans. Next, I pulled off the pink boy-shorts she was wearing underneath. I let my fingers gently trace over the curve of her ass and brush across her pussy lips. I stared for longer than I'd planned to at the beautiful sight of her lying there. Her hand moved slightly, sobering me up and back to work.

I pulled the pants up around her waist, taking as much effort as I had joked about it probably taking her. They were incredibly tight after all. I removed her shirt next, followed by the lacy pink bra underneath it. Her breasts were small and perky. They had never really caught my attention before, but I definitely wouldn't say they weren't nice.

I then proceeded to handcuff her hands and feet to each of the four bedposts. I made sure that she couldn't pull free, but that they also wouldn't hurt her or cut off circulation. I brushed the hair out of her face and placed the scarf in her mouth. Then, I kissed her on the cheek and whispered, "It's going to be ok." and turned to walk to her desk. I sat in the office chair, opened up her laptop, and passed the time until she woke up.

About an hour and a half later, she awoke and realized that she couldn't move. I don't think she hade seen me at her desk yet, and she continued to struggle against the handcuffs. Muffled screams came from beneath the scarf. They didn't generate much noise, but I was sure that if someone had pressed an ear to the door they'd have heard her, so I needed to quiet her down. I rolled the chair over to the side of the bad, and she looked up at me with the most fearful eyes I had ever seen.

"It's ok." I said calmly, "I'm not going to hurt you." She continued to try and scream for help. "But," I quickly added, "If you keep making noise I'm going to cover your nose." She stared angrily for a second. I heard her inhale deeply in preparation for the next scream. I moved my hand quickly to her face as the first half came out. It was soon muffled by my hand pinching her nose closed. She shook her head violently to try and break my grip, but soon ran out of air and began to slip out of consciousness again. As soon as she stopped struggling, I loosened my grip. "Please Katie." I said comfortingly, "I'm not going to let you go yet. Please don't keep fighting. It's just going to make you more likely to get hurt. I don't want to hurt you. Please."

I cautiously pulled my hand away and she just stared angrily at me. She mumbled something into the scarf that I couldn't understand. I'm sure it wasn't very nice, but at least it was quiet. I brushed her hair out of her face once more. "I'm going to be as gentle with you as I can. I promise." With that I slid my hand down her cheek, grazed her neck and moved it to her left breast. I gently massaged her tit, making small circles around her nipple with my index finger. I continued this with my right hand, while my left made its way up the bed and to her right thigh. Her face changed from anger to fear once more. I rubbed her thighs through the thin black material and bent my head down to lick her nipple, which was slowly becoming erect. I flicked it softly with my tongue, moving my right hand to her other breast. She whimpered quietly against the scarf.

I picked my head up briefly and said, "Now if I do anything that hurts, just shake your head, ok?" She remained motionless. "Ok." I responded, and returned my face to her nipple and placed it in my mouth. I sucked on it, stopping every few seconds to run my tongue around it in small circles. I gently pinched her other nipple with my right hand. Then, I began to nibble her right nipple, looking up briefly to see if her head was shaking. She had closed her eyes, but her head remained still. I continued lightly biting her nipples for a minute or so, then moved my attention to her lower body.

I kissed my way down her stomach, then stood up and placed myself between her legs. With my face close to her pussy, I began stroking it with my fingers through the pants. I traced every bit of it, being able to see it perfectly through her black pants. "I love watching you in these." I said, "They're my favorite ones." I leaned closer and kissed her through the pants, pressing my lips fairly hard against the moist crotch of her pants when I noticed something that excited me. Her pants were moist, and I could smell her juices from this close. On some level she was enjoying this.

"I'm going to take these off now." I said as I sat up. She shook her head at me and pleaded with her eyes. "I said to do that if I hurt you, remember? It's gonna be ok." I reached over to the desk and picked up the handcuff key. I unbuttoned the pants, and with several tugs pulled the waist down to her knees. I uncuffed her right foot, and she immediately tried to kick me off the bed. I knew she would, and was prepared to hold her leg down. Katie was a lot smaller than me, so she didn't really provide much resistance. I bent her knee up toward her chest and pulled the right leg of the pants off. After refastening her right leg, I began to uncuff her left when I realized that there was no point. The pants were out of the way, so I didn't need for them to be completely off.

I stood up and took another look at her spread out in front of me. She was an amazing sight, but I didn't want to get ahead of myself. One of my goals here was to have her enjoy herself too. I unbuttoned my jeans and took them off. My boxers came off next.

I repositioned myself between her legs, and softly blew on her pussy lips. She twisted her body away from my face, and I moved my hands to her hips to hold her in place. "Just relax." I said and leaned forward to flick her labia with my tongue. "Has anyone ever done this for you before?" I looked up to see her shake her head in response. "It's ok. It's not going to hurt. Just relax."

Oddly enough, her body relax, her hips resting calmly in my hands. I removed my left hand from her hip and placed a finger on each side of her pussy. I spread her lips apart, and began to lick her inner folds, up and down very slowly and gently. I heard another whimper come from the scarf, so I slightly increased my speed and pressure of my tongue. Her hips began to rock ever so slightly in time with my licks.

I pushed my face up against her now, and probed my tongue inside of her. She let out a soft muffled moan as I wiggled my tongue up and down. I began to fuck her with my tongue, sliding it in and out of her with my lips still pressed up against her pussy.

After a few minutes of this I returned to licking, and made my way up to her clit. I brushed my tongue against her folds, trying to tease her clit out into the open. It took very little time, and I began to lick her clit gently, making V-shaped strokes with my tongue. Her body shook roughly in my arm, and I could feel goosebumps begin to form on her legs. I continued licking, knowing that she would be cumming soon. She had never had anyone lick her before, so I knew she wouldn't last long. After three minutes of teasing her clit, her small body tensed up in my arm and she began bucking her hips against my face. Her whole body froze as she let out a moan into the scarf. I continued to lick her clit through her orgasm, feeling her cum a second and third time against my mouth.

I picked my head up and kissed her thigh asking, "Are you alright?" She didn't answer. She just stared at the ceiling at tried to catch her breath, her perky little breasts moving with each deep breath. I watched her for a few seconds, taking in how great she looked. Then I noticed something incredible. She didn't look upset at all anymore. She stared up with the tiniest smile on her face. It faded when she saw me looking down at her, but for a few seconds I saw it.

I climbed over her and positioned my legs between hers. I kissed a bead of sweat from her neck and said, "This might hurt a little, ok?" She shook her head at me with a nervous look in her eyes. I shifted my weight onto my left arm and took my cock in my right hand. I rubbed the head against her still dripping pussy until it was completely erect. I rested the head against her lips and leaned close to her ear. I whispered, "The hard part won't last long. Just try and relax once I'm inside, ok?" She shook underneath me and turned her body to the side, trying to avoid me penetrating her. I held her hips in place with my right hand and pressed my cock into her tight little hole.

Now, my dick is pretty thick, but this would have been a hard fit for anyone. I only managed to get past the head on the first push, and rocked my hips for a second try. Her screams came muffled through the scarf and I cupped my left hand over her mouth to try and stifle them a little. My full weight was on her now, and with one more push I was completely inside of her.

I slid the last of my cock into her and held her against me with a hand on the back of her head. "It's ok." I said, trying to reassure her. "It's ok. It'll be over soon." I held her there as her pussy continued to squeeze my cock inside of her. She was even tighter than I had ever imagined, and every time she tensed up it hurt a little.

After a minute of this she quit struggling, and instead started crying into my shoulder. I removed my hand from her mouth and her quiet sobs filled the room. "Shhh." I whispered. "It's ok now." I leaned forward and kissed her forehead. She laid still and gradually stopped crying. "I'm gonna start moving now, ok? I'll be as gentle as I can." She nodded her approval and I began to slowly pull my dick out of her.

She winced in pain as it pulled at her walls tightening around it. I slid six of my seven inches out of her, then slowly pushed back all the way in. She cried a little, but it almost seemed as if she was holding herself back for me. I continued fuck her very softly, feeling her amazingly small pussy begin to loosen its grip on my cock. I kissed her neck as I made love to her tiny body.

I began to increase speed just a little. I could see that she was no longer crying, and I took this as a sign that she wasn't hurting anymore and was ready for a little more. I began completely withdrawing my cock before pushing back deep inside of her with each stroke. She began to breathe heavily again and her face turned a little red.

I pushed my cock all the way inside her and began using short quick strokes, staying deep inside her tight little pussy. Suddenly, her grip on my dick tightened and she came hard, throwing her hips against me as she squeezed with all her might. I continued to fuck her as her orgasm ended, not sure how much longer I could last.

She looked up into my eyes and smiled. Then, I did something incredibly stupid. I reached my hand up and took the scarf out of her mouth. She could have screamed for the entire floor to hear. She could have bitten me or spit in my face. She could have done anything. But when I leaned forward and kissed her, what she did amazed me. She kissed back. I pulled my lips away and she looked at the handcuffs holding her right wrist. "Please." She asked. I reached for the key, and unlatched both of her hands. Again to my amazement, she stayed in place while I uncuffed her feet.

I expected her to try and run, and hesitantly watched her for a second, my cock staying motionless inside of her. She reached forward and touched my hips, and began to grind herself against me.

I returned to lying on top of her and began fucking her again, this time with a little more power in each thrust. She wrapped her arms around my shoulders and bent both legs up and around my waist. She sighed and moaned loudly as I continued to fuck her faster, moving every inch in and out of her perfect little pussy, feeling her squeeze me each time I pulled away. I felt my orgasm start to build, so I lifted my head and kissed her once more, deeply and passionately. Her tongue found mine and I held her tight, thrusting faster and faster into her until I couldn't hold out anymore.

I slammed into her one last time as every muscle in my body tensed up. I came harder than ever before, cumming for longer than I can remember. She breathed loudly in my ear as the last of my cum was emptied into her soft warm pussy. I kissed her softly again, and looked into her eyes. "I love you." she whispered to me.

I kissed her again, and we laid there for the next hour kissing touching. I was so happy that she was not upset at me and had discovered how much she liked sex. I had been her first, and she loved it.

I knew of course, that she wasn't really in love with me. Like I said, I was her first, and there comes a certain attachment with that. She was infatuated with me after that, and had completely forgiven me for the method in which I took her virginity. We kept our relationship a secret for a while, meeting at her dorm every couple of days to make love. Eventually Ann found out and left me. Katie never heard from her again either.

Katie and I stayed together for about nine months after that. We were ok together, but I knew from the start that we weren't compatible enough for anything to last outside of school. She ended up meeting someone better for her over the summer and I was happy for her. I finished school that fall and left town for work. That was pretty much the last I ever heard from Katie, but I still keep a picture of her to remember our first time, and how great it was.