4 comments/ 183974 views/ 13 favorites Being Kate By: xtcnymphette A widower hires nineteen year-old Stephanie to baby-sit his daughter while he plays squash. Her uncanny resemblance to his late wife finds her entangled in a strange but passionate encounter with another kind of virginity. I was shopping with my younger sister Samantha and her friend Tania when I saw him in the busy mall. He was cute in a kind of 'Ben Harper' way with dreadlocks pulled back off his face, tall and blond a strong but gently angular face, piercing blue eyes and strong athletic physique perhaps in his late twenties. 'Check out the Ben Harper look alike over there sis.' I said to Samantha and her friend. He seemed to be walking right up to us. Holding onto one hand was a cute blond little girl of about three toddling alongside him chattering. 'Oh that's Pete I do babysitting for him. He's kinda sad, he lost his wife to cancer about a year ago and lives with his little girl Sophie.' Tania explained. He smiled as he walked up to us and said hello to Tania. He couldn't help scanning three lithe late teen bodies barely covered in skimpy summer clothing. 'I was going to call you Tania, I have a squash game tonight for a couple of hours and needed your babysitting skills again.' He said. Tania looked at him and he kept glancing at me and smiling with a strange look on his face. His little girl also raced up to me as if she knew me and looked up at me and just screamed ' Mummy' at the top of her voice. Tania looked embarrassed and quickly introduced us. 'Oh Pete these are my friends Sam and Steph they're helping me shop for a party I'm going to tonight. So I kind of can't help you out its going to be totally cool sorry!' ' 'Oh, hi girls pleased to meet you. This is my daughter Sophie.' he said. I smiled and picked up the little girl in my arms. 'She's totally gorgeous, do you mind I just can't help cuddling such a cutie. How are you Sophie, are you helping daddy do the shopping?' Pete looked a little embarrassed. 'I think you look a bit like my late wife and she thinks you are her mummy.' He changed the subject quickly and I saw a small tear in his eye as he turned to Sam. I couldn't help being ever so slightly turned on by him he was so cute looking and the vulnerability of him made me feel like hugging him.' I don't suppose you could sit for me Sam, Sophie's not a difficult child.' 'I'm going to the same party. Sorry!' She said. "I don't mind sitting for you. I think it would be fun, wouldn't it Sophie?' I smiled at the little girl in my arms who proceeded to hug me around the neck. 'Would you Steph, I really have to play tonight it's a tournament and as you can probably guess I don't get out much.' 'Hey I'd love to I'll get the address from Sam and see you at what time?' 'Six thirty.' He said and I handed him back the little girl who clung to my neck and kept saying 'I want to kiss mummy Dada.' Pete took her from me and excused himself before the emotions clouded his lovely blue eyes. 'Wow he is totally gorgeous I'm going to enjoy babysitting for him.' I said as I watched his firm ass walk towards the shopping trolleys. 'You do look a lot like his wife, you know Steph.' Said Tania. 'I've seen her in photos and stuff and the resemblance is uncanny. Its kind of creepy don't you think?' I was so turned on by the thought of teasing this cute guy I didn't think too much about the idea that I looked like his dead wife even if his daughter thought so too. I was determined to get to know him better and babysitting presented just the opportunity to do that. I didn't think too much about the emotional damage he might have sustained, I was just totally turned on by the thought of him. At six-thirty on the dot I arrived at his house which was a street away from my own family home. I wore a tight slinky white halter mini dress that hugged my firm breasts and my curvaceous hips and just covered the white satin G-string underneath and revealed the long shapely legs that had always drawn attention to me when I walked down the street. I rang the doorbell and Pete answered, already dressed in white squash uniform, shorts and a polo shirt. Sophie was right behind like a little tornado. 'She couldn't wait until you got here.' He said. 'You hit it off with her in the first few moments in the mall.' 'Yeah, she's a cutie we're going to get on fine.' I picked Sophie up again as I entered the house and followed Pete to the living room. 'She's probably ready for a bath, a story and bed.' He said as he showed me to the bathroom and then to her little room full of toys. There were pictures of his wife Katie everywhere I looked and she did look eerily like me. When he'd finished showing me around he paused and looked at me holding her on my hip. My dress, which was too short in the first place, had ridden up and revealed a hint of the white panties beneath. I could tell he was scanning me lustfully. "Sometimes I wish I was sixteen again so I could date girls like you again.' He said. He must have thought I was the same age as Tania and Sam. No one had said we were sisters and I got asked for my ID at clubs so regularly I had lost count how many people thought I was younger than I am. ' Don't be silly I'm Sam's older sister I'm nineteen and I've dated older guys than you before.' I said indignantly. ' Oh I'm sorry, I meant that to be a compliment only you look so totally hot I have a good mind to stay home and live out every man's babysitter fantasy.' I burst into laughter. 'Thanks for the compliment, you go and play squash Sophie and I have some girls stuff to do, don't we honey?' Sophie just clung to my neck again and I just melted with maternal feelings mixed tinged with the sadness of knowing how much she must miss her mother. 'Maybe we can share a celebratory drink when I get back.' He suggested.' Big kiss for daddy Sophie?' She reached out and kissed him and pulled him towards me as I still held her in my arms. 'Kiss mummy too.' She pleaded. ' It's ok you can kiss me goodbye too. I understand.' He started to give me a quick friendly peck but when our lips met although only briefly the kiss was tenderer than I expected. He quickly exited a strange look on his face. I felt a little confused and a little horny too. One brief kiss had made me think of having sex with him. I tried to put it out of my mind while I played with Sophie. I fed her supper and took her to the bathroom to bathe in the bathroom we played with the makeup in the cabinet and I painted her face with fairy make-up then went to her room to play. Sophie encouraged me to try on the dress ups in her room which was full of what I imagined were clothes that had belonged to her mother. I stripped off my white mini dress and slipped into a sexy purple halter dress that fitted me like second skin. I adjusted my boobs in it and put on the matching hi heeled shoes to it. I dressed Sophie in a yellow fairy outfit and we played fairy games and I told stories for another hour until she collapsed in my arms. I tucked her into her bed and went back to the living room to watch TV not realising I was still dressed in the tight purple dress and shoes. When Pete came home a couple of hours later I was stretched out on the couch, feet up eating an apple. The tight stretch fabric of the halter-top purple dress crushed my tits into a sumptuous cleavage, my nipples outlined against the thin fabric. The dress had ridden right up and my white satin g-string panties were on full display. Pete came bursting in singing. ' I whipped their sorry arses, whoooo! Who wants a drink with the Second Valley Open squash champion....' He halted as he saw me on the sofa. He ran his eyes up and down my form and seemed to shiver as he looked. I took a bite of my apple and adjusted my hem so it covered my panties. 'Oh hi, congratulations!' I said as I sat up. The strange look I had seen when he left crept into his eyes again. He shook his head as if trying to wake himself from a dream. 'You look so pretty.' Is all he managed to say? 'Oh sorry, Sophie and I were playing fairies. Oh this is embarrassing I hope I haven't upset you I'll take it off immediately I'm sorry.' I stammered. Tears filled his eyes and I felt really insensitive. I couldn't help it I just reached out and drew him to me on the sofa and hugged him as he sobbed. 'It's ok, I'm really sorry.' He looked up at me and we said nothing and just kissed. Once more with tenderness I had never felt before. His fingers caressed my neck and traced outlines up and down my bare back. I found myself getting unbelievably horny. He moved a hand to my breast and cupped it gently until I began to moan softly. He teased the nipple through the tight fabric until it hardened then he squeezed it until my soft moans escalated and my breathing grew heavier. I could feel the dampness gathering in the small triangle of satin that covered my shaved pussy and the heat of our embrace rise with every touch every sweet, longing kiss. As I grew more excited he slid a hand onto my thighs and I eagerly spread my legs to encourage him to touch me there. As I shivered and cooed a 'MMmmmm yes.' He touched my gusset gently and traced the outline of my labial folds in the sheer satin until I began to shiver. When he found my clit I convulsed and began to cum wildly my kisses getting more urgent and as I came the fingernails that had gently caressed his neck and back bit into his polo shirt as I clutched him. One orgasm gave way to another as he slid the string aside and plunged a finger into my tight cunt, then another and he finger fucked me slapping his fingers into my wet hole with his palm and thumb manipulating my clit. I squirted wetness like a fountain as his fingers slammed into me. He pulled his fingers from me and stood up and peeled his shorts to the floor. His cock bobbed out larger than life. 'I haven't been able to get excited by anyone since Katie died. Look how excited you made me. I can't wait to fuck you.' And with that he moved toward me to enter me. I don't know what came over me I wanted his cock more than I'd wanted anything but perhaps it was force of habit or I just knew I'd get an even hotter time if I said it. 'I'm a virgin Pete be gentle!' he stopped and pulled me towards him and kissed me again, 'I didn't mean you to stop. ' I said pleadingly.' ' I want you to be my first.' I reached down and caressed his cock with my hand. ' I want you inside my hot little cunt, you do want me don't you?' ''God you are a tease.' I slapped his cock with my palm as I wanked him, feeling the veins throb and his cock grow even more under my attention. In a few moments he was gasping for air and at the brink of cumming I stopped and let go of his cock as a few drops of pre cum escaped. He slipped to the floor, tore off my g-string and spread my legs and attacked my pussy like a thirsty animal. He kissed my swollen pussy lips then lavished them in swirling tongue motions, flicking my clit until I was screaming again rubbing his lips hard against my folds as I gushed onto his face and was seized by another excited convulsion. He lunged his tongue into my hot hole and sucked at my clit until I was sobbing in ecstasy gripped by waves of cumming that seemed to intensify each time. His hands cupped my firm ass cheeks and he lifted me off the sofa. I felt his finger touch my ass hole which was already soaked by the juices that had slid between my crack. Somewhere in the midst of a powerful orgasm his finger entered my ass hole and I screamed in delight. No one had ever touched me there like that and I liked it. I liked it a lot and as his finger dove into my ass hole and his mouth brought me to successive orgasms I screamed out loud things that I had never said before. 'Oh God I want your hot cock, My cunt is aching for you. Give it to me. Fuck me hard.' When I finally stopped sucking me and took his finger from my ass I knew what I had to do. I stood up and guided him to the sofa. I kissed him as I fondled his over ripe cock that strained against my tight grip. I helped him take off his polo shirt and kissed my way down his muscular chest until I reached his straining cock. I cupped his swollen balls in one hand and held his shaft at the base with the other, then blew warm breath across the tip placing my moist lips within a hairsbreadth from his aching flesh. He moaned and I began to slide my tongue over every inch of him from balls to tip covering him with saliva until his cock glistened. I flicked my tongue across the tip teasing him as my fingernails touched his balls with a feather like touch. His breathing quickened his moans escalated. One hand clenched his shaft and began sliding over the wet trail left by my mouth the other teased his balls exquisitely. When I took him into my mouth finally he was over come with desire and screamed. 'Oh God that's so good!' It was like I was possessed I engulfed his cock like I had never sucked any other man before doing things I never thought possible. His cock slid down my throat deep throat style, my fingers squeezed and teased, my head bobbed up and down as I slurped loudly almost choking on the thick engorged flesh that impaled my mouth. He grabbed my head and rocked against me thrusting at me urgently. I stopped for a moment looked up at him with an evil smile reached to my neck and unhitched my halter, peeling it over my tits, then grabbed his cock and slid the tip around my nipple sensuously. The hard nipples teasing his sensitive tip. I even pushed the nipple against the hole at the end of his cock and he winced and moaned as I tortured his cock with my firm mounds. I placed his cock between my tits and he began to titty fuck me and we positioned ourselves so his cock met my wet mouth at the end of his thrusts. I pressed my small firm tits hard around his cock as he thrust it between them and met my eager mouth. As he got more excited I let them go and resumed sucking his cock hard and teasing it with my fingers. He exploded shooting great gobs of the sweetest tasting cum I had ever tasted into my mouth. I swallowed hard and then let a second burst spray my tits as he moaned continuously. I was concentrating so hard on what I was doing I didn't notice what he was saying and then I heard it. 'Oh god Katie, that was so good. I love you so much darling.' I was covered in cum his cock still throbbed in my hand and I let him drop and rose to kiss him. I tried not to let it bother me I ached for him with every part of my body and we kissed again. He relished the cum that stuck to my lips and ran down my chin. The sweet taste of a man who had not cum in a long time. As we kissed I squeezed his balls there was plenty more where that came from. ' Lets go to bed honey.' He whispered lovingly. I had no idea whether he was in a trance and still thought I was his late wife but I couldn't argue with him I wanted him soon. He cradled me in his arms and carried me to the bedroom. 'Put on the white nightie' I love that one.' He said, the glazed look I had seen earlier had returned. I decided to humour him and opened the top drawer of the bedside cabinet and there was a beautiful white silk baby-doll nightie and matching string bikini panties. I peeled what was left of the purple dress that had bunched around my middle to the floor and slid on the soft silk panties and then the short halter-top pausing to adjust my boobs in the halter. It fit perfectly I looked for the entire world like a bride on her wedding night and I felt like one too. I turned around after looking at myself in the mirror and Pete looked at me with a look of absolute desire. ''God I want you.' We kissed and fondled like school children for over an hour touching each other caressing and whispering hot things into each other ears. 'Mmm I cant wait for your hot cock. ' I would coo. 'Oh God I want your tight pussy so much.' He worked his magic fingers on me once more and my pussy was a mass of dribbling wetness. I had never cum so many times as I did with him nor been so wet that I could remember. When I could stand it no longer I reached down and touched his cock finding it as hard as it had been when I had sucked him so voraciously. ' I want you to be my first.' I lied 'I'm aching for your huge cock inside me. Fuck me now I'm sooooo wet for you.' And with that I guided his cock to my sopping panties. He slid them aside and touched his tip against my wet folds. I shivered as he parted them and the head moved into me. 'Do it' I screamed. 'Fuck me deep' He pushed into me gently and I tried to clamp down on his cock as he reached the non existent hymen. As he encountered the extra tightness I pulled him to me and kissed him saying. 'I want you fuck me hard.' He pushed into me deeply and I feigned a wince to let him think he had popped my cherry. It was short lived because the rush of pleasure of having him inside me consumed me totally and I was screaming for him to fuck me harder. 'Give me that delicious cock, fuck my hot cunt darling, make me scream.' Again words I had never uttered left my throat as I screamed wantonly for him to fuck me repeatedly. He rammed me like a prize stud bull. Manipulating my legs in all kinds of positions as he fucked me furiously and continuously. Like his mouth before him his cock triggered waves of glorious orgasms and with each one he changed position and repeated the explosion. His hands cupped my ass cheeks and I felt his finger once again creep to my ass hole now soaked in the juices that ran between my legs. My cunt was dripping with juice as he pummelled me wildly and shoved a finger into me. My cunt gripped him like a warm friendly hand tightening its grip around him with each climax pulsing with warm wet juices the finger inside me triggered wild screams. I loved it in there and he knew it as I screamed and shouted for him to fuck me. He pulled from me to rest my weary over excited cunt for a while. We kissed and calmed then he turned me to face the bed and bent me over the bed. I half knew what he was going to do and shivered. I had never had a cock inside my ass before. I had never even had a finger inside it. I was excited and confused. He slid his cock across the slippery chasm between my legs sliding from the front of my pussy to my ass hole in short sharp strokes until the tingles began once more. He stopped at my ass hole and traced circles around the tight buttonhole opening. I moaned as he pushed the head of his cock into my tightness. At first I almost regretted it as I felt my asshole stretch and tear a little as his cock entered me. A small sharp pain rose in me followed by a strange pleasure as his cock entered me deeper. I reached down and touched my pussy and began to masturbate myself as he forced his hot hardness into my tiny buttonhole. I felt his balls touch my ass cheeks and shivered as the pain turned to orgasms. I thrust at my empty pussy and he began moaning and panting as his cock was crushed by my tightness. He fucked me slowly increasing in speed until he was once again slamming into me in a frenzy of excited fucking. 'Oh God Katie your ass is divine, Oh I cant wait, Oh God! Oh God! I'm cumming!' He exploded in me shooting another hot load into my virgin ass hole I felt the warm shots course into my tightness and his hot cock burn into me relentlessly. I came too, screaming and shivering in waves of pleasure that took me to the core of my existence. Gripping me in convulsions as I screamed and moaned. 'Oh God that's so goood!' He clenched me tight holding my hips and grinding into my ass-hole shuddering each time his cock shot his plentiful jism into me. I didn't mind 'being Katie' if this is what Katie got. I wiggled my ass against him sensuously, his cock still buried in me I fell to the bed, with him on top of me, kissing my neck and urgently groping at my tits nibbling me biting me pulsing deliciously inside me while I shuddered. Being Kate 'Mmmmmm I love your hot cock in my tight little ass hole, tell me how much you love it! I commanded." 'Oh Katie your ass is so sweet, so hot, so tight, I never wanted anything so bad.' When he finally pulled from me we lay in each other's arms cuddling like we had been lovers for an eternity. We slept, and each time we woke I wore another pieces of Katie's sexy lingerie and we fucked our way into the small hours of the morning until woken by the little girl and then the three of us slept cradled together until late morning. Before I fell into a deep satisfied sleep I mused at how different our lovemaking had been. It was as if the clothing I wore drove me to do things like Katie or was it just that Pete saw me as Katie and just sub consciously responded how he expected. Either way I didn't care he was a cute gentle guy who was one of the best fucks I had ever had I was happy to be Katie for a little while longer at least. 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.