My first time sex
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.
‘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.