Jenny, My Stepsister:byJay©
From Love to Lust
I've had a strange upbringing to say the least. My mother left dad and me when I was very young. Dad got remarried to Betty and she already had a baby daughter, Jenny. She was born out of wedlock, the father had done a disappearing act when he'd learned Betty was pregnant. So there I was with a new mother and a new baby sister. I loved them both from the beginning and we grew very close, especially Jenny and me. Everything was fine for years, then dad upped and left to live with a younger woman. But to all intents and purposes, Betty was mum and Jenny was my sister so it was natural that I stayed.
This put me in the precarious position though, of being the 'man' of the house. Jenny had only ever known dad as her father and she was devastated when he left. I suppose because I was the only male left it tightened the bond between us even more and. touchingly, she told me after he'd gone, that I was now her daddy. Naturally she didn't call me that but she did change from calling me James to Jamie so that she had her own special name for me. But when we were alone cuddled up, watching TV or reading, she'd often call me daddy-Jamie and being some three years my junior, she always came to me for fatherly advice.
Mum was often away on weekends visiting her boyfriend leaving Jenny and me together and it was one of those times when the unimaginable started between us.
It was a Saturday evening and Jenny and I were at home together, I was reading a book and Jenny was flipping through magazines on the floor.
"Jamie" she called out to me, "can I ask you a very leading question?"
"Well it sounds like you're going to anyway, so get on with it, I want to read this book." I told her. But I wasn't prepared for what was coming.
She got up from the floor and came over to sit beside me. Fixing me with her big round, brown eyes she said.
"Do you think it's wrong for a boy put his 'willie' in a girl's mouth?"
"Bloody hell Jen," I shot back in surprise, "you shouldn't be asking me things like that."
"Why not?" She retorted indignantly and without any sign of embarrassment.
"You're my big brother and besides, I've got no one else to ask."
Even though she'd just turned 18 Jenny had the appearance of a 15 year old. Her college pals could easily pass for 20 or 21 but it was always Jenny that didn't have a chance of getting in to a pub. When she was out with a girl friend anyone would have thought she was with her older sister.
Jenny went on. "Mandy at college reckons she does it with her boyfriend all the time. She says she wants to stay a virgin for a while yet and also, having sex like that there's no chance of getting pregnant. She say's she likes it and gets a big kick when she makes him shoot his stuff in her mouth."
Stunned at the way this was going I asked. "Is that what you want to do, is that why you want my opinion?"
"Not really" she replied. "I haven't got anyone to do it with anyway. I just wanted to talk to you about it."
The subject was getting me hot under the collar so I did a quick side step. I told her we couldn't just isolate oral sex we'd have to talk about a lot of things. I promised we'd discuss it at length the following morning. I needed time to gather my thoughts and to decide just what we would talk about. Jenny seemed a little disgruntled but accepted that's how it was.
That evening was murder. The summer heat gave way to lightning and thunder storms so Jenny stayed cuddled up to me the whole time. I couldn't get the thought of Mandy sucking her boyfriend out of my mind and, even though a lot of girls of her age had lost their virginity, I was shocked that Jenny was so sexually aware. Before Jenny had brought the subject up I'd only ever thought of her as my little sister but now I knew what she and her friends talked about, I started to see her in a different light.
Suddenly I was conscious of her small breasts against my chest and I caught myself peeking for glimpse of her knickers when she shifted and her skirt rode up. Several times as she cuddled up, she put her hand on my thigh and I had to struggle against nature not to get an erection. It was hell and I was relieved when it was time for bed. I told Jenny I was going up and that she should too. Smiling, she kissed me on the cheek, said good night and went upstairs to her room.
I got into bed confused. I hated it but I had to confess, I'd been turned on by my little step sister. A ship in the night I thought, a one off, a human quirk which would soon correct itself. The morning, I told myself, would bring back sanity. But that morning didn't have a chance.
In bed I decided to read for a while longer to change the channel in my head. But about a half hour later the door opened and in walked Jenny. She came straight over and sat on the side of the bed. Once again she fixed me with her child like eyes and said. "The weather is horrible outside, I need a cuddle"
"Look," I scolded "you're too old for this and mum wouldn't like it if I let you into my bed."
"So what? She won't know and anyway she's off enjoying herself, she's no comfort and in any case, I'd rather have you." With that she lifted the duvet, slipped in and nestled her back in to my tummy.
Jenny was only wearing a vest and pants and I was naked. As she pushed back to curl against me, my cock started to harden. When I moved away trying to conceal my erection, she just wriggled back to regain her position.
I couldn't risk Jenny discovering my sexual excitement accidentally and frightening or even disgusting her so I just had to say something.
"Jenny," I spoke softly, "please don't be afraid but you're a young woman now and you being this close to me in my bed, arouses me. I think it's better if you go back to your own room and I'll explain everything when we have our chat in the morning."
Jenny swiftly turned around to face me, her lips almost touching mine. She put her small arms around my neck and said. "Don't be silly, I felt your 'thing' sticking in my back. You're my lovely big brother, you can feel anyway you want about me and do anything you want but please don't send me away."
Her words only served to make my erection bigger. Her small frame facing me had my penis rigid against her pants. On top of this she planted a kiss on my lips and flashed me a wicked smile.
I wasn't sure if Jenny knew what she was saying or how she was making me feel but she made no attempt to move away from the pressure of my 'hard on.' Her acceptance of my arousal and her closeness were too much for my will power to cope with and I was carried away with the eroticism of situation. In the heat of the moment I took one of her hands from around my neck and guided it down to my cock. I suppose it's about average in size but to Jenny's relatively small hand, I imagined it must have seemed huge, maybe even scary.
"Ooh" she sighed, it's so big and silky, I've wanted to touch it for so long, tell me what you want me to do."
I couldn't believe my ears, Jenny wanted to take things further. I knew I should put a stop to what was happening but she began to slowly rub me, pulling my foreskin back and playing her fingers over the slippery pre-cum on my knob head. The brotherly love I'd always felt for her turned to lust and I had completely lost control of my senses when I answered her question.
"I want you to do what Mandy does to her boyfriend. I want you to suck me. I want you to take me in your warm mouth. Will you do that for me darling?" I could hardly believe my own words and what I was asking my Jenny to do.
"I'll do anything you want if you let me call you daddy when we're like this. I'll feel safe then 'cos to me you really are my daddy. " I had no idea if she realised how kinky that sounded but the effect on me was electrifying, I almost shot my load into her hand. "Show me what you want me to do daddy, " she went on, "make me do what pleases you."
I was completely carried away. I kissed her lips and explored her mouth with my tongue, the sweet mouth that any moment would engulf my straining cock. My excitement was exhilarating and nothing short of a hurricane could have stopped me from having my young step sister. She was still gripping my rod as I put my hand behind her head and guided it down to taste the pre-cum seeping from the tip of my knob.
"Take it in your mouth baby" I told her. "Make it wet and slide it in and out. Do what Mandy does to her boyfriend."
Jenny willingly took me in her mouth and sucked me with love and tenderness, aided by my hand on her head guiding her up and down my shaft in a slow rhythm. It was the thought of who was doing this to me rather than the act itself which brought me quickly to the point of no return.
"Jenny darling," my words were strained. "I'm going to come but please don't stop, I want you to let me do it in your mouth, please let.....With that I had the biggest orgasm I'd ever experienced and I shot, what seemed to be, load after load into her sweet, waiting mouth.
Even after I'd come Jenny kept sucking and licking my prick, drawing the length of my softening member into her mouth and lapping the last drops of sperm from my small hole. But the sensitivity of my gland was too intense and I gently drew her up toward me. I pulled her close to my chest and she whispered. "That was lovely daddy, I adored it, I swallowed all your stuff. I can't wait to do it again."
Her words left me speechless. I put my arm around her neck and down her vest to fondle her small breast. As I teased one of her small nipples she sighed and laid back giving herself up to my attentions. I pushed my other hand down her pants to discover a soft, almost hairless mound and my fingers opened her wet, slippery crack.
I spread her pussy lips with two fingers, stroking up and down, sometimes inserting one finger in her virgin hole, then returning to slowly rub up and down with both fingers. Then I gently rolled her hard tiny clit between my thumb and forefinger which caused Jenny to buck and moan and I knew she was about to orgasm. Pressing my lips against her ear I told her. "Not yet baby" "I want you to come off while I'm licking your lovely pussy, take off your cloths for me darling, I want to feel your body next to me." She quickly slipped out of her pants and vest.
Holding her small, naked body against mine I told her. "I want you to feel wonderful, just the way you made me feel, do what daddy tells you and let me give you a lovely big come." It sounded strangely exciting referring to myself as daddy.
"Anything daddy, do anything you want."
"Open your legs nice and wide for me darling, daddy wants to get you all wet and ready to lick"
"Oh yes" she whispered, spreading her legs apart, "do whatever you want to me daddy."
I opened her pussy again with my fingers. She was already very wet and I could hardly wait to get my tongue down there and taste her but I didn't want to rush the moment. I took one nipple in my mouth and sucked on it playing it around between my lips and tongue. Jenny's small hand stretched down to grasp my hardening prick again and stroked it tenderly.
"Darling" I broke off sucking her nipple, "I love you playing with my cock and I want you to do it often but this is your turn. I want you to just lay back and enjoy what I do to you."
Jenny didn't say a word but let go of my cock and lay back with her legs wide apart. "That's my little girl, just do as daddy says."
I sucked and tongued her small breasts in turn while I shallowly finger fucked her tight little hole, for the moment avoiding contact with her clit. Grabbing a pillow, I moved down the bed, kissing her belly on the way, then her soft mound and finally licking inside the length of her soaking pussy lips.
I wanted to get my head between her legs so that I could suck on her delicious wetness. When I was in position with my feet on the floor for support, I told Jenny to draw her legs up and I pushed the pillow beneath her bottom. Now she was fully open to me and my tongue lapped at the love juices seeping from her silky hole. I slid my tongue up and along her soaking crack, then parted her lips with my thumbs to gain access to her inner sanctums. I pushed my tongue as far as I could into her slippery hole and then up to lick her small, erect clitoris.
Jenny's moans of pleasure told me all I wanted to know. She loved me licking her sweet pussy. She was in ecstasy and she was mine. I drew the tiny bud of her clitoris between my lips and tickled it with the tip of my tongue. Slipping two fingers into her I began to finger fuck her tight little tunnel while I increased the speed and pressure of my tongue on her clit. Within moments the shuddering of her whole body announced her first man and woman orgasm.
When her body calmed I pulled myself back up the bed and kissed my sweet little Jenny's lips, my tongue roaming her mouth, letting her taste the sweet tang of her own intimate juices. How much I loved her at that moment.
"Thank you daddy," she almost sobbed, "thank you for giving me such a wonderful come." Saying that she cupped my face in her hands and kissed me wetly, slipping her tongue between my lips. Her sweet words and kisses brought on an overwhelming urge, I had to take her, I desperately wanted to fuck my little Jenny.
I gently pushed her back and climbed on top of her. Positioning myself between her open legs I was fully intent on penetrating my little darling and releasing myself to her womb. She showed no sign of fear or rejection when I pushed the head of my cock into her slippery tight pussy but then sanity prevailed and I pulled back. I had no protection and I couldn't risk getting her pregnant. I flopped by her side totally frustrated.
" What's the matter daddy, don't you want to do it inside me? Please do it to me, I want you to fill me up, I want you in me."
I couldn't find the right words to answer her. For a while I just lay there in silence holding her for reassurance, hoping the intense pressure would go away. But when her hand found my cock and her fingers drew back my foreskin wet with pre-cum again, I knew I had to have her, one way or another. I made an incredible decision but luckily one I've never had to regret.
I leaned over my little step sister, my voice husky with nervous anticipation
"Darling, do you love me, do you trust your daddy?"
"Of course I do, you know I do. You want to do something special to me, don't you?" She guessed from my nervousness.
"Yes baby." I admitted. "I want to be inside you so much but until we can make it safe I'm afraid of getting you pregnant so I'm going to ask you to let me do something very special. But, if you say no it won't spoil anything between us, I promise."
"What do you want to do to me daddy?"
"Because I can't go in your front hole, daddy wants to go in your back hole, will you let me if I'm very careful and gentle?"
"You mean my bum hole?"
"Will it fit in there? Will it hurt?"
"Baby, daddy wouldn't hurt you for the world, if you let me I promise everything will be just wonderful and we'll have something extra special between us. You don't have to answer straight away but if we're going to do it, you'll need to fetch the Vaseline from mum's bathroom. If you don't want to come back I'll understand."
"Oh don't be so silly, if you want my bum you can have it. By the way, it can't be all that bad, Sandy's mum and dad do it, she heard her dad tell her mum he couldn't wait to get up her ass." Then smiling at me cheekily. "You're just the same, you can't wait to get up my ass can you?" She teased. Then she jumped off the bed and disappeared out of the room.
When Jenny came back a lot of the bravado had gone. She crawled into bed, passing me the topless tub of Vaseline and snuggled up to me. "Daddy, I don't mind if it hurts a little bit but please try not to hurt me too much."
"Of course I won't sweetheart, if it feels uncomfortable or you don't like it I'll stop, I promise. I'll make sure you're ready before I go inside you, lie on your tummy for me darling."
Jenny turned over and I moved down and kissed the small of her back. As I did I parted her soft small buttocks and revealed her perfectly round puckered hole. At the sight of Jenny's tiny anus given up to me, my excitement rose to an almost uncontrollable height. My prick seemed to be straining against an invisible grip and it felt harder and bigger than ever before. I began to worry that it was too big to penetrate her and that we'd never share this most intimate act of love and surrender.
Even though I didn't know if I would be able to go all the way, I desperately wanted to explore my young sisters forbidden place. I parted the cheeks of her bum wider and went down to kiss and lick her delicate spot. Jenny was completely passive as I licked around her rim but when I finally pushed my tongue past the rubbery entrance and just into her ass, Jenny let out a moan of pleasure.
The knowledge that I was pleasing my baby spurred me on. It was my first time as well and I loved the feel of poking my tongue inside her smooth, tiny anal opening. As my tongue probed and prodded Jenny's bum hole I could feel small muscular movements. Firstly contractions that prevented me from getting any more than the tip of my tongue inside. Then suddenly the muscle would relax allowing the elastic like rim to stretch and I could get further into her back passage.
"Oh daddy," Jenny's muffled voice came from the pillow, "that feels so wonderful"
As she spoke the muscle relaxed again and I made one last jab, forcing my tongue as far into her bum as I could, then I had to come up for air.
Jenny turned her head a little and told me " That was such a lovely feeling daddy. I want to feel your stiff willie in me now, push your big beautiful thing up my bum, up my ass, do it to me now, I need you inside me."
I hesitated for a moment, still doubting the wisdom of stretching her small hole that much but hesitation gave way to lust and I reached for the open tub of Vaseline. I scooped a load on my finger and whispered to Jenny to pull her bum open. She brought both hands round behind her and pulled her cheeks apart. I put the Vaseline on her hole and started to work it past her rim and into her anal passage. My finger was slipping in easily enough but I took another daub and worked that in as well.
I began to stretch the entrance of her ass with circular movements of my finger, pulling gently on the walls of her opening. There was more give than I had expected and Jenny didn't appear to be in any discomfort so I tentatively inserted two fingers. A small contraction gripped my fingers then immediately released them and I pushed on as far as my knuckles would allow. The sight of my fingers imbedded in Jenny's anus brought on a new rush of lust and I knew I had to go all the way.
I was so excited that I had to struggle to keep myself in check, I didn't want to cause my Jenny any hurt. I moved to kneel between her legs and supported myself on one hand while I took my ridged cock in the other to position it against her entrance. "Are you sure darling?" I hesitantly asked.
"Oh yes daddy, yes, please put it in." she begged. Then she pulled harder to spread her bum cheeks to the limit and I knew she meant what she'd said.
I pressed down but it seemed I was not going to make an entry unless I applied more force than I wanted to.
"I don't think it's going to work darling" I worriedly told Jenny.
"Push harder" she pleaded "please, you can't stop now."
But It didn't take much more. I pushed down as tentatively as I could and all of a sudden my cock head popped into her tiny ass hole.
Jenny took a sharp intake of breath when the swollen head of my prick invaded her sphincter ring and I immediately held back sensing her pain.