I grew up differently, my parents were very rich, and we lived on a huge estate with numerous staff carrying out daily chores from tending the horses to cleaning the fleet of cars and bikes. I cannot remember exactly how many staff we had in the house but I can remember from an early age always having several different Nannies to look after me.
It was normal to me, I knew nothing different. My parents were very busy, seldom at home and for that reason I was basically brought up by my Nannies. One Nanny in particular I will never forget, she was very strict and on more than one occasion I had wished she would resign because she wasn’t one to allow me to get away with anything. The other staff would turn a blind eye to my miss-doings but not Nanny.
Over the years I spent many hours with Nanny. I was about eight years old when she first joined us; she was about thirty at the time. She taught me a lot in more ways than one, as you will see.
As I got older the usual teenage problems occurred, Nanny helped me through all of them, except one at first. I had discovered that at times my adolescent penis would get very stiff and stand out in front of me, a tingly feeling inside if I touched the little stiff shaft. I was too embarrassed to ask anyone about it. Nanny used to bath me when I was younger and smile when she noticed my erections but she hadn’t seen my naked Penis in years, especially not since I had started growing hair around my balls.
I discovered through experimentation that if I stroked my shaft long and fast enough that I would suddenly feel a burst of pleasure down there, as I got older I noticed that a bit of sticky stuff would leak out of the tip. Gradually the amount of fluid increased until I saw spewing, what felt like, litres of thick goo from my penis whenever I played with it.
One day I was sitting in the kitchen with Nanny, by now I was way too old to need supervision by a Nanny but she and I were still very close. I was fifteeen and Nanny was getting on in years but still fit as a fiddle. She had put on a few extra pounds and I often teased her about her round bum. I watched her as she went about her chores, making small talk. I noticed that her cotton dress was slightly open in the front and that I could see between her large breasts when she bent forward. I stared mesmerised at the deep cleft between her mounds; I had not noticed Nanny’s tits before, maybe because her and I were so close that it never occurred to me. Now I could not keep my eyes off of her as she moved around.
I felt my cock swell and harden in my pants, the familiar feeling of the thick head growing to its full size. For the first time I fantasised about seeing Nanny without any clothing. She looked up at me and smiled as she realised the direction of my stare. I looked away quickly but it was too late.
“It’s ok for you to look if you want to, it’s only natural for you to be curious at your age.” she soothed.
I looked back at her chest shyly. Nanny bent forward for me to get a better look. The sight of her deep cleavage had my throbbing cock straining against my pants. Nanny noticed the large bulge.
“My goodness, you have certainly grown down there, are you having trouble keeping it all in” she quizzed me with a knowing smile.
I blushed and tried to hide the large lump but she took hold of my hands and held them away from covering my seething erection.
“It would seem to me that the time has come for you to learn a few facts of life young man” Nanny breathed. Her eyes riveted to my crotch.
She released my hands and reached up to the buttons which held the front of her dress closed. Nanny opened the front of her dress all the way down to her crotch and then, much to my surprise and consternation she pulled her dress open, exposing her large, firm tits to my hungry eyes. I gasped as I took in the shape of her dark nipples, sharply pointed and erect, unknown to me, a reaction to seeing the size of the lump in my pants.
Nanny cupped her breasts and took her stiff nipples between her fingers and twisted them gently, teasing them to an even harder state.
“How would my young stud like to taste Nanny’s nipples?” she whispered, her eyes almost closed with the erotic sensation of her stimulating her swollen nubs.
“I….I…” was all I managed to stammer before she moved forward and took me behind my head with her hand and drew my mouth down onto her waiting nipple.
It was amazing, the firm tip was warm in my mouth, I automatically began to suck on the swollen nub and Nanny gasped, I thought I had hurt her and stopped.
“No, no, young man, don’t stop. You suck like a seasoned lover; you carry on sucking Nanny’s nipple…. Please.” she begged.
I closed my mouth around her again, tracing the thick flesh with my tongue, feeling the little bumps on her areola rise up as the warm, wet sensation passed over them.
Nanny was panting, gripping the back of my head firmly, pulling me closer and trying to push her swollen tit deeper into my inexperienced mouth. My cock was pulsing; I could feel the wetness at the tip as pre-cum leaked from my aching balls. My asshole was clenched tight and I knew that if I didn’t do something about it there would soon be a big mess in my pants.
Luckily Nanny relaxed her death grip and I could pull away for a second. She reached up and shrugged off her dress, it fell to the floor around her feet. There she stood on a pair of panties which clearly outlined the shape of her bulging sex, the fabric pulled deep into the vertical slit of her pussy. On either side black pubic hair peeked out from behind the thin covering.
With out a word Nanny took hold of her panties and pulled them southwards to join her dress around her ankles. As she stood up again I saw her hairy pussy for the first time, her pouting lips held closed by her thighs. I could not take my eyes of her and didn’t move as she stepped forward and straddled my knees, her thighs parted and smell of her arousal hit me for the first time, a warm, welcoming aroma. Nanny paused a second, allowing me to look closely at her now fully exposed cunt. I could see her clitoris standing stiffly between her puffy lips. Nanny reached down and with her middle finger she rubbed the thickening shaft of her clit, retracting the pink hood to show me the little swollen head of her erection.
“See, Nanny has also got a hardon, just like you do” she gasped as she lightly teased her now fully exposed clit. With her other hand she parted her lips, giving me a view of her inner pussy, the thin lips bright pink and shiny from her lubrication.
Taking her hands from her pussy, Nanny reached down and before I could do anything began to undo my pants. The friction of her movements was heavenly on my cock and, although shy, I let her continue until I felt my thick member spring free.
“You really have grown!” Nanny gasped as my cock jumped out at her, she reached down and grasped my rod. It throbbed in her hand as she began to slowly move her hand downward toward my balls, drawing my foreskin back and exposing the thick, shiny head. I could feel my knob swelling further as she stroked the length of my shaft, her other hand back between her own legs, her finger pressing into the slippery slit, back and forth, each time drawing her warm cunt juice over her stiff clit.
I could feel my balls aching to explode and Nanny must have felt it too because she bent right forward until her mouth hovered barely an inch above my quivering tip.
“Ok my boy; I want you to cum, shoot your load into Nanny’s mouth. Don’t hold back, I want every last drop.” She crooned just before she sank down and enveloped my surging rod in her warm, wet mouth. She didn’t stop, I felt her take more and more of my hardness into her until I could feel the tight restriction at the back of her throat wrap around the crown of my cock. She held me there; her one hand cupped my twitching balls, her other between her own legs as she began to frantically masturbate her rampant clit.
There was no way I could hold back as her heat milked the length of my shaft, “I am going to cum Nanny” I bellowed just before I felt my anus clench and the first thick wad of semen erupted into her mouth. Nanny gently squeezed my balls as more and more sperm pumped into her, her other hand paused and her hips thrust forward as she gave over to an explosive orgasm of her own. My last few spurts of hot semen flooded into her as she moaned, her fingers invading her enflamed crevice as wave after wave of pleasure ripped through her pussy.
It seemed like forever before either of us moved, I moaned as Nanny slowly withdrew her mouth from my still very hard cock.
“Oh the wonders of youth” commented Nanny as she looked down at my thick erection “Just cum and ready for more, lets see if we can’t teach you something else today.
Straddling my knees once again, Nanny brought her pussy close to my face again. Reaching down with both hands she parted her pussy lips and opened up herself up entirely for me to see. The mouth of her open pussy contracted slightly and I could see her juices dribbling from inside her. I reached up and touched her slippery entrance. Nanny gasped as my fingers began probing deeper into her vulva. I could feel her pussy contract around my finger as I penetrated her, making her moan quietly. Nanny again took me behind the head and drew me forward until my mouth found her swollen clitoris. Again I instinctively licked and sucked on the firm bud as Nanny thrust her hips forward at the first contact of my warm mouth. I was getting the hang of this; I thrust my finger deeper into Nanny’s cunt, feeling her react by pushing her clit harder against my tongue.
I began to finger fuck her now dripping pussy hole, as my finger moved in and out of her willing opening so my other fingers came in contact with her tight asshole, she whimpered and squatted slightly to allow me easier access to her sensitive back entrance.
I could feel Nanny’s clitoris move in my mouth each time I re-inserted my finger into her, I sensed she was close to cumming so I quickened the pace of the friction of my tongue against the solid tip of her clit. Nanny was panting loudly, bucking her hips in time to my finger fucking her wanton pussy.
I could feel Nanny’s cunt tighten as she began to cum, I pushed my finger deeply into her and with my index finger I teased her convulsing anus. Nanny cried out that she was cumming and I heard a squishing sound as I moved my finger inside her. Suddenly feeling very devilish I applied more pressure to the finger teasing her ass and was pleasantly surprised when the end of my finger penetrated the tight opening.
“Oh shit yes, please don’t stop, I’m Cummmming!” she wailed and I felt a flood of hot, liquid pussy juice escape from inside her. I pushed my index finger hard up into her ass as her pussy clamped down on my middle finger.
“Oh fuuuuuuck” she whined as the peak of her orgasm ripped through her, both her holes convulsed in unison on my fingers.
Her pussy slowly relaxed and her anus tightened around my finger as her orgasm subsided. I sat back and looked up at her. Nanny smiled down at me and sighed.
“You are quite the little finger fucker, aren’t you.”
I slipped my fingers from inside her and looked down at my now raging cock. Pre-cum was oozing from the little eye at the tip and the need to grab hold of it and jerk myself of was overwhelming. As if reading my mind Nanny reached down, took hold of my shaft and again exposed my large purple helmet. She then squatted her cunt downward, guiding my thick head between her warm, slippery lips. She rubbed my cock along the length of her slit from her ass to her clit several times and then stopped with the mushroom at the entrance to her open pussy. She hesitated a moment before letting her weight lower onto the end of my thick rod. I felt her cunt hole stretch open as I began to penetrate her, her inner muscles tight around my knob. It was amazing, I actually felt the moment my cock entered her, my ridged knob popped up through the elastic entrance and began pressing deeper into her.
“Mmmm lover, I want to take that beautiful cock of yours all the way into my pussy, I can feel you moving inside me. You are so big; I haven’t been fucked for years. It is so nice to feel a man inside me” she purred as she lowered herself onto my pole. I felt her warm anus against my balls as she forced my cock the last few inches into her.
Nanny stopped a second, savouring the feeling of being filled by a young stud. I felt her rotate her hips, moving my shaft inside her, rubbing my hardness against the tight inner walls of her slippery cunt.
“Sorry lover, I cannot wait. We’ll take it slow next time. I need to fuck you – now”
With that she began to move my rod in and out of her hungry opening, I reached behind her and grabbed her ass cheeks, spreading them and opening her up to deeper thrusts of my cock. I could feel Nanny’s uterus hugging the crown of my cock each time she pounded her cunt down onto my shaft, impaling herself on me, thrusting her hips back and forth with each insertion to fuck her sensitive g-spot along the length of my cock.
Reaching further back I could feel Nanny’s exposed anus against my fingers as I stretched her ass cheeks apart. As I touched the puckered hole Nanny cried out.
“Yes, please, do it, don’t stop.”
I took this as permission to penetrate her ass again and had no problem inserting my finger into her due to her previous orgasms having generously lubricated her from ass to clit. I pressed deeper, feeling my own cock sliding in and out of her pussy as I stimulated her tight anus. I began to finger fuck her as in time to her stroking her pussy up and down my cock.
“Nanny, I’m going to cum” I warned her as I felt the first stirrings of semen build up behind the base of my cock.
“You go ahead my boy, you mess your sperm inside Nanny’s pussy. Make sure it’s a big load and don’t pull out until you have finished cumming inside me”
The first thick stream of semen rocketed up inside her “Mmm I can feel you shooting inside me” she purred.
After the second or third time I released hot globs of sperm into her willing vagina, I felt her pussy bite down on my shaft as she began cumming on my cock. My finger was tightly trapped in her anus as she pumped her hips back and forth, keeping me inserted deeply inside her pussy. I could feel her milking the semen from me, squeezing my rod tightly as she made sure that she injected every last drop deep inside her.
It felt like ages that my cock throbbed inside her, spilling warm seed onto her slippery inner walls. Eventually Nanny relaxed and I withdrew my finger from her anus. She sat impaled on my cock, feeling it soften inside her. I laid my head on her large breast and enjoyed the feeling of our mixed juices escaping from inside her and running between us.
I think we stayed like that for quite a while, my soft shaft still inside her.
I looked up at her and she smiled. I felt her pussy tighten around my knob and the familiar sensation of my erection returning as she massaged my cock with her cunt.
It wasn’t long before my thick knob was once again pressing against her uterus deep inside her pussy.
“Ready for round two?” she asked “This time we take it slow”
I shut my eyes and concentrated on the sensation of her experienced pussy lovingly teaching my cock the art of pleasuring a woman.