Perverts 'R' Us

Jenny's Awakening

By Jenny ( m/bgg, M/F/m/g, inc, 3some, cd, bi )

This story is true. It happened to me when I was a horny teenage boy growing up in central Indiana in the sixties.

I was 16 years old with my first car and payments for insurance to make. I took a job babysitting two pretty little girls ages 9 and 11 as well as a really cute little boy of 10 years. The girls were Christy (9 years old), and Lisa who was 11. The boy was Matthew. He was a very shy little boy of ten years who had a little stiffie showing through his pants at most any hour of the day or night. The girls both had crushes on me, "the older man," and I think Matthew was just a bit jealous.

On one particular day I was asked to sit for the kids, since their single mom had a date that night. She informed me that she would be very late and as such I would be spending the night. She also told me that the girls had been having bad dreams of late and might want me to lay down with them at bedtime until they got off to sleep. No problem! Being the perpetually horny teen that I was I figured I might get a look at one or both of the girls little pantied asses and hopefully a glimpse of their little camel-toes. I was still a virgin at the time and even the thought of seeing any girl's parts "down there" was very exciting to me. Needless to say I agreed to the idea of sleeping with two pretty little girls immediately. Little did I realize that I would leave there the next day a more educated young man indeed!

The job started off about 6:00PM on a Friday night, with the kids wanting to wrestle with me. The kids were supposed to take turns as each one won the match or lost, but of course it turned into a free for all within just a few minutes. As we all wrestled around on the floor I realized that the youngest girl, Christy, was spending a lot of time between my legs and doing a bit more squirming around on certain parts than was called for. COOL!

My young teen cock was soon standing tall, nearly touching my belly button above my pants. Christy seemed to spend a lot of time rubbing up and down the bulge in my pants, but horny as I was becoming I really didn't care. Besides, Lisa kept trying to wiggle her little bottom onto my face; not that I minded too much, it smelled really good and girly to my young nose.

All the while, Matthew seemed to be trying to help me "win" by hunching up against Lisa's back. All three of the kids were doing as much moaning and grunting as giggling and screaming. By the time the wrestling was at an end, both girls said they were sweaty and wanted to take a bath. Matthew agreed, but wanted to take one by himself.

I drew the bath water for the girls, with lots of bubbles of course. Matthew wanted to watch TV while the girls took their baths, so I turned on the TV for him and told him I was going to make sure the girls didn't flood the bathroom. When I got to the bathroom door, I stopped to listen and it seemed to me that there was no noise that should usually accompany little girls taking a bath. The door was slightly ajar, so I very carefully opened it just a crack and peeked in. I didn't see the girls at first and just panicked and burst in.

There were the girls and they had made the abundant suds into little bikinis, just covering their soft little bodies and were in a rather adult embrace in the tub, one on top of the other face to face and kissing each other. They quickly parted when I entered and turned to me as their faces turned red and they began to stammer out excuses. Meanwhile I was so surprised by their embrace and the view I was getting of the suds running down off of their little tittie-buds, over their tummies, and down between their legs that I could only stammer out that it was OK and that I was just worried about them.

They both smiled and looked at each other as they each put one hand over the other's little love nest and began rubbing up and down each others little pussy crack. Then as they slid back down into the water they looked at me and said it was OK and that they would have a little surprise for me when bedtime came. I returned to the living room with a large bulge in my pants to find Matthew lying naked except for what appeared to be a training bra and a pair of silk bikini panties, both pink, under a black nightie that was so sheer that I could see him rubbing his little cock under it and through the panties. His eyes were closed and he was moaning like a little slut in heat and his other hand was under his butt lifting himself up and down off the couch as he fingered his little boy pussy.

I had never seen anything like it before except when looking in the mirror in my bedroom while I masturbated myself when wearing any one of my "girl things". Oh, yes, I am trans-gendered and still love to dress up in sexy girl clothes and do any number of kinky things to myself. But that is another story.

Matthew was so involved that he didn't see me as I crept around to the back of the couch to watch him. I unzipped my jeans and pulled my extremely hard cock out and began to stroke it as well while enjoying the sight of Matthew pleasuring his little prick. My cock was becoming very wet and slippery from the pre-cum drooling from its tip when the girls walked (rather tumbled) into the room. Matthew looked up but returned to what he was doing not paying me any attention at all.

The girls didn't waste any time in coming over to me and pressing up against me began to unsnap my jeans and run their soft, hot, little-girl hands up and down my pulsing hard cock. At this point I wasn't about to say or do anything that would make them stop, so I just stood there as they slowly pulled my jeans down, only to reveal a pair of my sexiest blue bikini panties covering my hairless and tight teenage ass. They just smiled and proceeded to unbutton and remove my shirt to reveal my matching blue bra. The girls removed my shirt and jeans, leaving me standing there in only my bra and panties with a hard cock sticking out of the leg opening of the panties drooling pre-cum.

Christy came around to my front and began to rub her hot little tummy up and down my cock as I felt Lisa rubbing my panty-covered ass with her hands. As Lisa rubbed up and down and around, she began to slip her hands through both leg openings and caress my bare, hairless ass and probe my tight rosebud. Meanwhile, Christy had pushed me to my knees with Lisa's help, backed up to me and put my hard-on between her legs and began to hunch back and forth so that my cock was sliding back and forth over her hot little pussy lips. Her pussy had been leaking for awhile, because it was as slick as slick could be.

Her little pussy lips folded neatly around my prick and transferred their heat to my already-overheated love stick. I was in seventh heaven, feeling her hands guide my cock across her pussy lips and didn't mind when Lisa began to finger-fuck my opening with more and more speed. This day was getting better and better as it went along. Lisa removed her hands just long enough to pull down my panties and, I thought, resume her ministrations to my now dripping boy-pussy hole.

I was fast approaching an explosion of epic proportions when Lisa appeared next to Christy. I looked around and found Matthew now doing my pussy like he was born to it. He just smiled when he saw me looking and proceeded to meld his little body up against mine and begin pressing his little cock into my boy pussy hole. As I looked around front I found Lisa on her back with her face buried between Christy's little legs, making loud slurping sounds as she licked and sucked on her pussy. Christy was on her hands and knees wiggling her cute little ass in the air as Lisa licked her pussy and fingered her ass.

Christy then leaned out to me and, releasing her grip on my cock, took it into her mouth as far as possible, which was an amazing amount, considering I had a healthy 6 inches of hard cock and she looked as if she had half of it inside her mouth. I couldn't take it anymore and immediately erupted my sperm down her throat. To her credit, she swallowed most of it. Some of my cum dripped down onto her chin and she immediately got up off of Lisa's face and bent down to give her a taste of it.

Matthew meanwhile had pulled out of my boy-pussy and was furiously jerking his little cock and bucking his hips in time. Lisa quickly crawled over to him and engulfed his little cock with her pretty red lips just as he began jerking uncontrollably and groaning with abandon. When Matthew finished with his little-boy orgasm the girls each commandeered one of my legs, sat on it, and began rubbing their little hairless pussy along its length, leaving trails of sticky juice along the smooth skin.

By now my own cock had come back to life, and when Matthew saw it he eased over on top of it and began to work his little and very tight fuck hole onto it. He decided that his hole needed some lubrication though, and reached down to Christy's dripping little cunt hole and inserted fully three of his stubby little fingers into it and worked them around until his hand was dripping slippery pussy juice. He applied as much as he could onto and into his fuck hole. He then eased back down to where my cock was just beginning to find its way into his hot little ass and in one smooth motion sat completely down so that my cock entered him in one smooth thrust.

The feeling of his hot little-boy ass enveloping my throbbing hard cock was unbelievable, and from his deep sigh it must have been really good for him to feel too. His little pecker became immediately hard as a rock and stuck out from his small ball sack like a little spear. It looked as if he were fucking the air as he bounced up and down on my own love stick. I reached out and took his little three and a half inch cock in my hand and let him hunch my hand at the same time he was fucking his tiny ass onto my stick. I felt one of the girls begin to fondle my ball sack massaging it and rolling my nuts around in her tiny little hands like they were marbles.

As I looked back up at Matthew, I saw tiny hands pinching and rubbing Matthews little-boy titties, pulling on his nipples and rolling them between her fingers. Matthew moaned and grunted each time my cock hit bottom in his little asshole and every time it did his tiny cock-ette would pulse in my hand, leaking little boy precum out onto my fingertips.

His little hole was squeezing my cock each time he withdrew it from his butt and seemed to open back up to accept the insertion of it into him. I could feel my balls churning in Christy's hand as she rolled them around and suddenly knew I was about to cum. Matthew felt it too and in an almost whisper between moans asked me to please shoot my stuff into him, he wanted to feel the hot rush of cum shooting into his tummy.

I immediately began to unload what must have been a gallon of baby juice into his asshole. There was way too much to keep inside such a small place and my sperm began to find its way out around my cock. It ran out of his stretched hole and onto my ball sack as I kept cumming and he did as well. I'd never seen anyone have an orgasm in their asshole, but Matthew did and I felt it as his fuck hole walls pulsed around my spasming cock.

As soon as our cums had subsided, Matthew rolled off of me, only to have Lisa lock her mouth onto his ass as it dripped my sperm and begin to suck it out. At the same time Christy pounced on my withering but still leaking cock and began to lick and suck Matthews and my juice off of it. Matthew was groaning and humping Lisa's face as she sucked his asshole dry of sperm as his cock-ette never went soft, but just kept visibly throbbing and bouncing in the air. I immediately leaned over and sucked his dick into my mouth, tasting his sweet juices and making him squirm even more.

When it finally ended, all three of the kids lay out on the floor and smiled big smiles at me and asked if I liked playing with them as Christy slowly fucked my boy pussy in and out with two or three of her small fingers while Lisa stroked my cock. I could only whisper that I really did and would again if they wanted. They told me that they wanted to play really grown-up games with them that night and were glad that I liked wearing "pretty" clothes and would I mind if we all went to bed now?

Christy told me to wait until she came back from the bedroom so she could lead me in. About 15 minutes passed before Christy returned. When she came into the room where I was, she was absolutely stunning. She looked like a very short 20-year-old, with no titties under her too-big black silk nightie. She had some clothes on her arm that she told me I should put on and much to my surprise she had raided her mom's lingerie drawer and had garters with stockings, both black and with the old time seams running up the back of the stockings. Along with this she had a pair of white very small bikini panties (her mom liked them very tight against her "thingy" Christy told me) and a chemise top and some latex breast forms her mom used sometimes.

She helped me on with all these things in a very delightful and softly touching way, managing to rub my cock every chance she got. When we finished my dressing, she stepped back and smiled her pretty little girl smile and asked me if I was ready to go play big games with her and Matthew and Lisa. I could only nod my head and she took my hand and led me to the bedroom. When we entered I saw Matthew and Lisa head to toe slurping and sucking with such abandon that they didn't even hear us enter.

Christy promptly went over to Matthew and began to massage his tight little ass and squeeze his tiny little nut sack, much to his delight. I lay down on the bed next to the three of them and was immediately treated to a nice cock massage and an ass probing finger from Lisa as she continued to suck Matthews little cock in and out of her hot vacuum cleaner of a mouth.

Christy's face was now buried between Matthew's ass cheeks with one finger probing in and out of his hole. I felt Lisa move at the same time as she removed herself from Matthews cock. She went to the end of the bed where I couldn't see her and pretty soon returned and whispered into my ear and asked me if I liked being dressed up like a sexy girl. She then asked me if it would be OK if she did me like her mom's boyfriends did to Matthew and put her thing into my little-boy hole. All I could do was mumble "uh-huh" since Christy had taken up stroking my cock with both hands. I had no idea what Lisa wanted to do to me, but I was game for anything at this point.

I felt Lisa rubbing something slippery onto and, much to my delight, into my hotter-than-fire fuck hole. She shifted her little body, barely moving the bed and came around into my view to show me a moderate sized strap-on dildo that was, for the day and time, a realistic depiction of the real thing and must have been expensive. She smiled and said she would be easy with me and returned to her position behind me.

I felt her put the cock head against my little pucker hole and begin to rub it up and down and all around my sphincter. She began to push it in slowly and would wait every half inch or so for my hole to open up for her. As Lisa slowly worked the plastic cock into my slippery boy-pussy, I felt Matthew crawl under and between my legs. I felt his mouth engulf my hard prick as his hands moved up and down the shaft, bumping into my nut sack as he went. I was being fucked up the ass and having my cock sucked at the same time and now Christy pushed her little tittie buds onto my lips and begged me to suck on them, which I did with no lost time as she shoved two and then three fingers in and out of her own little pussy hole.

Christy's juice was running off her hand and down her skinny little legs as she humped her own hand and had her titties sucked and licked by me while my boy pussy was being fucked by little Lisa with her strap-on cock and my own boy-clit was being sucked and caressed by Matthew. We switched positions around several times during our little play time with Matthew fucking my boy-cunt, me fucking his asshole while Lisa and Christy sucked each others pussies or played with and fingered my fuck hole and just about every position four people could get into. We all eventually wore out and fell asleep on the bed silk bedecked and naked young bodies entwined and juice-soaked.

I awoke and found their mom on her knees sucking her date's cock deep into her throat while squeezing his big ball sack. She stopped when she saw me and asked if I had enjoyed her kids while she was gone and if I might like to join her and her boyfriend having fun with the kids someday soon, which meant today as it turned out.

To make it short, Christy wanted to be the meat in a sandwich of me and her mom's boyfriend. Her mom lifted her up and laid her on top of me while guiding my hard-again cock into Christy's little-girl cunt and then helped her boyfriend place his cock into Christy's tight little backdoor. All that Christy could do was moan and wiggle her tiny body around between us as she tried her best to get these two huge (for her) cocks as deep as she could into her young womb and tiny butthole.

I could feel his cock rubbing mine from the other side of the thin membrane separating Christy's backdoor from her silky, tight and hot pussy hole. Christy came again and again over the next hour, finally falling asleep right after we both shot our cum into her at the same time. As Christy slept, her mom cleaned her holes up by using her tongue, fingers, and lips on her daughter's pussy and asshole.

When we all came back to our senses, the kids' mom said she would buy me my own wardrobe of girl clothes to wear when we all got together, so long as her boyfriend could fuck my hot little-boy cunt too and if I was game we could get even kinkier with animals especially the big great dane her boyfriend had. She said he was well-trained and that she and her boyfriend would like to see me get fucked by the dog sometime.

Needless to say the year that followed was a fun-filled adventure for me. Naked little slippery wet bodies rubbing all over me, an exceptionally good-looking woman and her boyfriend using me as the woman I had always wished to be. My boy-cunt had lots of use that year and I have never had such a good fuck as Christy and Lisa and Matthew when they wanted to "play".

I am still trans-gendered and dress as a woman whenever I can. If you liked this adventure write to me at hrnytvjen@yahoo.com and let me know. I have many true-life sex adventures that I have had that I would like to tell you about. And who knows, maybe we could "play" grown-up games together sometime. Luv, Jenny.