Chapter One: I start a babysitting job

First I’ll explain myself. It was one more year ‘till I got my learner’s permit. I was a freshman, not masculine, slim arms and hips, narrow shoulders. I grew long dark brown hair that I kept hidden mostly under a cap or a beanie and sometimes in a ponytail so nobody really noticed how long it was. Brown eyes. I was pale, long legs, a few inches over 5 feet, fresh white skin with ruddy cheeks, (the zit demon had skipped me over). Hairless arms and nearly hairless legs, just a very light fuzz. I certainly didn’t shave yet. But I had a butt! I wore jeans and cords all the time and my butt looked good in the mirror, tight and round and kinda bulgy.

I was an only child. Mom didn’t pay much attention to me, but she was happy when I got a job and was out of the house. Dad ignored me once he figured out I wasn’t going to be a football player. I didn’t have many friends outside of school really. There were kids I talked to in class but I didn’t go to their house or they to mine.

Somehow I was offered a babysitting job for single woman, Twyla Morgan, so she could go out in the evenings. The Father was gone, divorced. It was a nice enough two bedroom condo, two story. She worked some during the day but not every day. They seemed to have money, maybe from the divorce settlement. Nice things in the house, a nice 4 door beemer in the garage, a big TV.

Cindy is a 5th grader. Curly Blond hair, blue eyes, cute kid, cute enough in fact to stare at but I made sure not to. We just sat on the couch as soon as I came in and both looked at the tv.

“I’m going out with the girls, not super late, I mean it’s a school night.” And then” Gotta look good!”

Mrs. Morgan checked herself in the mirror at the bottom of the stairs. She was tarted up in a leather skirt and sheer black nylons, hair curled, smelling good, feminine, sexy. It was her I was definitely staring at. She had hips! Hips and boobs and they were out on display! She was a little bit taller than me and with the black stack heels she was wearing towered over my head at least 5 inches! I felt quite small. I had met her a few times before but she was always in her around the house attire, sweat pants, flannel shirts, hair tied up. I thought of her as the same age and therefore the same basic whatever… as my mother, just a housewife. But now she was wearing a satiny blue blouse with the black leather skirt and black stockings. The blouse was open a bit and I could see cleavage. I could see a bit of the lace texture of her bra telegraphing through the satin. Her dangly earrings chimed as she got her things together and I gave her a good stare. This was a woman!

I had never touched a girl. Like sexually. I knew I liked girls, I just never had. Playing and laughing but kisses no. There was holding hands when I was much younger, lots of looking and smiling.

I loved looking at pictures, mostly the Sears catalog at the bra and lingerie section. Silk and satin and lace were invigorating to my young teen libido. I had seen my dads few playboy mags a while ago but they seemed to have been thrown out. The grown women with their shocking bush of pubic hair, soft focus and glowing skin and then pink inside made my face feel hot. It was a revelation to me. I liked seeing the female form with all those intimate decorations like stockings and garters, panties and bra cups, corsets and negligees, sheer satin, lace and chiffon. I wanted to know how it felt to the touch those things, what flesh and skin felt like through them.

I had begun masturbating a lot. My penis was not large, most of the time it was tiny. My little balls had no hair yet and my peenie protruded a mere two inches like a little finger. When I pulled it and rubbed it enough though it would get hard and extend to a pointy 4 ½ inches which I had measured. It was about as thick as one of the magic markers that came in the set of colors nd smelled like sweet things when you took the cap off. I liked rubbing it on things like my pillow and a fuzzy blanket. One or two times I tried rubbing with a pair of my mom’s underwear from the hamper and the silky texture felt thrilling on my boner but the conflict of it being my mother’s undergarment kept me from doing it very often. When I got her panties and put them on though it was always sufficient to make my pecker hard and tingly. When the sensations of rubbing and touching got too intense and I felt like I might pee by accident I would stop and relax and try again a little while later. When I was left home alone for a long time and I had some visual stimulation I could get to that feeling three, four, five times in an afternoon before I got tired of it.

One reason I took this job was the chance to look at Twylas underwear drawer and play with things when the girl was asleep and I had the whole place to myself.

She and I talked about nothing much, how bad TV was, school was “just OK”. Friends?, not a lot. Mom? “She’s ok.” Mine? “Doesn’t like me. Dad doesn’t either”. She looked fixedly at me and said “I’m sorry, that sucks.” I got a little jittery with her blue eyes drilling into mine. Her lower lip is a lot bigger than her upper lip.

I was watching the TV, studying the furniture, stealing a glance or two at Cindy on the couch beside me when I finally noticed, a few down in the stack of magazines… a Victoria’s Secret catalog! The Holy Grail! Now I had a plan! When Cindy went to bed I was going to play with myself looking at the gorgeous models on those hallowed pages, with their silky hair and longing eyes and perfect skin, luminous and cinnamon, and that lace and lingerie that looked good enough to eat, like frosting on a cake. And I was going to get into the drawers upstairs and rub myself with Mrs. Morgan’s panties! Plan!

“Do you like Victoria’s secret?” OMG she saw me! She pulls the catalog out and onto her lap beside me. “I think they’re sooo pretty” I gulp and answer “Me too!”. She flips the pages slowly and I’m riveted. Satin & eyelash Babydoll, lacie strappy-back slip, georgette halter negligee, lace and mesh teddy, lightly lined underwire cups, snap closure at bikini bottom, satin and lace halter gown, plunging neckline, open back, nylon satin and silk. My stomach felt fluttery.

Suddenly she just up and says “Do you want to Play dress ups?”

Cindy leads me upstairs to the larger of the two bedrooms and shows off the walk in closet full of clothes and her mom’s lingerie. There is an amazing amount of stuff, several drawers full in the dressers in the bedroom! Cindy seems intent on finding some outfit she has in mind while I take advantage of being left alone and run my hands over and through the wealth of silk and satin, lace and frill and stretch and mesh. This is Mrs. Morgan’s intimate clothing. This part cradles her ample breast, that strip of cloth touches her crotch. Everything smells of her perfume, actually combinations of several perfumes. It’s really sexy, intoxicating, I want to feel the things that touched her skin touching my skin. How would it fit on my body?

Cindy goes out, to her own room, and dresses up in something she found. She returns and it’s too big, I have to help her. It’s a blue satin bustier with sheer black panels on the sides, high cut on the hips with lace trim. There is a plunging V where her Mom’s sumptuous breasts would be. Garter straps connect to the sheer black stockings with lace tops that are pulled up only past her knees because they are so loose. The matching blue panties are bunched up a bit.

We find a few safety pins so the material can be taken in and not look so baggy and gets out of the way of her skin. My fingers brush against her body.

“You can put stuff on in the other room.”

I’m by myself in the walk in closet, surrounded by Twyla’s long dresses and short dresses, blouses, pants and skirts, jackets and suites, racks of shoes. I shuck my shirt and pants and then cotton briefs onto the floor. I’m so excited I can hardly breathe.

Her bras were very large with underwires. Even hooking it as tight as I could they were too big and only the straps held it up. I pull a pair of satin panties with lace trim up my legs and over my butt. Too big, too baggy, but it stays. I try several others but they’re mostly the same. French cuts, bloomers, boyshorts, only the tightest thongs seem to fit me.

I try tucking my small soft penis between my legs. It looks good, the flat abdomen sloping down with no protrusion. I turn this way and that in the mirror. I see thin hips but a juicy butt. It sticks out in the back if not the sides like a real girl. However, the tuck doesn’t feel as good like it looks. The tingly feel of silk on my balls and my pecker is missing. My balls rise up and inside me so small that it doesn’t matter that much. A skirt, a ring of frills just below the waist conceals me altogether. You would have to look really close.

Soon we are changing outfits and taking off clothes in the same room, digging through her Mom’s multiple drawers of lingerie. Turning away, giddily pulling off the last pair of panties and pulling on a pair of fresh cool satiny tap pants in bubblegum pink with a matching camisole. It fits me but it’s still loose around my straight hips and flat boy chest. Twyla’s sumptuous hips are way bigger than mine and her panties are huge on me, at least not snug and smooth and clingy like I want them to fit and feel. I look baggy and bunchy. I try on a bra. Only the shoulder straps keep it on. Her tits must be huge!

I find myself staring at Cindy and when she sees me she just stares back and a big smile forms. She’s all ribs and hip bones. Skinny legs but a cute curve to her ass cheeks and perfect creamy skin all over her body. Lace and blonde curls and golden fuzz of her body hair.

She jumps on her mom’s bed. We’re getting all bouncy and giggly together. Loose clothes that don’t fit are almost falling off as we get more rambunctious on the bed. I tickle her then fall off, flopping down, laying parallel, a short distance from each other, catching our breath from laughing.

“ You look so pretty.” Says Cindy. I can feel her breath on my face.

“ Really? I do?” The whole bed is silky and I roll onto my stomach and rock my hips a bit into the bed covers. It feels nice and stimulating and inside the pink satin my dick starts to chub a little. I shouldn’t do that. I’m staring at her, she’s smiling back. I feel silky.

Suddenly I’m hugging her, and my arms wrap all the way around her small body, she wriggles but snuggles in against me. I think I might be getting an erection in the loose silk shorts. I feel a little awkward and let her roll away. We lay on the bed, not too close, and she turns on the tv. She nuzzles into me for a second but then we pull away and she’s blushing and won’t make eye contact.

“I like to watch movies here”. We watch something and my penile excitement subsides. She falls asleep very close to me as I watch the screen. Maybe a couple of hours go past. Suddenly I’m bolting up and in babysitter mode, it’s past midnight.

“Cindy wake up, you have to put on your PJ’s.” She sits up, eyes mostly closed, slips off the bed and stands there like a little zombie in a loose fitting camisole and panties that droop down on her tiny hips.

“You have to take this off and get your pajamas on and go to bed.” I begin to undress her barely responsive body, pulling the cami up over her head. She holds her arms straight up. I go ahead and tug the loose panties down her legs as she stands in front of me. I glance at her little slit but only for a second. That’s not good, I shouldn’t be doing that.…and put her in her PJ’s, a fuzzy blue pair hanging on the door of her closet. Then she’s in her bed and I have to put Twyla’s clothes back in the drawers. I don’t dally because I’m a little freaked out by what we’ve been doing. I’m good at remembering where everything goes. I straighten up the bed after all that bouncing and wriggling. Back in the closet, I’m absorbing all the smells, multiple perfumes, clean laundry scents, musky dirty laundry smells that I don’t even understand yet. I try on a formal dress, dark blue hanging on the rack, rubbing my swelling cock on the satin and ruffles. I take a pair of her panties for my own. Black and lace trimmed they were in a neglected wad at the very back of a drawer where maybe she would never notice. She has much bigger hips and bottom than me but that means lots of loose fabric to fold around my prick. I put them on with my tighty whities over them and then my pants so as not to get caught. It feels silky.

I walk back in to see Cindy in her bed. I stand for a long moment looking at her soft cheek and then bend forward and kiss her sleeping lips before skittering downstairs. I settle on the couch and get my good long look at the Victoria’s Secret catalog. Chantilly lace, garter slip, add two cups push-up bra, halter babydoll, sexy luve lace and mesh corset, demi bra, dream angels satin teddy. My hand gropes down my pants and rubs the silky shimmer of Mrs Morgan’s panties against my hardened penis. Chantilly lace plunge teddy, sexy pleated baby doll, a sheer shape with a plunging front and crisscross straps at the daring low back. A tiny bow at the front adds a hint of sweetness. The tingly feeling was becoming a buzz and the tip of my straining prick felt numb.

The door clicks. I jolt up. I jump. The key was in the lock but not turning, and then not turning correctly. My hand was out of my pants, my shirt pulled down and I managed to get the catalog back in the stack when the door opened and Cindy’s mom stumbled through the door.

I can see she’s drunk as she starts to stagger up the stairs. It’s 2:30in the morning. She mumbles she’s sorry, shouldn’t be so late. I think she’s coming back down to pay me but after 10 min of silence I’m still waiting while my heart rate returns to normal. I decide to follow after her and find her in her bedroom passed out on the bed where Cindy and I had been laying and playing and napping. She’s on her back with legs slightly spread, one arm out and one arm over her head, covers pulled up but not completely over her.

“Mrs. Morgan?” I call out her name and touch her leg, shake her gently, then a little more. Her clothes are off I can tell. I slide the covers over just a bit and I can touch her breast. A real tit! And it’s big! Soft but not flabby. They must be real, a fake boob would feel like a balloon or something. If I touch lower and pull at the bed covers I could get to see the spot between her legs. I uncover her navel, then her lower abdomen and then the patch of hair above her slit, trimmed into a dark trapezoid. Her labia were darker than the surrounding skin and textured, wrinkly but hair free. Her inner lips were darker still and like a frill of meat protruding just a bit further.

She is totally passed out. My boner is streching my pants and my stolen silk treasure. All evening playing with Cindy, seeing her bare body, wearing all of Twyla’s underwear and lingerie, rubbing my penis on her slips and her dresses, feeling her stockings on my legs and her panties cradling my nuts. I could imagine Mrs Morgan to be a Victoria’s Secret model laying there, silky hair spread everywhere, body sprawled amid the fine sheets, the skin of her legs and her hips and her buttocks bare and gorgeous. I slide my hand along her thigh, not to wake her but to feel her skin. I pull the sheet down to her knees. I lean over the bed. I get my left hand in my pants and grip my stiffness, wrapped in silk and I drag my right hand down to her crotch. It feels moist and heated. I part the lips and reveal a bright pink slit. I’m touching my first pussy ever. My fingers get wet in her juice. It’s slippery and thicker than water or pee, it’s mucus I guess. I go from sliding them back and forth to pushing inside the wet tunnel. My cock can’t stand it. I can’t believe what I’m doing to this sleeping woman. I’m gripping hard and my penis head is buzzing and tingling and I suddenly feel my legs buckle and the muscle under my balls jums and spasms. The tendons down the inside of my legs twang like guitar strings. It’s painfull and uncontrollable and super amazing all at once. I pull my fingers out of Mrs. Morgan’s cooch and stand there bucking my hips and humping the air as the feeling recedes. I can feel some wetness has oozed out of my cock head into the satin panties. I’m suddenly super sensitive at the tip and have to let go of my pecker. I back out of the room, still staring at the half naked woman, a real woman, passed out nude on the bed. I touched her cooter! I’ve still got her juice on my fingers!

* * * * * *

I get asked to sit again just a few days later.

Cindy’s dressed in pink strechy short shorts, pink socks with lace trim and a ruffly pink halter top that just wraps her boob area. She has her hair in two loose pigtails with pink bows.

Twyla smiles and touches me on the shoulder. Her perfume wafts over the room. Her jewelry jingles. She is in a tight pair of designer jeans that look great on her full hips, high heels and a swishy blouse. She flounces out the door and Cindy and I sit for only a moment on the couch before she asks, excitedly if I want to play dress ups again.

More different outfits! I find a black lace corset with shoulder straps and garter straps hanging down and pink floral panels on the sides. Black satin panties that are cut high up my hips. I get some sheer black stockings and they stay up once I connect the straps.

Shoes! To my delight I find that Twyla’s feet and mine are the same size! Even though she’s bigger than me I guess my growing boy feet are matched to hers and I can slip on her shoes. Holy cow does she have a lot of shoes! I pick a black patent leather pair with spike heels and come teetering out of the closet to show Cindy.

She’s in a peach silk camisole that comes down far enough to cover her bottom but I can see she is wearing a baggy pair of Twyla’s panties underneath. Black I think. She squeals and beams at me.

“You look sooooo good!”

“Thanks!” I’m blushing and my head is buzzing a little. My outfit doesn’t fit very tight but the feel of it on my skin is great and looking at myself, especially as I spin before the full length mirror, I see that the high heels make my butt look really cute. I walk slowly, uncertainly, to where Cindy is standing and we look each other up and down. Her smooth shoulders and flat chest set against the peach silk is aglow with her excitement. She reaches out and touches my abdomen and the boning of the lace corset. She puts both hands on my hips, touching the loose silk and then pulling herself to me and we wrap in a tight hug.

“Let’s play grownups.”

“Ya?” I let my hands slide up and down her back, feeling her through the silk and pressing her into me.

“Like what they do at bedtime”

We lay down in her mom’s bed, face to face and she gave me a few light kisses on the lips. I felt like Cindy was trying to be more serious, more like an adult. She didn’t giggle and squirm as we pressed together. I pulled back and looked deeply into her eyes. Brilliant blue with flecks of gold and black. She was really really darn cute! She blushed and buried her face in my neck. I rolled over onto her and she squirmed a bit under me, her legs spreading and getting me centered. The skin on silk on silk on skin made our bodies slide around as I held myself up, trying not to squish her too much. I felt myself swelling in the black panties.

Cindy didn’t seem to mind that we’re both dressed in women’s lingerie. I’m the man and she’s the woman at this moment. I’m holding my weight up so I don’t crush her tiny body. My penis has straightened out and it’s aligned with her softest spot.

“sometimes the woman is on top” she tells me.

“ok”

I roll over and onto my back and Cindy crawls up on top of me, lies still. We’re just pretending after all but I feel her weight on me and her warmth. Her pelvic bone puts pressure on my slim dick. She grinds gentle circles and with a sizzling flash I cum in her mom’s panties. I convulse under her and she just looks at me, smiling.

Cindy doesn’t seem to get upset that I soiled the black satin undergarment. It’s ok she says, just put it in the dirty laundry hamper, Mom’ll never know. Maybe she already knows what semen is and what a male orgasm is all about but there’s no telling. She looks at me naked when I strip off the gooey satin undergarments and watches as I clean up the the sticky mess. She seems worn out or unsettled by what we’ve done together and silently goes off to bed on her own. I put stuff away and straighten up the bedroom and then check on her. She’s very asleep. I kiss her lips, longer this time and as I do I vividly remember cumming with her lithe body straddling my hips. I feel my dick twitching, and I want to rub on her again and get that buzzing and then shooting feeling in my prick but I don’t. I go down stairs and doze on the couch. Mom comes home, less drunk, and pays me this time. She still looks good, smells like smoke. I watch her big breasts in the sturdy bra shifting under her blouse. I think about last time when I touched her passed out vagina and I stare at the crotch of her tight jeans as she’s getting money out of her purse.

“Did everything go fine?”

“yes”

“I’ll have you babysit soon.”

Babysit.

. . . . .

The next time I come over we play more dress up, it’s obviously our favorite thing. I put on a merry widow in black lace with big stiff bra cups. Cindy throws balled up stockings at me trying to make a basket. I switch to a camisole top because Twyla’s big bras don’t fit and just look funny on me. It has little black polka dots, black lace across the chest, right above my nipples, and lace trim on the sides of the matching panties. She gets into a nightgown that would be short on her mother but looks full length on her. Tourquise satin with some bunchy panties underneath. I help her tie the straps of the nightgown together so the top isn’t so loose.

Cindy decides to show me her Mom’s dildo drawer and we’re amazed! Big ones that look like real dicks, little shiny plastic ones. I switch on a vibrating, rotating purple thing with weird feelers sprouting off of it. We collapse on the bed in unstoppable laughter.

“What is that?”

“It’s supposed to be a penis!”

“real penises don’t do that stuff! Do they?”

“No way!”

I turn the weird thing back off and drop it in the drawer. Cindy is on the bed, recovering from her laughing fit and I roll next to her.

“Mom uses those things a lot. I hear her late sometimes moaning and I try not to laugh out loud.”

“Have you tried one?”

“A little bit, not really…” She’s avoiding eye contact “well the buzzy kind feels good sometimes but I never stick it in.”

“Do you touch yourself? Rub your pussy?” I asked.

“Well… YES.” She smiled real big and I smiled back.

“Ya, I do too. I think panties are sexy and I like to rub myself with them.”

“Last time, when we were on the bed… you had a climax?” she asked, quizzically.

“Yes, I had an orgasm.” I said, trying to sound like I knew what I was talking about.

“That’s cumming?”

“Ya, it felt really good.”

We lay still and close for a while, I feel the warmth coming off of her body and the puffs of her breath.

“I want to touch your penis”

“I want to touch you down there too”

My hand slides down her body and she reaches out to my satin covered crotch. Feeling her exploring fingers on my penis turns it stiff immediately. With my hand I’m feeling her super soft parts through the panties. She sighs approving sounds and grips and tugs my erection. I separate her lips with one finger and push it inwards a few times and then she gasps. She feels gooey, stickey between her lips and not wet and slippery like her mother, er Twyla’s pussy did. We keep rubbing and touching and then I lean in and kiss her on the lips. Cindy responds with enthusiasm and after a few minutes we are opening our mouths to each other and flicking tongues together. It seems to make both of us hornier and the hand movements get more frantic. We each give to the other what it is we want in return and the tempo picks up to a fever pace. I don’t know if she climaxes but I tell her when I feel the straining and tingling get to be too much.

“It’s gonna happen, I’m gonna, I’m gonna… uh,uh!…uh!” I’m spasming in her hand and my whole body twitches and there’s wetness in the panties I’m wearing. She giggles and kisses all over my face. I feel a little sleepy as I relax back into the soft bed next to her.

I don’t remember Cindy getting up and going back to her room.

Twyla comes home drunk and finds me in her bed. I hear the click of the door and shoot straight up but it’s too late, I’m totally busted!

“Yes, I thought so!” she says, clicking on the light and walking up to the bed. “I found some sticky panties in my laundry hamper and several items of lingerie out of place. You’ve really been going to town it looks like. I hope you’ve been enjoying yourself.”

I’m paralyzed and speechless, my body feels icy cold.

“Now stand up for me. Let me see your pretty little body in those sexy panties.” My face is burning.

I gulp and stand up as she commands. I’m in so much trouble! There follows an inspection of me wearing her clothes, pink cami and matching knickers. My stiff little pecker has rocketed out as an unexpected result of this attention. Twyla seems to give her approval. She drags her fingers across my skin.

“You have beautiful legs and a nice trim tummy but it’s a shame your hips are so skinny, you don’t fill out my underwear very well.” She pinches me. “You do have a juicy little ass my dear.”

She goes on caressing me, finger hooking under the waist band, dragging across the tickle spot right over my hip bone. I jump. My heart is racing and my breath is shivery and uneven. She strokes down my crack and tucks a finger under the panties between my A hole and my tight little nuts. She grips my ass cheeks in her hands and kneels on the bed in front of me, eye level with my peter, pitching a tent in her purloined and recently soiled underwear. She slowly peels the satin away from my genitals.

Slightly sweaty and breathing deeply, her hot lips close over my straining pecker and I am suddenly enveloped. I think I forget to breathe. My penis is disappearing into her mouth and coming back out, dragging across her lips. It fits all the way in and then it’s out in the open again, swallowed in hot wet mouth heat and then emerging into cool air. She licks the head with her tongue and then gobbles it again like she’s hungry. The suction increases and she speeds up, groaning on my cock, vibrating it with her exhalations. I’m frozen but my legs are twitching, the tendons in my groin tighten and with a whimper I shoot a spurt into her hot heavenly mouth. A louder groan of lust and hunger erupts and she pulls my hips to her face and my cock towards the back of her throat, my tight balls smashed against her chin as I spasm and she sucks the scant drops down.

With a gasp Mrs.Rodgers falls back on the bed, gives me one glance of dismissal and rolls to face away.

Once my shock is gone I cast about and reassemble my clothes, the ones I came over here in. I’m down the stairs and out the door without a thought of payment or a goodbye. I got my payment. I wonder what she’ll say, what next?

---