My First Time with Bill , Cindy

My fascination with women's underwear started at a very young age watching my mom, grandmother and aunts dressing in front of me on a daily basis, never seeing them naked but in their white, beige, or black sixties typical lingerie style bras, high waisted girdles with garters, watching them roll a stocking up their leg stretching pointed toes as their hands gently guide the stocking up the leg, as it unrolled higher up the thigh, gently adjusting the top band to achieve the best fit and proper look, then how they precisely attached each garter to the stocking, strap after strap until all four garter straps on that leg were connected before repeating that process on their other leg, without knowing the women taught me just how to dress in their clothes.
Thanks ladies.
As I got older I began taking every opportunity to riffle through dresser drawers and laundry of my stepmother's friends when she would take me with her to visit them. Each of them having their own style of lingerie they preferred wearing.
They would be so busy talking, smoking and drinking coffee that they wouldn't miss me, probably happy that I wasn't bothering them and found something to do outside. Little did they know.
I've found that every woman has one drawer with nothing but stockings and pantyhose in it which made for an easy pocket grab.
The reaction my body went through just touching these clothes kept drawing me back, to feel the soft silkyness of the material, the clean scent of freshly laundered pantys in one hand, a stocking wrapped around my little dick with my other hand enjoying the feeling quickly as possible so not to get caught.
Occasionally going thru my stepmom's stuff but the other ladies things were more exciting, having the most fun taking place at my Aunts house whenever we visited for a swim at her pool. It was so easy when the women sat around the pool talking, drinking, smoking their cigarettes working on their suntan for me to sneak away into my step aunts bedroom.
Seeing all of them in the sun wearing swim suits showing all the oiled up cleavage shining in the sun sure helped drive my need to jack off.
My stepmom was mean but her sister, my step aunt was super nice to me and attractive for a woman in her late forties a few years younger than my stepmom.
My Aunt Patricia always treated me like I was her own son, she did have a daughter who was a lot older than me who was married living on the east coast, so I was like the son my aunt never had.
I think her knowing how mean her sister was in general towards me she tried being extra nice to me to make up for it.
Finally it was summer break, a few months earlier my Aunt had offered me a summer job taking care of her property, caring for home landscaping the pool and vehicles for room and bored to give me a break from her sister they kind of joked between them.
Her husband my step uncle had past away the year prior so things of that nature had been put aside, understandably. I was more than willing to help since I had spent a lot of my summer's there anyway helping out and enjoying the pool with my stepmom, and I can't forget her panty drawers took up most of the drawers in her dresser.
I couldn't wait I was so excited to take her up on the offer to actually live in her house and have access to explore all her clothes without being scared, not having to look over my shoulder because she would be at work.
When my stepmom and Aunt sat me down telling about their idea I quickly accepted for many reasons, first was that she was very sexy taking part in many of my fantasies thinking about her wearing the clothes I'd seen in her drawers supplying me with multiple orgasms over the years.
I had taken every chance available to me to search through her clothes, going drawer to drawer looking at her panties, bras, lingerie and stuff while I smelled them jacking off, so now being invited to live there was simply a no brainer.
Since her husband's death she worked longer hours from 5pm to 5am in hotel management on the Las Vegas Strip always wearing dresses or skirts with stockings and heels, looking professional but sexy at all times. She has always worked at her job but since his death, now she just prefer working over being home.
Now whenever I think about her it's obvious to me that she always knew about me playing in her clothes. As I grew older I often shot my load of cum in a pair of her panty or in a pair of nylon stockings that I used to jack off with then put them right back in her drawer. I didn't know until way later what happened when my cum dried in the clothes so she had to know someone obviously male did it and the only possibility of whom it could be was me.
Aunt Patricias neighborhood was upper middle class, all the homes were big with large well maintained yards, most having pools in the back yard in an area west of the city.
From my very first day living with her, just as soon as my Aunt left for work I raced to get Escort naked in her bedroom going through all her clothes, drawer after drawer pulling out items to put on. The scent of her perfume filling the air added to my excitement, my teen dick standing at attention eagerly anticipating the fun getting ready to take place.
Prior to moving in with her I really worked on collecting a good amount of lingerie and stuff from numerous laundry room raids of my neighborhood apartment complexes so I'd have a supply women's things to play in and not solely rely on my Aunts clothing.
Many mornings after completing some of my yard work I'd take a drive to gas up my aunts car making sure everything was always ready for her also looking for new nearby laundry rooms to add to my lingerie collection and to keep my secret from my Aunt as best I could.
I had built up a nice collection of mostly black colored lingerie, bras, panties, slips of all lengths, garter belts, stockings, thigh highs, pantyhose from my old neighborhood along with a couple nightgowns and long slinky black pencil dresses or skirts prior to moving in with her but I constantly looked for more clothes but heels were very hard to get but not impossible so my aunts high heel collection was a gift to complete my look.
Most every afternoon once Aunt Pat was ready to leave for work she'd track me down to give me a hug letting me know she was leaving for work, always thankful for the work I'd done and to quickly catch up on any going's on.
She was like the spark to ignite my excitement hearing her heels tapping on the ground as she approached then catching the scent of her perfume getting to see how good she looked, the heels she had on the stockings she was wearing my eyes examining every inch of her behind my dark sunglasses as she reached out for her hug.
Hugs from her always started the swelling to begin making my dick come to life.
After our goodbyes were said she'd turn to leave, watching her walking away my eyes traveled from her heels up her legs to her ass swaying side to side with every step, my hand uncontrollably cupping my crotch squeezing myself as I looked back down her legs then back to her butt, my fuse was lit.
Instantly my work day was over and after a quick swim I would start another night of role play, dressing up in different sexy outfits I'd put together from the things I'd stolen, then spend time in my aunts shoe closet visually checking out her high heels collection as her scent continued to fill the air while I played with my dick selecting a pair of her sex heels to wear.
Night after night I got to pretend, to role play around my Aunts house as if I was a woman, the clothes transforming me as they always have from a young age, the silky material riding me on the edge of orgasm, holding out as long as possible to enjoy the moment all of the effort it took for me to get dressed this way.
The night I discovered my aunts sex toy collection hidden inside a knee high boot box in her shoe closet changed things. I had previously found a box of xxx adult tapes hidden in the garage but never in my wildest did I imagine my aunt having a box of sex toys.
She did have a plug-in hand held massager kept in a hall closet and a small seven inch battery operated vibrator in one of her nightstands.
Not being a fan of women in boots I stayed away from that box for a long time because I like thin heeled high heels.
I began thinking fantasizing about her differently as I inspected each of her toys hoping to taste her pussy nectar as I sucked each toy, I visioned each of them in her pussy, her working it inside her making her cum made me explode uncontrollably shooting some of my load into her secret box.
Hard plastic vibrators in different shapes and sizes, a couple that resemble real dicks and one giant gag gift like dick with balls that was super heavy about the size of her forearm, then a couple of vibrating egg like things with wired controls and one that was hard plastic but more of a cockring having two half circles attached to the egg to grip the shaft of a dick or dildo with a three foot wire connecting it to a hand held controller.
This one became a favorite of mine, using a pair of panties or stockings to wrap around my dick then sliding this vibe over multiple layers of material the ring tightly gripping my shaft with the added thickness from the nylon.
Sliding the power switch up to turn it on, my dick jumped rock hard, the vibration focused directly on a half inch wide flexing plastic band encircling my shaft, a strong wave of orgasm takes over my body as cum forces it's way from my balls to the tip of my cock fighting its way thru the layers of material to escape my swollen mushroom head.
After the climax subsided I start to slide the vibrating ring up my shaft off my spent dick, twisting it slowly trying not to snag on the material as I slid it up my length caused the main egg location of the vibration Escort Bayan to rotate upward until the ring became blocked by the rim of my mushroom head, as I continued twisting it back and forth trying to clear the head of my dick it began to get hard again increasing the difficulty of removing it.
That find along with all of the others got me off multiple times that night barely having to touch myself by hand other than rubbing the different vibes that had working batteries against my nylon covered dick as I sucked others with my eyes closed.
Every afternoon once I was finished with work after a quick swim and shower with my Aunt at work I would dress up to look like the girls in xxx magazines and porn movies wanting to be one of them, eating their pussy, fantasizing about sucking guys dicks too, being the girl getting her ass fucked while I used one of my aunts vibrators in my ass giving me the most intense orgasms.
Night after night I'd lay out my things on the living room floor, walking around the house looking my best in sexy fuck me lingerie outfits, wearing a pair of my Aunts high heels, a few more pair laying on the floor among my other things.
Her box of toys opened on the floor surrounded by xxx mags opened to my preferred picture layouts usually of women in garter belts stockings high heels or a beautiful woman with her lips sucking some hard cock.
On the tv played a xxx porn movie, one of many I found in a box buried in the garage belonging to my late uncle. The sounds of sex filled the air from the action on the screen.
I would watch the movies while I dressed up in the living room, using one of my Aunts hard plastic toys to slide in and out of my ass opened a new window of pleasure for me then, a feeling that I really took a liking to.
At first just the probing of a toy around my tightly sealed hole would make me cum. Then the next time I'd break the seal, the intense sensation of the probing got me off.
Each night I would take a little more trying not to cum so quickly, training myself to resist, to lengthen the amount of time that I could enjoy the intense pleasure, feeling the hard plastic tip of the vibe move around inside me touching parts never explored.
Nightly I worked on my butt hole focusing more on it as I watched mainly anal movies to learn the art, night after night getting them deeper inside me, able to use bigger and bigger vibes.
I sucked on both her lifelike dick looking dildos as if they were real men, imagining that the dick was just pulled from my aunts wet pussy for me to suck, trying to find the taste of her somehow on the toy.
This became my normal routine for days. Soon as my aunt left for work I was pulling everything out into the living room, picking a movie, lay out a bunch of lingerie on the floor to dress up in, then to my aunts bedroom to grab her box of toys and a pair of sexy high heels before returning to the living room for a couple hours of solo sex then clean everything up in time for bed before my aunt gets home.
Then one night when I was having my fun, totally into what I was doing at that moment I heard noise possibly by the pool in the backyard, I looked towards the sliding glass door only a couple feet away from me, the curtains pulled back always open for the view, just the glimmer of the pool light lighting the yard but not thinking much about it I went back to riding the vibrator in my ass and watching a woman getting her ass fucked on the tv.
I heard a noise from that direction again only this time it was for sure a knock or tapping on the glass.
"knock..knock, tap...tap knock...knock."
Startled I looked over to see our neighbor Bill standing there staring down at me with puzzling excited look like a man at a strip club.
Up until then nobody had seen me this way. I was frozen in shock unable to move or breathe not even blink then catching movement lower down I break eye contact to look down, all I could see was his cock, looking at me as he was tugging on it slowly, watching it thickening in his hand, big shiny bulbous head looking at me as he moved his hand slowly stroking it.
He knocked again snapping me out of a trance only this time looking at me and pointing for me to unlock the door as he pulled on his shaft with one hand and at the door with the other.
I was frightened, scared and shocked to be discovered even though it had always been one of my better fantasies I always thought it would be my aunt catching me.
I couldn't take my eyes off his cock, the fat head pointing its eye at me, his heavy balls moving in rhythm with his strokes, his hand pulling, tugging on his man dick.
"Knock..... Knock!" he pulls at the sliding door handle again.
Hypnotized by the sudden situation, unable to take my eyes from his dick, I reached over for the lock flipping the latch up, unlocking the door as he pulled it open.
Quietly stepping in he pulled the door closed behind him, his Bayan Escort cock just inches from my face as I stared at it, the size, the veins its thickness was all so different than my own.
Bill and Cindy lived next door to my Aunt, they had been neighbors for years, most of the people in the neighborhood worked in the Hotel Casino industry.
I have had numerous casual conversations with both of them over time but not paying much attention except for Cindy. Since living next to them I even knew Cindy's work schedule so I could watch her leaving her home in the mornings, her long legs accented with high stiletto heels was her normal, walking down the walkway in short tight skirts, her blouses bursting to the extremes holding back her big round tits. Watching her was always a guaranteed orgasm for me, in the short time it took for her to walk from her front door down the walkway to her car parked in the driveway, watching her squeeze herself in her tight outfits to sit in her car, lifting her legs up high to not scratch her shoes on the doors jam then adjusting her outfit before closing the car door always got me off.
Now here I am, dressed up in women's under clothing, like I have done for years privately to play and get myself off, looking similar to the women in the xxx magazines spread out across the floor, except for my mustache, to me I looked like a woman with my dick bound by tight stockings and lingerie not easily noticed.
Now I'm on my knees wearing black sexy lingerie with a cock just inches from my face unable to speak, not breathing or even moving.
"Don't be scared!" he says.
"I'm not going to hurt you." he added.
"We've been watching you.... enjoying your show night after night...!" he says while still tugging on his manhood.
"Cindy my wife...um.. desided it was time for you to have a real dick!" he said as he continued slowly tugging his thick dick getting closer to my face.
I was frozen in shock the vibrator buzzing away inside my ass gripped so tightly so not to be noticed, my own dick seeming to disappear as I focused on the swelling dick in front of me, my jaw relaxed allowing my mouth to open for air, the sound of some girls voice on the tv talking about how big it is before the sounds of wet sloppy sucking filling the air, some guy's voice directing her actions.
Bill put his hand on top my head as I opened my mouth, his voice calming me, telling me how sexy I looked in my lingerie, that they had been watching me night after night and he couldn't resist me anymore, that him and Cindy would watch me fondling each other before taking turns while having sex.
As he spoke he stepped closer the tip of his dick brushing across my open lips, not moving as he rubbed himself placing the head of his man dick to my mouth and I opened it without a word.
I now had the mushroom head of his cock in my mouth, it was actually bigger in my mouth than I had imagined. I tongued on it like a big sucker or lollipop like the women in movies only focusing on the head as I attempted to do what a woman should.
"Go ahead.... suck it baby!"
"Enjoy my cock..... I'm really enjoying your warm, wet, young mouth." he says as he unfastened the waistband on his shorts.
His shorts dropped to the floor as he let go taking hold of my head with both hands, pushing himself towards me to get more of his dick in my mouth.
"We've watched you practice on your toys.... my wife figured that.... you'd love to have the real thing..... was she right?" he asked.
I was still froze, my mouth filled with the head of a man's dick, a real dick, our neighbor Bills dick.
My mind was racing with mixed emotions, intense fear and remorse as I stayed still trying to open my mouth more to accept his manhood.
"Do you want the real thing?" he asked.
"It will be better than those toys." he adds.
"I want you!" he tells me as I open my mouth wider as he pushes his hardening shaft into my young teenage mouth forcefully taking a little more of his cock in my mouth my lips stretching wide attempting to fit around him.
I could only see his well shaven pubic zone, the dark stubble, the scent of expensive musk cologne clouding my mind as I tried desperately to accept him.
His control of my head also controlled my entire body pushing me down farther on my Aunts vibrator forcing it deeper inside me as I fight for air with a mouth full of cock.
His dick was getting much thicker, stiffening as I attempted to know what I was doing, getting my knowledge only from watching porn movies at that time.
My mouth uncontrollably filling with saliva on its own, eager to perform like a woman should as I finally began to move my lips and tongue on bills cock.
"If you can't suck it..... you'll have to fuck it." he says pushing down on me now aware of the vibration buzzing in my ass.
"It's the rule.... once you start.... you don't stop till I cum!" he tells me.
"That's my rule... and you Will... follow... my... Rules!" he says in a very stern commanding tone.
He was now in total control, in a matter of minutes I went from playing around by myself like normal all alone, to now be submitting to our neighbors.