Uncles Lessons

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A young man goes to live with his Uncle.
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CXXXLewis
CXXXLewis
23 Followers

In '91' during my senior year of high school my folks split up. The whole thing was a mess, with me being sent off to relatives while my mom took my younger siblings to the gulf coast to stay with her parents. They sold the house and Dad moved to be with his new future 'ex-wife' outside of Dallas.

Since I am older by about 7 years, and was in high school I did not want to leave town in my last year. No way did I want to be sent off to someplace I did not know, and be the 'new kid' loser.

With no other options I was forced to go stay at my mom's sisters, 'Aunt Margie' out on a farm roughly 18 miles away from anything, and 30 miles from my school. It was not a great situation, and I was not happy with either of my parent's recent choices. To make things worse my Aunt Margie and her husband 'Uncle' Bob were infamous in the community as hardcore bible toting zealots.

The 'footloose' variety of swift water Baptists that don't dance, see movies, or have fun other than Sunday picnics. They were so hardcore that mom and Aunt did not speak for 3 years prior when the youngest of my Aunts 3 daughters moved in with her college boyfriend, and got preggo. My mom had told her to 'chill out and stop being such a bitch'. It was a monster fight, and ended in my Aunt leaving yelling about 'praying' for the children in such a house, and my Mom slamming the door behind her.

Looking back I am certain it was a painful call for my mom when she asked if I could come live with them for the majority of my senior year. It was also a morale victory for my Aunt who had predicted the event years earlier.

So it came to pass that I packed up and moved in with my empty nest Aunt and Uncle early that fall. I was given my Cousin Jenny's room in the corner of the basement since she had been married with kids and living a few hours away for almost a decade now.

I quickly hung posters, threw my stuff about, and made myself a nest the way teenage boys generally do. My Aunt complained regularly they will have to 'wall the door shut to keep the stink from spreading' when I move out.

Life was pretty mundane with the holidays rolling by, a few trips to see my Mom and Dad. Their house was filled with the girls, kids, and loser son-in-laws for the month of November and December it seemed, but then it all went quiet again.

My Aunt busied herself with church functions almost daily that spring. They were working with the local women's shelters in the area, and she got pretty wrapped up in fixing up an old farm house donated a town over as a safe house. She was gone most of the time, and my Uncle was always puttering around the various buildings, barns, and sheds full of equipment on property. He had stopped real farming long ago when they drilled 10 wells on his land and only did enough to keep him out of the house most days. With little or no supervision, and no cable TV, I spent a good bit of the time whacking off when not in town at school or hanging out with friends. I had always had an 'underwear' fetish, and been going into my mom's panty drawer for years at this point.


With all the turmoil of my parents divorce the urges combined with teem hormones seems non stop. It was not long before I was going through my cousins old things, wearing panties and stockings under my clothes on numerous occasions. I had snooped in my aunts drawers, but her staunch ways did not even allow for decent underwear, just big cotton things that were pretty much the same as guys minus the barn door.

One evening while my Aunt and Uncle were at a church function I was snooping my Cousin Sarah's room, the youngest wild girl of the three daughters. In the back of her closet I noticed a loose floor board under some boxes, and lifted it up to see under. It was like the movies with a stash of items dust covered and tucked in there from Sarah's younger days. There were a couple of diaries with just the first few pages filled with teenage dribble, some naughty Polaroid shots of her in pretty crazy positions wearing almost nothing, a set of big anal beads, and an old vibrating dildo with no batteries.

I had played with my butt more than once; using a well Vaseline'd two finger combo while jacking off in stockings and some of my moms heels, but had never had much more up there.

Dying to try it out I quickly abandoned my snooping and fled to the basement grabbing the petroleum jelly on the way by the upstairs medicine cabinet. I lubed up the beads and slowly worked them in, feeling that initial pain, and then intense pleasure once the tight hole relaxed. I did the same with the old 8 inch dildo, but it was more than I could handle and uncomfortable causing tears to well in my eyes when I first got it past the small entrance to my ass.

Over the next few weeks I had added a set of anal beads to my panties, hose, or stockings I would wear under my clothes. I even wore them a few times to dinner with my Aunt and Uncle in town, and to one of their friend's houses. I loved the way they made me feel full, and stimulated me while I casually strolled around the farm or out on errands.

Just after valentines, one Saturday, while my Aunt was gone working on the 'charity house' and my uncle was off doing whatever it was that he did. I decided to bust out my toys and play. I got on some white stockings I had bought on a trip to see my dad in Dallas, along with a little white silk thong that had tiny cherries on them. I had some nice 3 inch heels with ankle straps that were my cousin's from prom a decade prior. I also had an old skirt/blouse combo found in box of Sarah's things.

I take after my dad's side and am only 5'6" and 150lbs. I was a small 135lbs my senior year, so everything of my cousins fit me perfectly since they are more of the traditional farm girl types. I have to say I looked hot in that little skirt, and always got super horny by the time I fastened the tiny straps on her shoes.

I took the lube out and sat on the edge of the bed working my little butthole, and slowly sucking on the dildo. I killed more than a few afternoons like this and had only been at it just over 20 minutes when I heard a loud cracking noise, and looked up to see Uncle Bob had opened the bedroom door just staring at me. He had his hand on the door knob, but by the look on his face had clearly been there a while, and was startled by the noise as he stepped on a CD case entering the room to get a better view. The cracking case had made him freeze and pulled me out of my masturbation bliss to an incredibly awkward moment.

Me laying there, ass in the air with one of 5 anal beads hanging out, 4 inches of dildo in my mouth, and dressed in stockings, cherry panties, and my cousins heels from prom 10 years prior. It was one of those big record player screeches and the whole of time seemed to slow to a crawl.

I locked up, dildo in hand just staring at my Uncles large frame in the doorway. 1000 things ran through my head in seconds, and I was convinced I would be hitch hiking to Dallas with an embarrassing conversation awaiting me. Thanksgivings would be forever ruined, as the anal bead kid passed the turkey and stuffing.

I jumped in to movement, and flew to a stance next to the on the opposite side from the door, anal beads still in my ass. Dropping the dildo beside the bed I began moving my mouth and trying to stammer out some sort of explanation.

Mostly it was just "ah, ah, ah, I, uh, uh, I, ah, uh, uh" dripping from my pie hole, but no substance at all. I was brain dead, flat lined, and unable to summon more than a monkey's vocabulary.

My Uncle deep southern voice broke the air with a booming "Stop now!" He lifted his open palmed hands as if he was trying to talk a jumper from a ledge.

Slowly he began "Just what do you think you are doing boy?"

Dumbfounded I looked back at him. I was clearly wearing girl clothes and playing doctor with myself, but could only muster the kid answer of "I dunno." The feeble response was followed by an exaggerated shoulder shrug.

It was at this point I notice my Uncle Bob's massive hard on showing through the front of this overall. It was a good nine inches, with a wet spot of precum showing through already. Apparently he had been the longer than I had thought, and it aroused his monster trouser snake. It looked like he had a hammer in his overalls and it was about to shove through the front.

He caught me zeroed in on his bulge. Seeing that I was clearly fixated on the recent added element to what was already a strange afternoon. "You do this a lot?" asking in a lower toned whisper of a voice.

"I guess so" I said back.

"You like dressing like that?" He again used the very quiet tone.

I muttered "Yeah, I guess I do."

Uncle Bob began to walk around the edge of the bed towards me. "Turn around." Leaning to the side, "What do you have going on back there?"

I hung my head and slowly turned around. Knowing my Uncle would get a full view of remaining bright pink anal beads hanging between my ass cheeks just to the side of the little cherry covered thong. I looked at the floor, thinking this was going to be a pretty shitty situation when my Aunt got home.

Looking down it dawned on me in that moment 'My Uncle has a bonner!' He was excited by the site of me sucking and fucking myself.' I thought 'Holy crap his dick is huge!' I was still semi hard from playing with myself, but felt the blood almost gush to my little dick at this revelation.

Uncle Bob was behind me then and reached down to the end of the string hanging from the anal beads. He got very quite, and I began to get nervous. Thinking "He may be even madder it made his dick hard!"

I was sure I was screwed when he grabbed the hanging anal bead firmly with his fingers and seemed to tense up. I was looking at the wall still, and began to turn when his massive hand clasped firmly on the back of my neck. With my neck in one hand and the anal bead in the other he quickly cocked me over the edge of the dresser next to my bed. The things on the dresser were spilled left and right in a big crash as he pinned me down. I moved my hands trying to grasp his wrist to free myself, but it was of little use. Uncle Bob is 6' 4" and almost 300 lbs, strong as a horse, and did not even slow at my feeble attempts to stay his hand.

Pushing me hard against the dressed I could feel his massive boner up against my ass. I would feel the wet spot of precum, cool, and sticky on my skin. I was expecting him to rip the beads from my ass, then begin kicking my teeth in, and there was not shit I could do about it. I squealed and squirmed, but he held me down and shoved me higher on the dresser so my feet were tip toe touching the floor.

Suddenly with a turn of his wrist I felt the anal bead in his fingers pushed tight on my little lubed hole. He held it there while I wiggled in surprise, waiting for me to become still and stop fighting.

"Relax, just relax." He whispered slowly. "I wont hurt you."

Relieved, but still pinned hard, and feeling his cock on my backside I tried to calm myself while he applied more pressure on the little ball of plastic at my anus. With a little push he popped the bead inside me, followed by his very thick thumb. It felt amazing as he slowly worked his thumb back and forth in my ass. I could feel his big knuckle as it pushed past the small entrance and then pulled back.

I was already well lubed, but this seemed to heat things up quickly. Uncle Bob used his thumb, then one, two fingers to plunge my tight ass. My eyes rolled back in my head as I began to moan with every push. I could hear the clasps on Uncle Bob's overalls coming undone, and the top hitting my back as he moved to let them fall to the ground.

His traditional white boxers were soaking through, and felt wet as they slide past my legs, and landed in a pile on the floor with his overalls, and boots. I felt the heat of his cock touching my ass, and pushing up under the lifted part of the little cherry thong. Using the precum from his cock, Uncle Bob continued to lube my asshole until it was slick and smooth. His fingers were fucking me quickly while I made little noises as he pushed all the way to the bottom knuckle of his middle finger with all 5 of the beads still inside me.

In a very swift tug Uncle Bob pulled his finger, and then the beads, pop, pop, pop, pop, and pop in an explosion of pleasure that made me quiver and almost pass out. Releasing my neck he pulled my hip to him with the head of his cock touching my little ass pussy. Gently he would push, then back off, push again a little more, and then back off until his mushroom head was about to enter me.

As Uncle Bob slide for the first time in my cherry ass I let out a high yelp like a dog that had been stepped on. I had never felt so full, and he had abandoned the slow back and forth technique which allowed him entrance. Now that he was in the door he pushed hard and drove until he was balls deep inside me.

"Oh my god!" I screamed as he held his monster cock in me, deep as he could manage, for a full 30 seconds. I could not keep my breath as Uncle Bob began to fuck me long and slow with full strokes of his big shaft. Every time he pushed so deep it seemed to force the air from my lungs, and I would moan loud.

Faster and faster he picked up speed, but never shortened his stroke. My Uncle was smacking his hips against my ass with that unmistakable 'slap, slap, slap' sound ringing over my screams. He was going like he was a man thirsty from the desert, and planned on drinking his fill.

I could feel the sweat on his body running down to my stocking tops. The clicking sound of my heels with every thrust against the bottom of my cousin's old dresser was like a metronome to Uncle Bob's cock lead masterpiece. The panties pulled well to one side and soaked with my own sweat and precum as he pounded stroke after stoke to the root of his shaft. All of these things overwhelmed me, and without warning I started to cum in the front of my pretty panties until it spilled from around the edges and down the front of the top drawer. I bucked when it happened, and squealed wildly. I had never felt anything like it, and was awash in the intense pleasure shaking from head to toe.

Uncle Bob began to grunt and make deep animal like noises as I was still shaking from my own orgasm. His cock seemed to swell thicker and thicker in my ass as he continued driving hard. With a loud grunt and three long slow thrusts I could feel Uncle Bobs cock pumping my ass full of his hot cum. I could feel it shoot up in me, and feel the heat radiating with every flex of his giant mushroom headed prick. Slowly he came to a stop inside me, letting every last drop seed me. His massive had running up and down my legs, grabbing one of my heels pushing me hard into the dresser again and finishing with 5 giant final thrusts. He pulled out, and dropped onto the bed next to us with his large pole still throbbing and red, but looking quite relieved by its work.

I could feel his cum dripping from me, and down the insides of my legs as I let myself down from on top of the dresser. I could not really stand, and weakly dropped down next to him on the bed. Worn-out by my amazing experience my Uncle had provided me I fell fast asleep there next to him.

We slept like that for almost two hours, both of us too weak to move from where we fell to the bed. As my Uncle got up and began to dress himself, his cock still sticky, leaned over, and kissed me with his tongue "This is our little secret, right Missy?" followed by a smack on the ass.

Missy? He called me 'Missy'. That silly name turned me on so much I was wet in seconds, and I agreed it would be best to not share with anyone the fun we had.

My Uncle finished cleaning up, and went back up stairs leaving me spent on the bed. I could hear the shower running upstairs, and I beat off again thinking of how big and beautiful his dick was.

The rest of school went pretty much the same with my Uncle fucking me limp every time my Aunt left the house. I kept in tune with her schedule, and would dress up in his favorite outfits in the downstairs bathroom while she was getting ready to go upstairs. There were times she was in the driveway pulling out; he would already have his dick in my mouth or ass.

As I got ready to go away to college that summer we were going at it in the barn while my Aunt was inside making dinner. I would be eating at the table with her husbands cum running out of my ass into the panties he had bought me. With her talking about how 'Nice it's been that Robert and I get on so well.'

Uncle Bob would just grin and say 'Missy is not too bad to have around.' Making my Aunt think it was a joke calling me that.

Over the years there have been, holidays, fishing trips, family vacations, and I help on the farm every now and then. We always find time to play, and he always has something planned.

CXXXLewis
CXXXLewis
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AnonymousAnonymousover 3 years ago
Daddy Uncle

I went to live with my grand mom and grand pop.She was a retired teacher So i was home schooled thru high school.The were strange people she ruled the house and grandpop in every way.I started to notice he was wearing womens shoes and pants with stockings around the house.It was not long before things started to change with me.My body fell out my hair got long hips got wider and my butt got tighter.But most of all i now have female breast 36d.Grand mom started to transform me in to a girl.She would do my make up hair nails lips and eyes.She would lace me in to a tight corset panties stockings heels and dresses.She would make me dress all the time.Soon she would dress grand pop to.She had him on hormones as he has 38d breast also.She would make me watch as she fucked him with a strap on dildo.One night she told pop to make me a women.She tied me to the bed so pop could fuck me.From that time on they took turns having sex with me.I was made to suck his cock deep throat and swallow his loads.He would do ass to mouth and fill me with his cum.He would fill my ass also.She would have sex with me suck my cock and i would do oral on her as well as fuck her.

Stephanie_loganStephanie_loganalmost 5 years ago
I had a similar experience,

I'm now a older crossdresser. I had an experience similar to this one. As a man who discover a younger cross-dresser.

Thank you

BrendaNWBrendaNWabout 9 years ago
oh yeah

Love to get fucked like that.. long and deep and over and over again.. not sure I would ever leave

AnonymousAnonymousalmost 10 years ago
made me wet

im a crossdresser, i had an uncle take advantage of me, nothing like that but i really had to practicaly throw myself on him to get fucked. but he did and i loved it!!! great story please make ch. 2

stephanielegsstephanielegsabout 13 years ago
HOT HOT

I wish I had a uncle like that!

I'm an avide Crossdresser and it's my fantaisy to get fuck exactly like in the story.

This a great story!!!!

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