I remember I had just turned 18. Having nothing better to do that summer, I agreed to dog sit for a week at my uncle Dan and aunt Jane's house. They had a cabin at the lake. Dogs were allowed but this particular dog was older and didn't do well when taken outside his home.
I was alone in the house less than an hour before I began to get slightly bored. I decided to snoop around in some dresser drawers, a friend of mine said that his parents actually had a little stash of pot in their dresser that they used occasionally. Apparently when they were feeling frisky, they would partake before having sex.I thought what the heck, and started in uncle Dan's dresser. I found there were several pairs of different colored briefs of uncle Dan's. I always pictured him as a boxer guy. Although I wouldn't consider myself gay, I always felt attracted to uncle Dan. He was ruggedly handsome, and exceptionally hairy man with a very nice build. I always seem to feel nervous and self-conscious around him, no other man that I knew seem to have that effect on me. I guess you could call it a crush. Before I realize that I was even doing it, I picked up a pair of clean underwear and placed them in front of my nose, breathing deeply.I guess I hoped that they would smell like his cock, but instead just laundry detergent scent. Nevertheless, my cock began to stiffen in my underwear. As I stood there, I imagined that later this afternoon uncle Dan would be shirtless, sitting in his swimsuit next to the lake. The late afternoon sun shining through the thick growth of chest hair.
Moving right along I thought, back to my search for weed. I moved onto my aunt Mary's dresser, might as well check here. Two drawers into it, I found a drawer full of pantyhose and panties. For some reason, I have always found pantyhose and tights fascinating. The look on a woman's legs, the feel of the material and even the sound when two pantyhosed thighs rub together is intoxicating to me. Aunt Mary had very shapely legs, and seemed to wear dresses very often. My mom rarely wore dresses, so there were never pantyhose around my house. As I stood before the open drawer full of varying shades and colors of pantyhose, I felt an overwhelming desire to try them on. I picked out a pair of suntan Sheer to waist pantyhose, and held them up to my nose as I did uncle Dan's briefs. Once again, there was the smell of laundry detergent, but also a faint scent of aunt Mary's pussy. My cock once again reared its head against the constraints of my underwear. I imagined an scene with aunt Mary wearing them under a short skirt. Uncle Dan sitting next to her caressing her thigh, his fat cock hard as a rock wanting access to her steamy hot pussy. She reaches down, placing her hand on his thick forearm, enjoying the feel of the soft hair covering firm muscle. She kisses him softly, her mouth like yet another vagina to drive him mad....
At this point I'm holding my throbbing dick in my hand, realizing how lucky Aunt Mary really is. I decide that I definitely want to try on her pantyhose. I took off my shorts, underwear, and tshirt. I slid the silky pantyhose up my legs, and over my stiff cock. They looked and felt amazing. My body was still relatively hairless at 18, so my legs actually looked feminine in the nylons as I looked at myself in the mirror. I reached down and tucked my cock between my legs. I looked in the dresser mirror, impressed with how feminine I looked wearing pantyhose. My throbbing cock refused to stay tucked between my legs. Like a compass, it worked loose and pointed north. As it did, the feel of the silky, stretchy nylon pantyhose against it was intoxicating! I reached down, and lightly stroked it. A drop of precum seeped out of the head. I looked into the drawer again, and saw a sexy pair of pink satin panties with white lace trim. What the hell, I thought. I can launder anything I mess up. So I put them on over the pantyhose. I felt so sexy. Then, in the open closet I saw several pairs of high heel shoes. Fortunately, aunt Jane has large feet for a woman. I tried on the red pumps, and was amazed at the effect they had on my legs! They accentuated and elongated my calves, completing the feminine transformation that began with the pantyhose!
I stood there in the mirror, admiring myself and enjoying how everything felt on my body. I began to imagine myself as aunt Jane, getting dressed for an evening out with uncle Dan. I think how he might look over as he is getting dressed, noticing how hot aunt Jane looks in just her panties and nylons. He comes over, grabbing her by her hips, pulling her close to him. He kisses her passionately, pressing his now erect penis against her. She is bare chested, and his hairy chest feels wonderful against her breasts. She can feel her pussy getting wet...
As I ran that movie in my mind, with me playing the role of aunt Jane, I stroked my dick ferociously through the panties and pantyhose. About that time, I heard what sounded like footsteps in the hall. Then I heard my name being called out, it was uncle Dan! Sheer panic set in, as I turned to look for something to cover up with. My heart began pounding with fear.
That was when uncle Dan appeared in the doorway. "What the hell!" He yelled as he saw me standing there. His face was instantly red with anger. He started towards me, fists clenched. My heart already pounding, now felt as if it forgot to beat for a moment. I was paralyzed with fear. I thought, "he's going to punch me". Then, I began to see floating specks before my eyes. The room seemed to darken, and I had time to think "so this is what it feels like to faint" before my legs gave out. The last thing I was aware of was uncle Dan's hands grabbing me. He must have caught me as I fainted, lowering me to the bed.
I was brought back to consciousness by the sharp sting of a leather belt across my buttocks. "Wake up!" Barked uncle Dan. I was laying face down on my stomach across the foot of the bed. The belt came down once again, I moaned in pain. "Apparently, your dad hasn't spanked you nearly enough. If he had, you would know better than going through people's personal belongings!", he scolded. Once again, the belt cracked against my lingerie covered ass cheeks. It hurt so bad, I began to cry. I choked out a weak sounding "please.."
"Oh, you really are a little sissy boy. You're going to cry now?" He smirked. "What's your dad gonna say about all of this?"
"Please no, uncle Dan! I'll do anything you want, please don't say anything. I'll never do it again!"
A moment passed, then uncle Dan spoke. "Anything, huh? Careful what you offer, boy." There was what felt like a long silence between us, the tone of his last words caused my mind to race. My penis, which had gone soft during the recent turn of events, began to stiffen underneath me. Then, the belt cracked again, but not as hard this time. Still, I moaned out and my cock continued to swell. Almost involuntarily, my pelvis tilted forward grinding my hard on into the bed. Uncle Dan rested his huge hand on my lower back for a moment. Then, he slid his hand down between the pink satin panties and my pantyhose covered ass. "I think we can work something out" he said, pulling the panties down my legs. His finger tips caressing my nyloned legs all the way down.
I gasped in pleasure, grinding my now throbbing cock into the bed again. I could barely believe what was happening. Uncle Dan was apparently as turned on by how I looked in his wife's lingerie as I was! I turned my head, and saw the massive bulge in uncle Dan's pants. He unbuttoned and unzipped them, letting them fall to the floor. Then he pulled off his tshirt. My jaw nearly dropped when I saw him standing in front of me wearing only a pair of red low rise briefs. Not only was his cock longer and thicker than I had imagined, there was a wet precum spot forming at the fat head. I had seen his gorgeously furry chest before, but I had never seen his muscular thighs. They were covered in hair, like the rest of him! I assumed it wouldn't be long before I learned how to suck a man's cock. I was ready.
"I'm sensing that you are "up" for this, boy. That's good, because what It's going to take to keep me from telling your Dad might hurt." He said, caressing my firm ass.
"Your aunt is a wonderful woman, but she doesn't do anal. And since you like to dress like a woman, I guess you'll find out what happens to boys who wear girly things."
As turned on as I was at that moment, fear shot through me cooling me down. I rolled over on to by back, almost subconsciously protecting my virgin hole. I looked up at uncle Dan, but he didn't make direct eye contact. His stare was on my body only, not my face. Then he spoke.
"Did I tell you to roll over, boy? NO, I didn't!" He said aggressively. He grabbed me by the ankles, and flipped me back over forcefully. Even though I was terrified by the prospect of his huge penis invading my tight rectum, I was also surprised by how exciting it was being man handled by him. I felt like a helpless female at the mercy of
a rapist. I laid still, not sure what was next. He removed his briefs, tossing them onto the bed inches from my face. I could smell the precum. This had me so horny that I began to grind my erection into the mattress again. "That's right boy, flex that ass for me."
Uncle Dan then climbed on top of me, his hard pole nestled in my ass crack with only the thin suntan pantyhose between us. His hairy chest tickled my back deliciously, as he began to grind against me. He reached down and ripped the crotch of the pantyhose, two thick fingers heading straight for my hole. "Nice tight pussy, boy. It looks like I'm your first." He said while pushing the fingers in my hole. The pain of the fingers was bad enough, I feared what that elephant trunk of a dick might feel like. I pleaded "owww, please that hurts!" One huge hand went over my mouth and nose, it smelled like my ass. "Shut up, boy! Not a word out of you! I don't take sass from bitches". He held his hand over my mouth and nose long enough to where I began to struggle, I could barely breathe. About the time I thought I might pass out, he let go.
"You get my point", He said forcefully. Then he reached into the dresser, and pulled out some lube. He worked it up inside me. I bit my lip, afraid to make a sound. Then, he mounted me again. He pushed his fat cock head against my hole, "just relax, don't fight it". As the cock went in, I broke my vow of silence with a high pitched whimper. This didn't seem to bother him, he answered with "yeah, feel that cock you sissy bitch". He pushed the full shaft into me, I moaned louder now. "Oh, your pussy feels so good boy." The pain eased, and was replaced with pleasure as he found a spot deep within me. The feel of his hairy body against mine, and his hard dick pinning me to the bed was amazing! His cock thrusting inside me was powerful enough to grind my own erection against the pantyhose and soft blanket under me. I actually came before uncle Dan, though I doubt he had any concern for my pleasure. I painted every thing under me with my built up load. The force of my orgasm seemed to bring his, my hole seemed to massage the cum out of uncle Dan, as my whole body spasmed when I came.
He shot deep within me, moaning and breathing
in my ear. He laid on top of me, while his spent cock shrank. He pulled out, and only said one thing. "You can keep the pantyhose as a souvenir, bitch." Then he left the room, fetching the cooler that he had driven back for to begin with.
After that, at family gatherings he seemed slightly uncomfortable around me. I kept the pantyhose, and always hoped for a booty call from uncle Dan. It never came.....