My First Time With My Stepdad free porn video

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I was about sixteen years old when I started exploring my sexuality. I was slim, somewhat androgynous boy, and could have probably passed for a girl with some makeup and a wig. I never felt very manly compared to my stepdad, who was tall, fit and handsome, with well kept facial hair. I lived with him and my older sister, and had often time for myself alone in the house. My s*s Jenna was a few years older than me and liked to wear tight-fitting tops and sexy skirts around the house. I loved seeing her dressed like that, and had started to sneak into her room to try on her clothes when I was sure nobody was around. Her sexy thongs and little skirts were a huge turn on for me, and I took every chance I got to try them on myself.

Usually I put on my favourite black sexy thong, short plaid skirt, stripey thigh-high socks, and a nice tight shirt. I loved how the thong felt on my butt, and how feminine the skirt and socks made me look. I used to pose in front of her full-body mirror, sticking my round smooth ass out and wiggle it seductively to my reflection. I'd run my hands over my slim body, pulling the shirt tight against my body so my nipples would poke out, and lifting the skirt giving the mirror a nice peek on my round ass with a sexy black thong wedged in between the cheeks.

One night when I was crossdressing up again in my sisters room, I found a dildo under her mattress. It was 7-inches long, pink and shaped like a real cock with firm balls and veins on its surface. It even had a suction cup! I was surprised, excited, and incredibly turned on at the same time. I had thought about cocks before, but now I had one in front of me. I took it in front of the mirror and started my routine again. I ran the dildo across my body, brushing it against my nipples, down my slim stomach, under my skirt, rubbing against my thong and between my smooth butt cheeks. I was feeling like a slutty, sexy little girl playing with the dildo, but I wanted more. I kneeled in front of the mirror and stuck the dildo on it, right in front of my face. I closed my eyes, leaned forward and gave the tip of the dildo a kiss.

My erection was making a tent in the front of my skirt as I continued kissing the dildo, imagining it was a real cock. I loved feeling of it against my soft lips. My tongue traced the dildo from the balls up to the tip, following the veins on its surface and coating it all in my saliva. I twirled my tongue around the tip, thinking how it would feel on a real cock. Thoughts of girls I'd seen on porn videos on their knees sucking cocks ran through my mind as I wrapped my lips around the head of the dildo with my other hand under my skirt. I had never been this turned on before. Soon I felt waves of pleasure washing through my body. I let out a high-pitched moan as I shot my cum all over the skirt and panties, some of it even reaching the mirror. After recovering from the afterglow of the orgasm I realized that stepdad would be home soon. I quickly wiped the mirror clean so there wouldn't be any signs of my naughty play session and dressed up. Sometimes I left the thong under my boy clothes just for the thrill of it. This was one of those times. It made me feel so naughty hanging around my stepdad knowing I was wearing sexy thong under my jeans, and just moments ago I was sucking the dildo dressed up as a girl.

I started including the dildo in my dress-up sessions, playing with it and sucking it like it was a real cock. My fantasies started to include other men and their big hard cocks. I would be the girl in these fantasies, sucking the cocks and sometimes even getting fucked by them. I pretended to be like the slutty girls I saw on porn videos, giving a sloppy blowjob to the dildo, making it all wet and sloppy. My need to get fucked like a girl was growing, and I started experimenting with anal play. I sucked my fingers first, making them wet with my saliva, and reached behind me to rub them against my tight little asshole. I pushed my middle finger in slowly, feeling it slide in and stretch my virgin hole. I slid it in and out, fingering myself gently. I turned to look at the reflection in the mirror to see my finger disappear between my smooth butt cheeks. I was getting so turned on by this, but I wanted more. I added another finger and slowly pushed them in while still sucking the dildo at the same time. I wanted it inside me so bad.

I took the dildo and stuck it on the floor in front of the mirror; the perfect place to see myself riding it. I positioned myself on top of it, the tip of the dildo against my tight little hole, and started lowering myself on it. I looked so hot with my thongs dropped on my knees and short skirt just covering my erection. I felt the tip of the dildo pushing in and let out a moan. It felt bigger than it looked at first and hurt a bit, but I loved the feeling of it filling my ass. I pushed it in deeper slowly and soon felt the balls against my cheeks. I had it all the way in now. The hard cock I had dreamed of was so deep inside me, and it felt amazing. I started riding it slowly, feeling it slide in and out of my sweet ass and loving it all the way. I was moaning and running my hands on my body in front of the mirror as I kept riding the dildo harder. I really felt like a slutty girl riding cock like that. My moans got louder as I rode the dildo faster. I loved the feeling of getting fucked.

Suddenly I heard a faint creak in the doorway. I froze and tried to pull the skirt down to hide the dildo and my my cock from being seen. I was mortified as I turned to look at the door. The dark silhouette of a tall well-built man was standing there, looking at me dressed as a girl with a dildo deep inside me.

"I've got to admit, you look sexy showing yourself off in front of that mirror." I turned bright red, realizing he had seen everything. "So, you like to be a girl?", he asked slowly, his eyes scanning me as he stepped in the room. I was still completely speechless from the surprise and embarrassment. I broke the eye contact, looking down with a blush on my face, when I saw the bulge in his pants. It was crystal clear he got hard from watching me, seeing his cock bulging in his pants. "Do you want to try the real thing?" he asked and sat on the bed. I wanted to disappear, but something about his calmness and confidence made me feel safe.

"You're not mad or anything?" I asked after the initial shock had worn off. "Oh no, honey. It's all right to enjoy these kinds of things." He answered softly. "You could touch it if you want". I got up from the floor and took the dildo off bashfully. "Is that your sister's too?", he asked and I nodded my head. "We should get you your own toys sometime", he continued while I sat next to him, blushing fiercely. He placed his strong hand on my thigh and stroked it gently. "I like how smooth you are.", he said with a deep voice, which made my heart beat faster. I reached out and felt his hard bulge through his pants. I felt a rush of excitement when I realized I had made him this hard. His hands were exploring my slim body, his right hand running down my back and grabbing my ass, and his left one still stroking my inner thigh. I opened his zipper and took his hard cock out of his jeans. I loved how hot it felt in my hand, and how I could feel it throbbing. I started stroking it slowly at first, looking up to his eyes for approval. "That's good, baby. Keep stroking it."

His cock looked and felt so much hotter and real than the dildo I was playing just minutes ago, and I wanted to do everything I'd tried with the dildo with his cock too. "Can I try sucking it?" I asked shyly. "Yeah, if you want to. I'd love it." He replied. I bent down to give his cock a kiss, and felt him lift my skirt. His hands grabbed and played with my soft round butt while I kept teasing his cock, licking it and kissing it all the way from the bottom to the tip. I could taste his precum on my lips when I kissed the tip of his cock or flicked my tongue over it. I finally took it all in my mouth, and heard an appreciative moan from him, "Oh yes, I love it baby". He reached out to pick up the lube bottle from the bed and I felt the cold liquid drip on my ass. He started circling my pink hole with his fingers, prodding it at first, and when I pushed back against them, slid one in. I let out a moan with his hard cock still between my lips.

"Do you like it?", he asked with his fingers deep inside me. "Yes, daddy" I replied, lifting my head from his lap. "Do you want me to fuck your tight little ass?", he continued, "I can be gentle for your first time". "I'd like that", I said, my lust overpowering any feelings of shyness or embarrasment. I watched him take off his shirt and put my hand on his toned stomach, feeling his abs under the body hair.

"Get on your hands and knees on the bed", he commanded gently, and I obeyed. I got on the position, with my ass up facing him. "Oh god, you look amazing" I heard him whisper. I felt his strong hands on my ass again, spreading the cheeks and playing with it. He put his hard cock between my round cheeks and rubbed it against my hole. I loved the feeling of his cock against my slim body. He positioned the tip against my boy hole, and pushed it in slowly. Playing with the dildo earlier had warmed me enough so I could take his big cock in my tight ass pretty comfortably. His cock was thicker than the dildo, so the sensation of his cock filling me all up was amazing as he pushed it in deeper. I felt him slide his hands up my body on my chest to play with my nipples. He continued to thrust in a slow, steady rhythm. I was soon laying flat on the bed, my cock rubbing against the mattress and my hands grabbing the sheets as he kept fucking me. I felt so submissive under his body, his skin against mine, his heavy breathing mixing with my moans of pleasure.

His cock kept hitting me deeper and harder, and I felt a warm sensation starting to spread through my body. I was amazed by how much better this was than playing with just toys. "I'm going to cum soon, baby" I heard him whisper in my ear. "Please cum for me, daddy" I replied in between of my moans. He pounded my tight little ass harder until I felt him shooting his hot thick cum inside me, filling me with his seed. This feeling put me over the edge, and I came right after him, my ass contracting as if milking his cock dry for his cum and my cock spurting cum on the bed sheets. He stayed laying on top of me with his cock still inside me, telling me how much he loved me and my round tight ass until his cock softened and popped out. It was everything I could have hoped for my first time with a man, and it wouldn't be the last.

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Introduction: While a few details have been tweaked, this story is as close as I can remember it Prologue She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½, feet. Dark red&hellip, it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the...

4 years ago
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Sandy and RandyChapter 2 Daytime Funtime

After the close call and excitement, in more ways than one, of that first night together, Sandy decided they better cool it a bit so Mom wouldn’t get suspicious. Mom also went back on day shift, 8am – 8pm, so bedtime was less private, but days were not such a problem. Randy tried to act normal around Mom and of course, around Sandy, but he did have some issues like being quieter and more protective. Mom just thought he was getting older and closer to starting into puberty, especially now...

1 year ago
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Halftime Stranger

It was a warm October night and I was at a college football game with a few buddies. Throughout the first half of the game, I looked to my right and there was this hot sexy bald guy 3 sections to my right. He had huge arms and was wearing a black wife-beater and jeans. We kept looking at each other and at each time, he would show that bright smile of his.At halftime, I went to the restroom and used one of the stalls, luckily I was the only one in the bathroom. As I opened the stall, he was...

2 years ago
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Summertime In Colorado

Summertime In Colorado I absolutely love summertime. The hotter it is the less the girls wear. Instead of long jeans they wear short shorts. Instead of full blouses they wear skimpy tops. Coats are strictly out of the question too. Bikinis are popular even if it is just the top half with a micro mini skirt. Like I said I absolutely love summertime. Girls of all ages are wonderful to look at. Touching them might be a different story but looking at them is still legal. The problem...

3 years ago
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Summertime Blues

Summertime Blues Author's Note: This is an old story of mine which I self-edited using the great suggestions I been receiving. I will go back and edit it more. I want to see how well I could implement the suggestions which I got. Also, I want to give a thanks to all the people who had help me in my writing. It was a bright sunny Saturday afternoon in July yet it was raining in Joe's mind. This was for Joe was having a run of the mill bad day so he headed to the bar for a drink. He...

3 years ago
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Reese Witherspoon dommed

any of the actresses mentioned below. This story is written down for enjoyment purposes only. Reese witherspoon woke up with a headache. She didn't know where she was. All she could feel that she was blindfolded. Not only that, she was tied to the bed with duct tape, unable to move her hands and legs. She also noticed that she was nude. A duct tape covered her mouth so that she shouldn't shout. All she remembered was going to a producer's home for some script reading of a film they were...

2 years ago
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FaceTime surprise

I have a new job working away and I bought an iPad to keep in touch with the wife, it’s great seeing her when away I miss her so much so it’s great when I’m bored in my room. Jane and I for years have spoke about sharing? But she never comes through, it must be 4 years now we have had the same conversation about it and it’s always the same answer maybe! Jane is great in the sack she knows how to please, I keep telling her she needs to give it out cos it’s going to waste on me as I only last...

4 years ago
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Showtime for Teri

Showtime for Teri By Teri Franken Chapter 1 My name is Teri and I am 28 years old. I have been a closet sissy for as long as I can remember. My parents knew that I was not your typical child and they let me live how I wanted to and did not judge me, they just loved me unconditionally. I grew up loving everything that a little boy typically doesn't like, such as dresses and dolls. My parents were concerned that I would be a target for bullies, so I was home schooled, took my GED...

3 years ago
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Eagle in the Sunset 2019Chapter 29 Summertime for Us All

October 17th, 1995, 7:30 AM PT, Metro Plaza Hotel, Los Angeles, CA Miriam had been tossing and turning all night; she spent time just sitting in the chair in the corner of the room to try and let Baruch sleep. She was so upset she was oblivious to the fact that Baruch couldn’t sleep either, which was not in her nature. She was usually fully aware of what was going on with her husband. They thought together almost telepathically, and yesterday had been one of the first times in decades when...

3 years ago
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Timeless Beauty

TIMELESS BEAUTY BY PAUL G. JUTRAS Sam walked in the dorm house, looked at the lock and then in the dorm mistress's room. The plus size woman was dress in a black blouse and flats, black with white palm tree design jacket and skirt with dark brown nylons. She new there was only a half hour before she made her rounds and called lights out. Upstairs, roommates Chris and Alex waited on their beds. Like their friend Sam, both guys were petite and lovely looking. Being transsexuals who...

3 years ago
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First Time Sex With My Longtime Bestie

Hi everyone Akshay here, age 23 from Chennai. I’m a reader of ISS for the past 5 years, and it’s high time I shared my experience. This happened a couple of months back. It was with my longtime bestie. Her name is Vaishali. We know each other for around 6 years, starting from our college days. She lives half an hour away from my place. I’m pretty familiar with her parents. We got to know each other from our college days as we were from the same department. She had a sexy shape, which gave me a...

1 year ago
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Younger Than Springtime

The door was open. I had no reason to have it closed. We were all in this together. So I was sitting in the large chair as my nurse prepared to access my port to begin the first liter of Cisplatin. The cancer center had been busy today and I glanced out the doorway as several people passed by. Then I noticed a woman pausing as one of the nurses escorted her somewhere.It was Katherine. I recognized her at once even though it had been so many years ago. Then I heard her laugh as her companion...

College Sex
2 years ago
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I want my StepDaddy

I'm not sure when I started to be sexually interested in guys, but I'm going to guess about 11th grade, when I turned 17. I had always heard my parents having sex down the hall from my room, and would masterbate about them, but never about guys my age. I mean, I was attractive, with my 5'9", flat stomach, 40D breasted body, I knew I attracted the boys. But, I wasn't interested in them. I wanted my stepdaddy. It all started about the time of my 17th birthday. I would hug him, and he would hold...

Incest
2 years ago
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My stepdaddy

I've always had fantasies about my stepdaddy, what's so wrong about that? I think it started when I was only about six, not that my sexual fantasies started then but that was the first time I saw daddy's penis. He and mom were just dating and one day she told me to take a bath but I didn't want to take a bath so I thought I'd just get wet in the shower and fool her. I slipped into her bedroom and took my clothes off and was going to get in the shower when I realized that Carl was in the...

4 years ago
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My Stepdaddy

My Stepdaddy By: Bernice 14 Synopsis: Tyra, is a very troubled teen. With a lot of guilt and a lot huge secret that's bigger than her having been born as Terrance. When her mother brings home the latest boyfriend and she discovers that they are getting married all hell breaks loose. +++++++++++++++++++++++++++++++++++++++++++++++++++++++ Standing in the kitchen in just my panties and bra, I was thinking back to how all this began. It was only three years ago and I guess you...

3 years ago
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Master of All Timelines

Your name is Edward Richardson. You're 20 and you've been fascinated by history ever since you're 11. You're also good at making inventions as well. As you're growing up, you usually found that at various points in history of each country, things always turned ugly at many points. And you wanted to change that. You decided to use your intelligence you create the device called the T.O.S, abbreviated for Timeline Opener and Stopper, that can make you travel back in time and alter the histories...

Mind Control
2 years ago
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I was a wartime TV for the US Army

‘I was a Wartime Transvestite for Uncle Sam!               TJ Ryder                                            Chapter 1           Reform School Romance!     I couldn’t believe that all I got from my uncle Bill when he died after all he said to me about my being his favorite grand nephew was an old diary from World War II.    I mean I thought we got along pretty darn good, and its not like he had any money or anything, just another old geezer in an assisted care center who if he ever had...

4 years ago
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Wartime France

The funeral was a gloomy affair as funerals go. I am somewhat irreverent and remember clearly my twin brother and I giggling all through my Uncle’s funeral because his widow had the price ticket still dangling from the back of her hat. John and I shared a sense of mischief and humour. At our Grandfather’s funeral, we’d been unable to look at each other during the hymn ‘Praise my soul the king of heaven,’ because John had written an alternative verse that was utterly filthy and we both knew what...

Lesbian
2 years ago
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Wartime Passion

A few years ago, my wife was having a midlife crisis while I was away serving in Iraq. She was both lonely and horny. She had been without me for nearly 8 months and I still had four more months to go on my tour of duty. Char is an attractive 40 year old woman, 5'8" tall with blonde hair and green eyes. She keeps herself in great shape and still has a body to prove it, 36-30-36. Our sex life is absolutely wonderful when I am there, and I would not change a thing. She is a Hottie and we are...

1 year ago
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I was a wartime TV for the US Army

  'I was a Wartime Transvestite for Uncle Sam!              TJ Ryder                                          Chapter 1          Reform School Romance!    I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being hisfavorite grand nephew was an old diary from World War II.   I mean I thought we got along pretty darn good, and its not like he had any money or anything, just another oldgeezer in an assisted care center who if he ever had anythinghad...

Crossdressing
4 years ago
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Summertime Fun0

Summertime Fun After my divorce I got my daughter every other weekend and for the entire summer. Now that she was fourteen and developing quite nicely I was enjoying her even more. I also indulged her desire for sexy revealing clothing, since her mother wouldn’t. Holly was pleased that I had purchased a summer home alone the beach. We used to go to the ocean when we were still a family. Another thing that I did to piss my wife off after the divorce. It was a very nice place and I...

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