Loving An Older Lady free porn video

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When I was in my early 20s I was hired by a landscaper to do manual labor. Most of the work consisted of unloading pipes, carrying supplies, installing sod, hauling rocks, soil and debris and lots of other physical things. We also did lawn care which was mostly mowing lawns and raking weekly for customers with large yards. It was back breaking at times and in the summer was extremely hot work. But I loved it. With time I noticed that my body was really responding well to the heavy lifting and I was developing a nice, solid physique.

On hot days we would take off our shirts and tan as best we could. It was a great feeling, working outside, exposing our torsos to the elements, getting tan and ripped, and then going home exhausted to rest up, eat and get ready for the next day. By August, after a summer of heavy manual labor and working shirtless I was looking almost like a young body builder. It was during that month that I was assigned to take care of an older lady’s yard. She was one of our best customers. My boss was very explicit with me, “I want her yard to always look manicured and neat. You can show up more than once a week if needed. She always pays well.”

So, I looked at my schedule and carved out some time 1-2 times per week to show up and work on her yard. The first time I met her, she answered the front door bare foot and wearing a robe. It was kind of early in the morning. I introduced myself as the guy who will be taking care of the yard. She was nice and friendly toward me and stood there in her robe, I couldn’t tell if she had clothes on underneath, but it looked like there was probably nothing on under it. Her hair was turning gray and I guessed that she was probably pushing 60 or so. But I could tell that she was also somewhat fit, a little bit overweight but not too much, an attractive, slightly overweight 60-year-old woman. She was a widow. Although I was quite young at the time, and there was probably 40 years difference in our ages, there was something about her that made me horny.

I worked in the yard and as the day progressed, I was getting hotter and hotter. Frankly, I liked showing my newly sculptured physique, so I took off my shirt and kept working. The sun beat down while working and I worked up quite a sweat. I started fantasizing about this lady. It was such a turn on thinking about her and I started getting hard. As I finished up the job and was walking toward my truck, I noticed out of the side of my eye that she had been sitting in her front room watching me. It kind of made me feel flattered to think she had been staring at me the whole time.

The next week I showed up as planned. When I knocked on her front door, I heard her inside answer and say, “go ahead and work as long as you need to, I can’t come to the door right now.” So, I started with the job and as soon as it got hot, I took off my shirt. I was hoping she was watching me. I even started to get a bulge in my pants fantasizing about her. As I was raking, I looked out of the side of my eye and noticed through the window that once again she was sitting in her chair watching me. But this time I could see that she was sitting there only wearing a bra and panties. As I kept raking, I noticed that her hand was slowly caressing her legs and then her breasts. I kept raking and raking, it was a real turn on to see her in there enjoying herself. She had somewhat large thighs and it was obvious her tits were large as well. She also had a bit of a belly but not too large. I couldn’t tell for sure if she could see that I was noticing her. I finished up the job for the day and went home.

This continued every time I showed up to work that month. She would sit in her chair and fondle herself (but still leave on her bra and panties) and watch me work. By the end of the month I had reached the point that I was obsessed with her. I fantasized about her body, how it might feel, her smell, etc., and she was apparently fantasizing about me.

The last day of August was unseasonably hot. I showed up to work in her yard at the appointed time. I knocked on her door to let her know I was there to work. This time she answered the door. Once again, she was in her robe, but it was parted somewhat, and I could see part of her breast. I got the feeling she was showing me on purpose. She was well endowed and was quite attractive. Her hair was turning gray, but it was a flattering look for her. She smiled and said, “Would you like to come in for a minute? I’ve just finished brewing a pot of coffee.” I gulped and said, “Sure I would love to.” As I followed her into the kitchen, from behind I could see that she had nice, wide hips and her ankles and calves were shapely. She sat down at the kitchen table, crossed her leg and I could see that her legs were tan and shapely. Oh my god, I thought to myself. She is beautiful.

We talked for a bit about the yard and then she looked at me and softly said, “Did you notice I was watching you work? You are a very attractive young man.” And then suddenly she pulled back her robe and exposed her breasts. They were full, and her nipples were hard. I couldn’t believe I was staring at such magnificent breasts. “Go ahead,” she said. I gingerly leaned forward and kissed her left breast. She shuddered and grabbed my head forcing me on her breasts. “Go ahead and suck” she said. With that I began sucking on her engorged nipples. She leaned back and as I was sucking on her breasts, she let her robe come undone and I could see her large, shapely thighs. She spread her legs. Her pubic hair was partially graying. Something about that aroused the a****l in me. I went down on her. I licked and sucked her pussy, taking in her juices. The taste was even more arousing. She was leaning back, her legs open for me, I slid my tongue inside her. She moaned and shuddered. It wasn’t long before she was ready to squirt. I didn’t let up and she sprayed my face. I had never experienced a woman who squirts. I had some sexual experiences before but not from a hard squirter. After she squirted on me, she said something like “Do you like the smell of my juices?” I muttered that I loved it. We were both quivering at that point.

It was then that she stood up and let the robe come completely off and it fell to the floor. She started to tear at my clothes. I quickly helped her, exposing my tanned body. As I dropped my pants, my cock shot up rock-hard. She got on her knees and began sucking my cock, rubbing it against her cheeks, sucking and caressing my balls, moaning and worshiping my cock. I wanted to cum so bad. Her hands and tongue worked my cock and balls squeezing and licking and she moved on to my butt. She even put her tongue on my ass and licked me. This felt so amazing.

I leaned over and picked her up, she was a thick woman, but I could lift her, as I carried her to the bedroom, she said “fuck me good, I haven’t been fucked in ages” and I put her on the bed. We were like a****ls going at it. I worshiped her body, her thighs, pubic hair, cunt lips, I moved on to her ass and licked it good. Then I fucked her from every position I had ever imagined. We were both panting and breathing hard. She even rode me and managed to squeeze my cock with her strong vagina muscles. Somehow, I managed to hold the cum inside until she begged me to cum on her face and tits. I obliged and we both moaned in pleasure.

I stayed there another two hours that day and we fucked even more. She knew what she was doing. At one point I mounted her from behind and I tried slipping my hard cock in her large, flabby ass and she loved it. It brought her immense pleasure. I let my cum go inside her ass. It was amazing.

I had found the perfect sex partner. We became great friends and I would try to think up excuses to come back and see her after that. I lost track of the number of times we fucked that year. Ever since then I have been attracted to older women.

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After John retires he starts drinking wine all day. His wife tells him that he is starting to look like a glassy eyed little old lady. She requires him wear the clothes of a glassy eyed little old lady if he continues to drink wine and eventually he becomes one. Chapter One John and Teresa had been married many years. They never had children but took in some foster kids over the years. Teresa had always been a stay at home mom for the foster children and became very involved...

2 years ago
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love older pussy now i understand

I am 58 years old married with a very good sex life. Well I think I have a very good sex life and getting better all the time. My wife whom I love dearly gave me the green light to fuck around as long as I am careful, don't get caught by friends or relatives and don't fuck with anyone she knows. She to has the green light and fucks a friend at work but he doesn't know that I know he fucks her. She tells me how open she gets with him and does thinks that she could never do with me, like pee...

4 years ago
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Adventures of Sonny Red head boss lady

For the last two years I have worked at an manufacturing company on the assembly line making components for cars. The product that my company produced fit several makes and models. We had some job security even if the talk about tariffs did take place.It was decent pay I had my own sutdio apartment in a quite upscale area. No c***dren or girlfriend at the time. I was just working and rushing home to do nothing. I had an up to date American built truck, that blend in well with my southern white...

2 years ago
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Soma8217s Milky Adventure With An Old Lady

Soma, a beautiful busty young girl, got married two years ago to a well-known family in Kolkata. Soma and her husband Paresh have been separated from the family since the marriage. And 4 months ago, she had the good fortune to be a mother. For Soma, a 26-year-old young mother, it became increasingly difficult to work and look after her family. So, Soma’s mother decided to hire a housekeeper. Soon she found one. The housekeeper was an old-aged woman. Her age was around 56 or 57, a thin and...

Lesbian
2 years ago
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Swappy Lady

Swappy Lady Olga Turlovna So, I'll start by saying I used to be a guy who secretly wanted to be a woman. The fact you've found this story means you're probably the same way and I don't need to explain my feelings to you. But I'm beginning with that admission to emphasise God didn't create all of us with female inclinations equal, and I never considered actually transitioning. I wasn't motivated to go through the ordeal of years of expensive hormones and...

4 years ago
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The Perfect Little Lady

"The Perfect Little Lady" I could hear my aunt downstairs at the kitchen door talking then heard the door close. I stood near the upstairs window looking out through the curtains and watched as my new friends walked across the back lawn talking, roughhousing and tossing the football around as they made their way down the alleyway and out of site. I then heard my aunt returning upstairs to her bedroom where I was instructed to wait for her. She entered the room with purpose and...

3 years ago
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Green Beret Loves Asian Ladyboys

Demonde Scott woke up early most days.. He leaned over and kissed his girlfriend’s forehead. He threw on some basketball shorts, a tank top, and a pair of multicolored Nike Joyride Dual Run sneakers. The 5’11”; 200-pound man headed out of his small house on the compound where Westerners lived while working in the Kingdom. He stretched then launched into morning 2-mile run. The air felt thick on his skin. It was around 65% humidity at present, but the temp was good at a little over 80 °F.He...

4 years ago
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That aint no way to treat a Lady

“A fucking lady? No way; how, why?” I babbled, shocked.“Lady, darling; the word is always capitalised,” Cyn, my girlfriend of four months, clarified, “I’m Lady Cynthia Fortescue-Smythe, second daughter of Edward, the Earl of Battersea."“And you are me telling this, why?” I asked, as we lay, post-orgasmic, in her Knightsbridge apartment wrapped in sheets which were, apparently, cut from Egyptian cotton of astronomical thread count.“Royal Ascot silly; we are going tomorrow, and absolutely...

Fetish
4 years ago
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To serve and soothe the Lady

Another short tale. But only because my a.d.d. keeps me from writing long tales. As always, feedback is not only welcome but very much desired. To serve, and soothe, the Lady. The hour was late, or perhaps early as it was now past midnight, when she - who was not a she on the outside - closed and locked the door after the gentleman left. She liked this man, for he was not cold and cruel as some could be and treated her as a person with feelings. A servant, yes, but still a person....

3 years ago
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Education of a Ladyboi

Ever since I can remember I have been a sissy. As a very young boi, I loved playing with dolls and other girlie things. I avoided the company of other bois my age because to be honest, they frightened me. They just gave off a threatening and hostile vibe that I went out of my way to avoid them. Instead I preferred the company of the girls. I took a lot of heat all the way through school, and after puberty I began totally embracing my femininity, by overt means, such as, wearing makeup, girlie...

1 year ago
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The Wonderful World Of LADYBOIS

Oh god - I'm just sitting here, thinking about how lucky I am to have been born a femme! I love everything about femmes. Of course, getting to where I am today - a totally sexy and girly ladyboi - took a long and sometimes circuitous route. Being born male, and coming from the time and place I came from, announcing to the world (or even to yourself!!) was probably not the wisest thing to do. All I ever heard growing up were extremely negative things about anyone who wasn't straight sexually. It...

3 years ago
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91 AVIS AND HER LADYFRIENDS

91 AVIS AND HER LADYFRIENDS My friend Carol called me up one morning and asked if I would like to meet for some shopping and lunch. Since Jon and I would have the day to ourselves, I agreed and we met at the local mall. Carol approached me and unexpectedly kissed me there in the entrance way to the mall. "Good morning" she said as I looked back in mild shock. "Did I shock you?" she asked. I said I was a bit surprised, but then let it go and off we went shopping. Around noon we stopped at...

2 years ago
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Married Black Mans Ladyboi

Torrance Denkins was completely infatuated with transsexuals. He watched shemale porn constantly. He was married to his second wife. In total, he had five c***dren - three by his first wife and two by the current one. Torrance was forty-eight years-old. His betrothed was only 29. The homicide detective walked out of the precinct and got into his personal vehicle. He drove a black 2014 Cadillac CTS. Once he got settled in the car, Torrance started it up and then sent a text message to...

2 years ago
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the barlady

After a long day at work and a meeting with my boss that ended badly. I decided to dive into the local pub the young guys at work always talk about. I walk in and plat myself by the bar. Greeted by a young black woman. I pay no attention with my head down. Whiskey on the rocks.. Make that a double!! She slides my drink over asking.. Rough day? as I take off my tie. I reply with a negative voice.. You can only imagine. And that's when I make eye contact with her.. A pure beauty. Tied up hair in...

4 years ago
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Sex With My Ladyboss

An awesome moment with the busty manager. Hello friends, I am from Kashmir my first story in ISS hope you ll like it. I have been an avid reader of iss. If any women who seek no strings attached fun, or friends with benefit fun can contact me on please be assured of the safety, women’s safety is my first priority. About me, I am a fair handsome looking guy I am a single guy have a decent tool whose sole aim to is to satisfy women, I’m on the heavier side, funny guy. This story goes back in...

3 years ago
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THE CLEANINGLADY

I was just about finished cleaning the house for Mr. Gustavsson, the whole house had been out of a womans touch for years. I had recently got my driverslicense and this was my first real job. I lit lighter and waited for the familiar cloud of Smoke that came when i cigarrette fires up, while Mr. Gustavsson leanedaround the corner and asked if everything was O.K. "No problem Mr. Gustavsson all finished," I said,as i wiped my hand with an old rag , "I'll be out in a minute!"After gathering up...

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