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There are a few stories that I want to tell, these are all one hundred percent real experiences of mine. My name is Chris and I guess I can be called a bull. I recently learned the terminology of cuckolding. In so doing I have read other stories of hot wives and sissy husbands. With permission from some of my partners I thought I’d write an account of my experiences. I will not use the full names of the women involved, or where I live, because while some of them play with me in front of their husbands, most of them have been without the husband’s consent or knowledge.

I am a 28-year-old single white man with a very active sex life. It started when I was 18; there was a married woman who lived down the street from my parent’s house. Her name is Kimberly. She was, at the time, 35 years old. She was not a supermodel by any means but she definitely was a MILF. 5’6” tall and 130 pounds, shoulder length dark brown hair and perky c-cup breasts with no sag despite being a mother of 2.

I remember seeing her working on her flowers when I was 14 and going through puberty. She looked so hot wearing that tight shirt and shorts. I instantly was attracted and was crushing on her hard. I used to jerk off every night thinking of her doing naughty things, specifically with me.

Now I know that I am very well endowed, but when I was younger the only basis for comparison I had was my father, having seen him nude accidentally a few times. So when I was younger I thought it was the norm. But it seems like our family was blessed in that area.

Dad says it’s the Italian blood in us. Either way, thank you genetics.

So when I learned later that the average male size was around 4-5 inches, not sure where I heard that statistic but I did, my ego took one hell of a boost when I found out I was twice the size of the average man, being a thick 10 inches.

Of course I learned that, while size is a bonus, if you cant control yourself you might as well have nothing between your legs.

In that respect I will always love and be thankful to Kimberly. She was the one who started it all.

One summer, when I was 18, her husband Josh went away on a very big business trip for a month. Before he had left he asked if I wanted some extra cash for mowing his lawn once a week. Both of his sons, who were 14 and 11 years old at the time, were going to be at camp s his oldest wouldn’t be able to either.

He’d give me 20 bucks for each time being only a couple hours of work a week. So that would be 80 dollars, doing it once a week with his own mower and he made sure there was extra gas for me to use.

I quickly agreed, and he said that the following Saturday I could start.

The day came and I headed over to his house, went around back to his tool shed and started to mower up.

While I emptied the final bag I got a hell of a surprise, a light tap on my shoulder. I turned quickly to see Kimberly standing there with a wide smile and holding a glass of iced-tea.

At the time I had no idea that she was home, though Josh had not said it I thought she would have gone with him and taken a vacation…I don’t know maybe gotten pampered at the hotel while he worked. I don’t know what I thought but was just not expecting her to be home alone when everyone was gone. So when she tapped my shoulder, and since I hadn’t heard her coming, I nearly jumped out of my skin.

She giggled at my reaction and my heart raced, fuck she has a beautiful laugh. And when I heard her voice and saw her, this gorgeous woman in tiny little shorts and a bikini top, I got instantly hard.

Kimberly offered me the drink, and I stammered a thanks. Now I have had a couple of girlfriends in high school, I was in no way shy around females, but this one had me reverted back to an awkward kid just hitting puberty and crushing on his neighbor.

I asked her what she was doing here, stumbling over my words.

She pouted, “Well, that was a bit rude. Here I am giving you a drink and trying to thank you for helping, and all you’ve got to ask is ‘what are you doing here’?”

“S-sorry,” I stuttered. “I wasn’t expecting anyone one here, you startled me.”

She tittered adorably again.

I took the drink and another muttered thanks. It was hot as hell outside; I had already taken off my shirt when I started on the backyard. It was a very nice yard, there was an in ground pool and hot tub. It was a secluded and surrounded on all sides by trees so none of the neighbors would have seen. Not that I really would have minded, I was pleased with my physique. But deep down I was now embarrassed due to how sweaty and disgusting I must have looked to Kim.

In all, this place seemed like a great spot to have some very private outdoors fun. My cock twitched again at the thought.

From my downturned eyes I could have sworn that Kim’s gaze looked me up and down. I wanted to think that the look in her eyes was lust, but at the time I was not hopeful of that.


Her fingertips brushed up my arm, barely touching me but it sent a shiver down my spine and caused my cock to strain almost painfully against my pants. She leaned in and spoke softly to me, “I was watching from the window. Thank you Chris for the chance to watch such a young handsome man working hard.”

My first thought was that I had to get out of there, I was in such danger of cumming in my pants and totally embarrassing myself in front of this very sexy, and very married woman. I shifted uncomfortably, and laughed nervously. “Um, you’re welcome?” I murmured timidly.

She laughed more openly, “What’s wrong sweetie? Nervous?”

I pretended not to notice her eyes flick to the bulge in my pants.

“I should head home,” I almost whispered. “I am gonna need a shower.”

“Ok, sweetie,” she said and pressed herself against me, her chest brushing against my arm. “I’ll look forward to seeing you next Saturday.”

“Ok, bye,” I said and quickly put away the mower and took off walking home.

My mind was buzzing with thoughts. Was she just flirting with me? No, it couldn’t be. She was just teasing me. My cock was straining and throbbing, harder than I’ve ever been before.

I was in such a rush to get home and in the shower to rub one out; I didn’t even notice that I had left my shirt next to Josh’s shed. Oh well, no way in hell as I about to go right back there. I’d just have to grab it next Saturday…my thoughts trailed as I realized that id have to see her again…and again, and again.

How the fuck was I supposed to deal with that?

It got weirder a couple hours later when the phone rang, my mother answered. She spoke and laughed for a minute before handing the phone to me.

“Hello?” I asked into the phone.

“Hello, Chris…It’s Kim.”

I almost dropped the phone but my mother was there and I knew I needed to control any nervous reactions. “Oh, hello Mrs. A” (I will of course not be using real last names, but will simply go alphabetically. Her last initial is not A, just what I’m using)

“Listen carefully,” she spoke quickly. “I want you to sneak out at midnight and come over. Don’t be seen, use the woods if you have to. If you don’t I will tell my husband that you tried to come onto me.”

I felt like someone had kicked me in the chest, driving the air from my lungs.

She continued, “if you understand say ‘oh, ok’.”

“Oh, OK” I parroted.

She giggled, “good boy. Come around to the back door of the house. We’ll talk later ok. Now if your mother asks just say that I found your shirt you left behind after I came home and thought it was yours, and that I just wanted to say thanks. Now you say, ‘it was not a problem. I’ll be there again next Saturday, bye.”

I repeated the words and she disconnected.

True enough my mother asked what she wanted, I told her just what Kim told me to say.

My mother laughed, “and you didn’t notice that your shirt was left by Mr. A’s shed?”

I shook my head numbly. And she chuckled about how I would forget my head were it not attached.

I simply wondered what I was gonna do.

This is the first part of my series; these are going to be all true stories of my experiences with various married women. This was the start of the recounting of my first time with a married woman, and I will release the second half soon. I want to be a writer so I though write from experience and all. Please tell me what you think.

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I had never had my cunt licked to orgasm before I met him and the first time was a huge discovery of exciting new sexual pleasure for me. I loved the way he talked to me as he was licking and teasing my clitoris then my cunt lips as he slowly got me to a fantastic orgasm with his wet and strong tongue. He told me after as we were fucking he almost suffocated as I pulled his lips and tongue into my sopping wet cunt while he had his hands holding my arse cheeks. Every week after that he would...

1 year ago
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Manisha Koirala A Nice Experience

I am Raju aged 19. I am staying with my uncle in a posh apartment in Chennai. I am studying for Hotel Management course and was doing my training at one of the five star hotels in Chennai. I used to go to a Gymnasium.I was very good at swimming also and definitely I am a handsome young boy with well-built body and my cock was really 8.5" long and is really fat. It was rigid like an iron rod when it is in erected position. I know that to boy aged 18 that size was very rare. Here I am narrating...

1 year ago
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My First Swinging Experience

Although it has been a few years now, my first swinger experience was very memorable. There have been dozens of swinger couples since that first swinging experience but I remember it like it was yesterday. I had always had a strong sex drive but have never really considered swinging. That is, I never had considered it until a close friend revealed to me that they were swingers. When Beth said that she and Marcus were swingers I was shocked! I hardly knew what to say. Swingers!?? Beth and...

Swinger
3 years ago
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The Girlfriend Experience

It was a Friday afternoon in late spring. I was considering a dilemma that all seventeen-year-old boys face on a daily basis. Do I continue studying for my year end exams that were a few weeks off, or do I jerk off, fantasising about my latest crush?Amy was on my school swim team and we had started hanging out together during the last few weeks of practice. She had a pretty face, nice tits and a gorgeous ass. I was sure that she was into me, but I was too much of a chicken shit to ask her out....

First Time
3 years ago
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Mumbai Train Experience

For a pretty long time I have been reading other people stories, adventures and experiences so I thought of penning down my own experience, well a compilation of experiences actually. It doesn’t have much of fucking in it or even kissing but just experiences a common Indian guy would actually be in and to be more specific a common everyday day local commuter who has been using Mumbai’s local train a “Mumbaikar”. I am pretty sure guys in Mumbai would be able to relate to me. So here I go. First...

Gay Male
3 years ago
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Ani8217s Massage Experience

Hello all. Hope all are doing good. Yeah, lovers and haters are always there, but many thanks to ISS for helping me to connect to some broadminded and genuine people. For those who think, this is a fantasy/fake/true, you are most welcome to think the way you want to, cannot help or force anybody to think positive always. A little about me, I am Nishant, aged 30, from Bengaluru, offering massages to females and couples for nearly four years now. I have posted few experiences of mine here. You...

1 year ago
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Massage Parlor First Time 8211 My Real Experience

So first a little brief about myself. I’m 22 and with no real kind of experience with a female. From a long time I wanted to visit a spa/massage parlor to get this curiosity out of my system about getting physical with a female. This dream turned into reality when one of my good friend, let’s call him JJ, suggested that I should try out this massage parlor at a good locality in Mumbai. At first I was really excited and told him yes on the spot but later on I got the jitters and kept declining...

1 year ago
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Computer Institute Experience

Ye meri life ka jo first sexperience tha wo aaj aap sab ISS readers se pehli baar share kar raha hu. Ek ek word khud likha hai maine, kahi se copy nahi kiya isliye pls mere is exprnce ko dil se padna aur dil se mujhe response bhejna. Meri id hai – Hi Tough Guys. Hi all beautiful Girls & sexy ladies (I think married girls/ladies are sexier than unmarried girls but at the same time I feel unmarried girls are very very hot indeed! Ha ha ha. Me Clever na? dono ko pata raha hu!) Mera naam RAJ...

2 years ago
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Anna and my Swiss holiday experience

Anna and I have been best friends since university and like all best friends we have had our ups and downs mainly fuelled by far too much drink, my insecurities over Anna's stunning looks and her ability to attract far more attention from guys than I ever could, but despite this we have remained truly loyal to each other and as my best friend I really value that in our friendship. Anna and I are very similar looking and we are a simular size as well, (which has always been fab for swapping...

4 years ago
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Behan Ka Shadi Wala Experience

Hi mere pyaare doston, main Subham hu, aur main Delhi ka rehne wala hu. Meri umar 27 saal hai, aur meri chhoti behan ki umar abhi 23 hui hai. Uska figure 34-26-34 hai. To aaye kahani shuru karte hai. Meri behan ka naam Supriya hai. Wo graduation kar chuki hai, aur ab MBA karna chaahti hai. Main usko kabhi-kabhi padhne mein madad kar deta hu. Main meri patni, mummy, papa aur Supriya hum sab sath ek 3 bhk flat mein rehte hai. Supriya ko jab bhi koi doubts hote hai, to wo mere room mein chali aati...

3 years ago
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An Enhanced Experience

An Enhanced Experience Bzzzzzt ... bzzzzt... Good day ... MiriclSoft Support ... how may we help you? G’day ... me bloody screen’s gone all green ‘n’ yellow! And the letters are scrambled! I see. Sir, which of our products are you using? Orifice 2020.5.25 Very good, Sir. And do you have our new “365+7+24 AutoPatch” feature enabled? Huh? (Customer Support rep repeats question) Beats the ‘ell outta me? Is this something new? Oh, yes, Sir, quite new ... as of 2350 GMT, a system-wide...

3 years ago
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My wifes first interracial experience

This is a true story that took place a couple years ago. My wife and I had been married for a couple years at this point. We are both on our second marriage and couldn't be more happy with our lives. Our sex life was completely amazing and it wasn't uncommon for us to go at it at least three or four times a day. Amy is 38, 5' tall 115lbs with short blonde hair. She has beautiful fake large C cup tits and an ass that's out of this world. I always describe her as being built like a Russian...

4 years ago
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Checking Out New Experiences

It was a Friday morning when all the cogs and wheels appeared to be falling into place after nearly two years of talking about fulfilling this fantasy. Louise walked around her local supermarket assembling a collection of groceries, some staple, others for a special dinner with her partner. Tonight wouldn't be a triumphant demonstration of her culinary skills, but more a case of a simple and healthy dinner which would allow them the better part of the evening for relaxing and seduction,...

3 years ago
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Howto Strapon Training Experience

I found this somewhere and did a bit of clean up to it. Experienced strap-on trainers and Dommes, please feel free to provide feedback on this article. -tpbThe Strap-On ExperienceLike most masculine hetrosexual men, your husband or boyfriend is likely to strenuously object to and actively resist taking the strap-on at first. Just the idea of having something forced up his ass like that will feel foreign and unnatural to him. Treating his tight little asshole like it's just a hole to be fucked...

2 years ago
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My First Experience

Hi, everyone this is Sree and I am going to explain you my very first experience about having sex without even knowing it fully at a very tender age. I have been reading indian sex stories site since many years and never thought of sharing my experience with all of you. Today I’m revealing my experience to everyone. I’m going to explain you every part in detail since I don’t want to miss anything from my very first experience. Hope you like it and some might have similar experiences like me....

4 years ago
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An Erotic And Sensual Blindfolded Experience

Hello my horny iss readers!!! It’s been a pleasure sharing my experiences with you guys as you have shown a lot of love by writing to me with those wonderful comments and all kinds of requests.. It’s been a long time since I have shared my experiences with you as I have been a little busy trying to meet all the lovely horny girls and woman in this busy schedule who are waiting to be loved and pleased in the most special and unique ways.. For all the new readers let me introduce myself. I’m...

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