Cuckold Stories Blog

Real cuckold Stories posted by real cuckolds, hot wives and bulls!

Cassandra and Francis

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I was browsing through a bunch of paperbacks in the mystery department of Mulligan’s bookshop when I took my first notice of her. She was in the romance section, some shelves to my right. I never saw her enter the store. I must have been busy with the books.

She looked like a woman in her mid thirties. If I told you her cute face caught my eye first, it would have been a lie. Her face was in fact really pretty. But her body was much more than that, it was something to remember. The catchy, provocative clothes she had on made it clear she was well aware of her insanely appealing figure. The tight-fitting top she had on had trouble confining her massive rack, and that miniskirt barely covered the tight cheeks of her lovely butt.

A small wave of arousal passed through my loins when I noticed her sandals, toes open, high heels, toenails painted red. I had to bring all my self-restraining powers together to prevent myself from falling to her feet and licking these yummy toes.

The long brown hair she had was pulled back in a ponytail. Her style was all about a woman on a relaxed Saturday morning shopping round. Still, her dark eye makeup and lips, bright red, gave an impression it was more than books that she was looking for. This was exactly the female type that gave me the shivers and thrown me into uncontrollable panic.

My name is Francis Townsend. My mom gave me this name in honor of a war hero. It, however, did not prevent the bullies at Charles Gordon Elementary from harassing me. They had real fun mocking my female name. The fact that I was a short, thin guy with barely any effeminate features at all did not matter. As I was growing up I was always the target for never-ending playground jokes.

My older sisters, of which I had two, and their friends, always enjoyed dressing me up as a girl. I was always so humiliated when they finished their job and laughed about how totally convincing I looked.

Don’t get this wrong, I’m not trying to say I’m gay or transvestite. I am a heterosexual to the bone. I still have to admit I often fantasize about powerful, dominant women. I have a bit of foot fetish as well. But hell, everybody has his or her couple of kinks.

What I’m really trying to tell you is that I have never been the macho type, the soccer-playing hunk who attracts lovely girls. The girls like the one who was only steps away from me. Generally I try to avoid getting too close to such women. I feel scared shitless. But of course I do appreciate a cute face, a big sexy rack, and a well-shaped behind. Any guy who does not?

As soon as I noticed this super-hot goddess, I could not stop myself from taking secret peeps. I was really smooth at that. I pretended I was reading some preface while I furtively observed her with the corner of my eye. I was feeling like a naughty kid secretly staring at lingerie mannequins as he was walking through a big store, his mother grabbing him firmly by the hand. That was naughty, but I could not help it.

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Chattel

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Chattel – a slave and personal property

It was a bit past 4:30, I pulled into the horseshoe driveway just in front of Bill Robert’s house. I could see at least 10 cars already parked there. I took notice that my wife’s BMW was also there.

I parked my Ford Escape and looked around the place. I visited this house some time ago for an office party. But I seemed to have forgotten how luxurious Bill’s home was. He was doing great as an attorney obviously.

My wife was Bill Robert’s assistance in administrative matters. She thought Bill was a good employer. The salary he paid her was really generous, and the working atmosphere felt great. I used to hear a lot how she enjoys her job, and she also spent many long hours there.

There were these two partners Bill had, Rick Sullivan and Jerry Goodrich. All the three men were really handsome, in their early forties. Also, they were all divorced. Lindsey shared some information with me and I knew their marriages were destroyed because they had trouble with marital fidelity. She would not say this directly, but from the details she gave I realized all three of them were really accomplished playboys.

The company they had, Roberts, Sullivan and Goodrich, was a small but a very prosperous law firm.

Their office manager was Margo Williams. Lindsey told me she had just about as much power in the company as the three head attorneys. She was a divorced woman, late 30s. I once met her at the office party. Margo was a very graceful and elegant blonde, really attractive. I used to feel weak in her presence because of the air of authority all around her.

Each lawyer in the company had an assistant in administrative matters. All of these people were present at the party.

A girl called Trish Gilbert was Rick’s assistant. She was a young dark-haired woman. Her figure was of that kind many men would refer to as ‘soft body.’ I had a suspicion she would worry over her weight when she got older, but back then she was in her mid twenties. Her large breasts, perfectly shaped round ass and a narrow waist gave her a truly sexy, luscious look.

Jerry Conroy was Jerry’s assistant. You could say Lindsey and Jenny were almost identical, like sisters. Both of them were small-chested blondes, young, with slim shapely figures. Lindsey was 23 and I was to believe Jenny was of the same age back in the day.

Jenny was married while Trish was single.

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Unknowing cuck, unknowing bull

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Really, I could not believe this was actually happening. Even right now, looking back onto it all, with several months since that, it looks unreal. Thing is, it did happen, and the entire situation keeps changing and getting even more strange.

I have to say this first time on the boat at Lake Powell was a weird experience. As if I was looking at two people from a distance, through a soft focus lens or something. I can’t explain it. Probably booze has to be blamed at least partially.

There she was, naked, very much aroused, obviously. She gave out quiet moans as she was blowing me. During the day, I had really tried to fight her off. She had been teasing and daring me the entire day. She showed more and more of her body, rubbing against me in the narrow passages of the boat. She was rubbing the tan lotion into her skin slowly and asked for help with it. She would flash her pussy and touch herself bringing her nipples to a stiff, aroused, prominent state. I must say I had accepted her tease once. Earlier that day, I fingered her into a minor orgasm. I had thought it would scare her and make her back off. Wrong!

I was in the state of extreme arousal since early afternoon. She clearly knew it. My defenses were very week in the evening when she started groping me.

Ron and Kori were my best friends. I had bought a house next to theirs around 9 years ago. We had spent plenty of time together. We had also been on vacation together before. Last summer we took a houseboat trip with another couple and Kristi, my fiance.

Surely, there were lots of sex jokes on that trip, quite an amount of sexual tension and flirting. The sexual innuendo seemed to be perpetual. Nothing ever really happened though. The girls would go topless sometimes. We would also skinny-dip in the moonlight now and then, but that was truly innocent.

That trip was so cool we decided to repeat the experience this year. The other couple had decided not to go at the last minute because of a death in the family. We could not get our money back, and Kristi pulled another stupid shit which I will describe in more detail later. So, it was Kori, Ron, and me.

I had really attempted to avoid it all and have my share of money back. Ron and Kori were so insistent and persuaded me to come, saying I needed a getaway and some relaxation. They said they would really have no fun with just the two of them on the massive boat.

Another reason for my hesitation was Kori’s behavior. She had spent years daring me and doing embarrassing, arousing things to me. I really like her and Ron, I just wasn’t sure how much of it I could take. This was an obvious tease and nothing else, and she did enjoy seeing my embarrassment. I was pretty sure she would never go through with stuff like that!

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