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Introduction:

I know its been some time since I have posted a story but I'm back with a long awaited addition to the Cougar series
I woke some hours after Claire had drifted off. My mind was racing with thoughts of the plan to move. I couldn’t take my mind off that word “plan”. I had never had a plan in my entire life, and now somehow Claire was willing to include me in hers even though she barely knew me. And Gail had only known me maybe 72 hours longer than Claire. I don’t why but I felt this weight of responsibility on my shoulders, something I wasn’t used to. For those of you who don’t understand (yea I’m breaking the fourth wall here) I’m only 24, never had a family, nor a long-term job or significant other, I have never committed to anything in my life. It is definitely a shortcoming of mine but hey that’s the way I liked to live. I couldn’t understand why I was feeling this weight when it suddenly hit me. I cared about them. They’ve accepted me without any sort of quid pro quo, which was something I wasn’t used to especially Gail. She was like the mother I’ve always wanted and the wife I had hoped to find eventually. And she was unbelievably sexy with her voluptuous body, nice firm breast, lush curly hair, narrow waist, and wide well rounded hips. Maybe this won’t be so bad I thought.

I was still worried about other aspects however, for example Claire still believes I am Gail’s stepson and now we’re all to go to British Columbia where I am to meet a man whose wife I have possibly impregnated. Things were the most complicated they had ever been for me. I chuckled to myself “you have royally
fucked up”.

3 months later.

“Jack, I’m getting so fat” Gail said in a mocking manner, lifting her shirt to show her tummy.

“Ha ha, that’s not funny anymore” I said annoyed of that joke that she kept bringing up. After we left the small Yukon town, I thought I might have gotten Gail pregnant and when I asked her she laughed so hard she cried. I couldn’t understand what was so funny but she explained that while it wasn’t impossible at her age it was highly unlikely. I was relieved as I was not a fan of children.

“Alright fine, it actually kind of turns me on, the idea of having a baby with you, huh” she said sauntering over to me, shedding her robe as she closed the distance between us.

“Maybe, the very least we could have fun trying to make one” I said letting the fat cheeks of her ass fill my hands as she straddled me.

Gail wasted no time getting my hard cock out and in one quick motion she slid down the length of my pole.
“Oh god, ugh!” she screamed loudly bouncing up and down, riding my prick as if it were the first time. After she climaxed she dismounted, replacing her cunt with her mouth.

“Mmmm” she hummed swirling her tongue around the wide head of my prick and with a few rapid strokes of her hand I flooded her mouth with my warm cum. “yummy” she said in a sultry voice after letting my prick plop out of her mouth. She licked up the residual cum on my penis getting all she could. Her desire for my essence never ceased to amaze me.

“All right, off to work young man, have a good day” she said skipping off to the bathroom, she did that purposely knowing I like to watch her ass bounce.

I thought about what she said, about me getting her pregnant turning her on. It was, but I that meant I would have two women carrying my children.

Claire announced her pregnancy a month after we got to her home town of British Columbia. Her husband William was ecstatic that he was going to be a father but I knew damn well that it wasn’t his and so did Claire. Gail had no idea of course, then again she was still keeping secrets of her own. I was just surprised no one questioned Gail or I about being her stepson. I liked William though, he was a nice guy and very wealthy. He was a managing partner at an architectural agency. He liked me immediately and offered me a job. Of course I took it even though I didn’t have any education or experience in that area, but I did have some experience in construction. After a month of a training, William let me manage a small division of construction teams for a few projects they were working on.

I loved the work and Claire’s husband apparently liked my leadership abilities. Claire thought he took a liking to me so much because I was like an adopted son of theirs…..with the added dynamic that I was still fucking Claire.

“ugh…..ugh…ughhh!!, not so hard sweetie, I’m still sore from the other night” Claire moaned into her pillows, grabbing fistfuls of the sheets as I pounded into her from behind.

“Sorry, shouldn’t we stop this now anyway. I don’t like all of this sneaking around, William’s done a lot for me and you’re pregnant now”

“Do you really want to talk about my husband or do you want to feed that thick cream of yours to the woman carrying your baby” she said. Her words made my cock twitch and nearly made me blow my load. She always knew what to say to get my mind off the serious stuff. And I thought I was the one who seduced her.

“I guess I’ll take the latter” I said pulling my slippery dick out of her gaping pink hole. She spun around quickly taking me into her mouth and with the slightest of efforts she swallowed 3 quarters of my penis. With one contraction of her throat I erupted, shooting copious amounts of semen down her gullet and into her stomach.

“mmmmmm, always so good” she moaned.

“yes it is…..well we’ve got to get down to the club before your husband suspects anything, he told me to have you there like 40 minutes ago” I said getting up beginning to get dressed.

“relax sweetie, you worry too much” she kissed me and went into the bathroom and got dressed.

“Where have you two been, everyone is already here” William said as we entered the local country club. It was really just a place where old rich pricks come to brag about how much money they made last quarter.

“Sorry boss, you know your woman here couldn’t decide what to wear” I lied jokingly.

“Right you are my boy, c’mon let’s get a drink, the entire board of investors is here tonight”.

I played the part of the bragging, loyal company man for about an hour before I couldn’t contain my disgust for these men anymore. I headed to the bar, noticing
Claire chatting with some other wives in the lounge area. The men were pricks, but damn their wives were gorgeous.

I had a couple of more drinks before leaving to the bathroom to relieve myself.

I entered one of the stalls and started to empty my bladder when I heard someone else enter. I was either crazy or I swore that I heard heels clicking into the men’s restroom. The heels continued to walk until they stopped at my stall. I looked down beneath the door and saw two small feet seated in a shiny pair of red high heels. At first I thought it may have been Claire, but she wouldn’t have followed me in here. She was adventurous but not this risky.

And then as if the person was going to someone’s home door a soft knock was placed on the stall.

I really didn’t know what to do so I stupidly said “occupied” in an unsure manner.

And then another knock came.

“What the fuck” I thought to myself before just deciding to open the door. I swung it outward and a small blonde woman was revealed to me.

“Who the h….”

“Shh” the woman reached up putting her finger to my lips….”we don’t have a lot of time” she whispered before gasping as she looked down.

I’d neglected to put my cock away and now this little blonde woman was getting an eyeful. I couldn’t place where I had seen her before, obviously she was a member of the club but she was more familiar than that. She was a beauty that was for certain. She was maybe only 5ft even but she had nice plump breast that were pushed up in her cocktail dress she wore. She wasn’t old by any means but she may have had me beat by about 10 years.

“I knew you’d be big but gosh” she stared open mouth at my member.

“Look, I don’t what you’re doing in here but you need to leave lady” I said attempting to put my dick back in my pants.

“Let me take care of that for you” she said taking my dick in her tiny warm hand. She pushed me back against the wall closing the door behind her. For her small stature, she was pretty strong.

She moved down to her knees quickly before tugging my pants with her.

“such a beautiful penis” she said to herself with a look of lust as she licked her lips. She began to plant small kisses all over the bulbous prick head coaxing drops of precum to secrete from my hole. I had given up resisting, I didn’t know anything about this woman but she was on her knees now liking my meat from root to tip and that I was all I needed to know for now.
In less than 15 seconds later I was at full mass and I assumed that was the goal as she stood up.

She hiked up her dress and pulled her panties to the side. She turned to face away from me and backed her tight tan butt to meet my crotch. I knew our heights would conflict so I helped her out by squatting down.

I figured I’d let her do the work since she seemed to be the one calling the shots. She reached back to grab one of her delicious globes and lifted exposing her dark pink wet lips. I watched lustfully as she slowly lowered pussy to the head of my cock. She instantly met resistance but she was determined and with some force her tight lips opened around my meat, stretching to accommodate me.

“nghhhh” she grimaced a little but did her best to keep quiet.

She had the tightest pussy I had ever felt. It was like fucking a virgin. I wasn’t complaining, though I was never a fan of slow progress. To help her move things along I grabbed her hips and started to pull her down the rest of the way. This must have caused her some discomfort because she sucked in a sharp breath of air.

“It feels like it’s in my stomach” she moaned. She didn’t move, attempting to give herself some time to get use to the foreign invading member. But she soon began to grind her ass back into my crotch.

“Oooohhh, that’s so fucking good” she moaned louder and I was concerned someone might hear us. “c’mom baby cum for me, shoot that load deep into me. I need it, I fucking need it”

“Wow was she desperately horny” I thought but I wasn’t one to disobey.

I started to thrust up into her depths, rapidly causing her to breathe sharply as she tried to contain herself. With a final thrust I stood straight up, impaling her completely to the hilt, I released a thick load of sperm and injected it right into the womb of this desperate little housewife.

She whimpered and moaned all the while I continued to fill her up with cum and as soon as my cock began to wither inside of her soaked pussy I started to curse myself for succumbing to my lust. I let her down slowly before pulling out of her and making myself respectable.

The woman only adjusted her dress and exited the stall without a word. “nice to meet you too?” I said not knowing what else to say. My head spun, that must have been the most random and interesting of all my escapades, women don’t just do that…….ever, I thought. I went back out to join William and the others, conversing for another hour of exciting architectural affairs. We were about to call it an evening when the wives began joining their husbands coaxing them to leave. My heart nearly stopped when I made eye contact with the small blonde woman from the bathroom standing next to Claire. She barely acknowledged me and only gave a subtle wink before walking over to her husband, who just so happened to be a gentleman named Tom; along with William, Tom was a managing partner of the company.

“You have royally fucked up” I said to myself once again.

More to come.
7 comments

PikupmanReport 

2022-02-09 17:32:50
Really dude! 3 excellent stories and not one of them competed!!??

Anonymous readerReport 

2017-01-16 03:24:52
Good read

Anonymous readerReport 

2016-12-31 11:49:36
The stories are on a ride. It sounds like you are starting to create a whole town in Canada! Seriously these are great reads! Ta Ta for now~

Anonymous readerReport 

2016-12-10 13:18:06
This has been a very good series. I have a thing for older women myself.

Anonymous readerReport 

2016-12-04 09:03:37
Another good chapter. He may have done a hat trick with the blonde.

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