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Cuckold

All characters appearing or mentioned in this story are 18 years old or older. This story is a work of fiction and any reference or description to actual persons is unintentional.

If you are enjoying these stories, leave a comment about what you liked or didn’t, or things you want to ready more of. I’ll take advice into consideration when I’m working out the next parts of the LoP stories.

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Late August, 1998

With all the recent things that have happened in the last 8 months, and with all the transitions to not only becoming an official adult, and then a graduate, and then becoming rich through a clever invention I sold, I found myself overwhelmed as August 1998 drew to a close.

It wasn’t so much any of those things, but it was the fact that my previously dull and lonely social life was suddenly changed with the help of my best friend Amber.

Now that she was off in Florida pursuing modeling and acting, I found myself lonely again at times. And it was somehow showing through in my behavior as well it seemed.

Leila, my neighbor, switched to day shift for the last bit of nursing school so we now had time to hang out in the evenings. Ashley was taking classes at the community college but also made time to hang out with me. And yes, both women made sure that I was far from lonely.

Still, I had been thinking of moving away from southern California for a while now, just to see how other places would suit me. And Portland, the Silicon Forest, kept coming up in my searching in terms of people, activities, technology companies, and good housing.

“Why would you want to leave here,” asked Leila as she was straddled over me, impaled on my long, thick cock. I had told her over our take out dinner that I was thinking of moving but she didn’t say anything at the time. Bringing it up now seemed sorta weird.

“Huh?” I asked, trying to get her sliding up and down my pole again.

“Why move,” she asked again, staying firmly planted on my middle. “This place is great. My sister lives in Portland and it does not sound fun. Mostly rain and bad property taxes. Besides, ” she said as she ground down on my cock again, slowly moving her hips back and forth, “you would miss what you have here. This whole harem of willing women just aching to satisfy your lustful needs.”

I was temporarily lost in said lust as she kept sliding her pussy over my pole. I enjoyed this while she gained speed and pressure, build her own lust. After a few minutes of riding, she shuddered with an orgasm.

“Oh, FUCK!” she yelled, throwing her head back. Her shuddering jiggled her DD breasts hypnotically. I fondled them as she came down and some sense came back into the world. She laid down on top of me as the occasional after shock of her orgasm squeezed my cock delightfully.

“Yea,” I said, “I would miss everyone, including you.” I kissed her cheek for emphasis. “But I don’t know what I can do here. I mean, I don’t have to do anything really, but just hanging out isn’t a way to spend your life.”

“I can understand that,” Leila said. “You have to live your life as you want to. Even though I would miss your sweet nature, and, if I’m being honest, this great cock you have shoved in me.” For emphasis she squeezed her pussy around my cock firmly.

“And,” she said, “I think I can help you out. My sister is a realtor in Portland. A good one. She can find a good place for a good price.”

“Sweet,” I said, “I’d appreciate it.”

“Good,” she said, kissing me and getting off of me. “Now, get behind me. I want to feel you against my ass.”

I did as bidden as she got on her knees. She put her face against the sheets and proudly stuck our her beautiful, round ass, inviting me in. I lined up my still slick cock and entered her in one hard thrust.

“Oh, shit!” she exclaimed. I continued with long slow thrusts so that she had time for one more orgasm before I finished. After a few minutes she got on her elbows and reached for my phone.

“What are you doing,” I asked, confused. “Ordering a pizza?”

“No,” she said, dialing, “I’m calling my sister.”

“Now?”

“Why not?”

“Cause I’m fucking you doggy style right now.”

“And I am loving it,” she said blissfully, “but I love teasing her and having your giant cock in me while I do that is fun for me.”

Deciding it was best not to get into that too deeply, I continued my fucking of Leila’s ass.

“Hey sis,” she said into the phone. “I got a favor to ask. My friend is thinking of moving up there and wants to view some houses.” She paused a few seconds listening. I picked up the pace so that bed started squeaking audibly. Leila furrowed her brow at me but I just kept up the pace. “Yea, he’s looking for, something…what are you looking for?”

“I don’t know, I’m thinking of other things at the moment,” I told her, spanking her ass lightly.

“Huh?,” she said into the phone. To me she asked, “Whats your price range?”

I told her a number. grandbetting yeni giriş This made her eyes bulge a little. Her eyes bulged a little more as I took my thumb and lightly stroked her asshole, applying some pressure to it as I fucked her. She relayed the number to her sister.

“Yes, he’s serious,” she said into the phone. “I’ll have him call you with the details, I just thought you can get some ideas before. Huh? I don’t know, I haven’t talked to mom recently.”

Wanting to get Leila’s attention back to the here and now, I added more pressure to my thumb and started probing her asshole. Her mouth dropped open as this new intrusion.

“I don’t know,” she said through gritted teeth into the phone. I slipped my thumb up to the first knuckle, increasing my fucking pace. Her mouth was mix of surprise, pleasure, and annoyance. It was beautiful. I added gas to the fire by spanking her ass with my other hand.

“Hey, I gotta go,” she said to her sister. I started moving my thumb in and out of her ass at a slower pace than I was fucking her. With each thumb stroke I went a little deeper until my thumb was reaching up to the second knuckle inside her ass. My own orgasm was building as well, which spurred on my pace a bit. Leila noticed this, but was having a hard time between enjoying herself and chatting on the phone.

“Yes,” she said a bit desperately, “I’ll have him call you. No. Yes. No, you can call mom. I gotta go. OK? Yes. Bye.” She threw the phone down.

“Holy fuck!” she yelled. “That feels so fucking amazing. Keep fucking me in both my holes. Fuck. OOOOhhhhhhh” she screamed into a pillow as her orgasm took over. I could feel her pussy contracting around my cock and her ass squeezing my thumb with more pressure than I expected. She continued to moan for a few more minutes until I couldn’t take any more.

“Oh fuck. I’m cumming” I yelled. I pulled out of her pussy and ass. She flipped quickly onto her back and finished me off with her hand. My first ropes hit her neck and tits, covering them impressively (it had been a couple days so I was backed up a bit). The rest shot out as far as her stomach and covered her pussy. The intensity of it was amazing and I collapsed beside Leila, breathing heavily.

“God damn, dude,” she said, running her fingers through the lakes of cum I deposited on her tits and stomach. “I don’t think you’ve ever shot that much on me before. Even when Ashley and Amber were watching while we fucked in the backseat.”

“Glad I could impress,” I said through breaths.

“And the thumb in my ass? That was new. And awesome. And weird. And awesome. Where did you learn that?”

Remembering my initial dealings with Ms. Kane with fondness, I said, “I had a very good teacher. Did you really like it?”

“It was a shock at first, but I got used to it. And no,” she said in response to my turning to face her, “I am not ready to take that cock in my ass. At least not yet,” she said, smirking.

“Good to know. Anyways,” I said, rolling over to face Leila, “did you sister suspect we were having sex while you talked to her?”

“Ha, probably not. But she’ll help show you around Portland and show you some houses. I’ll give you her number and you can talk specifics. Just watch out for her. She’s crafty.”

“How do you mean?”

“You know how you absolutely love my tits?” she said, cupping her DD breasts, pushing them together for show.

“Yea. They’re glorious,” I told her, shamelessly staring.

“Well, my sister has even bigger tits, F cups I think. We have similar bodies but her tits are gigantic.”

Imagining even larger tits on Leila was a pleasant thought indeed.

“Just don’t make any decisions based on what Little Paul might be thinking,” she cautioned.

“Little?” I said, mock insulted.

“Well, relatively. Calling that monster little is like calling the Pacific Ocean a bathtub. Speaking of,” she said, getting up. “I need to rinse off. Come join me. The least you can do is help clean me off after giving me the firehose treatment.”

I got up and followed her (or rather, ogled her ass as we walked) to the bathroom.

#

Early September, 1998

The first week of September saw me flying for the first time in my life. My friend Kelly, who saw fit to make sure I looked the part of prospective home buyer with taste and money, helped me greatly in getting over my nervousness. She also helped me pick out a suit to wear; sans tie as it was business casual for plane rides. She also made me upgrade to a first class seat as that was what classy folks did apparently. My flight was on a Tuesday at 8pm, so I wasn’t sure how many classy folks traveled at night.

Turns out, that number was 1.

I boarded my flight and discovered that I was all alone on the plane. The two flight attendants were the only other souls in the passenger area, which didn’t bode well for the 2 hour trip.

However, one of the attendants, Maryanne, seemed to pick up on my nervousness grandbetting giriş and kept me company. She was tall, black haired, lightly tanned with sharp facial features, strikingly blue eyes and curves her uniform couldn’t possibly hide. The seats in first class were spacious, but she declined to sit down with me as she was on duty. But she stood by nearly the whole time chatting with me, bringing me drinks and snacks, and making me forget my nervousness.

Once we were back on the ground, she made sure I had my things. The overhead was stuck and she offered to help. I moved aside to give her plenty of space, however she more than a little bit grazed the front of my pants with her rear on the way to opening the compartment. Since my suit pants were tighter than I normally wear, and because her kind attitude and kick ass body were exciting, she was treated to a semi-hard bulge rubbing against her.

Once my bag was down, she slipped me a note.

“My phone number,” she said quietly. “Im home for the next 4 days so if you find yourself needing company, give me a call.”

She winked at me, turned, and strolled back to her station as I departed. I watched her go around the corner before I went on my way. I caught a cab to my hotel in downtown Portland and once in my room turned in early. My room was at the top floor, quite spacious with a large TV in the livingroom. A mini kitchen was by the door but I doubted I’d use it.

Stripping down and tucking in, my last thought of the day was that hoping Morgan, Leila’s sister, was able to find some places meeting my criteria. I’d never bought a house before so hopefully she didn’t try to screw me over.

#

Wednesday morning dawned bright and sunny. I dressed in my grey business casual suite (number 2 of the 3 I brought) and considered myself rather dapper looking. The shoes were being a pain, but Kelly said fancy shoes have a breaking in period. I’d have paid more if they already came broken in for the annoyance it was causing.

I walked the few blocks to Morgans real estate office. She worked for a large company but she did have her name on her door, which proved she was a good agent. I knocked and heard a business-like “Yes?”, so I entered.

The office was on the upper floor of a tall building in downtown, which already had great views. Morgans corner office made the view even more impressive. She also preferred impressive, antique, dark wood furnishings and desk. The office spoke of someone who was very good at their job.

Morgan herself was also impressive. Leila wasn’t exaggerating in her description. Morgan was the same height, the same brown hair and sea-green eye color, and same fair skin, but her hair was wavy rather than curly and in a tight pony tail. She was wearing wire-rimmed glasses that made her more sexy than geeky. And her chest, just as Leila described, was massive on her slim and curvy frame. But it looked like she took effort to present them well.

She was wearing a white button up long sleeve shirt that looked custom made for her so nothing was squished or weirdly shaped. Currently that was buttoned up to her throat. She also had on a knee length black pencil skirt and high black heels. She looked very professional despite her outfit being almost a cliche in terms of male fantasies.

She held out a hand as she came around the giant desk. “Paul, glad to meet you finally. I’m Morgan.”

I shook her hand. “You as well. Leilas told me…well…nothing about you. But I thank you for the work you’ve put in so far.” We sat down on the comfy chairs in the corner while we went over the folder Morgan prepared for me.

“So, since you’re in town for only a short while, I’ve blocked out the day to show you around these properties. It’s quite a collection to say the least, and they’re spread all over the city.”

I took the folder and started running through it. The pictures weren’t great, but the features were everything I asked for. “This all looks great,” I said, “when do we start?”

She stood up and went to her desk, giving me a few seconds to appreciate her fantastic ass. Turning back with keys in hand, she said, “Head down to the lobby and I’ll meet you there in a few minutes.”

I waited in the voluminous lobby as requested. It was barely 9:30 but the building was bustling with people coming and going. “Ready to go,” I heard from behind me. Turning I saw Morgan, but slightly different. She had removed her glasses and switched to low heels. She also changed her shirt to a short sleeve version that was buttoned up only to the top two buttons, which gave a tantalizing view of her collarbone.

She smirked when I looked her up and down. “Don’t be so surprised,” she said.

“I can’t really help it. Just a few changes made for very different results.”

We walked to the elevators and took it down to the underground parking. “I work in an office with a lot of men. And the vast majority don’t like me for 1 of 2 reasons. So I try not to give grandbetting güvenilirmi them something to ogle; it just makes things easier. But when I’m out, I like to dress more relaxed.”

“That sounds terrible,” I said. “Why don’t you get a job somewhere else? That corner office says you’re a good realtor.”

We exited into the garage and walked to her car. A nice looking white BMW. Of course she would drive something like this. It suited the image she was presenting.

“The money is insanely good here. And I am the top realtor by volume and profit. Thats one of the two reasons most men in the office hate me.”

“I’m curious what the other is,” I told her.

She looked over at me. “Maybe later. For now, we need to see a nice little row house in the hills.”

The viewings were all rather dull at first. I brought along a mini camcorder (a recent purchase, because in every skater group, someone has a video camera) to document the places and refer to them later. The first four were nice, but not really what I wanted cause they were all very disconnected from the city. In between viewings, Morgan and I chatted more about our respective lives. She moved out here a year before Leila moved to California, and loved everything about this place, so she was a great guide for local spots and highlighting the great things about Portland.

After the first 4 viewings we broke for lunch. She brought me to a greek restaurant downtown that had a giant purple octopus floating above it. It was weird but the food was good.

“So,” I said during a break in the conversation, “how did you become the top realtor in your firm?”

“Not the firm, the city,” she said. She took another bit of her gyro as if this was a common thing.

“I’m honored then to have the best showing me around. And well done.”

“Thanks,” she said. “And, if I’m being honest, it wasn’t wholly due to my skills, which are great. But it also comes down the fact that, as you might have noticed, I’m not at all bad looking.”

Even though she had a spot of tzatziki sauce on her lips, she was still insanely hot. “Yes, I would heartily agree with that fact.”

“Right, but you do so in at least a polite manner. I see you checking me out,” she smiled at me when she said this, “but a good portion of my referrals think I’m going to sleep with them. And, even though I am not proud of this, I may flirt with them more than a little to close a deal.”

“Hey, if you got it, flaunt it,” I said. “It’s a cliche, but it’s still good advice.”

She looked at me skeptically. “Did you get that from The Producers?”

I took a bite of my gyro to avoid answering.

“In any case, a third of my clients don’t even see me until signing paperwork. The rest…if they don’t know how to control themselves I’m certainly not going to change myself to suit them.”

“Good attitude,” I said. “I notice a lot of that in Leila too. She’s very confident in her manner; same as you.”

“Thanks,” said Morgan. “I’m gonna hit the restroom and then we can see the rest of the properties.”

I finished my meal while she was gone. When she came back I could swear something was different but I couldn’t place it. I could see, thought, that another button on her blouse was undone, revealing no small amount of cleavage. She smiled as I took notice. “Ready to go?” she said.

We paid the check and took a stroll through downtown for a bit before we continued on our viewings.

“Just out of curiosity,” Morgan asked, “are you and Leila dating?”

“No,” I said, “We’re just casual and we hang out. She’s good people. Why?”

“When she called about you moving here and needing a house, it wasn’t the first time I’d heard your name. And, when she did speak of you, she sounded very…content. Satisfied would be another word.”

“We help each other out sometimes,” I said.

“Good to know,” Morgan replied.

We got back to the car and went about seeing the rest of the properties. The last three were all in the city and all in southwest and northwest. The two in southwest were not impressive and one was in worse shape than Morgan realized. At this point my hopes of finding a nice place in Portland were dim.

The last place was in northwest, in one of the oldest parts of the city. The houses here were certainly better kept and the shops were more boutique like than strip mall, which was nice.

The house itself was a two story job with a basement that was divided into apartments at one point but had been empty for over 3 years. Going inside, I could see this as a nice place to live when it was built nearly 100 years ago.

“This whole area around the West Hills was where industry captains, doctors, and other well-to-do’s built their houses. This one,” she consulted her notes, “was built by the widow of a lumber and mill owner in 1904.”

Touring around the place, I trained my camera on various rooms, once or twice capturing Morgan in frame and lingering there perhaps a moment too long. She caught it a few times but always smiled at the camera before continuing the tour.

“I think I am going to buy this house,” I said excitedly. “I love it.”

“Great. It needs some work,” she said as we went upstairs, “but I figured with this being below your budget, you could renovate.”

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