The P.i.

[itsnatural82]

The strange man had been following me for blocks. I first noticed him when I came out of the coffee shop - I always notice a good looking guy on the street, and this one was right up my alley. Mid-40s, solid muscular build, scruffy facial hair. Nothing like my boyfriend, who is in his late 20s, smooth and athletic. Very hot, but very different from the man on the street. I saw him look away when I made eye contact with him, and didn’t think much of it as I turned and walked down the street. It was only when I came out of the convenience store a few minutes later and saw him a few doors down, pretending to be reading the paper, that I thought something was up. I kept walking, my gym bag slung over my shoulder, trying to shake the thought that he was actually following me. It’s not that it’s so unusual for men to notice me on the street - I’m good looking, 32, 6’1 180, with a very good body. So maybe this guy really was cruising me, only he’s a bit more shy than your average gawker. I was kind of excited by the prospect of being stalked like this, but I had plans for the gym, so I walked on.  I glanced back several times, and saw he was still there - I was sure he was following me now, and I wanted to find out his intentions. I turned a corner and sped along half a block and ducked into an alley. I allowed enough time for him to get close, and then emerged from my hiding spot, practically running into him in the process.

 

“What are you doing, man? Are you following me?”

“I’m sorry, Joey. I didn’t want you to find out this way.”

“What did you say? How do you know my name?”

“Its complicated, Joey. Maybe we should go someplace and chat.”

“No, dude. What the fuck? Tell me how you know my name.”

“Well, OK. Your boyfriend asked me to find out what you’ve been up to. It seems some of your activities lately have made him suspicious that you may be cheating on him. So he hired me, a Private Investigator, to find out the truth. Now would you like to go someplace and chat?”

I nodded, and we found a quiet coffee shop where we could speak privately.

 

***

 

“So Joey, it seems you got a little careless with your computer, and your boyfriend found some things that made him wonder. What he saw wasn’t conclusive, but he said it fit with a pattern of behavior lately, you being a bit less connected, a bit distracted, maybe not quite as attentive sexually. All that by itself wasn’t enough, but when he saw that you had been browsing craigslist m4m ads when you left it up on your browser, it got him wondering. And he loves you so much, he didn’t want you to be mad if it just turned out to be his own insecurities creating this worst-case scenario, so he hired me to help him find out. And I’ve been doing some research on you for a few weeks now.”

 

“But I never…”

 

“I know, Joey. I know. What I’ve found out is that you have an active fantasy life. You like to browse personal ads, even place some yourself. You like to chat with other guys online, even interacting on the phone and on cam with some. But based on what I’ve observed while I’ve been watching you, I believe you when you assert that you have never cheated.”

 

“Oh, good. So you can just tell him that and we can move on?”

 

“Well Joey, it’s not quite that simple. I promised him I would tell him what I found out about what you’ve been doing. And I think we both know he wouldn’t be very happy to find out about the things you’ve been doing, even if it’s only online. Isn’t that right?”

 

I blushed, and looked away. I know he would be devastated to find out about the things I’ve been fantasizing about, and the fact that I was doing it with random guys online. I felt a knot in the pit of my stomach, thinking that this could be the end of my relationship.

 

“So Joey, here’s what I would propose. I think there’s a way we could both get what we wanted from this, and you and your boyfriend could continue on as you have been.”

 

“Really?? How?”

 

“Well Joey, I’ve become quite familiar with your fantasy life lately. And I have to say, I think it would be hot to make it a reality.”

 

“Wait, what?”

 

“You heard me. I think that you’ve been holding back on your desire to act on your fantasies, and the only way to save your relationship and have me tell your boyfriend that you’re not cheating on him, is to actually cheat. With me.”

 

 

[MackyJay]

:DVery hot start.

[seaguy]

Fucking boner inducing start.  Can't wait for more.

[Guest JizzDumpWI]

keep it cummin...

[lungfucker]

Excellent start!  So many questions!  So many possibilities!  And the players seems so hot!  Excellent writing with wonderful set-up.  I look forward to the next chapter.

[daddybear]

great start!

[itsnatural82]

My head was spinning. So much was happening, so fast. I discovered this gorgeous guy following me, and admit to considering how hot it would be to fuck him. But that happens all the time, and I just add it to my fantasy bank. But then he tells me he’s actually a PI and has been following me, and he knows all about the stuff I thought was so secret? And he could ruin my relationship with the man I love and have been with for over 5 years. World crashing down around me, and now he’s flipping it again and saying if I actually live out my fantasy with a hot stud like him, I can also save my relationship?

 

“It’s really not much of a choice, is it Joey? Why don’t we go back to your place?”

 

I looked him up and down one more time. I hadn’t realized just how hot he was when I first saw him. He really fills out his jeans, and looks like he’s packing a huge bulge. He must be 6’3 and weigh 220. Nice and beefy. My cock jumped at the thought of being with him, and I realized that going along with this was my only chance of keeping my boyfriend. So I picked up my gym bag and said, “Let’s go.”

 

My boyfriend was away for the weekend, which he must have known. When we got to my place, as soon as my gym bag hit the floor, he pinned me against the wall and brought his face close to mine. He looked in my eyes and said, “Kiss me, Joey. Kiss your first new mouth in 5 years.”  And I did. I brought my lips to his, parted them, and shoved my tongue in his throat. I had wanted to do this for so long, to connect with a new man, and here was my opportunity. I wasn’t going to waste it.

 

I felt his hand on the back of my head, holding me close, and then I felt pressure on it, guiding me down to his neck. I slurped on his scruffy neck and then kissed down over his chest and abs through his shirt as he kept pushing me down, down. I finally reached his bulge, and felt his huge cock throbbing through his jeans against my cheek. “You feel that, Joey? That’s my desire for you. That’s the hard cock of another man, a cock that needs attention.”

 

I undid his fly and hauled out his enormous dong. It had to be 9 inches, far bigger than my boyfriend’s 6.5. My eyes bugged out, no doubt, but my mouth watered at the sight. He said, “Go ahead. Taste your first new cock in 5 years.”  I touched my tongue to the head, and quickly lost myself in the sensation of doing what I had been fantasizing about for months. I squeezed his shaft, tugged on his balls, tasted his sweet precum. I gave the best blowjob I’d given since the early days of my relationship. I wanted to swallow him whole. I went down as far as I could until I started choking, and then I felt his hand push me farther. I’d never deep throated anything that big, but in that moment I pushed past my limits and found my lips and nose nuzzled in his bush, his cock oozing into my throat.

 

When I pulled off, his dick was coated in mucous, and my eyes were streaming tears. I was a mess, but I had just swallowed the biggest cock ever, and I knew I wanted more. And so did he. He helped me stand and said, “Take me to your bedroom, Joey.”  I grabbed his hand as he stepped out of his jeans, grabbed them, and I led him down the hall to the room that Jake and I share. I hesitated only briefly before opening the door and leading him in. We both took in the surroundings - so familiar and home to me, and so clearly a room full of memories and a shared life that he was witnessing. He saw the pictures on our walls and dressers and bedside tables, the souvenirs from our travels, and he saw the bed that we sleep in together every night. Somehow he knew just where to go, and he walked to my boyfriend’s side of the bed and laid down. I stripped out of my clothes, giving him a little show as he lay where my boyfriend lays, stroking his cock as he watched me get naked.

 

As I approached the bed, he pointed to his jeans on the floor and told me to grab what’s in the front pocket. I fumbled a bit to find it, and then pulled out a condom.My heart sank a little, but knowing this was the right choice given what I was doing, I smiled and brought it to him, “Joey, I’m going to fuck you right here in your bed. I’m going to lay where your boyfriend lays, and you’re going to sit on my dick, you’re going to take another man’s cock inside you right here. I know it’s what you’ve wanted, what you’ve dreamt of every time you and Jake have sex. I’ve read your online postings, I know the scenario you have played out a thousand times, and we’re going to do it for real. Here. Now.” With that, he grabbed the rubber and tore it open, deftly sliding it onto his throbbing cock. I straddled him and stroked him, feeling how hard and ready he was to penetrate me. As I felt his head find my hole, I looked over at the full length mirror next to the bed - the mirror in which I had watched my boyfriend and I have sex so many times - and I saw myself poised to be fucked. And I saw him, this hunk of a man laying in my boyfriend’s spot, preparing to fulfill my every fantasy. So gorgeous, so new, awakening synapses in my body I’d forgotten could fire - the excitement of the first time all over again.

 

I bore down as I turned to look at him. I saw the lust in his eyes, as he no doubt saw in mine. I watched his expression as his head pushed into me, popping inside my tight hole. It had been years since I’d had anything close to this big inside me - I never had, actually, but Jake’s is so much smaller. It hurt, but I took my time, breathing, running my hands over his chest through his shirt - I was so focused on his cock I’d forgotten to help him get completely naked.  I concentrated on opening myself to him, on the way it felt to allow a new man into my hole. I tried not to think about how many times I had done this very thing with Jake, in this very spot. I knew what I was doing was wrong, but at the same time I knew it was what I wanted, what I needed in that moment. And this man was just about as perfect for the job as anyone I'd ever fantasized about. He understood my need, it felt like he truly knew me, maybe even better than I knew myself. I continued to take him deeper, feeling more full inside than I ever had before. Physically, he was hitting places that had never been touched before, and there was an added element of fulfillment too - finally giving in to the desires I had held so close for so long.  Before long, I could feel his bush against my ass and I knew one final push and he would be balls deep. I smiled down at him, and I pushed down against his enormous cock and felt his final inch enter me. I had done it - I had taken the biggest cock I'd ever attempted to take. And it felt amazing.

 

Then he started to fuck me. And oh, was he a good fuck. I had thought the sex with Jake was connected, bonding, emotional. But there was something about what I was doing that took things to a very different place, somewhere I wasn't sure I was ready to go. But he took me there with his thrusts. I'd never felt like I needed a cock inside me the way I felt like I needed his. When he would pull out, all I wanted was to feel it inside me deep again.  

 

And that's when he said, "Joey.. I gained access to more of your online life than what Jake knows about. It's my job to investigate and discover truths. And I know from your tumblr account about some of the other things that you fantasize about."

[MackyJay]

:DFantastic second part.  Getting better and better as it goes.  Need more soon for sure.

[sinfuljock]

Love this story! This is what I feel every time a new cock slides in me without my bf knowing.

[daddybear]

hope there is more!

[MackyJay]

:(The wait for more is agonizing.  

[itsnatural82]

And that's when he said, "Joey.. I gained access to more of your online life than what Jake knows about. It's my job to investigate and discover truths. And I know from your tumblr account about some of the other things that you fantasize about.

I know about the condom-to-bareback tumblr that you subscribe to, and how you visit it regularly and also search other sites for similar videos. I know that when you pulled the rubber from my pocket that you were disappointed. I know. And I know what you want to do right now. You and I both know. And this is about making your fantasies come true, right? So do it. Do what your heart tells you, Joey."

I couldn't believe it. He had seen the flash of disappointment on my face, he knew what I wanted when even I wouldn't have ever admitted it to him. And I knew it was futile to fight it. It was no longer about what my head might have said was right or wrong, it was all about what I needed in that moment. And he was right - I needed his bare dick inside me. I lifted off his cock and reached down. I put fingers on either side of the base of his shaft and found the rolled end of the condom, barely any roll left given his mammoth cock. I gently massaged and started to roll it up as I planted my hole back on his condomed head. I sat my ass all the way down to where the rubber covered, and then pulled back. I rolled it up a bit more, and then sat back down. The condom was only half on now, but I took his whole cock back inside me. I loved the sensation of the rolled bottom slipping past my ring, knowing the bottom half of his cock was bare in my hole. But I needed more. I lifted off him completely and then squeezed his shaft from the bottom, bringing my fist up and tugging at the condom as I went, until my fist was off his cock and I was pulling it free from his head. His beautiful bare penis stood glistening and throbbing. I smiled at him and then laid down next to him on the bed, tugging on his cock and urging him to climb between my legs. I never let go of him, guiding him to where he belonged, his precum-slicked cock head rubbing in my crack. It found my gaping hole and I pulled him into me. One hand on his shaft, the other reaching around to pull on his ass. I needed him deep and he sank in easily after he had opened me so completely before. And then he was in me - his huge 9" bare cock was buried to the hilt in my hole, right there in my bed. I couldn't believe it, and yet it felt as right as could be. It was as if my whole life led to that moment of taking his raw cock deep in my guts.

And then he fucked me. Oh, how he fucked me. And the sensations were amazing, even better than when he had been covered. I could tell he was enjoying it, we both knew that bare sex was so much better. I felt that now-familiar need every time he pulled out, that addiction to having his cock inside me. I was begging him to fuck me harder, deeper. I knew he could tell I was lost in a frenzy of emotions and sensations, bringing my every fantasy to life.

And that’s when he said, “Joey, I’m making all your dreams come true, aren’t I? I’m giving you the fuck of your life, fulfilling every fantasy you’ve played out online? Tell me you want me to make your fantasies a reality.”

“OH FUCK YES! Please, man. You are my dream man. You are fulfilling me in a way Jake never could, and I want it all from you. I love having your bare cock inside me right here in his bed, your dick so much bigger, so much better than his. I need you inside me, deep, in a way I’ve never needed anything before!”

“Joey, I know there’s another site you have been visiting more and more lately. I know what’s in your heart right now. And I want to show you something.”

[Guest JizzDumpWI]

oh man, don't stop now!

[seaguy]

I think I know what site it is ;-)

[Guest JizzDumpWI]

True, knowing the category this story is in... I am curious what happens with his mate at end....