Jan's Chicago Business Trip Pt. 03

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The continuing story of Jan in Chicago.
5.3k words
4.47
14.5k
17

Part 3 of the 3 part series

Updated 06/09/2023
Created 07/26/2019
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cuckold308
cuckold308
494 Followers

"Tonight was fucking epic. Absolutely off the chain."

Michael's words to Thomas and Jason as they were leaving our hotel room.

He was referring to the events recently concluded. Both men had fucked me (Jan) repeatedly, while Michael watched and took pictures.

Michael continued, "You know Jan and I will be staying here in Chicago for two more days? If you get my drift."

Michaels farewell words, a not-so-subtle invitation for an encore performance, still took me by surprise.

Michael had thrown down the gauntlet, only time would tell if the challenge would be accepted.

Although a bit flabbergasted, I wasn't disappointed. And why should I be? I had been serviced for hours by two of the largest cocks I'd ever seen, let alone fucked. The possibility of a repeat performance was certainly appealing.

It didn't take long for the challenge to be accepted.

Only hours later, Jason texted me, twice in fact.

My heart nearly skipped a beat reading the first message, "Last night - WOW! Encore? PLEASE? Hit me up."

The 2nd text, simply saying, "It misses U 2! Call me!"

The attached photo, a closeup of his huge uncircumcised black cock.

Seeing the astonished look on my face, Michael asked, "What's up?"

Handing him the phone, he read the text aloud, while looking at the picture.

After a brief moment Michael said, "OMG Jan, Jason wants to have sex with you again! I can't say I blame him. Last night was so hot. Personally, I'd love to see you fucked by his monster cock again. That said, it's your body, your choice."

My mind was riddled with conflicting thoughts of desire, and pangs of guilt. A decision needed to be made.

Was I interested? Hell yes! Fact is, I was getting wetter by the moment just reviewing his message and staring at his picture. Memories of that magnificent muscular body pinning me to the bed, but mostly of that huge cock filling my cunt so fully, giving me one epic orgasm after another.

Then there was the guilt.

Guilt of having sex with Thomas, a black business associate, without Michael's consent.

It went down like this.

At the conference just two days ago, Thomas was constantly flirting with me. I was flattered and did some flirting on my own. Thomas obviously took this as a sign, followed me into the hotel restroom. Although shocked by his bold action, I allowed him into my stall, sucked his cock, fucked him bareback, finally letting him fill my unprotected cunt with a huge load of cum.

And that was only part of the story.

Later that evening, Thomas came to my hotel room, fucked me god knows how many times. Spent the night. Fucked me again in the AM. Making matters worse, he took pictures of us. These very same pictures he later presented to Michael, followed by a bold proposal of a threesome. To my surprise, it was a proposal Michael accepted.

However, the threesome wasn't exactly what Michael and I expected. Thomas also invited his friend Jason to join in the fun. After some hot foreplay, in the hotel bar, the four of us retired to my hotel room. Both men fucked me repeatedly while Michael took pictures and video.

Now here I was, my desire now beginning to override any feelings of guilt. Michael certainly ready, this is ready to observe and film more action.

My decision made; I pressed the call button.

Jason answered on the first ring.

"Jan, so glad you returned my call. I hope your invitation to visit again, is the reason."

With my hands already shaking, answering, "It is."

"Awesome! I was hoping for that decision."

After a brief pause, he said, "Jan, I have been thinking about last night. Your beautiful naked body writhing beneath me, as I plunged my cock into you over and over again. Your cunt squeezing my cock as you orgasmed. The exquisite feeling of pleasure as I emptied my balls into you. I just had to be with you at least one more time, before you disappear back to Atlanta."

What could I say to such glowing accolades? My embarrassed response simply, "Me to."

Jason again, "FYI, Thomas's rude behavior was embarrassing. I'd like to meet with you solo unless you feel it necessary to have Thomas there as well?"

Although thoughts of being shared by two hung black men was what I had in mind, Jason was right, Thomas had been overly cocky, and especially rude towards Michael.

With that in mind I told him, "Just you alone would be great."

Jason asking, "And Michael?"

I said, "He will be there to watch and take pictures but will most likely not participate."

"No problem, I completely understand and respect his interests."

Adding, "Great, so it's a date then. Should we meet at the bar?"

Thinking back to the display our quartet put on in the bar last night, I said, "No, please come directly to our hotel room."

"Perfect. How about 7PM? That should give us plenty of time for playing. I'll bring the wine."

"7 PM works for us." I didn't bother to check with Michael. It wasn't necessary. The look of anticipation on his face telling me 7PM couldn't arrive soon enough.

Not much was discussed between Michael and I about the upcoming event. However, he was helpful in my decision about what to wear. In the end we decided on a minimalist approach, a G string and high heels. More clothing would only encourage additional socializing, possibly delaying getting to the main event.[[slnc600]]

As the 7PM hour approached, Michael readied the hotel room. Dimming the lights enough to be sexy, while still allowing enough for pictures. Checked the camera for sufficient memory. The last thing he wanted was to have to change memory cards in the midst of the action. Wine glasses in place. Nightstand stocked with lubricant.

Although sure my pussy would generate ample wetness, this was a huge cock that would be taking up residence.

I wasn't too worried, it fit fine last night. It would certainly do so again. The one difference being, tonight Thomas wouldn't be there to provide some initial stretching.

Besides there was always lubricant.

Condoms were not an option. Jason had already barebacked me, unloading his balls into my pussy several times. So why bother now. Even if I wanted him to wear a condom, which I didn't, it was doubtful we would be able to find one large enough.

As for me, I followed my normal beauty routine, only this time it was being administered with extra care. Showered, check, legs shaved, check, pubic hair neatly trimmed, check, hair and makeup perfect. Lipstick color chosen to standout in pictures, especially when my lips were wrapped around Jason's large black cock.

I was ready. Michael offering a glass of wine to set the mood and settle my nerves.

At 7PM precisely, a knock was heard at our hotel room door. We had decided earlier I would be the one to answer.

Opening the door to Jason smiling face, he obviously approved of my attire. Luckily no-one else was in the hall. Leaning in he kissed me, then gave a friendly nod of approval to Michael.

Entering the room he said, "Michael, you are a lucky man to have this lovely woman with you every day. Thank you in advance for sharing her with me."

Dressed in stylish slacks and tight-fitting shirt, he said, "Wow! Jan, I love what you are wearing, but I'm feeling a bit overdressed. Let me rectify that situation."

Without waiting for a response, Jason quickly stripped off his clothing, leaving only his tight underwear, the outline of his huge cock clearly visible beneath.

"Now we're on equal footing."

Without further fanfare, he scooped me up and carried me to the bedroom, laying me on the king-sized bed. The same bed where he and Thomas fucked me last night.

Rolling onto my stomach, I inched over to the side where Jason now stood. My goal reached, I ran my fingers over the stretchy fabric, tracing the outline of his huge manhood.

Reaching to the waistband, slowly pulled it down, just far enough to allow his cock to spring free. It was as huge as I remembered. Although not yet completely erect, it was still a sight to behold. At least 10 inches long, nearly thick as a Red Bull can. The uncircumcised foreskin covering a huge purple head. Veins bulging all over the massive shaft. Veins so large you could almost see them pulse with every heartbeat.

Attempting to wrap my fingers around his shaft was an exercise in futility, the girth just too great.

Nevertheless, I was able to grip his cock tight enough to pull the foreskin back, allowing the large mushroom shaped head to be revealed.

Pre-cum was already leaking from its head, forming into a rapidly growing droplet. Not wanting to waste any of the sticky sweet fluid, my tongue caught it just before it fell. Leaving my tongue extended, collected any remaining nectar directly from the source.

Michael, ever observant, caught sight of this, taking several pictures before I swallowed my sweet reward.

It was now time to suck this beautiful cock.

Pulling back the foreskin, I pursed my lips against the tip of his cock. Its texture spongy, yet firm. Parting them ever wider to accommodate his girth, I continued my descent. As the entire head entered my mouth, my lips had been stretched so wide they snapped down onto his shaft. Inching down further, my tongue teased the sensitive bridge of skin beneath the head.

Jason moaned in pleasure, as my mouth and tongue did its handiwork. Placing his hand behind my head, he began to fuck my mouth, urging me ever deeper. Able to control my gag reflex, I allowed his cock to pass over my tongue gain and entry to my throat.

Continuing my descent, my nose was eventually tickled by his kinky pubic hair. Knowing my goal nearly attained, reached out a final time with my lips, using them to drag me further inward.

Touchdown, I had successfully throated Jason's huge member. Careful to breathe only thru my nose, I continued to avoid triggering any tendency to gag. Remaining nearly motionless, his cock still fully encased in my mouth and throat, allowing both of us to savor our individual sensations.

For him, it was the feeling of his cock fully throated, for me, the thrill and satisfaction of taking a cock so deep.

Visions of a sword swallower entered my mind.

Eventually I began the slow extraction of this man's human sausage from my throat and mouth. Inch by inch, more cock reappeared from between my lips. It seemed to go on forever.

Eventually the huge purple head made its exodus, giving me an opportunity to widen my view. Looking up I saw the look of amazement and satisfaction not only on Jason's face, but on Michael's as well. I believe Michael was almost as proud of my accomplishment as I was.

Although I didn't see any camera flash, I was sure Michael would not let such an event go unrecorded. As if reading my mind, he held the camera up, gave me a thumbs up saying, "Got it."

Huge cock deep throated, check. It was finally time to give Jason the prize he came to collect.

Leaning over me, Jason hooked his fingers in the sides of my G-string. Raising my hips to assist, he eased them over my ass and down my legs, then tossed the thoroughly soaked garment to Michael.

Asking him with a laugh, "Do you think Jan is ready for me?"

Wearing nothing but heels, I began to kick them off, but Jason told me, "Please leave them on, it's so sexy."

Doing as asked, I then spread my legs invitingly, heels pointing skyward, providing a clear view of my dripping wet slit. Reaching down, I held my labia wide open, asking him, "Is this what you came here for?"

His smiling response, "Most certainly, and I can't wait to try it on!"

Before mounting me, Jason reached over to the nightstand. Taking the bottle of lube, liberally coated his cock with the slippery fluid.

"You might not need that; you've got me sopping wet already."

He said, "Maybe not, but I don't want to chance hurting you. I've got big plans for your pretty pussy tonight. I don't want any unnecessary soreness spoiling our fun."

Although I had taken his cock successfully last night, it had taken some time to adapt to his girth.

Feeling the shaft of his cock sliding up and down my wet slit, I braced myself for the inevitable stretching. But it didn't happen right away. Jason seemed content sawing the shaft of his cock up and down my gash, its head making intermittent contact with my clit.

The sensation more than I could bear, triggering my first orgasm of the evening. Bucking against his manhood like a bronco, I maintained as much direct contact with his cock as possible, prolonging the pleasure.

Shifting positions slightly, he deftly adjusted the angle of his cock. Finding its mark, the head of his cock lodged itself into the entrance of my vagina.

Last night his massive cock required a gradual insertion into my pussy.

This time, in a single slow stroke, my pussy yielded itself to the massive invader. His large meaty cock filling me completely. Before I knew it, he was balls deep, his kinky pubic hair meshed with my gooey blonde counterpart.

Looking into my eyes saying, "See, you've taken my all again. This time with only minimal resistance. How do you feel? Are you ready to be fucked?"

With a smile I told him, "The word full barely describes the sensation, but it's wonderful. As you entered me, I could feel my vagina willingly expanding as you sank ever deeper into me. The fit perfect. While I'm ready for you to fuck me, I'd like to just enjoy the sensation of my cunt filled to the brim, for a few moments."

Remaining motionless, Jason silently honored my request.

A few moments later, I flexed my pussy muscles several times.

Laughing now he said, "I guess that's my cue to begin."

Using short slow strokes and circular hip motions, he gradually re-stretched my cunt, allowing time to re-adapt itself to his amazing length and girth. It was obvious the man had fucked many a tight pussy, his experience showing how to provide pleasure without causing undue pain.

My cunt, a quick study, rapidly learning its new norm.

Last then a dozen strokes later his cock was flowing smoothly in and out of my cunt. Only now they were still deep, but full length. Their tempo and intensity increasing as well. His pubic bone striking my clit, balls slapping loudly against my ass. My cunt spewing so much lubrication, a splashing sound could be heard each time he bottomed out.

All I could do was moan incessantly, nearly screaming. Any words uttered were almost unintelligible.

At times Jason would pull back rapidly, completely removing his cock from my cunt, then a moment later, plunge back in. The re-entry as rapid as his exit. No aiming was necessary. It was like two magnets attracting each other, the alignment automatic.

Each time his cock exited my pussy, an audible pop sound could be heard, as air rushed in to fill the void. The sound akin to a muted version of a champaign bottle being opened.

His rapid re-entry produced an altogether different sound. The air in my cunt being displaced created a pussy farting noise. Embarrassing at first, but it soon became just part of the act.

Raising my head from the pillow, I watched in amazement as his thick black cock plunged in and out of me. My juices whipping up a white frothy broth, coating his shaft. Finally able to see what I had only been able to feel. The view, wondrous.

Although well aware my pussy lips were stretched tightly around his shaft, I was somewhat startled to see how far outward they were dragged with each stroke. The sight bringing to mind a miniature volcano spewing molten hot black cock.

Returning my head to the pillow, Jason abandoned his pushup posture, lying on top of me, his head alongside of my face.

The intensity of his assault on my cunt reached a crescendo. His hips moving at a frantic pace. The head of his cock repeatedly striking my sensitive cervix, causing intense stimulation.

This finally pushed me over the edge.

As I started to climax, Jason slammed his hips deeply into me one final time. His simultaneous groan, a sure signal he was about to unload his potent black sperm into me.

His cock now pressed tightly against my cervix, the warm contents of his balls beginning to flood my pussy. I could feel his cock pulse as he released spurt after spurt of hot cum into my waiting vagina.

Last night's experience had already shown Jason to be a cum producing machine. Some of his sperm was undoubtedly injected directly into my womb, the remainder trying to find empty space somewhere in my very full vagina. Obviously, the space insufficient, as cum spurted out of my cunt, even though my pussy lips were tightly wrapped around his cock.

Jason continued to hold my legs high, cock still balls deep in my vagina, his pubic bone pressing against my clit, all together the intense stimulation prolonged my orgasm.

It was glorious. Didn't want it to end anytime soon.

Then some reality crept into my mind.

Here I was, a huge load of cum trapped in my pussy, gravity causing it to puddle deep in my vagina. My extended orgasm triggering my cervix to automatically pulse, dipping into Jason's pool of sperm, sucking them up like a vacuum, then speeding the swimmers on their way to my uterus.

It was the perfect storm for baby making.

Pretty sure my birth control regimen was up to date; I chased these thoughts from my mind.

Now spent, Jason slowly withdrew his cock from my cunt. His cock so long it felt as if it would never end. Once fully extracted, he rested its huge head on my clit, then watched as his load began to flow from my gaped pussy. I could feel it flow over the rosebud of my anus, then down the crack of my ass.

It made for one epic picture.

In the spirit of creating erotic photos, I spread my pussy lips, revealing the huge cavern Jason's cock left behind. It was as if his cock had created an invisible speculum. The resulting gape so large, you could actually see my cervix.

Jason signaled Michael to get a picture of the current state of my pussy, saying, "Wow, Michael check this out! If this isn't an epic gape, nothing is!"

There was a look of shock and anguish on Michael's face, as he photographed the cave that was once my tight cunt.

Seeing his reaction, Jason reassured him, "Don't worry, Jan's pussy will return to 'almost' normal in several days. I guarantee it."

Later when we reviewed an extreme closeup, my cervix looked like a volcanic island surrounded by a sea of sperm.

The photo op over, at least for now, the three of us retired to the living room sofa for some sorely needed R&R.

While enjoying a glass of wine, my fingers found Jason's cock. Unable to resist, I gradually began stroking it.

Leaning over, I took that marvelous tool into my mouth again. My intention, to just enjoy this man's fantastic member, not deep throat him again.

Before long, my oral musing produced the desired effect. Jason cock again fully erect, ready for business.

Jason saying, "I'm ready. And you?"

My mouth full of cock, nodded my head in agreement, mumbling, "Me too."

Rising to his feet, Jason bent me over the arm of the sofa. His intentions very clear.

After applying a quick splash of lube, he loudly spanked my pussy with his cock several times, before sliding it up and down my sopping wet slit. The head quickly located its target, wedging itself in the opening to my vagina.

The single fast thrust that followed, found his cock buried balls deep in my cunt once again.

The sudden invasion expelling air from my lungs.

Now there was no delay of game, no time to enjoy the sensation of fullness. Jason just began fucking me doggie style, hard. Now getting exactly what I needed. I wanted to be fucked.

His hips crashing into my ass cheeks, heavy ball sack swaying, smacking my clit with every thrust.

Grabbing my hair, pulling my head back, Jason asserting his domination as he continued ramming his cock into my cunt over and over again. Now I was being properly fucked.

cuckold308
cuckold308
494 Followers
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