Several months had passed since Shelby and my first threesome with Dillon, and afterward, we became much closer. By June 2019, we decided to make our relationship official which made all our friends and family happy since we got along so well and Shelby was an amazing girl. Our common interests and sexual chemistry were making us want to spend much more time together and if I was being honest, I was starting to think this girl could someday be my wife. Simply put, I was falling for her on every level. 

I could tell I intimidated Shelby quite a bit at first in regards to my more extreme sexual past with my ex’s, however, she seemed to accept me regardless of what others might consider flaws. I know this because she communicated how she found it odd that I was not bothered sharing her with Dillon (see last two stories) and in her word I intimidated her at first. 

Allowing an older guy friend of hers to fuck her, then cum inside her while I watched was not difficult for me to handle at all. On the contrary, it was extremely arousing for me especially after learning this wasn’t the first time he’s had his older white cock deep inside my younger girlfriend. 

Recently, I have also started testing Shelby with interracial cuckold / hotwife porn, mainly to see how much she might enjoy sharing that kink of mine with me someday. It took several years to not judge myself for being turned on by it, and now I fully embrace the fact that I really did enjoy watching my past girlfriends being fucked by well-hung black guys. It might not have been my fantasy originally, however, I definitely adopted the desire to witness it again. 

Shelby, however, has shown zero interest so far in that part of my kink. I could tell she wasn’t too sure how she’d feel about it so I decided not to bring it up again unless she did. Maybe she wasn’t attracted to black guys I thought. I was fine with that since our role play about sharing her with her hung white older guy friends and co-workers seemed to be taking hold of her imagination in the bedroom as time went on. Also, I think my primary kink is watching my girl with any guy, young to old, black to white, especially if the guy had a much larger dick than mine. The bigger the more turned on I get while watching. 

In regards to the threesome with Dillon, Shelby didn’t seem to regret that night at all either. I think she felt awkward whenever we’d discuss her occasional girl nights out in LA alone with Katie, especially if I knew she would be staying the night at Katie and Dillon’s house. I would also occasionally tease her while she was out that she should fuck Dillon again without me and tell me about it later. I’d even jokingly tease that she should involve Katie in a threesome with her stepfather.

One night while Shelby & Katie were out for a girl's night, she tried sexually teasing me back saying they had met a group of, as she described, “Very hot, young, muscular, black guys.” In that text conversation, I teasingly encouraged her to fuck the group but she laughed it off. She would always say I was a trip but never showed any signs of actually doing anything wild without me present. Apparently that night two of the younger black guys from the group took turns fucking Katie as they spit-roasted her but Shelby swore to me she didn’t participate saying she simply went to bed. Apparently, the guys were well known in the Hollywood Hills area but she would tell me who they were.

During the summer, again before covid started, there were a few occasions out at nightclubs where guys would hit on her and I was present to witness. During those nights, I made attempts at arranging another threesome between Shelby, some of my closer guy friends like Nathan, as well as another group of very young-looking ghetto black guys in their early twenties. Unfortunately, I was unable to succeed in getting Shelby to have sex with any of them. She did thoroughly cock tease the young black guys though by sexually dancing with them, grinding her short dress covered ass against their crotches which was very hot for me to watch.

As time passed, Shelby was starting to let loose a bit more sharing more details about her past lovers. One question I always ask in all my relationships is which one of her ex-boyfriends had the biggest cock. I’m not sure why the size of my girlfriends ex-boyfriends turned me on to hear about, but I loved that she finally shared with me that an ex-boyfriend Chris was the largest cock she claimed to have to date. She showed me using her hands spaced apart how long she remembered him being and I laughed since her hands were probably twelve to fourteen inches apart. Clearly she was exaggerating. 

I also finally got the full story on why she wouldn’t let me film her. Apparently, Chris was the one who broke her trust and posted a sex tape they made together online without her permission. Ever since then she said she’d never make another sex tape again unless she controlled where it ended up. After asking for weeks for her to share their sex tape with me, she finally relented agreeing to try to find it. What I didn’t know at the time, while I was at work the following day, Shelby had texted Chris to ask him to send her the video they made together since she couldn’t find it on her devices. 

Something about her going out of her way to contact her ex-boyfriend really turned me on! I guess the part that turned me on the most is that I knew this guy must still masturbate to the video and Shelby contacting him must have stirred up a hornets nest. After that day I noticed Shelby randomly getting texts which she seemed to want to conceal from me seeming shocked.

Shelby was shy when talking about her ex and mainly told me how he was abusive to her and very rude to her family and friends. She did admit that his rough criminal-type demeanor turned her on a lot in the bedroom. When I dug deeper for more details she explained that he was a drug dealer and that he had been incarcerated several times throughout their relationship which lasted all four years of college. I couldn’t believe she’d date a criminal-type like that but it was college for her so I can understand the bad boy attraction.

I imagined a character similar to the one from the show Son’s of Anarchy when I’d fuck her. Plus, he was apparently a musician as well which all my exes have been attracted to for some reason. A few weeks had passed and she was finally willing to share the video they made and it goes without saying, I was extremely excited! 

The video started with my beautiful girlfriend sucking this strange-looking eight or nine-inch fat dark tan soft cock in a dark room of some type. The video camera light lit up Shelby’s face perfectly but the background was very dark. The cock in front of her wasn’t fully hard yet and looked smooth, slick and rubbery for some reason, making me think it was just a dildo. I thought at the time that she had made a fake video with a large dildo just to shut me up. Also, the way the shaft dropped beyond her closed fist made it look soft and fake. 

That was until the video zoomed out and to his left side and I could clearly see the guy’s leg tattoos, his shaven muscular pelvis mound, and the top of his prominent cum filled balls. My eyes shot to Shelby’s and I could tell she was amused at how shocked I was that the video was real.

This was clearly a real video and was in what looked like a van RV conversion. Before, the camera was pointed toward the front of the van so the phone light didn’t expose much detail. But when he filmed from the side I could clearly see the steel exterior frame of a van interior with what looked like metallic bubble wrap covering the window.

The reason his cock looked rubbery initially was a mixture of his shaft being soaking wet with my girlfriends saliva from one of her sloppy wet blowjob I love and the light from his phone camera. I could tell she must have just started since the guy was not even hard yet. You could also tell she had been deep-throating him since her makeup was running down her cheeks from the tears of choking on this guy’s big soft white dick.

The camera perspective moved away from his cock showing more tattoos over his muscular abdomen like you’d find on some gang banger, or musician, which only added to the criminal type appearance she had described. For context, I don’t have any tattoos and look innocent by comparison, however, to be clear, I’m Italian so I’m not a weak guy. I’m just not one that has to act or look tough. Disrespect me and watch out.

While we watched the video, Shelby pulled my cock from my jeans and sucked me while I watched the video on her iPhone. I had to ask, “Why did you not like this video again? Looks like you really enjoyed making it! Fuck, his cock looks big!”

Shelby laughed before explaining while stroking my cock, “It’s very big! Chris liked playing games online and the asshole live-streamed me sucking him while he played. He didn’t ask my permission which is why I didn’t like it! Just wait though, the best part is coming up!”

I responded, saying, “Ah, that makes sense.”

Shelby continued, “I guess what pissed me off the most was that he invited one of my girlfriend’s boyfriends to watch as well, which was super embarrassing!”

That‘s the reason she won’t let anyone film her today. The video she was sharing with me, however, she described as the one Chris and her made with sober knowledge before she learned about the other live-streamed videos from their mutual friends. Apparently after breaking up with Chris, one of his guy friends eventually fucked Shelby also before admitting to have watched her sex tape online. At that point, Chris’s secret was exposed and she learned the full extent of who she was exposed to without her permission. 

During the review of the video, Shelby also confessed that since he sent her these he hasn’t stopped texting her wanting to fuck her again. I responded, saying, “Maybe you should tease him back a bit! Maybe after he cums for you again he’ll lose interest!”

Shelby laughed then grabbed her phone to show me his texts saying, “Cums in me huh?” 

I responded with an entertained smile, saying, “Cums for you, I didn’t say in you! Guess someone has the Dillon situation on her mind!”

Shelby laughed adding, “I guess I had a Freudian slip.” Shelby was clearly getting turned on adding, “He definitely wouldn’t lose interest if I let him fuck me again though with his big cock!” She paused with a naughty grin on her face amused by her naughty word use before she continued, “Actually, maybe I have been teasing him! Would you like it if I sent sexy photos to my ex?”

Shelby took my cock aggressively back into her mouth with cock nearing its limit when I looked a into her eyes to gauge her seriousness before saying, “Fuck, yeah, suck that dick! No, you didn’t! Really? Fuck! Show me!”

Shelby lifted off my cock laughing before grabbing her phone again scrolling down while I looked at her phone with excitement. The first photo she brought up was of her topless flashing him but not showing her face. The picture was clearly very recently sent and I assumed was part of the negotiations to get him to send her the video they made together. She did tease him back already! 

The second text she showed me was a video Chris had sent her of him stroking his very nice limp cock while sitting in a nice cloth chair, clearly masturbating himself hard to the photos she had sent him prior. Even limp the guy looked huge. When his cock was short, it was smooth and a darker pigment, when he grew, it turned hard and a whiter shade. 

The video ended with Chris slowly stroking the tip of his shaft before unloading a huge, extremely thick white creamy load onto his tattooed abdomen while using his other hand hovering above his large engorged tip to control the violent spray. The deposit had to be the most volume of cum I’ve ever seen any single cock produce! It might have appeared like more volume due to the fact that he used his hand to concentrate the pooling area to just his lower abdomen, and that his cum wasn’t inside an orifice like my girlfriend's mouth or pussy.

Seeing her being sexually teased by her ex threw me into a frenzy and Shelby’s intensity increased as her blowjob became increasing wet and sloppy. In the texts following the images of my girlfriend were of Chris begging her to meet him so he could fuck her again! I was shocked but extremely turned on!

At that moment a really bad idea popped into my head and I started her camera app and started recording her to test if she would let me. Surprisingly Shelby didn’t stop me from filming her most likely due to it being from her personal iPhone and not mine. Shelby was unsure what I was doing but I helped her understand when I said, “Chris, so Shelby just told me about your text messages. I thought it’d only be fare if you got to watch her suck my cock as well.”

She was initially very shy but knew what I wanted and spoke directly through the camera lens to my amazement saying, “So… my boyfriend really enjoyed the video we made together. His cock isn’t nearly as big as yours but it’s just as fun to suck!”

Her words shocked me since I wasn’t expecting that. She never mentioned my size in comparison to any other guy before. Shelby immediately leaned forward taking my raging hard cock back into her mouth as she sucked me passionately while making direct eye contact with the camera. Her words and the mixture of imagining her sending this video to Chris sent me over the edge and I unloaded a sizable amount of cum over her face landing most of my cum in her hairline before she contained the remainder in her open mouth. I ended the video after my orgasm and handed the phone back to Shelby to see if she would send the video to him for real. Unfortunately, she refused sending the video but said it was really fun to role play as if she was going to. After I recovered, I fucked Shelby so aggressively that night she actually had multiple orgasms with me for the first time.

After that night, Chris would regularly send her flirtatious texts but nothing more as far as I knew. Shelby seemed to go in and out of interest with talking about him and I did the same. When I thought back to the video, I had noticed a few items out of place though. For example, next to his large cock, when he zoomed out using the palm of his hand to force Shelby's mouth to deep throat his cock, he had an Apple Watch on that I swore was the most current Series 5 released within the last year, the one with the always-on display! I doubted my memory and let it go but even the thought that this video was made recently during our relationship and that she may be cheating on me actually turned me on. I know that sounds strange but I’m weird.

For me, it all stemmed from being cheated on when I was seventeen. While on a river trip to Bullhead City, AZ, my girlfriend Sheena and I watched my best friend Trevor as he stripped down to skinny dip in the lake. When it happened I was confused why I was excited but in my head I imagined my girlfriend reaching out to stroke my friends cock hard since it was really close to her face when he stripped nude. We all skinny-dipped together and later that night by the campfire we watched him getting his dick sucked by the girl he invited for the trip while Shelby and I watched very closely, seated nearby. 

We were all very drunk but it was Trevor’s obscenely large cock that demanded all of our attention. Earlier in the day while skinny dipping he was maybe seven to eight inches soft, jokingly flopping his heavy rod thy to thy, however, during the campfire his cock grew extremely hard to approximately nine to ten inches long and very fat around!

Long story short, I eventually caught Sheena and Trevor one moonlit night in the bed of his truck during an off-roading trip off the 395 outside Los Angeles. Oddly since that night in the desert, I have always been turned on by my girlfriend fucking a big cocked guy behind my back. At first I thought Trevor was fucking another girl on the trip with us but when my friends snuck up on him to embarrass them by lighting them up with the flashlight, we all quickly realized he was actually fucking my girlfriend, not the other girl he brought on the trip.

For a young mind like mine at the time, watching his monster cock buried deep inside my young high school girlfriend’s pussy and their deer in headlights look, changed everything for me sexually that night. I was frozen as she in panic lifted her body off his mammoth rod and was the first time I had been speechless in my life. That experience is the core reason I started asking what my girlfriend’s secretly suppressed fantasies were early on. Perhaps so they wouldn’t feel the need to hide it from me and cheat on me.

The next night I asked to watch the video they made again and sure enough, I was correct, the guy had on the current Apple Watch Series 5 with the always-on display dimly lit. I looked at Shelby watching the screen with her mouth gaped in arousal as she masturbated next to me and I couldn’t believe how turned on I was that she actually cheated on me with her van-life, thug, ex-boyfriend. To be clear, I pushed her to see the video and she made what I wanted a reality.