Note: This story has elements of cheating and cuckolding. I understand this does not fit everyone's tastes. Please review the tags and decide for yourself if you want to invest the time to read.
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I always thought Julie was a nerdy-looking girl. We first met when we were juniors in college; she would always hang around my extended friend group. Her hair was always somewhat matted and unkempt. She wore oversized baggy sweatshirts, and huge plastic glasses nearly covered her entire face. She looked like the stereotypical female STEM major you would see in those 90s/00s Mean Girls Esque movies, which she was.
As the academic year progressed, Julie moved closer into our friend group, and I would see her regularly. I always got the impression that she liked me, purely through her mannerisms and the way she would smile and play with her hair when talking to me. As vain as it is to say, I wanted nothing to do with her romantically. She was a cool girl but lightyears away from the type of woman I would date or hook up with. I tried my hardest not to lead her on in any way, as I didn't want to break her heart, though it was hard when her female friends would pester me with questions on my opinion of Julie. Eventually, she did get the hint, and our friendship stabilized, more or less.
After we all graduated, Julie would go on to pursue her master's at the same university, while the rest of our friend group stayed local to the area to some capacity, either working or going to graduate school. We all remained close friends after college and would hang out regularly.
One night out, Julie would introduce us to her new boyfriend, Matty. Matty was an economics graduate student at the university, and they had met in one of their overlapping classes. Matty was the perfect fit for Julie. He, too, was a stereotypical nerd in many ways: average height, skinny, loved D&D, bragged about data science, and had a passion for anime. I was happy for Julie.
Several months later, the group planned a Vegas trip for one of our friend's birthdays, and Julie asked if she could bring Matty, to which we immediately said yes. We all liked Matty. Even though he had the geek vibe, he was a cool dude who kept to himself and didn't cause trouble, and if he was cool enough for Julie, he was cool enough for us.
At that time, we were still in the college budget mindset, even though most of us were making a decent salary. As such, eight of us booked two adjoining rooms at the hotel, with two beds in each room. We weren't above bunking up with one another to save some cash. When we all arrived at the hotel, Julie and Matty took one bed, and the rest of us paired up. Two of the other girls in our group shared a bed in the other room while the rest of the guys doubled up. I shared a bed with my buddy Johnny next to Julie and Matty.
We had plans to go to one of the clubs later in the evening, so after dinner, we all went back to the rooms to get ready. The girls took one room to change in, while the guys took the other. As we were getting dressed, we joked around with Matty, asking him if he was excited to go clubbing. Unsurprisingly, this was his first time going to a "nightclub," and as such, we all ensured he looked sharp.
When Sarah and Liz (the other two female friends) came out, they looked beautiful and sexy, all dolled up, as they usually did when going out. When we asked where Julie was, they said she was a bit nervous and wanted her to get out of her comfort zone. Earlier in the day, the girls and Matty had stopped at one of the outlet stores on the way to get Julie some new threads. The girls made us promise to not laugh or say anything mean. We, of course, said we would do no such thing while giving each other the confused side eye, as we all knew Julie dressed down, so anything would be a significant improvement.
When Julie walked out of the room, all the guy's jaws dropped, literally, including my own.
"God damn, Julie," said Frank. We were all thinking the same thing.
It was almost surreal looking at this woman before us. When we saw Julie not two hours earlier, she looked the way she always did. Hair in a bun, a big sweatshirt, and glasses that would constantly fall off the bridge of her nose. The person standing before us was not Julie, so we thought.
Julie looked absolutely stunning. Her hair was down and curled, she had put on contact lenses, and she had on a tight black dress, showing ample cleavage and a nice firm butt. All the guys were bewildered.
"Now it makes sense why you always wear those big sweatshirts, Julie," Johnny said, nearly elated.
Julie's large perky breasts were practically spilling out of her dress as her face turned beet red.
"Come on, guys, you're embarrassing her!" Sarah shouted.
"Sorry, it's just such a transformation!" I chimed in. Julie perked up when I said this, and I saw a warm glowing smile on her face.
As we walked to the club, I still could not believe Julie had that much potential after all these years. I remembered all those times she was nervously trying to flirt with me and how I softly shot her down each time. I was nearly kicking myself with regret.
I stared in awe at her long, toned legs, thick ass, and perfect waist-to-hip ratio as she strode confidently in front of me. And then, there was Matty, walking alongside her, holding her hand.
All the guys were thinking the same thing, "Matty gets to sleep with HER?" This girl went from wearing mom jeans and a sweatshirt to a drop-dead gorgeous supermodel just by putting in a negligible amount of effort. I wondered if Julie purposely dressed down all these years or if she even knew how sexy she was underneath the STEM persona.
At that point, I made a decision: I was going to fuck Julie. Maybe not tonight, but it was undoubtedly going to happen soon. I'll admit that I was engulfed with jealousy, knowing Matty got to enjoy Julie in all her glory. Perhaps this was karma for turning her down all those times? Who knew?
Johnny bought us all the first round when we got to the club. We all chilled in one of the corners as we mentally prepped for our night out. After a few more drinks, we all moved towards the dance floor, where I saw Julie grinding on Matty as he awkwardly held her hips and did some derivation of a white boy dance.
When Matty left to use the men's room, I approached Julie, and we started dancing. Her moves had become more sensual throughout the night as I grabbed her hips, and we danced in perfect synchrony. As Matty came back, he saw us dancing and awkwardly stood around. I approached him and motioned for him to continue dancing with his girlfriend, but he said he needed to sit down as he felt he had drunk too much. The truth was, we were all pretty hammered that night. We had only bought a couple drinks each at the club. The rest of the heavy lifting was done through a combination of flasks and pouches filled with liquor hidden on our bodies. Remember, we still had the broke college student mentality.
I sat down with Matty and mustered up the courage to ask him how he landed a girl like Julie. He didn't seem to understand where I was going with the dialogue, so I asked bluntly about the intimate details of their relationship. We were both pretty drunk, and he did not seem to mind divulging the details.
It turns out Matty comes from a devoutly religious family and is saving himself for marriage. He and Julie haven't had sex yet. Hell, they barely managed to get to second base. When I asked him how Julie felt about that, he said that she understood and respected his decision, though she does try to pressure him from time to time to go further. I knew for a fact, however, that Julie certainly had sex before. Maybe not a lot, but at least a couple of times. I even remember cheering her on one night in college as she drunkenly took a guy she fancied from a party back to her apartment for the night. She told us all the intimate details the following day at brunch.
I continued to talk to Matty about various intimate behaviors and asked him if he watched porn. He initially shied away from answering, though he did admit he does indulge from time to time. We talked about porn genres and what he was into; it was all vanilla, as expected.
At this point, I asked if he ever came across cuckold or hot wife porn. He said he knew what it was but never saw the appeal. He admitted the craziest thing he watched was a stepsister, AKA "quasi" incest, film. See? Vanilla.
Here is where I may have manipulated poor Matty for a bit. See, I was fixated on Julie. I wanted her badly. All I could think about all night was ripping her tight black dress off and going to town on her, giving her everything she needed... and deserved.
