"Over three hundred??" Bill asked his fiancée Cindy again in disbelief as they sat at the kitchen table. "How did you even have time to have sex with that many guys?"
"There were a few women," Cindy noted, "You asked, and I didn't want to lie. I had a bit of fun in my early twenties."
She has a point, Bill thought. I did open this can of worms. He knew Cindy was sexually experienced but did not expect to hear a number on this scale. He had thought his own number of thirty-two was fairly robust before now. But Cindy was a knockout, and would have certainly had no shortage of suitors. And clearly she had taken advantage of the attention.
"And you can't fix an exact number?" Bill asked, hand on forehead.
"Honest answer is no." Cindy explained. "There were some group and gang bang situations and I really wasn't counting." She put a hand on Bill's shoulder.
"Gang bangs... of course." Bill looked at her. "You were into that?"
"Not really. It was kind of a bucket list thing. They actually get a little boring," Cindy said.
Bill was conflicted. He and Cindy got engaged about six months ago, and were sharing an apartment. The wedding was in two months. Both were thirty-one, and this was the first engagement for both. He had met her through work, she moved to town two years ago and hadn't know many people. Bill had been pleasantly surprised when she invited him to her place on the second date - though he now wondered why it hadn't been the first date. She was very physically flirty with him from the start and had a great dry sense of humor. She was the whole package. Smart, check; funny, check; beautiful, big check.
She was the perfect woman. The sex had been phenomenal. She was uninhibited from the start, open to everything. And a world class dirty talker, which he particularly enjoyed. Now Bill had some perspective as to how these skills were acquired. He was distraught as the images played in his head. But he had to admit to himself he felt a twinge in his pants when Cindy mentioned a gangbang.
"Bill, honey, the things I did before I met you have nothing to do with our relationship." Cindy said.
Ahhh, the old axioms, Bill thought. "The past is the past", and "all those experiences made her the person you love today." It did make perfect sense logically, but did very little to remove the feeling from the pit of his stomach. Over three hundred! Could he ever look at her the same way again?
"This is just a lot to process. And it's leading me to so many more questions," Bill said.
"Well then ask away, I won't hold anything back," Cindy said with a smile, putting a hand on Bill's knee.
That's what I'm afraid of, Bill thought. "Did you have any serious boyfriends?" He asked.
"Four since high school. Assuming longer than six months counts as serious." Cindy said.
"Did you cheat on any of them?"
Cindy paused a second, "On three of the four. I was much more unsettled then. We're getting married; this is a whole different situation. I love you."
"I...love you too," Bill said, seeing in Cindy's face that she caught the hesitation in his voice. His head was buzzing; picturing men piling onto his bride to be made his stomach drop. On the other hand, she was an absolute catch by any measure.
"Ok," Bill said after a minute. "How about this? We'll table this discussion for now, and if I have any questions later I'll ask you."
"Sounds good," Cindy got up and gave Bill a kiss. "And I'll never lie to you."
Bill had some thinking to do. Cindy had been wonderful from the start; he really had no issue with her. Surely her sexual past couldn't derail their relationship. But his imagination was getting the better of him. With that many guys she must have done everything at least once; anal, bondage, fetishes...he couldn't stop picturing Cindy performing every possible sex act with random men. He needed another perspective on this, but whom could he possibly ask? He decided he would call Troy, his closest friend since childhood. Troy knew Cindy; they had double dated many times with Troy and his girlfriend Vicki. And Bill trusted Troy with his life; he knew he could keep a secret and wouldn't bullshit him.
"Wow," Troy said as Bill finished recapping his earlier conversation with Cindy. The two sat at a neighborhood bar that they liked because it served a great burger. "Well on the plus side, certainly sounds like she's being honest. But man, that number is tough to shake off."
"And that's my dilemma," Bill said, "She's perfect in every way, but I can't get the images out of my head."
Troy thought for a moment, "Well look at it this way. You didn't think she was a virgin from the start correct?" Bill nodded and Troy continued, "So whether it was a couple of guys or a couple hundred, you'd have those same images."
"Maybe it's more imagining her mindset in getting with that many guys. I know this makes me sound like a pussy, but how can feel like I'm special to her, or the One? She obviously hasn't been very discriminating," Bill said.
Troy thought for a moment, "Here's my take on everybody having The One, or a soul mate, or whatever; that's all bullshit. Think about it for a minute. There are what, roughly seven billion people in the world. Now chop that in half, you have three point five billion males she could choose from. Further, let's say only ten percent of those are in the appropriate age range for Cindy and aren't complete fuck ups or felons. That gives her a potential base of three hundred and fifty million possible guys. You only met her through random chance; she took a job at your company. If they didn't hire her, you would have a different life, probably banging a different woman and she would be with some other guy."
"So what is your point, other that explaining the randomness of human existence?" Bill asked, chuckling.
"I was getting to that," Troy said. "Guys are possessive of women by nature. Probably goes back to caveman days. You'd like to think the girl you're with has been waiting for you, and that any previous sexual experiences she had were with unfulfilling, tiny dicked losers that she had to sift through before she found her knight in shining armor." Troy took a drink and continued. "But in reality, as my 'back of the napkin' math shows, she has hundreds of millions of possibilities. So whether it was a couple of guys..."
"Or three hundred," Bill interrupted.
"...Or three hundred," Troy gave a wave of his hand, "The truth is, there are plenty of men in this world she can go out with, have sex with, and enjoy it. And women do. I don't like to think about it, but I'm sure Vicki has grabbed a past boyfriend, yanked down his pants and blown him in a parking lot. Because she pulled that move with me pretty early on, and I'm not arrogant enough to think I'm the only guy that's ever gotten her that horny. Cindy just took more full advantage of this than most women do."
"Vicki in the parking lot, wow," Bill said.
"Keep my girlfriend out of your spank bank, you dirty bastard," Troy laughed.
On the drive home, Bill felt a little better thinking about Troy's analysis. But the images still ran rampant through his head. He was afraid his imagination was worse than reality and would just continue to eat at him, corroding their relationship slowly over time. But he had an idea.
Bill got home and asked Cindy to join him in the living room. They sat together on the couch. He looked down at Cindy's perfectly toned thighs in her short dress as she sat next to him, "Tell me about the cheating on your boyfriends," he said.
"Like a particular instance, or..." Cindy said.
"Tell me the most sordid one. The one you are most ashamed of," Bill clarified, "Every detail."
Cindy took a deep breath and thought for a moment. "Ok, I was twenty five," She began. "I had been living with my boyfriend Peter for about five months. Our sex life was fine; he was a good guy. We went to a party one weekend. It was at a big house a bunch of people shared, we got invited through mutual friends. There was a guy there I didn't know at all and I kept catching him looking at me from across the room. For some reason, he didn't seem creepy. Probably helped that he was very good looking." Cindy put a hand on Bill's leg and paused, uncertain about continuing.
"So what happened," Bill asked.
"Peter was off mingling and I was talking to a couple of girlfriends, but watching this guy out of the corner of my eye," Cindy said. "I decided to tease him a bit just for fun. I ran my tongue a little over the rim of my glass before taking a drink. I scratched at my leg, lifting up my skirt a bit. Little things like that."
"And he kept watching you?" Bill asked.
"Yes, even more intensely. I wanted to test him, so I excused myself and stepped outside. It was night and there was a large patio in back of the house with a couple of outdoor lamps. Most guests were in the house, but there were a few people outside. I stood out at the edge of the patio and waited to see if he followed."
Bill didn't speak but raised his eyebrows in a question.
"He followed," Cindy continued. "At this point there was no avoiding eye contact. We stared at each other for a moment and I stepped out into the yard. The patio had a line of thick shrubs to one side coming out from the house. I stepped around those and walked up close to the house. From here, there were people on the patio only a short distance away, but I was blocked from their view by the shrubs. I didn't see mystery guy right away, so I turned to look in a small back window. I could see the main living room and could see Peter chatting with friends. It was well lit inside so the only way I could be seen was if someone stared out inches from the glass."
"So you're standing in the dark, peeking back in on the party you just stepped out of?" Bill asked, "And then?"
Cindy steeled herself. "So as I was looking in the window, he came up behind me. His footsteps made no sound in the grass, especially not over the chatter and soft music coming from the patio. I first knew he was there when I felt his hands on my hips."
"And this was the mystery man?" Bill asked.
"That's the thing. It had to be him but I'll never know for sure," Cindy went on. "I froze when his hands grabbed my hips. He leaned in and I could feel his breath in my ear. He whispered, 'Just say no and I'll walk away.'"
Bill shifted in his seat, and Cindy went on, "Then he grabbed a fistful of my hair with hand and ran the other up the inside of my thigh under my skirt. I said nothing as his fingers probed me over my panties. He tightened his grip on my hair pulling my head back slightly, but I still couldn't see him. He asked me, 'Do you want it?' At this point I was quivering and could only nod a quick yes. I'm not proud of it, but in that moment I just wanted him to fuck me. He took his hand from my hair and hiked my skirt up over my waist, pulling my panties to one side. You want all the details, right?"
