Derek lived by himself in an apartment complex. He had a good job as a software engineer, and a decent amount of friends. But despite that, he had a shameful secret. Derek was a virgin. Derek considered himself an okay looking guy. He was fairly tall, at 5'11", but he had a baby face, glasses and was somewhat overweight. Despite being 29, his beard was still sparse, and patchy. Derek felt like it was filling in though, and that it made him look older, and his jaw more defined. Derek often wore hats, either baseball caps or fedoras due to male pattern baldness. It was mainly at the top of his head, and his hair was short and curly, so it wasn't noticeable unless he took his hat off.
In high school, Derek had been extremely awkward. The main reason he escaped bullying was because he was tall for his age, and also smart. His size either intimidated the bullies enough to leave him alone, or he was able to avoid situations that could have ended up making him look bad.
Derek did have one girlfriend when he was in senior year. She was a sophomore and a couple years younger than him. He wasn't that attracted to her, she was pretty average looking and didn't put a lot of effort into her looks. He now felt he pushed her to have sex too soon, which caused her to break up with him after just 2 months of dating. Derek hadn't had a relationship since.
In College, Derek was far too shy to approach any of the girls. And while he still lived and home, and didn't work, he didn't feel like any of the pretty girls at his college campus would be interested in him or what he had to offer. He decided to put off dating until he graduated and got a job. But by the time that happened, Derek realized it was harder to meet girls than he thought. At his job, all his coworkers were other guys, and what girls were in his group of friends, were the girlfriends or wives of his buddies.
Derek had also told his friends long ago that he had lost his virginity in high school. So he felt he really couldn't come clean with how clueless he really was about girls. He always avoided questions about his relationship in high school. Just saying it was "during his senior year".
Derek had tried getting dates online, where he was more comfortable talking with girls. But it seemed like every girl was into him until he actually asked them out, which was when they told him they just saw him as a friend. Some of them would even unfriend him.
This all frustrated Derek to the point of where he wanted to give up. But he would eventually get horny again, and want to give it a try. He even considered seeing a prostitute, but was too nervous. Somehow it seemed better to have sex the first time with a girlfriend than a stranger who might laugh at him. Derek was also ashamed to let a girl see him without a shirt on. His dick was an average size, but he had a large belly and pubic mound. If he ever did get to have sex, he was definitely not going to take his shirt off.
Derek started spending a lot of time in internet chatrooms with other guys in his situation. Because he couldn't really talk about his frustrations with his friends, reaching out to other guys like him became a comfort, and soon a large part of his free time.
At first, Derek was looking for advice on how to get a girlfriend, or at least loose his virginity. But it seemed like the other guys in the chat rooms didn't have any idea how to do that either. Or they insulted guys like him, and said it was "easy" or that he should just work out more.
That's when Derek started to notice some of the posts guys were making about tricking girls into having sex with them. One of the posts read:
"No...Seriously. Like, after I roofied her drink, she turned into a total slut! It's like she was coming after me. Never not get laid from a date again!"
Or another:
"I've been drugging my roommate for months now. She's a total whore, gets drunk, brings guys home all the time. She's never refused a drink I've made for her! I've fucked her pussy so many times while she's passed out. Slut is so loose she never even realizes it the next day!"
Derek thought these guys were taking it a little to the extreme. Like, did he really have to catch a slut with her guard down to get laid? Even so, Derek was curious, and decided to make a post asking where he could get some roofies. He figured you never know when you might get an opportunity.
...
It was several months after this, that new neighbors moved in across from him. They were two female roommates. One was average looking, a little overweight, thin brown hair. The other was definitely a 10. Tan, blonde, with a great rack, but also really sweet and innocent looking. She was total fapping material, and Derek stroked himself to completion more than once thinking about her, and fantasizing about getting his chance to fuck her.
Derek mainly kept to himself, but his new neighbors were really friendly. Especially the pretty one, which surprised Derek. He found out her name was Zoe, and she worked at a department store and owned a cat that she was always talking about. It wasn't long before they would great each other coming in and out of the building, or hold packages for each other. Derek was amazed at how easy it was for him to talk to this girl. He even wondered if this could be the girl who would finally get rid of his virginity, though he had no idea how he would accomplish this unless she made the first move. He decided that the best way to work towards this would be by being as friendly as possible and hope that as she got to know him, he might get an opportunity.
...
One day, while going back to his apartment, Derek saw a cellphone on the floor. From its position outside of Zoe's door, he assumed it must belong to one of the two girls. He instinctually bent down and grabbed it. He checked to see if it had a lock on it. Maybe if he could get into it he could see who it belonged to. It wasn't locked. It must be a fairly new phone. He tapped the photos icon. Immediately he saw multiple nude photos of Zoe taken in her bathroom and bedroom. He quickly locked the phone and slipped it into his jean's pocket, his heart racing. Looking around and seeing no one, he quickly went over to his door and fumbled with his keys to open it. Just as he got it open, he heard the door from across the hall open.
"Oh hey Derek!" Zoe exclaimed, seeming happy to see him.
"Ohh...Hey Zoe, what's up," Derek said, hoping his voice didn't sound as nervous as it was.
"I'm such an idiot, I can't find my brand new phone. I literally just got it last week. You haven't seen a phone anywhere have you? I was hoping I dropped it coming back up from grocery shopping."
Derek felt like it was too late to hand the phone back now. She would be suspicious that he had pocketed it instead of knocking to see if it were hers.
"N-no. I haven't seen anything," Derek stammered.
Zoe smiled sweetly at him, and Derek couldn't help but glance at her cleavage, wanting to see more of what he had seen briefly on the phone.
"Awhh man..well, if you do find anything, let me know!
"W-will do!" Derek gasped before fleeing into the safety of his apartment.
Immediately inside, he set the phone to airplane mode so that he could go through the photos without worrying if Zoe would try to call it. He felt his cock hardening in his jeans just thinking about seeing Zoe naked. He quickly brought up the photos again.
If Derek had thought Zoe's body hot before, these photos left no room for doubt. Not only was she hot, but definitely a slut. Everything was on display in these photos. Derek plugged the phone into his laptop's USB port and started downloading the photos.
Bringing up several of them on his desktop, he unzipped his jeans, and started stroking himself. He got himself a few pumps of lotion from the bottle next to his laptop, and massaged it into his cock. His breathing slowed and deepened, his cock growing and twitching as it rose. His hand adeptly working his erection as he stared, fixated on Zoe's plump ass, and her perfect round breasts. How he wanted to shove his cock into that little shaved pussy of hers. Derek imagined fucking Zoe, right there in his apartment.
As Derek started panting in ecstasy from arousal, he remembered the roofies. Suddenly, fucking this slut seemed within his grasp. He envisioned having his way with her hot body, and his cock thrusting in and out of her tight little cunt. He closed his eyes, leaned back and groaned as his hot semen shot up and landed on the back of his hand. His stomach heaved, as his cock spasmed sporadically, more milky fluid flowing out with each twitch.
Cumming seemed to make Derek even hungrier to fuck Zoe. And that's when he came up with a plan to make it happen in reality.
...
Derek remembered that Zoe liked wine. So the next day, being Saturday his day off, he picked up a bottle of a kind he remembered her mentioning before. Taking it back to his apartment, he then cleaned up and made the place look presentable.
As his preparations were completed, Derek started to get nervous. What if this wasn't going to work? What if it all fell through and she rejected him?
But the potential payoff was too good for him to give up now. He decided to go onto his usual forum for moral support. He posted the story of finding the cellphone, as well as his plan to fuck Zoe. He decided to post her nudes so the other guys could get some enjoyment from them as well.
The other guys were super supportive, and it gave Derek courage. One comment stood out from the others.
"Post a video fucking her or it didn't happen lol"
The idea of getting video of himself fucking Zoe aroused and intrigued him. He definitely wanted to be able to remember fucking such a hot slut. This was going to be fap material for a long time and he wanted to remember it. Also, the idea of bragging rights on the forum filled him with pride. What a way to lose your virginity! From virgin to stud in the time it takes to fuck a slut.
Derek set his plan in motion. First, he turned Zoe's phone off airplane mode, and then turned it off. He had allowed the battery to drain so that it would seem realistic that it had been missing all this time and not in his possession. He then put the phone in his bedroom at the far end of the apartment. Taking a big breath, he went out of his apartment, and went up to Zoe's door and knocked.
To Derek's dismay, it was Zoe's roommate, Becky who answered the door.
"Oh hey, Derek right? What do you want," She said flatly.
Derek was put off, but stayed on his feet, "Uh...Yeah, is Zoe there?"
"She's busy," Becky said with indifference.
"Um...Would it be possible for me to speak to her?"
Becky sighed and rolled her eyes, "She's in the shower, do you want to leave a message?"
"Yeah, let her know I think I found her phone..."
"You found her phone?" Becky looked at him skeptically, "Well do you have it?"
"Uh...It was dead when I found it, so it's charging at my place," He gestured back at his apartment.
"Well fine, let's go get it," Becky said as she started to walk out of her apartment.
