Mike was 18, but relatively inexperienced in life. He was shy and socially awkward, and had seemed to pass through his high school years unnoticed by most of his classmates. When he graduated, he wasn't invited to any parties being thrown by his former classmates, nor did he even really hear from most of them. With a full summer ahead of him before he was to depart for college, he really had nothing to do and no one to do it with. So his mother decided that she would send him to stay with her sister, his Aunt Veronica, in hopes that he might have a bit of fun passing the time with her and her daughter, Mike's cousin Samantha.
It had been a couple of years since he had seen them, and when he arrived they both remarked that he had grown a lot in that time. For his part, he couldn't help but notice how stunningly beautiful they both were. Aunt Veronica, at 45 years old, was a tall and slender woman whose red hair cascaded down over her shoulders. Her breasts were enormous, and Mike felt a twinge in his groin as she embraced him in a close hug and they pressed up against his chest. Like most guys, he was very much attracted to breasts. Unfortunately for him, he had never had a girlfriend before so he'd never had a chance to touch any. The internet existed, of course, so if he ever felt like looking at some then it was not hard to do so. But he had never actually seen a pair, uncovered, in person.
His cousin Samantha, three years older than Mike and home for the summer before her last year of college, was a bit shorter than Aunt Veronica, but had an equally appealing figure. She was blonde, and though her boobs were not quite as large as her mother's, they were still large enough to be noticeable. Mike felt the same twinge when she hugged him, and he inwardly chastised himself. Was he so starved for female attention that just getting friendly hugs from his aunt and his cousin set him on edge?
Mike quickly settled in. He would be crashing in the basement, which was spacious and comfy with a pullout couch. He was also very much looking forward to spending some time out by the pool in the backyard, which wasn't too large but looked very inviting. Simply leaving the house and going into the backyard, one would find oneself on a patio that had several chairs--some normal, some the longer kind of pool chair that you could lay down on--set up around a table. There was even a TV set up.
The trio spent the next few days enjoying hanging out and lazing around the house and the pool. Any time Mike saw his aunt or cousin in their bikinis, with their boobs practically spilling out of them, he couldn't help but get hard. If he was in the pool itself he would wait until his erection went down before getting out, but it wasn't always quick to do that, especially since he couldn't bring himself not to look at them. If he was up on the patio, he just had to try to position himself so that they wouldn't see the effect they had on him. He really hoped neither of them had noticed.
On the third evening, they were having dinner together on the patio when Aunt Veronica began asking him about his dating life.
"So, Mike," she began, smiling sweetly at him. "I'm sure you've practically had to fight the girls off back home."
"Uh...well, not really," Mike said with a nervous laugh.
"What? You don't have a girlfriend?" she asked, surprised.
"No."
"I'm shocked. As cute as you've grown up to be, I would have thought they'd be flinging themselves at you."
Mike blushed a little, and just shook his head.
"Have you ever had a girlfriend before?" Samantha asked.
"Um...no," Mike said, a little embarrassed.
"Ever been on a date?"
"No..."
"Ever kissed a girl?" she asked, arching an eyebrow in interest.
Mike shook his head, blushing a bit more.
"So you're still a virgin?" Samantha pressed, smiling a little.
Mike's embarrassment grew exponentially at that last question. He was indeed a virgin, but didn't want to have to admit it out loud.
"Now, now, Samantha," Aunt Veronica said, coming to Mike's rescue. "We shouldn't be getting too far into Mike's love life." She turned back to him. "Tell us though, Mike, aren't there any girls from school you want to go out with?"
"Well...I mean, yeah, I guess there was this one girl..." Mike stammered.
"What is her name?"
"Evelyn."
"Evelyn. That's a pretty name. And why haven't you asked her out?"
"I guess I'm just shy," he said. He chose not to add that he had only even mustered the courage to talk to her once, and he wasn't even sure if she remembered him.
"Is this her?" Samantha asked, holding her phone up for Mike to see. Sure enough, with the power of social media, Samantha had found Evelyn by using her connection to Mike to look through his other connections and people who came up as recommendations to connect to.
"Uh, yeah, that's her," Mike said, blushing once again.
Aunt Veronica and Samantha looked through Evelyn's photos for a while. Mike supposed they were just curious. Every now and then, Samantha would glance up at him and look him over, as though she were analyzing him. If their eyes met, she would smirk. It was a sexy smirk, and Mike felt a familiar twinge run through him. He shifted in his chair, and tried to think about anything else.
The next day, Aunt Veronica received a request from her job to go on a work-related trip for a few days. It was unfortunate to see her go, but Mike wasn't too upset because it wasn't likely to impact his busy schedule of lounging around and doing nothing. At least, that's what he thought.
That evening after he and Samantha had eaten, she brought up the conversation from last night.
"Mike, you didn't answer my question last night," she said.
"Which question?" he asked, although he knew very well what she was talking about.
"I asked if you're still a virgin," she said, that seductive smirk back on her face.
"Oh...yeah," Mike said.
"Well?"
"Well what?"
"Are you a virgin or not?"
"Samantha, I really don't want to talk about this," he said, exasperated.
"Come on, you can tell your cousin," she teased, giving him a big hug. He felt her boobs press into him. "Besides, it sounds like you need help if you're ever going to ask that girl out. Don't you think I can help?"
"I mean...maybe? I don't know."
"Of course I can," she said matter-of-factly. She kept looking him up and down, like she had last night. Mike wasn't sure what it was, but there was something in that look that made him feel...exposed? It was hard to say.
"But Mike, if you want my help, then you're going to have to do what I say. Okay?"
"Like what, answer your intrusive questions?" he asked, trying to avoid revealing how uncomfortable he was in that moment.
"Not just that. You have to follow my instructions. Even if I tell you to do something that seems weird, you have to trust that I know best and go along with it."
"That's crazy. Why would I agree to that?"
"Because I'm going to help you get over being shy. So you have to promise. Okay?"
"I mean...yeah, fine, whatever," he replied. It seemed like the quickest way to just get to the end of this conversation.
"Excellent!" she said happily. "So, back to the question. Mike, are you a virgin?"
Feeling that he had allowed himself to be backed into a corner, Mike shrugged and nodded his head.
"There, that wasn't so hard, was it?" Samantha said with a smile. "Do you want to stay a virgin, or do you want to actually have sex at some point?"
"What kind of question is that? Of course I do," Mike retorted. "But it's not so easy for someone like me. Most people don't even notice me."
"Well, we're just going to have to work on that. We have to get rid of your inhibitions, so that you'll feel more comfortable around girls and less self-conscious. With my help, you'll be having sex in no time!"
Mike couldn't help but picture her naked. He tried to chase the image out of his mind as soon as it got there, but couldn't quite do it.
"So the first thing we're going to do is spend a bit of time together doing something out by the pool," Samantha continued. "We need to work on you being at ease with me, so we're both going to change first."