I pursed my lips, then slowly exhaled. This was heading into potentially dangerous territory. Jane was nineteen, so no dramas there. My marriage was at an interesting point, with Kirby and her new teaching degree working at a remote school in the middle of Western Australia. She had been home for a total of eight weeks over the last three years, and I was getting very frustrated on so many levels. Still, I was supposed to be Jane’s chaperon. I thought back to when I was her age. I was awkward around girls and dreamed of having one of the women wandering around the Uni campus take pity on me. Really, this was pretty much the same. My hesitation crumbled.
“Well,” I said carefully, “If it’s a request, I have to ask why? I mean, I’m twice your age. Surely you could find a good looking guy around your age who’d be happy to help if you want a bit of fun.”
She slumped down in the seat and chewed a nail. “I can’t ask anyone. I’m still a virgin.”
“Ah. I see.” I didn’t see. I wasn’t sure why that would stop her from getting a guy to do her. Being a nineteen year old virgin was probably unusual in our relatively small town, but hell, I didn’t get lucky until I was twenty-one. And that was a sympathy fuck. My confusion must have been obvious. Jane straightened up and rapidly tapped her knee.
“Ok yes, I’ve had offers but I don’t want to be just a tick in some dickhead’s box. And most of the guys I sort of know are dickheads. You don’t mind me swearing a bit?” she asked anxiously.
I laughed involuntarily. Jane was detailing why she wanted me to fuck her, and she was worried I might be offended by her language. “No, all good. You know what Jamie and Klint’s like on the court. I’m surprised the court hasn’t turned blue.”
That got a laugh out of her, which was good to see. “Yeah, they are a bit rough. I was horrified when I first heard them, but now – it’s just them trying to get under each other’s skin.”
“Pretty much. Well, I’m going to be blunt if we’re going to talk about sex. You don’t know anyone fuckworthy. So why me?”
She wedged herself against the door and turned towards me. “I want to lose it before I enlist. Going in a virgin would be embarrassing, and I don’t see it as a big deal. Insert rod into hole and BAM! Job’s done. And I like and trust you. You could do it and not post it on Insta. I don’t want to leave here known as the cheap town bike.”
I was starting to get drawn into her idea. “Well, thanks. I like you too. I think you might find the reality of sex is a bit different to what you think it is. From what I understand, the feeling of a real penis in your vagina is a lot different to using something else.”
“I’ve never used anything in there.”
That surprised me. “Nothing? Not even a finger? Or a tampon?” I blurted out and immediately regretted it.
“No, nothing. It’s a bit hard when there’s at least eight people living in our house, and two or three to a bedroom. No privacy at all. And I use pads. You think I’m weird.” Jane started to shrink again.
“Yeah nah, not at all. I guess it would be a bit tough.” I quickly replied. An idea was starting to form, something to try and drag a bit of confidence back out of Jane. We still had about a two hour drive ahead of us and stopping now for a quick fuck, no matter how tempting, just wasn’t going to happen. And I could sort of understand why Jane wanted me as her first. She just wanted to do it with someone who wouldn’t go around boasting about it until she left. Probably for good. “I guess you’ve never had any sort of orgasm then?”
“Not really. Well, maybe. I don’t know.”
“Ok. I think you need to figure out what you like before you let someone inside you. Look, you should enjoy sex. It shouldn’t be a chore, or a box ticking episode. Sometimes it can be ordinary, but mostly, it’s fun.”
“Ok,” Jane said slowly. “So you will… Fu… fuck me?”
I nodded, “Yes, yes I will. But there’s a couple of conditions. One, you need to jump back over into the rear and try and masturbate yourself to an orgasm. When we do it, I want you to guide me so you can hopefully come on my cock. It’s a big ask for your first time, but you never know. Sex is strange like that. Which leads to number two. I will only fuck you if you place in the top three. I know you can win, but if this is on your mind you won’t be focused on the game. So, no place, no sex. Deal?”
“Deal!” She launched herself over the centre console and hugged me. The car swerved violently as I momentarily lost the ability to steer. “Oops, sorry Andy. I won’t let you down. I’m going to win, and you’ll have to fuck me twice as hard.” Jane burst into a giggling fit. “That sounds so weird. I’ve never said that before.”
“Lucky there’s no one else crazy enough to be on the road this early on a Sunday. I guess today’s going to be full of first-time things for you.”
In another blur of arms and legs, Jane was over the back. “Is it ok to be naked while you drive?” she asked, her shirt halfway up her abdomen. A shocked look slowly moved across her face and she started to lower her shirt. “What do I do? I mean, I sort of know how but, you know…”
“You’re short on the details. No worries, I’m sure we can figure it out together.” That was another surprise, but I wasn’t going to ask about her masturbation history. “And I don’t think being naked in a car is illegal as long as you’re wearing your seatbelt.”
“Oh yeah.” She quickly clipped herself back in and sat up with her hands in her lap. I figured Jane now wanted me to instruct her.
“Ok, shirt off please.”
Jane licked her lips and smiled, and slowly removed the club shirt. She started to lift her crop top and I quickly said, “No. Wait. This needs to be sort of like a real make out session. Let me look at you while you run your fingers over your tummy and shoulders. Nothing else.”
She looked at me with a puzzled expression but did what I asked.
“Close your eyes. Just touch lightly, like someone is brushing you with a feather.” I adjusted the mirror so I could watch Jane and focus on staying on the road. She had filled out a bit over the years but was still thin. More athletic thin. I was pretty sure she would have been a great sprinter if she had decided on track and field.
“Take off your shoes and socks and put your feet on the centre console, please. Eyes closed.”
Jane nodded and pushed them off. A foot nudged me in the side and tickled as she wiggled her toes. I grasped it and gently squeezed. A barely audible sigh left her lips as I slid from toes to ankle, then back. They were quite callused, more than I expected and I had to press fairly hard on the ball to get a reaction. Her instep though – ticklish. One spot on her arch caused her to squirm and giggle. I eased away and started massaging each toe.
She was relaxing. I don’t think anyone outside her family had ever given her any serious physical contact. I somehow doubted Jane had got much from her family either. I may have had it wrong, but the very few times I had met either of her parents, it seemed like they felt their kids were an inconvenient outcome of sex. And her siblings were just ratty.