Chapter 1

“Why have you never had a girlfriend?”

The question left me dumbstruck, and more than a little ashamed. Sure I wanted to find a girl. At 16, my hormones were screaming at me. But it wasn’t just sex; I would stay up at night imagining the little moments I’ve never had. Dreaming of my girl, standing behind me, arms around my waist and pulling me close. Most days, I couldn’t get the girls at school to look at me though, much less embrace me.

“You’ve been lecturing me about the perils of girls and sex for as long as I can remember.”

It was a dodge, but it was still true. She had me at 15. She never told me directly that I’d ruined her life, and I had no doubt she loved me, but the number of warnings, rants and lectures I got from her about how sex could ruin my life made her position clear. She struggled as a single mom, but I think did a good job. I never saw her with a man, but she clearly enjoyed sex when she was my age. I always wondered if my surprise appearance led her to hate men, fear sex, or something else -- adults are hard to figure out.

“I know, I know. But I have been thinking, and talking to my friends...”

This couldn’t be good.

“You’re a man now, and you have needs...”

I scanned the room for a table to hide under. This was painful.

“And no matter how much I lecture, and watch, monitor your emails and check your drawers...”

Wait, what??

“I have come to accept that it’s going to happen anyway.”

If only I believed that.

“I mean, I know how I was at your age, and I was a girl. And not that you appear to really have anything going on in your emails, you’re social life is actually kind of ... well, anyways, I need to accept it’s going to happen.”

“If you can’t manage to attract a girl, eventually you’ll find another way. Find some prostitute on the internet and then you could wind up with a baby and the clap.”

This living room really needs a large table. I can’t push myself deeper into the couch cushions. And what the hell is the clap.

“Listen, mom...”

“No, I know you’d never tell me. But I see those sites you go on sweetheart. Don’t look at me like that, I pay the bills”

“But one day soon you’re just going to pop.” She paused for a moment and giggled at her own pun. “And then it’ll be too late. So I’ve decided to do something about it.”

“Uhhh ... what do you mean?”

This was the most bizarre conversation we’d ever had, and that is saying a lot. I was completely lost. She knows I need to get laid so bad it hurts. And that I have no real prospects or shot. But she’s going to do something ... to prevent it ... or help ... I was just lost.

“I’ve found you a girl, silly.”

“But what about what you just said? You found me a girl to um, and ... huh?? And this is dumb. I don’t need you to fix me up - you make me sound pathetic”

I was pathetic.

“Well sweetie, some people just take longer to learn. But you just wait, she is very special. And she is going to solve both of our problems. I realized I’ve put my life on hold, because for your whole life ... well after the diapers and wiping your cute little bottom...”

“Mom!”

“hmm? Oh don’t be bashful. I’m saying I’ve spent your life waiting for you to make the same mistake I did. And I don’t want to waste any more time on it.”

“On me?”

“Oh, toughen up, quit being a baby. You know what I mean. I mean, if I knew how you’d turn out, I probably wouldn’t have worried so much...” she trailed off.

That one hurt more than usual. She took me from uncomfortable, to ashamed, to mortified, to wounded in record time. She was a pro at softening me up.

“But no. I’m doing the right thing. I’ve found you the perfect girl. Elaine’s niece. She’s wonderful, but she’s had her own trouble dating. That’s ok though, we’ve worked it out. She’ll take care of your needs and all of my worries at the same time. And I can finally think about my own needs again...”

My head was spinning. Not least from the way she emphasized her needs. She already ‘worked out’ my relationship? This was crazy. My relationship ... could that really be possible?

“Mom, really, I’m not, I don’t want to meet her”

I was a charity case, but I had to pretend to put up a fight at least.

“Don’t be silly, she’ll be here in an hour. Clean that room of yours, and wear something cute.”

Cute. There was no arguing with her, though despite the nervous feeling in my gut I didn’t want to anyway. I headed to my room, which was just off the kitchen.

“Oh, and don’t forget fresh sheets!”

Rachael arrived 45 minutes later. I was still in the shower, and when I came down her and mom were giggling like old friends. She was stunning though. My excitement had been building -- just the idea of a girl who would want to spend time with me -- but as soon as I saw her it cratered. She was so far out of my league ... I mean I didn’t even know how to swing a bat.

“Oh, Ms. S - he is too cute.”

I was speechless.

“Why don’t you two get to know each other, I am going to just clean up around the house”

Rachael was giving me the most incredible smile I’d ever seen. Like I was in on something. With her. I didn’t even have space to process the weirdness of my previously abstinence-obsessed mother shuffling us off to my room, with the fresh sheets.

She shut the door behind us a pulled me into a kiss before I could even think. “We’re going to have fun.” She sounded as if I needed convincing. I smiled and went in for more.

After a few minutes or maybe hours, I grew bold enough to ask.

“Can we lie on the bed like this a minute? Here, yes you behind me like that, and pull me closer”

“Wow!” she said “I didn’t think you’d be anywhere near ready today. Your mom will be thrilled!!”

My confusion returned. And then as she pulled me closer - like I asked - like I had dreamed - my confusion spiraled. There was something firm poking from her waist. It nestled just in the small of my bottom. I froze.

“You’re going to love this. I promise. Eventually. I told your mom it’d be easy, but even I didn’t think I’d get inside you this quick.”