Playing Matchmaker

"James should have friends over more often. Guy friends of course. Well as long as you're here, why don't you come back inside and I'll heat something up for all of us."

"I'd love to Mrs. Alcott, but I already have plans." (guy friends only?)

"Please! It's Jill. You all aren't kids anymore."

"Thanks Jill. Maybe another night?"

"Just let me know when."

Driving away, I felt the situation was considerably clarified. Jill was clearly hot enough so that that aspect of it shouldn't be the barrier. The barrier was in James' head. For my plan to get James into his mother's bed to succeed, my job would have to be to loosen his inhibitions a whole lot more. Fortunately for me, I had a certain expertise with a great inhibition loosener called beer.

I wouldn't get my chance though for another week. I knew it was important to give James time, but I also felt it was important he get nudged on a regular schedule into taking the next step. The next Friday night, I got him back over to my place by telling him a friend had sold me a case of MGD and I had no one to share it with. We didn't talk "business" for the first few hours, I focused on getting James comfortable and improving his mood, which as usual was nervous and distracted. Eventually, we got bored of the Xbox and we went outside to my balcony to tackle the second half of the beer case.

"So," I started. "How's it going at home? You've been pretty quiet about that. Should I be... congratulating you yet?"

"You are just endlessly curious about me and mom, aren't you?"

"I won't deny I'm a little jealous of your good fortune." I raised my bottle in toast. "And I'll admit I enjoy living vicariously through your stories. Mostly though I'm just looking out for you."

"Thanks man." James clinked my bottle. "You've been the best advisor I could have wanted in this situation."

"So what can you tell me?"

"Nothing really happened this week - except, except in my head."

"What happened in your head?"

"Well it's like you said. If I keep forcing myself to consider my mom in that, you know, that way - eventually it starts becoming natural."

"I told you."

"And that's what happened. She's still mom. But now, when I look at her, I see her body,"

"Yep."

"I imagine what's under her clothes,"

"Uh huh."

"And I think about what I would do with that body. At first it was a struggle to look at her that way. Now it's like I can't help doing it even if I didn't want to."

"Exactly."

"And it goes without saying..."

"Yeah?"

James shifted around in his chair. "You know."

"What?"

"Well it's not easy to say. But, uh, let's just say mom is now making regular appearances in my head during those... special alone times."

"Jesus dude, you don't have to speak in code. Just say what you mean."

"You know what I mean."

"Well why can't you say it. Be proud of it. You jerk off to your mom."

"All right! Keep your voice down! We're outside."

"No one can hear us. And anyone in this apartment complex probably jerks off to their own mothers anyway, so who are they to judge?"

"All right, shhhh. Yes, whatever. I jerk off to my mom."

"And it isn't weird?"

"Yeah it was the first time. Then I don't know, I just got past that. Now it's just freaky and exciting. Intellectually it still basically freaks me out, but when I'm alone in my bed at night, I can just push all those rational thoughts aside and just enjoy it."

"I keep saying this, but, I told you!"

"Yeah yeah. So keep in mind, all this time, mom hasn't stopped giving me signals. And yesterday, she did something kind of bold."

"What did she do?"

"She asked me out on a date. Jill, - uh, mom, is taking me to a movie and dinner tomorrow. She says I've been moping around in my room too much and we need to get out of the house. In and of itself this would be a little unusual since before my dad passed the two of us would never have had an evening out like this. And then today she texted me to tell me to make sure I wear something nice for our date.

Notice that she never gave me a choice in the matter, she just told me we were going out. The movie by the way is a romantic comedy - I never got a choice in that either. So now it's really decision time. I can make an excuse and bail out of this - and I think that would really send her the message that I don't want her. Or we could have our date, which could be a "date" date", or just a fun outing."

"Wow." I smiled, "I thought your mom was pretty smart before, and now I'm certain of it. Look, this is definitely a "date" date. The fact that she told you a day in advance to dress nice for it and made the point of calling it a date removes any doubt there. But, to her credit, she is still giving you a way out. Yes, you could call it off. She can still pass it off as a regular movie night out with her son if she senses the mood is wrong. Jill is definitely moving things along here. First came the hints, now she's going to lead you by the hand. The only question is what you want to do about it. If I was a betting man though, I'd say your mom's going to get her way. Make sure you compliment her and buy the popcorn."

"Yeah, well I haven't decided if I'm going to go."

"What? You can't be serious! Of course you're going to go!

"This is a big step, Don. Fantasy is one thing, but I don't know if I'm ready for this."

"Do you realize how many guys would kill to be in your position? Your mom, your - pardon my saying - your hot mom, who's totally into you, is taking you out on a date and you haven't decided if you want to go??"

"It's not that easy!" James knocked back the rest of his MGD and then threw the bottle. "She's not your mom, she's mine."

"But this date will be like a guaranteed home run! The odds are 100% that you'll score!"

"Oh God. I can't deal with it."

"Of course you can. Just be a man."

"No."

"James, you're thinking about this the wrong way. I mean look, if this relationship with you and your mom has any chance of actually happening, then you need to know the real woman, and not just the mom you've always known. So a date might actually be just the right thing. It'll give you a chance to see her in a whole new light and overcome some of your fears."

"Shit." James was looking at his watch. "It's 11:50. Mom says she wants me home before midnight every night."

"Dude. Not that it's my business, but a woman who asks you out on dates can't also be the one giving you a curfew."

"Oh now we've found something that's not your business?" James got up and grabbed his sweatshirt. I got the definite sense that maybe I had pushed him a little too hard.

"Bud, just think about what I said, okay? You'll make the decision that's best for you and best for Jill."

"Whatever man. Thanks for the beers."

And that was that. I had done my best, and lord knows Jill Alcott was doing hers too. All I could do now was wait.

3

The next thing that happened was a series of text messages. I'll report them as I got them, word for word. The first one came at about three o'clock that morning:

"Fine. I'm going on the date."

The text woke me up and I tried to reply back with a cheering happy face emoticon, but groggy as I was I probably blew him a kiss by accident. That was it until 4:15 PM. I was in class, not one with James, when I got two vibrates from the Samsung:

"You better be around. I'm going to need a pep talk."

I wrote back: "I'm your wingman in spirit dude. You're gonna do great."

But I didn't get a call. 7:00 PM rolled around, and I knew that if the date hadn't started yet, then it was imminent. I had just walked through my front door when the next text arrived:

"She's primping in the bathroom. I'm so goddamn nervous."

Me: "Easy. Deep breaths. Compliment her. Tonight is about having fun. Repeat: FUN."

Him: "I know I know. I just can't believe it. I'm going on a date with my mom."

Me: "Yeah, there's a word for that. Lucky SOB."

Me again: "Well you know, not literally."

Him: "OK. Putting the phone away. Stay up. I'll call you later."

I figured at that point that the earlier I got that call, the worse the date would have gone. If I figured it right: two hours for the movie, another hour and a half for dinner, 30 minutes for walking and driving. That would have them home around eleven. So I figured the time of the call would tell the tale. It would break down as follows:

Call before 11 - the date had crashed and burned

Call between 11 and 12 - date went ok, but none or minimal fooling around back at the house

Call after 12 - date went great, James had gotten some nooky

I spent the evening web-surfing and watching TV, but I couldn't really concentrate. I was too excited. My little plan was on the verge of succeeding. I was actually on the cusp on hooking up my friend with his own mom! It all depended on James having some guts, and allowing nature to take its course.

Fortunately eight o'clock and nine o'clock rolled by with no call. Then it was ten. Then it was eleven. "Truth time." I thought. Then it was twelve. "Way to go Jimmy boy!" I gave a little fist pump to the empty room.

Then it was 12:30. Then 1:00 AM.

At 1:06 the phone hummed in my pocket.

"Dominos Pizza." I answered. "Can I take your order?"

"Hey." James said. "What's up man." There was obvious fatigue in his voice.

"Not much my friend. I knew you were going to call, but I didn't think it would be so late."

"Yeah, uh, sorry about the hour. Mom's asleep. I'm outside taking a walk."

"So tell me what happened? The last time I heard from you you were having a serious case of the butterflies. I hope you were able to get past that."

"Okay. Well, that was without a doubt the strangest "date" I've ever had. Here's what happened. I'll try not to leave anything out. First of all, I went totally casual. Jeans and just a simple button down shirt. But when mom came out of her bedroom I was in for a surprise. Mom went all out. She was stunning. Got her hair did. Wore makeup for the first time I can remember. And a tight black dress that looked like she was going dancing. It may have been new. I told her that she looked extremely good, and she thanked me and asked me if I was ready for our date. I said I was, and then she took me by the hand as we walked to her car.

Dinner was first. She picked a restaurant called Kona. Kind of pricey but she ended up paying for it, even though I offered. On the drive there we mostly talked about how I was doing in school. The only thing I'll mention about the ride there was that her dress rode up giving me a lot of thigh to look at. Intentional? Who knows. Once we were at Kona, we walked inside arm in arm. The reservation was in her name, and mom requested a booth. It was one of those curved ones and mom didn't lose any time sitting right next to me.

Part of me was completed relaxed, since after all I'd been out to eat with my mom hundreds of times. But then there was another part of me that felt like she was the predator and I was the prey. The conversation moved more to our situation - that she was proud of me for keeping us together and so close since we lost Dad. She said that she was ready to move on and not be such a recluse. I told her that she used to be the alpha mom, and that she'd be happier when she was back to a full social calendar in her free time. She said she knew that was true.

That's when I got direct. I knew we would have to talk about her love life. I said something along the lines of: 'Mom, in order to be happy, you're going to need to find a new man.'

'Oh I'm already working on that.' she replied.

I took a big swallow of Sprite. 'Yeah? Great. Do you, um, have someone in mind?'

'Oh yes. I've picked a guy already. He's not sure yet if he wants to be with me. But my mind's made up. The poor guy doesn't know what's coming to him.'

'That's the truth! I'd hate to be anyone who tries to get in your way when your mind's made up.'

'Exactly. When I set my mind to something I always get my way. Know what you're having for dinner?'

That's about as far as we got on that subject. I won't bore you with all the details of the meal, except just one. After our plates had been cleared, three ladies who I didn't know were entering the restaurant and they walked by our table. They recognized mom and stopped to chat. Turned out they were army wives too. They asked mom how she was getting along and mentioned how their husbands all missed my dad. Finally, one of said 'So Jill, aren't you going to introduce your friend?' My mom turned to me and said 'Gosh where are my manners? Ladies this is Jim. He's a student at the college.'

Not "my son Jim". Just Jim. Just a local college student.

'Nice to meet you Jim' I shook a round of hands. Then one of them quipped: 'My my Jill, he is a handsome thing.'

'Now come on', mom smiled back. 'Don't embarrass me Gina.'

'Oh I'll embarrass you all I want. Jim, you may not know this, but you hit the jackpot with Jill here.'

I tried to speak 'I...'

'Of course you must have some decent qualities yourself if Jill let you take her out. You two have fun tonight. But not too much fun...'

'Goodnight ladies!' - my mom shooed them away, still giggling.

'Mom!' I whispered as they moved out of earshot. 'You're just going to let them think I'm some guy you picked up at the college?'

'Oh who cares if we want to mess with their heads a little! Besides, you are my date for the night, so you may as well act the part. You could try being a gentleman. And a little romantic.'

As we left the restaurant, my confidence was once again shaken. The conflict came back into my brain. On the one hand it was mom. It was definitely mom. But on the other hand, I had my eyes on her ass as I followed her out the door. Once again I was checking her out. And worst of all, Jim Jr. decided to make an appearance, his first of the night, and threatened to tent out my jeans. I got in the car just in time so mom wouldn't notice. I wasn't in much of a talking mood on the way to the movie theater, even though mom kept up the chatter, and encouraged me to lighten up and not spoil the mood.

I remembered your advice about buying the popcorn. In the end she didn't want any. But she told me I was sweet for offering. The movie was two hours of a boring rom-com with Sandra Bullock, where my mother snuggled up against me any spent the whole time with her arm around me. It didn't feel like motherly affection. At the point in the movie where Sandra finally kisses the guy, mom made her move. With one arm still holding me close, she reached over with her outside hand and began stroking my thigh. She kept it up, gradually moving to my inner thigh, and then once or twice brushing the back of her fingers against my package, which as you might imagine was at full attention. There was no confusion about intention here. No subtlety. My mom had told me in the restaurant that she had picked a new guy and that her mind was made up about it. And my mom's mind is not easily changed once made up. And now here we were just two hours later and she was expertly letting me know exactly who that guy was.

As far as I was concerned the movie was a mile away. Mom - my own mom - Jill the soccer mom, army wife extraordinaire had decided that dad's replacement was me. She was claiming me, making her intention clear. Whatever hang-ups I have about incest, it was totally clear that she did not have them. I have no idea what kind of libido my mom has, I'd never even thought about it - but there in the movie theater, with mom making a pass at me and attempting to cop a feel - I suddenly got the impression that it would be raging and insatiable. My own mom. I couldn't deal with it. My cock, unfortunately, was fully on board for this new adventure, and mom could see it. She smiled and said 'Don't you just love happy endings?'

I couldn't even speak if I knew what to say. I did nothing to remove my mom's exploring hand. You need to understand Don, you might think this is great news, but my mind was reeling. The part of me that's not thinking straight was saying go for it, but the part that was still logical was screaming for me to fight back as hard as I could.

The final shock and embarrassment was waiting for me in the lobby. Two of my friends - you may know them - Alex Meyer and Ben whats-his-face - they bumped into us as we walked out. They were with dates. Now, me and mom holding hands like we were and coming out of the romantic picture, it's not like there was even a chance I could tell the truth.

We laughed about how unrealistic the plot was, although anyone looking closely would have noticed I was too shell shocked to really see the ha-ha in it. Then we made the introductions. I have no recollection what the girls' names were. But I remember what I said.

'Alex, Ben. This is... Jill. My friend. She's a, uh, telemarketer.'

Mom made up for my missing enthusiasm. 'Hey guys! The pleasure's all mine.'

'Likewise. Likewise.' said Alex. "James, isn't your mother a telemarketer?'

'Well, um.'

'That's kind of how we met.' said mom.

'Ohhhh. Gotcha.'

As the ladies walked on Alex pulled me aside. 'Dude! Way to go!' I started to stammer something but the words wouldn't come. Alex continued: 'The most Ben and I could hope for is to take out some juniors. You've got game, son! That is one fine piece of ass. I will definitely spread the good word!'

'No no!' I interjected. 'That really isn't necessary.'

'Don't be so modest! You're going to be a hero on campus. But I won't keep you. Based on how Jill was looking at you I don't think you'll have any problems closing the deal tonight. Good luck man.'

If it was possible for the knot in my stomach to get any tighter, it did. My classmate had called my mom a fine piece - right in front of me - then said he thought I'd have no trouble getting busy with her. Busy with my own mother. My god. First my mom's friends and now my own were saying they were envious. My mom was planning to take me home and take me to bed, and my own friends were congratulating me. How could I tell them the truth? What would they say if they knew?"

"Well obviously, you don't tell them" I offered. "To them, she's just Jill. Remember that."

"I know, I know."

"So then what happened."

"So we drove home. Mostly in silence. I knew there was no more delaying it. The time had come. Mom was going to make another move, and this time we'd be alone. She pulled her Jetta into our driveway, and we parked. Mom didn't turn off the engine. So we sat there. I felt I should say something, but I was at a loss for words. Mom took me by the hand and gave me a squeeze. 'You know,' she said, 'I may be rusty, but it's usually customary for the guy to tell his date he had a nice time.'

'Oh, yeah, I mean... I had a very nice time'.

'I did too,'

'And,' I forced myself to speak, 'And you really made an impression on my friends. They thought I was lucky to be on a date with you,'

'Really. Do you think you're lucky to be on a date with me?'

'I, yeah. I do. I am lucky.'

There was a little bit of a pregnant pause there, and then mom spoke up again. 'You know, it's also customary for the gentleman to give his date a kiss at the end of the evening.'

I felt, I knew, that at that moment, this was the point where there was no going back. To let her take me out on a date, and to act flirty, that was one thing, but to kiss her in a parked car - that was crossing a major line. After that, I would always be a guy who had kissed with his mother. There was no undoing that. But I also knew at this point, going backward was going to be more awkward for me than going forward - so that made it easier."