Free Two Sides of Terri by Ben Boswell

God, Bill, that’s crazy. What? We’d stake out his office and follow him somewhere?”
    I hadn’t actually thought it through that clearly. But now that she’d said it, it seemed to make a lot of sense. I warmed to the idea quickly.
    “Sure? Why not? Aren’t you curious what he’s up to? Whether he’s married? Has kids? Is still a player?”
    “So, what? We’d follow him into a bar and just be all, like, wow Chucky is that you, long time no see ?”
    “Well, you would at least.”
    “Oh, not the two of us?”
    “Well, it just seems. I mean, you know, if I’m there, it’ll be all awkward.”
    She laughed. “Oh right, because it won’t be awkward otherwise.”
    “Well, less so at least. Just two old friends running into each other at random.”
    “And then what?”
    “I dunno. I really don’t. I mean, maybe you just say hi and go your own way, or maybe you have a drink and catch up.”
    “So, let me get this perfectly straight. You want me, your wife, the mother of your children, to follow her old…” She paused. “Her old fuck-buddy into a bar and have a drink with him while he chats her up?”
    “You wouldn’t be leading him on. And you wouldn’t need to do anything more.”
    She grinned. “I dunno. I told you, Chucky can be very persuasive. I always did have a hard time saying no to him. What if he invites me up to his place?”
    My heart was in my throat, but my cock was also throbbing almost painfully.
    “You wouldn’t need to go. It would just be something for us. Just a little game. He doesn’t need to know. You wouldn’t be leading him on.”
    “You’re crazy,” she replied. But all I noticed was that she hadn’t said no.

CHAPTER 6:
EXPECTATIONS
    It was a harebrained scheme, and yet all the pieces came together seamlessly. His downtown office was close to the “L” and Terri noted that he used to live in Wrigleyville, so we assumed he either walked or took the train to work. All we need to do was stakeout the main entrance of his office.
    We picked a Friday and arranged to have the kids spend the weekend with my folks. I picked up Terri early. She was dressed to impress, wearing that same clingy party dress from her birthday. If the plan to ambush Chucky failed, we agreed to go out to dinner instead.
    We set up shop at Starbucks across from his office. Starting a little before five, his building started to empty out, and I was sure we’d never spot him in the crowd. But after just a few minutes, Terri gasped.
    “Oh my God, there he is.” She pointed at a tall, slim, dark haired man exiting the building and heading north on La Salle.
    “I’ll call if he goes somewhere close by,” I replied, dashing off after him.
    It wasn’t a long chase. A block and a half away, he ducked into a bar with a large happy hour crowd. It was a trendy place. Lots of nice suits, girls who’d obviously “freshened up” before heading over. A meat market, but classy or at least expensive.
    I texted Terri with the bar’s name.
    Are you sure? she texted back. She was asking about the scheme, not the address.
    It’ll be fun , I replied.
    You’re crazy , she answered.
    Chucky was at the bar, part of a small group of well-dressed men and women. Obviously a regular crew. They were laughing and trading shots. He seemed to be the elder statesman of the group, but definitely one of the guys.
    I had managed to snag a small high top against the wall. I had a good view of the bar, although frequently interrupted as people crossed in front of me heading to and from the dining room.
    I waited anxiously for Terri. I was about to text her, asking if she was backing out, but when I looked up from my phone I saw her. She approached Chucky and gave him an exaggerated reaction.
    Oh my God, Chucky, is that you?
    Terri, baby, let me buy you a drink.
    I couldn’t hear their conversation, of course, but that was the body language.
    Chucky seemed to introduce her to his friends, but as I’d expected, dreaded,