Two stations passed in silence. We were past the city center and moving towards the suburbs. The train was emptying. Another station passed, and there were only three other people in the car.
“Look at this,” Megan said, reaching over with her phone to hold it in front of me. Probably leaning closer than she needed to, her hand only a couple inches from my still partially-erect member.
I looked at the email on her phone’s screen and commented on a couple of points. As I talked, she lowered her hand until it was literally resting on my cock. The erection I had managed to lose was coming back full force.
I finished the point I was making and she nodded. She moved her hand back out of the danger zone, but not before pressing it against my cock one more time. As she moved her hand away, she slid it along the shaft under my slacks. Once, twice, three times. I almost came.
The rest of the ride passed in silence, and by the time we reached our station, I had managed to lose most of my hard on.
“I’ll be online as soon as I get home,” I said, looking at the traffic app on my phone as I walked my boss to her car. “But it may take a while.”
“Take your time, no rush,” she said, reaching for her car door. “I’m sure I’ll see you on camera at some point today….”
I nodded and was turning to go, when she added “…in your underwear. Can’t wait for the subway ride Friday.”
She winked as she climbed into her car and sped away.
PART II
It took me over an hour to get home. It gave me time to process everything that had just happened.
Sex between a direct report and a manager is out of line. If I didn’t put a stop to Megan, I would be out of line. Plus Megan was a friend of my sister, who got me the job. My sister would kill me. In fact, if she found out, she would probably kill us both.
But on the other hand, if she wasn’t my boss, I would be all over this.
It made my head spin.
I finally made it home and got to work. The rest of the morning (what little was left of it) was spent digging through emails, and the first part of the afternoon I was tied up in meetings – meetings that didn’t include Megan, my boss, thankfully.
Around 3:00 I had made my last cup of coffee of the day and was preparing for the final push to wrap up a couple things, close out some emails, and log off. No more meetings, just work. I put on some music, took my coffee cup into the office and got to to work.
It was summer, and since I was through with meetings for the day, I tossed off the work shirt and the T-shirt underneath and ducked into the bedroom to switch out the slacks for a pair of shorts. Better.
I started digging through my aching inbox. I was on the third or fourth reply when a window popped up on the screen.
Bligh, Megan: Hi Bryce, got a sec? We need to modify our deck for Friday again.
I sighed.
You: Sure. What do you need?
Bligh, Megan: Can I call?
I sighed again. A chat with my horny boss wasn’t on my agenda for the afternoon but what choice did I have.
You: No problem.
My computer immediately lit up with an incoming video call. Video, not what I wanted. I pulled on my work shirt that was still sitting on a nearby chair just in case.
Megan’s face popped onto the screen. She was still wearing her work blouse – thank God.
“What’s up?” I asked, trying to sound casual, not like she had been playing with my cock through my slacks that morning.
“No underwear?” she said, smiling. “Oh, that’s right, I was supposed to go first.”
I was about to object when, without even bothering to unbutton it, she pulled her blouse off over her head, revealing the bra I had been ogling on the subway. She stood up and unzipped her skirt and pulled it down. Underneath she had only a thong.
She did a pirouette to make sure I had an eyeful then sat back down.
“Stop,” I stammered. “You’re my boss. This is against company policy. We could get in a ton of trouble. I need this job. And if Jesse knew she would kill both of us.”
“I don’t think your sister would give a fuck either way,” she said. “If anything I think your sister would be jealous.”
“What?!” I spat. “That’s disgusting, and your misguided. Jessie prefers women over men, and she has no interest in me. I’m her brother!”
“Wrong” Megan sighed. “She’s not a lesbian, she’s a bisexual, so she likes both boys and girls. I bet she would love a chance to lick your lollipop.” She winked.
“Christ, Megan,” I said. “We are not having this conversation. Plus I have a girlfriend.”
“I’ve been your boss for two years now. I watched the relationship with your girlfriend deteriorate. You asked for a break six months ago so you both could sort things out and maybe see some other people to get a handle on your feelings for each other.”
“Right,” I agreed. “Exactly.”
“And you’ve been on how many dates?” Megan squinted at me.
“I just need some space,” I said.
“Space for…what?”
“To think.”
“Six months is more than enough thinking time. Maybe it’s time you stopped thinking and went on a date to actually sort out some of those feelings.”
“Um…maybe. But not with my boss…”
“Okay, then with who?”
“Um…” I scratched my chin.
“You don’t have to love me, let’s just have a little fling. You know, a little flirting, a little sex, get you back on your feet. What do you say? Ready to lose that shirt? You take off your top and I’ll take off mine.”
She let the straps on her bra fall down her shoulders and folded her arms under her breasts to hold the bra cups in place. She winked.
“I need to think,” I said. “Look, give me a couple days, okay?”
“Sure, no problem,” she said, pulling her bra straps back up where they belonged. “Trust me, I’m just trying to help. And I respect a hard ‘no’, so if that’s your final decision, I will honor it. But you’re a good guy, I hate to see you struggle like this.”
“I understand,” I said. “Thanks.”
I signed off and turned off my work computer. I tossed my work shirt in the laundry and wandered out to the kitchen for a beer. Flipping on the local news, I sat down on the couch and vacantly stared at the television, thoughts rolling around in my brain.
Maybe it was time to go on a date.
Maybe it was time to call my girlfriend.
Maybe it was time to join a monastery.
My thoughts whirled, finally to be interrupted by the sound of my phone ringing with an incoming video call. I glanced at the screen. It was my sister, Jesse.
“Hi,” I said answering the call. My sister popped up in the screen.
“Hi yourself,” she answered. “You okay?”
“Yes, I’m fine,” I said.
“I just talked to Megan, she said you sounded a little off.”
“What did she tell you?”
“Not a lot,” my sister said. I stared at Jesse for a moment. She was a year older than me, with dark hair and green eyes. She wasn’t slender like Megan was, a little curvier, but not fat by any stretch. She just had a bigger bust and slightly larger hips. She wore it well.
Jesse and I had always been pretty frank with each other, and we both knew that Megan had her moments. So I just dumped the whole series of events starting with the subway stroking all the way through the strip act on the video chat.
Unexpectedly, Jesse laughed. “That totally sounds like her. She’s kind of out of line, but if you don’t want to take her up on her offer, just tell her no. If she doesn’t take no for an answer, let me know and I’ll tell her to fuck off. But it wouldn’t do you one bit of harm. It doesn’t have to be a long term thing, just a couple of dates. A little light sex, you know.”
I sighed and nodded, looking around the room, avoiding eye contact.
Jesse continued. “Or, you know, if Megan doesn’t appeal to you, there are other fish in the sea.”
My eyes came back to the screen. For a moment, I thought she was about to add something, but she stopped. There was a long, uncomfortable, pause. The temperature of the call shot sky-high for a nanosecond as an old memory flitted through our brains.
“I am sure there are,” I said. “I’m sure there are.”
“Are you going to call Megan back?” Jesse asked after a moment.
I shrugged. “I guess.”
“Awesome! Let me know how it goes. Now do it right now before I lose your nerve. Hit her up on her private line. Get inside those tights of hers.” She winked.
Damn, my sister was pushy when she wanted to be.
I ended the call, then sighed. If I was going to do this, I was going to do it right. I pitched everything but my undershorts and grabbed my personal laptop, setting it up on the coffee table in front of me. I found Megan’s personal contact, gulped back the rest of my beer in one long swig, and hit the button. A second later she popped up on the screen. She was still in her office, still in her underwear.
“Hi Bryce,” she said. “Changed your mind? Ooh, you lost your shirt, you’re in your boxers, and it looks like you’re happy to see me.” The tent in my shorts was noticeable.
“Hi Megan. You said if I took off my top, you’d take off yours…” Go big or go home, I figured.
“You betcha,” she said. She slowly slid her bra straps down her arms then reached around and unhooked her bra. She was turning it into a show, and I guessed I didn’t mind. She did a slow tit drop, then tossed the bra to the side, cupping her breasts and pinching her tiny little nipples. Her breasts were small and pert, with tight, hard nipples pointing skyward. They looked like they would be delicious to suck.
“That’s better,” she said when she was finished. “Want to go further? My thong is dripping right now.”
“I need to add a ground rule,” I said. “No more public sex. No hanky panky on the subway, no sexiness on office computers. We keep this neat and above-board. I don’t need to get arrested for doing something in public.”
“Sure, deal. Is this about…?”
“It is,” I said. Megan had hired me and had been involved in my background investigation. There was a little blip in my personal history that I preferred not discussing. That blip meant it would be a bad thing if I got arrested. The fact that Megan knew Jesse and that she could vouch for me was part of the reason I got the job. That blip on my history made things challenging.
Megan cocked an eyebrow, then nodded.
“Deal,” she said. “Now are you going to take off your underwear or am I going to die of horniness?”
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