The Girl on the Video, Parts I – III by JackDRipper

PART I

“Seriously?”

I shook my head and looked at my boss, who was staring down at her phone.

“Unfortunately, yes,” she said, sighing. “They canceled at the last minute.”

“Ugh,” I said. It had taken an hour on the subway, going from one end of town to another, to get to the business meeting. We had managed to get an early start and miss the bulk of the morning rush, but now it was getting well into the rush, and the thoughts of dealing with the ride back made me cringe.

I had been at this job for a couple years now, selling cloud services to businesses, and I had done well. The worst part of it, though – in the business world, salespeople are the lowest on the totem pole. Folks with “real jobs” had no problem with jerking us around. I had spent four years in college as a marketing major, driving myself into debt with student loans – for this.

Megan, my boss, shrugged it off better than I did.

“Oh, well,” she said. “At least we had a nice ride on the trains today.” She gave a silly smile.

“Beats real work, especially since my boss knows I’m not out here slacking,” I shot back.

I liked my boss. She was fair, smart, and, had a great sense of humor. We bantered back and forth a lot, within the bounds of what was professional. It made working with her fun. She was friends with my older sister, Jesse, which was how I had gotten this job. I had known her for several years, even before I started the job.

Megan was easy on the eyes. She was perhaps six or seven years older than I was – I was just a couple years out of college – but she was a knock out. Pretty face, long blonde hair (now tied up in a business-like braid), fit, slender but with just enough curves to notice. She went out of her way when she dressed for work to minimize her figure, but you could still tell she was built. One time I caught sight of her as she was leaving at night to head to the gym, and she rocked the tights and sports bra.

But thoughts like that I kept at bay. She was my boss and, despite the fact that she was beautiful, I had to keep things professional. I needed this job and I felt like I would be letting my sister down if got in trouble on a job she got for me.

We made our way back to the subway station. It had been busy when we got there, the platform was jammed now. I fell in behind her as we threaded our way through the mass of bodies to the edge of the platform, where we waited for the next train.

My boss was busily typing emails on her phone while I kept a lookout for the next train.

“More bad news,” she said. “There’s a power outage at the office park, a cable cut. And the surge fried some of the equipment. It’s going to take awhile to get the juice back on. They’re telling people to work from home for the rest of the day.”

“Great,” I said. We had met at a subway station near the office with the expectation that we would be going back after the meeting. Now, in addition to the long ride on the crowded subway, I had a drive in rush hour traffic to get home. It just kept getting better.

Again, Megan seemed to be taking it better than me.

“Well, at least you get to work the rest of the day from home in your underwear if you want,” she said, smiling and laughing.

“As long as there are no video conferences,” I shot back.

“Or maybe if there are,” she laughed, peeking at me slyly from the corner of her eye.

I ignored her.

“No comeback?” she added.

We had had a good rapport up until this point, what could be the harm in a little light flirting, right? We were both professionals.

“Sure,” I finally said. “I will if you will.”

She laughed and smiled. “Deal.”

We crowded into an arriving train. There was a single empty seat next to the aisle and I let my boss have it while I stood nearby. The crush of bodies pushed me so my side was against the side of the seat where she was sitting.

I looked over to the window of the train. We were in a tunnel so the window was dark and my own reflection looked back at me, my boss in the seat next to me. She was glued to her phone. But in the reflection I let my eyes wander for a moment. Her blouse was gapped just right so I could see the curve of her breast and her white bra strap.

I had never taken visual liberties at work with her up until this point and I wasn’t going to start now. Megan was my boss. I forced myself to turn my eyes away from her and back to the front of the crowded train.

“They want to reschedule for Friday afternoon,” Megan said. “Does that work for you?”

“Yes,” I said, looking down.

She nodded, still not looking up. I let my eyes linger for a moment and noticed that the gap in her blouse was such that I could see the space between her breasts. I swallowed and turned back to the front of the train again. Inadvertently I caught the eye of someone standing in front of me, so I turned back to the side. Once again, my eyes found my reflection in the train window, and the growing gap in my boss’s blouse.

I felt a stirring in my slacks. This was not what I wanted. Not with my boss.

The train slowed as we came into the next station. The doors opened and more people piled in, pushing me closer to my boss. When the doors closed, the side of my hip was pressing against her shoulder.

My nerves were not helping my efforts to lose the budding erection. My only place to rest my eyes without coming into visual contact with other passengers was the window.

And in the window reflection, my eyes just automatically found the gap in my boss’s blouse. It seemed to have gotten wider. I could see the edge of her bra, and the gap between the bra cup and her breast. In fact, if I leaned a little to the right I might be able to see the edge of her nipple.

My hard-on was almost to the point where it would become noticeable. I was wearing slacks and boxer shorts, so there was little to restrain my growing erection.

“Jesus, Bryce, enough,” I told myself silently.

The train hit a bump and the crowd shifted. A woman near me moved slightly to adjust her hold on the overhead bar, bumping against me and forcing me to move so my boss’s shoulder was now pressed against the front outside of my thigh. She was barely an inch from my hard on that was about to tent my slacks. I pushed backwards slightly and felt my arm pressing against the breasts of the woman next to me. Not helpful!

Megan leaned forward slightly to reach into her bag for her laptop. As she leaned back into her seat, her shoulder brushed the tip of my cock.

I swallowed hard and started calculating batting averages for the local MLB team. I had to think of anything except my boss’s body.

Megan didn’t seem to have noticed, and had her laptop open, typing away. I closed my eyes.

“I think I want to change our presentation for Friday,” she said. “What do you think of this?”

I looked down at the computer screen and nodded. Without even trying, my eyes wandered back to the gap in her blouse. Was it getting wider? I could definitely see her nipple.

“Stop!” I screamed at myself in my head.

The train slowed and even more people poured in. I had to adjust my position again. My half-erect cock was now only a couple inches from my boss’s shoulder. If anyone moved…

The train hit a bump, and a passenger behind me shifted, pushing me next to Megan. My semi-hard cock was pressed against her shoulder. I tried to shift backwards, but to no avail.

My boss seemed to take no notice, still typing away at the computer.

I wanted to move, I wanted to pull away, I wanted to get the hell out of there, but I was trapped.

Not helping the situation, the train swayed gently as it moved down the tracks. That motion caused my cock to rub against Megan’s shoulder.

She blithely kept flipping through her slide deck on her laptop, making tweaks here and there, seemingly not even noticing my meat pressing against her shoulder. There was no way she couldn’t not know that my cock was against her upper arm.

“That’s better,” she said. Flipping the laptop closed and returning it to her case. When she leaned back in her seat, she pressed my cock partially between her shoulder and the seat back.

I stifled a groan. My slacks were now undeniably tented and partially squeezed between my boss’s shoulder and the seat. I looked down. Her blouse was gapped widely, and I could clearly see the cute little suckable nipple inside her bra cup. And as the train slowly rocked, she rocked with it, squeezing my cock with each motion.

I had no idea what to do. There was nothing I could do. My boss was giving me a…a…what would you call this? A shoulder job? What the fuck…?

The train slowed. We were moving out of the city center. I hoped the train would start to empty soon, so I could move the fuck away and get my dignity back.

No such luck. More people poured in. My cock stayed wedged between my boss’s shoulder and the seat. The train swayed and my cock throbbed. I closed my eyes and tried to find some mental gymnastics or safe zen space that would take my mind away from the fact that my hot boss was surreptitiously stroking me off in a crowded subway car.

Above all else, I didn’t want to unload in my slacks. They were light colored, and having jizz trickling down the inside of the legs would be obvious.

Another station. This time, thankfully, more people cleared out than entered. Even more thankfully, the person sitting on the other side of my boss moved out, opening the seat up. Megan preferred the outside, so I slipped past her and sat down, though when she stood up to let me in, she managed to shove her ass against my cock for one final thrill before we broke contact and I made my way to the seat next to her.

I took a deep breath. Safe. I shifted my cock down my pants leg and stared out the window into the blackness of the subway tunnel. I cleared my mind. My cock began to come down from high alert.

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?”

“You first,” I said.

Megan leapt up and turned, pointing her slender, trim ass at the camera and giving it a gentle shake. She pulled her cheeks apart, revealing the narrow cord of her thong poorly hiding her puckered asshole. Below her ass, the thong was puffed out by her vulva, the fabric soaking wet.

She turned back around and slid her hand into the front of the dripping thong, and rubbed herself under the fabric, sliding her fingers up and down her vulva, slipping one finger inside. She pulled her hand out – it was soaking wet – and lifted it to her lips.

After licking her fingers dry, she bent over and pushed the thong to the floor, standing naked in front of the camera. She slipped her hands between her legs.

“Now show me that cock of yours, baby,” she said.

I reached inside my shorts and pulled my cock out of the fly of the boxers. I wasn’t immense but I was slightly larger than average, checking in at just around seven inches. I gave it several slow strokes, bringing it to full attention, pointing it at the camera. A couple of more strokes and I was able to squeeze a few drops of pre-come from the tip.

Megan had moved back to her chair and was sitting naked with one leg over the arm of the chair while she slowly ran her fingers up and down her labia. She was an innie with puffy flesh around a tight slit and a tiny, almost invisible, clit. Her pussy was only rivaled by her breasts in cuteness.

“I want to see you come,” Megan said breathlessly. “I want to see you drop your load. I’ve come twice just since you called back. It’s your turn, baby.” She still was working her fingers up and down, in and out, of her slit.

I was already more than half way to the moment of glory. I kept stroking my meat as I watched Megan play with herself. The fabric of the chair she was sitting in – the same chair she sat in when she worked from home – was drenched, and her pussy was soaked. She took her other hand and squeezed her cute little tits. She was beautiful, she was hot, she was desirable. I lifted my cock straight up as I stroked, sliding slightly forward so she would have a good look when I came.

My balls tightened and a thick shot of semen rocketed from my cock, shooting up and over my shoulders. Megan moaned as a second load landed on my chest. She squeaked in pleasure.

The third and fourth shots landed on my stomach and the rest puddled on the front of my boxers. I sighed as Megan smiled at me through the laptop screen.

“Nice,” she said. “But are you going to take off those boxers so I can see the full package?”

“Not unless you come over here and take them off me.”

“Oooh,” Megan said. “I will be right over. Don’t move, don’t put on any more clothes, don’t do anything. I’ll be right over to rip those come-soaked shorts right off.”

The screen went blank. I closed the laptop and stared vacantly at the television screen that was now starting “Wheel of Fortune”.

“Wheel” had ended and “Jeopardy!” was just beginning when there came a knock on the door.

“Come in,” I called.

Megan entered. I gulped. She was only wearing the bra she had had on earlier in the day, and a pair of light colored shorts. The shorts were wet in the crotch, and underneath I could clearly see her still-soaked thong.

By the time she got to the couch, she was naked. She bent down, bit the sticky puddle of come on my shorts and sucked, then pulled them off me with her teeth. Then she stood up and straddled me on the couch.

She pressed her soaking slit against my burgeoning erection, pressed her pert breasts against my chest that was still sticky from my earlier ejaculation, and pressed her lips against mine. Our mouths opened and our tongues intertwined as she ran her hands down my chest and I ran my hands up her toned thighs to her firm ass. She was already gyrating her hips against mine, her vulva pressing my cock down against my thighs, making it harder and harder.

I leaned down, sucking her tiny, pert nipples into my mouth, sucking at the hard darts that perched atop her firm, small, round breasts. I had been thinking about those nipples ever since I had seen them inside her gapped bra that morning. I had been imagining what it would be like to run my tongue around the narrow aureoles and to suck the tiny erect nipples. They smelled of perfume and tasted of a salty sweat – the kind of sweat that builds up during a day of thinking about someone special. She was primed and ready.

Megan reached down and pulled my now-hard cock up between her puffy labia and slowly slipped her body down my cock, inch-by-inch. Her vagina was wet, soft, and just tight enough. I grabbed her ass and guided her down my cock until her pussy was pressed against the base of my meat.

She leaned down and we kissed as she started gyrating her hips around, up-and-down. The smells of fresh sex and the old remains from our earlier cybering session filled the room – pussy, sweat, and semen. Megan continued to gyrate her hips up and down my cock, swinging them gently with each stroke. Her motions started slowly, but then picked up. She kissed me again, then pulled back and braced her arms on the back of the couch for extra leverage. The hours at the gym paid off as she ramped up, cranking her body up and down my meat.

Sweat poured down her chest, between her breasts. Our eyes remained locked as she ground her cunt into my thighs, driving faster and faster until the only sounds in the room were our panting and the slap of her ass against my thighs. She slowed a tiny bit as I felt an orgasm waft through her body, but she kept going.

“Do you want me to…” I started, but she put a finger on my lips. She redoubled her efforts. I could feel the muscles in her hips, her ass, and her abdomen were all tight as guitar strings. She leaned her head forward, her hair trailing across my face and chest. She closed her eyes and worked my cock even harder.

I felt my balls tighten. I was almost there. She squeezed her pussy muscles tighter as she came again. That was the final straw. My balls squeezed and I managed to lift her off my meat just as a thick load shot out, eliciting a cry that came near to a scream from her lips.

She fell forward onto my chest, her forehead pressed against my shoulder as she shook with a final orgasm and my seed emptied across the skin of both of our stomachs.

The orgasm ebbed and she rolled off me, sitting on the couch next to me. We were both sweaty, naked, and covered in our own juices.

“That was….” I started.

“…fucking great.” she finished.

She leaned over and kissed me, then lay her head on my shoulder and her hand on my stomach. I wrapped an arm around her shoulder.

“Thank you,” I said.

“You’re welcome,” she said, and giggled.

“What’s so funny?” I asked.

“How shy and resistant you were to this,” she said, smiling.

I sighed. “I know, but I had a lot to process.”

“I know,” she said. “and not just about me, but about your girlfriend, and about, well, you know…”

“Yeah,” I murmured. The fact that she decided to bring “that” up right now was annoying.

“That” had been the incident when I was younger. I was sixteen and was caught shoplifting. It wasn’t just a pack of gum, it was jewelry. Exactly why I was shoplifting jewelry was…complicated…but suffice it to say I was caught. And because the value of the items I shoplifted was almost a thousand dollars, I was charged with a felony.

Video from the store showed that I came in with another person, who slipped away as soon I was caught. I refused to rat out my accomplice, which made it even harder on me. Everyone thought it was my sister, and she was arrested, but released due to lack of evidence. I was the only one who was charged, but I was hit hard because I didn’t cooperate.

So that’s why I ended up being charged as an adult and why I spent eighteen months in juvie and another year in a halfway house. My mom was crushed that her children could do something like this. I had never been close to my parents – my dad lived across the country and my mom – a local hotel mogel – was always work-obsessed and distant to both her kids. So when I was released from the halfway house I just went straight to college and dorm life. After college I spent a month living with a friend until Jesse helped me get this job and I could get a place of my own. I had spoken to my mom only a handful of times since I got out of juvie. And I would continue to be on probation for another few years, though I only checked in with my officer once a month by phone, and in person twice a year.

I had moved on, as far as I was concerned. It was in the past, and I was annoyed that Megan would bring it up right now, spoiling the post-coital afterglow.

And now she wouldn’t let it rest.

“Have you ever considered therapy?” she asked, rubbing her hand across my chest and playing with the gobs of semen that still coated both our stomachs and chests.

“Therapy? Not really.”

“You should, you’ve been through so much.”

“I’d rather not talk about it,” I said.

“That’s why you should see a therapist. Someone independent that you can safely talk to about things. Seriously, you should think hard about it,” she said softly.

“You sure know a lot about me…” I said, sarcastically.

“Jesse and I are close,” she replied. “We’ve talked about you some.”

“So just how close to my sister are you? You seem to know her sexual tastes.”

“I was bi-curious, and I knew I could trust your sister,” she said, smiling. “Plus I like her, and you too, so she was a safe person to take my feelings to. She has helped me sort through things some.”

“So what did you decide, do you prefer boys or girls?”

“I prefer boys, but I could go for the right girl, if I met her.”

“Is my sister the right girl?” I asked.

“I’m not sure. She might be, or you might be the right boy,” she said, kissing my cheek. “But before I can figure that out, I get the feeling that there is something that the two of you need to sort out before either of you will let me in.”

“What’s that supposed to mean?”

“I’m not sure. It’s just a vibe I am getting.”

Megan must have sensed that she had crossed some invisible boundary, because she backed off. She leaned back on the couch again and we flipped the TV to a sitcom we watched in silence, sitting naked on the couch still damp from our lovemaking.

Around 10:30 she disengaged from me and dug her phone out, doing a quick check of her email.

“Well, it looks like there is more damage to our power supply than just the cable cut. They are telling us to work from home tomorrow. I probably should go home because they will probably be calling me early and I doubt management will take kindly to me working from your house in my underwear.”

I suggested that we do dinner on Friday (rather than sex on the subway again). Megan agreed.

We kissed and said our somewhat gropey goodbyes then she got dressed and headed out.

I killed the lights, crawled into bed, and slept well for about four hours. Then I woke up and spent the rest of the night tossing and turning, thinking about Megan – and about what she had said about my sister and I.

PART III

I managed another hour or so of sleep before the alarm went off.

Thursday at work went uneventfully. Megan was busy, and we had no interaction except pure business. We were still working remotely because of the power cut and related damage, so we didn’t have any face-to-face time.

I had just wrapped up for the day and was considering what I would do that evening when my phone rang with a video call from my sister.

“Hi Jesse,” I answered. “What’s up?”

“Hi Bryce. I was wondering, do you want to come by for dinner? We haven’t just talked in awhile, or seen each other face to face. You’re my brother and the only living relative I’m close to so we should see each other in the flesh at least occasionally. I’ve got fixings for fajitas. You down with that?”

“Sounds good.”

I pulled on a polo and a pair of khaki shorts and was over her place by about 6:00. Jesse met me at the door in a short flowered sundress and we hugged. She looked really cute.

The fajitas were good and we chatted through dinner and a half a bottle of wine. After eating we wandered out onto her balcony with the rest of the wine. We sat down on a porch swing. The evening was cool and a gentle breeze was coming through the air. We sat in silence for awhile staring out across the city.

The words that Megan had said about my sister and I having things to work out had been churning in my brain all day. I knew she was right, my sister and I most definitely had things to work out.

I was working up the courage to broach the topic – a topic we hadn’t discussed in years – when she spoke first.

“I talked to Megan today,” she said.

“Yeah?” I said.

“She told me you too had fucked.”

“Ditto,” I said, taking a sip of my wine.

“You’re not jealous, are you?” she asked.

“No, not at all,” I replied, looking at her. “You?”

Jesse shook her head. “She also said…” she started, then paused.

I finished her statement for her. “She said she wouldn’t know how she felt about either of us until we sorted things out between us, right?” I asked.

My sister nodded.

“Is that why you asked me over tonight?” I asked. “So we could sort things out?”

She nodded again, nervously.

“I’m glad you did,” I said. “Last night I was thinking about that night, the night we were caught.”

“I think about that night a lot,” she said.

“So do I. I always wondered what our lives would’ve been like if that hadn’t happened.”

That night in question happened shortly before the shoplifting episode when I was sixteen and Jesse was seventeen. We had been at the neighborhood swimming hole with some friends and had come back late. We’d had some beers so we were a little tipsy.

We snuck inside without our mother hearing us, and made for her bedroom, where we intended to say good night then I would go to my room. Our aunt, who was visiting from out of town, was asleep in the guest room.

As we stood in my sister’s room, feeling silly and giggling, I went to hug her good night, but somehow changed my mind mid-stream and kissed her instead. She giggled and asked me what I was doing.

I had suddenly gotten nervous and self conscious, so I pulled back. But now that Jesse was turned on, she wasn’t taking no for an answer. We started undressing and one thing led to another. But suddenly, the next thing I knew, our aunt Brenda was standing in our room staring at us as we grabbed at our clothes and pulled them on hurriedly.

Busted.

Thankfully Brenda never told, though she would later exact an even heavier price – but that story was for another night.

“Never happened?” Jesse asked. “Do you mean if we didn’t make out or if we didn’t get caught?”

“Didn’t get caught,” I said. There was a long pause before either of spoke again.

“Who do you think Megan loves more?” Jesse asked.

“She’s your friend,” I said.

“That’s not what I asked.”

“I don’t know. I just know she said she wouldn’t know until we sorted out whatever was between us. I actually think she would love it if all three of us were a thing.”

“Do you love me?” Jesse asked.

“You’re my sister,” I said. “Of course I love you.”

“Not like that,” she said, turning towards me and leaning her shoulder against mine. “I mean, that night we were caught, did you love me? Do you love me now?”

“I don’t know, so much has happened since that night. I think I loved you then. I might love you now. I just don’t know,” I said, with a sigh.

“Megan is right, we need to sort this out,” Jesse said.

She turned even further so the side of her chest was pressing against my arm. She wasn’t lithe like Megan, she was curvier, though not fat by any stretch, she just had a bigger chest and wider hips. And her larger chest was now pressed against my arm. Her skin was soft and I realized she had no bra on underneath. I could feel her hard nipple underneath the fabric.

Something stirred inside me. Something I hadn’t considered since that night so long ago. Something that had been stuffed by juvie and by halfway houses and by getting the butt end of life for one tiny mistake.

I turned to her. The sun was setting and the breeze ruffled her dark hair. My sister looked gorgeous.

Inside my shorts my cock began to stir.

My sister spoke up. “Your relationships are going nowhere, my relationships are going nowhere, and Megan is suddenly in the middle of all this trying to decide her feelings for both of us. It’s fucked up and it’s probably not going to get unfucked until we sort ourselves out.”

“What if we decide we want each other and tell Megan she’s out of luck?” I said.

“She’s a big girl, she’ll get through it,” Jesse said. She put her hand on my thigh a few inches from my growing erection. “But more importantly, I really just think she wants us to be happy regardless whether or not she is in the picture.”

The strap on her sundress had slipped off her shoulder and was almost to her elbow. The front of the dress had slipped down and one of her breasts was dangerously close to freedom. She ran her hand up my leg to the cuff of my shorts, then slipped her fingers into the leg of my shorts until they encountered the tip of my stiffening cock.

I leaned down and kissed my sister on the lips. She pressed back firmly. We disengaged, then re-engaged with more gusto, our lips parting, our tongues intertwining.

I realized this was the moment I had secretly craved ever since that night we were caught.

She smelled of lilac perfume, and her fragrance mixed with my aftershave, creating a heady aroma. I ran my fingers through her long dark hair and then down to her dress. I pulled her breast clear of the fabric and softly brushed it with my fingertips, teasing the nipple and gently caressing the underside. Her long nipple was already hard. I disengaged my lips from hers and leaned down, running my tongue over the aureole. I could feel the nipple hardening under my touch.

Suddenly Jesse pushed my head away and stood up, retreating inside. I followed her in.

“Are you okay?” I asked as she stood in the center of the living room, head in hands.

“I’m just…not sure all of a sudden,” she said, pulling the strap of her dress up to cover herself.

“I understand, it’s a lot to process,” I said. “Maybe Megan is right. Maybe we should see a therapist before we take the big leap.”

“The problem with that is that any therapist would probably tell us outright that what we are thinking about doing is wrong. I need a more balanced viewpoint.”

“There’s always Megan,” I said, half-jokingly.

“Right, and on the other side of the coin there’s Megan.”

There was a long, uncomfortable silence, then Jesse shook her head and came to me, wrapped her arms around me, and laid her head on my shoulder.

“Jeez, Bryce, what the fuck are we going to do.”

The smell of her perfume and the conditioner in her hair, the feel of her body pressed against mine, her breasts against my chest with just two thin layers of fabric between us. I hugged her to me and felt my erection growing again. Underneath her dress I could feel her nipples harden.

She looked at me and we gazed into each other’s eyes for a long moment. Then our lips met.

Then Jesse’s phone rang.

“Fuck,” she said and disengaged, reaching for the phone on the coffee table.

“Speak of the devil,” she said, hitting the answer button. Megan’s face popped up on the phone’s screen. “Hi Megan.”

“Hi Jesse, oh hi Bryce. You guys hanging out? I didn’t interrupt anything did I?” she asked. I looked closely at the picture on the screen. Megan was calling us from the bathtub, bubbles piled high around her.

“Um,” Jesse said, looking at me, then at the phone. “We were just working on sorting out some things, you know, like you said we needed to.”

“That’s awesome,” Megan said. “I can leave you two alone. I was just dropping in to say hi.”

“Wait,” Jesse said. “Don’t go yet. We’re kind of, well, stuck.”

“Stuck? Do you want some help?” she said.

Jesse and I looked at each other, I shrugged.

“Yeah,” I said finally. “We could use some help.”

“I’m not a therapist,” Megan said. “But I might be able to help. I’ll be right over.”

The phone went dead.

“You know what this means, right?” Jesse asked.

“It means we are opening ourselves up to that three-way relationship,” I answered.

“Right,” she said. “I think I’m okay with that.”

“Me too.”

We sat down on the couch, side-by-side, holding hands. We both wanted each other, but we were holding back.

“We need to tell Megan the whole story,” I said.

Jesse nodded.

We didn’t say another word until Megan knocked on the apartment door a half hour later.

She was wearing a white spaghetti tank, nothing underneath, and a set of light colored tights, also nothing underneath. Her blonde hair was still damp and pulled back in a pony tail She dropped a bottle of wine on the table next to the one we had been working on and poured all of us fresh glasses, then sat down across from us in the living room.

“You two look beautiful together,” she said, looking at us. “You make a cute couple. So what’s the problem?”

“There’s some history you need to know about,” I said.

“So tell me.”

Jesse started before I could continue. “A couple of months before the shoplifting incident, when I was seventeen and Bryce was sixteen, we were caught getting ready to have sex.”

“Really, how far along on the ‘getting ready’ scale were you?” Megan asked.

“We were at the ‘I’m hard as a rock and hovering outside her pussy’ point,” I said.

“Wow,” Megan said. “That’s pretty far along. What happened?”

“Our aunt Brenda was visiting at the time,” Jesse said, picking up the story. “She’s a few years younger than our mom. She heard us and came into the room – didn’t even knock. We were totally busted.”

“Did she tell?”

“No, she didn’t…” Jesse trailed off, so I jumped in.

“She threatened to tell our mother,” I said. “She lorded that over us, told us our mother would hate us if she told, used that secret as a bargaining tool to get us to do whatever she wanted. Our mother was always distant, we didn’t want anything to hurt her, so we complied. Until one night. Brenda came to us and said there was some jewelry she really wanted but she didn’t have the money for. She said she had cased the store and knew where the keys were kept. She said she could provide a distraction. Said it would be easy.”

“Oh, fuck,” I heard Megan say. “The video they used to convict you showed a girl there. She was wearing a cut off hoody and sunglasses. Everyone assumed it was Jesse but couldn’t prove it.”

“Actually, it was my aunt Brenda. I wanted to turn her in, but I knew if I did she would tell my mom about what happened between Jesse and I. So I kept my mouth shut, and I paid the price.”

“So it was a no-win for you. Your mother would have pushed you away either way.”

“Right, but Jesse managed to keep at least the thread of a relationship with her, and I didn’t want to destroy that.”

“So Brenda got off scott free, you did hard time, and your mom thought that you were a criminal and was hurt.”

“In so many words.”

“Jesus, this is pretty fucked up,” Megan said. “Where’s Brenda now? Where’s your mom?”

“Our mom inherited several hotels around the city, so she has a little empire that she lives off of. She lives in an apartment in one of the hotels. She’s in her late forties and is a bit of a cougar, always chasing after the young men. She talks to Jesse maybe once a month or so. Brenda, well, she’s, um, interesting…”

“What do you mean?”

“Well, Brenda is about five years younger than my mother, and she’s a model,” I said.

Jesse interrupted. “Model is a really nice word for it. She does erotic modeling and she’s a camgirl, has her own website and an OnlyFans. She has a pretty popular cam show.”

“Wow, you come from a pretty fucked up family,” Megan said. “You should think about that therapy thing. And you should think about coming clean to your mom – and take legal action against your aunt.”

“Maybe, someday…” Jesse said. “But right here right now, all that is why Bryce and I are having…trouble.”

“Understood. So you thought maybe mommy Megan could maybe help ease you back to that point where you were so rudely interrupted so many years ago.”

“Yes,” I said.

Megan got up and pulled off her top, letting her small but perfect breasts come free. She moved the coffee table out of the way and stood in front of Jesse. I leaned in her direction but she held out a hand.

“You just watch for a few,” she said, smiling, running her hands down her perky little tits that were now hard as bullets. “Relax and do to yourself whatever comes naturally.”

She leaned down and kissed my sister on the lips. Their mouths locked their eyes closed. Jesse’s hands found Megan’s body as Megan pulled the straps of Jesse’s dress all the way down, tugging the fabric free from my sister’s large, soft breasts. Megan caressed Jesse’s breasts, running her fingers softly over them, teasing the underside.

Their lips disengaged and Jesse lowered her mouth to my sister’s tits, pulling her brown nipples between her lips, and running her tongue over the aureoles. She continued the motion, taking her tongue down into the valley between Jesse’s breasts and up onto the other one, sucking and licking at that nipple.

Jesse’s head was laid back and she had one hand on Megan’s chest and another between her own legs, caressing her slit underneath her dress she had hiked up. I realized for the first time that Jesse hadn’t been wearing underwear.

Watching my sister make out with a woman I had been fucking just 24 hours before brought my cock to attention, tenting my shorts. I was trying to be calm, resisting the temptation to start stroking, but Megan glanced over and saw me sitting there, still fully dressed, with a huge bulge in my shorts.

“You aren’t going to accomplish anything with that thing buried under all that fabric,” she said. “Get that thing out and get it ready. Your turn is coming.”

I didn’t argue. I pushed off my shorts and my shirt and sat their naked, my cock at full attention, stroking it slowly.

Megan turned back to Jesse and they continued their kissing and caressing session. She disengaged her lips from my sisters chest and slowly ran her tongue down her stomach, skirting down the outside of one of her thighs, before diving between them and into my sister’s tidy little pussy. Jesse moaned as Megan began slowly licking up and down her slit.

I stroked my cock slowly, trying to bide my time, but getting hornier and hornier by the second. Jesse had one of her legs propped up on the arm of the couch, spreading her legs as wide as possible and Megan worked her slit over. I could smell the fragrance of perfume mixed with a woman’s heady musk. Jesse moaned again, and Megan did the same.

Megan pulled back and turned to me.

“Your turn, loverboy,” she said, crawling on all fours and positioning herself between my legs. She reached out and grabbed my rock hard purple cock and began stroking it, pulling just the tip inside her mouth and sucking. She ran her lips down the underside, teasing that sensitive spot under the helmet, before slipping the entire shaft into her mouth. She flicked her tongue across the tip and stretched out a long thread of pre-come.

I gasped as she ran her lips up and down my meat and squeezed my balls with her hands. I watched her blonde head move up and down as she deep-throated my cock, then turned to my sister. Jesse was watching Megan fellatiate me and playing with herself frantically. I think she came while she watched.

Jesse rolled over onto all fours on the couch and pointed her cute, puffy little pussy at me.

“Fuck me,” she said. “Just fuck me. I’ve been waiting years for this, it’s time, please finish me.”

Megan pulled my cock from her mouth and smiled.

“Go get her, tiger,” she said.

I stood, my cock at full attention. In front of me my sister’s sopping wet pussy begged me to fuck it. I hesitated. Megan came up beside me and reached down, pulling Jesse’s slit open with one hand and stroking my cock with the other.

“This is as far as I can get you,” she said. “You have to do this final part yourself. You know you want her. Forget she’s your sister, just think about how much you love her and how much you want her. Don’t worry about what anyone thinks. Just do it.”

“For fuck’s sake,” Jesse moaned. “Just fuck me.”

I swallowed, gave my cock a final stroke, and slipped it into my sister’s slit.

“Oh fuck yeah,” she gasped. “Fucking finally.”

She was tight, wet, slick, and hot. I felt every inch of her cunt slide down my shaft, every muscle ridge, every drop of juice. It was intoxicating. I had waited for this moment, dreamt of it, prayed for it. The thought of this moment sustained me through my incarceration.

When my balls bumped against her clitoris, I felt fulfilled. Every doubt I had ever had about my relationship with my sister vanished.

This was right.

“Get fucking busy,” my sister said. I complied and began pistoning in and out of my sister’s deep, wet snatch. She moaned with every stroke I took. I started slowly, but Jesse started egging me on to go faster and harder, so I did.

Megan had moved to the chair across the room and was watching us fuck while fingering herself madly. I turned my attention back to my sister, reaching around and squeezing her tits. She moaned again as I felt an orgasm wash over her and my balls began to tighten. I increased the pace even more as Jesse tightened her muscles in her orgasm.

I knew I couldn’t last much longer. I didn’t want to come inside her, but I wanted her to come one more time before I did. I cranked up the pace until I couldn’t possibly go any faster or harder. My stomach slapped against her shaking ass as I pistoned in and out of her. Her juices washed over my balls and ran down my thighs. She let out a long slow moan as another orgasm crashed over her.

I couldn’t take any more. I pulled out just as the first shot of thick seed erupted from my cock. The first two pulses completely overshot Jesse and landed on the floor beyond. The next shot ended up in Jesse’s hair, and the rest coursed across her back, and then her stomach when she turned around to kiss me.

Finally.

Jesse and I lay entwined on the couch for several minutes. I glanced over at Megan who was smiling and looking at us.

“I’m really glad you two finally connected,” she said, smiling. “If you didn’t either see a therapist or fuck, I was afraid one of you was going to have an aneurysm. I love you both to death, so it was tough to watch.”

“Thank you Megan,” I said. “Without your help we probably would never have made it to this point.”

“Yes, definitely, thank you,” Jesse echoed, then gestured Megan over and the three of us shared a long embrace and kiss.

“So where does that leave us?” Jesse asked when we were through.

“What do you mean?” Megan asked.

“Oh, don’t be so coy,” Jesse said, reaching over and playfully slapping Megan’s ass. “You know what I mean. You have been angling for a three-way relationship for months.”

For the first time, Megan actually seemed a little embarrassed. She blushed, then nodded.

“Yeah, I guess I have,” she said, then peeked up at us with one eye through her disarrayed hair. “Did I succeed?”

I laughed. “I think at least we are willing to give it a try, a trial run.”

Megan smiled. “Awesome, thanks. I really do love you guys.”

“And we love you too,” Jesse said.

“Thank you,” Megan said. “Have you guys considered talking to your mom about what happened, and about your relationship, and how Brenda was the girl on the video.”

“No,” I said. “We have no evidence to back it up, and our mother already hates us enough for now without us risking her finding out about our dalliance.”

“Do you have a copy of the security video they used to convict you?” Megan asked.

“I kept a copy of just about everything from the trial,” Jesse said. “So yes. The police looked at it cursorily but didn’t go too deep into it. They figured they knew who the girl was, so they didn’t do much in the way of analysis.”

“Any chance you can let me take a look at the video?” Megan asked. “And do you happen to know the name your aunt goes by on her webcam shows and OnlyFans?”

“Yes and yes,” Jesse said. She fired up her laptop and in a minute said “It’s in your inbox. The attachment is the video clip and the OF/Insta/camgirl name is in the body of the email.”

Megan flipped on her laptop.

“Toxic-Whore-Brenda-MILF…wow…well I guess she got her name right. Okay, let me study the video, then maybe we can convene at my place tomorrow night for dinner and a strategy session?”

“Sure,” I said. Jesse nodded.

“I need to get home and get some sleep, and you should to,” Megan said, looking at me. “That client tomorrow afternoon has upped the ante. This could be a seven or eight figure deal. The CIO is going to attend, so we need to be on the ball. If you want to sleep in tomorrow, that’s fine, just be there by 11 or so and be ready to rock. Got it?”

“Sure thing, boss,” I said.

The next day I got to work a little after 10 and the rest of the work day was a blur. We skipped the subway and rode down to the client site in the CIO’s car along with a couple techs, so there was no hanky-panky. The meeting went well, we landed a 20 million dollar deal, and our bosses were ecstatic.

The three of us met as planned at Megan’s place after work. Nobody felt like cooking so we just ordered pizza. While we waited for the delivery, Megan dug out her laptop.

“So last night before bed, I did a little digging,” she said. “Where to begin…let’s start with the video. It’s pretty clear the cops didn’t spend a lot of time on that. Let me show you a couple of things.”

She queued up the security camera video and skipped forward to about twenty seconds in.

“Okay, so here’s where you guys enter the jewelry store. You can see your aunt start chatting up the sales guy. Now right here you’ll notice she follows him to the far corner of the store looking at a couple of diamond rings. This is the only time you can see your aunt’s ankles in the entire video. If I freeze it, take a look at the inside of her right ankle. What do you see?”

“It looks like a tattoo of a star,” I said. “She has one there.”

“Exactly,” Megan said. “Your sister has nothing there. So let me zoom and take a screenshot. That’s point number one. Point number two, is about forty seconds later, when she and the salesman have moved to the front store she turns just right and you can see the inside of her left arm. If I freeze it, what do you see there?”

“Another tattoo of a rose,” I said.

“Yep, and Jesse has no such thing. So if the cops had done their job, they would have known who the accomplice was, but they just assumed it was the perp’s sister.”

“Wow,” Jesse said.

“But wait, there’s more,” Jesse said. “Let’s take a look at your aunt’s OF page. I dropped twenty five bucks for an account, I sent you the credentials a few minutes ago. There’s something really interesting here.”

[TO BE CONTINUED]

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