Accountants Get It in the End

"Ooh, looks like I got it in. Let's try a little back and forth."

"I don't know about that – uhhhhhhh!" I groaned as she pulled it partially out, stretching me again and rubbing along my prostrate. More groans and my legs got wobbly as she ran it in and out. I felt her squirt more lube on.

"How ya feelin'?" she asked.

"I'm not sure" I replied breathlessly. I really wasn't sure. It wasn't so much painful as uncomfortable, but the sensation was like nothing I'd ever felt. "It's weird, but good. Kind of uncomfortable, especially – umph – when you push it in like that. Or, oh shit, pull it back out."

"You should see your butthole. It just keeps getting bigger and smaller. Lucky my finger isn't in there; it looks like it's squeezing pretty hard." I turned around and noticed she was stroking the dildo on her strap-on. Well, she wasn't so much stroking it as she was grinding it back and forth into her and her clitoris. I got harder seeing that.

"You looking at my dick?" she asked sweetly. "Maybe you need some of this bad boy. Let's get the toy out of the way." I could feel her pulling the plug out of me.

"Ow, ow, ow" I groaned as the large part slid out. Once that was done the rest shot out fast, leaving a hot feeling behind.

"Wow, your asshole is really big. Aw, now it's getting small again. I'm gonna fix that." I shivered a bit, knowing what was next. "Don't worry sweetie, we'll get you all lubed up." Again, the cool lubricant was a shock as she poured it between my cheeks and injected it into me.

I turned to see what she was up to. She was just coating her "dick" with lubricant, sliding it on the whole surface. Still breathing hard I told her, "This is weird but you look really sexy stroking your cock."

She just smiled and said, "I like it too. Ready? Here goes."

I braced myself as she pressed the head of the dildo against my ass. Gripping my hips she pressed forward, splitting me open again. I gasped and groaned as she effortlessly pushed into my rectum. "Ooh, I'll bet that feels nice," she purred.

I was surprised how easily it was going in. "You doing OK?" she asked.

Raggedly I answered, "Yeah. It's going in... pretty easy. I'm so fucking full!"

As she kept pushing it in deeper it started to feel uncomfortable. I could feel my muscles tightening on the shaft of the dildo but that didn't slow it down. I was panting and groaning as she filled my rear up and started noticing her doing the same. Just as it was getting really uncomfortable and becoming painful I felt her body bump up against my cheeks. She was fully in! I released my breath, not realizing that I had been holding it for the last few moments.

Breathlessly she said, "Wow, I'm in. You're being fucked in the ass!"

"I'm" – "so" – "fucking" – "full. Can you" –" Pull it back" – "Out" – "A little?'" "I'm cramping up" – "it hurts," I managed to get out.

"OK, how's this?" she said as she pulled back some.

"Better."

"So, how did it feel?" she asked

"Like you shoved a pole up my ass. How'd it feel for you?"

"I like it!" she exclaimed. "Ooh, that was probably the wrong answer. Oh, it's terrible for me – NOT!"

"I remember that. I guess I deserve it."

"You do. And now you deserve this." She reached around underneath me to grab my partially erect cock. "Hmm, thought this guy would still be hard. Let me see what I can do." As she started pulling out and pushing back into my rear, she used her other hand to stoke me back to a full erection. I could hear her straining though, but it wasn't long before the movement of her cock inside my anal canal and her stroking had me ignoring everything but the strange sexual sensations overwhelming me.

Finally, she slowed to a stop and said, "Umph, this is hard to do. It's so awkward."

After all this I didn't want her to stop. "I have an idea. Pull back out, I'll lie on my back and you can reach me easier."

I could see that little devious smile forming on her face. "OK, let's do it."

In her eagerness to try my idea she pulled out of me very quickly. I gasped and collapsed onto the bed, overwhelmed by the sudden rush, the heat from the withdrawal and all the sensations flooding through me.

"Ooh, maybe I shouldn't have done that! You OK?"

"You" – "are" – "a" – "fucker," was all I could get out. I could hear her giggling.

After just a moment I recovered and stood up. "Here, turn around and lay down on this side of the bed. Ok, now put your legs up and – oh yeah, there it is! You look like a girl about the get fucked."

"Gee thanks, that was really good for my male ego. Did you not notice this substantial difference?" I asked as I grabbed my now full erection.

"Wah, I got one too," she said as she grabbed hold of her erect dildo.

"You're making sure you keep your hands separate, right?" I asked.

"Yes. Left hand for dirty stuff, right hand for dirtier stuff like whacking you off. Don't you worry; I'll take good care of you. Are you ready to get all lubed up or would your male ego prefer we do it dry?"

"Nah, seems like that would hurt you more than me. Somehow."

"Whatever. Spread those cheeks wide."

Lying on my back with my ass completely exposed in such a submissive position was, well, weird. Hell, I'd just been sodomized by a woman with an artificial dick. My musings on how strange all this had become was suddenly interrupted by cold lubricant being inserted into my ass.

As Jessica prepared I could see her unlike before when I was face down. She was such a strange mix of innocence and wickedness – a beautiful, pixie like figure with a strap-on cock. She noticed when my cock twitched in reaction to my thoughts.

"Looks like somebody's getting excited. Are you ready?"

"Um, not sure."

"Well, it doesn't matter. Here it comes."

I tensed up briefly but by now I was able to take her dildo in pretty easily, at least most of it. Once she got to the threshold of pain she backed off a bit. "Good now?" she asked.

"Ok," I said, again breathing hard.

"Hmm, this is a lot easier to get to," she grinned as she grabbed hold of my erection. She leaned over and spit on it, then slid her hand up and down my now slick shaft. "Hold tight!"

She started bucking into me while stroking me intensely. I ended up holding my calves to keep my legs from swinging wildly as the sensation of being ass-fucked and jacked-off overwhelmed me. Although she tried to keep from going too deep just like I had, sometimes she accidently did. Somehow the brief feeling of discomfort seemed to heighten the pleasure.

It didn't take long before I yelled out, "Oh fuck, I'm cumming!" Jessica sped up both her hips and her hand. Within seconds I started spurting. I didn't care that it was flying all over my chest. Jessica's orgasm followed shortly afterwards, after which she collapsed on top of me.

We lay there spent for quite some time, breathing hard. I idly stroked her hair while she purred in contentment. Everyone once in a while she moved her hips to move the dildo in or out of me. We both shivered as the double ended dildo hit both our hypersensitive spots.

Jessica finally spoke. "Wow, that was fantastic. I've been dreaming of fucking your ass ever since you did it to me. So now we're truly even, partner."

"I'm glad I could make your fantasies come true. And by the way, you're still a fucker."

"So how was it?" she asked as she propped herself up on her elbows. Looking down we could see long strings of sticky cum trailing down from her breasts to my chest. I was a little embarrassed, but she just smiled and said, "Never mind, looks like I found the answer."

"So tell me, how did you like it when we did it before?" I asked.

"Well, I was scared and still upset about maybe getting caught taking that money. You blackmailed me into it, remember? But... yeah, I liked it and I'd like to do it again. What about you?"

"As long as you're not going to blackmail me into it," I smiled and rolled my eyes up in mock dread. "Yeah, sure, I'd do this with you again. And speaking of blackmail and why we busted each other, you know the longer we embezzle from the company the more likely it is that we'll be caught."

"Yeah, I know. I pretty much got everything I wanted," she grinned and smacked my ass. "Do you think we should stop?"

"Yes!" I said. "I like taking risks with you but I don't want to lose you."

"I don't want to lose you either. The money isn't worth it anymore," she said snuggling up to me.

As good as it felt to hold her eventually the dildo in my ass got really uncomfortable. With me propped up on the pillows so we could both watch she slowly pulled the strap-on out of my ass. "Whoa, that doesn't even look real," I said watching in fascination. "But you know, I thought the same thing when I was in you. So what's next, miss naughty?"

She pulled out completely and stood up, hot lube dripping from her dildo and out my rapidly closing anus. "Naughty, eh?" she said. She reached into a drawer behind her and pulled out the plastic ruler from my desk that she'd used to measure me.

"Hey, I've been looking for that!"

She walked back over to the bed and gave me the ruler, and then lay down across my lap with her lovely rear presented to me. The strap-on she was still wearing poked my thigh as she wiggled for the stimulation it gave her. Turning and smiling at me she said, "I have been naughty, stealing your ruler. Not to mention pegging you till you came. And probably a few other things. I deserve a good spanking."

"Hmmm... if you deserve a spanking I'm guessing I deserve a spanking too?"

"Oh yeah."

Our unusual arrangement had developed into an unusual relationship. I looked into her sweet but devious brown eyes and realized I'd found my soul mate.