Five Nights at a Conference Pt. 05

Note to readers: features a transsexual and male engaging in sex. If this isn't your thing, please move on to something you'd enjoy more.

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DAY FIVE

The final night of the conference, I felt like I had pushed my needs to exploit her as much as far as I needed. My mind had gone into some crazy places while it was adjusting to the shock of seeing that she had a dick, and figuring out how to deal with that. But the events of last night got me over that, and I figured we'd just get a nice long last night of fucking in. That ass, those tits, that mouth-they could make me feel plenty fine without needing to resort to any more baroque fantasies.

We met up in her room after yet another day of me trying and failing to restrain my fantasies during what would otherwise have been very inspirational academic sessions. She was more casual than usual: she was wearing a tight black knit longsleeve shirt, which held in and sculpted her amazing buxom rack. She wore faded jeans, which molded themselves sexily to her curves. I wanted to make sure she hadn't felt like we pushed things too far last night, so I asked her about how she felt about it in hindsight.

"Oh, it actually made me realize a few things about myself," she said. "No, don't you worry, I enjoyed the hell out of it. I was one satisfied lady after all those cocks. In fact, it made me realize that turnabout is fair play."

"Ha, what exactly does that mean?" I joked lightly. "I gotta admit I don't think I'm interested in getting gored through a glory hole."

"No, no glory holes," she said. "But tonight, our last night, I'm in charge."

"Oh really?" I said, smiling.

"Yes," she replied. "I'm in charge, or none of these tits for you tonight! All you have to do is trust me. I won't go too far. But I need you to agree to do whatever I say. Here, I'll give you a little taste," she said with a smile.

She lifted her shirt and flipped her bra cups up, to show off her amazing round breasts, protruding deliciously under the pressure of her shirt from above. Her nipples were already hard, and the light played off of their global forms seductively. She wiggled her torso back and forth, and her tits spun in hypnotic circles.

I eyed her (ok, just them) briefly, then agreed.

"You've got it—master!"

"Good," she said. She pulled the shirt back down. "You can start by putting these on."

She handed me two pairs of handcuffs.

"Actually, strip first," she said. "Then comes the bondage."

What the hell, I figured. I'd go for it. She had been a great fuck so far, no reason to go back now.

I stripped, and she had me cuff my arms to the bed posts, laying on my back. My cock hardened to its full size very quickly in anticipation.

She stripped down as well, revealing once again her impressive tits in all their naked glory, now removed from all impediments, as well as her flopping but still seemingly endless cock, which was itself free as a bird. She crawled over me, and dangled her nipples over my mouth teasingly, finally allowing me to lick at them. She pulled them away as they continued to harden, then brought them back just within reach of my tongue. After playing with this for a bit, I barely even realized her baton-like cock was bouncing up and down against my chest, oozing some pre-cum.

She languidly moved down on my body, and began to use those tits to manipulate my cock in heavenly ways. Back and forth she slowly moved them along my shaft, creating an almost excruciating joy, her nipples ribbing against my legs and pelvis. She looked right in my eyes, laciviously. My cock felt almost ready to burst already. Then she moved down further, and pressed on my perineum, releasing my instant urge to come. She then began to give me the slowest, most delicate blowjob of the week, using her lips and tongue to bring me to heights of ecstasy. She would occasionally put me deep into her throat, but was the opposite of a face fuck, it was slow and languorous. After long minutes of sucking, I was once again near the point of no return, and began to wonder where she would want me to come.

But just as I was ready, she once again pulled off.

"Ah ah ah, big boy," she said. "Now we get to the turnabout is fair play time. It's time you really dealt with my cock. No more just jerking me off, while you get to fuck my ass. I'm going to get some ass fucking in of my own this time, buddy. My cock wants to feel the heaven of a tight, hot asshole just as much as yours does!" She knelt back and jerked her pillar of meat suggestively a couple times.

Oh fuck. I wasn't sure I was ready for this. I mean, it had obviously arisen in my mind that this might happen. She had a cock. My cock had gotten close to her cock. I had jerked her cock off multiple times. But this was real now. Still, I couldn't ignore the fact that my own cock was hard as fuck from what she had been doing to it. And I was tied up with nowhere to go. She gave me another look, and I nodded. Let's see what the big deal is. It did look pretty fucking lustful, all hard and red like a piece of superheated iron pipe, pulsing in her hand.

I lifted my legs a bit to give her access to my asshole, but she shook her head.

"Nope, you're not going to want a cock like mine going in dry. You want to get it good and wet." She straddled me again, and brought her leviathan of a cock up to my mouth.

"Open wide!"

Somehow, this felt like even more of an intrusion than the idea of putting it in my ass. So personal. There it was, its head thicker than the rest, like a plum, and emanating a steady flow of pre-cum in a slow dribble that went down to the hollow of my neck. I opened wide, and she pushed forward. I tried to think of what I liked in a blowjob, and did my best to imitate that. Lots of tongue, lots of sucking, and very wet in order to get it maximally lubed up. One thing was for sure, my jaw was already straining and tired.

"Oh, fuck yes," she cried, and started pushing back and forth in my mouth, the rhythm building up to a regular fucking of my face. I couldn't relax my gag reflex to deep throat, especially with the thick head, although honestly I felt like it was kind of my duty to try. You can't go through life asking every woman who blows you to deep throat you and then not reciprocate. But as a first-timer, I wasn't having it. Still, she banged hard into the back of my mouth for a while. At least most of the shaft was thinner and more easily accommodated by my mouth in general, I didn't have to strain my whole jaw just to fit her in my mouth like she did with me. Again, my respect for what she had gone through to give me pleasure went up like a rocket.

"Fuck, I've gotta pull out or you'll make me cum. Nice job there, John, what a cocksucker you are! We'll have to revisit that later. But now, it's time for the butt. My cock has been looking forward to fucking some sweet ass for longer than you can know."

She moved back down, and I once again lifted my knees to my chest. She pushed forward on them to really open me up, then held her saliva and pre-cum-dripping ramrod at the base of my shitter. I tried to relax, and press out with my sphincter, and she pressed in. Even as thin as it was, it felt so fucking thick! If hers felt like that to me, I could only imagine what my much thicker cock felt like to her asshole! My mouth might have felt full of cock, but it didn't know dick compared to my asshole! She slowly pressed in a few inches, pulled back out a bit, then in again, repeating the pattern until all of her prodigious cock was filling my screamingly tight ass. I had never truly, really felt the muscles of my ass before, but I felt them now, all coiled around this invading snake monster that slithered up and down inside my internal tunnel.

Oh fuck I was filled up. But it felt fucking good, too. My prostate was getting an amazing pressure, and I could feel her all the way in my belly. She looked at me, and could see the pleasure in my eyes. But I'll tell you, it was nothing compared to the pleasure in hers. Her eyes started rolling in her head.

"God yes," she said. "Take my fucking cock!" Then she started to really fuck the shit out of me.

She slammed my ass hard, groaning with every stroke. It felt amazing. My sphincter felt on fire at first, then numb, then alive with a pure stretched warm pleasure that was hard to describe. After a while, she grabbed my cock, which was flapping on my belly, and started to jerk it off. Oh man, oh fucking man alive it was great. Honestly my cock was already primed and feeling great just from getting fucked, but with her hand action, it was like nirvana.

"Fuck, fuck!" I cried, "Your fucking cock is fucking amazing! Fuck me with your amazing cock!"

"Oh god oh god oh god I'm getting close," she said. "I'm getting fucking close!"

"Me too, me too. Oh god you're bringing me off!" I yelled. "Oh my god I'm going to come from getting fucked in the ass just like you did!"

She pulled her huge hose out of my ass, and started shooting her cum all over my stomach, massive blasts of thick white ooze painting my abs and my cock. When the underside of the head of my cock felt the first hit of sperm, it started shooting too, launching its own volleys of cum all over my chest. The two cocks seemed to take a couple minutes to finally stop shooting out. My chest looked like a Pollock painting, it was simply covered in criss crossing lines of sperm.

"Oh man," she said. "What a fucking climax. That was amazing. But here, bitch," she said, smiling. "Suck my cock. You don't make a girl cum like that without sucking the tip to finish it off. You know that."

She came around the side, and I dutifully sucked off her cock head, drinking in the last few dollops of sperm along with the shit taste of my ass. She groaned and her eyes pretty much rolled back into her head. I did know what it felt like—the fucking cherry on top of the sundae of a blowjob. Then she grinned and moved down to suck my own cock from below, while also putting a finger up my ass, which made my cock squirt out a couple more small drips of cum. She took my head in her mouth, and sucked in those last drops, bringing me to a final bit of maximal pleasure. Then she moved up my stomach and chest, licking up all the sperm that both she and I had shot there, her big tits and their long nipples running along my body, catching some of the cum as they moved, like street sweepers. She kept everything she collected in her mouth, ending up with a huge mouthful of both of our cum, her cheeks bulging wide. Then she came up to my face, and kissed me on the mouth, so that we swapped the sperm back and forth, a gooey mixture of hers and mine. After swapping it several times, and enjoying the swordplay of our tongues, we both swallowed a large amount of it, the thick warm mixture sliding down my throat.

She lay next to me, side by side, and we both just relaxed, breathing.

Soon she got up and unlatched the cuffs, freeing me.

"So, it seems like you liked that," she said.

"I guess I did. You've got quite a cock on you!"

"You noticed?" she joked. "I was hoping you'd notice earlier. But now we're going to make up for lost time."

I was already getting hard again, as was she. She played with her tits a bit, rubbing on the curves, pulling out the sperm-covered nipples.

"Let's try something a little more mutual," she said.

She laid me back again, then turned around so she was kneeling over me in the opposite direction. Both our cocks were hard as a rock now, and she lowered herself into positon for a 69. She took my cock in her mouth, expertly deep-throating it as I knew she could. There was only one thing I could do. I took hers in my mouth, and did my best to swallow. She occasionally took a break from sucking to give me some tips. I could pressure my left thumb in my fist, to get rid of the gag reflex. And damned if that didn't work! I was never letting any woman get away with not throating me now, if that's all it took! Her dick was hella long, but once I got the head in my throat, I figured I could just suck down the rest. I managed to swallow her inch by inch, breathing through my nose, until her bush was right up against my face. I had her whole fucking ten inches in my mouth and throat! That throat, I may add, had never felt so constricted. In the same way I couldn't imagine how full her asshole must feel, I couldn't imagine how she somehow managed to take my thick monster down her small throat. It must feel like her neck was completely full, let alone the tight point at the gullet! I could feel the friction and pressure as she fucked my esophagus. Luckily, she was gentle in the process. Until now, that is. Once I had her all the way in, she started bucking up and down on my face, turning me into a rapid-fire sword swallower, taking several hot inches in and out on every stroke. Of course, she was doing the same to me. I got the sense that she had been desperate for some good deep-throating, and was not going to let the moment pass by, just like any guy would do.

It felt goddamned amazing. Her blowjobs were so fantastic, like a tight vacuum around my dick, and I enjoyed giving her pleasure like that too. Having both just come, we took a little while to get to the brink again, but the whole thing was so sexy that it was less time than you'd think. Soon I started shooting my cum up into her throat, and then she pulled off a bit so she could savor the cum in her mouth. A few seconds later, she started cumming too, and blasted her load down my own throat. It was a crazy feeling. Then she pulled out as well, and shot the remaining loads into my mouth. She could come like a champion! It was hard not to gag from her overwhelming flood of cum, but I managed to swallow it all eventually, except for some that overflowed down my chin. The we turned and kissed and swapped cum once again. I was becoming a bitch to her extended horse-cock.

By this point, we were a bit tired, but we could both also tell that there was more to cum. We lay there for a while to reenergize, but eventually her hand started to stroke my cock.

"I want some more of that ass," she said.

I said, "I want some more of your own ass!"

We ended up taking turns fucking each other in the ass, one ramming the other, then switching up, bent over the bed, sitting on the other's lap, laying on our backs with our legs in the air.

It felt damn good to get reamed out by her. But I'm not gonna lie, I liked having my cock inside her tight asshole even more! But now I felt better because we were reciprocating.

This was a marathon session, since we had both already come twice. But eventually we had reached our limits. She turned around and got on her knees, and used her giant soft tits to finally bring me off. I shot a shockingly large amount of cum all over her tits and face, maybe even more than I had the first time. Then she stood up herself, sucked some of the cum from her nipples, then wiped a handful of cum off of her tits and face, then wiped it all over her cock as she stood in front of me. She jerked herself off, blasting on my face and chest. I sucked her cock head to give her a good finish, then wiped the cum from my face all over her tits, and sucked them again, in heaven. Nothing could be better than her thick gooey cum on top of her bouncing breasts and hard nipples.

For the first time, we slept together in her bed. We left the next day, knowing that we would make plans to meet up again at the next possible conference. There was no reason to let a golden opportunity like this pass us by. She was finally getting the chance to get her cock off like any guy would want, and I was happy to let her do so, while taking full advantage of her amazing body and skills.