Tales From the Help Desk - Part 2

“Harder, Jim, harder. Oh, God that’s good,” she panted, arching her back like she always did when she was about to cum. I had her on her side, one leg thrown over my shoulder, as I ground away, her hot, wet pussy clutching around my dick with every stroke. She closed her eyes as if in concentration. “Yes, oh, yes!” she cried, barely suppressing an actual scream. I wasn’t far behind her, and I let loose a torrent of semen, filling her—and then some. I dropped her leg, and collapsed on the bed next to her, amazed, and truthfully, a little proud, that I had managed to give—and have—three orgasms in just a few hours.

“Thank you, Jim,” she whispered, before getting up and starting to look around the room for her clothes.

“Anytime, Gina,” I whispered back, “anytime.”

“You know, I used to believe that,” Gina said, as she retrieved her underwear and stepped into them. “But I stopped by your apartment late two other times this week, and you weren’t home. I’m beginning to think I’m not your only girl anymore,” she teased.

Gina, my ex-girlfriend, and current friend-with-benefits, already knew she wasn’t my only girl. We had dated throughout our undergrad years at the university, but had decided to break up just before we graduated. Gina was now teaching at a private girls’ school across town and taking a few grad courses on the side. Our breakup had been amicable, and we would both occasionally drop by the other’s place for a beer, a chat, and a lay—no strings attached. That night, I had just barely gotten home from my part-time job supervising the university’s Tech Help Desk when she had shown up at my door, only somewhat thirsty and talkative, but very, very horny.

“So, who’s the lucky girl?” she pressed. “Am I going to have to start actually scheduling my booty calls?”

I sighed. Gina was open-minded and a good sounding board whenever I had any problems—with women or otherwise—but I wasn’t sure even she would understand my relationship with Paige Hotchkiss, better known around campus as “Professor Hot-tits” because of the x-rated fantasies she inspired among the school’s straight male population. The only reason I had been home when Gina dropped by was that Paige had attended a faculty dinner that night, meaning that we had been forced to move our fuck session up to earlier in the day.

“Come on,” Gina said, “You know you want to tell me.”

“Listen, if I do, no judgment.”

“Ooh. Juicy. Wait . . . you’re not screwing an undergrad, are you? One of your help desk staff? She’d better at least be legal, you son of a bitch.”

“Believe me, age is definitely not the issue. All three of us are consenting adults.”

Three of you? You might as well spill. Anything I imagine is bound to be worse than what you’re actually involved in.”

Somehow I doubted that, as I launched into the tale of how, for the past month, I had been screwing a very married Professor Hotchkiss with full approval from—and generally under the watchful eye of—her husband, who just happened to be Assistant Dean in the School of Computer Science, where I was currently pursuing my PhD.

It took Gina a moment to let what I told her sink in before she spoke. “So,” she said, “what you’re telling me is that you’re Hotchkiss’s fuck-toy while her husband is on sabbatical, and he not only knows about your relationship, but likes to watch . . . from 6000 miles away . . . in Switzerland?

“That’s about the size of it.”

“I should slap you upside the head and tell you this isn’t going to end well, but I suppose you know that already. Besides, I’m just too fascinated.” Gina had stopped searching for the rest of her clothes and climbed back into bed, pulling the covers up around her.
“Look, it’s just sex. It’s like you said. She uses me like a human sex toy, and her husband lets her because he somehow gets off on seeing her getting fucked by another man. That’s the deal. I get to do her. He gets to watch. Except . . . nah . . . it’s probably nothing.”

“Oh no, it’s definitely something. Except . . . “

“Except that Paige and I usually end up doing it once for show and then once, off-camera, for ourselves. She says it’s our little secret.”

Gina whistled, then misquoted Whoopi Goldberg in Ghost, “You in danger, boy.”

“Thanks, Gina.”


Fewer than twenty-four hours later, I was back fucking Paige, her husband Mark monitoring our every move remotely, and presumably jerking off to our performance. I had raced over when I got her call at the Help Desk, leaving a couple of my geeky protégés in charge in my absence, but when I arrived, I found her already in bed, legs spread wide, bound at each ankle to the bed frame with leather restraints. She barely noticed me enter the room as she was vigorously penetrating herself with a massive and—aside from its unattainable size—highly realistic dildo. As usual, she had gotten the party started without me.

She was moaning, and I could see how much the huge toy was stretching her, as could Mark, who was giving her instructions from his location abroad. “That’s it, baby. Punish yourself. You’ve been a very bad girl, haven’t you?” He continued, “Oh, I bet you like that, you filthy slut, don’t you? Only whores can take that much cock and still beg for more.”

“That’s enough of that,” I decided, switching off the flatscreen monitor that hung on the wall opposite the bed. I knew Mark was still there, watching, per our agreement, but I didn’t need to see him anymore, and I didn’t think Paige needed to hear him talking to her like that. Mark had told me privately that Paige liked it rough, but I wasn’t so sure if I had the stomach for it today.

Paige gestured to the restraints still lying on the nightstand, and understanding, I removed her hands from around her toy, and secured them to the headboard. Paige was now spread-eagled, her gorgeous body completely naked, with a giant ersatz penis lodged firmly in her pussy. I could only imagine how furiously Mark must be have been masturbating to such an image, and I was glad I couldn’t see it.

I quickly undressed, and got onto the bed. We had used the restraints before, even when we knew Mark wasn’t watching, and Paige enjoyed how vulnerable she was as I freely explored her body with my hands and mouth, causing her to writhe in anticipation. I would keep us on edge as long as I could before plunging my dick into her glistening folds, finally satisfying us both.

I knelt next to Paige, and prepared to remove the dildo, but she shook her head. “Leave it,” she said so low I could barely hear her. “It was his idea.”

I raised an eyebrow, but she just said, “Fuck my mouth, Jim. Make me choke on that luscious cock.” I heard the whir of one of the many cameras in the room being remotely repositioned to get a better view of the action to come.

I inched up the bed so I was kneeling over her when she brought her head up off the pillows and took my erection in her mouth. I had started to get stiff as I was tying her up, but now, being engulfed by her warm, wet mouth and bathed gently by her tongue, I found myself with a raging hard-on. I bent forward and supported myself on the headboard, arranging the pillows beneath Paige so she wouldn’t have to crane her neck so hard as she blew me. I knew I probably shouldn’t have been comfortable with a bound woman performing oral sex on me, but damn, Paige was a master at it, rolling her tongue around my glans and making me almost lose my mind before shifting tactics and deep throating me as I thrust into her, enjoying her take all of me, right down to my balls. Within only a matter of minutes, I was ready to climax, and she closed her lips even more tightly around me as I delivered a healthy load of spunk down her throat. I was afraid of actually gagging her, but I wasn’t going to give Mark the satisfaction of seeing me drench his beautiful wife’s face with cum, which is what I was sure he would prefer. “Later, Mark,” I said, as I withdrew my prick and reached over Paige to turn off the laptop that ran the program enabling him to witness the sex acts we performed.

“Now that he’s gone, let’s get you untied.” I first reached between her legs and carefully pulled out the huge cock, as thick as my wrist and topped with an even bigger head. Even with the generous amount of lube she obviously had used, I still couldn’t believe she had managed to get the monster inside of her, let alone thrust it in and out. She often liked playing with dildos and vibrators to warm herself up while she waited for me, but this was an apparatus I had never seen before.

“It came in the mail today,” she said, responding to my quizzical look. “All the way from Switzerland.”

Jesus,” I thought, as I worked to untie her, wondering not for the first time about their relationship and what kind of man wanted to see his wife used like this. I was beginning to think he had less of a cuckold fetish and was just kind of an asshole. And he had given me the speech about not abusing her. Were some of the disgusting things he wanted to see if I would do really fantasies of his? I shuddered a bit.

“Are you cold, Jim?” Paige had obviously noticed. “Come and lie down next to me.”

“Wouldn’t you rather be left alone? Aren’t you, uh, sore? I ran my thumb over the red mark the restraint had left on her right ankle, but I was really thinking of damage the dildo had to have done to her pussy.

“No. I want our special, secret time.”

I crawled into bed next to her and held her close. Her hands went immediately around my cock, coaxing me hard again.

“Paige, it’s okay if we don’t do it again tonight.”

“No, it’s not.” She sighed. “Jim, it’s clear you don’t understand our relationship, but I like it when Mark talks to me like that. I get off on pushing the boundaries . . .  exploring that thin line between pleasure and pain. If you don’t think you can continue to do this, I’ll understand, but I’d really like to keep seeing you. You allow me to explore my more ‘normal’ desires.”

With that, she put her leg up over me and guided me carefully inside of her. We lay like that for I don’t know how long, kissing and touching, Paige gently rocking her hips while I grew hard within her. A gentle orgasm would roll through her every so often as I softly kneaded her clit.

When she was ready, she shifted to her back, pulling me over on top of her. “Make love to me, Jim,” she said, her voice barely audible. She’d never said it that way before. “Fuck me, Jim.” “Rail me.” “Take me.” I’d heard them all before, but never, “Make love to me.”

Gina was right. “This isn’t going to end well,” I thought, even as my body obliged Paige, and made love to her.