My Fiancee & The Professor

After the morning that my fiancee, Tracy, caught me masturbating — and not just jacking off but down on my stomach, humped across a pillow, and fucking a rubber toy (see my story "Caught!") — I spent the rest of the day careening between arousal and humiliation as I waited for her to come home. She'd promised me that we'd "talk about it later," but I had no idea which direction that talk might go in. And even after she came home, she kept me waiting — avoiding me by busying herself with a few household chores and then making dinner and eating dinner, avoiding my looks, acting as if nothing was wrong. It was only after we'd finished dinner, chatting about her day, that she pushed herself back from the table and met my eyes.

"When I walked in on you this morning," she began. "I didn't know what to think. I was surprised, of course — hadn't imagined you were doing that while I was away at work! — but I was also a little sad and angry. Sad thinking that I apparently wasn't giving you enough to keep you satisfied, and angry that you were hiding this from me." Here she paused. "And also... a little turned-on, as I guess you saw."

"Up close and personal," I said, remembering how she'd pulled up her skirt and jammed her ass in my face while both of us got off.

She smiled. "Very," she said. "And that was surprising too, I think — my own reaction. And the more I thought about it today — and I thought about it a lot, I have to tell you — the more I decided that this was a good thing. We're getting married, and it's good to know one another — everything about one another — and if this is part of who you are and what you do.... Well, then, I want to know about it." She paused. "And I need to tell you something as well — a secret of mine. One that might explain my reaction this morning."

And that's when I learned something new about Tracy too.

***

When she was in college, long before I knew her, Tracy had had an affair with one of her professors — "a sort-of affair," she said, explaining, "That's part of it."

He was an older man, of course — in his thirties and married, but still handsome. All of the girls had crushes on him, Tracy said, but she was the one he'd singled out one afternoon, chatting her up after class, inviting her for coffee one day and then regular coffee dates, and finally admitting what she already knew, that he was attracted to her.

"How could I not know?" Tracy told me. "It wasn't just all that attention, all that conversation. Each time after we'd finished out coffee, he'd he stood up and I could see the bulge in his pants, where he'd gotten an erection just talking to me, just sitting across the table. It was funny to see how gentlemanly he was, how proper and... professorial, I guess, when all the time he had this raging hard-on. Several times I thought about just reaching out and touching it, letting him know I wasn't blind."

"Were you attracted to him?" I asked. "Were you in love with him?"

"Attraction, sure," she said. "He was handsome. It was provocative to think of a professor getting all hot over me — something new and tantalizing. But love? I wasn't entirely a silly schoolgirl, but it was flattering. I was interested, intrigued. But he was married, and I reminded him of that when he admitted he was interested in me — being coy really. At that age, I think I would've slept with him anyway. I didn't think about the effect I might have on someone else, especially a woman I'd never even seen before, and the fact I wasn't with anyone at the time, so I would've been game for it. But he took me seriously about my hesitation, and then explained that he had a plan."

The professor invited Tracy to meet him at a hotel room and she was interested enough to go, figuring that once they got there he'd drop his defenses and they'd end up fucking. But when she got there, he really did have a plan. He told her that while he wanted Tracy — desired her so much that he could barely keep his mind on his lecture when they were in class and then could barely keep his hands off his cock afterwards — he did not want to cheat on his wife, but he felt that as long as they didn't have intercourse, it wasn't really adultery. And so, would she just take off her clothes and let him jack-off in front of her?

"I'd had sex by that point, obviously," Tracy told me. "And I wasn't naïve about things: I knew that guys jacked off. But I'd never actually seen a guy do it."

"So you told him yes?" I said, and I could feel my own hardness growing as she continued her story.

"Of course," she smiled.

The professor had pulled down his pants in front of her, and she finally glimpsed what she'd online seen in outline beneath his pants at their coffee dates. He was already hard — an impressive cock, she thought at the time, even as she almost laughed at the whole thing, her professor in front of her with his pants around his ankles. He asked her to open her blouse a little and she did, revealing her bra, and then he'd begun to stroke himself, sitting on the edge of the bed, a hot, hard animal trying to release some of his tension. He hadn't asked her to strip down anymore, hadn't asked to touch her or for her to touch him. Instead, he'd just jacked himself off, spraying his cum across the floor, and then thanking her for watching — "for not judging," he'd said.

"It became a regular thing," Tracy told me. "About once a week. A tension releaser for him, he said. And as we went on, I got more into it: baring my breasts, flashing my panties, or even pulling my panties aside to flash what was underneath them. Soon, I'd pull my skirt up like I did for you this morning, let him look at my little asshole, and that always got him off hard. I'd lean over the dresser, pull up my skirt, and there in the hotel room mirror, I'd watch him behind me on the bed, imagining his face between my legs, his nose in my ass — kinky fantasies for me at that age, I didn't even know where they came from. Just his own kinkiness inspiring me, I guess, rubbing off on me. Sometimes, he'd get up on his hands and knees behind me there on the bed and just...." She laughed. "He'd just be yanking on himself like he was gonna pull it off, and I stayed cool and calm, urging him on. 'That's right. Tug on it for me. Cum for your little Tracy.'"

I was touching myself by that point, listening to her, rubbing myself through my jeans. I could picture it all, pictured myself as the professor.

"But you never let him lick your pussy or your ass while he was doing it?" I asked, thinking about her sticking her ass in my face that morning when she caught me.

"No," she said.

"And you never slept with him?" I asked.

"No," she said. "Which surprised me. I was sure we would fuck eventually — my pussy would get so wet every time — but we never went that far. But before long, we'd gotten even more daring. I'd let him cum on my tits sometimes, or on my leg. Once, he asked if he could hump my leg, and I let him. I'd rub my pussy juice on the side of my thigh to get it nice and wet and then I'd sit on the bed and then he'd straddle my leg and just ride it, like a dog. That was the closest we got. But that was such a turn-on too, seeing the effect I had on him, how much even my leg could get a man off like that. He asked me one time, riding my leg, 'Have you told anyone about this?' And I told him the truth, 'Of course I have.' And he asked, still riding my thigh, 'Your girlfriends, the girls in our class?' And I told him, 'Yes, they all know.' And he'd shot one of his biggest loads then."

"You really told them?" I asked Tracy.

She laughed. "Of course! You think I could keep something like that to myself?" And I pictured all of them giggling about it.

"And then what happened?" I asked.

She waved her hand. "I kept on like that for a while, and then it ended. I started dating someone else, stopped returning the professor's calls, forgot about it really, until.... Well, until I saw you this morning, humping that pillow, getting off like you were. And then it all came back. I was turned on watching you, turned on thinking of you like that professor, so hungry to get off."

***

I was hungry to get off again after she finished her story — my own cock was bulging against my jeans much the same way her professor's cock must have strained against his own pants. When she asked me, coyly, if I'd show her again what I'd been doing this morning, I was happy to oblige.

She had me bring my "equipment" up to the bedroom this time, where usually I'd masturbated in my office downstairs. I brought the pillows up and the little rubber pussy and the towel I wrapped it in and the lube. I brought up my laptop too, because she wanted to see again which images got me off. I'd expected she would do what she'd done that morning — hike up her skirt and shove her pussy and ass in my face — but she didn't this time. As I prepared my little masturbation scene, she scrolled through the browser on my computer and picked out some images, a series of blondes with smallish tits, which was interesting, I thought, since my fiancee is a redhead with larger boobs. It was interesting to see how she wanted me to get off to someone so different from her.

She laid the computer down in front of where I'd place the pillows.

"Pull down your pants," she told me.

I did and my cock stood at attention.

"Lube it up," she gestured toward the toy, wedged between the pillows.

I did that too.

"Now hump it," she said, quieter now, a sense of curiosity and awe and maybe arousal in her voice. And as she watched, I leaned over the bed and slid my cock inside the toy, my feet still on the floor. Slowly, I began to slide my cock in and out of my little toy, very slowly so I didn't cum too soon.

She watched for a while, moving around me like she'd done earlier in the day, examining what I was doing from every angle. I was getting turned on, of course — it was a fantasy I'd imagined even before our morning run-in, and now I was getting it twice in one day.

And then — what crappy timing! — her cell phone rang!

"Don't stop," she said as I turned back to look at her behind me, already pulling the phone out the purse on the dresser. "It's work," she said. "I need to get it." Then she leaned over me, pressing her tits against my back and her groin against my ass and whispered in my ear: "Don't stop. I'll be back in a minute." And then she stepped out of the room. "Hello," I heard her say as she moved down the stairs and out of earshot.

I did as she told me, trying to keep my pacing right so I wouldn't cum while she was away. But it was tough with all of the women on my laptop screen — a series of blonds in various windows and the computer scrolling through them: this young blond with her hands covering her nipples and a bush on full display; this one in a schoolgirl skirt, bending over and giving a peek of her panties; that one lying on her bed with a vibrator teasing the edges of her cunt; another with pigtails and a lollipop; and on and on like that. Visual overload.

Finally, I heard Tracy coming back up the stairs, and then her voice behind me: "You remember when I told the professor that all the girls knew what we were doing?" she asked.

And when I turned around, I saw that she wasn't alone.