Caught Again Has Its Benefits

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Masturbation, exhibitionism & my fiancée in a lesbian 69.
2.2k words
4.38
59k
7

Part 1 of the 2 part series

Updated 09/22/2022
Created 05/14/2009
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VAGradSch
VAGradSch
14 Followers

This is the third in a series of connected stories that began with "Caught!" and "My Fiancee and the Professor." While it's not entirely necessary that you read those two stories first, I did want to provide some context.

*

Here's the scene: After catching me masturbating earlier in the day and forcing me to finish in front of her, my fiancee Tracy shared a story about her own college days, in which she had regularly exposed herself while an old professor jacked off in front of her. After telling me her secret story, both of us were hot, and Tracy asked me to masturbate in front of her again like the professor had, and so there I was once more the way she'd caught me that morning: a rubber pussy wedged in between two pillows on the side of the bed, my pants around my ankles and my cock stuffed inside of the toy, a laptop in front of me on the bed, with photos of sexy young blondes showing me their tits and asses.

And then in mid-humping, my fiancee had gotten a phone call and stepped out of the room, only to return with someone else with her: her co-worker Natalie, who was suddenly in the doorway, her eyes wide and her jaw dropped.

"See," said my fiancee. "It's just like I told you."

"Even better," said Natalie and smiled. A seductive smile. A mischievous one.

***

Natalie is, I should tell you, a knockout. Where my fiancee Tracy is now in her early 30s, a tall, slim redhead, Natalie is probably only a year or two out of college: shoulder-length blonde hair, breasts that seem just slightly too large for her small frame, a great smile, a beautiful ass.

Despite the slight age different, she and Tracy had hit it off from the moment Natalie joined the office, and Tracy had come home often with stories of Natalie's latest romantic escapade, a new boyfriend or a new breakup or a hot new one-night stand in a club bathroom or the back of a car.

I couldn't help but remember these stories when I first met Natalie myself at one of Tracy's office happy hours, and I couldn't help but be turned on by how much she seemed to be flirting with me. "So you're at the university?" she asked me, bright and bubbly, and I told her yes, grad school, physics, and she leaned in closer, her shirt cut low and revealing sweet orbs beneath, and whispered, "I bet all the girls are really hot for you, huh? The whole teacher-student thing?" She winked.

I didn't have the heart to tell her that I wasn't on a teaching track, just research, just me and my experiments, and so I indulged her fantasy a little and then remembered it myself sometimes when I'd jacked off afterwards. But none of my fantasies had prepared me for her walking in with my fiancee and the two of them at the door, watching my bare ass as I humped a pair of pillows.

***

"Don't move," said Tracy, sensing apparently — and rightly — that I was about to jump up and hide myself.

"Yes," said Natalie, a little breathlessly. "Please don't move."

I stayed where I was, but stopped the humping I'd been doing when they came in. It was tough to stop, especially when I saw that Natalie was wearing a little plaid skirt and short little socks with black shoes. Her shirt, plain white, was literally bursting at the seams.

Tracy moved closer and put her hand on my back. "I went to lunch with Natalie," she said, "and I told her about what happened this morning, and then the story about me and the professor, about taking off my clothes for him, about how he got off just watching me. And I told her how I told several my friends and how they'd giggled about it and how a couple of us joked about putting on a show for him — a two-girl show — and about how hot it made me thinking about it and how disappointed I was that none of us ever followed through."

"And that's when I said that there's no time like the present," said Natalie, giggling.

"Can we?" asked Tracy.

And I nodded. "Sure," I said, and heard my voice break from my nervousness and excitement. My cock was harder than ever thinking about it.

Tracy and Natalie both laughed then, and Natalie handed my fiancee a bag. "I had an extra one," she said, mysteriously, and Tracy said, "OK, just a second" and told me, "Don't move" and disappeared into the bathroom.

While Tracy was gone, Natalie knelt down beside me, and I felt myself blush. She must have seen it. "Don't be embarrassed," she said, and her touched me lightly with her fingers. "It's really natural, I think," she said. "And I promise it'll be fun." She smiled and leaned down closer. "And Tracy said that if you don't cum from the show, you can have anything you want to get off — and that includes me." There was a twinkle in her eye as she spoke. "Now quick," she said. "Stand up for a second." And when I hesitated, she urged me again, "Quick, before she gets back.

I stood up quickly, and Natalie pulled out a condom and slipped it on my cock. "Nice," she said, as her fingers ran down my shaft. "This is just to slow you down, to make sure that you make it all the way through the show." And she used her hands to slide me back into place, giving my balls a little squeeze at the last minute. Tracy came out then and I saw what had been in the bag: a matching schoolgirl outfit, the plaid skirt just barely covering her pussy and her rump.

"Are you ready?" she asked me, and I nodded again as she and Tracy moved the computer over and sat down on the bed in front of me.

"Are you ready?" Natalie asked her, and Tracy nodded too, nervous herself I could see. "Then let's see what happens."

I'd wondered for a moment if they'd done this before — if those lunches they'd had were something more clandestine — but that question and the response seemed a clear indication that this was a first for everyone, and both Tracy and Natalie seemed a little hesitant and nervous as they reached over and started rubbing one another's arms and tentatively touching each other's breasts. But Natalie seemed the bolder of the two, and soon she began speaking to me, channeling not just Tracy's old fantasy but also the one she'd suggested to me at that happy hour.

"Do you like what you see, professor?" Natalie asked, rubbing a hand inside Tracy's shirt, tweaking a nipple. "All the girls think you're sexy," she told me. "All of the other girls are jealous that we get to do this."

I slowly humped my little toy. The sensation dulled tremendously by the condom but I couldn't help it and then I was glad for the extra layer, keeping me from cumming immediately.

Tracy kept stealing glances at me for the first few minutes, but soon her eyes were closed and she was locked in an embrace with Natalie, kissing her, fondling her breasts and her ass, the two of them pressed up against one another. A shirt was unloosened more and Tracy's breasts fell free; Natalie bent to kiss them, sucking each nipple into her mouth while Tracy moaned; then suddenly, Natalie turned to me. "Do you want to see?" she asked me.

Natalie spun my fiancee around then, so that she was facing me on the bed. She cupped Tracy's breasts as if offering them to me. "Nice, huh?" she said. "You've jacked off thinking about them before, haven't you? You always give her a better grade after you've jacked off over them, don't you?" Then she reached down and lifted the edge of Tracy's little plaid skirt. "And then the best grades are for this, aren't they? See if you can catch a little glimpse." And she pulled the skirt up higher and then reached down and eased Tracy's panties aside so that I could see her wet cunt beneath. Tracy moaned as Natalie's fingers brushed against the lips of her pussy. "You like it, don't you, professor? You want to fuck this instead of that toy, don't you?"

I nodded, breathing heavy, humping away hard.

Natalie leaned down then and gave Tracy's clit a little lick and then moved Tracy around for a better angle. I watched Natalie head disappear between Tracy's thighs and then bop up and down as she licked and licked.

Soon, Tracy spun Natalie around so that her head was close to mine and then climbed on top of her in a 69. When Natalie bent over to continue licking Tracy's cunt, I saw that Natalie hadn't worn any panties underneath her own skirt. Her own pussy was shaved clean and soon she pushed it down onto Natalie's lips, which had already been reaching up eagerly to taste them.

Based on how slow our own sex life had been recently in the midst of all the tension of wedding planning, I was hardly prepared for the lust I saw in Tracy then. And though my fiancee had never given me any indication that she'd ever had sex with another woman, she seemed to have no hesitation lapping up Natalie's juices. After a few seconds, she opened her eyes and looked back at me, the bottom part of her face buried completely between Natalie's thighs, but I could see how excited she was by it all, how happy.

Tracy reached up then and touched my face with her hand, rubbing my cheek and then pushing a finger into my mouth. I don't know if it was her juices or Natalie's, but I could taste the pussy on her finger and I liked it hungrily as Tracy rubbed it again and again against my tongue and the inside of my cheek. It must be Natalie's pussy I'm tasting, I thought then. Tracy must be getting off on seeing me taste another woman's cunt for the first time in all these years. But then I realized Tracy was just getting her finger lubed up, because she quickly pulled it out of my mouth, eased up Natalie's skirt, and begin tracing the sloppy wet finger against the younger woman's smooth little butthole.

Natalie responded eagerly. A little moan from where her head was buried between my fiancee's pussy and then a quick, urgent arching of her back to encourage what Tracy was doing. Tracy eased her finger into Natalie's ass just up to the first knuckle and then slowly kept sliding it in until it was buried completely within.

If there was any point at which I thought I'd completely lose it, that was it. Tracy had sometimes let me put a finger up her own ass, but never very far and never anything more. "No butt sex," she told me flat-out, but here she was penetrating another woman's ass with no mercy and no hesitation. I was bucking my cock into that little toy for all I was worth, rubber condom against rubber pussy. The latex smelled harsh, like it was burning, but I kept going, sure I was going to blow my seed any second.

But before I did, Natalie let out a low groan and then a giggle, and I saw her butt clenching, spasming against Tracy's finger. And as soon as it happened, I saw that look in Tracy's eyes too that always told me she'd reached her own climax.

I slowed down my humping then, waiting to see what happened next.

Gradually, the two women relaxed, their bodies settling down, and Tracy rolled off of my fiancee, exposing her well-licked pussy for me to see, it's naked folds glistening with moisture. Tracy smiled up at me and then closed her eyes, and we all lay there for a few moments in silence.

"Did you cum?" Tracy asked finally, but before I could answer, Natalie jumped up and moved around behind me.

"Let's see," said Natalie, as she pulled my cock out of the toy. The condom had bunched up halfway up my cock, and Natalie slid it free and then stuck her finger in it. "Looks like he held out," she laughed, and then stuck her tongue inside the tip of the condom. "Yep," she says. "He gets the prize."

"Whatever I want?" I asked.

Tracy nodded.

"I want anal," I said.

"Except that," Tracy said quickly, with a panicked look.

"I meant with her," I said then, and where Tracy had blanched, Natalie just smiled that same sexy smile.

"I'm game," she said and then added quickly, "I mean, if it's OK with you, Tracy."

Tracy hesitated at first and I could see her thinking about it. It was one thing for her to be with a woman; another thing for me to. And I knew what she meant; while I was turned on watching her and Natalie together, it would've been entirely different for me to see her with another man.

"It's OK," I said. "Don't worry about it. I'll just—"

"No," said Tracy, quietly. "It's OK. I... I want to see it, though."

"Absolutely," said Natalie, and I nodded too.

"After that," I said. "Anything."

"Anything?" asked Natalie then, and she reached into her bag once more.

I honestly thought the buttplug she pulled out was going to be for her.

VAGradSch
VAGradSch
14 Followers
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4 Comments
AnonymousAnonymousover 12 years ago

Nice beginning, but we need few more chapters to fill the story out.

klippertklippertabout 13 years ago

you Just knew that bag had other tricks in it......

klippertklippertabout 13 years ago
hehehe

you Just knew that bag had other tricks in it......

AnonymousAnonymousalmost 15 years ago
very hot

Hot scenario - a little different with the toy - and good descriptions. You seemed to mix up names a couple of times, which kind of broke the flow. Be more careful please, but WRITE MORE!

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