The Dungeon

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The wingman plays a game with the wing-girl.
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Irish Moss
Irish Moss
2,393 Followers

Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me.

I'm not sure that the room Hugh escorted us to should have been called a bedroom. Okay, technically, it had a bed in it and it was a room, but it certainly wasn't someplace I'd be comfortable sleeping. It was in the basement of the townhouse that he rented and if this was the second bedroom, I wasn't surprised that he didn't have a roommate. Of course, I don't know if Tracy and I were expected to sleep in this room since I assumed that he and Theresa were not planning to do any sleeping once they headed up to his bedroom. I was Hugh's wingman and I guess Tracy was Theresa's wing-girl so I'm sure we were just supposed to keep each other entertained while those two finally stopped talking about how much they liked each other and actually did something about it. Had I been alone, I would have left and gone home but I knew that Theresa had driven so Tracy wouldn't have a ride home. I didn't want Theresa to freak out if she came and found Tracy and me both gone because I assumed there must have been a reason that she'd had Tracy accompany her in the first place. I doubted that Tracy would want to abandon her friend even though she'd been banished to the dungeon.

"So, are you the wing-girl or am I the wingman?" I finally asked, as we tried to make ourselves comfortable.

"What do you mean?" she asked with a bemused smile.

"Did you get invited to entertain Hugh's ugly, annoying friend or did I get invited to entertain Theresa's ugly, annoying friend?" I explained.

"Am I ugly and annoying?" she asked, sounding genuinely concerned.

"No," I replied honestly, "you're cute and funny so it must be me. Waaaaahhhhh!"

"I can't believe we're expected to just wait them out in this dungeon," she said, sounding disgusted after laughing at my phony crying.

"What are we supposed to do?" I asked, "Are we supposed to hook up, too?"

"Do you want to?" she asked, with what sounded like interest.

"Let's play a game," I suggested, figuring we should just cut to the chase and try to make the most of the situation we were in, "Let's see how many orgasms you can have by the time Theresa gets done upstairs."

"What about you?" she asked, which was an encouraging response.

"Let's just focus on you for now," I replied.

"Why?" she asked.

"Well, this way, when Theresa comes back," I explained, "she'll learn that the ugly, annoying guy tries harder."

"First of all," she said, "you're not ugly or annoying but, second, I do admire your generous nature so I'm totally up for your game."

"Okay," I went on, "how about this: I manually stimulate you to orgasm until you ask me to stop, then I switch to oral stimulation, again until you ask me to stop, then let's call it traditional stimulation."

"So, finger me, eat me, fuck me," she concisely summarized, "sounds like a trip."

We reclined on a bed that made me think of a prison cot and, as I started to unfasten her jeans, she pulled my face to hers and kissed me. I kissed her back with equal passion because I actually did find her quite attractive. She was a brunette with nice sized tits and some real curves compared to her friend Theresa, who had long, auburn hair and was quite thin. They were both pretty but I'd bet that, when they were out together, Theresa got more attention than Tracy did. I thought that was a crime, which is one reason that I wanted this to be all about her...at least initially.

I slipped my hand inside her panties and through her trim bush until I found her juicy pussy and started to lightly caress her clit. She pulled her mouth from mine briefly to let out a moan but we were quickly making out again even more passionately as she started rocking her hips rhythmically. I mainly focused my ministrations on her clit but occasionally I'd slip my finger down into her pussy to use some of her abundant juices to continually coat her clit. It didn't take long before she was tensing up slightly though obviously trying to remain relaxed. When she pulled her mouth from mine and let out a gasping cry, her body started to tremble so I smiled as she rode out her first orgasm.

She took a minute to catch her breath after she'd finished cumming and looked up at me with a smile as I continued to stroke her clit. She didn't try to kiss me again and I realized why when she started to gasp, still with a big smile on her face but now with her eyes closed. I don't know if it was like dominoes, but once she had the first orgasm, the second one seemed to build up a lot more quickly. Her gasping soon became moaning as she started to tense up again and, moments later, her body was shaking again.

After this one, she didn't open her eyes again; she just went right back to breathing rapidly with that big smile on her face. I realized as I dipped into her pussy for more lubrication that her pussy had become a lot wetter and more engorged since we'd started. I was looking forward to eating her to lap up her juices and fucking her to feel that engorged pussy wrapped around my tool, which was currently trying to burst from my jeans. It took about as much time between the second and third orgasm as it had between the first and second, which was less time than it had taken for her to have the first. As her body trembled again while she moaned, I was wondering if she was going to cum so easily all night.

"Ready to move on?" she asked breathlessly once she'd finished cumming for the third time. I was so I slipped my hand from her panties and got up on my knees to start working her jeans and panties down. Her bush was trim and dark brown and already matted with her copious juices so I was soon kneeling beside the bed as she positioned herself lying back across it with her head propped up on the pillows placed against the wall. Her legs were spread wide so I kissed her smooth inner thighs before running my tongue up her slit. She grabbed my head and moaned again as I started to lap up her pungent juices, rocking her hips toward my face. I looked up beyond her jutting tits to her face and we made eye contact, though the passionate expression on her face didn't allow her to smile.

Slipping a finger into her to feel how snug and slippery she was, I redirected my licking to her clit and she immediately moaned even louder. Pumping my finger in and out, I licked and sucked her clit while feeling a lot more positive about our exile to this dungeon. There was no doubt that I would be getting laid and, based on the number of orgasms she'd had already, I also suspected that this would not be our only encounter. Not only that, but I genuinely was enjoying eating her pussy, though I doubted it was as much as she was enjoying being eaten. Her breathing rate rapidly picked up again as she moved her hips faster and faster. Still holding my head, she started to tense up again until she let out a low moan and her body started to shake as she came again.

The recovery time between orgasms started to diminish with me eating her until they were occurring almost on top of each other. I was pretty sure that when she stopped me and suggested we move on that she'd had five in addition to the three manual ones. I straightened up and sucked her juices off my finger then stood as she sat up and reached for my belt. She undid my belt and opened my jeans, then worked them down until my throbbing tool popped out in her face. She briefly wrapped her lips around it while caressing my balls and gave me a quick demonstration of her oral skill.

"So what position will make it the easiest for you to cum?" I asked when she slipped my cock from her mouth.

"At this point," she replied, "it wouldn't matter. However you slip your cock into me, I'll be cumming like crazy."

"Okay, well, my staying power will be greatly increased if you are on top," I confessed, "so why don't we start there?"

As I pulled my shirt off, she worked my jeans and underwear the rest of the way down and helped me out of both them and my shoes and socks. I sat beside her on the bed and helped her out of her shirt and bra, exposing a really nice set of tits topped with large areolas and hard nipples. As I moved the pillows and lay back, she straddled me and guided my cock to her pussy before sitting down on it. We both moaned as her hot, snug pussy engulfed my rigid tool, then she started to slowly ride me while I caressed her big titties. Her pussy felt incredible as wet and hot and slippery as it was but, due to the way she had elected to ride me, I was relieved that I didn't feel like I was going to cum immediately.

True to form, it only took a few minutes of humping my cock before Tracy started to shake again as she had yet another orgasm. She continued riding me and was obviously building up to the next one when there was a quick knock on the door before it suddenly opened.

"Tracy, do you want to..." Theresa started before trailing off at the sight of us naked and fucking, "Oh my God, I'm sorry."

"No, wait," Tracy moaned out before Theresa walked out but still riding me as hard as she had been, "what's going on?"

"It can wait," Theresa replied but now watching us intently rather than trying to bolt.

"No, I'm listening," Tracy said, "just one sec."

Tracy started to shake and moan again as she came and I just continued to fondle her tits. When she'd finished cumming, she looked over at Theresa while continuing to ride my cock.

"So?" she asked.

"Hugh passed out on me," she confessed, "We started fooling around and, bam, he's snoring. I was going to ask if you wanted to go, but it looks like you are in the middle of something."

"The middle?" Tracy replied, "I don't know if I could handle ten more orgasms."

"Ten?!?" Theresa exclaimed.

"Yeah, baby," Tracy confirmed, "you backed the wrong horse, but I bet he wouldn't mind helping you try to catch up. Would you?"

"Parking is currently available on my face," I replied thinking that the dungeon definitely wasn't turning out to be so bad after all. I think the moan that Tracy let out as she closed her eyes again helped Theresa make up her mind. She quickly whipped her sweater over her head, revealing a very sexy bra, then dropped her pants to expose the matching bikini panties. My hands were on Tracy's tits but my attention was on Theresa's as she slipped out of her bra and it remained riveted as she started to lower her panties. Her auburn bush was well groomed and her titties were swinging enticingly as she pushed her panties down to her ankles. As she was kicking them aside and moving toward the bed, Tracy started cumming again causing Theresa to pause briefly then quickly climb up to straddle my head.

I watched her lovely pussy approach while taking her taut ass cheeks in my hands. She moaned as soon as I started to lap up the juices flowing from her slit, which had a slightly different flavor than Tracy's. Tracy continued to ride me as her latest orgasm tapered off and I gazed up to see Theresa's tits looming overhead. I could not believe how this night had turned out and that Hugh was snoozing through it. I had to give him some credit for getting Theresa worked up, though, because I wonder if she'd have even considered this otherwise.

I slipped a finger up into Theresa's pussy to find it, much like Tracy's, very slippery and quite snug. I wasn't expecting Theresa to cum as easily as Tracy did but, with her anticipation of being with Hugh and their foreplay being interrupted combined with her walking in on us, she might be that fired up to prove otherwise. I didn't necessarily care if she came as many times as Tracy did, either, because I assumed at some point she'd be giving Hugh another chance and this night would become a memory. In the meantime, I expected to continue fucking Tracy, so her satisfaction was my primary goal. Regardless of all of this consideration, Theresa did surprise me when she started to tremble and her pussy was flooded with additional juices.

I'd never been in a situation where the woman I was trying to satisfy made it so easy on me, much less two of them. I continued working on Theresa's pussy while Tracy continued to ride me and, by the time Tracy was on her fourth orgasm as a result of fucking me, Theresa was on her third due to my tongue and fingers. I don't know if Tracy just needed a break or what, but she climbed off of me and suggested that Theresa move back to ride my cock. Theresa didn't waste a moment and was quickly guiding my tool through her auburn bush. I made sure to take in Theresa's figure, assuming I'd not have the opportunity again, and likewise reached up to fondle her tits. Tracy eventually came around to kneel alongside the bed near my head and we made out at Theresa rode me.

Again, though she wasn't cumming rapid fire like Tracy had, Theresa did cum pretty quickly after she'd started riding me. I could feel her pussy becoming more slippery and engorged, which felt even more fantastic than it had initially, then she started to tremble while moaning even louder. After she'd experienced this a couple of times, Tracy asked Theresa if she thought they should give me an opportunity to cum by focusing strictly on my pleasure. Theresa agreed and dismounted me. I moved around to lie across the bed, propping up on the pillows placed against the wall as Tracy had earlier, while they knelt on the floor together.

Tracy took my throbbing tool in her hand and lowered her mouth over it while pumping it. I moaned as her lips slid up and down, immediately feeling my own orgasm beginning to build even faster. After a couple of minutes, she let Theresa have a turn and her technique was equally pleasurable. They alternated back and forth while I lay there just trying to remain relaxed while enjoying the pleasure I was feeling. I knew that I owed Hugh big time, though I suspected he'd never hear the full story, but if he hadn't dumped Tracy and me in the dungeon then fallen asleep, I would not have two hot mouths currently taking turns sucking my cock. As much as I wanted to draw out the pleasure that they were providing me, there had been way too much stimulation so far, both physical and visual. That combined with their oral abilities had me on the brink of cumming very quickly. I relished the pleasure while I could but also relished the feeling of finally exploding into Tracy's mouth. She swallowed my load before passing me back to Theresa, who nursed my spent cock for a bit before letting Tracy do the same.

They climbed up onto the bed and sat on either side of me, also laying back against the pillows. I was still checking out both of their naked bodies as they reveled in the number of orgasms they'd each experienced.

"I don't know about you, Tre," Tracy said, "but I like this game and I plan on playing again."

"Oh my God, yeah," Theresa responded, "but I still want to see what happens with Hugh, so if we could keep this between us."

"What happens in the dungeon stays in the dungeon," I assured her.

"Well, in that case," Tracy said, "maybe we should get dressed in case he wakes up and comes barging in on us like you did."

Theresa went pale and quickly got up to grab her clothes while Tracy went over and locked the door. They started getting dressed while tossing my clothes over to me, but I didn't start pulling on my own clothes until they'd covered up the parts of themselves that I was most interested in. Once we were ready to go, Theresa went quickly upstairs to write Hugh a note before we left while Tracy waited with m.

"With or without Theresa," I told her, "I expect to be seeing you both soon and a lot."

"You bet your ass," she replied.

Irish Moss
Irish Moss
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Dick88Dick88about 7 years ago
I think he meant...

..."with or without, Hugh."

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