My FWB Dares Me to Fuck Her in My Girlfriend's Room While She's Sleeping: Tutoring Sessions Part 9 [F20sM20s] [Cheating?] [Striptease] [Sex Game] [Multiple Orgasms] [Cunnilingus] [Fingering] [Anilingus] [Vaginal] [Light Dominance] [Panty-gag] [Anal Fingering] [Cumshot] [Cum play] [Part of a Series]

Link to Part 1: https://www.reddit.com/r/eroticliterature/comments/1mhe231/when_fantasies_align_tutoring_sessions_parts_1/?ref=share&ref_source=link

Link to Part 8: https://www.reddit.com/r/eroticliterature/comments/1mmigvr/my_fwb_treats_me_to_a_show_after_a_night_of/?ref=share&ref_source=link

Part 9: Grace's Game

To my surprise, Grace didn't open her door, instead putting her ear to Tera's. With the door ajar, I could hear her snoring softly. Apparently Grace's and my conversation had done nothing to wake her up. I guess this was what Grace had been looking for, as she opened the door and pulled me into the doorway. She stood on her tiptoes and whispered into my ear.

"So here's the game: you are trying to give me as many orgasms as you can without waking Tera up." She gave my ear a little lick.

I whispered back, "so how do I win? Am I aiming for a certain number?"

"Playing the game should be its own reward." She said, fumbling with my buckle, so I started pulling my shirt up over my head. She got it loose and pulled my pants to the ground at the same time I got the shirt stuck over my face. I felt her give my cock a gentle kiss, but she stood up again by the time I was untangled. I now stood there naked before her. "But how about this: for each time I come before Tera wakes up, I'll give you a blowjob, anywhere, anytime you want. Sound fair?" Grace was right; I'd have played with no additional reward, but I nodded my agreement. She whispered in my ear one more time. "Two rules. First, we don't have any lube, so don't put it in my ass. Anything else is fair game. And second, I'm not going to hold back as far as making noise goes, so if you want me quiet you're going to have to make me be quiet." With that she stepped backwards into the room, shrugging off her shirt so that it fell to the ground at her feet.

I'm not usually excited by the idea of dominance, but something about the way she'd said it pushed me over the edge. I stepped out of my jeans, which together with my boxers were crumpled on the floor, into Tera's room, naked once again. I grabbed Grace just under her butt, picking her up entirely and moving her to the rug in the center of the room. I laid her on her back as quietly as I could, just a couple meters from where Tera lay sleeping. Though I was pretty revved up, I thought my best bet would be to start building some tension in Grace, so I forced myself to slow down. I knelt between her ankles, then lowered myself to my elbows. She craned her neck to look at me, an expectant look in her eye.

I began by ignoring her crotch completely, licking her thighs with a soft flat tongue. I started about mid thigh, giving long licks perpendicular to her leg that moved progressively closer to her panties. But when I got close, I would switch legs and start over. This seemed to thrill her a little bit, but she was still just watching and waiting. So after a minute, I decided to step things up. I limited myself to just her upper thighs, near the edge of her boy shorts. When I felt her shiver slightly, I moved even further up, feeling the lacy edge of her underwear against my tongue. Hardening the tip of my tongue, I pushed it into her soft skin and up towards the panties at the same time, and to my delight, I actually got it underneath. I closed my teeth on the panties and pulled, while moving my hands under Grace's lower back to pick her butt up off the ground. In a feat of oral dexterity I would forever more be proud of (and only sometimes manage to replicate), I pulled her panties off without touching them once with my hands. Grace waggled her eyebrows at me, which I decided to interrupt as her being impressed by my move. Her pussy now exposed and mere centimeters from my mouth, I went to work.

Grace was shorter than Tera, and her pussy was a bit smaller accordingly. Her lips were darker, just as rest of her was, and as I'd noticed the day before her only tan lines were here on her pelvis. I continued my earlier perpendicular licks from before, alternating sides and inching closer to the center until I was brushing up against her labia. They were large but only relative to her small pussy, and they opened eagerly as I pushed Grace's legs wider with my shoulders. I pulled one of her labia into my mouth, sucking gently on it, then gave the other the same attention, checking to see what that was doing for Grace. Despite her warning, she hadn't made a sound, and she was smiling at me but hardly looked to be approaching ecstasy of any kind. I resolved that I had to be a bit more direct, and starting lapping right between her lips, from just below her vagina and ending on her clit, which was small even compared to her diminutive vulva. This approach had worked wonders on Tera, but after a minute of this, with a little bit of clit sucking thrown in for good measure, all I was rewarded with was a little heavy breathing. Grace even gave me a thumbs up and a patronizing smile that seemed to say "Nice effort!"

I was nearly stumped, was this game going to go nowhere? Then I remembered what had done it in the shower, and could've slapped myself in the forehead if my arms weren't busy. I got up onto my knees, making a bit more noise than was perhaps wise, but I looked over at Tera and saw her expression still blissfully unaware. I made a "turn over" sort of gesture to Grace, then took a hold of her knees to help her do so. She gave me a real grin this time, and her eyes seemed to flash as she got on her hands and knees. Her pussy was well wet now thanks to several minutes of licking, so I had no trouble sticking two, then three fingers in, though I suspected that was as many as she could fit. The sight of her anus exposed in front of me was beginning to be a familiar sight, and I wasted no more time. I began my wide slow licks again, this time centered on her butthole.

Finally I was seeing results. Grace looked back over her shoulder and mouthed "Oh Yeah!" She started to rock her hips back into me, in time with my licking. After just a minute I felt the telltale shaking begin, and I pushed my fingers further into her vagina while firming up my tongue to roughen the licking at her sphincter. This had the desired effect, and she gave a soft wordless "eep" as she started to come on my fingers. She held one hand up off the carpet, holding a single finger up. I watched her anus clench and relax with satisfaction, but I knew from the night before that I could keep this going and get another orgasm out of her without too much more work if I kept at it. The problem was my neck was getting sore from craning. Thinking quickly, I got my feet under me and grabbed Grace by the hips, lifting her up onto hers. She looked back over her shoulder at me, but I just guided her over to the foot end of the bed, giving her a slight push in the upper back so she bent over with her hands on the comforter. I stole a quick glance at Tera again. She moved slightly in her sleep, but didn't wake. Not wanting Grace to cool down, I quickly knelt behind her and resumed my lingual assault on her ass. Much more ergonomic! I was even able to spread her butt with my hands now, letting my pointed tongue start to probe into her anus. Grace must have been surprised to feel me enter her, as she let out an "Oh!" in a decidedly non-muffled voice. I knew I was bending her don't-put-it-in-my-ass rule, but I stopped and glanced up and she waved for me to continue, so I did. Unfortunately this was causing her volume to slowly and steadily increased, and I knew there was no way Tera wouldn't wake up if this continued. My mind raced, I didn't know what to do. I couldn't reach Grace's mouth to muffle her from here... my eyes cast about while I thought quickly, and then I had it.

I stopped licking and removed my fingers for just a moment, and bent to pick something up from the ground. Grace started to stand feeling me move away, but by the time she had half turned I was ready. She started to ask something, but I interrupted by stuffing her panties into her mouth. Her eyes took on a look of surprise, but then quickly settled into hunger, and she turned back to the bed, presenting herself to me. Her eagerness took me by surprise, and it emboldened me. I had meant to resume the oral treatment, but seeing her presenting herself to me so openly took me past some internal limit. I'd been hard as a rock this whole time despite nothing touching my cock, and I couldn't help myself any longer. I stood behind Grace and shoved myself into her vagina with no warning. Despite the suddenness and her size, she'd already had one orgasm and was well on her way to a second, so she took most of my length with no trouble. She said something that might have been a "Yes!", but I couldn't tell through the panty-gag. Whatever she's been trying to say, it definitely fell under the column of assent, so I started fucking her with gusto.

Now conscious of the fact that Grace might not come without some sort of anal involvement, I spread her ass with one hand and wet one finger from my other hand in my mouth to fondle her asshole while I continued my vigorous strokes. Grace gripped the comforter in both hands, actually pulling on it a bit by accident. I spit in my hand, rubbing it into her asshole, and she started to shake again. Once again, Grace clenched around my cock while she orgasmed (though with her vagina instead of her ass this time) and just like last night I had just gotten started, or I would have come too from the extra sensation. So as Grace held up a hand with two fingers extended, I continued humping her, even harder now. Her asshole was still contracting and relaxing in time with the waves of her orgasm, and I found myself staring at it. I was beginning to be fascinated by that once-forbidden hole. By this point I had forgotten the game entirely, my brain in wild animal mode. The time between my having the idea and executing it was practically zero.

I withdrew my cock from Grace's wet sleeve for a moment, only to replace it with the thumb of my right hand. I used my left to stimulate her clit at the same time. Her vulva was soaked with her juices and my precum by now, and my thumb was quickly coated in them. Swapping my cock back in just as quickly, I resumed my fucking and spread her butt cheeks as wide as I could with both hands. Her unstretched anus was quite a tighter hole than it had been when she'd invited me to fuck it yesterday, but without another thought I pushed my dripping thumb inside. I definitely felt more resistance than with the full lube treatment before, but nevertheless my digit slipped right in up to the last knuckle, Grace's ass eating my entire thumb as if it was trivial. She definitely felt that, and I heard what might have been a snarl through the panties, but it was still pretty muffled as she had her face in the blankets as well. She made no move to stop me, so I continued my cock pumping in and out of her wet pussy with my thumb in her ass to the hilt. As I continued, Grace's moans grew louder and louder, to the point they were easily heard even through the gag and the blankets, and suddenly I realized the force of my thrusts was shaking the whole bed. The rational part of my brain seized control for a moment, and panicking I looked over to check on Tera. She still hasn't moved, but her eyes were open and she was watching me with a look of curiosity or maybe fascination. My expression must have shown what I was feeling immediately because she whispered in a low morning voice "Don't stop, just come over here when you're ready to finish."

Tera's consent of this tryst coupled with my having a pretty good idea of why she wanted me over there nearly sent me over the edge right then and there. As it was, I could feel Grace tightening up one more time, and she didn't seem to have noticed Tera was awake, what with her face buried in the covers and the moans of pleasure. So I focused as hard as I ever had on not coming while simultaneously pounding just a little harder into her willing pussy. After what felt like a lifetime but was probably a few seconds, I felt her convulsing. I wasted no time as I could feel I was going to come as well within a heartbeat or two. I pulled myself out of Grace's still pulsating vagina (and a little more carefully slipped my thumb out of her ass) and stepped over to Tera, her head at the edge of the bed.

I had expected Tera to simply engulf my cock and drink all that I had to give her, just as she had done with my very first orgasm with her, but to my surprise she took hold of my now pulsing cock and lay it on her cheek, slowly stroking me to maximize my pleasure. As semen began to flow out in bursts, she moved the tip around so that some was deposited on her lips, her nose, her forehead, even closing her eyes and allowing some to pool on her eyelids. As the last couple spurts leaked out, she released her grip and caught a few mL on her palm without opening her eyes again. It may not have been my largest load, but Tera's face was near coated in my hot cum. I stepped back, just admiring her in my post-orgasm blank-minded state. I didn't even notice that Grace had stood up and was right beside me until she spoke. She'd removed the panties from her mouth, they were balled up in her fist now.

"You look like a regular Jackson Pollock. You want some coffee with that cream?" Tera smiled slightly, but didn't open her eyes.

"Yes please, if you're offering." She replied. When she opened her mouth, more than a little cum had rolled in. She swallowed, then grinned bigger than before. Grace pulled her panties taught between her two pointer fingers, releasing them so they landed on my face, then walked out of the room holding up three fingers, only pausing to pick up her see-through shirt which she tossed into her own room before making her way, still naked, into the kitchen.

"God I love morning people." Tera said. "Thanks for this, by the way, hard to imagine a more fun way to wake up." She started rubbing the semen onto her face with both hands like it was some kind of lotion. "I've heard this is good for your skin, guess I'll find out." I sat down on the bed, suddenly realizing my legs were a little wobbly.

"You're welcome, I guess," I stammered. "So you're uh, not mad?" I asked extremely tentatively. In my post-nut clarity, Grace's faulty maths excuses seemed incredibly feeble.

"Oh definitely not." Tera had rubbed enough jizz off her eyes to open them, and when she saw me she gave me another smile. "I'd fuck Grace in the morning too, but she's always up and going well before me. It's probably for the best, or we'd both be trying to hog the bathroom at the same time." I really couldn't believe I'd just happened to meet this woman tutoring. "Hey Grace!" She called out towards the door, "I'm finished with the cream, where's that coffee?"