A College Threesome Beyond My Wildest Fantasies: Tutoring Sessions Part 6 [F20sF20sM20s] [Threesome] [Double Dildo] [Vaginal] [Anal] [Oral] [Cum Eating] [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 5: https://www.reddit.com/r/eroticliterature/comments/1mkvwg6/my_new_girlfriends_roommate_joins_us_in_some/?ref=share&ref_source=link

Part 6: New Horizons

Tera was still finishing toweling herself off as I rounded the corner into Grace’s room. I noticed three things in quick succession. First, the sign on Grace’s door, which read “Deliveries in Rear”, was starting to make more sense to me. Second, Grace’s room was a mess. The bed wasn’t made, there were clothes strewn all across the room, and her desk in the corner was covered in snack bags and empty soda cans. The third thing I noticed (and this was when I stopped noticing other things altogether) was that Grace was on all fours rummaging under the bed, her head and arms totally hidden from view. Her pussy on the other hand was on full display, as her legs were pointed right at me in the doorway and spread apart just enough to seem deliberate. Her lips were parted and her pussy gleamed pink in contrast to her light brown skin. I was still just staring when I realized Tera was now right behind me and could easily see what I was looking at. She raised an eyebrow at me, but it was Grace she addressed as we both moved into the room.

“Grace, you really have no shame, do you?” Grace wriggled backwards (which was something to see in and of itself), extricating herself before she answered.

“No I do not. But really it was for science. I wanted to see how he’d respond to the classic ‘stuck girl’ fantasy. I gave it 75% odds he just got down and started fucking me, given how revved up he must be by now.”

While the horny part of my brain (which was most of it by this point) had definitely thought about it, it definitely hadn’t seemed like an appropriate thing to do by any means. For one, I considered Tera my girl, I had no clue how Grace fit into that yet. I’d eaten her out because Tera told me too, I wouldn’t have done it otherwise. Moreover, the consent in that situation seemed really ambiguous, and that just wasn’t something that got me going. All that being said, horny brain was still mostly running the show. “I guess I missed that opening.” I said slyly. Grace stood up, keeping something from under the bed hidden behind her back. “Oh, we have a smart ass here! He goes perfectly with you Tera, being a tight-ass.” “And what kind of ass does that make you?” Tera responded without missing a beat. “An ass that’s open for business.” Grace said with an impish grin. Tera gave her a friendly glare, putting her hands on her hips. She was standing next to me just inside the room, and Grace was a couple meters away standing by her bed. We were all completely naked, and I took just a moment to reflect on how amazing a situation I had found myself in. Before I could get too lost in the moment, Tera spoke up again. “So, what have you got there that you’re hiding from us?” Grace's grin grew even wider, and she pulled her hand out from behind her back. She was holding a double ended dildo, about 40 cm long and pure black. She was holding it by the middle but it didn't flex much, and I could just make out some slightly raised ridges near either end. It wasn't incredibly thick but somehow it looked... Aggressive. I don't know, I hadn't been around a lot of dildos before. Apparently Tera felt similarly though. "Damn, that thing looks like you could bludgeon someone with it. I hope that's not what you had in mind?" "A personal defense dildo, that's an interesting business idea..." Grace replied, making a face like she was depressed in thought and tapping her chin with the dildo. " No, here's the plan: We give your man a show, then let him have his way with us. What do you say?" Tera and I responded at nearly the same time, I let her go first. She said "I really don't think he needs the extra encouragement." and gestures at my cock, still standing totally erect. There was no way this erection was waning around these two naked, at least not until I'd had an orgasm, maybe more than one if I was lucky. And something about my situation made me feel lucky. Maybe that's why I was willing to be patient. I corrected Tera quickly. "No no, I'm curious to see what that thing is for. I can be patient, I swear." Tera gave me an exaggerated side-eye, looking down to my cock and then back to my face. "Ok, but no touching yourself. If you waste that cum on the carpet you'll owe me big time." Now here was a girl who knew what she wanted. Both did really, and I was here for it. "Ok Grace, what did you have in mind? You want to have a deep-throating competition or something?" Grace shook her head. "Nothing so complicated as that, besides we both know you would win that easily. This isn't the right dildo for that anyway." She gestured offhandedly at a box shaped like a treasure chest tucked beside her dresser. I wondered just how many dildos Grace owned, as it wasn't a small box. Not surprising really, Grace wasn't a small-chested girl. I shook my head, I couldn't believe I was getting distracted. I looked back over to the girls. Grace had pulled Tera up onto the bed, where she had laid her on her back. Grace was explaining herself as she took up her own position opposite, her legs pointing towards Tera and her head pointed roughly my direction, though I remained back away from the bed for a better viewing angle. It'll be just like that third night in Mexico, with one major difference." Once her hips were aligned with Tera but half a meter apart, she took the dildo in her hand and gently pushed it into Tera's waiting vagina. She went slowly, but didn't seem to meet much resistance. Tera let out a soft moan, she'd seen it coming of course but it clearly felt good. Grace didn't stop there however, angling her hips until she could put the other end of the dildo in her own vagina. She grunted a bit as she inserted the black rod into herself, obviously having to work a bit harder to get it in. Without Grace having to say another word, Tera started rocking her hips back and forth, impaling herself on the shared dildo. She spoke softly between thrusts. "Mmmm, this does hit different with penetration." She continued rolling her hips back and forth, the section of plastic between the girls' vulvas expanding and shrinking. Grace was trying to match her rhythm, though she didn't seem to be enjoying it quite as much as Tera was. After a minute Tera spoke up again. "I do miss the pressure on my clit though without you rubbing against it." Grace gave a half shrug between thrusts and said "I should've thought of that, different dildo. Luckily we have someone who can lend a hand." That last sentence had been directed at me, and she gestured towards Tera's pussy. "Would you? I can't reach, and a real gentleman wouldn't make the lady do it herself." I jumped up on the bed without hesitation. While watching had been as hot as I hoped, Tera had been right, I was eager to get involved. I smiled at Tera, then rested one hand on her soft, shaved mound. I let two fingers curl around until they found her clitoris, then started gently massaging it. Almost instantly her expression went from one of pleasure to bliss. Her head dropped back, and she started to breath a little heavier. Looking back over to Grace, she gave me an approving nod, but still didn't seem to enthused about the process. After a minute she spoke up. "Now see, I still don't get it. Why would you want to use the vagina, when your ass is right there and it's so much more intense?" Tera took a moment to compose herself enough to answer. "It's not always about intensity. The rhythm of the thrusts, the way it feels stretching you out then pulling out again, it's magic. It's what your vagina was made for, right?" Grace looked unconvinced. Looking down and thinking about Tera's explanation, I noticed that the dildo wasn't actually moving in and out of Grace at all. Whether it was because her pussy was tighter or just less wet I didn't know, but I thought I'd see if I could help. Switching hands so I could keep rubbing Tera, I grabbed the visible portion of the dildo sticking out of Grace. I started gently pulling and pushing it into her, accompanying that with a slight twist on each thrust, remembering the ridges on the ends. Looking up at her, I saw that it was working. Her eyes widened, and her breath started to catch somewhat. She looked at me, and mouthed "Thank you" before closing her eyes and just enjoying the feeling. Tera however was still enjoying herself more. Though I'd intended to get Grace more riled up with my antics, it was of course the same dildo in Tera. She was biting her lip and moaning consistently now, gripping and pulling the sheets with both hands. My hand on her pussy slowly moved over to my dick, almost of its own accord, but Grace swatted at it, whispering urgently "no touching! Remember?". I contented myself to keep pleasuring the girls, but it turns out I didn't have long to wait. "Can I have his dick now, please I need it!" Tera pleaded between gasps. Grace looked like she didn't care either way. "Sure why not, I'm not going to cum like this anytime soon anyway." Grace replied. I released the dildo and she moved herself backwards, the dildo coming with her until she pulled it out. She rolled off the bed onto her feet, and I shuffled forward on my knees between Tera's legs. Without much ceremony, I replaced the artificial cock with my very eager real one. I had meant to start slow, but Tera was very much already revved up as high as she could go. I plunged all the way in on my first stroke, my balls smacking into Tera's ass as she let out another, louder gasp. Her back arched, lifting her up onto her feet and elbows, her head so far back it was resting on the bed. Enjoying the angle, I grabbed her by the thighs and continued my vigorous thrusting. After 45 minutes of teasing, the caveman in me was so ready to fuck someone. Tera's pussy felt like heaven, and I was determined to finish this time, even if later I would reflect that was fairly selfish. It turns out I needn't have worried about that. Tera's head start was making itself evident. Before I'd thrust two dozen times, she had clapped one hand over her mouth, muffling an "oh God!". Her body contracted and pulsed, and I felt her pussy clench around me as she came. After a couple of seconds, all the tension left her, and she collapsed onto the bed. I was still holding her thighs though, and the animal in me was not stopping. So needless to say when I felt Grace grab my hips and pull me backwards off of Tera, I was surprised and I'm ashamed to say I gave her a frustrated look as I demanded "What?!" impatiently. Grace just chuckled at my frustration. "Almost there loverboy. Now you make me cum, and then I promise you the best orgasm of your life so far." She gestured for me to get off the bed, which I did with only a tiny huff. My cock was practically pulsing at this point with how many times I'd been pulled back from the brink. Grace helped Tera to sit up, then laid her back down to both of our surprise, with her head off the bed. She then guided me around so that I was standing in front of Tera's inverted face. She reached up with one hand and brushed my cock, which was only a few centimeters from her face, and spoke softly. "This just seems like my turn again, not that I'm complaining. This thing definitely seems ready for me to empty it." She opened her mouth wide, sticking her tongue out, and I moved forward eagerly, clearly thinking the same thing. Grace put a hand on my chest, pushing me back and stepping between us. "No," she said, "it's my turn." With that, she turned so she was facing Tera, with her back to me. She inched forward until Tera's face was between her thighs (it was a fairly low bed), then leaned forward until she was lying on top of her in a sort of half-standing 69 position. "Oh," said Tera almost directly into Grace's pussy, "I think I see what you're going for. She starting licking it then, closing her eyes. I wasn't really sure what I was supposed to be doing though. I just stood there, enjoying the sounds of two girls eating each other out, I could have listened to it on a loop for hours. After a few licks Tera opened her eyes to see me slowly stroking my cock and just taking it in. It must have looked pretty odd from her angle, seen from below and framed by Grace's butt cheeks, because she laughed and said "Now that's an unusual sight. I like it, but it's definitely a new one for me." I grinned like an idiot, and might have just continued had Grace not lifted her head from Tera's pussy and spoke up. "You haven't figured out your job yet? Tera's got the front door, so you've got the back door. That bottle on the nightstand is lube." She gestured to a large glass bottle with a pump top just to my right. It was only about 1/4 full, I had a feeling it saw a lot of use. Not really sure how this was going to work, I pumped some into my hand. It was more viscous than I expected, but undoubtedly very slippery. I started stroking my cock with the lubed up hand, looking a bit nervously at Grace's ass. Hadn't I heard somewhere that anal sex was was really tricky? That you had to go really slow? I was very unsure of myself, and despite my earlier confidence in the longevity of my erection I felt it start to falter just a bit. I was still at full mast for sure, but was starting to lose some of the firmness I'd been sporting. I just stood there for a minute, stroking and staring, until Grace turned to look over her shoulder again and addressed me. "Are we going to stand around all day, or are you going to fuck my ass?" She asked, sounding impatient. I wanted to have a cool response, but I really just didn't. "Uh, yeah," I said awkwardly, and I stepped forward, placing my cock atop her right ass cheek. She widened her stance slightly, which caused Tera to mutter something that was muffled significantly by Grace's muff pressing down onto her mouth. The motion also served to spread her cheeks wider, and her anus felt like a judgmental eye daring me to do something. Despite my assurance, I still hesitated. "It's just, I've never done this before, and I don't want to hurt you..." Grace turned around again, this time looking less angry and more sympathetic. "You're sweet, but this is far from my first time. I'm already pretty stretched out, that's what the plug is for. Have you still got some lube on your hand?" I did, and I showed her. "Not enough, get some more. Good, now go ahead and put that right on my ass hole. Don't be shy, this definitely won't work if you're shy. Feel free to work it in just a little bit." I rubbed the lube all over her crack, which I guess wasn't strictly speaking necessary, before I said to myself "What's the big deal? I licked it earlier." Without giving myself more time to think, I ran my lubed up finger over her hole. Unsurprisingly, it didn't bite me and I wasn't struck by lightning. Emboldened, I passed my finger back and forth over it a bit, being less ginger now, until to my great surprise instead of passing over her anus my finger slipped inside up to the second knuckle. I was mortified for a second, but to my astonishment Grace gave a little purr and said "oh, yeah now you're getting it. A little inside as well." I supposed that going into her ass was the whole point. I withdrew my finger (a part of me very glad to see it was as clean as it had gone in), and pushed more of the lube I'd spread uselessly in the crack of her butt towards her ass hole. Now that I was trying deliberately, I was surprised how easy it was to push inside despite the fact that when I withdrew my finger the hole quickly closed back up. I could tell when Grace was as lubed as she was going to get. I withdrew my finger, and positioned my cock right in front of her ass. Grace must have known I was going to hesitate again, because without turning around she said "now just put it in like you're used to, only slowly. Use more lube if you feel resistance. I hesitated a moment longer and to my surprise I heard Tera's muffled voice from the bottom of the pile. "Go for it!" At least I think that's what she said. She also smacked my ass with one hand, or at least tried to. The angle was awkward and she caught the top off my thigh, but I felt her support either way. Taking a deep breath I put the head of my cock on Grace's anus and gave a gentle push. Just like my finger had, the tip slipped right in. I was now officially having anal sex. Not wanting to rest on my laurels, I went to work. I pushed a little harder, and my cock slid in another centimeter. Sensing the increased resistance Grace had warned me of, I pulled back out, pumped some more lube on my hand and drizzled it onto her asshole. I didn't bother with my finger this time, pushing it into her ass with my cock. I made it further in, so I figured just keep repeating the process until you're all the way in. I had to add lube 4 times, and each time I pulled out Grace let out a gasp, and she sucked in a breath again every time I reinserted myself. It was a slow and meticulous process, not really what I imagined when I thought about a wild sexual encounter. Still, the sight of my dick disappearing further and further into Grace's ass certainly had its appeal. It seemed like it was pulling me in at times, like it was hungry for my cock. All the lube meant I didn't feel anything as far as friction went which was odd, but there was definitely more pressure all around my cock than I was used to. I was certainly enjoying myself, I was having no trouble staying hard now. When I had about three quarters of my dick in Grace, Tera pulled herself off her vulva and spoke to us. "I'm finally realizing where they hold the camera to get this shot. Making porn must be weird." I thought about what she must be looking at from down there, Grace's pussy and thighs, my thighs and ball sack, the bottom of my penis and the shaft disappearing into Grace's rectum. Yeah, that must have been a strange view. Neither of us got to reflect on it for long, as Grace responded with a little strain in her voice. "Hey, I'm trying to do something that's a lot easier the more I'm turned on, so get back to licking, Tera." Tera did so, I could hear her lapping with a flattened tongue. She then addressed me, "And you, go extra slow at the end here. You're a lot longer than that plug was." I decided to take that as a compliment, and continued my process of adding lube and pushing a little further in. After a couple more goes, I was all the way in. Or at least as far as I could in this position, my hips were pressed against Grace's buttocks and there were a few centimeters of dick left I couldn't get in from here. I was more than content with that, however. Grace noticed I wasn't moving anymore. "Is it all the way in now?" She asked. "Great well done. For the record that barely hurt at all, so you did great." For a moment I thought that was a backhanded compliment, but she continued in earnest. "Now just go ahead and do what you'd usually do, only start slower. I saw you go straight to pounding Tera, let's get to know each other first. And feel free to add more lube as needed, if I never have to ask I'll be a happy gal." Now I was on my own, ass-fucking my girlfriend's roommate while she was getting eaten out by that same girlfriend. Hell yeah. I started with some short, slow strokes to get a feel for it, but despite Grace's warnings there was next to no resistance and it didn't seem as tight as when I'd started. I noticed a rhythmic tightening of Grace's sphincter (whether she was doing it or it was happening on its own, I didn't know) and I tried to match pace with it, so I was as deep as I could get when she was tightest. I continued this pattern while lengthening my strokes, which meant they were faster as well. Soon I was pumping nearly my entire cock in and out of Grace's ass every couple seconds. Grace was starting to let out a series of "oh yeah!"s punctuating her accelerated licking of Tera's pussy. She was already being louder than Tera ever was while we were fucking, and I had a feeling she was going to get louder still. I paused to add more lube, then continued at my previous pace, figuring Grace's cries of pleasure where a sign to keep doing what I had been. Grace, however, seemed to feel differently. She turned over her shoulder, whipping her hair around so she could look me dead in the eyes, and said "Is that all you've got, Big Boy?" In any other context I might have found that ridiculous, but riled up as I was by the two naked women and in the middle of fucking her ass, I immediately rose to the challenge. my hands had been on my own hips up until now, and I grabbed Grace's to pull her into me with each stroke, so that my hips slammed into her butt, making it jiggle wildly with each thrust, which increased in pace again. Later I realized this made it near impossible for Tera to keep licking Grace's pussy, but neither Grace or I took notice at the time. This seemed to be exactly what Grace had been looking for, as she tossed her head back and gave an even louder "YEAH!" than before. I continued my thrusts, and was rewarded a few seconds later when Grace began to shudder. I felt her anus contract around my cock and started to slow, but to my surprise Grace and Tera both called out some variation of "No! Keep going!" I was only too happy to oblige. I had almost come again when fucking Tera before, but the nervousness of preparing for my first anal sex had reset the clock apparently. Now, though, I was starting to feel the orgasm building again, and I had fulfilled Grace's request (command?) to make her come first. I immediately restarted my thrusting as hard as before, maybe a little harder now that I was heading for my finish as well. This time Grace and I were on equal footing. As I felt myself getting closer and closer to release, Grace began to call out louder and louder, to the point I was sure anyone in an adjoining unit could hear her easily, then she began to shudder once more. As her body began to pulse, I looked down to see her anus clamping down hard on my shaft then releasing slightly before clamping again. I was really starting to understand the anal appeal, and the combination of the feeling and sight of Grace's contractions on my cock sent me hurtling towards the edge. Right before I went over, I heard a voice saying something urgently and felt something hit my leg. I looked down, suddenly remembering Tera was buried beneath us. She slapped my leg again and repeated, "Pull out!" There was no time to think. My caveman brain was screaming at me to push in, push in (despite there being nowhere useful for these sperm to go), but I trusted Tera, she had never led me wrong. At the moment I started to come, I pulled out. As Grace yelled at practically the top of her lungs "FUCK YEAH!", Tera reached up and in an impressive act of dexterity, milked what felt like a cup of semen from the end of my cock. It sprayed with incredible force, coating Grace's ass, nearly filling her crack with cum that flowed down over her pussy, much of it falling into Tera's waiting mouth. After what felt like a minute, she released my cock as my orgasm started to wain, using her hand to push more of the cum covering Grace's pussy into her mouth. She lapped at it greedily, smiling as she swallowed it all. Grace meanwhile, who had been supporting herself on her elbows, had collapsed on top of Tera. She spoke up again after just a couple of panting breaths. "One more.... please." I was more than a little surprised once again, but I'm nothing if not a gentleman. I pushed my still rock hard cock back into her eager asshole, my cum mixing with the lube still coating her insides. I was pretty sensitive at this point, so though I pushed all the was back in I did so very slowly. It felt like there was practically no resistance at this point, which was good for me as otherwise I probably couldn't have handled the sensation. While Tera licked her lips and looked on, I slowly worked my cock all the way back out, reinserting it fully before pulling out again. Though there wasn't much friction or pressure anymore, I remember the stark contrast of the heat of Grace's insides against the colder air of the room. I didn't know how long I could keep this up, my erection was going to fail at some point having done it's job, but I didn't have long to wait. Less than a minute later, Grace began to shudder one last time and her mouth opened like she was going to scream, but no noise came out. Her asshole convulsed once, twice around my dick and then just relaxed, and she collapsed on top of Tera, basically falling off my dick. She was a mess, her butt covered with cum and lube both sliding down into and out of her gaping hole, which was this time in no hurry to close. I might have stood there staring for a while longer, but I heard a strained sounding Tera from beneath her. "Hey that was pretty awesome and all but my neck is killing me and you're squishing the air out of me Grace. Think you can move?" Grace muttered something unintelligible straight Tera's mons pubis, then tried and failed to push herself up. I quickly moved back behind her, grabbing her under the armpits and picking her up off Tera, who sighed with relief and rolled off the bed. Grace wasn't that heavy, but she wasn't really helping at all either and dead weight is dead weight. She fell back against me, and she turned her head towards me and whispered. "I appreciate the sentiment, but I think I need a little recovery time." At first I had no idea what she meant; then I realized my cock, though was softening now, was still erect enough to poke her in the lower back with her leaning back against me. "Sorry," I answered, "thing's got a mind of its own. Where do you want to go? Back to the bathroom?" "Is ok, thanks. No, I'll clean up later just bed for now please." I helped her over to the bed, not sure if she'd lie down or what, but instead she just sort of collapsed against it, half kneeling on the floor and half lying on the bed, arms outstretched. "I just need to rest for a bit..." She said, sounding sleepy. Tera was sitting on the floor leaned against the wall stretching her neck, and I slid down next to her. We both just looked across at the mess of Grace's ass as she began to snore. She leaned her head over on my shoulder. "Should we clean her up, get her into bed?" I asked. That just seemed polite. "You know what? No. I clean up after her all the time, and I'm tired of it. She can clean up after herself for once. Besides, I'm sure it's not her first time waking up covered in cum." I thought that sounded a bit cold-blooded, but I suppose Grace had had every opportunity to clean up, and I had even offered to help. "Besides," Tera continued, "look how much of your cum she wasted. That should've been mine. I'd say you both owe me." I stood up, then turned to take her hand, helping her to her feet. "Oh? And how do you intend to collect?" I said. "Why don't you come back to my room with me, and we'll find out?" She replied, turning away without letting go of my hand and pulling me from the room, turning the light off as she went.