49

It took a few minutes for the overlay to adjust and synch up. I slap my cock against the side of Mari's leg and then rub it along the slit and over the clitoral hood while I wait. Her body is already responding as I watch her nipples stiffen, and even her breasts grow slightly. I'm an equal opportunity breast guy, so I don't require huge melons like on Akeno and Shizuka, but I guess Mari still reacts subconsciously to add a little more meat to her buns.

It would be rude not to respond to such an offering, so I run hands up to the newly engorged breasts and give them a firm squeeze. The squeeze turns into a quick massage, bringing mewling sounds from the gagged succuvamp. Leaning down, I take a nipple in my mouth, roll it gently between my teeth, and press it with my tongue.

The overlay synchs up, and I smile at the dream Mari with a wicked gleam. I pull an Evil Piece from my collection and press a pawn against Mari's chest. We figured out that if I give them the piece before the sex, it'll heighten the energy draw, and we can break the effect keeping them from absorbing energy as it floods in.

As the piece merges with her body and connects us on one level, I reach a hand between her legs to see how we're doing. 'Flooded' would be the appropriate word, but there is one thing to be concerned about. She's fucking tight. Like, Rias's asshole tight. I spend the next several minutes working my pinky finger in and around the vaginal opening, hoping to loosen her up enough to even make it inside her.

"What's wrong?" Carrera asks.

"She's really fucking tight. Like, 'I'm not sure I can get in there,' tight."

"Wow. Really?"

"Yeah, I can't even get a second finger in without forcing it. Give me a few minutes. I'm going to try to loosen her up."

"Are you sure you're not in her asshole?" Shamsiel says.

I roll my eyes at her. "I don't know. Why don't you slide your asshole over my cock, and I'll compare the two."

Shamsiel gets up and starts over to me, but Carrera pulls her back.

"That was sarcasm, dummy," she says to Shamsiel.

I lower myself between her legs and get to work. Lips and tongue vibrate over her vulva and clit rhythmically. Her body responds. I can feel the muscles flex as she tries to move her pussy closer to my face. I pull her clit between my lips and flutter my tongue against it. I feel her vibrate, and pressure tries to push my finger out of her twat. I pull back my hand for a second as a torrent of juice gushes over my hand and arm.

I reinsert my finger, this time my middle one, and it slides in. I stroke her inner wall just inside while moving in a circular pattern. Aftershocks are still rocking her body, but she's a trooper in the Dreamscape. After a few more minutes of working and another orgasm, I'm finally able to work a second finger inside.

Using the two in tandem, I massage and work the vaginal opening until it has embraced elasticity. Damn, it took me close to twenty minutes just to warm this little virgin up enough to maybe get my dick wet. I'm not complaining; I actually like eating succubus pussy. They taste amazing.

I start working the head between her lower lips and look into the dream Mari's eyes to see how she is doing. As the head breaches the entrance and makes its way towards the barrier, I feel a slight shift in her body. My girth was a little much for the little bit of flesh, and it tore before any real pressure was applied to it, but when that happened, it's like a complete reversal occurred.

Whereas first, it was like her body was trying to keep me out, now the walls of her vagina pulsated in an inverse pattern pulling me in. As I slide in, I reach the natural end of her canal, a little less than halfway in. I check on Mari, and her eyes have rolled back in her head, and her body twitches and jerks in her restraints.

I pull back, and it feels like her insides don't want me to go; they squeeze and pull against me. I work my cock around, trying to build up a little room so I can thrust. I end up slowly rocking back and forth, scraping her walls as they hug hard against me. The rocking picks up and becomes more circular until I'm able to work my way back to the entrance.

Now that I've got some more room, I'm able to adjust my angle and thrust properly... sort of. It's still tight as fuck, but her insides are adapting quickly. After a few more minutes and three more orgasms, I'm able to enter with two-thirds of my length, and my thrusts come in quick hit every conceivable spot within her cunt.

Her juices drip from my balls like a waterfall, and both her dream self and her true body are moaning in ecstasy. Just as I'm approaching my climax, I lean forward, biting the tip of my tongue and shoving it between the ring gag. I paint the cute girl's mouth crimson while I paint her womb in white.

Her body seizes, and her biggest orgasm yet rocks through her body. I pull my tongue from her mouth just as she crushes the ring gag. Her tongue and mouth strain to get the tasty blood back, and I rip the gag away off of her.

Grabbing her face, I hold her still until her eyes settle and sanity seems to have returned... at least a little. "I'll get you some more blood. Hold tight."

I pull back until my cock springs free of the snug little cave spilling white cream down her crack and onto the floor. I turn to ask Carrera to bring the bottle we prepared, but before I can speak, I feel a mouth engulf my schlong. Shamsiel is on her knees, slurping up the remnants of the spooge and juices that are coating me.

Carrera just shakes her head and gets up. Holding the bottle up, she shakes it a little and walks towards the hungry succuvamp. "I got it, she says."

I nod. "Thanks."

She slaps my ass on the way by. "Hurry up. You still have three cherries to pop."

She's right; this is taking too long. I need to move faster, so we can kill Zolgear and make it home in time for dinner.

.

.

.

It took a minute to get Shamsiel off my dick. Eventually, Carrera grabbed her by the hair, dragged her over to Mari, and shoved her face into Mari's crotch to lick up any escaping cum. Mari seems happy with this turn of events since Carrera keeps feeding her small sips of blood and rubbing her tits simultaneously.

I shake my head and walk over to little pink Lolisa. I had a conversation with Lolisa before we started this, and she had a tiny request. She wanted to go before her sister, and she had some ideas on how to proceed. Who could turn down the adorable girl's request? Especially when it sounded fun.

Crouching next to the cute girl, I pet her lightly, paying a little extra attention to her. In the Dreamscape, Lolisa coos a little and leans into the touch. "I-I'm a little nervous," she whispers.

I smile warmly. "I know, sweetheart. This isn't exactly the how and why I'd like your first time to be, but it's the best option we have right now. I promise that soon we'll be able to take our time and maybe be a little more romantic."

She nods. "I'd like that," she says and, with a deep breath, adds, "I'm ready."

Reaching down to where the hand-foot pillory connects to the floor, I grab hold, snap the connection, and repeat on the other side. The device has her locked in a kneeling position with her face and chest pressed to the floor. Positioning myself behind her, I caress her ass and thigh before stroking my fingers over her virgin slit.

She's wet and ready, but just to be sure, I add a little of Maria's special lubricant that she gave me and rub it in. Testing the gates, I can tell she's at a normal level of tightness, unlike Mari. That doesn't mean I don't need to do some work here. After all, I am part fucking dragon, and a normal level of tightness would still result in pain.

While using one hand to massage her clit and opening, my other slides under her shirt to play along her soft skin and small perky breasts. One of the things I always thought weird about the harem stories I'd read in my previous life, most times, the girls in the harem were pretty much the same, sexually speaking. They all had giant tits and the same submissive demeanor in bed. Isn't the point of a harem variety?

Maria's cute and innocent appearance belies the truth of her lewd and sexually aggressive self, while Lolisa is genuinely innocent. While similar body types, Lolisa is a bit taller than Maria; they are polar opposites sexually... although, Lolisa does have one fetish that I hadn't expected, which could change the whole dynamic.

I look up at the girl opposite us. Kurumu, in both the real world and the Dreamscape, is panting, her head twisted so she can watch her sister being played with by me. Lolisa's cute little moans hit Kurumu like physical blows, and she even lets out her own whimpers and moans.

I lean down to Lolisa's ear and whisper. "It's time. Are you ready?"

To the best of her ability, she nods her head quickly and licks her lips. Sliding into position, I rub the head of my cock over Lolisa's pink hole a few times and feel her jump a little.

Suddenly, Lolisa calls out, "Sister! Are you watching? Can you see me?"

I look back at Kurumu. Her eyes are wide, and I can see the pulse in her throbbing. "She's watching," I say.

"Good," Lolisa says, sounding relieved. "Do it! Don't wait! I want sister to see you thrust it in."

"If I do that, it might hurt, Lolisa. You sure you don't want to take it slow?"

"I don't care!" she says. "I want sister to see you push it all in."

"You heard the girl," Carrera says.

I look over at her. She winks and measures out a little distance with her fingers and mouths, 'About halfway. Not too hard.' But out loud, she says, "Slam that hotrod deep inside her."

I return my gaze to Kurumu's horny and frustrated face, lost in lust and yearning. I shake my head, line my cock up with Lolisa's sopping wet pussy, and sigh. Don't judge me for the following line. Lolisa requested it specifically. "Watch your sister Kurumu. Watch as I make her a woman."

I hear Carrera snort, and I can't help but agree. What the hell kind of trashy web novels are these girls reading?

I plunge forward, breaking through Lolisa's hymen like the Kool-Aid Man, and bury myself halfway inside her. She lets out a shriek, and even Carrera winces. I fucking told her it was a bad idea, but does anyone listen? No, they think, 'Oh, I'm supernatural. I'm not a wussy little human. I can take it.' None of them understand that having a coke can thick rod shoved up through a nerve-ending filled flap of flesh doesn't care about your supernatural constitution. It will still hurt.

As her keening wail dies down, I ask, "That's almost halfway. Are you ready to take this slower now, Lolisa?"

She shakes her fool head. "NO! I can take it. Pound me, Issei. I want sister to see me take it all."

I look at Carrera, who just shrugs like she's washing her hands of the whole thing. Well, the lady asked. I draw back and start to piston in and out of the tiny wet cunt.

"Are you watching Kurumu? Can you see Issei's fat cock driving into me, sister? Watch me. Watch me. I-I'm gonna. I'm-I'm cumming," Lolisa commentates.

I slow while she's coming down from the major orgasm and take the opportunity to bond a bishop with her. "We're not done yet, sweetie. Are you still okay?"

"I-is she watching?" Lolisa asks, trying to catch her breath.

"She can't take her eyes off of you," I say.

"I-I want to see," she says.

I saw this coming—time for my upper body workout. I lift the pilloried girl and sit back on a bench directly before Kurumu. Lolisa is spread open like a Thanksgiving turkey right in front of Kurumu's face. She can see exactly how deep my cock I buried in her little sister's cunt. Poor Kurumu looks like she might pass out from overstimulation.

"S-she can't- She can't see all of me. Issei- Issei, make her see me," she says, sounding desperate.

I'm a little confused at first, but Carrera's got my back. She walks over and tears Lolisa's shirt wide open, exposing her tits and body. Kurumu jerks and Lolisa sighs. Not gonna lie; these girls have some deep-seated issues.

"Yes, watch me, sister. Watch." That's my cue to get to fucking, I guess. I turn the little loli into an onahole. I pull her up until only the head is left inside her and then pull her back down. Rinse and repeat to the rhythm of her moans and gasps interspersed with demands and interjections.

"OH! Yes, watch me, Kurumu. It's so deep. I feel it. I feel it churning my pussy. Deeper, Issei. Shove it in me deeper! Oh! Watch me! Watch me, sister! I'm cumming again! I'm CUMMM-IINNNGGGG!"

I feel the squirt of fluid drip over me, and despite, or maybe because of her cheesy dialogue, she is turning me on. She's like a cliched live-action hentai—way over the top but oddly erotic. Just for variety, I start rolling her hips as I move her on my Johnson to great effect as she enters a period where words fail her, and she just whimpers, moans, and gasps.

I got a little overly enthusiastic when I reached my own climax, and I may have slammed her down a little harder than I meant to. As I plow deep inside her, I feel her insides stretch tight, and the cum burst from the tip into her. Even Shamsiel's eyes widen as Lolisa hits a shuddering gasp and then goes limp.

Pulling her off my dick, I break the pillory, holding her in position, and let loose her limbs. Leaning her against the back of the bench, I check to see if she's okay. She is awake if still dazed, but the crazy part is she touches my cheek gently with a languid smile and then looks past me to Kurumu. "Thank you, Issei. Now I want to see you fuck my sister. She needs it."

I look over to Kurumu, who also has a dazed look on her face, and I can see the puddle of liquid below her feet and the juice flowing down her legs. I guess that was foreplay for her. I stand up and step to her. She's in the standing pillory, so it must have been hell on her neck to watch that whole show, but she was a trooper and kept her eyes on the prize. The prize, in this case, was her sister's pussy, but still, the effort was there.

I push her head down, my hand stroking the tense muscles and tendons of her neck until my fingers get tangled in her blue hair. Then gripping, I yank her head back so that she's eye to eye with Lolisa. Her mouth hangs open, and her tongue lolls out like an erotic ahegao.

"Maybe a little taste of your sister's pussy will get you on your feet again. How about it?" I say, rubbing my cum covered cock over her tongue. I angle myself so that I'm not entirely blocking their view of each other and thrust my rod in her mouth, stretching her jaw and the wall of her cheek.

Looking for Lolisa's reaction, I roll my hips in a gentle thrust. Lolisa doesn't disappoint, smiles lewdly, and starts rubbing her clit and dipping her finger into that abused cave.

"Look, sister. Did you see me cum? Look how stretched I am. That's going to be you soon. Issei is going to fuck your pussy and make you cum," she says. "Issei, did you know I watched sister masturbate once?

She didn't know I was there, but I heard her. I heard her calling my name. When I looked in her room, she was there, naked, with clamps on her nipples and moaning lewdly. Make sure to pay special attention to her breast and especially her nipples. Those are really sensitive."

Kurumu lets out a low moan muffled by the cock in her mouth. I smile. "Sure thing Lolisa. I'll take good care of her."

Popping my dick out of her mouth, I circle back behind the pilloried princess. Flipping up the skirt to reveal her cum dripping pussy. There is ample evidence she's orgasmed several times already, and her opening is expanding and contracting as though the aftershocks haven't ended yet.

Slapping her legs further apart, she squeals a little in shock as her hips drop down slightly. I grab her meaty ass and dig my fingers in slightly. She lets a cute little 'mmph' as I readjust her position some more.

Sliding my dick between her ass cheeks, I lean forward and whisper, "Did you like watching me fuck your sister's tight little pussy. She's just so cute, I was going to go easy on her, but you know what she said? She said she wanted you to see her get her sweet little pussy pounded. She said she wanted you to see her get fucked. Not 'have sex' or 'made love to,' but fucked. Hard."

Kurumu let out a shuddering breath. I reach my hands up as my pelvis starts to rock against her ass and grab her breast in a quick, firm grip. The breath becomes a gasp. "You know Kurumu," I say. "Since you and your sister are my women now, there is every chance in the world that you will end up in bed with her regularly."

One of my hands snakes back to check Kurumu's cave and to loosen the entrance, while the other takes a grip on one of her nipples between the thumb and the side of the forefinger. I'd palmed the other Bishop piece and let it merge into her. I start gently rolling the nipple, increasing the pressure slowly until I've fully clamped down on it. Guiding my dick to her hole, I work the head around the entrance in slow circles working the juices all over.

Kurumu goes still. "Do you like that idea? Do you want to caress her soft skin and taste her sweet lips? You've already tasted her love juice; you'll be able to taste it again soon. As I fill you both with my cock and cum over and over again. Just... like... now."

On the word 'now,' I thrust forward. Quick and easy, like ripping off a bandaid. At least that's the way Kurumu put it when she told me she wanted a quick first thrust and then to move at my leisure.

Incubus Insights is pretty useful, though. I know the exact moment that her body is ready for that thrust, and I am rewarded with Kurumu having a body-rocking orgasm right off the rip. As the orgasm starts to slide, I start moving, causing Kurumu to squeal. She's far too sensitive right now, but a sex-dazed Kurumu is precisely what Lolisa wanted.

Lolisa slides off the bench and crawls over to Kurumu. She reaches out and takes her face in hand, and plants a gentle kiss on her lips. "it's okay, sister. We're together now. We can be together, forever, and Issei will be there with us, and we'll have lots of other sisters too."

Oh, yes. Yes, indeed, little Lolisa. Lots and lots of sisters. The two sisters stare into each other's eyes and clasp hands. It would be a sweet moment if not for the fact that one was moaning and gasping in time to the rhythmic smack of pelvis to ass cheeks.

I think how great it would be to have a view of Kurumu's face right now before I remember that the Dreamscape is overlayed with the real world, and I can do whatever the fuck I want there. So, I create a couple of perspective monitors to get more angles, including one of the sisters' faces.

"Oh, wow," Mari says. "I wish we had some popcorn."

"Hush, child," Carrera says. "Drink your blood and enjoy the show."

Peanut gallery aside, Kurumu's face, which had been red, to begin with, was starting to get slack. It's a little too much stimulation for the poor girl and coupled with the difficult position she's been placed in for days... She just didn't have much left in the tank.

I pick up the pace. Kurumu has already had four orgasms, not counting however many she had watching her sister getting plowed and used as a fleshlight. I watch her face on one monitor as I watch Lolisa masturbate, standing right in front of Kurumu's face in another.

I can see Kurumu's pupils dilate and eyes widen as I piston inside her. "We're almost there," I say. "Lolisa, pinch your sister's nipples while I finish."

"Okay!" she says in a bright cheerful voice, happily ducking under the pillory and attacking her sister's breasts. Eliciting a sharp groan from Kurumu and a quick pulsing of her pussy walls. Pushing me to my limit. A few more thrusts, and I deposit a thick load in her womb.

Taking a quick breath, I snap the lock on the pillory and pull Kurumu and Lolisa into my arms and plant a kiss on each of their foreheads.

Before anyone can say anything, I call out. "Zest?"

Immediately, she appears in the window of the cell. "Yes, master?"

"I need these five to be taken out of here before I cut Albedo free," I say. Albedo's binding isn't as easy to work with as the others. I'm surprised she isn't in worse shape from it. If she pulls too hard, she'll either break the rod or cut herself in half. No easy access to fuck her sane either. I let out a long sigh. "Five down, one to go. This one's going to be more a fight than a fuck I think."