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Chapter 24 by Wolf Keeper Wolf Keeper

Large or small?

The large

Realising just how much of what she planned is still going on. The thought of trying the smaller dildo first is appealing. Though with how horny you are, it's clouding your thoughts. Wondering how the larger dildo will feel, and if you could really take it. You decide if you're going to try it, you're going to trust Jane in that you're not going to be hurt, and that this will feel as good as the plugs.

"I know you've been wanting to use one of the dildos on me for a long time, and I've always said no. However, if you're sure that the plug will have stretched me out enough to try these two dildos, then I trust you."

"Oh Mary you won't regret it. We'll take it slow and I promise, this will feel wonderful for you."

Quickly getting up from the bed, your wife grabs the lube from the toy chest and puts in on her bedside table. She then motions for you to get on your knees on the bed, where she starts to kiss you while taking off your blazer, then taking hers off. As your kissing gets per passionate you start to unbutton each others blouses as quickly as you can, tugging them out from the waist band of your skirts. Topless other than your camisoles and bras, you unzip each others skirts letting them fall to your knees as you life each others camisoles up to take them off. Breaking your kiss only for a brief moment as you take them fully off before resuming again. You reach behind each other and unclasp the bras, and as you go grab the straps of your wifes bra. She pushes you back on the bed while grabbing your bra straps first and it slides off you as your falling back.

Letting her own bra fall down her arms before throwing both of them to the side, along with your blouses, blazers and camisoles. She then lifts your legs and fully removes your skirt, throwing that aside as well. She reaches over and grabs the dildo off the bed from where it fell from her dropping it to the side. She leans over and kisses your clitty, that is still very hard in your panties. After that she slowly kisses her way up your stomach, then your chest between your fake breasts, then your neck, before finally giving you a kiss on the lips. You see her holding the dildo close to her mouth, where she gives the head a quick suck, before she then moves it to your mouth expecting the same.

After a slight moment of hesitation, and a soft look from Jane, you open your mouth slightly. She gently pushes just the head of the dildo into your mouth for a few seconds, before pulling it back out and giving it another suck herself, taking it slightly deeper than the head this time. She then returns the dildo to your mouth and gently pushes it slightly deeper like she took it. Repeating this a few times until your able to open wide enough to stop your teeth from blocking it going any further. You eventually start to take it almost effortlessly, before you start to gag as you can't take it any deeper. She doesn't push it any further than that on each suck. This goes on for several minutes until she stops, leans back and pulls you up with her and then points to the dildo on the headboard.

"Now that we've sucked this one. Let us suck the one on the headboard next. After all, we gotta make sure that we get it nice and went for when it goes into us. A dry fuck is just no fun at all."

The twinkle in her eyes as she says that, with that ever familiar impish smile over the last few days reappears on her face. You look at the dildo stuck to the headboard. Unlike the one you were just sucking that is purple, fairly smooth, and that ends with an easy grip handle. This one is black, and veiny with realistic looking balls on at the base of it.

"It'll be just like the purple one, only this time we'll be sucking it in the right position. On our knees having to bend over to give it a blowjob. An you wanna be a good girl for me and this big black dick don't you?"

Moving you in front of it, Jane has you lean over to suck on it first. Moving up beside you so that she can coach you on how to give the dildo a blowjob. You open your mouth as she holds the dildo up for you. As you move forward and it enters your mouth you feel Jane place her hand gentle behind your head. As you keep moving forward on the dildo from the slight pressure of her hand, you reach your gagging point. She holds you there for a few seconds before letting you pull back on it, but only so far as to keep the head in your mouth.

"Now, what I want you to do during this is imagine it's me giving you a blowjob. The way I lick my tongue around the head of your clitty, and have my tongue run the length of you when I suck you deeper and pull back. Replicate that on this big black cock for me Mary. Give him the blowjob you want me to give you."

Feeling the pressure from her hand again, you try to replicate what she said to do the best you can. As you get pushed foward, the texture of the fake veins on the dildo almost glide along your tongue. You also feel them on your lips are you keep them tightly closed around the fake cock as you go back and forth. Each time you hit your gagging point, Jane holds you there slightly longer. Telling you to relax your through and breath through your mouth, you can tell she wants you to be able to deep throat it.

After what feels like an hour, but is actually only 30 minutes. You eventually do manage to take it further and into your throat slightly. You can't hold it there for long before you start to struggle and she lets up the pressure. Looking at her to your side she has a big smile at you getting that are and starts to push you down again. This time you get further and do stay for slightly longer. Eventually with enough of this she does get you to take the entire fake cock down to the base, with your nose almost pressing the headboard and you being able to stay there for almost 10 seconds before needing to pull back.

"Oh my sweet darling sissy, I'm so proud of you taking that nice big cock like that all the way down your throat. You looked so sexy sucking that black cock that I'm practically dripping right now."

She shoves a hand of yours into her panties and you can feel that she is wetter than you've ever felt. Turning you in what is affectively a cocksucker has turned her on alot.

"Now that you've gotten our big black friend here all nice and wet. I think it's time we both got fucked, don't you?"

Having taken off her skirt before she got into position to coach you. She lays you down in the middle of the bed and has you lift your legs and hips up to remove your panties. She then removes her own before she gets on her hands and knees with the black dildo positioned right behind her.

"What is going to happen now is. I'm going to fuck our black friend here, while you are going to watch him pleasure me. After I'm done with our friend, you're going to get fucked by him."

With that, she has you get underneath her so that your head is under her pussy. She wants you to see the black dildo going into her as she fucks it.

"Mary I want you to reach up and grab that nice big black cock, and I want you to hold it at the entrace to my tight white pussy. That way we both know it's not going to have any trouble entering me. Can you do that Sweetie?"

Almost in a daze with how turned on you are with the racial and size implications that Jane is making. You reach up and grab the dildo, then holding the head at the entrace to her pussy as instructed. You see her start to back up onto it. She then shifts her legs back to make sure that when she pulls forward, it's not going to leave her pussy. You also realise that the bed as been pulled away from the wall by a couple of feet. As when your wifes feet go through the gaps in the headboard they aren't pressed against the wall as you'd expect.

Before you can continue with your current train of thought. Jane starts to push herself further back on the dildo above you. The contrast of the black dildo to the white skin of her pussy is turning you on more than you thought it would. You can see the way her pussy is stretching around it's girth as she slowly goes deeper on it. Eventually she bottoms out on the dildo, which surprises you. While she has enjoyed the purple dildo in the past, she has never been able to take it to the hilt before.

"Oh Mary, he's so deep in me right now. Deeper that you've ever been. He's also stretching me wider that you've ever stretched me as well. It's a whole new feeling for me, and I love it."

Starting to pull herself off the dildo, you can see a just how wet she is by how much wetter the dildo is. As she reaches the near the tip to where just the head is in her pussy. She starts to move back faster on the toy, reaching the base of it much quicker. As she pulls herself off it this second time, just as slowly as the first time. You feel her start to play with your clitty. She's not stroking it, nor is she giving it a blowjob. She's just rubbing the underside of the head.

"So that you can have some fun while I enjoy taking this big black cock. I'm going to play with your clitty as if it is a clit, while a slowly fuck myself for a few minutes."

True to her word, while she's slowly picking up speed with each stroke, she is rubbing your clitty the entire time. Eventually she has to stop though, as she starts picking up enough speed to where she needs to keep both hands on the mattress to get the leverage for her thrusts back. At this point she is not holding back as she really fucks herself on the dildo.

"Oh my sweet precious sissy, you'll soon be feeling the pleasure that I am from this cock. It's so big, and powerful, and it's not going soft like you do after I've had my orgasm. I bet if this were a real black cock, they could fuck me for far longer than you ever can."

Feeling slightly stung by her words, but by no means less turned on. You see just how much pleasure she's getting from fucking that toy, and start to wonder if you'll feel the same way from it. After seeing her shake and moan through at least 3 orgasms now, and looking at the clock and realising she's been fucking herself on this dildo for at least 30 minutes now. As you wonder if she's going to ever stop, she suddenly pulls off the dildo and collapses ontop of you. Clearly having gotten herself off to the point where she couldn't take it anymore.

"That was one of the best fucks I've had sissy. An you'll see experience it yourself when that big cock is inside you. Which is going to happen very soon, once I've gotten my breath back."

Unable to move as she lays there recovering her strength. You raise your head up and look at her pussy between her spread legs. Seeing that she's still wide open from the dildo and hasn't closed back up like she normally does after you finish fucking her. You wonder whether the same will happen to your arsehole once you've been fucked.

Taking only a short rest. Jane gets up, leaves the bedroom, and you hear her walk down the stairs. After only 2-3 minutes you hear her walking back up the stairs before she comes back into the bedroom holding two water bottles from the fridge. One is already 3/4 of the way drunk, while the other is still sealed.

"Sorry sissy, I had to get a drink after all the juices that I must have been releasing drained me. Now I have one final surprise for you tonight Mary. Seeing as I want to have you below me, looking up into my eyes as you lose your virginity, and I want to use our big black friend here to do so. I brought myself a strap on harness that our toy can be fitted to."

The realisation of what she's saying hits you. She said you were going to get fucked by it, and she said that you were going to feel what it's like to be fucked. You now know that she's going to be the one fucking you, as you lie there and take it.

"That's right sissy. I'm going to be fucking you tonight. I'm going to be taking the final virgin part of you tonight, and it's going to be the same night you were dressed as a sweet innocent school girl. Who is still wearing her over the knee socks I might add."

Giggling at her last comment, she reachs down into the toy box and lifts out what you can only assume is the harness for the dildo that is currently still above you. Laying your head back onto the cushions, you hear her getting into the harness. Once she has the harness fully on, she climbs onto the bed on her knees and moves up and over you to detach the dildo from the headboard. When she does this, you can see that the harness she's using looks like a part of panties with several straps on the front. There also appears to be two bulges in the crotch of the panty harness. The first is a long thin one which would be roughly where a womans clit would be while wearing it. The other is a larger one which would be lined up with the entrace to her pussy. This harness must have a dildo that goes inside the wearer to help stimulate them when fucking someone else.

As you're looking at the panty harness, you miss her getting the dildo fitted to the front of it. Moving back from the headboard and down to where she can get you to life and spread your legs. The dildo looks more intimidating now that she is wearing it, than when it was stuck to the headboard. Once she's in position between your legs, she picks up a towel from the bed that she must have gotten while putting on the harness. She then has you lift your hips so she can place the towel underneath your bum. Reaching for the plug she pulls it to where it's just barely about to pop out, and then pushes it back in. Eliciting a moan from you, she does this a few times while adding lube to make sure your wet enough to fuck.

Finally pulling the plug free, you hear her drop it onto the drop before she picks up both and moves them over to the side. Then she moves forward so she's now in the position to fuck you. With your legs spread wide and your hips slightly raised, she ask you to pass her one of the pillows you done use to sleep on and places it under your hips. Next she puts some lube on the dildo for good measure and then positions it at your arsehole.

"Here we go Sweetie. You're about to lose your anal virginity tonight, and find out the pleasures of being made love to like a women. I'm going to go slowly at first, and not rush this. I want you to enjoy this as much as I hope you will. When you feel me start to press, I want you to relax and push yourself open like you did when you took the plug earlier this morning."

Slowly feeling increased pressure from the head of the dildo. The sensation of it trying to enter you is very foreign to you right now. You try to open up like Jane said to do from taking the plug, but it's not making it any quicker. Then suddenly, as the pressure builds you feel yourself give way and the head slides in along with a couple of inches. The sensation of this dildo, this fake cock entering you are unlike you've ever felt. It feels like the plug, but more intense, more dominating.

"It's official my beautiful Mary you're a virgin schoolgirl no more. You have now got 4 inches of big black cock inside you, which is more than I'd thought you'd be able to take from the first push. I guess that plug really made you into my anal girl."

She withdraws until just the head is inside you, before she pushes back in slightly deeper this time. She is slowly building up the depth with a steady pace as the sensation and pressure of the dildo against your prostate. You can feel the ridges of the head, and the veins of the dildo against it every time she withdraws and thrusts back into you. The pressure that is building up is making you start to leak from your clitty very heavily, and while you've been so focused on the feelings inside you. You've been moaning this entire time, which has been encouraging Jane to pick up the pace slowly with each thrust.

"Oh my darling Mary I knew you'd love being fucked, I don't know if you realise it, but you're thrusting back against me. I knew that deep down inside you, there was a girl that was begging, no, craving to be fucked. I'm so happy that I can give this to you. That I can show you how it feels. Share the experience of you being fucked like the sissy you are."

Her words, combined with everything you're feeling right now, causes you to finally cum. The feeling of this orgasm though is different from any you've experienced before. It's not a short violent rush of energy that attacks you with pleasure and then vanishes. No, this is more powerful, more deep in your body, and far longer than your typical orgasm. It's like a tsunami of pleasure has crashed into you, enveloping your entire body in multiple bursts of pleasure, as it collides with every nerve from the tip of your clitty, through your prostate, and all the way up your spine to your brain.

When Jane sees you orgasm it triggers her own, as she thrusts her dildo as deep as she can and holds it there. You both collapse from your respective orgasms, with your wife again falling over onto you, with the dildo still buried inside of you. Her head resting on your fake breasts. You pass out from the orgasm, while your wife recovers enough energy to with draw the dildo, then reinsert the plug into you.

Taking off the harness, and placing it on the towel that the plug was on, she puts it down the side of the bed, before she crawls in next to you. Even though you're asleep, you subconsciously wrap your arms around her as she gets besides you and lays her head on your chest.

Final aftercare before sleep.

More fun
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