Anal Training - Lesson #02

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Woman continues her preparation for anal sex.
2.4k words
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Part 2 of the 3 part series

Updated 11/02/2022
Created 01/24/2009
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Jack597
Jack597
171 Followers

We decide to meet at a hotel, as both of our houses are busy lately with the kids being at home and our spouses off. It's been a while and both of us are anxious to get together. You've been using your butt plug trainer for a few weeks and now think you're ready for the next phase. I know I'm ready to take you there.

We meet in the downstairs lounge for some adult refreshment before going up to our room. You look as lovely as ever and are dressed to kill. It's a warm summer night so you are sans nylons, but you're wearing a very cool pair of strap-on heels that are open all around. Your nail-polished toes show, and your heels are exposed except for a thin black leather strap. Your ankles are bare, as are your luscious calves and knees. Your short skirt shows off your beautiful legs. Also, because it's so warm, you're wearing the skimpiest little top that barely conceals your obviously large and overflowing bosom. When you walk the flesh is moving in so many directions it's impossible to concentrate! What a pleasant distraction you are.

We sit at a small table to chat. You tell me that you've been using the smallest butt plug to stretch yourself, but explain that it's now too small to be effective. You need to go to a bigger model. I nod approvingly, pleased at your progress. I want to make tonight's lesson as new and exciting for you as I can. I'm not sure though who's going to enjoy this more, you or me.

It's not long before we decide it's time to go upstairs. As we walk arm-in-arm across the lobby to the elevators, heads are turning to watch the vision of sex beside me. Your gorgeous legs, that fabulous ass, and your jiggling mammaries are any man's dream. When the elevator door closes us in, you turn to me with those bedroom eyes of yours and stand up on your toes to kiss me. Your moist mouth and active tongue soon have me in a whirl. With your tits against me, you reach down to feel my cock, checking it's status, running your hand along its length through my pants. It responds to your touch. You can feel it growing in your hand as we kiss. I bend down to put my mouth on your exposed tit flesh above the neckline of your blouse as we hear a ding. We've arrived at our floor.

Inside our room we quickly resume our embrace. I turn you around and bend you over with your ass against me. My burgeoning cock is riding right in your crack through my pants and your skimpy skirt. You push your plump cheeks against me, imagining how it would feel if I were to enter your ass like this. We gyrate together for a minute, then I tell you to take off your panties and sit on the bed. I drop to my knees and crawl over to you as you spread your legs to greet me. Your pussy is glistening, just begging to be eaten. I work my tongue along your inner thighs, then on to your luscious cunt. I can't get enough of your juices, your fragrance envelopes me. I want all of your pussy in my mouth. You lift your legs up in the air as I tongue your clit. Then I move down across the lips until my tongue finds your other little hole. You love to have me there. My hot tongue darting. My breath on your most private parts. This is where your essence resides. Here, between your legs. And I am ministering to it. Paying homage to it.

With your legs already up in the air, I push your knees back further toward your chest, which exposes more of your asshole to me. I plunge my mouth onto it, then penetrate it with my wet tongue. Flicking in and out. You moan. You are breathing harder. I've reached your inner being. You feel like you are going to cum. It's a strange feeling because your cunt is not being stimulated at all right now. Just your ass. But it would feel so good, and so right, if you could cum like this.

I pull butt plug #2 out of my pocket. It's a half inch larger in diameter than the first one I used the last time we met. I put it up to your mouth to lick, to lubricate. You do it eagerly. You can't wait for it to enter you. I press it up against your hole. You relax into it nicely. I can tell you've been practicing. It slips in smoothly when I apply enough pressure. Then disappears as you close around it. Your asshole is now stretched more than before though. The base is a half inch wider. It feels large to you. Like really intrusive. You feel completely plugged up, clear up into your abdomen. You aren't, of course, but that's the feeling.

I hold the base and pull it very slightly out. Just enough to stretch your hole a little, then to relieve it as the bulb moves back in. You moan, it's uncomfortable, so I let it be for now. I want to kiss you for being such a good girl. You are still aroused, of course, and want me to fuck you. I decide that that would be a good thing to do now to help you through this phase.

I stand up and pull down my pants. My cock is fully hard. I get on top of you, missionary style, and put the head of my cock between your wet pussy lips. While we do some deep french kissing I slip into your hungry cunt. I'm fully into you and my balls are against the base of the butt plug. You feel their weight against it pressing it into your ass. I begin to stroke in and out. As I thrust in you feel my balls banging on your ass and the ass plug. It's very pleasurable to you, particularly after enduring the insertion of the butt plug. In fact the combination of my cock and the butt plug gives you the fullest feeling you've ever had! You love my cock plunging into you while the ass plug vibrates with each impact of my swinging balls. You are getting banged big time. And it's wonderful.

I continue to pound you. I'm going deeper with each thrust. Our tongues are going at each other the same way our genitalia are. We are in a full fuck now. Humping like beasts. Grinding and thrusting against each other. The passion rising with each stroke. You feel yourself welling up, you are going to come apart. It feels like I'll split you in two. You want release now! You have to cum. You heave and pant. You're going mad! Involuntarily, your mouth opens wider, we lose our lock as you gasp for air! Nearly choking as you convulse. Shuddering at the hips. Cumming huge! "Oh!" "Oh!" "Oh!" "Oh!"

Then your mouth is back on mine. More tongues as you writhe to the last of your orgasm.

I'm hotter than a pistol but don't cum. I have other plans for us that will take care of that in due time. I just wanted you to get off as a little reward for being such a good girl with your anal training. You've made very good progress in a very short time.

After you've calmed down I tell you to stand up. I tell you to walk around the room with the butt plug in place like you did in lesson #1. I watch you as your cheeks surround it as they bump along with each step. That is a lovely sight. My pecker, having calmed down some after pulling out of you, perks right up again. I tell you to lay on the bed while I cuff your ankles, then your hands behind you. I tie your legs together just above the knees. The skin on your legs is silky smooth and I want it to stay that way so I don't bind you too tightly, just snug enough so that you can't separate your knees. I then put a ball-gag in you pretty little mouth and fasten the straps on your head. You're new to ball-gags so the sensation of being gagged is unfamiliar. I love seeing you like that. Helpless, really. At my beck and call. And so-o-o hot!!!

I would love to fuck you in the ass right now, but I must let you complete your training first. I grab your hair to pull your head back. Saliva is beginning to appear around the edges of the ball-gag. You'll be drooling soon. With you on your side, I put my cock between your magnificent tits, pushing them together. They are heavy and oh so fleshy. Your nipples are fiery red. And hard. You love my cock there. You wish I'd put it in your mouth, but of course the ball-gag makes that impossible. I put my mouth on one of your nipples. Suck it hard. Nibble it with my teethe, flick my tongue over it. You moan in the ball-gag. I put the head of my cock on your nipple, put the tip of your nipple in the tip hole of my cock. "O-o-oh." You love my precum lubricating your nipple. Now the other one. Then I wave my cock over your face to tease you. Let my balls drag over your face. Oh how you'd love to lick them. I grab your hair to pull your head back so I can rub my cock over your lovely neck. My balls dangle onto your throat. You are getting the full sense of my manhood, but you can't do what it is you want to do the most, and that is put your mouth on it.

I roll you over onto your stomach for a birdseye view of your luscious rump. So full, so fleshy. M-m-m-m. I grab some of your ass flesh. Bite it. Knead it with my fingers. Jiggle it to see it ripple. Play with your ass like it was my own private play toy. You love your ass being fondled like this. I spread your cheeks to get a good look at the butt plug in your little hole. So delectable! I lay my now fully hard cock between your cheeks, right across the butt plug. You feel it's size and mass as I slide it up and down your crack, my balls trailing over the back of your legs. I grab your hair again, pull you back hard and stick my tongue in your ear. Saliva drips from the ball-gag. My hot breath in your ear sends you. You're overwhelmed with my closeness. Your pussy and your ass are now longing for my cock. You'd love to have me enter you right now!

I slap your ass. You recoil. I slap it again. It wiggles with each blow. You mumble through the ball-gag to do it again. I slap it again. And again! Your muffled squeals tell me you're loving it. You're under my complete control. But you trust me completely so you're not afraid. You love me doing this to you.

I tug on the butt plug again. I don't pull it all the way out, but just enough so the bulb is stretching you again. "O-o-oh," you groan. You feel like you're going to split. I let it slip back in. Then I tug on it again. "O-o-oh," again. Then a few more times. You are doing wonderfully with this. Beginning to enjoy it now. Finally, on the last tug I pull the butt plug all the way out. Your lovely asshole gapes open momentarily before closing. God that's gorgeous!

I remove the ball-gag; your lips and chin are covered in saliva. You are so hot, I can't resist. Our mouths gobble each other! I place the head of my cock right on your hole. Your fabulous ass cheeks grip a couple of inches of my shaft. Then I slide the tip of the head in just enough to stretch you back to the point that the butt plug achieved. You like the warmth of it so much better than the coolness of the butt plug. If it wouldn't hurt, you'd love to have me ram it all the way in. I let it sit for a minute, then pull back a fraction of an inch so that you close some, then push in to expand you again. Then repeat many times. It feels like you're being fucked in the ass, but without full insertion. You love it! It's incredible! You feel so hot. Your gasping again. You moan, telling me how fantastic it feels.

I tell you that you can cum this way if you wish. You can have your first ass orgasm with a cock stimulating you. And you can be in control. "Oh god, thank you," you say. You push against me, stretching yourself then relaxing back, then pushing again. It's having the same effect as when I was pushing on you. You are gulping now, panting and gulping. You can't believe the sensation in your ass! You are going to cum again, and cum oh so good!

Your ass cheeks shudder, the flesh shaking like jello. God what a sight! I think I'll explode with you. You groan a deep groan, "ooooooh!" Finally, quick spasms take you to the final height! You cuuuum...oh sooo good! Your beautiful green eyes roll back in your head as you are in pure ecstasy!

Now I'm having spasms of my own. The sight of you in such bliss with your ass cheeks gripping my shaft as you convulse is just too much. Cum shoots out of me before I can even think about controlling it. The hot stream injects your ass! It's flow warming and lubricating your hole. Which opens slightly more with the pressure from my head. "Oh gawwd!" you gasp! "Oh gawwd!" Now it's all in your crack too. And down your leg.

I rub my cock in it, then offer it to you to lick. You clean me with your talented tongue, curling it around the head and lapping along the shaft. "Mmmmmm," you coo. But I don't hear you, as it is now I who is in ecstasy.

Finally sated, I uncuff your hands and your ankles, and untie your knees, giving you a soothing massage of the bound areas. I lie down next to you with my arms around you. We kiss. We snuggle for awhile. You are so beautiful like this. You look so content and so satisfied. I never want to let you go.

Jack597
Jack597
171 Followers
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