We’re out for a date night.  We just had dinner and shared a bottle of wine and then we go for a walk along Broadway.  You’ve been flirty with me all night and trying to make me horny... which you know is definitely working. You’re wearing a dress and I keep sliding my hand up your leg to feel you, exposing a bit of your ass before you swat my hand away and continue to tease me.  As we’re walking, you notice a sex shop on the other side of the street.  

“They are still around!” You say, as you grab my hand and walk towards it.  I laugh and follow.  

As we enter, I say “It’s been so long since we’ve been in one of these!”.  

We both casually start looking around.  There’s a lady watching the counter. She looks at us but gives us space to look as we please. We browse the DVD section and laugh a bit that it still exists.  You pick one up and start looking at the back and it’s about a woman who’s husband takes her for walks naked, through trails and then fucks her whenever he wants.  I start to rub my hand up your leg and rub your wet pussy with my thumb.  We’re hidden behind the DVD stand but you try not to make a noise.  You rub my crotch for a few seconds through my pants but then stop.   We make our way over to the sex toys and start looking at some of the options.  You pick up a butt plug and show it to me.  I jokingly pick up a rather large one and show it to you.  

You laugh and we’re both startled to hear beside us a lady saying “it’s actually totally doable and enjoyable if you work up to it”.  

It’s the lady from behind the counter. We must not have noticed she had walked up to us to offer assistance.  

“Really?!?!” You reply.  

Then she hands you a pamphlet, opens it up and points to “Anal for Beginners”.  

“We have in house seminars for anal sex among other things if you guys would be interested. No matter how big your husband may be, we can get you up and ready for him in no time.” She says.  

You pass back the pamphlet and say “I think we’ll think about it…” at the same time that I ask “how much is it?”.  

She insists that you keep it, so you put it in your purse and she replies “$35 per person and classes usually take about an hour.  I’ll let you guys think about it and if you decide you want to sign up, just give us a call.”  

She walks back to her desk and we look at each other laughingly and hang the oversized butt plug back on the wall.  

We leave the store and jump in a cab.  We’re both so horny, I’m feeling you up in the cab.  You almost cum by the time we make it home.  We pay the cab driver, run inside and I pull your dress up, push you over the bed and slide my cock into your pussy.  I thrust quickly into your wet pussy, bringing you right back to where you left off, and as you know I’m close to cumming, you tell me to stick it in your ass.  I moan in excitement and take my cock and press it against your tight asshole.  You rub your pussy fast with your hand and press back, painfully but willingly accepting my cock into your ass.  You move back and forth, stroking my cock, wanting my cum inside you.  You cum from rubbing your clit and your ass tightens.  I continue to thrust slowly and grab your ass as I cum inside you.  I lay on the bed beside you, still inside your ass.

You turn around and kiss me and say “lets do it… it might be fun… lets see what the seminar has to offer!”.  

I’m surprised but agree and we call right then and book a class which is running the following week.     ​ The night of the seminar you're getting dressed. You put on a dress and I convince you not to wear any panties. We both have no idea what to expect but think it should be a fun experience. You tease me about getting to fuck your ass later after the seminar. You can tell that I'm incredibly horny. The tickets say 7:00 so we try to hurry. We arrive at 7:05 and open the front door. We glance in and the lights are off to the front of the store which is closed now. We hear voices from through a door at the back. We walk in and through the door and see about 8 people sitting in chairs facing a man up front. There's 3 other couples and two single guys. We quickly sit down in the back. The man up front is dressed in a dress shirt and dress shoes with nice pants. He looks very sharp for someone about to host a sex seminar.

He looks at us and says "Welcome! What are your names?".

I reply "I'm Bryan and this is Clare".

He walks over and passes us a booklet that says "Anal for beginners". I open it as he continues to talk to the group. We browse through it and it's basically occasional diagrams with lots of pictures of close ups of anal sex. It looks pretty amateur but shows things like a picture of an asshole before and after anal sex. The after picture definitely has cum leaking from it.

We look back up at the demonstrator and he says "So, a little about me. I'm 38 years old, I've been teaching sex seminars for about 3 years, sex is a hobby of mine and yes, that's me in those pictures."

Everybody laughs and then pretty well everybody glances back at the pamphlet. Then he continues "The woman in the pictures is one of the other sex educators. Usually she does these demonstrations with me but unfortunately she's running a bit late. Hopefully she will still make it and join us soon."

Then he starts talking about the importance of lube. He talks for about 5 minutes about preparation and how enjoyable it can be if done right.

"Can I get a volunteer?" He asks.

Everybody is quiet so he calls on a woman sitting beside us.

"How about you?" He says.

She shyly stands up and says ok. "Which of these do you think is a reasonable butt plug?"

He hands her a few different sizes. She holds up a small one and he replies "Great! Reasonable is relative to experience, but after today's seminar and some practice, I think you will change your view and pick this one pretty quick." Then he holds up an almost comically large butt plug.

"Ok, you can go ahead and sit back down. Thanks for your help."

He then looks at his watch and then the door and starts to talk some more, seemingly trying to kill time. Then he starts to ask around the room what people's anal sex experience is. Everybody says they've never tried it or maybe have tried a finger.

When he comes to us, he asks me. I reply "I've put myself in her ass and had brief anal sex." You start to blush and look at me and then him and nod in agreement.

"Great!" He replies. He seems genuinely excited by that. Would you mind if she comes up as a volunteer?

"Sure" I reply and look at you.

He moves a chair right to the front and center. You slowly walk up and he grabs your hand and rolls back a padded table from the front. You wonder what you were volunteered for. You stand facing the group, and he grabs you by your shoulder and turns you around. You turn your head and look at me as I'm now standing beside you and I smile at you and nod in approval. He tells you to relax as he glides the table up to you and presses on your back. You put your hands on the table and he points to your ass.

"Do you mind?" He asks me again.

"Not at all" I reply. I grab the bottom of your dress and pull it up, exposing your ass, as you're not wearing any panties.

You turn your head again to look at me in shock.  I give you a smile showing that I’m finding this funny but am also enjoying it.  Your legs are tight together and shaking a bit in nervousness. I smile at you and you quickly look away to hide your beat red face from the crowd. He presses one hand on your back again and with the other he pours warm oil on your ass cheeks.

"Let's start with a warm oil massage." He says.

You feel my hands on your ass rubbing from your lower back down to your lower thighs. I guide your legs open a bit more so I can get between them. He tells me to make it a very deep massage and to really dig in to relax the muscles. You're still in shock that your exposed like this and had no idea this was coming.

Then he says "great, you can have a seat if you'd like" and I sit down in the front chair.

He reiterates the importance of relaxation and arousal.

"Do you mind if I...?" He asks me again.

"Not at all!" I reply.

You turn your head to look at me, surprised, as he stands behind you and starts to work the oils from your ass up your back. He vigorously moves up and down from your ass to your upper back. You can feel his hardening cock through his pants pressing up against your butt when he reaches forward. It is a great massage though, but you find it hard to relax.  He presses a bit harder and you’re forced to relax your body.  Then he reaches far, hikes your dress up higher and starts massaging your tits.

“It’s important to involve the whole body and all the erogenous zones too fully arouse your partner” He says.

Now you can't help but get aroused, but at the same time you feel exposed and embarrassed.

He stops suddenly, takes a look at your ass, pulls your legs apart a bit to check your pussy and then says "I think she's good and ready!"

You hear him snap on a latex glove but you're distracted by a tickle down your thigh as your pussy starts to drip. You're confused because your mind is terrified but your pussy is undeniably incredibly wet and horny. You suddenly feel warm oil pouring on your asshole. Then he starts to talk again about starting slow, he presses a finger against your asshole. You turn and look at me, exposing your tit as you lift your side. You see me watching intently and I look at you and smile reassuringly. You can see that my hand is on my lap and I'm uncomfortably hard. You scan the room as he's talking and see that one of the women has her hand down her partner’s pants, trying to be discrete but it's quite obvious. Your attention is quickly pulled back to the demonstrator as he slides a finger inside you. You can barely focus on what he's saying you're so distracted. He didn't even go very slow, he just slid it straight and all the way in. Now he holds it there. You put your head back on the table and grab the sides. He talks very matter of fact about the anus and how it just needs training which sometimes only takes one session to achieve orgasm through anal sex. Your pussy has a steady stream of juice trickling down your thighs now. He explains how the sight of a penis can actually help with making an asshole more accepting. Then he asks me to come up and remove my pants for you to see. I come up and stand beside you and drop my pants, freeing my erect cock. You can see that the tip of it is soaked from precum from sitting and being so aroused. You look at it and as you stare, craving it, he pulls his finger out and replaces it with two.

"Great! You can have a seat now if you'd like." And I return to my seat.

"Do you mind if I get a bit more comfortable?" He asks.

"Go right ahead" I reply.

And he removes his fingers, takes off the glove and removes his pants, showing that he is clearly enjoying this. You take a moment to reach down and feel your pussy which is totally drenched, and then return to your previous position. He puts on another glove and states how important involving the vagina is at the beginning to ready the asshole. Then he slides one finger in your asshole and two in your pussy. You feel him rub them together inside you and it's like he has total control over your body. You scream and moan, trying to resist but instantly orgasming. You feel embarrassed for getting off in front of everybody. You turn and look at me and I'm stroking my cock slowly. Now, he slides two fingers in your asshole and just one in your pussy. It's uncomfortable but then he pulls your ass cheeks apart and it feels ok. Then he slides two more fingers in your pussy.

He starts moving his fingers up and down and you uncontrollably cum again. You feel his cock repeatedly run against your ass cheeks as he goes about his business. Your pussy aches every time you feel it. You don't want to be so horny but you can't help it. The people watching let out a cheer encouraging him. He removes the glove and reaches up and massages your tits again. This makes your ass stick in the air as if you have no control over it. As he leans in, you feel his cock rub against your soaked pussy lips. He turns and looks and me and asks if I want to take over.

He says "I think she's ready!".

I reply "well you've done all the work... you may as well show us how to follow up!"

You don't even fight it. You just grip the table and he slides inside you. He doesn't even touch your pussy. He just thrusts the full length over and over bringing you to another screaming orgasm. He continues to assure the audience that once the woman is this aroused, you can fuck the ass just like a vagina. Your legs are like rubber but you just try to keep your ass in the air.

"Wow I'm turned on. She's really great" he says.

He pumps a few more times and grabs your tits, pulsating his load at his full depth inside you. With each pulse his balls tighten, stimulating your clit. It feels different - you can feel his cum hit the inside of your ass over and over. Your ass must be way more sensitive to temperature too, because you can really feel the warmth as it pumps inside you. He quickly pulls out and steps aside to show your gaping asshole. He reaches under the table, grabs a reasonably large butt plug which is see through glass and inserts it inside you. He tells the crowd that these plugs are available for $39. He looks at me and says this one is on the house. I get up and shake his hand and thank him for the great demo and then help you up. The crowd comes up and all starts thanking him and telling you that you did great.

You pull your dress over your tits. You're still in a daze and your pussy is still incredibly horny. As you stood up, it feels like you're leaking cum, but you reach down and you're not. The butt plug is firmly in place. You sit down in a chair because your legs are wobbly. I seem to take forever talking to people and taking compliments about how well you performed.

You get up and start to leave and I follow. You grab my hand as we walk and place it up your dress on your pussy, not caring who sees at this point. We get to the car and you open the back door and ask me to get in first. I get in and you pull my pants off and climb in on top of me. You slide me into your pussy and it immediately soaks my cock right down to my balls.

As I penetrate you, you asshole widens. The butt plug must be filled with air or a liquid, because as my cock displaces it through your pussy, the base of it grows. My cock is rock hard and you know I was close to cumming already. You bounce up and down, and your pussy feels so tight on my cock with the butt plug still inside, widening your asshole. It hurts but your pussy is so hungry and in need. You ride me fast, quickly cumming. You know that your pussy is incredibly tight for me, and being horny as I was, I quickly fill you with my huge load. As soon as you pull my cock out of your pussy, my cum leaks out, and at the same time it comes pouring out of your ass. The butt plug had stretched your ass so wide that now that my cock is out, it’s not enough to keep the cum inside.

You get out into the parking lot quickly, dripping cum from both your holes. When you’re ready you pull your dress back down and climb back into the car and we head home. On the way, I mention that there’s another seminar next week on oral sex... and I ask you if you want to attend.  

Note: Hope you enjoyed! Upvotes and comments/feedback are read and appreciated!