We rinse and dry each other off, then walk back to the bedroom. I pour a glass of wine, and we begin discussing anal intercourse.

“I know you’re concerned. You’ve never done anal, you’re a virgin in that sense, and you’re afraid you might hurt me. Honestly, if it’s too much, I’ll tell you, okay?”

“Now, tell me, lover, what have you done regarding anal, and what are you afraid of?”

“Nadine, the most I’ve ever done is what I did to you earlier—pushing a finger in. No woman has ever let me do more than that.”

“Brian, are you saying you’ve never kissed an ass, rimmed a woman, or tongue-fucked one? And no woman has ever given you that pleasure?” I reach out and hold his hand as he looks down at the floor. “Well, we’re changing that. You’ll experience all that joy—not only in giving but also in receiving. I’ll rim you and tongue-fuck you.”

I glance at the clock and gasp. It’s nearly 5 a.m., and of course, it’s a school day. “Brian, why didn’t you tell me it was so late? I have to be at school in less than two hours. There’s no way I can keep my promise to you now. I’ll have to keep it tonight. Is that okay with you?”

Brian smiles and says, “Nadine, my sweet lady, that will work out perfectly. It’ll give me a chance to read up on the right ways to please a woman and how not to hurt her. Before you go, can you give me some hints on where to look and anything I should get?”

“Brian, you’re so sweet. I don’t have time now, but I’ll either call or text you today.” After saying that, I put on my blouse and skirt, pick up my underwear, and head for the door. Thank goodness it’s still dark outside—no one will see me skipping back to my house.

I enter and head straight to my bedroom to get ready for school. I realize I have nearly an hour and a half before I need to be there, so I take the time to give Brian a few ideas on how to prepare for my visit tonight. I sit down and start composing a text with everything I can think of to calm him, keep him excited, and make him want me there now.

My list includes all the typical advice: lube—lots of thick, high-quality lube for both him and me. That’s the most important item for him to get. I also suggest that since he’ll be enjoying some personalized anal play, he should get a small-to-medium anal plug and insert it about an hour before I come over. I’ll do the same.

I ask that he have plenty of body wash for afterward, as well as wet wipes for cleaning up. Finally, I recommend he read “A Sex Therapist’s Beginner’s Guide to Anal Sex”. Feeling good about the list I have sent him, I dress in my schoolteacher clothes, eat a hurried breakfast, and head out the door.

The day flies by in a blur. I’m still on a high from last night’s session and looking forward to tonight, fulfilling my promise.

I get home around four in the afternoon. Brian must have been watching because I’m barely through the door when he calls. “Nadine, if you’d like, I’ll prepare us a meal. It’ll be ready around seven. Will that be okay with you?”

“Brian, that’s so sweet. Of course, I’d love to have your home-cooked meal.”

“Great! I got everything on your list, and I spent the afternoon reading the beginner’s guide.”

“Brian, tonight will be a night to remember forever, I promise.”

We hang up, and I slip into something comfortable because I have a few errands to run before getting ready and heading to Brian’s.

With my errands completed, I return home and run a warm bath. I soak, then shave, leaving no hair on my body except my head. I step out of the tub, dry off, and rub body lotion over myself, enjoying the sensation.

Last night, I went over dressed plainly, not sexy at all, well not on the outside. Tonight, I’m dressing to seduce. I want him so turned on he’ll struggle not to cum the moment I walk in. He’s told me he likes stockings and garters, so of course, I’ll wear those, along with a thong, a fishnet dress, and four-inch heels.

The dress, stockings, and garter are white, but my thong and heels are black. I dress and check myself in the mirror—I have the look I want. I look like a working prostitute.

That will be my first gift to Brian tonight. I pack my bag with extra clothing and the goodies I picked up during my errands. Grab my overcoat and head to the door, then realize there’s no way I can walk across the lawn in these heels. I take them off, put them in my goodie bag, and slip on a pair of flats. I close the door behind me at 6:55 p.m. and walk into a night of pure excitement and sex with my new lover.

I stop at Brian’s door, slip off my flats, and replace them with my heels. I ring the bell, and when he opens the door, I’m taken aback. He stands there in dress slacks, a button-down shirt, and a sports coat. His hair is combed to perfection, and he’s holding a glass of wine for me. I take the wine, hand him my bag, and ask him to put it in the bedroom without peeking. When he walks away, I remove my overcoat and stand there, looking like a pro waiting to be picked up.

He returns and stops, a smile spreading from ear to ear. He licks his lips and says, “Nadine, I know I said it yesterday, but you look good enough to eat.”

I smile, lean in, kiss him, and say, “I expect you to do just that.”

He takes my hand and leads me to the table, where a meal straight out of a French magazine awaits. It’s not a lot, but it looks delicious: oysters, shrimp, crab cakes, and a salad. We sit, and he serves me—what a gentleman.

As I sample the food, I discover Brian is not only an incredible lover but also a fantastic cook. As we eat, Brian tells me about his day. He read the beginner’s guide and went out to purchase not only lube but also a set of anal plugs, from small to large, and even anal beads. I’m amazed—my anal virgin clearly wants to learn and experience everything he can. As he talks, I grow more excited. Since I’m wearing a fishnet dress, my nipples have hardened and are now poking through the netting.

Brian notices and is clearly captivated. He asks, “Will it hurt when I take your dress off?”

I giggle. “Oh no, lover, they’ll slide right out. Watch.” I stand and pull the dress over my head.

He gasps as I stand before him in my garter, thong, stockings, and fuck-me heels. “Nadine, you’re beautiful, sexy, and I think you have experience in having men please you.”

I sigh and say, “Now, my love, I do have some experience and I do hope you will give me back as much if not more pleasure. Let’s see what you’re hiding under all those clothes.”

I reach out, remove his sports coat, undo his belt and pants, and let them slide down. I look and see Brian is wearing a dark colored thong, just similar in color to mine. While mine has a wet spot at the base, his is tented upward with a wet spot near the top. Brian strips off everything except the thong, revealing his incredible body.

“Let’s go to the bedroom and explore each other. Then you can eat me like you promised.” As we move, I notice Brian’s walk is a little stiff, and I ask about it.

He responds, “Nadine, I pushed a plug into my ass. I thought, since I’m a big guy, I’d go with the largest one. It felt odd and hurt, so I took it out. I can always put it back when you want.”

I giggle and say, “Honey, it’s okay. Soon you’ll know the joy of anal play, and opening yourself up will pay dividends, I promise. But since it’s your first time, you shouldn’t start with the biggest one, you need to get used to them.”

Once in the bedroom, I pull down his thong, and his beautiful, hard cock begs for me to suck it. But before I can do anything, Brian grabs my thong and pulls it down, revealing my smooth pussy. He moans and says, “Shall we both enjoy our first snack of the evening?”

Brian picks me up, lays me on the bed, crawls over me, and licks my pussy, savoring its natural cream.

“Nadine, I hope you don’t mind, but I’d love for you to keep on your garter, stockings, and heels—it’s so hot. You’re so erotic, and honestly, you dressed like a prostitute, which is so hot.”

“That’s the look I wanted for you tonight, and I’m glad you like it. Now, turn around and let me suck that sweet cock while you eat my pussy until I scream.” He turns, still atop me, and lowers his cock toward my face. I take it with both hands, stroke it slowly, and then open my mouth to take in just the tip. As I do, his hands slide under my thighs, pulling me open, and his lips and tongue feast on my pussy. The moment he starts, I begin to moan. I suck just the tip, sliding it in and out of my mouth, letting the edges of his cockhead graze my lips. I feel more than hear his moans as his mouth remains pressed against my pussy. This position is perfect—his tongue works my clit like a magic bullet. I begin thrusting my hips upward, craving more of his mouth.

I’m furiously pumping my body into his mouth when my first orgasm hits. I scream with his cock in my mouth and push myself further up, wanting more of his incredible touch. Just as orgasm begins to recede, his hand reaches up and pushes my plug. This triggers an even more intense orgasm, something I can’t recall experiencing so quickly after the first. As he pushes, I thrust back, feeling the plug slide deeper in and out of my ass. I open wide, scream, and his cock fills my mouth, his balls now the only thing not inside.

Trapped, I feel him begin to slide in and out of my mouth. Then he pumps one load after another into my throat and down into my stomach. It’s as if we both instinctively know how to pleasure each other, and this is only our second time together.

He pulls out, and I breathe, but his lips are still on my now hypersensitive pussy. As he goes to lick and suck more, I beg, “Please stop. I need to rest.”

We crawl into each other’s arms and kiss. I taste myself on his tongue, and I’m sure he tastes his cum on mine. As we lie there cuddling, I whisper, “You know it’s Friday, and we have the entire weekend to ourselves. My family comes home Monday, so we can just be ourselves here until then. Is that okay with you?”

“Yes, Nadine, that’s perfect. I not only bought the lube but also enough food to keep us indoors until Monday.”

“Brian, you’re my hero thinking of all of that. I’m rested now. Would you like to begin your lessons and lose your virgin status, or do you need more rest?”

“I’m ready. I’m so ready.” I detach myself from him, roll over onto my stomach, and get on all fours.

“First, my sweet man, you need to examine my ass and tell me what you see.”

Brian gets behind me, and I feel his hands slide over my ass until they meet over my jeweled plug.

“I see the most beautiful ass in the world, with a large jewel coming out of it. Is there anything I should do?”

“Well, since we’re playing, why don’t you start by kissing your way all around? Don’t be shy—I won’t bite.”

I feel his lips on my cheek, then he moves, kissing every spot on my ass except the plug.

I giggle and say, “Brian, it’s okay. You can kiss the plug, and once you do, grip it and slowly pull it out.

“Oh yes, Brian, just like that. Tell me, what do you see?”

“I see your rosebud, but it’s open. Is it supposed to be like that?”

“Yes, it is. The plug has relaxed me a bit so I can take all of you more easily. But first, kiss my rosebud.

“Oh yes, that feels so nice. Now treat my rosebud like you do my pussy—lick it.” As I feel his tongue, I moan. “Yes, lick my ass. It feels so good.” His tongue sends shivers through my entire body.

Brian gets past his initial shyness and begins licking my backdoor with enthusiasm. My moans grow louder, and I start pushing my body back against him. Then he surprises me, and I feel his tongue snake into my tight hole. I push back, craving more of his tongue. He grips my ass, pulling me apart as he begins to seriously tongue-fuck me, lubing me with his spit.

As he fucks my ass with his tongue I reach down, find my clit, and start rubbing. The sensation is so intense I have to slow myself down—I want my orgasm with his cock inside me, not just his tongue.

Between moans, I tell Brian, “My dear, it’s time. I’ll keep playing with my pussy. You need to lube both of us up. Put some on your fingers and slowly insert one finger into me, making sure it’s well-lubed.”

I feel his cool, wet finger on my asshole, and he slowly pushes it in. He pulls it out, then he’s back bringing more lube. He stops, and I feel more lube—this time with two fingers.

“You’ve got it down. Now make sure you’re lubed too, my dear, and then mount my ass. Fuck me—start slow, go a little at a time, then rest, then push again.”

I feel the head of his cock at my entrance, and he pushes in just a fraction before stopping. I push back when I’m ready, and he begins again. It all snaps into place—his head finally pushes through, and we both sigh. He slowly pushes in as I push back, taking more of him. We move slowly, adding more of him into me until I feel his body against my cheeks and his hands gripping my hips tightly.

“Brian, my dear, you’re all the way in. You’re no longer an anal virgin.”

“Nadine, I’ve never felt anything like this. It’s soft but so tight. It’s like your body has surrounded me and is holding me forever.”

“That, my sweet, is the magic of anal. Now that you’re all the way in, it’s time to fuck my ass. As you do, I’ll work my pussy with my hand. I’ll feel you through my fingers when I go inside myself.”

He slowly pulls back and pushes forward, and I hear him moan, “So sweet, so tight. I’m in love with your ass.”

“If you love my ass, fuck it like you mean it.” He begins pounding into my ass, pushing forward while pulling me back with his hands on my hips. I feel his balls hitting my body as he thrusts in and out.

Every time he slams into me, it’s like the breath is forced out of my lungs. He slows down, gripping my hips tightly, pulling me deep onto his hardness. He moans, “I’m going to cum. I’m going to fill your ass with my cream. Are you ready, my sex goddess?”

I can only moan a “yes” as I feel his cock with my fingers that are deep inside my pussy. Then he pulls me in, and I feel his hot cum pound into my ass. That feeling and my fingers send an explosive orgasm through my body, it’s an experience one gets only when both holes are filled at the same time. It’s a truly incredible experience everyone should have at least once in their lives.

Brian slowly pulls back, and my ass pops when he pulls out completely. I feel his cum start to slide down the inside of my leg and say,

“Brian, I have to run, or there’ll be a mess all over our bed.” As I rush to the bathroom, he yells, “Everything you asked for is the vanity. I hope there’s enough!”

I see everything and begin cleaning up. As I sit and let things drain, I think, Brian, you really know how to show a girl a good time. Soon, I’ll be returning the favor.