Sir commanded me to wear a mini skirt, button down blouse, no bra or panties and my garter belted thigh highs for dinner. I chose a special black leather flared mini skirt and a satin blouse for the night. My heels were high and red bootie shoes. I came out of the bathroom of our room nervous, but ready for Sir's inspection. Our eyes meet and I smile nervously. Standing with my legs spread, hands behind my back and wait for Sir to approve of my outfit. His smile is warm and soothes my nervous energy.

"You look beautiful, my Enola."

"Thank you, Sir."

Sir circles me and runs his hands around my body. I skin is still tender from being fucked so hard earlier in the afternoon, but his fingers softly touch my lips and find them slick with our combined juices. I can still smell the sex all over me and I love it. Sir takes my hand and leads me to the desk in the room. I bend over and Sir smooths skirt up to expose my ass.

"So beautiful my sexy slut." Sir says as his hand glides over the globes of my ass.

I feel the cool liquid as it slowly slides down the crack and into my bud. His fingers working the lube around as he inserts a finger into my ass. He gently moves his finger in and out spreading the lube evenly. More lube and then a second finger. His rhythm is slowly, but steady and confident as he works me up. My breathing is picking up and I whimper as his other hand holds me in place so that I am not able to move. I have my hands in front of me gripping the edge of the desk as Sir continues to prepare my ass. I feel something cold replace Sir's fingers. I startle a little at the contrast and Sir hushes me and strokes my back in comfort.

"Sssshhh, my sweet Enola. I promise to be as gentle as possible."

"Yes, Sir." I say in a whisper.

"Do you trust me?"

"Of course, Sir."

"Good. Now I am going to go slow as the plug is a little bigger and I want to make sure that you are well lubricated and comfortable. I want you to relax and push into the plug as I insert it, okay?"

"Yes, Sir. Thank you, Sir."

"That's my good girl, Enola."

I preen at his praise. It warms me from the inside when Sir calls me his good girl. I feel the bulb of the plug expanding me, the tightness burns slightly, but is not unbearable. Sir maneuvers in and out going deeper with each push in. I do as Sir instructed and push back as he slides the plug I further. I feel more lube and finally the plug is in. I feel stretched and full. I'm breathing heavy with the intense desire that has consumed me. Sir runs his fingers down my slick pussy and inserts his fingers pumping in and out a couple of times. They slide easily in and out from the combination of my wetness and the excess lube that has slid into my opening. I'm so heady at this point. Breathing deeply, almost panting.

"Please Sir."

"Please what my Enola?"

"Please help me, I need..."

"I know what you need" Sir says

SMACK

Sir smacks each globe of my ass. Not too hard, but just enough to make me purr. Sir then inserts the second little toy for the evening. The remote-control vibe slides easily into my pussy. Sir moves it deep into place. I sigh as it feels snug in its new home, as if it was always meant to be there.

"That's it, Enola, it's time to go." Sir says as he helps me up.

Sir smooths my skirt down and into place. As I stand and face him, Sir kisses me deeply, cupping my breast in one hand and squeezing it in a sign of ownership and affection. Sir kisses my nose and then my forehead.

"You humble me with your trust, my sweet baby girl."

"I still can't believe that we are finally here, spending the night together. It feels like a wonderful dream that I don't want to wake up from." I admit.

"I know baby girl. We will spend our night as we are. Sir and Enola, lovers, friends and so much more. Now let me show off my sexy slut." Sir says with a big grin. 

I grin back and take his hand as we head out to dinner.

Sir and I are standing out in front of the hotel waiting for our car to be brought around and I'm fidgety. The plug feels snug and slippery at the same time. Sir used a fair amount of lube and the weight of the plug when I walk makes me worry that it might slip out, even though I know that it won't. Either way I keep clinching my ass just in case. At the same time, I worry that the vibe will slip too. Walking is becoming a serious challenge. Standing there has me shifting my weight between my feet trying to ensure that they both stay in place.

"Stop fidgeting Enola." Sir says with a chuckle.

"I'm worried one of the them is going to slip out when I walk."

"I know you are." And Sir full on laughs.

"It's not funny you jerk." I protest, even as I smile because let's face it, it kind of is.

I'm self-conscious because the skirt is so short and my blouse under my coat is rubbing against my swollen nipples. Sir spent quite a bit of time on them this afternoon and they are super sensitive. I know that when we get to the restaurant and I take my coat off, they are going to be hanging low and on display. As we stand there, the wind picks up a little and blows my skirt. I struggle to keep it down and my sweet Sir steps behind me to keep protected from the eyes of the people around us.

"I've got you baby girl. You are mine and I protect what is mine." He whispers in my ear.

"Thank you, Sir." I sigh in relief.

"Of course, baby girl"

The car pulls up and Sir helps me in. After we get settled in, I feel something begin to vibrate and I snap my head to look over at Sir. He's grinning that shit eating grin that makes me laugh.

"Nice." That all I can say. Let the games begin.

"Open your coat Enola." Sir instructs.

I do as I'm told and Sir reaches over to exposure my breast so he can fondle it.

"Now open your legs wide and show me what is mine."

Again, I do as instructed and pull my skirt up opening my legs for Sir. He is careful to keep his eyes on the road, but at the stop light he leans over and kisses me hard. There is a car next to us, but my eyes stay focused on him.

"Good girl."

I smile wide at his compliment and then his goes to his phone. That's when the vibe goes up a notch and I whimper from the vibration between my legs. The light changes and we are off again.

"Touch yourself Enola. Show me how wet you are."

I reach between my legs and run my finger across my soaked folds. Then I offer my finger to Sir and he sucks it into his mouth.

"Mmmmmmm. Now that is some sweet nectar baby girl. I could make a meal of that all by itself." He praises.

"Now pinch those beautiful nipples for me. Draw them out and show me how much you love it."

I open my blouse wider and expose the other nipple and pull on them equally. Drawing them out and twisting them hard. Purring with satisfaction and desire. Wishing it was Sir's fingers and not my own. I can feel my juices slowly sliding out of my folds and down my ass where it pools on the inside of my leather flare skirt.

"My Enola loves all this stimulation, don't you baby?"

"Yes." I whimper.

I'm so turned on. The vibration goes up a notch again and I look over at Sir in desperation.

"Please Sir. I need to cum."

"Not quite yet baby girl. You still have to get through dinner."

"No, please Sir. I need this ache to ease. It's ... I ..." I stammer.

"I know and you will just need to breathe through it. No cumming until I say so. Tell me you understand."

"Yes, sir. I understand." I say pouting in frustration.

"Good girl."

We pull up to the restaurant and the vibration stops. I'm so relieved and I close my blouse as Sir comes around the car to helps me out. I exit the car as gracefully as I can while trying to hold the plug and vibe in place. Walking once again, squeezing my ass and clinching my inner muscles. This is such a delicate balance to walk gracefully next to my Sir and still be confident that everything will stay where it needs to be.

Sir hand is at the small of my back as we are led through the restaurant to a small booth at the back. It's a quiet corner and we seem to have some privacy from onlookers. As we settle in, Sir pulls me close to him and nuzzles my neck. The host smiles knowingly and hands us our menus.

"Enjoy your dinner." The host says as he walks away.

"Oh, I intend to." Sir says quietly into my ear with a chuckle.

The vibe turns back on in a high vibration...

"Bastard."

The vibration is driving me to the brink. I try breathing through the need to orgasm. I'm sitting there and my body seems to have a mind of its own.

"Babe, if you don't let up. I am not going to be able to control this orgasm." I say. All casualness has gone in my voice.

"Go ahead baby girl. Let it happen, but be quiet about it." Sir says with a grin.

"Are you serious? Right here in the booth?" I whimper.

"Yep, you can orgasm as many times as you like. I'm not turning it down until I feel like it." He says with that grin still planted on his face.

I really want to smack him right now, but I can't. I'm so flushed because the headiness has me at my limits. That's when the waiter decides to come to the table to take our orders. The low hum coming from the vibe is all I can hear as my mind spins in a whirl of sensations.

"Have you two made any decisions on dinner yet?" Our server asks.

"Well I have, how about you Enola?" Sir turns to me with his arm around me and gives my ass a squeeze.

I'm panicked because I can't speak. I'm trying to focus on not cumming in front of our server and so I aimlessly stare at the menu.

"Enola?" Sir asks again with another squeeze of my ass.

I glare at him and he just chuckles. I look up at the server and he smiles expectantly at me. I inhale deeply before speaking.

"I will have the have the top sirloin steak cooked medium rare with the sautéed vegetables and the loaded sweet potato. The house salad with the gorgonzola vinaigrette." I say evenly with an exhale.

I'm quite proud of myself actually. I've managed to hold off the orgasm as Sir orders his steak. Our waiter smiles and leaves the table.

"Very good baby girl. Was that hard?" Sir says with a satisfied tone to his voice.

"Yes, please let me cum now Sir?"

Just then the vibe is turned off and the sensations fade.

"Noooooo." I whine.

Sir chuckles and we fall into an easier conversation for a while. I snuggle into his side as we sip our drinks and begin to eat the salads that arrive. Everything is calm and relaxed. I love that our conversations are never forced. We are comfortable with silent stretches as we eat. I shift a little as the plug is feeling slightly uncomfortable, but I don't want to change anything. The evening is going so well.

Sir nuzzles my neck and I feel the vibe start up again on a low speed. I purr in satisfaction as the feeling starts low in the core of me. I reach over and grab Sir's cock in my hand and rub him through his pants. He growls at me and I grin in satisfaction. I also notice that he doesn't tell me to stop either. Hehehe. I nuzzle my nose and nip his earlobe. Another growl of approval. Our steak arrives and Sir is kind enough to turn the vibe off again. I'm grateful because the food is superb and I am truly enjoying eating tonight. I hadn't realized how hungry I was. We eat and laugh picking at each other. I can still feel the plug and it is growing slightly more uncomfortable as the lube seems to have dried up a little. I fidget and shift again and wince at the irritation, but try to recover.

"Are you okay Enola?" Sir asks in concern.

"I'm okay, Sir." I say. I don't want to disappoint him. I want to be a good girl for him.

I shift my weight again to try and ease the discomfort.

"Enola? What's wrong?" Sir warns. He can tell something isn't right.

"It's just that the plug is feeling a little uncomfortable, but it will pass I'm sure." I say.

"Enola, when you are uncomfortable in a sexy way, that is one thing. But when you are uncomfortable in a painful way, I expect you to tell me honestly. Do you understand?" Sir scolds me.

"Yes, Sir. I'm sorry. I just don't want to disappoint you Sir." I admit.

"I know Enola, but I also know that anal play is a new thing for you. I have to trust that you will be honest with me when you are not comfortable." Sir is kind and sympathetic in his tone.

"Yes Sir."

"Now I want you to go to the bathroom and remove the plug. Does the vibe still feel good?"

"Oh yes Sir. I don't want to take that out please."

"Very well. Before you go, would you like me to order desserts?"

"Oooh yes please Sir. Can I have the chocolate mousse?"

"Of course, Enola. Now go." He commands

I hurry off and do as I'm instructed. I'm careful to wash it and put it safely in my purse. I check myself in the mirror again and make sure that I look good for my Sir. I always want him to be proud of me. Proud to call me his. I smooth my skirt back into place and head back out to see Sir.

As I am walking back to the table, I am caught off guard when the vibe is turned on full hilt. I squeak in surprise and stumble a little. I catch myself on the back of the chair of a gentleman that is with a small group. He looks up at me in surprise, but smiles at me with a glint in his eyes. I swear, he can hear my vibe. I straighten up and try to compose myself again. I smile weakly at him and take two more steps, but my legs have gotten weak from the onslaught of vibrations going through me. I stop again and try to compose myself. Oh God. I'm going to cum right there. I can feel it and I seek out Sir's eyes. The cocky grin is almost laughable. I knew I was going to pay for not being honest, but this??? Really??? My entire body is glistening in sweat. The familiar tingle traveling up my legs. I really can't continue to move.

I'm going to cum right in front of this table of men and Sir is going to allow it. Oh my God. Just as I think I'm done for and the orgasm is going to take hold, the vibe stops. I don't know if I should scream in anger and frustration or just laugh at the lesson Sir just taught me. I straighten back up with as much dignity as I can muster and glare at him as I finish walking back to the table.

"Nice." I say sarcastically.

"Your dessert is here Enola. Enjoy." Sir says laughing.

"Sometimes you can be such an ass, ya know?" I say with a slight chuckle.

"Yeah, but I'm your ass and you love it." Sir says smugly.

"Yes, I do. I love you."

"Now, the next time you will tell me when something isn't working for you. Won't you Enola?"

"Yes, Sir." I say.

"That's my good girl. Now let's enjoy our desserts."

We dig in and I purr in satisfaction. I'm really looking forward to going back to the hotel for our session