Speed Dating

"Have fun," she called over her shoulder as she disappeared into the house.

Yesterday Bernie told me I'd be happy, and he wasn't wrong. Because for the first time in a while, I was looking forward to a night out.

"You ready buddy?'

"I suppose. You?"

"Not really. I'm nervous as hell. Kelly's just...well you know. She's..."

"She's what? Look Bern, she's a good-looking lady, but don't get all revved up. It's a date. Play it cool. Let things happen naturally and see where they go from there."

"Easy for you to say. You always have women hanging off of you."

"I know. That's why I carry the taser."

Bernie had no idea about Evelyn, so he was joking about the amount of woman I haven't been around for the longest of times.

We pulled up at the restaurant and got out of Bernie's SUV. He took a couple of looks at himself in a pair of different mirrors and asked, "how do I look?"

"Best it's gonna get, buddy. Best it's gonna get."

"What do you think, if she gets frisky, should I try to hook up with her?"

"Yeah, run off to the bathroom for a couple of minutes and I'll cover for you."

"Fuck you, Jack."

I pulled the door open to let him in before me and was about to ask who Kelly was bringing with her, but there wasn't a need to. Michelle was seated beside Kelly at one of the many tall bar tables.

True to his word, Bernie paid for everything.

The night went better than I expected. We all had a lot of laughs and chirped one another like we had hung out together for years. No, we didn't win any prizes for our trivia knowledge, but we had fun. I would have liked to have given Bernie and Kelly some alone time, but the bar kept a tight schedule to keep the game moving along, so it was unfortunately a "friendly" evening.

Pulling a trick out of a very old playbook, I sipped at my last drink. I told Bernie and Kelly we would meet them outside, and I asked Michelle to wait with me while I finished up the drink, giving the "daters" some alone time out in the parking lot.

"Slick."

"What? I wasn't finished my drink."

"Finished? You were done with it thirty minutes ago. It's probably warmer than bath water."

Pushing the half-filled glass away from me, I smiled and told her she was correct.

"He's lucky to have a friend like you."

"Yeah. It seems we have each other's backs a lot lately."

"I know the feeling. Kelly and I are like a couple of old hens some days."

"Well, you both still look like spring chickens."

"Thanks. I'll take that as a compliment."

"Please do."

"I will, even if it isn't true. Not sure if you know this, but compliments can be very rare these days."

"Come on. I don't wanna call bullshit, but..."

"But what? The last compliment I got was from a woman I work with. All the guys who talk to me want something they can't have. I know it sounds vain, but they only want to be with me so they can say they were with..."

"Chad's wife? There are lots of shitty people in the world. Don't let them get to you."

"Get to me? I wish I could let something get to me. Look out there," she pointed out the window, into the parking lot. "It's their first goddamn date. Look at them for Pete sakes. Kissing like teenagers in a bar parking lot."

Turning to see what she could see, made me smile. Kelly was sitting on the hood of Bernie's SUV, while their faces and arms moved all over one another.

"What, you think it's funny?" she asked.

"I don't find it not funny."

"Aren't you the least bit jealous?"

"No."

"Why not? I mean, I am. I want...I would...just once. For the love of God. Just once, I'd like someone to care enough about me to kiss me like that."

The tips of the fingers on my right hand twitched. I was nervous about my next move, but what had happened at Evelyn's gave me some courage. Moving my fingers up so they touched her smooth cheek, and my thumb brushed her chin, I watched as her eyes widened with surprise.

My hand on her face startled her and my lips surprised her even more when they pressed against the softness of her full, lush, deep red lips.

I half expected Michelle to pull away from me, but she didn't. Instead, her fingers combed through my hair and over my neck. Lost in the moment, her fingers gripped the collar of my shirt as she held on tightly. Our friendly encounter somehow skipped past being a simple kiss, to one where my lips parted, and her tongue darted. And much to my surprise, it ended up in my mouth.

We moved a bit closer. Her chest touching mine. My legs parting as she pushed her thigh between them. Her grip on my collar and hair tightened and her face seemed to burn under the touch of my fingers.

The only thing shocking me back into reality was her purse dropping on my foot. Somehow, in the heat of the moment, she had lost her grip on it. Not being able to hold my collar and the purse at the same time, she had to drop one of them. Her purse landed directly on my toes.

"Jack...oh my god. I'm so...Jesus Christ."

"It's fine. Nothing is broken."

I bent over to pick up her purse and when I stood back up, I noticed how much she was blushing.

"I'm sorry for being so forward but thank you. It was the most beautiful kiss ever."

She pulled the small, but heavy, purse from my hands and tucked it under her armpit.

"It may have been 'beautiful', if I hadn't begged for one and you didn't do it out of pity."

My fingers found her free hand and grabbed it.

Moving between the now mostly vacant tables of the bar, I led her out into the parking lot. In the distance, I could see my ride home. The two adults, who had been mauling each other like teenagers, were still unaware of anything around them, and appeared to be in no hurry to leave.

Finding shelter under an old palm tree, I turned so I could look into Michelle's eyes as I spoke.

"You have the pity thing all mixed up. Never. Not once, was there ever even an ounce of pity in my mind or heart when I reached out to kiss you. You said, 'just once', and I took it as an opportunity to kiss the prettiest girl in the bar. I hope I didn't embarrass you."

"No, Jack, you did the exact opposite."

Still holding hands, we looked in each other's eyes. Perhaps looking for answers to unasked questions. With neither of us willing to say the wrong thing, we stood silently for the longest time.

The slightest of movements. A step forward. A lean in. Her head started moving toward mine. We were going to kiss again, but it wouldn't be tonight.

Kelly had pulled up behind us and sounded the horn. Window down, she called her friend over. Seconds later, Kelly's Mazda pulled onto the street and disappeared.

*****

Friday night was a quiet one. Bern and Kelly hooked up for a date. So, neither Michelle nor I were required to attend another round of Speed Dating.

I hoped to connect with Michele at some point after Wednesday night. I wanted to. I planned to. But I couldn't. Neither Bernie nor I had her number, and he had forgotten to ask Kelly for it. So, I would have to wait for Michele. If she wanted, she would get in touch.

*****

Saturday night at eight, I got another "UNKNOWN CALLER" call. I anxiously picked it up.

"Hello."

"Hey baby, are you playing hard to get?"

"No."

It wasn't Michelle.

"Then why haven't I heard from you?"

"As much as I would have liked to contact you Evelyn, I don't have your number."

"But you know where I live darling."

"I do. But dropping in unannounced might draw the ire of your roommate."

"My 'roommate' is my pet. I decide when and if she is truly angry."

"I see."

"Do you, Jack?"

"Partially."

"Partially is better than most, I must say." Evelyn paused for a very long time. I could hear her sipping and swirling a drink around in her mouth. "We missed you last night."

"We?"

"My pet and I."

It was my turn to pause. I waited and apparently, I waited too long.

"Come to us. Come for us tonight. We'll have so much fun."

I looked at Ben half asleep on the floor playing and switched my phone to text and sent Millie a short message. Seconds later she replied, 'sure. Bring him here. I'm alone tonight. And I could use the extra money.'

"What do you have in mind?"

"Anything you want baby. Remember what I told you last week? Treat me right, and all the world is yours for the asking."

"When?"

"We need an hour or so to get ready."

"I'll see you at ten."

The call ended as suddenly as it started.

I raced around the house collecting everything Millie would need for Ben. I jumped in the shower and surprised myself. Like a teenager filled to the brim with excitement, I was standing under the water with a hardon, and it took everything in my power not to get rid of it.

*****

"Thanks, Mills. See you in the morning."

"No problem, Uncle Jack."

Leaving my son behind, I headed off for another night of debauchery. My second in as many weeks. And for the first time in many years, I was feeling very good about myself.

*****

The dark blue door opened almost as soon as I knocked.

Evelyn stood before me with a smile on, and not much more. She was dressed in the smallest of leather vests. The kind with no sleeves and a collar that stood up on her neck with the metal clad points aimed forward like arrows. Below, she wore a spiked, leather thong. One which barely covered her most valuable assets.

I admired the cleavage of her titties as they had been pulled through the split of the vest and the sight of her pussy lips pushing to escape the confines of the leather pouch holding them in place.

My Leather Queen held a pair of glasses in one hand. The way she stood, with two fingers and her thumb on the insides of the glass, touching the amber liquid, was one of the sexiest things I had ever witnessed.

"Just for you baby," she said with a gravelly, whiskey raw voice.

Reaching behind me, she closed and locked the door. Then nuzzled herself up against the back of my neck and pressed her nose onto it.

"Yummy. You smell so sexy."

Evelyn moved. Touching my hand as she went, so I followed her into the center of the room and noticed Dina sitting sideways on the sofa, legs tucked up, and under her butt.

Dina, like Evelyn was almost naked. Unlike Evelyn, there wasn't a piece of leather anywhere near her. No, Dina was dressed far more delicately. She wore a sheer pink robe with a feather boa and feather sleeve cuffs. The robe did nothing to hide her plain white lingerie.

Taking me by the hand, Evelyn pulled me toward her housemate. Rising her glass, Dina and I followed suit.

"To an evening of love and lust. Cheers, my babies."

Bending down, she kissed Dina. I watched their tongues probing one another. When they broke apart, Evelyn stood and kissed me in the same fashion.

I could taste the mixture of Evelyn's whiskey and a hint of Dina's white wine. It was not unpleasing.

"Now her, baby," Evelyn told me. Pointing at Dina.

Suspecting I might catch a slap, I took my time. But waiting for me to move in for a kiss, wasn't the Dina I had met twice before. This Dina had plans for the evening, and her plans involved me. This Dina grabbed the collar of my shirt and pulled me to her. And if I was being completely honest, her kiss was softer, yet far more earnest than Evelyn's. Open mouth. Loads of tongue. Loving, but in a very sexual way.

"See baby. Not so bad after all. Was it?"

Both Dina and I looked at Evelyn. Neither of us was sure who she was speaking to.

Picking up the bottle of whiskey and an ice bucket containing the almost full bottle of wine, Evelyn looked toward us and motioned for us to follow.

"We can start out here, but we all know where it will lead us. So, we may as well set-up camp where we'll be most comfortable."

I put my hand out and Dina smiled and took it.

*****

The master bedroom was cool in temperature with instrumental music playing softly in the background. Both ladies had set down their drinks and turned their focus on me.

"You have far too many clothes on. So, let's get you undressed and ready for the party, Big Boy."

Four hands and two sets of lips worked at undressing me. Buttons opened. Belt and pants were undone. Pieces of clothing dropped and were tossed to the corner. My watch was removed. My nipples and bellybutton were licked. And when the girl's cold fingers tickled my scrotum, it instinctively tensed, making me shiver.

"Do we scare you baby?"

"Shitless," was all I could say.

My head tilted back on its own. The soft lips and hands working me over felt like nothing I had ever felt before.

The wet tugging at my balls could only be one thing. A mouth. And the wet tunnel sucking my shaft into it could, at this point, also only be one thing. Another mouth. Daring to look down I watched Dina working me as far down her throat as she could. Inch after inch she sucked until her eyes watered. Evelyn on the other hand was having no problem alternating between sucking and soaking my nuts.

For more than five minutes I watched Dina watching me. She could tell the affect her efforts were having on me. I bit my bottom lip between my teeth and tried willing myself not to cum.

The once cool room was now heating up. It smelled alive with the vibrant scent of Dina's and Evelyn's sex. They had come alive. I could hear the squelching sounds of Evelyn's finger as they pushed in and pulled out of a woman's vagina. The woman who was sucking my cock.

"Fuuuuuck. Dina, it feels so good."

I had to stop myself from looking at her. My eyes focused on the ceiling. I stared at the oversized, palm leaf, ceiling fan turning slow clockwise revolutions. I counted each one. It was the only thing stopping me from busting a nut into Dina's mouth.

"Do it, Jack. Fuck her face and fill her mouth. Show my little slut who's in charge. Show her how men do it."

Evelyn taunted me for a few more seconds. She was pushing me to do what was already a normal instinct. I wanted to.

When her teeth, not so gently, squeezed one of my wet balls, the taunting had ended. Fucking Dina's face was now an order.

My fingers wrapped in my cock suckers long curled hair. They touched her ears and clamped down. Pulling her head to my groin I watched as her eyes widened and watered. With her small cute little mouth, there was no possible way she could get every inch of me into her face. I held her there until a look of panic appeared in her eyes.

"Gaaawwwd," screamed Dina as she gasped for air. But it was only for a second before she was pushed and pulled back to the limit of my cock. As her lips, tongue and throat caressed my shaft, I could feel my body building up to the greatest sensation that it would ever have, ejaculation.

"Do it. Fill her bitchy mouth with your cum."

The entirely weird vibe of these two ladies was working me over enough to make it happen.

Easing up on my death grip, I let Dina slide into a place more comfortable for her and looked down. She could tell by the look in my eyes I was ready, so she nodded her approval, and I emptied myself into her waiting mouth. Gulp after gulp, she swallowed glob after glob of my spend. In my whole life, I had never been a part of something so...invigorating.

Dina's wet lips pulled up and off of my throbbing cock, but they weren't lonely for long. In a matter of moments, Evelyn was having a taste of what I had deposited into her lover's mouth.

"Ummm...the salty, sweet taste of a man. Did you like it baby?"

This time, I knew she wasn't talking to me.

"Did you?"

Dina shot back instantly.

"I did, but I've almost had enough of you showing off for your man."

"Lucky for you, pet, it doesn't happen very often." Evelyn gave her partner a death stare. "You know what to do next," Evelyn told her pet.

When Dina didn't move fast enough for Evelyn's liking, Evelyn reached over to the bedside table and picked up a leather looking fly swatter. Dina scrambled at its sight, but she wasn't quick enough. With a slap, the leather found a home across her right ass cheek.

"Ouch, mistress."

"Quiet, or the next one will be harder."

Not a single drop of blood had left my cock. This was something completely foreign to me. Something brand new and without compare. Everything about it gave me a thrill. My excitement was at peak levels.

Evelyn used loose silky shackles to tie Dina's arms and legs to the bed. She then tried to put a blindfold on. One made of the same material. Dina resisted, and for her efforts, received another swat from the strap.

"Please Mistress, I want to watch."

A third smack. Lighter this time, but on a far more delicate spot. Dina's left breast.

"Sit, Jack. Enjoy your drink while our sex toy pleasures me with her mouth."

Evelyn started to climb up and over her bedmates head, but I pulled her backwards to where I stood.

"Jack..."

Evelyn fought, but not very hard. She wanted to be in absolute control, but the fight was over when I pushed my hardon into her. Her body betrayed her by accepting the pleasure, yet in her mind, she was upset because she was losing control of the game.

"Stop, Jack. You need to..."

"What Master? What is he doing to you? Let me see. Let me watch."

Although blindfolded, Dina could hear the sounds of adults having sex. The wet sloshy noises. The slapping of skin. The grunts and groans.

The look I received from over Evelyn's shoulder told me to stop. She wanted me in her, but she also wanted something else. So, I took my hands off her hips. Releasing my grip allowed her to make her way back to another waiting lover.

Lowering, she let Dina get a taste of what she was waiting for. It was a big helping of wet pussy.

With her hands on the headboard and her head hung low, Evelyn immediately seemed to be enjoying her ride. Her hips moved and gyrated in time to the sexy jazz playing in the background. In a sexually induced shudder, Evelyn requested I tear Dina's panties from her 'fat ass'.

The tiny white cotton panties were very sexy, but they weren't covering a fat ass. In fact, Dina was much smaller than the woman sitting on her face.

Sliding the moist cotton panties down her smooth legs, I got my first look at Dina's pussy. It was perfectly waxed. Not a stray hair anywhere to be seen. And her lips were far more pronounced and protruding than those of her partner's. I was aware I had been instructed to sit in the chair, but I lowered my chest to the bed anyway.

As my tongue parted Dina's wet wonderland, I heard both women moan out loud.

Dina's tangy sweet wetness filled my nose and mouth. It sent my senses into overdrive. I worked on her. She worked on Evelyn yet moved her hips to maintain contact with my face. And Evelyn humped her pussy onto the tongue below her. Teamwork.

The bed shook. Evelyn spasmed as she came. Dina groaned so loud it sounded painful. And I slowed my licks so as not to overstay my welcome.

Moving just in time, I missed the first of two slaps Dina's pussy absorbed.

"Honestly, you should be ashamed of yourself bitch. You call yourself a dyke, but you let yourself climax from his tongue work? And now you want to hurt me saying a man sucks your pussy better than I do."

"No, mistress. Please, let me try again."

It was too late. The leather fly swatter found skin three times in a row. "Ouuuuuuch. Thank you, mistress, it hurts so good."

I highly doubted it hurt. In fact, Dina's hips were grinding against an invisible lover. She was so aroused she was fucking the air.

Spinning off her lover, Evelyn's face found mine. She kissed and licked at me to get a taste of her partner's essence. Pulling away, I moved my head down until I captured one of her rock-hard nipples in between my lips and teeth.

"Fuuuuuuuuuuuccccck...Jack," Evelyn cried out.

"What, mistress? What is he doing to you?"

With half of my focus on the nipple in my mouth, I used the other half to reach around and find what I was looking for. Seconds later my fingers touched the smooth mound of her pussy and slid between the meaty lips of Dina's gash.