The 3rd Annual Dare to Dream Gala...

January, 27, 2017

JACK

“Yes, I hear you, Neil, but we can’t cut the fee any further. We’ve already come down as far as we can. If your budget doesn’t allow for twenty models, then maybe you consider fifteen.”

I could tell that the client wasn’t thrilled, but he’d already hammered and chipped at this negotiation more than I typically allowed. We’d been at the proverbial ‘bargaining table’ for two and half hours, and I’d given in more than I ever had. 

My phone pinged. I glanced at the screen to see that it was a test from Beth along with a photograph attached. Tonight was the 3rd Annual Dare to Dream Gala to benefit GLSEN. Noting the event would be starting in two hours. Over breakfast this morning, Beth said that everything was going smoothly. I wondered what she could be texting me about. Was it a photo of the venue? Had she changed her mind as to which dress she was going to wear? I thought we’d decided the red dress was the perfect one. Had she changed her mind and gone with the blue one?

Unable to deny Beth anything I picked up my phone. “Just a moment,” I said to stubborn man and opened the text.

I wasn’t prepared for the photo that opened on the screen. Beth had taken a picture of her standing in front of our bedroom mirror wearing a red, satin corset and pair of tiny, red, lace panties. On her feet were the red suede Christian Louboutin’s that we bought to go with the red Alexander McQueen off-shoulder gown. 

Some might say that for a 46-year old woman, she looks fabulous. I thought she looked out-of-this world compared to all women of all ages. Her curves were in the right places, and there wasn't a shred of awkwardness in her. In the beginning she used to be a little self-conscious, but these days, she held herself with a fearless confidence that was as sexy as any part of her body. The corset was a new surprise.

As I drank in that image, my phone pinged again with a message from Beth. “Do these 👠 go with my skivvies? 😈”

Oh, she was in a mood. I guess the day’s planning was all in order for the gala or she wouldn’t be so cheeky. I texted back, “I think I need a closer 👀.”

“C’mon, Jack. We go way back. Can’t we make the twenty work?”

“Huh? Twenty. Yes, fine. Done. I’m sorry, but I have to go.” 

I quickly signed the contract Neil and I had edited and excused myself, asking my secretary to show Neil out. I put in a text to my favored driver from the car service I held on retainer and collected my coat from my office then made my way down to the ground floor. I hoped that the traffic wouldn’t be too heavy and I could make it home before Beth put that gown on. 

BETH

Hearing the front door open and close, turned up the dial on my excitement. I glanced at the clock to see he’d made it home in just twenty minutes. He must have let no time lapse from the text I sent. 

I tried to calm my self as I leaned in to put the finishing touches on my makeup. Well, except for the lipstick. I didn’t want to smudge that. I’ll save putting on the lipstick for the ride to the gala.

Three years ago, I might have been afraid of over-exciting Jack. At the first Dare Gala, Jack collapsed from a massive heart attack. After surgery and rehab, the man was as good as new. True that the surgery did make for a less than thrilling honeymoon, but the three weeks we spent at his, our home in Barbados was relaxing and rejuvenating—just what the doctor ordered. We’ve made up for any lost time since then, and his virility hasn’t crossed my mind since then, except when he’s eating too much red meat, or drinking too much scotch. I will always worry about his health, but I preferred to worry from the prevention side of things, rather than the recovery. Sex—well, that was akin to exercise, something his doctor recommended.

With each deliberate step he took up the curved staircase my heart thumped louder, making the corset feel tighter. I loved teasing this man. When his steps stopped, I knew he was standing at the door as I dusted my nose with the finishing powder. I schooled my energy and said as nonchalantly as I could, “Oh good, you’re home just in time to help me with my gown.” 

I stood and faced the most amazing man that came into my life just three and a half years ago. My knees almost buckled from under me. I always had that reaction when I looked at him, especially when he was looking at me the way he was looking at me now. 

“Mrs. Morris-Stevens. You are quite the naughty minx,” he growled, walking—no stalking me, like I was his pray.

Stand your ground, Beth, I cautioned myself. I knew I had the upper hand. I always did, even if Jack was holding the whip. But sometimes, his personality was too much for me and I caved to his will—or I gave him the power, if you will. 

“Now, now, Jack. We don’t have time for that. We have to get to the—”

“I called Becca. I told her we’d be late,” coming to a stop, standing just before me.

The space between us crackled. I gazed into his warm brown eyes and his dilated pupils showed just how aroused he was. I swear that look practically brought me to orgasm.

“M-my hair. I just had it done. I don’t want it messed,” I squeaked. Baiting Jack has become my favorite past time, but sometimes the way he looked at me, I lost resolve. 

“It’s beautiful,” he said, not looking at my hair, but his attention was now all focused on my chest, and the new strapless, red corset I wore, which he was tracing the top line where my breasts threatened to spill over, with his fingertip, igniting sparks along the path that finger took. 

Jack seeing me in my unders was nothing new. He’d often make me walk around our home clad in just that. In the beginning I was self conscious. That was no longer. Being with Jack has turned me into one helluva confident woman, and I loved it! And this corset made me feel bad-ass.

“Knees,” he simply said. I couldn’t help the smile that emerged on my face, nor could I help but follow his command.

I placed my hands on his chest for balance and I slowly lowered myself, enjoying the strong man under my fingers. When I was on my knees and directly in front of his cock, I let my hands explore the thick, hard length behind the Tom Ford suit pants.

“Don’t toy with me,” he warned, his voice strained with need. “I need to feel my cock in your mouth.”

I looked up at him through my eyelashes, and watching his face, I unbuckled his belt, and unfastened his slacks. Slowly, I worked them down, taking the boxers with them, and released his cock. I wrapped my hand around his shaft and worked it up and down a few times, reveling in the satiny smooth heat. Jack’s eyes closed and his head dropped back.

I leaned forward and licked the salty tip, enjoying satisfaction from the groan that escaped his throat. His hands reached for my head, but I grabbed his hands and laced my fingers with his. “Not the hair,” I reminded him. Although my pixie style was easy enough to style, truthfully, I just wanted to maintain some of the upper hand.

Now that my hands were occupied, the art of pleasuring my man was a bit more challenging, but I’d been here before, and I knew just what to do. I leaned forward and took his jutting penis into my mouth, letting it hit the back of my throat before closing my lips around him. 

“Fuck!” he growled as he gripped my hands.

Slowly and deliberately I worked his length over, using my teeth on his shaft from time to time, and swirling my tongue over the crown. Alternating the suction and speed, I felt him grow in my mouth and knew it wouldn’t take long to send him over the edge.

Do I let him come? Or do I make him wait? I didn’t have much time to think about it, so I decided to go with my original plan. And, it was getting hard for me to breathe within the confines of the corset. I pulled off of him, not letting him reach orgasm, and I stood.

He looked at me aghast! “You didn’t! You wouldn’t!” 

“I can’t be late. I’m the organizer. You can’t be late. You’re the host. Now. Help me with my dress. We’ll finish this later.”

“Oh, we’ll finish it later alright. But next time will be on my terms.”

“I’m looking very forward to that,” I retorted with a wink. 

JACK

How I was able to get dressed, I’ll never know. I almost threw Beth over the end of the bed and fucked her good and hard for the stunt she pulled: the text, and then still being half naked when I got home, and then the incomplete blowjob. But she enjoyed a good game of cat-and-mouse. She wanted to play? Game on. 

On the limo ride over, I set my ‘game’ into action. We’d only just left the townhouse when I slid to my knees in front of her.

“Jack!” she admonished playfully. She knew the glass between the front and back seat was too opaque for the driver to see anything, but she still played the coy mistress every time. I loved it. Seductively, I pushed her gown up revealing the garter that held up her stockings. God I loved those things! The sexiest piece of women’s lingerie second to a well-fitted corset.

I ran my tongue up along the inside of her thigh. I loved the sound of her breath faltering and the feel of her quivering under my touch. When I was almost at her sweet smelling junction, I stopped and switched to the other side, repeating the action from the inside of her knee all the way up to the edge of the red laced panties. 

Carefully, I pulled the thin, narrow strip of fabric that covered her from me. I looked up at her to see her biting her plump lower lip. She was so eager for me to lick her and taste her. She wiggled her hips urging me onward. I couldn’t help myself so I leaned in and with feather-light flicks of my tongue, brushed her opening and flicked at her clit. She was pleading, and while I was playing her game, I needed to taste her myself. If I were honest with myself, I wanted nothing more than devour her and make her come, but when I sensed she was as close as I had been, I stopped. Teasing is a truly enjoyable sport. 

I reached into my pocket and pulled out a small, U-shaped, pink silicone device.​

I pulled the crotch of her panties back into place and patted gently. I pulled the skirt of her dress back over her knees then said, “Sit up.” Like the obedient lover that she was, she sat up and I could see her wiggle her hips, gaining friction from the pad sitting on her most sensitive spot. “Now the magic,” I whispered. Pulling my phone from my pocket, I found the app on the last page where I’d installed it. I opened the app, then pressed the play button. 

“Ooohh!!!” Beth cried out, grabbing the seat under her. I let the vibrator go a moment, then played with the settings increasing the intensity and changing the vibration pattern. “Oooowhoooa!” she groaned, her cheeks growing more flushed. Then, just as she was really getting into the sensations, I powered it off. 

“Hey!” she pouted, but she knew exactly what I was up to. “So, I’ll just have to hang around you all night?”

“No need. This thing will work if we are on different continents.”

“You’re kidding!”

“You know me better than that.” 

The limo stopped, and we gathered our coats. A few seconds later the door was opened and I slipped out then helped my beautiful woman out. Paparazzi were right on cue. The flashes were blinding and the shouts were deafening. In the past, Beth would clung to my arm, still shy around the cameras, but now, she was graceful. She’d wave to the crowd and flash back with her amazing smile. 

After a few minutes of photos, we made our way inside to finalize the preparations for the start of the ball in less than an hour.

Inside, we checked our coats and went off to meet up with the band to make sure everything was good with them. Brad, Zach and Angie were working with them, a group the trio discovered while filming their first feature documentary about the real life of musicians. While Angie and Zach continued with the sound checks, Brad and I spoke briefly about their new production company which I was a silent partner. I was proud of their dedication and only too happy to help, if they were connected to Beth or not.

“Hey!” Phoebe said coming up to us with her movie star boyfriend, Chase Smythe, (known to us as Charlie) right behind her. She hugged her brother and me, then interrupted her mother quickly to say hello. The band was suddenly star-struck when they saw Charlie, but he put the group at ease with his incredibly amiable nature. There was a time when he was Hollywood’s bad boy, but since he and Phoebe had started seeing each other, Charlie grew up a lot and was quickly becoming one of Hollywood’s most respected actors, and soon to be directors. 

Next to arrive was Greg, Beth’s ex-husband, and his husband, Tanner. That was a bet I’d lost. When we met the couple in 2014, Beth swore they’d marry. I didn’t see it, but a year and a half ago, Tanner made an honest man out of Greg. Their wedding at a Napa Vineyard was a special day indeed. Beth had been harboring some guilt that she’d already re-married. She also felt badly about leaving him, but seeing him so happy with being his true self, a married gay man, eliminated any lingering bad feelings that she’d left Greg without full cause.

“Just need Carter to make the group complete,” Phoebe pouted. Her brother, the middle Fairchild sibling, was unable to make it as the publisher of a book he and his wife, Caterina, had just published sharing incredible discoveries in Pompeii, where the two worked as archeologist. 

“Beth!” Becca said rushing up to us. “Wow. You look stunning!” she said, stopping in her haste to admire Beth’s gown. “Alexander McQueen?” she asked. Beth nodded. “Listen, we have a slight glitch with the seating. Mind if I borrow her, Jack?” 

I acquiesced graciously and off the two went. I let Phoebe and Brad catch up and I made my way to the bar for a glass of wine. While I sipped my glass of red, I admired how Beth and Becca got along so well. Once the seating snafu was smoothed out, they started chatting about God-knows-what. I decided to have a little fun. I pulled out my phone and the app to control the vibrator that was still in place in Beth’s pussy.

“Whoa!” Beth exclaimed loudly, drawing the attention from the waitstaff that were bustling about making sure all the final touches were just right. She fixed her eyes and me, narrowing them with a warning. Oh, this was too much fun! Returning her warning look, I increased the speed and watched as she lost her senses a bit. She fought to regain her faculties, but Becca looked both concerned and confused. She started fussing over Beth, but My Girl waved Becca’s offer to sit off, and I watched Beth struggle to form sentences. I lowered the vibrations and then turned the device off.

BETH

Maybe I'd gone too far, teasing Jack the way I had with the picture and incomplete blowjob. But this gadget he had me outfitted with was both menacing and magical. For one, even without Jack turning it on, knowing it was there and what it could do was exhilarating. When I walked, there was a gentle friction that kept me in a constant state of arousal. Thankfully, Jack was being a little kinder when he chose to turn the vibrator on by not doing so when I was speaking with important people, or my ex-husband and his partner, or my children, or when I had food in my mouth. I’d tried to remove the dang toy once, but he followed me into the private ladies room back behind the scenes, not the one that was being used by the customary line of other women waiting for the main restrooms.

I was wrapping up my thank you speech, thinking I was in the free and clear, when Jack pulled his phone from his pocket. He had told me my speech was too long last week and he found an effective way to make me shorten it on the fly. I cut to the chase and introduced the band. Jack rushed to the edge of the stage and up the stairs to help me down as the band started up. 

“You’d better help me down the stairs. I can barely walk,” I panted as he led me toward the dance floor. 

“Let’s see how it makes you dance,” he said pulling his phone out to re-initiate the vibrations. 

“No, Jack, please. I need a break. As it is I’m about to drag you back to the band’s set up room and make you do unspeakable things to me.”

Jack twirled me into his arms and we started to sway to the song, but the direction was not to stay on the floor. Once we were off the floor, he took my hand and swiftly led me out of the ballroom and into a dark and private hallway back behind the scenes. He pushed me up against the wall and kissed me until I could hardly breathe.

Whenever I was with Jack, I was turned on, but his using this device several times this evening brought my excitement to a new level. And feeling how turned on Jack was, even through his trousers, only added to my arousal. I stroked him through his pants until he pulled his mouth from mine.

“Enough. The game ends now.” Jack pulled his phone from his coat pocket and opened it.
“No,” I protested. “I want you, not the toy. Let me take this thing out.”

“Remember? I said this was a couple’s vibrator.” He tapped the app and the device buzzed to life again. Swiftly, Jack unzipped his slacks and then pulled up the hem of my dress. Securing my left leg up around his hip, he pulled the fabric of my panties aside and then, in one thrust, entered me.

Oh.
My.
GOD!

All the vibrations inside and out, plus being full of Jack.

“Holy fuck!” Jack groaned, dropping his head to the crook of my neck. He slowly pumped into me. “This feels amazing.”

Amazing was an understatement. But I could understand what he meant. But there weren’t any words to describe this. On the one hand, I wanted it to go on for ever. On the other, I was so desperate to come.

“Don’t stop,” I pleaded, opting for the latter. 

Jack picked up the pace and exploded in me. He slowed, then pulled out the app and turned off the buzzing.

“That was…Wow…And…Right?” Jack panted.

“I wouldn’t know,” I practically scowled. 

“Oh? You didn’t…? I’m sorry.” A wicked smirk spread across his gorgeous face.

“You are infuriating.”
He pulled his softening length from me, and the device with it. Immediately followed by a dribble down my leg. Jack pulled a kerchief from his breast pocket and wiped me up, then himself a bit before tucking himself back in. He wrapped the U-shaped thing in the kerchief and tucked it into his pocket.

“Don’t worry. I’ll take care of you when we get home.”

He placed a sweet kiss on my lips and we straightened then returned to the party.

JACK

It was two in the morning when we finally came through the door. Beth looked exhausted, so I swept her off of her feet and carried her up to our room. I loved nothing more than carrying her anywhere. With her head rested on my shoulder and I felt so whole. This woman completed me in a way I never knew was possible.

We talked about all the amazing moments of the night, the featured speaker, transgendered boy who had had the support of GLSEN for years and was just elected class president of his senior class. It’s really wonderful what that organization does for these young men and women. It really gave both Beth and I hope for the future. 

In our bedroom, Beth laid the dress over the edge of the sofa and went off to brush her teeth in her sexy-as-fuck corset. 

I stripped down, and met her in the bathroom where we brushed our teeth, but all I wanted to do was to bend her over the counter and fuck her while we both watched in the mirror. However, after teasing her as much as I did this evening, she’d earned more than a ‘fuck.’ 

Instead, I slowly unlaced her corset from the back, ignoring the busk-front closure. Once she was freed, she sighed and took a deep breath.

“I hadn’t realized just how constricting that thing would be all night,” she remarked. 

Slowly, I trailed my hands all over her body. I watched Beth’s face as I my fingers reveled in the well know and loved curves of her body.

We finished up and I led her to bed. I worshiped every inch of her body in sleepy hunger with both my fingers and mouth. Almost effortlessly, I brought her to orgasm, without any teasing. We’d had enough of that for tonight, 

But I was looking forward to using that vibrator again.