20th Anniversary Ch. 03

It was a couple of weeks before Katie brought up Jessica again. We'd just settled down for a quiet dinner, fettuccine alfredo with grilled shrimp and broccoli and a nice glass of wine. Katie had been unusually quiet today, and we were eating in silence.

"I can't get Jessica off my mind." Katie finally blurted out.

"In what way?" I asked cautiously. Katie had never indicated wanting to be with a woman before, and while she enjoyed Jessica's fingers, I never got the impression she wanted to take it further than that. Or was it picturing me with Jessica that was slowly eating away at her?

"I just feel bad for her! Regardless of what transpired between us, she's a sweet girl and it really bugs me that she's so lonely, and only has work and school to keep her occupied!"

I twirled some pasta around my fork as I thought about how to respond.

"I just wish there was something we could do for her!" Katie continued.

"What, you want to play matchmaker for her?" I asked. "We know nothing about her beyond this snippet of her life. I also agree that she's a nice girl, but we don't even know anyone in that area, let alone who would be a good match for her!"

Katie didn't say anything, but I could tell she was still wrapped up in her own thoughts. We finished dinner, and I helped clear then excused myself to go upstairs to bed as I had an early morning at work the next day. Katie gave me a kiss goodnight, but said she was going to stay up and watch the news before turning in.

I woke up the next morning and quietly slipped out of the house so as not to wake Katie. The day flew by as I had so much on my plate, and before I realized it, it was quitting time and people were heading home.

Katie greeted me at the door with a kiss, then dragged me into the dining room where she had prepared a nice dinner for us. I sat down and she brought me a glass of wine, then sat down and gave me a big smile.

"Guess what!" she said, excitement in her voice.

"What's up? Something's got you excited!"

"We're going back to New York this weekend!" she squealed. "I booked us a room for Friday and Saturday night!"

"You did?" I asked cautiously, not sure what was coming.

"I did! I couldn't get it in our usual hotel, so we're just down the block at the Marriott!"

"Ok...?" I responded. "What's the occasion?"

Katie blushed a little. "I told you I can't get Jessica out of my head. I want to try and hook her up, so we're going to introduce her to Steve and see if we can get them over the friendship hump!"

I wasn't sure this was a good idea, but I know my wife and there was no way I was going to convince her otherwise. I did need to understand the rules though.

"What happens if they're not into each other? We have a history with both of them now, and we set boundaries to protect both of us."

Katie looked at me as if that hadn't even occurred to her. "Oh! I wasn't thinking that we would be involved, other than introductions and maybe some suggestive conversation!"

"I don't know... we have to be pretty careful here."

"Don't worry! We'll be fine!" Katie stated, ending the conversation. She shifted to other topics, asking about work and other idle topics as we enjoyed the rest of the evening.

The rest of the week was a blur, and I cut out of work early Friday to find Katie waiting in our driveway with the car packed. We didn't say much of substance on the way down, just the usual banter of two people that had been married for over 20 years.

We arrived at the Marriott and gave the keys to the valet and checked in to our room. It was bigger than our room at the other hotel, with a great view of the city. We didn't spend long there though, heading out for a casual dinner a few blocks away.

After dinner, Katie suggested we go back to our old hotel for drinks.

"So, what's your master plan?" I asked as we strolled through the city arm in arm. "Obviously you're hoping to see both of them at the bar, but then what?"

"I'm not sure." Katie replied. "If Steve is there, I'm sure he'll be happy to chat with us. The problem is Jessica. She's going to be working, which means she can't really join us. What we need to do is get them out of there and in a social setting together."

"But where?" I asked. "When her bar closes, I suppose we could go to a different bar, or if she's not working tomorrow could try and set something up with both of them. But aren't they going to be thinking along the lines of last weekend?"

"They might, but that's ok!" Katie giggled. "Whatever gets them thinking about sex, then we just have to steer them towards each other!"

We entered the bar and made our way over to a table in the back. It felt weird being back so soon. We only sat there for a moment, when I saw Jessica come out from behind the bar and head over to us. I couldn't help it, my eyes locked onto her chest as she strode towards us, picturing them bouncing above me as she rode me.

Jessica squealed when she realized who we were and ran the last few feet to our table. Katie stood as she approached, and Jessica grabbed her in a big hug. I rose, and Jessica turned and gave me a hug as well. I could feel my cock twitch as the vaguely familiar scent of her hair filled my nostrils.

"What are you doing here?" she asked excitedly.

"We wanted to see you!" Katie replied, hugging Jessica again. "We love the city so we decided to come back for the weekend, but we couldn't do that without saying hi!"

"I'm so excited you stopped by! But I'm working... what are your plans for the rest of the weekend?"

"We're completely open right now." Katie said. "If you're free after work, or tomorrow? Whatever fits your schedule!"

"Sounds great! Are you going to stay for a bit? I'll take a break in about 30 and we can sit down for a few!"

"Sure!" Katie smiled. Then she leaned over and whispered something in Jessica's ear that made her grin. Turning, she whispered back in Katie's ear.

"The usual, right?" Jessica asked, breaking away from Katie. "I'll be right back!" and she flounced off towards the bar, returning moments later. She set the drinks down with a flourish, then winked at Katie as she headed off to assist other customers.

"What was that about?" I asked.

"I asked her if Steve had been around at all." Katie stated. "I told her I really wanted to introduce her to his thick cock!"

It was my turn to choke on my drink. "You didn't!" I gasped. "That was awfully forward of you!"

Katie giggled, and leaned towards me. "She's had her fingers in my twat!" she whispered. "I think we can say pretty much anything to her!"

I couldn't argue with that, but I spent the next 30 minutes distractedly talking with Katie, while visions of her and Steve, and me and Jessica, and Jessica and Katie danced through my head. By the time Jessica came over to join us, my cock was as hard as a rock and I knew I needed to get Katie back to our room soon!

"I only have a 10-minute break!" Jessica exclaimed, as she approached the table with refills for each of us, plopping down in one of the empty chairs besides us. "I was able to get tomorrow night off if you guys want to do something!" She turned towards Katie. "I know you wanted to see if Steve could join us, I might be able to reach him, but I don't know what I'd even say!"

"If you can get his number, I'll take care of that!" Katie replied confidently.

Jessica went back to work. A little later, she stopped by and dropped a card on the table.

"I found his business card. He had entered one of those 'Free Lunch' contests and I knew we had it somewhere..."

As she left, Katie pulled out her phone.

"Hi, this is Katie from a couple of weeks ago. Would luv 2 c you again tmrw!" she typed out, then hit send.

It was only a few minutes before her phone pinged. "Luv 2, same place? What time?"

Katie giggled. "5 PM - but @ Marriott across street" she texted back, adding a winking emoji.

"Well that's all set!" Katie exclaimed, putting her phone back down on the table. Waving Jessica over, Katie told her to meet us at 5:30 the next night at the Marriott. Jessica nodded nervously but agreed to be there as planned. Then we got our check and headed back to our hotel.

As soon as we were in the room, Katie attacked me. She pushed me onto the bed, the grabbed my jeans and with some help pulled them down to my knees. Immediately she climbed on top of me, hiking her dress up just enough to slide her panties to the side and sink down on me. I gasped as I felt her hot wet pussy envelop me - she was soaked! Leaning forward with her hands on my chest, she started to urgently ride me, slamming herself down on me with each stroke. It only took a few minutes before she cried out in orgasm, causing me to lose control and explode inside her.

"Wow!" I exclaimed as she collapsed onto me, breathing heavily. "What got into you?"

"I don't know!" she panted. "Just the thought of tomorrow has me SO.TURNED.ON! Boy I needed that!" Then she kissed me before rolling off and lying next to me, still breathing heavily. Soon after, we rose, stripped off our clothes, and finally got to bed.

I awoke late the next morning to an empty bed. I rose and wandered around the room curiously. Katie wasn't in the bathroom either. I didn't know what was going on, but I needed a cup of coffee so I padded over to the Keurig to brew a cup. There was a note sitting next to it. "Morning, went shopping, home by noon!" it read.

It was almost 11 and I was starving, so I dressed and popped downstairs and had a quick bite at the restaurant in the lobby. I returned to the room and found Katie there, looking out the window.

"Morning sweete! Have fun shopping? Whatcha get?" I asked, crossing over and wrapping my arms around her from behind.

"Morning hun! Just went out to pick up a few things. I'll show you later! Right now I want to go out and see the city a little!"

We spent a few hours sightseeing, then returned to the room and showered in preparation for our evening. We got dressed, and at 4:30 headed down to the bar. We weren't there long when Steve wandered in, his eyes darting around looking for Katie. He looked a little flustered when he realized I was there sitting with her but crossed the room towards us.

"Hi Ted!" he said, extending his hand.

"Hi Steve!" I replied, shaking his hand in return. "Why don't you join us?"

Steve turned and said hi to Katie without reaching for her, then sat down. "What's going on?" he asked. "I guess I'm a little confused; I thought last time was a one-time thing?"

"That remains to be seen!" Katie replied.

My heart skipped a beat. Was she serious? I thought we had set boundaries?

"I gave my husband the same gift that he gave me. We've invited her here tonight, and tonight will depend entirely on how she feels." Katie continued.

Steve looked confused but didn't ask any more questions. He nodded, then asked what we'd like to drink as this round was on him. We have him our ususals, and he headed up to the bar to order.

As we was up there, Jessica came wandering in, looking like a million bucks. Seeing us, she smiled and quickly crossed the room. Katie stood as she approached, then gave her a big hug, and told her to sit down. Jessica sat, reaching across and taking my hand in hers and giving it a quick squeeze before turning her attention back to Katie.

I sat in silence as they gabbed like old friends. I couldn't believe how quickly and strongly this bond had built between them, but I don't question the ways of women. I looked over at Steve, still waiting at the bar. The bartender put some drinks in front of him, and Steve dropped some bills on the counter before picking up the drinks and turning around to carry them to our table.

His eyes got huge when he realized Jessica was sitting at the table with us.

"Jess?" he asked incredulously as he got close to the table. "You...?" he trailed off, not certain of the polite way to ask if she'd slept with me.

"Hi Steve! It's great to see you!" Jessica said, rising from the table. Steve put the drinks down and gave her a hug, then both sat back down at the table.

We chatted for the next half hour, everyone avoiding the inevitable topic of where the night was going to proceed. Eventually the conversation slowed, and I could tell what was on everyone's mind, but nobody wanted to come outright and say it. Except Katie.

"We have the most incredible view of Times Square!" Katie announced. "Let's go up to our room and we can show you!"

We all looked around for a second, then with unspoken agreement gathered our things and headed for the lobby.

We headed upstairs to our room in silence. The sexual tension was palpable, and I think all of us were nervous to some degree. The elevator arrived on our floor, and we wordlessly walked down the hall. I slid my keycard in, the light flickering green as I turned the handle and walked in. I held the door open as Katie, Jessica, and lastly Steve entered the room.

"Who wants a drink?" I volunteered, and everyone raised their hand halfway, dropping it back to their side. I pulled out a couple of small bottles of wine out and handed one to both Katie and Jessica, then grabbed a couple of nips for Steve and me. Steve and I both downed our pretty quick, while the girls took a couple of sips of their bottles. We were all glancing around, not really looking anyone else the eyes, uncertain of what to do next.

Katie put her bottle down and whispered something in Jessica's ears. Jessica's face flushed, but she nodded.

"We have a surprise for you boys; sit down and we'll be right back!" Katie announced, then grabbed Jessica's hand and they walked off to the bathroom and closed the door behind them. I looked at Steve and shrugged, but I sat down on the loveseat by the window and Steve sat in the chair by the desk.

As the bathroom door opened, the lights in the room suddenly went out. Katie or Jessica must have flipped the switch by the door, plunging the room into darkness, illuminated only by the glow of the thousands of lights way below in Times Square.

Jessica and Katie emerged from the shadow of the hallway, and I gasped. They stood their both covered in matching silk robes. They both looked slightly shy and embarrassed, but I could see they were both excited by the telltale points of their nipples pushing against the silk.

Katie walked over to Steve while Jessica walked over to me.

"Untie me!" Jessica whispered, and I heard a similar sentiment from Katie near Steve. Reaching up with shaking hands, I grasped the tie around her waist and tugged on one end, the bow falling apart. Her robe fell open just slightly, giving me a glimpse of white underneath before she spun around. She and Katie moved in unison, backs to us as they shrugged, allowing the robes to fall off their shoulders. I took a deep breath as I realized they were wearing matching outfits! Both had on lacey white bras, and sheer matching panties. White stockings ran from their feet to their upper thighs, ending just before reaching their panties.

Jessica giggled when I groaned aloud. Katie bent over, her ass towards Steve, and looked back at him.

"Do you like what you see?"

Jessica mirrored her moves, and I looked at her tight ass barely covered by the thin material. I reached up to touch and she spun around and slapped my hand.

"No touching!" she admonished, wiggling her finger at me devilishly. I put my hands back down meekly, and Jessica bent over in front of me, her breasts hanging deliciously underneath her. She reached down and started to pull my shirt up, so I raised my arms and let her pull it over my head and off. Then she turned around and slowly lowered herself into my lap, rubbing her ass slowly up and down my stomach. I glanced over and saw Steve, shirtless, getting the same treatment.

Jessica ground against me for a couple of minutes, then turned back around and knelt between my legs, unbuttoning my pants and tugging them down. I lifted my hips, and she pulled them past my ass and down to my knees but left my boxers on. I had an obvious tent in mine. Looking over I could see Steve was now also in his boxers, his thick cock already poking out the fly!

Jessica got up and turned back around, grinding herself back on me. I could feel moisture but wasn't sure if it was from her arousal or pre-cum leaking out of my cock! I leaned my head back and moaned, but still made sure not to move my hands from besides me.

Jessica continued to grind for a couple of minutes, then stood up and sauntered forward a few steps. Katie joined her and stood behind Jessica. Slowly she lowered the straps from Jessica's shoulders, then led them down her arms. Steve and my eyes were locked on Jessica's breasts as they slowly came into view, first her creamy skin, then the hint of her areola, then finally her rock-hard nipples.

Katie dropped the bra to the floor, then reached around from behind Jessica and slowly cupped her breasts, then slowly slid her fingers up over the surface. Jessica gasped loudly when Katie gently pinched her nipples between her fingers, her eyes closing in pleasure.

Katie gently rubbed Jessica's breasts for a second, then moved to the side. Turning away from us, she bent over at the waist, reached back and grabbed the waistband of her panties, slowly peeling them down off her ass. I could see the glistening wetness from where I was sitting, and her lips had started to part with arousal.

Jessica leaned over Katie and slowly ran her hands over her ass, rubbing gently circles on her cheeks. Suddenly she pulled her hand back and gave Katie a firm smack on the ass. SWACK! Katie gave a light squeal, then unconsciously gyrated her hips as Jessica resumed rubbing. Jessica gently ran one finger up Katie's moist opening, and Katie's knees buckled as she groaned.

Jessica pulled back, and Katie stood up and turned back towards Steve and me. Their faces were full of lust, and their eyes darted back and forth between us. Jessica's was naked from the waist up, Katie naked in the middle, and both still had their stockings on.

Katie walked to me and knelt between my legs, and Jessica got down on her hands and knees and crawled over in front of Steve. Steve's eyes got big; I don't think he expected Jessica to be the one coming towards him!

My attention immediately shifted back to Katie as she grasped my cock in her hand.

"I told you last time was a one-time thing!" she said quietly. She nodded towards Steve and Jessica. "We just needed to get them past their fear of each other!" With that, she lowered her head and slowly sucked the head of my cock into her mouth. I closed my eyes and leaned my head back, enjoying the feel of her lips sliding up and down my shaft. I felt her hand close around my balls and gently roll them back and forth, stimulating them while my adrenalin soared, right on the edge between pleasure and concern she'd squeeze a little too hard!

I was enjoying this, but I NEEDED her. I grabbed her head and pulled her off my cock. I pulled her towards me and kissed her, tasting me on her lips. As we kissed, I reached around her back and unsnapped her bra. She pulled back from me, and her bra fell forward into my lap. Reaching down, I gently caressed her breasts, then pulled her up so I could run my tongue around each nipple, gently sucking each one into my mouth.

Katie pushed against me, her breathing heavy in my ears. Lifting her up further, I spun her around and eased her down into my lap. She reached down and grabbed my cock, guiding it to her soaking pussy. I slid in with no resistance. She was on fire, her heat surrounding me. I reached around her, one arm just under her breasts, the other hand dropping down, my fingers burrowing into her folds so I could start rubbing her clit.

Katie bounced up and down on top of me urgently as my finger flew back and forth across her clit. I couldn't see her face but knew that her eyes were locked on Jessica and Steve, and whatever they were doing was fueling her lust. Suddenly she sank down on me as far as she could go, her body jerking forward out my arms as she cried out in orgasm. Her pussy gripped me tightly and I focused all my energy on not cumming immediately as she shuddered in my lap.