Five Dates Ch. 07

It was Friday. I had to admit I was surprisingly nervous about Saturday. This was a trip that I had wished to make with my wife so many times, each time I suggested it she declined. She said if she wanted to just spend three days having sex, she didn't have to fly halfway around the world to do it. She could just lock the door and turn off the phone. Somehow it wouldn't be the same thing and it had never happened either. To be planning this trip with Liz, was, well, difficult. But it was also the best way I could think of for the two of us to explore each other. I had to admit I was having some difficulty concentrating on work, so having Liz come into my office was a welcome distraction. The fact that she closed the door behind herself would have suggested that maybe she wanted something private, like sex? The look on her face was anything but happy and joyous at our impending trip, which I had only hours ago sent her the details on, or at least as many details as I was willing to share for a surprise trip.

"Michael, we have a problem," she said in a serious tone as she walked to my desk.

"We do?"

"We do. A serious problem at that."

I leaned back in my chair and looked over my computer monitors at her face as she stepped to my desk and leaned on it with her hands. "What kind of a problem?"

"I was trying to figure out what to take on the trip last night. I mean I didn't know exactly where we were going, but you said warm and beachy, so that gave me some ideas. Well, while I was packing I realized that one of us just isn't dressing appropriately for our relationship."

"Not dressing appropriately? I don't see anything wrong with what you wear."

"I wasn't talking about me," she said seriously. "I was talking about those fuddy-duddy boxers you wear. They just aren't going to do."

"They aren't?"

"They are NOT!" she said, breaking into a grin. "Now, I need you to stand up and take your underwear off."

"My underwear? I kinda have to take my pants off too."

She smiled broadly. "I know."

I shook my head. It wouldn't be the first time I was naked in my office with a woman, and since it was with Liz, I wasn't going to complain. I bent over, took my shoes off and then stood up, undoing my pants. I slid them down and stepped out of 'em. I slid my boxers off, freeing my now-growing dick, and held my boxers out for her. "So, now what do I wear?" I asked as she took them from me.

She reached into the pocket of her dress and pulled out what looked like the bottom of a bikini and held it out for me. "These." She said simply. "Go ahead. Try em on!"

"Ladies underwear?" I asked, looking at the very small pair of red bikini briefs.

"Nope. Men's," she answered. "If you're gonna be a hot, sexy guy you need to wear the right clothes."

"And this is the right clothes?" I asked as I stepped into the tiny red briefs. I pulled them up my thighs and up as far over my dick as they would go, a significant portion still sticking up o ut of the nearly see-through red underwear. "I don't think they're quite going to work."

"Oh, I think they're going to work just fine." She grinned. She turned and walked to the door. She opened it and called out to Darleen, and then held the door open so anyone who wanted to look in could see me standing there half-dressed. I was just glad that the tail of my dress shirt covered the important parts. Darleen walked in and Liz closed the door after her. "We need another opinion. Michael doesn't seem to think the underwear I want him to wear is appropriate. What do you think?"

Darleen walked over to me. "Lift up your shirt tail so I can see?" I rolled my eyes and pulled the bottom of my dress shirt up to my stomach, exposing the tiny red underwear and the significant portion of the hardon protruding up out of them. "Oh hell. Those look perfect to me. May I?" she asked looking over at Liz.

"Feel free," Liz said with a smile. "Just leave enough for him to finish me. I don't think I can last until tomorrow."

"Oh, that's easy," Darleen said as she stood up. It took her only a few moments to get rid of her dress: the only thing she was apparently wearing. "The best thing about a pair of briefs like this is how easy it is to get access." Darleen whispered as she pushed the front of the briefs down in front so that they hooked under my balls, leaving me completely exposed. She turned herself around and used my dick as a handle to get me close to the desk, where she bent over. She guided me to her pussy and rubbed my head up and down. "Come on. Don't be afraid. I know you like fucking me."

I looked at Liz who was stripping her dress off. She just smiled and said, "Go ahead."

I still didn't quite understand her, which, I guess, was the reason we were going on this trip. To understand each other better. I shrugged to myself and held Darleen's hips while I pushed my dick slowly into her, getting a long, deep moan from her as my cock forced its way into her several inches. I didn't need any coaxing to start stroking, using short little jabbing strokes at first, lubricating both of us with juices from her depths. In and out I stroked as Liz stepped up to me and pressed herself against my side. She turned my head and pressed her lips to mine in a long, hot kiss that lasted several minutes, all the time, still fucking Darleen. Liz's hands roamed around my chest and back and butt while we kissed and I fucked my secretary, Liz seeming to become more and more excited as each moment passed.

Quite suddenly she pushed me back, pulling my cock from Darleen. "Sit on the desk," she ordered Darleen. "Right there," Liz said, coaxing Darlene to stand up and turn around to sit on the desk edge she had just been bent over. Liz stepped to her and leaned down, kissing her chest and breasts while pushing her ass out at me. "Go ahead. I'm ready for you to make me come," she said over her shoulder to me before turning her face back to Darleen's chest. "I haven't tasted pussy in a while," she said to Darleen as she bent lower and dipped her head between Darleen's thighs. I stood there, staring at the two of them as Liz started to lick and tease Darleen's pussy, drawing gasps and moans from her.

Darleen leaned further back and lifted and spread her legs, sticking them in the air so Liz could fully access her. "Come on. Fuck me lover!" Liz said without pulling her face from Darleen's pussy. Between having just been in Darlene and now watching Liz licking her, I was hard as an iron rod. I stepped to Liz and pushed my pussy-juice-covered dick easily into her. I moved my shaft in and out of her, eliciting moans from her that seemed to just increase the pleasure Darleen was feeling. I reached over Liz as I continued to stroke in and out of her pussy, reaching for Darleen's big, soft tits with both hands. I grasped her nipples and pulled and stretched them as Liz worked her pussy closer and closer to the climax that I had already started teasing with my dick. In and out I stroked, getting more and more turned on by the moment. I could feel my cock swelling inside Liz, sure that I was going to explode in her at any moment, unable to hold back much longer.

The sight and sound of Darleen starting to climax pushed me over the edge. With a grunt my body spasmed and jammed into Liz with a massive gush of cum. I stood there, pinching and pulling Darleen's nipples while my body shuddered and jerked, filling Liz with my cum.

Darleen and I both started to settle from our mutually-timed climaxes, Liz pulling her now cum-covered face from between Darleen's legs. She pulled off my softening cock and turned to face me. She wrapped her arms around me and pulled us together. She kissed me, her lips and face tasting of Darleen's cum, though neither of us seemed to mind. We kissed for maybe two full minutes before she pulled away from me. She grinned and gave me another short quick peck on the lips before walking to where she'd hung her dress over the back of the other chair in my office. She dug in the dress pocket, pulled out a pair of underwear and stepped into them. She pulled her dress on while I stood there with my cock dripping, and Darleen sat on my desk panting. Dressed, Liz stepped to me and kissed me on the lips again. "I have more of those underwear for you. Why don't you come down to my office after Darleen cleans you up? I'd really like it for you to start wearing those instead of the boxers. Would you? For me?"

"Sure," I breathed as she broke away from me and started for the door. "Hey, wait a second. What was this about?" I asked, feeling a little confused.

"Just wanted to see if you liked seeing me making love to another woman. Now I know better what to pack."

"You do? How does this impact that?" I asked as she opened the door.

She stopped halfway out the door and smiled back. "You'll see," she said before turning and walking away, leaving the door wide open. "Boys," she acknowledged with a nod as she walked past Mark and Jerry, both staring through the open door at Darleen's naked body. She squealed as she slipped off the desk and rushed to the door, trying to cover her boobs and pussy at the same time. She pushed the door closed and leaned her back against it, letting her hands fall away, her face flushed red as she panted.

"I'll get her for that." She said after a few seconds. She pushed away from the door and walked back to me. "I guess I do have some cleanup to do," she said with a grin as she walked toward me again. "I wasn't expecting any of that."

"Neither was I. I don't think I quite understand her."

"I know I don't, but if the price to let me fuck you is to let her lick me like that, well, I'm not going to complain." She knelt in front of me and took a few short minutes to get my dick licked and sucked and starting to harden again before she declared me done. She tucked me into the red underwear and stood up. She dressed while I put my pants back on. "Guess Mark and Jerry got a good look," she said as she looked back at me. "Maybe one of these day's I'll give them something really hot to watch."

"I wouldn't go too far out on a limb. Mark may invite you over for dinner with his wife."

"Is that a warning?"

"It could be. Just saying," I said as she opened the door.

"Hmmmm. After this it might be fun to see," she said as she headed back to her desk.

I waited some time and then headed down to Liz's office to collect my package of underwear she said she had. To my dismay, she took great pleasure in giving them to me, one at a time, not in the privacy of her office, but on the corner of her secretary's desk, giving all four of her female engineers and her secretary a nice look at each one, leaving me blushing brightly at the size and exposure of some of them. She made me promise to not pack any underwear but those, and then gave me a very long, very wet sensual kiss right in front of everyone, her hands roaming over my body, including my crotch, the entire duration, almost as if she wanted the girls to see me get a hardon. At least I knew I wasn't going to have to worry about an adverse employment action due to the significant PDA. But I just didn't quite understand what she was thinking.

Saturday morning found me at her doorstep, ringing the bell with more than a little trepidation. After Friday's little show I wasn't sure what to expect. She'd seemed to be more private and discreet before that, but on Friday she acted quite the opposite of what I had expected, so I didn't know which Liz I was going to get. The sexy, seductive, soft, sweet, loving Liz, or the slutty, exhibitionist-tending Liz. I almost breathed a sigh of relief when she answered the door in a very sexy, but not overly slutty pale-green sun dress. It was sleeveless, cut very deeply down between her sexy breasts, but also covered everything nicely. The skirt portion came to the middle of her thighs, showing off her long, sexy legs above a pair of very sensible-looking athletic shoes. She walked out onto the front porch and wrapped her arms around me before leaning to me for a soft, sensual kiss.

"Good morning," I whispered as we broke the soft kiss.

"Good morning sweetie. So, are you ready to sweep me off my feet and carry me away to a fantasy getaway?"

"I am, as long as I don't have to carry you all the way." I chuckled.

She smiled and gave me another quick peck on the lips. "Let me get my bag." She turned and stepped back in and in moments was rolling her suitcase out the door. She locked up behind herself and I pulled her suitcase to the car, letting her carry the purse she had over her shoulder. Two hours to the airport, another hour waiting at security and an hour at the gate saw us on our way to Miami. It was a boring flight which we both spent reading, her a book and me my Kindle. We landed and barely had time to make our connection due to a slight delay we had waiting for a thunder storm to clear before we could land. The next leg was a three hour flight on a modest-sized jet. It had three seats on each side of the aisle, with Liz and I in the two aisle side seats of our row, about three-quarters of the way back. Another woman, about Liz's age, had the window seat, so instead of being trapped between them, Liz took the middle seat.

We pushed away from the gate and then we sat. And we sat, and we sat. For almost an hour we sat on the tarmac waiting for the traffic that had bottled up due to the short storm made their way to the runways to take off. The whole time Liz and the woman in the window seat chatted quietly. I couldn't quite hear their conversation, but I couldn't help but notice her look over at me periodically. We finally took off and climbed to cruising altitude and we both settled back for the flight. Well, almost. As soon as we got into the air, she decided she needed to go to the bathroom. I let her out, and on the way back she asked the stewardess for a blanket for her legs. When she got back to sit, she had me move over and sat in the aisle seat. She spread the blanket over her legs and in the next few minutes she lifted the armrest between us and snuggled against me. She pulled the blanket over so it covered my lap as well.

"Liz, what are you doing?" I whispered as her fingers started working on the front of my shorts under the blanket.

"Playing," she whispered.

"Here?"

"Uh huh. Gotta get you hard if you're gonna fuck me," she whispered, her breath blowing into my ear and making me shudder.

"Here?"

"Never heard of the mile-high club? I've been fucked just about everyplace else. Why not up here?"

"We could get caught."

"What are they going to do, throw us out of the airplane? If you look out there it's all water."

"Good lord," I groaned as she worked my shorts and briefs down my hips and butt enough to get my dick free, which was, surprisingly, already getting hard.

"Come on. Feels to me like someone likes the idea."

"I didn't say I didn't like the idea, I said I didn't want to get caught."

"So we try not to get caught," she whispered as she stroked my hardening dick under the blanket. "We just get up to go to the bathroom and then slip into the same one. No one will know the difference."

"With all the people on board?"

"All the more fun. Just make sure you come quietly. Sometimes you can be so loud when you come," she whispered.

"Me?" I asked in surprise. "I think that's you."

"Oh, yeah. Well, me too." She giggled. "You ready?"

"With my dick hanging out?"

"Uh huh. Your polo shirt is more than long enough to cover it. As long as your shorts don't fall down."

"Yeah, and how do I keep that from happening?"

"You'll think of something. But do it quickly, cuz I'm taking the blanket off in about ten seconds," she whispered as she let go of my dick. It wasn't even ten seconds and she pulled the blanket off, leaving my hardon completely exposed to the woman in the window seat. I pulled my shirt down to cover my hardon and my open fly, but not before she had a considerable look at it. I suddenly wondered if that was part of the discussion Liz'd had with the woman, since she didn't seem to be at all upset or likely to call the stewardess. "Come on," she whispered, climbing out of her seat and standing in the aisle expectantly. I did the best I could to keep myself covered while I got out of mine, and then prayed my pants wouldn't fall all the way down as we walked past the ten or so rows between our seats and the bathrooms.

If you've never been in an airplane lavatory, you haven't learned the definition of cramped yet. Liz opened the door, pushed me inside, made me sit down on the stool seat before anyone could notice and then stepped in after me. She pulled up hem of her skirt all the way to her waist and pushed down the tiny pair of panties she had on. "I didn't want to wear any, but I didn't figure it'd be a good idea to leak your come down my legs up here," she whispered as she leaned her butt back and started to sit on me. I grabbed my dick and aimed it at her pussy. As long as we were already there...

"Ohhhhh yes," she moaned as she pushed down on my fat head. "I've been thinking about this since I got the idea last night."

"Yeah?" I asked as she started to lift and lower herself on my lap, sliding me in and out of her hot, wet pussy.

"Uh huh," she moaned softly, the sound of my cock sliding in and out of her pussy making a soft squish into her depths. "I got to thinking about places I hadn't ever had sex. I wanted to find someplace special that would be all yours."

"Why is that?" I grunted as her sexy pussy started to push my level of arousal quickly up. I reached up and cupped her tits through her dress, only to have her move my hands. She pulled the shoulders of the dress apart and the top slid easily down all the way to her waist, leaving her tits completely exposed. "Someone was thinking," I whispered as I cupped her tits and squeezed her nipples between my fingers, drawing a gentle moan from her lips.

"Because I wanted to have sex with you one place that was just you," she panted. "Oh fuck. I'm going to come," she moaned softly as she bounced a little faster. "Come for me. Let me feel you come."

"Almost," I panted as she slapped her ass hard against my legs a few times, the material of my shorts keeping us from making an audible slap. "Ohhhh yeah. Almost there. Ohhhhhh so close," I groaned as there was a knock on the door.

"Just a minute!" she gasped out breathlessly. "Almost done!"

"Uh huh," I whispered as I closed my eyes moments before my cock erupted inside her. She pushed herself down on me and stifled a moan of pleasure as her pussy clenched around my spurting cock. I could feel her depths squeezing my shaft, trying to milk my cum from me, as if it needed any help. Half a dozen times my body surged into her before I was left with only a gentle drool into her pussy.

There was another knock on the door. "Hang on a second. I gotta get my clothes back on!" she snapped at whoever was on the other side of the door. She stood up and fixed her dress and pulled up her panties, trapping my cum in her pussy. I barely had enough room to stand and pull my pants up, but managed to lean back against the wall to accomplish it. Dressed, she unlocked the door and stepped out, right in front of a stewardess with her arms crossed across her chest. Liz gave the woman a coy little shrug as I stepped out behind Liz, the woman glaring at me now.

"This kind of thing is not allowed!" she snapped quietly. "If there's any more trouble from either of you two, I'm going to turn you in when we land."

"Yes ma'am," I said quietly, glad that she was at least not being overly loud and drawing attention to us.

"Now you and your wife need to return to your seats. You're lucky I have a soft spot for newlyweds!" the stewardess snapped quietly. "Next time, wait until you get to the honeymoon hotel!"