Kasey's Conundrum

I put the box back on the shelf. Hell, I thought, might as well live dangerously.

There was a chain motel next to the Walmart, so we checked in.

"Why don't you get your shower and get cleaned up and we can go grab a bite to eat," I suggested.

"Why don't we take a shower together, fuck, and then go grab a bite to eat," Kasey countered.

We agreed that her suggestion was a better one. Kasey knew that this first time would go quickly. My stamina was no match for her youthful beauty. By the time we soaped each other up, taking a survey of the territory as we went, we were both primed and ready.

Despite my age and previous marital status, I still felt kind of clumsy where sex was concerned. Kasey seemed to sense that and patiently guided me to achieve the desired end. I entered her from the rear. The view of her gorgeous ass made it impossible for me to last very long. I think she knew that going in and was why she wasn't concerned about a late dinner. The good thing was that she came just after I did--or else she faked it really well.

"Faked it, my ass," she said. "There ain't nothin' wrong with that thick cock of yours. It did just fine what it was supposed to do." She turned and embraced me, looking into my eyes. "You need to understand that you turn me on, Mr. Riley." She punctuated her statement with a long wet kiss that would have made me hard again if it weren't for the fact that I'd just dumped a load of sperm into her.

We dressed quickly. Kasey didn't take long. She was only wearing two items of clothing, a wife-beater tank she'd cropped that fit like skin, and a pair of booty shorts. No underwear. Prominent camel toe. The booty shorts hugged her ass in a most delectable fashion.

"How do I look?" she asked, probably reading the look on my face.

"Good enough to eat," I said.

"I'm going to hold you to that," she said with a sensual smile.

We walked to the steak house. Kasey took my hand and held it as we walked. I felt like I was in high school on a first date--except that we'd already had sex. I was really looking forward to round two. The smell of searing beef wafting on the breeze brought me back to the here and now.

The steak house wasn't very crowded. It was still early for dinner. We followed the hostess to our table. She was wearing yoga pants and following her was a pleasure, though I felt a tad guilty as though I was cheating on Kasey. The hostess smiled and said our waitress would be right with us.

I caught Kasey watching her ass as she walked away. "She's got a really nice butt, doesn't she?" Kasey asked when she realized I had been watching. "Be honest," she reminded me. "I know you saw that ass."

"Yeah, she does," I answered.

"Will you think less of me if I admit thinking sexually about other women?"

I realized that Kasey was going out on a limb telling me this. There was no way I was going to shut her down. "No," I answered.

"Do you ever think about guys sexually?" she asked.

I shook my head.

"Really?" she pressed. "No shemale fantasies? You never wondered what it would be like to take a dick up the ass?"

"Well, yeah," I admitted sheepishly. "I wasn't thinking about shemales."

"Hi! I'm Brittany. I'll be waiting on you this evening. Can I get you started with something to drink?"

"Hi Brittany," Kasey said, sweetly. "Do you have sweet tea?"

"Sure," Brittany said. "Is that what you would like?"

"Yes. Thank you," Kasey answered.

"And you, sir?"

"Do you have anything on tap, or just bottles?" I asked, while noticing Kasey studying Brittany.

"We have Modelo, Sam Adams, Miller Lite, Michelob Ultra, Bud Light, and Blue Moon on tap," Brittany answered cheerfully.

"I'll take a Miller Lite," I answered. I noticed that Brittany had a nice figure, too. In particular, her ass was gorgeous, and she was wearing yoga shorts which really showed it to good advantage.

"I really like your lip gloss, Brittany," Kasey piped up. "You look like you'd be a great kisser."

"Thanks," Brittany said agreeably. She was the most cheerful person on the planet, apparently. "I do my best," she said, studying Kasey more closely. "Let me get those drinks and I'll be back," she said, still cheerful.

"Would you consider it cheating if I made love to another woman? Brittany, for example?" Kasey asked when Brittany had gone.

I had wondered if Kasey was going there when she first brought up same-sex attraction, but I honestly didn't think anything would come of it. I wasn't expecting to have to answer that question so soon into our relationship--if we actually had a relationship.

"I think if I was cut out of the loop I might. If I could be a part of it, even just watching, I wouldn't feel like I was being left out."

"So, you're okay with me have sex with another woman as long as you can watch?"

"I guess," I said. "I'm not really sure how I'd feel until it happens."

"And suppose Brittany is cool with it and offers to let you join in, should I be okay with it?" she asked. "Before you answer that, imagine the reverse scenario: we pick up a shemale--you okay if she slips me the salami?"

"That's a tough one," I answered. "On the one hand, watching it would be sexy as hell, on the other hand, I might be jealous. I tend to be possessive."

Kasey unwrapped her silverware and smoothed out her napkin.

"I get it," she said. "I'm not sure I'd feel comfortable with you boffing Brittany, but I am gonna suggest we try it. If we're both involved with having sex with a third person, we should both be able to take part in the experience equally. That's really what doing it together would be about, right?"

I could understand her logic, that we'd be bound through the togetherness of the experience and that limiting that experience to one of the participants automatically had the effect of cutting the other person out of it. Since I honestly didn't think it would become an issue--I couldn't picture such a scenario actually coming to fruition, I agree with her that nothing would be off limits in the event of a threesome. Then Brittany came back with our drinks.

"So, are you two a couple?" Brittany asked hesitantly while placing our drinks on the table.

"We are," Kasey said. "But we both think you're gorgeous." Brittany's cheeks colored at that.

"Have you decided what you want to order?" she asked professionally.

"Jack said he'd be content just to watch if you don't feel comfortable," Kasey said smoothly. "I just wanna know if you taste as good as you look." She said this while peering down at her menu. "I'll have the petite ribeye. Medium. And the baked sweet potato."

"And you, sir?" Brittany said, seemingly unrattled.

"I'll have the king ribeye," I answered. "Medium and sweet potato, also."

Brittany asked, "Are you just in town for the night?"

"Yes. We're staying at the Fairfield," Kasey answered.

"Ok, I'll get this order put right in for you," she said and left. I watched her go. She did have a really nice ass.

"You like her, too, don't you?" Kasey asked. Apparently, discretion is not my forte. "I don't mind if you look at other girls," she said. "But that's not a license to fuck anyone you want."

"Understood," I said, feeling busted.

"Feel free to share the experience with me. I like to know what makes you hot. If you see a hot girl, we can share the experience together. Because you now know that I like hot girls too."

I didn't know how to respond to that, so I just kept silent. Kasey was full of surprises. I thought back to the truck stop manager's warning that "this kind's always trouble" and hoped that my instincts, rather than his, would be correct.

"Your dinners should be up shortly," Brittany said, appearing beside our table suddenly. "Do you need a drink refill or anything?"

"Yes, please," Kasey said, smiling.

"And another beer, sir?" she asked.

"Just call me Jack. And I'd love another beer. Thank you."

"Okay, Jack, and you are?" Brittany directed the question to Kasey.

"I'm sorry, babe," Kasey said. "I've completely forgotten my manners. I'm Kasey."

"Pleased to meet you both," she said. "I'll be right back with your drinks, and your dinners soon." She turned and sauntered away. I watched her ass jiggle as she walked. It was a great ass."

"Would you lick that ass?" Kasey asked.

"Without hesitation," I answered.

"Good. We're on the same page." She took a sip of tea. "Would you let me tie you up?" she asked.

Startled at the change of subject, I blurted out a confused, "Huh?"

"Sorry. I was just thinking how much fun it would be if you were tied up and Brittany and I could have our way with you. We could make you lick both our asses."

"You don't have to tie me up to do that," I said.

"But don't you think the element of helplessness would add so much to the experience? I've often fantasized about being tied up in a room full of men who then have their way with me."

"That's rape," I said.

"Well, it would be if I didn't consent to being tied up," she admitted. "But the consent changes everything--but there's still the element of helplessness and you're not responsible, directly at least, for all the things they do to you or make you do to them. See?"

"I suppose," I said letting out a sigh.

"I warned you that I knew things," she grinned.

"Hi folks," Brittany said with hands full and another waitress carrying a tray. "I've got your drinks and your dinners."

Brittany put the drinks down and then served dinner. Her helper left, but she stayed to chat.

"Make sure the steaks are done to your liking," she said. "We close at 9, but I have to stay until my tables are cleared. It could be after 10. Is that too late for you guys?"

Kasey looked at me, knowing that I would have to make that call. But it wasn't like I was going to let an opportunity like this pass me by.

"Not at all," I said. Kasey smiled.

"I know this is a lot to ask," Brittany said hesitantly, "but, would you mind if Heather came with me? She's the hostess."

Kasey and I both looked at each other. Heather was the hostess with the ass we were both drooling over on the way in.

"You understand we intend to have sex, right?" Kasey blurted out. Brittany blushed and looked around to make sure no one heard.

"Yeah. Sure! Heather and I are... friends," Brittany explained. "But we like to do... other people together."

"Is everything all right here?" Heather asked. She had seen Brittany talking to us and wanted to make sure she was okay, and probably to check us out again herself.

"It's great!" Kasey said with a smile. "The food is excellent, and the service is even better!"

Heather and Brittany exchanged glances.

"Our after-hours service is even better," Heather said, looking directly at me.

"We're looking forward to the experience," I said.

"Great! We'll leave you two alone to enjoy your dinner. Make sure to give Brittany all the information she needs." She walked off with that fantastic ass.

I couldn't believe my good fortune. This day just kept getting better and better. First, I got a girlfriend, now I was on my way to having my first foursome with three girls who were all knockouts. I was starting to worry I wouldn't have enough dick to go around.

"Remember all that crap I said about boffing Brittany being, okay? I'm having second thoughts. Heather wants your cock. I'm a little bit jealous about that. I'm not saying you can't give it to her. I'm just saying, I wanted her first and the fact that she wants you is a little irritating."

"Are you sure you want to go through with this?"

"Are you kidding? Both of those girls are gorgeous. To be with both of them is a dream come true. And since I can only eat one pussy at a time, it makes sense for you to share the love. No. We're doing this. It'll be epic."

Brittany came to check on us and we gave her our room number and a number to text us at. She smiled and said she was looking forward to it. We finished our dinner and paid the check, adding a generous tip, and walked back to our room. As we walked, we passed a liquor store and Kasey suggested we pick up some booze for later. So, I picked up some Captain Morgan and Tito's and mixers to go with.

"Are you still going to love me after you have your dick in Heather?" Kasey asked as we walked.

"If it's going to bother you, I won't do it," I said, though it pained me greatly.

"I wouldn't deny you the opportunity," she said. "I'm just being a whiny bitch because I'm insecure. I know she has a better body than I do." I didn't say anything. I wasn't going to fall into that trap. "It's okay for you to admit that," she continued, sensing my discomfort. "Always honest. Remember?"

I stopped and turned her toward me and kissed her. She met my kiss with surprise that turned into passion.

"Heather does have a great body," I admitted, "but she's not you. You're not just a piece of ass to me," I said, struggling to put my feelings into words. "I will not stop loving you. Ever." There I said it. I pulled her to me and kissed her again. This time there was nothing in her kiss but passion.

"If you keep squeezing me like that, I'm going to wet myself," she said, breaking the spell. "Sorry. Really bad timing, I know."

Playfully, I squeezed her again, pressing my crotch into her.

"I'll piss all over you if you do that again," she threatened.

"Go ahead," I jibed.

Then she took the bait. I heard the spattering before I felt the warm wetness soaking into my jeans. I felt my cock growing harder. For some strange reason, her pissing on me--in public, no less! --was a huge turn on. I reached my hand down and cupped her crotch as the last bit of piss flowed out. I pulled my hand out and sniffed, then licked it. Bitter, but not horrible.

"Aren't you the kinky boy," she said, rubbing my crotch and sensing the bulge there. "So, you like being pissed on, eh? Imagine how good my piss will taste going down your throat," she said with an evil flare to her voice. "But your pants are a mess. Let's get you back and cleaned up."

It was only a couple blocks from Kasey's "accident" to our room, but I was the one that got the stares. My crotch was wet, and it showed, but because of the fabric that her shorts were made of, hers looked dry. Fortunately, our motel had a small laundromat and Kasey threw our soiled laundry in the machine, including the ones she was wearing. She walked back to our room naked--and our room was street-side and outdoor accessible.

"You're crazy, girl!" I scolded.

"Yup. Thanks to you I'm able to embrace my inner slut. Speaking of which," she said, plopping on the bed, "I think you should eat my ass and pussy until the girls get here."

"But they probably won't be here for another couple of hours,"I observed. Kasey gave me a "so what" look that made me realize my folly, so I had her scoot to the head of the bed and got busy.

Admittedly, I was out of practice where cunnilingus was concerned, but Kasey didn't berate me for my clumsiness. Instead, she patiently gave constructive instruction. It must have worked. She came three times, squirting the last two of them. As far as anilingus goes, I was a novice. My ex- wife was far too uptight for me to even consider asking her. My desire had remained unfulfilled until today. Kasey had a luscious asshole, nice and clean from our earlier shower, and it was a pleasure to see how far up her ass I could stick my tongue. She diddled herself while I munched her ass and soon, she was squirting on me again. I suspected she was doing it on purpose, but I didn't care.

"That was pretty intense," Kasey said afterwards. "I've never had my ass eaten before. I obviously liked it. Sorry about all the squirting," she added. "I've never done that before either."

"Well, I guess it's a night of firsts for both of us," I said on my way to the bathroom to wash my face. When I came out, Kasey was answering the door, stark naked. Of course, given that I walked into the room in my birthday suit I had no room to talk.

Seeing Heather and Brittany standing there made me realize that I had never stood naked in front of so many women at the same time. I felt my cock stirring to attention.

"Hi, Jack. I see you're glad to see me," Heather said. I felt my face redden and my cock get harder.

Kasey looked at my rigid cock with a look of concern. No doubt she thought it was the result of Heather, but it was really just from standing naked in front of so many strange women. (I had known Kasey for less than twenty-four hours; she was still strange as far as my cock was concerned.)

"We have some rum and vodka if you want a drink to take the edge off," Kasey offered.

"I just need a good orgasm to take the edge off," Heather said.

"So how do you want to do this?" Brittany asked. "Are there any rules we need to be aware of?"

"Nope," Kasey said. "We both just want to enjoy you both. And just so you know, Jack likes pee, so, if you have to go, don't waste it."

"How do you feel about sucking your man's cum out of my pussy?" Heather asked Kasey.

"I'll do it," Kasey said enthusiastically. "I might even try your pee if the occasion arises."

"Let's get started, then," Brittany said. "I want to kiss you so bad. I've been wanting to ever since I saw you."

Kasey and Brittany engaged in a kissing frenzy that was impressive to watch. My attention was drawn elsewhere however, given that Heather wanted my full attention. She had already shed her clothing and was leading me to the bed, by the cock!

Heather sat on the edge of the bed and began giving me head. I'd only ever had a girl do that to me once in high school, and she wasn't very good at it. Heather was. She did everything right. Watching my cock disappear into her mouth was quite a thrill and it felt wonderful.

Heather was a petite girl with a perfect figure, tight ass, and pert breasts that were as firm as Kasey's but larger. Her lob haircut and golden blonde hair completed her cheerleader look. In short, she was about as hot as they come. And I was about to. Sensing this she stopped.

"Baby, you need to cum in my pussy so your woman can suck it out. I want you to shoot a big load up my cunt, okay?"

I didn't need to be asked twice. She leaned back on the bed and spread her legs wide and her pussy lips open and I slid right in. She was wet as hell, so there was practically no resistance. Still, I could feel her vagina squeezing my cock as I filled her hole. Sadly, I was only a few thrusts in before I shot my load. She had expected as much and had been fingering her clit the whole time. Consequently, she came--quite forcefully, too--just after I did. She pulled me on top of her and we made out on the bed.

"Hey, babe," she said suddenly, "we need to get your girlfriend over here to suck the cum out of my pussy before it drips down my leg."

Kasey heard her and looked up from Brittany's juicy cunt. Brittany moved to the head of the bed. Heather began eating her pussy. Kasey laid under her and slurped my cum from Heather's cunt. I stood back and took in the scene of the three beautiful women engaged in cunnilingus. It was like a real-life porno movie. After a few minutes, the attraction of Heather's ass perched up in the air was more than I could resist. I moved over and began tonguing her ass. I couldn't tell if she liked it--she couldn't say, but she didn't complain, either. (I learned later that she did, indeed, enjoy it very much.)

After a few moments, Brittany began writhing in the throes of orgasm. Actually writhing. Uncontrollably writhing--to the point that I began to be afraid that she was having a seizure. She wasn't, but Heather knew her cunt very well, and with everything that had gone before, Brittany experienced the most intense orgasm she'd ever had.

While Brittany recovered, Heather turned her attention to Kasey. Kasey told me later that she'd never had her pussy eaten so masterfully before. I would have been put out, but Kasey assured me that it was only because she was a woman and had a cunt of her own that she was so good at it. "Don't worry," she told me, "I'll give you plenty of opportunities to improve. Who knows? Maybe someday you'll be as good."