On the Way to Columbus

I had some work to do in Columbus, Ohio, so we headed that direction. I probably would have driven all day to get there, but it would have made for a long day and I wasn't in that big of a hurry, so we decide to just go as far as New Columbia, Pennsylvania and spend the night. Now that I was with Sarah, a girl who'd volunteered to be my girlfriend to escape her miserable home life, spending the night meant more than just dinner, a shower, and bed. I wanted to get into a hotel just after check-in time so that I could enjoy the entire evening with her.

On the way, we talked, of course, about the previous evening. I asked her why she let me fuck Ashlynn.

"Was that bad?" she asked, concerned. "You didn't seem to mind."

"No, it wasn't bad," I answered. "Ashlynn was great. I was just surprised you were willing to share me."

Sarah chuckled at that.

"What?" I asked, curious as to why it was so amusing.

"Just the way you said, 'willing to share me,' like you were some prize fuck that I couldn't bear to let anyone else experience."

I wasn't sure how to react to that, but I tried to explain. "I just meant that, you know, if we're a couple, that means we're exclusive."

"Oh, we are, Bob. We are. I promised you I would be faithful, and I meant it—except for the occasional other girl, which you said you were okay with. But I wouldn't be a very good mistress if I kept my little fuck-slut all to myself. Sharing, is caring, Bob. Me sharing you is different from you sharing me—trust me."

"Well, I guess I'm the jealous type, and greedy. I just want you all to myself."

"It's not that I don't want you all to myself, Bob. I do—as far as relationship goes. But, sexually, as your mistress, I have to do what I think is best for you and that's going to require getting other people involved. You just have to trust me."

That sounded kind of ominous to me, but not so much so that I was worried. Maybe Sarah intended to share her girlfriends as she had Ashlynn. That wouldn't be so bad.

"Speaking of trusting me," Sarah continued, "last night, that dress I wore, with nothing underneath ... you were okay with that?"

"Yeah, I thought you looked great," I answered, not understanding what she was getting at.

"Well, the waiter thought I looked great, too, as you yourself noted. You're okay with that? Because," she paused, "I kind of get off on dressing sexy. I did tell you I was messed up, right?"

"I'm fine with you dressing as provocatively as you feel comfortable," I answered. "Other guys wanting you doesn't bother me. It would be you wanting other guys that would be the problem."

"Great!" she answered happily. "As long as you're sure I won't be an embarrassment to you running around next to naked."

"Well I don't want to have to bail you out of jail," I cautioned, "but if you never wear underwear again I won't be the one complaining."

"Awesome," she said, obviously pleased.

"I have to admit it was pretty damned hot watching you eat Ashlynn out. Especially the part where she pissed down your throat."

"Right?" Sarah agreed. "That's why I get you, Bob. We have more in common than you would have guessed. I don't believe in chance, Bob. It was Fate that brought us together. You can roll the dice, but Fate always determines what numbers come up."

"Yeah?" I asked philosophically. "You don't think we're in control of our own destiny?"

"Well, we feel like we are, but we're really just doing what was thrown out there by Fate."

"And by Fate you mean God?"

"I suppose you could call it that. A higher power, anyhow. Someone with enough clout to make everything happen just the way it's supposed to."

"What about when things don't go the way they're supposed to?" I asked.

"Things always go the way they're supposed to. That's what I'm saying. Now we might not like the way they go—but it's not our call. Fate calls the shots and things always go just how they're supposed to go, whether we like it or not. Can't be helped."

"Where did you come up with this philosophy" I asked. "You're barely out of high school."

"I think deep thoughts, Bob. When other girls are wondering who they're going to the dance with, I'm pondering the mysteries of the universe."

"You are just full of surprises," I said as we pulled into a Quality Inn.

"Oh, you have no idea," she said dismissively. "How come we're stopping already? I thought you needed to go to Columbus."

"I do, but I'm in no hurry. We could make it tonight, but by the time we got there it would be late and there wouldn't be any time for us to enjoy one another. This way we can relax, have lots of sex, and, besides, I hate driving in the dark."

"Fine by me," she said. "I've got no place to be but with you."

I really liked the sound of that. I loved the sound of that. After all these years, I finally had someone who had no agenda other than just being with me.

We checked in and, having already eaten lunch on the road, we decided to check out the outdoor pool. My eyes almost popped out of my head when I saw what Sarah was wearing. Three triangles of sheer fabric covered the parts of her anatomy that the law required to be covered—there was nothing in the back at all except for the thin strap that disappeared between the cheeks of her ass. To her credit, she wore a coverup, but it was as sheer as the fabric in her suit, so pretty ineffective in terms of modesty.

"What?" she asked in response to the look on my face. "You said you were cool with me wearing slutty clothes."

"I also said I didn't want to have to bail you out of jail."

"I wore this all last summer and didn't have any problems."

"Let's hope they don't start today," I groaned.

It turned out to be rather interesting. I watched with amusement as people pretended not to stare. But they all did. I couldn't blame them. Sarah may not have been voluptuous, but she was well proportioned for her lithe form and the fact that it was all clearly visible made it impossible not to stare. She took off her wrap and laid it over a lounge chair and hopped in the pool. I just sat in the chair next to the one she had chosen. When she emerged from the pool, any pretense of wearing clothing had disappeared. She was as good as naked.

I watched as a tall blonde woman who had just come out to the pool with a man, whom I assumed to be her husband, went up to her and exchanged words. I couldn't hear what was said, but the facial expressions and body language indicated a favorable exchange. Then they all walked towards me. The woman was attractive, wearing a white one-piece that was both low-cut in the front, and high-cut on the sides, meaning that most of her shapely ass was visible and her breasts, too, shy of showing nipple. It wasn't as risqué as Sarah's, but still head-turning. The man with her was small framed but looked fit. He reminded me of Navy Seals I'd know when I was in the Navy. They didn't generally look like the sort of fellow who could kill you with their bare hands—even though they could.

"Bob," Sarah announced when they drew near. I stood, sensing an introduction was imminent. "This is Jennifer and Kyle Biggs," she said sweetly. "Jennifer said some very kind things to me regarding my swimwear," she explained. "I asked them to join us for a drink. You don't mind, do you, love?"

"No. Of course not," I answered. I wasn't lying, but probably would have if I did mind, since Sarah hadn't really given me a choice. I sensed she was in mistress mode again. "Why don't we move to that table over there," I said pointing to one nearby.

"Great!" Kyle said. "First round's on me. What's everybody having?" We all gave him our orders and he went off to the bar.

"Sarah mentioned you two were still getting to know one another," Jennifer said taking the seat next to me.

"It's been quite the experience so far," I said, grinning.

"She seem quite adventurous," Jennifer said, looking at Sarah but directing her comment to me.

"She did warn me," I answered.

"Kyle and I have been together about a year, now," she said. "We have an open relationship. It's been fun."

My face clouded over with confusion. An open relationship? What the hell was that? And why was she telling me this?

"Kyle and I have sex with other people sometimes. Often in group scenarios," Jennifer said as though she could read my mind.

Sarah smirked in the seat to my left. "Bob's not much of a player," she said. "Poker, that is. You can read his face like a book."

"I see," Jennifer said, knowingly. "This might be the perfect opportunity for you, Bob," Jennifer said. "Kyle and I are experienced in the lifestyle and know how to stay withing proscribed limits. And, since we're all traveling, you'll probably never see us again—should your experience not be to your liking."

"Wait," I interrupted. "What experience?" I felt like the kid in school who was the only one in class that didn't get the joke.

"Kyle and Jennifer will be joining us tonight," Sarah explained. "I've invited them to our room and we're going to play some games."

"Games?" I asked, starting to understand and being very afraid about what sort of games we might be playing.

"Bob," Sarah said surprisingly sternly, "I invited Kyle and Jennifer to join us. Jennifer and I want to enjoy each other's company. Kyle is going to enjoy you. And you are going to do this to please me. It's not optional."

"Yes, mistress," I said with only a little sarcasm. Too much might warrant punishment.

"I'm impressed, Sarah," Jennifer said. "How long have you known each other?"

"Since yesterday," Sarah said smiling broadly. "But Bob and I are a perfect fit. He even likes to drink pee like me."

Jennifer's eyes widened ever so slightly at that revelation.

"And, he's the best ass-eater on the planet," Sarah bragged.

"Well, now I want to try him out," Jennifer said.

"Of course," Sarah said, as though I had no say in the matter. "Bob's tongue is at your disposal."

"Hey everybody, I saw that the drinks were small, so I ordered two for everyone. Hope that's all right."

"You're a sweetheart, Kyle. Thank you," Jennifer said.

"Yes, thank you, Kyle," Sarah chimed in. I verbalized my thanks as well, not wanting to be the odd man out.

"Kyle, darling," Jennifer said, "Sarah is off limits as far as fucking is concerned, but you can bring the crop and put it to good use on her tits and pussy while she's eating mine."

"Great!" Kyle said as though he was genuinely happy with that arrangement.

"Kyle, Bob has never been with another man before," Sarah divulged. "He would never do this on his own. He is doing it because I want to watch him suck a cock and swallow cum. I want to watch you drill his asshole with your hard cock. Is that okay?" Sarah looked at him with an expression that said his answer had better be 'yes.'

"Oh, sure. Sound like a good time," Kyle said, again sounding weirdly pleased.

Me? I was wondering what the hell I had gotten myself into. There was no way Sarah could have known them from a previous time. And she didn't even know we were stopping until we got here. How was it that these people just invaded our lives this way? How had Sarah arranged it in a conversation lasting less than five minutes? And what was this nonsense about me sucking Kyle's cock? And having him fuck me in the ass? And I don't even get a say? Part of me was indignant.

Another part of me, a part that I normally kept very buried was secretly rejoicing. I would have to suck another man's cock in front of my girlfriend and another beautiful woman who was, essentially a stranger. I would get fucked in the ass while they both looked on! I would be used and humiliated! I felt a stirring in my loins. Jennifer noticed the movement as my cock swelled up beneath my swim trunks.

"Bob, lift up the leg of your swim trunks and show me your cock," Jennifer ordered.

I did as I was told. Discreetly, I pulled the leg of my trunks up until my hardening cock was exposed to fresh air. That made it harden all the more.

"May I?" Jennifer asked—Sarah, not me. Sarah nodded approval.

I felt Jennifer's hand on my penis. Right there at poolside. We were the only people out there at the moment, but anyone could walk by at any time. My cock swelled in response to her touch. My cock was too hard now to remain concealed. It stood proudly at attention.

"That's a damn nice cock, Bob," Jennifer remarked. "Look at this nice cock, Kyle. It's good, isn't it?" Kyle only nodded, seeming less pleased than he had been about other developments. "Would you mind letting me have him?" she asked Sarah, as though I were nothing but an animal.

"I wouldn't mind," Sarah said, "but I think that should be a reward he only gets if he does his other tasks well."

"Understood," Jennifer said. "Probably the same call I'd make with Kyle."

"Well, let's go upstairs. Shall we?" Sarah suggested. "You can just lead Bob up by the cock. Use your hand to conceal it."

"Sounds like fun," Jennifer said. She stood and gave a gentle tug on my cock, indicating I should do likewise.

I followed Jennifer, who followed Sarah back up to our room. I had no choice since she was leading me by the cock through the hotel. Fortunately, the route from the pool to our room didn't go through any populated areas, but only deserted hallways. Still, the fact that at any moment someone could come out and see me being led by the cock down the hallway was a bit unnerving, yet strangely stimulating. My cock was rock hard when we entered the room.

"Kyle's up first," Sarah instructed.

"We're just gonna let Bob's raging hard-on go to waste?" Jennifer asked.

"He's gonna have to earn cumming privileges," Sarah stated. "I'm pretty sure he really would like to fuck you, so it's good incentive for him to do a good job."

"Well, then, let's get this show on the road," Jennifer said. "Kyle, get undressed and stand out there on the patio."

Our room had a sliding glass door that led to a small concrete patio facing the parking lot. Being on the second floor, any activity on our patio would be clearly visible to passersby. No doubt this was figured into Jennifer's calculations. Kyle stood in the center of the patio and Sarah positioned me, naked, on my knees in front of him. Both girls pulled up patio chairs so that they could relax and watch.

"Start sucking, Bob," Sarah ordered. "Do it like you'd want it done to you. Make love to that fucking cock."

For the first time ever, I touched another man's dick. I felt it harden at my touch, though it was still pretty flaccid. I took the tip into my mouth and tasted a drop of pre-cum that leaked out. I thought it would disgust me, but instead it fed that part of me that thrived on humiliation. It was like a switch flipped on and suddenly I wanted nothing more than to suck Kyle's cock until it blasted cum down my throat.

Kyle had been down this road before, but he later said that breaking my cherry was quite a turn-on for him. That explained why his cock got so hard, so fast. It couldn't have been because I knew what I was doing.

I felt Kyle's cock harden and it spurred on my desire. I wrapped my lips around his shaft and sucked that cock for all I was worth. I ran my tongue over and around its tip in my mouth and even tried swallowing it, but my gag reflex got the better of me. Nonetheless, Kyle seemed to enjoy it.

I was prepared to suck it until Kyle climaxed, but Sarah stopped me. She explained that if Kyle came in my mouth now, he would be no use as far as assfucking me. And I needed to be assfucked, she said while applying a generous amount of butt butter to my asshole and worked, first one finger, then two, into my asshole.

"It's all yours, Kyle," Sarah said.

"Make me proud, Kyle," Jennifer chimed in.

I winced as Kyle pressed the head of his rigid cock into my asshole. Fortunately, Kyle was patient and gave me time to relax and accommodate this intrusion into my virgin ass. What began with discomfort soon gave way to pleasure as Kyle gently probed the depths of my ass with his cock. After a few minutes, Kyle was drilling my ass like a porn star, balls deep.

"Don't cum in his ass," Sarah cautioned. "Bob's going to take that cum in his mouth so we can see."

"Ass to mouth?" Kyle asked.

"Yessir," Sarah affirmed.

I processed this mentally, but by this time, my depravity had taken over and this new development only enhanced my humiliation, and therefore my excitement. Kyle pulled his cock out of my ass and moved around to my face

"Do it," Sarah ordered.

I opened my mouth to receive Kyle's cock in my mouth, fresh out of my ass. I took solace knowing that it was my own ass it came out of and not someone else's, but it was still disgusting. This only amplified the feelings of humiliation I had, kneeling in front of two attractive women while sucking a cock that had just come out of my ass. Leveraging those feelings, I sucked Kyle's cock voraciously.

After a few moments, Kyle pulled out and bade me open wide. Sarah and Jennifer looked on as he shot jets of sperm into my mouth. Sarah told me not to swallow until she gave permission. After she felt as though I'd had enough time to savor the taste of Kyle's sperm, she allowed me to swallow it.

"Clean that cock off until he pisses down your throat," Sarah ordered.

I complied as ordered. Piss drinking, by this time, was not a problem for me. I preferred it to come from the lips of a beautiful woman, but, in the throes of depravity as I was, this only heightened my arousal. By the time Kyle finished emptying his bladder down my throat, and all over my body for visual effect, I had a raging hard-on.

"I want that cock, Bob," Jennifer said, grabbing it and leading me inside.

Unceremoniously, Jennifer stretched out on the bed and offered herself to me, spreading her legs, and her labia, wide. I entered her easily and enjoyed fucking her, feeling the shame and humiliation I had experienced fall away like leaves from a tree in late autumn with every stroke. Jennifer was a beautiful woman, Kyle's woman, and I was fucking her. In some way, when I came inside of her, it seemed to undo the humiliation I suffered at Kyle's hands.

When I finished, I became aware of my surroundings. Sarah was sitting in a side chair masturbating and Kyle stood next to her, naked and flaccid, watching me fuck his woman.

"Sarah, darling, come suck Bob's cum out of my pussy," Jennifer ordered. "Kyle, go find a switch and show Bob what to do."

I followed Kyle and steered him to the belt in my pants hanging on a hook in the closet. It was about an inch wide, leather, and fairly flexible. He said it would be perfect. When we returned to the girls, Sarah was stretched out, spread eagle on the bed and Jennifer was perched atop her face. Sarah was flicking her tongue in and about Jennifer's vagina.

"Sarah has been quite the bitch today, hasn't she, Bob?" Kyle asked.

I saw where he was going with this. This was the part where Sarah got her payback, a payback not unwanted, nor unwarranted. I watched as Bob smacked Sarah's tits with the flat tongue of the belt. It made a satisfying thwacking sound punctuated by Sarah's whimper of pain. Kyle spanked each of her exposed titties while she sucked on Jennifer's cunt. After about a half-dozen swats, he moved down to her pussy. Sarah's legs were spread wide, leaving her pussy vulnerable and exposed. Kyle gingerly used the belt to swat her labia. Each swat left them a deeper shade of pink. Sarah did a remarkable job of remaining accessible and not giving in to the normal reflex to cover up and stop the pain.

"Take over, Bob," Kyle said handing me the belt. "You need to be the one doing this."

I grabbed the belt. I knew what to do with it. I just wasn't sure I could bring myself to actually do it. That hesitation only lasted a moment as I watched Sarah spread out on the bed. I gave her pussy three small whacks with the end of the belt, testing my aim, before bringing down a final blow with some force. That got Sarah's attention. Her legs shot up reflexively simultaneous with her cry of pain.