Chelsea's Trip Ch. 2

If you haven't read Chapter One of this story, refer there for background information.

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I left the limo driver sitting in his car, and quickly checked my baggage. I was anxious to get on the plane and relax. I was still dead tired from lack of sleep the night before.

I found my gate and sat there for a while, fighting drowsiness. After half an hour or so, they said my row could begin boarding, and I quickly made my way onto the plane. I had a middle seat, which I was not very happy about. I saw a kid about my age walking down the aisle, stop at my row, look at the number twice, then motioned to me that his seat was the window. I didn't feel like getting all the way up, so I let him squeeze by me. He was slightly pudgy, so he had a bit of difficulty wedging himself into his seat. He also shoved his rather large ass into my face as he went by. I was slightly annoyed by his unorthodox movements, but didn't say anything besides "Hello" to him.

The next person to sit down was a man about fifty, and had the aisle seat to my right. He was a fairly normal looking, business traveler, a suit and tie on. His hair was a fading gray, his skin just beginning to hang off his face. He looked awfully tired, but noticed me and nodded hello.

The plane departed, they served us some shit for food that I immediately threw out, and then I went to sleep. I slept for about a half an hour, and then I needed to go to the bathroom.

I woke to the sound of the man next to me snoring, and I did my best to get by him without disturbing him. But I was unsuccessful, and he woke up to the site of my ass in his face.

"Oh! Jeez, you startled me." He said to me.

"I'm sorry sir, I didn't mean to."

"It's quite alright." And I continued on to the bathroom.

When I returned, he smiled at me, and I decided to give myself a challenge. If I could make that limo driver cream all over the front seat of his car, maybe I could make this guy cum in an airplane full of people. So, in order to tease him, I'd have to give him a little more skin. I had been wearing a baggy sweater the whole time, because I had on my super-tight shirt on under it, the one I had put on in the car. That was the perfect garment to tease him in, so I whipped off my sweater, and his jaw dropped. I could tell he was attracted to me from the beginning, but now he was in a trance. My nipples were quite visible, standing in the center of my perfectly round, youthful tits. I opened the overhead bin that was directly above him, and leaned toward it to put my sweater away. I exaggerated my leaning, because I wanted to but my breasts as close to his face as possible. I would guess they were less than a foot from him, and he was making no effort to move back away. I struggled with my sweater for a few moments, and then successfully got it into the compartment. He started to get up to let me back to my seat, but I wanted him to stay where he was.

"Oh, no, don't bother getting up, I can climb over you." I said, as I put one leg over his, facing him. I paused, grinning slyly as I watched him looking at me. In the moment I was standing there, directly in front of him, a jolt of turbulence hit our plane, sending me onto his lap. I didn't purposely do this, but my boobs went right into his face, his nose going between them. My hands, trying to support my body, instinctively went to his thighs.

"Oh! I'm so sorry! I—" I stammered to him when I realized where my hands were. Seemingly innocent, I moved my right hand onto his crotch in an effort to push myself up. When I put my hand there, I felt a rock hard cock, pushing back up in his pants. I used my other hand to pick myself up, but squeezed his cock a few times before I got up. I all happened very quickly, and he couldn't assume I meant to put my hand there.

"I'm alright, I'm alright, are you ok?" he said to me.

"Yes, I'm fine, you broke my fall. Thank you for catching me." Even though he didn't.

All the commotion in the seat next to him woke up the teenager sitting in the window seat on the other side of me. He saw me without my sweater on, and his pudgy face was locked on me. I sat down in my seat, and reached up and turned on the air vent above me. The cold air felt good, and I pointed it right for my chest.

"Phew, rough flight eh?" I said to the window seat kid, turning towards him.

"Uugh, yeah. It is." Even though it hadn't been until that moment. I knew my nipples had already reacted to the cold air, and they were practically popping out of my shirt. I looked down, and my areola were visible as well, encircling my nipples. After a few more minutes, the flight attendants came around with drinks, and I ordered only water.

"Miss, would you like a blanket? You look cold." The attendant asked.

"No thank you." I didn't want to cover up just yet.

After she left, I asked the two guys: "I wonder why she thought I was cold? That's interesting."

They both said simultaneously "I dunno, you don't look cold to me." And looked at my chest. We all got our drinks, and the aisle guy fell asleep immediately after drinking his cocktail. I elbowed him a few times and found he was a sound sleeper. The window kid was listening to music, and not paying any attention to us, so I decided to do a little more than bump the old guy.

I slid my hand under his food tray that his drink was on, and traced the outline of his cock. I found he was fairly well hung, about seven inches and good width, and rubbed and squeezed him a few times.

The flight attendant was walking down the aisle, so I stopped molesting this guy and asked her for the blanket she had offered earlier. She quickly returned with it, and I spread it over my lap and legs. I wanted to keep my breasts visible.

I saw the kid to my left looking out of the corner of his eye at me, so I leaned over toward him, pretending to be looking for a magazine in the seat pocket in front of him. My left boob was pressed against the back of his hand, which he kept on his armrest. I leaned farther over, pinning his hand under my tit. To my surprise, he pulled his hand away. I thought he would never have washed that hand again, but apparently I didn't have the effect on him that I predicted.

After a second, he slid his hand back under me, this time palm up. He just wanted to feel my round breasts in his hand. He squeezed me a few times, and then I sat back up, not acknowledging he had blatantly squeezed my tit. He was perplexed. I turned my attention to the sleeping man next to me.

He was still out like a light, so I figured I could mess with him a little more. I very, very gently picked up one of his hands that was sitting on his lap, and moved it over to my lap. I waited a few seconds, then when I thought he was used to having his hand there, I gently moved it onto my tanned thigh. Again, I waited a second, then extended one of his fingers, and moved it under the hem of my short khaki shorts. Then I slowly pushed his finger closer to my nearly hairless pussy; until I felt his finger tip slightly enter me. I put the blanket over me and waited a few minutes, acting like I was asleep. Then I nonchalantly elbowed him just hard enough to startle him awake, and continued to act like I had been sleeping the whole time. I heard him awaken, then realize where his hand was, and pull it back quickly. I thought about awakening then, and asking him why his hand was in my pants, but I was more interested in what he would do if I didn't know.

He was obviously baffled as to how his hand got there, but he liked the fact that it was there. He thought for a few minutes, and then I felt his hand back under the blanket, working its way into my shorts. His large fingers awkwardly got to my crotch, and he pushed one of them deep inside my tight slit. I had never been very fond of being fingered, and he wasn't great at it either, so I "woke up" while he was still there and pulled his finger out. He thought I meant I didn't approve of him being there, so he started to remove his hand. I had other plans for him.

I unbuttoned my shorts, and slid them down slightly. He put his hand inside them and played with my clit a little, then I moved his hand underneath me, to my tiny little asshole. He was pleasantly surprised, and I lifted myself up with my arms, and he positioned his middle finger pointing straight at my brown hole. I dropped down, impaling myself on his finger.

"Mmmmm, that feels gooood." I leaned over and whispered in his ear.

"I bet it does." He started to pump his finger up and down, without making it noticeable to everyone else on the plane.

"You know, I've never had a cock in my ass before." I said to him quietly, with a sly grin on my face.

"Well, I've had my cock in plenty of asses. Yours is far better than any of theirs though."

I sat in pleasure, with his finger pistoning up and down in my butt hole for a few minutes, and then decided to bring the kid to my left into the fray. I picked up the blanket that was on my lap, and put it over my body the rest of the way. Only my head was visible. I lifted my shirt until my breasts were exposed, and held it up with my right hand. Then I reached over with my left hand and grabbed his right. He looked at me, puzzled, but when I brought it under my blanket and placed it on the hot flesh of my round tit, he knew what to do. He squeezed and kneaded my big tit while the guy on the other side of me pumped his finger in and out of my ass. Neither of them knew what the other was doing, but both were ecstatic.

Now I let them both go to town, and I brought my hands down and rested them on my lap for a few minutes. I lolled my head back while these two lucky bastards molested me. Soon the man to my right was so horny that he violently pulled his finger from my asshole and headed straight for the bathroom, I assume to jack his cock. I saw him licking and sucking the dirty finger that he just took out of my forbidden hole as he almost ran to the bathroom. My buddy to the left was still in heaven, playing with my titties. He didn't notice the abrupt exit of the other man. I figured I could help him relieve himself, so I put another blanket over him, brought my hand down to his pants, slowly unzipping his fly, slowly pulling his cock out of his white underwear. He was not well hung at all, a mere five inches long and three-quarters of an inch in diameter. But he was still young; maybe he would grow to have a big cock when he was older. Anyway, his mini-cock was hard as a rock, and I squeezed it to his delight. I had jacked a few guys off in the past, and I knew my way around a dick. I brought my hand up to my mouth, sucking on each finger slowly, and spitting a big wad of saliva onto my palm. Then I brought my hand back down and rubbed the gooey slime all over his cock and his sparsely haired balls. I wrapped my little hand around his little shaft and pumped him a few times, then grabbed his balls and squeezed them. At first apparently he liked having his grape-sized balls pressured by my hand, so I continued squeezing harder and harder.

"Ow, Ow, what the hell?" He said quietly as my hand clamped around his nuts. I liked the power I had over him, and wanted to see how far he would let me go if I gave him some encouragement. I let up a little, so he wouldn't yell, and then made my proposition to him.

"Okay, you think I'm a pretty hot girl right?" I still had his balls in my hand; I was rolling them around in my fingers.

"Of course I do, I don't know what that just was a second ago though."

"Don't worry about that, I've got a game to play. To you want to play along?" I whispered to him in a soft, sexy voice.

"Yeah, sure." He said eagerly.

"Ok, if you win the game I will do anything you want for you. I mean ANYTHING, I will be your slave for ten minutes in that little airplane bathroom up there." I pointed to the front of the plane, where the other man was right now.

"What's the game?"

"Its very simple, I have to be convinced that you want me enough, you have to prove that you would do nearly anything to have me."

"I don't think that will be a problem."

"Ok, just concentrate on the goal." With that I grabbed his balls in my hand and squeezed them harder than I had before, he nearly jumped off his seat.

"OW!" He yelped.

"Shh, I forgot part of the game, you have to be quiet too."

"Hhh, okay."

I took his balls in one hand and his cock in the other, and pulled, hard.

A look of terror came across his face, but he didn't say a word and settled down after I let go.

"Good job stud. Did I ever tell you how small your cock is? It's really quite pathetic. Anyway, I've got a challenge for you now." I took a brush out of my carry-on bag at my feet and showed it too him.

"You must jam the handle of this brush into your asshole until it can go no further." His jaw dropped. The handle was not huge, but pretty big to go into a virgin hole. I correctly assumed he had never taken anything up the ass. The handle was about 1.5 inches in diameter, and there was about 4 or five inches of it. There were little tiny knobs that would stimulate his hole, but also make it more difficult to insert. Before handing it to him, I slid it in and out of my little pussy a few times, lubricating it with a think coat of goo.

He took it from me, looked at it for a while, and then looked back at me.

"I dunno…this is really gross."

"You don't have to, just remember what you are missing." With that I lifted his hand up and placed it on my soft tit.

"Ok, ok, I'll do it." He arranged the blanket so it covered all of his lower body, and then slid his pants down to his ankles. He spread his knees apart, and brought the brush down to his crotch. It took him a while to find his hole, and he started to put pressure on the object entering him. He wasn't making any progress, so I suggested he try to push it in with one hard shove. He grimaced, and then went back to work. I looked around, saw all the people around us were sleeping, and then ducked under his blanket. I wanted to see this little asshole take that big handle. He breathed in deeply a few times, then jammed the brush toward his rectum. No luck, he didn't have it right in the center, so it wouldn't go in. He tried again, and this time I guided it directly in. He stopped halfway, took a breath, and then continued until the little burrs that usually combed my hair were touching his balls. His hole was stretched way out, and looking at his face he was in obvious pain. I have never taken anything bigger than two fingers up my ass, and this wasn't the best encouragement to try anything more.

"Ok, ow, can I take this out now?" He said as I sat back up.

"Just give it a few seconds, maybe you'll grow to like it. Try rotating it so the little nubs massage your prostate." He didn't seem too interested, but did as I said anyway. At first he started very slowly, then began to speed up. After about 30 seconds, he seemed to be starting to enjoy it.

"You like that? I bet you've always dreamed about some big manly guy filling up your butt with his big cock. Haven't you?" I teased him as I sunk back down under his blanket. After a little while of watching him pleasure his asshole, I said, "I think its time for a little reward don't you? You aren't there yet, but you are getting close." He nodded furiously. I didn't want to make him cum, so I only licked his cockhead a few times with my little tongue, then sucked his balls for a few seconds.

After a few minutes, I said he could take out the brush, and he gingerly handed it to me.

"There is only one more thing for you to do. My brush has your shit smell all over it. Clean it off."

"I can't believe this." He said in disgust. He started wiping off the brush with a Kleenex he had, but I quickly corrected him.

"Uh, uh uuuhh, you can't clean it like that. No hands."

"What?"

"You heard me, suck that shit off."

"Goddammit. This has crossed the line."

"You don't have to, but don't you want this?" I slipped my shorts down and pointed to my sparsely-haired cunt lips. "And you have to clean it while it is..right..here." I put it in between my legs, next to my pussy. "It'll be almost like you're giving me a blowjob, except the brush is my cock."

"Alright well let's get it over with." He leaned down and brought his head under the blanket. I saw him go down slowly, I assume on the brush handle, then come up quickly and gagged for a second.

"Come on you can do it." He went back down, then quickly bobbed up and down about five or ten times, then popped out and coughed a few times.

"That's good enough." I said to him. "Good job. I bet you give good head." I laughed.

"Shut up."

"Ok, I'm yours, do with me what you will." I said to him.

"Hmmm, first I have something in mind for you." He paused, the reached over to me and folded my shirt up so it exposed my stomach. He brought it so high up one could just barely see the bottom of my tits.

"What are you doing?" I said, perplexed.

"Just giving you a taste of your own medicine." He pinched my nipples so they got hard as rocks. "You've got to get up out of this seat dressed like this, and walk back and forth in the aisle of this plane."

"Oh god."

"You aren't ashamed are you? You don't seem like you are."

"No I'm not ashamed. I never said I wouldn't do it." So I did, I got up and walked around with my tits almost hanging out of my shirt, my stomach exposed. I got quite a few looks on my way down the aisle, and started to enjoy it. On the way back I felt like showing a little more, so I stopped next to a man who had been staring particularly hard, and bent down at the waist, nearly touching his arm, which lay on his armrest, with my ass. The shorts I had on were tight, and my bending down showed this guy my ass quite well. Then I felt a poke in my shoulder, and looked up to see one of the flight attendants, with a slight grin on her face.

"The captain would like to talk to you, miss."

"Sure, I would love to speak to the captain." I said.

I sauntered up to the front of the plane, and the flight attendant let me into the cabin. The pilot and co-pilot were sitting in their chairs, and turned to look at me as I walked in.

"I understand you are causing quite a commotion back there with your choice of clothing. I can see why." The pilot said. He was a man about thirty, short blond hair and fairly well built. The co-pilot was black, 6'4" or so, and more attractive than the pilot. I walked in between them and leaned against a panel with a bunch of dials, my back to the front window, facing them.

"I apologize sir, I was just holding up my end of a bet." I looked at the pilot with my best set of puppy dog eyes; he began to smile. He was glancing every few moments at the bottom of my tits that were exposed to the air, and I saw a tent growing in his pants. I quickly looked over at the co-pilot, who was looking me up and down, from my tan legs to my luscious tits. I did a double take when I saw his reaction to my body. There was no tent in his crotch area, but when I looked at his left thigh, I saw a massive bulge that went at least halfway down his long thigh. It was enormous.

"I don't know what we are gonna do with you, you can't go back out there dressed like that." The captain said.

"Oh, I'm sure you'll figure something out, I'll just stay here for a few minutes." I sat down on the pilot's right armrest, facing the co-pilot, then leaned back, putting my arm around his neck. My right breast was pressed against his chest and his eyes lowered to my tits. "Oh, I am sooo tired!" I exclaimed as I lifted my arms over my head and yawned, my shirt lifting, exposing my boobs entirely. "OH! I'm so sorry, I bet you could just see my…my…" and I trailed off, smiling at the pilot.

"I forgive you young lady, but you should really be more careful."