Ann: A Love Story Ch. 22

But here it was Friday...and as usual, I was getting nervous. It wasn't the sex with Tina itself. It was all the sneaking around in a small town, while being engaged to a woman I was falling more in love with every single minute. I didn't need anyone finding out. And while I felt Tina and I had been relatively discreet, with the exception of our fucking in front of the window in her darkened shop late one night, I generally got butterflies on Friday just thinking about what might happen.

Certainly part of it was the act itself, but a bigger part was the anticipation of what Ann had in mind. Tina was right. Ann did seem to have a little bit of a kinky side to her, but it wasn't overt. It was more like she wanted to keep me on edge and wondering. It was almost like an adventure.

Yet the nervousness I was feeling at that moment was something totally different altogether. I wasn't going to be hooking up with Tina at her shop that weekend. I was heading out of town.

Standing in an Airport in Fort Wayne, I waited to board a plane for Washington DC, with a layover in Cleveland. I was flying to Dulles Airport, since it was the closest airport to the destination I was heading. I had a series of extensive job interviews scheduled for most of the day Saturday. I had reservations to stay in the DC area in Virginia, and I'd be driving the hour or so the next morning to the site of the new manufacturing facility being built. I'd fly home Sunday morning, arriving late that evening. It was going to be a long weekend.

~*~*~*~*~*~

The phone interview Wednesday night with the Manager, Jeff, went very well. Well enough that a whirlwind of activity took place almost instantly to set me up for the interviews that very weekend. They offered to fly out my fiancée and me for the weekend, so that I could be interviewed, and she could tour the area. I never told them about Ann living in California. I only told them I was engaged. And at the time, I told them I would have to check to find out if she could make it.

Ann had called me an hour or so after I'd finished the phone interview, and when I told her about that part, she said. "So, you want me to fly out to Indiana and then fly out with you, all in a day?"

"Well, now that you say it out loud, it does seem a little unrealistic, doesn't it. But I thought before I turned down the extra ticket, I'd at least ask you."

"Well, I can't make it, honey. If I took time off work just to fly out for a potential job, then all I would be doing is delaying when I get to move to Indiana. They'll already want me to work longer before I quit. They ask me every week to delay my end date, and I'm not going to do that."

"All right, when Jeff calls tomorrow, I'll tell him it will just be me."

"And my SISTER!" Ann said, as if inspired by a stroke of genius.

"What are you talking about?"

"No wait! Make it my STEP sister...Tina!"

"Ann, that's nuts. I can't take Tina. They may think she's you. What if they want to meet her?"

"That's why you tell them up front. Tell them I can't go, but I want her to go so she can look around. You know, so I'll know if the place is somewhere we want to live."

"But that's lying."

"Only about her really being my stepsister...but she could be. I've told you she's like my long lost sister...why not a stepsister instead?"

"Oh, and you'd let your stepsister fuck me?"

"Apparently I already am," she giggled.

"Ann..."

"Neil, seriously...take her. I'll call her and ask if she can go. She really can look around for me. And I think that's something we should take advantage of. If you're interviewing all day, she can look around and let us know what's there, and if we'll like living there."

~*~*~*~*~*~

I was never a graceful flyer. I didn't hate it, but I didn't really like it either. By the look on Tina's face, it didn't appear it was her favorite way to travel either. Of course, it didn't help that two days earlier there had been a plane crash in Iowa, where a jet had hydraulic issues. It took a miracle and an extra pilot on the plane to even get to the airport, and another miracle that a lot of the passengers lived through it. But there were a lot of deaths as well, and that was the part that weighed on both of our minds.

As we stood there, waiting to board a smaller puddle jumper prop plane to take us to Cleveland, there was a television camera, with a reporter. He was on the tarmac, interviewing a couple that got off the plane we were about to board.

Tina leaned over to a woman that worked for the airlines and said, "What's that all about?"

"They were on that flight 232 that crashed in Sioux City a couple of days ago. They live near here, and the news crew knew they were coming in this afternoon."

I don't know which would have been harder, having to relive the event for the news crew, or flying again just a couple of days after the crash they survived. I did find it interesting that we heard the woman say, "Why would God let us live through the first crash, just to take us in another one? It seemed safer to fly afterwards than it did before."

With that kind of logic and bravery on display before us, it seemed silly to be nervous anymore about flying...and I actually turned a corner when it came to boarding planes. It didn't seem like that big of a deal. Tina didn't share my sentiment, but she took my hand as we boarded and took our seats.

The flight to Cleveland was short and uneventful. I was grateful, since Tina had been digging her nails into my arm since we taxied onto the runway before takeoff. I could only imagine how painful it might have been had we encountered some turbulence. We had a two-hour layover to switch planes, and Tina begged me to take her to a bar so she could get a drink and relax. As we sat down in the darkened pub, Tina gulped down the first swig of her beer and took a deep breath, sighing as she tried to calm herself down.

"I don't know why I ever agreed to do this," Tina said as she looked at me.

"Why did you?" I asked, wondering myself.

"I don't know. I've never really been anywhere before, and Ann made it sound so exciting."

"How many times have you flown before?"

"Counting that last flight...once."

I shook my head in disbelief and sipped my own beer. Ann certainly had a way of getting people to do things outside of their comfort zone. But getting Tina to pretend to be her stepsister just so she could tag along with me on my interview seemed like a pretty big stretch, even for her.

"So, why did you come...really?"

"Ann asked me to. She just has this way of getting under my skin."

"You say that like it's a bad thing...why would you do this if you really didn't want to?"

"I never said I didn't want to. And it's not a bad thing. Not at all."

"So what are you saying?" I asked.

"Well, Ann really does want me to check out the area to see if it's somewhere she might like to live. And, she wanted me to keep you company."

"She doesn't think I can make it out there without help?" I asked, not really believing that, but wanting to draw out some of what Ann had planned with Tina.

"No. She just doesn't think you should go a week without sex, and she didn't want you to have to look for some strange pussy. She wanted you to have your mind clear for the interview."

"Somehow, I doubt she put it like that. And I've gone longer than a week without sex before."

"True, but that was before you met her. She must think those days are over. At least according to Ann...I'm just the mouthpiece here, so to speak."

"So, you're supposed to use your mouth on me, eh?"

Tina blushed a little and said, "If you want. I'm supposed to do you on the plane. She said something about the two of us joining the mile high club."

"I'm not sure that's a good idea. I don't need to get kicked off the plane and miss the interview."

"Well, we have to fly back too. And besides, I just have to get you to cum. There are a lot of ways to do that."

"What about you?" I asked, half kidding.

Tina turned sideways on her barstool and spread her knees a little. She was wearing a white pleated miniskirt, and it rode up her thighs, offering me a quick, brief glimpse of her wet, pink slit.

"No panties?" I said softly as I stated the obvious.

"By the order of Ann, our travel agent. Her itinerary was pretty specific, including no underwear allowed."

"I'm wearing underwear," I said in mock defiance.

"You're allowed. I'm not. But feel free to join me if you like," Tina said with a laugh.

We finished our beer over some high octane flirting, and made our way to our gate to wait to board the next flight. As we sat there, I thought of the oddity that I was experiencing. Sitting in an airport in another state with my hairdresser, who was my former fuck buddy, but now was a sexual stand in for my fiancée until we could be together again. None of it made any sense. The least of which being Ann, the orchestrator. But the more things became absurd, the less I cared and the more I let go. Ann wanted our lives to be a wild ride; I was more than willing to take a window seat.

And that was exactly what I did on the plane. Tina wasn't thrilled about sitting next to the window, so I took that seat and she sat next to me. We left the arm rest up between us, and Tina leaned into me to cuddle as we sat at the terminal. It was a pretty empty flight for a weekend going to DC. No one sat in the seat next to Tina, or across the aisle as we pulled away from the gate and headed to the runway.

Once we were in the air and the seatbelt sign went off, I told Tina I had to go to the bathroom, and I got up and walked down that aisle to the back of the plane. I didn't really need to go, but I wanted to up the sexual ante a little and see where it would lead. If Ann wanted us to join the mile high club, which I seriously doubted we'd do, I was at least going to let Tina know I was game. I took off my boxers and put my loose khakis back on. Neatly rolling up the underwear into a tight little package, I put it in my pocket and walked back to my seat.

By that point, I was semi hard just from the excitement of what I had done, and my cock was certainly more noticeable to anyone that cared to look. But I doubted anyone really cared. As I walked back down to our row in the middle of the fuselage, I was looking at the other passengers, all of which were busy with things to keep them occupied. Many of them had to have the plane crash on their minds, just like it had been on mine. That kind of event lingers for a while. It's human nature.

Tina seemed uneasy as I approached our row. Being left alone must have put her on edge again, and not in a good way. She needed to get her mind off the flight. As I got to the seat, I turned my body so that she'd be eye level with my crotch. The state of my cock, now getting harder by the second, caught Tina's attention. Flexing my groin to make it flinch didn't hurt the appearance. I reached into my pocket and pulled out my boxers, handing them to her.

"Now were even," I said with a smile.

"You're being a naughty boy."

"That's because you're always a naughty girl. I'm just trying to keep up with you."

Tina spread her legs to let me pass, showing me her wonderful slit, shimmering from the dim cabin lights. I smiled at her sudden brazenness, but I shouldn't have been surprised. I had fucked her in the front of her store, so it wasn't like she wasn't capable of a little flashing in public. But she also knew enough to be careful. We didn't want to cause a scene or get caught doing something inappropriate. Tina quickly stuffed my boxers into her carryon bag under the seat in front of us, and then sat back.

I sat back down in my window seat, and Tina snuggled up against me again, turning her body towards me. She quickly unbuttoned the top two buttons on her tight black blouse with her right hand, while her left hand found my lap. I couldn't help but wonder how much practice she'd needed to become so proficient in undressing one handed. A skill like that tells a lot about a woman. I knew most of the story behind Tina. But that didn't mean my natural male curiosity didn't want to delve deeper inside to find out more.

Exposing the insides of her big tits to my personal view, Tina giggled as she saw my eyes dip towards it. "You men are all alike. Show a little cleavage and you can't help but stare."

"I like to think of it as an invitation. It would be impolite not to RSVP."

"I suppose my spreading my thighs was another invite then?"

"I looked, didn't I?"

We were about to launch into some more heavy flirting, dancing around the subject of sex and whether either one of us had the guts to actually try anything there on the plane. I pictured a never ending game of teasing each other to pass the time, but Tina, emboldened by the charge that Ann had given her, wasn't about to just tease.

She turned and lifted her hand off my lap just as a stewardess stopped by to ask if we needed anything to drink. Tina asked for water with crushed ice, and asked if she could also have a blanket. I took a ginger ale, but having always been a cruncher, I requested cubes instead. In a couple of minutes, the stewardess was farther down the aisle serving other passengers. Tina quickly put the blanket over the two of us, and then lowered the trays to put our drinks on. With her right hand, she gulped down all of the water and set the plastic cup of ice back onto the little tray. I was so busy watching her I didn't notice her moving her left hand to my zipper. Before I could say anything, my cock was out of pants and firmly in her hand.

"That's better," Tina said as she slowly started stroking me.

"It is? Are you sure about this?" I said, suddenly having a case of the jitters.

"No. But Ann is. And I've yet to be disappointed when I follow her lead."

"So what is she, some kind of Svengali?

"Only if you think this is evil. I prefer to think of her as my sexual mentor."

"I knew you before Ann, Tina, and I'm not really sure you need one."

"Sure I do. I wouldn't be doing this if it wasn't for Ann," Tina said as she worked intently on the head of my cock.

I sighed and said, "Okay...I was wrong. You do need a mentor!"

Tina leaned over and kissed my cheek as she continued to stroke me. Under normal circumstances, I last quite a while. But this was anything but normal. I was worked up more than usual, and Tina had a knack for finding just the right pressure and rhythm to make me squirm. The pre-cum was oozing from my tiny hole. She would grip and squeeze my cock, forcing more out so she could use it to lube the head.

Using her palm, Tina rubbed the very tip as she reached down with her other hand and pulled my balls out of my pants as well.

"Fuck! I love how big this thing gets when it's really excited," Tina whispered into my ear, licking at my lobe. It had an electric effect on me, as I bucked my hips. Grabbing my balls, Tina forced me back in my seat. "I wanted to get a rise out of you, stud. Not have you go into orbit up here. Do I need to make you put on your seatbelt?"

"No. I'll be okay. You can stop crushing my nuts now."

"Sorry. It's a reflex. Now sit back and relax. I don't want to torment you. I want you to remember this fondly."

"I'm pretty sure I will, Tina."

Tina picked up the pace a little. Not enough so that we'd be noticed, but enough that I could feel my load start stirring in my balls. Tina knew that too, since she was playing with them as they started to tighten.

Purring into my ear, Tina asked me if I was getting close. All I could do was nod and try not to scream out. She let out a little giggle and took her hand off my balls to grab the glass of ice and bring it under the blanket. Tina was holding the cup so close I could feel the coolness of the ice against the very tip of my cock. She was working on the shaft, leaving the tip alone. That slowed the accent towards my orgasm just a little, but I was in no position to complain.

"Cum for me, stud!" Tina pleaded as she bit playfully at my earlobe. That little bit of encouragement was all I needed. Well, that and the fact that she shocked me into my orgasm by slipping the cup forward, making the very tip of the head of my cock touch the ice. My mouth flew open, and I was about to scream out. I grabbed my cup of ginger ale and took a big gulp, moaning in my throat as I started shooting. After swallowing my scream, my eyes bugging out from the intense combination of cold and pleasure, Tina licked at my ear.

"That's it...cum for me baby," Tina pleaded again as she hissed her hot breath into my eardrum.

My cock answered for me, spurting shot after hot shot of molten sperm. Just as I started to cum, Tina moved the cup, burying the entire head of my cock into the crushed ice. The sensation was electric. It hurt, and felt incredible at that same time. I felt a shiver run into my balls and through my body up my spine. It was the groin equivalent of a brain freeze, but it was so much better.

Tina let out an evil little laugh as she continued to pump my shaft, milking every drop she could. When the spasms in my cock started to subside, she gently gripped my balls, forcing a little more spunk to rise and spurt out. Finally, she gripped the base of my shaft and slowly pulled forward like she was working a near empty toothpaste tube, squeezing out every last drop.

Patting my cock, Tina took the cup from under the blanket and looked at it. "You never disappoint in how much you can cum, stud. You amaze me," she said as set it on the table in front of her. She continued to play with my dick, which was back to half hard. "So, how was that?" Tina asked as she winked at me and settled back into her seat. She seemed much more relaxed than when we started the flight, and certainly she was better than the first flight. Having something to occupy her must have taken her mind off where we were.

"More than I expected. The ice thing was a first."

"As if getting jacked off at 30,000 feet wasn't. Did you like it?"

"Yeah. I wouldn't want it every time, but it felt amazing."

"Good...then it was worth the risk."

"Your turn!" I said as I reached over with my right hand and slid my fingers up her thigh.

"No, please," Tina said, trying to talk me out of providing her some of the same pleasure she'd just given me. But her body language told a different story. No girl I'd ever met meant 'no' when they spread their legs as wide as they could to give you better access. But Tina continued her protest right up to the point where I slide my middle finger gently through the folds of her pussy, running it from near her cute little asshole up to her already throbbing clit. I barely touched it, and yet I swear sparks flew from Tina's eyes as her back arched.

I spent the next half-hour teasing Tina, bringing her close to orgasm and then stopping or moving so that she didn't quite explode. It was something I'd done to her a couple of times in the months we'd been fucking each other, and it never failed to drive her wild with lust. Tina always insisted that she hated being teased, saying she always wanted her sex hard and fast. But on the occasions where I'd had the chance, she really got off on having the build up to an orgasm dragged out as slow and agonizing as possible.

Over time I had learned that if I could keep her from having her first orgasm for over twenty minutes, not only would that first one be that much more intense, but every one after would be even more so, increasing in force. The way Tina was trembling, I knew we were in for one so big that might make the rest of the passengers on the plane think we hit turbulence.

I became a little concerned at that point, since Tina had always been extremely vocal when we had sex. But she was doing a remarkable job of bottling all of that in. She moaned quietly, but she never said a word after those initial attempts to 'stop' me. Every time she felt the urge to scream out, she would grab the cup in front of her, and let some cum covered ice slip past her lips. Chewing on it to appease her, and she was able to control her emotions. Try as I might, there always reached a point of no return with Tina. She wasn't one of those girls whom you could tease and play with and never allow them to cum. There was always a boiling point where, once you reached it, steam was going to have to release somewhere. Tina was there, right in that magical sweet spot.