A Learning Experience Ch. 02

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Flying high before the storm - Jack & friends join the Mile.
6k words
4.55
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Part 2 of the 10 part series

Updated 06/07/2023
Created 06/14/2013
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Joscelyn2tg
Joscelyn2tg
225 Followers

This is chapter 2, Kinda short and sweet, we have a couple more things about our characters to learn, have a nice flight... and don't worry, chapter 3's coming right behind this and its where an awful lot starts happening to Jack... Cheers! -- Joscelyn

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I had absolutely sworn to myself that I would never reveal that I had the feeling I should have been born a female for as long as I could remember and that even if subjected to torture, I would never tell this secret to a living soul. Well, as it turned out, one small bong of marijuana was all that was needed for me to blab my secret to three of my college friends, including what was now probably my ex-girlfriend. Mel (or Melissa) had continued to be just as close as always, but I knew it would only be a matter of time. I mean, what girl would want to be involved with a cross-dressing guy that just admitted he'd really rather be a woman?

And so it was with extreme anxiety that a few days later on a rainy Friday, just before noon, I walked into the Music Club's offices. I was really hoping to find Mel, but it turned out that she wasn't there, so I then went looking for Andy in his office. I knew that's probably where he'd be, in fact, he rarely went to classes, but somehow he never seemed to get in any trouble for it. Usually he was hanging out in his office, either talking to new groupies (club members) or getting stoned, or else having sex. More often than not it was all of the above. I had spent a long morning going through contract negotiations to finish up all the details in getting David Bowie to perform at our college for the first time.

"Hey Bro!" I said as I poked my head around the open doorway of Andy's office.

"Jack! There he is, the man of the hour!" Andy yelled loud enough to be heard all over the building. He was sitting at his desk and had been reading something.

"Umm, were you able to talk with your dad, and set things up for me?" I asked quietly, so he might lower his voice a little.

"Ok, you heard him... pay up!" he said to someone I didn't see, so I went ahead and walked into the office, and saw his girlfriend Cindy sitting over on the couch.

"Shit! That's incredible, if I hadn't been here and heard her say it, I wouldn't believe it!" Cindy cried out, then reached down for her purse.

"Oh... Hey there Cindy, sorry, didn't see you. Umm... what are you guys talking about?" I tried to ask, even though I knew that whatever it was would probably just embarrass me for their amusement. Especially seeing the huge grin on Andy's face!

"Well Jack, we had a little bet, I bet Cindy that even after your whole morning of contract negotiation, with one of the country's top concert promoters," Andy began, "and then finding a problem with his contract that made him shave 25 grand off of it for you, that the first words out of your mouth to me, would be about seeing my dad!"

"Oh yeah, well we did get Bowie for the cheapest he's played anywhere on the east coast," I stated matter-of-factly, then added, "That should certainly please our advisor." It was just then that it hit me, Cindy had referred to me as 'her'! But I was tired, and I wasn't sure if perhaps I had just imagined it, and decided to let it drop.

"I would hope so!" Cindy exclaimed, as she finished writing something on a slip of paper she had gotten from her purse. She then folded the paper up and threw it over to Andy at his desk.

After unfolding and reading the note, he said, "Yee-ow, thanks baby, I'll look forward to that!" I was going to ask Andy what it was, but decided better of it.

"So... what about your dad?" I tried asking again.

"No problemo, dude!" Andy replied in his usual glib response, "Its all set up, you'll be hangin' with us for the weekend, we'll play a few arcade games, watch some TV and listen to some tunes. Then, in the afternoons, my dad will want you to stop by his office and he'll have you take a few tests, talk with you for a while, and give you some things to read for later. Then you can go home Sunday night and he'll call you later on in the week with the results and his recommendations... Sound good?"

I gulped at the sound of 'tests', and almost squeaked saying, "T-This weekend?"

"Sure, that's what we talked about, wasn't it?" he asked rather puzzled.

I sighed, realizing I'd committed to this, and had to follow through, "Yeah, I guess so, I'll have to let my folks know... and get some stuff for overnight from home"

"Ok, why don't you split now and take care of that, and when you get back, we'll head for my place?" he suggested.

"Yeah, sounds like a plan." I replied, and then added, "Have you seen Mel at all today?"

"Sure, she was here all morning," Cindy said quickly, "at least, long enough to hear about your 'Bowie miracle'! Ha, ha... Then she left on some errand or other."

"Oh. Ok, thanks. If you see her, can you tell her that I'll call her tonight?" I asked.

Both Cindy and Andy answered almost in unison, "Sure!" which got me laughing and the fact that she had been here this morning helped me feel a little better, but I was still worried that she was upset with me. Maybe she was so upset that she had decided to drop out of the Music Club. Wasn't it her Friday afternoon class that she said her old boyfriend was in? My mind was flying off in tangents that always led back to one place, Mel dropping me because I'd admitted my cross-dressing to her.

"Alright, I have to file all this contract paperwork and stuff, then I'll be going home, I'll call you when I'm heading back here for ya, ok?" I proposed.

Andy's brow arched as he thought about that, and said, "You should just lock it up in Mel's desk out front, she'll take care of it when she gets back. That's her job now after all, plus she's been working hard getting those files to make sense."

Completely surprised by this, I said, "Wow, I didn't know she had been able to devote that much time already, that's great... ok, I'll do that. See you later Andy, and um, bye Cindy, have a great weekend!"

Both Andy and Cindy giggled for some reason, then Cindy said, "Oh, I'm sure we will, but thanks hun, you're so very sweet! Buh-bye now!"

I left them and went to my office to get ready to go. So maybe Mel wasn't leaving me after all... well, I'd have to hope for the best. Putting all of my junk back where it needed to be, then grabbing the contract in one hand and my backpack in the other, I shut off the light and locked the door. Walking over to Mel's desk in the front office, I unlocked the drawers and put the contract on top, along with a quick note on a yellow post-it that I attached to the corner, that said, "Pls file for me when u can darlin", and then I'd added a little heart at the bottom. So very much had been happening to me lately, emphasis on 'to me'. I was beginning to think I might actually be in love with Mel, but was it really love, or something caused by all of the other emotions that I now had running through me?

I shook my head as I began walking out of the Music Club offices, to see if it would clear my brain a little bit. I could hear Andy still laughing and talking in his office and I again remembered Cindy's voice as she was telling me I was so 'very' sweet.

Cindy's commanding tone and sexy emphasis on the phrase 'very sweet' gave me an uncomfortable feeling that left me with a dry throat, and a twitch in my cock as it became semi-hard. It triggered a sexual fantasy that I've rarely even admitted to myself, much less anyone else. It went far beyond simple cross-dressing. I had to quickly shut it out of my mind. It was, very much, my dark side, my alter ego, and it was a side I couldn't ignore, yet was so ugly I despised myself whenever I submitted to the pleasures it provided. It came and went in a lightning flash, really nothing like the crashing wave type feelings I would have around cross-dressing.

And yet this brought such extreme sexual release, that I couldn't resist its temptation for long before I would slowly, surely, start seeing the fantasies chasing through my dreams again, over and over until I would have to bow to its powerful pull on my libido. I would see myself wrapped in beautiful white cord, straining all my muscles in order to rip myself free from its hold. At this point in my life, I wasn't sure exactly what it was all about, but I had seen it in porn magazines, only bits and pieces really, that I could just barely place, but it was apparently all part of a fetish called 'bondage'.

For me, there was something completely erotic about being 'en femme' and also being tied up. For that matter, just seeing someone else, another female tied up, was usually enough to push me over the edge. Sometimes just the thought of tying a female up would trigger an orgasm. For some reason it was just that one specific act that would do this, usually with ropes or cord. I was never interested in anything else, in fact during most S&M videos, the use of whips or other 'toys', would turn me off, it was only the act of putting, or being put, in bondage that I found arousing.

The biggest difference between the sexual release I would get from cross-dressing and bondage, was that after I'd use bondage to achieve an orgasm, I would feel disgusted with myself for 'giving in' to the fetish, and felt terrible about myself for some time, until I would get horny enough to want it again. The fact that I had a fetish that could cause me to lose control like that made me uncomfortable with myself, almost as if there was a part of me that I shouldn't trust, because the cost of this pleasure just might be too high. Various situations would trigger this response, and I wasn't sure how Cindy's simple sexy phrase made this fantasy explode into my psyche, it must have something to do with her personality, but I couldn't sort it out right this second, I had to get home.

The rain was changing over to snow showers making the roads a clogged mess, but somehow I managed to get home just in time to meet my dad, who had also decided to come home from work for lunch, which was nice as we hadn't seen each other much lately. I was the youngest in the family, and my dad was in his late fifties now. We had a lot in common of course, but it seemed like we were never able to really talk to each other about... well, about much of anything. As bigoted as they came, he made Archie Bunker look liberal! So I knew better than to mention anything about my gender 'issues' to him, as it would be the surest way of being called awful names by my own father.

So, as usual, we just talked about the weather, our cars, my classes that day at school, my friend Andy, and then finally I got to the part where I let him know that I'd been asked to stay at his house over the weekend. I explained that since he lived so far away, it was hard to spend any time there unless I stayed overnight. And I also told him that Andy's father was a doctor and lived in a huge house on the Main Line, so it wouldn't be a problem for them to let me stay. That seemed to make it all right with dad, he just said to be sure to leave a number where I could be found if they needed me.

You might expect him to warn me about driving in such snowy weather, but he was the one that taught me to drive, he had also watched me race on the weekends at local dirt tracks and SCCA racing at Pocono raceway. If anyone respected my driving ability, it was going to be my dad. But it was just another of those funny little things he did, he would never tell me how much he thought of my abilities, he'd tell my mom, and then when he was out of earshot, she would tell me everything he'd said! Better than saying nothing, I guess, but jeez... they could get me crazy sometimes.

So I ran up to my room and packed a small bag with a couple shirts, underwear, a toothbrush, shaver, etc. Then I dumped my books out of my backpack and just put back the couple I needed for homework assignments, and the rest of my Malawi weed. Finally, I called Andy to alert him I was on my way, and then drove back to school. Like so much of the north-eastern US's weather, with storms that would come and go like unwelcome guests, by the time I was on the road, the snow had gone and the afternoon sun was hitting the wet roadway with a reflection so bright that it required sunglasses.

When I got back to the Music Club offices, I was very concerned because the front office looked dark and deserted. As I opened the door, I saw someone standing behind the front desk, but couldn't make them out. The light switch was on the opposite wall, so I called out for whoever it was to identify themselves, and when they didn't answer, started thinking maybe it would be best to go get security.

At that instant the lights snapped on and Andy, Cindy and Mel all yelled, "Surprise!"

Mel tossed some paper confetti onto the figure behind the desk. It turned out to be a full size cutout figure of David Bowie, done up as 'ziggy stardust'. Then she ran up and jumped into my arms, and after a long kiss, she said, "Congratulations sweetie! As soon as I heard, I went out and bought it for ya. You can keep it in your office if you want!"

"Oh no, I wanna put him behind my desk, so I can fool people that come looking for me, ha, ha!" Andy declared.

"Well, I'm speechless..." I said, then tried to continue, "This is... you guys are the best, really. Thanks." then I looked at Mel and said, "And thank you darlin', thank you for the Bowie, but mostly... well, mostly just thanks for understanding."

Which restarted our previous lip-locking session, generating catcalls and wolf-whistles from the 'gallery', in this case Andy and Cindy. Finally Cindy finished with the obvious, "Why don't you two get a room?"

"Ok, ok... c'mon you two, we're burnin' daylight here!" Andy yelled.

"Huh? What are we doing now Bro?" I asked.

"Its celebration time, and we're gonna get you into the Mile High Club." Andy added.

"Never heard of that club, is that a new one on campus?" I asked.

"Not really. It's been around almost as long as human's have been flying!" Andy said.

Finally it hit me, that crazy grin on Andy's face meant that he would take us flying in his dad's Cessna twin-engine airplane, and then we'd have sex one mile in the sky!

"You're kidding!" I exclaimed, "Is there enough room in that plane to... well, to do that?"

"Sure, its cabin has a huge back seat, drop down the luggage divider and it's almost a bed!" Andy replied.

At this point the girls were staring at us as if we'd both just grown second heads, neither of them had known us when Andy and I would go flying for a couple hours, once or twice a week, last fall. Usually this meant buzzing the campus while scaring as many students, faculty, and farm animals as possible.

"Alright kids, here's what's up," Andy now began explaining himself to the girls, "we're gonna go flying for a couple hours... have a little party in the air, well everyone but me, the pilot of course. So... you girls wanna go flying?"

It still took a minute or so for it to sink in, but the smiles began getting wider, then...

"You... have a plane?" Cindy finally exclaimed, ending in a giggle.

"Of course!" Replied Andy, then looking over at me, we both said in unison, "We're sure not gonna get very far flappin' our arms!"

Once the laughter died down (ok, it was actually more like groans), we got everyone organized and out the door, it was almost 3pm, so while we would have to hurry, we could presumably get a couple hours of 'flying' in. Andy had called the small local airport's tower earlier that afternoon and requested weather information, the snow squalls were dissipating and the forecast was for partly cloudy and clearing. Then he called the ground crew that worked on his dad's plane, and asked them to top off the fuel tanks, then remove the plane's cover and tie-downs, get it ready for take-off.

On our way, Andy insisted we stop off to get a cooler, ice, water, juice, and, of course, champagne! Fortunately the airport wasn't far from school, so once we got there, Andy and I pooled our cash for fuel and filing a flight plan. We then hastily ran through the pre-flight check. Andy had already taught me most of the basics, and I'd even landed once, so I felt pretty comfortable in the little Cessna. Our two passengers on the other hand were starting to have second thoughts.

"Are you guys sure you know how to fly this thing?" Cindy whined.

Andy was still getting the instruments set up, so I said, "Me? Well, not so much, but trust me on this, Andy's a very good pilot, he's been flying since he was 12." Then looking back at Andy, I quipped, "It's been a good 3 weeks since then, right Andy?"

Once all the pre-flight was complete and the engines were both running good, I looked back at Cindy and said, "Cindy? Why don't we switch now, I'll come back there, then you can sit up front with Andy, ok?"

Cindy only nodded at this point, both girls had very uncertain looks on their faces, as if any minute they might abandon ship! I crawled back between the pilot and co-pilot seats, and helped Cindy make the transition up to the co-pilot seat.

I then helped get the girl's seatbelts hooked together right, as Andy began to taxi over to take-off. I took hold of Mel's hand and it seemed to make her feel better, then I gave her a little kiss just to keep that vibe going. When I realized Andy was going to need both hands to take off, I reached up and grabbed hold of Cindy's hand too. She smiled back at me and just then Andy put the throttles to maximum, and within a few seconds we were in the air and headed for the clouds.

There's really nothing like flying, soon we could see a flock of geese headed back north as Andy pitched between cloudbanks, trying to avoid turbulence. Once we reached about ten thousand feet, Andy could engage the autopilot and I could then turn over Cindy's hand to him. He pulled her over and gave her a long kiss as well. I used this as a good excuse to give the same attention to Mel. As I came away from our kiss and looked out the window, I asked, "Isn't it beautiful up here darlin'?"

"Oh yeah, absolutely beautiful sweetie!" she answered. But I couldn't help noticing the way she said it was very sexy. Which made me sort of cock my head to one side and I realized that her eyes were only on me as she said it. Her hands were already exploring inside my shirt, and I knew I better get the luggage divider down... now!

Once I found the lever, the center section of the large padded back seat folded flat, then I laid out a couple blankets out to make it softer for Mel. I then laid down myself, with my legs towards the tail, and my head towards the nose of the plane. Mel got the idea and lay down next to me as we began ripping each other's clothes off.

"So sweetie?" Mel asked, "Have you ever had sex while flying before?"

"Nope. Usually, with my bong," I answered, "I'm flying while having sex! I guess we'll have to wait and see which way's better!"

This got a good giggle from Mel, but I soon realized why she was so focused on having sex, it kept her from thinking about being a mile up in the air in a tiny two engined aircraft, with a couple of college-aged goof-offs... and no parachute!

Mel soon had my shoes, socks, pants, and underpants off and I finished myself by pulling off my shirt, and then went to work on Mel. I had to help get her white knit pullover off, revealing a pink floral bustier. Then I pulled her jeans off which gave way to matching pink fishnet stockings and pink thong panties. It was as close to a wet dream come true as I'll probably get in this life, and my eyes simply glazed over as my cock, even after reaching its maximum, kept twitching, trying to get itself even longer if it possibly could.

Those beautiful hands with the French manicure, reached down and began stroking both my cock and balls, forcing a long moan from deep within me, but as I went to lean over to kiss her, she was already scooting down to line up her gorgeous mouth with my genitals. Now she began concentrating on the bell end of my circumcised cock, bathing it liberally, before starting to lick it exactly like an ice cream cone.

Joscelyn2tg
Joscelyn2tg
225 Followers
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