A Learning Experience Ch. 01

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Going to college sometimes reveals more than you would like.
7.4k words
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Part 1 of the 10 part series

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

Hello!

I stumbled upon Literotica by accident one day, a few weeks after my transgender partner of 4 years, and the love of my life, died of an accidental drug overdose. Still out of my mind with grief, I found the TG stories on Literotica to be such a healing essence that I became completely enthralled by them. Because writing and editing have been an important part of my life, I wanted to try to give back a little bit. This is my first effort, it describes some of my college life, and how I was able to eventually transition. I have 'enhanced' much of the narrative, including 'punching up' the sex scenes, changed the names of everything, etc. But for all of that, what's here is still the essence of what really happened. Believe it, or not.

This is chapter 1, there is a lot of back-story here so there isn't as much drugs, sex, and rock & roll, but this will increase through the next several chapters, so enjoy... Joscelyn

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It was shaping up to be one gorgeous march day, spring seemed to be breaking into our dull boring winter and I was so sick of grey ugly days, that I only wanted to cheer it on. The sun was warm and bright on my face as I walked through the parking lot and along the quad toward the arts building. Unfortunately the heavy backpack I carried, stuffed with the books and materials I needed for classes, reminded me that I probably wouldn't be outside much to enjoy it.

After graduating (barely) from high school my parents had given me two options, I could go to one of the three colleges that had offered me scholarships. They were all music scholarships that gave a very limited amount of the needed tuition, so I'd end up working at burger joints at night to make up the difference. Actually most of my friends were in the same boat, but that grinding 24/7 workload would probably not have any kind of good outcome for me. All work and no play meant Jack would probably flunk out, for one reason or another. My second option was the local community college, but either way I was 'going' to college! Because we were still 'involved' in Vietnam when I was making this decision, going to college became mandatory, then if I was drafted, I could claim a college deferment and at least not be shipped off to that hellhole immediately. Hopefully I'd be drafted just as we sign a peace treaty with North Vietnam, so I might even miss it altogether. In any case, it was off to the community college for me, to try and get an education of some kind or another.

I was always on the thin side and about normal height at 5'9" just a week after my 18th birthday. Mom always described me as 'lanky'. I was terribly self-conscious about my lack of body hair, especially on my chest and face. Because I was a natural blond, even the hair I did have barely showed, so I tried to make up for it by growing the hair on my head as long as I could. So far I'd been able to grow it a few inches past my shoulders, which fit in great with my music gigs. After all, most rock musicians wore it long at that time to show their 'rebel spirit', or at least I could convince everyone, including myself, that was why I was doing it.

Of course, my mother hated long hair, but surprisingly Dad backed me up, reciting something about how Norman young men in the middle ages, just after the battle of Hastings, rebelled against their elders by wearing their hair long like the English. Sometimes my Dad's love of history really rubbed off on me! The girls I dated seemed to like it long too, but mostly because it pissed off their parents, I was often used as a dating 'bad boy'. They called me 'cute', when I would have preferred 'handsome'. But I took what compliments I could get, as I knew my body would have to develop a lot before girls would admire my 'handsome' features. I did inherit my dad's blue eyes, which became a lighter shade of blue when my pupils would dilate, giving the impression of lighting up when I became angry or excited. While my chest and arms had average muscles, my hips and legs appeared bulked out and hard, as if chiseled from stone, due to playing goalie for six years on the school's varsity soccer team.

Because of the lack of development in my upper body, along with the long blond hair, I was sometimes taunted in high school about my feminine appearance, I had the term 'sissy' thrown at me so often that I ended up in more fights than I can remember. It's also why I still get angry just hearing that term used in normal conversation. But after getting my nose broken twice, and earning my varsity letter from soccer, I'd finally managed to gain some grudging respect from my schoolmates. What they didn't know, and I would never have admitted even under torture, was that while I was very attracted to women, I also felt an intense longing to be one myself. In fact, in my dreams, I'm always female, even my 'wet dreams' are always lesbian orgies! Ever since the age of four I've felt that I should have been born as a female and these recurring dreams only reinforced that feeling when I reached puberty.

At the age of six, on my very first day of first grade, my teacher divided the room into girls on one side, boys on the other, and of course I'm sure you can guess which side I went to. The laughter of my new classmates brought me the very first sampling of the humiliation that comes with taking action on the feeling of being the wrong gender. When my teacher sent me home with a note, my mother lectured me that such thoughts were 'perverted' and must be fought against.

And so I did, although mostly I just tried to ignore them, I hid my true feelings for the next 10 years. My natural attraction to females, and not males, made that easier for me than a couple of my male classmates. Because they were gay, and only attracted to males, the ridicule they dealt with was awful. I'd inevitably stand up to whatever bully was attacking them, which almost always ended badly, getting myself in even more fights and eventually breaking my nose for the third, and hopefully last, time. You would think once I'd reached puberty, all those male hormones would have blown any effeminate thoughts or dreams right out of my head. Instead I found myself longing for a more feminine appearance, and so I began indulging my cross-dressing fantasies.

Now, after 4 years of experimenting between my mother's and sister's closets, as well as a few pieces I'd acquired on my own. I was desperate to go out in public, to really be seen and accepted as female. At least part of me was, the rest of me was horrified that I might actually go through with it and be 'made' as a cross-dressing male. That fear of discovery was so overwhelming that just the thought of it could produce beads of sweat running down my face. There was no sexual titillation involved for me when it came to the humiliation of being discovered, it was nothing but the pure terror of seeing a lifetime of work building this facade of masculinity, come crashing down around me.

I had worked so hard my whole life to be seen as all male, I could ID any car you could point at, and even give you its year and how well it was running. My nails were always dirty and I worked summer jobs at local garages and machine shops. Racing cars was inevitable, starting out on local dirt track ovals and drag strips, and then finally SCCA competitions, and even an NHRA Alcohol 'Funny Car'. I would take dares from just about anyone for just about anything, the rougher the better and I could curse like a gob-smacked sailor while doing it. But I just couldn't avoid getting that 'feeling'. It would completely overwhelm me sometimes, and then suddenly I had no resistance. I had to have that feeling of femininity, even if it only provided the shell of being female, I had to at least try to achieve that. Like so many that feel they are the 'wrong' gender, and certainly at this point in time for me, I was deeply conflicted.

Because of the Christmas holiday, the pressures of my second term classes, along with other, more recent demands that I'll explain later on, it had been several weeks since I'd attempted any cross-dressing, had sex, or even masturbated. The 'urges' were starting to get pretty strong. It always seemed so funny to me, when I would hear people claim that being gay was a chosen lifestyle! Hah! Who would ever choose to deal with all of this crap? But now that I'd thought of it, once again I was asking the same old question, was I gay? As I dismissed this again for the billionth time, I found myself walking through the front doors of the arts building, reminded of my first day of college.

It was in this building, where I'd first started college last fall while registering for first term classes, that I met Andy Goldmann. He was as loud and boisterous as I was quiet and shy. He came up to me with the old line, "Haven't I seen you somewhere before?" Eventually we realized that he must have seen me at one of my old rock band's concerts. As I said, music was more than just a hobby for me, and I'd managed to get a couple music scholarships. Being first seat trombone on the number one high school stage band in the state got me noticed, and I had been in several local rock bands as well. I'd started out on drums, but moved to keyboards once I could afford them.

And it wasn't long after we met that Andy had one of his 'foolproof' plans pop into his always-scheming mind. Eventually I would learn that his foolproof plans were those that even a fool would stay away from! But this time I listened to him, and his plan actually sounded logical, so I told him we should give it a try. Once a year, at the beginning of the fall term, all of the college 'clubs' would have their annual elections for club officers. One of these was the Music Club, which just so happened to also be the most popular club to get elected to. Andy figured that between my experience with contracts that were used in the music business, and his ability to fund our election campaign due to the fact he was rich, or to be more specific, his dad was rich, we should be able to win. What I found out as we campaigned, was that the Music Club was so popular because it took care of scheduling and signing all of the performers that would be appearing at the college for the coming year. They had a huge budget for getting top-notch talent, along with the budget for the college's local radio station.

As he had promised, Andy paid for posters, flyers, and bumper stickers, so that our names were eventually plastered on everything and anything that could possibly be seen by a member of the voting school body. He even bought the services of a professional jingle creator and had professional sounding ads running 24/7 promoting us on the school's radio station. He had also already decided who would be president (him), and who would be Veep (me), but I never liked publicity anyway, and frankly didn't think we had a chance in hell of winning, so I didn't mind being second banana.

Next thing I knew, we were 'in', as they say, and we were in it big. We had won in a landslide, and it turned out that we had a cool 3 mil in concert money to allocate for the year. Of course, we had a teacher advisor that we had to have sign off on all of our ideas, but she was pretty cool. So we were going to be having a grand old time in college this year! Think about it for a second, tell any college-aged female that you can get them backstage to meet David Bowie, or Elton John, or Carlos Santana, and then 'not' get laid. Yeah, it was impossible, and eventually we had a queue of groupies, or 'club members' to select from, it was something like teenaged nirvana.

As my mind returned to the present, I vaulted up the main stairway, three steps at a time as usual, to our second floor Music Club offices. I see two girls run giggling out of our hallway towards me. When they saw me, their eyes became saucers and both let out a surprised yelp, then one of the girl's yelled back to me over her shoulder as they passed me going down the stairs, "I think he's got her trapped, you'd better hurry!"

Then they fell back into their giggling and ran out the doors that I'd just come in. My first thought was, 'I wonder who his new target is' as I remembered Andy's penchant for chasing groupies he imagined to be virgins. Then I realized I better get this situation under control, our advisor had already given dire warnings about 'one more incident'.

When I reached the office door it wouldn't open, there seemed to be something jamming it from the inside, only allowing it open about an inch or so. As I tried to figure out a way in, I suddenly heard a girl scream, and instantly found the upper body strength, propelled by my legs, to push the door completely open.

Now that I was in, I saw a tall girl with blond hair, but could only see her from the back. She was trying her best to keep the front office desk between herself and Andy. He had obviously been chasing her around the desk and they were both gasping for breath and seemed to be at an impasse. On the small side at about 5'6", Andy had longish black hair and looked for all the world like one of the hobbits in Lord of the Rings. However, you could tell by the lump at the front of his jeans that he was big in 'other' areas, in fact, overly excited in that area at the moment.

"Andy," I began, looking straight at him while trying to sound just as frustrated and pissed-off as I felt, "What the hell are you doing, trying to get us thrown out of here?"

Then as the blond turned her head to look at me, I quickly shifted my gaze, and realized it was that very pretty new club member who had begun helping me last week with some of the office tasks, named Melissa. I had met her in some of my classes and knew we were both about the same age. She was pretty close to my height, and with her 4" stiletto heels, she appeared to tower over Andy. She had that classic Nordic beauty, with long blond hair, blue eyes, and silky opaque skin, only now her hair was a tangled mess and her pink flowered shirt was pulled out of her close fitting black jeans.

Conflicting emotions began surging through me. Andy wasn't chasing some groupie around a desk, he was attacking a girl that I really cared about damn it! Well, I guess I really hadn't told her yet how much I cared. But after all this craziness, and with that frightened look on her face, I'd probably never see her again anyway. Then, as if reading my mind, once Melissa saw the fully opened door, she left the protection of the desk, circled behind me to the doorway, and made her escape.

For some reason Andy's smile had only grown bigger from the moment he saw me, seeming almost relieved that I was there he replied, "Sorry Jack, but I just 'had' to do something! You've been grumpy as hell lately..."

Shaking my head in utter frustration I said, "What the fuck does..." but was cut off.

"And ya know Melissa?" Andy continued, "Well she's been telling me she wants to get to know you better." His hand was now casually brushing away stray hair from eyes that seemed to be twinkling with mischief.

I also abruptly noticed Cindy, Andy's latest full-time companion, sitting in a chair on the other side of the room, grinning like the proverbial cat that just ate the canary. Cindy was just a little taller than Andy, with curly auburn hair and green eyes that seemed to look straight through you. Like Andy, her size belied her strength, and she was very quick witted. Her dark hair matched her olive complexion, making a very sexy combination. One odd thing was her age, as she certainly acted older than most first year college students, yet she looked quite young, if I had to guess I'd say around 25, but for all I knew she was the same age as we were.

Just then I heard the door shut behind me, but it was the unexpected snitch of its lock that made me quickly turn on my heel. I thought Melissa had taken the obvious escape that I'd provided and was surely long gone. Instead I found two beautifully manicured hands starting to unbutton my shirt, then raised my eyes to gaze upon two gorgeous pools of pale blue looking back at me, I was close enough to smell her perfume and watch her bite her glossy red bottom lip as she continued disrobing me.

"You... have... the most beautiful eyes," she whispered, "and my friends call me Mel."

I gulped long and hard as there wasn't anything more for me to say, I'd been conned, this whole crazy thing had been set up for my benefit, or rather my embarrassment, and I was now too stunned to even move.

Jumping up to shut the blinds on the window of the front office that looked into the hallway, Cindy then moved over next to Andy, and also started disrobing. During all of this, Andy had been laughing at the results of his latest foolproof plan, while pulling off his own clothes. Once Melissa had gotten my backpack and shirt off, her hands caressed my chest, stroking my nipples as they both became erect instantly. She then took a couple steps back and with my undivided attention finished unbuttoning, then removing, her own shirt, throwing it over a nearby chair. I gasped at the sexy black underwired bra with little pink ribbon between the cups that supported her C cup sized breasts. The large areolas provided a backdrop to the hardened nipples just peaking over her lacy bra cups.

She quickly stepped out of her black patent pumps, just long enough to peel off her jeans and reveal some incredibly stunning black fishnet pantyhose with attached crotchless panties. Something was definitely catching up with the whole situation down near my own crotch at this point. After Melissa, or Mel as she now wanted me to call her, had her shoes back on, her own quick glance at that area of my anatomy produced a lustful grin.

With this encouragement she minced up to me putting both arms around my neck and seductively asked, "see anything you like?"

There are times when you have to suspend your role of being a 'gentleman' and just go for it, this seemed to be one of those times. As much as I might have wanted to sort this whole thing out logically, my male hormones overrode all logic and rang the engine room for 'full speed ahead'. My abstinence timer had expired, and my body wasn't giving my brain any more time to consider how surreal this all was.

Our lips collided, with my head tilting one way, and hers the other, then our tongues did battle in and out of each other's mouth. In the meantime, my hands found the clasp for her bra, instantly removing it and heaving it on top of the filing cabinets. Then I dropped my hands down to her ass, each one grabbing a cheek of that beautiful bubble butt, and pulled as if I was never going to let her go. In response her legs encircled my midriff and we kissed like that for several minutes. When we came up for air, I saw Andy and Cindy just disappearing into his office, with Cindy winking at us, and Andy giving a 'thumbs up'. The best I could do was acknowledge with a head nod.

I flipped off my shoes, unbuckled and unzipped my jeans, letting them drop, along with my black cotton briefs. Stepping out of both I carried Mel, as carefully as I could in the circumstances, over to a medium sized sofa that was also a futon and quickly pulled it out with my foot, turned around and sat back on it with her long legs still encircling me. She then pushed me back, so I was lying down and she was kneeling on top of me. As she started to bend over to kiss me, I instead began to blanket her body with small kisses, starting at her neck and then moving to her incredible breasts, I started pinching her right nipple while I sucked on the left, making her moan, then switching around to attack the left with my fingers, and soothe the right with my tongue. For several minutes I swapped my technique between her lovely mammaries as she held and caressed my head with both hands.

Joscelyn2tg
Joscelyn2tg
226 Followers
12