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I've used RPGSolo for a while. But now I want to try an actual, documented game. I'm starting a new game of Vampire:The Masquerade, using a mishmash of the 1st and 2nd Ed rules. Beyond that, I begin with no idea of what I want to play:

Creating a new character. I'll use the "Question & Answers" section to guide my character creation.

How old are you? I want to begin the game in 1991 (year of the 1st Edition). I'll assume my character is in his mid-20's at the time of his embrace. Was I in my mid-20's when I was embraced?

(50/50 | 5[d10]) No, but...

Not in my mid-20's, but around there. Am I older?

(50/50 | 2[d10]) No

So, I'm younger. Early 20's. I'll say roughly 22. This may shift based on later determination. How long have I been a vampire? One year?

(50/50 | 7[d10]) Yes

I've been a vampire for a year. Next, I need to focus on "what was unique about your childhood?" I'll use Complex Questions to help narrow this down, when needed.
Did I go to public school?

(50/50 | 4[d10]) No

I went to private school. Was it an elite type school, or a local private one?

(50/50 | 1[d10]) No, and...

I phrased the question wrong. Looking at the first part, "elite type school" is the relevant question. So, I went to a local private AND. And what? It wasn't a terribly GOOD private school. Instead, it was one of those "last chance" schools for all the trouble makers and problem kids.

Was I a good student while I was there?

(50/50 | 7[d10]) Yes

Did I have a lot of friends?

(50/50 | 2[d10]) No

No. Whatever got me sent there, I was a good student and hung out with a small group of others who were actually concerned with our grades. 

Who were my parents?

Oppress / Extravagance

They were pretty well off, though not as well off as they wanted people to think. The house and cars and vacations were all based on "keeping up appearances." Mom had a new Mercedes, and I had new designer clothes, but there were plenty of times we barely had enough to eat. Parents cared more about appearances than actual relationships--no wonder I "acted out" and got sent to Pembroke Academy. (That may be a real place. I have no idea, name just popped in my mind.)

Did I have siblings?

(50/50 | 8[d10]) Yes

A lot?

(50/50 | 7[d10]) Yes

Did I, generally, get along with them?

(Unlikely | 4[d10]) No

Parents were absent, and us kids constantly fought among ourselves. We had plenty of toys, but they were abused and mistreated, and we were always breaking each others favorites in games of petty revenge. 

I imagine my friends at school were the one place I felt safe, and accepted.

Did anything bizarre, supernatural, or downright odd happen in my childhood?

(50/50 | 5[d10]) No, but...

I was always fascinated with tales of fantasy, of vampires and wizards and other worlds. 

Smart, lonely kid whose fascinated by sci-fi. Really breaking grounds here on a PC Smile

Anything else particular about my childhood?

(50/50 | 10[d10]) Yes, and...

What was it?

Attach / War

Parents eventually divorced. Us kids were caught in the middle, becoming pawns between both parents, driving even further wedges between my siblings and I. 

Did I go to college?

(Somewhat Likely | 9[d10]) Yes

Was it a really good one?

(50/50 | 6[d10]) Yes, but...

Not "Ivy League"/MIT level, but still a top notch one. 

Was I a good student at college?

(50/50 | 8[d10]) Yes

Did I go (or intend to go) to grad school?

(50/50 | 6[d10]) Yes, but...

But, I was turned into a freaking vampire before that could happen. What did I study?

Create / Tactics

"Create" makes me think of the Arts--writing, sculpting, theater, etc. Tactics, though, is more of a "business" thing. I'm actually ok with this. I majored in an Art, with a minor in Business. Maybe as a fallback, maybe as a deliberate choice since I wanted to be in control of my own "business," even if that business is a photography studio. Let's narrow it down. What are some good art majors? Looking online, I come up with this list:
1) Writing
2) Photography
3) Theater
4) Art History
5) Studio
6) Graphics
7) Craft/Material
8) Fashion
9) Cinema
10) Dance

Let's roll a d10 and find out.

8 = 8[d10]

You know, I'm not sure fashion is where I want to go, based on his background. I'm going to roll twice more and see what strikes me.

6 = 6[d10]

5 = 5[d10]

After I rolled this, I realized that none of these spoke to me. In fact, I had already played my subconscious hand earlier--he's going to major in Photography. Business was his backup plan, though knowing some accounting is always good for a freelancer. 

Did I have a lot of friends in college?

(50/50 | 6[d10]) Yes, but... +Event: Punish / Technology

Huh. "Punish Technology." I'm not sure what that means. I had a good group of friends but... If this was today, I'd say most of them were online. But, when I think about it more, I think it's some I did with my camera that ruined my friendships. 

Let's say I was always the guy with a camera, taking all kinds of impromptu photos. To the point that my friends sort of accepted the camera being there. When it came time for my final project/grad school application, my adviser loved these and encouraged me to display them. Of course, they were displayed at the Student Center, and one even got into the student paper. And it showed all their sins. The drugs, the hookups with their exes, everything that should have been kept private. I got into grad school, and even got a scholarship, but lost most of friends in the process.

Was I a good person?

(50/50 | 2[d10]) No

I learned a lot from my parents and siblings. I didn't even feel bad about the "betrayal." They knew what they were doing, after all. I did make them do those things.

When did I first meet a vampire?

Failure / Liberty

In jail. It was a BS DUI thing, and I had to spend the night in holding. The person I met was annoyed they were there, but totally confident they'd be out, with charges dropped, before dawn. We got to talking, and I was fascinated by them. I kept think I saw them again after. At the exhibit, around campus, at the studio I worked taking photos of bratty kids. We "accidentally" ran into each other a few times, and would spend hours talking about, well, everything.

Is my sire a woman?

(50/50 | 6[d10]) Yes, but...

She was beautiful and exotic and fascinating, but every time I felt myself ready to fall in love with her, something struck me as wrong. She would lean against a post, and seem like a limp doll. She would wait for me, and just stand in one place, unmoving, like a mannequin, until I approached her and then she would have an energy and vitality that seemed exhausting. She was everything I ever wanted, but there was always something that screamed at me to run away.

Who was my Sire?

Release / Jealously

Wait, that was a Complex Question. I wanted a Complex Description.

Hacking

Lazily / Aromatic

Casually elegant with the best makeup and perfume. She truly seemed utterly detached from the world.

When she embraced me, did she seduce/prepare me for it?

(50/50 | 1[d10]) No, and...

It was brutal, and painful. The night started off like the rest did--a random meeting, a catching up, long walks around town, longer talks. When it got late, I had to beg her off. I had just started Grad School and had class the next day. she pouted and harped on me to stay. I did, and followed her to where she wanted to--a seemingly abandoned factory at the edge of town. I tried to leave, but she compelled me to stay. I followed her in, and she took me into the basement. 

I didn't want to go, I begged her to let us leave. She insisted, and she got physical. She was all of 5'8 and couldn't have been more than 100lbs soaking wet, but her grip was like iron. She threw me into the storage room, and locked me. 

The next several nights were just darkness, and pain. She would visit me, and feed on me, and leave me just enough food to keep me alive. She forced me sign letters...withdrawing from school, to my family, to my remaining friends. "Opportunity of a lifetime," "Couldn't pass it up," "I'll get in contact when I can, though it will be a while." That sort of thing. I knew I was never leaving that room alive.

And I didn't. After an unknown number of days, I was dying. The bloodloss, the cold room, the darkness. It was too much for me. She came and took what was left of me, and then abandoned me. She left the door open, a last, mocking gesture. I had my freedom, and with it, alone, I died. 

But I wasn't fully alone. She had left the smallest drop of herself in me. And so, the next night, everything changed.

I'm assuming I'm a Toreador, right?

(Sure Thing | 10[d10]) Yes, and...

My sire is actually pretty prestigious among the Toreador. 

How did my sire treat me afterward?

Aggressively / Strong

She is extremely controlling. She insists that I do things her way, or not at all. 

Why did she pick me?

Sniper rifle

Deceive / Opulance

(The sniper rifle was me click the wrong button. Ignore it)

Deceive Opulence though is interesting. Did she think my family had money? No. They put on a show, but not a good enough one to fool a vampire. And beside, even if they had money, the "one heir out of many" isn't going to get a lot. Instead, it's the EXHIBIT she loved. How my photos exposed the lie behind the perfect, glittering facade of life. For all her monsterosness, she actually did love my art.  Her aggression is to push me to get even better (SHOULD HAVE LET ME FINISH GRAD SCHOOL THEN, KAREN!), and to show me off at all her parties as her "new favorite."

And yeah, "new." I decide there are a few other childer of her. Each was her favorite darling for a few months or a few years, but then cast aside when her attention drifted elsewhere. 

Was I presented to the Prince?

(Very Likely | 9[d10]) Yes

How did that go?

Antagonise / Dispute

"ANOTHER one?" The Prince asked, as I was introduced to him. My sire has been creating far more vampires than the Prince is happy about. She has enough clout to get away with it, though. So, his anger was directed at me. I received a brutal lecture from him about how we are SUPPOSED to behave. It was...not an impressive first meeting.

Where is my haven? I assume it's my same, crappy student apartment, right?

(50/50 | 6[d10]) Yes, but...

I was planning on paying for this place with my scholarship/grant money. Decent 2 bedroom in a crappy part of town, with one of the bedrooms being my darkroom (this is '91, before digital cameras). So, no grants, no scholarships, no job (can't take family or wedding photos at night), I'm in a bit of a tight spot.

Where did I feed?

Rudely / Rotten

Off the homeless and destitute of the city. My sire HATES this, and does her best to force to learn to behave "properly." What is proper, though, for a monster that survives on the blood of the living? Like my mom, my sire puts appearances ahead of anything else.

Motivations:
Do I have any enemies?

(50/50 | 8[d10]) Yes +Event: Violate / Weapons

Yup. Part of my trying to get money. I work for an off brand porn magazine, but I also go to crime scenes and try to get the sensational photos to sell as a freelancer. One of them was a gangland killing, which caught some of the gang members in the pic. They hate me, as does the vampire behind them.

What do I truly wish for?

Guide / Failure

I want to understand. What is this world I've been cruelly brought into. Why are there vampires? What are we, truly? Where do we come from? Why do we exist? What is our purpose? What is mine? It can't just to be to drain the life of those cast aside and document the cruelty of the world, can it? Sure there must be more. There must be.