It's always scary when you get a new roommate but Jona seemed perfect. No drinking, no smoking, no drugs, no girls, at least in our room. He likes the same games as me, but does homework first. And he's generally a nice guy. But, as usual, there was a catch.

I found out when my last class was canceled and I was “home” two hours sooner than I normally would be. He'd brought a girl to our room. And a very pretty one at that. Definitely my type, in a flirty leather dress, a high black ponytail, slightly slanted eyes, and fiery red lips, beautifully painted. Then long legs in fishnet stockings ending in spiked heels.

A flash of jealousy hit me hard, that my roommate had a girl that I would die for to have on my arm. And he knew it, because we'd talked at night, while in bed, about our fantasy girls. She was nothing like the cute curly redhead with a nice size rack that he had made me believe was his type.

I don't know where he was, as the girl seemed to be by herself, and she seemed a bit flushed, like they'd just made out. Or maybe she had been playing with herself? That thought made me feel excited when I had to be mad. And that made my “Who are you?” come out much friendlier than I had meant.

In a way it was better, because she smiled, and it was so sweet. “I'm Joanne. You must be Greg? Jona had told me you wouldn't get back for another hour or so, but he allowed me to wait for you here. Happy early birthday!”

My birthday wasn't for another three weeks, but was she here for me? She nodded, saying she'd met Jona the Saturday night before, and he'd told her that she looked like his roommate's fantasy. And since she'd never been someone's fantasy before, she had wanted to meet him. Me!

And where I'm normally too shy to ask a girl out for a date, the way we met this way gave me somehow an extra confidence, and before we knew it we were chatting like old friends. Jona had told her I like leather and heels, and since that matched with her own style, she was even more eager to meet me.

And I, who never had a real girlfriend, just female friends, started feeling lucky. Very lucky. And suddenly we were kissing.

She was clearly more experienced than me, and after she first invaded my mouth with her tongue, she invited me into hers. And I learned quickly, enjoying the fresh taste on her smooth teeth as much as the strength of her tongue exploring me. Our first kiss lasted five minutes, and by then I was rubbing the leather on her butt, as she moaned into my mouth.

Suddenly she became serious. Apparently she liked what she saw in me, but she wondered if we were compatible on certain sexual matters that were very important to her. That worried me a bit, but I wasn't going to tell her that I was still a virgin. Yet, a slight hope got into me that maybe, just maybe, I would no longer be a virgin by the time I turned twenty.

Only one way to find out, we concluded, and she asked me to drop my pants. A slight nagging feeling wondered if she was part of a nasty prank, but I had already determined she was simply too nice for that. So, I took the risk, and thirty seconds later I stood before her, my dick sticking out more than I had thought, but she had that effect on me.

She licked her lips, and sat on her knees, right in front of me, and she started worshipping my monster. Okay, it wasn't that big, but for me it was. And from the smile on her face I could tell she wasn't disappointed, and suddenly she opened wide and her lips sucked it in like a cigar.

So yes, I was a virgin in more than one way, and this was my first blow job, but so much better it felt than when I masturbate myself. I could feel myself growing and she started bobbing up and down on me, with some smacking sounds. It started feeling better and better and I knew that I would soon reach the point of no return. That's when she started fingering me.

So, not really knowing what to expect, I had already enjoyed her fingers stroking around my scrotum, then behind my balls, and around my anal hole. I never realized it was so sensitive there, and even pleasurable. And when her finger pushed in my hole, while I was hot already, her touch erased the start of uncomfortable thoughts. And I couldn't help it, but when she pushed in a second finger, a moan escaped from my mouth.

That moan changed the game for both of us. She was maybe a bit careful before, holding back, but now she took my dick as deep in her throat as her fingers went in my ass. And I, overwhelmed by new feelings, pushed back at the intruders, with a loud moan. And I lost the last bit of control that had prevented my orgasm. And thus I came, harder than ever before, as she sucked a vacuum around my dick, while drinking every drop.

My knees went weak, and if it wasn't for the extra support she gave me in my rear, I could have collapsed onto her. With my hand carefully on her head I held myself up, as she slowly pulled away from my dick, her lips scraping off every drop. And as she pulled her fingers from my insides, she got up with a huge smile on her face. And then she kissed me again.

It was like earlier, our tongues twisting and touching. But now it wasn't clean freshness, there was a new taste, and I realized it was some of my own cum that moved between our mouths as our tongues moved back and forth.

When you masturbate and you catch your load in your hand, it's always messy, sticky, slimy stuff that is hard to wash off. And in a way that's what I felt on our tongues. Did it taste bad? Not terribly, it was more awkward really. But Joanne clearly liked the stuff, as she tried to suck it all back into her own mouth, and just because I thought that was funny, I gave her a hard time, and stole it back from her.

It became a sweet, passionate war between lips, mouths and tongues, and we both couldn't stop laughing as we slowly swallowed our gains. And when we finally pulled back I wished we could do it again. And that were exactly her words, as she said how much fun that had been. I thought that her first worry about sexual incompatibility was probably resolved.

As she cleaned her fingers, and I got us some water, I wondered if there was more that needed resolving, but she didn't say. So I basically told her that I had never experienced such a wonderful orgasm, but I was a firm believer in equality and I wanted to return the favor. And as I saw her eyes light up I thought that was maybe her other worry, and I planned to give her everything I got in me. Problem was, I had no clue what to do.

To make things easier on me… I think, she suggested that she drop her skirt, but I said no. I really wanted to smell the leather on her, so I asked if she was okay with my head under her skirt. The flush of her face told me that maybe I'd taken another worry away, both of us loving leather. But I had a second reason, that I didn't tell her. I had never seen a pussy up close, and I didn't want her to see me trying to figure out what to do.

To give me access she did drop her panties to the ground and she stood in front of me, challenging me to do my thing. So it was me now, going on my knees, and moving between her legs, the smell of her leather mixed with femininity urging me in.

So yes, I had worried for nothing. There was no pussy between her legs. She had a dick under there, very similar to my own. Erected in anticipation of what was coming. But in a way I was even more clueless on what to do now.

It is amazing how fast your brain can work a problem when you need an instant solution. This girl was so perfect and I had boasted about equality. Add the leather smell, and the way her totally hairless dick and scrotum actually looked quite feminine, and a decision was made. I don't even think she had noticed my hesitation, as I opened my mouth and took her in.

I didn't know what to expect, but definitely not a very female silky skin, wrapped around a meaty sausage, with veins just under that skin, pounding against my tongue in the rhythm of her heart. In less than a second any other thought that may have lingered in my mind was gone. And I suddenly understood the worship Joanne had shown to my own dick, early on.

I squeezed the base between my thumb and finger, as I moved my lips across the skin, slowly sucking a vacuum. And immediately she grew inside my mouth, the skin a bit less silky, the meat a tad harder. And as I tried to remember the things she'd done to me, I took her deeper, then let her go a bit, my lips putting pressure on the length.

I suddenly remembered her fingers tickling my scrotum, and as my fingers tickled her balls, once more I was amazed how soft they were, due to the lack of hair. I spread my fingers out and I heard her soft moan, as she was caught up in the erotic experience. And when I thought of rubbing around her anal hole, I met something hard. It was semi-dark under her skirt, but it looked like a sparkle and I wondered if it was some piercing. But it was too big for that, and when I used more force it moved softly around inside her. Something was pushed in her hole already and each time I pushed on it her moan became louder.

I tasted a fluid leaking from the tip of her dick, and I knew her system was getting ready, the pre-cum still very thin. And as I squeezed the base with my whole hand now, and my other hand pushing on the thing in her rear, I heard a soft cry a second before she exploded. I could only swallow the now sticky goo, as I recognized the taste from just minutes ago.

There wasn't a huge amount and I left a good glob in my mouth, as I pulled her dick that was rapidly deflating from my mouth, my lips cleaning it off. I could feel her hands resting on my shoulders and I realized she was the one with weak knees now. And as I finally pulled from under her skirt both our smiling faces were anticipating the kiss.

Once again we did a small war of mouths, but it was more gentle now, knowing there was enough for sharing, and more than enough available from where it came from. And when we finally pulled back, my belly fluttering from butterflies, she said in Jona's voice, “I knew you'd pull it off my friend. You were perfect!”

It was a shock, but somehow I wasn't surprised. It was much easier to accept than a stranger he had met two nights before, with whom he shared the most intimate details about me, and who had decided to have a sexual relationship with me in mere minutes of meeting me.

But I had to ask. “Why?”

And, after a slight hesitation, Joanne was back, her voice that is. And she explained that she had been a cross dresser, slowly realizing she was really transgender. And she had not been sure how to deal with a roommate. She had secretly dressed as Joanne when I had late classes.

As a young man he'd realized how lucky he was with me, thinking very alike, and putting our studies first. But as a young woman she saw me again as perfect, but this time my looks, my wits, my fantasy of my perfect woman, but in the end the fact that I never had a real girlfriend.

And Joanne started fantasizing about me, buying the leather dress that I had my fantasies on, and combining it with her own wardrobe that matched my description so well, up to the high ponytail and high heels. And today, in what she thought was her perfect look for me, she'd played with herself while dreaming of me, and suddenly I was there.

When you cross dress, and even when you realize that you want to be part of the other sex, you're always aware of getting caught or found out. And it teaches you to think fast, in case your biggest fear comes true. So, when I came in that door, her “Saturday night” story formed while she was already explaining herself.

But, the sexual desires or needs that she had spoken of were real, and the way I responded made all her fantasies about me slowly come true. Up to the point even that I gave her a blow job back. And the big question right now was, what did I think of her now, knowing that she really was my roommate Jona?

That was an excellent question. How did I feel about this? And in my head I started ticking off the goods and the bads.

She still looked like my best fantasy. Good.

I came harder than ever before. Good.

And that was from a blow job. Good.

But I really hoped for a pussy before my birthday. Bad.

Unless… Wait, that is a gay thought. Is that good or bad?

I sort of liked giving her a blow job. That's good right?

She's a magnificent kisser. Definitely good.

The smell of leather. Another good.

She can be my girlfriend. Sounds good.

Does that mean we can have sex every night? Good, as long as it doesn't affect our studies.

We can go out together. Good.

Hmm.. can I take her home? That's probably a bad, knowing my dad. But what about mom?

What if I fall in love? That should be good…

Why do I feel butterflies already? It feels good!

I lost count, but there were definitely more goods. But the gay thing worried me. As if she could have followed all my thoughts, she said “I will be Joanne, as often as I can. You won't be dating Jona. Or having sex with him. So, that's not really gay.”

Hmm, our minds were in tune as well. That's definitely good too. I guess the smile on my face gave it away, as she moved closer and pushed her body against me. And suddenly we were kissing again, and both our minds were made up.

“Listen”, she said, “let's take this slow. But there's more to it than just kissing and blow jobs. I know you haven't had experience with a pussy yet, but as a transgender girl we have two options. I have heard other trans girls talk about their anal hole as their pussy. That may seem gay but I wear a butt plug as often as I can, simply because it feels really good. And I imagine a real dick, your dick, would feel even better. I'm just as much a virgin in this as you are, but I'm willing to save it for you. Until you're ready.”

That was a thought. It felt gay but it sounded sweet as well. I wondered what the other option was. Again she guessed my thoughts. “Alternatively, I could wear an artificial pussy. With a good quality you'd be able to penetrate me even. Not sure how good it will feel for me, and of course my dick would be hidden, so no pleasure there, but I'll be happy to wear one for you.”

That sounded wonderful to me, she'd be a “real” girl. Even my dad wouldn't know she wasn't. But, in the back of my mind it didn't sound right. She was willing to give her pleasure up, to make me feel better. That is very unselfish of her, but it would be selfish of me. That's not me. Unless…

“Can we try both? Until we figure out what gives you the most pleasure? If you are going to be my girl, then I want only the best for you!”

It was that last statement that made her nod and smile. “I like it! Being your girl…” And that's how we moved from then on. She'd be my girl, every night and on the weekend. It was fun to make plans together. Like how we could sleep together. I suggested we throw the mattresses on the floor, and we sleep in a big bed, under one of the high bed frames. But she suggested we move both high framed beds together in the middle of the room, so each could get out still without having to climb over the other. It seemrd that could work perfectly.