It all started in Women's Studies. I was chatting with some half-closeted freshman who couldn't be bothered to come out and say what he wanted - to fuck my little sissy ass - when the professor started calling around the room for answers to a question I hadn't even heard.
I turned to my roommate, Dylan. He was 6'4" and built like Superman, and I'd have let him fuck me in an instant...but of course, he was straight as an arrow. He always sat next to me in this lecture, since I was the only guy he knew, and even an effeminate fag provided better solidarity than sitting alone.
"What did she say?"
He leaned over, smelling like sandalwood aftershave and drug store shampoo. "Name a way that men could put themselves in a woman's position out in the real world."
I laughed. As a full-on sissy bottom who wore panties every day and owned several miniskirts, I didn't have any problem putting myself in the feminine position. In fact, if this dumbass 18 year old ever got his shit together, I'd be taking some pretty feminine positions this afternoon.
But that wouldn't fly for this class. The professor made it clear from day one that she wasn't going to give me a pass for being queer; even gay boys need to learn about patriarchal oppression and all that.
So, when she got to me, I said, "If men really want to know what it's like to be a woman, they should try shaving their legs. It's a huge pain in the ass and totally uncomfortable most of the time, but you can't know what it's like until you do it."
The professor seemed genuinely impressed that I'd contributed something useful, so I buried my nose in my computer until the end of class to compensate. The freshman disappeared in our chat, but he might come back later. I think he must have really cum all over himself after I sent him the photo of me getting fucked from behind by my ex. If that didn't bring him back, he probably was straight after all.
I flinched when I noticed Dylan looking at my screen, but I don't think he saw anything. Everyone else was packing up while I was waiting for a reply from some desperate kid so he could come over and fuck me... maybe I was a little desperate too. I hadn't had a regular dick in my life for six months now, and the dildo I kept in my bedside table just wasn't cutting it anymore.
"So which one are you going to do?"
I closed my laptop and looked up at Dylan. "Which one what?"
He smiled handsomely. "The exercise she assigned? Go out and do something to experience life as the other gender?"
I missed that part. "Oh. I guess she wants a write-up too?"
"You got it," he said. "Describe the experience in detail, and all that."
"I'll come up with something," I said. Probably, I'd fake it at the last minute. I had other things to do before then.
"Oh, okay." He looked a little off, but I didn't pay it much attention. Did he want to do it together or something? I wasn't really interested.
Later, I was holed up in my room, trying to reel in my latest catch. Fresh meat had come back after all, but he was still reluctant to meet in person. He kept asking to see me with the dildo in my ass, even though I was just about begging him to come over and give me the real thing. I'd encouraged him to masturbate to me, but I wasn't a porn star. In this instance, I actually wanted my audience to come participate.
That's when I heard Dylan knock at the door to my room. We were lucky to find an apartment that we could both afford and had functioning locks on the interior doors. Otherwise, it might have been hard to stop Dylan from entering and seeing me in all kinds of compromising positions, though I've found myself wishing he would more and more these days. I really needed to get laid.
"Uh...hey, Felix? Are you in there?"
"Uh, yeah, Dylan?" Of course I was in my room. He'd seen me come in here.
"I, um, I could use your help with something."
I looked down at my naked body and the butt plug I had inserted to loosen me up while I tried to convince my chat buddy to come over and be my fuck buddy for the evening. "I'm kind of in the middle of something. Can it wait till later?"
"...no, not really. I think I made a mistake."
He sounded kind of scared. I wasn't sure what he'd done, but if he was nervous or embarrassed, it was probably for a good reason. Still, I didn't want to give up on my booty call, so I grabbed a tight fitting thong to keep my plug in and threw on soft shorts and a t-shirt. With any luck, this wouldn't take more than a minute and I could return to seducing shy, young gay boys.
I opened the door and found a mostly naked Dylan with a panicked expression, a pink razor, and a bare patch of thigh with several nicks that welled with bright red blood. A mere towel was the only covering between his muscular form and my hungry eyes, and I thought I could see the barest outline of his cock against the fabric.
"Can you help me?" He was frank in his plea, although I don't think he knew how provocative his appearance was to my already excited body.
"You're shaving your legs," I said, dumbly.
"Yeah," he replied. "You said it was a good idea, for the assignment?"
My brain took a minute, but it caught up. "Oh, right. Holy shit, you're actually doing it?"
He blushed marvelously! He adjusted his towel with nervous energy, and my heart started beating out of my chest. "It seemed like a good idea..."
This was a once in a lifetime opportunity. My totally hot, totally straight roommate was asking me to help him shave his legs. This meant I'd be watching him, nearly naked, as he tried to remove hair all the way up to his groin probably. Did he want me to do it for him? My mouth watered at the thought of getting my hands that close to his cock.
Then again, he was still straight and probably going to tear his skin to shreds if I didn't help him. He didn't need me perving out on him when he was freaked like this.
"Okay, just head back in there and give me a second. I'll be right there."
He smiled with relief and scampered back to the bathroom while I tried to think. I still had the plug in my ass and a total hard-on. I probably should have removed it, but the entire situation was making me even hornier than I'd already been before. When I was finished helping him shave, I was going to come back here and pound my ass with the biggest dildo I owned.
Dylan was sitting on the toilet lid, waiting mostly patiently, though his leg was bouncing up and down with nervous energy. He was still clutching the pink razor, and a bottle of shaving cream sat nearby.
I did my best to avoid staring at his crotch, but his muscular torso wasn't much better on my straining cock. "Okay, first things first: did you shower and exfoliate before you started?"