My bisexual journey started with my housemate, but not in the way you would expect. Jay and I had been friends at school, and he came out as gay after we had graduated. We got pretty close and moved in together, sharing a house with two girls, Sam and Kate, that he'd met through work. The girls kept mostly to themselves, but Jay and I spent a lot of time together. If we felt social, we'd leave the door to our room open, and we'd wander into each other's rooms and hang out fairly frequently.
Jay had left his door open one afternoon, and I felt like a chat, so I walked right on in. He turned guiltily away from his computer screen, and I assumed he'd been watching porn. I was half right, it looked like some sort of explicit chat room. I asked him what he was looking at, and he kind of shrugged and closed it down.
"It's a gay dating site. You search for guys in your area, and you can send them messages and stuff." This was before the days of tinder, grindr, or any of the many dating apps that people use and abuse these days, so I was intrigued. He said that he'd been chatting to a guy over this site and was going to meet him at a gay bar later that evening.
"You found someone that quickly?" I was surprised, in my experience dating was a week or two of texting before really getting anywhere.
He laughed and said "It's pretty straight forward. I can login any time and meet up with someone within a few hours." We chatted about other things; he invited me out, but I declined as I had to work the next day. We ate dinner together, then Jay headed out with the girls to meet his online beau.
I chilled out, and watched Will and Grace on dvd. I wasn't expecting to see my housemates again before I went to bed, so I was surprised when the front door opened around nine. I could hear Jay's voice downstairs, and I figured that his surefire internet date had stood him up. I left my room and headed for the stairway to razz him a little- he'd been pretty smug about how easy it was for him to find a date. As I got to the landing, I heard a second male voice- looks like his date had shown up, and things were going well. I didn't want to kill his buzz, so I ducked into the bathroom and locked the door. I heard the two of them come upstairs, then Jay tapped lightly on the bathroom door.
"Hey man, you in there? I thought you'd be asleep by now." Of course, I'd left my bedroom door open. So much for making myself scarce.
"Yeah dude, I was just about to take a shower. I'll be a little while if you wanna use the downstairs bathroom." Jay whispered to someone on the other side of the door, followed by some giggling and shushing noises.
"All good, take your time man." I enjoyed lengthy showers, and it had become a bit of a running joke among my housemates. I heard the two of them move down the hallway to Jay's room and with not many options, I ran the shower and hopped in. I kept it short, only about ten minutes or so, just enough time for Jay and his date to become preoccupied with other things. Towelling off, I opened the bathroom door and headed back to my room. Mine and Jay's rooms were shared a wall, but I slept with earplugs and the walls were thick.
As I approached his door, I noticed that it wasn't latched properly and swung open a crack. I could hear rhythmic moans and grunts coming from within. Jay and I were pretty open with one another, but I didn't think he'd be comfortable with me perving on him during sex. But I couldn't resist sneaking a glance as I walked past and opened the door to my own room. Jay had his date both had their backs to the door; Jay was holding tight to the head of his bed frame while his date was energetically thrusting. So Jay was a bottom? A minor mystery cleared up, he was always cagey about his exact preferences.
I got into bed and lay there by myself, wishing I knew of a similar website that catered to heterosexual men. I fondled myself in the dark, but I wasn't thinking of women. I was imagining how it would feel to be in Jay's shoes, clinging to my headboard while someone entered me from behind. It wasn't the first time I had flirted with the idea, but I was surprised with how much it aroused me now. When I'd first moved out of home I'd been curious and bought a dildo, but the couple of times I'd tried it had been frustrating, unpleasant and on one occasion when I was feeling bold, painful. I kept it in a cardboard box in the top of my wardrobe, and hadn't taken it out in a long time. Without my ear plugs I could hear Jay and his date in the next room and on an impulse, I took the shameful box down.
I opened the box and pulled out my rubber lover. I'd been too shy to spend much time picking one out and too cheap to spend much money on it, so I'd grabbed a pretty basic toy. It was 7" long and as thick as three of my fingers, a veiny purple rubber monstrosity. In retrospect, if I'd spent a little more and purchased a more modestly sized toy, I might have enjoyed myself more. I drizzled some lube over the tip, drew my knees up, and placed the tip up against my tight hole. I pressed gently, rubbing the tip back and forth while I stroked my cock- I had more or less given up on getting it inside me. My hole started to relax and I was able to get a little of the head inside me. That small pressure was enough to satisfy me and I came quickly, shooting jets of hot cum over my stomach and chest. I wiped myself off with the towel and wished that I'd done this before my shower and so, a little sticky, I went to sleep.
A few weeks went by, and I fantasized about getting fucked every few days, bringing my dildo out of its box and rubbing it across my throbbing hole. The pressure and movement aroused me and it always made me cum quickly, but I wanted more. I was too shy to ask Jay about it, and worried that he'd want to get involved- he'd made passes at me before, but I just wasn't interested. If I was going to hook up with a guy, it wouldn't be him.
Some discrete searching turned up a forum offering advice for first-time bottoms, and I learned a little about how to open myself up and relax more. I wasn't convinced that this was something I wanted to try, but decided to have a go at exploring myself with my fingers. I discovered my g-spot and that maybe became a BIG yes. The forums recommended a smaller toy to begin with, but I wasn't brave enough to go and buy another one, so I persevered with my cheap rubber cock.
I still remember the night I finally got it in- I'd been drinking with my housemates, and talk turned to everyone's first time. Jay and the girls talked about their first cock, and how it had felt inside them, and I wanted to know how it felt. I was buzzed and horny when I went to bed, and I pulled up some porn to jack off to. All this talk of cocks had aroused my fantasy of being fucked, so I pulled up some gay porn and started to stroke my cock, imagining a hard dick entering my willing hole. I got close to cumming and stopped- I wanted to know what it felt like. I took out my dildo and lubed up my hole with my fingers, working up from one to two. Normally I was super nervous and tense when I did this, but in my tipsy state I easily relaxed and was able to fit not just three, but all four of my fingers inside my tight asshole. I moved them around, marvelling at the feeling of fullness but wanting to feel something deeper inside myself. I lay back on the bed, applied a generous amount of lube to my dildo and asshole, and started to press the toy against my hole. I kept up an even pressure and felt the tip start to slide in easily- it startled me, and I tensed up. I breathed out and tried to relax, resuming the even pressure against my asshole and once again the dildo started to slide inside me. I could feel myself relaxing, but I couldn't quite get the head completely inside. I withdrew the dildo and started to jack off, and I could feel my asshole throbbing with each stroke. One more try. I breathed out again and pushed the dildo into my asshole. It stuck for a second at the base of the head, then with a popping sensation it slipped inside me. Success! I lay still for a second, enjoying the feeling. It was uncomfortable but not painful, and gave me a delightful feeling of fullness. Slowly, I pulled the dildo back out of my ass, then pushed it back in. It went in more easily this time, and I pushed a little more of its length inside me. It was about the same length as my own cock, although a little thicker, and I wanted it all the way in. I withdrew it again, feeling little electric thrills as the rubber veins massaged my asshole, and covered it with a generous dollop of lube. I was doing it!
I pushed the dildo into my ass, loving the feeling of fullness and being stretched that it gave me. On my computer screen the porn was still playing, and I tried moving it in time with the actor's cock. Too fast, too hard, not fun. I slowly moved the dildo in and out of my ass, gently stroking my dick in time with the thrusts and trying to angle the head so that it would rub my prostate. It felt good, but the sensation was strange and almost intrusive. I stopped moving the dildo, pressing it up against my g-spot, and stroked myself to a huge orgasm. Much to my surprise, my ass contracted as I came and the dildo shot out of me painfully quickly. A little sore but satisfied that I'd finally gotten it in, I went to sleep.
I played with my dildo on and off over the next month or two, although truth be told it was a little too big for me, and each time I fucked myself with it was a bit of challenge. I still regularly fantasized about getting fucked, but I wasn't going to act on it. All the gay guys I knew were friends with Jay, and I wasn't ready to be outed as bi yet. I wanted it though- getting down on my knees to service someone, drawing my legs up and feeling someone between them, offering up my ass and feeling a warm, throbbing cock pushing at my eager hole instead of hard, unyielding rubber.
I hadn't given much real though to making my fantasy a reality, until one evening when I had to work. Jay had parked me in, and he'd already headed out for the evening. I gave him a call, and he told me to take the keys from his bedside table and move the car myself. I headed up to his room and grabbed the keys, glancing at his computer screen as I did so. He'd left his computer on, as he usually did, and the browser was showing the login screen for his gay dating site. That gave me an idea, and I scribbled the url down on a piece of paper and shoved it in my desk drawer. No harm in checking it out, right?
