My Bi Journey

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 Bolu Escort 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 Bolu Escort Bayan 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?

Work absolutely dragged by that evening- all I could think about was that site, and how easy Jay claimed that it was to find someone for anonymous sex. I wasn’t going to meet up with anyone obviously, but why not create an account and see what was out there? I agonised with indecision for my entire shift. I was going to create an account and see if I could find someone that I wanted to fuck. No, I wasn’t gay, that was crazy talk. But I could just login and see what it was like, right? That wouldn’t mean anything.

I got home late, around midnight, and sat in front of my laptop. I was going to do it. It’s not like I was actually going to meet up with anyone, I was just seeing how it worked. I entered my email address and created an account. The site prompted me for some personal details- fortunately a photo was optional, and I elected not to upload one. The details got more personal: position? Versatile, I guess? HIV status? Big negative. Cock length? Oh wow, they just get right in there. I filled out the minimum amount of information, wrote a bio mentioning that I was a first timer, and clicked save.

I found myself on some kind of home page, listing all of the guys that were online in my area. There were a lot, but fortunately there was a search function.

I filtered to people roughly my own age and had a browse. It was obvious why I had thought that Jay was on a porn site, most of the profile pictures were very explicit nudes. A notification popped up: I had a message? Damn, that was quick. I opened it.

It was from a guy about thirty years older than me, and only said one word: Suck? It wasn’t clear if he was asking to suck me, or if he wanted me to suck him. Not interested. A few more messages arrived in quick succession. Let me fuck your tight hole one read- nope. Want me to destroy that ass?- hard nope. Most of the messages were making me super-uncomfortable; they were pretty aggressive, and not really from the demographic that I’d had in mind. A little overwhelmed, I closed the website. It seemed like looking was easy, but finding someone that I might be interested in was hard. I watched some porn, jacked off, and went to bed.

The next night I went out with Jay and the girls- we got trashed at a cheap bar in the city, then went to a gay club. The girls left early, and I tried unsuccessfully to help Jay pick up. I didn’t try to find someone for myself at all, my initial brush with dating in the gay community had kind of scared me off the whole idea. We got home, and I tried logging in to the dating site again. I had about forty unread messages, but I didn’t even read them. I browsed some guys that were online, checking out their profiles and ogling their nudes. I imagined messaging someone and taking a cab right over to their place. Pushing them down on the bed and lowering myself onto their throbbing cock. The fantasy turned me on, and I jacked off with my fingers inside me.

I got pretty busy with work and uni, and I didn’t have a lot of time to spend on sexual fantasies. I kind of put the whole thing out of my mind for a couple of weeks- it was just a temporary thing, I wasn’t gay and I was glad that I hadn’t acted on it.

I made plans to go out with Jay one Thursday- a bar that we liked did a super-cheap student night, and we planned on getting written off. Jay had been seeing some guy semi-regularly, so we hadn’t spent as much time together in the past few weeks. He came after work and immediately got showered and changed. I was a little confused, we hadn’t planned on heading out for another few hours.

“What’s your hurry? I figured we’d have dinner before we headed out.” Jay didn’t reply immediately, just let out a lengthy groan.

“I’m sorry dude, I forgot that we had plans. I’m meeting Stu for dinner in like fifteen minutes.” Of course he was; Jay was a good friend when he was around, but he was flaky as fuck. I told him that I didn’t mind, although I kind of did, and that I’d make some other plans. Jay apologised profusely, dressed hurriedly, and was gone.

I wandered the house a little aimlessly. The girls were out; Sam had gone to her parents’ place, while Kate was out with a friend from high school. I thought about ordering a pizza, but I wasn’t really hungry. I headed back to my room and tried to find something to do.

I browsed Escort Bolu the internet for a bit before deciding to log back in to Jay’s dating site. I was curious to see how many new messages I had received. I opened up the screen, and checked the messages page. There were about sixty unread messages now. Wait, make that sixty-one! I opened the message; it was fairly polite, asking if I had made plans that evening. I had, but then my friend flaked on me. I decided to reply to this stranger, and told them what had happened with Jay. They replied almost immediately- That sucks, it’s a pretty shitty thing for a friend to do… but does that mean that you’re free this evening??. I laughed out loud when I read their reply, it was pretty smooth. I checked out this guy’s profile, and he was nothing special. He was thirty, about ten years older than I was, average weight and height. But he had a kind-looking face, and his profile was well-written.

What did you have in mind? I sent back after a few minutes. I figured that he’d come back with something sexually explicit, and that would be that. He came back fairly quickly- I could give you a massage? His profile had mentioned that he was a masseur, and I’d never had a professional massage before. I started to type that back to him, then stopped. We weren’t just talking about a massage here, this guy would probably expect sex too. I opened his profile and checked him out again. He was cute enough, if a little older than I had been planning for, and he had some additional pictures that were locked. I sent him an unlock request along with the message “Can I see your pics?”. He obliged and unlocked them, and asked if I could send some pictures through. I checked out his pictures first- they were mostly dick pics, and it looked pretty good. Based on the photos he would have been about 6″, a little smaller than my dildo. It was straight and in my inexpert opinion, a nice-looking dick. I started getting hard- I was looking at another guy’s cock here on my computer screen, with the very real possibility of it being inside me. What should I do?

I got up and left the computer screen, pacing back and forth. Shit, what should I do? I wanted this, didn’t I? But what it would mean for me if I went through with it? Randomly meeting a guy over the internet, then heading to his house and jumping on his dick? I didn’t do that kind of thing. I sat back down in front of my laptop. I was just going to jack off, using his pics for inspiration. But it hardly seemed fair.

He’d asked me for a picture, and if I was going to use his pics to make myself cum then I should at least return the favour. I sent a message asking him to hang on and fetched my camera. I had never tried to take nude pictures of myself before, and it was harder than I thought. Eventually I got some reasonable pics of my cock and derriere, but it took me about twenty minutes of posing and deleting. I sent the pics through.

It took him a little longer to reply this time, and I thought that maybe he had logged off. HOT pics, I’d love to give you a rub down tonight if you’re free. He was still online; I reviewed his pictures again and imagined how his cock would feel going inside me. The idea was hot, but the reality made me nervous- what if it hurt? What if I had trouble relaxing, like I often did, and we couldn’t fuck? How would he react?

Sex was definitely off the table, but if he was happy just to give me a massage, where was the harm in that? I messaged him back, asking him where he lived and he replied right away. He was close, only about a fifteen-minute drive. I got up from my computer again and paced around my room, filled with nervous energy. I told myself that I could just go over there for a massage, but I knew that he would want more than that, and the truth was that I did too. I flip-flopped back and forth- I was going to go over and fuck him. I was going to go over to his place, get a massage, and leave straight away. No, I was going to close the site and jack off.

As I agonised over my decision, my phone went off. Jay had sent me a message asking if I would be home tonight, as he and Stu were coming back to our place. I texted him back telling him I would be out tonight, and sat back down at my computer.

I’d love a massage, what’s your number? My hand hovered over the enter key for a good thirty seconds, then I sent my response. I got up from my pc and used the bathroom; his response had arrived by the time I got back, giving me his phone number. I entered the number into my phone and sat at my desk, filled with nerves. After a minute, I sent him a text asking for his address. He sent it to me and I looked it up- not too far away. I told him I would be there in about half an hour.

I got up from my desk and headed to the bathroom-if I was getting a massage, I should probably have a shower first. I cleaned myself off, and had a shave. I inspected my naked body in the mirror, critically checking out myself out. My ass was a little hairy, and on an impulse I decided to shave it. As I did so, a little voice in my head kept asking why I needed a smooth asshole to get a massage, but I ignored it. I didn’t want to admit it to myself in case I freaked out and bailed, but I wasn’t just getting a massage.