An Honest Man

This story takes place maybe eighteen months after my first same-sex experience, which I have also written about. After my first, very positive experience with gay sex I had continued to test the waters, using the same online dating site that I had used to find my first partner. I met up with a couple of guys, some of whom I slept with. I had some pretty average experiences, and a pretty bad one with the last guy. He kind of just jammed his dick into me without any real foreplay or lube which hurt A LOT, and then got upset when I didn't want to continue. This turned me off the idea of dating a guy, and shortly afterwards I met a girl at university, started up a semi-serious relationship, and put my bisexuality on the shelf.

I was pretty happy with her as we had a lot in common, but after about a year she grew distant, and I felt that she was losing interest in me. We split up, and within a few weeks she was dating a guy from her work. I still lived with Jay, Sam and Kate and they did their best to help me drink my troubles away.

After a year of exclusively heterosexual intercourse I was eager to resume my exploration of gay sex, and I reactivated my dating account. After my last experience I wasn't sure if I was ready to start same-sex dating again, but I thought that I might test the waters a little.

It was on this website that I met Justin. Unusually, his display picture was a head shot rather than a blurry nude, and he was VERY cute. I opened up his profile and read about him- he was 23 (I was 22 at the time), about my height, athletic build. I was in pretty good shape, 5'11" and 74kg, and I exercised regularly, but I usually preferred guys with a dad-bod. He wasn't my usual type but as I say, he was very attractive. His profile said that he was a top, but didn't list much more detail than that.

It was a Thursday afternoon, and he was online, so I decided to send him a message. This was also a little out of the ordinary for me, as I would usually just trawl through the guys who had contacted me and respond to ones that caught my eye. As I said, I'd had some bad experiences which made me a little picky when it came to finding guys. I messaged him something casual and uninventive like Hi, how's it going? and we started talking. Like me he was a student, though he went to a different university, and we chatted about our studies and flirted a little. I mentioned that I was looking to get back out there, and we talked a little about our sexual preferences. It was going well until I mentioned that I wasn't really into big dicks- he replied and told me that he was pretty well-endowed, so he probably wasn't my type. I asked how well-endowed, and he told me that he was about ten inches.

Mentally I immediately adjusted this to eight inches, because in my experience most guys exaggerated by an inch or two. This was still a little bigger than I was comfortable with, particularly after such a long hiatus, and so I agreed and told him that we probably weren't sexually compatible. He took this in good humour (I'm guessing he'd heard it before) but pointed out that we didn't have to do anal to have fun.

He was very cute, but I wanted to ride a dick and made a pretty non-committal response about meeting up sometime. I figured I'd be able to find other plans pretty easily, but I did ask for his number. Why not hedge my bets?

I browsed the site for another couple of hours on and off, chatting with a few guys and not really making any progress. I logged off around dinner time, hungry and sexually frustrated. I was working Friday, Saturday and Sunday night, so if I was going to have any fun this week it would be tonight. I ate dinner with Jay and Kate, both of whom were planning an early night, and mulled it over. Would I rather stay at home, watch tv and jack off to porn, or meet up with Justin and 69 each other?

It probably says a lot about my character that this was a real struggle for me.

I decided to eat my pride and send Justin a message. Worst-case scenario, I have to stay at home anyway right? It took him a little while to respond, and by the time he did I was in bed watching tv.

Hey sorry for the late response. I'm out with some friends from work.

Serves me right. I messaged him back telling him it was cool, we'd catch up another time. This time he replied straight away.

Or you could meet us out 😉

That gave me pause. Meeting up with a guy I had never met and socialising with his friends seemed like a lot of work, though Jay did it all the time. I resumed watching tv and lay back, it definitely sounded like too much effort. Five minutes went by, and I was bored out of my mind. Fuck it, I could use a drink.

I asked where to meet them and he told me they were at a bar about half an hour from my house, on a street full of trendy bars and restaurants. I got dressed quickly in a collared shirt and some jeans, then went and begged Jay for a lift, mostly because parking in that area was a pain in the ass.

I hadn't come out as bi yet, so I told Jay that I was meeting some friends from uni and hoped that he wouldn't want to come in for a drink. Fortunately, he didn't; he had work in the morning and wanted to get to bed early. Honestly it could have gone either way, Jay was a loose cannon.

I walk inside the bar and it's very crowded. I'm not sure how I'm going to find Justin and his friends, so I pulled up his photo from the dating site on my phone. After a few minutes of walking I catch sight of him sitting at a table with a few other people in the back corner, and I head over. As I approach the table, I make eye contact with this girl standing next to Justin and she smiles at me, assuming I'm coming over to make a pass at her. She's wearing a tight dress and stripper heels, with long brunette hair and she is quite drunk. She comes toward me a little as I get closer.

"Oh heeeeeeeey" she tilted her head to one side and flashed a wide smile, staggering a little as she did so. Behind her, Justin recognised me and stood up.

"He's here to see me actually Liz" He brushed past her to greet me, and her face changed to a scowl.

"The cute ones are always gay" She said as she sat back down, a comment that Justin and I ignored.

He looked as good in person as he had in his pictures, and not everyone does. He introduced me to his friends, all of whom were surprisingly attractive, and it turned out they were all bar and promo staff, most of whom were part-time actors or models or both. I kept in pretty good shape back then but am otherwise pretty average-looking, and I felt a little out of place in this group of confident, sexy people.

I sat down next to Justin and we chatted briefly before he offered to buy me a drink. It was an expensive place so I agreed, and he left to go buy me a beer. The brunette girl was sitting at the next stool over, and she shifted closer to me. She started to ask me questions about being gay, and whether I had always known, and I replied and told her that I wasn't gay, I was actually bi.

"Reeeeeaaaaallly" she drew the word out and punctuated it with a long sip from the straw of her drink. Justin came back with our drinks and the three of us chatted a little. Justin and Liz had a seemingly bottomless well of funny stories from the bar that they worked at, and I laughed along with them.

I got up to use the bathroom and get a second drink- Justin was still nursing his and didn't need another, which was fortunate for me given the prices. As I came back to the table he and Liz were still talking, but Justin seemed to be a little annoyed by her now. I sat back down and they abruptly stopped the conversation, and Justin I started talking about our musical and tv preferences.

He seemed like a nice, genuine guy and we really hit it off. Neither of us brought up sex, although I could feel a mutual attraction between us. After a while he got up to freshen his drink, and Liz slid back over next to me. She had sobered up a bit and was a little less obnoxious now, and my impression of her changed a little.

She started talking to me about my bisexuality and while I was uncomfortable at first, it felt good to share it with someone. I was still very much in the closet about it and had never really had the chance to discuss it openly with someone before, and I enjoyed the opportunity. Justin came back and got drawn into a conversation with a pair of guys on the other side of the table, although he kept shooting anxious looks my way. I think he was worried that Liz was going to scare me off, though it's possible he thought that I'd end up going home with her.

I didn't mind, I was enjoying myself. We talked about sex, the things we liked guys to do and what we didn't like, and it was really refreshing to be able to talk openly with someone about all of this. As our conversation got more specific and explicit I started to get aroused. I was sitting here talking about how much I like getting a rim job, and a few feet away was someone who'd probably be willing to make that a reality. I started to get a little hard thinking about it.

Justin came back over and we talked and joked and drank. I started to get a little buzzed and my conversation with Liz had made me horny. He got up to use the bathroom and my eyes followed him lustfully.

"Are you going to fuck him?" Liz just came out and asked it. I thought about it for a second before answering.

"I don't know, maybe?" I really wanted someone to fuck me, but an 8" dick was a little bigger than I was comfortable with.

"I heard he has a HUGE cock. Think you can take it?" Liz was smiling at me, enjoying how uncomfortable her questions were making me.

"Honestly? Probably not, like I said before I like a more modest cock in my ass."

"So don't put in your ass. You suck his dick, he eats your ass, everybody wins!" That actually sounded like a great idea, and I made my decision. Justin was standing over at the bar, waiting for service, and I got up to go over to him.

"Good idea. Bye Liz!" I stood up and winked at her. As I went to walk away, she grabbed my hand.

"Wait, can I have your number?" I was surprised that she'd asked. I'd had a good time, and it occurred to me that I'd spent as much time talking to Liz as I had talking to Justin. I briefly flicked my gaze over her, taking her in from head to toe. She wasn't my usual type; when it comes to women I like tits, hips and blonde hair. Liz was slender, flat-chested and had brunette hair almost to her waist; but she was very attractive, although her aesthetic was a little makeup-heavy for my taste. I held out my hand for her phone and entered my number.

"Justin owes you a drink." I told her before I walked off. It was true, she'd pretty much talked me into it.

I headed over to Justin and leaned in close to his ear.

"Did you wanna get out of here?" He turned to face me, a smile on his face, and nodded enthusiastically. He lived nearby, a long walk or a short drive, and we elected to take a cab. We both sat in the back seat and I looked over at him appreciatively. He was less muscular than me and a little shorter, with glasses and a clean-cut aesthetic. He was well-dressed in a collared shirt and blazer, with tight jeans which showed off his package just a little.

"Hey, I hope Liz didn't make you too uncomfortable. She can be a lot." His tone was apologetic.

"Not at all, I enjoyed talking with her, though she did ask me some pretty intimate questions." This was a bit of an understatement, but talking with Liz had actually made me feel much more confident. He chuckled a little before replying.

"Yeah, you know how some guys are totally into Lesbian porn? Liz is like that with gay dudes, she has a total fetish for it." He paused for a moment before continuing. "When you first arrived, she was trying to convince me to let her watch if we ended up sleeping together." He laughed and shook his head a little.

I was a little surprised, I had thought that Liz was just being a good wing-woman for Justin, but it sounded like she might have had an ulterior motive. I wondered idly if she was disappointed that she wasn't getting to see the live show.

We arrived at his place and quickly made our way up the stairs to his apartment. It was a tiny studio, just a bedroom with an ensuite and a kitchenette, which explained how he was able to afford rent in this part of town. I moved quickly to his bed and lay down, patting the mattress beside me invitingly.

He needed no encouragement, straddling me immediately, and I pulled him down for a long kiss. I could taste the wine on his breath as we kissed, and I could feel his cock pressing up against me through his jeans. It felt big, and I reached down to check. It felt very big, and a little flutter of anxiety passed through my chest.

He unbuttoned my shirt and kissed his way down my chest before opening my fly. He smiled up at me questioningly and I nodded quickly. His mouth found my cock and I moaned in pleasure, his lips moving up and down my shaft as his tongue explored the head. He gave really god oral which surprised me a little, as some tops don't do it at all. His head bobbed up and down on my rock-hard dick and I started to leak a little pre-cum.

He moved back up to kiss me again, and I rolled him over so that I was on top. My turn now. I unbuttoned his shirt and kissed my way down his chest as he had with me. One hand reached down the front of his pants to grasp his cock while my other undid his fly. Oh my god, his dick felt absolutely huge! With some difficulty, I pulled it out of his pants.

He hadn't exaggerated at all, if anything he'd undersold it. This was a legendary cock. It would have brought no shame to a horse. It was easily ten inches long, and thicker than three of my fingers side-by-side. As it came free of his fly I just stopped and stared; I had never seen or expected to see a cock this big in real life. Naively, I didn't think that dicks could really be this big- they only existed in porn films, the product of gifted actors and trick photography. I had no idea what to do with it.

"I know, it's a lot." Justin laughed at my reaction, but a little nervously. "We don't have to do anal or anything you aren't comfortable with." His voice wasn't the confident voice of a guy with a big dick, but rather the uncertain voice of a guy with a monster dick who is worried that his chances of sex are vanishing. I regained my composure after a second or two and smiled back at him.

"Putting this dick in my ass would be many things, but comfortable isn't one of them." I ran my tongue up and down the length of his cock before taking the head into my mouth. It was simply enormous, it was a challenge to fit it in my mouth, and as I worked my head up and down my teeth gently scraped the sides a few times. I took hold of it in both hands, working them both up and down the shaft while my mouth worked on as much of the head as I could comfortably fit. He lay back and moaned in appreciation, but I was pretty confident that I wasn't doing as good a job on him as he had on me. I felt a little bad, it was going to take me ages to make him cum like this, but there was no way I was going to let him fuck me with it. It was a little disappointing, I had really wanted to get fucked and talking about riding dick with Liz had made me want it even more. But in the back of my mind there was a small part of me that wanted to try; I felt like if I could conquer this mighty dick, then no subsequent dick would give me pause.

You can probably tell where this is going.

After a minute or two I came back up and kissed him, pulling my pants all the way off. He did likewise and I straddled him, rubbing my hole up and down the length of his cock. His cock was still a little slick from my mouth and I teased the head of his dick with my hole as we kissed. I slid over to lay beside him and started to stroking his cock with my hand. He reached down and teased me with his fingers, circling my hole. I let out a little moan and he licked his fingertips before easing them into me, just a little. I took his cock in my mouth again as he fingered me and worked my hands up and down the shaft. After a few seconds he asked if I'd like to try a toy, and I nodded enthusiastically. He reached over to his nightstand and produced not one but three butt plugs of increasing size. The smallest was only a little thicker than my finger, whilst the largest was almost as thick as his enormous dick.

Gee, I wonder what we'll need those for?

He caught me staring and looked a little uncomfortable.

"They belonged to my ex. Don't worry, I've cleaned them" he reassured me. By way of answer I rolled over and got on my knees, offering him my hairless asshole.

"Start small I guess." He knelt eagerly between my legs and drizzled a little lube over my asshole. I was very nervous, and my asshole was correspondingly tense. Fortunately, the first butt plug was small, and after a few seconds of gentle pushing I was able to take it in. I'd never used a butt plug before, and it surprised me a little the way my ass drew it in after we got past the half-way point. He worked it in and out a few times, opening me up a little, and I shivered with pleasure each time it entered me.

"Use the next one." I moaned, and with a smile he complied. The second toy was a little thicker, and more like what I thought of as regular cock-width. It was a little harder to get in this time, but with a little extra lube my ass soon yielded to the gentle pressure. There was a slight curve to this one that pressed on my g-spot and I gasped in pleasure as he moved it inside of me. Precum was leaking from the tip of my cock now and I tried to will myself to relax, not wanting to cum too soon. There was still another toy to come, and I wanted to at least try it. We spent more time with this one, gently moving it in and out of my ass until I relaxed enough to accept it easily. I looked back at him and smiled a little.

"Try the big one now." This last butt plug looked very thick and was longer than the other two which meant that fortunately it started off quite small. I'd never tried to put anything this big inside my ass before and even though I was already pretty relaxed, it wasn't going to be easy.

He eased it into me and we reached my limit about two-thirds of the way in. He stopped and held it there, allowing me to push back against it. I dropped my head to the mattress and spread my knees as wide as they would go and was rewarded with another centimetre or two in my ass. I breathed out and tried to relax, pushing back against this toy. I could feel my asshole spreading wider than it ever had before, and wondered if it was even possible to fit this butt plug inside me. Another breath, another push, another centimetre.

He withdrew the toy and rubbed my lower back.

"Wanna try the smaller one again?" I looked back at him and shook my head. My asshole was tingling but it didn't hurt, and I wasn't ready to give up yet. He held it out for me and I pushed my ass up against it, trying my best to relax. It got further in this time, and I could feel that I had it nearly all inside me. I breathed in and pushed back again, and with a pop and a flash of pain it was inside my ass. I yelped in surprise and breathed heavily. He rubbed my back and soothed me a little before slowly withdrawing the enormous toy. I let out a shuddering moan as he eased it back inside me, slowly overcoming the resistance offered by my asshole. He moved it around, easing it slightly in and out of me, rotating it a little. The sensation was overwhelming, the feeling of being stretched was almost too intense. The medium-sized butt plug had felt much better. I looked back to see him stroking his enormous cock; filling my ass with these butt plugs must have been driving him crazy and there was a steady stream of precum leaking from his tip.