Brian: Taking Courage - 13. Up the bum

Connor strolled across the office and perched on Gordon's desk. Gordon was curious, what had come up to bring Connor out of his tech hub? The guy was in t-shirt and shorts, his standard gear no matter what the weather. There was a mass of hair escaping from the sagging neck of the t-shirt and a distinct bulge at his crotch, but as far as Gordon knew there had been no repeat of the jock-strap incident, though Toby was coming in tomorrow so things might get interesting.

"Could I have a word?"

Gordon looked up at him, "Sure. Now?"

Connor looked around and dropped his voice, "Not really. Look it's not work related, it's kind of personal. Could we meet after work?"

"Hang on, I need to check", Gordon looked at his and Brian’s shared calendar on his phone. This was an essential part of their new life together, with everything logged from shopping expeditions to Ares meetings, school events and Toby’s social life. "Sounds OK. Toby's having his tea with his Gran, so Brian and I could meet you for a quick drink. You did mean both of us?"

Connor flushed at the implication, "Sure. It's nothing underhand. It's just well, advice, you'll probably know more about it being, gay and all."

With that Connor returned to Star Ship Enterprise, leaving Gordon none the wiser. He and Brian chatted about it over lunch but still had no idea. As far as they knew Connor was 100% straight and would hardly seem to need to come to two gay men for relationship advice and neither felt comfortable mixing work and personal advice if it concerned something more complicated, such as Connor actually not being 100% straight and starting to find his gay side.

There was a pub a short distance from the office, and it had tables outside. Inside it was rather down-at-heel, but the beer was good, and the tables were away from the road, so it became their go-to place if any of the team fancied a quick drink after work. They settled down with their pints, then Gordon looked enquiringly at Connor.

"This is kind of embarrassing, but I couldn't figure who else to ask. I wanted advice about taking it up the bum."

Both Brian and Gordon stared at him, "You want to do it with a guy?"

Connor laughed, embarrassed, "No. Bloody hell. No offence, but guys aren't my thing."

"Then what?"

"Me girlfriend and a dildo."

Gordon grinned, "Ah, pegging."

"Yeah. Can you sort of give advice? We’ve looked on-line, but I figured it’s better to talk to someone that’s actually done it."

Gordon blinked and looked at Brian who shrugged, "How come you're interested if you've no experience?" Neither of them embarrassed Connor further by pointing out that not all gay men had experience of anal sex, it didn’t automatically come with the territory.

"I read about a bloke getting fucked by his girlfriend, and wondered whether this was a thing or not, but I wasn't keen to talk about it in case it sounded a bit too gay", he gave an embarrassed shrug, "Sorry. Anyroad, the girlfriend and I were on holiday in Ibiza, and we got friendly with this other couple and, well long story short, we got pissed and had a foursome. At some point the other girl had both of us doing her, front and back. It was awesome”, he gave an embarrassed grin, “Talking with them the next day, we found out that they did that sort of thing regularly, both him and her, and that he liked taking a dildo up his arse.

"I talked to the girlfriend about it, and she was willing to give anal a go as long as I was. Bloody hell. And she'd talked to a mate of hers who's a nurse and found out all about how you stimulate a guy's prostate. Thing is that I'm willing to give it a go, like, but worry about doing damage if I stick something up my bum or stick my dick up my girlfriend’s for that matter."

Brian was trying not to laugh but had to give the bloke credit for being open minded enough to consider something new, and with the balls to be able to talk about his sex life with his work mates. "OK, that's quite a lot to consider. But we can give you some pointers."

Connor looked relieved, "Thanks. I think the girlfriend's quite keen."

"Right. Well there are a few things to consider", Gordon enumerated them on his fingers, "getting your arse clean, practising with something small, and not being ambitious. When it comes to being clean, a lot of blokes simply make sure they've taken a shit and give everything a good wash. But", he shrugged, "accidents happen."

"Shit."

Gordon grinned, "Precisely. Probably piss your girlfriend off no end, so you'd best use an enema, and just the same for your girlfriend if she takes you up there."

"And what the fuck's an enema?"

"Well, some guys find them a turn-on", Gordon shrugged, "takes all sorts. You shoot water up your bum, into your bowels then shit it out again and do it repeatedly till it's clean."

Connor's face was a picture, Brian added a bit more information, "Warm water. I gather it's not unpleasant, just a bit strange."

"But very effective. So, no accidents."

"OK, and the practising stuff?"

"Well, fingers are good."

"Christ, me girlfriend's got fingernails like talons."

Brian smiled, "So, you'd better use your own. A lot of blokes do; finger themselves whilst having a wank. I imagine you're not keen on getting a mate to do it for you?"

Connor laughed, "Not bloody likely. So, I finger myself?"

"Yeah, use plenty of lube. Works a treat, try one finger then two and so on."

"Alternatively, you can go for gold and simply start with the smallest dildo you can find. You go easy and gently, don't force it and go slowly, let your arse gradually get used to it. Once you are through the ring."

"Ring?"

"Yeah, there's a ring of muscles that, well, stop stuff falling out. Once you're through, you let it rest, let things get adjusted."

"It all sounds a bit strange and painful when you describe it, but I assure you, once you're used to it and you get the dildo rubbing against your prostate then the feeling is fantastic."

"And the third point."

"Even when you're confident, don't go too big too quickly. Don't buy a dildo modelled on some porn star's wang, it's bound to be bigger than you can cope with. I assure you, when you're starting out, you’ll find the smallest dick or dildo feels huge when it's up your bum. And remember that women are usually build smaller than men, if you take your girlfriend right off, you’ll do damage. Finger her good."

"And always start small, each time you do it; get your bum used to it again. The muscles need warming up just like anything else."

"Poppers are good too. They're a muscle relaxant. Not everyone likes them, but it might be worth a try. Might be an idea to talk everything through with the girlfriend."

"You reckon? Even the shit?"

"Everything, so she knows what's involved. If it freaks her out, then it's better to find out sooner rather than later", Gordon smiled, "I used to have a mate who reckoned he serviced a steady supply of straight blokes who were keen on getting it up the bum and whose girlfriends wouldn't countenance it."

Connor smiled, "Bloody hell. Look, can I ask you a dodgy question. You can say bugger off, but do you two do it?"

Gordon nodded, "Yep. We do each other, always have done. I started messing with me arse when I was in my teens, used to use one of me Mum's cucumbers."

"A cucumber?"

"Yeah, they make a decent dildo. I used to wash them down and then put them back", he grinned, "No one ever knew!", the other two grimaced.

Brian shrugged, "I was a late starter, never tried things like that. Then I had a drunken hook-up, and the guy just took it for granted. Bit of a shock for me, and I was bloody sore afterwards, but I knew I'd do it again."

They chatted a bit more, but Connor was keen to get off, though he assured the two that he would keep them posted.

The advice session had left the two of them feeling rather horny. Truth to tell, all three of them left the pub with significant bulges. Once back at the flat, they had plenty of time, but made sure the bedroom door was well closed.

"Christ, all that talk of taking it up the bum, certainly gave me ideas", Gordon grinned as he stripped off. "Now that's a fine sight", he looked down at Brian who had already laid back on the bed, his dick projecting into the air.

Gordon climbed on, going head to tail with Brian so that Brian had his face pressed into Gordon's arse as Gordon applied himself to Brian's dick. He started with the piss slit, teasing it with his tongue then worked his way round the huge head. They took so much time, that they never reached the main act. Brian's phone pinged, letting them know they had 15 minutes to Toby arriving. So Brian slipped his hand round to Gordon's dick and stroked it whilst his tongue was deep in Gordon's hole. They came together, almost.

"Fuck, I needed that."

Gordon grinned, "Well, not fuck, actually."

Brian smirked, "There are different sorts of penetration, we don't have to use dicks every time."

"Cucumbers?"

"I don't think we need to descend to that level."

"What about a dildo?"

Brian shrugged, "Not sure I see the point, when I've got your dick on tap."

"Maybe something bigger?"

Brian's eyes widened, "You mean stretch things a little?"

It was Gordon's turn to smirk, "Well, I'm sure your muscle tone is good."

"Maybe. Something to think about."

"Pervert."

They both grinned.

Sitting in bed, later that evening, Brian brought up a website selling dildos. Some looked alarmingly large, some were long, none seemed remotely feasible.

Gordon laughed, "Perhaps we should take measurements of my dick as a starting point."

Brian shrugged, "Or go somewhere and ask if we can try them before we buy."

"Ew, don’t. That's gross. I think we should follow our own advice."

"Don't get too ambitious."

"Yeah. So, we measure my dick."

Brian leaned over and kissed him, "But not now, I want catch up on what I missed out on earlier."

"I thought you said there were other types of penetration."

Brian gave a smile, "Maybe, but I still want to feel your dick inside me. It's where it belongs."

"My thoughts exactly."