Middel Aged Overweight Newbie Alert!

[Eribiste]

Practice changing an inner tube on the back wheel of your bike in the comfort of your home and garden,better than in the pissing rain at the side of the road and finding you dont know how to get the tyre on the rim and the wheel back on the bike.

Excellent advice here from User46386.

I'd do your rides little but 'fairly' often. Take your time and let the distance endurance come to you. If you are going to ride on colder days I can heartily recommend a Merino wool base layer. If and when you start to extend the distance that you and your chum ride, I'd have some flapjack bars or similar in my back pockets so that you can treat yourselves when you achieve a particular distance or some such goal.

As someone has already said, pictures are needed!

 

[EnPassant]

Learn to put your typo's in the middel of the text, they are less noticeable then.

I was exactly where you are now a bit ago. All the advice here is excellent, and yes, it was my arse that surprised me, it gets better with more miles, you don't think it will, but it does.
I expected and got, tired, out of puff, frightened by cars etc. and was ready to deal with those as they came up. The rear end? That was a shocker to me.
It really does get better after a bit of time in the saddle, a few weeks maybe, I don't really know why, I've looked in the mirror and it doesn't look any different (not a picture you will want to hold in your head for long...) but somehow it does improve. Just one of those things.

If the reason is primarily weight, and you're a target driven type of person, keep a log, it drives me on on those days I don't really feel like it.

 

[nickyboy]

Practice changing an inner tube on the back wheel of your bike in the comfort of your home and garden,better than in the pissing rain at the side of the road and finding you dont know how to get the tyre on the rim and the wheel back on the bike.

This

Every experienced cyclist has their own idea about what clothes to buy, what tools to take with you etc etc and they will all be slightly different

But 100% of them will say learn to change a puncture with the minimum of fuss. You will get a puncture, everyone does. If it's raining or cold or dark or, worst of all raining, cold and dark you need to be able to deal with it. So as @User46386 says, have several practices at home when it's light and warm outside. You will be surprised how much quicker your attempts will become and you'll be confident doing it at the roadside when you have to.

I did this when I bought a chainbreaker a couple of years ago (it's a tool for fixing your chain if it snaps mid-ride). They're tricky so I had a couple of dummy runs at home. When the chain did snap on a ride I was able to sort it at the roadside without too much swearing

 

[Nigelnaturist]

@nickyboy my last front tyre wore out before it had a puncture 12,000 miles or so, rear did 7,000+ before it got one.

 

[adamangler]

essentials

bike fit (either yourself or pay)
Good saddle - try a few
correct tyre pressures
Padded shorts - yes they are essential imo (good quality ones)
bottles/cages
lights/mudguards (when applicable)
spare tube or 2
tyre levers
multitool
chaintool
spare few links of chain/powerlinks
bit of money, (i keep a tenner in my saddle bag, its been there months but you never know)

learn to do basic maintenance, punctures, set up gears, adjust brakes etc


sure ive probably missed something