The bore on the jugs is the same, yes. I asked the difference to my builder and he showed me the pistons (these were CP pistons, not the HD). IIRC, the oil control rings on a 95" piston actually pass over the wrist pin hole where the piston for the 103" kit has the oil rings above the hole. I think the overall difference in piston height after you attach them to the connecting rod would be your problem unless the HD cast pistons don't have this difference.
Can the kit for a 07 103ci make a 88ci into a 95ci ?
NO!
The bore size IS the same BUT the piston in the 103 kit is for the stroked flywheel (different piston pin height) also 88's have a square ended rod, the stock rod on a 96 is tapered, the kit pistons have the same taper on the pin boss and will not go on a square rod.
Hog-doc summed it up for ya there. That piston won't work with your 88" crank/rod assembly. 3.875 is the right diameter, but the wrist pin location is what hoses you.
I had gotten the kit for my 07 FLHTC and have run into money problems. I had a friend want it for his 03 Softail. So I still have it just not wanting to use it without putting compression releases in when I do it.
I put the 103 kit in my 07 SG don't really think it needs compression releases. I also installed 255 cams ,got factory down load all seems well. It won't help money problems though.