Hi Ms. Angel,

I recently hooked up with guy, and he’s got the biggest dick I’ve ever seen. I don’t know if I can handle it. We tried, but it was too painful, and I got scared off. We did other stuff, but I could tell he was disappointed. I’d like to try again. What can I do so it feels better next time? – Bruised Bottom
Dearie, you are not the first to have this issue, and the large number of readers who are likely jealous of your situation should be a sign that this is a very surmountable problem.
The first step is to relax. You want this, he wants this, it will just take some time. Going in butt cheeks blazing is a certain way to end up struggling to walk for the next few days. Your ass is naturally going to be tight, meaning you’ll need to stretch it like any muscle. This is something you can try on your own, either with your fingers (if you’re that flexible), or toys. Dildos coming in many sizes, and even starting with one smaller than your friend can be a good way to get used to new sizes.
With your toys and boys, be sure to use lots and lots of lube. Honestly, it’s almost impossible to use too much. Find one you like. Water-based is best to use with toys and condoms. Silicon-based lube can last longer, but can damage toys and condoms. It also leaves stains, so be sure to cover your bedsheets.
When you and your friend next become amorous, spend more time in foreplay. Have him lube up his fingers, and warm you up that way first. Get comfortable, relax, and feel good about what you’re doing and who you’re with.
When you’re ready, different positions can make anal feel so much better when there’s a size issue. Trying being on top, which allows you to control the depth and the pace. Missionary can also be good, as it’s easier to relax and control how deep the cock goes.
Be sure to speak up about what you’re feeling. If this guy is worth it, he’ll go slow and get you comfortable. Don’t feel forced to go faster than you want. Pain should be planned, not pressured.
However, if this doesn’t work out for you, please send this guy my way. He sounds like my type.
With love,
Ms. Angel Food