Ugh. Exit only. Not for fun.

massaging the prostate is much more pleasant and even more pleasant with a dedicated sex toy

It’s not “exit only,” but that’s a typical and somewhat ridiculous response. Using a cucumber for the first time you try any sort of anal play was a ludicrous choice. Start with a single finger. Lots of lube. Don’t just stick it in to the hilt. Play around the rim of your hole. Maybe that’s the limit the first time or two. And if you’re worried about “making a mess” pick up an enema at the drug store. Don’t squeeze the whole thing in. Use half, sit on the toilet and let it empty naturally (don’t force it), and then use the other half. Jump in the shower and wash up thoroughly. Lay down a towel (because you’re better off using more lube than you think you need rather than less) and massage your asshole. Stroke your cock while you do it. Maybe you slip a finger in to the first knuckle and play around with putting pressure around the sides. As you get more comfortable, slip more of the finger in. Start feeling around for your prostate. At first you might only notice an unusual pressure. It’s an awkward stretch to get the right angle, this is when you might want to move on to a small vibrator, dildo, or butt plug. Slowly work your way up. Jamming a cucumber up your ass on day one will cause big pain and major cramping. The sphincter is designed to stay closed. You can’t just undo that because you have something smooth and lubed. Take your time. As you get accustomed to sliding things in, experiment with the angle until you find the best one for prostate stimulation as you jerk off. Bate bros can even take control of the anal toy to help you out or you can take turns helping each other out. Whether a solo or buddy activity, it can be extremely intense when you cum while stimulating your prostate.

@mchammer My anus relaxes itself when I insert a prostate massager. I remember the first time I massaged my straight lips with my finger, my eyes were big and my lips were a pleasant surprise.

@kolowskibro Prostate massagers tend to be slimmer, but that’s a rarity rather than a consistent experience. Most sphincters need a slow entry at first. If you’re more experienced, then relaxation becomes quicker. But it should never be forced.

@mchammer I like to dominate myself. If I don't feel pain, I do it quickly to turn on the vibrations and let out the fun with myself

@mchammer Nope. Nope. Nope.

@binoculary 🙄🤷🏻‍♂️

Rimming is very good when clean. Only done it with chicks. Years ago we had great full service Asian places and it was a great part of their routine.

As already been said, start small and work up if you feel it's necessary. Personally, I like a finger in a lubed vinyl glove, than upgrade to a sharpie pen, in the glove with the cap still in place. Don't need anything bigger, finds the spot which is all you need. Thanks to the glove, I can slide it in all the way knowing it won't disappear, and I give it a little wiggle and slowly rotate it at the same time.