Having him wear a butt plug for an hour or longer before you strap him helps.It also needs to be consistent so that you can get him in the right frame...of mind. He needs to expect it and know it’s going to happen whether he likes it or not.You want to stretch out his fuckhole to the point where after you lube him up, and press the dildo up against it, there is just that initial resistance to penetration, so that you have to kinda maintain the pressure, and then when you thrust forward it just. ‘Well that’s good at least. They seemed like they had fun.’ He ran a hand over his hair, stretching and smiling with a yawn. I walked over and wrapped my arms around him, resting my cheek against his back. ‘You okay honey? You look exhausted.’ I asked. ‘Hmm? I’m alright. Just tired. And my shoulders are sore from driving home.’ He replied with another yawn. I felt slightly guilty, even though I’d driven us to the park that morning. ‘I’m sorry baby. Tell you what, you finish getting ready for. More

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