I told him I'd apply some lube if he needed it. No playing, just helping my love. It was a little red and I applied lube a couple of times a day for h...m. It seemed to be working.Late Saturday night we decided to go to bed. He went to the bathroom and I ran and put on a strapon and got into bed before he was done. When he got in the room and turned off the light, I asked how his little hole was. "Getting better, still a little raw", he said. "Want some lube?" "Yeah, I guess."I grabbed a glove. UGG" as my cock head fought against her resisting ring. I could feel the ring was starting to relax, ever so slightly. She could sense it too, and she started crying out from exertion and fear as the ring slowly relaxed loosing the battle. I pushed harder and suddenly her anus lost the battle and parted as my cockhead forced it’s way in. Her whole body arched and jerked, her head going straight back as she emitted an agonized scream, "OMG! OOOOOHHHHH! AAAAAHHHH! OOOOOOHHHHH! AAAAAAAHHHHHHH!",. More

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