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Tom even took time to suck on Rose’s left earlobe, which really started to drive Rose wild. Well that and Tom’s hand caressing the entire crotch region on Rose’s pants. Rose decided before Tom had contributed to any additional moisture seeping into her panties and pants, as the sweet smell began to emerge, to shed both of them at this point. Tom was very happy to see every part of Rose’s body from below the breasts down. Tom then asked ‘Do you want me to lick you tonight or start with the fingers?’ Rose said ‘Start with the fingers, you might not want to go down on me tonight’, since she wasn’t sure if she might not be starting to flow that night. Tom brought his fingers out and there was a bit of blood, and so Tom decided that not going down was a good idea that night. So Tom proceeded to work Rose’s clit and her lips, with some teasing of where the leg meets the crotch, which for Rose is notably sensitive to Tom’s touch, and becomes quickly warm any time he strays to caress the. As I started to push, I realized even the tip was thicker than her finger and when it breached my hole I closed my eyes and sighed. It actually slipped in quickly for a moment since the glass was frictionless with the lube. I removed it and repeated the motion. Slower this time it started to slide in. Bit by bit, I was pushing up towards my stomach. As it got wider and wider I could actually feel my anus stretching. Trying my best to relax I kept pushing ever so slowly. It was only half-way in when I stopped and had a moment when I felt I had to ‘reset’. So I squeezed my ass tight and pulled it out completely. By this time Jenn was now kissing my chest, licking my nipples and stroking my hard penis, but still quiet and supportive. I still had my eyes closed, but I heard her whisper “Please don't hurt yourself babe.” After a few hard squeezes of my empty anus, I was ready to continue.With a quick breath, I pushed on my opening with the toy again and it made a much smoother entrance.
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