With no hesitation he pressed forward, Hayden trying to relax herself fully, feeling herself stretch to accommodate him, with a sudden shot of pain as he stretched her to the max as his head slid through her tight back hole. The moment he felt the sudden stretching of her sphincter he immediately pressed home the advantage, pushing himself firmly into her arse, hearing her yelp at the sharp pain and clench down on him, but he was in now and she would just have to take it for a moment, breathing hard as he held still.“Just take a few deep breaths baby, it’ll pass,” he said reassuringly, holding still to let her recover, feeling her spasms subsiding. She tried to relax and gave another little jolt of pain, feeling him holding her firmly, clearly not letting her get away now as his hands slid up to her firm, perky breasts, giving them a good fondle and playing with her nipples, partly to help take her mind off things and partly because he wanted to. Hayden gradually relaxed, enjoying. Everyone assumed he was just gay but although he preferred men, Lauren was in a sweet spot for him. At 5’6”, flat chested, and toned from years of playing and coaching basketball she looked like a textbook tomboy. She kept her brown hair short and didn’t wear much makeup. On top of all of this, Jimmy knew that Lauren had only been with one man. If he played his cards right he could take her anal virginity and break her streak.He slowly agreed, “I can help, I’ll give you a list of stuff to buy to start training but, what you really will need is somebody pushing your limits.” Lauren nodded along but didn’t look comfortable. Jimmy continued, “Nothing crazy, but if you train this coming week, I might be able to give you a hand next Thursday or Friday. We can play it by ear from there.”Lauren agreed and finished her drink. She’d barely reached the door when her phone buzzed. Jimmy had listed out a couple butt plugs, a 9 inch dildo, and more lube than she thought could possibly be.
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