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“Relax Tim. It won’t hurt as much if you don’t fight it.”“That’s easy for you to say.” He winced as Jess applied a little more pressure.“Maybe not. Just relax, you’ve seen it work for Jess.” He must have relaxed a bit because the plug started to slip inside him. Jess kept up a firm but gentle pressure and I watched as Tim’s asshole expanded to let the plug inside. His eyes widened as the widest part of the plug stretched him open, then moaned as the diameter shrank and he could close around it. Jess tugged to test the insertion and his grip.“That’s better, baby. See, it wasn’t so bad after all.” Jess teased. Tim’s cock was now fully erect and Jess was stroking it with her hand. I suspected she had a plan, and I was right.“Get in here and fuck me, Rich.” Jess ordered.Who was I to refuse. She lifted her ass and I knelt behind her and slipped my cock into her cunt. Jess bent back down to taste Tim’s cock, then looked at him, “You can’t come yet. I’ll tell you when.” She. The first time I'd worked with Gary had been another one of these "Erotic" trade shows. Most of the guys bought a few things, but there was also a high admission charge. Inside there were a lot of girls like me, attractive, naked, and trying to sell the items. Actually, you always wore something, but it usually left your tits and crotch exposed. You got a good fee for just being there. If you were friendly to the customers you got asked back. If you sold stuff, you got a hefty commission. I quickly discovered that a barter system was in full swing without any overt haggling. The men weren't supposed to touch your exposed genitals, or even your tits, but did surreptitiously if you let them. I like getting fingered so it was a win-win. The men felt obliged to buy something, and the ones who sank a finger deep inside me usually bought the more expensive items. It was funny because they could have gotten laid by the regular whores at the brothels for what the evening was.
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