"I bet she planned to keep this empty." as you enter me, thrusting my cock quickly into me. My ass nearly splitting in pain as you yank it back out, t...e pain dulls. " she is so squeamish" Caitlyn said. " kind of a disgrace for her to be a women." " She's learning, and i am slowly breaking her in. She will love this stuff by the morning, i am sure." you reply. As Caitlyn slowly patters foward, You thrust yourself into me again, deeper than last time, ripping my ass open. As it sears through me,. Inside was a pair of skimpy ladies white cotton panties and a silky nylon camisole with lace trimming around the top. He explained that when his sister had left for university a few weeks before she had left some of her old underwear."I thought you would look nice in these darling," he said. "I've spent a lot of time choosing the outfits for our first fuck. Put them on". I whipped off my clothes, desperate to pull on the undies. Michael just stood and coolly watched me. I pulled the panties on. " Lucy smiled almost sadly, "I'll see you at ten or will that be too early." Ten is fine," I replied, "put some wine on ice and we'll make a real day of it."Later that night I asked my wife about her 'trip' to Ascot with Gordon, we ended up having a steaming row which ended with her storming off to bed while I fumed quietly in the living room. There was a man I knew who had contacts with a detective agency and I called him then and there, thankfully my friend didn't keep office hours and was. I was a little stunned to say the least and unsure how to handle the fact that with out a word this cute guy had sat on my dick and was riding me as I got closer to orgasm. I told him I was getting close and he just grunted as he continued to bounce on my throbbing cock. I grabbed his hips and pulled him down hard onto my cock as I filled his ass with a huge load of cum. After I released him he got off me and thanked me as he walked away with out a backward glance."Wow," I thought to myself as.