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We tried this a few times and I became quite good at slipping it in my bum, I knew that it got painful and then subsided once I was past the wide part. Once inside it felt really nice and made my erections even harder and a couple to times Alan watched me lie back on the sofa with my knees up, showing him the plug in my bottom as I masturbated for him.One weekend late that summer, Alan asked if I wanted to go out on a day trip to a local museum and I asked my pa***ts and they were completely fine with it. We were going out for the afternoon and planned to get back in the early evening. I went round to Alan's house and before we went he asked if I fancied meeting one of his friends who was a bit lonely and would enjoy seeing me. I thought it sounded ok and although I was still a bit worried about people finding out about what Alan and I did together he reassured me that his friend was very discreet and hardly ever met anyone else. Alan asked if I would clean up and insert the plug as. ." Enough!" Barb stops her. "He's uh whore. I got it." I am not uh whore." I was not in the mood to discuss the merits of my past sexual conquests. "Ya'll act like I did 'em all in the same night." You didn't?" Barb teases. "Oh relax. I'm sure if you treated them the way you treated me, they were all very happy." If that were true, I'd still be with one of 'em." I groused."So why aren't you?" Barb prodded."Missy..." I pause. It still bugged me that I gave her a ring and she gave it back. "Wasn't ready to settle down." I finished a bit lamely. She nodded and waited for me to go on. "Michelle was jealous of Trina. Trina..." I glance at Alex just as he looked at me. His expression falls and he mumbles and apology. "Trina was a high school thing. That's all. Actually, she's married an' due with her first kid already." I reach for my glass and find it empty. "Most of the rest just dates, not girlfriends." What? No teachers? Nobody's Mom?" I glance a Barb and find her grinning back at me..
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