The challenge was how to hide the fact that I would pop a woody every time Debbie gave me hug. That's the last thing I needed to show through a tight fitting dress when I was at work.Meanwhile it was now six weeks later. I knew if I ever had a shot at asking Debbie out it was now. She was alone by the water cooler. This was my chance. I took a cup and poured myself a drink."So um Debbie," I began. "You know, I um, don't wear a dress all the time. I can be, you know, normal. "She threw her cup away and gave me an odd look. "What are you telling me this for?" she interrupted. (Uh-oh)"Are you coming on to me?"(BUSTED!)"Because if you are I'm OK being with a guy who likes to wear a dress."(Is she throwing me a lifeline?)"In fact I think it's kind of kinky"(YES! YES! YES!)For our first date Debbie gave me a tour of Pleasant Town's club district. It was early evening in mid July the sun was just starting to go down. I wore a light brown sleeveless dress while Debbie had on a. I started to lick her. She was overflowing with juice.She grabbed my hair.Sis: Stop it, bro, don’t tease me.Me: Hmmm, what happened?Sis: I can’t wait any longer. Please, fuck me.I took the coconut oil and rubbed it on my dick. She spread her legs wide open. I positioned myself between her legs. My dick was near her pussy.Me: It’s gonna hurtSis: Don’t worry, I can take it, now put that thing inside me.I pushed my dick inside as hard I could. But only the head part entered into her pussy. She screamed in pain. I got scared and took it out.Me: Are you ok, sis? Do you want me to stop?Sis: No, don’t stop, continue, please.Again I positioned myself and told her to close her eyes. She closed her eyes tight. I kissed in her lips to stop her from making a sound. Then with all my strength, I gave a big push. Half of my dick entered her pussy, and she tried to scream. But I stopped it with my lips.Sis: is it fully in?Me: It’s halfway inside.Sis: Then come give a big push like the last.With.
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