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A little follow up, I did meet him there the following weekend and countless times after for our weekly meetings as we called it, his name turned out to be Brad and the meeting after our first time he smiled and said do I even need to ask for your permission as he pulled down my sweat pants, why no not at all be my guest I replied and when he did it revealed that I was wearing a neon pink pair of bikini panties. He gasped and smiled saying well now look at you sexy, I picked these especially for you Brad oh my God you did he exclaimed do tell. As he licked the head of my cock through my panties and proceeded to tease the hell out of me and wickedly enjoyed every minute, I told him of my cross dressing days and my obsession with lingerie of all types. He stopped and said oh your such a kinky man I love it will you model for me some day he asked. You don’t even have to ask I most definitely will. He finally decided play time was over and got down to business he took my almost fully erect cock in his mouth sucking and bobbing his head up and down on my cock, momentarily stopping to suck on the head of my cock while pumping my shaft. He went back down on my cock and skillfully sucked on my cock without using his hands. I moaned I’m cumming baby, I’m gonna cum giving him fair warning as I had it drilled into me by all the women who went down on me over the years all but a very few of whom were not cum swallowers. This however was not the case with Brad, he sucked even harder and bobbed his head faster until he brought me over the edge, and I exploded in his mouth. He skillfully did not lose a single drop. I pumped what felt like a quart of cum into his belly and when I finally finished and thought I was going to pass out he just looked up and me with my drained cock still in his mouth smiling, but instead of allowing me to remove my drained now super sensitive member from his mouth his kept his sucking and bobbing his head I started gasping and panting and looked at him as if to say what the fuck are you doing barely muttering holy fuck what and he produced a condom from his pocket handing it to me. I now knew he planned to get me fully erect and when I was, he wanted me to fuck him in the ass. Something I mentioned to him once about fucking my wife up the ass. So, Brad continued his masterful and extremely sensual cock sucking he later told me how incredible a feeling it was having my cock grow in his mouth back to full hardness. He sucked and licked the shaft of my cock and licked and sucked my balls and looked up at me and smiled I’m ready was all he said he got up and bent over the picnic table offering me his ass. I tore open the condom wrapper and slipped it over my glistening cock I rolled it down the shaft and made sure it was all the way down being a magnum sized condom person Brad knew his cocks and provided me with the right size rather than some super tight torture device.
With my cock now fully protected I slowly slid the tip of my cock into Brad’s ass which by the way was absolutely perfect, round full and firm the ass of one who took very good care of himself. With one hand holding my shaft and the other on his ass cheeks I slowly slipped the head of my rock hard cock I entered him, he let out a soft moan, oh yes! he cried that’s it, yes that’s it fill my ass with your cock. I had both hand on his hips as I pushed my cock deep into his ass until I was balls deep. He lets out a moan saying oh my God you fill me up with your cock now fuck me please fuck me. I started to slowing pump my cock in and out of his ass as I had done with numerous women before but never with a man and never with such a nice ass. As I fucked his ass, I could feel my balls slapping his against his ass. As I fucked him, he was encouraging saying oh yes that’s it you feel so good, show me how you pounded all those bitches in the ass give me your load. I started to respond telling him I was going to rip the rubber off and fill his tight little ass with cum. Oh yes give it to me please give me your load he begged. I was ready to pull out and tear it off but without even giving a though to why he wanted me to wear a condom I just kept fucking his ass. I could feel myself getting ready to explode and I blurted out fuck I’m cumming and just let out a grunt as my cum started filling up the condom I kept pumping until I had nothing left and just stood there with my drained dick in his ass. We both caught our breath for a moment when he said ok take it out. I slapped his ass pretty hard saying when I’m good and ready bitch. He laughed saying no seriously please take it out. I did as he requested and when the head reached the opening, we both heard a popping sound. He laughed and turned around got on his knees pulled the condom off and licked my cock he then took the condom and squeezed its contents into his mouth. He smile and said much to yummy to waste. Enjoy was all I said.