Finally on this night I grew a pair and asked her out for coffee. She said yes, which made my cock flinch because I know I’d be fucking this woman tonight. She is a mature Bbw. When I say Bbw I mean Bbw. Tall, 6’, big shapely ass. Huge tits that had big nipples that you could see through her shirt. Short black hair, glasses, not really that attractive 56 yrs old Big older women turn me on. We went for coffee and had a good conversation. Things are going well. I can feel the vibe from her. She “accidentally” bumped me with her leg or foo a few times. So she suggests we go back to her place for another cup. I couldn’t stand up any faster. At her house she tells me to have a seat wherever. I position myself on her couch so as to invite her to sit next to me. Hoping she doesn’t choose the chair across the room. Luckily my plan worked. As we start chatting and getting along well, I reached and touched her arm. She didn’t flinch. More talking and I move in for a kiss. She happily opens. So with a bit of determination and help from my dad, I built myself up kind of. I wasn't bulking, but I gained some girth. I went from a lanky kid with a lithe form to a half-assed athletic guy with a bit more muscle to attract some girls. That was a whole other story however. Despite my new look, and a tiny shred of self confidence added, my love life was basically none existent. I had secluded myself from the thought of actually getting to know someone decent. I'm sure I met plenty of girl who'd be happy to hook up with an insecure and more or less feminine guy, but I never thought I had a chance. That was until I met Hailey. She was the complete opposite of me in almost everything. She was outgoing and genuinely a great person. What made me nervous about her was the fact that she was a bit "aggressive" when it came to her sexuality. Not abusive, but more commanding and sometimes had strange requests like: crawl towards the bed before sleep, only having her serviced and denying me.
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