[Shawna](https://www.reddit.com/r/gonewildstories/comments/9vkr3d/the_time_i_had_car_sex_with_a_woman_i_met_in_a/?st=JP8HWCPZ&sh=94144491) wasn’t the only woman I’d end up picking up from the club I worked at. One night I was working a bachelorette party, being friendly, sociable and trying to leave the club with a nice tip. Like I said in my earlier stories, while my friend was manager there, the money was good. The clientele were pretty open-handed, and when they reserved space for a party, they usually ordered bottle service, which was guaranteed gratuity.
One lady was among the guests, and she was even more alluring than the bride-to-be. She was a BBW, medium-brown skin, high cheekbones, standing at about 5’11” — my height, so we could literally see eye-to-eye. Damn this woman had curves, impossible to hide in the black ankle-length dress she wore. Tits and ass for days, with a tattoo over her left breast, and when she talked, I noticed a tongue ring and a hint of a Jamaican accent. I noticed she was definitely older than I was by about a decade (I was 25 at the time), so this lady, Mary, had to be in her mid- to late-30s. I didn’t mind, I actually like older women.
When I wasn’t doing my job, I was making eyes and flirting with Mary, and she was definitely reciprocating. At the end of the night, I had a pocket full of money, a serious case of fatigue — and Mary’s number in my phone.
I didn’t seal the deal right away. Life intervened, including a trip to [California](https://www.reddit.com/r/gonewildstories/comments/9uyoad/making_california_love/?st=JP8HX1WE&sh=d92164f3) where I sampled the swirl, but while I was out there, and when I got back, I let Mary know I fully intended to see what was up.
I made the trip to her place across town. She lived in a nice condo building, which reminded me of *The Jeffersons*, and it was even sweeter inside. Mary had dressed down, T-shirt, panties, and robe. I thought we’d just get down to business, but no, she wanted to sit on the couch and talk. She wanted to get to know me — and make me anticipate it.
Being close with her like this, in the quiet of her place, no people, no loud music, definitely turned me on, and she could tell. I caught her sneaking glances at my crotch, and as the talk got more heated, I asked, “Would you like to see it?” She straightened up and said brightly, “Yes, I would!” I stood up and whipped it out. As I expected, her eyes went wide. She was clearly impressed — and a little intimidated.
“Uh-uh!” she exclaimed. “That’s a man’s dick! What are you doing with that?” I dared her to take me to her bedroom and find out. She took me up on that challenge and I soon myself on top of her, both of us naked and kissing. Freed from the confines, I saw that Mary was a true BBW; her curves flared out magnificently. In addition to the tattoo on her breast and tongue ring, she had a tattoo on her lower back and a nipple piercing. I couldn’t wait to be inside her.
She’d told me she couldn’t cum from just regular sex (don’t be surprised; a lot of women can’t), and she really liked having her pussy eaten. Well, I had no intention of disappointing a lady, so down I went.
Mary did not shave, but I refused to be turned off by that. My friend (the same one who got me the job that I met this sophisticated lady at, BTW) once told me to “move it all out the way, and get in there!” With his words in mind, I went to work. She was vocal during oral, which was good for me; as I licked her pussy, I used her verbal cues to figure out how to get her off. Once I heard her say, “You’re gonna make my pussy cum!,” I focused on that spot until she couldn’t take any more and pushed me off her.
“Come here. I want that dick!” Who was I to refuse a lady? I put the condom on and got on top. She squeezed her eyes shut as I penetrated her pussy. She felt even better than she tasted. I enjoyed nailing her to the bed, but I had to get at that humongous ass of hers, so after about ten minutes, I ordered her to turn over. Knowing what was coming, so to speak, she asked me to go easy on her. I had to respect a woman who knew her limits and let her lover know what she wanted and didn’t want.
If you can believe it, her pussy took me in even deeper from behind than from when I was on top. Each pump generated waves through her cheeks, and it was a fucking sexy sight. I was relishing the feeling of power I had over this older woman, and she was practically tapping out by the time I hit my climax and came inside the condom.
I was hoping to get a second round in eventually, but I’d worn her out. I’d have to wait till next time. Still, we settled into a nice friendship with benefits; we never brought stress into each other’s lives, we could spend time together, talk, laugh, and when we were both ready, fuck like it was going out of style. I learned important lessons about the value of patience and communication in the bedroom, and what women are likely to expect from men as they get older. Mary, in many ways, made me the man I am today.
Source: reddit.com/r/gonewildstories/comments/a2pwmd/mary_the_cougar_from_the_club_mf