I was at the gym on a Friday morning, just trying to get a sweat going. It had been a long workout, not one of my best, and I was finishing up with some work on my triceps. I had my sleeves rolled up, and I was looking in the mirror to see what I was working on, when I felt a sudden smack on my ass.
"Nice butt."
The weights dropped with a clang, and I turned around to see May, a spunky, little Latina woman I had come to know a little from around the gym. She wore tight, black, Lululemon yoga pants, a black and white sports bra, and a Giants hat. I smiled playfully as I took her in, lingering a little longer on her abs and the curve of her breasts peeking over the top of her bra.
"Hi, May. How are you?"
"I'm good, honey. What's new?"
We small talked for a little while, getting a little closer; I grabbed her arms to check the process on her biceps and gave them a little squeeze. She laughed and tried to push me away, but her hands slowed down and felt along the lines of my abs, then slightly brushed my cock through my shorts as she dropped them. While we had flirted before, it had all been innocent up until now, and we both became awkwardly quiet. I smiled at her, she smiled back, and it turned into a very provocative stare. She grabbed my hands and put them on her shoulders, saying, "I worked my shoulders today. Now I'm sore."
"So I guess I'm your masseuse now?"
"You don't want to?"
I spun her around forcefully and began rubbing her shoulders and upper back. I rubbed along her spine all the way down to her lower back, spread my fingers out along the top of her pants, then quickly stopped and gave her butt a firm slap, causing her to jump with a shriek.
"Fair is fair," I said.
"So what are you doing tonight, cutie?"
"Nothing. How 'bout you?"
"Let's go out."
After a quick run along the beach to clear my head and get the endorphins flowing, I went back home to get ready. I stripped out of my running shorts and underwear and started the shower. I took extra time to get ready, then stepped out to air dry. I tried to see myself in May's eyes. I'm 5'11", 185lbs, shaved head, light blue eyes. I played soccer in college, and vanity mixed with insecurity made me feel obligated to keep in shape. I never felt confident enough to say anything about me looked good, but the girls I dated all seemed to favor my legs and butt. I turned around to look at my ass, felt it to see how I was doing, then turned back around to look at my front. My cock was thick, but I never felt incredibly confident about its length, but out of obligation to full disclosure, it stands about six to seven inches when hard. Girth was definitely an area I felt a little better about.
May's image flashed through my head, her naughty smile from earlier inspiring me to dress to impress. I knew from previous conversations that she considered herself quite the flirt and liked dressing quite sexy. I decided I had to try to compete. I slid on some boxers, then decided against it, and dropped them to the floor. Even if she never knew, I'd be feeling naughty all night. A little fun always helped a date. I slid on some nice, dark jeans, a fitted white undershirt, and a dark, pinstriped button-up shirt.
At her apartment, I knocked on her door and saw her open the door wearing jeans that looked plastered to her thighs, a tight shirt that showed ample cleavage, and suede boots that reached her knees and had about three inch heels. I let her walk in front of me to the car, using it as an opportunity to stare at her curvy, Latina behind. I was suddenly reminded I wasn't wearing underwear. I let her into the car, shut the door, and readjusted myself as I walked around the back to get in the driver's seat. She was laughing a little as I got in.
"You okay," she asked, giggling.
I blushed, but tried to play dumb. "Yeah, why?"
"Looked like you had a little movement."
"You saw that? How embarrassing."
"Don't be embarrassed. I'm okay with it."
We flirted throughout dinner, then walked to a local bar. The upstairs was completely empty, and we walked up. Walking behind her, my eyes were glued to her butt. I was starting to get excited. We sat next to each other in the corner at a small, round table, our thighs touching. We held hands on top of the table, stared into each other's eyes, and leaned in for a slow, soft kiss.
"I've been wanting to do that all night," she said.
"Why didn't you do it earlier then?"
"Cause that's the guy's job."
"Well, let's keep going then." I leaned in and kissed her. She had amazingly soft lips, and I pulled away, amazed I had never noticed how full they were. Her eyes smiled at me, and I leaned in for more kisses. For the next half hour we barely touched our beers, but my hands found her thigh, her's found mine, and I moved mine to her stomach. Her toned abs got me even more excited, and I could feel myself straining against my jeans. It was sweet agony to feel it, anticipating what might happen.
She leaned in close to my ear and whispered, "I want to tell you something." She paused and bit her lip. Then whispered, "I'm shy though."