An Older Woman on a Bench

It was a warm beautiful summer day in the city.

I had to go workout, so I decided to kill two birds with one stone. I thought I could get a good workout in and talk to some very unique, and scantily clad women at the same time. I knew just the place to go.

I headed to the gym in the low income area of town. It was a small gym, and you don't have to buy a membership, which means you can drop in whenever you want and pay to use the facilities for that day. I've been there in the past, and I've always found some unique woman who were on the poorer side.

I love women who are from the lower socio-economic status, because their whole mind set, demeanor, and attire are different from the pretentious snobs who frequent the higher end gyms. The lower income women aren't fake, and they wear what they want, even if its inappropriate, and they won't have a problem if you turn a conversation to a sexual nature.

Excitement coursed through my veins as I thought about going there. I put on a special pair of small thin soccer shorts, which appeals to the exhibitionist side in me, and I hopped in the car to make my way there.

It was an off day at the gym, and while my workout was good, there wasn't anybody else in the gym except me. The gym itself is very small, and its part of a larger community center which tends to get used more often then the gym itself.

I finished my workout and left the facility with a feeling of disappointment from not seeing any women at all.

I wasn't ready to call it a day yet, so I thought I'd try me luck on the main street. My plan was just to walk down the street in my special shorts, to give myself a small exhibitionist thrill, and hopefully come across some scantily clad women to ogle at the same time.

While walking past a bench I heard a woman say "nice shorts". I looked back to the source of the comment. I was surprised that I hadn't noticed the woman sitting on the bench before she made the comment. She wasn't what I was originally out looking for, and that's why she hadn't caught my eye. She was older, and dressed in a more conservative outfit. She had short curly hair, a red blouse and a red skirt, with high heel shoes. I would have never struck up a conversation with her on my own because I wouldn't think a higher class person such as herself would be accepting of me striking up a conversation with her.

I stopped dead in my tracks trying to figure this woman's comment out. "Thanks" I said and gave her a big smile.

"Your pocket is out at the back" she said, pointing to my butt. I turned and looked behind me and sure enough the back pocket had been turned inside out.

"Thanks again" I said as I shoved the pocket back in. As I did that I took a closer look at her and realized something was off. Her make up was put on pretty heavy and it wasn't applied evenly. Her clothing was way too tight and way too dressy for the setting. We were on the main drag of the low income area and the average person wore old shorts and T-shirts.

"I'm Mary" she said and reached out her hand to shake mine. I took her hand and shook it, feeling the warmth in her hand which sent a signal directly to my cock. She looked deep into my eyes and smiled while she held my hand, which caused my cock to move in my shorts.

I was intrigued by this woman's forwardness, and I was curious as to what her intensions were.

My growing cock was at eye level with her eyes as she sat on the bench. I didn't want to develop a full fledged boner, because that would be embarrassing and might frighten her, so I willed myself to keep it under control. Yet the more I tried to maintain control, the hornier I became.

"What are you up to today" I asked in an attempt to figure out this woman.

"Nothing, just trying to pass the time by sitting out here", she replied.

"You must be waiting for a date" I said in a teasing tone and making an obvious reference to her being dressed up.

"I haven't been with a man, or had a date since I was divorced 15 years ago" she said.

"What?" I said, unable to hide my genuine surprise.

"Yep" she confirmed.

"I don't believe a beautiful woman like you hasn't had a date in 15 years" I said in an attempt to push the boundaries a bit and take in her reaction.

She smiled and blushed and looked genuinely flattered. I knew I was given the green light to pursue this conversation in the direction that I wanted to. Before me was a women who had the same qualities I was out to find in a lower class woman. She wasn't fake, and wasn't easily offended if I pushed the boundaries of the conversation a bit.

I was intrigued at why she was sitting out dressed up on a bench on main street. Was she actually trying to pick up a guy like this? Was she that desperate? Was she mentally unstable? The possibilities fascinated and excited me.

"I used to be a teacher and now I like to tutor people. I can tutor anyone any subject you know?"

I didn't know what to say to that. I was taken so off guard by the directness of her comment. My mouth went dry and my heart began to beat hard in my chest. This woman before me was offering me an opportunity on a silver platter.

"You are a tutor?" I managed to get out.

"Yep, I really enjoy helping people with any subject... are you a student?" she asked.

It was almost too much for me to take. My head became overcome with excitement and my cock wanted to me to give it the permission to develop into a full fledge boner. I was using all my strength to keep my cock from reaching full mast, but it was a losing battle. It was slowly, but surely growing in my shorts. The excitement was becoming overwhelming.

I realized that the source of the excitement wasn't so much the woman herself, but the situation, and the opportunity.

I knew that this woman was incredibly lonely and desperate for affection, from dressing up, sitting on a bench and making comments to a complete stranger, who happened to be much, much younger. The more I thought about it the more I realized she might be crazy, but I didn't know for sure. The enigma before me captivated my mind and made me want her. I knew I could lie and say that I was a student. I knew that I could say anything and she would be all for it because that's how desperate or crazy she was. I knew I could tell her I was taking an anatomy class and I needed help, but now was my only free time. I knew I could ask her if she could teach me at her place at that very moment, and that she'd eagerly accept. I knew that in her place I could ask her to explain the male reproductive system to me, and focus on the sexuality part of it, particularly asking about how erections occur. I knew I could play dumb and ask her repeatedly about what she was talking about and ask her to draw diagrams. Finally I'd ask her if she'd be open enough to use me as a prop to point out the anatomy she would be trying to explain. I'd reassure her that it's all in the name of education and I knew she'd agree. I'd slowly pull down my pants showing her the straining boner pressing against my white briefs. I'd slowly pull down the briefs letting my hard cock spring out, and take in her reaction as she'd look at it. I'd hold my cock at the base letting it become even more engorged and hard. We'd talk about my cock and I'd point out parts of the boner to her and tell her how it felt, and I'd take her hand and let her feel it. I'd tell her to explain to me the process of ejaculation and I'd move her hand slowly up and down my throbbing cock as she explained...

I realized I had not said anything to her for that split second because I had all those thoughts running my head.

My heart felt like it was going to beat out of my chest. I was so incredibly horny not only by seeing her body in that tight outfit of hers, but also by the opportunity the situation presented to me. I know I could pursue it. I know I could do it. I know I could fulfill my fantasy.

I also realized that my intention had always been just to tease my fantasy. I know I could never have my fantasy because I am married. I had always meant to walk down the main street and talk with another person for a few minutes to give myself a snippet of what I truly wanted. I knew that this was the moment at which I needed to bid her a farewell and leave, keeping with me the memory of our interaction and the fantasy which I'd develop from our meeting.