After college graduation, I decided I was going to Portland. I didn't have a job lined up, but I was going. That summer, I worked my final campus job and logged plenty of overtime. Everyone told me I needed more money. I cut back my expenses, and ate Burger King for lunch and dinner. I even cut out the beers. But it was still not enough. I was paying too much in rent.
With the help of my boss, who knew everyone in town, I found a place to house sit. The house, a green and white Colonial home, was located in an affluent part of town. It had a full front and back yard. plenty of trees, and a screen covered patio. I met the owners, an elderly couple that had been together for half a century. They traveled every year. This summer, it was a month-long trip to Europe.
They got to know me a little, and then they left. My job was to rake, mow the lawn and water the plants. Aside from two hours every week, I basically had nothing to do but read and jackoff. That's when I started to go a little nuts.
At my job, I looked at every woman with desperate desire. Didn't matter if she was old and wrinkled, or a hundred pounds overweight. My friends were gone, my ex was gone, my family was 3,000 miles away. I was one screwed up son-of-a-bitch. I have a feeling my coworkers recognized the deterioration. The poor guy's a zombie, neither dead, nor alive, graduated but not gone. Ignore him. He looks at all the women like that.
The masturbation only made the loneliness worse. In the evening I returned to an empty house. I'd bring out my magazines, and, standing up or lying down, I'd stroke myself into a lull. The hours vanished. I began to worry about my pathetic routine. I finally got it together and came up with a plan.
I borrowed the computer in the house, and with the aid of an AOL disk, I got back online. I went to the personals. I read hundreds of them. After a while, I figured out what the codes meant, and how to search for people in the area. I branched out and looked at surrounding towns. The ads didn't have pictures. It didn't matter. They were descriptive enough.
Pretty soon, I started answering them. A few at first and then more and more. I looked for couples and single women. I didn't mind if the husband/boy friend wanted to look, or whether they were young or old, black or white. All these things excited me, I found out. It felt like I was breaking taboos just thinking about it.
I got plenty of replies, some portraits, and many naughty pictures. Middle aged and overweight women on all fours, guys with panties pretending to be women, torsos without faces, and bunch of crooked white penises.
I replied to every ad that looked promising, but, it was no use. The couples wanted couples or single women. You had to bring something to the table. Tit for tat. Others were looking for someone with more experience. A 22 year old had to be broken in. No one had the time for that. I needed results. They needed to run tests, have dinner, consult with their partners. I got discouraged.
And then, Karen emailed me. She told me she was 43, and lived a few miles away.
She was a divorced Jewish woman; owned an art gallery; had two grown up kids, none of them at home. She enjoyed trips to the city; loved sushi, walks in the mountains and going camping. Dislikes: mean people, airy ice cream, and bad coffee.
She attached a portrait and asked me to email her back. I told her about my plans. She sounded interested and asked to for a photo. I sent her my set and got a reply minutes later. She attached more pictures. One of them was of the Sears Portrait Studio variety. Cloudy blue background, beige blouse, head slightly tilted, a nice smile, a large neat mass of brown hair crowning a slim face. Traditional, old fashioned. Really old fashioned. She was nice looking. I smiled thinking about this woman on the prowl. The sexy boudoir pics told me about her other side. A dark teddy with a feather boa curled around her neck and arm. A stark white face with dark shadows, large eyes and black thin lips. Her hair was free, teased into streams that merged and dissolved with other streams. Ringlets curled around her forehead and down her cheeks.
In some pictures, she laughed. In others, she shut her mouth into cold slivers of lipstick. She had nice breasts, beautifully defined cleavage that emphasized the little bones of her rib cage.
However, there was a conspicuously too much makeup, too much lace and smooth stocking. Here was reality: it seeped in through the shape of her face, the elongation of her thighs, everything that lacked realness or was conveniently hidden. I figured she must have been very beautiful once.
I thought about what it would be like to be with this mature older woman. I imagined holding her hands, kissing her breasts. I thought about the feel of her skin and the suppleness of her lips. I projected what I knew about age and filled in the gaps. I thought about her sex, like they say in the books. Was her pussy tight? Did her breasts defy the incessant pull of gravity?
Could she still fuck?
I wrote to her, and complimented her on her pictures. I told her she was beautiful and sexy, and that I wanted to meet her. I waited for a response. She wrote back. She wanted to speak over the phone, and find out more.
I gave her a call later that night.
"Hi. Is this Karen?"
"Richard? I wasn't expecting you to call so soon."
"I'm sorry, I can call later. Tomorrow?"
"No, no, right now is fine. I was just putting away my dinner. Give me a second."
I leaned back on my swivel chair and waited. I drew some pictures.
"Okay, I can talk. You still there?"
"I'm still here. What are you doing?" I asked.
"I was going to take a shower, read a book, and then go to bed. What about you? What are you up to?"
Jerking off. Reading. Playing with the piano. Jerking off, again.
"I think I might watch a movie," I said.
I avoided talking about what I really wanted to talk about, what she knew this was about. I told her I had to take it easy with my money. I couldn't afford drinks, couldn't afford to show her the good time she deserved. I felt cheap, but honest.
She came up with the idea of coming to my place on Saturday. I agreed. I'd cook, and provide the music and entertainment. I told her I liked her plan.
I wished her a good night and told her I couldn't wait. I hung up the phone. I was filled with so much nervous excitement. I loaded her pictures on the computer, sat back, unzipped my pants, and jerked off into a shirt that I then threw into the washer.
I stayed up late masturbating to pictures of naked older women. I found out I had a thing for them.
The next day, I woke up earlier than usual.
I did my chores, mowed the lawn and raked the leaves. Afterwards, I showered and looked through my suitcase. I found the shirt with the fewest stains and set it aside. I spent hours fixing up dinner and then ruining it. I still had a lot to learn about cooking spaghetti and boiling potatoes.
I decided to go to the local market and buy kosher food from the deli. The guy looked at me funny. Don't combine milk and dairy in the same meal, he told me. Why not, I asked. It's not kosher, he said. You feeding this to a Jewish person? I took my food and walked back. I stopped by the wine store and-- damn it all--put down twenty bucks for a bottle of red wine. On my way back, it started to rain hard. I ran home.
I came back drenched and with only a few minutes before my date. I changed into my shirt, and a dry pair of pants.
I had just enough time for a quick one in the toilet. I finished with a splash of cologne. While I was doing this, I heard a car pulling into the front of the house. I looked out of the blinds and saw the dark form of woman getting out of a Mercedes. I ran down the stairs and into the dining room. I made sure everything was set.
The doorbell rang, followed by a knock. I ran to the door and opened it.
She stood under the awning, a sophisticated woman drenched in rain. She wore a dark pair of glasses, bright red lip stick, and a buttoned up rain coat. Streams of water poured down on the wooden deck.
"Do I have the right place?" she asked with a smile. "Richard?"
"Hi, Karen. Come in."
I moved out of the way. Her shiny black strapless shoes clicked when she stepped in. With her heels, she was about as tall as me.
"Let me take your jacket," I said.
I got behind her, and her jacket slipped into my hands. I hung it on the rack by the door and walked back. I stuck out my hand. She took a step forward, turned her face and with one arm behind my back, pulled my cheek to hers.
She was warm. My heart raced.
She took a step back and held my shoulders at arm's length.
"Richard. You're even more handsome in person." I made a quick study of her.
She had on a strapless black dress, pleated around the bust and tight around the body. She was trim, with toned arms and a narrow almost long neck. The dress went only half way down her legs, didn't even come close to her knees. A black pair of sheer pantyhose bent the light around her thighs, knees and ankles.
She put her hands to her shoulders and gave me two tilts of her hips.
"Well, am I what you expected?" She caught me off guard. I didn't know what to say.
She took off her glasses and I noticed her blunted white nails, and then her eyes, green with specks of yellow. They locked into mine. I had to force myself to look away. She had my number.
She shook the rain from her hair, which was tinted into a dark brown.
.... There is more of this story ...