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.
"Nice place you're house sitting." she said and looked all around her. She was still standing by the entrance.
"I'm sorry. Come in. Can I offer you a drink? I have red wine," I said.
"Yes, please." She pulled out a bottle of white wine from her tote. "I guess we'll be drinking tonight," she said.
She handed me her bottle.
I walked into the kitchen and grinned as wide as I could.
I came back with two glasses. "You look great," I told her.
"Thanks, Richard. A woman likes to hear that. I don't mind you saying it as often as it comes into your head."
I blushed. I had to watch myself. This was a woman. Nothing like my other female friends. I knew that from the moment she walked in, she had me mastered.
"The people you're house sitting for have very good taste," she said.
She stepped down into the dropped down living room and walked along one of the walls. She paused in front of a watercolor. She stood with her back to me and looked at a picture of a schooner. I took in the shape of her ass and the smooth tone of her calves.
"I know this artist," she said, turned her head around, and smiled. "He's a good friend of mine."
I nodded at her and took a drink of the wine. At that time, I hadn't developed a taste for wine. It went down hard. I hoped it was good. I hoped she liked it.
She walked around the room and looked at all the artwork. She turned at the end of one of the sofas and sat down. I walked toward the center of the room and sat on the recliner opposite her.
"We're not going to start like that, are we Richard?" She made room on the sofa and patted where she wanted me to sit. I walked over and sat next to her.
"You look nervous," she said.
"A little. Maybe a little excited to have a beautiful woman like yourself in an empty house with me." Idiot. I wanted to choke myself.
She smiled with gentle appreciation of my nervousness.
"At least you're honest." She moved in closer and put her arm around me. I turned to look at her.
She looked into my eyes and asked, "Is this is your first time?"
Her perfume was getting to me, subtle, discreetly arousing. It was the only thing about her that wasn't overt and aggressive.
"First time with someone you met online?" she asked.
"First time," I said.
"Well, don't worry. I'm not a man." She laughed. I chuckled and finished with a grin.
"How about, is this your first time with an older woman?"
She dissected me and found her answer without much effort.
"Yes," I said, as a matter of fact.
"Well, you can relax. It's easy. Just like any other date. I just happen to be more experienced, and open." She pressed her legs against mine "So, what do you think?"
"I think I like you." I said.
She knocked me with her knee.
"How about you? Do you do this much?"
"Sometimes. Depends. I check the personals every once in a while. I liked yours. I like the way it was written. Not many people take the trouble of writing so eloquently about themselves."
I was curious. "How long you've been doing this?" I asked.
"A long time, Richard."
"Of course. But first, how about dinner?"
She put a hand on my lap, and got to her feet. She bent over. Her hair fell down in front of me. It cut the room into bars of dark and light. She lowered her face to mine and softly breathed on my mouth. I tasted the sweet tackiness of her lips.
She walked away and climbed the step before I got off the couch.
"It's not what you think." She took a sip. "The fact that we slept with other people had nothing to do with it. My husband and I drifted apart, we became different people. People change, Richard. You wont be who you are now, 20 years into the future.
"So, Richard tell me something. This is a very exciting time for you."
"You mean with you here. I think so."
She laughed with food in her mouth. "That's not what I meant."
I laughed, too.
She jabbed a piece of bread in my direction.
"What are you doing in Portland, Richard? Do you have family there? Do you have a job lined up?"
"No, I don't have a job. I don't know anyone. I'm going there to be a writer."
"A writer? Now, that sounds fascinating. You want to work for a newspaper or magazine? Maybe one of these new online magazines?"
"No, I figured I'd get a job-job and work on my writing, try to publish some stories.
"Am I going to end up in one of these stories?"
I had her going. "Depends." I nodded.
She threw a croûton across the table. It swerved in midair and landed a yard away.
"I was a writer once," she said.
"What did you write?"
"I wrote articles for a swinger magazine, The Lifestyle. I wrote up meeting notes, calendar of events, profiles on people, that sort of thing. I did it for about ten years. A few hundred pieces later, I got tired of it and quit. I went back to my first love, painting. I did that for a few years. I realized I wasn't good enough to make it professionally, but still wanted to have a foot in the art community, maybe help young artists stay the course."
"So you started an art gallery?"
"I started that with my husband. I kept it going after we split up. It's a lot of work, but I love it."
I listened to her and followed the sound of her voice.
"So." She paused. "Do. What. You. Love. I'm so happy for you, Richard." She moved away her plate and took a sip from her glass.
I ate the last bit of rice and chicken on my plate and wiped my mouth with a napkin.
"Let me help with the dishes," she said and came over to my chair. She put a hand on my shoulder.
"Thanks for dinner, Richard." I looked up a her face. "It was thoughtful of you to get kosher food. I don't maintain a kosher diet, but I love the food anyway. So, thank you."
She leaned over the table and grabbed my plate. I enjoyed watching her move away. I kept my eyes on her behind. I didn't think she was looking, but that's where women have it over guys. They know.
She reached back and grabbed the hem of her dress. She lifted the material to about waist height and leaned forward. I caught a glimpse of her panties before she pulled down her skirt.
"Did you take a good look of that?" she asked and shook her derrière.
"Not nearly enough. I think I missed a thing or two." I got off my chair and walked over. I stood a few feet away.
"Oh, like what?"
She shook her ass again. I pulled her close and kissed her mouth.
"The panties," I asked. "were they blue or black?"
She turned a thigh to me. I moved my hand along her hip. She grabbed her skirt and hiked it again.
I bent down to the crotch of her panties.
"Blue," I said. "Dark blue."
"Are you sure? Take a closer look."
I got both my hands on her hips and stared into the middle of her crotch. Straggly hairs escaped her panties, down her two legs.
I put my lips to the material between her legs and kissed it.
Her nails pinched my scalp. I squeezed her ass and stroked her thighs.