The Craig’s List Ad

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The Craig’s List ad under W4M read, “5’6″, tall, fit, active red-head (with bottle help), 55, educated, set in her ways, looking for non-clingy, non-smoking, active, passionate man. Occasional dinners, trips to the museum, cooking together, quiet evenings and lots of active surprises. Not every day. Pic for Pic. Tell me about yourself, I’ll answer your questions. Kids grown and gone but caregiver for adult. Right person will know what that means.”

I had given up on ever finding someone again. I had never answered such an ad or ever seriously looked for a FWB. For some reason, this ad was different.

Hi Red,

Yea that’s me in the picture two months ago. My ego tells me I’m more handsome that that. I’m a caregiver too. Vacillate between running away and giving up to being a martyr. I’m in the black humor stage. Interested in everything, too active, shoot pool, take care of house and yard, writer, active in museum and zoo. I miss touching and talking the most. Second, I miss dining out and having a friend to share passions with. Don’t smoke. My doc, 20 years my junior, says I’m healthier than he is. Years ago, I was an electronics engineer and then used MBA to do well in management. Enough about me, now, it is your turn. Pic? Your passions? Your stage? Food you like? Do I challenge you to a cooking contest? Educated, it shows, but in what? Please call me Jim, if you answer back.

I looked for an answer for three days. None came. That was not unusual on Craig’s List; so many ads are scams, bots or phishing.

About eleven p.m. I relieved the baby sitter. My pool playing had only been average but I blew off enough steam to keep from going postal for another couple of days. When I checked my email, I got a pleasant surprise.


My junk mail program blocked you. Damn I’m efficient. Found you today among Viagra ads — shouldn’t the name Sharon be a flag? Big East Coast University, B.A. in communication. Now I text message and email so much, I don’t even remember how to spell. …………….

Her email was long, informative, made her sound very interesting, strong, opinionated and playful. My kind of girl. She gave of herself but wanted some answers that would surely drive her away. What the hell. I started my reply:


Yes, I’m married. I’ve been the caregiver for my wife for fourteen years. She has Parkinson’s, is in a wheelchair, heavily medicated and has lots of related medical issues. I have nursing help so I can schedule getaways. I’m a little older than you, but you will not be able to keep up with me.

After my deal breaker “I’m married,” I continued and answered all her questions. We seemed to have a lot in common. I told her about hiring women to be my date for business, dinner and social functions. I told her that once I took my niece but got the “dirty old man” looks from all the up-tight museum bitties. Then I took my shot:

Even with all that baggage, I’m going to ask you to have an early breakfast with me some morning on your way to work. You name the place and I’ll be there. My name is Jim Carlson and I live in the northwest part of the city.

The next day she responded, “You don’t waste any time do you?” and to my surprise she agreed and we met a few days later for breakfast. She was delightful, bright, pretty, sexy and wonderfully female.

“Sharon, you did not answer some of the things I asked you in my emails.” She knew exactly what I was asking, yet she said, “What did I not answer?”

“Who do you provide care for, where do you live, all that stuff.”

“I too am married. My husband has Alzheimer’s. We live with his sister. She cares for him while I am at work. My income and insurance keep us afloat. Tom’s care has sapped all our savings. We live almost in the center of town; we have three kids — a girl and two boys. None of them live within a hundred miles or want any part of helping with their father’s care.”

There was a note of bitterness in her voice. “I’ve been to several conventions. I’ve always been amazed how few families are involved. In fact, many people with diseases are going it alone or are in care facilities. I’m sure it is even worse with Alzheimer’s. Does Tom know who you and his sister are?”

“Honed right in didn’t you? Most of the time. He is right at that stage.”

“I’m sorry I didn’t mean to hit a nerve. That must be horrible.”

We talked for quite a while then Sharon asked, “Do you have to rush off?”

“Not at all, but I know it is a work day for you.”

She excused herself from the table. When she returned she surprised me, “I called in saying I would be late today. I hope you do not mind visiting a while longer.”

I had not enjoyed breakfast so much in years. When Sharon finally had to go to work, I walked her to the car, took her hand and looked into her eyes, “Thank you.”

“Thank you for what?”

“For being who you said you were. For looking like your picture and for giving me your company for a wonderful breakfast.”

Her Maltepe Escort eyes teared up. “Jim, I wanted to say exactly the same to you. Can we meet for breakfast again?”

“Yes, we can. Today is Thursday. Can you ever get away on the weekend?”


“How about we meet for a picnic at the rose garden on Saturday? I’ll bring everything. You just bring you so I can look at you and talk with you. Until then I’ll ………”

“You’ll what?”

I could see the concern in her eyes that she must have uncovered a pervert. “I was going too far, too fast. I enjoyed this morning too much. I was going to foolishly add, “Dream of your company until Saturday.””

Sharon, leaned forward and kissed me lightly on the lips, got into her car, rolled the window down and cranked the engine. Before she put it into gear she said, “I’ll email you about Saturday.”

This could have been a big mistake, but I reached into my pocket and handed her my card, “Call me on my cell instead. Use a pay phone if you do not want me to know your number.”

She looked puzzled as she drove away.

I did not hear from her on Friday so I figured the picnic was off. About nine a.m. on Saturday, my cell phone rang, “Can we have the picnic this afternoon about three?”

“If you are going to be there, I’ll be there at two in the morning.”

“You are silly but sweet. Thank you for wanting me to feel safe with you.”

“You are welcome. Today, I’ll answer anything you ask me. I want you to run away soon, if you have to. Before I completely fall for you.”

There were a few moments of uncomfortable silence on the phone, then she said, “Jim, I felt it too. Scary. It happened so fast. I’ll see you at three at the main gate of the garden.”

I had barely hung up when she called back. “I’ll be out near your house later. Do you want me to pick you up?”

“Great idea. You can see where I live. Come by when you are ready.”

Sharon loved the house, the water feature with the koi pond, the garden and was shocked by the art in my office. For the time being, I offered no comments. My wife was asleep but Sharon did meet her day care companion.

Sharon was quiet as she drove us to the park. I think she felt safer driving.

The picnic basket was a fun treasure hunt for her. I served her and treated her like royalty. She blushed when I removed her shoes and rubbed her feet briefly after she had sat down on the soft, thick blanket that served as our table and chairs. We were comfortable in the shade under a weeping willow tree, on a knoll, in a secluded section of the park. It seemed cool but it was in the mid-eighties. When I opened the second bottle of wine, I asked her, “So do you have any questions for me?”

“Why do you think I have questions?”

“Do you?”


“Then ask me while we are relaxed, alone and have time for long answers.”

“Have you done this a lot?”

“No. I haven’t been with a woman for five years. I haven’t been with any woman other than my wife in twenty-five years. She has urged me to go out, find someone but I haven’t.”

“But you were reading the ads and answered mine?”

“Sex was a major part of my life until my wife got sick. I’ve found a hundred ways to keep the fantasy and my interest alive. I have read ads, erotic stories, written stories for the internet, corresponded with people who provided feedback to my stories, gone to strip clubs, flirted and gone to lunch with female friends but that is all.”

“You seem so confidant with me and everything. You seem well off?”

“I was successful in business, still own a couple and have real estate holdings so I was able to retire at 50 when my wife got sick. I am used to being in charge. I am dominate sexually and really enjoy female company. I am not intimidated by the opposite sex.”

“All those erotic pictures in your office?”

“Mostly fantasy. I like mermaids as you saw. Almost every picture was the inspiration for a story. I’ll give you a couple of sites that I write for and my pen names. You can read some of them and then run for the hills.”

“Why do you keep thinking, I will run away from you?”

“I gather that sex fantasies are not comfortable for you? You probably think I’m a pervert and I scare you. I grew up in foreign countries. Usually, I keep my own counsel because sex is as natural as breathing to me. I’ve heard these questions before and usually my answers do not put me in a good light.”

“It’s just that I’ve never been exposed to such images.”

“You’re married with three kids, have grandchildren, a computer, female friends and an imagination. What could have been new to you?”

“The kids are Tom’s; I’m the late blooming step-mom and was a spinster schoolteacher up until then.”

“I didn’t realize that Sharon. I like your company and I like looking at you. Please let me slow my too blunt answers down.”

“Don’t do that, just answer things for me. Bondage and pain? Are you into İstanbul Escort that?”

“No, definitely not. You are thinking about some of the Sorayama prints. I like the idea that a woman might trust her lover enough to lie back and say, “Do anything you want to me, just please me and make me cum.”

Sharon recoiled noticeably and blushed.

“Did you and Tom have a good love life before he got sick?”

“I was not very experienced. I think I expected too much and did not know what to do. Tom worked long hours and our intimate time together didn’t last long. He always seemed satisfied.”

Her answer spoke volumes. I had started in the middle and possibly done a lot of damage to our young friendship. Might as well finish it off.

“Sharon, relax with me. Say, “Stop.””

She really looked puzzled, “Stop.”

“I’m easily controlled with that word but I am hard to get started again. I will not hurt you under any condition. I have no diseases. I’m very oral and I am just dying to kiss you.”

I pushed her down onto her back, closed her eyes gently with my fingertips and stroked her neck, hair and ears lightly. She was expecting a kiss. It was coming, but not yet. My lips followed my fingers across her neck, face and ears. Her body was already betraying her mind. I pressed lightly on her chin until her mouth opened slightly. Our first kiss was soft and sweet. As I pulled away my tongue flicked out and tickled her lips. That surprised her and she inhaled. I helped her breathe by pressing my lips to hers and letting my breath fill her lungs. As that sensation waned, I slipped my tongue into her mouth with one word, “Suck.” Tentatively, she nursed. “Now, give me yours.” Sharon liked her tongue in my mouth and I sucked and licked at it. Over the next few minutes we learned to kiss and enjoy each other’s tastes. Still she was holding back. Afraid she would offend, do something wrong or lose control. I rolled over pulling her on top of me.

“Kiss me, Sharon, if you want to. Any way you want to.”

She was puzzled but let her lips copied what I had done. She swallowed a lot, self-conscious of her saliva.

“Don’t swallow. Let me taste the wonderful wetness of your mouth.”

Tentatively, she kissed, shared her tongue and when I sighed because her juices flowed into me, she became more bold and assertive. Her tongue explored under my upper lip. When our combined wetness trickled on my cheek, she felt it flow from us and reached up to wipe it away. “Leave it. I enjoy feeling us flow together. Tasting us together. Your body feels wonderful on top of me. You are warm, soft and desirable.”

She forgot our kisses for a moment. She had been too preoccupied to feel our bodies touching. She liked what she felt, relaxed, breathed into me, pressed her body into me and lowered her lips to kiss even more passionately. I guided her head, letting her senses fill with the smells and taste of my neck, lips and skin. I did not touch her body with my hands, still she froze for a moment when her hips rolled and her belly pressed into my hard, pulsing cock.

I whispered into her ear quietly so my breath would urge her body on, “I enjoy what we are doing but I felt you recoil from me. It is ok. Stop, if you want.”

Sharon said, “I do not want to stop” and gave her mouth to me demanding my tongue. Her breasts thrust into my chest, asking to be caressed. At first, I touched only her left nipple, rolling it in between my fingers and my thumb. Her kiss urged me not to stop.

“I want to look at you. Sit on me, beautiful.”

Again she surprised me, she straddled my hips, letting the hot, humid spot between her legs grind into my imprisoned, twisted dick.

I reached up and slowly unbuttoned her blouse, slipping my hands inside to touch the newly exposed skin after each button opened. Her bra clasped in the front. Her naked breasts pushed proudly into my hands. Her hands were gripping the skin and hair on my chest for balance while she rocked her hips into me. Her eyes were closed. She arched her back, held my hands away from her chest, wanting to show me her naked breasts. I understood why. They were two perfect small C-sized cones with beaconing stiff, red, half-inch high erasers toping a half dollar sized bumpy pink circle. My mouth was watering.

“They are beautiful, Sharon. Lean forward, push one into my mouth, so I can learn to please you.”

Her eyes stayed closed, she pressed her hips hard into me, arched her back even more and leaned forward. I shifted under her so her aim would be true. The right one must be the most sensitive. It responded to my tongue more than my lips. The nipple liked to be licked all around and flicked. I held it lightly with my lips and batted it with my tongue. Her reactions did not change. I pushed her nipple gently against my front teeth and then sucked gently. She said, “Yes” and pressed into my face.

I was half-way sitting up. My stomach muscles were complaining. I rolled her Anadolu Yakası Escort over. She helped. We were a good team. Her legs spread wider; my hips pressed my now rigid cock hard into the damp crotch of her slacks and I curled enough to properly worship first one breast and then the other.

Her breathing was becoming labored; she was limp under me willingly taking my efforts to tease her. I rolled to her right side, leaving my right leg over hers keeping her spread.

“Let your body lead, turn off you mind. Let me please you. My pants will stay on today. I only want to see you fly.” With my last word I cupped her wet pussy through her slacks. The heat surprised me. She thrust against my hand and held her hips off the ground. The button opened easily and the zipper slid down on its own. Her thin blue panties were low cut and offered no resistance as my fingers slipped over her belly button, down over her neatly trimmed red hair, paused on her clit, pressed, stroked and then moved farther down. My middle finger never slowed as it slipped smoothly to the hilt in her inviting sheath. After a few strokes in and out slipping across her button, I added a second finger. This was better for her. Unexpectedly, she moaned and began to cum. This orgasm was from bottled up need. It wasn’t a massive earth-shattering event. It just ebbed through her, leaving her still near the top.

Sharon’s cunt was still spasming, when I pulled my fingers out of her. Her hips followed, but I needed both hands to push her slacks and panties down off her legs leaving her nude, wet, exposed to the cool, shaded wind.

She started to sit up, “Someone ……..”

“Yes, they might. Let me worry about being seen. You enjoy. I need to taste her.”

“No, I might not be clean ………”

“Relax, I know what I am doing.”

That seemed to take her last resistance away. She thrust when my fingers entered her again. She thrust again when I pressed into her g-spot. She had almost relaxed when my lips closed over her clit and suckled. That caused her body to curl and her hands to settle on the back of my head. She pulled me tightly to her as I licked and nursed in time with my fingers’ short thrusts, pushing her clit from the inside to caress my lips.

Today, I would not tease her. Her body was too needy. I did not vary my strokes or the matching rhythm of my lips. Again all too quickly, she gasped, moaned, arched and wetness flowed from deep inside her body. I licked away all I could find. The more I tasted her, the drunker I felt. I needed more but she was sensitive and tried to hold me still.

“Work though the pain. I need more from you.” I could feel her struggle to endure, surrender and give me what I asked. In moments, she was helping, thrusting hard in time with my fingers. I changed my strokes to long, faster and rougher. This climax would be harder for her. I felt her tighten and I stopped all but my gentle kisses and tugs at her pussy’s lips. I could feel her frustration and resignation as her hips relaxed back into the blanket. I licked her clit, sucked it and thrust now three fingers into her. Again she curled. Again I was still until she relaxed.

Her thoughts must have been, “Will he stop again,” as my fingers began to move. She was holding back, sure I would stop. I licked and sucked at her wetness, but out of time with my fingers. Different, confusing. Soon her body did not care. It drooled, contracted, arched and groaned. Now, I timed my strokes and my sucking on her clit. Her hot thighs closed around my head, muffling sounds and warming my ears. Even so, I heard her scream. She heard that one too, but she screamed again and did not hear that one. Her body went limp, her cunt was in full spasm tugging at my fingers and pushing wonderful juices out to flow down, wasted on the blanket. I knew she could not feel it when I pulled my fingers from her and licked at her slippery tasty nectar. Her taste had me insane now. My mind traveled inside of her, licked the walls, found a fountain and I slumped down drunk with my face glistening. My hips pumped into the blanket and I started to cum in my pants. I did not care. My mind was inside of her, my taste buds were full of her and I pictured, even felt, her sucking cunt swallowing my cum.

I laid my head on her sleeping belly and enjoyed the layers and layers of beauty that filled my thoughts. I hoped she was feeling the same and would not laugh that a mature man came in his pants. No, it was ok if she did, as long as I could taste her again.

I recovered, licked across her pussy again. She did not react. I covered her with the blanket and began to clean up our picnic, leaving the last of the wine. She would be thirsty when she awoke.

In about thirty minutes, I raised her head and slipped under her. She was trying to wake up but was groggy and started to speak. “No, pretty one, stay quiet, rest in my arms, drift and enjoy the feelings in your body.”

After another twenty minutes, her eyes opened, she snuggled but did not speak.

Finally she spoke, “That was amazing, but it was all for me.”

“No it wasn’t. You let me touch you, kiss you, taste you. Your body took control of me and gave me it greatest gifts. You made me cum with just the taste and sight of you.”

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