A fictional story.
At the age of 58, I found myself alone for the first time since college. My initial impulse was to throw caution to the wind, and bed as many women as I could. But after sleeping on it, I realized that route would be dangerous at best, and decided to give myself time. Several months passed, and I was able to get my finances in order along with my home. I felt the need for female companionship, and had given a lot of thought to what i wanted. A nice lady to date, and possibly to have sex with, was where I wanted to start. Also, I wasn't interested in anyone local. For one, none of the singles near my age interested me, and for another I didn't want my personal life spread around town. An Internet search turned up several websites claiming to be able to connect me to my perfect match. With a healthy dose of skepticism, I gave a few of them a trial run.
The results were mixed, at best. I chatted online with several women, and went on dates with a few. But, it became clear right away that most were looking for husbands, money, or both. Some were willing, even eager to have sex with me, but only if I was willing to commit to them. This soon became a headache, and I gave up. I wasn't ready for that. One day online, I came across a reference to Craigslist Personals, and being bored clicked on the link. Sure enough, in with the cars, truck, motorcycles, job opening, etc, there a was a Personals button. Once in, I selected Women Seeking Men, and there was a long list of women in my area seeking men. Right away, I saw that most were bogus, but a few read like real people. Scanning through those few, I found this one:
Tall and curvy mid 40's, dark hair and brown eyes. Would like to meet a nice guy for drinks and maybe more. Nothing long term, just casual fun with no strings. Work nights, so prefer weekdays before 5 PM. Weekends are possible, but rare. To prove I am real, it's a beautiful day, but there is a chance of rain later in the day.
No pictures were attached, but the wording and location caught my eye. I decided to respond:
Hi, sounds like we are looking for the same things. I'm 58, single, and live 20 minutes from you. Would love to meet you for drinks. Yes, today is beautiful.
I added a few details about myself, like height and weight, and sent it on it's way. An hour later, I was back online, and saw I had an email from Craigslist. Opening it, I saw it was from her. She was interested, but was cautious, and asked for some verification, simple things that I provided without hesitation. I sent a response back, and this time included a picture of myself, a "selfie" in the mirror. In a few minutes, I had another email. She thanked me for answering her questions, and said I could text her if I wanted to. Her number was included, and also a picture. She was an attractive lady, with a round expressive face, nicely styled hair, and big dark eyes.
We spent the next hour texting back and forth, asking questions and gradually becoming more comfortable. Her texts became more playful and suggestive, and I responded in kind. She asked what kind of body shape I liked. I responded that I liked all kinds, but I preferred women with curves. Then I asked if she had any pictures she'd be willing to share. A few minutes passed, and I began to think I had offended her, or that maybe she wasn't real after all. Then my phone chimed with a new message. It was a picture of her in the mirror, of her back side. She was in pink bra and panties. She was tanned, with a broad round ass and thick waist. I decided to raise the stakes, and took my clothes off. I was already hard from excitement, and took a full frontal picture, my 7" cock standing straight up. I sent it to her, thanking her for her picture, and saying I wanted to show her what her picture did to me.
A couple of minutes passed, and my phone sounded off. I eagerly opened up her text, and stared at the two pictures she'd sent. One was from the waist up, one arm cradling her nice boobs, a shy smile on her face. Under the picture, it said they were C cups. Her boobs were tan like the rest of her, with erect pinkish brown nipples. The other picture was two fingers spreading her outer pussy lips, showing an erect little clit over a moist pink interior. The caption under that picture said she was fingering herself and looking at my hard cock. I grinned at that, and stroked my cock until I blew a load, then took a picture of my cock with a string of cum hanging from the tip. I sent it off, wiped my cock, and dressed. It was several minutes until she sent back a text. She wanted to meet me in person, and named a bar in a college town a half hour away. I replied that I wanted to meet her as well, and we set up a time for the next day.
I arrived early, and was halfway through a beer when she walked in. I stood up and caught her eye, and she crossed the room to the booth I'd chosen. She was tall, almost the same height as I, and very curvy. She was wearing black tights with a loose top that came to her hips, and I like how her thighs were thick, but tapered to slim calves below her knees. She was a big boned lady, with a very pretty face, makeup put on just right, hair styled to soften her face, and a cute upturned nose. We embraced, her soft body pressing into me, and I held her for a moment, drinking in the scent of her cologne. She let go and stepped back, giving me a naughty grin.
"Hmm, guess yesterday wasn't enough, huh?" as she looked down at the bulge in my jeans.
"Uh, yeah, I mean no. Oh hell, let's back up a little and get acquainted. Hi, I'm Sam." I stuck out my hand, and she giggled, and we shook hands.
"Hi, I'm Debra, but call me Deb, 'cuz most everyone does."
We sat down and I ordered a drink for her, and we spent the next hour chatting. She had a lively sense of humor, and I laughed out loud at several of her comments. The talk turned to family, and she became a bit evasive, finally saying she had a teenage son living with her. When i asked a couple of times about her marital status, she finally said she was separated. Something didn't feel quite right about it, but she changed the subject and soon we were talking about sex, blowing away my misgiving as she talked about a threesome with a former boyfriend.
Time flew by, and she had to leave for her job at the hospital in town. I walked her to her car, and she hugged me again. I took the opportunity to kiss her, and it was definitely electric! Our tongues were darting and probing, and my cock jumped to attention. She broke the kiss and looked at me, laughing. "Doesn't take much to get him going, does it?"
"Only with the right person." I said. She slid her hand down between us, and gave me a squeeze.
"I'd like to see it, and the rest of you too."
"I'm game. How about tomorrow?" She stepped away from me, and thought for a second.
"Sure, that works, how about the same time as today, at the hotel down the street?" That was odd. Why at a hotel? She saw the look on my face, and said, "That way I can have more time, before I have to go to work." That made sense, so I agreed, and said I would take care of the hotel.
The next day, I arrived early, took care of the room, and sent her a text with the room number. I took a shower, pulled on a pair of shorts, and sat down with a beer. A few minutes early, there was a knock at the door, and Deb stepped into the room. She was in a t-shirt, sweat pants, and flip-flops, no make up, and her hair was wet. Setting her bag on the floor, she wasted no time, flopping down on the bed next to me, and giving me a long wet kiss. This time, there was no holding back. I pulled her lush body tight against me, and slid my hand under the waistband of her sweats and across her broad ass. No panties! Cupping her fleshy ass cheek, I held her in place while I ground my cock against her. For her part, Deb tongued and kissed me eagerly, and threw a leg up on my hip, letting my cock rub against her mound at a better angle.
We dry humped each other for a couple of minutes, sucking on the other one's tongue and moaning. I moved my hand off her ass, and pushed it up under her shirt so I could fondle her boobs. They were nice, not the biggest, but nice with hard nipples under my hand. She liked having them played with, and showed her appreciation by grinding her mound against my cock even harder. Fun as it was, I wanted her out of her clothes, so I let her go, sat up, and took hold of the t-shirt. As I started to pull it up, she grabbed my hands.
"No, I don't want you to see me."
"Why not?"
"I'm not happy with my body, that's why, especially my belly. Turn around." I did as I was told, and could hear her rustling around, and felt the bed shake as she squirmed out of her clothes.
"Okay." she said. I turned around, and she was under the sheet, and had it pulled up to her shoulders. My body isn't model perfect, but I'm not ashamed of it, so I hopped out of bed, and pushed my shorts down to my feet so I could step out of them, then turned to her, my cock standing up so hard, it almost hurt. She smiled with a gleam in her eye, and held her arms out to me. Instead of laying down, I got on the bed on my knees, next to her, and waited for her to get the hint.
Again she smiled, and sat up on an elbow, taking my cock in the other hand and giving it a few slow strokes. Then she leaned closer, and gave the head a wet lick, swirling her tongue round and round.
"Aaaaah, that's good." I moaned, and pushed it closer to her. She knew what I wanted, and engulfed the head, sucking it into her warm wet mouth. She knew how to suck cock, and soon had me bubbling close to cumming. I had other plans for my load, so I pulled my cock away from her, and crawled under the sheet. Her lush body was warm and soft, and I let my hands roam. Her belly had some folds, a noticeable tire around her hips, but she wasn't obese, and I told her so.