This story comes from a man who contacted me asking me to tell his story. I offered to help him publish it himself, but he was shy.
I was cruising Ashley Madison (AM) late at night, as cheaters often do when I came across a profile of a woman in her early 70s. There wasn’t much of a write-up, but she said she was a lonely widow. I was intrigued, and although I don’t message singles, I sent her a nice priority message.
A few minutes later I received an email saying she’d opened my message. I’ve been reading Teresa for a while, so know it’s best to strike while the iron’s hot, so I messaged again —
I’m up if you want to chat
I didn’t expect anything back, but she replied and said sure. We chatted for about 45 mins, and wow!
The first few minutes were the normal back and forth, but we quickly escalated to sexting. She’d been toying herself and telling me how wet our chat was getting her. She paused while she orgasmed and then came back. By the end of it, she’d sent me some pics and I’d sent her a masturbation video.
I can’t believe how we’d gotten each other so horny so quickly.
The next day we had our first phone call. Over my time as a cheater, I’ve had very few phone calls, and never so soon. I’d never been with a single woman before, so this was probably why we could talk. Only I had to be careful on my end. When both are married, the window narrows significantly.
Over the next few days we chatted, getting to know each other, and despite our age difference (I’m almost 50), we had a lot in common. We had both worked for the State Department and had done overseas postings to the Middle East and Europe. She to Iraq and London in the ’70s and ’80s, and I, to Jordan and Berlin in the ’90s and ’00s.
I asked her about being a widow and learned she’d just written that, but had never been married. She was just looking for a friend on AM.
For me, what stood out was the connection we formed in just a few days that went beyond the obvious chemistry that was burning us up. I was fascinated with her and her life. The more I learned the more I wanted to know.
She had a math degree, which frightened me because math was never my thing. I’m in awe of anyone who could get a degree in it. I’m an art’s man, who’d lost interest in math with algebra in eighth grade.
To say I was taken with Monica would be an understatement. There was definitely new relationship energy happening, and maybe I’m kidding myself, but I felt something more from the start.
Monica was not only single but also retired with a pension and a comfortable country home on a few acres in Virginia. Living a little over an hour from me in a direction I rarely go, I did have a friend out that way I could use as a cover story.
We agreed to meet during the day a few days later. It was a weekday and I piggybacked our meet on a doctor’s appointment I already had. I figured no one would miss me at work or home for a couple of extra hours.
Of course, on the day of the meet it snowed!!
Not a lot, but enough to snarl traffic and mess with my plan. Arriving at my doctor’s late, they fit me in an hour later because of a cancellation. I kept looking at the time because the window was closing and I didn’t want to cancel.
Monica and I agreed to meet at her place. We skipped the coffee date, and thought if we got along, we could move to the bedroom if the chemistry was there.
When I finished the appointment I told her I was coming. I still had an hour's drive, but that would only leave me an hour with her at the most.
She texted back — Are you sure you’re still coming?
Me — Hell yeah!
I couldn’t think of anything but Monica for a week, we’d sexted, gotten sexy, and by that point, I wasn’t letting anything stop me from seeing her.
Driving the lightly snow-covered country roads was ok, and I took it easy, but Jesus, I felt the time evaporating as Google Maps took me to her. Pulling into the driveway I parked and the garage door opened. She waved me in, and once in the foyer, the first thing I noticed was her eyes.
They were a beautiful pale blue, like glacial meltwater pools. Her hair was a short silver that suited her perfectly. I was immediately taken by her elegance. She wore a flowing robe that was slightly open to the waist.
As she welcomed me in I continued to check her out and very much liked what I saw. She was as sexy as she was sophisticated, and for me, the chemistry was there 100%.
I prayed she liked what she saw.
My cock instantly hardened when I noticed a nipple through the sheer nightgown she wore under her open robe. What happened after that was a blur but when I got dressed I found my clothes from the doorway of her bedroom to her bed.
When undressed, I stood before her as she sat on the side of her bed. I wanted to go down on her, but needed to see her chest since seeing that lone nipple.
Standing her up, I picked up the hem of her nighty and pulled it over her head, revealing her. Kissing her, I took her nipples into my mouth one after another, as she gasped. She was beautiful.
Sitting her down again she hugged my waist and pressed her cheek into me, and held me for a moment. It was sweet.
I knelt before her and motioned for her to lay back. I spread her legs and leaned in to taste her. Her pussy was so good I couldn’t get enough.
She’d told me she needed a trim, but I’d earlier asked to shave her so she’d left what she had. Sadly the weather stole our time. I was so looking forward to shaving her as I played with her pussy, but there was no time.
I only had an hour by the time we were in her room, and I was going to use the whole thing. And hair doesn’t bother me.
I needed her so badly at that point because she’d gotten me so horny.
I played with and ate her, exploring her pussy for what must have been ten minutes, before climbing onto the bed with her. We hugged, kissed, and touched before I put her on her back and mounted her.
Her pussy hugged my cock perfectly and felt so good. I held myself off of her so she wouldn’t have to hold my weight, and I watched her face as I made love to her. My pace was steady and I made sure to bottom out each time, rhythmically fucking her as I went.
Laying there, under me, her cheeks blushed and her breathing was ragged. Exhaling in gasps, then holding her breath, her head turned from side to side as I fucked her.
“It feels like you’re hitting my g-spot,” she uttered at one point, and in response, I continued to do what I’d been doing. When it comes to sex, I like to do what the lady likes. It’s the best way to get a call-back.
I have no idea how long I was on top of her, but I pulled out and rolled over to take a break. I wasn’t ready to cum and was getting close so needed to switch it up.
Laying there, she began sucking my cock. Her mouth felt as good as her pussy and she looked beautiful from the side. Wanting more of her pussy, I pulled her into a 69 and continued exploring and devouring her from below.
“This is like face-sitting,” she said between sucks. I’d asked when chatting if there was anything she wanted to try, and she said she wanted to sit on my face. I had offered, but she said we’d try it another time.
We 69'd for a few minutes before she rolled off.
“Can you do me from behind?” she asked.
“I can do whatever you want!”
She got on her hands and knees on the bed, I stood on the floor behind her and entered her easily. Her hands grasped the blankets in front of her and I proceeded to fuck her, enjoying each stroke as I looked down over her body. God she was sexy and I wanted so much more but time was closing in on us like a nightmare.
I was disappointed that I couldn't give her an orgasm, but as I held her hips and gave her what she asked for, I knew it wouldn’t be long for me.
“I’m gonna cum,” I uttered, and let go, deep inside her, holding her firmly until I was done.
I hate to cum and run but I had no choice. The weather had cockblocked us, but I knew we’d have a great sexy future if this is what our first date was like.
Sadly, it wasn’t to be.
She knew I had a girlfriend, though we’d not seen each other since Thanksgiving seven weeks or more before. I didn’t want to give her up. We’d had a lot of history and affection for each other.
Monica told me flat out she didn’t want to be number three. She was ok being on the side because I didn’t get sex at home, but she didn’t want to share me.
That came in the days after our meeting. After a heated exchange, we calmed down and agreed it would be best if we didn’t talk, and went cold turkey. I think it was for the best, but honestly, I was heartbroken.
It was a short, intense ten days. Everything was there for me intellectually, sexually, and emotionally.
It took more than a month to get over her. I was confused by what I was feeling because it hurt so much more than I’d expected, and I longed for her as she faded from my heart. I’d never connected with an affair partner like that, and am not sure I will again.
It hurt too much letting her go.
We’ve had a few email exchanges since then, and I still get horny thinking of her. I’m ok now, but I’ll never forget the one that got away.
The feels are real, aren’t they? That’s why I like this story and agreed to run with it. I know it doesn’t always work out, but that doesn’t mean the people who pass through our lives don’t leave a mark. No matter the differences — age, expectations, desires, or the length of time we spend together.
And now for some comic relief to perk us up after that sad tale —
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© Teresa J. Conway, 2022