RolandLord, Author at NSFW story — Page 5 of 5

Surviving [M]y First Craigslist Encounter [F] (Pt 5)

But she couldn’t wait much longer. She ran both sets of fingertips up to the waistband, tucked them underneath, and pulled down. The waistband hooked on the head, and as a result, my cock started to pull away from my stomach. When she realized what was happening, she pulled up and released me. Before I knew it, she had pulled my underwear all the way down, exposing my entire shaft.

Somewhere in the back of my mine I realized this was only the second time someone other than my wife had seen my erect cock, and that voice asked why I wasn’t already climaxing. Indeed, this was the most exciting moment I’d had in many years.

And in the midst of all this excitement, another voice in my head reminded me that I’d just met this woman a half hour ago, I didn’t even know her last name. How well did I know her? How did I know that she didn’t have some man-hating agenda in mind, that her goal was to get me in a vulnerable state, and then do something horrible? Was a jealous husband or an angry brother waiting in the back bedroom? Or maybe once I closed my eyes she’d render me unconscious and I’d wake up in a dumpster without my kidneys? I was certainly vulnerable at that moment, couldn’t have been more unless I was handcuffed to her bed. Read more »

Surviving [M]y First Craigslist Encounter [F] (Pt 4)

Her fingertips danced over the twin bulges in my jeans, and I knew she was not going to stop there. She wanted to touch me as much as I wanted her to. Just how she was going to do it, the anticipation was nearly painful.

I groaned loudly, and she smiled wickedly. She let her fingers dance back and forth, running them over the sensitive surface of my balls, just a bit of cloth separating her skin and mine.

She continued to brush her breasts against my legs, knowing that the visual was continuing to arouse me. She hadn’t really thought much of her breasts, her husband had never given her a second look, and as many middle-aged women, as they started to lose their firmness, she became unhappy with them. But suddenly she realized that her own point of view was not only limited, but not necessarily shared. As she teased me, seeing how she was turning me on, I could see her nipples harden, showing her excitement as well.

Surviving [M]y First Craigslist Encounter [F] (Pt 3)

We dry-humped for a few minutes, my hands on her hips, balancing her, guiding her, then slid my hands up her sides, to her ribs, and slowly began to caress her sides, making sure not to actually touch her breasts.

Her breasts were big and round enough that they stretched the sides of her camisole, and it was actually difficult to run my hands up her sides without making intimate contact. Somehow it’s one thing to be hugging or grinding, and quite another to actively use your hands, isn’t it? I began to caress the round sides of her breasts, very lightly and carefully, waiting for a reaction from her, wondering if she’d decide that I’d just reached a line, that she didn’t want to go any further.

But that signal never came. I continued to run my fingertips along the sides of her breasts, and then started to draw a line underneath her mounds, determining just how large and soft they were, and then suddenly she daringly pulled both of her tops off, exposing her bare breasts for me.

I gasped.

Surviving [M]y First Craigslist Encounter [F] (Pt 2)

She motioned for me to sit down. She sat down next to me, turned, faced me and kissed me again. We quickly realized that at our age, our bodies weren’t as supple as they needed to be in order to neck while sitting next to each other. She sat up and then in one smooth move, daring in retrospect, spun 180 degrees and crawled on top of my legs, straddling me, facing me. At the same time, I slid down the couch a bit, slouching, lying back at nearly a 45 degree angle.

Her arms fell naturally to her sides, my hands naturally moved to her hips, and we looked at each other, examining the nooks and crannies of each others faces.

“So, hi!” I grinned.

She smiled, and without saying a word, leaned forward and began to kiss me again.

First my forehead, then the bridge of my nose, the tip, over to one cheek, then, finally, brushing her lips across mine, softly, almost imperceptibly. I lay back, enjoying her attentions, enjoying the ability to be 100% the recipient for once.

Surviving [M]y First Craiglist Encounter [F] (Pt 1) (LONG)

(This is part one of many parts, and as such, it’s not for everyone. It’s for those with an attention span.)

My marriage was falling apart.. I kept hoping for a rebound, hoping that she’d snap out of her funk, but as the years approached a decade, I was losing patience. I’d tried everything, being kind and understanding, being aloof and standoffish, being demanding and stern, but she kept distancing herself from me. Time after time I heard, “You’re just not important to me.” I couldn’t believe my ears the first time I heard it, but after the seventh or eighth time in a couple of years, I realized it wasn’t a one-off. And I became lonely, very lonely.

So I posted something on Craigslist, as our rift approached the second half of a decade. A last ditch effort to keep myself sane while staying in my marriage.

“Man, I wish I were 10 years younger! FUNNY ad, and I hope you find someone.”

Well, I answered, asking how old she was and why the age difference was a problem for her, and we ended up chatting back and forth and trading info about each other pretty quickly. Read more »

She surprised me – and herself – on our first meet [FM]

Cathy and I met online, and flirted for a few days, getting increasingly sexual, but nothing overt. Finally we found a time to meet for a drink. She was wearing a very tight black tube dress, short enough to show most of her thighs, and a high neck that helped accentuate her sizable bustline. I was disappointed about the lack of cleavage, but the tightness almost made up for it.

We flirted at dinner, innuendo and suggestive talk. I stood up to go to the bathroom, and pretending to adjust my jeans, to make sure she saw how tight they were. And when I returned, having made sure I was nice and thick after I tucked it back in, I stood in front of her again, hoping she would notice the bulge. She didn’t say anything, but I suspected that she was pleased to catch an eyeful.

We left and as we turned the corner, I grabbed her and we started making out by the side of the building.