A Cougar’s Story Ch. 02

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After my indiscretion with Bob that Oktoberfest weekend, Jim and I’s sexual activity increased considerably, mostly if the truth be told, because of my initiating ‘fooling around’.

There was no doubt about it anymore, at least for me, that the night with Bob had reawakened a part of me that wouldn’t go back to sleep. One evening, after Jim and I had finished a very delightful 69 session, I lay with my head on his thigh, enjoying the cleaning I was doing of Jim’s cock after he had climaxed.

He had gotten me off, as well, to be sure; few men I’ve ever been with can eat pussy like Jim. I always told him that in a previous life, he had to have been a lesbian; we always laughed at that analogy. But, the truth was, that my body craved a bit more, craved a long and serious fucking and somehow, Jim knew that; Jim always knows.

So it was in that moment that Jim asked me if I’d like to go out of town the next weekend, to a larger city, a major Midwestern Iconic city, and perhaps, if I’d like, go trolling for a younger stud for an evening of fun and games. I said that as good as that sounds, it’d be a stretch to think I could walk into any bar or club and walk out with young studs sniffing at my heels.

He disagreed but understood my trepidation at the ‘trolling’ thing and offered up an alternative. He then suggested that, if I was in agreement, we’d do a bit of looking on a swinger’s site that we had used in the past, when we were active in the lifestyle. There’s always ads of singles looking to hook up with a couple and such. I thought about it for a bit as my tongue finished licking his cock, then holding his cock in my hand, I lifted my head, looked at him and said that I wouldn’t be opposed to ‘just looking’ at the site along with him.

As I was falling asleep that evening, in Jim’s arms, I remember thinking that if we found an ideal candidate for fun and games, that I hoped it would live up to my current fantasies that were running through my mind.

It did.


A quick note to all of you singles guys out there who advertise on swinger sites and the like; posting pictures of just your cock is not a turn-on, despite what you might think. People, women like me, want to see the face, the eyes, the smile, that’s what will normally attract attention, not an image of your hard-on.

Just my own opinion.

Jim and I were looking through the site one night after we had had that conversation, quickly discarding those without facial pics, and there were a lot of those. Narrowing it down to four or five that had good facial photos, we ended up sending off an email to only two of them, choosing those whose written ad indicated that they had a modicum of intelligence, if the written word can be used as a yardstick.

Both responded the next day, and I wrote back this time, since I was the one who was the ‘target’ for a playmate; and yes, the fact that they answered our response to their ad, knowing that I was fifty-something, turned me on, it turned me on, a lot.

Jim was out of town that evening and I was at the computer when I had received an IM message; it was from one of the guys that we had contacted.

We, Greg and I, began a live IM session with very normal, non-sexual, electronic conversation. Slowly, our messages became a bit more sexual in nature, though not pornographic, if you know what I mean.

Greg gave me a site to go to where we could have a live session, both of us able to use our web-cams to stream video of us both as we ‘chatted’. Asking him to give me a moment, I told him I’d join him on the illegal bahis site after I fixed myself a drink.

Now, for you doubters out there, I assure you had Jim been in town, I would have still had this interaction with Greg on the computer. I am, and always have been, able to separate lust and love; that’s of paramount importance if one chooses to participate in the swinging lifestyle. Those that can’t, usually wind up in horrible personal situations. Jim and I have been very fortunate that we’ve been able to avoid that.

I did fix myself a drink, but I also ‘freshened’ up a bit, combing the hair, checking the makeup, though I use hardly any cosmetics beyond lip gloss and a little blush, but still.

Logging into the site, Greg and I were connected in a few seconds, and when his live-video appeared, I was somewhat shocked that he looked as young as he did. His pics that accompanied his ad showed him to be a bit older-looking than what I was now seeing.

He, on the other hand, greeted me with a ‘Wow’, and he commented on my attractiveness; and yes, that pleased me greatly, though I tried hard to cover my little bit of thrill that he thought of me as so.

I had changed tops to one that allowed what little bit of cleavage I have from my B-cup breasts to show, to my advantage, obviously.

As we chatted, growing more comfortable with our interaction, the thought of meeting with him cemented itself with me. He acted very much in a gentlemanly, albeit, sensual, manner. Simply said, my crotch reacted very favorably to his image, and his words.

No, there was no total strip-down by either of us, no mutual masturbation, or anything like that. Both of us, as we chatted, did have one of our hands out of sight of the camera; I can’t speak for him, but mine was playing with Ms. Priss, under the computer desk. Agreeing to call him after Jim and I checked into our hotel in the downtown section of his city, we signed off.

The masturbation, for me, occurred after we had signed off and I had gone to bed, thinking about the possibilities.

When Jim came home, the next day, I was upfront with him about Greg and I’s webcam chat of last night. He was pleased that I seemed to be fully on-board with the upcoming weekend.

That night, Jim and I had a very memorable oral session, pleasing us both, immensely.


We called Greg, after checking in, setting up a time for him to meet us downstairs in the hotel’s lounge. As I prepared for the evening, I was a bit a-flutter with excitement, truth be told.

Greg was 31 and quite attractive, more so in person, than in pictures or on the webcam. He is single now, divorced with no children, and an IT manager for his firm. His conversational ability was exceptional and in person, just as on the computer, every bit a gentleman. He knew that Jim would be with us when ‘the deal would be sealed’, and was very comfortable with that, as well.

We settled into our drinks and conversation, letting the vibes settle down between us, falling into a comfortable zone very quickly with each other. He asked me to dance when the small Jazz combo began playing some very good, slow, Bluesy-type tunes, the kind that make you want to dance, you know?

He was a good dancer, easy to follow, nice to hold onto as we glided across the semi-crowded floor. His arousal, through his dress slacks, couldn’t be hidden or ignored, and I leaned against his hard-on purposefully, enjoying the feel of his hardness against my body.

I danced with both Jim and Greg for about an hour or so, and as my illegal bahis siteleri last dance with Greg ended, I dropped my hand between us, giving his erection a tender squeeze, the heat from his cock penetrating through the pant material. He looked at me, smiled, and moved his own hand between us as he held mine from dancing, letting his fingers brush across my braless breasts, my erect nipple, a bit of a speed bump.

We walked back to the table holding hands, neither saying anything, just enjoying the moment. Jim smiled at us, and suggested that perhaps the three of us should go back to our room, actually a ‘suite’ with the bedroom separate from the common area. We were all drinking Scotch and water and had a bottle and ice in the room.


The ride to our room in the elevator was a nice one, both Jim and Greg taking the opportunity to kiss me, both lustfully which I returned with equal passion. Jim volunteered to fix us all drinks while I changed into something a ‘little’ more comfortable.

Being on the thin side (5’8″ a pair of running shorts, snug and tight to my butt, and a ‘wife-beater’s’-type shirt, both soft to the touch.

Jim sat in an armchair, facing the couch, a coffee table between us, while Greg sat on the couch with me. We talked for a short while, letting the Scotch work its magic on us, letting the mood take on its own life. Jim made sure that both Greg and I understood that we were free, at any time, to forget that he was even in the room; that we should take it from there.

He also made sure that Greg would be comfortable with him joining us in the bedroom or not, Jim hadn’t made up his mind about that quite yet. Jim already knew that I was okay with him watching; been there, done that many times in our past.

With all of that out in the open, I started the ball rolling by leaning in to Greg and kissing him, my hand on the side of his face as our tongues found each other’s, his hand finding the route to my breasts, as we kissed with increasing passion. His hand slipped under my top, finding and caressing my breasts as my own hand moved to his erection which was pushing hard against his pants. As Greg and I continued to kiss, touch, and fondle each other, I unzipped his fly, reached in and pulled out his rather nice cock, running my hand up and down its hardness.

While I continued to stroke him, I bent down and took him into my mouth, deep-throating him very quickly; some women can’t deep-throat, but I’m not one of them, and I enjoy it very, very much.

It was just Greg and I in that room in that moment, my total focus concentrated on pleasuring him as his hands fondled me with great skill. I could sense that if I continued sucking him, he’d soon climax and I didn’t want him to, yet. As I lifted my head from his cock, he pulled me to him and kissed me, his tongue having its way inside of my mouth.

Breaking from the kiss, I stood and pulled him from the couch and towards the bedroom. Looking over to Jim, he was all smiles and had a very nice erection going on inside of his own pants, which brought a smile to my lips.

Greg and I helped each other out of our clothes, kissing, nuzzling, touching the whole time. Dropping to my knees, I took him into my mouth again, totally swallowing all of his cock which brought a contented sigh of pleasure from Greg. Standing, I kept my hand on his erection, leading him to the king-sized bed.

I totally surrendered my body to his skillful hands and mouth as he made love to me in a very skillful manner, bringing me to brink of orgasm several canlı bahis siteleri times but not quite letting me reach it. Was he teasing me? Of course, but I loved it!

Finally, he mounted me, sliding easily between my parted legs as I wrapped them around him; slowly, tenderly, he began fucking me, the feel of his hardness inside of me a thrill beyond imagination.

He was long-lasting, thankfully, allowing me to have multiple orgasms, the last one a real mind-blower which brought a small cry of joy from my lips. As his speed increased, as he concentrated on his own climax, I glanced over to the small settee in the bedroom and saw Jim sitting there, naked, stroking his rock-hard cock. Just as I smiled at Jim and his hard-on, Greg came. Greg came with a forceful thrust that brought me another, small orgasm as his diminished.

Looking over towards Jim and smiling, I told Greg to roll onto his back, that I wanted to suck him clean; he did and as I moved between his legs, I kneeled on my legs, positioning my ass and pussy for Jim. Leaning on an elbow, I guided Greg’s semi-flaccid cock into my mouth, licking and sucking on him, tasting the mixture of his cum and my juices.

I felt Jim’s weight on the bed as he kneeled behind me. I knew he knew what to do with my upturned pussy, and he did. His thick, hard dick slipping into me, his thrusts strong as I felt Greg’s cock getting hard again from my sucking and licking.

My favorite thing to do with two guys is to suck one while being fucked by the other. I loved it when we were ‘swinging’ and I loved it even more since it had been quite a few years since I’d had two men like this.

The thrill of Jim fucking me like he was twenty years younger and of Greg’s cock in my mouth sent me over the edge to another climax; my moans of contentment spurred both of my guys to their own orgasms, their voices crying their own joy of completion.

We collapsed onto the huge bed, smiles all around, except for me; I was smiling alright, but my smile was framed by Greg’s cum on my lips, lol.

We rested for a while, and then Greg did the bartender thing this time, returning with fresh drinks for all of us. We sat against the headboard, totally naked, and my comfortability with that surprising even me, after such a long time since my last threesome.

Jim excused himself, encouraging me to have another go-around with Greg, ‘one for the road’, so to speak.

We did, Greg and I, have another incredibly satisfying fucking session. Several more climaxes available to me, which I took, whole-heartedly. Resting afterwards, I thanked Greg for an incredible evening of sex, and of his gentlemanly behavior, which I found so endearing.

Jim and Greg shook hands, Jim having gotten dressed again, and thanking him as well, Jim walked Greg to the door. When he returned to me, still standing in the common room, we smiled at each other, embraced, and shared a wonderfully, erotic kiss. Turning out the lights, we went to the bedroom.

I showered, then he did, and we climbed into bed.

We talked about the evening’s events, of course we did; one of the most fun things we both liked about the swinging lifestyle is the sharing of flings with one’s partner, even if the fling was the same.

We both agreed that we were surprised at Jim’s sudden return to his ‘studly self’-his words, not mine-and how great it felt for the both of us when he was inside of me.

I remember his words that night, just before we fell into a well-earned sleep; I remember as if it were said to me today.

“You know, baby,” he said, “If a side benefit of you having a fucking from a younger guy results in a repeat of what happened with me tonight, I’d be pretty fucking happy about that.”

Yeah, I would be too; I was thinking exactly the same thing when he said it.

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