[M] A Married Man’s Confession #2: I Tricked a [F] Squirter from Craigslist into Meeting Me

I hereby offer up my second confession. I am now past 65 years but this took place a good 16 year ago.

My wife could have been a squirter if she were not afraid to just let herself go. But she has always been sexually repressed, though does enjoy it when I eat her. It never seems to take more than 5 minutes for her to lurch into an orgasm when I eat her sweet pussy, and finger her just so. Too bad she never enjoyed sucking cock.

When we first became intimate, and I would eat her, she would orgasm in short order, and I would want to keep licking and eating but would she push my head away and say No! I am about to pee, please stop! I was not experienced at this time, so did not understand what I think I do now — that she was repressing the urge to squirt. I did understand though that she needed to let loose, and I would have loved it if she had. I was ready to take a facefull of … whatever juices she was willing to give me. I don’t have a pee fetish. I just wanted her to enjoy herself to the limit.

But she never did.

Years later, after I had seen enough porn and heard and read enough to know about squirting, but had still never experienced it … not even after two plus decades with my wife, who over time lost that urge to ‘pee’ … I posted another ad on craigslist. This was after the ad I described in my first confession. The subject line read, ‘My fantasy is … ‘ and you had to click on the ad to read the rest of the sentence ‘… to be with a woman who squirts.’ The rest of the ad listed my age, body type, and the usual initials (DDF, HWP, like that).

Well, this would not be a story if I did not get the response I was looking for. A charming woman answered, well spoken, and said she might be willing to give me ‘a little squirt or two’. We exchanged a few emails, then began writing with our ‘real’ accounts, not through the craigslist anonymized method. Her email handle included the word ‘puddles’ — very promising! She said she enjoyed fulfilling the fantasies of older men. I was past 50 and she was in her early 30s. We set a time to meet over drinks. The meeting took place on a spring evening during a time when our city fills up with tourists for a major, well-known event that lasts several days. The conversation went well enough, up to a point. We talked music and local politics, and she bragged that she personally knew Craig .. yes, that one, of cragislist fame. She was a creative, artistic sort, interesting and sexy with long brown hair and thick kissable lips. I wanted her.

But I was upfront with her about being married, so she demurred, saying something about once being surprised by an angry wife while fucking her husband. I could not reassure her that this would not happen with us her. And I had not figured out the logistics of getting a room, with all the tourists booking everything in sight. So she left me disappointed. I admit that I was very saddened by this unexpected turn.

But wait! There’s more. A year or so later, I posted another ad, pretending to visiting from out of town again (see my first confession on this forum). And who should I get an answer from but her? I recognized her spirit, and soon I recognized the email address. So I wondered how can I make this work this time? Clever boy that I am, I found a way. I wrote back from a hastily created new email account, copying and pasting our crailgist emails and putting quotes around then. Anyone looking closely could have noticed but who looks that closely? And I shaved off my short beard that I sported when we first met, removed my glasses and crossed my fingers.

We arranged to meet at a Whole Foods downtown among the fresh fruits and veggies. She said she’d be wearing a sexy red dress and black pumps. She looked great, got lots of stares and knew she was putting on a show. She smiled when I approached, and happily for me gave no sign of remembering our earlier non-encounter. She did ask why my face was a bit red (I had not shaved in a long time so my skin was sensitive), and I made up some story on the spot about having to use my host’s shaving cream because I had left mine at home, and there must have been a slight allergic reaction. It all worked.

I paid for some well-chosen blueberries and cherries and a chocolate bar, to complement the wine I had in the car. She followed me in her car to a nearby hotel and I secured the room.

This hotel has rooms that open directly outdoors, like a motel but somewhat better. Just the kind I like. I made the mistake of getting a non-smoking room, but she was able to smoke on the balcony. We had not discussed that.

As for the sex … it was lovely! She was rich in experience, said she’d been broken in by an older man when she was in her late teens who taught her her how to be a geisha. She never self-penetrated, she said, with her fingers or toys; that was part of her training. Her tits were warm and wonderful and she let them and her long hair brush against my stomach and cock as she lay above me, between licks and kisses. When I ate her, she insisted that I only lick her clit… that was the one way to move her. She would reach for a cherry or blueberry, take a bite and then rub her pussy juices on it before lifting it to my lips. and did the same with pieces of chocolate. She was adept at role-playing, and spoke in different voices as the evening wore on, sometimes talking in the voice of an innocent young college student seduced by an older professor. I mention it to give you a sense of her style and talents. She was beyond creative, magical in her gestures and words. And yes, she did squirt, a sweet, musky liquid that turned me on enormously and made my cock grow so hard. This was pre-viagra, alas, or I would have fucked her deep, deep into the night. But we enjoyed ourselves.

She told me enough about herself for me to figure out her real identity though some internet sleuthing. I am scary good at that. But I never saw her again or emailed her or anything, and just wanted to satisfy my curiosity. All these years later I look her up online on rare occasions to get a sense of how she is faring. And I certainly never told her that this was not our first but second encounter! I would not mind running across her someday, and can’t imagine that she’d recognie me after all these yeers, especially since i almost always have a beard. But I”d know her and would contrive some way of engaging her and then see where it takes us.

Another craislist adventure in another city led to a another woman who did squirt in geysers. More on that in a day or two.

Thanks for reading!

Source: reddit.com/r/gonewildstories/comments/hu0kgy/m_a_married_mans_confession_2_i_tricked_a_f