How clueless were you?

[Baztrachian]

What’s the furthest you’ve been from fun while it was right under your nose?

When my second wife Rae was 15 I had utterly no idea that she had a massive crush on me. I'll be honest that she was almost invisible to me as even being female at the time.

A few years later I run into her after I'd been through a divorce. There were a couple missed connections and then one day she's at the door of my apartment. Long story short, I fucked her. She came to my place wanting this and she got it in spades.

Frankly, I damned near messed up the best thing to happen in my life. Fortunately she didn't run out on me and instead fucked me right back once she knew I wasn't just going to cut out on her.

Before that I ran into a local weather girl in Sacramento and had utterly no idea she was interested in me. I ran into her years later when she recognized me in a major city on the east coast. We had some drinks and she told me she'd been depressed when I had rejected her years before. I clarified and she felt better after finding out that my being oblivious to her sly approach was not a rejection. Not at all. I'm glad life went well for her. Five kids and three grandkids so far.

 

[smoothwiener]

Former Lady friend of mine, that I was sleeping with for a while pointed out when we were out picking her a new laptop on the various women she saw looking at me when my gaze was elsewhere. I brushed it off until I caught one doing it. Did wonders for my ego, being I was already married it was far too late to help in the dating scene.

 

[LusciousLili]

A woman in the locker room I talked to sometimes: "You're lucky to have such nice breasts, I love your skin." She asked politely for a feel and I let her. She was maybe 35. I remember she touched it for 5-10 seconds.

I didn't think anything of it til a year or two later I told a friend. "That girl wanted you" she said, lol.

 

[HornyLittleDevil2026]

Many years ago, I was driving through town a day or two before moving across the country when I spotted two women at the bus stop. Small community and I had nailed both of these girls fairly recently. One was an ex-girlfriend, and one an ex-FWB, who were friends with one another. I stopped and offered them a ride. They gladly accepted, I got them to where they were going, and that was it. A year or so later, while corresponding with the ex-FWB, I learned that they would have done a 3-way with me as a "goodbye" if I had only asked, and they had expected that's what I was going to ask for in return for the ride. DAMMIT!!!

 

[Beholders_Eye]

Years ago, when I was in the (?) grade in school, there was a social meetup in a local secluded spot; a makeout area. I had a pretty little date, and we did a lot of kissing. At one point she said touched her head and said she had a slight headache. I drew back, whereupon she said "Don't let that stop you". I was so naive that all I did was some more kissing, and she lost interest. Have often thought about that moment....

 

[Isinlarsa]

Years ago, when I was in the (?) grade in school, there was a social meetup in a local secluded spot; a makeout area. I had a pretty little date, and we did a lot of kissing. At one point she said touched her head and said she had a slight headache. I drew back, whereupon she said "Don't let that stop you". I was so naive that all I did was some more kissing, and she lost interest. Have often thought about that moment....

I had a similar misadventure when I was 17. We were at a drive-in movie making out. Things were getting pretty hot, so I thought I would be responsible, and said. "We better slow down or we may do something we regret." She immediately responded "No we won't." Only later did I realize she meant we wouldn't regret it.

 

[write_or_wrong]

Years ago, when I was in the (?) grade in school, there was a social meetup in a local secluded spot; a makeout area. I had a pretty little date, and we did a lot of kissing. At one point she said touched her head and said she had a slight headache. I drew back, whereupon she said "Don't let that stop you". I was so naive that all I did was some more kissing, and she lost interest. Have often thought about that moment....

My college roommate told me his GF told him that orgasms cured her headaches. He happily ate her a lot. Win-win!

 

[HornyLittleDevil2026]

My college roommate told me his GF told him that orgasms cured her headaches. He happily ate her a lot. Win-win!

No shit! I would have been like, “Honey, I’d like you to meet my cock, Mr. Tylenol, and my tongue, Mr. Ibuprofen.”

 

[Suckharder55]

When my second wife Rae was 15 I had utterly no idea that she had a massive crush on me. I'll be honest that she was almost invisible to me as even being female at the time.

A few years later I run into her after I'd been through a divorce. There were a couple missed connections and then one day she's at the door of my apartment. Long story short, I fucked her. She came to my place wanting this and she got it in spades.

Frankly, I damned near messed up the best thing to happen in my life. Fortunately she didn't run out on me and instead fucked me right back once she knew I wasn't just going to cut out on her.

Before that I ran into a local weather girl in Sacramento and had utterly no idea she was interested in me. I ran into her years later when she recognized me in a major city on the east coast. We had some drinks and she told me she'd been depressed when I had rejected her years before. I clarified and she felt better after finding out that my being oblivious to her sly approach was not a rejection. Not at all. I'm glad life went well for her. Five kids and three grandkids so far.

I was 18 and picked up two female hitch hikers (Late 1979?). They had no money and wanted me to buy them beer and they had an empty house to themselves.
pass…What an idiot!
I still jerk off to what might’ve happened if I said yes

 

[HornyLittleDevil2026]

I was 18 and picked up two female hitch hikers (Late 1979?). They had no money and wanted me to buy them beer and they had an empty house to themselves.
pass…What an idiot!
I still jerk off to what might’ve happened if I said yes

I know what you mean. I once picked up a cute hippie chick hitchhiker and did nothing more with her than bring her from point A to point B, with scenarios of us fucking or at least me getting a blow job, running through my head the whole time, while in reality, only chatting about the weather and other nonsense. I jerked off for a long time fantasizing about what could have been.

 

[Baztrachian]

I was 18 and picked up two female hitch hikers (Late 1979?). They had no money and wanted me to buy them beer and they had an empty house to themselves.
pass…What an idiot!
I still jerk off to what might’ve happened if I said yes

Sounds like a great story idea!