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re: Looking back at times where you missed out on an obvious opportunity for sex

Posted on 9/10/21 at 11:41 am to
Posted by soccerfüt
Location: A Series of Tubes
Member since May 2013
74897 posts
Posted on 9/10/21 at 11:41 am to
quote:

When I was 17 one of my moms friends, whom I’ve known for most of my life stopped by our house for a visit (back when people use to show up to visit unannounced) but my mom wasn’t home.

She was in her early 40’s, face wasn’t all that great but body looked nice with a set of natural DD’s. I answered the door in swim trunks, no shirt and invited her in. I told her my mom was in Little Rock for the day. She asked where my dad was, and I told her he’s on a work trip.

She says well I haven’t seen you in months and gives me a hug. As she released the hug slowly, she let her fingertips go down my back, stopping at my lower back and gently rubbing it. The whole time she’s looking at me while doing this and I just take a quick step back like a bitch. I don’t know if I was more scared of that older pussy or my mom finding out.

I regret to this day not going in for the kill.
Probably your birth mom.
Posted by rockchlkjayhku11
Cincinnati, OH
Member since Aug 2006
36755 posts
Posted on 9/10/21 at 11:41 am to
i wont go into boring details on specific instances but on a more philosophical level, the few times that this happened to me, i remember thinking shortly after that "there will be another time" or "i'll do things differently next time i see her" or something similar, but there never was another time for the couple of girls im thinking of.

it's so weird how that happens. i feel like i don't even remember the occasional instances where there actually was another time and things did go differently and we hooked up. those first encounters that i completely fricked up become meaningless due to the second chance, but they weren't any different to begin with.

now, all i remember are the opportunities that were squandered. brains are cruel.
Posted by BRIllini07
Baton Rouge, LA
Member since Feb 2015
3206 posts
Posted on 9/10/21 at 11:45 am to
I feel like there are many categories of this, each with their own level of pain.

1) Young, stupid, and not able to read a sign
2) Young, know how to read the sign, but don’t know how to act
3) Pass on an OT7 because you think you have a shot at her OT9 friend - lose out on both
4) Pass on an opportunity because you think the window will be open for a while, window slams shut the next day
5) Try to be faithful early in dating, dating relationship with the other girl ends a few weeks later

….I think I’ve checked off all of these boxes
Posted by MBclass83
Member since Oct 2010
10270 posts
Posted on 9/10/21 at 11:50 am to
I'm pretty sure girls have had these moments too.
Posted by chinhoyang
Member since Jun 2011
26069 posts
Posted on 9/10/21 at 12:08 pm to
quote:

I'm pretty sure girls have had these moments too.


With my luck, it would be tigergirl.
Posted by greenbean
USAF Retired - 31 years
Member since Feb 2019
6394 posts
Posted on 9/10/21 at 12:36 pm to
In an Asian county in the late 80s. A roll in the hay (with a good looking native hottie) was usually $20. I was at one time presented with a proposition of two girls at once for $30, for whatever reason I passed (i think to t---ty frick a large breasted gal), I've always regretted that.
Posted by terriblegreen
Souf Badden Rewage
Member since Aug 2011
12300 posts
Posted on 9/10/21 at 12:44 pm to
Once I almost missed out, but redeemed it.

I was in the Guard in college and after drill on a Saturday went in this grocery store to buy beer in uniform. I ran into a girl I knew from high school who was working the checkout line. She says "you look good enough to frick". I was so caught off guard I just laughed and left. As soon as I walked out I realized I was retarded. I ran home and called the stored (this was in the 90s) and asked to talk to her. I asked her to hang out after she got off. We hooked up and my earlier frick up ended up working out.
Posted by KiwiHead
Auckland, NZ
Member since Jul 2014
37608 posts
Posted on 9/10/21 at 12:47 pm to
shite, baw. I had one come out right before I got married and out and out told me. She used to come to my apartment in college to go over biology notes . She was best friends with my cousin and actually lived about a half mile away when we were growing up and what is worse, I had the hots for her in high school. She became a doctor.
Posted by RoyalAir
Detroit
Member since Dec 2012
7500 posts
Posted on 9/10/21 at 12:48 pm to
Worked with a very good looking and overly flirtatious older Hawaiian woman when I was single. She calls me up and says a bunch of friends from work are going out on her boat for that Saturday. I show up, and it's just the two of us. I don't think too much about it, cos I'm not too bright, and, cos she was married. I could have been Jody, easily. Thought about it, but I didn't want to be the guy that this ultimately happened to in the future.

Now, had she said her husband was cool with it? Prolly woulda given her some disappointment.
Posted by dagrippa
Saigon
Member since Nov 2004
12171 posts
Posted on 9/10/21 at 12:49 pm to
In hs I met up with my girlfriend that was house sitting with her friend. Her friend kept sucking on my fingers like she was gonna blow me and what did I do? Nothing.
Posted by Jor Jor The Dinosaur
Chicago, IL
Member since Nov 2014
7467 posts
Posted on 9/10/21 at 12:49 pm to
quote:

A roll in the hay (with a good looking native hottie) was usually $20. I was at one time presented with a proposition of two girls at once for $30
BOGO half off?
Posted by jchamil
Member since Nov 2009
19502 posts
Posted on 9/10/21 at 12:53 pm to
quote:

I don't think too much about it, cos I'm not too bright, and, cos she was married. I could have been Jody, easily. Thought about it, but I didn't want to be the guy that this ultimately happened to in the future.


So what happened? The two of you just awkwardly hang out on her boat by yourselves?
Posted by CatfishJohn
Member since Jun 2020
20343 posts
Posted on 9/10/21 at 12:56 pm to
Girl I knew really well, total friend zone in high school and college, climbed into bed with me in college and took her shirt off. She was very attractive. I had passed out drunk early on at her house in her bed on top of the covers fully clothed.

I was so drunk I didn’t realize what was going on and said “oh sorry I’ll take the couch”.

Next day she told me what happened and said she tried to hook up and I turned her down and “probably for best anyway, might’ve ruined our friendship”. We are no longer friends anyway.

I think about this so much more than I should.
Posted by Matador
Member since Oct 2012
276 posts
Posted on 9/10/21 at 1:02 pm to
I was on military leave for a week visiting home and I messaged this HS friend on MySpace straight up “when do you want to smash?” With nothing to lose. Since I was going back out of town I would likely never see her again and didn’t have to face rejection, the courage was high. She replied back and to meet her up that night at a mutual friends house. My other cockblock friend that I was hanging out with that night wouldn’t drive me by and we ended up just getting drunk.
Posted by El Segundo Guy
1-866-DHS-2-ICE
Member since Aug 2014
11653 posts
Posted on 9/10/21 at 1:06 pm to
My buddy in the Army had his sister in town and he set me up with her. Things were going well then we all go back to his house and as we're getting heated, I notice she had a jayhawk tattoo above her ankle.

I couldn't do it. Just couldn't. I even thought about grudge f ing her but the thought was repulsive after what they pulled against my fellow Missourians in the 1800s.

Posted by Comic_Tiger
Member since Jul 2020
1277 posts
Posted on 9/10/21 at 1:06 pm to
was at a LSU Rugby Halloween party and I was after this cute girl that was always hanging around. I had my heart set on her and in retrospect she had hers set on someone else. Still I pursued. And I totally ignored this very friendly, very pretty blond that was sending me all the right signals at that party that night. Yeesh.

When I was older, worked a night shift at a job with a beautiful mature tall blond who was very well, almost perfectly endowed boobs. She would make all sorts of unprofessional little quips or comments to me when no one was around. It was obvious she was waiting for me to make a move. I never did. And I know at her age she was experienced, knew what she wanted and knew how to please. Ugh.
Posted by SlidellCajun
Slidell la
Member since May 2019
16419 posts
Posted on 9/10/21 at 1:08 pm to
I’ve had a few but there is this one that was so incredibly hot that it actually bothers me to this day. I was younger than her by 2 years so admittedly I was intimidated.
She had a boyfriend too and I was worried about him because he and his friends were sort of a badass and they definitely would have messed me up. But she was soooooo hot and we were very intimate for about 2 weeks. we messed around a good bit and then it ended. Her boyfriend came back and it just ended.

I think back to one night where it was on. She met me out and we went back to my place at her request and it was so on. I gave her a foot massage, then her while body and she massaged me and it was totally erotic but we didn’t go all the way. It kills me.

I admit that I’ve tried to look her up to see what she looks like today but I can’t find her. Deep down I hope that she aged poorly so I won’t feel so bad.

She was so friggin hot
This post was edited on 9/10/21 at 1:23 pm
Posted by Tom Joad
Member since Sep 2021
192 posts
Posted on 9/10/21 at 1:10 pm to
quote:

Years later, I run into her gay younger brother. We were talking about his sister (with whom he apparently had a falling out) and he said "she would have fricked your brains out all summer if you hadn't have been so busy treating her like some Princess."



So you mean that you hooked up with the brother instead?
Posted by greenbean
USAF Retired - 31 years
Member since Feb 2019
6394 posts
Posted on 9/10/21 at 1:12 pm to
quote:

BOGO half off?


IKR? I'm a dum azz
Posted by Tom Joad
Member since Sep 2021
192 posts
Posted on 9/10/21 at 1:20 pm to
I was about 28, playing in a bar band and on a break this really hot girl about 19 invites me come with her to uhh smell some powdery stuff. So we go to her car and do so and start making out. She’s totally into it and for some stupid reason. , probably the alcohol, I advise her that a young lady shouldn’t allow all those older guys to be fawning all over her in the club. She gets pissed , gets out of the car, and heads back in. Later during the next break her less attractive sister comes up to me, pats me on the shoulder and just shakes her head snd walks off. That was just stupid as hell. Never saw her again after that night
This post was edited on 9/10/21 at 1:23 pm
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