One that Got Away...

[cubbyfire04]

Met her at a concert... We hit it off. She was a bit older, gorgeous, and clearly interested in hooking up. Her friend was definitely going back to with my friend, too.

I proceeded to indulge in far too many substances (I had a phase, ok...) and I blacked out and wound up in a hotel with her and her friend in my buddy's bed. All 3 of them naked. I was informed when I woke up that this was supposed to be a 4-some but I wound up being carried from the cab to the room. Apparently the 3 of them fucked all night right next to me with the lights on and I missed the whole thing .

 

[HoldYouDown]

A few of these...a female friend of mine who broke up with her bf (who was also a friend). She moved to my neighborhood. He lived far away. She basically threw herself at me but I was too strict on not banging my friend's ex. Looking back, I hardly talk to either anymore, both have families. I should have lightened up.

Also there were a few girls in college who made it painfully obvious they wanted me, but I was going through a low confidence phase. (I got action in college, but could have had much more.)

More recently, a girl who liked me but was in a relationship and wouldn't cheat. I made a move and she turned me down. At least I tried but I will always wonder.

That said, women are like buses, one leaves, another comes along. (Men too.)

 

[jakie69]

For me it’s a girl I dated at college, she had a reputation for being a slut and being very very kinky. She was such a sweet girl though, very very pretty and loving. When we were together she would tell me about her past and experiences and was open and honest with me about what she’d done and who she’d been with (both male and female) I didn’t care I was smitten and loved her, plus the sex was amazing. We had a pregnancy scare and things went downhill quickly. We started arguing and eventually we went out seperate ways. Never forgot that girl and she’s one of my regrets, the one that got away. I’ve seen her since and she has kids and is settled down but we got talking over coffee and she said I was her one that got away and her first monogamous relationships. She also dropped it on me that she knew my wife quite well which I didn’t know

 

[Nightspeed]

Her name was Trish, and I had a crush on her all through high school. We dated a few times, but nothing ever went beyond necking in the car. We even went to college together for a short time, but she dropped out and moved back home.

During that time, she began dating an asshole from our high school, but she "thought she could change him" and all that shit. When he left for the Army, we started hanging out again, but it was all very chaste and buddy-buddy. Until one night in the summer of 1985.

She was mad at her long-distance asshole boyfriend and so we went down by the river and I just let her vent. We had a bottle of Southern Comfort that we passed back and forth. She smoked a joint (I never got into weed) and we were damned near naked in 30 minutes. We ended up driving back to her house and I completely blew the only chance I ever had with her because in my inebriation I suddenly became all chivalrous and shit, deciding that I wanted to see if she felt the same way sober and then I'd know it was finally the right time for us. She did not feel the same way sober. In fact, she didn't speak to me for a year.

Now she's a far-right extremist white nationalist "Christian". I finally had to cut her out of my life entirely. I still daydream about "What if" and such, had things turned out differently. But she's definitely the one who got away.

 

[screwher]

I don’t have a “one that got away” story. But my wife does. Mrs. Screwher has confessed she was attracted to her now former GM. We hadn’t entered the hotwife lifestyle at that point. So she insists that nothing happened between them. Which is too bad. I know she would have loved hooking up with him after hours. Maybe bent over his desk. Or better yet, an illicit meeting in a hotel room.

But...something may still come of this. She did reconnect with him when he visited the offices right before covid. They exchanged contacts. And as I said, she has confessed to wanting to fuck him. So she knows she has my blessing and full approval. So when she’s ready, I hope he’s still available.

 

[Hand_solo77]

I don’t have a “one that got away” story. But my wife does. Mrs. Screwher has confessed she was attracted to her now former GM. We hadn’t entered the hotwife lifestyle at that point. So she insists that nothing happened between them. Which is too bad. I know she would have loved hooking up with him after hours. Maybe bent over his desk. Or better yet, an illicit meeting in a hotel room.

But...something may still come of this. She did reconnect with him when he visited the offices right before covid. They exchanged contacts. And as I said, she has confessed to wanting to fuck him. So she knows she has my blessing and full approval. So when she’s ready, I hope he’s still available.

I wish I was the GM, I have been in a position of leadership for quite a while now, but have always restrained myself to be respectful, but I have admittedly wished a few of my team members would take it past the point of no return. Unfortunately it's not happened and I am not going to be the initiator. The intensity of a work affair would be intense.

 

[screwher]

I wish I was the GM, I have been in a position of leadership for quite a while now, but have always restrained myself to be respectful, but I have admittedly wished a few of my team members would take it past the point of no return. Unfortunately it's not happened and I am not going to be the initiator. The intensity of a work affair would be intense.

Then my wife is the one who would have to take the initiative. But only after we were 100% sure that you were returning her attraction. And don’t worry, she would want discretion as well. So you visiting our place on the weekend would be best.

 

[BillTheKatt90]

Her name was Trish, and I had a crush on her all through high school. We dated a few times, but nothing ever went beyond necking in the car. We even went to college together for a short time, but she dropped out and moved back home.

During that time, she began dating an asshole from our high school, but she "thought she could change him" and all that shit. When he left for the Army, we started hanging out again, but it was all very chaste and buddy-buddy. Until one night in the summer of 1985.

She was mad at her long-distance asshole boyfriend and so we went down by the river and I just let her vent. We had a bottle of Southern Comfort that we passed back and forth. She smoked a joint (I never got into weed) and we were damned near naked in 30 minutes. We ended up driving back to her house and I completely blew the only chance I ever had with her because in my inebriation I suddenly became all chivalrous and shit, deciding that I wanted to see if she felt the same way sober and then I'd know it was finally the right time for us. She did not feel the same way sober. In fact, she didn't speak to me for a year.

Now she's a far-right extremist white nationalist "Christian". I finally had to cut her out of my life entirely. I still daydream about "What if" and such, had things turned out differently. But she's definitely the one who got away.

From what you describe at the end, that sounds more like a "bullet dodged" than a "one that got away"!

 

[DennisB]

Her name was Trish, and I had a crush on her all through high school. We dated a few times, but nothing ever went beyond necking in the car. We even went to college together for a short time, but she dropped out and moved back home.

During that time, she began dating an asshole from our high school, but she "thought she could change him" and all that shit. When he left for the Army, we started hanging out again, but it was all very chaste and buddy-buddy. Until one night in the summer of 1985.

She was mad at her long-distance asshole boyfriend and so we went down by the river and I just let her vent. We had a bottle of Southern Comfort that we passed back and forth. She smoked a joint (I never got into weed) and we were damned near naked in 30 minutes. We ended up driving back to her house and I completely blew the only chance I ever had with her because in my inebriation I suddenly became all chivalrous and shit, deciding that I wanted to see if she felt the same way sober and then I'd know it was finally the right time for us. She did not feel the same way sober. In fact, she didn't speak to me for a year.

Now she's a far-right extremist white nationalist "Christian". I finally had to cut her out of my life entirely. I still daydream about "What if" and such, had things turned out differently. But she's definitely the one who got away.

I don’t think she is the one who got away. I think you are very lucky to not have gotten her pregnant and then stuck with someone like her for at least 18 years of your life! Not to speak to you for a year!!! Who does that?!?! She doesn’t find you attractive sober but only when she is drunk and high?!?! She is not the one who got away!! She is the type that you never want to catch!!!

Just my opinion.

 

[Nightspeed]

I don’t think she is the one who got away. I think you are very lucky to not have gotten her pregnant and then stuck with someone like her for at least 18 years of your life! Not to speak to you for a year!!! Who does that?!?! She doesn’t find you attractive sober but only when she is drunk and high?!?! She is not the one who got away!! She is the type that you never want to catch!!!

Just my opinion.

Oh, you're very likely correct. But "you may say I'm a dreamer" and all that. I still wonder "what if" sometimes when I come across an old photo of her back in the day.

 

[Hand_solo77]

Then my wife is the one who would have to take the initiative. But only after we were 100% sure that you were returning her attraction. And don’t worry, she would want discretion as well. So you visiting our place on the weekend would be best.

Then I look forward to her advancements, and I agree on discretion, but as we get know each on a more personal level she would probably have to go on some work trips, and I never close the curtains at the hotel.

 

[screwher]

Then I look forward to her advancements, and I agree on discretion, but as we get know each on a more personal level she would probably have to go on some work trips, and I never close the curtains at the hotel.

I wish my wife’s career took her away in the occasional business trip. It would give her plenty of opportunities for some evening time fun with other men in her hotel room. Maybe guys she meets in the hotel lounge. But more likely with you in your room. The bed in my wife’s room remains immaculate the whole trip. But the bed in your room would need daily sheet changing.

 

[svengali_decL]

Her name was Trish, and I had a crush on her all through high school. We dated a few times, but nothing ever went beyond necking in the car. We even went to college together for a short time, but she dropped out and moved back home.

During that time, she began dating an asshole from our high school, but she "thought she could change him" and all that shit. When he left for the Army, we started hanging out again, but it was all very chaste and buddy-buddy. Until one night in the summer of 1985.

She was mad at her long-distance asshole boyfriend and so we went down by the river and I just let her vent. We had a bottle of Southern Comfort that we passed back and forth. She smoked a joint (I never got into weed) and we were damned near naked in 30 minutes. We ended up driving back to her house and I completely blew the only chance I ever had with her because in my inebriation I suddenly became all chivalrous and shit, deciding that I wanted to see if she felt the same way sober and then I'd know it was finally the right time for us. She did not feel the same way sober. In fact, she didn't speak to me for a year.

Now she's a far-right extremist white nationalist "Christian". I finally had to cut her out of my life entirely. I still daydream about "What if" and such, had things turned out differently. But she's definitely the one who got away.

mmm, good ol' Southern Comfort... fuelled a few fires of my own...

 

[Nightspeed]

mmm, good ol' Southern Comfort... fuelled a few fires of my own...

Southern Comfort, Boone's Farm Strawberry Wine, and Everclear! Woohaa!!

 

[Not Normal]

There's one here on Lit from back in the old days, and one from college.

and maybe one other

 

[daytr1pper]

At the time I thought it was a loss, a missed opportunity.

Looking back I realized it was a dodged bullet. It would have been a total disaster.

I was raised to wait until marriage. My "one that got away" is me. I missed my chance to be the whore I was meant to be.

I didn't have sex before marriage. My bf and I swore a vow to one another that we wouldn't

The closet I came to being full-committed to breaking my vow was a girl a year and a half younger than me. I was 19, she was 17 but turning 18 soon. I had no self-confidence, poor self image, wasn't cool, etc. and this incredibly hot long haired girl showed an interesting in me (mutual love of a hobby) and we started hanging out. Kissing, heavy petting, etc. She then let me know she wanted to do the deed. I told her she was under 18 and I could get in big trouble so she'd have to wait the month til her bday. My bf and I chatted and he was amazed at her beauty and told me to go ahead.

A few days (week?) before her birthday, I got as sick as a dog. 102+ degree fever for over a week. I was sick over her birthday. While I was still recovering she started summer school (wasn't the sharpest tool in the shed) and found a guy she was interested in.

Looking back on it, I credit God with saving my arse! If I would've had sex with her and then she dumped me, I would've been messed up!!

I had several other opportunities. I didn't then, but now I regret not pursuing them.

One in particular was a strawberry blond with 44DDs. Her face wasn't particularly attractive but the hair and tits, oh my. We've kept in touch and for years into my marriage she still wanted to be a FWB. She'd send me pics of her in lingerie. She'd tell me about the toy she used and how she'd gush thinking of me. I did titty-fuck her once. But that was as far as I'd go at that time. Right about the time I say fck it, let's do it, her libido disappeared and she's no longer interested. Dodged bullet?

 

[goldenknights54]

week before college graduation and got a call from an old High school female friend who was going to be on campus to interview for grad school. She wanted to get together for dinner after her interview. we were friends but never anything beyond that as she was a cheerleader and I was on the basketball team so we traveled a lot on buses to and from away games. Very sweet and gorgeous with great body and was dating one my buddies so never did anything with her. Turns out she was single and even better looking than I remembered. She got a bit drunk and flirty and began to touch my arm and ask about my love life, if I was dating and where I was going for grad school. Went to her hotel where she drank even more and kind of got sloppy so I suggested she turn in for the night. She asked me to take her to her room which I did as she needed help and opened the door and got in and she wanted to lay on the bed for a "minute". She kissed me and then kind of fell asleep. She had on a pretty short skirt and her panties were showing. I was so hard and wanted to touch her but I did not do anything except pull her skirt down, take off her shoes and tuck her in. I actually stayed and slept next to her to make sure she was ok and we woke up and she was really embarrassed. She apologized for being so drunk and thanked me for "not taking advantage of me" and she smiled. Then she got up, went to the bathroom and came out and said "Shit, I gotta leave or will miss my flight". And I hugged her and was on my way. Six years later, I see her at our high school reunion and she is with her husband and still looks amazing. We talked alone for a minute and she simply said " thank you for being a gentleman that night... I may not remember much after dinner but I sure know you made sure I did not do anything stupid. You are a great friend but if I wasn't so drunk who knows what would have happened". And she smiled and kissed me on the cheek. Damn.......

 

[Greytruck]

A girl I met in college. She was several years older than me.
strawberry blonde hair to her butt, small breasts. Cutest face ever.
make me say let’s make love.. we did not fuck
she was beautiful and kind and so sexy.
our first time on her living room floor with van Morrison record playing.
I screwed it up.. being younger and a guy. Young and dumb
she wanted a commitment but I wasn’t ready.
she left and broke my heart

 

[HumpDayHoratio]

My best friend through HS worked at a grocery store. He started dating this cute little thing that had crazy curves in all the right places. She was living with her grandparents that summer down at the beach as her parents were going through a nasty divorce and we’d go hang out with her down there. She’s one of those girls every guy just falls in love with. Especially when you’re spending a whole summer together. Just us three mostly.

It wasn’t long before she starts letting me know, she wouldn’t mind if I started seeing her on the sly. Which would have been impossible that summer as we all were connected at the hip. We would all sit together in the front seat of my ‘65 Ford Galaxy 500 and we’d all three smash in close and she’d always make sure my arm would be positioned just right on her tits. She’d give me the bed room eyes when my friend would look the other way or if he would be gone for a few minutes.

She entered a JuCo in town with my friend and I went away for freshman year in another part of the state. I came back one weekend and brought some “party Goodies” from the Party Fairies at the university. Her grandparents were out of town so we had the beach house to ourselves and I get there early. My friend still had classes or work so she and I had a couple or three hours alone. We partook of the mystical powders and both very horny and her with those bedroom eyes again…

All of a sudden I got a wave of chivalry, and ignoring my raging hard on, told her we couldn’t do this to our friend. For his part, he really loved this girl (we both did) and it would have devastated him if we would have gone behind his back.

So, yeah. She got away.

Fast forward five years. She’s long gone but another girl I introduced my friend to, well they decide to get married. They come up and stay in my apartment at school for a long weekend and we’re doing much the same kind of stuff like back at the beach.

This is when he proposes we have a threesome with his fiancé! She backs out but I start thinking…if he was going to do that, why the fuck did we NOT do that with the girl we both really LOVED!

 

[StrongMaster7]

I lost my virginity to my first girlfriend. I was so much into sex, I put up with a terrible relationship fro two years. Huge fights every day, then make-up. Repeat.

For me 'the one that got away' might have been all of the girls I could have fucked, who wanted me, but I was faithful to my gf. She would cheat on me the first chance she got, btw. Live and learn.

 

[Crownvic]

I lost my virginity to my first girlfriend. I was so much into sex, I put up with a terrible relationship fro two years. Huge fights every day, then make-up. Repeat.

For me 'the one that got away' might have been all of the girls I could have fucked, who wanted me, but I was faithful to my gf. She would cheat on me the first chance she got, btw. Live and learn.

Good advice...Amen..

 

[lil_jenni]

My Hubby is the first person with whom I ever even thought about having a relationship, much less a long-term one. I had a GF for a lot of last year, and that grew into an emotionally intense relationship, but nothing like I have with Hubby. So, I don't have "one who got away".

On the other hand, I have been told (via social media) by four different guys (one I knew in HS and the other three from college) that I was the "one who got away." I barley remember the guy from HS and do not believe anything sexual ever happened between us. Of the three from college, two of them only received BJs as onetime hookups. And one of those I didn't remember until he reminded me.

The third guy I actually hooked up with on three different occasions (a rarity for me -- I was a one and done hookup girl back then). The first was a BJ only. The second was mutual oral because he wanted to do it (he was not proficient in giving ). The final time we actually had intercourse. It was meh. Best I can say is that it didn't hurt like intercourse usually did for me when I wasn't drunk (I was pretty buzzed, however, so that probably helped). He was a nice guy going through a tough time, and I was helping him through it. At least that was my motivation. So, I was surprised when he told me no other woman has ever compared to me on any level, but especially sexually. I had no idea what to say to that, so I just told him that his memory of me was probably idealized.

 

[BillTheKatt90]

our first time on her living room floor with van Morrison record playing.

By coincidence, I lost my virginity to the song "Brown Eyed Girl"!

 

[soflabbwlvr]

I had known this girl for a few years, but I always had a girlfriend or she was otherwise unavailable, so I never even thought of getting close to her. Then one summer I was suddenly single and she was very single also. She was pretty, with reddish brown hair, skin the color of cinnamon, and a body that belonged in a magazine. I wasn't in love with her; I just wanted to fuck her. She had the reputation of being slut, and that only attracted me to her more. Not only was she a slut -- she also had the reputation of being a size queen. I'm only average size, but that didn't intimidate me. What I lacked in size I more than made up for with skills. So one Saturday night we were both free and I asked her out. She quickly said yes, and I made plans. I was ready to give her the time of her life. Saturday night rolled around and I'm ready to go. She lived just a quarter mile away, so I was waiting a few minutes before I went to go pick her up. About five minutes before it was time to go, the phone rang and it was her. She cancelled on me. Some flimsy excuse I don't even remember.
We never did go out. That night I went to a party with my cousin, got totally drunk and met the woman who later became my wife. Never saw the other woman again.

 

[ZfrkS62]

I might be in the middle of it right now. We're supposed to have out this weekend, but sure to get being sick for the last week and a half, I haven't talked to her and fear she's snapped out of it.

It's been one of those things where you don't just vibe with someone, you resonate with them.

I'm *hoping* she finds me on here.