You wished you fucked

[live4thebj]

Thinking back to the past: young, younger, very young (have to stay within the rules) who would you have fucked if you knew then what you know now?

Me it's a toss up between 3 actually:
1. My cousin's ex-wife but was his wife at the time. She used to show up at the house in mini-skirts and fishnet stockings.
2. The mom that lived in the neighborhood and I was friends with her son. She was so hot and an ass you could recognize in a crowded room. She caught me more than once staring at her and one time it was at her crotch; she actually smiled when I did. I swore she would shake her ass on purpose when I was behind her.
3. My sisters friend whom I walked to the car once after a party and we were both drunk and another time she let me sleep in her room. She was tossing up signs left and right but I didn't know anything back then.

 

[coacheric]

A friend had two sisters. I had the hots for the older one when the younger one wanted me so bad I would not even had to ask. So blind to the other that I missed my chance. Actually got a small chance at the older one years later. Drunk at a party. Found out as I all up inside her shirt and pants that she was ingaged and he was on his way to the party.

 

[live4thebj]

A friend had two sisters. I had the hots for the older one when the younger one wanted me so bad I would not even had to ask. So blind to the other that I missed my chance. Actually got a small chance at the older one years later. Drunk at a party. Found out as I all up inside her shirt and pants that she was ingaged and he was on his way to the party.

And did you stop or at least try to get a quicky?

 

[coacheric]

I tried to get a quickie. She found some morals before I got any further. Heard that they didn't stay together long.

 

[newhere2learn]

Few come to mind

Former boss, twenty years older than me. Real subtle milf vibe, neglected by husband too.

 

[rocketeer50]

If I had known my marriage would break up after a couple of decades, I wouldn't have passed up on a few sure things that came along in the three years were still "dating". Two and a half of those years we lived in different cities before we moved in together.

One sure thing was a woman in town on business, who was referred to me by a college friend (and one-time bedmate). I took her out on the town and after dinner we went to a music club where we were very handsy with each other. When I took her back to her hotel I got it into my head that despite this sure thing, I wanted to prove to myself that I could turn it down. I said good night to her in the lobby and left. SMH

 

[suckonsimon]

On a field study in Brighton, England. We guys heard there was a disco full of gals from an art college who'd had a day out on the coast and weren't heading back till late. So we dove in there. Two of them dancing like there should have been a pole attracted me and my mate's attention so we joined them, me smiling at the sassiest one as we homed in close and fast. That chick's the only woman who had the measure of my boner before she knew my name. Hot or what. God did my tongue hurt.

Then fucking hell the gals' coach had arrived and they needed to hit the road back to London. My consolation was her being the last lass on the bus, my pals stood around on the pavement, the driver saying, "Likely lad, leave off we got to hit the road!" I needed her to have a sore tongue and an imprinted ass before she got to her seat. But how she wanted in my pants!

 

[NightOfPassion2]

First was a fellow physics student. We went on a trip to an area to do star gazing...and have so great times...

Her and I went to see some stars.. To this day I remember her smiling ...she was laying down looking at the stars...and I was slightly leaning over...laughing..smiling. We were alone

I should have gone the next step...

 

[Funnbrandy]

Who....

A much older guy from when I was younger, he use to hit on me all time and was really hot, but I just didn't have the confidence to follow through, but he's still handsome as hell, successful and I know for a fact great in bed.....no regrets, but I've often thought what if!

 

[kismet999]

a co-worker who left the company and then returned for a visit. She kept hanging around my cube but I had duties and deadlines for the day. She was so sexy. Swimmers thighs and ass, cute face. I should have asked her to go to lunch with me and then let things develop but no, I was a company guy and have regretted it ever since.

 

[Iwantitnowpleas]

I was dating a much younger and very wild girl about twenty years ago. She had a good friend who was gay and let me know he was into me. I'm sure now I could have had a threesome with those two. Part of me was scared I would like cock more than pussy.

 

[soflabbwlvr]

There were more than a few. In most cases, I just didn't interpret the signals properly. But in one case, I made the decision not to pursue the opportunity.

One of my buddies had an older sister who was gorgeous and extremely wild. That girl loved to party. One day she came on to me, but closed her proposition with the statement " if we're going to do this, we have to do it right now because my boyfriend gets out of jail tomorrow." That did it for me. I passed. She ended up fucking another friend of ours.

 

[satin_and_lace]

I wish I fucked my high school boyfriend. I was such a good girl back then, I wanted to wait for 'true love'

I also regret not fucking this guy I met on a ski vacation. There was a group of us in a hot tub, having some drinks. His hands started to wander and they found their way into my bathing suit bottoms. He pulled me onto his lap and fingered me while I continued my conversation with my friends. It was hard to keep a straight face when his fingers were inside me We eventually moved the party back to the condo, where everyone paired off into a bedroom (naughty bunch of friends). We ended up making out on the cough, but I made him stop before we went too far, I was in a relationship at the time and I felt guilty. Now I'm left with the regret of passing on the opportunity to have vacation sex.

 

[jackstud]

mmmm kisses your Ass Satin

 

[mijbob79]

you wished you had fucked

My best friends wife, still think about her 35 years later, My high school girl friend, played around but never did her.

 

[mikendel]

Young security kid from Macy's when I worked there. He would walk me to my car at night. Didn't think a younger man would back then. Now I know.

 

[Jaime_H]

My first girlfriend.....

We were far too sensible....

 

[Ralf913]

Wished I fucked

My best friends wife, still think about her 35 years later, My high school girl friend, played around but never did her.

Last girlfriend in high school Patty.The nite before I joined the Marines,we went out ,we kissed,felt her up over her clothes.I want to fuck her so bad.But I was real shy nothing happen. In boot camp she moved away.Now 2 days ago wife and I with friends go to restaurtant bring ur own booze .went next door bar/package goods.Got my beers then a woman says Ralph Iturned around it was Patty(this40 yrs later)talked for a few minutes she was looking for her business card.My wife walked in looking me I took to long .Did get phone number.

 

[soflabbwlvr]

Here's another

I lived with my girlfriend during my second year of college. A friend of ours from high school was also attending the same university. I'll call her Karen. Karen invited the girlfriend and I over for dinner one night. Girlfriend had to write a paper that was due the next day, so I went alone. Karen and I had a nice evening, mostly reminiscing our high school days and catching up on old friends. Toward the end of the evening her younger sister popped in. I never knew Karen even had a sister, let alone one with a gorgeous face and smoking hot body. Little sister brought a bag of weed, and the three of us proceeded to get stoned. Eventually, little sister adjourned to her room and went to bed. I was dying to join her, but despite some flirting I never detected a signal indicating she was interested in THAT. I got ready to leave when Karen took me by the hand and said she had to ask me a question. "Do you think I'm attractive?" she asked. "Of course," I replied. I knee she was coming on to me, but at that moment in history I was more interested in little sister. So I gave her a hug and a kiss and then left.

In retrospect, I should have taken her up on her offer. Little sister was prettier, but Karen surpassed her by miles in personality and intelligence. (The girlfriend and I ended up going our separate ways at the end of the semester). Of the three women I might have slept with that night, I choose wrong all the way around.

 

[hogdoc]

I used to hang out with a friends girl friend when he was working nights, nothing more than making dinner, drinks movies and conversation, she was smoking hot and we, for the most part, got along better than they did, but she was his girl. They split up after about a year and she moved away. Years later he asked me if I ever slept with her, when I said no, he said, you should have. Had I know he was OK with it, I would have fucked her all summer long!

 

[wetisme]

When I lived in an apartment building there was a guy about 30 years older than me that lived across the hall from us that used to make cute flirty remarks when I'd see him in the hall. One day I saw him in the hall in his pajama bottoms and I don't know what he was doing but judging from the pup tent sticking through his pants to say he was a little aroused is an understatement. I couldn't help but look down briefly and of course he caught my glance and we both smiled and wished each other a good day. When I get back to my apartment I masturbated myself silly thinking about that encounter and now years later I still take that memory out from time to time when I masturbate. It's making me wet now as I think about it

We never did anything and I eventually moved away but I bet it would make him crazy to know a young woman had a thing for him and yes now in retrospect I wish we would have had the chance to fuck each other.

 

[LeeFL]

So-Called Best Friend

There was a good friend (girl) I did a few trips with because we were both single.
She was 4 years older than me - so at the time during college, I was thrilled to have a working woman (out of college) hanging with me.

A close times we have messed around - but only once we had this masturbation session (both oral and hand). Just wish I had fucked that pussy!

 

[kc_sweetNsour]

I have to abide by the rules of the forum. But I would say there was somebody in a state sanctioned position of authority, over me, that I could have easily gotten with.

 

[WifeLender]

Clinical educator

When I was at uni and we were in our intern years, there was a cute married clinical educator that I had a crush on. My friends convinced me not to have a crack, but year later I find that I should have ...damn

 

[FunKinkguy]

Would have been my high school girlfriend who was a virgin and wanted to lose it to me in the worst way. I knew I wasn't going to date her long so I didn't want to take it from her. Wish I would have.

Dated another virgin in college that I viewed more of a hookup but she was really into me. First guy who she let finger her and lick her and she wanted to see what sex was like. On second hand she was a bit crazy so maybe it was good I didn't have sex with her, lol.

There have been a couple here and there along the way but those are the two that pop out in my head.