We have discussed the first, best and other sexual encounters so how about the most frustrating? Mine was when I was in college and I had given a girl in one of my classes some photos of birds to illustrate a report she was writing for a class (I was and still am interested in wildlife photography). She got an A for the report and wanted to thank me. She was a beautiful 6 ft tall well built wench who just exuded SEX. We discussed something we might do and she asked if I like to fish. I was wildlife management  major and said , of course. We decided to go cat-fishing at a nearby creek. So one night armed with rods, reels, bait, beer and a blanket we were off.
I built a fire,and with poles and lines in the water never to be noticed again until we left. We drank beer, toasted some marshmallows, started necking, groping and having a hell of a lot of fun. With her slacks pulled down she wouldn't take them all the way off. She couldn't spread her legs far enough for me to get much in the way of penetration. Unfortunately I didn't have a foot long dick so couldn't get off. I was too naive to ask for a bj. I never saw her again but I'll never forget that encounter

We went through the motions for about fifteen minutes before she exclaimed in frustration:  We just aren't turned on by each other anymore.

She was right.

I suppose you could call that your Sexual Comancipation Day. Do you properly celebrate that day? 8o)

It was my senior year of college.  I used to take "Party Pics" at Sorority and Fraternity parties, and was in a house myself.  One Saturday I was assigned to shoot a Dorm party, the worst types by any standards.

Well there I was shooting away when this tall, strawberry blonde with huge tits, kept insisting I take pics of her and all her friends, which I obliged.  Late in the evening I asked if she would like me to take pics of only her (these were days before digital so unless you had a Polaroid, nudes were no,no).  She agreed.

The next Wednesday afternoon we got together and we shot in several locations on and off campus.  When were were done we went and got pizza and consumed several pitchers of beer.

We ended up in my room at the Frat house and listened to music. I had some Playboy Centerfolds tacked to the wall and she commented on them, asking me if I could photograph her that way.  Hell ya I said. After some kissy face, huggie bear, I started to group her tits.  She responded with some inviting moans as I kissed her.

Just then the  phone rang (pre caller ID).  To this day I question why I answered the damn thing, it was my mother from home.  As I was talking and trying to get the call ended, I felt a pair of hands reach around my waist and travel into my pants so as to play with my cock.  Most MidWestern girls of that era were not that forward.  Try talking to "Mom" while some hot coed is stroking your cock through your pants.  

I hurried to get off the phone and had my backed turned to my bed.  Once I hung up I turned around and she was naked, playing with her tits and pussy.  Micheal Jackson's "Off the Wall" was playing on my stereo.

As her hips gyrated to the music she asked if I thought she was as pretty as the centerfolds, "Hell ya you are...."

So I got naked, sucked her tits and ate her pussy.  Man was she aggressive spreading her lips with her fingers so I could suck her clit.  

Time to go in for the kill and have the fuck of my life, but there was one problem, I had Beer Dick. It had never happened before.  In fact, I drank before fucking so I could last longer.  Beer was my friend---not tonight.  WTF, my pecker was napping on the job.  I thought to myself, "Oh no, I want to violate that mound of redish blonde hair...wake up...WAKE UP".  Mr Happy refused.  

Needless to say she was not happy, got dressed, and left.

To this day I will never, ever forget that moment.  An opportunity lost and so embarrassing.  At least the gal had the class not to tell my frat brothers on the way out

Yep that is one great frustration. After I was married and working on an advanced degree I had only one night a week for any relaxation and that was when I bowled with a teem from my Dept. After bowling we would have a beer or two or three or more. When I got home I was always horny. My wife was always in bed and when I snuggled into bed she would turn over with open arms. She knew what beer did to my cock, it was hard and lasted for a long time. She had no complaints about my coming home sloshed.

That's horrible but one hell of a good story.

It is all true, I swear.  I comfort myself by thinking if we had done the nasty, she  would have gotten pregnant.  I was out of condemns at the time and was going to fuck her regardless.

At least that is what I keep telling myself.

That's not frustrating, That's a f*cking DISASTER!!!!!

No Charge No Sex

I can only think of one frustrating episode, and that was the first time with my ex-wife, who was a virgin. Extremely difficult to penetrate her. Fortunately, we didn't let that dampen our spirits concerning trying again! Had a pretty tremendous sex life for many years after that.

Melissa you are definitely on the wrong side of this state! I would never let you run out!

Sorry to be late to the party, but my most frustrating sexual experienced occurred a couple of days ago with a provider. Saw her ad on BP, middle thirties and nice pictures, although the face was blurred.  A few days later she had a couple of good reviews on TER, both 8's.  Did a google search and she seemed real. Decided to take the plunge. I get an appointment and arrived at her hotel. She wore a revealing sun dress. We talked a little bit and then got undressed. Her body is gorgeous. Beautiful natural D cup tits. She has a thin waist and a flat tummy and beautiful legs. I thought I hit the jackpot. Just looking at her brought on a stiff erection. After a deep French kiss, she looked at me and said: "You smoke. That's very bad". She had me sie down on the bed. She used a lubricant on my cock and started a really sensuous hand job. It was so good that I thought I was going to loose it. Asked her to stop because I did not want to cum. She replied that there was lots of time. I told her that I am basically a one shot guy and wanted to make it last as long as possible. She tried to continue, I told her that I wanted to eat her pussy. She said:"You are a smoker. No licking and no kissing". WTF. I started to loose my erection. She let me know if my erection did not return she would get dressed. I said: "That's it. I'm leaving". I got and got dressed. Neither of us said a word. I said good bye as a left without a reply. I left the donation. Her ad should have had a statement about not seeing men who smoke. Almost makes me want to quit.

With all due respect for your decision to smoke.  Deep down don't you know she is right? I quit many years ago and it was hard. My father dying of lung cancer after smoking from 16 to when he died at 59 didn't make me stop immediately. It took me 2 years to finally stop. I know it's hard but I'm glad I did. Now at 82, I despise the smell pf cig smoke and to kiss a heavy smoker is like licking an ashtray. I agree 100% that she should have advertised her attitude toward smoking. I don't why she couldn't finish with BJ

My (civie) date & I removed coats & she joined me in the rear of my SUV in a sleeping bag...  I figured I was about to get lucky.  She took offense at my erection...  so I turned MY back so she could get out of the sleeping bag.  I took her home.  She later told her brother (who was a friend of mine) that I tried to RAPE her.  She was certainly a cock tease.   I said we'd had a misunderstanding but would have humiliated her (& not helped my case) if I told her brother we were in a sleeping bag together.  

I don't know why you could get the job done with her pants on...  I used to get the job done with my HS GF in lazy doggy.  Jeans only down to upper thighs.  Penitration was not deep but damn she was tight.  Once, I was doing her in her family room when her Dad came down stairs looking for her.  Girl has to bend & stick her butt out some.   Lazy doggy was our favorite in the backseat of a souped up Dodge.  

My ex & I tried the steps of her sister's pool when they weren't home...  it was fun but lack of friction was frustrating.  Non-completion.  
Same ex & I were out horseback riding in deep woods, she wanted to get banged.  Bridles are not strong enough to tie with (if they break, horses run off & you walk home) & halters were left tied to the rail at the ranch.  So we tried to hold the critters & standing F*ck but it wasn't working

No way would I DFK a smoker who tasted like an ashtray. Have some respect for the lady who has to kiss you. You want all the goodies, then make an effort and clean that mouth!

I agree that kissing a smoker is disgusting. With heavy smokers even if they brush their teeth, use mouthwash and take breath mints they still stink because their lungs are also a source of tobacco stench. (:

Dating a girl for about a month. We had a wedding to go to. I thought that might be my lucky night. We were slow dancing and she whispers in my ear that she had gone to Victoria's Secret the day before an she couldn't wait to show me what she bought. Got back her to her place. Kissing an groping an ripping off our clothes. Her VC outfit was super sexy. When we were completely naked she said she wasn't ready an couldn't go through with it. frustrating