Failures-Flops-Turn Offs-Disappointments

[1michael]

I found out that hanging out at my buddy's BAR it was easy to pick up the girls, unless I waited to closing time or showed up there later! But some of the girls would pop in there and many of them were Good for the last thing to enjoy at the end of the night!
I found a few girls could be standby's, just in case I had No Luck at the BAR, so this one night I didn't! So what I did was drive to this one standby, who is a very Busty girl named Carol. I would also count on her from being out on the week-end and coming home late in case she didn't go to the same BAR!
I didn't hang around long in front of her house before she showed up and was parking her car, then I pulled up along side her car as she exited.
She got into my car and I drove off to a nice secluded place so we could have a little sexual pleasure! Not wanting to waste much time on just Kissing, we both went to doing some handy work on each other!
The only thing that really caught me by Surprise was going for her Huge boobs, there was No BRA on her and I got exposed boobs! I had to ask her where is her BRA, because I never had seen her without wearing one mostly cause her breast were so Huge! She gave me some Lame excuse that she took it off and put it in her purse as she pulled it out to show me! But now my mind started to wonder about what the Real Truth was, did she meet another one of my buddy's that all knew she was Good for SEX and gave great blowjobs? Or maybe there was some other guy that I didn't know and she enjoyed him while he did the same on her?
with my mind working in this direction I got a little turned off, but still wanted some sex but had to be careful just in case she still had some leftovers that I didn't want!
So rather than going all the way, I had her stick to just doing a blow job with a finish that was suppose to land on her tits but I caught plenty of her face too!
After she done plenty of clean up mostly on her face and just covered up her tits with her blouse, she wanted to try for more Kissing but I said it was getting late and I have a long ride home!
I can say Carol was never a regular date, but when the time came she was always great for the SEX!
Even for the turn off, it worked out Ok and maybe she had a Double dose that night? lol

[explorer98]

Originally Posted by DiegoJames

Absolutely!

And it can be a look, a phrase, an action they've done 100 times before and yet...this time...wow!

Or it can be a little, secret thing they do with their internal muscles. My other half is one of five girls and I once overheard her in conversation with the youngest. It was something to do with how long she and my BIL had been going at it one night and how she'd lost interest as it had gone on too long.

J (my partner) asked; "So did you do that thing we do...?" to which R (her youngest sister came back; "Of course - never fails!!"

Wondered how many times she'd done that to me over the years??!!!

[triedandfailed]

I have a fail that happened to my wife and I about 6 years ago. I have gone through all the range of emotions on this one myself. But this is almost so ridiculous that it's hilarious if you can just bare with how long the story is until the end.

Since I was younger I had always been mesmerized by the older woman fantasy. Unfortunately I grew up in the wrong era when those type of encounters were few and far between and I never got to live out my older woman fantasy. So fast forward - I met my beautiful wife, we fell in love, had and raised children, bought our dream house, and truly had a very good and healthy relationship with each other. I pretty much had everything I ever wanted.

Now my wife isn't some overly sexual person. She is sexy and beautiful but she's always been more on the conservative side in that regards. However, she was aware of the older woman fantasy that I have had since I was younger. And as we grew into our early 50s we began discussing that fantasy more and more during cuddle sessions. But we weren't discussing it in terms of me being with an older women, but more how she is an attractive older woman at this point and how every younger guy wants to be with her.

I could tell that she was enjoying talking about these ideas. It was just pillow talk between her and I but it would turn us both on. We talked about all sorts of different scenarios - some of which she enjoyed listening to and some of which were too much for her. When I asked her if there were any scenarios she'd ever be open to trying, she thought about it for a moment and said, "the one where she gives a younger guy a blowjob." She said that it was more on the harmless side compared to the other scenarios I would describe and that she would be more comfortable being in control of the situation. So I brought it up over and over until she reluctantly agreed one day.

So we put an ad on craigslist asking if any guys in their early-20s would be interested in getting a blowjob from my beautiful wife. We probably got 200 replies in just a few hours. There were many options for her to choose from. So my wife looked through all replies and choose her favorite one. A normal-looking 23-year-old guy who sent a face picture and had a well-written response talking about how he loves older women. He wasn't particularly attractive or anything, but he wasn't full of himself like many of the replies we received were. So him and I exchanged emails back and forth for a week or so and finally setup a time for this to happen.

We invited him over to our house on a Friday night. My wife made dinner. I urged her to wear a fancy silk blouse that she had. It was a shiny, silver, collared button-down blouse that she had bought for work, but she only wore once because it was too fancy for her office. But she looked incredible in it and it added to the whole older woman appeal. It made her look extra important and definitely sexy.

The doorbell rang and my wife answered the door. She told me his eyes lit up when she answered. That was the first time he was seeing her. He never even saw a picture of her in the emails. My wife invited him in and was friendly to him. She hid it, but she said she was nervous because it was weird meeting someone and knowing that she'll be going down on him. He was very nice and cordial. He took off his shoes and told us what a nice house we had as my wife showed him to the kitchen.

I handed him a beer and we all talked for a bit. He seemed somewhat shy or nervous, which sort of helped my wife's confidence grow a little as she became more outgoing and even slightly flirtatious with him. He told us about his job, where he was living, where he grew up, etc. We carried the conversation on through dinner and I could tell that my wife thought he was nice, polite and cute enough. It seemed like it was actually going to happen.

She after dinner my wife asked the guy if he still wanted to do it. We go to the living room. My wife kisses him on the lips and they begin making out. My wife grabs his hands and places them on her butt. He's now squeezing and feeling her butt while they are making out. Then she unbuckles his pants and pulls out his dick while she's still making out with him. She pushes him onto the couch, gets on her knees and pulls his pants and underwear completely off. My wife is kneeling in front, touching and holding his dick. Then she does it. She puts her mouth around his dick and sucks him.

She does it for about 2 minutes and then tells me I have to leave. Our deal was that I got to watch the beginning of it, but she got to do it alone with him after that. She thought he'd be uncomfortable if I watched the entire time and she wanted it to be about him, not about me. So like I agreed to I went upstairs to leave them alone. Now, it really didn't matter because our living room is wide-open and two stories of the house high. So it was easy for me to peek from the upstairs balcony and see everything anyways. So that's what I did.

Ten minutes go by and she's still going down on him. I'm beside myself rock hard watching from the upstairs balcony. Another 10 minutes goes by and she's still going. She's not bobbing her head or doing a sloppy blowjob. Her move is to gently suck on the tip and to massage around the tip with her tongue. It's an incredible feeling. And she's looking up at him while she's giving it. By now he's playing with her hair and tucking it behind her ears for her. Another 10 minutes goes by and I'm wondering how long it's going to take. I busted a nut all over the carpet watching already. But my wife is still on her knees diligently giving a sensual blowjob.

I take a mini break for the bathroom and come back and I see him holding his legs up in the air. It looked to me like my wife was licking his ass, but she later told me he asked her to kiss and lick his balls and the spot between his balls and his ass. Damn, she's never done that to me. He keeps lifting his legs higher and higher trying to get her to actually lick his ass, but it's the one thing my wife is resisting doing. So instead she tickles him with her fingertips in those spots and tried to get him to lower his legs down, but he's enjoying it too much. So she keeps kissing his balls and tickling his ass. And then he outright asks her to lick his ass and sort of pushes her head down a little bit. I can tell she didn't want to must have just gave in and did it. He was in an awkward position using his elbows to hold his legs back and his hands holding my wife's head so her face was literally buried in his ass. It was quite the sight but it was more than both my wife and I had bargained for. I thought about stopping it but didn't. It was approaching minute 50 of the oral session.

Then after a minute or two of that he frantically says, "I'm gonna cum, I'm gonna cum." And he lowers his legs and tries to get his dick back into her mouth. But before that can really happen he shoots his load. All over my wife's face. Huge stripes. All over her hair and fancy blouse too. My wife just closes her eyes and pauses as if in shock. Cum already covering her face and he's still shooting loads out. He took her pausing in front as an invitation to finish the rest of his loads onto her. So he crouches up off the couch and finishes the rest of his shots onto her. It took a good 30-40 seconds for him to finish cumming and he must have shot 15 loads no lie. I could honestly see the loads still coming out from where I was. It was honestly impressive in a way and somewhat comical.

I could tell my wife was furious though. She didn't say anything but her hands were tensed up like she was beyond pissed. The guy didn't pick up on that though. He sort of laughed and mentioned how he hadn't cum for a week leading up to just now. My wife stands up and can barely see. She has one eye barely open trying to see where she's going. The guy then looks up and notices me on the balcony before grabbing his clothes and getting dressed. And as my wife musters herself upstairs she crosses my path on her way to our upstairs bathroom. Her face completely covered. Her blouse also drenched. And several thick white stripes stuck to her hair and the top of her head. It was honestly like the aftermath of one of those fake porn movies online. Two days later she told me she could still smell the cum on her as it got in her nose somehow.

When she passed me in the hallway she angrily whispered, "get him out of here." So I went downstairs and tried to downplay it when he asked if she was mad. "Sorry, it was an accident when it started and then I thought it would be ok to finish it," he mentioned. And I just said it was fine and as I'm getting ready to walk him to the door he just casually asks, "Your last name isn't so-and-so is it?" He says our last name. I kind of look at him quizzically but figured that he had our address and looked us up before he came over. But then he points to the big family portrait on the wall that he was in his clear view while he was getting head and says, "Is his name so-and-so? I think I went to college with him." Says my son's name. The portrait was a few years old, but I nervously asked him where he went to college. He said the same school that my son had a semester left at. My heart sank into my stomach.

I didn't answer his question, I just sternly asked him if he could keep what happened here as a secret between all of us. Even though I knew that was unlikely if not impossible for a single 23-year-old to not tell his friends about what happened. He nodded as if to understand but also asked, "can we do this again sometime?" All I could say was "maybe," but basically knowing that my wife would never ever do that again. Then I guided him out the front door and that was that.

My son went to college 45 minutes away and the idea never occurred to me that this was even a possibility. I debated telling my wife what I just learned but realized that wouldn't help anything at all. She was already beyond furious with me when I went up to check on her. She stayed in the shower for about 2 hours, even after the hot water ran out. The next day she went out and cut her hair. She also threw away her $300 satin blouse. When I suggested she should donate it instead her response was, "it's cursed."

About a week later I emailed the guy pretending to be friendly, thanking him for coming over and saying it was fun. But really I was hoping for assurances from him that he would keep the incident discrete. But I got no response back. A month later I tried again. Same thing, no response. The amount of stress I had trying to figure out if my son would ever find out was unbearable. I could barely even focus on normal stuff for months. My wife and I have barely spoken about this since it happened and to this day she doesn't even know about the college thing. However, she did mention several months later that she was getting an unusual amount of facebook friend requests from guys at our son's college, but weren't actually connected as friends to him. But she didn't know enough to connect the dots and I didn't have the heart to tell her.

My wife hasn't given a blowjob since.

[SixPointFive]

Couple of examples from my younget days, both ends of the spectrum:

1. Final Year at Uni I shared a house with 5 others. 3 lads, 2 lasses and we were all pretty close. 1 of the girls had a full on boyfriend (I think they are married now, some 25 years later) but one drunken afternoon /evening we ended up making out for no other reason that we could and did. I had no real interest in this girl but add alcohol to the situation and the 21yo me was prepared to do anything. We were making out, I had my had up her top and she responded by putting her hand down my pants. The only problem was that my dick was having none of it. Not so much as a slight stirring and this girl was basically just masturbating my small, flaccid cock. She said something like "that's disappointing" to which I agreed and we stopped there and then never to be repeated.

2. Living in my first apartment post uni I had another drunken afternoon with a good friend of mine. We had made out before, she'd jerked me off a couple of times when we were in our late teens but generally we were mates who hung out together. This drunken afternoon led to a make out session and her jerking me off on my bed. I was getting close to the point of no return when I stopped her for some reason (no idea why). I think I had gotten into my head that I wanted to finally have sex with her and that cumming then would have ruined it. What happened next was that I spent the next hour absolutely on the verge of cumming as we lay there watching TV and chatting. Then I stupidly decided we SHOULD have sex and I came the instant I entered her. I tried manfully to continue but the sheer weight of my orgasm caused my cock to soften immediately and there was absolutely zero going on. That was our last ever encounter and she went away with the impression that I was awful in bed (always had good feedback from other ladies lol) and it's always annoyed me that I didn't get another opportunity to properly showcase my talents

[Gee_Star]

I got reminded of something today.

One thing I've learned is that respect goes a very long way, it's cliche as hell but it's true, that's why I didn't get offended when I got a lecture from a nice couple at a nudist camp for having an erection. That situation taught me a lot about respecting people's space and lifestyle choices but what always turns me off is when guys think that they want to participate in swinging or partner swapping and all of a sudden they start flipping out halfway through and things get awkward, if not violent!

One situation was a couple who were in their mid to late 50s, they were small business owners and former military. The wife was a very beautiful and sophisticated woman. The conversations were great, we were on the same page about everything. I gave them the pictures of me they asked for (full nude front and back and penis close-ups) and I got the STD testing that they requested with them present for the testing.

Everything was fine, we all went to dinner and we seemingly clicked but one night things went off the rails, earlier me and the husband, the wife and another lady had gone on a double date, and we went back to the couple's house to have sex. He went to the other bedroom with the other lady, while me and the wife went to the master bedroom. We put on some music, we poured some wine and we slow danced, eventually, our clothes came off and we were still dancing, kissing and I eventually led her to the bed and begin kissing her legs, belly, and pussy.

All of a sudden, the husband busts into the room and is upset, the other woman's ex-husband called with an emergency involving their child. I'm startled and I stand up and ask him if he's ok, he explains the situation, and his wife immediately tells him to join us but he looks at my penis and asks me why I'm not wearing a condom and I explain to him that she and I had just undressed and hadn't done anything yet and furthermore I reminded him that both he and his wife saw me get tested and that condom usage would be the choice of his wife.

He still was pissed and eventually, his wife mentioned that she was comfortable anymore and I apologized (his wife whispered in my ear that I wasn't the problem and gave me a kiss on the cheek as I was getting dressed). Later me and the wife exchanged e-mails and went into detail telling me that this whole thing was their first time doing any "open marriage" related activity and she wasn't entirely sure that he was comfortable with the whole thing.

I eventually lost touch with the couple and it's been about 12 years now, they are probably in their 70s now but the lesson I took from the whole situation, is that if I'm going to deal with an open marriage/swinging/partner swapping couple, the people HAVE TO BE veterans of the lifestyle.

One of the best situations I was in was a 60-plus couple that had been swinging since 1978 and both had nearly 400 sex partners between them, I was respectful, I respected boundaries and I had a great time having sex with a busty 60-year-old.