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My Sexual "Fails"

My Sexual "Fails"

First of all, if this story doesn't make you horny, I hope you get a smile out of it.

One time I put a golf ball up my butt (age 9) and had to wait several days before it would come out. That was scary (for some reason I thought it might dissolve and poison me) yet exciting to know I had a golf ball up my ass and nobody knew.

At age 12, my best friend and I were jacking off together one day, as we did everyday at that "cumming of age" period. He asked me if he could "put it in my mouth for just a minute". I agreed and took his dick in my mouth and started sucking. Within a minute or so, I felt my mouth fill with what I thought (and hoped) might be my own saliva. After he came, he raced off with me chasing him asking him if he just came in my mouth. He denied it, but I knew he had, and I kinda' liked it. I eventually ended up sucking him off about once or twice a week over the next few months. Then my hormones took over and I became obsessed with girls and women. That bisexual part of my life took a backseat in my life, but came roaring back in my early 20's.

Around age 14, I was looking at my big brother's Playboy and Penthouse magazines in my room, in the basement of our house. I was so horny, I decided I'd try to suck my own cock and got into position up against the wall, with my legs flung over my head and straining to reach my cock with my mouth. I was also jacking my dick and could feel the cum building up, ready to blow any second, just an inch from my face and mouth. All of a sudden, I heard a rapid knocking on my window just above me... and it was my Mom, peering down straight into my asshole from the garden near my window. I thought I was going to be sent away, maybe to a hospital for the sexually insane, but she never said a word, so I convinced myself at the time that she didn't see anything. But I know she did.

Around age 18, I met a really cute girl in the park and we set up a double-date with my friend Jerry, and her little sister. We ended up at Jerry's house, my date and I were in the front room on the sofa, and Jerry and my date's little sister were in his bedroom. My date and I were kissing and "petting" (I felt her tits and put my fingers in her pussy) and that's about all. After a couple hours they decided they had to leave and did so. We had kept the lights low, so it was pretty dark in Jerry's house, and pitch black in his room. After the girls left, Jerry and I went into the bathroom and turned on the light... and Jerry's face was just covered ear to ear in bright red menstrual blood. We both started howling with laughter! He had spent the last couple hours eating cherry pie, and didn't even know it.

When I was 19, I started having an affair with a woman from my workplace. She was 25 and married and we had a 3 year affair, fucking every chance we got. Early on in our relationship we went to a drive-in movie and parked in the very back, and started getting frisky. She told me that she was determined to give me a blow job that night, and even told me that she wasn't very good at it... yet. She also told me that she had never given her husband one, because "he wasn't into oral sex". Maybe that's why she was having an affair?

Well, we were both naked and in the front seat (bench seat, no console, unlike the cars now). She brought a rubber dildo with her and used it on herself in a very exhibitionist way. Then I ate her out for a while (and she had the thickest, blackest bush I'd ever seen, even in magazines. It was seriously like carpet). Then we fucked for a while, and eventually she moved down to take my rock hard cock into her mouth. Her mouth and tongue felt wonderful and it was one of the first blowjobs I had ever received, and had never yet been given one to completion.

Pretty soon, I started to feel the cum building up in my groin and let out a long moan, giving her an opportunity to decide what she was going to do with all my cum, and I could tell, there was going to be a lot of it. It felt soooo good, and then I let go, spewing spurt after spurt after spurt after spurt of thick cum into her sucking mouth. She paused for a few seconds, then flung the door open... and threw up.

It was very traumatic for me (and embarrassing for her) and I was always worried about receiving blowjobs after that, until my second wife. She just loved giving head and really enjoyed swallowing my cum, and would do it at least 2 or 3 times a week. God bless her.

At about age 22, my bi-side came roaring back and in a very awkward way. But I guess everyone has a learning curve.

I was 23 and recently divorced (I married my pregnant wife at 17, she was 16, but that's an entirely different story*). I was in the magazine shop looking at the flesh mags and getting very horny, when a young black guy kept gently bumping into me. He ended up taking me to his apartment. He dropped his pants and sat down to have me blow him. I knelt between his legs and started sucking his long black dick. After about 15 minutes he said, "You don't know what you're doing" and showed me out. (He was a very macho star football player at the University of Utah, and I think he didn't feel "gay" if he wasn't sucking me. That was fine "bi" me. Homophobia was rampant back then, including me.)

I was determined to perfect my "bisexual" technique.

A couple years later, I was a manufacturer's rep for an equipment distributor and covered a 3 state territory. I had a co-worker that helped me and we often traveled together, by car. One time, we were in Denver and had spent about 3 hours drinking in a couple of bars and then went to an Adult Bookstore for another hour of arcade porn. By the time we got back to our hotel room, we were both incredibly horny.

He was determined to get an escort and while he looked through the yellow pages, we both started jacking off. Pants around our ankles, sitting side by side on the end of the bed with both of us jacking our own cocks. I bent down and took his dick into my mouth and started sucking. He totally FREAKED OUT and pushed me to the floor. He glared at me as if I had just murdered both his parents. I apologized profusely and told him "Sorry, I'm so drunk, I don't know why I did that, I'm sorry, I'm soooo sorry". We had to drive 8 hours the next day, in the same car, and without a word to each other. AWKWARD!

About a year later, I had a good friend that let me "practice" sucking his cock whenever we would go out drinking. I sucked him 3 different times before he finally got comfortable enough to cum in my mouth. We never did it again (I guess he wasn't into it) but we stayed friends for several years afterward.

I'm guessing we've all had things go wrong in this department, right? Anybody else have any "fails"?


*About my first wife. We got married when I was 17 and she was 16. We had sex twice in 6+ years of marriage... once before the wedding (which resulted in pregnancy) and once after, immediately after catching her fucking my best friend in our bed. Her response to me catching her was, "I hope you don't think you're going next." I did. And I've enjoyed sloppy-seconds ever since. God bless her, too.
Published by FiftyPlusPage
6 years ago
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dirtyoldbiman
interesting. I really sucked my 1st cock and swallow at 65 or so. couple of teenage fumbles don't really count. didn't know where a clit was until 2nd wife showed me. tough luck for the 1st wife, or bitch. LOL
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Drfeelgood6 6 years ago
Very interesting!
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