Disappointments

[philos]

We all had to start somewhere. I'm sure my first would be able to say something similar about me but with time, some reading, some teaching and a lot, I mean a lot of enthusiasm, I did get better

 

[swtrthnhoney]

Once had a bf that claimed he had a velvet buzzsaw. Big disappointment for me. It may have worked on others before me but it didn't do it for me.

My first experience with sexual intercourse was very disappointing. My then bf was an almost doctor (had to pass a board test or somesuch). We had discussed the fact that I was a virgin and all that. Thought he understood what was necessary (since I really wasn't sure about any of it). Nope, it was wham bam. He even insulted me by telling me I couldn't be a virgin because my hymen didn't bleed. At which point, I wanted to slap him or something. So I let the good doctor know that he needed to take me home, that I had lost my hymen to a tampon while riding a horse at 13 yrs of age (truth) and since I never had sexual intercourse (or done anything other than heavy kissing and petting) I was a virgin, and that his being a doctor didn't make him very smart.

 

[philos]

Once had a bf that claimed he had a velvet buzzsaw. Big disappointment for me. It may have worked on others before me but it didn't do it for me.

My first experience with sexual intercourse was very disappointing. My then bf was an almost doctor (had to pass a board test or somesuch). We had discussed the fact that I was a virgin and all that. Thought he understood what was necessary (since I really wasn't sure about any of it). Nope, it was wham bam. He even insulted me by telling me I couldn't be a virgin because my hymen didn't bleed. At which point, I wanted to slap him or something. So I let the good doctor know that he needed to take me home, that I had lost my hymen to a tampon while riding a horse at 13 yrs of age (truth) and since I never had sexual intercourse (or done anything other than heavy kissing and petting) I was a virgin, and that his being a doctor didn't make him very smart.

That sounds horrible. I've never been with a virgin so I can't comment on that but you think he would have learned a little sensitivity along with anatomy.

 

[NestleSnipes]

Everyone is always posting about the firsts and bests. WHat are some things that just disappointed?
Personally I remember my first time not being all that spectacular. I just thought "Is that it? Not really worth all the mental energy I gave it."

My biggest disappointment would have to be the time I turned down a girl I had courted for over 2 years. It wasn't because I shouldn't have turned her down but the fact that she didn't live up to my expectations or standards.

We were friends for most of high school and she was 2 years younger than I. I had graduated and was living in my own apartment. She was a senior and about to graduate. We picked up our talking quite a bit for about 3 weeks before we decided to have a date. The first date was incredible. We had something to eat, we played pool at my place, watched a movie in bed and ended the night having our first kiss(another disappointment in a way. She wasn't that great).

The second date we had just two days later was led in the same direction. However, our making out led to 2nd base. Touching and grinding led to me giving her head. I was happy with it ending right there. I was happy knowing we we're "pretty much" in a relationship at that point and we had gotten as far as we did.

Then came the kicker when she said "I want you inside me".

Most guys would have blew their lid at that statement especially for the talent that she was. However... I was completely turned off. All of this innocence and good girl nature that she had put off for years in our friendship was the reason I was into her. She wasn't easy or a quick lay and yet with me she chose to throw it at me.

I said no. She got uncomfortable. She never replied to any follow up's that I did to make sure we were on good terms. Friendship ended that night I guess.

Disappointing.

 

[Silly_Goose]

My first time was FANTASTIC. It's almost like it's been all downhill since my first lover. =S
But the most disappointing thing ever was having sex for the first time with this guy I really liked who hadn't had sex in about 6 months... he came after maybe 10 seconds. Dx
The runner up is a guy who had the SMALLEST dick of ever. Not just short, but skinny as hell. xP Men, it's not the length, it's the thickness that counts.

 

[ElectricGinger]

My first time was somewhat of a disappointment. I hadn't planned on losing my virginity that night or any night back then, and was kind of pushed into it. But that wasn't the biggest disappointment... The sex just wasn't good. I remember thinking, "What was the big deal about?" It was really boring, to be honest. And it lasted way too long. An hour and 45 minutes of boring sex I didn't even want to be having.

After that the biggest disappointment I can remember was when I finally accepted that I would never be able to cum via just sex without a ton of work, seemingly too much work for it to even be worth it. My body has so far only ever been able to get there via clit play, ever since I was little and taking care of myself. Really huge disappointment when all you've ever been told by media is that the "g-spot" is the way to go.

Good thing I have a man who's incredible with his tongue ;-)

 

[philos]

I wonder if this thread wasn't a mistake. Is it unhealthy or unwise to dwell on the negative? I sort of started it in a moment of frustration, anger and of course disappointment. Now I wonder if I should have just sucked it up and taken a more stoic approach. I guess I'll just let it be and see what others think.

 

[Red_and_Mackie]

I wonder if this thread wasn't a mistake. Is it unhealthy or unwise to dwell on the negative? I sort of started it in a moment of frustration, anger and of course disappointment. Now I wonder if I should have just sucked it up and taken a more stoic approach. I guess I'll just let it be and see what others think.

I think it was a great idea. I like to read about the experiences others have had, good or bad. Lit can sometimes be a deep fantasy world where everything is erotic and sex is perfect. So it is nice to have "real" threads like this to balance things out.

 

[lonelysmile]

My biggest disappointment is the fact that I've only had sex with one person - and that wasn't particularly exciting :/ I'm too self-conscious to pursue someone I like (mostly b/c I'm afraid they'll be crazy like my ex and stalk me after we break up :/) and I can't wrap my head around a one-night stand. ugh!

I'm also a little disappointed that I didn't have sex with this guy who offered to have sex with me when I was 18ish ... I was dealing with coming out issues and stuff, but just knew I liked girls - I didn't really come to the conclusion that I could possibly like girls AND boys. Still - he may have been a manwhore but holy fuck he was hot. damn.

 

[philos]

My biggest disappointment is the fact that I've only had sex with one person - and that wasn't particularly exciting :/ I'm too self-conscious to pursue someone I like (mostly b/c I'm afraid they'll be crazy like my ex and stalk me after we break up :/) and I can't wrap my head around a one-night stand. ugh!

I'm also a little disappointed that I didn't have sex with this guy who offered to have sex with me when I was 18ish ... I was dealing with coming out issues and stuff, but just knew I liked girls - I didn't really come to the conclusion that I could possibly like girls AND boys. Still - he may have been a manwhore but holy fuck he was hot. damn.

I think anything we did or didn't do in our teens shouldn't count. I know if I started listing the mistakes I made during those ages I'd be at for days.

 

[Cinner]

Another time, another lady, we were enjoying ourselves by the fireside on the floor. We were anticipating a long weekend together inside. In the middle of the Friday night afterglow she gasp and begged me to keep my eyes closed. She got up, was gone for like a minute, then came back with a warm cloth and (still begging for me to keep my eyes shut) cleaned me. Yes, the monthly curse. We were both disappointed.

This happened to me in August (two months ago) when I took my holiday from work - a completely wasted first week! Several of my Lit friends have assured me that that wouldn't have stopped them, but it did stop my Partner and me.

 

[darkbeast]

Wow. So many. Anyone who really knows me knows that sex is not a casual thing for me so one night stands have been ultra rare but have happened. Most of the disappointments relate to those moments where I think "yes, this is going to be great with this woman because I think she is so hot and I dig her in so many ways" and then she lays there and doesn't respond. If we talk it is "Oh, i thought you liked submissive women." There is a huge difference between submissive and passive. Always made me feel icky and feeling like "hell, I could have just masturbated and not have had to worry about the awkward morning after."

 

[philos]

This happened to me in August (two months ago) when I took my holiday from work - a completely wasted first week! Several of my Lit friends have assured me that that wouldn't have stopped them, but it did stop my Partner and me.

Seems to happen every vacation. Does relaxing or change of routine bring it on?

 

[okayterrific]

when i was in college i used to be on another message board, and after a few weeks me and a woman that i talked to decided to meet and hook up. i suppose an important part to this story is that prior to meeting up we never exchanged pics. she turned out to be short, fat, and ugly but i had sex with her anyway. i was so disgusted with myself that while she was in the bathroom i sent a text to a friend and told him to call me in 5 minutes. when he called i pretended that he was my dad and that his car broke down so i told her i had to go and help him out.

 

[ItsKittyBitches]

I'd say the worst experience I've ever had was doing it with a guy who couldn't keep it up. It was super embarrassing, and I refused to hook up with him again after that.

Sigh :c

 

[HeatedWand]

how could that be!

I'd say the worst experience I've ever had was doing it with a guy who couldn't keep it up. It was super embarrassing, and I refused to hook up with him again after that.

Sigh :c

How can a guy not keep it up being with a hot sexy lady such as yourself?
That is ODD!

 

[muffalo]

Philos, I think this thread is great! Sex isn't always the best, let's face it. It's fun reading other people's stories.
My first time was great! Probably the best I'd say. I just got real into it and started fucking her hard and deep. We both came, in fact she kind of milked me dry as she tightened up.
One of my disappointments would definitely be going down on a girl, then her saying she's too tired. I mean, there are those times when that's okay(cause I like eating pussy), but this was clearly not one of those times. I had been worked up all night and she knew it. Aargh.
Unfortunately the only other disappointments had to do with me. I mean, the fact is, there have been times where stress, or the fact that I jerk off a lot, prevents me from getting it up. However, I always do my duty as a compassionate man and go down on the girl, cause I do love it! And I always make it up to the girl later with awesome sex.
Overall, I think even if the sex isn't the best, it's still pretty good. My disappointment is when the sex never happens

 

[philos]

Sound like the old saying "what's the difference between good sex and bad sex?
there's no such thing as bad sex." Not that I subscribe to this but I guess maybe there is good sex and better sex and on that rare occasion mind blowing, toe curling, unbelievably good sex.

 

[mytwinsister]

First time wasn't great at all, nor was my second time. That guy knew nothing about women even though he claimed being great in bed.... great moron yes!

Another disappointment is that fuck friend I was with years ago who didn't want to do any cunnilingus but I HAD to go down on him all the time. It ended quickly.

 

[tkinsc]

I met a girl in college one night and we started talking. She was cute, blue eyes, and small tits. Somehow we ended up talking about sex, and it turns out she had only had sex once before. The next night we were drinking in my apartment, me more than her. We took a walk and kissed on a bridge at the pond on campus. We continued to make out on the bridge and I continued to get drunker. We ended up back in her room; I had her shirt up sucking her tits and a hand down her pants fingering her. Then I passed out.

We dated for several months and I never got that far again. I wonder what would have happened if I had about five less drinks.

 

[philos]

I find this hard to understand. How can any man not love having his face between a woman's legs? Some days I can't talk right because of my tongue's activities the night before.

 

[JasonGuitar]

I lusted after the same girl for 4 years in high school. It never happened and then we wound up bumping into each other a couple years ago. We fooled around and wound up fucking. It was quite lackluster. How disappointing.

 

[philos]

Why does this seem to happen so often? The fantasy is so much better than the reality. I guess the good thing is that sometimes the opposite happens. You think it will be lackluster and mediocre and are shocked when it knocks your socks off.

 

[JasonGuitar]

Why does this seem to happen so often? The fantasy is so much better than the reality. I guess the good thing is that sometimes the opposite happens. You think it will be lackluster and mediocre and are shocked when it knocks your socks off.

I've definitely had that before too. I dated a girl that was cute, but kind of straight laced, and really sweet. Once we had sex, she just lost it and became a freak...in a good, but tiring, way.

 

[liv21]

One of my big disappointments, which happens more often than I'd like, is when I'm hot and bothered and ready for a hard fuck, and he tries to put it in me with only a semi. It doesn't feel good, and really hurts my self-esteem. It's like, how many times did you just get me off? I was feeling pretty sexy. And still I can't get a rise out of you (pun sort of intentional).

And here are two disappointments rolled into one night.
One time my fiance and I were hanging out at his house. We dropped acid. Now I'm sure not many people here have done it (or even approve of it), but psychedelics are very sexual. For me at least. I'll eat a tab and have sex and masturbate for most of the 12 hour trip. Well it wasn't until about three hours in that my fiance and I started to get frisky. He started off by fingering me, which was amazing. I was so ready for sex, maybe oral if I was to get lucky, when our friend showed up at the door. We were expecting her of course, but the timing was just awful. Most intense cockblock ever. I was aching and even shaky. After an hour or two of conversation and trying not to be awkward, I had to excuse myself to take a shower. I'll give you three guesses as to what I did in there.

The next bit I've described elsewhere on the boards.

Later that night things didn't get any better. Every time our friend would leave the room, my fiance and I talked about how awful it was that we couldn't get down to it. I should mention I totally have a crush on this other girl, too, which isn't helping my libido. He's telling me to make a move on her and that she wants me too, but I'm too chicken to do anything.

My fiance graciously set me up for an opportunity by fingering us both at the same time. I was in heaven. She wasn't that into it. I'm easy to please--her, not so much. I still wanted a lot more though, and he took me up on that. We had sex in front of her. She watched and even masturbated to it! Shit, I was in such a trance that I didn't get to see that bit. It would have been so easy to get her involved. Instead of indulging my biggest fantasy, something I crave right now, I just had regular acid sex. Which is fine, but still. I'm still kicking myself for not taking the chance handed to me.