What was your most disappointing sexual encounter

this hot cheerleader in hs i was a jr and she was a sr and she broke up with her bf because he was an asshole jock. we hung out bc i went to church with her best friend. anyways we went out a number of times and sex was amazing but she never wanted me to go down on her and she had given me blowjobs many times and she was a swallower. finally we 69'ed and she just tasted bad and smelled bad. she really liked it too and all she wanted was her pussy eaten and it was bad like by far the worst i have ever been around. i mean she was one of the hottest girls in the school and i was just an average dude. we split when she went to college.

 

I was 26, he was 28 i'd been trying to get this guys attention for a while and with our hectic schedules it was difficult to set up a date but we finally got a night that worked went out for dinner and we were vibing real good, he was hot and i fully intended on fucking him on the first date, at the end of the night i invite him in for drinks, we start making out on the couch and he starts getting hard, i'm getting hornier by the second and from what i' feeling hes got a sizable cock, i unzip his pants, pull it out and give it a few tugs before spitting in my hand and i swear i only got a few strokes in before he tensed up, let out a groan and unloaded like a horse, i didn't want to laugh but i didn't know what to say, he quickly started apologizing saying it had been a while, i was so horny i didn't care i told him it was fine and went down on him and started sucking but he wasn't getting hard again and i eventually gave up, he wanted to spend the night but i sent him on his way as i clearly needed to get myself off.

We tried again and i insisted we skip the foreplay, he insisted on wearing a rubber which i figured may slow things down but it really didn't even with me on top he only lasted a few minutes, that time i let him spend the night, figured maybe he'd recover and be good for a while, even after a few hours i woke him up and he was only good for like 3/4 chub, tried one more time in the morning, he was good for maybe 10 minutes but had no clue what he was doing, only reason i got off was because i was vibing my clit.

after that i cut ties with him, it was quite disappointing.

 

That's sucks. Sorry you had a bad night

 

You should have pursued further and taught him how to overcome his premature ejaculation. It can be easily remedied.

 

Hate to day it, but an online woman lied and was fat as fuck. I was there and said, I'm gonna try, but couldn't get hard no matter what. I had to leave. I'm not fat shaming, but I can't get excited for it

 

We often hear that this should not be a problem, that women give birth to children and that, consequently, man's size is never a problem.
In reality, at least for what is my experience or some articles that I have read, it is not exactly like that. It depends on many factors. First of all, we are not all the same, both men and women, and, above all, the circumstances can be different and change over time. For example, my girlfriend is tighter at the end of her menstrual cycle, when we resume having sex.
Especially for the woman I think it is something very subjective. I was said for example, that some women with retroflexed uterus don't like a deep penetration.
I remember more than once some occasional partners who did not want us to have sex in the missionary position with their legs raised on my shoulders for this reason.

It happened to me sometimes that few of my partner in the past had their hands clasped at the base of my penis to prevent me from penetrating them deeply.
It is true that probably I am quite large in circumference and that at the base of the penis it is even larger, but, as I said in another post, I lived that experience as it was more a refusal, a distance and little interest and participation in the relationship. They were occasional relationships and, given the nature of the situations, I do not believe that it was up to real physical problems but it was due to a lack of complicity and involvement. I had the impression, and felt it, as a rejection of my person so I decided to let it go.

I know that each case is different from another and that we cannot fully know all the personal situations, so we must not generalize and immediately get to easy conclusions. But I think this is precisely the key. Beyond the physical aspect of the problem, other, equally important if not more, factors also come into play.
A strong mutual chemical attraction. The fact of feeling comfortable with someone. The climate of trust that can be established. The emotional involvement of both.
Yes,it's true, this does not change the fact that two people are physically very different even in their private parts. However, the approach to this kind of difficulty is different. There is on the one hand the willingness and desire to experiment in an atmosphere of trust and awareness that the other is attentive and considerate, and on the other hand the attention of the partner, the fact of understanding any fears and being empathetic. All this not only because one is good and gentleman, but for the achievement of an objective that is also sinful and linked to lust.

I'm sorry it went like this, but as Barry said, sometimes it's better to find an other partner if it doesn't work. I too have been disappointed in the past, albeit for reasons other than size.
Fortunately, with my current partner, it went differently. Perhaps because of the kind of affinity and mutual interest that I mentioned above and that has tied us from the beginning.
When I met her I was immediately attracted to her personality and, observing her, I thought "what an incredibly pretty and well-made little doll, I am troubled by the fact that she is so tiny and ,at the same time, with those pronounced shapes".

Yes, because it is something that presents itself immediately, when it comes to starting penetration.
About the length, for the most part, if there is some issue, it can occur when you are already inside. But if you don't push abruptly with all your might like a battering ram, it's something you can handle more easily.
In these cases of great physical disparity, as in the case of me and my partner, the way of making love and, above all, of starting sexual intercourse, changes a little compared to other more balanced situations, which are most of those I found myself in.
One can avoid going on the subject but then comes the moment when you get intimate and undress. The partner's reactions are not always the same the first time you see each other naked.
My partner was very focused on her fear of not looking beautiful in my eyes due to the particularity of her physical appearance, while I was going crazy to see her naked breasts so disproportionate to her tiny body and that delicious little well-groomed tuft between her legs. But then, when I also undressed, I was very excited and all the attention shifted to my erect sex which, objectively, appeared to her out of proportion compared to her body. It is not said that we should immediately get to the point and luckily one can talk, joke about situations and make things lighter and more fun anyway. This served to divert some attention to this thing, to relax us and to make the atmosphere more relaxed.
In these cases the erotic experience is already very strong during foreplay. Maybe it's a phase that lasts longer than usual . However, it is a well-spent and pleasant time. I love to grow my partner's desire to the limit, with allusions, caresses, kisses on her body, mutual explorations, until she loses her self control and litteraly she craves for it, she becomes impatient and nervous, almost aggressive. She wants to feel it inside, and then it becomes inevitable to move on to the next step.
The moment of penetration takes longer, but all the feelings that accompany it are highly erotic. Dealing with a woman who is hungry for sex is always an extremely involving experience when I am in the right mood. At other times it could also frighten if unprepared. Then there is the visual aspect that has a big impact. Seeing how things look together when there is a big difference in size has an impact on libido. Probably more for the man than for the woman.Then the sensation of contact comes into play, the actual act and the effort required to insert the penis. At the beginning it requires slowness and some tricks like relaxation, using lubricant even if she feels that she is moist, applying it generously both on the penis than at the opening of her vagina. The key for us is to go slowly enough, depending on her level of excitement, to allow her vagina time to stretch over my penis. Sometimes it happened that she reached orgasm at that moment, during the first thrust, for everything that happened before and because a further stimulus was enough to trigger it, or perhaps also for her physical conformation down there.

Of course, that feeling is wonderful for me too, well wrapped and kept tight in all the length that can enter inside. In addition there is the sensation of the tip of the penis which is elastically pushed from the bottom of the vagina. But, especially after prolonged and repeated intercourse, it can cause a little burning and redness to me too the day after.From her point of view she told me that the sensation of excessive dilation at the beginning and of pressure during deep thrusts is compensated by the feelings of pleasure and completely overcome by orgasm. The sense of soreness that she feels in the following days is more similar to what one feels after intense physical activity, especially when you are not trained.

 

I just wondered if some women feel it is an achievement taking a huge dick, and maybe discuss it with their friends

 

I would fit into the initiate slowly with comfort being the guide. The male need to relinquish control of the speed of insertion to the female. I think some porn sites make you think causing a bit of pain on insertion is OK and erotic. Has definitely not been my experience. Sure fire way to not get any repeat sex. If the girl sees your penis and you hear phrases like "I have a short vagina" or "be easy with me" take it as a hint.

Coconut oil has to be the best lube I have found yet. Water soluble so cleanup is easy. Very slick, the closest to real pussy juice I have found.

 

I believe it is something subjective. Maybe, unless special cases of size queen, they do not say it explicitly. I remember, when I was a boy, that sometimes the girls from the university, or even those from the parish, talked to each other about their boyfriends or their adventures. Maybe I was sitting not far away and I happened to hear their speeches unnoticed.
I remember that there was one girl in particular that was one of the most enterprising in the group. She was always informed of the latest news and, when there was some new boy around, she always wanted to be the first to know him. Especially if the new one was particularly handsome or had some leadership characteristics. The champion of the local football team, the one with the most trained physique in the gymm, the front man of the local musical group, the guy who had been studying in London and was the most elegant and cool, the one with the prettiest Harley Davidson and the most eccentric tattoos and so on. Even though she was small in stature she had on her side the fact that she had an important bra size and that she was young and pretty in her 18 years. She had a cute face and a sexy physique, she vaguely resembled Christina Ricci, to get an idea. She certainly did not go unnoticed.
In short, a group of friends from a parish family arrived on vacation one summer in my province. Among them was a black boy from New York. He was a very tall guy with a nice, sporty physique, and, to say the girls, very nice and with a great smile. He was good at playing basketball, I saw him in the field behind the church oratory sending the ball into the basket without effort. Thanks to the summer, the young age, the charm of the foreigner, and who knows how many things we still don't know, a story began between the two, an adventure that lasted all the time of the holiday. It was sad for her the day he had to return to his country. One evening, it was already autumn, but there was still good weather, the girls met in the pub.
A friend of mine was engaged to one of the waitresses in the bar and we were at the counter. Behind us the girls at the table were talking, and the topic of size also came up, among other things. The girls were very curious about the matter even if, from what one could understand, the envy was more for the fact that she had been with a very handsome boy.
However, the girl confirmed that she had never actually had such a gifted boy before and that it had been an unusual experience. The girls asked for details and how the experience had been.
I would say that, in that case at least, there was some interest in the subject. Then I don't know if all the friends wanted to try that experience. At least they talked about it, not much differently than men do.

 

for this reason I am of the opinion that in these cases positions with the woman above are better. In this way she has freedom of movement and can decide when, how, at what angle, how deeply, with what rhythm.

Yes, I agree, whatever the real reason why she says it.
If it is an excuse because she does not want to do it, then it would be wasted time and it is better to leave it alone. If instead it could be a problem for her or simply a fear of her because the situation is new or because she has had bad experiences in the past, it is important to reassure her. If it is she who has the initiative and is in control of the situation especially with regard to position and movements, the climate becomes much more relaxed. Even her body relaxes and above all she does not put herself in that situation in which, presaging unpleasant sensations, she contracts instead of relaxing, right in the wrong area. Maybe if one turn the attention away to the penetration itself and manages to get her excited in another way and bring her to orgasm, the probability of success greatly increases.
When I was younger, there was a time when I dated escorts with a certain frequency. I was young, shy and at the mercy of hormones. I am not saying this to justify myself, but failing to have relationships in another way, it went like this for some time. I was looking in the ads and, most of the time I didn't know who I would be facing unless I returned to the same escort, if she hadn't already moved elsewhere. More than once it happened to me to find myself in front of women with very small frame, often of oriental origin, mostly Chinese, sometimes even a little more chubby but still very small in stature and with very small hands. When they saw me naked and especially when they proceeded with the ablutions for which they had it in their hands, they often said to me phrases like the ones you mentioned above. Clearly, the level of complicity and intimacy that could be there was limited by the type of situation. However,after a little pampering in which, as far as possible, I acted as if they were truly mine girlfriends and, without rushing things and leaving them the freedom to decide on the position and movements, in the end I managed to get to an intercourse.
Once she had accomodated me, the most was done and, usually, she began to move slowly over me holding on with her hands on my shoulders or holding my hands that I offered to support herself. And I was already happy to be able to satisfy my intrusive need.

 

I haven't had a disappointing sexual experience, other than the one I didn't have. My wife and I had been dating seven years, were engaged, and had enjoyed exploring each other's body, mutual masturbation and everything except oral and penetration sex. I had promised her not to have sex with her until our wedding night, not realizing at the time that she had been having sex with other guys. Anyway, one night we were deep into our make-out session. She was nude and I was dry-fucking her. She opened herself and said, "i want you inside me." In an act of utter stupidity, I said, "No, I promised you I would wait, and I will wait." So I didn't do it. She didn't offer again until our wedding night.

 

Last year I was meeting with a potential "sugar daddy", safe to say it was a disappointment. He was really old, slow, and came in me after the first pump. Every subsequent time was boring and quick but I benefited in the end so oh well lol.

 

One night I was drunk with my girlfriend and we were dancing all night and we were both sexing each other up and there was so much build up that we just had to fuck. Only our bodies didn't really comply. Barely got hard, dry mouth both. Sucking and licking was a no go. And I couldn't orgasm at all. She on the other hand came so fast.

 

Does she have a reason? Is she getting old and drying up? Do you stick around long enough for her to get laid too?

 

I met a younger woman online and we agreed to meet at a motel in her town.
On that day I met another woman hours earlier, a lucky and unplanned thing. She thanked me with a blowjob, it was luck, and selfish me could not turn it down.
Wow, she deepthroated me, didn't hurry to finish me so she sucked me long enough and took it deep a few times. Then she swallowed me and kept going a bit longer.
I felt the after effect for long after that, thinking I was lucky, and luckier since I was going to meet the other one.
Skipping everything in between, she arrived in my room, gorgeous, eager to meet an older guy and feel used - her words.
I didn't go for intercourse right away but when it came to it, I had some difficulty getting hard. I knew it was from the awesome blowjob from earlier.

I got all hard and it felt so great inside that younger woman. I started thrusting and I felt I was going to cum VERY soon.
I pulled out to prevent an early finish, my cock bounced and throbbed several seconds. Well, I WAS FINISHED when it comes to using my cock.
It went soft and it killed the mood. She didn't feel like staying and receive oral or anything else. She left and we never met again.

 

Wow! One Thrust? At least I get two or three in! Lol

 

What a wanker

 

Bummer!
And like said, at least a few thrusts or more, for the first time around.
Now for the second go around, you'd really be in for it.

 

Gal I met at a party .... she was drunk and gave me a hand job. She was very aggressive and I realized she had cut me with her fingernail. Blood was all over me.

 

Too bad...