Anal sex on first date?

I went on a date. We’ve been flirting around for a little while but this was our 2nd sexual connection. We did have sex but I did not reach orgasm with him. He wanted to know
if he “was enough for me” I felt terrible.

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Plus I was put on-the-spot to answer an uncomfortable question. What the hell should I say?

I had to reassure him. I did tell him that oral sex is important for me. Not to mention I forgot to take my tongue ring out. I couldn’t taste him, the way I wanted. I do like oral sex, give and receive, I like how a man taste, but he did not give me any of his juice to taste.

He said he was, “holding back.” Wow! Why? I was distracted by the tongue ring & also he did not go down on me… He did not perform oral sex on me. He did not even try.

On our 1st sexual encounter I tried to get anal. He refused citing he’s “never done it & didn’t know how.” Never? He’s 50 years old. Another wow! I felt he didn’t want to stop his momentum to try something new.

Whatever! Of course I will keep chipping away at this man until his dick starts to grow again…

In the meantime, I am wondering am I the one who fucking this up? Label me: babbling fool, but: What can I do to improve this man’s sexual experience with me? Continue Reading…


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I think I am misunderstanding something… Do you want to improve this guy’s sexual experience?

I think he is the one who should do something about your never happened orgasm. He should improve, maybe should go down on you for start, and you can direct him how to perform oral sex on a willing pussy.

I understand him on anal sex. I am not big fun of anal sex either, however if it requested I do not have any problem to “give”… Continue Reading…


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Is there an emotional – spiritual intellectual connection? Does he find you attractive?

Maybe you could concentrate on that more & the physical connection will come. He may just be nervous. Could be more “green” than you are. Continue Reading…


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Intimate conversations are often difficult but if you want enjoyable sex you have to need to open your mouth and communicate with him.

You already know that. Do you really expect him to be a mind reader? Continue Reading…



I love anal sex and his penis size would be perfect for anal sex but he says anal sex is gross

Is she into anal sex? If yes, for anal sex than do an anal vaginal double penetration with a dildo and your dick

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I would recommend “brutal honesty”. I’m not talking about being mean and aggressive but a grown up conversation between two adults.

From the situation that you described it sounds like you are more experienced sexually than he is, and he is uncomfortable with much beyond “vanilla sex“. So talk to him about it but with you clothes on.

I say with your clothes on because he is probably already feeling insecure and will likely feel more vulnerable when he’s naked.

Definitely do it face-to-face, over a drink or something. Let him know what turns you on
and find out what he’s willing to do and at what pace.

He may cut and run, or he may be willing to expand his horizons, but you’ll never know unless you ask him.

Continuing down the path you’re on, just sounds like continued sexual frustration. Continue Reading…

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There is more than one inning to any good ball game.  If you like the guy and think he’s listening to you then communicate with him. If it does not work, then “train” him to your taste. If he is not “trainable” than forget him and find more experienced sex partner.

A lot of guys would be more than happy to make you reach that big O… Continue Reading…


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I like man’s juice too! Sounds like he has little experience, is possibly intimidated by you, or perhaps, your enthusiasm!

Could it be, he’s only been with inhibited women, and doesn’t know quite what to do, or how to respond to you? I think the above lady got it right. Train him!

The poor guy seems to have led a rather sheltered life, until now! You might need to work on his “training” hard, but never know hard work usually pay off! Continue Reading…


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I think at one time or another we have all been there… Do not want to hurt feelings, but honesty is the best bet.

Some of us are on a different level of playing field when it comes to sex. I just tell them they are not right for me, and if they give me the Spanish inquisition, then I tell them you are not satisfying in bed, because of…

If they are really willing to please, they will do some research and try new things. Other wise they will stay stuck in there boring sex life forever, and have sex with boring  females…

Thus never really satisfied sexually. A male and female ego is very fragile, but if they want to learn new sexual techniques to please,  they will.

The trade off is, if they learn new techniques, sex will be better and both player will reciprocate more. Continue Reading…


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I have met a few guys who made me feel I was doing something wrong and they just couldn’t get it done or when they did it was a big let down.

The first time it happened I was crushed….! That is, until my sex god hubby reassured me
it wasn’t me.

I had to quit meeting with one guy who never really performed at an acceptable level….

It’s not you, believe me. By the way, the guy I’m speaking of is a wonderful person otherwise, handsome, great personality, etc. Just too much work to teach him, what he should have learned a long time ago…

He left me frustrated many times, and finally I replaced him… You should do the same. Continue Reading…


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Actually if he really had never tried anal sex, I can understand why he didn’t want to try it on your first encounter. It was something unknown to him and the last thing he wanted to do was “fail” on your very first sex session.

First impressions are so big. Might have been a better idea to approach anal on a later play.

However, he’s being pretty insecure. Who the hell asks if they were “enough” for you right after sex? It’s like a guy asking, “Didja cum?”

ALL men know not to ask that, right? It puts the other person in an uncomfortable spot.

All in all, it sounds like he has some real confidence issues  and, at age 50  they’re pretty established. If you have a nurse complex, he’d be a good one to try and “cure”. But I’m guessing it would be a long process. Continue Reading…