First Time Anal Sex Tips – A Quick Guide to Ease It In!

The thought of first time anal sex can be daunting.  A quick guide can be very helpful. Anal sex is often perceived as the ultimate type of gay love making.

First Time Anal Sex  

Everyone has to start from somewhere.  It’s best if you have the knowledge before you progress into anal sex, so you know what is going to happen!

Surprise…anal sex can hurt at first.  It might well be termed as something uncomfortable at the beginning.

If you want to try it though, here are some tips on how to begin and how to experience it.  You might think that if you’re not doing it correctly, or think negative thoughts like “You are not normal.”


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Is Anal Sex Really for Me?  

Many gay men have loving relationships and excellent sex lives without anal sex.

It is important for you to spend time on discovering your anus before having sex with others.

Have a relaxing bath and stay naked.  Go to your bedroom and put some lube on a finger.  Work it around the outer side of your anus, while relaxing, and start pushing it in.  Sometimes watching a porn video, is the perfect sex education.

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Photo: Male Diagram for Anal Sex – Tips for First Time Anal Sex

Tips For First Time Anal Sex

Here are some tips to help ease you into your first time anal sex experience.

  • Relax

  • This is key to anything anal.  The sensations at the start might already be quite intense.  If you want, use your other hand to masturbate.  Allow yourself to enjoy all the feelings.  Relax and feel free to fantasize anything you want.
  • Explore

Explore the new experience and get a sense of the muscle inside you.  Make sure your fingernails are trimmed if you are using fingers.  Ensure all anal sex toys don’t have any sharp edges.  Especially when using metal butt plugs or dildos.

  • Use your fingers

When you’re comfortable, try inserting a second finger.  Rest assured that your anus can certainly receive 2 fingers.  Withdrawing your fingers might feel uncomfortable and that you want to go to the toilet.  This is normal as it is just a reflex reaction.

  • Experiment

You might also want to experiment with something more life size.  If so, use a proper dildo and not homemade products or a cucumber.  You don’t want to scratch the thin membrane of your anus or have something nasty break off in there.

  • Use Lube

When using the dildo, begin again with your fingers and use a lot of lube.  Silicone based lubricants are the best for anal play as water based lubricants are absorbed into the body through the rectum.  As soon as you bring silicone anal toys into the equation you will have to stick with Superslyde.  Most silicone lubricant’s will deteriorate silicone toys due to chemical interaction.

How do I Relax during First Time Anal Sex? 

It can be a bit daunting.  Stigma surrounding anal sex alone attached to anal play can be enough not to relax someone.  Research and relaxation are the only things that will calm you down.

You need to find a relaxed position and relax the muscles of your anus.

Sitting with your ass to one side can work well.  Try laying on your left side.  Bring your right knee up to your chest.  Keep your left leg straight. It will make it a lot easier for a sex toy or penis to slip into the anus.

If you’re standing, make sure your legs remain relaxed. Your sphincter will tense too if your legs are tense.  Push it in slowly and let it slide.


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When you feel resistance, pause and relax.  Push your anus towards the dildo, as if you were pushing faeces out.  You might find you open more easily.

Still, however gently you go, you can expect a bit of discomfort. There might be a moment of pain.   After this, the rest will probably slip in a lot more easily.

Anal sex can have very intense sensations as if every part in your body and brain just started firing.  Your instinct might be immediately to masturbate and cum in a way more exciting than you ever have before.  Enjoy the experience of gay anal sex.  It is a comforting and mature gay experience.

Exploring First Time Anal Sex Toys 

With anal sex toys try the more intermediate toys over beginners. Your anus has the ability to easily take more than a small finger sized toy!!

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Some people might disagree with my stance on going to intermediate rather than Beginner anal toys.  But my reasoning is solid.  Start with fingers.  Warm up to it and then move onto bigger and better items.

For instance, I  started on the Rocks Off  “Naughty Boy” 7 Speed prostate stimulator.   I thought this was the bees knees when beginning.  Now I’m already up to our UR3 Straps and Hoodlums!

Tips for Using a Dildo

  • Move the dildo slowly

Give yourself time to get used to it.  It might be that’s enough for the moment. You might want to experience a faster pace for as long as it would take you to cum.  If it’s the second, you want to be careful.

  • A dildo feels different to a penis

A dildo can go as fast and as hard as you make it.  It does not feel the same as a penis.  Loose skin around the shaft of a penis will lessen the friction on the anus.  Feelings may become intens. You might start groaning and moaning.

There comes a point when it is as if there is a barrier to cross. A feeling of being about to explode might make you stop.  Or you can cross that barrier to find a further degree of elation.

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Image: Euphoria – Tips for First Time Gay Anal Sex


Finally, there is the point where you finish at.   It is as if a plateau has been reached and no further level is possible.

  • Pause if you need to

You might want to stay there a little while, as it were to admire the view.  Then pause and prepare for the final excitement, which is when you withdraw.

  • Withdrawing the dildo

There might be a mess.   In order not to feel anxious about this, have a towel down.  Do it over a toilet or an easily cleaned surface.   Keep in mind though that after the high, there is a downside.

  • After using a dildo

Your anus might take time to close.  Spend time sitting on the toilet relaxing and calming down.  Mentally, you might feel unfocused and ‘spaced’ for hours to follow.

Will I Have to use a Douche or Enema Kit? 

There is a massive array or douches and enema kits available.

You want to clean out as much fecal matter as you possibly can.  This makes anal play feel a lot better.  It will clean you out and remove the fear of poo or anything like that coming out.

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Be prepared to make further discoveries about yourself and your partner.

On the one hand, if you’re the bottom, you are showing something intimate about yourself.  You are experiencing ecstatic sensations.  Making those noises and faces with your partner watching you.  You have to want him to do that.

Or you’ll be seeing someone else working his way towards orgasm totally different to what you’ve see before when masturbating or giving and receiving head.

Be prepared for the feeling of passivity if you are having anal sex with a lover.  If you resist being passive and not wanting to be the bottom, perhaps thinking that makes you less of a man.  Then no matter your preparation, you’ll be in for a bad time.

If you accept all the feelings involved in having gay anal sex, then it can be something unique.  Exploring each others body is a personal and very sensual thing. Anal sex is fantastic when it comes to bringing that next level of intensity to a relationship.  You will feel closer not only physically but emotionally.

Choose the right toys, the right partner, the right time and anal will be a blast!!


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Gay Online Dating

Online Gay Dating is an easy way for gay men to find partners with the help of online gay dating websites.

It is important at the beginning to do your research on the gay dating websites you are thinking of joining.  Find out if that website is suitable for you and can satisfy all your needs.  Dating Apps such as Grindr, Scruff and Recon.

You’ll notice that there are particular websites that cater to different types of men and fetishes.  Sign up to multiple various gay dating websites with the same interests as your own. Generally find  something in common before you even start searching.

When you do start searching through your chosen websites for potential partners and/or fuck buddies you can then spend a little time looking over the hits.

Who Uses Online Gay Dating? 

Online Gay Dating websites are mostly meant for both gay women and men.  Some websites do take care of the needs of male and females separately. And gay couples looking for someone of the opposite sex.

Gay men have the opportunity to meet their future partner with ease.  You just have to check out that the site offers singles a chance to hook up with someone of their choice.  It is essential for you to look out for your benefits.

Should I Use Online Gay Dating? 

Do you have any other options? Are you a social individual and go to various social events throughout the year?  You’ll have an even better chance of finding someone to settle down with.

Either way it is certainly worth it to try out a gay online dating website.

Social restrictions and obligations take up so much of everyone’s resources these days.  There are people who do not have enough time and confidence to go out and meet a possible partner.  Particularly those whom have only recently come out and find the scene a little too intimidating.

Accept to meet someone without any obligation.  Feel free to find your future partner just like anyone else.  You can also search for gay men any time since the websites are there for you 24/7.  Be anonymous while you getting know of the person whom you met online.

Should I Pay for Online Gay Dating Sites

Before paying for anything, it is recommended that you try out four to five website.  Check their services and then make a decision.  Many offer a free trial.  It is advisable to do this first.

Some factors to consider

  • The number of singles available in your section on different sites.
  • Your comfort zone.
  • Availability of your email accounts and chat rooms.
  • Most importantly, location.

After considering all these factors choose the website that is perfect for you. 

It is better to use the free membership of other websites too.  Because this wil allow you to share your profile with new gay men out there.

Today, gays seeking gays have found an easier way to find their future partners.  It is as easy as checking your email account after you have joined up.

Wait for those messages to flow in!!

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Make Sure You have a Good Profile

After you have decided to join a Online Gay Dating website like Gaydar or Just Say G’day and you need to write a profile.

All online gay dating sites will have over thousands of unique personal profiles.  Gay singles listing their characteristics, likes, dislikes and personal preferences.  Promoting yourself online can be challenging. You have to make sure that you will attract the guys you are interested in.   And make them stay and reply to your profile.

Online gay dating community is very competitive so your gay personal ad has to beat the competition.

Important Things to Know When Writing a Profile 

  • Know what you are looking for

Simply saying that you are looking to find a gay man for dating will attract all the gay men of the site.  Imagine your profile getting bombarded by messages from tall, short, fat, bald and other gay men.  You need to make your online dating experience better by eliminating the gay men you don’t like.

  • Make a list of your preferences

Qualities you want in a gay man, such as age, height, likes and hobbies.  This may seem superficial.  Why waste your time with people you don’t like?  Focus on the positives that you’d like in a potential mate.

  • Don’t list the things you don’t want.

This is limiting.  It often comes across as arrogant, racist and insulting.  Even if your preference is not a particular type of person, you may find that you’ll still fall for them anyway.

Online Gay Dating world is already harsh enough without adding to the pressure of being a particular type of Male.

  • Maintain a certain level of anonymity

All gay men using the website, must have an online profile name.  Be creative and choose a nice and creative name.  BigTool4U may seem like a cool name.  But you’ve just listed your big dick as your best quality.

Not necessarily the right impression you want to give on a dating site.   But if you’re after instant sex it might serve you well!

  • Upload a Good Photo

A photo is the best way to promote yourself.  Most new gay men seem to think that posting X rated pictures is the ideal way to attract attention.  At the start you will receive a large number of responses.

Are you looking for quantity over quality or are you looking to meet a nice guy? Think about that when selecting a photo to upload.  Be mysterious and keep the X rated photos to the bedroom!

  • Include a catchy profile headline

It can determine whether someone will read your profile or simply move on to the next guy.  Gay men are looking for the one profile heading that will stand out.  Put some fantasy into it, making it interesting and as original as possible.

Make sure your personal ad has useful, interesting information about yourself! Be honest and truthful.

By now you should be ready to write the perfect gay personal ad and find yourself a new partner.





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