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QUESTION: I am a 53 year old male and was interested in trying having sex with another man both oral and anal, but i am nervous about receiving anal for the first time. My quetion is are there any anal toys which could prepare me as to how the anal sex with the man would feel and which one is the best for my situation. Thank you.

ANSWER: Hello Steve,

Thank you for your question.

Yes, there are toys that can prepare you for real anal sex with a partner.  In fact, it is a very good idea to try anal pleasure by yourself for the first few times, to ensure that you  can go slow and enjoy it, and so you don't feel pressured by a partner.

With that said, you could start with an anal training kit.  Since it is your first time, this is a good option, because a training kit starts you off with a very small, slim butt plug first. Then you can gradually increase size as you grow more accustomed to the feeling of having something in your anus, and feel more comfortable with that.

I recommend Dr Joel Kaplan's Anal Dilator Kit to start with.

As you can see the kits starts off with a very small, slim butt plug and then gradually increases to the largest size (5 length x 2 girth).  With the average penis size being 5-6" in length and 3 1/2" girth, the largest size should get you used to being penetrated by something almost the size of an actual penis.

If you are looking for something a bit more realistic and which would feel more like a real penis, I would go with a flanged dildo that can be used for anal penetration.  You want to make sure that any toy you choose has a flared or flanged base, to protect you from it slipping inside.

The American Whopper is a very popular dildo and has an insert-able length of 5 1/2" with a girth of 4", so slightly larger than the biggest anal plug in the kit above. This would allow you to get a more realistic feeling of what a real penis would be like and help prepare you better. You only have to insert as much as you like, or feel comfortable with, so you don't have to worry about it being too big to begin with.  Only take in what feels good and go slow.  Also, the head is slim and it gradually gets thicker so this allows you to slowly stretch the anus sphincter, to where-ever you feel comfortable, going more gradually each time.

The Whopper is here-

Also, the Whopper has a slight curve which helps aid in prostate massage and thus your pleasure as well.  And, it features a suction cup base, so you can stick it to a chair for hands free penetration.

Please also read my article on Anal Sex for Beginners-

It goes into detail on how to prepare, safety issues like wearing condoms, and things to do and not do during anal sex.

I hope this information has helped you.  If you have any further questions, let me know and I'd be happy to answer them for you.


---------- FOLLOW-UP ----------

QUESTION: Thanks Domina your answer was very helpful,the only other question i have for u is the place u gave me for the toys (they looked perfect to start with) how discreetly do they ship them to u? Thanks again

Hello Steve,

Glad I could help.

This is from the site:


Discreet Shipping

Products are shipped in plain boxes or envelopes with a nondescript return address.


So you see, the shipping is very discreet.  I buy stuff from there all the time, and the boxes are just plain and ordinary.  No one but you would know what is in them.


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I am your Personal Pleasure Guide and I can answer questions about any sex toy on the market, including toys for women, men, transgender, bi, gay, lesbian or other. My specialties include women's sexuality, sexual pleasure and sex toys for women, including the G-spot, body safe lubricants, sex toy materials, including those to avoid. I also know a lot about men's sex toys include dolls, c-rings, prostate stimulators, anal toys, and masturbators. I have extensive knowledge about bondage and kink toys including proper and safe usage, as well as sex toys for couples and romance products to help spice up and enhance your relationship. In addition to sex toys, I am very knowledgeable about sexuality, the sexual response cycle, and sexual anatomy, so can advise you on the best toys for specific body parts and how to use them for maximum benefit. I have tested numerous sensation and stimulating creams as well, so can advise on these type of products, if they work, how to use them, and what products to avoid. If you are wondering about a product comparison, I can give you my honest opinion on many varieties of a similar toy type, including pros and cons of each. In addition to sex toy questions, I do have a lot of knowledge about human sexuality and relationships as well and have answered questions about open relationships, erectile dysfunction, and other issues. If I don't have the answer myself, I will find it for you, as well as other resources to check out. My G+ Profile is here-


As as pleasure consultant, I have worked for 6 years in various sex toy shops, including brick and mortar shops where I advised customers on what types of toys they may like to purchase, as well as educating them on the toys and sexuality in general. For the past 5 years I have honestly reviewed over 1000 sex toy products, including creating a guide to body safe lubes (paraben and glycerin free), written articles on sex toy materials and some known toxins, sex toy safety, glass toys and their safety, Eco-friendly sex toys, sex toys for women, men and couples to share. I have an established sex toy review blog with over 5000 articles, reviews and sexual information posts, and have gained a reputation as a sex toy expert.

Society for Human Sexuality, San Francisco Club Cal Exotics Xbiz Real Sex Toy Reviews

Publications, Sex Life Canada,, the Sex Carnival, Whiplash!, SMUT, Divine Caroline, Carnal nation, Good Vibes magazine, Lover Magazine, Broken Pencil, AltSexTalk, Ezine Articles, Real Sex Toy Reviews, Boinkology, Examiner,, and many more.

6 years working in the sex toy industry 5 years reviewing sex toys and writing articles on sexuality BFA and a BA Numerous workshops on sexuality and sex toys in general.

Awards and Honors
Governor General's Award for the highest GPA

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My main emphasis is writing sex educational review of sexuality products for the adult public via my blog and various other publications. I have also written articles and product descriptions for various sex toys shops including, TabuToys, Pink Cherry, Babeland, Good Vibes,, MyTickleSpot, as well as numerous specialty shops and manufacturers of quality sex toy products. Manufacturers include Lelo, We-Vibe, Cal Exotics, Pipedreams, Sportsheets, Ruby Glass, Happy Valley, Fun Factory, Vibratex, Liberator, Adam & Eve, Dr Laura Berman Intimate Basics, Big Teaze Toys, Tantus and more.

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