Mentoring, self-help and submissive exploration

Rayne Millaray is a wild, 30-something, sex enthusiast who’s been “just one of the guys” for as long a she can remember. She’s been having sex since 1996, blogging about her sex life since 2005, advocating for a sex-positive society since 2008 and working in the adult industry legally since 2010. Her writing is published on various blogs around the web, including her personal site Insatiable Desire. She used to write a weekly column for Albany’s #1 rock station. And she was once Editor in Chief of SexIs Magazine. Rayne is, without a doubt, the girl your mother warned you about. Chaos incarnate. And she loves it.

21 responses to “Anal Play: Beginner to Stretch in No Time”

  1. marie

    You sound a lot like my Master. I am still far from convinced. He has been working on my ass for almost two years. Yes, he started slow enough to not cause great pain. At the same time it has never gotten better then uncomfortable. No amount of plugs,lube and streching make it any better. Even the smallest plug is unpleasant and makes it difficult to concentrate on his work on other areas of my body.

    He is not giving up on my ass, so time will tell.

    1. Big-Peazy

      One very important thing that people don’t realize about anal sex is this; One must be genetically predisposed to even be able to take anal and enjoy it. Two years should have been the clue your master took to realize you just can’t do it. Not just any one can unfortunately. If everyone could, anal wouldn’t be the taboo subject it still kinda is today. Now bot as taboo as it once was but still a little. Good luck and hopefully for your sake I’m wrong ans you and your master will finally get all the pleasure that anal can offer.

  2. Sunny Stream

    Thanks for your honesty.

  3. Pixie

    For more info check out the book Anal Pleasure and Health by Jack Morin PH.D. Its a wonderful resource with insight from real people, as well as a very knowledgeable author, in over coming inhibitions and health concerns and learning how to find more pleasure in that part of their body.

    The emphasis is largely in health and has great info even if you never do anything about anal pleasure. And the pleasure, it focuses not on intercourse, but in finding out what kind of anal stimulation you enjoy. A great read for anyone regardless of gender or sexual orientation.

  4. snowflake

    just remember in anal play (especially if this is new) to communicate greatly. it will always hurt at first, and for some like marie above it always hurts. this can be true though with vaginal play as a good friend of mine no matter how much lube, what kinds of toys, anything beyond a finger just happens to hurt her. So communication becomes extremely important. As submissives (general term) we all want to please Ours and so sometimes do not speak up when we should. if it hurts be sure to say something after all you only have one rectum and damaging it, not a pleasant thing.

  5. Susan

    Great article, thank you. My first encounter with anal was with my vanilla husband (Ex) causing extreme pain and tears. We never ventured back. I have always been submissive; unfortunately he was not a Master. I was always eager to try new things but was about as green and uninformed as it gets. Thereafter my curiosity was always peeked but not enough to venture there. Once separated, my eventual first lover knew of my curiosity and proved to me it was possible and even enjoyable. Believe he said I screamed “oh-God” with each stroke. (But those were screams of excitement.) I have always had ONE major rule of play (vanilla or not) and that is… whatever we do cannot create injury necessary for hospital emergency care!

    My training with Master has included much on female anatomy and function. I cannot believe what he knows of our nervous system. All the things WE never knew… even to ask about!! We have a “B” gland (not “g” spot) and the friction of this glad lubricates not only the vagina, but the anal canal too. Amazingly it somehow helps to clear/clean and lubricate the anal opening. I can tell you that I am spastic waiting for Master to get his hands on me come October and experience first-hand all his “Master” level knowledge has to offer this subbie!!

    I am lucky to have a Master find me as I do not believe I could have tolerated anyone less. As everyone agrees, it must be slow, consensual and well lubed (naturally or artificially). What’s the rush… a good patient D/M knows his/her rewards will be multiplied exponentially!

    Aspire to Inspire before you Expire

  6. JPsub

    this is my first time to this site and i am finding good information here. the sex i had with my x husband wasnt good at all. zzzz…. eventually i stopped giving my x husband sex because i gave everything to him outside of the bedroom and got nothing in return. my master/bf is a lot better and has introduced me to new things. he knows how to be patient with me and helps me understand things better than anyone has ever done in and out of the bedroom. i was nervous about being with him for the first time because he has had a lot of women and i had only a few men. i feel i am not worthy of him and feel like a virgin again because i do not have half the knowledge he has, sub or not. he gives to me and i happily give back. we havent done many things yet and am scared because i had no support and wasnt shown about sex. i knew the basics and to go any further about talking was taboo. i had anal with previous men and hated it. i am so tight in both areas that it needs to be stretched, something i didnt know until my master. he has me stretching all the time and drinking fluids to not be dry when we have sex. he wants to loosen me up and it does work. thanks for the article and it makes me feel better since i am new to being a sub. maybe anal sex will be enjoyable because my butt cringes when i think about it.

  7. Anal Training Tips | Little White

    [...] and here are two sites that goes over the basics of training yours or a lover’s [...]

  8. bottomarthur

    yes it takes training in order to be fisted but i enjoy the experience very much

  9. Polly Northman

    I think anal sex is cool and I fell pleasure with anal estimulation, including enemas. I just have a troube with the guys not letting me anywhere near their anal area! This so unfair! They want to have my ass but say their asses are forbidden. How come that? Well, I think I have to look for better men! ;D

  10. Ron

    I’ve been doing anal with my ladies for many years and actually prefer it to vaginal.
    Where I meet psychological resistance with a newbie, I always instruct them to start out on themselves, to overcome the clenching factor. I suggest they start out with warmed-over cucumbers or zucchinis, inserted slowly in the privacy of their own bedrooms. Once inserted they should masturbate in the normal way to combine the two sensations. Over a few days they can increase the size of the vegies in preparation for my penis. When the time comes, I ask them to back onto me, rather than me doing the initial thrusting. Where resistance was common in the first instance, over time it disappeared. I can’t say they all loved anal, although some did, but they mostly liked to please me, and if I made the whole process easier for them, then so much the better.

  11. Angie The Serial Dater

    The only time I tried anal, with a big sized partner, it was under very inappropriate circumstances and I never thought about giving it a go again. I am fine with guys inserting a finger in my ass but that’s as far as I went until I met my Dom. He wants anal, I told him I don’t enjoy it, but he has been very patient and understanding about my terrible experiences with others that I told him I wanted to reward him for his kindness, so he asked me to give anal sex another go. This time around, I was upset because my hole is so tight that he couldn’t enter me at all (even with lube) and his cock went limp, but I wanted to please him so bad that I told him to insert his fingers there. He used two and was very gentle so I enjoyed it a lot, and that is quite a progress because before then, I couldn’t take one without wincing in pain.

    1. FatherJon

      I’ve been down the’anal road’ with subs many times. Mostly newbies, I always found it best to tutor them before trying the real thing. Firstly, I suggest relaxing in bed in the privacy of one’s own room. Take to bed a medium size zucchini or cucumber, pre-warmed in a bowl of hot water. Make sure that the rectum is well lubed, then slowly insert the zuc little by little. The sphincter eventually eases allowing gentle entry until it becomes quite comfortable. I always say that the first sphincter is the worst – once in, it’s plain sailing.
      This should be done regularly before allowing your Dom to have anal sex with you, increasing the size of the chosen vegetable until you can safely and easily accommodate the average or even larger than average, male penis. Women mostly do some clitoral stimulation to orgasm once the zuc is safely in place, so you have an idea what a successful anal experience can be, for both participants, once you go into ‘real time’ with your Dom.
      As a pure spanker I’ve always been pleasantly surprised by the almost 100% association of spanking with anal sex, from both males and females. Just wish I’d realised all this as an adolescent youth with uncontrollable anal urges.
      I hope this has been of some value to potential anal players….good riding!


  12. Jason

    I love how detailed you get! Very accurate and although *I* am not a first time anal adventurer, I think this article will help a lot of people interested in exploring the area :) And yes, use LOTS of lube, more than you think you’ll need, and reapply because it always ends up getting spread a bit thin! Keep up the great posts!

  13. selenite

    I’m a sub whose first experience with anal was also with a vanilla ex-husband, and it was anything but pleasurable. In fact, it hurt a lot. I never did let him go near my ass again. When my next boyfriend attempted it, he approached it more gently and it was then that I realized it can be an enjoyable experience for women.

    But I must respectfully disagree with the person who posted as Ron and FatherJon (I assume they are the same person based on the advice given). If you are new to anal and you TRULY want to be able to learn to enjoy it DO NOT use a cucumber or zucchini! First, while zucchini might be slim enough to not be too painful, there are tiny little fibers (for lack of a better word) on it that will be quite irritating to your tender anus, further cementing the fact that you don’t want anything to do with anal stimulation. Second, unless you’re using an English hothouse cucumber or one that you’d use for pickling, a cucumber is going to be way too big for someone who is an anal virgin. If you’ve absolutely got to use a vegetable, try a carrot. Definitely clean it first, and definitely don’t use it straight out of the refrigerator because the cold can be rather shocking.

    I really wouldn’t suggest using ANY kind of food, unless you’ve scrubbed it and rinsed it well with distilled white vinegar (and then maybe again in clean water) and you’ve put a condom on it. Still, that aside, those vegetables are entirely too large for someone who is going to be exploring anal for the first time.

    Your finger is a much much better size. They also make very slim dildos and vibrators that would be of an appropriate size for getting used to the feel of something in your ass. And definitely use a lot of lube.

    Even though my first exposure to anal sex was so painful, I have learned to enjoy it. Even better is that I know how much my Dom enjoys using my (His) asshole, and His pleasure always intensifies mine.

    1. FatherJon/Ron

      Top marks for detective work, yes, Jon and Ron are one and the same. I tend to get my IDs mixed up late in the evening. But I still assert that zucchinis are best for that first anal experimentation. Carrots too though, so it’s up to the individual what’s in the vegie drawer of the fridge. Just don’t put it back in the drawer after use!

    2. FatherJon

      I just came across this link about anal sex which I thought might be of interest to the group:-

      The Riddle of the Sphincter

    3. FatherJon

      Regarding cucumber size, I suggest that Lebanese cucs are probably best for the novice. They come in a variety of sizes. Just don’t add them to the salad after use.

  14. Kit

    Respectfully disagree on using ANY veggies for anal play. Rule #1 is LUBE, Rule #2 is no flange = not safe. You don’t want the risk of something disappearing up your ass that can’t be easily retrieved without injury. Cocks, fingers, toys – great. But leave the salad fixings for the recovery snack.

    1. FatherJon

      You give no reason why vegies should not be used for breaking a novice in to anal sex.
      I always instructed my girls to use warmed up zucchini or cucumbers of varying thickness and size to familiarise themselves with objects in the rectum.
      Lube is, of course, essential as is total relaxation. That’s why it’s best to do it alone in a bedroom safe from any interruptions.
      In the unlikely event that a veg cannot be retrieved – although I’ve never heard of that – the worst that can happen is that it would rot and come back out that way. The smell might be a bit off-putting, but it’s hardly likely to be dangerous. Certainly safer than some of the commercial dildoes and strap-ons available in adult shops.

  15. Ham Sandwich

    Cukes and Zukes are way too girthy for a virgin ass. A smaller vibrator would be better, but be careful not to push it in too far. It can reach the point of no return and slip in all the way, and then it’s an embarrassing trip to the emergency room to get it removed. Don’t ask me how I know this. I just do, OK? A small diameter butt plug is probably ideal, after having become accustomed to a finger. And a soft, warm tongue across her bottom is the best way to convince a woman that anal can be very pleasureable!

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