Author: Shady Lady
BEFORE YOU GET STARTED
Before you even get naked and start playing around discuss what both of you want. It is very easy when highly aroused to say yes to something that you later regret, far better you talk it through rationally first. It should be something that both parties enter into with an open mind and a determination to give each other pleasure.
There is an old saying, "What's good for the goose is good for the gander," and when it comes to pegging it remains very true. Ladies if you haven't tried anal and enjoyed it then do you really think that you are in a position to give anal to your partner? If like me you enjoy anal then you will also know some of the 'pitfalls' such as the pain an over-enthusiastic partner can bring to the party. Please bear that in mind when you start thinking about "fucking his brains out" when it's his first time.
When I was researching this guide one man made a very interesting comment about how vulnerable he felt and how he had only trusted a couple of women that much. Now that got me thinking. As a female, my view of penetrative sex is that it is perfectly normal and no vulnerability is involved yet I guess from a heterosexual male's point of view this is a step into something totally new.
Every woman out there has a story to tell about when they lost their virginity. It will either be of how the man took his time, built you up slowly and then deflowered you as the waves crashed on the rocks, the angels sang, the earth moved etc. etc. (or something like that). Alternatively, it will have been a heated fumble in the back of a car or behind the bike shed, a stab of pain and there it was gone.
Ladies now the boot is on the other foot so give him something good to remember. If your partner is a virgin take your time, relax him, get him ready before you deflower him for the first time. There will be plenty of time to fuck him senseless but make the first time gentle and loving.
One of the common misconceptions about pegging is that the man must be gay or bisexual at least. Total rubbish, sure some men will be bisexual or bicurious at least (nothing wrong with that) but for others, it is giving up something that is most dear and opening themselves up totally to someone they love.
Another misconception is that a man who enjoys pegging also dresses or desires to dress in women's clothing. There are men that love that idea and get a great deal of enjoyment out of it, (again whatever floats your boat) but for others, it is not something that even crosses their minds. For example, my first husband was 6'3" and 240lb and as he always used to say, "Julie I would make a bloody ugly woman." Disconnect cross-dressing with pegging, they may go together they may not but don't assume.
Whether we like it or not (some do but not my thing) there is waste matter coming from your ass. If you are into anal with your partner with the woman being on the receiving end then you can probably skip over this bit as you will already know most of it. Just bear in mind there is a woman's idea of clean and a man's idea of clean so ladies I would suggest a joint shower the first few times and get him well cleaned. Most men have no idea about douches so this is something a female will often have to help her male partner with. You can buy a kit online for around £10/ $15 and they are pretty easy to use.
Tell the guy you want to try 'rimming him.' Since most men have no idea how to bathe their junk, let alone their ass, under the guise of shaving that thing, clean him. Both in the shower, lather his ass (while lathering his dick). Scrub that wrinkled eye well (bacteria will cause bumps after shaving), then squat behind and shave it. Shave from the centre outwards, in other words from the anus out. That will match the grain and they won't get itchy razor bumps.
Now that you're down there, keep stroking his cock and at the same time clean his anal crypt. The anus is built like this; the wrinkled eye of skin, a void behind it called the anal crypt and the sphincter. When we have a solid bowel movement, the sphincter actually protrudes out the anus. When we don't (or with leakage), human waste (serious bacteria), contaminates the anal crypt. So, soap up your finger, stick it in just past the skin, and fish around in the crypt cleaning it. Do it more with just water. DO NOT enter the sphincter.
Rim him and jerk him off, he'll love it and want more. After a couple of times, he'll learn how to bathe himself, and so in future times, he'll be clean for even a few hours after he bathes. Avoid enemas, they remove the mucous which makes it all easy and can lead to him getting infections.
After you have finished pegging always remember to clean your toys well, if they will take it, (check the box) then popping them in the dishwasher helps, though don't forget to remove them before the mother-in-law comes round for tea.
The final note on this area is, 'accidents will happen!' I have no idea why this seems to be more with men than with women (I have used a strap-on on both) and I guess there is some medical explanation but I have no idea. If they do happen, just get on with it and don't make a big thing.
There can never be too much lube. If you are cleaning then lube the nozzle of the douche to make it slide in easier. It can be something you do together or something he does in preparation for your session. When using your fingers make sure you use lots of lube, remember ladies he doesn't produce any natural lubricant so you have to help. When you move from fingers to the strap-on, coat the strap-on liberally and not just the head, all along the shaft as well. As I used to lube it I would often talk at the same time telling him what I was going to do and get him to verbalize what he wanted.
Get them used to it and go slow. Tension is the worse thing here as if they aren't relaxed then you could hurt them. Hate to say this but you know those wonderful talons you have taken ages to grow, well they have to go and any false nails as well, you don't want to lose an acrylic where the sun doesn't shine. A cut can be painful as well as unhygienic so trim a couple of nails reasonably short. One or two fingers is normally enough to start with and once pegging becomes a regular part of your sex life then his ass will respond with very little penetration. If you are desperate to keep your nails then buy a cheap pencil vibrator/dildo about the size of your finger and use that, though personally, it's not as intimate to me.
ORAL SEX AND FINGERING
I often used to find oral sex with fingers was a great way of getting him relaxed and ready. Again personal preference but the first few times I would be very much focused on him rather than mutual, but if it helps him relax go for it.
To start with put on a latex glove (fingerprints are abrasive and fingernails scratch) and have some good lube ready. Start sucking his cock, and although you may give the greatest blowjobs in the world, we're not really sucking cock, we're teaching him to relax his ass.
Work the blowjob slow and sensual for a couple of minutes. Start tracing the outside of his anus with a dry glove. A minute or two of that, lube up ALL the fingers. Using one finger, circle the anus and slip one finger in JUST into the anal crypt. Softly, feel around and learn how the sphincter is shaped. Anal sex REALLY hurts when a guy rams like mad and if the whole thing is done wrong he will cramp badly, and you'll likely never do it again.
As you check how it's built (just like a cervix), you'll find a depression in the center, and can tell that's the entrance to the sphincter. Apply pressure... DON'T push... he will eventually relax enough it will slip inside. Once inside, slowly move in and out, with your fingertip NEVER pulling out of the sphincter. Once you can get it all the way in, feel around.
A sphincter CAN NOT be stretched. If it could, none of us would be anal-retentive after we use the bathroom. But, we can train ourselves (or someone else), to relax, and even open ourselves up at will. Someone who is experienced in anal sex can, without lube, get fucked in the ass at the drop of a hat with no pain but as mentioned above, use lots of lube to start with.
Once he's relaxed enough, while still sucking cock, pull your finger back until just the tip is inside, and slip your middle one through his anus, and slowly once HE opens up, add it to the first. You can now reach in deeper and work those glands. If he's good with all this session (or perhaps the next) add a third finger. Enough times of sucking cock and massaging internal glands, you'll be able to add all four fingers and slip it in past your knuckles to your thumb. You can even eventually by rolling your thumb into your palm with your hand curled get the whole thing in, and now you're fisting. Of course, if that's not your thing, then stop at two or three fingers.
Older men are often heard complaining about their prostate in later life and how they have to get up to pee during the night. However that wonderful little pad of flesh can be the source of great pleasure, think of it as the male version of the g-spot. Remember the first time you found your g-spot, or it was found for you, how wonderful that felt and the pleasures it gave you. If you haven't found your g-spot yet find yourself a nice friendly lesbian and she will happily show you where it is.
The sensations are not dissimilar for a man and a skillful manipulator can make a man cum with any touching of his cock. The easiest way to find it is by using your fingers and feeling for a spongy spot, he will tell you when you have found it, trust me he will tell you loud and clear. I have given more than one blow job in my time where a helping finger has been used and can produce some powerful orgasms.
Just doing the prostate massage with your hand, you can get a guy to start surging out semen in numerous floods for a half-hour or better. Think of riding the beginning of an orgasm, not the crest, for a half-hour. So, if we move right pegging, we can do the same and even if he's into it add some psychological perks. Once you know where your man's spot is having found it with your fingers keep that mental position in your head for when you start using the strap-on.
POSITIONS AND PENETRATION
The easiest way to do anal the FIRST time is with the receiver on their back, and after a few times he should be ready for on his belly, and he can rise to all fours during, or not.
Rim him, tease him, but DON'T stick fingers and so forth in. Once you remove something that is only in briefly, it tenses up even more. Have a towel underneath him, take time lubing up his ass, then the dildo. Put it against his anus nicely centered, and stop. Let him grind against it. In other words, impale himself on it, you are just holding it in place, he'll raise up and push back, and HE will align it so you don't mess up.
From this moment on you will NOT take the head out of his sphincter. It's hard to do with a dildo, a guy can feel with his dick, we can't. Start rocking slowly. Don't push in, just apply pressure. Eventually, you'll feel him give up resisting. Don't just slam it in at that point. In a little, back, in a little deeper, back. Keep doing it until you work it all the way in and add lube to his ass and the shaft in increments.
Once all the way in, hold it there and talk to him again as it suits the style of the pair of you. This can range from loving tender words of endearment through to telling him how you have always wanted to fuck his ass and now you are going to do it. Replay the words that have been used when he fucks you and you will find that is often the way he wants to be talked to when he is fucked.
Pull back till just the tip is in, raise up a little to angle down and push in pressing the tip towards his front as you go deeper. Remember how deep the prostate and seminal vesicles are, we don't want to press past them. When you pull back, lower to not squeeze out what we just pushed up. Slowly, over and again. Each time it will squeeze his seminal fluid up into the vesicles which will stretch like a balloon with water. In just a few minutes you can get a LOT of fluid up in them.
Once you've done that a bit, fuck him some, being very careful to NOT point the tip down when you pull back. Whether you're jerking him, or he is, make him hold back as long as possible. Alternate fucking him with what we did before, pushing up more fluid.
As you get experienced and he is comfortable, by bending your legs and altering both the angle and the depth you should be able to get the head of the dildo to rub over his spot and send him to heaven.
When he is ready to cum, you'll reverse the above, ONLY seconds before he does, otherwise, he'll just seep a lot. Push in straight PAST the glands, rise up and hold it applying pressure to the glands. As he starts to cum, or a second before, pull back dragging the tip against his front, squeezing out what we just filled. Lower, shove in, rise up and back out. 3-4 times will be it. He WILL gush five times more cum than he ever has.
There is always the question of who plays with it and when. Firstly depends on the position as although a 'reach around' sounds like fun depending on your relative body sizes may not always be possible. With him on his back then the touching is much easier and I would often 'stop' him touching himself and would play as I fucked him slowly. On all fours, he would play with himself sometimes but more often than not he wouldn't touch himself as it wasn't necessary to do so for him to achieve an orgasm.
WIFM (WHAT'S IN IT FOR ME)
This is often thought about but not always talked about. The fucking action will make your ass and thigh muscles tighter and you will start to appreciate the efforts he (or the 'giver' in the lesbian world) goes to. You will see that you can get strapon attachments that give a small insertion for the women or they will have a plate with bobbles on that will stimulate your clit. At first, I would suggest you avoid those until you are both comfortable with what you're doing and what he likes and doesn't like. It could cause a lot of problems if the first time you take his ass you find yourself cumming and slamming into him without any caution. Once you have got used to the action then stimulation is a great thing and I was a big fan of the bobble bits that stimulate the clit.
THE WAY FORWARD
Once you have decided to bring pegging into your sex life keep talking about what you like and don't like. It is very easy to start thinking "I know best" or "He will tell me what he likes or dislike." As you change things talk about how things will change, e.g. a bigger dildo, and how do you both feel about it.
There is always the temptation to watch a movie on pegging then buy a dildo the size of a horse. Think of the first time you took a cock in your ass, how big is his cock and how did that feel? I would go for a harness that can take a variety of sizes so after you have got used to it there is always the opportunity to move up to something bigger, but just take it in small steps.
Remember the worse thing (from the male perspective) is there is no feeling in a dildo. This means the first time you know you are hurting your partner is when he starts screaming. Similarly, there will be times when your concern for his well being means you are too timid. It is important that the man lets his partner know how he is feeling with comments such as 'faster', 'slower' or 'deeper'. After a while, you will get used to what turns him on and what makes him spurt so he will need to guide you less.
I am not talking about two strangers here, but a couple who wants to share and grow together so enjoy it. Be prepared to talk about it and above all only do it if you are both enjoying it. I wish you every luck and enjoyment in the world.