Showing posts with label #Edging. Show all posts
Showing posts with label #Edging. Show all posts

Tuesday, January 8, 2019

What Does A Typical Edging Session With You Look Like?

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temptingdominance:

Well I would hope that nothing is ever typical. I want each session to be filled with new experiences and evolving dynamics. But that being said, I will share how I would generally approach a “garden variety” edging session.

I would normally restrain a boy.

It is certainly possible to edge a boy when he lays flat on the couch or the floor. However, what is the fun in that? It helps to heighten a boy’s experience when you take away his mobility, when you put his body entirely in your care. I lean towards tying a boy to the bed, spread-eagle. That way, I have as much access as I would like. If he likes to squirm or may test the bonds, I may add the leather mitts to keep his hands to place.

Obviously get him naked before you restrain him. It is a pain in the ass to deal with clothes once you’ve locked him down.

He will be blindfolded and perhaps gagged.

Always blindfold a boy. It augments his other senses. It makes me keen on the sensations you are applying to his body. If he is overly chatty, loud, or you just want him to be quiet, a gag is a good addition. A ball gag will do or even just stuffing his mouth with his own underwear. However, if I want a boy to focus on the fact that his mouth is made for sucking cock, I will use the pecker gag.

Pro-Tip: Have your gear already set out next to the bed on the floor covered by a towel (so he doesn’t see). This will help you be ready to go once he is restrained. And you don’t waste time.

I start by just touching his body

Remember that edging is about teasing a boy. You want to stimulate him. You are in no rush. You want excite him. Running my fingers all over him. Getting his boy dick nice and hard.

Remember that verbal communication is just as important as touching.

You need to talk to a boy throughout the entire session. You want to get inside his head. You want him whimpering. Tell him what is about to happen to him. Tell him you are going to help him learn to be a good boy. Tell him that his is your fucking little play thing.

Slow Strokes and Listen to his Body

Don’t go quickly. Use lots of lube. And stroke his boy dick. All while talking to him. One of my favorite activities is to make a boy countdown the number of strokes, especially if he has to mumble through the gag.

Listening to his body is so important. The purpose of edging is to bring him closer and closer without letting him cum. One of my frustrations with edging porn is that the guys often just jerk and pause, jerk and pause. Then he just falls over the edge and cums. No. Go slowly. Listen to the body. Teach him to hold it and breathe.

You need to be the person that decides when he releases. (And he should ask for permission).

Play with his hole

Almost always during an edging session, I will play with a boy’s hole. I think it adds to his stimulation. At a minimum, I will finger him. I will usually set out some toys to use on him a well. Or keep him plugged while I stroke him.  Or an aneros which I will use in conjunctions with vibrating toys.

Toys on his boy dick

I love my magic wand. It is one of my favorite toys. It is so helpful in an edging session. And when I want to see him struggle, I will put the device right on the head of his boy dick. He will certainly tug on those restraints. You can also use a vibrator or any other stimulating toys.

Plan for a little more

I do like to incorporate other elements into the edging session. Just to keep a boy on his toes. It makes it more fun for the both of you. Add the nipple clamps. Use some clothes pins. Drag the riding crop across his body. Use ice cubes on him. A little icy-hot on his boy balls. Again remember the point of an edging session is to stimulate him.

Take a Break

Sometimes when a boy does get really close, I put a cool towel on his boy dick and leave the room for ten minutes. The come back and start all over again. This can be really good for driving a boy wild and making the session last. Note however, some boys once they go soft during an edging they may not get hard again. You just need to recognize this risk. Edging can cause a sensory overload.

Cumming with your permission

When you do get to the point that you want him to cum, make sure you have him ask and you grant it. Then stroke firmly until he explodes. Do NOT stop stroking when he starts cumming. As a Dom, you need to work out every drop. It will be sensitive. He might trash around, but you need to empty those boy balls.

Clean Up His Mess

Finally, you do not untie him until he has cleaned up his mess. Take out the gag and feed it to him. Make sure he swallows every drop.

Pro-Tip: His mouth may be dry from being gagged. It might be difficult for him to swallow. Have a glass of water near by for the boy.

There you have it. That is typically what would happen in a edging session with me. I hope it is helpful to you Doms.

To you boys reading this right now, I know you are drooling.

Thursday, January 3, 2019

Discipline, In Detail.

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A major part of many kinky dynamics is a focus on discipline. While “discipline” can be a fun part of your everyday activities, it can also mean something more specific in terms of punishment. “Punishment” differs from the general sense of discipline in that it has a specific goal to focus on that changes a submissive’s behaviour.

Many people engage in what can be called “funishment,”—punishment-type activities, like regular spankings or other forms of play, that are not meant to alter the behaviour of the submissive but rather to provide enjoyment to either/both/all parties. However, it is important to distinguish the difference between playful discipline and serious punishments. Punishments are consequences of negative actions, whether this is based on officially-written regulations or unspoken general behaviours like brattiness, defiance, or dangerous behaviours.

The idea of punishment is based largely on psychological research in the area of behaviourism. It consists of techniques that are supported by science to effectively alter the behaviour of an individual. (If you want to learn more about the research behind punishments, look up B. F. Skinner’s work in this area.)

Two types of punishments exist: positive punishments, which add undesired consequences to the behaviour, and negative punishments, which take away desired privileges.

Now, before I get into some specific ideas for punishments, there are some important key points I’d like to make. Please be sure to read all of these before deciding on a specific punishment.

Punishments do NOT negate the right to a safeword. Some people are mislead into dangerous situations by being told they cannot safeword during a punishment. This is completely untrue. All parties have a right to safeword at any time during any kind of play or punishment. Taking away the right to safeword equates to abuse, plain and simple. Don’t ever tell your partner they cannot safeword or ignore their safeword for the sake of punishment. This is not effective and is extremely harmful to your partner’s mental and/or physical well-being.

NEVER punish out of anger. Anger is never a healthy motivation for punishment. Punishments are meant for the submissive’s benefit, at the core. If the submissive’s behaviour has made the Dominant angry, they should have a cooling-off period where they can calm down, think about an appropriate punishment, and resolve the matter at a later time, after healthy discussion about what happened.

Limits are NOT to be used as punishments. Many people have activities they don’t particularly enjoy that aren’t on their limits list. Some people have specific ideas for punishments that suit them best. However, regardless of you or your partner’s experience with punishments, it needs to be understood that hard limits are not punishments. Hard limits are never to be used for punishment’s sake because “hard limit” means “I do not want to do this under any circumstance.” Using a hard limit as a punishment would be an abusive act, as hard limits come with an automatic safeword attached, since they are specifically stated as things the person does not feel comfortable with. Never, ever, threaten or use hard limits to punish a submissive.

Use healthy discretion. This one should seem obvious, but don’t follow through with punishments if rule-breaking was out of the submissive’s control. Say the submissive has a 11PM bedtime, but they recently suffered a trauma or loss and can’t sleep. Let them engage in healthy coping skills instead of punishing them for something they aren’t doing on purpose. Above all else, make safety and well-being a priority.

Make the punishment fit the crime. Punishments that are relative to the defiance are much more effective at changing the behaviour than random punishments. For example, if the submissive cums without permission, try a punishment from the “orgasm control” section. This will better reinforce the reasoning in the submissive and more effectively guide them to make better choices in the future. There are also punishments that work best for specific dynamics like for littles or pets, so be sure to read into those, below.

Aftercare is absolutely required. Like any kind of play, aftercare is required at the end of the scene. This is especially important during punishments because often times, the submissive is consumed with feelings of guilt and disappointment. After a punishment, Dominants need to give their submissives aftercare that includes a conversation about why they were punished, how proud the Dominant is for them taking the punishment so well, and that there are no negative feelings between them. The submissive should leave the punishment scene feeling forgiven for their mistakes and proud of themselves for making things right with their Dominant. Do not leave your submissive alone after a punishment without aftercare, ever! This is highly abusive and can seriously harm your partner.

Humiliation

A great way to get a submissive to stay in line is to humiliate them when they’ve done something wrong. There are several ways to go about this, depending on your dynamic and kinks, but it’s an effective and amusing way to get the message across.

Clothing Restriction

Clothing restriction can be done both domestically and in public. Restriction can be as much as not allowing any clothing (in legal or private settings), ordering a certain amount of skin be showing, or choosing a specific outfit or collar for the submissive. For shy submissives, clothing restriction can be intense. This is an especially good punishment for submissives who have said negative comments about their bodies.

Diapering

For ABDL or little submissives, this can either be a reward or a punishment. Depending on the comfort level with diapers, they can be used as a punishment that ties into humiliation. Making them relieve themselves in only the diaper for a set amount of time or wearing it around the house as their only clothing can be very humiliating for some people.

Sissification

Sissification is a kink that is most common in submissive men. It’s the act of dolling a man up like a girl and humiliating him based on his presentation as such. This can be very effective for some people but can be very problematic to others. Be careful not to use this kink as punishment with trans or gender non-conforming subs without their explicit consent, as it can very easily trigger dysphoria and cause severe emotional problems.

Public Humiliation

Public humiliation can be done in any subtle way that embarrasses a submissive without breaking any obvious laws. Some examples include making them wear an anal plug or remote-controlled vibrator to dinner, public leashing, or making them kneel at social gatherings. Work this idea into the submissive’s specific kinks and limits to be sure it’s just enough to embarrass them, without making them unbearably uncomfortable.

Orgasm Control

Orgasm control is simply that—controlling the submissive’s orgasms. Most of these types of punishments are used for submissives who break rules about orgasms, be it without permission or when they were told not to touch themselves. Controlling orgasms is an amusing way to teach the submissive who their orgasms belong to.

Edging

Edging is the act of getting your partner right to the edge of orgasm, then denying them release. This can be done multiple times, even in short amounts of time. It’s a little psychological torture, best for those who cum without permission.

Toy Restriction

For a submissive, like myself, who is accustomed to using toys during masturbation or play, toy restriction is a very effective punishment. This is especially good for submissives who have a difficult time reaching orgasm without toys, as it makes things very frustrating very quickly. An evil punishment may even combine toy restrictions with a quota of orgasms for the day that they must reach in order to get off restriction. Desperation will sink in very quickly and this lesson will be easily learned.

Forced Orgasms

Forced orgasm is another great punishment for submissives who cum without permission. It turns a great sensation into a torturous experience very quickly. This is especially great with toys like the Hitachi or a Sybian. Focus on a goal—either for number of orgasms, or a specific amount of time. An hour spent riding a Hitachi can really be the most agonizing thing for some people due to heightened sensitivity after each orgasm.

Denial

Denial is the complete opposite of forced orgasms. It’s like edging, but there is no orgasm at the end of the scene. This can be doing while using toys and not allowing the person to orgasm or it can be done by restriction orgasms or even touching oneself for a longer period of time.

Chastity

Chastity, much like denial, is the refusal of orgasms. However, with chastity, the submissive is completely unable to touch themselves, even if they wanted to. Devices for people with penises and vaginas are available to purchase online to assure your submissive is following orders properly.

Domestic Discipline

Domestic discipline includes things that can be done within the home. Some of these include behaviour modifications or restrictions. While some of these can be done outside the home, these are good examples of things for couples who live together can do for punishments.

Chores

Chores not only benefit the entire household, but they can also be an effective punishment for unruly subs. Added chores can be especially fun if you make her clean the bathroom with a toothbrush or make him do dishes with nipple clamps on. Combine with other punishments for your amusement!

Furniture Restriction

Especially fun for people into pet-play, furniture restriction involves limiting where the submissive can sit or lie down. Require that they sit on the ground instead of the couches or sleep on the floor next to the bed if they’ve been defiant.

Caging

Another good one for pets, especially. Caging can be used to make the submissive reflect on their reasons for being punished. Be sure to use a cage small enough to confine them, but still large enough so they aren’t going to hurt themselves by spending too much time in the cage.

Bedtime

A great one for littles! Bedtimes are good for college students who don’t do their homework, or easily distracted adults with work to do. Set up rules that require all obligations get done and enforce an early bedtime to be sure they are well-rested (and easily frustrated) when they don’t follow these rules.

Time-Out

Another punishment for reflection. Time-outs are good for brats and littles because it makes them analyze what they did wrong. Put them in a corner or a special “time-out chair” so they know they are being punished. Increase the time or add in other punishments if they break rules more than once.

Sensory Deprivation

Sensory deprivation is a lot like time-out, but can be used for added psychological torment. Plug the submissive’s ears or use headphones, blindfold them, bind them to a bed or chair, and completely ignore them for a set about of time. This desensitizes them and not only makes them reflect on their reasons for punishment, but makes it very uncomfortable, assuring they won’t want to end up in isolation again.

Objectification

Objectification is fun for Dominants who like their submissives in service to them during punishment. Make them kneel and become your footstool or coffee table while you watch TV or catch up on work. This is even better when you make them do it completely naked and/or in front of guests.

Dietary Restriction

If a submissive has done something against the rules, you can make them follow a strict diet. This is especially useful for those using behaviour modification to lose or gain weight. However, be careful to ensure the submissive is still getting enough nutrition. For littles, see how much they want to be a brat after you take away their dessert privilege. For pets, try making them eat out of a bowl on the floor for each meal.

Speech Restriction

For disrespectful submissives, punish them by taking away their right to a personal pronoun, making them refer to themselves as “this girl,” “Your slut,” “Master’s puppy boy,” or anything else you want to use. You can also make it a rule that they must refer to you by your Dominant title at all times, even in public. Having to remember their restrictions on speech will keep them thinking about their punishment all day.

Corporal Punishment

Corporal punishment is enforcement by physical contact. These types of punishments involve pain, which is a tricky subject for punishing. Typically, pain punishments don’t work as well to change behavior, especially if the submissive is also a masochist. Be sure to carefully choose what kind of pain if you’re going with one of these methods.

Impact

If your submissive likes thuddy pain, use stingy pain. If they like stingy pain, use thuddy. Push their limits carefully, but make it clear this is a punishment and not for fun. Have them apologize as you strike them. Tell them why they are being punished and make it clear that they are to be good and learn from their mistakes.

Rice Kneeling

Kneeling on uncooked rice is an age-old technique that leaves painful marks. Be careful with time, as this can scar if done for long periods of time or used constantly. Be present during this to be sure the submissive can take it and listen carefully for safewords. Use this as a time out or have them recite an apology to you as you do this.

Figging

Figging is done by carving a plug out of ginger and inserting into the anus. This causes a stinging pain that ranges in intensity depending on the person. Frozen ginger is a milder form of this punishment.

Writing Assignments

Writing assignments are usually meant to bore a submissive into obedience. Whether it’s writing lines or a random homework assignment, the punishment focuses on making it undesirable for the submissive to misbehave.

Lines

Writing lines is effective if you use it reflectively. For example, for a submissive who is disrespectful, you can have him write, “I will always be polite around my Sir,” a hundred times. For a submissive who cums without permission, you can order, “I will ask permission from Mistress before I cum,” until they fill up five pages. What’s even more fun is making them be stuffed with a toy or on their knees with nipple clamps on while they write.

Apology Letter

An apology letter is a simple task meant to make the submissive think about what they have done, analyze why it was wrong, and have them apologize formally by writing it down. Have them read their letter to you our loud or crumple it up and put in their their underwear for that added perk of remembering all day that they were punished.

Essay

An essay is a good assignment for submissives who don’t seem to understand their rules. Make them come up with reasons as to why these rules are in place and write a formal essay about the reasoning and purpose of these rules. Making them analyze the fact that this is for their benefit will remind them that rules are not just there to be mean, but to guide them to healthier behavior.

Homework

Especially fun for people with school girl or teacher fantasies, assign a random homework assignment. Ever wonder about a certain subject but never have time to actually research it? Assign a paper to your submissive about a subject of your choosing and have them report back to you—because knowledge is power! Grade their paper and reward/punish again as necessary for the quality of their work.

It’s important to remember that reinforcements are also important in addition to punishments. When your submissive follows directions, reward them. Give them a treat or praise them and thank them for being so good. If you mix positive reinforcement with punishments when necessary, they’re sure to be trained in no time!

Friday, December 28, 2018

Master Domonic's Protocols For a New Submissive

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bondagebudtx: Have subbed for years and am about to Dom for the first time. We discussed it being your basic tie down spread eagle (got cuffs and a great wrought iron bed), with TT, CBT, maybe some electro, edging and milking, and I’ll set up safe words and cover limits, but how do I prepare for the session to ensure it’s good? Do you have a plan/roadmap of activities or do you play it by ear? How long should I plan for? Build in breaks? He is pretty experienced.
This is why I always like subbing. Domming is hard work!

________________________________________________________________

Master Domonic:


You’re off to a great start, by being communicative with your study buddy, before the session. Remain communicative during, as well. My sessions run from an hour and a half, to maybe three hours. Some go longer.

Once the guy arrives, I always take a few minutes to sit and talk, to go over a few things.

1) The first thing I tell the guy is thank you for being here, immediately followed by the “Don’t-Try-To-Impress-Me lecture.” I explain to him, “Once the session has started, do not try to impress me. I’m already impressed; right now. You’re here. You’re willing to try. You’re ready to trust me. So, trust me: I am impressed already.” I continue with, “so after we start, if something is pinching or biting or tingling, but you assume I’ll be annoyed that you’re whining—don’t impress me by saying nothing.” “If you hear your cell phone buzzing, and you need to check the messages, but you’re worried I’ll be impatient to untie you–don’t impress me by saying nothing.” “If something is taking you out of a good/fun/pleasureable place, don’t assume I’ll think less of you if you speak up–don’t impress me by toughing it out.” “Its your job to let me know if something is taking you out of a pleasurable head-space. Let me know if something is beginning to cross that line from pleasure, into a pain that is distracting you from the fun we’re having.” “Its my job to correct the problem; I’m not a mindreader; you’ve got to speak up and let me know if something is beginning to go in a wrong direction.”

There’s nothing the guy can say or do during a session that might lessen the respect I have for them. I’m thoroughly impressed by every guy that’s lent their trust to me for a few hours. When the guy shows up, and is ready, willing to try: I’m thoroughly impressed.

2) I give the guy his SAFE WORD(red) and his TIME-OUT WORD(yellow). I also show him my safety scissors; and place them at an easily accessible spot (window sill, counter top, my jeans back pocket) where they won’t be covered up by gear or ropes or shoes or socks, etc. He understands that if he calls RED, it means he’s panicked, scared, or in excruciating pain and I am to immediately cut the ropes and end that part of the session. I do not pause if he calls RED, to ask: whats wrong, are you ok? RED means STOP NOW. If he calls YELLOW I know there’s something that’s not going great, and he needs to let me know. YELLOW means: pause the session; discuss the isuse; adjust what’s not great; and resume the session. He can moan, groan, plead, struggle hard… if he’s not saying RED or YELLOW, its all music to me ears.


I do not attempt to push a guy until he calls RED or YELLOW. Those tools are in place to a) give him the confidence that he will be taken care of at any point the need may arise. And b) it allows me to not have to pause every 40 seconds to ask: are you ok? Are you ok now? How about now, are you ok? Is this OK? OK? OK? OK? Are you still OK?

Ok.

Because the guy has promised me he is busy NOT IMPRESSING ME, and I know he can use Yellow or Red if necessary; all of this allows me to move him along through the session, confident that he’s good with it.

3) I give the guy another tool we can use together: “The 1 to 10 Scale.” When I’m putting him through some CBT or Nip tease, or edging him with instructions–Do not cum yet, I explain that he is to use numbers to let me know how he’s holding up. If the intensity is mild, he can tell me he’s at a 1 or 2. If the intensity should suddenly spike up, he can let know by stating his nips are at a 7, or his balls just went to an 8. If he calls 9, this means he’s on the verge of calling RED, unless I ease him back.

Using the 1 to 10 system, at any point during the session he can communicate clearly how he’s holding up. He can tell me the hogtie has his shoulders at a 6….I’ll flop him on his side, and stroke his dick…”how are your shoulders now?” His mind is distracted… the shoulders are suddenly fine. Or if the ball stretcher has him at a 7, so in response, I’ll hang a weight to his nip clamps, and miracle of miracles, his balls are suddenly no problem.

When I’m edging him, he can call out numbers as he gets closer to cumming. A 7 or 8 means hes almost there. A 9 means if I don’t stop now, he can only hold it back a few seconds longer.

The “1 to 10 Scale” is invaluable for partners who are curious about bdsm, but don’t want to hurt each other. When they both understand the tied up sub can at any moment let his partner know if something is getting too intense by calling a number, it allows the dom partner to erotically “torment” his subby partner, with confidence. The dom is relieved to know he’s not going to hurt his sub, because the sub can give out numbers, 1 to 10, letting his dom know how he’s doing. Or if the sub is worried his dom partner is “clumsy” or too excitable to be trusted, the 1 to 10 scale can keep the overly zealous novice horny dom, in check.

4) Lastly there is my 15 Minute Rule. When the guy is in a tough position, working hard, I keep an eye on the clock. I don’t necessarily tell him this. But if his hear rate’s been up a while,, breathing hard,, balls sore, nips aching,,, I’ll give him relief from the stress. I’ll change his position. We’ll take a restroom break; sip some water. Or I’ll keep him restrained, but with no major challenges to contend with while he catches his breath and his heart rate can settle down. I can also ask him to “give me a number, 1 to 10, where are you at?”

I also can ask the guy, can you stay in this predicament 10 more minutes? If he’s busy NOT impressing me, he’ll answer truthfully. And once he knows this challenging situation isn’t going on forever; when he knows there’s an end in sight, he can relax and cope. Fear of the unknown is a buzz kill; in life; and in bdsm. A little suspense and surprise is hot.

Communicate before the session, and during. Demystify the experience.

Thursday, September 17, 2015

For Tops: Preparation and Seduction, Before Fucking A Newbie's Ass

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Papa Tony:


UPDATE: Wow - This page is in line to become the most-popular article that I've written so far, 24 hours after posting it. It's going really viral, in the USA, Malaysia, Poland, Canada, the UK, Taiwan, Germany, Singapore, France and the Philippines!  Clearly, this is a message that needs to get out there.  I suspect a lot of men are sending this article to their boyfriends.

UPDATE 2:  Here is the audio from the follow-up discussion on this topic.  We have some GREAT new stars among us!  Last time I checked Google Analytics, this article has been read over 300,000 times.


My goal is to teach the reader how to be a superb Top, with eager bottoms singing his (or her) praises.  The steps that I list below can be accomplished in a few short minutes, or it may take months, but the end-result is a piggy, grateful bottom that can take a cock of any size without drugs, stretching, harm or pain of any kind.  Being a gay man, I write from that perspective, but not with any intent of trying to exclude anybody.
Question: In the event that you play with a bottom who is very inexperienced and hasn't bottomed much (or at all), do you give him a some time (a few minutes or so) to get used to you when you first start to fuck, or do you just thrown him into the deep end of the pool and take him to pound town?
If somebody takes an inexperienced bottom and intentionally takes him directly to Pound Town without negotiating exactly that beforehand, then he deserves to be chased away with rocks thrown at his head.  Why?  Because I have spent the last four decades helping damaged, frightened men to get back in touch with their assholes as sexual playthings, after years of avoidance.  

Too many men are doing what dogs do, which is to jump on, pump, squirt and then jump off. It's great for the Top.

It can easily be terrible/traumatic/damaging for the shy, new, eager and inexperienced bottom.  I speak from direct experience.  I've always had freakishly large, attractive rump-muscles.  My nickname used to be Thunder Buns. So, in my younger days experimenting with gay sex, I'd let men fuck my ass.

I'd bite the pillow, bleed, suffer for days afterward, and regret having given up pussy for dick.  I figured it was somehow MY fault, because I wasn't keeping up. Then, one day, my life changed:

I was off-duty (Navy) and staying off-base in an apartment building.  It was laundry day, and a small, mousy and not-all-that-attractive man was working HARD to get me to have sex with him.  I finally gave in, figuring that I'd throw him a thrill.  Oh, I was so wrong.

He rocked my WORLD.  I basically became his butt-slave for three weeks.  I'm naturally inclined to be a Top, but I wanted to learn from the obvious expert, and he taught me some deep wisdom.  Here is a summary, for those of you who want to be a popular, well-rated Top, with plenty of word-of-mouth referrals:

• ASSUME that the guy you're about to play with, is eager, inexperienced and needing some seduction.  Don't assume that he's an experienced porn-actor who can take anything from anybody. Be pleasantly surprised if he proves otherwise, but it's never a bad idea to start slow and careful.

• Stick a well-lubed finger up his ass, with a SHORT, SMOOTH NAIL.  If I see heteroporn with a woman sticking blood-red talons up a guy's ass, I cringe.  The flesh down there is delicate. There are multiple, excellent reasons for sticking a lubricated finger up there:

• Check to see if he's relaxed and ready.  If his outer ass-ring is CLENCHED, he's not ready yet. The problem is not down in his ass, it's between his ears.  Maybe he's afraid, or he's been hurt before, or he doesn't trust you yet.  So, it's your job to seduce him into relaxing.  More below.

• Adding some well-needed lube.  Dry fucks, using nothing but "spit and determination" are classic porn-video fantasies, but again, we can't assume that our newest partner is at that advanced stage.  As we used to say back in the 1970's, "if it's not dripping off of the ceiling, it's not enough lube!"


• Finding his prostate, AKA "Joy Buzzer #1".  The prostate is a rounded mound on the other end of his dick, inside the ass, and its location can change quite a bit (deep vs. shallow) from man to man.  Its job is to generate the fluid that his sperm swims around in. Properly stimulated, a prostate will generate enough additional fluid to give the bottom "blue balls" after a while, leading to eagerness for more delightful butt-sex. YOUR job is to take careful note of its location, and then to please the hell out of it.

• Checking to see if he's got any poop up there.  Yes, from an aesthetic standpoint, it is unpleasant, but from a relaxed-butt standpoint, it's very unhelpful.  I don't know how scientifically accurate this next assertion is, but it's what I learned a long time ago from some VERY advanced players: There is a bundle of nerves at the base of your spine, that keeps you from pooping when you walk.  If there is poop in your lower bowel, your asshole will clench, whether you want it to, or not.  There are zillions of articles on the Internet on how to douche an ass.

Let's talk about Operant Conditioning, in the context of butt-sex:

I'll call it "Positive Reinforcement", instead.  To train a shy, new, eager bottom to CRAVE more, I have to take him through many steps, with patience and respect, giving rewards for behavior that moves the ball forward, and gently ignoring the stuff that doesn't work at the moment.

As a high-quality Top, MY job is to seduce the bottom.  What does this mean?  Establishing Trust with a Capital T.  Being true with my feelings and thoughts, from moment to moment. Staying in communication.  NOT using "Porn Dialog" ("Fuck Yeah.  Fuck Yeah"), if it's not truly what I'm feeling.

Every one of us has a voice inside our heads, telling us to beware what is happening, or to tell ourselves that we are surely going to fail, or that maybe the guy we are playing with thinks our dick/belly/ass/back is too hairy/big/small/old/whatever. That noise is also in your new bottom's head, and it wants to tell him that he is heading for a brick wall.  YOUR job is to talk openly, honestly and affectionately about your feelings and desires from moment to moment.  Why?  Because it silences and stills the voice inside his head, and he's GRATEFUL for the relief.

If I'm playing with a man's ass for the first time, I reward him for each stage that he attains in his new status as a piggy bottom:

• If his ass is tight enough to sharpen pencils, I will stimulate the OUTSIDE with pleasurable attention, using tongue and fingers.  The dick does NOT show up at this stage.  Oh, no. We don't want any panic at this early stage.  I will praise how well he is doing, no matter how small the accomplishment.  I tell him that I'm okay if we DON'T actually fuck until the second or third date (or a month!), which takes the pressure off of him to catch up faster than he is prepared for, mentally.  It also gives him the pleasurable knowledge that there is more to look forward to, with this REALLY nice, respectful Top.

• If he's starting to relax a bit, I will use the phrase "Breathe me in", while starting to penetrate him with my smallest finger.  If he clenches/spasms, STOP MOVING.  No pulling out, no pushing in.  It's a normal response.  Once his ass stops spasming, praise him for relaxing, and help him to know how he is progressing.

• If he has taken the smallest finger well, slowly pull out, re-lube and then bring it on back in.  There shouldn't be any spasming at this point.  Praise him for being looser than before, but only if you mean it.  He can spot bullshit. Your goal is to take him through the stages, with no rush or pressure.
Why am I taking such a (literally) "slow-poke" approach?  Because of the possibility of PTSD.  Too many men have been damaged by inept Tops.  Always assume that he is begging you to help him get past it.  Continuing:

Here is an animation of me, flaring my nostrils.  Back when I was a kid, I sat in front of a mirror, and kept practicing, until I found the mental "switch" to flare my nostrils.  Here I am, half a century later, and I STILL know where that switch is.

It's the same with an ass.

Normally, we poop (and occasionally, fart) with our asses.  We are NOT born with the knowledge of how to relax our ass.  How do I know?  If I order a man to "RELAX THAT ASS", there is no telling what he'll do in his attempts to comply.  He might get it right, and, many times, he won't.  It's your job to help him find the switch inside his own head, so that his ass can be receptive, welcoming and eager, any time.

To accomplish this noble goal, we generously use praise, when it is earned.  If he graduates to your longest finger, have him go on hands and knees and switch to your thumb, with a nail that is equally smoothly-trimmed and sandpapered.  This is where it gets really FUN.
DON'T offer him drugs, including poppers. They cause the scared part of his brain to get ignored, sure, but they also cause the pain-receptor part of his brain to keep from screaming "DAMAGE!" I'd rather have 1% of true, connected and ecstatic sex, than 100% of the fake shit involving drugs. I remind the reader: I started having sex (with thousands of men) in the 1970's, with the hardest of hardcore players. I know about drugs, and the cost. They truly are not necessary.
So, it's thumb time:  Your goal is to EROTICIZE ass-play for this man, and many times, it will be his first experience of such a thing.  You are doing him a world of good, so press onwards.  Lube up his cock really well, insert your thumb in his ass, and start (gently) twiddling his prostate. Rub in circles directly on top of it.  Or, press on the closest part of the prostate, and rub from side to side.

If he complains that he needs to pee, accept it graciously, but chances are very good that he needs no such thing. He's so unfamiliar with prostate-stimulation that he can't sub-divide the sensations enough to tell what he's feeling.  This will pass.

If your thumb is comfortably, non-painfully inside his ass, order him (in a no-nonsense manner) to start playing with his dick.  If his prostate gets all swollen and rock-hard, tell him to leave his dick alone, because that is a flashing-red-light signal that he is about to cum.  That means that you are being successful in teaching him that his ass is for sexual pleasure. Keep supporting more and more excitement, and edging him closer, but not necessarily to orgasm.

However, if he DOES cum with something up his ass, tell him "Don't hold back!  Give me everything!" Why?  Because you are training him to be delighted that his ass is a source of sexual pleasure.  If he cums as a direct result of what you are doing, you're a hero in his eyes.  This is all to the good.

The next part is up to you:

Your goal is to get him ready for the Main Event, whether it's your cock, or a dildo, or whatever.  If you have a sizable object to insert, the bottom has to be comfortable with a certain number of fingers up his ass first, matching the diameter of the Object of Desire.  This may happen on Date Number One, or it may take patient, multiple trainings over weeks, using ever-slightly-larger toys, or groups of fingers, starting with two fingers, and moving up to three if necessary.

Keep being patient, and keep using the techniques I mentioned above this.  This is training and seduction.  You're creating beautiful new possibilities for a man that wants VERY much to earn your respect, and to give you every kind of pleasure.
What porn does NOT show you: That skinny twink has to get his ass ready with a series of ever-larger dildos, sometimes for hours, before he can take that monster cock.  That process never shows up in the video, because it's not sexy.  However, it's crucial.
You may have noticed something in my writing - I haven't talked about the Top's orgasms.  There will be plenty of those, and they'll be great, because you'll soon be fucking an eager, butt-hungry bottom-boy who LOVES what you do.  First, you have to get the bottom TRAINED.  Set it as a goal that he will NEVER endure even the slightest pain.  He will repay you many times over, and you'll be SUCH a happy Sir!