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Not that all bottoming is painful, but generally, there is some discomfort, especially at first, and especially with larger penises. But the discomfort usually goes away quickly with enough lube and is replaced with this subtle feeling of being stretched or filled.

And that is what I love—that pressure. It makes me hard and builds the longer and harder I bottom. The feeling eventually takes over, until it's all I can think about is that pressure against my prostate and in my penis until I orgasm.

I can feel my prostate being hit and massaged. Anal sex feels like that first glass of unsweetened iced tea on a hot summer day.

It feels like the hot shower after a weekend camping trip. Those first moments are filled with a slightly uncomfortable sensation mixed with bits of euphoria.

During this time, you are bordering between regret, eagerness, anxiety, and pleasure. After a deep breath out and an inhale of determination, time passes and the meal cools.

You then enter a state of delicious consumption, as your booty devours their penis. United States. Type keyword s to search.

Today's Top Stories. The 50 Most Unique Gifts for Guys. What anal sex feels like for the insertive partner a. Hugo Prostate Massager.

You may be able to find the same content in another format, or you may be able to find more information, at their web site. Zachary Zane Zachary Zane is a Brooklyn-based writer, speaker, and activist whose work focuses on lifestyle, sexuality, culture, and entertainment.

This content is created and maintained by a third party, and imported onto this page to help users provide their email addresses.

You may be able to find more information about this and similar content at piano. You want to be sure you have a supply of magnum condoms as well as regular size.

I like to put the condom on the guy myself to guarantee proper placement, fit, and to guarantee the reservoir tip is directly over the hole to catch all his cum.

I once hooked up with this black man named Randy who I met at a bar and we ended up back at my place. He was very well hung and neither of us had any large condoms so we just used a regular sized one I had in my drawer.

I should have listened to my instincts when I had trouble getting it on him. Eventually, he was holding my ankles while furiously pounding me in the missionary position and when he unloaded his spunk, I thought I could feel the warmth of it while he was shooting.

When he pulled out, I was horrified to see the condom was completely broken and the only thing left on his dick was the rubber ring around the base of his shaft next to his pubic hair.

Randy had completely shattered his rubber because of the size of his dick and the friction of my tight asshole. I have also had the complete opposite happen to me.

The first time I allowed this waiter named Tim to fuck me; I put a large condom on him because he had a long penis. Even though he was about nine inches in length, he was very thin in girth.

He fucked me for quite a while in several different positions and because of the duration and him leaking so much precum, his rubber completely slipped off inside me.

Once again, we didn't know it until after he came. It took a couple of minutes after we had finished for me to find it and pull it out.

Whether you are going to use a condom or going bareback, you need to use lubrication. Most of the time, you want to use a water soluble lube like Astro-gluide or KY Jelly.

These types of lubrications will not interact with your latex material and are easily expelled. Occasionally it is nice to mix it up and use baby oil, Vaseline or something creative.

I once was at this guy's apartment that had just moved in and most things were boxed up. I was giving him a blowjob on his couch when he got so horny and needed to fuck.

We looked around in boxes for anything to use and the only thing we could find was peanut cooking oil. Surprisingly it worked very well and we were able to kill two birds with one stone because he ended up pulling out and cumming in my mouth and that mixed with the oil taste was not bad compared to when it is mixed with regular lubrication.

I find it best to lubricate both, his cock and your own asshole. There is really no reason for both of you to get lube on your hands so decide which one of you will do it.

Most of the time, I am the one who greases up my partner's dong with some stroking and then I slather my own asshole by sticking my fingers in and swirling them around.

I personally like to do it myself because one, I can control the amount of lube and second, it prevents him from having it all over his hands and he won't accidently smear it all over your hips, ankles, or waist when he is holding on for leverage.

Semen is a great lubrication. Of course it can only be used if your partner has the stamina to fuck you twice or if you're involved in a threesome or an orgy.

One time I was involved in a threesome where both guys came twice. After the first guy blew his load in my ass, it was lubed well enough to last the total sex session with both men.

After taking 4 loads in my butt, I did feel as though I had a cum enema and not once was there any trouble getting them in and out of me.

Entering Once you are clean and both of you are lubricated properly, it is time to fit him inside you. This is the hardest part. If a guy has a large dick or even just a large head, it can start out very painful.

Your lover has to be very careful and patient. If he has a smaller to medium sized cock, I will allow him to insert it my rectum but if he is extremely large or just has bulk, I like to control the entrance.

If I am unsure, I will error on the size of large. If your lover is the one that will be doing the inserting, it helps if you reach back and guide him.

Place his penis head up against your hole, take a deep breath, and relax your sphincter muscles. When he pushes, keep your breathing smooth and controlled while you allow the mushroom to pop in you.

Your anus will stretch but it still is quite painful in the beginning. Try to hold it as long as you can and if the pain gets too unbearable, have him take it out.

At this time is when many people give up on anal sex but you have to be persistent. The second or third time he slides his head in your butthole, the pain will be a lot less.

Your hole will eventually adapt and accommodate his size but it takes time. This is why I say your partner has to be patient. This is another reason I like to be in control if my partner is hung.

Once he is inside you, and the pain has subsided, then allow him to feed his inches into you slowly. This can also be painful and this is why he needs to be patient and well lubricated.

I prefer he goes ahead and buries his cock all the way in me until his pubic hair is touching my ass crack as soon as he can because this allows you to get acclimated to all of it and there are no surprises later on.

Once you are ready, he can begin his thrusting. Now if your partner has a large dick, you have to approach it differently because he can do some serious damage to you and this is why I like to be in control.

After I have sucked a guy to full erection, I will have him either lie on the floor or sit on the edge of a chair so that I still have access to put my feet on a hard surface.

I will hold his hard cock where it is pointed straight in the air, squat down on top of it, place it directly against my asshole, then ease myself down on it until it is tolerable.

Sometimes, it may take as many as three or four times of you pulling off and then getting back on it. Eventually, I will be sitting on his lap with his huge dong buried in my rectum.

If you're properly lubed, stretched, and able to take his size, then you can have him fuck you. I like to bounce on him for a while just to get everything adjusted and then switch to different positions of his choice.

You can always finish by going back to the original position of riding him until he cums. I will tell you that a large dick can make a difference inside you.

When your butt is completely stuffed with a huge dick, the length of it feels like it is up in your intestines and the suction can put air in your stomach and give you cramps.

When fucking a well hung man, you need to take his cock out of you periodically during your sex session. Don't wait too long before you get it back in so that your hole is still stretched and ready.

The largest guy who has ever fucked me was when I was in college and he was a black linebacker on the football team.

His dick was absolutely huge. It was about 12 inches long and as big around as a Pringles can. If he struck out with the ladies on the weekends, he would call me over late at night and give me his monster.

It was so big; I could barely give him blowjobs. I would have to open my mouth as far as I could just to fit in his head, and after that I could only get a couple of inches in my mouth.

I basically could only jack him off with both of my hands while blowing him and when he would finally shoot his load, I could barely take it without choking.

You could imagine my horror and excitement when he wanted to fuck my ass with that tree trunk. The first time, I had to take a pain pill just to get relaxed and prepared to handle Vinny's monster.

The fact there were a few girls around who he had fucked, used to tell people that there was no way anyone could take it in the ass.

Hearing this actually excited me and made me want it even more. I was ready to accept the challenge. That first time, it was about in the morning and I used Vasoline and lots of it to prepare myself for him.

Vinny was really drunk but didn't have much trouble getting that huge dick hard. I had to sit on him and really work it around until it finally plopped in me and the pain was overwhelming.

I thought I was ripped and pulled off immediately. I repeated this several times before I was able to handle it. Eventually I was able to sit all the way down on that dick and I swear it felt like it was up inside my belly.

You always hear or read when people say that a cock that large feels good but that is a total lie. You never get completely used to a cock that big.

You can eventually tolerate it but you make sure you are fully lubed up and say things that can make him cum quickly. When fucking a large cock, air builds up inside your anus and it can form suction upon withdrawal.

On another night when Vinny came over drunk and extremely horny, I ended up on my back while he pumped so hard that his balls ended up leaving red marks on my ass from the repeated smacking.

I know it sounds made up but his balls were also huge and hung extraordinarily low. After he finally came, he just rested for a couple of minutes with that huge cock still in me.

Even though his dong had deflated a little bit, the suction had built up so much that when he finally pulled out, a string of cum squirted out through his legs and across the carpet.

It looked like it had squirted out of a water bottle. Taking the Cock Now that your asshole is acclimated to his dick, it is time to get screwed.

There are many positions that can give you just as much pleasure as the guy pounding you. If you are flexible like I am, then lay on your back, with a pillow under your ass to position your hole more upward, and have him put your legs behind your head.

He can hold your ankles to give himself leverage while he pumps straight down. In this position, you can reach around his ass and kinda hold him steady so he doesn't slide away if he is on his knees.

If he is young or strong, he can also stand on his feet and fuck you without sliding away. This position really feels good on your prostate and also allows you to feel his warm cum as it squirts in you.

I can tell you that it feels better when you feel his cum shoot further up you and that is why I like pulling his ass toward me he cums.

Another good position that I use which has many benefits is when I get on my knees on the couch facing the back of it.

I put both my hands on the back with my legs spread. This allows my lover to stand comfortably and be at a perfect height for him to insert himself inside me without having to squat.

If he is taller, he can just spread his legs wider to make himself shorter and yet his feet are flat on the floor to dig in for better traction.

This is also a good position because you can hold on to the couch no matter how forceful he pumps you. This position is also very convenient if he is a pull out cummer.

He literally doesn't even have to adjust himself if he chooses to pull out and shoot it on your ass or back. If he likes to pull out and give you a facial or cum in your mouth, it is a very easy and quick transition because he can pull out and all you have to do is swing one leg over and immediately you are in a setting position at the perfect height to his dick.

If he is wearing a rubber, this will also give him time to pull it off. Now you are ready for his load without wasting much time at all.

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