Gay Anal Virgin Made For My Personal Pleasure!


Three years ago, I used to listen to one of the local community radio stations. This particular night was different from every other night. A deeply masculine and soothing voice spoke “I am a married man secretly searching for an experienced mature gay man for a massage. I am an anal virgin made for your personal pleasure.”  I was instantly turned on by his offer. Plus it was free, so why not?  He continued “If you are interested in popping my tight cherry, contact the radio station for more details.” I hurriedly contacted the radio station who told me to meet him at the local docks in New York.

That night, I arrived at the docks and looked for him. The radio station told me to look for a man wearing a gay colour coded handkerchief in his right pocket of his jeans. I walked down the docks and looked for the man. I saw him first and watched him from a distance. He had short blonde hair with a fringe, his muscular body was perfectly outlined through his tight white shirt and tattoos covered his arms. Our eyes met for the first time, he smiled through his beard and adjusted his shirt in hopes that I would be the lucky candidate he had asked for.

I walked up to him and we spoke for a long time. I found out that he worked on the docks and frequently traveled out of New York. He had been married for five years but fantasized about his previous sexual encounters with his childhood friends. The sexual experimentation with his friends went no further than peeking at each other’s penises. Ever since then he had countless sexual thoughts of experiencing anal sex with a gay man for the first time. He appeared uncertain about what he was doing, he was so timid and almost powerless.

Since he was a beginner, I did not want to rush him. I decided to invite him over to my house for a drink and personal massage to see if he would like things to progress. I have worked professionally as a part time masseuse for the past couple of years and I had found that it is an extremely pleasant, nonthreatening approach to become more acquainted with somebody. We drove over to my place.

I gave him a cold beer and we chatted for some time until he was relaxed. At that point, I led him downstairs to where the massage table was. I instructed him to undress while I retrieved the oil and towels from another room. When I got back, there he was on the table, absolutely stripped and spread out like a smorgasbord. I took a gander at his ass knowing nobody had ever been in there before. I salivated.

I gave him one of my best and most sensual massages that I possibly could. He began to moan with every stroke. He rolled over onto his back and he placed his hard erection into my hand. I made him spread his legs with my free hand and plunged my mouth onto his cock. I slowly licked, slurped and drooled my way down to his rosebud.

I became harder knowing nobody had ever rimmed him before. I began to do my specialty, he lifted his legs lifted off the table which allowed me to get my tongue into his sweet asshole. He was squirmed and groaned in absolute delight as I twisted and moved his ass checks down into my face, almost like a dog in heat. When he was overwhelmed and could scarcely talk, I slid my tongue right into his rose bud and moved his body back and forth. I stroked his cock until he was about to cum. I quickly placed his cock down my throat and he came in immense spurts down my throat which I was pleased to swallow. As he rested, he groaned with relief.

I was in sweats and my shirt was soaked through. As he got dressed, he told me that nothing he had ever experienced before compared to the massage. He noted down on my calendar the times he was available. As he exited my house, he swore he’d be back.

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Early the following week I got a call from him. His wife was going away, he needed to come over and see me once more. He asked “Would it be okay if I spend the night? I’d truly love to.” I of course said yes.

On Thursday, he appeared at my doorstep. He gave me a big embrace and laid a sweet kiss on my cheek. We talked for some time, this time he appeared to be exceptionally eager so I took him down the stairs for another massage. When I got him downstairs it was obvious he wasn’t there for another massage, if his erect cock was any guide.

I ate him out again until he was on the verge of moaning. I peeled my garments off while I went down on him. I placed some SuperSlyde lubricant onto my fingers and inserted them inside. I began to finger him, moving them in and out. He groaned as his ass tightened around my fingers. I slowed down, moved my mouth to his ear and said “Do you want me to top you?” I inhaled into his ear. “Would you like to get fucked by a man?”

“Hell yeah!” he replied. I was hard as stone from listening to him groan and his words simply made me harder. I got the lube and rubbed it on my cock. I moved up on the table and settled between his legs. I pulled at his hips until he was up on his knees with his face still on the table. I gazed down into his totally gaping ass. His hole was a bit red and swollen from the fingering I’d effectively done. It almost sparkled in the low light with the lube I’d placed there. It looked like heaven’s door to me and he moved his hips forward and backward. His gape opened and closed as if it were winking at me. It opened and shut automatically as he knew what was about to happen to him. I grasped my cock at the base and swiveled my hips forward. The tip of my cock touched the wet entrance and simply kissed his gaped ass.

“Alright, I’m going to slide in. Push out, as if you’re taking a dump.” I said.

He kindly pushed out and when I saw his little gape open, I quickly began to squeeze the tip in knowing this would be his very first gay anal experience. At first I felt the resistance, but it began to give way which gave me a chance to slide it further into him. His little gap was only able to tolerate the head of my prick. When I popped it further inside, he snorted like he’d been punched. I halted totally still for a minute and he began to move his hips once more. He backed into me and pushed a couple of inches of me into his cherry butt. He whimpered a bit under his breath. His back was completely covered in sweat, the inches that he inserted had inspired him to push even deeper back onto my cock.

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I was completely inside of him, my balls were tight against his ring and my pubes scratched up against his butt cheeks. He groaned and gasped for a moment or two. I kept still and absorbed the mind boggling warmth and tight hold of his virginity. I ran my hands up his sides and down his spine which calmed and unwound him to get him prepared for more. I was going to ride his virgin ass hard, however I needed him to be completely invested so that he could always remember the hot and steamy moments of his first time.

I stayed still until he began to move under me. Then I slid myself out by only an inch and inserted it once more deeply inside. I rested as his hot ass grasped onto my hard cock. After every two breaths, I would move out and then back in. He groaned even louder and snorted each time I thrusted into his virgin cheeks. Each time I would go as deep as possible, with a throaty snort I rammed my cock right up into his pelvis. He began to move his butt once again into me and countered my strokes. His back broke out in shivers.

I was delicate with him but I used incredible power. I needed him to realize that it was a man in his rear end, that his virginity had been taken and there was no retreating. He angled his bum up into my groin with a full stroke and made a higher pitched groan. He did it again and made a little snort when it bottom. He was somewhat freer now, his virgin gape took me in more easily and it was beginning to feel great. The floods of joy were beginning for him and I knew the time had come to turn up the power a bit.

I lifted him up a little on the following stroke. This time I massaged my cock over his prostate. He made a startled sound. He moved once again into me and I pushed somewhat harder back in. His head swung to the side, his eyes were shut however his mouth was open and a little dribble spilled out the side of his lips which wet the sheets. I went into him quicker and harder this time. His body quivered under the blow, yet he continued to groan.

I thrusted in hard, his head lifted off the table somewhat and he groaned louder. I reached around his waist and held onto his prick which was rock hard. It spilled out with pre-cum. I massaged his pre-cum everywhere on his cock head and stroked it with a tight grasp. He intensely shivered as he yanked his head back hard when I pummeled into him.

After a few more hard strokes, I hauled my cock out of him. He grunted as I dragged him off the table and I pushed him down over it. I kicked his lower legs apart and slid into his rosebud with one hard stroke. I continued to stretch around and jerk his throbbing prick. I used his own pre-cum as lube. I fucked his butt for the following 20 minutes, blending short hard thrusts and long moderate strokes. He adored every moment.

At long last, his groans got louder and higher pitched. He thrusted back into me harder on every stroke. His head was going here and there on every stroke. I fucked harder into him, his prick swelled significantly harder and it knew it wouldn’t be much longer. I wasn’t too far away myself, I could feel my nuts tighten and the humming sensation that lets you know it will be a huge load.

All of a sudden he was there. I extended my body over him, I beat my hips into him and jacked him hard. With a profound snort, his prick spasmed in my grasp. He raised his head back. He spurted and spurted all of his seed over my massage table. His rosebud held me inside as firmly as it had when we’d initially begun. He discharged cum out everywhere on the table, his entire body writhed like a snake and his ass spasmed on my cock.

I beat two more strokes into the tight grip his ass had on me. I held myself hard and deep inside. I hammered out a hot and substantial load into his virgin ass. I shivered and gasped. It felt sweat and smooth. My cock pulsated in him as his ass drained out the last drops of my cum. I held him tight in my arms, one hand placed on his chest and the other cupped his balls. I lay forward over his back and simply inhaled into his neck for a minute. I rubbed my facial hair against his delicate skin for a minute.

He turned his head and looked at me. He wore a grin of a sexually fulfilled man – a bit timid, however extremely fulfilled.

That was the story of how a man of the docks lost his cherry for the very first time.

Gay First Timers Sex!

two men spooning

Have you got out of the closet recently and are you thinking about having sex with another guy for the first time? If this is true then you might have some concerns and questions about whether you are ready and how the experience will be like. Sex can be very important, so it is best to make sure you are ready so that you can receive a positive first experience. But how can you tell you’re ready? One way is to ask yourself some questions like:

Are you ready for your first time having gay anal sex?

Chances are if you are reading this it means that you are thinking of having sex. But are you ready emotionally except of physically? Have your looked into the intimate ways available including rimming, oral or do you know what is bottom or top? Its obvious how to top or bottom. One person will penetrate and the other will just receive. But, how do you know if you’re a man that likes top or bottom? And even then, are you a good on top or bottom sex positions? And, are you prepared to do either? Some guys can enjoy physical sex without experiencing emotional connections. Others, however, prefer some level of emotional bonding before being intimate with another partner. Have you thought about where you lay on? Do you want to have sex just to please yourself? Am I having sex with the appropriate guy? Or do you want to be emotionally attached to the person you want to have sex with? Am I comfortable showing my partner my likes and dislikes? Will this lead to something serious? Do I want a relationship or just sex?

You should also keep in mind that society puts a lot of pressure on the first time sex as well as the consumption of pornography as well where people place unrealistic expectations on sexual experiences. As a result, teens can have high expectations about what they want from the experience. But the first time people have sex doesn’t always feel like it is something special. Often the first time you have sex it is more of a process for discovery. Having sex with a man for the first time can be challenging, especially for teens that got out of the closet recently. You can always use the internet and find information on how to have safer sexual intercourse with a man or you can find some techniques that can help you learn or improve your oral sex and other intimate acts. Sex may seem simple like you give, receive and relieve pleasure. But, sex can be far more complicated, especially if you’re not prepared.

Always remember that sex should be enjoyed and not pushed and done fast. Discuss with the man you are having sex with, and tell him that you want to follow your pace. There are no fast rules and everyone has a different definition of sex. Tell him it’s your first time. This is important because he may push things without realizing that you need a little warm up, and vice a versa. We shouldn’t assume here that your first time will be about bottoming! Let him know that he needs to take it easy and be gentle with you as it is your first time. If it’s his first time as well, then you need to be relaxed, gentle and pay attention to his body and what he is saying and feeling. Discover his body and his emotions and let him discover yours. Sex can be important for anyone, so you should always take it slowly and make sure that you are emotionally and physically ready for having sex with another man.

There are some simple rules which are to tell you how to begin, where to continue, when to finish and how to get the maximum pleasure from your gay anal sex. Once you’ve chosen to have sex, there are a number of ways to reduce the risk of contracting sexually transmitted diseases. You need to know about safety measure these days as you can’t be too safe or sure a guy is clean and healthy by the way he looks or from what he says. Please follow these simple rules to make your first time as easy and enjoyable as possible.

Rules for your first time having gay anal sex

  • You should always buy and use condoms. One moment of unprotected intercourse may make you suffer for the rest of your life.
  • Use water or silicone based lubricants. Both oils and petroleum jelly  reduce any condom protective capacity quickly, the latex deteriorates under the oil. You may lubricate your dick itself or the condom. Remember, you can never have enough lubricant.
  • You can always start off with oral sex to make foreplay fun. Pace yourself to make your partner or yourself relaxed.
  • Turn foreplay into a game because you have a lot to discover.
Use a condom
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If they are above average in girth or length you may need to take some extra precautions by warming up first with some kind of anal toy. That will be the only thing that matters when it comes to penis size. The thinner it is the less pain you’ll feel, though some people can tolerate the initial pain much better than others.  The romantic and slow approach by the person you know is the best remedy from the majority of pains during gay anal sex.

Take your time and do everything the slow way and let your body and senses guide you and let go. Go with the flow. Try not to get anxious because there is no one right way to do it. Start with one finger; lubricate the anus with the lubricant chosen. If your penis is not extremely thin wait when you partner’s anus can hold 2 fingers. After this try to enter your penis and when you have entered it move slowly. Move it back and forth just a bit, go deeper slowly. If your partner feels pain, tell him to relax his anal muscles and try to push your penis out, as if he was going to the toilet. Use particular sex positions which let your partner stop the anal intercourse if you are too rough. If you do consider your penis as too small against your partner’s ass, then you are able to raise the pleasure by using one of the following positions:

  • The bottom is lying with his knees under his stomach, with his ass is slightly raised and his anus maximally open. When he lowers his ass, your dick will be squeezed.
  • The bottom partner is lying on his stomach. Climb up his ass and enter your penis. In the process, change the penis direction from vertical position to horizontal one.
  • The bottom partner is lying on his back; his legs are thrown over your shoulders. Raise his ass and enter it from the front.
  • The receiving lover is lying face down, with one knee under his chest. The other knee is taken aside; the leg is stretched and slightly bent. Slide it inside.

Some men like to have their penis squeezed. Well, squeeze your ass muscles to make him feel the ultimate sexual pleasure. Some men prefer the minimal pressure so relax your ass fully to let your partner go deeper and deeper. Other men just really like to have both and the pressure being alternated. Try all 3 approaches to find what the best is for your partner. It’s easy to get the simultaneous orgasm for both lovers. When your partner reaches near orgasm, let him stimulate your penis by getting him to jerk you off with the reach around or simply do it yourself. Use some lubricant to reach the full pleasure. The impact on both his penis and your prostate should make you have your orgasms at the same time. Though, if it doesn’t work out that way – do not panic just keep rocking it!

Not all gay men like anal sex!

Despite the common myth, not all gay men like anal sex. Take into consideration that while some gay guys enjoy anal sex, a whole lot of others don’t. Some mature gay guys just aren’t into anal. They might enjoy oral sex with a partner, mutual masturbation, rimming, frottage and body rubbing or role play. These types of non-penetrative sex can be used as foreplay or to complete intimacy. Sex is more than just anal penetration and the first time you have sex with another guy doesn’t have to be the first time you try out every sex act you have ever heard of. Sex can be very important for you. Hopefully, having more information will help you have the safest and most enjoyable experience during your first sexual encounter with a man.

Author: Stephen Smith – BA Of Social Sciences, M.EdSave