Fun and Games Ch. 02

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I thought briefly about my first time getting nailed and how his size was perfect for popping my anal cherry. He was sort of thick and somewhat long but once I got used to it, the feeling was great. It was a "full" feeling that took some getting used to, but his initial insistance that we go slow was sage advice; had I sunk down on that thick penis too quickly, the entire experience would have been very different. More than likely I would have been in discomfort from the beginning, a feeling which most likely would have intensified as time went on. I briefly wondered how many people, men and women alike, had a bad first time with receiving anal and vowed never again.

That being said, let's face it: anal sex is hardly a normal activity! No matter if you are man or woman, having a penis shoved into your rectum is not something nature intended for your body. As a result, it is necessay to use copious amounts of lubrication and to allow one's body to adjust to the invasion. The truth is that the anus, rectum, and prostate are loaded with nerve endings, making this region exceptionally sensitive to stimulation, but these areas are also susceptible to incredible amounts of pain if individuals are careless on either end, so to speak. After Tim's thick cock popped out of my ass I was stretched and a little sore, but allowing my body initially to adjust made all the difference.

I could hardly blame anyone if they had a bad experience and decided to avoid it in the future, but I was living proof that, even with a substantial dick like Tim's, getting anal can be a lot of fun with enough patience and lubrication. At first glance and first feel Tim's penis certainly appeared as if it was just going to be something to be endured but that was not at all how I experienced it. I guess for anyone out there wondering about it and afraid that it's just going to be a flat out painful experience, I suggest you go super slow, give yourself plenty of time to adjust and slowly accommodate your partner, a toy or whatever goes inside you. If it hurts, something needs to change; the speed, the depth, lubrication. If none of those things helps then in my opinion it needs to stop. But a little patience goes a long way. In my case it went about seven inches deep...over and over and over again.

As I got behind him, I did have a few twinges of pain; my anus had been stretched wide and he had driven his cock very deep inside me when he was ejaculating. Despite the mild discomfort, it was exciting to think that a few hours from now I would need only to tighten up my anal muscles to re-live the ass banging I just received because surely the weird, invasive feeling would linger. I later learned that, in fact, a full day later such a memory can be invoked with stunning clarity. Bear down, feel the feeling, and re-live the spectacle, then enjoy a furious masturbation session.

He glanced over his shoulder and said, "you don't have to be gentle with me once I get used to it. You can bang me pretty hard if you want to. I want to feel your balls slapping mine once I'm comfortable."

He didn't have to ask me twice. I greased him up and I treated him with the same patience he treated me, allowing him to flex and spread as my cock slowly inched into and out of his tight asshole again and again in shallow, deliberate motions. Slowly I pulled the tip of my cock out repeatedly dipping just an inch or two into his ass, leaving it in for a few seconds and then retracting it and lubing it up only to sink it past his tight, pink ring a fraction deeper each time. The escalating depth and volume of his moans were clear indication of each stage of readiness, making it simple to determine when he was ready for successively deeper plunges. After five minutes of playing and stretching, his hole was slippery with lube and exiting and entering was easy and painless.

I knew Tim was prepared for greater alacrity when re-entry gasps became sighs of relief. He was ready for a randy banging and I began to moan as I sunk my thick tool into the depths of his body, slicing and plunging deeper and deeper. Doggy anal was something I'd done before, but having a big cock sticking out the other side was another matter entirely, as were the huge bag of balls below his ass. As I began to slide in and out more rapidly, his sac began to swing and sway, and deeply pounding his ass had the added effect of slapping my balls against his, my scrotum acting like a bell clapper. It was barely audible but a faint smack could be heard when I did so, and coupled with the scratchy feeling on my own balls the feeling was incredibly good. Tim was definitely a man who liked a good ass fucking and groaned loud as I began to increase the speed and intensity of my pounding.

I got up on one knee and began to fuck him like a two dollar whore. "I feel like such a bitch like this" he said, almost whispering. "I love your cock up my ass. Your big fat dick fucking my ass like this makes me feel so cheap."

"Your ass is so tight", I said panting and moaning. "Your tight little asshole loves my cock! You good?"

"I love it. I love you fucking me hard. Get those big balls swinging. I want to feel them! Pound my ass with your big dick!" He continued muttering and it was very cool and very erotic. I love dirty talk and it notched me up closer to orgasm quickly.

"I want you to feel something", he said. "Slow down, go deep inside me and then stop", he said. "I want to feel your heartbeat." It was so cool! I could feel his heartbeat pulse and it was fast. My pulse was racing too. I just let my cock sit in his ass for a few seconds then resumed a nice slow stroke-in, stroke-out rhythm. I pulled out a few times and wriggled it past his asshole. It felt nice to slip out and then have his tight ring grip and gobble my cock head again. He loved it however I gave it to him, fast and slow, and as hard and deep as I wanted. I didn't feel the least bit guilty pounding his ass hard because he was in fucked-in-the-ass land of ecstasy.

As I held onto Tim's ass and fucked his super-tight asshole, I began to contrast something in my mind. Women, regardless of how fit they are, carry their extra weight in the butt. Men, on the other hand, Tim and myself included, are very lean in the legs and ass despite their size. When I was fucking him in the ass I had this thought that even when I closed my eyes and imagined fucking a chick, that's not the way it feels because they are not that muscular in the ass and legs. It was just an odd thought that went through my head, but I couldn't help think of it while I put the meat to my new friend.

He pushed his balls back with one hand, and now with one elbow and his knees supporting him slid down with his butt high in the air. I gave it to him slow, fast, deep and shallow and we loved every second of it. My initial thought that I was going to explode quickly had been dead wrong; I was super-excited which, for me, delays orgasm. I knew I was going to be able to fuck for a nice long time, and I was hoping that Tim would last another ten or fifteen minutes with my penis buried inside him.

He motioned that he wanted to change positions and lay down on the bed on his left side. He took a break for a minute and then I mounted him from behind and this was a nice position. I couldn't go as deep but it had a really nice feel to it that was somewhat tighter in the deeper depths of his body, which I really enjoyed. After 5 minutes or so of that, he got on his back and pulled his legs up. He got a pillow and put it under the small of his back while I lubed up again. In this position the pressure was on different parts of our bodies and it felt really good. I held his legs up and fucked him slow, then a little faster, then I really hammered him for a few minutes. He winced from the drilling he was getting and when I would slow down and he would say, "no, no, I like it. Keep going deep. It feels good." Far be it for me to disappoint him so I pounded his ass with reckless abandon as they say. This position and action provided a nice balance to the earlier things I had done and I was glad to be fucking him pretty hard right now, dominating him.

It was really weird watching his dick slap against his body as I fucked him! But I got used to it pretty fast and it was sort of cool in a very different kind of way. I was sort of wishing I had a video camera at this point because I would have loved to had video of him getting his asshole pounded by my cock. But then again being on video having sex with another man...not something either of us would want to see out on the internet!

I was really going at it and I didn't want it to stop, but after nearly 20 minutes his asshole was red and raw. I gave this poor guy a drilling, ass-pounding, fuck session the likes of which he'd never experienced. He told me to slow down and said, "this is the most I've ever been fucked in the ass at one time and I simply can't take any more! I'll get you off with my mouth. My ass is so sore I'm not going to be able to sit down for a week!" He kind of laughed and I did too as I slid out of his tight asshole.

I pulled out, went into the bathroom, snapped off the condom and thoroughly washed my cock and pubic area. He could hear the water running and he knew I was going to emerge with a rock hard cock that would be settling up in his mug. I came out of the bathroom and he was sitting on the floor with a few pillows and motioned for me to sit on the bed.

"I'm ready when you are", he said.

He was without a doubt the best cocksucker I have ever had in my entire life and in this position he outshined his previous 69 work as a true master fellatrix. He sucked hard, putting a small amount of vacuum on my cock as he played with my scrotum. In this position both his hands were free to play with my cock, balls, perineum, and asshole and he used every square inch of his hands and fingers to assist his expert mouth. I rocketed toward orgasm.

He allowed my cock to snake deep into his throat as a thick finger snaked its way up my ass. Obviously skilled in the ways of sucking cock, he extended his tonge along the curved front ridge of my shaft while his finger began to dance on my prostate. I'd never experienced so much stimulation so quickly and my body decided it was time to release.

He looked at me and said, "Come in my mouth", and re-corked his mouth with my hard tool.

Within seconds of penetrating me and stimulating my prostate the first few spurts of semen spat hard into his mouth and trickled down his throat. He quickly pulled back a few inches, dragging his tongue along my shaft and stopped when my cock was about two inches inside his mouth, my cock head resting on the meat of his tongue. I literally screamed as I ejected huge streams of semen into his mouth, over his tongue, dribbling on his lips and chin. He moaned my semen flowed out of his mouth and over his fist which was now clenched around the base of my penis. My come and his saliva made a slippery, slimy whitish trail down my shaft and over my balls. He sucked my cock like a whore and continued to finger me like one.

The sensations were amazing as his tongue, lips, and fingers continued to stimulate me to incredible heights. The room was spinning and I became dizzy on orgasmic overload as I realized I was experiencing another orgasm, something that's only happened to me a handful of times. But given the sheer volume of stimulation my body had been subjected to up to that point it was not surprising. After the second orgasm I felt like I had been run over by a truck and Tim licked his lips, his face and chin spattered with thick, white gobs of semen. A thin trail of semen started halfway down his neck and made a perfect line all the way to his left ear. Despite how much come was on his face he had done a great job keeping up and managed to swallow the lion's share of my salty come. He continued to lick his lips and gently pump my cock to fan the dying embers of my orgasm. A final droplet of semen sat atop my penis and he gently bent down to clean it.

"I love come", he said quietly as he swallowed. "I like the idea of it more than the taste." He looked me in the eye. "The idea of getting such a reaction. It's so violent, so sexy, so dominating and dominated...all rolled into one. It's unequaled", he said as he softly licked and caressed my softened penis. My balls were still super sensitive and he bent down to lick them all the way round. It was a fantastic feeling, his rough tongue dragging over the soft skin of my testicles, occasionally tickling them by dragging his tongue over and through the light, curly hairs.

Reflecting on my semen filling his eager mouth, I thought that if I could talk this guy into letting me pound his ass and then come in his mouth again some time I would be a very lucky guy. He certainly had no problem with either activity, and continued to lick up stranded blobs of semen from the base of my cock and testicles. It was just too much - eventually I had to ask him to stop licking and sucking my cock because every flick and lick was sending shocking electric bolts through me.

"Tim, that was amazing but..."

"I know!", he practically yelled. "I know, it's too much. OK, I'll stop. It's just that the cleanup...it's my favorite thing."

"Isn't that what they say? Do what you love?", I said mockingly with a bit of a snicker.

"No doubt that I love this. Being nailed and getting a guy off with my mouth. That is a winning combination."

"Well if that is what you like then I think I can help you. Any time you feel the need for either or both, please don't hesitate to call me!" I said as I sat there, naked, with my soft cock inches from his face.

After I calmed down a bit more I went into the bathroom to get cleaned up and get dressed. Tim did the same.

I walked toward the door and was ready to get home.

Tim said, "So I guess it's safe to say that we want to keep this confidential. I mean, it's not like you are out in the open about this. I respect your privacy and if you want this to remain confidential, it will."

"For now, definitely", I said somewhat relieved.

"Well, I had a good time. I hope your first time wasn't too terrible."

"Not terrible at all. It was pretty cool. I was hoping we could masturbate together but I guess, you know..."

A few seconds of silence passed and then he said, "Maybe, you know. I don't know...maybe next time if there is one."

"If you wanted to meet again I would be up for that some time."

"Cool", he said. "It's not like I want you to be my boyfriend or something. You're not my boyfriend."

"Oh, definitely, I get that. You're not my boyfriend either. I'm not interested in you in any other way than what we just did. Strange as that may seem."

"OK, then I guess we have an understanding. Maybe sometime we can, you know..."

"Fuck?" I said laughing. "Yeah we can do that. I still want to jack off together because I think that would be a lot of fun."

"Yeah, that would be cool. We could do that."

"Thanks for letting me do you after you came. I was terrified for a minute there! I thought, oh, no he blew the wad now I'm going to be asked to leave! Funny."

"Oh, yeah of course. That would be rude, so I wouldn't do that. Now you know I can pop and then you can still count on me to keep going. You may get to that point, too."

"It's hard to imagine getting to that point honestly!", I said. "But I have to say all this was something I didn't expect and had no idea, quite honestly, how much I would enjoy it. I really did enjoy it! It sounds weird to hear myself talking about it."

"I remember the first times", Tim said. "No doubt about it, it's strange. You will learn a lot about yourself in the next few days", Tim said, smiling.

"What do you mean?"

"You'll think about what you did. I think it's normal to reflect on it and question why you did it."

"Yeah, definitely I can see that happening!", I said laughing. "I'm questioning it already!"

"It can be very good for you in ways you never really imagined, too. For me, I learned that I could enjoy this and that it didn't 'make me' anything. I'm just me. I'm unique and this is one of the things I like to do."

"Apparently it's one of the things I like to do, too", I said. "I loved, you know...I really had a good time. Everything you did was really great." I looked up, away, anywhere but at Tim. "This is the weirdest fucking conversation I have ever had!" I laughed.

"And on that note, I'm gonna roll. See ya around Tim!", I said.

"Yep, OK, man. See you later."

On the drive home the dull pain deep in my ass, literally, left no mistaking what I'd done. It reminded me that only an hour ago I had a thick penis sliding into my body. My jaw was aching a little and tiny residual flakes of dried come were on my face and hair, enough that I could smell it, and a light taste of semen remained in my mouth. It was a rush. I could hardly wait to do it again.

***

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Riki1942Riki1942almost 4 years ago
First Time

Great story and I loved the detailed descriptions of how it felt, psychologically and physically. I can really relate to most of it in both ways.

The first time that I got fucked was was by a guy that I had been talking with for some time. I didn't experience any pain because, although he was a good seven inches or more, it was rather thin; probably only about an inch thick, all the way to the base of his cock, and I had been using dildoes larger than that. I'm not into pain and I still don't prefer really thick ones, but I do love feeling full really deep.

The thing that I remember so well is the unreal feeling that it was finally actually happening! Of course it felt completely different and infinitely better that a dildo, but it was that knowledge that it was the real thing, a real guy was fucking me and the self affirming component that I was really and truly confirmed as gay. Not only did he fuck me, we did it bareback and he came deep in my ass! It made me feel like such a faggot and I loved it!

He was recently divorced and it was his first sex with anyone since his wife and his first time being with a man. We continued doing it bareback until he moved away because of his job. I have had a couple of long term relationships since and we fucked bareback and my current fuck buddy always does me raw.

Being on top and riding is one of my favorite positions. I like to make my partner feel good too, but when I am more in control I can also do more of the things I really love to feel whenever I want and as long as I want. Sometimes I just need really rammed for a bit, and then I can slow slow down and feel those long, slow and full strokes all the way to the base of his cock and then slowly out until just the head is inside me. When I so that I am more able to concentrate on that delicious feeling of his cock sliding back and forth through my ring. Also, I love to stop, sit down all the way to the base of his cock, feel it filling me up so full and grind my ass around on him and feel it stirring around in my belly. That sideways pressure on my ring while grinding drives me crazy too.

Riki

AnonymousAnonymousabout 9 years ago
Great writing

Thanks for the very descriptive storries.

You are a fantastic writer.

Please keep writing stories like this.

They help me come to terms with myself.

burnie4434burnie4434over 10 years ago

I remember the first time I got fucked like it was yesterday. It was the day after I had sucked my first cock and with the same guy. The night before I had sucked him off twice and then once in the morning. He asked me to stay with him for the two weeks I was going to be in town and I accepted his invitation. He asked if I would like to suck some different cocks and I said yes if he didn't mind. He then told me he would send a couple of guys over during the day. He ended up having 4 guys come over and I loved sucking all of them. When he came home, he bought another guy with him and I sucked him off too. The three of us went to dinner and then Phil and I went back to his house. I told him that I appreciated his sending the guys over, but that I really wanted to suck his cock again. He said he would like that, but that he would rather fuck me. I told him that I didn't know about that. He laughed and said that less than 24 hours earlier I had never sucked a cock and now had sucked six guys off. He told me that if I told him to stop, he would. He started by lubing may ass hole then fingering me. He ended up fingering me with 4 fingers and it felt wonderful. I then felt the head of his cock at my hole. He slowly pushed it into me a stopped to let me get used to it. I took him about 29 minutes to get his 71/2 inches into me. It had hurt a little, but then began to feel really good and I found myself fucking him back. He ended up really pounding my ass and I loved every minute of it. He then came in my ass and finally pulled out. I was a little sore, but felt empty. I told him that I hoped he would fuck me again while I was staying there and he did.

AnonymousAnonymousover 13 years ago
Thanks, again!

I enjoyed it almost as much as the first one. Again, very hot! Keep up the great work

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