Fun and Games Ch. 02

The next day was odd as I reflected on what had happened, but I was so excited that I couldn't resist calling Tim. I came up with some excuse to stop over in the middle of the week to watch a game, but we both knew that wasn't why I was going to be there.

After some polite conversation I just blurted out, "I'm ready Tim". He of course knew exactly what I meant. We got undressed and were in the bedroom in a minute or so. I got down on my knees by the bed and he scooted over to allow me to suck his cock. I took his cock in my mouth again, sucking hard, then releasing it.

"Yes, I am definitely ready. I want you to explore me. I want to feel this inside me", I said with his cock still in my hand.

He got up on the bed on his knees and was waiting for me to get into a doggy position, but with nonverbal suggestions I encouraged him to lie down on his back.

"I am going to mount you facing you", I said, feeling like a total whore, hardly believing the words that had just tumbled from my lips. He was lying down now and I was sort of hovering over his abdomen.

"Yeah, that's fine" he said quietly. "Just make sure you go slow. It feels great if you take your time but if you don't you can tense up."

"What would happen then?", I asked with obvious trepidation in my voice. He had a big cock and I was getting a little scared. I only had anal sex with one girl many years ago and she loved it up the ass, so subtlety wasn't necessary with her. She was not a virgin to anal and loved it pretty hard. I of course was new to this and his dick was so big I knew I had to be careful.

"It won't feel good if you go too fast. You need some time to relax. If you're not ready..."

"No, I'm ready. I want to do this", I interrupted. "It's just...a little scary."

"You'll do fine" he said, assuring me with his calm voice. "Just remember...relax, slow, calm, gentle, easy."

Oh, god I was really doing this. I was on some guy's bed and we were both naked and we're openly talking about anal sex. I was so nervous. But I was so ready! I was ready to do it.

I said, "If you come first will you be OK with me penetrating you later? I want to do that. I mean, I think I want to!"

"Yes, definitely. I want you to have an enjoyable......you know..."

"First time", I said with a smile. "My first time...doing this." I couldn't bring myself to say 'have gay sex' or 'get fucked in the ass' but that was of course the unspoken truth.

I figured having him on his back would be good because in this position I could control how much cock I fed into my ass and at what rate. This turned out to be a good decision. He slid on a condom and I lubed him up and played with his hard cock for a few seconds. I was shaking as I nudged the fat tip of his cock at my asshole, but he moved his cock aside and lubed up his fingers. First, very slowly a finger slipped inside me. He moved it up to the knuckle and moved it back and forth inside me for a few seconds. It was slowly withdrawn and joined by another finger. It felt great. Two fingers was definitely a little wider and I moaned in approval. This continued for a few achingly good minutes as combinations of one, two, or three fingers probed and readied me, relaxing my muscles. After a few minutes my body accepted three thick fingers into my back entrance, slipping effortlessly inside me. I knew I was ready and I was about to make it happen.

I was about to get fucked in the ass and I was very nervous for good reason. Everything was so new and different; the choices and minutes were whizzing by. I was scared that I was going to get pounded too hard or it was going to hurt. Tim's penis was thicker and longer than any of my dildo toys so I was rightfully concerned. I guessed him to be about 7 inches long with a girth that my hand could barely grip, so I needed to make sure he didn't go crazy and split me open. I looked behind me to assess the size of his penis in relation to his fingers. His other hand was working his cock and my stomach sank. His cock was a good bit wider than his three fingers! I faced the wall and closed my eyes tight, wincing in near terror, then opened them again and glanced back again to see the digital replacement, hard and twitching. He was ready, too...ready to plant that thick tool deep inside me, but he was patiently waiting for me to get it started. I gently tugged on his wrist, encouraging him to let his fingers slip out of my body, indicating that I was ready to take it to the next level.

Involuntary sounds reflexively leaped out of my mouth as the tip of his tool nosed into my tight, virgin ring. Only the head of his cock went in but it felt very wide but only hurt a little bit. My mouth was dry and my heart was pounding as he pulled out, re-lubed and eased the tip in again. This time it felt warm, thick, wide. He slid in a few inches and out again, and lubricated his penis again. My body very slowly was beginning to accept his thick tool easily and without pain.

"Oh my god you're so thick", I said. "Your fucking cock is so big, please go slow", I begged.

I was amazed that my hole was yawned open so wide and yet it felt so good. Slowly I was being stretched but it didn't hurt and his cock was very warm and somewhat flexible even though it was really hard. This was very different than dildos of course and I noticed how much nicer it was. His big cockhead and shaft were plenty snug, and I smiled thinking about pleasing him. This submissive aspect was radically different than sex with a woman and it was weird at first but I started to like it. Tim entered me slowly again, sliding a few inches deep and then remained motionless, waiting for me to move. It was cool because the tiniest motion of either of us continued to pitch his dick further into my body and it felt absolutely wonderful. It was warm and deep and there was nothing about it I didn't like. I closed my eyes and moaned, saying how much I was enjoying him inside me.

"Oh, god, it's so big", I said in a whisper. "Your cock is so thick. It's so warm inside me. You are stretching me but it feels so good."

"Just take it slow" he said. "Just go slow, don't hurt yourself. You feel awesome, it is just great", he said quietly.

"It's thick but it feels really good", I said. "Dude, it's really warm! I like it!", I laughed out loud. I slowly slid almost all the way down, devouring its length deep into my body.

"It's longer than I thought it would be. It's so deep", I whispered in a husky voice, eyes closed, as he bottomed out to the root up my tight ass.

"Yeah, it feels great, but go slow. Get used to it all the way in."

With that, he nudged his thick rod all the way balls deep into me. It created an almost sickening sense of fullness that was uncomfortable, and the thickness at the base was more than I could stand, splaying my tight ring to a painful diameter.

"Oooowwwww!", I yelled. "Too deep!"

I rose a little, letting some of his meat exit my body. I opened my eyes and pulled my balls off to the side to get a good look at his cock lodged up my ass. I was getting fucked in the ass, or rather, I was fucking him with my ass. His cock was thick and warm and filled me to the point where it was weird; there was the nice entrance feeling but all the way down it was like my insides were being compressed in ways not intended by nature. Duh! This is of course true because it is not natural to have a seven inch thick cock plowing up inside you! I was stretched wide and it was a bit painful when his penis was all the way in. It was super thick at the base so I was careful not to bounce down on it because that caused a flat out uncomfortable stretching of my no-longer-virginal anal ring.

Tim moaned as I slowly pulled up and rode down on his ridgid rod. After about ten minutes my ass became accustomed to the invasion and from then on it was enjoyment for both. In order to maintain good feeling, I repeatedly slid all the way off, adding lube and letting it slide up inside me again and again, almost taking him to the base but being careful not to go too deep.

"Oh, yes, that is so good", I moaned as I got into a nice but slow fucking rhythm with his big dick up my ass.

"I am loving your huge cock up my ass", I said in a low voice.

I began to vary my motions with his thick penis probing and exploring various areas deep within my body, becoming more adventurous and swirling my hips slightly as I moved up and down. Each new angle of penetration cast a net of unexpected and wonderful sensations, and Tim enjoyed every variation as much as I did. He began to move his hips, meaning that sometimes his cock popped out of my ass and we had to nestle it against my ring and work it back inside me. These moments were the most enjoyable to me, but I knew that going deep inside my body for Tim was probably best for him, so I mixed it up, popping his cock out of me from time to time repeatedly penetrating only a few inches then allowing him to slip almost all the way to the hilt over and over again.

"I love you fucking my tight ass" I managed to moan, eyes closed and deep in thought. "It feels so good in my tight virgin ass."

"It feels great", he said.

He lubed his warm hands and began caressing my cock and balls. Of course it felt terrific. Having his thick tool inside me while he was stimulating me with his hands was an acute assault of pleasure unlike any previous experience.

With each passing moment Tim's invasion became increasingly easy and pleasurable. After ten minutes of anal sex, I had widened up enough that he could pull out and pop right back in with no pain at all and, in fact, it felt really great, especially that first inch or two. In fact, as time went on I enjoyed teasing his thick cock head at my anus and then letting it slide inside me very slowly.

I was totally enjoying myself and my focus was clear and bright and I was ready to bring him to the edge and beyond. I opened my eyes and said, "I bet you feel pretty good you got to pop a virgin ass, don't you?"

"Yes, I do. Oh, wow I feel so lucky you wanted this."

"Wanted what?", I hissed, sliding down his thick pole.

"Wanted to have...wanted to do it with me."

"Let's be honest", I said practically panting, "fuck me in the ass. Splay my ass open with your thick cock, that's what we're doing here", I growled as Tim breathed deeply, heavily.

"You like fucking my ass don't you?", I said.

Initially I had my hands to my side but we had crawled and bounced our way near the headboard, which had some spindles and a top rail that I could grasp. I was leaning on the headboard arching over him. In this position I could lean all the way back and rest against the top of his thighs, his cock sliding to a perfect depth just shy of being buried all the way inside me.

"Yeah, I do. I love fucking you in the ass", he said. "You're tight and hot and I am loving burying my thick cock in your tight asshole. It feels so fucking good."

I felt like a genuine whore and it was exciting to be dominating the act but submissive in action. Although I was controlling the pace and tone, he was still the one with his big dick buried deep inside my body. I slipped his cock in my ass in a few short strokes, then I pulled it out, re-lubed it and tried something new.

With his slippery dick knocking at my back door, I began to gyrate my hips in a circle while keeping light pressure on the head of his cock. His head popped back inside and soon I was being internally explored by a thick cock at an excruciatingly slow pace and at more severe angles than we had enjoyed up to this point. The friction, the probing, the depth, pulling his rod out of me and burying it in me repeatedly...it was as much as he could take.

"Oh my god dude I love this but you better slow down or I am going to come!", he said. "This is incredible! I can't believe you have never done this!", he screamed.

"Yeah, but I've thought about it!", I said loudly as I continued spiraling down, gobbling his penis with my body. "Come in my ass!", I demanded.

My cock was rock hard and he was still slowly stroking it, my balls tightening as he invaded my hole with my sprial downard motions. I was gyrating up and down like a screw, impaling myself in a clockwise twisting motion. At the end of a downward ride my balls were sliding against his body and it felt amazing. My balls are really sensitive and I knew that if he kept stroking my cock and touching my balls I would come and I didn't want to yet, so I gently moved his hands away from my penis.

I began to step up the pace and intensity of my motions on his thick tool, sliding and slicing and screwing its way deep into my body over and over. A strange feeling gripped me and I was totally focused on him to come inside me. In the simplest terms it was a control thing although I doubt that makes much sense. Heavy breathing, the wet smacking and crinkling of a rubber, and the greasy sounds of his thick cock sawing and surging up my ass splintered the silence of the room. With surprising suddenness his orgasm began. For the first time since we started fucking he grabbed my ass cheeks and pushed deep inside me, and my balls came to rest on his abdomen. A scream found its way past my lips as I was impaled deeply by Tim's rock hard thick cock. The pain escalated quickly as his warm tool thickened and plunged deeper, all the way to the hilt of his cock, forcing my anus wide open. I was frozen in place with his cock lodged inside me, and he was bucking, driving his meat inside me only a fraction of an inch but with a great deal of pressure. His dick was so thick at the base it was like having forceps repeatedly widening my asshole. This was not at all a pleasant experience but even as I was getting split I was thinking I'd definitely do it again because it was so different and exciting. At least next time I'd know what to expect when we had anal sex and I could mentally and physically prepare to be gored. Up to that point he'd been very gentle and allowed me to control everything, so I figured a few seconds of pounding my ass was tolerable.

His orgasm boiled from his balls all the way through his body in a massive, consuming convulsion. I couldn't move much with his grip on my hips, and his cock was buried so deep inside me my balls were getting tickled by his wiry pubic hair. He jerked and spasmed a few more times, wretching the last blobs of semen into his rubber. Tim's cock thickened even more as he climaxed and drove every millimeter deep into my body. My ass yawned open to a diameter I had never experienced, one in which nerve endings were stretched, rubbed raw as I struggled to maintain his large tool deep within my body as it flexed and spat come into its rubbery sheath.

As he continued to orgasm and slip his thick, hard penis deep within me, his cock was bulging and stretching my body, probing me at angles and in ways that were very different than I had experienced when using dildos. One big difference between using a dildo and getting fucked by a real cock were the various angles that his penis tracked as it dipped and slipped inside me, especially when he was wracked by orgasm. As he came, he screamed, pounding me hard, and as he pulled out even a few inches when it went back in it was different every time. Sometimes his penis scraped my prostate, sometimes it felt like it was driving into my stomach! But every time he went inside me it was not exactly the same as the previous penetration. As a result the sensations were different every time, too.

Another difference was the sheer unpredictability of it. With a dildo, you always know excactly how deep and how fast it's going to probe and prod you because you are in control, so you know exactly what to expect. Getting fucked in the ass by a hard cock attached to another brain was an incredibly different experience because every action was a complete surprise. When he was in the midst of orgasm, I had no way to know how hard he was going to fuck me from second to second, or how he was going to twist and jab his cock inside me. Even though I was on top of him, he was still able to buck and fuck me and it was a mix of extreme pleasure and moderate but tolerable pain.

As he continued to orgasm I silently wondered why I had waited so long to be penetrated by a real live penis. I had enjoyed dildo play for years and this radically different experience was so pleasurable it was an absolute certainty I'd do it again and again, either with Tim or with someone new.

In these waning seconds of his orgasm I also realized I was totally detached from him as a friend or companion, and the only real thing we had in common at this moment in time was sharing incredible pleasure by fitting our bodies together. He could have been anyone. Although I've had one night stands with women, there was always something, no matter how slight, that resembled caring, warmth, and love. I was never one to just flat out fuck a woman and not care about her at least somewhat, even if we didn't feel strongly for each other. It always enhanced the experience, even for women I never met again, to kiss, caress each other...to show that for these minutes or hours your partner cares, even if it is only about pleasure.

Although my experience in this area is admittedly rather limited, what my female partners had in common is that they all wanted a little something more, and I was always happy to give it, even if it was just a warm thought, a gentle caress, or a tender kiss on the cheek. In that way, my experiences with women didn't seem cold, and they weren't limited entirely to physical pleasure in a manner of speaking. Maybe I romanticise what women felt for me but that's not likely, and I raise this point for one reason only: this experience had absolutely nothing in common with those experiences.

As his orgasm ebbed I realized this with perfect clarity, objectifying him in a way that I had never, ever experienced doing so to a woman. I was taking advantage of him per se despite the fact that he just wrenched out an orgasm deep inside me. It is difficult to describe my emotional state other than to say that as soon as he came, I began to think of what my next action would be. I had wanted him to come inside me because it was just another activity, another experience I wanted to have and enjoy. Oddly enough it had nothing to do with him personally. Again, I doubt this makes much sense except to those that have experienced this level of emotional detachment, and that's something that's quite honestly not as common as many Cassanovas may imply or have you believe.

Slowly he calmed down and let go of my ass cheeks and I slid up and off his softening tool. In my mind, I began to put into words this experience on which I'd reflect in the next few days and weeks, maybe years:

> Some dude popped in my ass.

> Some guy I barely knew fucked me up the ass.

> A friend of a friend and I went to a concert, came back to his place, and he jammed his big cock up my ass and orgasmed.

> Some guy came inside me as I rode his hard cock all the way down to his hairy balls.

> I decided to have a gay experience so I sucked some guy's cock and then let him push his cock against my asshole and penetrate me.

All these thoughts were true. As his penis slipped out of me I silently wondered how I would summarize and reflect on this first time experience ten years from now, or if this reflective moment itself would be the summary.

His tool flopped against his abdomen and it looked huge even soft and I marvelled that I had just had sex with it. I felt a little sore but OK enough and I was eager for reciprocation.

"How do you feel?", he asked with genuine concern.

"I feel like I just got fucked up the ass with a big dick for fifteen minutes", I laughed.

"I feel fine, Tim. I'm OK", I said smiling. "I'd do it again. But let's talk about what we're going to do now. He knew exactly what I meant. We separated and he got into a submissive position on all fours and I could hardly wait to drive. I was excited and I wanted to come. I can recall few times being so keyed up and I knew I wasn't going to last long.