Second time with Tim
- 2 years ago
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Third Time With Tim free porn video
This is the third part of my encounters with Tim, and is an immediate continuation of story 2, so you may want to at least go back and read the second encounter with Tim, if not the first and second to get a full feel for our encounters!
**
We got upstairs, still covered in each other’s cum as it was starting to dry on is a bit and the heavier amounts dripping some down our legs. We headed into my bedroom, which was the master bedroom of the house, and then into the bathroom. Neither really said a word.
I leaned into the shower and turned the water on as hot as it would go so it would warm up fast. After all, it was cold out!
“It will probably take a few for the water to warm up” I said to sort of ease the tension that was growing, now that both of us had already blown our loads and gotten the horniness out of us that had been building since the last time we fooled around.
We stood in silence, both really unsure of what to do, and now suddenly acting shy as if we were both embarrassed by our actions, eyes avoiding each other. I then decided to break this silence and try to ease us both. Mostly for me, to be honest, and not even really concerned with his feeling on our current situation.
“This is weird isn’t it. Like, now that were done, it feels weird when a few minutes ago, it felt like nothing was strange at all and that it was as if we did this kind of thing all the time…”
“Yea…” Tim was staring down, acknowledging it was weird. “All I wanted to do all week was fool around and now that we did, I feel like we did something wrong and that I’m going to regret doing that. I mean, now when someone calls me a ‘cocksucker’ as an insult, in my mind, I’m gonna be like ‘Well, yea, I kinda am’”.
“I know, I felt like that the first few times. And then suddenly you notice people saying things more and in the back of your mind you think ‘Oh shit, do they know?’ And then I still feel strange the next morning. Even if I’m just fooling with myself, or web chatting online, I feel like I did something wrong. But then a few days later, I want to do it again so bad.”
Tim seemed more relaxed that it was not just him feeling like this. Truth is, as much as I had now fooled around in my life, I still felt strange about it. Like, regardless of how much I wanted to play with another guy, and no matter how much I enjoyed it, I still sort of had that regret in the back of my mind.
The water was now hot, so we both moved into the shower, carrying on our conversation as we started to wet our bodies, slowly washing off the now dried cum.
“Honestly, ever since my old friend Mike, who I first started playing around with moved, I have felt a bit strange about messing with guys. When he still lived here, and we planned to fool around, and we had our fun in secret, it felt more normal. But then he moved and I fooled around with another guy or two randomly, and it felt regretful, whereas it never felt that way once we started fooling around a lot. Guess because we both were holding onto that secret.”
Tim relaxed a bit. “Well, I guess I have been your new Mike the past week then, do you feel as regretful?”
“Don’t take this the wrong way, but yea. Like, I know you were curious, but sort of feel guilty pushing you. I mean, we’re washing each other’s cum off our bodies in the shower together. I don’t think you quite envisioned this the first time was were naked together. Did we take this too far?”
“Nah, I’ve been fantasizing about this kind of stuff way too much to have ever held back. Just needed someone to push me along a little, and I’m glad we did fool around. Certainly fulfilled some fantasies I never thought would happen. I guess it was just so unexpected, it feels a little strange. Like, fantasizing about a dick in my mouth while I watch a video of a guy jerking of is one thing. To actually taste a guys is so much different.”
“Again, don’t take this the wrong way, but I’m really glad we aren’t real good friends and just sort of started hanging out not long ago, makes this feel way less awkward.” We were both now relaxed and having a casual conversation as we continued washing up.”
“Yea, I’m really glad that it worked out the way it did. I mean, if I expressed any of these thoughts to anyone else in this group of friends, I’d probably never have heard from anyone again.” Tim seemed to be warming up more to the concept of us fooling around, and it was starting to warm me up too on the idea.
“That’s actually the best way you could have described it, I don’t feel nearly as bad about this now. I just feel like I may have pushed too much because I miss what Mike and I used to do. Maybe this doesn’t have to feel so weird and we can just have a little fun sometimes when we over do it at the bar.”
Tim was now stepping out of the shower and grabbing a towel to dry off as he responded much more up beat. “Yea, that would be pretty cool, I mean, not doing it all the time, just here and there when we just get really horned up, or real drunk and stuff just happens. Just gotta be sure it’s never anywhere near anyone else.”
It seemed we had now set terms and as I finished drying up, we headed back down stairs, now clean of cum and freshly showered, yet still naked.
We got down stairs and saw our cloths s**ttered about.
“Now what” Tim said, sort of confused of the next steps here.
“Um, I don’t know, it’s not even really that late, this is usually like a 4am kind of event and I just pass out” I sort of laughed a bit as I trailed off my sentence. And really, that was the case. It was always time to crash at this point, but here we were, around 1am, before we would have even got home from a bar.
“Yea I know, guess we were just so excited, we only got here like 30 minutes ago. Didn’t take us long to get off.” And just like that, Tim had started talking much more casual about our little experience.
“Yea true, well, after the last time, we kinda just left it wanting more, so the second we started, it was like trying to fight it back the whole time.”. And that was really the truth. After the first time, all I wanted to do was get my lips around Tim’s cock. And once I did, I was primed to explode. “Guess that means next time we can go slower and savor the experience better. I mean, if you want to fool around again still, no big deal if not.”
“Oh of course I do! Now that the little awkwardness is over, I still feel a bit weirded out, but I don’t feel like its something I DON’T want to do again.”
“Good, because I definitely do” I snapped back laughing. “I would be quite upset if I didn’t get to feel that cock again.”
We were both now sitting on the couch next to each other, naked, cocks limp. It was silence again for a few moments.
“So do you want to try having some fun again now, or is that too sudden? I mean, we just came, we definitely won’t blow our loads that fast again, maybe just hands this time?” I was now reenergized since we became more comfortable and wanted nothing more than to get hard with Tim again.
“Actually, yea that would be fun, I’m strangely past all the jitters now and getting sort of horny again being naked with you!”. Tim started to touch his limp dick a little bit, trying to stimulate it.
“Maybe we should get some porn on or something, to give us a boost here.” I then grabbed the remote for my smart TV and navigated to Porn Hub. “What kinda stuff do you watch? I’m pretty open here.”
“Well, I mean lately I’ve just been watching guys jerk off since that had been my fantasy, but now that we’ve done that and I can just turn my head and see you… How about just some pussy, maybe anal too?”
“Sure, good for me”. I went under the ‘Anal’ category and in no time a smoking hot brunette was taking a guys dick deep into her pussy, and then in her ass. We had started stroking ourselves, and we had worked ourselves both up to about 75% hard, occasionally glancing at each other, but more focused on the TV.
“So what sort of porn do you normally watch? I know you said you’re open to basically anything, but if you were alone, what would you have gone for?”
“Probably either lesbian or blowjobs” I replied back, and that was absolutely my preference. Strange that I enjoyed guy on guy so much and my go to porn was girl on girl. However, never hated mixing in a nice cock getting sucked.
“Cool, like those too myself.” We continued talking porn a bit as we kept stroking, now acting just like stroking buddies moreso than guys that fooled around. “I love pussy, but sometimes watching anal is better, seeing how tight it is, and after the dude is so lubed up from her pussy, it slides right in.”
“Yea, wonder if they prep ahead of time for it to make it slide in easier, like, use a dildo, or another guy to warm the thing up so its maybe a bit looser?” We were now debating how anal worked in porn. Strange topic.
“Well,” Tim continued, as if he was some expert, “as tight as it looks it couldn’t have had too much action, I mean, in the beginning, it was just a tight little pink button basically, looked like it hasn’t been touched in the slightest.”
I still had to imagine that there was some sort of ‘warmup’, and that a girl doesn’t just take it by surprise and not even wince in these videos. “I Don’t know, I mean, that’s just what assholes look like regardless, kinda universal. Like, she doesn’t even react when it happens.”
Tim got suddenly defensive. “What, are you saying all assholes are created equal? Because they certainly aren’t.”
“I mean yea, they’re a bit different, like larger people are gonna have a different situation going on, or hairy people are gonna have something different going on, but an asshole is an asshole, they’re all little pink buttons.”
“Wait, hairy body? Like guys? Are you comparing a guys asshole to a girls?”
“Yea, same thing, haven’t you ever seen a guys asshole? I just assumed when you said you’d been watching guys jerk off lately that you’ve watched a tad more than just a guy jerking off, maybe some more guy action…” I had absolutely assurance in my mind that Tim had not just watched porn of a guy jerking of, but guys doing all sorts of stuff, including anal. Apparently I was mistaken.
“No, I literally just watched guys jerk off. But now I’m curious, can you find pics of a guy’s asshole? I still can’t believe it would look exactly the same.”
I did my best on Bing to find some images and then there we were, stroking our cocks with pictures of guys assholes on the screen. Tim seemed confused that it really did look very similar.
“Wow, didn’t know that. Basically the same thing, especially the non hairy ones. Like, is mine like that?”
Then a leap was taken with us. “Bend over and let me see and I’ll tell you.”
Tim then stood up and bent over and spread his legs a bit. He wasn’t very hairy anywhere on his body, so his was fairly similar to everything we’d been looking at. “Yep, nice smooth little button back there!”
He sat back down, still a bit confused. “Really? Can I see yours?”.
“Sure” as I shifted to all fours on the couch, spread my legs a bit and then used my hands to spread my cheeks, making things seem even pinker than they probably should, half showing it of, half trying to prove a point.
“Holy shit, it looks so pink and tight, damn.” As Tim sounded surprised and then trailed off as I held my pose.
“Does it stack up tot eh ones you see on girls?”
“Hell yea, it’s nicer than some. Damn, its so hot.”
“Glad you like” as I continued to hold my pose a little longer before I returned to my sitting position. I noticed Tim was now rock hard. “Wow, that really did get you hard, must have really liked what you saw.”
“Hey, like you said, an asshole is an asshole. Is it as tight as it looks? I mean, you couldn’t get a toothpick in there.”
“Haha, trust me, can fit way bigger things than a toothpick.” As I made it loud and clear that I have had some anal experience one way or another.
“Really? Like, you’ve put something in there? Like, a finger or something?” Tim was really locked into this now, but he didn’t quite get what I meant.
“Yea, a finger or two, handle of a kitchen spoon.” I started with that and then paused a bit before finally saying “And a cock.”
Silence.
“Really?” after a little pause. “You’ve had a guys cock in your?”
“You can’t tell anyone, like, that would be social suicide there. But yea, Mike and I used to do a lot of anal.”
“Wow, didn’t know you guys went THAT far. That’s like. Wow. I’ve never even thought of guy on guy anal.”
“Not really any different than guy on girl, I mean, for the guy that’s sticking it in. You ever do anal with a girl?”
“No, always wanted to but never did.” Tim was clearly an anal fan, but apparently this was another fantasy that he had never tried.
“Well, certainly not going to push this one hard, because it’s a damn big step, but if you ever want to try it, I wouldn’t mind feeling you in me.” We paused a bit and just sat there jerking off, pondering the situation.
“I mean, I really do but at the same time, I really don’t. That’s like a major line….”. Tim was beyond nervous about this, and I really was too. If we crossed that line too fast, then there is no going back and it could crush the fun we had been having.
“Oh I know, absolutely no pressure, you tell me, but know that it is always an option.”
“Like, how would it work, you bend over, or on your back, or what?”
“However you’d want, I can sit and ride you, bend over, lay on my back, whatever.”
We had another little silence.
“Can I see it again?” and with that, I got back on all fours and quickly spread my cheeks. It really seemed like Tim was thinking about trying it tonight and I was now rock hard at the thought. “It looks so tight, I can’t believe I’d even fit in there.”
“You would, and it would be real tight. Like, it would grip your cock hard. Probably won’t last long to be honest.”
“I just came a little ago so I can last long. Can I try? I can’t even believe I’m considering this, but it just looks so nice and tight”.
“How about I suck you a bit to get you a little lubed up and then I can bend over the couch and you can try.” As I finished talking I was already moving to take Tim’s cock into my mouth. It didn’t take long to get Tim’s now throbbing cock nice and slick. I then stood up, walked over to the side of the couch and bent over the arm of the couch, spreading my legs a bit.
“I can’t believe I’m doing this” Tim said as he walked over, positioning behind me. I could hear him take a big, deep breath, before I felt the tip of his cock touch against the inside of my cheeks. Slow and steady, I could feel the head of his cock pushing into my hole, griping every bit of him as he slowly made his way in. We both started groaning as he continued.
Now with just the head pushing inside, Tim moved his body closer, now pressing his hips toward my butt. Every little bit he pushed in with forced a loud moan from him. Meanwhile, I was feeling every little bit of him slowly entering in, nice and slow and steady, which was actually perfect for me to adjust to having it in me.
As he slowly continued forward, I could feel more and more of him sliding into me, as he continued moaning as the entrance of my hole gripped the shaft of his cock as tight as it could. Little by little his entire cock disappeared into me. At first Tim kept it all the way in, slightly probing around with his shifting hips until he started with withdraw, again nice and slowly. The slow, steady feeling was amazing, as it had been quite a while now since I’ve felt a guy’s cock in me.
Tim now started to slowly move in and out, his cock sliding back and forth through the entrance of my butt, which was gripping and tightening along the entire length of his shaft as he shoved his dick deep into my ass, only to just as quickly pull back so that his head was just barely still in. He began thrusting in and out like a pro, as if he had done this a million times. Truth be told, it was probably no strange action to him, same movements as with a girl.
We both began to moan louder and louder, more and more often. “Oh god, it’s so tight” Tim was able to blurb out in the process, clearly enjoying it. He kept pushing deeper and deeper it seemed, thrusting harder and harder. I could feel every inch of him pushing in, feeling my hole tightening harder and harder, squeezing every bit of him.
“Can I fuck you on your back? I want to see your cock.” Tim sort of surprised me, I had figured bending over for him would be best, since this was so new, but now in the moment, it seemed he had zero inhibitions. I also liked the idea of it too, so I started to move around as Tim’s dick slid out of him, I repositioned on the end of the couch, on my back, legs spread up. Tim propped them against his shoulder and then slid right back into me.
At this point, my cock was rock hard, shifting back and forth as Tim pushed in and out of me, balls swaying back and forth. It felt incredible, and the image, of looking down and seeing the end of his shaft at times, while my cock was bouncing around was amazing. Tim was staring straight down at the3 scene as he said, “I’m not gonna last long”.
“Don’t hold back or think about it, just cum, I’m not far myself.”
Tim started to speed up his thrusts, pushing harder and harder each time, faster and faster. We both started moaning louder and panting harder. I grabbed hold of my cock and started stroking, as I got closer and closer. And just then, Tim let out a loud grunt as I felt his movement stop and a blast of warmth inside of me as he shot his cum as far as it would go into me. Wave after wave, I could feel his cock pulsing as another blast unleashed. It felt like even more cum than earlier.
As he finished draining, as my hole was squeezing out every last drop, I couldn’t hold back any longer myself and a stream of warm, thick cum poured from my cock, spilling all over my chest. Tim slowed his movements, his cock still hard inside of me, as we both came down from the ecstasy.
“Holy shit, that felt amazing” Tim said as the silence broke. At this point, the whole shyness factor was gone.
“Yea, that was absolutely amazing. I can’t remember the last time anything felt that good.”
Tim pulled himself out and away as my legs relaxed down. I could feel his cum slowly starting to fall out of me, so picked up a leg and moved a hand under to catch it. “Woah…” I heard Tim gently say as from his view, he could see a bit of his cum dribble out of my now mostly closed hole.
“Should probably go clean up again, well, at least me” I mentioned as this would probably continue to dribble out a bit here and there still.
We headed back upstairs and hopped in the shower for the second time that night. This time, the attitude was far different, and more relaxed and talkative.
“Does it hurt?” Tim asked
“At first a little, as you first start to go in, but then it starts to relax and then suddenly feels amazing.”
“Maybe we can try it the other way around some time. You just seemed to enjoy it so much I’m a bit curious, but I don’t think I’m quite ready.”
“Sure!” I was happy to hear he had now a positive attitude and was no longer nervous on this topic at all. “You should play with it yourself a tad at home and see how you like feeling something in there, then it won’t be such a shock to try out.”
“Good idea, maybe I’ll try that”.
We chatted a bit more that evening in the shower and after drying off and getting our cloths back on. Then, we simply went our separate ways, headed off to bed, with no longer any curiosities on the encounters we were having. We continued to meet up after the bar like this over the next month or two, much the same as the last two times. Then, eventually, things changed a bit… (TBC)
**
We got upstairs, still covered in each other’s cum as it was starting to dry on is a bit and the heavier amounts dripping some down our legs. We headed into my bedroom, which was the master bedroom of the house, and then into the bathroom. Neither really said a word.
I leaned into the shower and turned the water on as hot as it would go so it would warm up fast. After all, it was cold out!
“It will probably take a few for the water to warm up” I said to sort of ease the tension that was growing, now that both of us had already blown our loads and gotten the horniness out of us that had been building since the last time we fooled around.
We stood in silence, both really unsure of what to do, and now suddenly acting shy as if we were both embarrassed by our actions, eyes avoiding each other. I then decided to break this silence and try to ease us both. Mostly for me, to be honest, and not even really concerned with his feeling on our current situation.
“This is weird isn’t it. Like, now that were done, it feels weird when a few minutes ago, it felt like nothing was strange at all and that it was as if we did this kind of thing all the time…”
“Yea…” Tim was staring down, acknowledging it was weird. “All I wanted to do all week was fool around and now that we did, I feel like we did something wrong and that I’m going to regret doing that. I mean, now when someone calls me a ‘cocksucker’ as an insult, in my mind, I’m gonna be like ‘Well, yea, I kinda am’”.
“I know, I felt like that the first few times. And then suddenly you notice people saying things more and in the back of your mind you think ‘Oh shit, do they know?’ And then I still feel strange the next morning. Even if I’m just fooling with myself, or web chatting online, I feel like I did something wrong. But then a few days later, I want to do it again so bad.”
Tim seemed more relaxed that it was not just him feeling like this. Truth is, as much as I had now fooled around in my life, I still felt strange about it. Like, regardless of how much I wanted to play with another guy, and no matter how much I enjoyed it, I still sort of had that regret in the back of my mind.
The water was now hot, so we both moved into the shower, carrying on our conversation as we started to wet our bodies, slowly washing off the now dried cum.
“Honestly, ever since my old friend Mike, who I first started playing around with moved, I have felt a bit strange about messing with guys. When he still lived here, and we planned to fool around, and we had our fun in secret, it felt more normal. But then he moved and I fooled around with another guy or two randomly, and it felt regretful, whereas it never felt that way once we started fooling around a lot. Guess because we both were holding onto that secret.”
Tim relaxed a bit. “Well, I guess I have been your new Mike the past week then, do you feel as regretful?”
“Don’t take this the wrong way, but yea. Like, I know you were curious, but sort of feel guilty pushing you. I mean, we’re washing each other’s cum off our bodies in the shower together. I don’t think you quite envisioned this the first time was were naked together. Did we take this too far?”
“Nah, I’ve been fantasizing about this kind of stuff way too much to have ever held back. Just needed someone to push me along a little, and I’m glad we did fool around. Certainly fulfilled some fantasies I never thought would happen. I guess it was just so unexpected, it feels a little strange. Like, fantasizing about a dick in my mouth while I watch a video of a guy jerking of is one thing. To actually taste a guys is so much different.”
“Again, don’t take this the wrong way, but I’m really glad we aren’t real good friends and just sort of started hanging out not long ago, makes this feel way less awkward.” We were both now relaxed and having a casual conversation as we continued washing up.”
“Yea, I’m really glad that it worked out the way it did. I mean, if I expressed any of these thoughts to anyone else in this group of friends, I’d probably never have heard from anyone again.” Tim seemed to be warming up more to the concept of us fooling around, and it was starting to warm me up too on the idea.
“That’s actually the best way you could have described it, I don’t feel nearly as bad about this now. I just feel like I may have pushed too much because I miss what Mike and I used to do. Maybe this doesn’t have to feel so weird and we can just have a little fun sometimes when we over do it at the bar.”
Tim was now stepping out of the shower and grabbing a towel to dry off as he responded much more up beat. “Yea, that would be pretty cool, I mean, not doing it all the time, just here and there when we just get really horned up, or real drunk and stuff just happens. Just gotta be sure it’s never anywhere near anyone else.”
It seemed we had now set terms and as I finished drying up, we headed back down stairs, now clean of cum and freshly showered, yet still naked.
We got down stairs and saw our cloths s**ttered about.
“Now what” Tim said, sort of confused of the next steps here.
“Um, I don’t know, it’s not even really that late, this is usually like a 4am kind of event and I just pass out” I sort of laughed a bit as I trailed off my sentence. And really, that was the case. It was always time to crash at this point, but here we were, around 1am, before we would have even got home from a bar.
“Yea I know, guess we were just so excited, we only got here like 30 minutes ago. Didn’t take us long to get off.” And just like that, Tim had started talking much more casual about our little experience.
“Yea true, well, after the last time, we kinda just left it wanting more, so the second we started, it was like trying to fight it back the whole time.”. And that was really the truth. After the first time, all I wanted to do was get my lips around Tim’s cock. And once I did, I was primed to explode. “Guess that means next time we can go slower and savor the experience better. I mean, if you want to fool around again still, no big deal if not.”
“Oh of course I do! Now that the little awkwardness is over, I still feel a bit weirded out, but I don’t feel like its something I DON’T want to do again.”
“Good, because I definitely do” I snapped back laughing. “I would be quite upset if I didn’t get to feel that cock again.”
We were both now sitting on the couch next to each other, naked, cocks limp. It was silence again for a few moments.
“So do you want to try having some fun again now, or is that too sudden? I mean, we just came, we definitely won’t blow our loads that fast again, maybe just hands this time?” I was now reenergized since we became more comfortable and wanted nothing more than to get hard with Tim again.
“Actually, yea that would be fun, I’m strangely past all the jitters now and getting sort of horny again being naked with you!”. Tim started to touch his limp dick a little bit, trying to stimulate it.
“Maybe we should get some porn on or something, to give us a boost here.” I then grabbed the remote for my smart TV and navigated to Porn Hub. “What kinda stuff do you watch? I’m pretty open here.”
“Well, I mean lately I’ve just been watching guys jerk off since that had been my fantasy, but now that we’ve done that and I can just turn my head and see you… How about just some pussy, maybe anal too?”
“Sure, good for me”. I went under the ‘Anal’ category and in no time a smoking hot brunette was taking a guys dick deep into her pussy, and then in her ass. We had started stroking ourselves, and we had worked ourselves both up to about 75% hard, occasionally glancing at each other, but more focused on the TV.
“So what sort of porn do you normally watch? I know you said you’re open to basically anything, but if you were alone, what would you have gone for?”
“Probably either lesbian or blowjobs” I replied back, and that was absolutely my preference. Strange that I enjoyed guy on guy so much and my go to porn was girl on girl. However, never hated mixing in a nice cock getting sucked.
“Cool, like those too myself.” We continued talking porn a bit as we kept stroking, now acting just like stroking buddies moreso than guys that fooled around. “I love pussy, but sometimes watching anal is better, seeing how tight it is, and after the dude is so lubed up from her pussy, it slides right in.”
“Yea, wonder if they prep ahead of time for it to make it slide in easier, like, use a dildo, or another guy to warm the thing up so its maybe a bit looser?” We were now debating how anal worked in porn. Strange topic.
“Well,” Tim continued, as if he was some expert, “as tight as it looks it couldn’t have had too much action, I mean, in the beginning, it was just a tight little pink button basically, looked like it hasn’t been touched in the slightest.”
I still had to imagine that there was some sort of ‘warmup’, and that a girl doesn’t just take it by surprise and not even wince in these videos. “I Don’t know, I mean, that’s just what assholes look like regardless, kinda universal. Like, she doesn’t even react when it happens.”
Tim got suddenly defensive. “What, are you saying all assholes are created equal? Because they certainly aren’t.”
“I mean yea, they’re a bit different, like larger people are gonna have a different situation going on, or hairy people are gonna have something different going on, but an asshole is an asshole, they’re all little pink buttons.”
“Wait, hairy body? Like guys? Are you comparing a guys asshole to a girls?”
“Yea, same thing, haven’t you ever seen a guys asshole? I just assumed when you said you’d been watching guys jerk off lately that you’ve watched a tad more than just a guy jerking off, maybe some more guy action…” I had absolutely assurance in my mind that Tim had not just watched porn of a guy jerking of, but guys doing all sorts of stuff, including anal. Apparently I was mistaken.
“No, I literally just watched guys jerk off. But now I’m curious, can you find pics of a guy’s asshole? I still can’t believe it would look exactly the same.”
I did my best on Bing to find some images and then there we were, stroking our cocks with pictures of guys assholes on the screen. Tim seemed confused that it really did look very similar.
“Wow, didn’t know that. Basically the same thing, especially the non hairy ones. Like, is mine like that?”
Then a leap was taken with us. “Bend over and let me see and I’ll tell you.”
Tim then stood up and bent over and spread his legs a bit. He wasn’t very hairy anywhere on his body, so his was fairly similar to everything we’d been looking at. “Yep, nice smooth little button back there!”
He sat back down, still a bit confused. “Really? Can I see yours?”.
“Sure” as I shifted to all fours on the couch, spread my legs a bit and then used my hands to spread my cheeks, making things seem even pinker than they probably should, half showing it of, half trying to prove a point.
“Holy shit, it looks so pink and tight, damn.” As Tim sounded surprised and then trailed off as I held my pose.
“Does it stack up tot eh ones you see on girls?”
“Hell yea, it’s nicer than some. Damn, its so hot.”
“Glad you like” as I continued to hold my pose a little longer before I returned to my sitting position. I noticed Tim was now rock hard. “Wow, that really did get you hard, must have really liked what you saw.”
“Hey, like you said, an asshole is an asshole. Is it as tight as it looks? I mean, you couldn’t get a toothpick in there.”
“Haha, trust me, can fit way bigger things than a toothpick.” As I made it loud and clear that I have had some anal experience one way or another.
“Really? Like, you’ve put something in there? Like, a finger or something?” Tim was really locked into this now, but he didn’t quite get what I meant.
“Yea, a finger or two, handle of a kitchen spoon.” I started with that and then paused a bit before finally saying “And a cock.”
Silence.
“Really?” after a little pause. “You’ve had a guys cock in your?”
“You can’t tell anyone, like, that would be social suicide there. But yea, Mike and I used to do a lot of anal.”
“Wow, didn’t know you guys went THAT far. That’s like. Wow. I’ve never even thought of guy on guy anal.”
“Not really any different than guy on girl, I mean, for the guy that’s sticking it in. You ever do anal with a girl?”
“No, always wanted to but never did.” Tim was clearly an anal fan, but apparently this was another fantasy that he had never tried.
“Well, certainly not going to push this one hard, because it’s a damn big step, but if you ever want to try it, I wouldn’t mind feeling you in me.” We paused a bit and just sat there jerking off, pondering the situation.
“I mean, I really do but at the same time, I really don’t. That’s like a major line….”. Tim was beyond nervous about this, and I really was too. If we crossed that line too fast, then there is no going back and it could crush the fun we had been having.
“Oh I know, absolutely no pressure, you tell me, but know that it is always an option.”
“Like, how would it work, you bend over, or on your back, or what?”
“However you’d want, I can sit and ride you, bend over, lay on my back, whatever.”
We had another little silence.
“Can I see it again?” and with that, I got back on all fours and quickly spread my cheeks. It really seemed like Tim was thinking about trying it tonight and I was now rock hard at the thought. “It looks so tight, I can’t believe I’d even fit in there.”
“You would, and it would be real tight. Like, it would grip your cock hard. Probably won’t last long to be honest.”
“I just came a little ago so I can last long. Can I try? I can’t even believe I’m considering this, but it just looks so nice and tight”.
“How about I suck you a bit to get you a little lubed up and then I can bend over the couch and you can try.” As I finished talking I was already moving to take Tim’s cock into my mouth. It didn’t take long to get Tim’s now throbbing cock nice and slick. I then stood up, walked over to the side of the couch and bent over the arm of the couch, spreading my legs a bit.
“I can’t believe I’m doing this” Tim said as he walked over, positioning behind me. I could hear him take a big, deep breath, before I felt the tip of his cock touch against the inside of my cheeks. Slow and steady, I could feel the head of his cock pushing into my hole, griping every bit of him as he slowly made his way in. We both started groaning as he continued.
Now with just the head pushing inside, Tim moved his body closer, now pressing his hips toward my butt. Every little bit he pushed in with forced a loud moan from him. Meanwhile, I was feeling every little bit of him slowly entering in, nice and slow and steady, which was actually perfect for me to adjust to having it in me.
As he slowly continued forward, I could feel more and more of him sliding into me, as he continued moaning as the entrance of my hole gripped the shaft of his cock as tight as it could. Little by little his entire cock disappeared into me. At first Tim kept it all the way in, slightly probing around with his shifting hips until he started with withdraw, again nice and slowly. The slow, steady feeling was amazing, as it had been quite a while now since I’ve felt a guy’s cock in me.
Tim now started to slowly move in and out, his cock sliding back and forth through the entrance of my butt, which was gripping and tightening along the entire length of his shaft as he shoved his dick deep into my ass, only to just as quickly pull back so that his head was just barely still in. He began thrusting in and out like a pro, as if he had done this a million times. Truth be told, it was probably no strange action to him, same movements as with a girl.
We both began to moan louder and louder, more and more often. “Oh god, it’s so tight” Tim was able to blurb out in the process, clearly enjoying it. He kept pushing deeper and deeper it seemed, thrusting harder and harder. I could feel every inch of him pushing in, feeling my hole tightening harder and harder, squeezing every bit of him.
“Can I fuck you on your back? I want to see your cock.” Tim sort of surprised me, I had figured bending over for him would be best, since this was so new, but now in the moment, it seemed he had zero inhibitions. I also liked the idea of it too, so I started to move around as Tim’s dick slid out of him, I repositioned on the end of the couch, on my back, legs spread up. Tim propped them against his shoulder and then slid right back into me.
At this point, my cock was rock hard, shifting back and forth as Tim pushed in and out of me, balls swaying back and forth. It felt incredible, and the image, of looking down and seeing the end of his shaft at times, while my cock was bouncing around was amazing. Tim was staring straight down at the3 scene as he said, “I’m not gonna last long”.
“Don’t hold back or think about it, just cum, I’m not far myself.”
Tim started to speed up his thrusts, pushing harder and harder each time, faster and faster. We both started moaning louder and panting harder. I grabbed hold of my cock and started stroking, as I got closer and closer. And just then, Tim let out a loud grunt as I felt his movement stop and a blast of warmth inside of me as he shot his cum as far as it would go into me. Wave after wave, I could feel his cock pulsing as another blast unleashed. It felt like even more cum than earlier.
As he finished draining, as my hole was squeezing out every last drop, I couldn’t hold back any longer myself and a stream of warm, thick cum poured from my cock, spilling all over my chest. Tim slowed his movements, his cock still hard inside of me, as we both came down from the ecstasy.
“Holy shit, that felt amazing” Tim said as the silence broke. At this point, the whole shyness factor was gone.
“Yea, that was absolutely amazing. I can’t remember the last time anything felt that good.”
Tim pulled himself out and away as my legs relaxed down. I could feel his cum slowly starting to fall out of me, so picked up a leg and moved a hand under to catch it. “Woah…” I heard Tim gently say as from his view, he could see a bit of his cum dribble out of my now mostly closed hole.
“Should probably go clean up again, well, at least me” I mentioned as this would probably continue to dribble out a bit here and there still.
We headed back upstairs and hopped in the shower for the second time that night. This time, the attitude was far different, and more relaxed and talkative.
“Does it hurt?” Tim asked
“At first a little, as you first start to go in, but then it starts to relax and then suddenly feels amazing.”
“Maybe we can try it the other way around some time. You just seemed to enjoy it so much I’m a bit curious, but I don’t think I’m quite ready.”
“Sure!” I was happy to hear he had now a positive attitude and was no longer nervous on this topic at all. “You should play with it yourself a tad at home and see how you like feeling something in there, then it won’t be such a shock to try out.”
“Good idea, maybe I’ll try that”.
We chatted a bit more that evening in the shower and after drying off and getting our cloths back on. Then, we simply went our separate ways, headed off to bed, with no longer any curiosities on the encounters we were having. We continued to meet up after the bar like this over the next month or two, much the same as the last two times. Then, eventually, things changed a bit… (TBC)
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