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This is the 3rd part of the series Well, we did it again!
Tim and I met up at a coffee shop before heading over to Fred’s place. We are trying to figure out how we can double team Fred. It’s not as easy as one would think. Due to his anatomy, anal sex is totally off the table. I’ve seen him doubled over in pain, a few hours after being vigorously finger fucked. So, gang banging his ass is out of the question.

Guess that means, we’re going to have to concentrate on his other orifices. This could be fun. We agreed on a plan, time to head to Fred’s place. When we get there, Fred rings us in and we find him in his usual condition. Nude, watching porn and stroking his wonderfully talented man meat. Tim decides he will be our spokesman and tells Fred that today, we’d like to turn the tables. “Today, you will be our sub.”

Fred just smiled and said, “Wondered when you two would sample my other talents.” I half expected some resistance but nope, Fred was once again, one step ahead of us. “Why don’t you boys get a little more comfortable by removing all those restrictive clothes.” Ok, we’re slow but not that slow, 30 seconds later, Tim and I are standing in our birthday suits in front of Fred. Fred grabs a bottle of lube he keeps on the end table. He gets off the couch and kneels on the floor in front of us. He reaches out and grabs my wee willy and pulls me closer to him. He takes my half erect willy into his mouth and turns on his cock sucking vacuum cleaner. Holy shit! A tight, wet, velvet glove engulfs my member. I wanted to start pumping my cock into his mouth but no, let him do the work.

Fred reached out to Tim, to bring him into range. Fred pulled his mouth off my cock and swallowed Tim’s. He turned on the cock vacuum and Tim groaned in pleasure. I felt Fred’s hand pushing my right leg further apart, Ok, maybe my cock had been too high, so I slid my foot over a few inches, he pushed me some more, ok, a few more inches. Then the cock vac was back on my dick, Yes! But I kept my eye on him and noticed he did the same thing with Tim’s left leg, spreading both of us out. What’s he up to?

He moved back to Tim’s cock, and then I saw it, he was lubing up his hands. This could get interesting. I saw Fred’s right hand move up between Tim’s legs, followed by a grunt from Tim. The hoover is back on me, and I could feel Fred’s left hand move up to my ass. A finger finds its way in, and straight to massaging the prostate it goes. I now understand Tim’s last grunt. Fred knows his way around ass holes with his dick and fingers!

From here on out Fred alternated his blow job between us while increasing the finger count to two. Terrific head coupled with prostate stimulation, Tim and I were doomed. Fred moved back over to Tim and tilted his head up so he could stare straight into Tim’s eyes, with a mouthful of Tim’s cock. That did it for Tim, he cut loose and forced Fred to swallow some spunk.

Fred finished Tim off, then turned his attention to me, I felt the third finger enter my ass. He used his fingers in my ass to pull me in and out of his eager mouth, he literally face fucked himself with my cock. OK, he wins, my balls draw up and I loosen a torrent between his warm wet lips. Fred doesn’t miss a drop, pulls off and smiles at me and Tim, and says “you guys are just too damn easy.”

Fred, with a couple more strokes on our prostates, removes his fingers from us. That’s when I noticed, Fred had 4 fingers in Tim’s ass. I remembered Fred’s remark to Tim last weekend, “I want you tight, today”. Guess he wants Tim a little looser now! Let me go clean up, Fred says, meet me in the bedroom boys. We took it as an order.

When Fred came out the bathroom, his demeanor had changed back to his old Dom self. Bob, he said, we’ve had a change in plans. Tim and I spoke this week and Tim confided in me that he wants to experience a double anal penetration with a double cum dump. I told him we would be happy to fulfill his request. LOL. How do you feel about that Bob?

Well crap, now I will have to voice my age induced limitations. “Fred you’re 48 and Tim’s 33. Both of you can recover your stamina in 10 to 20 minutes. I’m nearly 70, I just shot my wad 10 minutes ago, I can probably get wee willy to rise for the occasion but a second cumming will probably be out of the question. I hope you are not going to be too disappointed, Tim?” Tim smiled and looked at me straight in the eyes and said he'll will be happy with anything I could give him. Well, damn!

Fred laid out on the bed and suggested his cock was feeling neglected and that I should rectify that situation. I crawled onto the bed and positioned myself between his legs and started giving him head. He patted me on my head and turned his attention to Tim. He told Tim to straddle his chest and feed him some of cock. Well, Tim was happy to oblige, but Tim didn’t notice Fred had his handy bottle of lube.

Fred slipped both of his arms between Tim’s legs so he could attack Tim’s ass with both hands. I changed my position slightly so I could get a better view of what Fred was up to. Fred lubed up his fingers, he inserted two fingers from his right hand into Tim’s ass. After a brief warm up, two fingers from his left hand joined the party. Tim, put up a mild protest, that actually sounded like he said “more” so, Fred buried all four fingers. When he would pull them out, he would spread his fingers, really stretching that hole open. My face is only 15 inches from the action, wee willy is fully awake!

I was very happy preforming my duties while watching Fred’s manipulations. Fred stepped up his game by adding a third finger on each hand into Tim’s ever-expanding orifice, Tim actually howled in pain. But he couldn’t go anywhere. His cock was locked in Fred’s mouth and Fred continued to punished Tim for another minute then rolled both Tim and myself off him.

Time for a new position, Fred had me lay on the bed on my back with a pillow lifting my butt. Ok, looks like I’m going for a ride, but no, Fred tells Tim to crawl on top of me, with his legs outside mine. Tim grabbed willy and guided me into his not so tight hole. Then sank down burying willy to the hilt.

Fred got between our legs. I could feel Fred’s cock squeeze in on top of mine, Tim begged Fred to go slow, I think he sobbed a bit. Fred slowly worked his dick all the way in but the moment he started withdrawing, my cock would pop out. We tried it a couple times, just couldn’t get it to work, my “average” dick was just too short.

So, we rearranged our bodies. Fred on the bottom, Tim in the middle and me knelling in the space between their legs. I rather liked this new position, as I could see Tim’s anal ring pull out every time Fred withdrew. I grabbed the lube and squirted a stream onto my cock, which dripped down on Fred’s and into Tim. Yes, we’re sliding very well now.

I managed to keep wee willy moving in and out of Tim at a very slow pace. A round trip was taking nearly a minute. Meanwhile, Fred has steadily ramped up the speed. This is putting a huge amount of attention on Tim’s prostate. I pretty sure things are going to boil over very soon. I’ve been watching Tim’s back, at first his muscles were very tense, and his moans were kinda sharp. But after a couple minutes I saw the tension leave his back, he actually looked pretty limp, and his moans had changed to yes, more, don’t stop! Fred’s and my cock weren’t pressed as hard against each other. I added more lube and started picking up my pace, don’t want Tim too relaxed!

About that time Tim cried out, “I’m cumming!” It’s a beautiful thing when a bottom comes without anyone touching their dick. Well other than Fred’s stomach that is. I keep my cock buried in his ass, I loved the feel of it clenching, squeezing Fred’s and my dick together. As if on cue, Fred and I both started ramming Tim’s ass. We were just out of time enough that sometimes we were both plunging in together and at other times one in, one out. Tim was starting to lose his mind! It was delicious!

I think each of us, Fred and myself, were trying to wait the other one out. For once, I had the advantage, I had already cum and still needed some recharge time. Fred must have been boiling over because he went straight into “rape that ass mode”! I added more lube and held still buried in Tim’s ass. Fred jackhammered Tim for a solid 30 seconds then let out a roar that drowned out Tim’s whimpering. Suddenly it got very slippery in the cum slut’s ass. Fred, laid still, fully impaling Tim on his magnificent 8” cock. It was my turn; I have to get my load off before Fred slips out.

I pull wee willy all the way out of Tim’s ass. I just fed in 3”, I’m going to need more stimulation if I want to cum. I start jack rabbiting that 3”, all the way out, then slam it back in. Boy! Tim’s anal ring is bright red! Willy pushing back in past his stretched out sphincter muscle is just enough extra stimulation to move me into firing position, time to add some more lube to make up for my light load. Torpedo way! Tim’s sunk! I rested in Tim’s ass for a couple seconds and felt Fred’s cock slip out. Holy shit, I’m not even touching the sides. Our boy is fully gaped! I pull out and Fred puts Tim in a bear hug.

I’m looking at Tim’s gaping hole, it is still open the size of half dollar. I just couldn’t help myself, I grabbed the lube and put it on my hand and pushed 4 fingers into Tim’s abused ass. He didn’t even grunt or moan or anything…might as well try squeezing the thumb in. That got his attention, but Fred still has him in the bear hug. I applied a little pressure and began rotating my hand back and forth. It is slowly sinking in, past the 2nd knuckles.

I keep the pressure and twisting action going, Tim started moaning again but Fred put a lip lock on him, and they start to get a little passionate. I’m right at widest part of my hand. Tim breaks the lip lock and begs me to stop.

Have you ever played with a butt plug? Remember how you struggled to get the widest point in? Remember how the moment you pass that point your butt just sucks it in? That’s where I’m at with Tim, just the slightest push and his ass will eat my hand. What do you do?

I stopped pushing, and still twisting my hand, slowly extracted it from Tim’s ass. My god what a gape! Bordered by his bright red anal ring. Looks like someone put lipstick on it, it is so red.

My desire to fist fuck him was real but my duty to maintain Tim’s trust is more important. Hopefully, Tim will want to try this again in another session. Main thing is, I hope he realizes we respect him and his limits.

Fred and I help Tim to stand, a slightly tan slurry begins dripping out of his still dilated hole. We steady Tim and walk him into the bathroom. He sits on the porcelain throne and farts all our cum out. Tim says he wants a shower and since I tried to shove my hand up his ass, I volunteered to provide aftercare. Sounds like a winner to me.

I adjusted the water temperature, and we step into the shower. I have Tim turn so he is leaning against the far wall, I spray him down with the hand sprayer. Then I grabbed the soap and washed him down from the crown of his head to the balls of his feet. I had Tim turn around and repeated the process with his front. After I rinsed Tim off, I knelt in front of him and took his semi hard cock, with the beautiful mushroom head into my mouth. I began bobbing up and down on his shaft, but Tim reached down and gently pushed me off his cock.

He said, “Please stand and hug me, then we need to talk”. I stood and we embraced. Tim told me how scared he was as I tried to enlarge his back door. It wasn’t so much the pain of being stretched that far, it was more about his desires and shame. Tim said “I really wanted to feel your fist in me, having two cocks was wonderful but then I became so ashamed of what I was becoming! I panicked! Bob, do you understand?”

I hugged him tighter and said yes, I do understand. We pushed some major boundaries today, the last was without any discussion. I apologized for taking advantage of the situation. I explained just how wonderful his ass had looked, dilated to the size of a half dollar. I couldn’t stop myself. I told him just how close he came to sucking my whole hand into his greedy hole. He laughed, and said it felt like I was trying to shove a football up there! We hugged again, and he thanked me for stopping and pulling out. Then he leaned in and kissed me with such passion it almost had me walking on air. How the fuck does he do that?

When we finally came out of the shower and dried off, I found some Vaseline and liberally coated his poor abused anus. Ok, maybe a finger or two slipped in momentarily but it was medicinal. When we came out of the bathroom, Fred was waiting for us with a shot and a beer chaser.

So, he said, does anyone have plans for next weekend?
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