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Playing with my best friend

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So this happened to me recently, and it was on my bucket list of sex acts to do, the funny thing is that it happened unexpectedly and caught all involved by surprise. Heres the situation, I am a 50 year old married bi male and occasionally partake in having sex with Tim, a 49 year old male friend of mine, at his home close by. He is divorced from his wife of 20 years, but has a girlfriend, she does not know that either him or I are bi, my wife is also unaware, and that he and I like to play together. His girlfriend does not live with him, so when he calls me up to let me know she is out with her friends for the night and will not be there, I head over for some male fun. It's easy for me to get out, I just tell my wife I'm heading over to Tim's house to help him with a hotrod he is working on, this gives us plenty of time to play and usually get some work done on the car afterwards. On this night, it had been quite some time since we were able to get together, so we were both excited to play. He instructed me to just come in when I get there, and that he would be ready and waiting for me upstairs. I should tell you that we have done very little more than just suck on each others dicks, on occasion we would finger one another's back door, and once I got in far enough to stimulate his prostate, that was the last time we got to play, and he has said in a few conversations recently that he would like to pursue this some more in our upcoming play date's. I arrived at his house and parked in the ally by the garage, went in through the kitchen, and wasted no time going upstairs. When I reached the top of the steps, I stopped right there to strip down before entering the spare room were we play ( he has a bedroom with nothing more than a queen size bed in it ) I walked in with a raging hard-on, and what I saw made it even harder than it already was. He was naked and spread eagle face down, and somthing was shoved in his ass with a tube coming from the middle of it and a squeezable bulb ( like a blood pressure cuff ) laying on the bed between his legs. I said "what is this fun toy you have here" he told me it was an inflatable butt plug, and that he has been using it for about a month now. He then said "I left it for you to pump up, and stretch me out" I asked if this was his way of telling me that he wanted to get fucked by me? He said "I want you inside of me" I wasted no time jumping on the bed between his legs, grabbed the bulb, and began to slowly pump it up. He started to moan and grunt, so I asked him if he was ok? His response was a stammered yes, but then he said to let it down and pump it back up again. I did as instructed a few times, then he said when it's down pull it out about halfway and slowly pump it up again, when I did this it must have been out to far, because it came all the way out of his ass. I pushed it back in and slowly pumped it up to stretch his opening. When he said he was ready for me, I pulled the plug out and he turned over to suck on my dick for a little bit. He was slowly but surely taking my fully erect cock all the way down to my balls. I said "easy there, I thought I was going to fuck you" he responded by grabbing a condom he had under the pillow, and began to slowly roll it down my shaft. I said "how should we do this?" He moved to the edge of the bed so his ass was hanging over it just a bit, spread his legs in the air,and said "put it in, put it in now" but I couldn't resist, with his dick erect, lying there touching all the way up to his belly button, and oozing pre-cum. I had to bend down and suck on it for a minute. As I was tasting the pre-cum from his obvious excitement, we thought we heard a noise from down stairs, he said did you lock the door behind you? I said that I had not. But it was to late, the noise we heard was from upstairs not down. In a startled voice, his girlfriend Pam was in the open doorway of the room, and said "oh my god, what are you two doing" Tim and I both stood up in surprise, but with no clothes in the room, and nothing else to cover up with, we were standing there in complete vulnerability. Tim just started saying "babe, what are you doing here, I thought you were out with Carol" she said " don't babe me" then looking at me she said "does D know about this?" D is what most people call my wife, short for her first name. I said "no, and please don't tell her" looking at Tim she said "I can't believe you two, do you suck his dick to?, How long have you been doing this?, and who else are you doing? " Tim told her that we have been doing this with each other since we were in high school, but that I was the only one he has ever done it with. Pam asked him agian "so do you suck his dick?" "Yes" he said. She asked him if he was screwing around with anyone else at all, and he swore that he was not. I again asked her not to say anything to D. She told me "I won't, but you need to do something for me" what mite that be, I asked, and she replied "I want you to suck his dick as I watch" with her catching us, both of our dicks had gone limp, and I can't say what Tim was thinking about the situation, but I wasn't sure what to do at that point, seeing how embarrassing it was getting caught sucking her boyfriend's cock, and standing there completely naked in front of her. Then she said with a bit more authority "come on suck that dick" as she pointed to Tim's crotch, leading me to look at his now hardening limp dick. I knew it was turning him on. She then reached down and grab him, and began to stroke his dick to an erection for me to suck on, saying "come on, get down on your knees, and suck it" Well this is what I was talking about at the start of the story, my bucket list sex act, a male friend and a woman who joins in on the fun. My dick started to get fat with the instructions given by Pam, and I looked at Tim to see what he mite be thinking. Well it didn't take a rocket scientist to figure out what the expression on his face meant (go for it) so I got down in front of him, reached around both sides of him and grabbed his ass, one cheek in each hand, and let Pam guide his cock into my mouth. She started to get excited also, you could hear it in her voice as she said " yeah, that's hot, suck that dick" she keep pumping on his cock as I took as much as I could in my mouth. She asked Tim "is that what you like, another guy sucking you?" He didn't answer her with words, just moans of pleasure. I would have been on the verge of climax if it were my dick being sucked along with her giving me a hand job at the same time, but not Tim, he was very good at control, and I knew he would make this last as long as he could. So I didn't want his spinkster to tighten up on me from the long time that has gone by from stretching it out with the butt plug, witch had fallen onto the floor, and slightly under the bed, so I slid a finger into Tim's ass to keep it loose, at the same time I pushed the butt plug out from under the bed with my knee, to see if Pam would notice that we were playing around with it. That worked because she said "oh shit, is that my butt plug? are you two using my plug? We're you going to fuck him? Is that why you had a slicker on? The questions came fast, and Tim answered her the best he could by saying "Yes it is, and he was just about to" "oh my god, I want to see that, will you fuck his ass for me?" I said that I had to put on a new condom first. Pam ran out of the room and came back with a hand full of them, opened one up with her teeth and grabbed my dick with no inhibitions, rolled it down my shaft, and said "there you go". My mind was all over the place with excitement, (one for the fact that Pam just grabbed my cock and put a rubber on it, and two that I was about to fuck my best friends ass for the first time) Tim spoke up and said "your going to need this" as he reached under the pillow again, and handed Pam a bottle of lube. She said "oh yes we can't forget this" Tim added "lots of it please" Pam opened it and began to slather a liberal amount all over Tim's butt hole, sliding a finger in to get his hole ready in and out. Then she told me to come over to her. As I walked over to her she graded my cock from below, cupping it with her left hand, and poured a long stream of lube all over the top of it, letting it flow over and into her hand. She then put the bottle down, and now with both hands she started to stroke me, and spread the lube over every inch of my very hard dick, then she said "let's do this." With that comment, I went right between Tim's spread legs and started by rubbing the tip of my dick on his hole, and it was definitely lubed up well, I couldn't get my dick to enter his ass, it just keep slipping either above or below his hole. So I grasped my cock closer to the head, and pushed slow and easy right over his opening, and I got the tip to enter him with ease. His moans let Pam know that I had entered him, and she began to get excited right along with Tim and myself. As I started to push my dick further in his ass it felt more and more wonderful, so with a little more lube dribbled on my exposed part of my dick, I began to slowly pump it in and out of him. I was getting into a nice rhythm, pumping his ass, and looking down at his cock as I did. I wanted to suck him so badly at the same time, but that was impossible. Pam on the other hand, would have had a great opportunity to do so, but instead she grabbed his dick, and started to stroke him. Then she must have been so turned on by all that was happening, as she stood up and began to take off her clothes. I got so excited seeing her naked that I almost blew my load, so I had to just stop fucking Tim for a few seconds to hold back from cumming. Pam is a beautiful woman with small tits and an ass to.... well, let's just say I have never seen a naked ass in real life that was that nice. Then she stood above tim, infront of me as she lowered her pussy right down on his face, she looked right at me and said "fuck that ass for me, fuck it faster" so I started pumping in and out again, and in the heat of it all, I reached out to grab Pam tits, and her very hard nipples. I leaned in to put one of them in my mouth, she didn't resist at all, and actually started to moan. I don't know if this was from her titty in my mouth, or from Tim licking her cunt at the same time. This rekindled that very good feeling brewing deep inside of me, as I felt I couldn't hold it any longer, I pulled back from Pam, as well as take my dick out of Tim, and reached down to rip the condom off just as I started to cum, blowing my load all over his cock and balls , now I had the chance to suck him, as well as clean up after myself. I went right to town on licking up my own cum from his balls and cock. Pam watched for a little bit, but repositioning herself, she moved down to sit on Tim's now very hard and engorged cock. Then she said with a moan " keep licking that cock! " I didn't hesitate, this gave me the opportunity to lick his dick and her clit, as she glided her cunt over Tim's Dick and pushed it inside of herself, I could do nothing but suck on his balls as she began to ride him harder and faster, and that soon became impossible to do as she bucked and fucked his shaft. I was able to slip a finger in his well lubed ass and let the motion from Pam's cowgirl ride do all the work for me, it wasent long before Tim exploded inside of her, filling her pussy full of his seed. That's when I got the best surprise of all, Pam slid his Dick out and told me to clean her up, I went right to work, licking and sucking as much of Tim's cum from her cunt as I could, she started moving faster and faster as she rubbed her clit all over my face, when she had an orgasm she quickly pulled away from me, and began to finish herself off with her hand, I turned to Tim's now limp Dick that was still covered with her juices and his cum together, and cleaned him up all the way down to his asshole. Pam reached over to just lightly massage Tim's dick and balls, and announced "what a great surprise I walked into, can I attended another one of your fuck sessions" without hesitation Tim and I said in unison "hell yeah" we just laid there for awhile to recover from the great time we shared. Pam then said "are you sure D wouldn't want to join in, I wouldn't mind having some fun with her as you two do your thing" I again asked her not to say anything, but if she could get D to play with her and I walked in on them, maybe we could have some fun and work Tim in as well and let things happen, she wouldn't be able to say anything right. Pam just said "lets see what we can do" More to cum in the future I hope.

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