Saturday morning after breakfast and a run, I let Ryan wear jeans, his padlock and chain, and his new buttlock, cockring, collar and harness. We drove over to his place and packed clothing he needed for work. I did let him pack a pair of shorts t-shirt, some tight jeans and sneakers, but I told him he would be naked most of the time my place.
He had a very nice condo that was more than he could afford on his salary which is how he got into financial trouble. I said we’d talk about what to do with it. I was thinking he could rent it and pay off his mortgage that way. He wasn’t going to bars or entertaining chicks, more savings. He could probably sell his vette too, but I kind of liked it myself.
While we were packing his doorbell rang and it was a friend from his gym who missed him and wanted to see if everything was ok. I told Ryan it was kewl and he buzzed him up. When he arrived at the door it was muscle god number 2. Needless to say my fantasies were in high gear... My gaydar was buzzing and I wondered what the story was. Ryan introduced me to Bruce as a friend who he was moving in with.
The friends name was Bruce (of course). Bruce was agog at Ryan’s attire and said “I like the look dude. Very nice. May I touch him, sir?” Bruce had addressed me, not Ryan. How astute. I nodded my consent. Bruce traced his finger over the collar and harness “Totally hot dude.” I thought I noticed Bruce eyeing Ryan’s bulge, but he resisted groping it. He just said “Nice basket too bro.”
Bruce gave us a hand loading Ryan's clothes. He was curious why Ryan was just taking dress clothes and Ryan said there was some stuff already over there and he would get stuff as he needed it. Bruce suggested some black leather jeans would look good. “Good idea Bruce. Is there a good store that can fit them properly? I want the bulge to be properly displayed, not too tightly compacted.” Bruce said there was a good leather store on First Ave.
Bruce said he would give me his number if we ever needed anything. I thanked him for his concern and number and said we would be in touch.
I gave Bruce credit as he had quickly picked up on the hierarchy of our relationship. From the get go he deferred to me. When Bruce left I said who the fuck was that god? Ryan said “I should have told you, but things have been happening so fast I just.... “
“So tell me now.”
“Well Wednesday night when you told me to shave I was doing it in the shower at the gym. I’ve seen guys do it there before so its no big deal. Bruce was there too and he offered to help me get some of the places that were hard to reach.
“I just know him from the gym but we’ve never hung out or gone to bars together or anything. I just seen him around the gym. I’ve noticed him checking me out a few times but he never made a move on me so it was cool, but I wondered if he might be into guys.
“I did accept his offer to help out with the shave and we were the only ones in the shower. I got up the nerve to ask him if he ever messed with guys. He said yea but he assumed I was pretty straight. I said I was but a friend wanted to mess around. I said it’s a long story, but would you mind giving me some pointers?”
He laughed and said “Yes I’d be happy to give you my pointer. Shall I accidentally drop the soap?” He was just kidding but I’m sure he’d like to give me his pointer for reals.
“He told me about fucking with guys and if I was going to be top or bottom. I wasn’t even sure what that meant or what I was going to be. So he told me being a top was pretty much the same as anal with a guy and a girl.
He asked if I had ever had it in the ass and I told him no but I thought that was what my friend wanted. So he told me about douching, lubing up, fingering and relaxing like I was shitting. Arching my back. That stuff. He told me it would hurt til I got used to it just like you said.
As he shaved my butt, his fingers were soapy and he played with my hole. He told me to relax and let him give me a little preview. He slipped one finger in and it was wierd but it didn’t hurt. He put another in that was ok too. The third finger hurt a little and a fourth just a bit more.
“See its not that bad. Not to be too crude but a cock is about the same size as what goes down the chute every day. The butt is a kind of trained to be a oneway street til it learns how to be two ways.”
(Well so Ryan wasn’t a total virgin; he had been fingered. But I was his first fuck. I think that still counts as getting his cherry.)
Then once you’re loosened up a bit, he will enter you with his cock. It will take some getting used to, but feel this - he massaged my prostate a bit. That’s your prostate and it is where the pleasure comes from when you cum. Just rubbing it feels great. That’s what you get out of getting fucked! Some guys can actually cum when they get fucked.”
He said alot was mental. If you’re real turned on by a certain guy and really wanted it bad it would be easier. I told him it was someone I liked but never thought about sexually. He said try not to be too negative about it, I might really enjoy it. Alot of guys couldn’t get enough.
I asked Bruce if he was a top or bottom and he said he was versatile, mostly a top but he would do me either way if I wanted to try it. I was tempted to try letting him do me since he already fingered me and it wasn’t that bad but I passed saying right now I had enough on my plate. He was real kewl and I appreciated his advice. “I’m sure he came by because he was curious about what happened. Was that alright master?”
I told him he handled it perfectly and he was right to be discrete. I was happy to have been the one to get his cherry...
I said I had something to tell him as well. I told him some of my friends were coming over this evening. It had been planned for a couple weeks and while I considered cancelling it I decided it would be a good chance to show off my new toy.
I wasn’t sure if toy was better than slave but I was curious about the details of the evening.
We were just about ready to go and he said we could talk about the evening on the way home.
He told me it was a gay affair and he intended to show me off,,, naked. I would be wearing my new harness, lock, chain, slave collar and a bow tie, but not the new chrome cock ring or butt lock. I would greet the guests at the door and serve drinks.
Apparently a few of the guests had “boys” and likely one or two would assist me in serving drinks and snacks. He told me that it was likely that the guys would want to grab a feel and that I should generously accommodate them. Consider it complementary. He said I may even get a finger in the ass but that was likely as far as it would go.
I wasn’t comfortable at all, but I didn’t say so cuz I had agreed to be his slave and obey anything he said. I guessed I may as well get used to his lifestyle.
My friend Scott and his boy John will be coming over this afternoon to do most of the preparations and we would help.
I was just thinking that you could invite Bruce? In fact I’d like it if you would. I knew Ryan wasn’t keen on having his friend seeing him on naked butler duty but he’d do it if I really wanted him to. I said tell him your role and ask if he would like to join you. Gay guys love to show off.
When we got home Ryan called Bruce who wouldn’t turn down any invite from Ryan. Ryan was pretty surprised. Bruce told him he even had experience “entertaining” and would love to join him. He said he could come early too and help with the prep. Gay guys are pretty talented at entertaining.
Well things were shaping up. I knew I was going to have a great time.
I had a few more surprises for Ryan but he’d find out in due time.
Scott and John arrived first. When the doorbell rang. Ryan jumped. I said its not your mom go and answer the door. I knew it was Scott and John. Ryan let them in and was taken aback at their oo’s and aahhh’s over him. Scott was a year or 2 older than me John in his 20s athletic, not nearly as built as Ryan and one might say gayer... Scott was dressed casually and John was in shorts and T. At being greeted by the naked butler John joked about spending the whole morning picking out an outfit only to come over dressed! Everyone laughed. Even Ryan.
A few minutes later Bruce showed up in sneakers and shorts - no shirt, but a black leather harness similar to Ryan’s. Everyone laughed again when he said he couldn’t decide which shorts to wear! I was agape at his harnessed torso that rivaled Ryan's. Hairless outstanding pecs and abs with rings in his nipples. (That was actually my surprise for Ryan. One of my friends is a vet and I asked him to bring his piercing kit to do Ryan's nips at the party.) Bruce gave Ryan’s chain a yank and said he loved his outfit as well! Ryan blushed with em,, bare-ass,, ment.
I introduced Bruce to Scott and John. John commented that he and Bruce were both over dressed maybe they should get more comfortable since they were the “help.” Both stripped and Scott and I sported hardons in our pants. I’d seen John before. He was fine but Bruce and Ryan were to die for. Bruce was cut and very well hung. He was wearing a thick chrome cock ring around his pubeless junk. I’m sure that wasn’t missed by Ryan.
I asked if Ryan and Bruce could do some heavy lifting and they said sure. I said to go up to the bedroom and get the cross and gibbet (the 6’ x 6’ x 18” platform or riser for the cross). Ryan apprehensively led the way and Bruce followed admiring the smooth round ass he’d shaved only 2 nights ago. Bruce asked Ryan if he was the entertainment. Ryan just shrugged and asked Bruce if he was into this kind of stuff. “Oh fuck yea! I love it” was Bruce’s reply.
As they brought the items down I rearranged some furniture in the great room and put the cross at the head of the room. I told Bruce he might look good on the cross. His reply was immediate. “I sure do!” Well we’ll have to give you a turn then. He responded “Be happy to sir!” My cock jumped and I wondered if he noticed.
We were pretty much ready and had some time to relax. I thanked Bruce for helping Ryan shave and giving him a few pointers about gay sex. “I was wondering if you might like to give him another lesson. I think you have time for a quickie.”
Bruce was speechless. “You mean you want me to fuck Ryan?”
“Well if you don’t mind an audience. It’s the least we can do to thank you. And it would get us into the mood for this party.”
“O fuckin A! You have no idea how many times I’ve had this dream. This will be awesome.”
“Ryan why don’t you lay on the coffee table and grab your ankles. Go easy on him he’s only been fucked a few times.”
Bruce went easy but he was a bit bigger than me. Ryan did his best to accommodate his friend’s dick. As Bruce fucked harder and harder, Ryan’s head tossed from side to side moaning with both pain and pleasure. When Bruce finally came, he shot a hot steamy load deep in Ryan’s ass.
“Damn I knew he’d be an epic fuck. Anytime he needs a refresher, give me a call!”
I put a plug in Ryan’s ass so he wouldn’t leak.
We got ourselves together and prepared for our guests. I had a small box with several bowties for the “help.” I distributed them to the boys and said they’re pre-tied since no one knows how to tie one. There were some extras just in case more “help” showed up.
People began to arrive and Bruce kind of took the lead with Ryan in tow. There were a couple dozen people there and a half dozen were naked “helpers”. All the boys put their names on slips of paper and their names were put in a hat to be drawn for entertainment. The daddies did likewise in a second hat. There was a third hat that had “Jeopardy” cards in it.
When the fun started, Bruce’s name was drawn first and he was promptly secured to the cross. The daddys names were in another hat and their names were drawn too. Their job was drawn from a 3rd hat and they would have to whip, jerk or blow the boy on the cross. The guy drew whip. We were getting off to a great start and Bruce would certainly be a hot whipee. Bruce played it to the hilt. He protested, and he struggled but he got no pity. The whipper layed into him. He actually knew enough to start easy and gage the guys ability to take it. It was clear that Bruce was no novice and he wad totally boned by the third stroke. The whipper didn’t avoid his cock rather he laid on some stingers. Bruce hooted and hollered but was given no mercy.
Bruce was getting close and asked for a favor. He asked if it would be alright if Ryan whipped him to a climax cum. Everyone applauded and Ryan was given the whip. Bruce whispered to him to go for his cock. Ryan was a little shocked but took over and did as he was asked. Bruce took it for a good 10 minutes - direct hits to his big dick and it throbbed and dripped pre-cum. Finally he let loose with an epic cum.
It was amazing and even hit Ryan who was nearly 10 feet away. Everyone clapped and hooted. Bruce was a real hit. He was released from the cross and given a drink. He went over to Ryan and thanked him for finishing him off. He said his cum was the most intense orgasm he ever had and kissed him square on the mouth. Bruce confided to Ryan that he has lusted for him from the first time he met him and the scene they had just done was the stuff of his dreams. He kissed him again.
The other guys had their turns but none were as spectacular as Bruce. Finally Ryan’s name was drawn. He was secured to the cross and I pre-empted drawing a name. I called on my vet friend and announced I had something special for my boy Ryan. I’ve asked Dr Derek here to put rings in his nipples. Its gonna hurt and your free to scream. Do it Dr Derek.
Ryan broke out in a sweat and Dr Derek painted his nips with disinfectant. He placed a circular forceps on the nip and inserted the pointed hole punch. Ryan took the clamp but couldn’t hold back when the piercing tool went in. He let out a blood curdling scream and I knew some of the guys came. I noticed that Ryan was rock hard. The first nipple was done and the process repeated with the other. Ryan was able to take the clamp but with the actual piercing he wailed. I felt kinda bad but noticed he was still hard as a rock. The rings were not the wire thin starters normally used. I had given Derek little luggage locks that were maybe 5 or 4 gauge. The lower the number the thicker the ring.
I quietly went over to Bruce and asked if he would like to do the honors getting Ryan off after the piercing. He asked if I had any suggestions he would eagerly do anything. I said well he’s rock hard and he’s had enough pain so how bout a blow job. Bruce was ecstatic at the prospect of getting Ryan's cock and eventual cum in his mouth. He couldn’t wait. With the piercings done and rings in I sent Bruce in to go for the kill.
As Bruce approached Ryan he whispered that he got his done the same way so he knew it hurt. But now you’re mine and I got you and your magnificent cock just where I want you. I’m going to give you an epic blow job. Your ass is full of my cum and now I’m going to suck out every drop of your cum. I’ve had this dream a thousand times too and now its coming true. I’m going to drive you fuckin wild and make you beg to get off. Bruce took the hard cock all the way down and he was a pro. He edged Ryan for half an hour and Ryan was begging to get off. When Ryan came the scream was akin to the piercing scream but this time it was pure pleasure.
Ryan looked like he had died on the cross. He was given a few minutes rest and there was a line of boys who wanted a go at his cock. What the hell. Go for it guys. Six guys sucked on his cock for almost 2 hours. He came dry for the last 2 guys and I gave them rain checks.
We finally let Ryan down and Bruce asked for another turn. He said he wanted to be drained just like Ryan had been and when they were done he wanted Dr Derek to give him a PA piercing. Wow what a party. As Bruce was being crucified for the second time I consulted with Dr Derek I told him to use the large hole punch big enough to accommodate a regulation gym padlock. I had a plan... I was going to put a padlock in Bruce’s cock and keep the key. Diabolical huh?
I went to check on Ryan who was recovering with a now rare drink. He said it hurt like hell but he’d be ok. I told him he was a trooper and that I was proud of him. I asked if he was ok with Bruce’s role in the party and Ryan rolled his eyes and said he almost killed him with that blow job - it was awesome. I said I knew most of his friends were straight and it might be good to have a gay friend now that his lifestyle had changed. He agreed and said he didn’t know Bruce that well but he certainly knew his way around the gay scene more than he did and it would be good to have a peer to talk to. Then you’re ok with having him over on a regular basis? Ryan said it was my decision but he was fine with it.