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Both opened up showing some of my load in each of their mouths. "Kiss each other". They did and were as happy as clams. I don't even think they noticed when I got up, grabbed my shorts and t-shirt and left.
Clyde and Todd settled into a once or twice weekly kiss and suck situation. Clyde confided in me that he had always had the hots for his son-in-law but never thought of pursuing anything. Todd was quickly gaining experience and Clyde said that at the right angle, he could get about 7 out of 11" down his throat. "I need to get him to relax and stop fighting it. I know he wants all of my big cock and I'm trying to be patient." Clyde also stated that Todd's ass was prime, virgin hole as he was sure that Todd has never had anything up there besides maybe a finger or two. Todd confessed that he had gotten Kara to lick his hole a few times and he absolutely loved it. Clyde stated that this was WAY too much information as he didn't need to know that his daughter wasn't as vanilla as he had thought.
Clyde then said he needed my help, yet again. "Jeff, you have been a great friend and I owe you so much. Do me another favor and it will be worth the effort." Clyde continued that he had fingered Todd's hole a few times and the boy went wild. "I know he wants to be fucked but is way too embarrassed to ask. How do you feel about popping his cherry?"
As we were conversing, my cock was hard as a rock. While I never even considered Todd as a sexual play thing, I had to admit to myself that he was damn cute, with a tight little body, and I could only imagine a tight little asshole.
"Sure Clyde. Let me see what I can do." I texted Todd and invited him over for a drink. I think he was a little scared and hesitated but I reminded him that we go back a long ways and it was just a friendly drink. He finally agreed. I then texted Brad and told him that I needed a 'fluffer'. Brad was intrigued. I told him that I wasn't sure how this was going to play out and asked if he was willing to be patient. I told him to come to my house around 5pm and I gave him the door code and told him to be extra quiet.
Todd arrived at 4pm. We had a drink. Unbeknownst to him, I had laced his with a viagra. We chatted for a good 40 minutes when I gave him a refill. I could tell he was getting horny as he kept touching his hard cock through his pants. I went to the bathroom and when I returned, Todd was on his phone texting. I came up behind him and squeezed his shoulder and then ran my fingers through his hair. I heard a low moan. I then reached around and lightly squeezed both of his nips through his shirt.
Another moan. I took his head and gently turned it around and kissed him. He went wild and immediately kissed me back basically trying to swallow my tongue. I looked up at my kitchen window and saw Brad peeking in. Fortunately, Todd had his eyes closed and didn't see Brad. I put my finger to my lips indicating to Brad to be quiet. I also then motioned him to come around to the front door.
At this point, Todd was so turned on, I probably could have convinced him to do anything. I asked him if he wanted to go to my bedroom and he said yes, with absolutely no hesitation!. We got to my bedroom and we started making out again. He was like putty in my hands. It didn't take much to get him naked. His tiny nub of a penis was rock hard. I felt sorry for him having to go through life with such a small cock. Certainly Kara couldn't be satisfied. But then, that was not my problem. My goal was to take his virginity although I wasn't going to rape him.
While we were kissing, I reached back and started fingering Todd's hole. Surprisingly, it was very clean and he was going crazy. Did he anticipate getting his first cock in his ass? Did he clean out thinking something might happen? "I think you like your hole being played with Todd." He turned three shades of red. "Don't fight it man, the asshole is a very sensitive and sensual part of the body. Have you ever been fucked?" He said no. "But you've thought about it haven't you?" He avoided looking me in the eyes. "HAVEN'T YOU? Be honest." He reluctantly admitted that he had indeed thought about it many, MANY times. He was too worried that it would hurt too much, especially with a big cock like mine. I told him that a big cock would be his father-in-laws and mine was nothing in comparison. He got even more embarrassed. "You've thought about your father-in-law's cock in you, haven't you. Tell me the truth." After kissing him some more, he finally admitted that yes, he has thought about it but that Clyde's cock would rip him apart and was sure that Clyde was only into getting blown. I did not let on that his father-in-law was a kinky, horn dog and was into a hell of a lot more than just getting his cock sucked! I told him that he needed to be broken in and how it was all about the preparation and foreplay. He looked at me with a puzzled look.
Brad walked in and Todd was so startled that he immediately covered up his small but hard cock. "Don't be embarrassed. My good buddy Brad here has some amazing preparation skills." I pushed Todd down on the bed and spread his cheeks. I winked and nodded at Brad and Brad took the clue and immediately went to Todd's hole and gave it a long lick. Todd just shuddered. "Relax Todd. Just enjoy it." He squirmed and squirmed as Brad got more acquainted his hole and started tongue fucking him. This is going to be easier than I thought, I guess you can't rape the willing!
After a good 10 minutes of top notch ass eating, Todd was a hot mess. He was groaning something fierce. I whispered to Brad that I would let him fuck Todd but I wanted to be the one to pop his cherry and be the first one to breed him. Brad just nodded.
"Feels good Todd, doesn't it? My buddy here is a pro." Todd just continued to groan and admitted it was better than anything he had ever felt. We had him! The viagra was certainly doing it's job. "You want something bigger in there than a tongue, admit it." Brad continued lapping on his hole to the point the saliva had him totally wet. "Tell me what you want BOY." "Ummm, ok yes, I want your cock but I'm scared."
"Nothing to be scared of. I am patient and will go slow and Brad will keep you lubed up." He replied "I don't know. It will hurt too much."
"I'm not going to lie to you Todd. It will hurt at first but eventually you will love it." Brad continued his ass eating. Finally Todd exclaimed "Yes, give it to me." Music to my ears. I grabbed the bottle of lube and out an extra amount of it on my cock and worked even more into Todd's hole. I then ran my cock up and down his hole until he was squirming out of control. I put the head of my dick against his hole and pushed a little. FUCK his hole was like a vice grip. "Relax buddy. If you fight it, it will hurt even more. Push out a little." He did and my cock went in a few inches. "OW OW OW, it hurts, take it out." "Relax buddy and with that, I pushed in a few more inches. He yelped. I looked at the video camera and said "Fucking prime A cherry boy hole." I immediately pulled out as I didn't want to be too aggressive...at least not yet!
I motioned Brad to his hole. He went down on it again and I just nodded and told him to go for it. "Ok Todd, it's all about a steady progression. Brad is going to get you opened up for me." He started to struggle. "Relax BOY, Brad will go slow." Brad lined up his cock and teased Todd's hole and then pushed in. Todd gasped but didn't struggle as much. "See, Brad has the perfect size cock to start off with". I again whispered to Brad no cumming in him yet and I again promised him sloppy seconds. "and you can eat the cum after we're both finished!"
Brad got into some long dicking and Todd seemed to be enjoying it. I was so fucking hard, I couldn't wait any longer. "Ready to size up?!" "Yes SIR, if you go slow." Love it when a boy calls me SIR without me making him! "Ok bud, I will go slow but be warned, once I'm in, I'm not pulling out until I cum." Todd just nodded. Brad pulled out and went down on my cock again giving it some more lubrication and licked Todd's ass again. "Here we go." I slipped in and he started to struggle. "I lied, it's too big, take it out. PLEASE." "You were warned Todd. It's not coming out." I held Todd's arms down and he just gasped as I inched in more. "Don't fight it. You know this is what you want and if you ever want Clyde's cock up there, you need practice. On that note, I pushed in to the hilt. Todd yelled. Brad then went to Todd's head and forcefully kissed him. I whispered into Todd's ear, "I'm all the way in buddy. You have 8.5" of prime meat fucking your hot ass. You're doing great." The pained look on the boy's face finally turned to one of complete bliss. I knew I wasn't going to last long and told Todd while I looked up at the camera "Here it comes, I am going to breed you like a bitch." And with that I shot one of the biggest loads of my life into my ex-assistant's hole. He was in a trance, convulsing like he was having a seizure. Later I learned he had a hand's free orgasm. I pulled out and motioned to Brad to step right up. Brad took the clue and plunged his cock into Todd in one thrust. Within 2 minutes, Brad moaned and got the sloppy seconds I promised him. I leaned down to Todd's ear and said "That is how you pop a cherry. You will learn to please many men with that hot ass."
Brad pulled out and immediately went to the freshly fucked, no longer cherry hole and ate it with gusto. Todd was enjoying it too much and was a complete mess.
We eventually stopped and I told Todd to go ahead and shower as I didn't want him smelling of man sex when he got home to Kara. Brad and I went downstairs and I poured us both some wine. 'Fuck Jeff, you never cease to amaze me. You have turned into such a good friend and a true partner in crime!" I just winked at him. Todd came down and I offered him some wine but he said he needed to get home. I told him that he would be sore and walking funny for a few days but his hole would return to normal (well as normal as it could even be after having two cocks in there for the first time!) Todd walked over to me and kissed me. I pulled Brad over and we shared a few minutes of a three way kiss. HOT!.
Todd left and after a second glass of wine, Brad left too. I immediately went to my computer to watch the video. I don't think it ever dawned on Todd that I would film the loss of his virginity. The video was perfect and I shortened it a bit and then emailed it to Clyde with the subject line: Mission Accomplished!
Within 30 minutes, my phone rang. It was Clyde. "Oh my GOD Jeff, you are a stud, that was hotter than anything I've ever seen. I certainly would have liked to be the one to give him his first breeding but I would rip him apart." I responded "First world problems." We both laughed hysterically. I told him to turn up the volume and fast forward to 8:04 where Todd admits he wants Clyde's cock in him. Clyde thanked me and said that he would be in touch.