This is a follow up to my story 'Good Neighbors' in which I, Jim, get introduced to Bobbie, a young fellow who lives in a nearby apartment with his mom. He was a virgin when I first met him and I opened him up in one of early get togethers but also got him all excited about fucking a woman for the first time. He does have one problem and that is that his cock is less than four inches and skinny when hard. I talked a girlfriend of mine, Sally, to introduce him to fucking in return for us letting her watch me fuck his ass but made her promise she wouldn't make any smart-ass comments about the size of his dick. She agreed and this is my recollection of that event
*****
"Bobbie, Sally is going to be here in an hour or so but I need you to take care of this now."
As I was saying that I had opened my robe and my half-hard cock was beginning to point at him.
"Jim, tell me what you want me to do for you. You know I'll do whatever you ask." Bobbie replied.
"Why don't I let you surprise me and use your imagination on making me feel good?"
I walked over to the living room sofa and Bobby followed like a sheep. As soon as I sat on the sofa he was on his knees in front of me and was reaching for my tool.
It had been a couple of weeks since he gave me his last blowjob and I think that he missed that as much as I did. He soon had his tongue going around the head of my cock and stopping every now and then to slip the tip of it in my pee hole. While he was doing this he had moved a hand down to my scrotum and was squeezing it ever so lightly.
"Does that feel OK Jim?"
"Oh you are doing just fine. Keep it up."
He then began licking my shaft from the tip down to base. He had let his tongue get all slathered up with his saliva and was using the fingers on one hand to slide up and down the shaft as his tongue was doing its magic. He was really jacking me off with the hand but with the moisture from his mouth it felt more like I was slipping my cock into a warm wet pussy. Damn, it felt good.
"Take me in your mouth Bobbie."
That was all it took. He went right into his deep throat routine. His very first move was to drop down on my cock so it was banging against the very back of his throat and then he pulled up as he began to gag on it. He then went part way up and down on me before dropping down to the base again. This time he went down a lot slower and eased my cock all the way into his throat. I'm, a solid 7 ½ inches and he almost had my entire cock buried.
"Oh yes Bobbie. You are going great. Start pumping me."
Pump he did. He would go almost all the way up and off before dropping down to the base before repeating the action. His hand was lightly massaging my balls as he was doing this.
I rested a hand on the back of his head and kept up a slight downward pressure as he was doing his thing. Every now and then I would exert more pressure and on that downward thrust he would go all the way to the deep throat position again. Mmmm this kid is a keeper.
"Bobbie, get up and get in the bedroom and drop your pants. I am going to fuck your ass once before Sally comes over. I want you loosened up before she watches us in action."
He was on his hands and knees on the bed almost before I got that entire sentence out. My cock was still wet from his mouth and I positioned myself behind him with my cock aimed at his tiny puckered asshole. I held his hips as I gave a little push and opened his love canal with the head of my cock before I pulled him back against me hard and threw my hips at him. I went in to the base with that one motion and he let out a little scream about me hurting him.
"Shut the fuck up. You know you're my little whore and I can do whatever I want with you. Throw your ass cunt back at me and fuck my cock without me having to make a move."
"OK Jim but I didn't think you would hurt me like that."
"I told you to shut up and get busy and have me splashing your anal canal with my joy juices. I've got a big load to fill you with."
A few more thrusts and I was shooting my white hot come up his tender ass. It was only three or four weeks ago that I opened his cherry ass wide open and we both loved it.
He was lying flat on the bed as I reached around and took his small cock in my hand and started to massage it lightly.
"Oh God Jim, you've never done that before."
It didn't take long before he was hard as a rod and his four incher was trying to poke a hole in the mattress.
"Turn over on your back Bobbie."
I slipped down and took his small thin shaft in my mouth. He was so small there wasn't any problem at all taking all of him. I bobbed up and down a few times and could feel him tense up. The young fellow was going to pop his cork quickly.
It wasn't long before he was shooting a decent sized load in my mouth and I slurped down every drop as I slipped my hand around to his ass and inserted a couple of fingers deep inside of him. We just lay there chatting a little and I reminded him that Sally was going to be over soon and was going to want to see me fucking his ass just before she let him put his little cock in her.