Be Careful What You Hope For Ch. 03

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Deeper and deeper into my first time.
1.4k words
4.55
32.5k
5

Part 3 of the 7 part series

Updated 09/22/2022
Created 08/04/2011
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Craysee
Craysee
17 Followers

I kind of dazed off for a little while, just trying to let what just happened soak in. Bob just laid there next to me and let me be quiet for a little bit. Finally, it occurred to me that I was being terribly rude. This man had done so much for me already and I had not even rubbed on him in any kind of way. I wasn't sure that I was ready to suck a cock or anything but I knew that I wanted him to get off. Shoot, I hadn't even seen his cock yet. I was eager to know how big it was. I finally spoke up,

" I guess it's your turn now, right?"

Bob asked, " What do you want to happen next?"

I said," I want you to fuck me."

Bob tried to remain cool, but it was obvious that he was giddy with excitement. He got up from the bed and walked around to my side and stood before me. He took off his t-shirt and let it fall to the floor. Then the next thirty seconds seem like a slow motion movie. He unbuckled his belt and then un-snapped his shorts. He slowly pulled his shorts down. He was wearing boxer briefs and was sporting a pretty massive bulge in the front. I could see an outline of his cock, shaft and head. He wasn't fully erect at all though. I couldn't help but wonder how big it was going to get. He then took hold of the waistband of his underwear and pulled them down and stepped out of them. When he stood back up, I was jaw dropped. His flaccid, un-cut cock was hanging there like a big chunk of meat. It must've weighed pounds. I thought that he was semi hard or something in his underwear, creating that bulge and shape. Nope. He was just being contained by his boxers briefs! And then he let the monster out.

I'd be lying if I said I wasn't nervous. That thing was a one-eyed beast staring at me. But I figured, that the worst that could happen for me is that it was a little painful and we quit. I figured I'd leave it up to him. After all, he was my new teacher. He climbed on the bed and moved between my legs. He started to rub my cock again and I grew hard. He swung his legs around to engage in a 69. He sucked my cock into his mouth and got to work. He edged his hips closer to my face in hopes of me doing something with his dick. I reached up with my hand and gently touched his hardening cock. It twitched with delight. I wrapped my fingers around the shaft and couldn't believe that this man carried this thing around with him everyday. It was really starting to take shape at this point. I started to jerk him off, using his ample foreskin. I knew that he really wanted me to put his cock in my mouth....

So I did. I opened my mouth as wide as I could and let his cock in. It had a taste that I never encountered before. I wondered if my cock tasted the same way. I did my best for a few minutes but I knew that I wasn't really getting it done. I did manage to get him to a fully erect sate. I estimated that he was a full 10 inches. Not an exaggerated 8 inches.. a full 10 inches. His cock was easily 2 inches in diameter. As far as a blowjob was concerned, my first blowjob, I was way overwhelmed. But I was pretty sure that I could manage to get that into my ass. So, I asked him....

"Are you ready?"

He sat up and said " I'm going to do my best to make this the most pleasurable time you've ever had"

He reached over to his nightstand and open the drawer. He pulled out a little plastic container that was sealed with plastic wrap. He also pulled out a little glass bottle that looked like medicine or something. I asked what those were.

He said, " well, this is a big boy condom. No offense, but I'd have a hard time getting the rubber you brought on my cock without worrying about bustin' it. This is built big and strong. And these are poppers... another little something to take the edge off."

He explained poppers a little bit more and I was sold. He asked if I would like to put his rubber on for him. I was more than happy to oblige. I stroked his cock a little bit more and then opened the little plastic container. I pulled out a sloppy wet balloon of a rubber. This thing was the Cadillac of rubbers. I slowly unrolled it down his monstrous cock. I asked him how he'd like to take me and he said that he wanted to look into my eyes while fucking me, so I laid back. He then grabbed a bottle of lube and then proceeded to get me all sorts of slick, prying my ass open a bit more with his fingers. Once I was ready, he grabbed the bottle of poppers and took a whiff, then offered it to me. I inhaled deeply and laid back again. He started to rub his cock head against my asshole, applying gentle pressure. His cockhead felt massive compared to any of the toys I had used before. He started to push in harder and told me to push back against him like I was trying to shit. So I went with it and his cock started to manage it's way in. I took another whiff of the poppers as I adjusted to the size of his huge cockhead. It was a bit painful at first. He waited for a few moments and then proceeded to push more. It was this crazy mixture of pain and pleasure at first. He was staring into my eyes, reading my every response to his movements and size. He knew he was huge, he loved that he was huge, and he loved sharing that we me. As he was holding my legs up, working his cock into me, I started to relax. He then started to fuck me... short strokes at first... gradually getting longer. I still had no idea how much of his cock he had gotten into me. I asked him and he said that we had a ways to go. He continued to fuck me and gradually went deeper and deeper. He was a master.... Each time he went a little deeper it hurt but then the pain was soon replaced with pleasure. Then he'd go deeper for more. I started drifting off in to the most amazing zone of pleasure. I loved what was happening to me. I loved Bob's cock. I wanted as much of it as I could take. I'm usually pretty quiet in bed but not this night.

"Come on, Bob. Fuck me. Fuck me. Oh, God, yes! " He really turned it on then. He started fucking me furiously. I then realized that his balls were slapping my body with each thrust. I was actually taking his whole, monstrous cock. Every once in a while I'd get this crazy jolt run through my body from his cock bumping my back bone or something. I was in heaven when he asked,

"Are you ready to come again?"

I didn't really know what he meant. I was loving getting my ass fucked but hadn't touched my cock at all, and neither had he. He then changed up his angle and really started working my prostate over with his huge pecker. I was in utter disbelief that something could feel so good. He was fucking me so good. I just totally gave in and let him do his thing. I started squeezing his cock with my ass which drove him crazy. He started yelling,

"Oh, God! Oh, yes! I'm gonna cum! Keep squeezing my cock with that ass! I'm gonna cum!"

And in seconds, I felt his cock swell larger! My own cock started to jerk and spew cum all over my chest. He froze and I could feel his cock pulse and spasm. I could feel a warm spot in my ass where the condom was filling with his warm seed. I clinched his cock with all of my anal might! He collapsed on top of me and I wrapped my arms and legs around him. His huge cock was still impaled in my ass. We just laid there like that for a while.....

Craysee
Craysee
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6 Comments
dinkybootsdinkybootsalmost 12 years ago

yay fucking spot on.?

AnonymousAnonymousover 12 years ago
Hot as hell!

I had a similar experience years ago. It seemed to take forever for him to work my ass and relax me to the point where I could take his cock, then, like you described, it took a lot of work on his part to get ever inch of those 10 true inches up inside. But the reward was well worth it. The only difference was that he took me bareback, we didn't worry about aid's those days, the clap was about the worst thing going around and he was married too, so I wasn't worried about the clap. Jim fucked me off and on for several years after that and I moved about 100 miles away and that sort of killed the relationship. I've often wanted to see if I could find him again.... ;-) Thanks for the great story. Too bad you couldn't take him bareback. It is one hell of an experience feeling that cock spitting all that sperm deep up inside your ass!

AnonymousAnonymousover 12 years ago
hot,,,

Can remember with joy the first time I took one that size, I had been taken by a couple of smaller ones, but, this was something altogether different, and as it was pre-aids it was bareback, and the feeling of him spurting into me and the feelingh of it inside me even hour l;ater wasfantastic, oh happy daysw.

Please continue so that I can re-live my debauched youth and sexual education by my well hung tutor who was 25yrs older and knew it all.

blueboy1957blueboy1957over 12 years ago
keep writing baby....

keep the story alive. are you looking for a good teacher or...pupil?

AnonymousAnonymousover 12 years ago
You were

so lucky wish I was there.

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