It had been 2 years since the massage before I reached out again.
I revived our chat and he was keen to go again. I laid out a few things about last time that did and didn't work for me. I gave a loose script/sequence/fantasy of what I'd like and he was down.
...
We did it semi same as before, starting with a full body massage. This time I started on my front and when he got to my ass he did a very small amount of stimulation, just to lubricate and tease my sphincter. I then flipped to my back and he continued the massage.
Eventually getting to my cock and slowly progressed from hand job to blow job with deep throating and a did of prostate stimulation again. This was slow and gentle though, still more akin to foreplay than trying to get me off.
I'd mentioned in our messaging that I didn't want him to get me off this way, but rather when he felt I was ready he could take my anal virginity.
As I got closer to my climax he withdrew his hand to get himself ready. He slowed and stopped touching my cock before I felt some more lube and his cock at my entrance.
This was the moment of no return as I felt his head pop in with ease due to the previous loosening/massaging.
He got about half of his cock in before he started rocking back and forth slowly driving himself deeper with each thrust.
I felt the gentle rubbing on my prostate and I knew that this was going to be worth it to finally get some real stimulation. After a few minutes of small rocking and getting used to his size he slowly increased his movement. Making proper thrusts with his depth, I encouraged him that this was feeling great and my muscles were involuntarily flexing as he grazed past my prostate.
As his speed increased he held onto my thighs, my mind started drifting as the sensations took the front seat. I started moaning as the pressure started to build. I wrapped my legs around him I pulled him closer, deeper and asked him for more. He really started pounding into me and following his thrusts through with his weight. I was completely out of it at this point, strings of my precum was getting everywhere.
When we'd discussed in our messages how I'd like it to progress I'd said that I would love to cum handsfree if possible. If it wasn't working for me and got tired then he could finish me off with his hand but that wasn't even close to being the case here. I'd mentioned that once we get to this point then it's time for him to have his own fun and to do as he pleases.
He stopped for barely a few seconds as he rolled me back over to my front and went straight back to pounding me from behind. This put a lot more pressure on my prostate as he thrust past it.
Not more than 2 minutes on my front with him pounding deep down into me with his weight smothering me did I cum all over his bed. I was in pure euphoria as he continued to use me. I was still coming down from my climax, still squirting and clenching down on him when he let out a loud grunt as he drove him self even deeper, I screamed out in pain and pleasure as this took me by surprise, I didn't think he could have surpassed the depth of his pounding but the thrusts as he climaxed felt impossibly deep. He made several thrusts like this as he came in me raw; a grunt paired with a deep thrust to deposit his seed in me, countered by my screams turned whimpers as he slowed and his forceful thrusting weakened.
As he came down from his climax, his weight relaxed onto me while he stayed inside. I savoured the euphoric and smothered moment as we got our breath back.
This was where our plan originally ended as we didn't think more than one climax was on the table.
But I wanted more like a dirty slut.
I clenched around his girth several times eliciting a moan from him. I could feel him softening so I knew if I let him out he wouldn't be getting back in until he was hard again.
I slowly rolled him over so that I could keep him in me and rose to a seated position in his lap. I felt like a proper horny slut pulling off this maneuver, a big tangent from when we'd started.
I grinded in his lap to see what his reaction would be while he was still collecting his breath. And he disappointingly said that he was ready for a shower
He sat upright so I was still in his lap but rather than push me off he reached around and fondled me from behind, not taking long for me to grow a semi.
As I'd done barely any of the work up to this point my energy was still pretty high.
The whole idea in my head about maneuvering and keeping him inside me was the horny, slutty idea of going straight to round two of his pounding without him ever leaving my ass. But as the horny adrenaline subsided and I came to my senses I realized that is more fantasy than realistic (though I'm sure it could be done with better communication but that was absent here)
So abandoning this, I slowly rose and let him slip out of me, he'd definitely shrunk a lot by this point but I still enjoyed the feeling as he slid out past the sphincter.
He was still holding on to my semi hard cock as I turned to face him. He lay back down and spread his legs, suggesting that if I wanted to I could have a turn with his arse.
He continued to gently stroke me. His cock was covered in cum and lube and for the first time ever I grabbed another man's cock. It still didn't really do anything for me, I was alternating between stroking him and myself trying to transfer his slickness to my own.
I'd only done anal once before at this point (that same girl I mentioned way back) so still a massive amateur. When I was fully hard again I squirted additional lube and placed myself at his entrance.
I pulled myself into him slowly, admiring how his ass seemed to just swallow my cock. I copied the movements he did on me earlier and slowly ground further into him, before long I was jack hammering away at his arse like it would be my last time.
We switched positions so he was on all fours and this is when I really drove it into him. I gave the last of my energy as I came inside of him. It was a powerful orgasm that sucked what little life I had left. I pushed him forwards onto his chest and fell forward into him as I continued to paint his insides. I was still hard when I began to remove myself but I then stopped and forcefully thrust back in which got a few good moans from him.
I rolled over next to him as I softened and began gathering my breath.
The "conversation" if you can call it that was literally him asking me how I was? With my response of ”Like I've just finished a massive workout and in need of a massage.”
I'd meant it as more of a joke but that's exactly what he started to do. He was slow and gentle working over my whole body as I was drifting off to sleep.
I don't know if I ever lost consciousness as all I remember is the feeling of his head pushing inside of me bringing me back. This time, he was a lot less gentle and was fully inside and pounding away with just a few thrusts. I was groggy and couldn't do anything as my ass freely accepted him inside.
I was pretty sore but when I tried telling him to take it easy I couldn't get the words out. I weakly tried pushing him off me but he swatted my hands away and then pinned my wrists. I think my weak resistance just spurred him on further as his thrusting intensified.
It felt like I was getting rapidly punched in the guts which helped bring me back faster. Though I actually began to get aroused by the situation.
With each thrust he pushed me further up the bed till I was banging my head against the headboard. This broke my mood and my erection began to subside and I finally managed to tell him to stop as my head and ass was too sore.
But he didn't listen, said "just a bit more" through gritted teeth and kept on going. I wasn't in any position to stop him so all I could do was wait him out. Thankfully he didn't take too much longer as he came in me for the second time with grunts and deep thrusts, seeding me again with cum.
...
This incident was a few months ago, now we're regular fuck buddies and I get bred every week.