Well then, let’s try and put in words my first fuck; anally with a guy I mean. It happened when I was at university and whilst having a ‘relationship’ with a guy called Mike. For a few weeks we had been playing around, wanking, licking, sucking; just general fun. We had even progressed to fingering each other’s ass sometimes, but not too often.
Then one morning as we were playing with each other’s cock, and I was fingering Mike’s asshole, he said, totally unexpectedly, that he wanted my cock in there instead of a finger. I had often wondered what it would be like to fuck a guy, so I asked him if he was sure and he replied that he was. He asked me if I was agreeable with that and I remarked that I was if he was. He stated that he had some Vaseline, so he got up and arrived back with a tube of it. Returning to bed, he assumed the doggie position. As a virgin at this I was a little nervous but I smeared some, well actually loads of, Vaseline all over my, by then, hard and pulsing cock and some on and in Mike’s asshole.
I knelt on the bed behind him, between his calves and moved in. Again I asked him if he was sure about doing it and he groaned a “Yes”.
So I held his arse cheeks and pulled them apart, seeing in full stare his arse eye. Then releasing one hand I took my hard cock and placed the purple head against his hole. I wiggled my arse a bit and tried to move my hips, and consequently my cock, forward. I wanted my cock helmet to enter the dark cavern within. However he was so tight; closed in fact, so that I couldn't get in at all. His sphincter muscle had closed up solid. He was frightened and I was very apprehensive. So I tried again, telling him to relax and again nothing. However on the third attempt my cock tip just entered through the start of his anal gate. My cock end and cum slit moved in a little stretching his ring slightly.
Mike moaned a grunt, not out of joy, but out of pain. I was a little frightened but he said to carry on. So I moved in further and my cock head started going into his ass. Half my cock-head at first as I moved in slowly. I held his hips as, by now, my cock knew its way in. Another little shove and my cock-head was fully past his ass ring. But as it popped in, Mike said it was too painful so I pulled out all the way. My cock isn't long but it is quite meaty. By then it was a solid rod, bouncing in front of me with every free move I made. I put some more Vaseline on it and moved back in once more. Again, I got into his ass entrance and soon I was cock-head deep in him humping his asshole but just with my glans deep. His tightness had forced my foreskin to roll back exposing my frenulum, that horny sweet spot which I love being rubbed. I moved in another inch but having my foreskin pulled back so far made it start to hurt me. As his ring grip on my cock was very tight we were both in pain; oh deep fun!!
I pulled out again and after readjusted my foreskin. I moved back into my desired target. Again my cockhead skin cover rolled back but this time I put up with the soreness. Things i.e. his ring, seemed looser this time so I pushed a little further into his ass tunnel and then another fraction as I slowly moved in deeper. Little by little, and gently, I inserted my penile staff until suddenly the tightness eased and my purple pal was deep into Mike. At that point the grip loosened a little and it seemed that getting my cockhead through the guardian gate and into Mike’s inner core was like popping a cock; tight, tight , tight, then, pop! Easy.
Mike was slowly getting used to the swell of my cock in his ass, filling him, stretching his anal ring. So I slowly moved in inch by inch until all my cock was inside his ass. I was fully docked in him. Through not a lot had been said we were both moaning and groaning, and an occasional swear word was uttered. I leaned forward over Mike’s back and reached around for his cock. I wanted him to enjoy this too but it was soft. I tried to wank him but it wasn't the best position so after massaging his balls for a while I sat back up straight again, kneeling between his thighs with my cock deep in his ass. I stayed still like that for a short while enjoying the 'power' sensation I had over Mike. Whilst I was fully within him I hadn’t started moving yet, but I was fucking him, and he was almost my slave. My hard cock was deep in his ass!! "Fuck me Mark," was all he said. So I did as he bid.
Slowly, and gradually, I started moving in and out of his ass, starting a steady rhythm of fucking. In and out, to and fro with a sensual, slow, pace. I held his hips tight as I told him that this was good. So fucking good. He didn't reply but still moaned. I started fucking him picking up the tempo, faster and faster until I was sweating; fucking his ass so hard, slamming my cock into him. Just as a cock in an ass loves to do. I kept looking down and all I saw was Mike’s back and my shaft appearing and then disappearing into his colon. So horny as I thought about the forbidden hole!!!)
As I fucked him I felt the tension of his anal ring around my shaft. As I pumped in and out, his sphincter tightness felt so good on my cock but it also meant that I wasn’t going to last too long before exploding into him. And that’s the way it turned out. I fucked his ass for maybe three or four minutes (ok maybe more; I wasn't counting). And then telling him I was cumming, I froze, then spasmed, as I shot my cream. Warm cum deep into him. That first volley into his depths was followed by more sharp, small, forceful thrusts as I shot my seed into his ass. Maybe five or six or seven more spurts of spunk went deep into him as I cried out in elation. Oh I was in joy; it was so good to cum in him. The orgasm still overwhelmed me as my spurts stopped but my seed still flowed from my cock slit into him. Maybe I was no longer ejaculating but just cumming. Flowing cum. Until my thrusts, spasms and feelings died away and I finished pumping him.
After my breathing returned to normal, I slowly withdrew my shrivelled cock and it cam out with another ‘pop’ as the head passed back through his ring. We flopped and collapsed next to each other on the bed and he grabbed some tissues and cleaned the cum running out of his ass. Such sticky tissues!
After a while I took hold of his cock and I wanked him off. He came after a while, shooting his cum onto his stomach and chest. My cock was still slimy with Vaseline, sticky with goo and the remains of my cum. As he lay on his back, stomach covered in cum, he remarked that more of my cum was seeping out his ass. He was cumming both ways! I remember we had a good laugh at that. After a while though he admitted he didn't really enjoy the fuck. It was uncomfortable and the position wasn't good. And at times it hurt him.
However about a month later I fucked him again. This time he was on his back with his legs on my shoulders as I fucked him. And as I did so I got his cock hard and jerked him to climax just before I came in him. He found that position, and his feelings, much better.
Well I hope my reminisces are good enough to give you the flavour. I got so hard writing that story at times. Hmmmmm…
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<a href="https://www.lushstories.com/stories/first-time/my-university-male-relationship-part-2.aspx">My University Male Relationship - Part 2</a>