Budding Sexuality with Glen

It seems easy in the porn mags and videos, so why wasn't this working? I thought to add spit and made it slippery but I was still too tight as Glen continued to push. Suddenly Glen pushed a bit hard. I felt a sharp pain of stretching skin and the ring of my anus, "Oww, stop, pull back," and he did right away.

Glen said, "I wasn't in yet."

"Okay. It hurt though. Try again, slower."

Breathing heavily, Glen said in a respectful tone, "Okay." I'm not sure Glen was experienced in taking a virgin gay cherry. He spit on his hand and rubbed his cock with it. This time I had an idea of pushing out with my ass like the times I played with myself. I was so intent wanting him in me I again forgot to relax. All my pushing out didn't do much. Finally we just stayed in that position for a bit, with his head just outside stretching me, and he started to stroke my thighs and legs and soothe me into relaxing, "You need to relax."

That was when I had the first mind meld with my ass. After a minute or so I said, "Okay, try now." As I barely was in control of my ass I was able to push out a little and Glen felt an opening and pushed forward. His whole head went in and I felt some pain, but it was more tolerable than before. I said, "Wait." before he pushed any further so I could take a mental and physical pain check. After a minute or so I said, "Let try again but slow. Pull out first." As he did I felt the dry stretching and pulling with slight pain, but then felt an odd empty feeling. I used some spit to coat my hole and poke a bit inside. Glen used some spit on his dick to help. Feeling a sense of urgent, raging horniness and wanting to be fucked I said, "Okay, go on but slow."

Glen started to move his hips in very short back and forth and side to side movements and then felt his head pop in with barely any pain. This felt awesome and I grunted a soft moan and giggle of approval, but my ass didn't want him to go in any further yet. I felt the second ring just inside not wanting his member to go further - carrots and handles worked, so why didn't his cock? - I was still tense. Glen couldn't help but keep his cock wiggling barely inside. My hole had grabbed his cock and as he moved back and forth it was like he was masturbating using my hole. I didn't care and it didn't feel the best, but I wanted it. I was rock hard and loved what he was doing to me. He maybe got two more inches in and it still felt like he was at the entrance. He barely picked up the pace and started to grunt as I felt a little more of dick slip inside me. He must have reached far enough that my internal lubrication started to creep up inside as I felt a little slipperiness around his head, but not enough for him to fully penetrate me at my entrance.

Forgetting about my own dick, now in a fluctuation barely-hard state, I felt down to feel his cock at my hole, and I smiled and laughed at the sexiness of me being fucked. My fingers formed a V over his cock that was in me, and I started to gasp and breathe heavy as I loved this new feeling. I wanted him to cum, I wanted to make him happy and show him how I could do that for him.

His slow rhythmic thrusts changed started to pick up again for the 2-3 inches he got inside. My hands clasped behind his neck as I started to get flushed - that's new! - when the pain mostly subsided. With low slow tones I started just naturally moaning, "Oh, oh Glen, fuck me. Uh, yeah, fuck me. Fuck me. God I love it. Oh, Glen, yes, oh, oh, fuck, this feels good. Fuck me. Ohhh." I wasn't totally out of it, but talking was making it feel better and it actually did!

My arms went back lazily over my head as I gave myself fully to Glen. He picked up to a piston rate with his cock still only 2-3 inches in. My moaning matched his pace knowing what was in store and I wanted his cum in me - not because I wanted to feel it, but because I wanted to make him happy. With a loud gasp and a single grunt, he started cumming. I was so tense I didn't feel his cumming inside, just that his cock seemed harder and it was pulsing quickly, 4, 5, 6 times and more! I smiled big, laughed a bit, and was so proud I made him so aroused and horny that he came in me! I wrapped my arms as far around him as I could to bring him close to me, hugging him and squishing my precum soaked semi-hard cock between us.

My cock was sensitive to the slippery feeling of our bodies together, but stayed semi-hard. I felt mostly satisfied, but wanted to cum at some point. Glen stayed in until he was done, and as he pulled out I immediately felt heat, wetness and a little pulsing pain. I also felt that my hole was still open and it made me want him more. Even with all those feelings, I knew I wanted to do this again as it had to feel better. He asked, "Are you okay."

I said, "Yeah, it hurt a little. But I hope you didn't get me pregnant!" (That became a running joke with us). "Did you like it?"

He laughed and said, "Oh, yeah. Do you want me to take care of you now?"

With a bit of embarrassment, sudden confusion, and wanting it to be about making him happy and not about me I said, "No." I felt a slight squish between my cheeks (new but happy feeling) as I got down from the freezer with my almost soft cock bouncing carelessly in the air. I clumsily pulled up my pants enough to cover my ass, and kept my boxers in my hand so I didn't soil them with my wet pre-cum soaked crotch and squishy backside. I made my way to the bathroom saying, "I'll be right back I'm going to clean up."

I got to the bathroom quickly and jerked off at the urinal with a barely hard cock. Within a few strokes I had a massive orgasm, shooting load after load and feeling my ass hole pulse, but not fully close, with every shot. Never had I cummed without being super-hard, nor felt the pulsing as intensely from my ass as I did then. I then had a natural urge to sit on the toilet because I felt the need to let Glen's load out of me. As open as my hole felt, it was still tight as I had to poke a finger in to drain the cum from me. I felt intrigued by the smell, but loved the slipperiness around my hole when I wiped myself clean. I smiled about the idea of cum inside of me, which started making me semi-hard again.

After a thorough cleaning at the sink, (I couldn't leave traces for my wife to find!), I went back to the storage room where Glen had cleaned up. He said a little incredulously, "You know I could have taken care of you too. You didn't have to do it yourself."

I said, a bit shy and dumbfounded, "Well, I don't know how this works. How about next time?" I was very confused about etiquette and just about the whole situation.

"Oh, there will be a next time? Well, this time was fun."

"Yeah, but hopefully I will be more ready and it doesn't hurt."

"Sorry!" Glen exclaimed. I could tell he felt a bit bad, but I wasn't holding it against him. "Still want to go to the party?"

"No, I'm going to head home. Don't worry, it's nothing you did. I had fun and want to do it again. As long as I'm not pregnant!"

Glen laughed, "I can get you pregnant if you want me to. We just have to do it more."

We hugged a quick goodbye and I left for home.

On the drive I thought about going to the adult book store for something other than the straight porn magazines I was getting before my marriage. Gay porn mags didn't turn me on, but maybe they had a gay version of Penthouse Letters? I also realized during my drive I was a little sore and still very horny. I felt a continuing arousal I had never experienced, and a pulsing and increasing wetness around my new broken cherry. I thought, wow, was this what it meant to be left wanting more?

I got home about the usual time as if I had gone to a party and went to the bathroom to get ready for bed. My increasingly hard dick wouldn't go down and had sprouted full again. So, I jacked off with one hand and circled my ass hole, that was hot and had self-lubricated, with my fingers while replaying the night I just had. I came into the sink within a minute! As I orgasmed I felt these wonderful contractions of my asshole on my finger and wanted Glen's dick back there. I think I was hooked. It was the first time in my adult life I came twice in an hour, and realized that with a little bit of Glen's cum still in me that my ass had also self-lubricated! I cleaned up and waited a few minutes before I could crawl into bed without a hard on.

I snuggled up to my wife, who was in a deep sleep, and drifted off to sleep with thoughts about what Glen and I could do next and a flood of guilt for waiting until after I was married to sexually explore.