Don’t get hung up on size, no pun intended. Just find a guy you connect with for a truly memorable first time experience.
I was in my 50's when I got my ass cherry popped. I was probably like
@Lpsgyeeee - did it
not because I was attracted to guys, but mostly curious just to see what it was like and prove to myself that I could take it. I searched for several months before I found a guy that I trusted would not only be considerate and respectful but give me an overall good experience. The guy I chose convinced me that he had broken in quite a few virgin holes, and we exchanged several emails as he described how he would deflower me, and how I would most likely react at each step. I got enough information about him that I could verify a lot of what he claimed about himself, and I could trust him.
He made certain I understood:
- I would be fucked "like a girl" (on my back, thighs spread and legs up)
- I would be kissed
- His cock would be bare
- It would probably hurt
- I would receive a natural insemination
- I would probably experience both the physical, and mental, sensations of a virgin girl getting her hymen broke and her vagina split by a cock for he very first time
And that's what happened. He prepared me well with plenty of foreplay. I thought the kissing would be the worst part, but it was actually quite enjoyable. As he told me beforehand, virgins never REALLY relax. He put a folded pillow under my hips to make my hole more accessible. As I watched his cock get into position, knowing what it was going to do, I felt a puzzling mixture of embarrassment, anxiety, eagerness, fear, curiosity, desire, and nervousness. I'll never forget the "OUCH!" moment. It hurt at first and I cried a little. (That's typical for most of our first times, regardless of size, though I'm sure it's more painful if the guy is especially thick, or very long.) It was a strange and very unique sensation to feel the cock going up inside me - it felt like he was almost all the way up under my ribs. I'll also never forget receiving his semen deep inside my most personal and intimate hole.
I had four surprises from the first time taking it in my ass:
- Once he popped me, and his big cock head was just inside my sphincter, I was still hurting but I really WANTED him to fuck me, and I wanted to give him as much pleasure as possible.
- At the end, he pushed deep, I yelped again, and I felt his cock jerking inside me. At first I didn't know what was happening, but I quickly realized he was cumming inside me. The surprising part was that I involuntarily, instinctively, wrapped arms and legs around him to feel his body shuddering and to keep him deep inside me.
- When he finished twitching, he pulled out and immediately went down on me. I had lost most of my erection when he broke through my sphincter. Even though I was mostly soft, I exploded into his mouth on the second stroke of the blowjob. I had NO IDEA that I was THAT CLOSE to cumming!
- I have been with only one virgin girl, but after my anal defloration I think I understood what she felt when my cock broke her hymen, and why she cried through the whole first fuck (and it wasn't entirely because of the pain), and why she wanted to do it again just an hour or so later.
You don’t want a hung top for your first time. I don’t consider myself hung but have been the first for many lads and it’s been disappointing, for both of us, most of the time. Rarely is a virgin able to take a hung top on his first ride.
It's sad to hear that both you and your partners were disappointed. My first guy's equipment was probably similar to yours: just a little longer than average, and definitely thicker than most guys, but not "huge". My first time was embarrassing, painful, and I yelped and cried but I was NOT disappointed. It was a very significant and satisfying experience. Afterward I learned that one reason he did virgins bareback was so he could finish quickly if the bottom had difficulty, though (as he said when he apologized for cumming when I was just starting to really enjoy it) virgins are always tight and tops seldom last long inside them. And I realized that he put me in missionary position so he could watch me as he put it in - the grimace, the flinch and squirming, the yelp, my hands clutching the blankets, etc. I think he got special satisfaction knowing he was my first.