Surprise First Anal Experience

I was 21 and had just finished at university. I knew I was into cock and had sucked one before but had been too nervous to take one in the ass. To me it felt like crossing a threshold into being gay that I wasn't sure about.

I had been chatting to a man called David online, who lived in my town for months by this point, and he made me feel comfortable enough to explain my anxieties about taking anal. He was very understanding and didn't try to push me into anything at all. He had sent me pics though, and was my perfect guy. Older, early 50s, tall, slim, bald, and with a sexy strong jaw. He sent me an underwear picture where I could see that he was obviously well-endowed.

David one day asked if I wanted to come round to his and I could use his dildos and he would just watch or leave me to it if I wanted. I was feeling particularly horny, and so I quickly said yes before I lost my nerve. I showered, shaved (everywhere!), and douched myself clean.

I arrived at his house feeling nervous, but he had said not to worry if I wanted to leave at any point, so I knocked the door and he answered looking tall and sexy in casual jogging bottoms and a vest. He invited me into the living room. There was some daddy-twink porn playing on the TV, which I had told him was my favourite, and there were 3 dildos of varying sizes and some lube laid out on the floor invitingly. I was nervous, but really turned on.

He asked if I wanted to sit down first or get straight to it. In my head, I thought "if I don't do this now I'm going to bottle it!" So I told him I wanted to get started. He asked whether I wanted him to leave or stay. I said whatever he preferred. He laughed and said he'd obviously prefer to stay, and sat down on the sofa.

I went to investigate the dildos. There was an enormous one, which must have been about 11 inches, which turned me on, but terrified me. There was a much smaller one, perhaps 4" with a vibrate function, but I liked the look of the 7" one that had all the veins like a real cock.

I was aware that David was watching, but trying to act like he wasn't there to stay on top of my nerves. So I kicked off my shoes, followed by my trousers and t-shirt, and then finally my underwear, until I was totally naked. I heard David moan a little, but pretended not to. I grabbed the lube and lay down on the other sofa, facing up with my bum propped up on the arm rest. I squeezed some lube onto my fingers and reached down to rub it around my hole and then pushed a finger in. As I glanced over I saw David with a hand down his jogging bottoms, starting at my ass, stroking what looked like a rather large cock.

The fact that there was a large hard cock in the same room as me was a massive turn on, considering I'd been mostly too nervous up to this point to put myself in this position, but I wanted to carry on with my plan to use his toys. So now that my bum was nicely lubed, I grabbed the 7" dildo and squeezed some onto it. I stroked the dildo to make sure it was covered in the lube, then I placed it down to my smooth hole. I tried to relax as I pressed it against my hole and I felt the head start to push in. Initially the thickness came as a surprise as I was only used to my fingers, but very quickly I wanted more.

As I gradually worked the dildo further and further in, I felt more relaxed in the situation. I was enjoying myself and it didn't feel wrong. I looked over and smiled at David, who was still playing with his cock. He asked I was enjoying myself. I said "yes" breathing heavily as I pushed the dildo back and forth. He asked if I was satisfied. I shrugged and said it's still just me doing it on my own so it was nice, but could be better. He said if I wanted, he could work the dildo so it felt more like the real thing. I shrugged nervously and smiled.

He got up and crossed the room. I could see his large erection through his jogging bottoms. And it looked large. He asked if I minded him wanking himself off while he does it. I said no. So he dropped his trousers and his full manhood sprung up. It was beautiful. About 7.5 inches, veiny, and perfectly smooth. He put some lube on his hand and started stroking it. I let go of the dildo, which was fully inside me, and he stood at the end of the sofa and took a hold of it. He told me to hold my legs up and lean back and shut my eyes and imagine it was a real cock. So I did.

He started moving the dildo slowly. And immediately I felt so turned on about giving away control to someone else. He sped up and eventually was going at quite a pace. I opened my eyes to take a peek at him wanking himself off. His cock was glistening now from the lube, and looked incredible. Then I shut my eyes and leaned back, enjoying the feel of the dildo inside me. He asked if it felt good and if I had any requests for faster or slower. I told him it was up to him and that he could do whatever he wanted. After a few minutes, he told me to totally relax, as he was going to pull all the way out and then put it back in. I did as I was told, and he pulled the dildo out, and I felt my smooth hole gaping wide open, then after a second he pushed it all the way back in. It felt incredible. Then he did it again, and again, and again. Every time I gasped and whimpered.

He told me to keep my eyes shut and imagine it was a real cock. I did as I was told. He carried on, and after 9 or 10 times, when he thrust it in, it felt like more of a stretch. I assumed I had clenched, and concentrated on relaxing, but the next time felt different too. Then the time after, I felt his legs touch my bum cheeks. I opened my eyes just in time to see David pulling his cock out of me.

He looked down and smiled, but he could see I was a bit rattled by what he had done. He immediately apologised and said he thought when I said he could do whatever he wanted, that meant I wanted the real thing. I had a million thoughts running through my head but couldn't verbalise them. I had pretty much crossed the threshold I had been so nervous to cross and I couldn't deny that it felt amazing. So I embarrassingly just said "I don't know..." I became conscious that the tip of his hard cock was pressing against my hole, and it felt so tempting. He asked if I wanted him to stop. I shrugged. So he gently leaned forward and I felt it slip inside me again. I thought "what the hell!" and leaned back as he started thrusting, gently at first and then gradually harder and harder, until I could feel his balls slapping against my ass.

Damn it felt good. Why had I waited so long??!! Finally, I was gay! And I wasn't a virgin any more.

He asked if I wanted to turn over. I said OK. He moved me into position where he wanted me. Bent over the side of the armrest, him stood behind me. I felt his cock push against my hole and slip back inside and he immediately started thrusting hard.

I could have stayed in that spot forever with him pounding me. But it wasn't long before all of a sudden, without any warning, he grunted, and I felt the warm sensation of his cum squirting into me. It felt incredible. I was addicted.

I hung around for the rest of the evening, and David helped me try a number of other positions. But that was how I lost my virginity, and set me on the path to being quite a little cum slut.