First time I[M] did anal with my GF

When me and my girl first got together and started fucking on a regular schedule. I was always curious how it would feel to go anal. I asked if we could try it out and to my surprise she said yes. I didn’t think she was prepared for anal so I got a condom. I spend a few minutes trying to shove it in but she kept saying take it slow and I was being rough. I won’t lie and say I was rock hard, it was a little intimidating going into something so tight, so I got some lube and used a fuck ton of it. I started to thrust my half erect cock inside of her and as I got the tip in the grip it had on my dick started to get to me and I got harder and harder. My cock started to grow bigger and bigger inside of her and the increasing pressure from the both of us only made me want to start thrusting her from behind. It was only when I was fully erect that I slowly started to push in slowly inch by inch. She stopped me before I got balls deep and moaned how big my cock felt inside of her and how she could barley handle it. So I pulled out and took the condom off. Just like that it was over. I asked her how it felt and she told me. That it was a new experience and that she started to like it but that maybe another time would be better and she could be more prepared. We cuddled for the rest of the day until we got hornet again and fucked vanilla.

Creepy Fantasy [MF]

So my Ex GF was a freak and loved to do really crazy sex acts in public. We would go around and fuck in pretty much anywhere we could get away with. While out in a jog we stopped at a small family restaurant and decided to fuck in their bathroom, it was about 7 in the morning and everyone was there for breakfast except for us. She goes in to the bathroom first and I tell the staff I’m gonna wait out here till she comes back out. After 5 mins nobody’s paying attention and I walk in as well to find her waiting asking what took me so long. We were both pretty sweaty from jogging but she pulled her shorts down and I couldn’t resist. I pull my cock out and grab her leg and lift it to about the height of my waist then I enter her. She’s trying to keeps silent because of the people out side and I’ve never had the issue of involuntarily moans. After we fucked for a few minutes I come out and go straight to the men’s restroom and then I message her letting her know she can leave and I’ll follow her out of the restaurant. So we continue on our jog and we get back to her house both pretty exhausted and thirsty we get a drink, then she starts to talk about how what we did reminded her a creepy fuck fantasy she wanted.