Over the last 5 years I have met up with hundreds of guys on Grindr. I usually give them a bj and go on with life. Occasionally I will get this thought about Anal Sex. So I go searching and I find a guy and he totally doesn't know what he is doing and hurts me very badly. I then don't have anal again for a month and this keeps repeating. I have always got Mr. Stabbys.

Well then came today. I had Anal at a local Adult Theater for the first time last weekend and it was okay he wasn't huge so it didn't hurt to bad and he was gentle. Anyways I'm searching through Grindr today and I get a few guys to message me and as always most eventually stop talking to ya. I was going to call it a day on Grindr and just go home.

Then a Blank Profile as I was closing Grindr started sending me pictures and a nice "Hey" text. I open it back up and say what the heck. He is Latino so he is my type I go for. We talk for an hour. I'm at a coffee shop and people left and came left again. I was getting anxious that it was going nowhere. He say give him some time he needs to get ready. I agree. I sit in the shop for another 30 minutes and he finally sends me the address.

I jump in my car and he was only 3 minutes away. Like seriously right down the street no more than a mile. I pull up and message that I'm there. He comes to the door to let me in and he was so hot. His pictures didn't do him justice he was a twunk of a man. We set down and he could tell I was nervous. He was just so hot I couldn't believe he would be interested in me.

I finally calm down after we do some recreational things. I finally mustered up the courage to start feeling him up while he was talking. He kept talking for a bit and then he finally said "Well I guess you really want to start sucking my cock". I blushed and nodded my head. I really love Oral. Probably my favorite thing.

He warned me he wasn't going to cum from Oral he said he would finish himself or if we did anal he could definitely cum. Over the next Hour and half I sucked on his shift having so much fun. He was enjoying it but you could tell he really wanted my ass. I was nervous and way to tight to do it I told myself.

I don't say you should do this but he offered Poppers I had only tried them once. But they work I calm way down. I took a few Sniffs and I started to relax. He tried to Throat Fuck me but by this time I kept gagging because I had sucked his cock for so long. Not much suction left at this point. Also all I could think about was his cock in ass by this point.

He again warned me he was still far away from Cummings. I finally say "alright you win let's go do butt stuff". I have to stop the story for a minute and say I had warned him about my past experiences and that if he must stab away then okay. He said "Its not supposed to hurt I will show you". Okay back to the story. He takes me to his bed and gets me into a doggy style position and again I calm down with poppers because I was shaking. I was very Nervous this was going to be bad.

He poured some lube on himself and on my ass. He started by grinding on my ass intill his cock was rock hard again. He played with my ass and poured more lube in my ass. He had gotten me pretty relaxed and he said he would go very slow.

He pushed up against my entrance and I clinched up. I took another wife of the stuff and calmed my nerves. He tried again and I was relaxed he slowly pushed in about 2 inches. He waited and asked if I was in pain. He told me never enough lube and poured more on his cock.

He finally said "Are you ready?". I answered back and said "let's give it a go". I took a deep breath and he slowly stocked in and out going a little deeper. I was shocked as this felt amazing. I was moaning so loud. He was talking his dirty talk and it was turning me on.

He pulled out and lubed up his middle and index finger. He inserted them in my ass and started twisting them around. It drove me insane. I was moaning very loud and begging him to keep doing it. He was enjoying being in control.

When he reinsert his member he went in at a different angle and pulled out. He moaned in pleasure and so did I. He was pushing up against my prostate. He did it 3 or 4 times and it was oneof the best feelings in my life. I was grunting and moaning for more.

I guess it had really got him close to cumming after he had just said this could go for awhile. Because he pulled out and nibbled on my ear and gave me a few sloppy kisses. He then went back in with is cock but he was already to close. He said I'm going to cum and thrusted 5 or 6 more times as I could feel his cum inside me.

He lays on me for a second and then pulls out we both lay on our backs for a second intill he offers a shower to clean up. I accept and we take a shower to get clean. He had some things to do but he told me we need to meet up again this coming weekend.

I'm telling the truth more tops need to learn how to please a bottom because if they all fucked like that I would be having anal every night of the week.

If you have read this far thank you! I'm new to reddit but I have found I want to tell these stories so maybe one day I can come back and remember them! If you want me to tell you what happens this weekend let me know I will probably update or make a new post about it!