Anal for the First Time

This is a true story that happened a couple of days ago. Of course I changed the names of the people involved but otherwise this is everything I can remember.

My name is Paul. I am 40, tall, athletic, handsome and masculine. I consider myself straight in that I am rarely attracted to guys and can't see ever having an emotional connection with a guy beyond friendship. However, I have always fantasized about fucking, sucking and getting fucked by a guy.

I have a very cute 21 year old (open relationship) girlfriend named Michelle. I am usually very dominant with my women sexually and Michelle is very submissive. For the last few months however we have occasionally reversed roles. Every few weeks, Michelle has been fucking my asshole with a strapon. She is extremely open minded and we are very in love. She has opened me up to the idea of actually getting with a guy and has told me she really wants to see it happen. We often talk about having bisexual threesomes with both guys and girls.

Michelle's been away traveling around South America with her friends for a for a few weeks, so I figured this would be a good time to meet some guys to eventually make our bisexual fantasy reality. I posted an ad on Craigslist being very specific about what I wanted: only masculine, cut, athletic and tall guys, preferably straight or Bi. I said I was looking for myself but at a future date it could lead to a threesome with my girlfriend. I added a picture of my very good body and another of my 6.5 inch beautiful, cut cock.

You can imagine I got a ton of replies. One guy, John was particularly interesting. He sent a picture of his cock and body and it was great. His cock was about the same length as mine, beautiful and very, very thick. We emailed for a few days and on Saturday morning he invited me over for a hot tub.

I said to myself, "Fuck it, I'm going to finally do this." I told him I'd be there in a half hour, cleaned my asshole and texted Michelle telling her to call me. I wanted her encouragement. As I was driving to meet John, Michelle called. She ended up getting me really horny and even though she was far away her encouragement really helped me to take my first real assfucking.

Our conversation went something like this...

Me: Guess where I'm going?

Her: Where!!?

Me: I'm going to meet a guy at his house for a hot tub.

Her: Oh my god baby, that's awesome. I wish I was there. What are you going to do?

Me: I'm not sure. I have to see if I like the guy.

Her: What if you do like the guy?

Me: I'm still not sure, I'd like to feel his cock and maybe suck each other's cocks. What should I do?

Her: You should take his whole cock in your mouth and you should both cum in each other's mouths.

Me: Should I eat his cum?

Her: Fuck yeah, you should eat all his cum. Are you gonna fuck?

Me: Sweetie, I won't if you don't want me to because I know you want to see me get fucked for the first time.

Her: Oh, baby I really do want to see you get fucked but I don't want to hold you back either. If you really want, you should do it. Did you get your asshole ready?

Me: I cleaned it out but I didn't have time to loosen it up. You think I could still take his cock?

Her: Oh my god, that's so fucking hot. How big is his cock?

Me: It's like 6.5 inches but looks really, fucking thick.

Her: Oh baby, I know you can take it like a man. You always do such a good job taking my cock. He'll just loosen your tight little asshole up with his cock. You'll take it really good and I bet you're gonna love it too.

Me: Thank you, I needed to hear that.

Her: I'm gonna be so proud of you for taking a big cock in your asshole.

Me: Should I let him fuck me hard?

Her: You should let him fuck you really hard and rough. I know you'll take whatever pounding he gives you really good.

Me: Fuck, you're getting me so horny. If he's hot, I think I'm going to actually let him fuck me. I want his dick in my asshole real bad now.

Her: Fuck that's so hot, I hope this guy fucks your asshole really good.

Me: Actually, I think I'm at his house now.

Her: God Paul, have a really good time.

Me: Thank you. I love you so much.

Her: I love you so much too. Please call me and tell me what happens.

Me: I will of course.

John's house was very nice. It was on a hill with a view and very private. He greeted me at the door and instantly made me feel very comfortable. He was about 6 feet tall and thin but muscular enough to not be skinny. He was in his 40s and handsome. He had dark salt and pepper hair and heavy stubble on his face.

He invited me in and offered me a drink. We went to his couch to talk for a while. We chatted mostly about sex. After about 10 minutes, I decided I wanted to see him naked so I suggested we go to his hot tub.

We went outside and undressed. His body was good with a nice amount of hair in the right places. His dick was soft but I could tell it was big and thick. We sat in the tub facing each other and talking some more. John and I both began caressing each other's legs. It felt good and I started playing with my cock. I could see John's cock growing under the water so I reached over and began playing with it. It felt amazing to have another man's cock in my hand.

John shifted over so we were next to each other and could stroke each other's cocks. At this point everything started to seem like a dream. We started jacking each other off. After a few minutes I got so horny I felt kind of possessed so I put my head under water and took John's cock in my mouth. It felt fuckin hot and it turned me on so much. Unfortunately the hot tub water tasted like chemicals so I came up and suggested that we move inside to John's bed. John got us towels and we made our way into his room. I was holding his studly cock the whole time.

When we got into his room we rubbed our cocks together for a bit then I got on my knees and began sucking John's cock again. It tasted so fucking good and manly and it felt amazing in my mouth. It was way too big to get the whole thing in without gagging. But I managed to get about two thirds in, all the while playing with John's very large ball sack. One of my favorite parts was licking and sucking his balls. I could tell he had a big load waiting for me and it was really hot to wrap my mouth around his cum filled balls.

After sucking him off for a while, John wanted to return the favor so he told me to lay down on the bed and began sucking my cock. As he was doing so, his hands massaged my balls and I kept pushing my legs higher and higher hoping he'd get the hint to touch my asshole. After a few minutes, he began to touch it.

This got me so worked up I said, "God stud, I want you to finger my asshole."

With that John put some lube on his fingers and began finger fucking me. At this point I knew for sure I wanted it all and said, "Will you fuck my asshole baby."

John simply replied, "ok". He then pushed my legs up and began licking my asshole. After a minute or so, he began working his tongue in and out. I loved it and I was starting to get ready to get fucked.

So I asked John, "Do you think I'm ready to fuck?"

He replied, "Yes, if you think you are."

I said, "I think I am, please fuck my asshole."

John simultaneously put a condom on and smeared a bunch of lube on my asshole. He stared at my asshole the whole time wide eyed. I just looked at his beautiful cock. My legs were in the air and I was about to get anally reamed for the first time by a real dick. It was really exciting.

John pushed the head of his big cock against the entrance to my asshole. It felt so fucking hot I couldn't believe it. He was an expert fucker and was able to push his cock in without any issues. I was really tight and his cock was really thick so it hurt a little at first, but he was gentle. He left only the head at the entrance so I could get used to his girth.

Then he asked, "Are you ready for more?"

By this point I was and responded, "Yes, fuck my little asshole."

With that John began pumping his very thick cock in and out of my ass. It felt really wild. Looking up and seeing another man fucking me was amazing. He was gentle yet firmly fucking his whole cock in and out of my asshole. I could feel his heavy balls slapping against my ass. I could also feel his beautiful dick rubbing against my prostate and I started jacking off. It felt amazing.

John was holding my legs and looking at me with intensity. I could tell he was really into it and loved fucking my ass. He breathed hard and grunted in a very masculine way. He was going slow but deep and hard. He was being very gentle but at the same time very assertive. He was fucking me hard enough so he was dripping sweat and my body was being lightly pushed with each in stroke. I was grabbing his hips and his ass to pull him in.

I wished I could take it harder and rougher but this was my first dick and it was very large. I could feel that if he went really hard it would hurt. So I encouraged him to keep fucking me like he was.

I said, "Oh god baby, keep fucking me. You are fucking me so good. I love it. You are such a stud." I then asked him, "Am I taking it good?"

He responded, "You are taking it really well. Lets try a different position."

With that, he began moving my hips. He managed to roll me over so I was face down. Somehow he kept his dick in my butt the whole time. He pulled up my hips so he could fuck me doggy style and began pumping in and out again even harder than before. From this angle his cock was going super deep into my bowels.

It was so hot and even though there was some discomfort I loved it. I looked over my shoulder and reached for John to come kiss me. We had a really deep tongue kiss while he kept jacking his cock in and out of my bowels.

I wanted even more so after our sexy kiss I told John, "Fuck me really fucking hard."

This got him going instantly and he began pounding my ass as hard as he could. I loved the feeling of being pounded but unfortunately it hurt too much. So after a few seconds, I had to ask him to stop. He took a little break and then went back to fucking me firm but slow for a few minutes.

He then said, "Lets cum."

With that, he pulled out of my asshole and took off the condom. I turned onto my back again and spread my legs. John put his dick right next to my dick and we both began jacking off. It was really sexy seeing John getting himself off. I told him to cum all over me and after a couple of minutes he released his heavy load all over my stomach and dick. I licked up a little of it and liked the taste, but for some reason did not eat his whole load, something I regret a little bit.

For the next 15 minutes or so we laid on John's bed together and had a very cool talk. I don't really remember our conversation but I do remember us both saying we should do this again. We also discussed having my girlfriend Michelle involved next time. When I called Michelle a little later, she was proud and happy for me and she definitely wants to be part of things the next time.

I sent her a picture of John's body and cock and she responded, "Wow, I can't believe you took that."