Trying New Things

by Mark (Tennessee)

I’m a 63 year old man who just recently had my first gay encounter and I wish I could have experienced it long ago. Me and my wife’s sister had just dropped my wife off at the airport and was driving back home about a 2 1/2 hour drive, not quite halfway back she tells me she needs to pee and I jokingly tell her I’ll stop on the side of the road and you can open your door and squat right there, she says why so you can watch me.

I said of course I’ve always wanted to see a redheads pussy, she tells me they all look the same and maybe one day she would just show me, I say I look forward to that, I stop at a rest area and by then I needed to pee myself, we go to the bathroom and I’m at the urinal and some man a little younger than me walks up to the one next to me and I just curiously looked at his cock when he pulled it out of his pants.

He noticed and says I like the way your cock looks, I’ve never been in a situation like that before and I look at him again and now he’s slowly stroking himself and I started getting a hardon which freaked me out and I can’t stop staring at his cock, he tells me I can feel it if I want, I watched myself reach over and wrap my fingers around his cock and was amazed at how it felt, I stroked it a few times and he says we can finish this in my truck if you want to, I was confused and turned on at the same time.

I explain I have my sister-in-law with me and if I was by myself I would take him up on his offer, he tells me he will be here for a couple more hours if I change my mind, I put my hardon away and walk back to the car, she’s waiting for me and we get in and she says I thought you might be having rest stop sex with a man, I look at her and say what, she reaches over and squeezes my stills hard cock.

I tell her what just happened and I couldn’t understand why I got hard and if she wasn’t with me I would have went to his truck to have a little fun, she tells me I can never tell anyone but she has had lesbian sex with a friend for a couple years, Im speechless, I’m married to her sister and she says I should find out for myself, I might like it and she would never say anything to anyone.

I’m sitting there with a hardon from a man who wants to have gay sex with me and my sister-in-law is telling me to go for it, I tell her I will go to his truck and see how things go and she tells me if I decide to experiment and do anything that I should record it on my phone and when we get back home we can watch it again together, she then tells me her pussy is soaking wet thinking about me sucking a man’s cock.

I get out and find his truck and knock on the door and he tells me to get in passenger side, I’ve never been in a big rig before and I got in and he opens this curtain and there is a queen size bed with a refrigerator and a tv mounted on the wall, he hands me this folder with dvds and says pick a movie out, I look through and choose one called Boys just want to have fun. He puts it in and hits play and when it starts it’s a group of 12 or 13 naked men and everyone of them is sucking someone’s cock or getting theirs sucked and getting fucked and he asks if that turns me on.

I tell him I’ve been married for 33 years and I’ve never watched gay porn in my life and I didn’t quite know why when he was talking to me at the rest stop that I looked at his cock and got hard, he tells me he’s married too but for the last 7 years he started experiencing gay encounters and it just happened, he tells me we should get naked together and see what happens, as I take my shirt off I tell him about what my sister-in-law said, if we have any type of gay sex she wants me to record it, he tells me he doesn’t care.

I get naked and I watch him get naked and he points at my cock and says I must like what is going on, I tell him I’ve been hard since the bathroom and I’m excited, confused and horny and could I feel his cock, I set my phone up to record us and he tells me to do whatever I want, I get closer to him and I grab his hard cock and I love how it feels in my hand and right away I know I’m going to suck my first cock.

I lay down with my mouth just inches away from his cock and slowly stroke it, it was now or never so I opened my mouth and put the head of his cock in my mouth and he moaned and said it feels great, I put as much as I could get and he asked if I wanted him to suck my cock at the same time and I said yes, we got into the 69 position and he took my cock in his mouth and I thought I would explode right then.

I tell him to stop or I will cum to fast and he says he’s going to let me cum right now and then the next one will be longer, he pushes me onto my back and starts deep throating me and I started cumming in seconds and my orgasm was the best one I’ve ever had, he swallowed my cum and my cock stayed hard, I tell him I loved that and he asked if I wanted him to fuck me in my asshole, I would do anything you want, he grabbed some anal lube and made sure my phone was getting everything.

He asked if I wanted him to wear a condom and I said no, he lubed his cock up and then started finger fucking my asshole, every time He went in me I shuddered, he started with one finger and worked his way up to 3 fingers in me and after 10 minutes or so he said I was ready, I was on my back with my legs in the air as he got between my legs and I could see him getting ready to put his cock in me.

My cock was oozing cum and twitching and bouncing around and then I feel his cockhead touch my asshole, all of a sudden I’m wondering what the hell is happening to me, I forgot everything when he slides the head in me, he asked how I was and I say fine, he tells me to push like I’m shitting and it will help, I feel him pushing more in me and I feel full but he comes pushing, he stops and tells me it’s about half way in and I say put all of it in me now.

He thrusted just as I bucked and I thought I was dying from pain and he tells me it only lasts a few minutes and he slowly pulls it almost all the way out and then slowly back into me, after a few times I started feeling more pleasure than pain and I say I’m ready for you to fuck me now, he reposition my legs over his shoulders and starts fucking me and the pleasure keeps increasing and my cock is just dripping with cum and he tells me I’m really tight and he wants to cum in my asshole.

I tell him absolutely and after 10 minutes or so he tells me he’s cummin and I reach down and start stroking my cock as he fills me up with his cum, I cum all over my face and chest and there was so much cum, We rest a few minutes and then I ask him how did you know I wanted to experience gay sex and he tells me that a lot of older men don’t have much sex with their wives after being married for decades and he was hoping I was one of them.

I tell him that my wife and I have always had a great sex life and still have sex 2 or 3 times a week, he then tells me I must have always deep down wanted to try gay sex and I tell him never crossed my mind, but for some reason when I looked at his cock it aroused me and deep down I wanted to see how it felt, he gave me a washcloth and I cleaned my face off but I left his cum on my chest.

I got dressed and grabbed my phone and I looked at how long it recorded and it was 38 minutes of my first gay encounter and I couldn’t wait to get back home so my sister-in-law could watch it, I got back to the car and got in and she smiles at me and says I bet you let him fuck you like a woman, I look at her and tell her I bet there are 2 cock suckers in the car now and she asked if I recorded it and I tell her 38 minutes worth of my gay encounter and I raise my shirt up and show her the dried cum on me and she says I’m a cum slut too.

We take off for home and 10 minutes she wants to watch a little bit because she’s horny as hell, I give it to her and all I can do is drive and listen, I hear her unzip her jeans and then she slides them down around her ankles and tells me how fucking hot I look sucking his cock and did I like it, I tell her it felt so good in my mouth, she tells me she can’t wait until we get home she’s going to finger fuck herself right now and I say that’s not fair because I can’t see anything.

She turns enough that I can see her almost naked pussy and buries her fingers inside and the wetness of her pussy and she tells me she’s going to cum, I look as much as I can without killing us and now my cock is hard again and I tell her she’s making me hard and she says when we get to the house and start watching the video we can both get naked together and record our sex encounter, I said deal!!!