Should I Go All The Way

I’m a straight-ish guy, but enjoy anal play for some years now. I’ve been sexting with this guy and he really wants to fuck me. I’m honestly at the point of giving in and just going for it. I am just am unsure if the fantasy of it all is more exciting or if the real thing is truly what I want.

Comments

Anonymous

by Anonymous on Jan 13, 2025 at 4:46 AM

There is no going back, I’m a married 65 yo str8ish man, masculine and most people don’t know or would they believe I enjoy sucking cock, swallowing cum, submission gay sex, even gay bondage , I’ve done so many kinky gay things over the years, and yes I’ve bottomed some too, it’s prob more exciting as a fantasy than reality until the right top knows what he’s doing and you cum from his top skills handsfree, I have only cum 5 times handsfree from the deed, if are burned into my mind and still fantasize sometimes at night as I run the thoughts through my mind, I will leak pre-cum too.
But most times are not that great, I do have a dl buddy that I suck off very often and from time to time I suck him and a buddy of his, his buddy tops me most of the time

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Anonymous

by Anonymous on Jan 13, 2025 at 5:29 AM

I’m a married man with kids and grandkids and about 60 year-old. I have topped and bottomed, and much prefer being bottom. I absolutely love sucking guys off. My biggest kinks are, bosses, doctors, and clergymen. I do have a couple bosses that I do suck regularly. I will tell you this, it amazes me how easy it is to find guys to mess around with. Once you start, you’re not gonna stop.

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Anonymous

by Anonymous on Jan 13, 2025 at 5:49 AM

I'm still trying to process " straight-ish " guy. LMAO.

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Anonymous

by Anonymous on Jan 13, 2025 at 6:30 AM

My first time taking it up the ass I was 12 years old. Me and my best friend had been having oral sex for weeks. He and I were always jacking and stroking each other and it just felt too good for us to stop so it was something we did daily.
We both lived out in the country so we had plenty of private spots outdoors to go and play around and suck each other off. Neither of us could cum a whole lot at that age but when we sucked each other we came in each others mouth and it was pretty easy to swallow suck a small amount.
One day down in our favorite spot in the woods we were naked taking turns on our knees to suck each others dick and it was always so much better if we were naked. He was on his knees sucking my dick with his hands on my naked ass and he put his fingers in the crack of my ass and spread me open. He pulled me into him and with my nuts pressed to his chin he touched a finger tip to my asshole.
I pushed forward and grabbed his head and made a weird sound or two as he poked his finger in to my asshole. I guess he could tell by the way I was acting that I liked what he was doing so he pushed his finger in my ass. I went nuts when he did and his finger went up my ass more and more and I was grinding my hips in to him with my nuts running on his chin and he made me cum like in ever came before.
He kept sucking and licking on my dick and balls with his finger still up my ass. He looked u at me and asked me if his finger felt good and I told him it felt great. He asked if he could keep doing it and I told him sure why not. Once I told him that he started trying to reach around to get at my ass a little better. Before he was finished my feet were widespread he was reaching in between my legs from the front fingering me and playing with my dick with his other hand.
I had my eyes closed and just let him have his way with me. I felt his mouth on my dick and he was sucking me off again while he fingered my asshole really fast pushing his finger as far up my ass as he could and he made me cum again.
We were in no hurry so we sat around there talking and I kept telling him I liked what he did and told him I could do it to him. He kept saying maybe later you can do it to me. Both of us had a hard on again and he said can I ask you something? I said sure why not. He said don’t get mad but I just wanted to ask if you might let me try doing that same thing with this. And he put his hand on his dick.
I wasn’t expecting that but right away I thought why bother it. So I told him sure let’s try it. I could tell he was very anxious so we got started and I ended up face down in the grass with him on top of me holding his dick yo my asshole trying to put it in me. It was very difficult and since we both wanted to do it I tried to help out by spreading my ass open with my hands. We still needed a little help so he backed off and started to spit in the crack of my ass and rub his spit around my asdhole with his finger then he stuck his finger up my ass then two fingers. When he tried to put it in me the next time it went in pretty easy and he wasters no time going all the way in and he was laying on top of me with his dick up my ass and it felt great. He asked if I liked it and I said it really feels good.
He started to move his hips and push harder and the more he did the better it felt. Before long he was going in and out and he was fucking me in the ass and my dick was rubbing on the grass as his dick fucked my asshole. He got too excited and didn’t last near long enough for me and he came in my asshole.
I asked him not to get off of me and to not take his dick out. We just laid there talking and both agreed it felt good and I told him I wanted him to do it to me some more. He said he wanted to do it some more too.
I’m a few minutes after him laying on top of me humping on my ass moving his dick around inside of me he got very hard and started to fuck me again. This time it lasted awhile and he fucked me much harder and he came in my ass again and I came too.
We were 12 then and he fucked me for about 7 or 8 years and we sucked each other off all the time. All thru my school years it seems there were a lot of very horny boys that didn’t mind having sex with other boys if they could get off. So I had no problem at all having several friends that could keep a secret and I let them fuck me all the time.
I as a very straight tough kind of boy football player baseball worked on a ranch and had girlfriends but anytime one of my friends came around wanting to put his dick in me I was always ready for that. Many times I did it with 2 or 3 boys at the same time and a few times a Saturday night party or camp out turned in to a gang bang with several boys taking turns on me.
The first time I tried it with two boys I loved it. Being naked with two boys both taking turns fucking me and being watched and both of them getting off inside of me was just pretty fucking hot. I still remember one day after school in the 9th grade I met two of my friends in the woods and we all got naked and one started to fuck me from behind on my hands and knees and the other was just watching stroking his dick. He got all worked up and was standing in front of me watching the other boys dick going and out of my asshole and he got to his knees and asked me to suck his dick.
Man you talk about hot. Getting my ass fucked and the other boy holding on to my head fucking my mouth was more excitement that I had ever had. As soon as the one fucking me started to cum up my ass the other boy started to cum in my mouth. Damn man it was the best feeling ever and it wasn’t the last time I let two boys take me at both ends at the same time. I think they call it spit roasting these days. lol
Anyway I am 66 years old now and I have been letting men fuck me for years. It don’t happen with a strange man very often but I have 3 close friends that line me don’t get sex at home we are all married family men but we hang out together and we all have sex with each other. I am
The only bottom in our private little discrete group so when all 4 of us get together to drink and party I hat gang banged after a lot of group sucking and beer drinking. Since we are all
Married and only have man sex in our private group I let them all cum in me and I like taking all that cum up my ass and getting spit roasted is pretty common when we get started. They like to tie me to the bed face down at times and take turns fucking me. I like that too. I really don’t care what they do as long as they fuck me. Two of them have really nice big dicks. Long and thick and one has a huge head that feels great in my ass.
The only one I can take all the way to the balls in my mouth is the smaller guy and it is great to suck him off while the other two big dick guys fuck my asshole. I have had a couple of huge cocks over the years and I will never forget them. Mexican men have nice dicks and they fuck great. When I was younger in my late 20’s early 30’s I tried big black cock a few times and the biggest cock never had was a black man that I met in a bar and I drank beer with him for weeks before he shared his secret that he was bisexual We struck up a conversation and he told me he loved to fuck white men and when I asked how big his cock was he smiled and told me it’s very thick Then I asked how long and he smiled again and he said let’s go find out.
We went to his house and had sex all night long and he said it was 12.5” and I sure believe it was and yes it was very thick. Biggest cock I have ever taken up my ass but I took it quite a few times during that year I was working in that city.
So like the one response said if you ever let a man fuck you up the ass you will always want it. I know that for a fact. If I were you I would try it. Use plenty of lube and just enjoy it. If he cums in you you will go back for more I promise.

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Anonymous

by Anonymous on Jan 13, 2025 at 9:11 AM

Look at it this way, if you don't like it don't do it again you will never know if it's for you unless you try it. I am in my 60's now I had cock way before pussy. I like both I look at it this way it's about pleasure so why limit yourself to just one gender for pleasure. It does take practice receiving anal but once you master it, it is very pleasurable.

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Anonymous

by Anonymous on Jan 14, 2025 at 2:10 PM

IN response to the OP's question, IMO, there's only one way to definitively find out. Let this man fuck you up your ass. If the result is disappointing for you, don't do it again. If it fulfills the promise of your fantasies abolut getting anally fucked, then you've opened up a, entirely new aspect of your sex life.

BTW, I'm confused more than a bit by your the "straightish" comment as well. Have you had any other male-on-male sexual experiences before? If so, how did that work out for you? I would think that the answer to that should give you at least some indication as to the results of this one.

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