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First time anal?

  • Thread starterrataver
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Started sucking my HS friend who I was 15, it naturally progressed to him fucking me. I loved it. I made it a point to not touch myself or let him touch me because I’d cum immediately. Since then, I’ve been able to cum a few times hands free and it’s magical.
 
this was a few years ago, I was preparing for this with a rubber penis, when it happened, the dick quickly ended up in my ass and took advantage of it, then the man came in my mouth, I really liked it and I repeated it many times
 
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rataver said:
Any cucks here who had a dick in their ass? How did it happen? Feeling?
We’ve evolved a bit out of the cuck lifestyle but still dabble. I allowed my wife to peg me with some encouragement from a member on here. We both loved it and it opened my mind to more.

During this time of adjusting my wife had a slightly less than bi sexual bull. While my wife was in the shower I watched him laying in my bed while playing with himself watching porn. Wife came out of the bath to me on my knees giving him a bj in bed. The evening culminated in him trying to get his enormous black cock in my ass for a half hour. Ended up getting in but it was so painful I didn’t try again for a couple months.

In the interim I met up with a guy who for a short time was fucking my wife. At least a few times a week I’d meet him and give him a bj. Wife thought we were just good new friends. He was pushy with my ass as he would rub it and finger it while I blew him. One day I gave it to him and over time it got more pleasurable. A handful of times in it got to where he would be able to bend me over or I’d hop on him with no lube and just saliva. Once I relaxed it was better and cumming became a regular thing.

My experiences with him made me go on a little tear there the next few months. Ended up meeting a couple and having some very wild times with them and some of their friends.

For reasons I don’t know I just kinda got out of it as it didn’t quite feel right with the way I was living. The last time I was fucked was by the friend I mentioned earlier and there was an unfortunate occurrence I won’t t get into.
 
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Rickyrick said:
I started early! My best buddy started fucking my ass in middle school and continued until I left for college!
not the same but similiar
 
samanthaNwilli said:
Wife tried to do it for our boyfriend when he first started visiting regularly. After a while they could tell he was just too big for her that way, and after they had tried the last time, he told me that I needed to learn to accept.


The next time he was here, they were having sex on the couch. After they finished, when I started sucking, he told samantha to get the lube. As soon as he was hard again, he stopped me and said "it's time, willi"
He told me to lean over the end of the couch. I don't really know why, I don't think I really even thought about it. I just did what he said.
I felt the lube. Then I felt it. Then I felt him starting to push. It just barely went in. He pulled back and pushed harder. It went a little bit more. He kept pulling back and pushing harder every time. It was barely going in a little bit more every time. It seemed like it went on forever. Eventually, when he had it maybe half way in, it was like something just changed, and it started to go. As soon as it started to go, the next push he just pushed it all in. I have trouble not really being stiff enough, but I realized when he pushed it in I was totally stiff. He just stayed all the way in until he was done. I was totally stiff the entire time.

Then he pulled back and they went to the bedroom.
Did she ever manage to accommodate him anally? Or is that still just your job (with him, at least)?
 
I never thought it would feel so good,after he fucked my wife and she was cleaning up he slipped into me,well not really slipped,it hurt like all fuck at first but soon he was all the way in and pounding hard.I couldn't stop from cumming when i knew he was about to cum.The best feeling ever.
 
airhorn said:
Did she ever manage to accommodate him anally? Or is that still just your job (with him, at least)?
he is just too big for her that way
 
srx said:
The best feeling ever.
I completely agree. There is no cumparison at all with ordinary orgasms in terms of length, intensity, or how many you can have in a row.
 
First time felt strange but nice
 
He first gave ne a massage and he got into of me and started running his cock between my ass chicks. As a first timer I was nervous. He took his time relaxing me and slowly starrted playong with my assjole wirh his dick.first reaxtion was to close it but eventually he started pushing slowly until I could accomodate him. He then let me have it
 
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Disco-cuck said:
I was deflowered about 8 years back. I met a JO and suck buddy online and we'd just do stuff at his place. One day he said he wanted to shave and rim me, and expertly did both. I was laying there with my legs up. He stood up from tonguing my ass and slid his cock straight into me. I was so surprised and turned on. I immediately started 'dirty talk' as allowed him to fuck me. Within a minute of him pounding my virgin ass, I orgasmed one of the most intense orgasms I've ever had. I don't get back there often but when I do, I get the same treatment. He's now talking about having another friend over to fuck me as well, and possibly film it. I can hardly wait.
I was lured back there last week. When I arrive we always kiss and make out like crazy which gets me horny. I then shower and douche deeply, towel dry and we go onto his bed and 69. We then kiss more, then 69 over and over. He then gets out the oil to massage me as a lie there stroking. He slides down and begins to rim me. I am trained to hold my legs up and my ass open as he licks me out. He then stands and slides his cock in. I really went crazy telling him to pound my ass good. We fucked for at least one hour. I was sore for days, but I'm aching to go back again this week for another pounding.
 
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I have always enjoyed anal in some form over the years. Objects lying around early on, then toys and plugs. Not all the time, just once in awhile.

After I married the first wife shortly after college, I found out that a good buddy from college was gay. I know, I guess i did not have gaydar back then as I never thought that about him.

I was supportive. And then one day I had to be in the same city as he was, and wanted to catch up. I would be there for a few days waiting on a parts repair so he invited me to stay with him instead of a hotel.
I will admit the weeks before making that trip I was wondering.....what would the real thing be like?

We talked, visited, caught up etc, and had a few drinks. I just screwed up the courage to offer myself for the weekend if he wanted it or needed it. That moment where you just have to do it or forever hold your peace. The tension in the air for me was great.

He said he wanted it, not just for the sex, but because he had thought about it with me before, those college years.
A mix of relief and panic, he said yes, but now what? I can't back out now, have to follow through. Thankfully he just took control and told me what to do.

I spent that weekend naked when in the house at all times. I sucked him, and he fucked me. He did not allow me to cum myself. That first time he put his beautiful cock in my ass, I knew that the real thing was far better then any toy could be.

I just let go, did whatever he told me to do, and discovered that serving and pleasing can be much more rewarding then getting to cum. It progressed from there over the years.
 
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All-In said:
I have always enjoyed anal in some form over the years. Objects lying around early on, then toys and plugs. Not all the time, just once in awhile.

After I married the first wife shortly after college, I found out that a good buddy from college was gay. I know, I guess i did not have gaydar back then as I never thought that about him.

I was supportive. And then one day I had to be in the same city as he was, and wanted to catch up. I would be there for a few days waiting on a parts repair so he invited me to stay with him instead of a hotel.
I will admit the weeks before making that trip I was wondering.....what would the real thing be like?

We talked, visited, caught up etc, and had a few drinks. I just screwed up the courage to offer myself for the weekend if he wanted it or needed it. That moment where you just have to do it or forever hold your peace. The tension in the air for me was great.

He said he wanted it, not just for the sex, but because he had thought about it with me before, those college years.
A mix of relief and panic, he said yes, but now what? I can't back out now, have to follow through. Thankfully he just took control and told me what to do.

I spent that weekend naked when in the house at all times. I sucked him, and he fucked me. He did not allow me to cum myself. That first time he put his beautiful cock in my ass, I knew that the real thing was far better then any toy could be.

I just let go, did whatever he told me to do, and discovered that serving and pleasing can be much more rewarding then getting to cum. It progressed from there over the years.
I hope this story is true,it sounds so good,life changing event ,and like me,you wasted so many years without it.
 
srx said:
I hope this story is true,it sounds so good,life changing event ,and like me,you wasted so many years without it.
It is true, we got together whenever we could over the next 20 years, prob 2 or 3 times a year.
 
Disco-cuck said:
I was lured back there last week. When I arrive we always kiss and make out like crazy which gets me horny. I then shower and douche deeply, towel dry and we go onto his bed and 69. We then kiss more, then 69 over and over. He then gets out the oil to massage me as a lie there stroking. He slides down and begins to rim me. I am trained to hold my legs up and my ass open as he licks me out. He then stands and slides his cock in. I really went crazy telling him to pound my ass good. We fucked for at least one hour. I was sore for days, but I'm aching to go back again this week for another pounding.
Part 3 - I went over last Friday morning and got right into it. This time he blindfolded me as soon as I got in. He stripped me down, had me lay on his sofa and got my body massaged and oiled. I was rock hard by the time he started flogging me and spanking me. He then led me into his bedroom and tied my wrists and ankles to his bed. I could her the camera clicking and video being shot while he was throat fucking me and sucking me hard. He finally loosened the leg restraints enough for my knees to come up to my chest and he fucked me until I begged him to stop as I was getting raw. I orgasmed onto my own belly as he pounded my ass. By the time we finished our session we were at 4+ hours. I was exhausted for the rest of the weekend. He sent me pics and video clips which was hot. He's already got a guy lined up to spit roast me next time I'm over.
 
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TimKnowsPlaceMWM said:
i should add that if you are on female hormone regimen, the womanly orgasm will be even more intense ... but even without the female hormones, the prostate is a very sexy and sensitive erogenous zone, that most boys don't ever find out about ... unless they end up in some prison somewhere :p
I have a massage guy who massages my prostrate! It is so erotic! I never planed to do him but I did!
 
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I discover getting butt fucked very early when a school buddy said he “ wanted to show me something”. I lost my ass cherry to him that night and ended up with an ass full of cum! After that I taught my best buddy how to butt fuck me and he fucked my ass every wee for the next five years!
 
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Rockford said:
I discover getting butt fucked very early when a school buddy said he “ wanted to show me something”. I lost my ass cherry to him that night and ended up with an ass full of cum! After that I taught my best buddy how to butt fuck me and he fucked my ass every wee for the next five years!
Once over that initial hurdle ,taking cock just gets better.
 
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srx said:
Once over that initial hurdle ,taking cock just gets better.
Yes it does! Once your ass gets broken in it feels for sexy to to get butt fucked!
 
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