First time receiving anal

[LustyScribe]

My first time was with a pretty trans woman I arranged to meet for a week (we were both hoping a lasting relationship would result). Her cock was smaller than average about 4 1/2 inches hard.

Good thing because I thought that she would take her time working her cock into my hole but instead she rammed the length of it up my ass in one fierce thrust. When I felt her penetrate me, I was literally in another dimension. I could not believe that I was bent over being fucked by a hard cock.

It did not take long before her hands grabbed my hips as she pushed in as deep as she could go. I knew that she was about to unload in my ass and I could feel her stop and start moaning while she had her orgasm. I couldn't feel her shoot her cum but I knew that she was filling my ass up with her jism.

Here I was within five minutes, I not only had my first cock in my ass but I had the first hot load of cum injected into my bowels. After she had cum, she stayed in my ass and leaned up over me to tell me to wait and that she would get hard again. So we stayed in position like two dogs tied up together with her cock in my ass. It only seemed like a minute or two before her cock was getting hard and she started to thrust back and forth a little.

Then she was completely hard and ready for round two. She was now fucking in earnest pushing her cock balls deep into my ass and pulling back but staying in my ass. It was lovely feeling her hardness in my ass as she got excited again and her movements increased in intensity.

She had just finished pumping a load of her hot milk into my bowels but now she was getting ready to ejaculate again. Again she stopped her thrusting as she bottomed out in me and she cried in ecstasy as her cock throbbed and spurted her hot semen into my hole. I was being bred like a bitch and she was completing our mating for the second time. What a top she was, fucking her bottom to completion twice without getting her cock out of my hole. Her penis may have been small but it was powerful for its size and she used it skillfully to dominate me.

Even though our relationship did not work out, I was hooked on the experience and I vowed to find a trans woman with whom I could have a long and fulfilling relationship.

Wow! That was hot! Thanks for sharing that!

 

[ChloeOfCascadia]

I'm so sorry that's the reality you have to deal with. The intolerance, ignorance, fear and stupidity in this world... I'm in the U.S., which seems to be ground zero for all that is bad right now in terms of how human treat humans. Hopefully, when MY generation dies off, they'll drag a lot of this nonsense to the grave with them. Maybe I'm a hopeless romantic, but I hope you find THE right person for you.

I'm 42 and not in a great geographical location or financial situation.

I need that one in a million person who sees me as someone worthwhile and is willing to look past the difficulties in seeing me, to see me.

It's worth hoping for, and I can be persuasive or seductive, but I do still need to find the right person and, somehow, get her attention.

No easy task, not even on this website.

But let me not bum everyone out- @LustyScribe, a BIG thanks for your humanity and morality being screwed on correctly.

I hope you and everyone as kind as you find exactly the happiness you deserve as well.

 

[NumbMom]

well it bring back memories. My first time was when I was a teenager. I have seen in porn and I wanted to see if it was fun so I put a finger inside while in the shower. At first it was slowly but the. I wanted fast. I found out that burn after and my butt was hurting like heart beat pulling so I found out that the way is slowly. After a while I put 2 fingers and after another while I needed something bigger. I didn’t have a BF at the time so I found that if you get a cucumber and put a condom you have something to play with, so I did that and ohh boy didn’t had some fun.
When I had a BF I was able to experience the real deal and even thought he went slow at first he got me in doggy styled and old my hands behind my back and went as fast as he could. And what I experience was amazing. I came a lot but when the rush was over I wasn’t able to sit for a while. After that I really enjoy it just as much as pussy sex.

 

[Gazzspeed]

well it bring back memories. My first time was when I was a teenager. I have seen in porn and I wanted to see if it was fun so I put a finger inside while in the shower. At first it was slowly but the. I wanted fast. I found out that burn after and my butt was hurting like heart beat pulling so I found out that the way is slowly. After a while I put 2 fingers and after another while I needed something bigger. I didn’t have a BF at the time so I found that if you get a cucumber and put a condom you have something to play with, so I did that and ohh boy didn’t had some fun.
When I had a BF I was able to experience the real deal and even thought he went slow at first he got me in doggy styled and old my hands behind my back and went as fast as he could. And what I experience was amazing. I came a lot but when the rush was over I wasn’t able to sit for a while. After that I really enjoy it just as much as pussy sex.

BF must have loved your tight ass! Glad you enjoyed! You do sound fun!

 

[NumbMom]

BF must have loved your tight ass! Glad you enjoyed! You do sound fun!

He did he was the first one there and he knew it

 

[ChloeOfCascadia]

well it bring back memories. My first time was when I was a teenager. I have seen in porn and I wanted to see if it was fun so I put a finger inside while in the shower. At first it was slowly but the. I wanted fast. I found out that burn after and my butt was hurting like heart beat pulling so I found out that the way is slowly. After a while I put 2 fingers and after another while I needed something bigger. I didn’t have a BF at the time so I found that if you get a cucumber and put a condom you have something to play with, so I did that and ohh boy didn’t had some fun.
When I had a BF I was able to experience the real deal and even thought he went slow at first he got me in doggy styled and old my hands behind my back and went as fast as he could. And what I experience was amazing. I came a lot but when the rush was over I wasn’t able to sit for a while. After that I really enjoy it just as much as pussy sex.

I am glad the experience was enjoyable, I would heavily credit your own experimentation and masturbation with a large anal toy for that.

No experience or experimenting and then an entire cock, is not a good first time experience. Not often, for sure.

 

[Gazzspeed]

He did he was the first one there and he knew it

That would be so hot....extra hot being the first... he would have cum so hard! Lol... at least I would have, and I am pretty sure he found you as hot!

 

[NumbMom]

He did cum a lot inside me

 

[Gazzspeed]

He did cum a lot inside me

Did you enjoy feeling him cum inside you?

 

[Gazzspeed]

Was his cock bare?

 

[NumbMom]

Did you enjoy feeling him cum inside you?

Yes

 

[gtnlynn]

As I have posted on here before, my wife's first and only anal experience was in college. She was having consensual sex with her fwb when he pulled out and rammed his hard cock into her unlubed anus. No warning, no prep, just "BAM." It hurt like hell, bled a bit, and didn't last long since she screamed and kicked at him. She has never let any other man come close to doing anal on her again.

 

[NumbMom]

Was his cock bare?

Yes

 

[ChloeOfCascadia]

He did cum a lot inside me

I have been honored with being the first person to give anal sex to three of my girlfriends.

I was always so happy to have been chosen and trusted and it was always incredibly erotic.

It was also, a moment for her, not me, so I just focused on giving her a good experience, not cumming.

Later, when they became more experienced, and really liked the activity and wanted to go a little faster and rougher- well worth the wait.

I find this activity incredibly intimate and a beautiful trust building exercise, and yes I put my money where my mouth is on that.

One girlfriend, took my anal cherry with a toy. I trusted her, she was kind and gentle with me. Worth it.

 

[Gazzspeed]

Yes

Lol... I am envying your friend!!!

 

[NumbMom]

My first time for anal was a bit rough. The guy was from a nearby college, about 15 minutes from mine. We had met through a mutual friend. He was a virgin when we met, but his virginity did not last long around me. We had been seeing each other mostly for sex for about a month and things had progressed. He was a quick learner and was becoming one of my regular FWB’s. We had had about half a dozen really good times. He wanted to try anal and I was game, neither of us had ever tried it.

He rented a room at a motel since we both had roommates. We were doggy style on the bed, he had a condom on, and we used plenty of KY. No matter what we did, I just could not seem to relax enough at first. He kept pressure on, kept trying, and eventually he got in past the tip. It still was not pleasant. I kept thinking that it would get better, but there was no improvement, in fact it started to feel really weird. Finally he pulled out, saying that the condom was coming off. We headed to the shower, showered and returned to bed for regular sex.

About 6 months later he and I got the idea to try again. This time was WAY different. We were in missionary and had sex without a condom. After he came, he withdrew slowly and immediately began teasing my ass with his tip. As I was draining out, he was able to use our fluids in combination with his still wet cock to start slowly working his cock into my ass. The excitement of the moment had me wildly horny, and everything just seemed to work perfectly.

He took deep, slow, short, and gentle strokes. As he did, he used his thumb on my clit and pussy opening. I had 3 very intense and memorable orgasms as he worked. He needed little recovery time from the previous sex, and it didn’t take long for him to unload a second time, this time in my ass.

Glass

You sound lovely

 

[Dimented]

My first time for anal was a bit rough. The guy was from a nearby college, about 15 minutes from mine. We had met through a mutual friend. He was a virgin when we met, but his virginity did not last long around me. We had been seeing each other mostly for sex for about a month and things had progressed. He was a quick learner and was becoming one of my regular FWB’s. We had had about half a dozen really good times. He wanted to try anal and I was game, neither of us had ever tried it.

He rented a room at a motel since we both had roommates. We were doggy style on the bed, he had a condom on, and we used plenty of KY. No matter what we did, I just could not seem to relax enough at first. He kept pressure on, kept trying, and eventually he got in past the tip. It still was not pleasant. I kept thinking that it would get better, but there was no improvement, in fact it started to feel really weird. Finally he pulled out, saying that the condom was coming off. We headed to the shower, showered and returned to bed for regular sex.

About 6 months later he and I got the idea to try again. This time was WAY different. We were in missionary and had sex without a condom. After he came, he withdrew slowly and immediately began teasing my ass with his tip. As I was draining out, he was able to use our fluids in combination with his still wet cock to start slowly working his cock into my ass. The excitement of the moment had me wildly horny, and everything just seemed to work perfectly.

He took deep, slow, short, and gentle strokes. As he did, he used his thumb on my clit and pussy opening. I had 3 very intense and memorable orgasms as he worked. He needed little recovery time from the previous sex, and it didn’t take long for him to unload a second time, this time in my ass.

Glass

Damn!!

 

[Dimented]

Being adventurous and trying things is good, and just because they do not go perfectly the first time does not mean they shouldn’t be tried a second time….. or third..,.. sometimes practice is required.

Glass

Experimenting is a must, we all have to evolve at some point.

 

[liqueur]

Rural Norway,
and international travel, with governments, plural, persecuting trans people,
and me being trans also....

Makes this HIGHLY unlikely and super dangerous.

I'm in northern Maine, US. In pretty much the same boat.

 

[ChloeOfCascadia]

I'm in northern Maine, US. In pretty much the same boat.

Oh no....

I was born in southern NH, lived in northern NH, took a vacation in coastal maine in the winter, and Jumpin fuckin' Jesus no.

It feels cold and lonely, I'm so sorry.

It's fine if you have someone but when you have NO ONE.

I feel you, regardless of your sex/gender or orientation, I wouldn't wish that on anyone.

 

[liqueur]

Oh no....

I was born in southern NH, lived in northern NH, took a vacation in coastal maine in the winter, and Jumpin fuckin' Jesus no.

It feels cold and lonely, I'm so sorry.

It's fine if you have someone but when you have NO ONE.

I feel you, regardless of your sex/gender or orientation, I wouldn't wish that on anyone.

I grew up in central Vermont at a time when it was truly rural. Our nearest neighbors were a half-mile away. My first 8 years of school were in a one-room school house. Every spare minute of my time, when I wasn't in school or working on the farm, was spent in the woods. So rural is my natural habitat. I spent time in cities when I was a young man, and enjoyed it, but I always ended up “coming home” to the country. At 75, now, I don't think I could thrive anywhere else.

It's a “choice,” I know, if thriving is a choice— but it's one that seems to virtually eliminate the person of my dreams.

 

[ChloeOfCascadia]

I grew up in central Vermont at a time when it was truly rural. Our nearest neighbors were a half-mile away. My first 8 years of school were in a one-room school house. Every spare minute of my time, when I wasn't in school or working on the farm, was spent in the woods. So rural is my natural habitat. I spent time in cities when I was a young man, and enjoyed it, but I always ended up “coming home” to the country. At 75, now, I don't think I could thrive anywhere else.

It's a “choice,” I know, if thriving is a choice— but it's one that seems to virtually eliminate the person of my dreams.

I think I could be okay with it when I'm 75 but I am actively trying to find someone to spend the next roughly 40 years of my life with, and I can't do that where I am, middle of east Bumfuck Norway, or, probably rural Maine. Or Vermont. Or anywhere in New Hampshire to be frank.

That's why the internet is what i got and I am using it to talk to people.

I understand not wanting to be part of a big city, for me, the only benefit is jobs.

Again, a concern for 42 year olds, not 75-

But I get where your priorities are and I concur you should be where you feel comfy.

For me, it isn't here in the middle of wheat fields and highways.

I need a person and I'd love it if it wasn't so bloody cold.

 

[liqueur]

For me, it isn't here in the middle of wheat fields and highways.

I need a person and I'd love it if it wasn't so bloody cold.

So what keeps you from going to Oslo or some other populous area in the South? Seems (from my distance) like there's a lot going on there.

 

[ChloeOfCascadia]

So what keeps you from going to Oslo or some other populous area in the South? Seems (from my distance) like there's a lot going on there.

Money, jobs, residence.

Can't get a job there without the residence, don't have the money for it, because I don't have a job.

It's expensive to live in a city and I have to do it on my own.

I just exited a marriage where, I actually physically hurt myself in order to help our family, became slightly disabled, continued paying every bill, and ended up with zero money remaining.

And an inability to work 40 hours a week. And because of a paperwork error I was not responsible for, government red tape means I do not qualify for any assistance whatsoever. And EU inspections on vehicles meant my last beater car, did not pass, so I don't even have transportation right now.

Or money.

Or a job.

Or a perfectly healthy back. I'm working on that.

But a year with no income and paying bills will destroy you financially.

I'm avoiding debt, but I'm in a bad way.

 

[Wag_that_tail86]

I think I could be okay with it when I'm 75 but I am actively trying to find someone to spend the next roughly 40 years of my life with, and I can't do that where I am, middle of east Bumfuck Norway, or, probably rural Maine. Or Vermont. Or anywhere in New Hampshire to be frank.

That's why the internet is what i got and I am using it to talk to people.

I understand not wanting to be part of a big city, for me, the only benefit is jobs.

Again, a concern for 42 year olds, not 75-

But I get where your priorities are and I concur you should be where you feel comfy.

For me, it isn't here in the middle of wheat fields and highways.

I need a person and I'd love it if it wasn't so bloody cold.

Hugs, Chloe