First time receiving anal

[live4thebj]

First time doing anal. Tell us about it. Did you plan it? Did you fantasize about it? Spur of the moment thing? Forced? Surprised? Etc. Details!

 

[kccasey]

First time anal was with phallic items I could find around the house. Handle of tools, glass vials, etc. Then I got a dildo, wow, what fun I had.
But you want to know about first time another person fucked me, don't you? Well, the first time was when I was 21, I heard about a bar downtown which was showing porn movies in the bar. Had to check that out ya know. Long story made a little shorter, I met a TS girl there. She turned out to be a prostitute, but I was so horny I went for it. I sucked her cock, and she fucked my ass. She had a nice cock, about 8" and slender, did not Strech me uncomfortably. Anyway, I took her cock and loved it. The feeling of another person fucking me, sliding in and out, pushing deep, the sounds our bodies made, god, it was such a turn on.
I was so turned on it frightened me. Oh no I though, I must be gay. This was around mid 70's, so society was still frowning on homosexuality. I denied my urges for years. Did not have anal sex for long time, except with dildo's. married, but no kids. Could not orgasm with with women most of the time.
Now I am a sexless marriage and looking for a FWB with a big cock.I have worked up to large dildo's.

 

[SweetCuriousDarling]

This is actually one of my most arousing experiences. I was with the only man I've ever truly trusted, sexually. We have amazing sexual chemistry. He knew I was very nervous about trying anal, and had some hang-ups about it due to some bad past experiences. He understood that the only way to make it happen was to ensure that I had no choice but to completely let go.

We started our encounter as we had many before. He dressed me up in some lingerie, so I would feel properly sensual. It's a nice, kind of foreplay ritual that begins to get me into the correct headspace. Then, while kissing and caressing me, he began to bind me to the bed. We'd played with bondage before, so I wasn't surprised by this. This was another ritual that served to adjust my headspace, and turn me on.

Once lightly bound on my back on the bed, a spreader bar between my ankles and my wrists above my head, he went down on me. He's exceptionally good at this, and it wasn't long before I had an explosive orgasm.

Thoroughly lost, now, in the pleasure of the sensations within my body, not thinking and kind of coherent thoughts, I was only dimly aware as he turned me over and fixed my wrists to my ankles. I was completely immobile at that point, my face buried in a pillow, my ass up in the air.

First, he fucked my pussy for a few strokes, knowing how delicious it feels for me to be fucked directly after an orgasm. But then, he began to penetrate my ass. It was shocking, and I know I tensed a bit, but he rested his hands on my ass and held me fast. While he wasn't rough, he also didn't go slow. He'd made sure everything was well-lubed, and before I had time to get back into my head enough to form any objection, he had his cock buried inside me. Then he just held himself there.

He asked me if I was okay. I don't know if I really knew, but I did know I wanted him to keep going, so I just made a motion for him to hold my hand. He did, and then he kept going. Bent over me, he fucked my ass for the first time, grunting softly in my ear, telling me what a good girl I was, until eventually, he pulled out and came all over my cheeks.

I was crying a bit as he came around to cradle my face and kiss me, emotionally overwhelmed. But it was a beautiful experience. Still a masturbatory go-to for me.

 

[lily_wall_]

First time doing anal. Tell us about it. Did you plan it? Did you fantasize about it? Spur of the moment thing? Forced? Surprised? Etc. Details!

First time was my finger because my friends and I had a conversation about anal earlier that day. Didn't really care for it. I tried a few more times, just one finger, but couldn't get my juices flowing and never understood how people orgasmed with just anal. But I didn't hate it either

Fast forward, tried a small toy with a friend guiding me. She eased it slow and opened me. Apart from the initial pain, nothing exceptional. But once I started taking the toy deeper... *Chef's kiss*

 

[DuchessOfDutch]

First anal experience was with a friends dad. He was 52, I was 19. He was an absolute Daddy, and all the girls in the grond group had a bit of a thing for him.

One night I went over to their house, pretended that I didn't know my friend was away for the weekend. Asked if I couldn't come in for a sec (the Gods were smiling upon me; it was raining) and wait for the rain to pass.

One thing led to another, led to me bouncing on his cock, after he gave me several of the most mind blowing orgasms I've ever had. He then wanted to fuck me from behind, and who was I to say no such a tempting offer, so I got face down/ass up in front him, and he started slamming into me, gave me another orgasm or two and probably some bruises from where he gripped my hips. Suddenly I felt his hands leave my hips and I heard a bottlecap opening, but then he put one hand back on my hip, the other right above my ass...

I felt his thumb go down towards my hole, and before I could say no, or get up or anything, it had slipped all the way in. I was about to protest when he slammed his cock into me again, and started fucking my ass with his thumb, alternating with his thrusts, and I came harder than I ever had before. The moans that left my mouth!

The rest of the night passed, without either his thumb, finger or tongue leaving my ass.

The first actual cock I had in my ass was also him, but that was another night. When I knew my friend was away again, I went back for more, and I sure got it!

 

[pilotguy123]

For me it was my ex’s anal plug. It was long and thin and hot my prostate nicely. After that I got myself a prostate massager that I use regularly.

 

[NathanP3163]

First anal experience was with a friends dad. He was 52, I was 19. He was an absolute Daddy, and all the girls in the grond group had a bit of a thing for him.

One night I went over to their house, pretended that I didn't know my friend was away for the weekend. Asked if I couldn't come in for a sec (the Gods were smiling upon me; it was raining) and wait for the rain to pass.

One thing led to another, led to me bouncing on his cock, after he gave me several of the most mind blowing orgasms I've ever had. He then wanted to fuck me from behind, and who was I to say no such a tempting offer, so I got face down/ass up in front him, and he started slamming into me, gave me another orgasm or two and probably some bruises from where he gripped my hips. Suddenly I felt his hands leave my hips and I heard a bottlecap opening, but then he put one hand back on my hip, the other right above my ass...

I felt his thumb go down towards my hole, and before I could say no, or get up or anything, it had slipped all the way in. I was about to protest when he slammed his cock into me again, and started fucking my ass with his thumb, alternating with his thrusts, and I came harder than I ever had before. The moans that left my mouth!

The rest of the night passed, without either his thumb, finger or tongue leaving my ass.

The first actual cock I had in my ass was also him, but that was another night. When I knew my friend was away again, I went back for more, and I sure got it!

Such a hot story Duchess assuming all was well with you

 

[DuchessOfDutch]

Such a hot story Duchess assuming all was well with you

All was VERY well with me after that!

 

[NathanP3163]

All was VERY well with me after that!

Sounds like you had a ton of orgasms. At least 4? So hot thanks for sharing

 

[pilotguy123]

First anal experience was with a friends dad. He was 52, I was 19. He was an absolute Daddy, and all the girls in the grond group had a bit of a thing for him.

One night I went over to their house, pretended that I didn't know my friend was away for the weekend. Asked if I couldn't come in for a sec (the Gods were smiling upon me; it was raining) and wait for the rain to pass.

One thing led to another, led to me bouncing on his cock, after he gave me several of the most mind blowing orgasms I've ever had. He then wanted to fuck me from behind, and who was I to say no such a tempting offer, so I got face down/ass up in front him, and he started slamming into me, gave me another orgasm or two and probably some bruises from where he gripped my hips. Suddenly I felt his hands leave my hips and I heard a bottlecap opening, but then he put one hand back on my hip, the other right above my ass...

I felt his thumb go down towards my hole, and before I could say no, or get up or anything, it had slipped all the way in. I was about to protest when he slammed his cock into me again, and started fucking my ass with his thumb, alternating with his thrusts, and I came harder than I ever had before. The moans that left my mouth!

The rest of the night passed, without either his thumb, finger or tongue leaving my ass.

The first actual cock I had in my ass was also him, but that was another night. When I knew my friend was away again, I went back for more, and I sure got it!

Sounds like a wonderful expwrience

 

[Leelee43]

We talking sliding my cock in a women or her using her dildo on me sucking my cock
Both wa amazing

 

[DuchessOfDutch]

Sounds like you had a ton of orgasms. At least 4? So hot thanks for sharing

I lost count, and it's been years since that happened... All I remember is he screwed my brains out, have me more O's than any guy ever gave me before that

Sounds like a wonderful expwrience

One I'll never forget! He's definitely responsible for making me a butt-slut

 

[Pabiporffor]

Funny enough I've just had a story published on that https://www.literotica.com/s/anal-awakenings

Mostly it involves alcohol and teenage curiosity, it just seemed like a good idea at the time. And like most thing that seem a good idea when you're young and dumb it was fucking brilliant . The stories pretty true but some facts have been altered for entertainment value.

 

[pilotguy123]

I lost count, and it's been years since that happened... All I remember is he screwed my brains out, have me more O's than any guy ever gave me before that

One I'll never forget! He's definitely responsible for making me a butt-slut

I’ll have to remember this

 

[BillyWalrus]

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.

 

[ChloeOfCascadia]

This is actually one of my most arousing experiences. I was with the only man I've ever truly trusted, sexually. We have amazing sexual chemistry. He knew I was very nervous about trying anal, and had some hang-ups about it due to some bad past experiences. He understood that the only way to make it happen was to ensure that I had no choice but to completely let go.

We started our encounter as we had many before. He dressed me up in some lingerie, so I would feel properly sensual. It's a nice, kind of foreplay ritual that begins to get me into the correct headspace. Then, while kissing and caressing me, he began to bind me to the bed. We'd played with bondage before, so I wasn't surprised by this. This was another ritual that served to adjust my headspace, and turn me on.

Once lightly bound on my back on the bed, a spreader bar between my ankles and my wrists above my head, he went down on me. He's exceptionally good at this, and it wasn't long before I had an explosive orgasm.

Thoroughly lost, now, in the pleasure of the sensations within my body, not thinking and kind of coherent thoughts, I was only dimly aware as he turned me over and fixed my wrists to my ankles. I was completely immobile at that point, my face buried in a pillow, my ass up in the air.

First, he fucked my pussy for a few strokes, knowing how delicious it feels for me to be fucked directly after an orgasm. But then, he began to penetrate my ass. It was shocking, and I know I tensed a bit, but he rested his hands on my ass and held me fast. While he wasn't rough, he also didn't go slow. He'd made sure everything was well-lubed, and before I had time to get back into my head enough to form any objection, he had his cock buried inside me. Then he just held himself there.

He asked me if I was okay. I don't know if I really knew, but I did know I wanted him to keep going, so I just made a motion for him to hold my hand. He did, and then he kept going. Bent over me, he fucked my ass for the first time, grunting softly in my ear, telling me what a good girl I was, until eventually, he pulled out and came all over my cheeks.

I was crying a bit as he came around to cradle my face and kiss me, emotionally overwhelmed. But it was a beautiful experience. Still a masturbatory go-to for me.

That was beautiful to read. I think a person's anal experience should be emotionally uplifting, safe, and welcoming. It should be intimate and trusting.

I know for some partners, it would be unsafe and degrading and they won't respect your boundaries.

For me, if I have a woman in my arms, and she is trusting me completely with her body, all of it, it is my responsibility to make sure she has a very safe, loving experience where we are both equals deserving of respect and loving kindness.

If I take her ass, she should feel protected, adored, and that I am making love to her, and that she is free to relax and just enjoy. And if it were uncomfortable, it would stop. All she has to do is say so.

I want her to feel overwhelmed by the sensations and also the tender loving gentleness of it. She should feel naked and exposed and vulnerable and it should feel erotic, and it can be a very submissive experience, but, she should also feel she is submitting and offering all of herself to the right, loving partner.

Someone who is taking her on this journey toward intimate erotic pleasure, and she can feel safe with, before, during, and after.

There should be lots of kisses and hugs and snuggles and cuddling after.

She is my good girl. She deserves to be treated like a precious, beloved woman. When I make love to her in her ass, I want her to feel like she belongs to me in a physical way, but also an emotional way. She should feel as though we are bonding, and that I accept every part of her body, her personality, her mind, her humanity.

It is a truly romantic and loving act, with the right person. And also, incredibly erotic.

It should be.

And unfortunately when someone is with the wrong partner or the man has no idea what he is doing, he ruins the experience and shatters the trust of this precious beautiful person who trusted him.

The beauty of a wonderful experience brings tears to my eyes, and the tragedy of someone breaking that trust or hurting a woman, also brings tears to my eyes for other reasons.

I have been several women's first time experience and they all asked me for more.

I was always so honored to have been chosen. I remember each person so vividly. It was such an incredibly emotional bonding experience.

I miss this so much. If any woman wants to contact me and just talk about this topic, please do. Even if you're not otherwise interested in me. Or if you just want a friend.

It has been a long time and I miss the human connection. Please someone reach out to me. (women only please, if I were romantically attracted to men, I promise, I'd welcome it... I'm just not)

 

[ChloeOfCascadia]

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.

I am jealous of your experience and would, also, like to experience this from a trans woman.

 

[BillyWalrus]

I am jealous of your experience and would, also, like to experience this from a trans woman.

You don't have to be jealous. You can make it happen.