First time anal

[lowcollar]

I had fucked her in the ass a few times. I also told her that I would try anything at least once. The fourth time, she said that she wanted to fuck me in the ass with a strapon. I thought she was joking. The next time we met at my place, she showed with her video camera and a strapon dildo about the same size as my dick (7"). "Your turn". I was really surprised. Do i get to hold the video tape. "Sure." We set up the camera, got naked and she strapped it on. We had some lube from Spencer's Gifts which she used liberally. At that point, the only thing up my ass prior was one finger. My knees were on the floor and my chest on the couch. She firmly pushed her way inside me. It hurt like hell as I had never remotely opened that far. I was far too proud to say a word. She grabbed my hips and pumped inside me over and over again. The pain did not subside. I heard myself moan deep in my throat as she invaded me. I could feel her smiling."Fuck on it you bitch" she yelled as she fucked me at a furious pace. She fucked me for a good twenty minutes. It hurt nearly the entire time. When she was finished with me, she sat on my face and I ate her to repeated orgasms while I jerked off.
We later watched the video. I ate her while she amused herself watching her dominance over me.

 

[Mickyb9669]

I had fucked her in the ass a few times. I also told her that I would try anything at least once. The fourth time, she said that she wanted to fuck me in the ass with a strapon. I thought she was joking. The next time we met at my place, she showed with her video camera and a strapon dildo about the same size as my dick (7"). "Your turn". I was really surprised. Do i get to hold the video tape. "Sure." We set up the camera, got naked and she strapped it on. We had some lube from Spencer's Gifts which she used liberally. At that point, the only thing up my ass prior was one finger. My knees were on the floor and my chest on the couch. She firmly pushed her way inside me. It hurt like hell as I had never remotely opened that far. I was far too proud to say a word. She grabbed my hips and pumped inside me over and over again. The pain did not subside. I heard myself moan deep in my throat as she invaded me. I could feel her smiling."Fuck on it you bitch" she yelled as she fucked me at a furious pace. She fucked me for a good twenty minutes. It hurt nearly the entire time. When she was finished with me, she sat on my face and I ate her to repeated orgasms while I jerked off.
We later watched the video. I ate her while she amused herself watching her dominance over me.

Wow some horny pleasurable experience

 

[LaceLavender]

First time taking it in the ass and/or first time fucking an ass. Tell us about it. Man or woman.

It was with my first lover; I don’t remember him ever actually asking for it; I suppose men like him never do. It was after three years of our bodies already sharing that most intimate language before it started; it began with ‘accidental’ brushes—the tips of his fingers would linger a little too close and too long when lifting me up. And his fingers would press ‘just there’, especially when I moved above him or when we tasted each other’s secrets simultaneously. One evening I deliberately guided his fingers closer and whispered "Here... if you want to." The way that his breathing changed told me everything. He took such care, soft strokes first, barely perceptible, then, as I began to arch into his touch, he rewarded me with an intrusion of a single explorative finger. He would compliment me on my personal/sexual growth, "Look at you," he would say, "opening up so sweetly." And oh my, I did—spread wide and shivering, yet utterly safe in his hands.

It was weeks later, after savoring perhaps two glasses of wine, something I wasn’t used to at the time, and during our more familiar dance of desire, and after he’d unravelled the deepest rhythms of my surrender three times. I brazenly turned onto my stomach and invited him to "take me there." The silence thickened as his fingers, slick from my arousal, worked me open with agonizing patience, crooking just so until my whimpers turned breathless. When he finally pressed forward, the burn melted into unbearable fullness—his palm pinning me gently but firmly as he murmured encouragement to me, calling me his ‘little dancer,” a name which always made me feel so dainty and delicate. Each thrust rubbed that secret place until I sobbed into the sheets, his fingers circling my pearl with practiced ease. This time my release didn’t gently break, it fractured into blinding light, launching me to the stars. Afterwards, he gathered my trembling body against his chest, lips tracing my ear as he whispered sweet carressing words to me. I never felt more ‘his’ than in that moment, nor felt such pride at my own daring surrender.

 

[Treeview]

A bit of this

https://imaglr.com/post/44818148#google_vignette

 

[HampshireBoy]

Two stories for the price of one, the first time I tried and the first time I succeeded.

My first wife had a couple of friends who raved about anal sex, she used to tell me their stories and it was obvious she was tempted. So one weekend when my MIL had the kids to stay and we were planning a lot of sex we decided to try. I'd already spent a lot of time licking her pussy and she'd had a few orgasms. So she positioned herself on all fours I used lots of lube on her arsehole, working my way up from one, to two and then three fingers, she said that she was enjoying it and it was time. So I lubed my cock and knelt behind her but her arse was so tight and she found it really painful as I tried to push in, after a few tries she asked me to fuck her normally. We tried on a couple of other occasions but she reckoned my knob was just too big.

After our divorce I was seeing a married woman, basically it was a FWB arrangement. Every couple of weeks she would come and stay for 2 or 3 nights and we'd fuck the entire time. At the beginning she had been adamant that she wouldn't do anal, her husband was an inconsiderate lover and had tried without asking and without lube so she wasn't going there again. Then one night, we were spooning in bed, having already has sex a couple of times, pressed against her lovely plump bum cheeks I started getting hard and she took and guided me. I was pressed against a tight hole, but her pussy is very tight and I didn't think alot about this as I wasn't thinking about anal. She urged me to push gently, which I did with steady pressure, she felt very tight then suddenly seemed to open and I slipped in. We hadn't fucked in this position before so it was all new. At first I slowly fucked her, slow out and slow firm in, building my pace. Such a lovely tight hole, and it wasn't long before I came inside her. It was only when I pulled out and she said there might be a mess that I found out that I'd taken her anal virginity. After that anal sex became a regular feature, maybe once in a 2/3 night visit.

 

[Mickyb9669]

It was with my first lover; I don’t remember him ever actually asking for it; I suppose men like him never do. It was after three years of our bodies already sharing that most intimate language before it started; it began with ‘accidental’ brushes—the tips of his fingers would linger a little too close and too long when lifting me up. And his fingers would press ‘just there’, especially when I moved above him or when we tasted each other’s secrets simultaneously. One evening I deliberately guided his fingers closer and whispered "Here... if you want to." The way that his breathing changed told me everything. He took such care, soft strokes first, barely perceptible, then, as I began to arch into his touch, he rewarded me with an intrusion of a single explorative finger. He would compliment me on my personal/sexual growth, "Look at you," he would say, "opening up so sweetly." And oh my, I did—spread wide and shivering, yet utterly safe in his hands.

It was weeks later, after savoring perhaps two glasses of wine, something I wasn’t used to at the time, and during our more familiar dance of desire, and after he’d unravelled the deepest rhythms of my surrender three times. I brazenly turned onto my stomach and invited him to "take me there." The silence thickened as his fingers, slick from my arousal, worked me open with agonizing patience, crooking just so until my whimpers turned breathless. When he finally pressed forward, the burn melted into unbearable fullness—his palm pinning me gently but firmly as he murmured encouragement to me, calling me his ‘little dancer,” a name which always made me feel so dainty and delicate. Each thrust rubbed that secret place until I sobbed into the sheets, his fingers circling my pearl with practiced ease. This time my release didn’t gently break, it fractured into blinding light, launching me to the stars. Afterwards, he gathered my trembling body against his chest, lips tracing my ear as he whispered sweet carressing words to me. I never felt more ‘his’ than in that moment, nor felt such pride at my own daring surrender.

Wow a tender first butt intrusion

 

[steelringsXXXX]

My first anal was on my wedding night, I was 22.
My (now ex-) husband was a big guy, and we had regular anal throughout our marriage.
I've enjoyed it with other partners and with toys ever since.

Suction cupped cock in the shower?

 

[SigmaJay]

My wife and I tried anal a few times over the decades. I could never get in very far and it was painful for her.

Fast forward to 2026. She is post-menopause and on hormone replacement therapy (HRT). Most of her friends are nearly sexless save one. Her one sexually active friend (female) is 60 years old and likes receiving anal. She and my wife talk about sex over the phone frequently. My wife's friend kept goading my wife to try it. This year she finally did. Of course I had to video the momentous occasion:

https://postimg.cc/kBZrRQvx

 

[Samantha47]

My wife and I tried anal a few times over the decades. I could never get in very far and it was painful for her.

Fast forward to 2026. She is post-menopause and on hormone replacement therapy (HRT). Most of her friends are nearly sexless save one. Her one sexually active friend (female) is 60 years old and likes receiving anal. She and my wife talk about sex over the phone frequently. My wife's friend kept goading my wife to try it. This year she finally did. Of course I had to video the momentous occasion:

https://postimg.cc/kBZrRQvx

Anal feels so good

 

[Mickyb9669]

My wife and I tried anal a few times over the decades. I could never get in very far and it was painful for her.

Fast forward to 2026. She is post-menopause and on hormone replacement therapy (HRT). Most of her friends are nearly sexless save one. Her one sexually active friend (female) is 60 years old and likes receiving anal. She and my wife talk about sex over the phone frequently. My wife's friend kept goading my wife to try it. This year she finally did. Of course I had to video the momentous occasion:

https://postimg.cc/kBZrRQvx

Wow brave woman but I bet she loved it.

 

[lovethebeach2007]

My first time having anal sex was with my step dad. The two of us went on a weekend trip to tour some colleges in a neighboring state, and when we got back to the hotel room one night he said he wanted to try something special. We ended up making out on the bed and he fucked me for a bit, but then he put me on my knees, pushed my head into the pillows so my ass was sticking up, and tied my hands. I think he squirted some kind of lube on my ass because it felt really warm and slippery there, then he fingered me for a few minutes until I opened up a bit. I know he wanted to grab me and screw me senseless, but I’m so thankful he was gentle. Between the fingering and the lube, plus my pussy juices all over him, it still hurt and felt incredibly intense the first time he pushed his cock into my ass, but everything slid in so nicely and he took it slow until I could adjust a little, then he really started pumping me and enjoying the new hole.

I won’t share everything that happened, but it was truly such an incredible experience. A little pain, lots of pleasure, and plenty of trust building and lust between my step dad and I. He’s taken my ass several times since then, and it’s always amazing.

 

[Mickyb9669]

My first time having anal sex was with my step dad. The two of us went on a weekend trip to tour some colleges in a neighboring state, and when we got back to the hotel room one night he said he wanted to try something special. We ended up making out on the bed and he fucked me for a bit, but then he put me on my knees, pushed my head into the pillows so my ass was sticking up, and tied my hands. I think he squirted some kind of lube on my ass because it felt really warm and slippery there, then he fingered me for a few minutes until I opened up a bit. I know he wanted to grab me and screw me senseless, but I’m so thankful he was gentle. Between the fingering and the lube, plus my pussy juices all over him, it still hurt and felt incredibly intense the first time he pushed his cock into my ass, but everything slid in so nicely and he took it slow until I could adjust a little, then he really started pumping me and enjoying the new hole.

I won’t share everything that happened, but it was truly such an incredible experience. A little pain, lots of pleasure, and plenty of trust building and lust between my step dad and I. He’s taken my ass several times since then, and it’s always amazing.

Wow brave but very pleasurable, opened up a new world to you.

 

[Samantha47]

Wow brave but very pleasurable, opened up a new world to you.

Mine was with stepdad first time anal

 

[Horny2019]

My first anal was on my wedding night, I was 22.
My (now ex-) husband was a big guy, and we had regular anal throughout our marriage.
I've enjoyed it with other partners and with toys ever since.

I definitely like when a woman likes anal mmm

 

[Mickyb9669]

I definitely like when a woman likes anal mmm

Join the gang

 

[Mickyb9669]

My wife and I tried anal a few times over the decades. I could never get in very far and it was painful for her.

Fast forward to 2026. She is post-menopause and on hormone replacement therapy (HRT). Most of her friends are nearly sexless save one. Her one sexually active friend (female) is 60 years old and likes receiving anal. She and my wife talk about sex over the phone frequently. My wife's friend kept goading my wife to try it. This year she finally did. Of course I had to video the momentous occasion:

https://postimg.cc/kBZrRQvx

Wow well lubed up. Pure pleasure for her

 

[Mickyb9669]

It was with my first lover; I don’t remember him ever actually asking for it; I suppose men like him never do. It was after three years of our bodies already sharing that most intimate language before it started; it began with ‘accidental’ brushes—the tips of his fingers would linger a little too close and too long when lifting me up. And his fingers would press ‘just there’, especially when I moved above him or when we tasted each other’s secrets simultaneously. One evening I deliberately guided his fingers closer and whispered "Here... if you want to." The way that his breathing changed told me everything. He took such care, soft strokes first, barely perceptible, then, as I began to arch into his touch, he rewarded me with an intrusion of a single explorative finger. He would compliment me on my personal/sexual growth, "Look at you," he would say, "opening up so sweetly." And oh my, I did—spread wide and shivering, yet utterly safe in his hands.

It was weeks later, after savoring perhaps two glasses of wine, something I wasn’t used to at the time, and during our more familiar dance of desire, and after he’d unravelled the deepest rhythms of my surrender three times. I brazenly turned onto my stomach and invited him to "take me there." The silence thickened as his fingers, slick from my arousal, worked me open with agonizing patience, crooking just so until my whimpers turned breathless. When he finally pressed forward, the burn melted into unbearable fullness—his palm pinning me gently but firmly as he murmured encouragement to me, calling me his ‘little dancer,” a name which always made me feel so dainty and delicate. Each thrust rubbed that secret place until I sobbed into the sheets, his fingers circling my pearl with practiced ease. This time my release didn’t gently break, it fractured into blinding light, launching me to the stars. Afterwards, he gathered my trembling body against his chest, lips tracing my ear as he whispered sweet carressing words to me. I never felt more ‘his’ than in that moment, nor felt such pride at my own daring surrender.

Wow such a beautifully written account. So enchanting and erotic to read.A piece of pure magical poetry

 

[nottee_1]

I consider my ass a virgin. But not without ever trying.

My late husband and I had tried only a couple times, when I was very drunk to please him... But he couldn't get the tip in.. We were dumb... No line, no pre-stretching.. just raw dog..
And after a few failed attempts, we just gave up.

A few years later, after we separated, I hooked up with a guy who had the biggest cock for a white guy I'd ever seen ...
Vaginally I took him fine..
One night him and I tried.. he didn't know what to do either.. But, he pushed and he said he got the tip in... But I cried very much because it was very painful !! He pulled out, and comforted me because he felt bad...

That's my experience, and I still consider my ass a Virgin!

 

[RCav8tor]

First time taking it in the ass and/or first time fucking an ass. Tell us about it. Man or woman.

I published a story called Lake House. The names and setting are altered but the story is non fiction

 

[RCav8tor]

I published a story called Lake House. The names and setting are altered but the story is non fiction

https://www.literotica.com/s/the-lake-house-17

 

[RCav8tor]

I put the story link here. https://www.literotica.com/s/the-lake-house-17

 

[fredjone]

The first time I had anal sex was with a girl I had just started seeing. We were making out and she started to stroke me and play with my balls. She looked at me and with a devilish grin whispered in my ear that she liked anal. I about lost it when she said that. I remember saying that I had been dying to lick her ass and to bend over because I wanted to rim her. I actually rimmed her before I ate her pussy. We were in her little sisters clubhouse and I was sitting on the oversized beanbag. She pulled down her shorts, turned around, spread her cheeks and sat back on my face. I still remember the smell of her ass and the heat of her hole as i stuck my tongue in. After a good ass licking and eating out her pussy she asked me to fuck her ass. She was in doggy and I took my time and it was so good. Then another time we went to the movies and she had a skirt on and no underwear. She kept fingering herself then letting me taste her pussy. Then she would stick her finger in her ass and let me lick that too. After the movie we went back to her place and she spread her legs and told me to sodomize her. It was so crude but so hot. I really pounded her ass and shot my load in her. When I pulled out it was gaping open and the cum was dripping out. I couldn't help myself and I went in to lick it clean.
The first time i got fucked was with my wife on vacation. She was on her period (of course) and we went to a sex store and bought a strap on. I remember laying back on the bed feeling that dildo slide in me all the way. When my internal sphincter finally opened up it was such a overwhelming experience to have that so deep in me hitting all the right places. I came so hard that night.

 

[cougarwantscocks]

It was something I had never thought of before, but it came up once in conversation with an ex-lover, a rather casual, "have you ever been curious about?" sort of conversation. I remember replying I had never really thought about it much. The seeds were planted and I was encouraged to explore it myself with toys and porn, etc., for a time. I remember enjoying it and us moving to fingers and toys for a few weeks until one night it was too much and I wanted the feel of a real cock. Let's just say it was amazing and I do not regret being eased into as it were. The orgasms were addictive!

 

[Wonderer67]

Two stories for the price of one, the first time I tried and the first time I succeeded.

My first wife had a couple of friends who raved about anal sex, she used to tell me their stories and it was obvious she was tempted. So one weekend when my MIL had the kids to stay and we were planning a lot of sex we decided to try. I'd already spent a lot of time licking her pussy and she'd had a few orgasms. So she positioned herself on all fours I used lots of lube on her arsehole, working my way up from one, to two and then three fingers, she said that she was enjoying it and it was time. So I lubed my cock and knelt behind her but her arse was so tight and she found it really painful as I tried to push in, after a few tries she asked me to fuck her normally. We tried on a couple of other occasions but she reckoned my knob was just too big.

After our divorce I was seeing a married woman, basically it was a FWB arrangement. Every couple of weeks she would come and stay for 2 or 3 nights and we'd fuck the entire time. At the beginning she had been adamant that she wouldn't do anal, her husband was an inconsiderate lover and had tried without asking and without lube so she wasn't going there again. Then one night, we were spooning in bed, having already has sex a couple of times, pressed against her lovely plump bum cheeks I started getting hard and she took and guided me. I was pressed against a tight hole, but her pussy is very tight and I didn't think alot about this as I wasn't thinking about anal. She urged me to push gently, which I did with steady pressure, she felt very tight then suddenly seemed to open and I slipped in. We hadn't fucked in this position before so it was all new. At first I slowly fucked her, slow out and slow firm in, building my pace. Such a lovely tight hole, and it wasn't long before I came inside her. It was only when I pulled out and she said there might be a mess that I found out that I'd taken her anal virginity. After that anal sex became a regular feature, maybe once in a 2/3 night visit.

Great story!

Love the realistic descriptions of sex between couples.

 

[Oldsucker]

First time anal. Four days ago. I have been curious about it for some time. I have tried experimenting on my own and found it ok but not particularly pleasurable. I have been sucking cocks for a small number of years and absolutely love it. I crave it, the cock and the balls that need licking and the ejaculation in my mouth….and the taste.
Four days ago a guy was coming to me, I thought in order for me to suck him. Well. I did. Briefly. Then he said he needed to fuck me. I said yes only with a condom. Thing is, I was not prepared. An event like this, I would prepare, douche thoroughly and lube until loose and slippery. But there was not time. He put on the condom, lined up, and pushed slowly into me. There was a little resistance. Not really pain but there was a lot of friction. I felt his stiff cock slide into me. My first anal fucking. When he was fully inserted, he started to thrust. That felt ok. I arched my back for him to go deeper .This in the doggy position.
He thrust. I felt him moving inside me. After about five thrusts he ejaculated, and withdrew.
Overall, in the circumstances, it was fine. But after a lifetime of not being fucked, I want try it again, be fucked for longer and experience it with lube. Will I really begin to enjoy it? The thought of getting fucked again is arousing me a lot.
After this first time, I want to be fucked and it’s more than curiosity now. More like lust, or need.