First Time Anal Giving Or Receiving...Keep it between the Lit Ditches!

[FGB]

Keep it between the Lit Ditches!
Let's don't get this Thread killed off!

This is a repost from another thread...

This beautiful nineteen-year-old brunette rang my doorbell at four o:clock one afternoon and when I answered it she was all over me.

Backed me up into my living room kissing me and rubbing my Dick and asked me to "Tie me up and Fuck My ASS!"

Well!

I had never had the pleasure before because I had not found a willing Woman. She thought because I had taught her a great deal about how to seriously fuck that I would know all about it.

I did...just had never actually done the deed.

Boy Scout training kicked in so I grabbed some eighth inch braided nylon line and pop some helpful slip knots with stops in it.

I took her into the bed room,stripped her down and secure right wrist to right ankle and left wrist to left ankle with just enough slack to not make it uncomfortable.
By this time her pussy was dripping! She had been drinking and smoking and watching Porn all day and decided that the ass fucking on there was something she wanted to do and SOON. So she went to the guy she trusted the most....Me.

I ate her pussy until she came ...that did not take long. As i was doing that I worked some good Lube in her asshole and loosened it up. May have been why she came so fast and hard. I fucked her until she came again. She was on her back with her legs open and well exposed.
I had warned her that once I had the head in I wasn't going to stop until I shot load into her.
She said that if I stopped, she would never fuck me again.

I am only a little above average in length and girth, so I knew i wasn't going to hurt her if I started slow.

I popped the head in and added another half an inch or so and stopped until her sphincter muscle settled down from clinching and unclenching my dick.

She was moaning softly and saying, "Oh God,Yes!"

I'm not going to lie about I almost came right then!eek: I felt a little jet of cum leave and waited a minute because I knew from that point I fuck for a good while.
I added more lube and started going deeper with each stroke. It wasn't long until I was balls deep in some hot tight ass and she was urging me on.

I am not sure which one of us started cumming first all I know for sure is that I was like a runaway locomotive red lining going in and out of her.

We were both making noises and cumming her squeezing my Dick and me shooting what had to be rope after rope of hot cum deep into her ass.

I almost passed out.

I managed to get her hands free, and we just laid there for a while her head and most of her upper body on my chest.

I have tried to write what happen those many years ago now but feel I am inadequate to the task.

We lost Lisa back in the mid-nineties.

She was a hell of a woman!

Love ya Babe!
RIP! Somewhere over the Rainbow.

 

[Shaglus_Ziegler]

What fun!!!

 

[DarToon]

TGB, what a beautiful tribute to a lady you might now miss!
No disrespect intended.

 

[Cardinal]

Was with my wife a couple of times, eh it was okay, not great, been there done that. I’ll take that pussy any day unless she wants to do it again

 

[Wickettoby1]

My GF had went down the anal road in the past with other partners, she didn't give a raving review. Every time we had sex I would talk about how badly I wanted to put my cock in her ass. One night we were in doggy (knees position as she calls it) and I started fingering her ass but didn't take it any further. The next day she mentioned that she didn't think I would stop at just a finger to which I responded that I didn't "see the 3rd base coach waving me in" . Her response was that I must not have been looking closely enough.

The next time we were together I decided to go for it. Once again in "knees position" I grabbed the lube and started with my middle finger. After a min or two of my finger I decided it was time and swapped my finger for my cock. As I eased my cock into her ass the sensation was amazing, her pussy is plenty tight but there was just something different about how this felt. I've never been with another woman who has vaginal orgasms so effortlessly so I was hoping that trend continued with anal. After a couple minutes so she could relax and get used to my cock she started rocking back and forth, I was letting her control the stroke, the depth and intensity. Much to my delight she really got into it and after a couple minutes she told me to start fucking her ass with the same vigor as I do her pussy. Fast forward another few minutes and she has the first anal orgasm of her life!!! She didn't know how to describe it to me, she said it was very different from a vaginal orgasm. I was really getting into the penetration so I added a little more lube and really started giving her my all. After an intense couple of minutes of her moaning and screaming to "give it to her" I blew a massive load deep in her ass which she said was an absolutely amazing feeling. Needless to say we have now implemented anal into our regular sex routine. She hasn't yet asked me to fuck her in the ass but it's only a matter of time......I hope.

 

[soflabbwlvr]

My first experience with anal was my high school/college girlfriend. Neither of us were virgins when we got together, but we were not terribly experienced, either. Over the 3+ years we were together we tried new things, practiced with each other, and learned a variety of skills. Toward the end of our relationship I became obsessed with anal, and after some discussion she agreed to try it. The first time did not go well. Could not get it inside her. We didn't know anything about lube (didn't need it for fucking), and all it did was made her cry and me frustrated. We tried again a few months later, and same result. We tried a few more times before we broke up, but never succeeded.

A year later, when I was 22, my housemates and I were hosting a house party. That evening a woman I knew from class but with whom I had no interest showed up. She brought a friend with her, and the second we were introduced we sparked. The friend had a bob haircut, huge brown eyes, heavy tits, and a perfectly curvy body. I had various hosting duties, but later in the evening I found the friend getting a beer. I asked her if she wanted to go up to my room to do some coke. She agreed, and we went upstairs. We did a few lines, started kissing, and in minutes our pants were off and we were taking turns going down on each other. I got between her legs and fucked her, filling her with a load of cum. We paused to do a few more lines, and by the time we finished I was hard again. I got between her legs again, rubbed the head of my cock up and down her cum filled slit, and then got an idea. I pressed the head against her asshole. I paused for a second and looked into her huge brown eyes. She looked up at me, but she didn't say anything. So I pushed it in. Much to my surprise, it slid in with very little resistance. I pushed it all the way in and and fucked her until we both came for a second time. When we were finished I pulled out, we got dressed, and she said to me "let me go down first, I don't want my boyfriend to see us together." We never really talked about the fact that I had just fucked her in the ass.

 

[gtnlynn]

My wife's first time receiving was in college. She was having sex with her date, a friend with benefits, when he pulled out and rammed his cock into her ass with no warning, no lube. It hurt like hell! She never let anyone, including me come close to fucking her anally again.

 

[Wickettoby1]

My wife's first time receiving was in college. She was having sex with her date, a friend with benefits, when he pulled out and rammed his cock into her ass with no warning, no lube. It hurt like hell! She never let anyone, including me come close to fucking her anally again.

One asshole ruins it for everyone

 

[gtnlynn]

One asshole ruins it for everyone

Yep, including for himself. He lost all benefits.

 

[TonyF862]

My first experience with anal was my high school/college girlfriend. Neither of us were virgins when we got together, but we were not terribly experienced, either. Over the 3+ years we were together we tried new things, practiced with each other, and learned a variety of skills. Toward the end of our relationship I became obsessed with anal, and after some discussion she agreed to try it. The first time did not go well. Could not get it inside her. We didn't know anything about lube (didn't need it for fucking), and all it did was made her cry and me frustrated. We tried again a few months later, and same result. We tried a few more times before we broke up, but never succeeded.

A year later, when I was 22, my housemates and I were hosting a house party. That evening a woman I knew from class but with whom I had no interest showed up. She brought a friend with her, and the second we were introduced we sparked. The friend had a bob haircut, huge brown eyes, heavy tits, and a perfectly curvy body. I had various hosting duties, but later in the evening I found the friend getting a beer. I asked her if she wanted to go up to my room to do some coke. She agreed, and we went upstairs. We did a few lines, started kissing, and in minutes our pants were off and we were taking turns going down on each other. I got between her legs and fucked her, filling her with a load of cum. We paused to do a few more lines, and by the time we finished I was hard again. I got between her legs again, rubbed the head of my cock up and down her cum filled slit, and then got an idea. I pressed the head against her asshole. I paused for a second and looked into her huge brown eyes. She looked up at me, but she didn't say anything. So I pushed it in. Much to my surprise, it slid in with very little resistance. I pushed it all the way in and and fucked her until we both came for a second time. When we were finished I pulled out, we got dressed, and she said to me "let me go down first, I don't want my boyfriend to see us together." We never really talked about the fact that I had just fucked her in the ass.

Did you ever see/do her again?

 

[notmy1strodeo]

My old flame knew I’d never done anal and she always wanted to be the one that let me scratch that itch.

One July weekend many years ago, while her husband was away for the weekend for a friend of his’ stag do, she invited me over for one of our far too infrequent hook ups.

It was as intense and charged as always, but this time she surprised me. She looked me in eye while she was stroking me and told me to “fuck me up the ass” (I’ll never forget that phrasing lol) I didn’t need much convincing, so I obliged her request. Twice.

 

[soflabbwlvr]

I simplified the facts a little. The woman from my class lived in a house on the same block as I did. The woman I fucked moved into that house, replacing a woman who moved out between semesters. So I ran into both of them frequently on the street walking to and from class. I never had the opportunity to fuck her again, unfortunately. I did fuck the other woman, but that's another story for another thread.

 

[masterslave00]

Giving - me 25yo, she 35yo MILF - she thought her pussy was too loose (was not) after two kids, so offered me her asshole.

Receiving - me 29yo, she 19yo med student - she was practicing anatomy on me and ended with her finger at my prostate... When she realised that I loved it, she took out a dildo and fucked me with it.

 

[Wickettoby1]

Giving - me 25yo, she 35yo MILF - she thought her pussy was too loose (was not) after two kids, so offered me her asshole.

Receiving - me 29yo, she 19yo med student - she was practicing anatomy on me and ended with her finger at my prostate... When she realised that I loved it, she took out a dildo and fucked me with it.

I hope she started small with the dildo???

 

[masterslave00]

I hope she started small with the dildo???

Was the same I bought her for the times when I was not available - roughly same size as my dick, so not exactly small... And since I had fucked her asshole already few times, I think it was fair for me to take it without any complaints

 

[Wickettoby1]

Was the same I bought her for the times when I was not available - roughly same size as my dick, so not exactly small... And since I had fucked her asshole already few times, I think it was fair for me to take it without any complaints

Look at you taking it like a champ!!!

 

[masterslave00]

Look at you taking it like a champ!!!

Nowadays (will be 63 in 12 days), my 33yo FWB can make me cum completely hands free just by pounding my asshole... That girl so long time ago got me completely hooked on it.

 

[Wickettoby1]

Nowadays (will be 63 in 12 days), my 33yo FWB can make me cum completely hands free just by pounding my asshole... That girl so long time ago got me completely hooked on it.

Sounds like a "good" addiction to have!!

 

[masterslave00]

Sounds like a "good" addiction to have!!

Just shame that there are too many people who think it is too gay or sissy and don't understand that even hetero and often dominant types can indulge in such an activity.

 

[TonyF862]

Just shame that there are too many people who think it is too gay or sissy and don't understand that even hetero and often dominant types can indulge in such an activity.

The thought of my wife "taking" my ass is a real turn on. We have "dabbled" with pegging, but I have yet to find as position/technique that really puts me over the edge. Outside - yes - licking my ass is a huge turn on and I've jerked off to her rimming me, but full-on ass fucking me, I'm still trying to find that sweet spot.

Thoughts from the more experienced on the thread?

PS When I have played solo - or the few times she's pegged me, my dick stays limp (which is VERY rare for me, as I'm always hard when playing). Would love to hear if those of you who are regular pegg-ees stay hard or can cum with a flaccid cock?

 

[Wickettoby1]

Apparently the old saying that there's a first time for everything is true. The other night my GF was in "knees position" and I was putting in some solid work with my cock in her ass. She starts screaming that she wants it harder and deeper and faster so I do my best to oblige. I up the effort on my end and start giving her all I got. After about three min she lets out a whail and damn near goes limp. After a min or two she comes too and tells me that she just squirted from anal. While squirting is very common from vaginal penetration this was a first during anal.

 

[live4thebj]

Giving. I was dating my ex-wife at the time and told her I was curious what it feels like to fuck an ass and she became curious. Was tough in the beginning but once I was all the way in and she had time to give her ass time to adjust she found it enjoyable. Led to other anal activities after that.

Receiving. I was curious about it myself and had her finger me one day. She was totally grossed out by it so 98% of my anal thereafter was self-inflicted by finger and/or toys. 2% was with woman other than her.

 

[4yourpleasureiam]

Keep it between the Lit Ditches!
Let's don't get this Thread killed off!

This is a repost from another thread...

This beautiful nineteen-year-old brunette rang my doorbell at four o:clock one afternoon and when I answered it she was all over me.

Backed me up into my living room kissing me and rubbing my Dick and asked me to "Tie me up and Fuck My ASS!"

Well!

I had never had the pleasure before because I had not found a willing Woman. She thought because I had taught her a great deal about how to seriously fuck that I would know all about it.

I did...just had never actually done the deed.

Boy Scout training kicked in so I grabbed some eighth inch braided nylon line and pop some helpful slip knots with stops in it.

I took her into the bed room,stripped her down and secure right wrist to right ankle and left wrist to left ankle with just enough slack to not make it uncomfortable.
By this time her pussy was dripping! She had been drinking and smoking and watching Porn all day and decided that the ass fucking on there was something she wanted to do and SOON. So she went to the guy she trusted the most....Me.

I ate her pussy until she came ...that did not take long. As i was doing that I worked some good Lube in her asshole and loosened it up. May have been why she came so fast and hard. I fucked her until she came again. She was on her back with her legs open and well exposed.
I had warned her that once I had the head in I wasn't going to stop until I shot load into her.
She said that if I stopped, she would never fuck me again.

I am only a little above average in length and girth, so I knew i wasn't going to hurt her if I started slow.

I popped the head in and added another half an inch or so and stopped until her sphincter muscle settled down from clinching and unclenching my dick.

She was moaning softly and saying, "Oh God,Yes!"

I'm not going to lie about I almost came right then!eek: I felt a little jet of cum leave and waited a minute because I knew from that point I fuck for a good while.
I added more lube and started going deeper with each stroke. It wasn't long until I was balls deep in some hot tight ass and she was urging me on.

I am not sure which one of us started cumming first all I know for sure is that I was like a runaway locomotive red lining going in and out of her.

We were both making noises and cumming her squeezing my Dick and me shooting what had to be rope after rope of hot cum deep into her ass.

I almost passed out.

I managed to get her hands free, and we just laid there for a while her head and most of her upper body on my chest.

I have tried to write what happen those many years ago now but feel I am inadequate to the task.

We lost Lisa back in the mid-nineties.

She was a hell of a woman!

Love ya Babe!
RIP! Somewhere over the Rainbow.

I need someone in me now. No regard for my pain or pleasure, just their need to fuck and perhaps make me cry with pain.

 

[PhiloDaddy]

I was dating an older woman I had met through my mother. We watched Last Tango in Paris. We started talking about it on the way back to her place. Out came the A&D ointment and we played until we both came. I'm not very long but she was a slim Asian woman and she said she enjoyed it. However, she broke up with me and ironically started dating a younger guy and I suspect she really just wanted someone taller and longer.

 

[hulmule]

Old GF ass was better than her pussy...never told her though...