First anal

[karlhein]

I 've related part of this story previously. I was at a wine and cheese party after a humanistic lecture at a local church. These events were popular with the local professoonal crowd, and had a bit of the singles and swingers mingle ablout them. I got to talking to a lady, recently divorced, 2 kids, a few extra pounds but still attractive. I knew her from previous meetings but had never gone out with her. I the process of our conversation another huy joined us. She seemed happy to have two guys essentially hitting on her. The wine was magnified the sensations, so she was a happy MILF, the center of attention of a couple of younger guys. Eventually we both started rubbing her back, then kissing her, then really kissing her, then someone suggested she take both of us home.

We got home, got naked and she proceeded to blow and fuck both of us, with us carefully staying at opposite ends of her (gay phobia). We had another glass of wine, and began rubbing on her again. He had cum first when fucking her, so he got hard again first, so she leaned over to blow him. I was happy watching her suck his cock, I'd not been inside a porn show very many times, so it was interesting watching.

Before very long I was stroking my own hardening cock, abd moved my hand down from her back, to her butt, which she lifted in the air. My fingers slid unter her into her very very wet pussy ( fucked by two guys for the first time, our cum leaking out of her pussy, blowing one of the guys cocks for the second time, and the other huy rubbing her clitty....you bet it was wet down)there. I alternated fingering her clitty and finger fucking her, with first on finger then two fingers, which had her butt sticking up on the air. She was beginning to moan around the sudesxof the guys cock, tryingvto say fuck me, fuck me with a mouth full of cock.

Well fucking her was an option, but for some reason, while finger fucking her I began to watch her butt wink at me, so I began to use my thumb to rub her asshole. As might be expected, with her ass winking, my thumb slid in, at first just a little, then all the way in. I thing they call it the bowling ball grip, two finger in her pussy and my thumb in her ass. To say the least she liked it, pushing her butt up against me. Abiut this time she xame and the other guy came, mostly on her face as she had stopped sucking. She said ...OMG that feels good, fuck my butt please.

Well we had no lube, but her whole bottom was soaked, so I got on my knees, took my fingers and thumb out and put the head of my cock against her butt, and my cock slid in pretty easily. Between the 3 way, having watched her suck him, having had her cum on my had, I didn't last long in her ass, but my cumming in her ass set her off again.

She later tild ys that this was her first anal experience, but she hoped it wasn't the last. We both had her again, several times, both separately and together, and she always seemed to like it, but moreso when she was with us both and sucking one off after a preliminary round of fucking her pussy.

[explorer98]

I've been fortunate enough to participate in a number of ladies' first anal sex over the part 40-odd years but I think only two occasions merit entry here.

The first was long ago when we were both 19. We hadn't been together long and out first sex had been quite eventful when the young lady very confidently dropped herself astride me in the back of my 1970 Mini Van, promptly launching herself vertically as I invaded more of her 'personal space' than she'd anticipated, almost reshaping the van roof in the process!

Note to our transatlantic friends at this point; a 1970 Mini Van in the UK wasn't like an Astro/Aerostar/Voyager kind of thing - it was a nasty, little box on wheels, derived from Alec Issigonis' 1959 automotive masterpiece. Google Austin Mini Van and you'll see what I mean.

Anyway....

Some weeks later while babysitting for her sister, Jackie and I ended up pretty much naked and exploring each other after the small types had gone to bed and somehow - with her on all fours - I found myself fucking her cute little ass - and this didn't give her the slightest problem!

From that day forward, she was always more easily able to accommodate me up in her tight little ass than she ever was in her pussy!

Fast-forward 23 years or so, by which time I was very involved with the delightfully GILFY Amelia and between us, up to all kinds of mischief!!

She was having a change-round in her office (Head of HR doncha know!) and was moving the furniture. She asked if I'd help with the heavier pieces and of course I obliged. She must have been feeling particularly mischievous that day because every time we came within arm's length of each other, she grabbed my cock through my trousers and gave me a squeeze or a rub!

I could see the minx in her face and at one point 'warned' her; "DO that again and that will be going right up your arse!" We'd tried anal once before - her first experience at 57 - and I just couldn't get inside her without hurting her too much so we'd abandoned it.

Two years later and here with are in her office - between the Managing and Technical Directors - and she's playing up for all she's worth!!

I'd got the tall filing cupboard across her doorway and she very delightfully unzipped me, took my cock out and very quickly brought me to a size I hadn't experienced in a long time!! She gave me that slightly 'coy-but-naughty' look from under her eyelashes (she has SUCH expressive eyes) so I really couldn't help but respond!

I pushed her face down across her desk and flipped her long skirt up around her waist. She was wearing the customary thong underneath which I pulled to one slide and slipped a couple of fingers into her.

She was soaking wet as usual!!

I slid my cock into her going full depth in a single stroke, gave her a couple more to make things well and truly juicy then pulled out before embedding myself balls deep in her delicious arse!!

Using her own juice as lube was delightful and she barely flinched as I forced my way fully home inside her. Probably for the best considering the two guys resident in the adjacent offices (would have made for an interesting disciplinary!) and I fucked her quite firmly across her own desk.

Her first (successful) anal sex at 59!!

It wasn't long before I was pumping cum deep inside her and I have to admit there was a certain perverse delight about leaving the lovely lady just fucked and pumped full of hot cum at 2 in the afternoon with another three hours to go! All she could do was carry on as if nothing had happened while my cum tried to make its way out of her!!

Glorious!!!

[1michael]

During our normal married life I don't thing that I asked my wife to give it a try, but when we made a change to put the Spice or Spark back into our long married life I did ask and her response was NO!
Her main thought was that after having her asshole stretched out for a hard cock to get inside, it might not go back into its normal shape and then she would be embarrassed that nobody would want to see her from the rear side! But no matter how much I begged, she told me that I was getting my anal sex from Carol ( the neighbors wife ) and I should be Happy with that~
I found out that most of the women at least here have some stuff they just won't do or try and for neighbor Carol, she wouldn't let you CUM in her mouth! I think that was another reason we got along so well with our neighbors, cause I would get my anal from Carol and her hubby got to CUM in my wife's mouth! lol
There came a time at my wife's Birthday party that Carol got a bit intoxicated and went down to enjoy my wife crotch after a few guys made their deposits inside her and Carol wasn't thinking straight!
Carol came up to me and told me that my wife's pussy tasted the Best ever today for some reason? I told her it was because she had CUM inside there too and that Carol never tasted that before in her mouth~
She looked bewildered for a moment then she asked me to go with her to my bedroom. Once there Carol asked me to let her do oral on me and for me to CUM in her mouth! I didn't want to take advantage of her drunken condition, but being able to CUM in her mouth for her 1st time won me over~
When we got done Carol told me not to tell anybody at the party what she done, cause then more guys might want to do the same on her! I told my wife later that night in bed and she didn't appear to believe me for some reason?
The next morning my wife went to the neighbors house and got to talk with Carol and her hubby about maybe what she had done? Carol told my wife that she did and it even kind of gave her hubby a shock look too!
I guess for some reason women don't like being outdone by other women, so my wife asked Carol's hubby if he wanted to try to do anal with her? He was Happy to, so they all went to their bedroom and after a little finger play and some stretching Carol's hubby was enjoying anal with my wife but didn't last long before shooting his CUM inside! Carol got to watch the entire session and also was amazed by my wife's actions. When my wife got home she told me about it and I was a bit skeptical, until she dropped her bottom clothing and showed me some CUM still Oozing out of her asshole~ lol
After that 1st time, my wife has done many more anal sex deals and I'm glad that she was over her thoughts on it so I could do anal with her too~

[kajuk]

Originally Posted by KimmyB

I remember my first time receiving anal... it was a pain in my ass!

HAHAHAHA!!

[karlhein]

I had, by sort of an accident, had a FMF with Sam and Sabrina, wine party, both got to kissing on each other, about the time folks were saying "get a room", she took us home to fuck, suck and give her her first anal experience. We did that with her several times, both with just har and one of us and with the 3 of us together. Later, I had been invited to the house of Sam's normal squeeze, who wanted a 3 some. Anyway, Sabrina's good frient, Cindy, heard of our adventures, and let it be known that she was down for some action. The problem was, that she was dating my roomate, Howard, who was a real dork. Even though she hinted rather broadly that she wanted 2 dicks, Howard was having none of it. One night, when I knew that she was coming over, I invited Sam to our shared house, just to see if I could stir things up.
We had dinner, and some wine (always wine to open a ladies legs). About the time the second bottle started, I said to her "Cindy, you are looking so good tonight, if Howard wasn'there, I'd be all over you". She got a big smile on her face, and leaned over to kiss me, with, a good bit of tongue. A minute later, by preaarrangment, Sam said, damn woman, you look good enough to eat. She got an even bigger smile, and leaned over to give Sam a kiss, that lasted for a while. Howard, realizing what was going on, said well guys, she is good enough to eat, but she's mine. Cindy kissed him too, but said, Howard, a woman can choose for herself, and I want all 3 of you. With that, she kissed Howard, long and wet and deep, where we could watch the tongue action. No sooner than they broke, she kissed me again. In addition to kissing her, I felt some tit, and could notice Sam reacing up under her dress, and up her leg, as he waiting for his kiss.
Soon we were all over her, and soon we had her nakked, and soon all 3 dicks were out, Howards; was smaller and softer, by a lot, that Sam and I. Soon, she was taking turns, moving around the table, sitting on our cocks. Howard popped his cork and went soft, so she alternated getting fucked and sucking Sam and I. We knew what was going on, and had jerked off in the afternoon, so we both lasted a long time, something like 30 min. She popped her own cork several times and stayed dripping wet. By the time we were done, Howard was hard again, so she 'Had dessert".
The night didn't end there, she got the same anal experience that Sabrina did, from both Sam and I, and Howard got his little dick into her ass too.
The lesson was that, done gently, many ladies like multiple guys hitting on this, and can wear 3 young guys out every easily.
Here's a picture from the OCC feed, no digital cameras back in those days, to give you a sense of the evening.[/LIST]