Long story short, my wife can only get off from anal, cock in her pussy does nothing for her, but it in her ass she cums almost instantly; we've been anal only for years. One of my best friends confessed he never tried anal, his first wife and current wife will not even try it. So I had the idea of maybe just kind of joking/kind of curious asking her to let my friend do it to he. After a little discussion on it, she actually thought about it but declined. She was okay with him hitting her ass raw and busting his nut in her ass but was saying how she thinks it would be awkward and weird after, especially when we go over to hang out, talking to his wife know he shot a load up her ass without his wife knowing and how it just would be too weird (she doesn't really like his wife, thinks she a bit of a snob so I think that is also why she gave it some thought). Any advice on how to convince her?

My roommate keeps teasing me with her orange shorts her ass hangs out and makes me hard 

I once got with my ex’s best friend, who was really only interested in me because my ex told her I liked to eat ass.This is a long story, in a far away time.I was living at Job Corps at the time, I was broke and fresh out of college and needed a place to stay. I entered college my junior year of high school, so I was still pretty young for a college graduate.

The ex would never let me do anal, sometimes she would let me finger it a little, but she loved having her ass eaten. After we broke up, her friend would sometimes tease me between class. Me and the ex weren’t super serious or anything, so we all pretty much stayed friends after we broke up, but by then the ex was already with another dude, so I didn’t really hang out with her much.

One day, Friend was like, “I hear you like to lick ass” and laughed, and I said, “Yeah, I do”. She was taken aback, like she expected me to deny it, I guess.
”Don’t you know that’s gay!?” she said, and I said “No, I don’t know that”, and continued on my way.

Later on she came up to me in the cafe and said, “Are you going off-res tonight?”, it was a Friday, and we were allowed to leave for weekends if you lived in the dorms. I hadn’t been planning to, but I asked, “Why?”, and she said, “You should go off-res and take me with you”.She didn’t have to ask twice, I was now planning on it. I wasn’t sure what she wanted, but I definitely had my hopes up!

Being broke at the time, most of my stuff was still with my parents, but they weren’t going to be home that weekend, which is partially why I wasn’t going home, I had no ride and I usually hated taking the bus.

But I now had a reason, and decided I’d be taking her home that weekend. I half expected her to be bluffing or messing with me, but nope, she showed up to the bus and got on with me.We didn’t talk much on the ride home, really, and I was still half-expecting a prank or for her to want something from me.

We then had to take a city bus to my house after the first bus dropped us off, and I expected her to balk or mock me, turn around and leave or something, but she just got on with me. I was at least decent enough to pay the fare for both of us, hey, two bucks, it was the least I could do. We chatted a little about nothing in particular this time, but my mind was racing a mile a minute. What did she want? Just to get off campus for a bit? Everyone knew I always had weed, maybe she just wanted to smoke?

We got home and I met a snag in my plan, because for some reason my younger sister was still there. She was supposed to have been gone, too, staying at her friend’s to go to some concert the next day or whatever.

Once she saw that I was there, and with somebody, she made it a point to be a huge pain. “What’s going on!? Why are you home!? Who is this!?”, wouldn’t leave us alone, kept asking annoying questions, kept hovering.

Friend and I were hanging out in my room and I could hear my sister hanging around outside my door, constantly walking back and forth for no reason, nosing around, it was infuriating, what would she think was going on, and why would she want to know if anything was, anyway. We were usually cool, too, so it was really bothering me that she was behaving this way.

My sister was supposed to leave that night, but she wound up staying the entire night, I’m pretty sure it was just to be annoying, just to fuck with me. I wound up staying on my couch and let Friend sleep in my bed just so my sister wouldn’t hassle us all night, not like she should have cared, it was really out of character for her, and again, infuriating. I kind of never forgave her for it, just for how uncalled for it all was. To this very day I harbor some small resentment over it, really. Gotta be honest.

I woke up the next day and took the world’s quickest shower because I was worried my sister would drive Friend crazy and I walk out to find she left or something. Eventually my sister did leave, but she dragged it on for as long as possible, just to mess with me, and again, for no reason, we were all adults, it was really odd. I was positive that Friend would be totally bothered and disgusted with me, too. If not just for my sister’s obnoxious behavior.

Once my sister left, Friend hopped in the shower and I sat on my couch seething with rage, expecting Friend to be planning her exit.

Friend came out of the bathroom in just a towel, and walked over to me.“I’ve never had my ass licked before”, she said. Well, that was unexpected. I stood up and started lowering her towel, and she let me.

Worried my sister might suddenly burst back into the house or something, I took Friend into my room, locked the door, and got her up on my bed on all fours. She had a small butt, but it was pert, and perky. Really nice, and looked especially good bent over. Perfectly pretty little butthole, too, very tight and pink.

I spread her cheeks and started eating her ass, making my way to her pussy as well, but focusing on her ass. Hey, it was why she was here!

After a while, I was good and worked up and quite ready to fuck her. I didn’t have any condoms so I had to rely on the honor system, “I’m clean, are you clean… !?”, I asked. She said yes and I was too horny to second guess her, almost as soon as she answered, I was inside her. Warm and tight, shaved, she had a nice innie pussy.

After a while she asked if I had any lube. Fortunately, I had an old bottle in my top drawer. “Yeah, I do”.
“You can fuck me in the ass”, she whispered.
Her gorgeous ass was incredibly tight and I kept having to stop so I wouldn’t cum, I was very turned on by how quickly things had escalated.
As I pulled out and stopped, clenching my gut tightly so I didn’t bust, she turned around and started stroking me. “Wait, wait, stop” I stammered, not wanting to shoot just yet.
I laid her down on her back and fucked her ass missionary for a while, I wanted to suck her big tits while I fucked her. When I was kissing her she would lightly bite and suck my lips and tongue, it turned me on even more.
Eventually I was really close and pulled out saying, “I’m really close”.
She had these big, pouty lips and she just sat up, opened them and nodded, not saying anything but moaning in agreement.
”I’m going to cum in your mouth” I said, stroking myself to climax, “I’m going to come in your mouth”.
She puckered her sexy lips waiting for my throbbing member, I kept stroking it while resting the head on her soft bottom lip, she started pursing her lips, sucking and flicking her tongue around my cock saying, “Cum in my mouth, cum in my mouth”, and I couldn’t hold back any longer, pulling back a little and repeatedly shooting thick streams all over her pretty lips and face and into her gorgeous mouth, pushing my cock between her eager lips once I was drained, my post-orgasm shaft spasming inside her mouth. She kept sucking after I came and my whole body shook with pleasure and pain.

We fell back onto the bed and just kind of laid there holding each other and breathing heavily for a while before I eventually got up to get her a towel. While wiping herself off she said, “I’ve never had my ass licked before, all my boyfriends always said it was gross or gay… “. I was going to ask if she liked it, but that felt kinda corny, so I just left it at that. This was before ass eating was a huge mainstream thing, she kept calling it “licked”, instead of eaten, but I thought that was pretty sexy.

We took a shower together, I groped and played with her luscious, wet body, soaping up her tits and ass, rubbing her up and down. Somehow she looked even better, wet, I don’t know why that’s always the case, maybe it’s just a me thing.

Afterward, we hung around watching TV for the rest of the night. We made out and groped a little, at one point she put her hand down my pants and kept fondling my nuts, but we didn’t fuck again.
Later on out of nowhere she said, “My ex was huge. Like, really big. He liked anal and it hurt. It didn’t hurt as much, with you”.
Gee, thanks, I thought, but didn’t say anything.
We chatted randomly and cuddled, before she eventually fell asleep on top of me, later on I conked out, myself.

We had a normal Sunday morning and left for the bus stop that afternoon, luckily my sister didn’t come back home at any point. At that time I would have been happy to never have seen her again, I was still so angry.
We pretty much rode both buses in silence, got back to the center and went our separate ways. I wasn’t sure if she would tell anyone and suddenly everyone would be talking or gossiping or whatever, but as far as I ever found out, she only told my ex, who Friend claimed didn’t care, and who I don’t think cared to tell anyone else, really.

But a few weeks, maybe a month later, my Ex walked up to me in the hallway and said, “Just so you know, I only ever came when I was on top”, out of nowhere, for no reason. I’m not sure if it was out of some kind of spite or revenge for finding out, or if she just felt the need to throw that at me in the moment, but all I could think to say was, “At least you came at all!”, before walking off. It didn’t bother me much, especially since during our TV talk, one of the things Friend had told me was, “I was curious, since ‘Ex’ told me you were good in bed, and that liked to lick her ass”. Hey, thanks for the good word, Ex!

Me and Friend were still cordial, but we didn’t really hang out again after that, and we (unfortunately) never hooked up again, I’m not sure if it was because of the Ex, or if she had just, gotten me out of her system, or what. All the flirting had pretty much stopped, too, and I tried to convince myself it was just a thing that happened, she got what she wanted and was done with me, guys do it all the time for instance, but I can’t deny it was a bit of blow to my ego. The little flirting thing we had was a lot of fun, I was a little sad to see it end. And I couldn’t help but thinking that perhaps she had found my sexual abilities substandard. Not like I’ve had many complaints or anything, but hey, you can’t please everybody!
Her and my ex found a new group of weirdos to hang out with, and they weren’t too fond of me and my friends, so we all kind of drifted apart, entirely. I saw Friend in passing at a rave and didn’t know it would be the last time until it turned out it was. I saw the ex one more time, the day I was leaving the program, and she ran up to me and gave me a huge hug and said a very heartfelt goodbye out of nowhere, I hugged her back and we chatted for a bit, I eventually left, and that was the last time I ever saw her.

How would you use her hanging udder?

Back in the day, I got with my friend’s ex, behind his back. They weren’t serious or anything, and he would constantly complain about her to me. Plus, I knew her first, so I didn’t see it as much of a thing.

Me getting with her wasn’t exactly unprecedented either, before they had even met, she and I had been flirty and sort of dancing around the sword, I’m actually the reason she was hanging around and they met in the first place, I was talking to her but we hadn’t done anything yet, there were a few women I was courting at the time, and one random day he just asked her out, first. I wasn’t mad about it or anything, totally fair play, but I did think he had perhaps done so to, undercut me, kind of show me up or something, but it didn’t bother me. Hey, I had irons in the fire!

But he would always bitch about random problems he had with her that were either completely minor, or invented, like he was just taking issue on purpose to be difficult. He kept complaining that she was annoying and the sex “wasn’t even worth it” because she was “too freaky”, I kept telling him stop being a prude and experiment, go with the experience, but it would actually bother him, he would get angry for real, so I stopped and just let it be.

After maybe three months they broke up, I was surprised it even lasted that long, and I did ask if he would be bothered if I picked up where she and I left off and make a move, and he actually said yes, he was mad that I asked! Considering how poorly he treated her, I figured it was hardly his place to take issue. So I resumed talking to her, anyway. She was surprised that I was still interested and didn’t consider her “sloppy seconds”.

We never formally dated, but very soon after that we were hooking up. She was kinda freaky, I will say. In a good way, though. Nothing too far, at least for me. She liked anal more than vaginal, which had been a huge problem for my friend, but no issue for me! It was a total plus! Hell yeah!

This was back before anal became the mainstream thing it is today, but I’ve always had a thing for it, and I’ve been really lucky to mostly find women who were into it, too, or at least willing to try it.

Other than that she like some very light bondage, barely even bondage I’d say, liked to have her hands tied, liked to be held down, like, shoved down, pushed into the bed/floor, spanked fairly hard on the ass and sometimes slapped in midsection during sex, really minor stuff like that.

The freakiest thing was, she liked to be peed on, sometimes. I also had no problem with this, it’s not exactly my thing, but if it turns you on, it turns me on! She would kneel in the shower and close her eyes and I would piss all over her pretty face, or she would bend over and I would piss all over her ass and back, sometimes she wanted it on her feet, or her tits and stomach. She didn’t drink it, she never tried to make me play with her while she was covered in it, and she never asked to piss on me, I might have let her, hey, I’m adaptable!

We hooked up off and on for the next year or so, it was great because she was down for anal every time, sometimes I wouldn’t even fuck her ass as a form of teasing. My friend never found out, at least as far as I know.

I’m not really a prude but I’m not much of a kinkster, myself, other than anal and ass eating, which were once considered semi-kinky, I’m pretty much a “mostly normal sex” dude. She was probably the freakiest girl I ever hooked up with, and it wasn’t even that freaky in the grand scheme of things.

She had cerebral palsy, and a few years later, I
hooked up with another chick who also had cerebral palsy, and she also preferred anal (never found out if she liked being pissed on, though!) and it’s kind of given me the probably-false stereotype that all women with cerebral palsy prefer anal. Sometimes I’ll watch one of those comediennes who have cerebral palsy and assume they prefer anal. Let me have my fantasies, okay!?

My confession for the day...I can't cum having sex unless it is with a fat chick. Am I the only one like this??? And when I say fat, I mean fucking huge. I used to date this one skinny chick. she was about 5'3" and 125 lbs with big tits and a ghetto booty. Problem was that when we had sex, I just couldn't cum. Hell, half the time I could barely get hard for her. I was seriously thinking that I had erectile dysfunction. Then while living with this girlfriend, I met a chick that was working at the corner gas station. I posted her pic and as you can see, this bitch was fucking huge. She was maybe 5'2 and +400 lbs. of fat over hanging belly, thighs as big around as my waist, calves the circumference of a fire hydrant, and this massive ass. Come to find out she lived just 2 blocks from my house, and she invited me over one night even though she knew I was living with someone. So, I "went for a walk" that night and ended up walking to her house. My god, that woman had my dick rock hard the moment she dropped her leggings and when she bent over on the bed, the fat in her gigantic cheeks rolled like waves at high tide beckoning me to bury my cock inside her. I easily slid balls deep in this bitch's sloppy loose cunt and when this bitch started throwing all that ass back on me, I lasted about two minutes before I was burying my seed inside her pussy. I was so embarrassed how fast she made cum that I apologized. She said it happens a lot. After that we started fucking weekly and it was the same thing. My skinny girl couldn't get me off, but when I went and fucked the fat cow, I was lucky if I lasted 5 minutes with her. And it wasn't just the ass that got me off. Watching her massive belly jiggle when I fucked her missionary made me cum just as fast.