# T: Does your ass get fed something every day?

Dear T.,

I wear my buttplug inside my ass every day, all day long, and every night in bed too. When I need to I remove it to use the bathroom and then put it back up my ass. So I only remove it when I'm doing my daily anal stretching routine exercises and challenges, or when nature calls, then wash it and put it back inside my ass where it belongs.

In the morning, when I wake up, still wearing by my buttplug, I might remove it temporarily but then I go about my whole day wearing my buttplug, just like I do every day, I always go to work wearing my buttplug inside my ass throughout my workday, at meetings, conferences or visiting clients. After work I usually go shopping and I choose a vegetable or fruit or object that will stretch my ass wider and bring it home for my daily routine of anal stretching exercises that will be recorded for the purpose of being viewed by people such as yourself!

Being anally plugged throughout the day calms and relaxes me, and at night in bed, it helps me fall asleep and rest better. I can't remember the last time I wasn't wearing a buttplug unless it was to be penetrated in my ass by something else bigger or to use the toilet.

When I go out at the weekends with my girlfriends or with my master, I like getting in the mood by having a drink or two before going out to party and dancing, as usual going commando and wearing a plug up my ass. When we are at the dance club I like 'accidentaly' flashing my pussy or my buttplugged ass on the dancefloor then running to my man or to my girls pretending to be ashamed.

On one ocassion I went out with my girls dancing at the club. Mdma really makes girls loose their shame, and this club is nice for us girls, security guards know us and stand right beside us and they also enjoy the view, but no one dares bother us, then two of the girls wanted to try on the rosebud butt plugs I showed them, got lubed and went up their asses, they all went commando and joined me dancing and flashing at all the guys at the club!

After the club, on our way back home walking through the park, I like to flash my pussy at random lucky guys, my master lifts my skirt and ask a stranger if he would like to see more, I might show him how I take out my buttplug and then put it in my mouth. He stops me in front of a bunch of guys drinking and sitting in a bench, walks over to them and has a chat, he comes back and turns me around bends me over and lifts my skirt, he spreads my ass so all the guys can have a good look, I give them a little show while they're cheering me on, but are very respectful. Because he warned them that if anyone were to be rude the show would be over and the rest of them must agree to forcibly stop and slap up anyone who would dare be rude, no one ever has been rude, works all the time! Once I brought a double ended dildo in my handbag out with me, I took it out in front of ten or fifteen teenagers, I removed my buttplug and held it safely inside my mouth while I shoved the whole dildo deep inside my ass, all the way in and I kept it inside my ass while I put my buttplug up my ass too, meanwhile they kept cheering me on. Then I flashed my plugged ass spreading my pussy and ass cheeks at the guys while the dildo was still all the way up my ass plus the buttplug! Big applauses and cheering. I walked away on my man's arm, every so often he lifted my skirt, flashing my plugged ass at them, they shout and whistle and are thankful and grateful, it's so much fun! Some guys at the park already know me and sit and wait at the park when the night clubs are closed! My little fan base! I love to show off!

Prolonged long-term constant buttplug wear, as long as it's done properly, safely and with appropriate lubrication is completely fine and has never had painful consequences for me, I know by experience. Some individuals like me choose to wear a buttplug for extended periods, it relaxes and calms me since the anus is a receptacle of much tension in the body, sustained dilation of the outer and inner anal sphincters releases such tension and individuals like me benefit from it, not to mention the sexual benefits from the capacity to enjoy anal sexuality to its full potential.

I love to show off pictures and videos of me stretching my ass to as many people as possible! Please enjoy the pics and videos of my anal exercises that I make for your enjoyment and also mine! Just come and visit my profile! I really love to read comments and opinions, it is a big turn-on! It makes me totally wet and gives me desire to make more videos and pictures of me being a total anal slut, undeniably loving being widened and deeply penetrated up my ass with various objects, vegetables, fruits, bats, etc.. all the way deep inside my ass then all they way out very fast each time, in and out repeatedly and very fast, so my ass makes loud plop noises and stays gaped and I orgasm thinking about how so many people like you will watch and hear me! You will know it is true I love it up my ass! As you will see so clearly in my videos, I really enjoy being an anal slut and proud to show off! Also, if I’m lucky, I might enjoy a comment and your opinion about what a dirty anal slut I am and how it is so obvious and undeniable that I really am a natural born anal slut who clearly loves to have her ass stretched for everyone to see!

P.s. Guess where I put my buttplug while it's not inside my ass! Here's a clue... zoom in and look closely at those bitemarks on my buttplug! Yes! I'm also an ♡ ass to mouth slut ♡ and I also eat all the fruits and vegetables that I put up my ass in my daily anal stretching exercises! A vegetable or a fruit up my ass also fills my tummy and keeps me healthy and my slutty ass happy every day!

open your heart, open your ass

K xoxo

I'm a 22 year old girl, I think I might be a porn addict or something. I'm horny so often and I spend hours edging myself every day. I have a bunch of taboo and fucked up fantasies like incest (though not with any of my actual family members), rape, drugs, drunkenness, age play, older men etc. I know I despise any toilet stuff or like, actual violence(though I def love more hardcore sex). I know im definitely submissive and I'm the younger/innocent/victim in all of these. My issue is that I've have one drunk hookup after a nights out and that's literally it. I've made our with some guys at parties but that's where my real life experience ends. 
i know this will never lead to meeting up with someone in real life, I'm in Sweden,  but if you wanna send me fucked up fantasies, or dick pics or whatever I'd honestly love that, and know I will be reading/watching/fantasising with my vibrator to them!

Now this is an odd one, and a bit complicated, I will try to explain.

I have a woman working for me, a sort of right hand (wo)man. Now listen to this, besides being hot, she is my sister in law's best friend, so she is friends with my wife, while in the mean time, she used to be in a 7 year long relationship with my best friend, who is a godfather to my kids.

Of course, no one in his right mind would try anything with her, so neither would I, even though I have thought of her that way, more than once. It is her younger sister (she is 37, her sis 33), who we all know.

She is, and I can't point this out more bluntly, a 10. Just a 10.

Luck had it, that we found ourselves at the same pool party, in the mountain resort I have a condo in, I won't go into boring detail, but I was there with some people I know, she was there on some kind of a work seminar, and decided to crash that party with a co worker.

Her friend got lost somewhere, so she stayed with me, since I was the only person she knew, and we were drinking, joking, and I couldn't get my eyes off of her body. We ended up in a pool, and started messing around, like a bunch of kids, I used the opportunity to press against her body, and she didn't mind. In a minute, I had a full on erection, made sure she felt it pressing against her during our "messing around", and she pressed back.

I didn't want to lose the initiative, so I called her up. We were in bed in under five minutes. I licked her cunt and ass, and oh my God, it tasted like heaven. She came, while moaning loudly. I was up, ready to jump on her, when she got on her knees, and took it in her mouth.

I had never gotten a bj from a 10, I wanted to fuck her, but it felt so good, and it looked perfect, since she was maintaining eye contact, and I didn't last long.

She hit the shower immediately, and I was left there, with an emerging second boner. When she got out, I came on to her again, but she said no. Why? "It would be too much".

And she just left.

It has been more than a few months since then, and I wanted to make some contact, find some answers, and eventually, I saw her in the city, and stopped her.

She thinks it was nice, that nothing wrong happened, but that we can't go further, for the sake of everyone around us.

And that is true. Yet, I still masturbate to the memory of that night, and I think I will never stop.

I was into this man from work, for almost ten years now. He is a few years younger than me, I am 45, and we are both married.

The disaster of a marriage I am in, is one of the reasons I found this place, but not to go into details, we practically have separated sex and social lives, but we keep appearances, for some reason, that we forgot in the mean time, so I know that he has a woman he sees, and I have had a few adventures as well, but nothing long term.

My colleague, the one I was into, is a wide shoulder, slim, tall man, with dark hair and thick, trimmed beard, dressed to impress, and I was throwing hints his way, for a long, long time, a touch on the shoulder, a joke, etc. I know he was looking at me in that way, since, not to sound over confident, I am still a good looking woman, especially for my age.

So, on Friday, at our Christmas party, I did my best to impress him. Little note, we do not bring our spouses to these things (Europe), so I danced with him, all night, and he was returning the signals, and, we ended up in a hotel room.

As I said before, I had a few adventures since my marriage practically seized to exist, but there is a reason I used past tense in the first sentence of this confession. While, all my life, men were pretty weary around me, I don't know if it is my looks, my overall vibe or something, but most men would be quite careful and vanilla with me. He wasn't, he was mean, rough, and disrespectful. It was mostly anal, with unnecessary roughness, insults, hair pulling, slapping, spitting... I never felt so dirty and humiliated in my life.

I felt great deal of shame after it was done. I didn't like it, and my crush on him just went away, but Friday night, I had the most intense orgasm of my life.

And before you ask, I will not do it again, but I do recognize that the physical pleasure I felt, was sweet and bitter at the same time, yet not sweet enough, to make me want the replay.

Sucked off a co-worker in his car after the company Christmas party tonight. Been years since I been with another guy, but damn it felt so good to have a cock in my mouth again, wish he lasted longer but he did give me one of the biggest loads I can remember swallowing. Hoping it’s not a one time thing. 

Wife told me a friend of her was getting harassed at work from male coworker,I’ve said something stupid then she told me she was sexual harassed before we met she was 20 at the time her boss was older she said ,kept on bugging her to go out she said no would schedule working at night when he work at night then one day coworkers party wife said she had a few drinks in her again bugging her last thing she remembered was talking to her friend about leaving she said next thing she new woke up at his place and said she felt like she had sex and saw to condom wraps on counter had to tell her to stop and pretend I was upset for her but I was actually turn on I know it Despicable and degenerate of me to get turn on 

I had anal sex only once in my life, and I still remember it, every detail of it, till this day.

We were graduating hs, so, legal of age, and she was the girl everyone lusted for. Tall, very beautiful, dark hair, top girl in the school. I was dating her cousin, who was also kind of hot, but not on her level. It was prom night, and, little detour here, in Europe we don't do these like in the US, prom night is for the graduates only, and you can come with another graduate as your date. So I asked her, since I knew her, we were kind of friends, and my gf, her cousin, was at the entrance of the hotel, where friends and family gather to clap and cheer for the graduate couples going into their first "grand" party of their lives.

I was all over her, all night long, dancing with her, feeling her up, and she didn't object. We drank a lot, and at the end of the evening, we all went out, to go crazy on the streets. After some time, we got to a secluded spot, and started kissing. I wanted more, but she was reluctant, she said that even this is too much, that it is a betrayal of her cousin, that she made a mistake, that she hates me since I never told her how I feel before going out with her cousin, since she was into me, for years. And that was it.

Afterwards, my gf called me, angry as hell. She confessed to her, and all hell broke loose, even some punches were exchanged, and nothing good came of it. Two month later, I moved to a city, for uni, and all I knew is that she moved to a different city.

She did text me soon after, and we renewed our contact. She obviously wanted me, but she was still reluctant, and, after almost three months of going back and forth, she invited me to come see her.

So I did. We got out, and she was wearing one of those tartan skirts, with pantyhose underneath, and we ended at her place, with her room mate in the other room, drunk and horny. We ended up on the bed, and I pulled her nylons down, and just went to town, from the spooning position.

She was ready, she was wet, she looked amazing, and, with one of the thrusts, I missed a little, and pressed against her ass. Got back in the pussy, and next time, I did it on purpose. I backed up a little, and, seemingly clumsy, tried to go back in, but I went to the place I wanted to be, slowly at first. She moaned really loud, but didn't protest, so I continued.

At that point, that was the highlight of my life, ass fucking the hottest girl from school, and the best part is, when I am drunk, I can go for days.

After few minutes, I started going faster, and deeper, and harder, and it ended up as a 20 something minute hard, anal session, while she screamed from pleasure.

We had sex three more times that weekend, and when I got back to uni, I thought I found a woman of my life. Only I didn't.

She told me she just can't do it, since her cousin, what are the odds, reached back to her, two days after I left, and she can't blow that opportunity, since they were very close.

I still think, that that wasn't the case, that my lust, and that night of anal, made her second guess me as a choice, even though she clearly enjoyed it.

And no, I never felt remorse for how it went, I would trade that one night of sex with her, for the sum of all my sexual experiences, it was that good.

Okay, this will probably be a little weird one, at least it was for me. Given that this is Motherless, who knows it might even be tame, but still here goes. First things first, I am a 52 year widowed overweight bisexual man who is out of the closet, decades ago. Last week I had been invited to a birthday party for a friend of mine. It was a cross-dressing party. And I had been told to bring a female dressed as male, as I had to bring a plus one. At first I thought of not going as I knew no-one but he managed to convince me to come anyway. 
I did not have a dress to wear as I had never gone cross-dressed or whatever the correct term is. He was kind enough to give me a dress to wear that fit me.
And I found a pair of sandals that I added a little flower on each to give them that feminine touch.
The dress was a very casual dress, looked like something from the seventies. I ordered an Uber as I knew all of the cabbies, for work related jobs. My driver was a young man who was quite taken aback by my visage but he still opened the door for me like I was a proper lady. I sat up front with him and even though I was early he actually started to flirt with me. And eventually he even put his hand on my thigh. 
I was well aware of that I was not fooling anybody as I still looked like a man. I  did not mind him putting his hand on my thigh, nor did I mind him touching my by now hard-on. He asked me if we could pull over so he could 
do more, if we had time. 

As I was in no rush, I accepted his offer. 
He pulled over and leaned over my crotch and just went down on me. And he knee what he was doing. 
He used his tongue like a master and when I felt that piercing i came quickly. He swallowed everything I had and continued to lick me clean.

I asked him if he wanted something more than that and he looked like a kid who had just been given permission for a once in a lifetime experience. 
He told me that he would love to fuck me but he did not have any rubbers with him. I showed him a tube of lube and leaned over and kissed him on his cheek and told him that I liked it bareback, if he wanted to do me like that. He told me to get out of the car and pull up my dress and my panties down. And he would give me the fuck of a decade, his words. And so I did get out, hiked up my dress and that was it, as I was 

He followed suit and got out. Now, he may not have been hung like a horse, thank goodness, but whatever he had was good enough.
He fucked me so hard that I accidentally made a dent in his car. But he did not give a crap. When he eventually came, we were both exhausted.
After that fucking, we both got back in the car and drove to the party.
As I was about to pay him for the drive, he said that he had already been paid in full and he would gladly drive me home after the party. 

The party was so-so. But at least my friend was happy to see me. Needless to say, the rides home were a whole lot more exciting. And I say rides. Because he rode my ass like a steamroller. 
When I eventually came back home, I could hardly walk properly, but I was OK with that.
He used a card of a "demented viking" as a business card. Never knew that was a thing. 

I confess that sometimes I really just need to be taken advantage of and have my tight ass fucked..

Last time I did butt stuff was about a year ago when I sent this photo to a guy friend one Saturday night after leaving a house party with our friends.

We've hooked up before so I knew he would be the perfect fit for me.. he wasn't too big or girthy. Buttt I was eager to get pounded.

My snap to him just said "cum over ;)" and I swear he must've been right down the street because in less than 5 minutes he was entering my room.

He saw the bottle of lube I left out on my dresser. He grabbed it and walked over to my behind and slid to the side my thong. I felt his index finger slide deep into my asshole and he prepped my ass with lube. He slid a second finger inside and began spreading apart my asshole.

I pushed back against himm.. relaxing my ass then squeezing hard against his fingers deep inside of me.. his fingers then slid out and I felt a short moment of relief followed by him getting behind me, mounting me, and sliding his cock deep into my asshole.

I leaned forward resting on my elbows now and he was going to town on me. I reached down to my pussy with my left hand and felt how gushing wet I was.. I reached further back to feel his balls pressed up against me as his entire shaft was inside of me.. I began fingering myself and rubbing my pussy.. not long after I felt him throb deep inside of my ass.

See, here’s the thing. I have a choice. I have an old jerking buddy who’s going to be in town this weekend and I have a chance to get off with him. More than jerking, he’s one of the ones I can suck and 69 with. We’ve done it every couple of years for a few years now.

On the other hand, there’s a GILF who comes into my place of work. Tiny thing. 70+. 5 foot. Maybe 110 pounds. Great taste in clothes. Former New York party girl circa 1970. I complimented her shoes yesterday, these great patent leather and calf loafers. Black. High dollar. Bright socks. She told me about them. I told her I thought they were kinky and she said, “Kinky, huh?” and then she asked me out for a drink.

The problem is that my buddy will be here for just a few hours on Saturday evening on his way through. Not even for overnight like he usualloy is. My GILF friend asked me out specifically for the same few hours. I can either risk turning her down and go for a sure thing and cum with someone who knows how to get me off OR I can hope to get to strip my little gremlin granny down to her loafers and get kinky. Hinted at but not a sure thing. Something I’ve been wanting to do for a while now. 75 or no, she’s fit and tight. I’d like to see just how tight.

I confession that I can’t decide. Cock or cunt. I haven’t had this problem since I was a lad, banging a brother and a sister (No, not and never at the same time).

Ok, so this might be a bit of a wall of text but I have a lot to unpack and think over regarding a situation with my mom.

For background, my mom is single and wealthy enough that she doesn't have to work following her and my father divorcing ten years ago. I rent and live in an apartment that's attached to her house. 

Just over a year ago she received a diagnosis that will eventually be terminal. At the moment she is absolutely fine and there are zero signs or symptoms but it will become progressive but nobody knows for sure when. 

Since the diagnosis, she has basically been living life and doing everything and anything she wants to. It's like a zero fucks given attitude which I totally get. 

She has a good social life with friends who are always out, drinking and partying. That's absolutely fine in my eyes. 

She doesn't have a partner and states she doesn't want one given the situation. 

While out partying, she makes no secret that she enjoys a bit of coke. Again, that's fine as I take it from time to time. There has been a change in her behaviour with it though and, to be blunt, I'm 99% sure she is making sexual advances on me. 

She sent me some pictures "by accident" of her in different underwear and she has started talking a lot about a fried of hers that I hooked up with a few years back.

She has also mentioned things from long ago too, like when she found her used panties in my room while I was a hormonal, horny teen! Making jokes and suggestive comments. 

It came to a head 2 nights ago. She had clearly taken a few lines and as I walked in to the lounge to sit and have a drink with her, she was clearly playing with herself under her robe after coming out the shower. She didn't stop immediately and I pretended not to notice but it was plain to see what she was doing. 

She's an attractive woman and I just don't know what I should realistically do. I know what the fantasy part of my imagination wants but would it realistically be a good idea to pursue this?