Chapter 3

For a long time after my daughter was born, and even after I was supposed to be able to have sex again, I was really sore. My boyfriend, Michelle’s father, tried everything to ease me back into things. But no matter what, I just couldn’t have sex. Any sort of pressure hurt, and the few times we really tried to have sex it was excruciating. I just couldn’t do it.

About four months after giving birth, Phillip, who is about four years older than me, suggested we try anal. Now, I’ve never been against any form of sex in my life. Even back then. Whatever you want to do is fine with me. But having a big cock in my ass – he isn’t as big as you, but he is big – was not exactly something I wanted. But I was young and wanted to please him. It’s how I was raised. The women take care of their men, submitting, regardless of her wants. Well, after about a month of him asking about anal I agreed.

The first night we tried it he had me on my back, my legs were pressed against the mattress and my arms were wrapped over my thighs. I am extremely flexible, like I said, and it was his favorite position. He liked it, he told me, because I could see his cock going into me when we had sex. Anyhow, I was bent over double, holding myself in position and watching as he lubed up my ass. Gentle as he was, it was disconcerting to watch him stretching out my ass with his fingers. Not that I could see it all that well. But I could see enough of his hand to get the basic visual.

At first, with only one finger inside me, it was mildly unpleasant. It felt like I had to use the bathroom. But the more he fingered my ass the better it felt. Pretty soon he had two fingers inside me. That felt even better. When he started working on my ass with a third finger I had an orgasm. Both of us were shocked. But it was very encouraging, and it made me want to continue as much as it made him want to, as well.

He worked me like that for a long time, making me cum over and over. Finally he asked if I was ready for him to fuck my ass. I nodded and told him I was. That was when I knew pain. The moment his cock entered me I thought I was going to die. But I held my position and didn’t try to stop him.

Phillip was slow, at first, and I was crying. But as he got going the pain eased. Really, it didn’t take too long before it started feeling good. That was as strange a moment as I can recall experiencing with him. My body wanted to cum. I was on the verge for a long time. Only the pain kept me from it. But then, all of a sudden, the pain went away. That’s when I had the first truly intense orgasm of my life, and I nearly blacked out. But he wasn’t anywhere close to cumming. So, of course, he kept going and I kept cumming. By the time he came I was exhausted from so many orgasms.

The next day, before he left for work, Phillip fucked my ass again. This time he didn’t stretch me out ahead of time. It hurt so bad I could hardly take it. Not that it stopped me from cumming. It didn’t. It was, though, an overall unpleasant experience until the pain eased and orgasms started. Later, when I explained how much it hurt, Phillip informed me he wouldn’t have time to stretch me every time. He liked morning sex. Since he had to go to work first thing there was just no way he could take the time to stretch me out. He was fine with taking his time at night, though.

For about the next month I put up with the horrible pain in the morning. One day, unable and unwilling to take the pain, I refused to let him fuck me in the morning. It just hurt too damned much. So he tried to have vaginal sex with me again. That was almost as bad, so I ended up giving him a blow job. That was before I could deep throat, and I wasn’t very good at it. Still, it satisfied him.

Later that night, when he came home from work he presented me with flowers and a gift. He tended to do things like that when I was mad. Not that I was mad, but he did know I would forgive him for anything if he brought home flowers. Well, the gift turned out to be a set of butt plugs. There were three: A small one, a medium one, and a big one. The largest of them was about as big around as my wrist.

“You’re going to start with the small one and then move up to the biggest one,” I was told. “That way I don’t have to worry about stretching you out every time I want to have sex.”

Needless to say, I was appalled. I was even more appalled when he told me I had to wear a plug all day, every day. It was humiliating and degrading. But I was trained to be a good girl – obedient to a fault. So, I did exactly what he told me without complaint.

For the next couple months I worked my way from the small plug to the biggest one. At first, it was pretty miserable. My ass would ache at being stretched out for so long. After a while, though, I got used to it. The worst part was having to clean them up. But I did it. And, truth be told, it did make it easier when he fucked my ass.

It probably took about two months before I got to the big plug. I was putting off using it when he asked me how the small plug was working. I told him it was going okay, and then let him know I was using the medium plug. We were in the living room. He had just had dinner after work and was watching television when he asked how long I had been using the medium plug.

“Probably a month,” I told him.

He asked if it ached anymore – I had told him about the aching – and when I said it didn’t ache he told me to get the big plug. He wanted to watch me put it in.

It was a humiliating experience. I’m a shy girl. I don’t like being naked around anyone unless we’re in the shower or in bed, or having sex. Even when I have sex, if it’s not in the bedroom, I prefer to have some sort of clothes on. I don’t know why. Anyhow, he had me strip and bend over the couch. Then he had me take the plug out of my ass and put it in my mouth. He didn’t want to hear me complaining, he told me. I probably don’t have to tell you I hated putting that plug in my mouth. It was gross and disgusting. But I did it anyway, thanking my stars I had gone to the bathroom before he got home from work. The plug, much as it could be, was clean. Thankfully, it didn’t taste like ass.

So, there I was, bent over the couch, one plug in my mouth and one plug in my hand, waiting for him to tell me what do to. But instead of having me plug myself he came up behind me, spit on my ass, and eased himself inside. Caught by surprise, and already pretty stretched out, there was no pain. I came instantly.

You should know that Phillip was never quick. Any time we had sex it took about a half hour. Sometimes it took longer. This was no exception. I came over and over, nearly passing out before he came. When he was finished I was in a state of mild delirium. I could barely think. After a while, I collapsed on the couch, suckling the plug in my mouth – something I only realized when I recovered my wits.

When I finally sat up, Phillip told me how good it was. Then he asked how I liked it. When I started to take out the plug to speak, he told me to keep it in. He liked my mouth plugged, he said. It kept me from rambling on. Then he asked if I liked being his ass slut. The words made me recoil, but it did turn me on. So, what could I do? I just nodded.

“Good. Now, let’s get that big plug in your ass,” he told me.

I had all but forgotten the big plug, which was on the couch beside me. When I spotted it he told me to put it in my ass. “And hurry up about it,” he said. “I don’t want cum leaking out of your ass and on to the couch.”

So that’s what I did. And for the next couple hours I sat beside him on the couch, naked and plugged at both ends. It was humiliating and horrible. But it still excited me. I hated that it excited me.

There were other nights like that. Those nights he would have me take the big plug from my ass and suck on it. Then he would fuck me until he came. I always had to plug myself when he was done.

For about the next three years, or so, I was kept plugged. We never had vaginal sex again, and pretty much we had anal sex two times a day. Once in the morning and again at night. On the weekends we would do it three or four times. Not that I minded. I loved it. Anal sex gives the best orgasms.

The only down side to the whole thing was how loose my ass seemed to get. The plug was as big around as my wrist, and his penis a little bigger. So my ass was constantly open. Humiliating and upsetting as it was, though, I never fought against it. The one time I asked him to let me have the plug out he refused. Since I was a good little girl, determined to be a perfect girlfriend – hopefully his wife one day – I didn’t argue. I really had no complaints other than how loose I was. The sex, truly, was absolutely amazing.

I stayed with him until he got abusive to me and Michelle. If he hadn’t have gotten abusive to us – especially Michelle – I would never have left him. My ass would still be plugged and I would probably have no control over my bowels. That’s scary, when I think about it. But it’s true. I know it.

After our breakup I stopped using the plug. I was a little worried, truth be told, that I would have a horrible accident. Thankfully, that never happened. The only thing that was an issue was how it felt not to be plugged. After so long, it seemed normal. Having my ass empty was very difficult to get used to, oddly enough.