Introduction:
We had been having sex almost from the beginning. It was a relationship where you were having sex before you actually considered yourselves to be dating, despite not seeing anyone else at the time. We met at a time when she was separated from her second husband, with a divorce pending. Whatever the quality of her sex life was in both her marriages in the beginning, in the end, it was dismal. Both her husbands ended up being emotionally and physically abusive. At best, the way she described sex, it seemed to be a ‘wifely duty’, endured but not enjoyed, and often silently loathed. At worst, she never said, but I can only assume sex was taken from her unwillingly and abusively.
But when I met her, I would have never guessed that she had such poor sexual experiences for the past 10 years or more. We had gone out a few times, and at her home one evening, it began with gentle kissing, caressing, and ended with sweet love making. I guess I came across one of those women that was just starved for good sex with someone who cares about her, which I did very much, and everything really was wonderful.
We grew a lot together, sexually speaking. Living out fantasies or playing on desires that had never been realized before. We never went so far as anything sadistic or masochistic, didn’t introduce others into our sex life, and never did anything that we didn’t think the other wouldn’t like. It ranged from lovemaking by soft music and candlelight, to mutual and lone oral sex to orgasm with no penetration, mutual masterbation, to rather hard-core fucking porno-movie style.
But early in the relationship, while talking about sex, she mentioned that she thought anal sex was wrong, implying it was a moral sin of some sort. I held no such belief, even though on only a very few occaisions I had done such things. A few months later, discussing previous sexual encounters (and trying to avoid admitting to have had anal sex with another woman), she bluntly asked me if I had had anal sex before. I couldn’t lie, so I told her I had. Wow, the next few hours were less-than-pleasant with her. Despite having a quite open relationshiop and free discussion of limits of sex, even when referring to previous partners, she didn’t much appreciate my previous sexual acts in this arena, regardless of the very minor exprience I had.
She told me again how it was wrong, and even said it was ‘dirty’. Not ‘dirty’ in a provocative or sensual manner. She said ‘dirty’ in a way a mother chastizes a child for wanting to handle or investigate a dead bird. ‘Dirty’, as in the mere matter of being near the creature would bring disease or even death upon the one in the dead animal’s presence. With that in mind, I never approached her with any prospect of anal sex.
So, despite a deep and wanton desire of anal sex, I never actually asked for such action. Anal sex has always been a form of gratification that turned me on. I really have no idea how or why…it just did. But, knowing her stance on the matter, I kept the fantasy to myself.
But somehow she must have known. In our open attitude towards sex, I guess one evening she felt compelled to let down her predujice and let her body be used for my unspoken desire.
She came home rather drunk from an evening out with a friend of hers. I had worked late (but she came home later), and was already in bed, naked as usual. She sweetly snuggled next to me ‘spoon’ style as I lay, almost asleep. I knew she was drunk and more horny than usual, but I had had a long day, and had to be at work early the next day again. I would have been content to fall back asleep with her in my arms in the few minutes it would normally take. I have no idea why or where it came from, but she whispered to me:
‘Will you have anal sex with me”
So, I immediately went from a few moments from deep sleep, to instantly aroused. In my mind, I knew she was just feeling particularly happy to be with me, and wanted to do anything to please me. I think the thought of her wifely duty from her previous husbands may have been running through her mind. But the sudden pressure between my legs took over control and didn’t particularly care that she would likely change her mind once I were inside her backside.
Weakly, I sputtered, ‘Honey, are you sure”
I knew I didn’t particularly care whether she said yes or no, but hearing her say ‘yes’ loosed my inhibition.
I was still somewhat tired (having been in bed for a while by the time she came home), but figured this was a very rare moment. I tried kissing on her neck and shoulders to entice her, but I’m sure my actions were clumsy. It wasn’t long before I reached for the KY we kept in the bed’s headboard cabinet. I tried to be romantic as I lubed my hard-on and her anus, but I doubt I was.
Since I had little experience with anal sex, I didn’t know what advice to give her as I pressed my cock to her puckered ass. I pushed myself into her, maybe past the head of my penis. At this point, I tried to evaulate her response. She had never been very vocal or verbally response to anything I did to or for her, so I had to ‘sense’ whether she liked it or not. Now, with only a small part of my cock inside her backside, I sensed she might not enjoy this. However, I still hoped that the initial feeling of discomfort and inhibition would pass for her. She didn’t object, and so I pressed myself more fully into her.
She didn’t exactly stop me, so I started sliding myself back and forth inside of her backside. Knowing how much she loved vaginal sex with me, I caught on quickly that this didn’t feel as enjoyable to her. I don’t know why, but it didn’t stop me. Her tight, virgin ass felt so exsquisite to me, I thought I would cum inside of her in a moment or two. I actually hoped that I would orgasm quickly so that I could have my wish so fast that it wouldn’t hurt her too much to want to try again some day. But, my heart knew that her pleasure wasn’t the same as mine. It was like trying to get a kiss on the cheek from a girl I knew didn’t want me to kiss her at all.
But, I was already inside of her. My cock was half-deep inside an ass I had wanted to fuck for months. I wanted to be gentle, and sweet, and loving…but it was almost like it was too late for that, and I would never have a chance to try again. I grabbed her hips, and pushed against them until I felt my hips against her buns. She winsed, and tensed up. At this point, I knew her body was no longer as willing to accomodate her love for me as her mind was a few minutes earlier.
Again, I was already inside of her. Her tight asshole squeezed around my cock in a way I had never felt inside of her before. From her body language, I knew that I would never get this chance again. I figured she relapsed into the feelings of having to endure sex with someone that she experienced when she no longer enjoyed sex with her previous husbands. I still held her firm, my full cock inside her ass. She ever-so-softly whimpered.
Something came over me that I had never felt before. I was actually angry with her. I felt inside that she deserved to feel pain or discomfort for even asking me to do something she knew I wanted to do but wasn’t really hoping I would accept the proposal of. Even though I loved her, I wanted to fuck her in a way she didn’t want to be fucked…and I didn’t care.
In this spooning position, with my cock inside her dark, ‘dirty’ hole, I wanted to fuck her out of my own deep desire…but wanted to fuck her even more because she didn’t want me to be inside her like that any longer. Never before had I felt like that, but knowing she wanted me to stop, turned me on even more.
I started sliding my cock back and forth in her ass, feeling the urge to fuck her until I came, and the thought of doing her this way made me even hotter. I knew I was hurting the woman I felt very deeply for, but I just didn’t care. I wanted to fuck her tight, tender asshole until I filled her with all the cum I had. It envigorated me, and I began thrusting harder and deeper inside of her.
Then, something that I didn’t expect happened, and it turned me on even more than I coul d have imagined. She cried out:
‘Baby, you’re hurting me…..please, stop.’
Hearing her on the verge of begging me to stop made me want to fuck her ass all the more. I wanted to make her hurt, I wanted to make her beseech me to not cum inside of her bowels.
And then she said it. She whimpered:
‘Honey, stop it….please don’t. Don’t cum inside me like this. I don’t want it. Please, baby….please…’
With those words, I couldn’t hold back. Something inside of me wanted to punish the one I so dearly loved with the most painful and intrusive sex she had ever known. I thrust myself harder and deeper inside of her ass, mercislessly pounded her virgin hole without remorse. I fucked and I fucked and I fucked her asshole. To my surprise, and dark appeasement, she began whimpering tears and choked pleas.
‘Please, honey….pleeease. Don’t. Please, stop. I don’t want this anymore. I’m sorry. Anything for you, but please stop. Please don’t cum inside of me like this. Baby, please stop. Please, baby……pleeeeaaaaase.’ I could feel her body quiver as she quietly began sobbing in pain and sorrow.
Despite all the feelings I had for her, I didn’t want to stop. The tingling and excitement I felt at both the physical feeling and dominance I felt was too much to let go for her sake. I knew it would only take another moment or two and it would all be finished. And then she said what I wanted to hear:
‘OOOOoooooooowwwwwwwwwww- uuuuuuuuucccccccchhhhhhhhhhhaaaaaaaaaaaa!!!!!!!!!! It hurts so much, honey, pllllleeeeeasssseeee don’t cum!!!’
With that, a vibrating sensation sprang from deep within my loins. It started with a pressure somewhere near my bladder, and I felt my balls contract as the pressure exploded from hips, to my ass, and then from my cock to inside of my lover’s bowels. I couldn’t stop it then, and wave after wave of orgasmic release jet inside her beautiful body. I quivered and pulsed, allowing the full pleasure my orgasm fill her dark side with more of my cum than I could have imagined. I felt my own warm fluids begining to escape from her full backside and fill the area between her backside and my hips pressed against her.
In near exhaustion, I wrapped my arms around her, clutching her close to me. I kissed her still quaking shoulders and held her, hoping to show her that I still loved her. I was still inside her as she openly sobbed in pain and disappointment. I tried to withdraw from her as gently as I could, but at this point, any care was useless.
I wanted to hold her and tell her ‘I’m sorry’ but I knew any apologies would be of little comfort to her. The moment she was free of my embrace, she rolled to the other side of the bed, and got up. She hurried to the bathroom, where I heard a bath being drawn, and quiet crying. My guilt kept me in bed, hoping she would come back, so that I could muster some sort of apology.
It must have been an hour or more later when she came back to bed, and even then she stayed well out of reach of my soft, cuddling apologies. We must have laid in bed for two or three hours before she rolled over to face me. I was never good with explanations of bad behavior. So, she began:
‘Honey,’ she said, ‘I’m sorry. I know you like that sort of thing, and I wanted to please you.’
‘Its my fault,’ I said, ‘I pretty much knew you wouldn’t like that. I should have just not said ‘ok’ when you asked. Baby, I’m really sorry. I know I hurt you and I would never do that intentionally. I would never ask you to do something you didn’t want to.’
The next few hours were spent apologizing back and forth, each trying to make it more our own fault than the others’. Just before dawn (when I had to get up for another long day of work), we finally made amends. We both agreed that we were both sorry and had forgiven each other, and that no one was actually at fault.
After another long day of work that day, we went to bed together, and had the softest, most gentle and sweet ‘make-up sex’ we had ever had. We fell asleep very happy and content, in each other’s arms.

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