Category: Anal Stories

Unexpected Encounter

by karelan©

I'm a 42 year old professional woman, reasonably pretty, with very long, straight, dark hair. In my late teens and early twenties I had a fairly wild time, but since then I've settled down a bit, and been in a couple of long term relationships, though I've never married - that final commitment just isn't my thing. These days I'm carrying about 20lbs more than I should, though I don't look too bad overall. Let's just say that I don't have a shortage of offers from the opposite sex, which does my ego good even though I seldom take advantage of any of the opportunities!

However, one unexpected encounter I did have about 2 years ago made such a mark on me that I felt I just had to write about it.

I was away at a major conference in the US, along with a number of colleagues, including a few from one of our local affiliates. I'd vaguely noted that one of the men was rather attractive, but as Stephen was some 7-8 years younger than me, I thought no more about it. However, that night, as I was in the bar after the conference dinner, he came over to talk and we ended up chatting for ages, and getting on really well. It got to about 1am, and we decided to call it a night, downed our drinks and both headed for the lift. I pressed the button for my floor, and had to insert my key to activate the button - I'd been lucky enough to be allocated a room on the executive floor. This occasioned a bit of teasing about how come I'd managed to get a 'posh' room - were those for Head Office people only - and what was the difference in the room facilities? The lift stopped at his floor and he bent over to give me what I expected would be a brief goodnight kiss on the cheek - which turned into something more. The lift doors closed again and we arrived at my floor, with me slightly bemused at what had just happened!

"I'd like to see the difference in the rooms..." Stephen suggested.

Was I going to fall for that one? Well, my reckless side got the better of me, so I stifled my doubts and conscience, twined my fingers in his and led him down the hallway to my room.

Once inside and the door closed, Stephen wasted no time in taking me into his arms again, and we kissed whilst his hands undid my trousers. They fell to the floor and he disengaged from me long enough for him to pull my top over my head and unclip my bra. I'd just about managed to unbutton his shirt and unbuckle his belt by then, so he completed undressing himself whilst I kicked off my shoes and stepped out of the rest of my clothing. Then I looked at him again, my eyes were drawn down to his cock, and I think my jaw must have dropped. He was bigger than I'd expected, not so much in length - he was probably about 8", but he was wonderfully thick, and as I reached forward to caress his cock, my hand was nowhere near closing around his shaft.

I couldn't help it, I dropped to my knees to kiss and suck his beautiful cock. I licked him from base to tip and sucked the head and as much as I could of his cock but there was no way I could take all of him into my mouth.

Stephen grabbed the back of my head and started to fuck my mouth, thrusting the blunt head of his cock against the back of my throat, making me gag and struggle to breathe. Suddenly, he withdrew from my mouth, pulled me up from the floor, and pushed me face down onto the bed. I felt the bed move as he knelt behind me, and spread my legs. He pulled my hips up until I was on my hands & knees, and he could see my wet and swollen pussy lips. The rough handling was obviously turning me on, and I was more than ready to be well fucked.

Oh god, he was so big! His cock felt so wonderful as, with no more preparation, he thrust it deep into my pussy, stretching me all at once, hitting my cervix and making me cry out in shock. Fortunately I was so aroused and wet that there was only minimal pain at the rough entry. He thrust in and out, the angle of the penetration stimulating me beyond belief. There's something about being fucked from behind that really turns me on, I think it's the vulnerability of the position, about knowing that the man fucking you is in complete control. All I could do was kneel there, my head buried in the pillow, and take the rough thrusts of his huge cock, and it felt so wonderful that I found myself begging him not to stop and to fuck me even harder. His thrusting brought me to orgasm, and I came harder than I'd ever come before, and as he continued to fuck me it felt as though I was coming again and again, my now sore pussy contracting around his hard cock.

Stephen thrust as deep as he could inside me and leant down across my back. "You're such a dirty bitch that I'm going to fuck you in the ass" he hissed in my ear.

I felt my belly clench in fear. I'd been sodomised by a few men in the past, and though I'd thoroughly enjoyed my previous experiences, I knew there was always some pain involved with the initial penetration and stretching. Stephen's cock was twice as thick as any cock I'd taken up my ass before and so I was terrified and yet desperately aroused as I anticipated him thrusting his cock roughly into my rectum.

He withdrew from my wet pussy and I felt the massive, blunt head of his cock nudge between the cheeks of my ass, and then press against my anal pucker. He gripped my hips tightly and forced the head of his cock into my anus with one vicious thrust.

I cried out in agony as I felt my anal ring tear, the pain and burning making my knees go weak. I instinctively tried to pull away, but Stephen had obviously expected that and simply pulled me back onto his cock. He forced his cock further into me, stretching my rectum beyond belief and then, without a pause to let me adjust, rammed his cock in until I could feel his balls tight up against my pussy. The agony of being fully impaled on his massive cock was unbelievable, it felt like I had been ripped apart, and I couldn't move, only moan helplessly. He drew back, making me cry out again in pain as the base of the head of his cock stretched my anal ring again. Just before popping out completely, he drove his cock violently back into my anus, and then began to thrust in and out of my violated rectum. My head and upper body had dropped to the bed, and I gripped the sheets desperately and cried and whimpered each time Stephen rammed into me, it felt as though the head of his cock was hitting a barrier deep in my bowels, bruising my insides.

Stephen let go of my hips and grabbed my buttocks, spreading them as far apart as he could so he could drive deeper into me. I screamed with agony as the wide base of his cock tore my anus even further while the head of his cock ripped past the barrier inside me, entering where no man had ever been before, his cock causing excruciating pain with each brutal thrust.

I kept expecting the pain to subside as the pleasure built, but this time, probably because Stephen's cock was so big, and the initial entry had been so violent, the pain never went away, but became part of the ecstasy of the experience. I felt complete submission to this man who was ramming his massive cock roughly in and out of my bowels, giving me more pain and pleasure than I'd ever imagined possible. I suddenly realised that I was moaning with lust and desire and I began to push back against his vicious thrusts, accepting his huge cock as deeply as possible into my bowels.

"You love it don't you" Stephen crowed. "You must be a slut, as only sluts like it hard up the ass."

"Oh god yes!" I moaned, "Fuck my ass and make me beg, like the slut I am."

Yes, I moaned and begged for him to continue sodomising me, shocked and horrified at my desire and my acceptance of the violation. But gradually the pain overwhelmed me again, and just as I thought I couldn't take any more, Stephen ripped his cock out of my anus, flipped me over onto my back and knelt astride me. My eyes were drawn inexorably to his majestic erection, streaked with blood from my anus and rectum. He fisted his cock, gave it a few rubs, and then came all over my face and breasts. He collapsed beside me, panting and sweaty.

I lay there with him, my head spinning, marked with his semen, my pussy well-fucked and sore, and my anus & rectum torn and burning from his violent penetration. All I knew at that moment was that, despite the pain, I would want Stephen to fuck me in the ass again.

Written by: karelan

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Story Tags: anal, oral, torn ass, pleasure, pain

Category: Anal Stories