Cole Ch. 02, or Breaking and Entering

Story Info
Another first time, another body part.
1.2k words
4
63.8k
1
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I'd always said I hated anal sex, would not even try it. The one time I had, I thought I'd die--might as well have had a red-hot poker jammed up my ass. There was no damn way anyone was going to talk me into it again.

Needless to say, it was Cole who broke me in, and made me like it in spite of myself. Another of our little mind games ended around 5am one workday after he had thoroughly but with a surprising tenderness, fucked my butt, better yet because it was the first time a woman had allowed him to, unless he was lying of course.

At this point in our relationship, Cole almost always fucked me doggy-style; he seemed to have a penchant for it. And almost every time he had me on my hands and knees he'd ask, or just plain beg, for me to let him try my back door. Since he was who he was, these requests were usually really obscene, with such terminology as, "brown eye," "ass-fuck," "sexual chocolate," "fudge pack," and "your pooper." I'd been hearing this line of talk long enough that it were non-offensive to me and even kind of sexy. It had always been a fantasy of mine to fuck two (or more) guys at the same time; by simple arithmetic, I'd never accomplish that feat without putting my other hole into play. So Cole was the man for the job.

He didn't know what he was doing any more than I did, but he seemed to have the instincts for it. I let him go on with his playful complaining routine longer than usual while he fucked me, all the while running his forefinger lightly over my unused hole, and finally said he could, still playing doubtful. I also made him agree to as much lube as I deemed necessary. Squirting a generous wad of slick shit into my hand, letting it warm, I got out from under him and smeared it all over his upward pointing cock. This man's penis really did have a life of it's own. I could lead it from side to side with my hand without even touching it; he could make it jump; he could even make it look like it was talking by tightening and releasing some internal muscle. His glistening tool was in fine form, covered with a thick layer of grease and rock-hard. Because it also got bigger and bigger as he got more turned on, and it was looking pretty large already, I was more than a little leery.

Cole positioned me as usual, head down, ass up, facing away from him. I felt the tip of his prick touch my asshole and flinched. "Just relax," he instructed. "I won't hurt you. Slide it down when you're ready; I'll let you control the movement." This was not his normal tack. I felt a rush of heat, probably just in gratitude. My only other experience had been akin to rape, the unwanted kind, and he knew it.

I backed slightly, feeling the tight anal band beginning to stretch, then burn. I stopped. "Put your head down more," Cole suggested. That helped. Without having to think about holding my torso up, I could relax somewhat. He started messing with my butt; running his hands over it and my haunches, and up and down my lower back. Loving this attention, I loosened gradually, grabbed what courage I had, and backed onto him a little more. Now the whole head of his cock was in; putting it in had hurt, but I was getting used to it. Cole gyrated his hips in such a way that he wasn't forcing anything more in just yet. He wanted to know if I liked it. "Um?" By then he had me by my hips, his long hands holding on firmly, wanting it all. Taking a deep breath I told him to push it all in, but slowly.


He did. His well-oiled shaft probed me further and further; like walking backwards, the feeling was unnatural, like no one had any business being where his dick was, and was extremely exciting. If I didn't want to be hurt or even injured, I had to submit, to be slack. We weren't even playing 'power;' he would have quit at any time, but there I was in my own bed, allowing him to more or less de-virginize my ass.

When his cock was in to the hilt, surrounded by my extremely tight anal muscles, Cole leaned forward, pressing his lanky torso against my back, one arm coming down on each side of me. His long dirty blond hair, the same shade as mine, brushed my shoulder blades. He reminded me of how so many people thought we were brother and sister because of it. This was the pinnacle of affection for him. He tweaked one of my nipples, then the other.

"Spread your legs more; get down," he directed, and began to draw his cock back. I gasped at the new sensation, almost like taking a shit but again with an unnatural object. After easing nearly all the way out, his oily member pressed back up my ass again, drawing another choked-up noise from me. It still burned like hell but I didn't mind anymore; even kind of liked it. Our movements sped up little by little till soon Cole wasn't much more subdued than when he fucked my pussy. It was a little rough for me, but, I figured, might as well get used to it sooner as later. The rub on the backside of my cunt, like Cole's penis was stroking my G-spot through a thick rubber sheet, wasn't going to make me come, but it sent me up to the plateau that precedes and that was fine. Cole smacked my ass, first on one side then the other. Squealing in a high pitch, I moaned, "Spank me!" and he did it again, making it a three part burn: right, left, center. The pain of it, along with the intense turn-on from both the feeling and the forbidden-ness of it, made me grunt like a horny little sex pig with every thrust. Cole put one hand over my mouth and yanked me back by the hair with his other hand, slamming into me so hard that his balls hit my clit, scratching and rubbing at it, & somehow, ass on fire and my dripping pussy not filled, i spewed woman-cum all over us.

He couldn't hold back any more (I was in enough pain to be relieved), but he slowed back down & got all languid, milking his own cock with my sphincter. In his usual manner, when he did at all, Cole began to verbally tick off the steps of his oncoming orgasm, letting me know how tight his balls were, that he couldn't wait to blow his wad, that he was going to shoot so much come into my asshole NOW, which he did. No one ever shot as much semen as Cole. His ejaculation was strangely cooling and it seemed to go on forever, while I grunted and squeaked at the way his very engorged cock was rammed into me just then. He withdrew slowly; he was shaking. Besides the fact I'd just let him do what he'd been wanting to for months, I think that holding back made it even more pleasurable.

*************************************************

(if this story turned you on, you might like to read another about cole over in the erotic couplings section. that night, when he stumbled in at 3am, he wanted a virgin, and i was to be his cherry-popping party)

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

story TAGS

Similar Stories

A Category That Is: Loving Wives An author's personal view on a very controversial category.in Reviews & Essays
Fucking My Brother-In-Law My brother-in-law didn't know I was there...in Erotic Couplings
A Small Indiscretion Ch. 01 A small indiscretion...and decisions to be taken.in Loving Wives
The Submissive Babysitter Wife shows husband how obedient babysitter can be.in Group Sex
Two King Beds Two married couples are forced to share a hotel room.in Group Sex
More Stories