Amber and Sara's DemandbyAkireon©
**Author's Note: This chapter in Amber's life follows the 'Amber in the Rain' stories, but is still well before her National Nude Day exploration. It's also a slightly different direction for her. Please, tell me what you think.
Ouch. First times with anal sex kind of suck. I got over it, but owee. Well, the truth is, it didn't hurt all that much going in, or coming out. The pain was later, after it was all over.
The boy's name was Tom. I'd dated him a few weeks. He was a little too Christian for me, a little too stuffy about some things, like gays, alternate religions, and other things people should be allowed to explore. I'm not saying what's right and wrong, mind you, but I think very few of us have the wisdom to truly say something is wrong and should be forbidden. I eventually broke up with Tom, but before that, several weeks before that, he asked me out to a movie.
I can't remember what the movie was, but in one part, a guy had to take it up the ass. I remember wincing, and later, when we were sitting alone in a diner and joking about the movie, I brought it up along with how it must have sucked.
"It's not really that bad," Tom answered with a straight face.
I gasped. "What? You've tried it?"
It was perfect. He blushed as red as the checkered blocks on the diner's table-cloth. I chuckled.
"No," Tom said. "I..." He leaned close. "I did it with an ex-girlfriend. She said it was pretty hot, once she got used to it."
I blinked. Tom? This Tom? Did a girl's ass? I wasn't sure I believed it. "Okay."
"We can try it sometime, if you want," he murmured. "I promise you'll enjoy it, as kinky as you are."
He had no idea. He didn't know anything about my relationship with Sara, my roommate and girlfriend. Yes, I know, dishonest of me to not tell him, but why should I punish our relationship with information that would only make Tom angry? Or jealous, which amounts to the same thing? Or greedy?
I'd let both Tom and Sara play with my ass before, a little. I had never been too excited about it, other than the pure kinkiness of having someone else's finger in my asshole, because no one had made any sort of deal at all. Both of them had played a little, from time to time, and that was that. Now, Tom was proposing to put his cock right up there. A finger was one thing. His prick was quite a bit larger, and I found the notion daunting. But he said his ex was okay with it. Did I have to live up to her? I figured I did, if I wanted to keep Tom around. What would Sara say?
She'd say go for it. She let me spy on her with her boyfriend from time to time; he still didn't know about she and I either. He fucked her ass sometimes, if she was in the mood.
"All right," I said. "Tonight is your one shot to prove to me how it isn't so bad, but keep in mind, loverboy, if it hurts too much, I'll be pissed."
I was slow to anger, Tom had learned, but violently loud and scornful when provoked. He winced at the 'pissed' part.
After dinner, we went to Tom's apartment. He was a senior, and roomed with two other guys, but everybody had their own room, so it was all good. We crashed on his bed after locking the door and flipped on the TV. I didn't care what it was, I just wanted some background noise to cover our inevitable sex and conversations. I'd streaked from the roof of my dorm down to my dorm room the first time I'd had sex with Sara, so I wasn't exactly afraid of nudity or sex any more, but still, I didn't know those other guys, and I didn't want to share my personal life with them.
So, we laid there for a while, and then Tom started kissing me. He was a little more forceful than normal, a little more determined. Maybe it was the whole anal sex thing, or maybe it was the fact that we'd already discussed having sex tonight. He kissed his way down my neck, something else he and Sara have in common, and I let him strip off my shirt and bra when he was ready. He kissed and sucked on my nipples, lying over me, and slowly slid his hand into my panties from under my skirt. If I'd been on a date with Sara, I wouldn't have worn panties at all, but hey.
I pushed him away long enough to strip. He did the same. Once we were naked, I pulled him up to me. His attention on my nipples and his finger on my clit were as arousing as ever, and I could feel that layer of slimy goodness budding between my pussy lips. His cock jutted between us, hard and twitching. He smiled softly when he looked down at me, and then started to reposition. I stopped him, held his face near mine.
"I've got a new condition," I whispered. I reached for his prick, loved the feel of his head in my palm, pre-cum smearing over my fingers, his bush against my thumb.
He waited, a curious glint in his eye.
"You have to lick my pussy, or I won't let you do the other."
He swallowed. Tom loved sex, but he'd never gone down on me. What is it about men? They want their dick in your mouth, but they're not willing to return the favor. I never had that problem with Sara. It really was too bad she was in love with her boyfriend, Jeff. And too bad no state allowed same-sex marriage. Of course, we could get by without the marriage, but it'd be nicer.
"All right," he said, which was a testament to his determination. I'd tried to get him to lick me off nearly every time we've screwed around.
"And one more thing," I added, gently stroking his prick. "Any lubricant you use has to come from my pussy and your tongue. No fingers in my ass until I'm good and wet."
He blinked. "You want me to lick your ass too?"
"If you want to do this right, and get me really wet inside, then you're not only going to have to lick it, you're going to have to put it inside me. If you can stand that, then I can stand your prick in there. Got it? Other wise, I'm ready to go home."
Ouch. He was troubled. I'd raised the stakes three steps. No sex if he failed in my conditions was a clincher, so he finally nodded.
"It'll be worth it, Amber. You'll see. Sally said it was like nothing she'd ever done before. Nothing."
I shrugged. "Let's find out, lover."
With hesitation, Tom crawled down between my legs. I sighed luxuriantly at the drifting of his breath across my pubis. He kissed my soft belly, made a wet trail with his lips down to my pubic region, where I shaved myself bald. His lips sliding down onto the closed furrow of my cunt made me shiver with lust. Then, after all my anticipation, and all the things he'd done right so far, he completely skipped over my clit and pushed his tongue into my pussy. Now, I'll be honest, it felt good, but it in no way made up for the absence of attention to my pulsing, throbbing button. I so badly wanted him to lick up there, but instead, after he had tongue-fucked me for a while, he shifted down to my ass. He lifted my pelvis off the bed with his hands and eased his tongue up against the clenched bud of my anus.
While he dabbed at my hole with the tip of his tongue, tasting me I imagined, he slid two fingers from one hand into my drenched pussy. When they emerged, slimy with my steaming nectar, he trailed them down to my ass, coating me with my own fluids. I squirmed as he eased his index finger into my anus. It hurt at first, but when he realized that, Tom was more gentle. After a few moments, more pussy juice, and more of his saliva, he was gently but quickly fucking the first digit of his finger in and out of me. I'd been pretty close to this stage before. It was wicked and kinky and very dirty.
Tom rolled me over onto my side, curled my legs up in front of me so the position would hold my cheeks open better. He continued to play with my ass, adding more fluids from both of us, and slowly easing his finger farther and father into me. At one point, he had the index finger of one hand in my pussy, and the middle finger in my anus, both buried to the second knuckle. By then, I was starting to get turned on by the whole process. His fingers eased in and out, opening me, the long slide in, a comfortable stop, and then the long slide back out. He brushed my clit with his knuckles and I exploded. White fire cascaded around my sight, while the wrenching flames of an orgasm slammed me back and forth on the bed. I think I actually kicked Tom.
Eventually, it was over. Tom retracted his fingers and I sat up, grinning. My legs were shaky, but I turned over onto my hands and knees and stuck my ass and pussy at him as provocatively as I could.
"All right, you did good, lover. I'm ready."
Tom smiled, wiped his mouth on the back of his arm, and climbed up on the bed behind me. He touched my butt and hips, easing me into a better location on the bed. His cock drifted against one of my buttocks, trailing a thin line of his pre-cum goo. I shivered. What was it going to be like, this anal sex thing everyone's been so love/hate with for so long? If it was like his finger, I could get addicted.
I lowered my upper body down onto my elbows. It was sinfully wicked to put my ass in the air like that, my cheeks spread to reveal my cunt and anus in all their glory. Well, they were glorious to me. I hoped Tom felt the same. I knew Sara did.
True to his word, he was slow. He started by teasing the tip of his prick across the up-turned lips of my genitals. My moisture lubricated him well, and he slipped into my pussy about half way. It was a sharp angle, somewhat uncomfortable, but he didn't push in far, just far enough to get himself good and wet. My flesh spread around him, and I suddenly yearned for full penetration. I shuddered as he pulled out. I thought he was going to put it in my ass right then, and I was ready for him, at least emotionally. But he didn't. He rubbed his wet cock over my asshole. It was odd, feeling his heat there, rubbing along my groove. I moaned.
Eventually he got around to putting his head against the tight ring of my anus. It was frighteningly large, and at once stunningly erotic. Yet, he had loosened me well, and the head slipped into me almost as easily as into my pussy. I stretched around him, felt the helmet-shaped head pass the first, outer ring of my sphincters.
Tom pulled completely out of me, then slid into my pussy again, re-coating his soft, thin skin with my abundant lubricant. He sank in deeper this time, almost to the base of his cock. I loved being filled by him, even though the angle was strange. Had he been fucking me that way, his balls would have rasped against my clit, a slow, soft tease to orgasm. If he didn't cum first, that is. But he wasn't fucking me down there. He pulled back out and pushed into my ass once more, this just as slowly, but deeper, more smoothly. He pushed in far enough for me to feel his curly hair on my ass-cheeks. I willed my ass to relax as much as I could around him as he pulled back out. This time, he stopped at the tip, then slowly eased his way back in. My tightness dried us out about half-way, so he slid back out and soaked in my pussy again before easing his full length back into my anus.
"This feels unbelievably good, baby," Tom whispered, leaning over my back to kiss my shoulder blade. "I'd love to make it last, but I don't have the willpower."
I laughed. "Go slow. I'll take care of the rest."
He began fucking my ass in earnest, then, taking his time, and often mixing in short strokes that didn't caress his sinful length so effectively. I reached down between my thighs, found my clit with two fingers, and pinched it lightly between them. I was used to my body, I knew the ins and outs, so to speak. I knew how to prod my little button just so, driving myself wild even as the wickedly erotic thrusting of Tom's manhood into my ass rounded out the bouquet of lust building in my cervix.
I have to admit, the sensation was somewhat appealing. It was a lot like regular intercourse, in a way, his penis swelling my ass with every thrust the same way it would have in my vagina. I fought the urge to squeeze him with my sphincters; I knew it would mean pain if I squeezed him while he was moving. I fought the urge, willed my anus to relax, willed all my inner muscles to relax.
All that in and out left me panting, squirming, and fighting the natural tendency of my innards to clench. In doing so, I rushed headlong into my second orgasm without even realizing I was close. My finger diddling my clit sent me into a sudden outburst of vivacious moaning as my body once again became a fireworks of flesh.
At that point, I could help it no more. As my rectum spazzed in response to my orgasm, my ass clenched down of its own accord. I cried out in anticipation of the pain, but we were so slick and slippery that all it did was heighten the sensations driving through my ass. Out he went, a long glide against the ring of my hole. Back in he came, a long slow slide gently filling me. I thought I could feel his veins as he thrust into me, the soft ridges on his sides, the flare of his cockhead. My release doubled upon itself, another orgasm ripping through me on the heels of the last.
The tightness in my ass was too much for Tom. He grunted, lowering his head against my back, his own orgasm taking him as he thrust into my squeezing rectum. His first spurts of hot fluid splashed across my insides, making us even more slippery, more sloppy. The second and third shots came quickly after, filling me with his seed. I'd seen porn with Sara about a woman with an ass-full of cum, but it felt nothing at all like I had imagined. It was hot, gooey, and seeped out of me in spite of my momentary decision to hold it in. What would I do with I? Why keep it? And strangely enough, I found the sloshing dribble seeping from my ass all the more erotic.
When he pulled out finally, I wiped his cock off with his sheet, then sucked him to yet another load of semen. In spite of my inclination to gag, I swallowed it, because I knew he liked it. Some women hate that about us, that we'll do the distasteful just to please our mates. I'm really glad Sara wasn't one of those. I knew from before that she had problems sometimes in pleasing me. I tried to make things as easy for her in that department as I could.
After Tom was happily sleeping, I cleaned up in his bathroom and left. When I got to my dorm, Sara was asleep. She rolled over just before I slipped into my bed. She left the light off, but joined me under my sheets. She was naked, and very warm from sleep. I was on my side, so when she curled up against my back, I snuggled against her. Her nipple teased my spine even as one of her hands crept down between my thighs.
"My," she whispered. "Somebody smells like sex. Nasty, dirty, sex."
"Shut up," I giggled, "and put your finger in my ass."
I talked like that to her. Sometimes she did it, sometimes she used the other hole. This time, the hand between my thighs slowly crept around to my butt. Into my crack she went, and when she got there, she gasped.
"It's like a Louisiana swamp down there, girl," she whispered, probing her finger into my anus. "You let Tom do you in the ass, didn't you?"
She laughed. "Well, since we share everything, I want to do it too." I didn't mention that we technically didn't share everything. I'd never touched her boyfriend erotically. Maybe I could get her to change that some day.
I let her roll me onto my back. She lowered her tongue to my pussy from a sitting position, so I reached down and played with her butt-cheek while she sucked the remnants of my earlier orgasms out of me. I came in a quick torrent of fire and head-lolling before she was finished. She got on her knees on the side of the bed, pulled my hips over to her, and parted my cheeks enough to lap at my rectum with her tongue. Man, but that was lovely. She was softer, gentler, and far more skilled than Tom. Hot, soft slipperyness glided across my nether opening. She had me swooning, and I never noticed where she got her strap-on, but then somehow she was wearing it and once again a cock was worming into my anus.
Just like with the tongue, Sara was better. She was slower, smoother, used our lubricants better, and while she fucked me, she played with my pussy, making me squirm until I was cumming all over again on the end of her fake dick. She reached up with one finger, wet with my syrupy juices, and teased one of my nipples with the wetness.
Sara lowered herself down across my body. When her face was only inches from mine, she eased her dildo into my cunt with a practiced thrust. We'd fucked like this many times, over the past month, but this one seemed special to me, even when she didn't really start going. Instead, she just lay there before finally kissing me deeply. Her lips were softer, far softer than Tom's, and smoother. Luscious. I sucked her tongue into my mouth, sucked it and played with it with my tongue even as I lifted my legs and wrapped them around her back. This had the wonderful effect of turning my pussy up to her fake cock, letting her deeper into me, deep enough to brush my cervix. I loved her so deep inside me, loved it in ways I'd never shared with Tom.
I loved just as much the way her hanging nipples quivered as she trembled. I could feel them because they were brushing against my own. She was chuckling silently.
"Oh, no," she laughed. "No sleeping. Not this time. You have to do me now. In the ass." Her eyes were bright, excited, in the weak light from the window.
She was up in a flash. I heard her un-strapping her cock, which she handed to me. I grinned, took the rubbery prick and slurped my own fluids off of it. I could still taste Tom on there. I then reversed it. This was one of those kinky toys that penetrated both women, so I sucked Sara's cream off her end before I slid it into my pussy and tightened the straps. It fit mostly like a regular strap-on, but with amazing stimulation to my clit. Some days, I like Sara and this toy way better than any man. Certainly better than poor Tom. Yes, I'm a fickle slut.
I turned the light on, because I dearly wanted to see everything. Sara was on her knees on my bed, so I slid up behind her. We were close enough to the same height that I could approach her on my knees and still line the rubber dick up with her ass. She parted her legs and let me get between them, and then just as I had done with Tom, she lowered her chest to the bed and flaunted her anus and pussy at me. She shaved both holes quite close, though how she didn't get razor-burn on her ass I'll never know. It was a secret she never shared, but I had never been that interested in finding out. I'd touched her there a few times. How could you not, as often as we screwed around, but it had never been my interest. Now, though, I had to see what it was all about, had to know everything.
Sara's anus was mostly dry as I brushed my fingers down over her buttock, into her crack, and then up against her sweet, chocolate hole. Her skin was hot, though, with just a bit of sweat. I thought back to what Tom might have been going through, so I figured I could do no less. I slid my finger into her pussy, then brought it and a healthy smear of her fluids up to her perfect little anus. I pushed my finger in against her sphincters, expecting resistance. There was hardly any at all. All those months and maybe years of practice with her boyfriend, I supposed. My finger squeezed into her. Her hole was different than a pussy, smoother, tighter. A lot tighter.
"Ooooh, that's nice," Sara whispered. "I'm glad Tom got you into this."
I found resistance around the second knuckle, so I withdrew, and gathered more moisture from her pussy. Then I remembered what I had made Tom do. Fair was fair, I thought, so I backed away enough to lean down. I had smelled Sara's ass before. You can't eat a girl's pussy as much as I had and not sometimes end up with your nose in her rear. She was clean and shaven, but without razor-burn. Her pucker was smooth against my lips as I tentatively tasted her hole. She was sharp, there, bitter, a taste I can't relate to anything else, a taste I savored as unique to her, and unique to this latest depravity.