Anal initiation

“What did he say?” Anna fixed her eyes on her old friend, in that way that had always made her spill whatever secret she was trying to keep.

“He said... he wanted... anal...” muttered Taylor, trailing off at the end and blushing scarlet.

“So what did you say?”

“No, obviously. Then he said I was a prude, and a daddy’s girl, and... ohhh. I don’t want to talk about it any more.”

Anna was stroking Taylor’s shoulders, and found her hands tensing up, almost squeezing too hard. She breathed deep to keep her body in check. That little bastard, trying to pressure her into something she didn’t want to do.

“OK, the problem here is that you made your boundaries clear, and he walked up and pissed on them. Tay, that’s not...”

“But then I got thinking. And part of the reason I was attracted to him was to shed the part of me that... doesn’t want to. I do want to. Well, it’s more the idea of doing something taboo.” Taylor was sitting cross legged on the bed, gazing away from Anna out of the window. Though she was avoiding eye contact, Anna could sense her determination.

“But it’s for the wrong reasons. Look...”

“So I was thinking. Maybe you could show me.”

“...”

Unusually, Anna found herself speechless. Her friend was propositioning her for sex? After all these years? She had to say no, obviously. Taylor was feeling vulnerable, it would be unthinkable to take advantage of her.

But Taylor always looked before she leaped. Even when she was leaping into something a little wild...

“Are you sure, Tay?”

“Well, I think so.”

“Well, if I’m doing anything you don’t like, speak up, ok?”

Anna had been in similar situations with apparently straight girls before, and she usually had no difficulty with helping a girl explore, especially cute redheads with freckles and white underwear. But they were usually both quite drunk, and they usually weren’t childhood friends. Anna felt uncharacteristically shy and unsure how to proceed.

“Here. Maybe a glass of wine will help,” Taylor said, and pulled a bottle of cheap white from her handbag. Anna smirked at her: it was the brand they had selected as having the best alcohol:taste:price ratio. The study had been a culmination of working together to their strengths: Anna with her dedication to drunken mayhem, Taylor with her love of gathering data and applying appropriate statistical techniques.

“I don’t have any glasses.”

“We can drink out the bottle. Or we can pour it on each other and lick it off. Isn’t that what lesbians do?”

“Sometimes...” Anna muttered, flushing at the idea of wine flowing over Taylor’s lovely breasts.

Taylor leaned back on Anna’s lap. It was a position they often assumed when watching TV. Anna gave herself a little internal shake. “Get a grip of yourself.” Taylor was extremely hot, and one of her personal tenets was not to turn down a hot person because of stupid things like common sense and trepidation. It didn't work, she was still terrified. She and her friend had practised kissing together, a long time ago. And they had always had open discussions about masturbation and sex (Anna knew when Taylor was going to lose her virginity before the gentleman in question did). But stripping her naked and making love to her beautiful body, and introducing her to the world of anal pleasure... it was a different proposition to say the least.

Her thoughts slowly unsnarled themselves, and relaxed like ripples gradually disappearing on a placid lake. Taylor had started to massage her shoulders and neck. That girl sure knew how to use her hands... she would make a good lesbian. Anna allowed Taylor to smooth out the knots in her upper back, then lay on her front, asking her to massage the rest silently. Taylor straddled her ("!" thought Anna) and began to work on her lumbar region. Anna had terrible posture, so the attention to her tortured lower back released moans of relief and gratitude. Taylor went on massaging until she could detect no more tension in her friend, and noticed that her breathing had become slower and deeper.

The wine and massage had done their work. Taylor rolled Anna over, revealing the smirk she recognised as the sign that she was on the rampage. Anna placed her hands on Anna's waist, returning the lower back massage. She gazed up at Taylor's body, all creamy skin and freckles in her smart, conservative blouse. It felt completely natural to sit up, and kiss her. Taylor kissed back joyfully, grabbing her friend's back and squeezing a little. They kissed for a little eternity, stroking each other all over, exploring, running hands through each other's hair.

Taylor stood up for a second and removed her blouse. Slowly. Anna gazed, hypnotised by each button popping open. When her soft, beautiful breasts were revealed, Anna moaned a little. Taylor smiled, turned her back and leaned over, pulling away her trousers as she did so. Her bum loomed into view, covered with cute little boyshorts. The sight of her arse flaring out just so from her hips, and the way her shy friend was taking charge of the situation, drove Anna wild. She undid the clasp of her bra, and ran her tongue down her spine. Taylor gasped in surprise at this action. It seemed so... wanton, like Anna was hungry for her and couldn't wait to taste her. Her bra slid off, and Taylor turned round, allowing Anna to take one pale, sensitive nipple into her mouth, rolling the other between her fingertips. Taylor moaned so loud that she felt briefly paranoid the neighbours would hear. But she was soon beyond caring, as Anna sucked as much of her breast into her mouth as she could, tracing her other hand down, tracing the roundness of her belly, before touching her, gossamer soft, on her pussy.

Taylor sat back down on the bed, her parted legs showing how rapidly she was dampening in response to her friend's attentions.

"Your turn to get naked."

Anna obligingly pulled her top up-- she wore no bra, so Taylor was immediately delighted by the sight of her tanned tits, her areolae plum with paler pink points. She gave one a lick, and was rewarded by a moan. Anna removed her skirt, and then her underwear. Taylor was inexperienced with girls, so was rather shocked at the intense craving she felt when Anna exposed her cunt. She wanted to taste her, fondle her, feel her spasm around her fingers. She had almost entirely forgotten she was here for a gentle introduction to anal. She was sure they would get around to it, but not before she had touched and licked and stroked every inch of this luscious creature’s body.

Anna took control again, kissing her friend deeply, relishing the feeling of their tits against each other. She pulled Taylor’s underwear down her legs, revealing her entirely. Taylor spread her legs instinctively, but Anna didn't immediately dive to taste her (as she would have done, she admitted to herself). Instead she gazed at her lying spread and innocent on her bed. Taylor felt suddenly very exposed and vulnerable.

"You're so beautiful. I can't believe you're naked in my bed."

"I know I said I wanted anal instructions, but..."

"... that's not all? Don't worry, I intend to give your bum the time of its life. But I'll be giving that to the rest of you too, babe."

Taylor purred as Anna turned her attentions back to her tits, sucking each nipple alternately for a few seconds. Her hand stole back down to her crux, sliding between her lips, feeling the wetness of her cunt and scooping the wetness back to her noticeably swollen clit. She rubbed at it in slow, teasing circles. The combination was delicious. Taylor allowed her mind to empty. The fingers of Anna's other hand reached into Taylor's cunt, crooked, and stroked at her G spot. The feeling of the other woman's hands and mouth as well as the excitement brought Taylor to the edge. At first she couldn't breathe, such was the intensity, but then she started gasping and bucking, letting Anna know her appreciation by coming around her fingers. When she opened her eyes, Anna was grinning at her.

"So you liked that, huh?"

"Y... yes"

"That just the hors d'oeuvre. No, that was just the bread they bring round beforehand."

Taylor smiled wide.

"You didn't touch me there. And I didn't get to taste you."

"You want to... go down on me? Wow, that's some advanced lesbianism. I thought you just wanted your anal cherry popped in a secure environment?"

"Aw, Anna. I don't know. I just know what I want to do."

"Well, like I said, we've only barely begun. Haven't you got a nine o'clock lecture tomorrow morning?"

"I'll be very disappointed if I'm in any condition to make it."

Anna chuckled.

"OK. So you want to go down on me. May I suggest ze soixant neuf? Ze soixant neuf, weeth a tweest!"

"Enough of the stupid accent, you fanny."

The banter was interspersed with Anna positioning them into the classic position, with Taylor on top. Taylor squeaked in joy at the sight of her friend's treasure. It was slick with wetness, though it hadn't yet been touched. The hair was closely trimmed, and she had a sharp, barely musky scent. Taylor leaned in to taste her first woman.

Anna let out a silent scream as her friend tongued her, experimentally, curiously, but more and more greedily. Taylor’s wet cunt and nether hole, suspended temptingly above Anna’s lips, twitched in arousal at the taste and feel of her. Anna slid a finger in her cunt to better feel her contractions before withdrawing and circling that finger around her arse.

“Oh, that feels weird. Not in a bad way, just different...” said Taylor, her words rather muffled and indistinct.

Anna said nothing-- she had far better things to do with her tongue. She ran it up and down Taylor’s slit, tasting the moisture that came from the orgasm she had given her, and her excitement at tasting her best friend and then slid her tongue higher, until its tip was teasing around Taylor’s hole.

Anna noticed the sensations on her clit dissipating, as Taylor concentrated on these new sensations. Anna went on tenderly licking around the rim, hearing Taylor’s little gasps of disbelief and amazement. Then, tired of messing around, she ran her tongue into her arsehole as deep as it would go. Anna felt the muscles of the shocked woman spasm around her, but she started fucking her slow and deep with her tongue. Taylor started moaning, easily loud enough to be heard through the thin walls, but to hell with her flatmates. Anna started stroking Taylor’s clit again, the way that had been tried and tested last time, and with her remaining hand reached down and grabbed a niipple, roughly pinching and squeezing until Taylor moaned out her second, even larger orgasm. Anna kept her hand gently moving on her friend’s pussy until the contractions of her orgasm subsided.

“Fucking... fuck.” said Taylor. Considering she barely said “damn”, Anna thought that indicated that she had enjoyed her experience, together with her collapsing on top of her. The buxom girl was squashing her rather, but she wouldn’t complain for anything.

“So you liked that then?”

“Kiss me,” replied Taylor. “She’s insatiable” thought Anna, not unhappy. She kissed her friend with abandon, their tongues sliding over one another and their teeth clashing, as they shared and enjoyed each other’s flavours. The kiss became gradually more tender, until they came to, lying in bed, gently stroking each other’s hair.

“You didn’t come.”

“I barely care, that was in-fucking-credible.”

“But I want you to come, my love...” Anna’s heart almost stumbled at the words, my love. My love, my love, echoed in her ear. How could she say no to such an angel?. Anna turned round so that Taylor was spooning her, and guided her hand to her cunt, still wet from their travails. Taylor began to rub her clit, using a fast but light motion that took Anna’s breath away. She reached the edge unusually quickly, spasming at Taylor’s touch, before falling back into her arms. The feeling of her full tits on her back and her arms around her, was bliss. All her worries seemed somehow far away and inconsequential.

“I could never move again,” said Anna.

“We don’t have to, till morning,” replied Taylor, kissing her nape.

The art of fellatio.

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Seducing my boss's wife.

The highlight of my rather dull working day is when my boss, Simon, comes in, his cycling jersey and shorts giving an unparalleled view of his firm chest and legs. Nudging fifty but appearing at least ten years younger, he is the very definition of a DILF. He's also a good boss: he never behaves discourteously and treats everyone with equal respect. He nodded as he passed my desk. Mmm. I didn't know whether the view of him coming or going was better. I sighed and got back to my spreadsheet.

His wife, Claudette, was no less hot. She was tall and statuesque, with a narrow waist flaring out to wide hips in the back and an impressive bosom in front. She had olive skin, highlighted dark brown hair, and gleaming green eyes. On the occasions she came into the office, she gives me a crinkly, cheeky little smile that melts my insides and leaves me feeling gooey. Given the choice, I couldn't decide which one I wanted to fuck more.

I would never have imagined that I wouldn't have to choose.

That night, our regular office pub quiz night, the boss and I were sitting together, three sheets to the wind. I mustered my Dutch courage and murmured.

"You're lucky, going home to a beautiful woman tonight."

"Yep, you don't have to tell me. I don't know how I ended up so lucky, but here I am." He gave a big, goofy grin. I resisted telling him the reason he had such a hot wife was because he was incandescently gorgeous himself.

I sipped my beer and steeled myself.

"Is she the sort of woman who likes fooling around with girls? Because I'd be totally up for that." I pitched my voice to make it sound like joking banter, but hope glimmered deep in my heart. He raised his thick, perfect brows nearly to the ceiling, and then said:

"Not since college, as far as I know. I keep telling her I'll bring her home a girl to play with, but I never get round to it."

"You can't keep promising her something and never follow through on it."

"True. Well... we'll see. Maybe we won't feel the same after the beers have worn off."

I smiled and nodded, but I knew that I had a tiny finger hold in his mind. And hopefully, if the stars aligned, I would get to play with his gorgeous woman and watch him take her like a true alpha male.

The alignment happened rather sooner than I had expected. They were having a party, ostensibly to celebrate opening that year's batch of home made mead, and everybody from our small office was invited. (The kids were at Granny’s). I dressed down, putting on denim shorts over black tights, a band t shirt over my braless small tits, and throwing a plaid shirt over the top. I glanced in the mirror. I looked boyish but cute, and my pierced nipples were tantalisingly visible through my shirt. I would do.

The party was pretty quiet, and since it was a work night, people didn't stay late. I tarried, on the pretence of helping to clean up. Claudette tried to stop me, but I was a glass collecting, hoovering machine. I told her to put her feet up and relax. Simon was on the sofa, enjoying a last glass of mead, and pulled her brown skinned, red nailed feet into his lap. She gave a little moan as he expertly manipulated them. I stopped for a moment to watch. I've always had a thing for men's hands, especially large, capable looking ones like Simon's. I took another breath and sat beside her on the couch, put my fingertips on her full hips, and rolled my thumbs around either side of her spinal column. She was so relaxed from her husband's attention to her feet, she barely acknowledged my stroking of her beautiful body. We continued to rub her body, him including her calves in his travails, me running my hands all over her back and onto her neck, which I guessed was super sensitive judging my the little squeaks she made.

"So honey, what do you think of the girl I've brought you?"

She looked behind her shoulder, and gave me that wicked smile.

"I like her very much." Then, oh God, her lips were on mine. I felt my cunt tightening at the feeling of her mouth gently exploring mine, and suddenly realised how wet I was. My eyes flickered open, letting me see Simon quietly watching, not disturbing us. I wrapped my arms around her, still behind her, and started gently kissing and nipping her neck. I was desperate to take one of her wonderful tits in each hand, but made myself be patient. Sex is never the better for being hurried. I enjoyed the delicate taste of her skin and the gentle quickening of her breath, and noticed the outlines of her nipples becoming more distinct behind her soft silk blouse. I ran my fingers around the full buds.

She turned round and renewed her attention on my lips. I loved her passion, and couldn't resist stroking her tits with my hands, before clumsily unbuttoning her top. She wore an expensive looking black lace bra, which was front fastening. She unsnapped it, and then her gorgeous, full, golden skinned tits were bare in front of me. For some reason, the way that they had obviously been used to feed an infant, their fat nipples and slight droopiness, made me even more horny. She was a fully grown woman. I felt like a rosebud next to a full blown bloom, or a fleshy, fertile rose hip. I wanted to explore every inch of her. I glanced over again at my boss, who was still watching us intently. I rather liked the aspect of putting on a show for him (I admit, I'm something of an exhibitionist). I squealed excitedly as her warm, soft hands travelled up my shirt, discovering my nipples and tugging on the rings. I have sensitive tits, even for a girl, so this attention made me lose any sense of reason, grabbing her hips to me and dry humping her like a horny teenager.

"Let's go to the bedroom," said Simon, taking us both by the hand. I was gratified to see his cock nearly bursting out of his trousers as we walked through. Claudette stripped off the rest of her clothes when we entered the room, removing her open blouse and bra, then her skirt, stockings, and finally black lace knickers which matched the bra. Her pussy was covered in lush dark hair. I removed my t shirt, feeling wonderfully exposed. Claudette's eyes gleamed at the sight of my perky tits and pierced nipples.

"Didn't it hurt?"

"Yes, but... ooooh... I like... a little pain..." I stuttered. Simon was behind me, his cock pushing painfully into my back, his large hands covering my tits before pulling on the rings. The sight of his hands on my body was delicious. I removed my nether garments so that I was as naked as she, and Simon wasted no time stripping down either. He looked amazing out of his clothes, with his firm, densely hairy chest and toned legs. His cock, as thick as my wrist, had a saucy upward tilt which promised to tantalise my G spot. I planned to focus on Claudette tonight, but if possible I wanted to ride that cock too.

Claudette lay on the bed, beckoning us over. She clasped me in her arms, and I felt enveloped by her soft skin, with her full tits pressing into me deliciously. Simon came and lay behind me so that I was sandwiched between them. I adored the contrast between her softness and his rough, hard body. Simon leaned over me, resting his cheek on mine to kiss his wife. We stayed in this embrace, Simon’s cock gently pulsing against my bum, Claudette occasionally brushing my lips with hers in between kissing her husband. She started tugging on my rings again, smiling at the gasps I produced in response. Simon moaned too as my hips started bucking against him, creating friction against his cock. I imagined I could feel the dampness of his precum on the small of my back. I longed to take him in my mouth, but took my cues from the couple who had invited me to their bedroom. For now, Claudette seemed to be enjoying teasing me, and Simon by proxy. I felt fingers, I don’t know whose, dipping into my dripping, horny cunt and swirling around my clit, bringing me to a shuddering orgasm in their arms. I collapsed, suddenly realising I was covered in their, our sweat and my wetness had travelled down almost as far as my knees.

I have a long standing fantasy of eating a girl out while she’s being fucked. I outlined this dream to Simon and Claudette, and Claudette responded by getting onto all fours and wiggling her bum at us seductively (and what a bum it was). Simon (whose fingers it had been, evidently) held his fingers to Claudette’s lips, allowing her to lick my juices off with her sharp pink tongue. The sight made me horny all over again. I  scooted underneath her, so that her hot, wet cunt was right over my face. I couldn’t resist licking her from her puckered hole to her clit, eliciting an approving moan. I could see Simon’s lovely thick cock lining up with her opening, delving into it as he must have done thousands of times before. I began licking Claudette, focussing on her clit but licking all over her glorious pussy. I couldn’t resist licking the base of Simon’s cock and his balls as he pushed in and out of her. I could hear them kissing as they fucked. I fingered my clit as I licked, on course to cumming in my boss’s face.

It took far too little my oral attentions on her clit before she started spasming, crying out as she clenched around Simon’s cock. Simon thrusted even harder, I switched my attentions to swirling my tongue around his balls, which had pulled up tight into his body. He grunted as his cum flowed into his wife. Their salty combined juices tasted so good. The perversion of the situation, together with more unidentified fingers in my cunt and an exploratory fingertip on my arse made me orgasm yet again, squirting a little this time.

Claudette lay back, smiling that smile of hers. “That felt goooood... so, did you like licking my husband’s balls?”

“Very much, ma’am.” I had no idea where that ma’am had come from, but it felt right. I laid my head on her breasts, and she wrapped her arms round me. I felt like I was in a warm cocoon, completely safe and content.

“You can have the morning off tomorrow,” said Simon. He caught my eye and smirked. I suspected he’d be taking the morning off too.