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.