First Anal

Nervously, Jan replayed the conversation in her head. Had she said too much? Had she somehow given him an unwanted advantage? He had a knack for getting her to admit more than she wanted to, and the way he seemed to file away information in his head made her nervous. Then again, what did she know? When your boyfriend is an older guy -- already finished college! -- you sometimes have to trust that he knows what he's doing.

Well... technically, he never used the word "boyfriend," but they'd been on a few dates and she'd had sex with him on every one, so she knew they had something special, regardless of what he wanted to call it.

The conversation had started out so innocently, and before she knew it they'd been talking about fantasies. And then he somehow got her to admit she'd always wanted to make out with a girl. And not just any girl, he'd managed to get her to admit she had a specific crush on Amber! Amber was Brian's age, and Jan's opposite in so many ways: cropped blonde hair in opposition to Jan's long, brunette do; so confident and outgoing where Jan was shy; tattooed and pierced, while Jan would never consider doing that to herself. It was no wonder Jan wondered what it would be like to kiss Amber; to run her fingers through that short hair.

She already knew Brian's fantasy, he did't have to tell her anything, because he'd never made any secret of it: he wanted to do her in the butt. Gross! She blushed at the thought of it. What kind of girls let guys do them in the butt? (Maybe Amber? Jan quickly pushed the thought out of her head.)

Jan already regretted spilling her secret to Brian. He and Amber were acquaintances, and now she was afraid he might tell. She would be so embarrassed if Amber found out!

He called her that night and suggested they meet at their usual hotel. He said he had a surprise for her. She hated to admit it, but it gave her a secret thrill to be meeting her boyfriend -- or... whatever -- at a hotel. While her other college friends were hooking up in their dorms, trying not to make too much noise or get caught, she was going to a nice hotel, where they could make as much noise as they wanted. Not that she made much noise, she couldn't really bring herself to be loud in bed. But he was so good at cumming at the same time she did, and it always brought a whimper from her.

(Good thing he'd had that vasectomy, so he didn't need to use a condom! He'd been sure to tell her that the first time they had sex. It was especially lucky since he was allergic to latex.)

She put on his favourite black dress and checked herself in the mirror before stepping out the door. Much too short and tight for her liking, it left nothing to the imagination. At least she was lucky to have nice skin, since so much of it was showing at the back! But he liked the dress, and she wanted to please him. She slipped on her high heels and was out the door. It wasn't usual for them to go straight to the hotel, he usually treated her to dinner or a show or something, but she knew this must have something to do with the surprise.

He opened the door with a grin. He took her in his arms and kissed her, and she could feel that he was already hard. She blushed but kissed him back, exploring his tongue with her own. Sex wasn't a big deal with older men, she reasoned, so if he wasn't embarrassed to have an erection she shouldn't be embarrassed either. Soon it would be inside her anyway! She blushed even harder; she was feeling so naughty tonight!

"Come in," he said, shutting the door behind her. "Your surprise is waiting." He led her to the bed and had her lie down. "Close your eyes," he commanded, and she complied immediately. She didn't want to ruin the surprise by peeking, though she was confused when she heard the bathroom door open. What did he need from the bathroom?

As she lay there, eyes closed, wondering what was coming next, he bent over to kiss her, but his kiss was different. Softer, somehow. And she didn't feel his stubble.

As the realization hit her, her eyes flew open and she found herself staring into Amber's baby blue eyes. Amber was smiling when the kiss ended, and reached up to run her fingers through Jan's hair. "Hey baby," she said softly, "I'm your surprise. Want to have some fun?" And before Jan could answer, Amber closed her eyes and kissed her again.

Too surprised to do anything other than kiss Amber back, Jan felt so confused. So warm, and she had to admit that not all of the warmth came from her blush. Amber's kiss was so tender, and her breath was sweet. Her eyes were beautiful.

Amber eventually stopped kissing Jan, and leaned back to show off her flimsy nightie, with nothing underneath. Jan tried not to stare. She'd fantasized about being with Amber, but even in her fantasies she hadn't realized what a sexy body Amber had.

She'd completely forgotten about Brian, and jumped slightly when she heard his voice from behind, right in her ear. "Amber's your surprise," he whispered, lips brushing her earlobe, sending a shiver down her spine, "But you have to do it our way." Jan wasn't sure what "their way" was going to be -- and when had they worked this all out, anyway? -- but the sight of Amber, right there in front of her, so beautiful, so sexy, was working on her. She'd do what they wanted, for now.

Brian didn't need her to answer, he could see by her face that she was along for the ride. He stood before her and reached out his hand. She took it and he helped her up; she almost lost her balance, so dizzy from Amber's kiss. He stood behind her, and over her shoulder he asked Amber, "Want to see what you're in for?"

"Oh yes I do," Amber responded. She sat in the chair by the bed, crossed her slender legs, and waited for Brian to unwrap Jan for her.

Jan was standing right in front of Amber, Brian behind her, so when he reached down and pulled the dress up over her head, Amber had a perfect view of Jan's trim body. In an instant she saw Jan's perfect breasts -- Jan didn't like to wear a bra in that skimpy dress, though the lack of one made her feel a bit... dirty -- and her black, v-cut panties. Jan instinctively wrapped an arm over her breasts, but not before Amber noticed how erect Jan's nipples were. Jan was also blushing, and blushed even deeper when Amber said, "My god, Brian, she's incredible!"

Jan wasn't sure she liked being judged like a... like a stripper, but the compliment from Amber definitely made her feel good. The rush of blood she felt extended all the way to her nether regions.

"Your turn, Amber," Brian said, at which point Amber got up from the chair and discarded her nightie. Her nipples were also erect, and Jan allowed herself a moment to picture what it might be like to take one into her mouth.

Amber came back up to Jan, placed her hands on Jan's waist, and kissed her again before letting her lips trail across Jan's cheek to her ear, where she whispered, "Now the fun begins, Sugar." She moved past Jan, letting her hand trail across her tummy, heading toward the bed. On her way she gave Jan a playful slap on the ass.

She lay down on the bed. "Come and get it, Sweetie," she said, and with a very slight prompt (via Brian's hand on her back), Jan started to head toward the bed. As she got to the edge Brian halted her long enough to slide her panties down her legs.

"You won't need these," he said.

By this point her embarrassment at being naked in front of Amber was almost completely worn off. She just wanted to kiss some more, and the sight of Amber's breasts, pointing at the ceiling, was intoxicating. She lay down on the bed, beside Amber, and tentatively leaned over to kiss her again.

God, it felt so good! So natural, so tender, but so... dangerous. So different. She reached up with her hand and made a second part of her fantasy come true by running her fingers through Amber's hair.

"Mmm," moaned Amber, "I like that." She turned on her side, so that the two girls were facing each other, and reached out a hand to stroke Jan's back, cup her ass, explore her muscled leg. She moved a bit closer and Jan felt their breasts touch, almost perfectly nipple-to-nipple. She instinctively moaned; another woman's naked breasts were touching hers! She was really having a girl-on-girl encounter!

But Amber wanted to take it even further. She rolled back on her back, taking Jan with her, so that Jan's naked body was on top of hers. Now their breasts were fully pressed against each other, and Jan almost gasped out loud when she felt Amber's clit against her own. Amber wrapped a leg around Jan's, resting her foot on Jan's calf, and reached up a hand to wrap it in Jan's hair, wrestling Jan's tongue with her own.

Jan was now lost in the world of Amber's body, pinned under her own. Her daring increased, and she reached up with her hand toward Amber's breast... but before it could get there Brian took it, and pulled it near the bedpost, where he shackled it into a fuzzy handcuff, which had obviously already been there, though she hadn't noticed it. For the first time in the evening she felt frustrated; she hated it when Brian wanted to tie her up, but more importantly she'd wanted to touch Amber's breast and see what it felt like! Would it be like hers? More firm, or more... jiggly? Dammit, if she was going to explore another girl, she wanted to do it right!

She didn't have time to give it much thought, however, because Amber slid down under her, a bit, to take Jan's breast into her mouth. A spark of pure electricity lit up Jan's pussy as she felt Amber suck her breast into her mouth. Her clit was now against Amber's tummy, and she closed her eye as the feelings overwhelmed her. Almost subconsciously she started to grind her clit into Amber, while Amber sucked and occasionally nibbled her nipple, and grasped Jan's ass in her hand to help with the grinding. She was far past caring when she felt Brian encasing her free hand in another handcuff, on the other bed post. She cared about nothing but her clit and her nipple, as Amber expertly steered her toward orgasm.

"Oh my... oh... oh my GOD!" she screamed, when her orgasm finally hit her. She could feel her whole body shaking; it was so good. She started to come down then remembered that she was with another girl, which sent another convulsion through her body.

She still didn't care when she felt Brian pulling out her legs and slapping cuffs on them. She was now perfectly spread-eagled on top of Amber, panting, trying to catch her breath. Amber got back up face-to-face with her, taking Jan's face in both of her hands to rain gentle kisses all over her face. "That's right, baby, it feels so good doesn't it? You feel so good, your skin next to mine," she whispered into Jan's ear, and kept whispering similar sweet nothings as Jan came down from her orgasms.

As Jan started to get her faculties back, she decided that she didn't like being tied up spread-eagled like this. It was one thing when Brian wanted to cuff her hands -- though she didn't even like that -- but to be so completely helpless made her uncomfortable. She opened her mouth to ask him to take the cuffs off, but before she could Amber kissed her again, passionately, and she felt a finger slithering along her wet pussy. Barely recovered from her climaxes, it was easy for Amber to wriggle a finger inside.

God! Amber knew what she was doing! Brian had never touched her like this! Her pussy, already excited from her orgasm, responded immediately to Amber's touch. With her arms and legs bound she couldn't move against Amber like she wanted to, all she could do was enjoy the sensation. Amber's free hand grabbed Jan's ass, and held her in place while she worked the pussy. To Jan's surprise she was already quickly starting to build toward another climax, when she felt that Amber was no longer just holding her ass. She was... spreading the cheeks apart?

Then she felt Brian on top of her, and realized that he was positioning his cock at her asshole. She was immediately out of the moment.

"No!" she shouted, and would have bolted straight up if she hadn't been tied down. Her eyes were as big as saucers. "Not funny, Brian! Get it away from there!" She clenched her asshole as tightly as she could, though even if she hadn't it would have done so instinctively on its own.

"Shhhh..." she could hear Brian in one ear and Amber in the other, both gently reassuring her. "You've already got your surprise," Amber whispered, "now he's getting his." His cock was still pressed against her asshole, not trying to push in, just pressed firmly against the entry. (Or rather, exit!) He wasn't attempting to enter her, just leaving his cock there, as he "shhhh"ed into her ear, and nibbled her earlobe from behind.

Amber was still whispering into the other ear. "Don't worry, baby, I'm right here, and it's going to feel so good, you're going to feel so full, and I'm right here and we can cum together..." As Amber whispered these sweet nothings into Jan's ear she continued to finger her pussy, and Brian continued to nibble her other ear... all the while keeping his cock firmly, but gently, against her clenched asshole.

Despite her distraction, Amber's ministrations against her pussy, not to mention the feeling of being sandwiched between two naked bodies and Amber's tender kisses, were having an effect, and she started to feel an orgasm building. "Don't do it Brian," she said, softer, giving way to the feelings in her pussy in spite her intentions. "It's not funny! I don't want it in my ass, you can't do... you can't do... that... god..."

As her orgasm hit her head fell forward, nestled in Amber's neck, while Amber continued whispering in her ear and occasionally kissing her neck. But Brian's cock was still there, against her asshole. As her orgasm hit and she started to convulse and shudder, he pressed a bit more firmly, waiting for his chance. The moment came, and as her body rode through the orgasm he felt a momentary relaxation in her ass's clenching. He pushed forward, not quite able to get it in; a moment later he felt it again and pushed, and this time the head pushed inside her.

"OW!! Oh God! Oh fuck, take it out!" Jan screamed, orgasm forgotten. The pain was incredible, and her ass felt stretched beyond capacity. Tears sprang from her eyes at the invasion.

Brian didn't attempt to push any further, just left the head of his cock implanted in Jan's ass, while she cried and begged him to pull it out. Amber continued to "shhh" Jan, as she kissed the tears away from Jan's face. This painful invasion brought her orgasm up short, and yet she was still riding through it when he pushed into her; the pain and the pleasure were messing with her mind.

In a few moments Brian reached up and cupped one of Jan's breasts in his hand, and pushed to slide a little further into her ass. He felt Jan gasp at the further intrusion, though it worked against her because the jump when she gasped actually pushed her ass even further onto his cock.

Amber reached up to stroke Jan's hair, Brian continued to cup her breast and take her nipple between his fingers, and then he pushed a little further. Jan felt more full of cock than she'd ever felt before, and was surprised every time Brian pushed deeper; every time she thought she'd taken all she could take, he would push a bit more cock into her stretched ass. She was relieved to realize, however, that the head of his cock had been the most difficult part; once that was inside, getting more and more of the length of him inside her wasn't so bad.

Almost on cue, Amber began to kiss Jan again, passionately this time, and Brian began to gently rock his cock in and out her her ass. He was fucking her; she was truly getting fucked in the ass! Amber began to work Jan's pussy again, and added her thumb to Jan's clit. Occasionally a tear would roll off of Jan's cheek onto Amber's, but they gradually subsided as she got used to the cock in her ass.

Jan didn't know what to feel; she was on sensory overload. Amber's kisses felt so nice; Brian's hand on her breast was wonderful, and Amber's fingers in her pussy were amazing. Her ass felt like it had a red-hot poker in it, but... the pain was starting to go away. And she had to admit, it was incredible to feel so full.

Eventually, the sensations were too much for her, and she knew she was going to cum again. She'd never cum so hard, or so often, in one night! "Oh... Ohhhh... Mmm... Oh, Oh, OhOh... Oh Amber! SHIT" As her orgasm hit her, with the jumble of mixed emotions, the pleasure of her orgasm and feeling Amber's body with the violation of being fucked in the ass against her will, in Jan's confusion she felt it was Amber's cock in her ass.

Amber waited for Jan to come down, and then she whispered into her ear, "Now it's my turn, baby." Jan didn't know what she meant, and when Amber wriggled out from under her Jan felt cold; the loss of Amber's body heat confused her orgasm-addled body. Brian was still gently fucking her ass.

She realized what Amber had meant when Amber's pussy presented itself in front of her face. Jan hadn't expected this! Her fantasies had included kissing, naked skin against naked skin, maybe touching of breasts, but not... putting her mouth on Jan's... youknowwhat. Jan had never actually seen one in person, not even her own, and she found that it looked very different than she'd expected, based on how hers felt.

Amber wasn't going to wait around forever, though. "Come on, Sweetie," she said, "time to earn your keep." She reached down and brought Jan's face closer to her pussy, and Jan could smell Amber's juices. It didn't smell like she expected either; wasn't it supposed to be like honey?

Tentatively, she stuck her tongue out and licked around Amber's lips. She heard Amber's gentle moan, and was spurred on to continue doing so. She tried to put herself in Amber's place; tried to remember what she liked. As she got more bold with her tongue she could taste more, and realized that the taste was different from the smell. She flicked her tongue right inside Amber's pussy, licked up the inside of the lips, and then noticed the little nub at the top of Amber's pussy. That must be it: the clit. Again, it looked so different from what she'd expected!

She circled slowly, working her way up to it. She didn't like it when guys rushed things too much; she thought Amber might be the same. Amber's moans told her that she was probably on the right track.

"Oh, you bitch!" she heard Amber say. "You're teasing me, aren't you! You were born to do this!" To her surprise, she was glad to be called Amber's bitch, and she circled in ever closer... until Amber couldn't take it anymore, grabbed Jan's head, and pulled her right into the pussy. She took the hint, and started to work the clit madly with her tongue; her chin started to get covered in Amber's juices.

She had her face buried in a girl's pussy, and had pussy juice running down her chin. She had a cock in her ass, and it was almost starting to feel good. Well... it wasn't hurting as much, anyway. She'd never felt like such a slut. Without even thinking she actually started to rock her ass back and forth, fucking Brian back. He and Amber noticed, however, and exchanged a look, before Amber went back to concentrating on her clit, and moving Jan's head where she wanted it moved.

Soon Amber was getting ready for her own orgasm. She held Jan's head still and fucked Jan's face with her slick pussy.

Brian, of course, could see Amber's face, and began to fuck Jan's ass harder to time his orgasm with Amber's. As he felt (and heard) Amber cumming he came as well, groaning as he filled Jan's ass with his seed. Jan couldn't feel it the same as when he came in her pussy, but she could feel his cock throbbing inside her and knew he was coming, and a small part of her was at least pleased that she'd been able to please him. She wasn't focused on that, though, because the combination of Amber cumming on her face, Brian cumming in her ass, and her clit and breasts rubbing against the bed, were having their cumulative effect, and she came once more.