Date night

Friday, after work you popped back home and put on a collar shirt and tight kakis, then hopped in your car to go meet Megan for the date. First the two of you went on a long walk around downtown, just talking about your lives and goals. At one point you snuck behind a bush to eat Megan's ass, just to help clear up the sexual tension. In the air both of you could kind of feel that something was going to happen tonight. After the walk you felt like you had grown a little bit closer to Megan, like you actually might be catching feelings for. Holding hands, the two of you went to a nice fancy restaurant later that night where you and Megan's conversation got more intimate and romantic, and she even made you laugh a few time. Overall it was a nice date, the restaurant was beutiful and the food was delicious. After you were both wined and dined, Megan didn't even bother to ask you what you wanted to do next, taking your hand and walking you back to her house.

When you got there she led you to the couch where she put another glass of wine in your hand, she got her own and sat next to you, sliding her hand across your shoulder. Your conversation was nice for a bit, but quickly devolved into a makeout sesh, with you straddling her lap. You reached down and started to massage her cock through her skirt, "Mmmm baby..." She moaned. You leaned in, kissing her aggresively and stroking her cock. Feeling her hot cock through the skirt you felt an impulse, getting on your knees in front of her you put your head under her skirt. Finding her constrained member you kissed it affectionatley, you reached up and slipping her cock out from her frilly panties you started to lick her fat cock gently, "Yeah, get my cock ready for you, that's right." She said, you got butterflies in your stomach when she indirectly mentioned taking your ass. You kissed and lapped at her cock for another minute or two, when Megan got impatient. "Okay, let's go to my room." You felt yourself get nervous, but excited as you realized what was coming.

When you got to her room both of you took off all your clothes,Except Megan left on her panties and went to the drawer and got a bottle of lube. She gave it to you, "Well? Get me ready, unless you want me to go in dry." She wanted you to get her cock ready to fuck you. You got on your knees taking her cock out of her panties, and kissing it. You dripped some lube along the top of her cock, and took a hand and rubbed it in, making her member shiny and slick. Once you were finished you stood back up. Megan took you into a deep kiss, running one of her hands down your back to your ass where she twisted your butt plug a bit, and then popped it out of your ass making you moan into her mouth. She moved away from your kiss for a second to put the butt plug in her mouth right in front of you. You giggled, tipsy on the wine, "What?" She asked, "You're such a freak." You said, "Oh shut up you little slut." She said teasingly, clearly also feeling some of the wine. She pushsed you over to to the bed where you ended up on your hands and knees. Your ass had never felt so loose and ready to be filled, she had been playing with it all week trying to get you ready. Megan got up behind you her, her big fat cock slid between your cheeks as she gently dry humped you. Finally you felt Megan press her cockhead against your hole. You gasped as her cock head slipped easily into your asshole. The walls of your ass pressing down on her from all sides as she slowly pressed herself into you, groaning softly at the sensation of your hot slippery ass. You took shallow breathes as she deflowered you, you felt yourself expand around her slippery cock. Because you had been prepping your ass all week, and had lubed Megan's cock well, she was actually sliding in fairly easily and painlessly. Your face and chest felt hot as waves of pleasureable heat travelled through your body from your ass where here she hilted her cock. Her balls rested against yours, pubes tickling the inside of your cheeks. Your ass clamped down on on her cock, like it was trying to suck it in deeper. You were almost embarresed at how easily her cock had slid inside of you, and how good and right it felt to have her balls deep inside of your most private area. She stayed still inside you for a second, just letting you feel her cock massage your butt. You pressed yourself back against her, moaning pitifully as you went down on your elbows to arch your back more. "God your cute little butt feels so hot and wet, it's sucking on me like a pussy." You felt her pull back slowly, you gasped and moaned softly at the sensation of emptieness. It made you want it to be filled back up. Once she had pulled out about halfway she slowly slid back in. "Oooooh oh my god." You moaned out, the feeling of your asshole being refilled was like an almost unbearbly pleasurable tingling. "You like tha huh? Are you a good little girl?" She asked, you were lost in the sensation of this womens huge cock being deeper inside your ass than anything else ever had been. She slowly humped you, fucking you gently while you adapted to the feeling. You whimpered like a slut beneath your girl as she slowly picked up and pace. Her ass starting a steady rolling motion as she slid easily in and out of your love tunnel. As she fucked you ever so harder, the powerful feelings in your ass ramped up, your groin started to pulse with pleasure from her big cock pounding your ass. making you start to moan out loud like a bitch in heat, as your hung your head pushing back against Megan. The bed started to creak beneath you, in time with the smacking sound of her hips on your ass as she started to get a good pace going. She was starting to properly fuck you. drawing her cock out a little farther each time. Overcome with feeling you tried to reach back and stroke your cock, but Megan slapped it away, "You don't get to use that now." She said, finally drawing her cock almost all the way out of you, and then sliding easily all the way back inside you. You let out a high pitched whine, feeling yourself quiver around Megan's flagpole as she planted it deep inside of you. She drew her cock back again, "Oh fuck, fuck me Megan!" you moaned out, as she bottomed out in you again. She started railing you, thrusting herself deep inside of you, pounding on your prostate each time. "Oh fuck you're so good baby! Your ass is so tight!" She cried out. You felt your ass and cock start to pulse as you came, your cum sprayed all over the sheets. You arms came out from under you, leaving you face down ass up with your tongue hanging out as an orgasm rocked your body. Megan brought her foot up next to your face so she could mount you better, grabbing onto your waist and bringing herself slightly over you body over you so she could rail you into the sheets. You started to kiss and lick her foot a show your submission. You cock was flacid now, but it felt so good you felt another orgasm on the rise anyway. Your useless little cock flapped around beneath you while Megan flexed her ass gyrate her hips, bouncing her big pretty cock in and out of you, driving you into her bed. "Call me daddy you little whore." she ordered as she pounded you, "Fuck me daddy! Oh daddy!" You cried out as you licked her foot, and sucked her big toe. Megan picked up her foot and planted in on your head smushing your face into the bed while she pounded away, making the bed sqeak wildly. Heat radiated through your body at the humiliating position in which she was popping your cherry, the feeling of her foot pressing into the side of your face, her weight pushing on it. As ashamed of you were of it this just made you like it even more. You closed your eyes and perked your butt up for Megan to do with as she pleased, as you felt her cock alone make you start to orgasm for the second time, this time it felt even more intense, like it took everything out of you. Letting out nothing but moans, your soft cock starting to let out quick spurts as you quived around Megan's cock. That drove Megan to the edge too, she bottomed out a few more times during your orgasm, "God you such a sexy little girl, you got such a hot tight ass! It belongs to me now, your ass is mine you cockslut. Oh God I'm cumming!" Megan drove the whole length of her shaft up your butt one more time, grinding on you as her cock pulsed, you whiggled your ass against her a little while she dumped her load deep inside your honey pot. After that she held that stance for a little bit, getting her breath back while she emptied her balls. Eventually, she slide her cock out with a *pop* and took her foot off your head, and slapping your ass with her cock. She flipped you over and crawled up your body before she put her softening cock in your mouth. "Make it nice and clean for Daddy okay?" you obediently cleaned her with your tongue. Lapping at her cock and sucking her balls as she basically teabagged you after taking your anal virginity. Finally she drew away, getting on her side and pulling you in to spoon, she draped her leg over your waist and pulled you in snug where you quickly fell asleep.