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Ladies Night [All Parts]
🕑 Added 2023-01-16 00:05:01 +0000 UTCPart 1: https://youtu.be/7wStRFBbSHU
Part 2: https://youtu.be/Nm_yYt8nTZI
Part 3:
"I'm not wearing this, it's way too revealing. I just need something simple," I said. "Relax, I'm not gonna make you wear it to the bar. I just want you to see how it feels is all," she said. "Yeah, I'm just going to the bar... not a club," I said, sliding the slick black fabric up my legs.
Just like when Cheryl touched my legs, crispy waves of erotic pleasure washed through my body as the thin material came to rest around me. I adjusted the straps until my bra showed the least and ran my hands across the dress. I fought the urge to say anything. I'd already given Cheryl too much ammunition with my involuntary moans.
"How's that," She asked.
"It's alright," I lied. It was better than alright... it was great. The little black dress felt like the softest thing I'd ever touched. The way it hugged my body made me feel sexy as hell and I immediately recognized the many reasons why women wore shit like that.
"Just alright, you haven't stopped touching yourself since you put that on either. I have a feeling you like it more than just alright. Here, see if this one fits," She said.
"Just a minute, I haven't even seen how this looks," I said still rubbing the dress.
"Yeah, just alright huh," Cheryl said closing her closet door. I checked myself out in the full length mirror, turning from side to side. I inspected how nice my ass looked and how awesome I looked with tits. I couldn't believe how much of a difference a little makeup made and how much different my face looked with long hair.
"Okay... it's better than alright, like this is really nice," I admitted.
"Here, try this one," She said handing me a soft pink bundle of fabric.
I held the wad of soft material up to look at it and fold after fold of fabric dropped into the biggest skirt I'd ever seen. It looked like something Alice in Wonderland might wear if her colors were pink rather than blue. Thick tulle pushed the skirt out into a wide bell and the top had the cutest little sleeves that looked like they were only held on by a thread. The back tied into what looked like a corset with wide lace ties. I pulled the puffy dress on quicker than I thought possible and spun a little circle even before Cheryl could tie the back up.
"How does all this stuff fit me so well," I asked as she pulled the ribbon tight and tied a bow behind me then adjusted my sleeves off my shoulder.
"Everything's been kinda stretchy and this can go bigger or smaller with these ties on the back," she said.
"This is really elegant, I feel like I should be going to prom or something in this. Do you have anything less... um formal," I asked.
"You could wear this black skirt and a blouse if you want. I've probably even got some cute shoes that'll work. Do you still wear a seven," she asked.
"It's supposed to be a dress though. Do you think a skirt will work," I asked.
"You'll be good in a skirt, I promise," she said.
"Okay, let's go with the skirt then," I said hesitantly shucking the pink prom dress to the floor.
Cheryl tossed me a black pencil skirt and a white button down top that felt wonderful in my hands. I couldn't wait to see how it felt against my skin so I quickly pulled it on and started buttoning it up.
"Hey, this shirt is backwards," I cried. Cheryl just laughed.
"That's how girls shirts come," she said.
"They come with the buttons on the wrong side, seriously? How is this the first time I'm hearing all girls shirts button on the wrong side," I asked.
"It's not all of them, some button just like a guys shirt does but the dressier and more feminine blouses button on the other side," She said.
"What good does that do," I said struggling to button the top with the wrong hands. I felt completely inept at dressing myself and thought the only way it'd be easier is if I was dressing a woman for her.
"Do they put them like this so guys will have an easier time undressing their girls or what," I asked.
"I don't know bro, maybe... okay, tuck that blouse in and try these flats" she said.
"Flats, why aren't they just called shoes," I asked.
"They are shoes but they're not high heels... they're flat so they're called flats," She said explaining the logic.
I stepped into the plain black flats and flipped the heel up. They were a little tight but not so bad I was going to cry. I looked at myself in the mirror and couldn't believe how normal I looked from the neck down. With the wig, I looked like I worked at an office where everyone partied the whole day and had I been wearing a brown or blonde wig instead, I'd have made a completely convincing woman.
"You don't have, like a brown wig or something do you. I look like I work for a rave company or something," I said hoping she had something a little more conservative.
"Nope, that's all I have left after Isaiah left me. He took all the fun stuff we bought. This is all I have left," she said.
"Wait... what?"
"Yeah, Isaiah's the one that introduced me to the fact that men liked to feel pretty sometimes too. Before that, I had no idea a man would have wanted to wear a dress, or even experience sex like a woman," she said.
"What, sex like a woman... what the hell do you mean by that? Isaiah is one of the manliest guys I know. Are you telling me he is gay," I asked.
"Oh god no... he's as straight as they come. He just likes his ass... well, he liked it when I'd peg him," she said. When I gave her a look like I didn't have the slightest clue what she was talking about she explained.
"It's simple really... I wear a strapon and fuck him rather than him fucking me," She said pumping her hips mimicking how a man might fuck a woman from behind.
"That sounds gay as hell," I said in disbelief.
"Well it's no more gay than a man wanting to feel pretty, or desirable, or wearing clothing that makes him feel good. It's no worse than jacking off or fingering yourself. God, you could even have sex with a man and that doesn't make you gay. You're gay when you're only attracted to men silly," She said.
"That's weird. Why would any guy want something in his ass unless he was gay," I protested.
"Look, I'm not going to get into this with you. If you think the only way you can have an orgasm Is with your penis, you're dead wrong. You can actually have better orgasms through your ass whether you want to believe me or not," She said.
"I doubt that," I said shaking my head.
"Your friends are probably waiting for you. Don't you have to go," She asked.
"Oh shit, will you give me a ride please," I asked.
I didn't really want to walk the half a mile to the bar dressed the way I was and once I got to the bar, I'd get a ride home with Mike. Cherry nodded her head and grabbed her keys. I shuffled behind her as fast as I could but the pencil skirt seriously limited my stride. The skirt rubbed against my legs and just the feeling made my cock strain inside my panties. I was glad the pantyhose held my cock tight against my body or I'd have been sporting some serious wood. Even sitting in the car felt good. It was like I was covered in the softest most sensual things known to man and my cock couldn't get any harder.
Cheryl stopped on the street in front of the bar. My guts tightened and I finally realized what I was about to do when I saw Mike in line. He didn't disappoint but he was nowhere near as made up as I was. He had a big flowered dress on over his jeans and sneakers. Even his tee shirt poked out the arms of the dress and his wig was cheaper than mine.
"Go ahead, there's Mike," She said beeping the horn.
"Jesus, don't honk. Now everyone is looking, I cried.
My palms were slick and my heart was pounding as I gripped the handle and pushed the door open. Mike was still watching the car but he looked confused when I stepped onto the sidewalk. I leaned back into the car.
"Thanks sis, wish me luck," I said.
"Good luck, call me if you need a ride home or if you need me to rescue you from all the men that are going to be hitting on you all night," She laughed as she pulled away.
I couldn't believe what I was doing. Mike had obviously not done anything near what Cheryl did for me and neither did either of Mikes buddies. I expected to see the normal crew but they totally didn't show. As I was approaching Mike in line I passed the doors to the bar and the bouncer just waived me inside along with two other women. He handed all three of us a punch card that gave us ten free drinks. Mikes jaw hit the floor as I walked passed the line of guys.
I could barely breathe as I stepped up to the bar. I knew the bartender would see through my disguise and call me out but all he did was punch my card and ask what I wanted. I looked around to see if Mike had made it in or not and when I looked back I totally caught the bartender looking at my chest. I chuckled and wondered what he'd say if he knew they were just foam inserts and that I didn't have a pussy.
"Shot of Tequila please," I said with my voice just one octave higher than normal.
He set a shot glass on the bar and filled it with Tequila then pushed the glass in my direction. It worked, it totally worked... I was drinking for free on a Tuesday night. I didn't even have to pay the cover charge and the punch card was easily worth $50 in free drinks. More if I continued getting shots.
"Hey, who are you, where's Morgan," Mike asked.
"Who's Morgan," I said in my higher girl voice.
"Holy fuck dude, is that really you," Mike exclaimed.
"I don't know this DUDE you're looking for. I'm Mandy, what's your name," I asked.
"It's me... Mike," he said like I actually had a hard time telling who he was in his cheap costume.
"You're so fucking hot man. I can't believe they just let you in like that. They totally made us pay even though we're clearly wearing dresses and wigs. It's such shit," he continued as he pulled the wig off and flipped his flowered dress over his head.
"Oh, you actually are a man under that dress," I teased. "I thought Mike was a really strange name for an ugly girl like you anyway," I laughed.
"Hey, I was cute," he elbowed me in the arm.
"You should stick to being a guy, you're much better looking not wearing a dress," I elbowed him back.
"My god, you look phenomenal! Are you actually wearing a bra," he said tracing the thin black strap running across my shoulder.
"It's just to hold my boobs in place," I said.
"And pantyhose," he said touching my leg.
"Yup, Cheryl's idea," I said.
"Don't tell me you're wearing panties too dude," Mike said trying not to look shocked.
"Well, you'll never know unless you buy me a drink now will you," I laughed nervously.
"Fuck that shit, you have the free drink card," he said.
"Maybe you should have put in a little more effort. Maybe you'd have a card too but the fact still remains that I don't have a drink in my hand and if you want to get lucky tonight, that had better change," I winked.
"I'm not trying to get lucky with you tonight, not that you aren't hot enough but I know you're packing more than just a purse. Maybe Dane will take you home," he laughed pulling his friend from behind him.
Dane wasn't wearing pants under his blue and white striped dress and his wig looked like a single dreadlock was beginning to form on the top. He wasn't a bad looking guy other than his choice of clothes.
"That's a nice dress Diane," I winked.
"Yeah, borrowed it from my mom. I sure wish I wore shorts under this though. Maybe then I could get changed," he said tugging on the short dress as though it would magically get longer.
"You look good, at least this way I'm not the only one still wearing a dress" I said as Mikes other friend flipped his dress up over his head.
"Well I can't pull it off like you do," he said.
"Why don't you let me get you a drink since you're the only one who actually understood what we were supposed to do," I said holding my punch card up.
Two shots later I definitely felt the effects of the alcohol losing my inhibitions and the dance floor started looking more and more fun, only I didn't have anyone to dance with. I tried to get Dane to come with but he was a lot more nervous about things than I was at that point.
A fast song with a great beat came on and I felt my hips moving in ways I had never been comfortable dancing as a guy. I also found the girls on the dance floor were a lot less intimidated by me, as they started getting closer and closer until they were practically grinding against me. Had my cock not been completely flattened by both my panties and the pantyhose I'd have been tenting harder than ever before. I couldn't believe how freaky girls got with each other right out in the open. One girl, a hot brunette in a miniskirt was rubbing her crotch so hard against my leg I swore I'd have a wet spot either from her pussy on my leg or from me cumming.
Luckily the song ended and we didn't have to find out but the dance had made me beyond horny. I tried to get the girls number but I got shot down. She was apparently into dancing and grinding on girls but only into dating guys. I failed to mention the fact that I was actually a guy and by the time I thought to tell her she had moved along and a group of guys was vying for her attention. She had all the right curves in all the right places and she had rubbed her crotch against me of all people.
"Holy shit man, that girl was totally humping your leg," Dane said as I sat back down.
I was huffing and out of breath and still rock solid. I needed to get the hell out of there so I could get home and take care of my throbbing tool. I finished my punch card with a round of shots for me and Dane. It was official... I was as drunk as I'd ever been and when I felt Danes hand on my thigh I was too far gone to do anything about it. Besides, it felt really fucking good.
He leaned in close and his hand ventured further up my thigh until he was close enough to whisper in my ear.
"Forget about her, I'd let you play with me anytime you wanted," he said.
My head did a little somersault and I felt my cock twitch at the thought of having sex with Dane. I thought back to what Cheryl said earlier. I could even have sex with a guy and not be gay. I already knew I liked wearing women's clothes and being a girl in public. Maybe she was right about everything too.
"Are you a top or a bottom," he asked.
"I don't even know what those are," I said feeling his hand brush across the head of my stiff prick. I moaned and squeezed my thighs together.
"Have you ever been with a guy before," he asked pausing with his hand against my cock head. I couldn't answer, I was too distracted by how great his hand felt and the fact that I realized a guy was making me hard.
"No," I whispered.
"Do you want me to stop," he asked.
"No," I whispered.
Dane continued rubbing the head of my dick through my skirt. We were secluded enough from the rest of the bar that Dane thought he could get away with lifting his dress up. I could see the bulge in his boxer shorts and couldn't look away. I knew I was looking at his erection but couldn't bring myself to return the favor and touch it even though I could think of little else at that moment until...
"Hey dude, I'm fuckin' hammered," Mike mumbled as he fell into our table.
Dane yanked his dress back over his boxers and leaned away from me. I was obviously flustered and didn't want him to stop. Had I not been drunk I'd have been in my right mind but all I could think about was what was hidden under that blue and white striped dress.
"Yeah, we're drunk too," I said.
"What happened to the dress dude," Dane asked.
"Those fuckers wouldn't give me a card so fuck em' the ass holes, but this little hottie got a fuckin' card didn't she," he mumbled.
Dane just nodded his head and looked at me. I couldn't help but look at his crotch and wonder if he was still hard or not. The whiskey made me drunk as a skunk but has steered clear of my dick and I wished Mike would just stumble back wherever he came from and leave us alone.
"I'd fuck her, what about you dude, you think she's hot enough to fuck... wait, you're gay. You don't even like chicks do you," Mike yelled over the music.
"Quit being a dick dude," Dane said. I felt like he was protecting my honor if I even had any that needed protecting.
"It's a good thing she isn't a real girl huh, cause she's still on the market," he laughed.
"You know, you can eat a dick dude," I tried to say but something else came out that sounded a lot closer to, "You know, I'm nna eat a dick dude."
"I'll bet you are, I'll bet you are," he laughed so hard tears ran down his face.
I covered my face with my hands as Mike laughed. I could feel Dane place his hand on my back as he leaned across the table to give Mike a piece of his mind.
"Hey fuck head, if you remember right, this was all your idea but you decided not to show up in a dress. You just threw one on over your fucking clothes ruining it for those of us that did actually put a little effort into getting a fucking card and then take it out on us. Maybe next time you come at us with one of your hair brained ideas, you prove your commitment before anyone else follows your lead, now get fucked dude," Dane yelled.
"Yeah whatever man, y'all have fun," he said stumbling away.
"God, I thought he'd never leave," I laughed.
"Yeah, such a jerk," Dane said placing his hand back on my thigh. It felt nice but the magic of the moment had passed and it all felt a little too weird to continue. His fingers slowly worked closer to my cock head but it felt wrong.
"Hey, I've got to go. I've got class first thing in the morning," I lied.
"Come on... one game of pool before you leave," he said.
I think deep down I wanted him to keep pursuing me even if he was gay. I think I needed to find out if what he and Cheryl said was true or not. My cock sure knew his hand felt good.
Dane racked the balls and I did my best to aim down the stick and deliver a great break but I'd never been much for pool and being as drunk as I was only made my aim worse. I hit the cue ball with the side of my stick and it careened away from the rack and fell in the bottom corner pocket.
"Um... that's a fowl, it's my shot," Dane said.
"Wait wait, gimme one more chance. I can get it, I just need to focus better," I said.
"Lemme help you," Dane said stepping in behind me.
He wrapped his arms around me and leaned over my back. I could smell his aftershave. His body pressed against me and I realized how cold I'd been and how warm his body was. He grabbed my hands and directed my left hand to support the stick. He grabbed over my hand and pumped the stick forward and back a couple times.
"You seem pretty good at that movement," I teased.
I felt his cock press into my ass as I pushed back into him. He lined the stick up and pulled the stick back. Just a moment before the cue shot forward he pumped his hips into me and the balls shot all across the table. Three balls went in and I cheered as he stepped back to watch.
"I could show you how to be that good too," he winked.
I wasn't sure if he was talking about breaking or something else but I liked it either way. I lined up for a super simple shot that I couldn't miss and shoved the cue forward. It scooped the cue ball up and threw it off the table in Danes direction almost hitting him right in the gut.
"Careful there, I don't want you accidentally hitting me in the nuts," he said.
"Oh calm down, I'd kiss them better," I said.
I immediately looked around to see if anyone heard what I said but we were still mostly alone. Dane smiled at me and started looking for a shot. I knew if he was as turned on as I was that I could probably use my body to distract him and maybe I'd win the game. He lined up a great shot from corner to corner and I slow danced as as much like a stripper as I could imagine but the ball clunked in the pocket anyway.
"Fuck, that was a good shot," I said.
"I always find the hole," he said.
He lined up for another shot and I attempted to shake my big fake tits toward him and he drained another ball. Nothing I did was working. It was like he was a pool shark. I had to get creative. I had to think about what would fuck him up so when he lined up again, I leaned in close and whispered in his ear just as he pulled back to strike the cue.
"What hole will you find on me," I said feeling super slutty.
Dane completely missed his shot and knocked in two of my balls. He'd turned a visible shade of red and I felt triumphant for getting under his skin. I had him beat for sure if I could just drop a few balls on my own but I missed again.
"It's okay, we're still tied up. What are you gonna do when I beat you," I taunted him.
"Oh, you want to make this interesting do you," he smiled.
"Yeah, what do I get when I win," I asked.
"Whatever you want. Hundred dollars, a back rub, a blow job, whatever you want," he smiled at me.
I knew his weakness. I knew I could beat him so I could offer him whatever I wanted. He wasn't going to win. "You win, I'll let you pick the hole you drain those balls into," I smiled looking down toward his crotch.
Dane got an evil look on his face and completely shot me out. He ignored me for the next three shots. All he had left was a two ball and the eight ball. I had to pull out all the stops or he'd really be unloading his balls somewhere inside me. I leaned in and whispered the dirtiest shit I could think of in his ear.
"If you make that shot, I'll suck your dick right here in the bar," I said hoping and hoping that he'd miss.
Clack... and he missed!
"Back in the game," I hollered.
I had three balls left and the eight ball. Magically I drained the shot I was aiming for and accidentally knocked my other two balls in bringing me into the lead. All I had to do was sink the eight ball and not scratch. All I had to do was win whatever I wanted from Dane but I wasn't sure what I really wanted. Did I want to loose on purpose so I could say it was because of a bet or did I want to win and take what I wanted because I wanted it.
"What do you want if you win," Dane asked.
"You'll find out soon enough," I winked.
I was almost laughing. Dane leaned in close and whispered in my ear. He used my own dirty attack against me and threw me way off my game.
"If you miss, I'll know it was on purpose," he said and he backed away.
If I missed, it'd be on purpose. But if I won... I couldn't lose. The shot was too perfect. If I missed, it would have to be on purpose. A huge smile grew across my face. I pulled my stick back and drove the cue ball forward at a tremendous speed smashing the eight ball right into the corner pocket.
"I win, I win, I win," I sang dancing circles around Dane.
"Wait for it, wait for it..." he said.
I had no idea what he was talking about and didn't really care either. I'd won fair and square, but my heart dropped and I finally registered what he was looking at. The cue ball had hit nine bumpers and was slowly tracking toward the exact pocket I'd dropped the eight ball into. He started jumping even before I'd lost but I knew it was over even before the cue ball disappeared leaving nothing else but the two ball on the table.
"What was it I got when I won," he asked.
"You know what it was," I sulked. I couldn't believe he won on a technicality. He didn't win, I lost. He didn't beat me, I gave it to him and now I'd really have to give it to him.
"You did that on purpose didn't you," he said.
"Maybe... maybe not. We'll never know for sure will we," I said hanging the stick back on the wall.
"Double or nothing," he said enticing me to pause with the stick still in my hand.
"If that was an accident and you actually did beat me, I'll give you the chance to get even, but if you meant to lose and want to pay up, hang that stick back up and let's get out of here," he said.
I held on to the stick for a moment as I thought about actually beating him. I thought about what we'd be doing if I didn't play another game and I thought about doubling my current bet.
"If I lose, you get to drain your balls in whatever hole you want... twice," I asked.
"Yup, two times, but you can avoid all that by just beating me this time," he said.
I knew I couldn't actually beat him. The only decent shot I'd made all night was the eight ball and I still scratched. I was always garbage at pool and Dane was actually good. It was getting late and if we were going to do it, I'd rather do it a little drunk.
"If you make me like it, I'll let you do it twice," I winked and hung the stick on the wall.
"My place or yours," he said.
"How far away is your place," I asked.
"Couple blocks."
"Yours, but maybe buy me one final drink just to calm my nerves," I asked.
We both downed another shot of the same drink that kicked the whole night into gear and stumbled out into the darkness arm in arm. My pantyhose swished against my pencil skirt and my cock got even harder thinking about what he was going to do to me. I gripped his arm as we climbed the two flights of stairs to his apartment. He twisted the key in the lock and I felt ready. I wanted to feel his body against mine.
Dane flipped his blue and white dress over his head. The single dreadlock wig fell on top and he was in nothing but his boxer shorts. He rubbed his palm across his cock and I watched it grow to full length. He was much larger than I was and easily the biggest cock I'd ever seen except for in the various pornos I'd watched. His cock curved toward his belly button and finished out right around seven inches. I could barely breathe when he pointed at the floor in front of him.
"Lemme try that mouth girl," he commanded.
"Is that where you want to cum," I asked.
"I'll let you know after you get going," he said as he stroked himself.
On autopilot, I dropped to my knees and opened my mouth. I was excited but beyond nervous. What if I sucked at... sucking. What if I used too much teeth, what if I liked it and he didn't, I'd want to keep going and he wouldn't.
All my thoughts were cut short when Dane grabbed the back of my head and guided my face to his upturned cock. My lips met the underside of his pecker head first and I planted a nervous little kiss on his dick. I'd done it... the worst part was over. I'd felt another man's cock on my lips and all there was left to do was to suck.
I spread my lips and took just the head into my mouth. It tasted like velvet nothingness. Hot velvet... thumb or arm or skin. The taste didn't surprise me as much as the texture and the warmth. His shaft was smooth and forgiving while also being hard and unyielding. It was a total mind fuck as I took him further into my mouth. It felt good against my tongue and almost natural in my mouth even though I'd always considered myself a straight guy.
I was on my knees wearing women's clothes and a wig with a man's cock in my mouth and I was doing it all by choice. I reached up and cupped Danes nuts as I swirled my tongue around his cock head. I always liked my balls held and even fondled during masturbation so I knew Dane would like it too. He responded by pulling my face into him harder as he moaned his approval.
"Awe, god that's good," he moaned.
I couldn't say anything with his cock buried in my throat other than, "aaaghhhan eh," as I gagged.
My own cock was splitting like an over cooked sausage and had I rubbed it just once, I would have sprayed cum all inside my little black panties. I couldn't believe how close I was just from sucking a cock and when Dane pushed my face away from his wonderful tool, I almost cried.
"Was I doing it wrong," I asked sitting on my haunches.
"Oh no, that was something else... like you are a natural born cock sucker," he said.
"I thought you wanted to cum," I asked.
"Not there," he said.
"Uh... where else then," I wondered already knowing the answer.
"I think you know, why don't you get a little more comfortable," he said.
Dane helped me unbutton my top when I couldn't stop fumbling with the buttons and I finally understood the uses of backward buttons. My top fell to the floor and I unzipped my skirt letting it pool around my ankles. Dane gently traced his fingers from the clasp on my bra down the small of my back and across my ass. His fingers dived inside my pantyhose and forced them off my butt. I clumsily pushed them down and almost tripped stepping out of them.
"You look really hot in panties," he said gently cupping my buttocks in each hand.
"Thanks... I guess," I said.
"No, thank you," he said running a single digit into my crack.
"Should we maybe... go to your room," I asked not wanting to do what I thought he was going to do in the living room of his apartment.
Dane took my hand and pulled me down the hall. He shouldered a door open and twirled me inside the small room catching me before I tumbled to the floor. It felt nice being cradled against his hard body and I felt my pulse quicken when he started kissing my neck. He pushed me backward onto the bed and fell on top of me. His weight made it hard to breathe but I couldn't think of anything better than having him on top of me. His lips worked gentle little kisses across my neck and down my shoulders.
Danes hands worked the clasp of the bra with expert hands and my bra fell to the floor with the big teardrop pads. My nipples felt the heat of his mouth and a long moan spilled from my lips.
"Oh god, mmmmm," I cried.
He rolled me over onto my belly and started kissing the back of my neck and across my shoulders. Excited shivers rolled through my back as he started needing my arms. Dane sat on my upper legs as he massaged my back. His stiff prick nestled its way between my butt cheeks and slid up and down every time he moved.
When he worked his massaging down my back he slid off of my ass and I almost missed the feeling of his hard cock pressing between my buttocks. When he reached the small of my back, he hooked his fingers in my panties and slid them down my legs kissing each new visible inch of flesh until the panties fell off my feet. He listed the soles of my feet and worked his mouth up the back side of my legs until he reached my ass cheeks again.
"You have the most gorgeous ass," he said placing wet little kisses along the cleft of my ass and leg.
I was about to say thank you when he spread my ass cheeks apart and kissed my puckered little raisin hole. My body tensed up from the unexpected sensation even though a slutty moan fell out of my mouth. He followed the kiss up with a gentle lick across my back door and pleasure washed me into compliance.
"Hold your cheeks apart for me," he insisted.
I reached back and stretched my ass cheeks farther apart than I'd ever pulled them. Dane lifted me onto my knees leaving my chest and face on the bed. I imagined how slutty I looked with my face smashed into the bed and my spread ass high in the air. Dane massaged the insides of my ass cheeks as something warm and wet squished around my hole. It felt better than anything I'd experienced up to that point and I wanted more.
"Oh god, that feels so good... keep going," I moaned.
I felt one hand move to massage the small of my back while his other hand remained between my ass cheeks. I was still holding my cheeks apart when I felt a little pressure against my hole. His digit kneaded my spit slick hole until I relaxed enough for it to slide in under minimal pressure. My body involuntarily tensed up but Dane persisted and massaged me back into relaxing. His finger felt huge inside my anus but good at the same time. I wanted it... but he was just moving so slow.
"Give me more... more whatever you're giving me," I exhaled.
Dane spit on my puckered hole and pressed his finger inside me. Fire erupted in my ass but I pulled my cheeks apart further and pushed my ass back into his manual assault until he touched something deep inside me and my cock started dripping clear fluid.
"Oh fuck, what are you doing to me," I cried.
"Does that feel okay," he asked.
"Oh yeah... that's great, keep going, keep going," I moaned.
Dane added a second finger. He worked his hand in and out until I relaxed enough for it to start feeling really good again. He could tell it felt good more from my moaning than the constant stream of fluid leaking from my cock.
"Roll over baby," Dane said pushing my hips sideways.
Danes fingers slipped out of my ass and I instantly missed the full stretched feeling. His cock mimicked mine by leaking clear fluid from the tip. I flipped on my back and sat in the big puddle of my prejizz. Dane slid my ass to the edge of the bed and the spunk smeared all up my back.
"Are you ready for this," Dane asked stroking his big curved shaft.
"I think so," I mumbled.
"Tell me you want it," he said.
"I want it, give it to me," I copied.
"Beg for it," he insisted.
"Please give it to me, I really want to see what it feels like... please," I asked.
Dane placed the tip of his cock against my hole and paused.
"We're gonna have to work on your begging," he said as he applied pressure.
My ass instantly stretched beyond what I thought possible and a stinging burning pain radiated from my ass, down my legs and out my toes. My fists gathered big balls of bedsheets as I cried out and Dane stopped pushing.
"Please don't stop, keep going, just get it in. Don't stop please," I begged.
"That's more like it," Dane said pushing until I thought I might burst.
He didn't stop until his pubic hair was touching my balls. I expected it to hurt a lot worse than it did but mostly because the one time Christina let me try to put it in her ass, she flipped out and screamed the whole time. In reality, it felt pretty good feeling filled and stretched but when Dane pumped in and out he started hitting a most pleasurable spot near my belly button. My cock dripped a new puddle on my stomach and I wanted it harder.
I wrapped my legs around Danes ass and forced him to pound me harder. I was right at the edge of cumming and I hadn't even touched my tight cock. I couldn't believe how good Dane felt inside me and I couldn't believe that I liked it as much as I did.
"Fuck, I'm gonna cum," Dane growled.
"Mmm... me too, just keep going, harder, harder," I cried.
"Awe fuck," Dane cried. He gripped the base of my cock and jacked me two times. My ass clamped down on Danes cock and my nuts unloaded pure pleasure onto my belly and chest. I could feel his cock twitching inside me and moments after, a slick wet feeling dripping out of my ass. His cock was still inside me when he collapsed on top of me and smashed my cum across our belly's.
"Mmm you could keep going," I said pulling his ass cheeks to get him to keep humping me.
"That's not how it works," he said.
I felt him soften and slip out of my hole. A rush of warm goo fell from my ass that I assumed was Danes load. His deflated cock rested against my hole as he kissed my ears and neck.
"How was that for your first time," he asked.
"I think I'm in love with your cock," I moaned.
"Now that's gay," he laughed.
"Mmm... not if I'm the girl," I teased.
I missed class the next day because we spent the whole day fucking and within a week I was his live in girlfriend. Cheryl helped me become the woman I am today and I couldn't be happier that I exploited an advertising loophole just to get free drinks.
The end...
