Ladies Night

"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...