Eager First Times

by Betsy Locke

  Then nobody would lose the bet.

  They wouldn't be able to confirm it.

  I sat and bided my time, drinking beer after beer. Soon I was all alone sitting at the bar. There was a slight wrench in my plan. Not all my friends had left yet.

  John was out on the dance floor with his hands on the hips of an older woman. I needed to at least make an attempt or else John would be able to relay everything to the guys tomorrow.

  I ordered a shot of tequila and downed it straight. My eyes scanned the bar and found a MILF that would be perfect.

  It was now or never.

  Chapter Two

  She wore a tank top that hid the large breasts underneath. Her short brown hair danced around her shoulders.

  “You can do this, Zachary,” I said to myself. “Deep breaths.”

  I inhaled sharply and walked over to the empty seat next to my target with my half-full pint of beer. I sat down and had no idea what to say. Should I open with a joke? A pick-up line?”

  What would my friends do in a situation like this?

  Definitely a pick-up line.

  But I didn't know any.

  I turned to the woman and offered her my hand. “My name is Zachary,” I croaked out. My voice was wavering and I knew she could tell.

  The MILF turned her head to me and reluctantly took my hand. Her eyes scanned me up and down and it almost looked like she was going to laugh at me. “My name is Alice,” she replied.

  I gulped. She could tell I was no good at this. “Would you like me to buy me a drink? I mean you.” Sweat was building on my brow. “Would you like me to buy you a drink?”

  She raised her martini glass that was filled to the brim. “I'm okay, thanks.” She faced forward and tried to ignore me.

  That just about summed up my entire history with women. I never got past the introduction part. They always ignored me afterwards.

  I looked back at the dance floor and John was still dancing. I couldn't give up just yet. Not until John had left.

  “So Alice, what brings you to this bar?” I took a long sip of beer while I waited for her answer.

  “I'm sorry but I'm not going to go home with you,” she replied, standing up and leaving me all alone at the bar.

  Another strikeout. I was amassing quite the record with women.

  I nursed the last bit of my beer and stared at a tray of peanuts next to me. It was better than staring at all the older women who would never give me the time of day.

  I felt like I was just making a fool of myself by sitting here all alone. I should just go home and concede defeat. At least I wouldn't have to endure anymore humiliation.

  I took out my wallet and was prepared to pay my tab when a woman tapped me on the shoulder. I turned around to find the sexiest MILF alive standing before me.

  She had to be a model or something. The black dress she wore clung to every curve. Her large breasts were spilling out of the top almost begging me to kiss her cleavage. Her long blonde hair was definitely not her original hair color but it looked so good on her.

  And those red lips! I already imagined them wrapped around me as I fed my cock to her.

  “I see your drink is almost empty. Can I buy you another?” she asked.

  I dumbly stared at her blue eyes for minutes without responding. Why was this true MILF talking to me?

  I turned to my glass of beer and saw that it was empty. I swung back to her and nodded. “That would be great.” My heart was beating so hard that I thought my chest was going to explode. What the fuck was going on?

  The woman sat down next to me. She got the attention of the bartender immediately. “Can I get two whiskey and cokes?”

  The bartender nodded and got to work.

  “What's your name?” she asked.

  My eyes were glued to those perfect tits. I watched them swell with every breath. I could even see a hint of the lace black bra that she wore.

  “My name? It's Zachary?”

  The older woman laughed and her boobs jiggled. “Is that a question?”

  “That's my name,” I replied more confidently. The stiffness in my pants throbbed. I had to keep my legs spread to prevent from crushing my swollen balls.

  “It's nice to meet you, I'm Victoria.” She gave me her hand and I shook it, admiring her red nails that matched her lips.

  The bartender returned with our two drinks. I quickly swallowed my whiskey whole out of nervousness. Victoria thought I was challenging her and drained her drink. “You know you're kind of cute,” she said.

  I looked behind me to see who she was talking to but nobody was there. I turned back to her and pointed at my chest. “You mean me?”

  She laughed again, revealing perfectly white teeth. Victoria nodded. “I think you should go home with me.”

  If I had any liquid in my mouth I would've spit all over her. “Did one of my friends put you up to this?”

  Victoria stood up and put a hundred dollar bill on the bar to cover the tab. “Get your stuff and let's go.”

  I watched her walk away and her ass bounced up and down in that tight dress. I was frozen for a moment and then realized that it was now or never.

  I was going home with a MILF!

  Chapter Three

  Victoria brought me to her white BMW 5 series. She unlocked it with a beep and I jumped into the passenger seat. The car smelled just like new. She probably leased a different expensive car every year.

  We drove through the night and I had to keep wiping my sweaty palms on the nice leather seats. “This is a nice car,” I said over the radio.

  “Thanks,” she replied, turning the dial down. “Do you do this often?”

  I sat up in the seat. “What?”

  “Go to bars and pick up on older women,” she continued with a wink.

  I blushed and couldn't hide it. I didn't want to tell her about the bet. I didn't want to jeopardize the night. “I haven't done this before.”

  The BMW sped up. “Good,” she replied.

  We pulled up to a high-rise apartment building and she gave the car keys to the young valet. I followed her into the elevator and we took it up to the top floor in silence. I had no idea what I should say or how to act around her.

  We came to her door and I took in a deep breath. This was going to happen. I'd never been with a woman before and my first would be a knockout MILF.

  We entered her modern-looking apartment with a view of the city in the distance. “Would you like something to drink?” she asked, entering the kitchen and turning the light on.

  I followed her in and put my hands down on the island with white marble. “I'll take whatever you have.”

  I watched as Victoria reached up to grab two glasses from the cabinet. Her dress was just short enough that I got a peek at the underside of her ass. I almost creamed my pants right there. I had to pinch my thigh to bring me back from the edge.

  Victoria poured two glasses of rum with sprite and handed me one. She raised her glass into the air and I did the same. “To an eventful night,” she said.

  I clinked my glass to her and sipped the rum. It burned on the way down but I could feel it already warming me up. I looked at her and saw a little bit of liquid escape the corner of her mouth and run down her neck and into her cleavage.

  My cock pounded against my pants. The urge to come was unbearable. I tried to think of anything else to keep it at bay. Thinking about not being able to perform for her made the feeling fade away.

  What if I did something wrong? What if I was no good?

  “Shall we go to the bedroom?” she asked, already walking towards it.

  I followed that ass like a lost dog looking for its next meal. The bedroom was white with a large king-sized bed with a white puffy comforter.

  Victoria faced away from me and cleared her golden hair from the back of her neck. “Can you unzip me?”

  I tentatively reached out and held the silver zipper between my fingers. I slowly pulled it down, revealing her bare bac
k and the strap of her black bra. Her tanned skin looked good enough to eat.

  Victoria took over and pulled the dress down over her shoulders and down to her waist. She turned around and showed off that perfect curvy body of hers.

  My balls were like two hot coals waiting to unload. I stood frozen as she took a step towards me. I didn't know what she wanted me to do. We hadn't even kissed yet.

  “Don't be nervous,” she said. Victoria took my hand and placed it on her boob over her black bra.

  I squeezed her breast and it was everything I hoped it to be and more. So soft and squishy and she still had her bra on. I felt her up with both hands, squeezing her tits together and watching the canyon of cleavage develop.

  Victoria leaned her head back and moaned. “You like these big boobs?”

  I reached behind her back and felt around the strap. Was there some way to unlock it? I had no idea how to take off a bra.

  Victoria smiled and turned around for me. “Find the spot where the two straps hook together. Unhook them and pull them apart.”

  I found pinched the spot where it all connected and the hooks came undone. Her bra fell off and she turned back around. Her tits were two gigantic melons that were still so perky. Her pink nipples were hard and erect.

  Victoria could tell exactly what I wanted. “Go ahead,” she said.

  I buried my face in her chest, my tongue running over every inch of her ample cleavage. My mouth found her wanting nipple and sucked on it, chewing on her until Victoria cried out. I pressed my fingers into her soft skin and massaged her tits.

  I came up for air and that's when Victoria hit me with her plump red lips.

  It was my first kiss.

  We were locked together, our mouths parted. I put my hands around her waist and clenched her dress that was still scrunched up around her hips. I pulled her against me and I could feel her warm body against my pulsing cock that was still trapped in my pants.

  Victoria broke away from the kiss and got down on her knees. Her fingernails deftly undid the button on my pants and unzipped me.

  Holy fuck. She was going to suck my cock.

  Chapter Four

  Somebody pinch me because I must be dreaming.

  This was a fantasy come true.

  The goddess of all MILFS was about to wrap her lips around my hard cock.

  Victoria pulled my pants down and my boxer briefs along with it. The only thing left on was my button-up shirt.

  My stiff rod stood straight up, bouncing up and down with every pulse. “This looks so good,” she said, her fingers tracing around her lips and then moving to my crotch. She gripped my thick cock and I braced myself from the sudden injection of pleasure.

  She locked eyes with me as her tongue ran over the head of my penis, collecting the little beads of pre-cum. “Fuck,” I said over and over again. I couldn't believe this was happening.

  “You want to be in my mouth?” she asked with a knowing smile.

  “Oh god, yes. Please, Victoria.”

  She opened her lips wide and put me into her moist mouth. I grit my teeth as she shoved me deep down her throat. She stroked me while bobbing up and down. I slipped my fingers through her hair and held the back of her head as she blew me.

  The pleasure was getting to much to handle. My breathing quickened, my balls tightening up. I was close. I couldn't get a word out to warn Victoria. I didn't want to come this quickly. I was about to shoot my load right into her mouth.

  But Victoria had all the experience. She knew right when to stop.

  She let go of my shaft and pulled me out of her mouth. She wiped the drool from the corners of her lips. “We don't want you finishing too quickly.”

  Victoria stood up and stepped towards the bed. She pulled her dress down her legs and stepped out of it. A black thong that accentuated her curves was the only thing left preventing me from taking her.

  “Get over here and on your knees,” she ordered me.

  I happily went to her and got down onto the carpet. Her pubic mound was just inches from my face. I could smell her sweet scent.

  “Take off my panties,” she said.

  I gulped and pulled them down, revealing freshly shaved pubic hair. Her thong rested around her ankles. My hands ran up her tanned thighs, kneading them.

  “Eat my pussy,” she commanded.

  I was waiting for her to say that. I shoved my face in her crotch, my tongue starving for her wetness. Her nectar tasted so sweet. I lapped at her pussy, drinking it all in.

  Other than feeling around with my tongue, I wasn't sure what I was supposed to do.

  I knew women had a clitoris but I had no idea where it was or what I was looking for. My friends always bragged about making women have multiple orgasms when going down on them. What the hell was I supposed to do?

  Victoria's hand grabbed a tuft of my hair and pulled my head back. Her moisture was spread across my face. She spread her lips with two fingers and pointed to the little bulb. “Put your tongue on me right here.”

  I pressed against her clit and Victoria's grip on my head tightened. I swirled my tongue around, feeling for every time her body jerked to my touch. I listened to her breathing and moved faster if it increased.

  “I'm close, Zachary. Make me come!”

  Victoria bucked against my face as she came hard. I continued to pleasure her clit until her legs relaxed and her grip on my hair loosened.

  “You're pretty good at that,” she said. Victoria sat down on the edge of the bed and scooted back until she lay against the headboard. “Take off that shirt.”

  I wiped my mouth and stood up. I slowly unbuttoned each button, showing more and more of my skin. Victoria bit her lip as I exposed my hardened pecs and thick arms. I watched her chest expand and contract as she watched me.

  I discarded the shirt on the ground and stood completely naked for Victoria. I felt self conscious as her eyes inspected every bit of me.

  “You must work out a lot,” she said, biting down on the tip of her index finger.

  My friends and I always challenged each other to go harder at the gym. It looks like all that hard work finally paid off.

  “How much do you want this?” Her finger trailed down her neck and in between her massive breasts.

  “So bad,” I replied, wanting to stroke my cock and come all over that body of hers. I just had to be patient.

  “Get over here and mount me what that big hard cock. Show me how much of a real man you are.”

  I crawled onto the bed and got on top of Victoria. Her body was warm beneath me as my cock was only inches away from her hole. We kissed and I squeezed her boobs, weighing them in my hands. I loved the way they felt.

  Victoria was so fucking hot.

  Chapter Five