The Wingman

All characters are 18 or over

The weekend was finally here, and I just wanted to drink, watch TV, jerk off, and sleep. Unfortunately for me, my roommate had other plans. The sun hadn't set, yet he still dragged me out of the house. 

It was a short walk to a neighboring park where there was some kind of music festival happening. It was just a few local musicians performing in different sections of the park. The crowd was mostly young couples and families milling about. 

We weren't there five minutes before I glanced at my watch, trying to figure out how much time I would give it before I bailed on Mike. When I looked up, he was frowning. "C'mon Nic, you can't leave me tonight. You owe me!" he declared. 

"Why do I have to be here anyway?" I raised a brow. "You can definitely handle... this," I gestured to our surroundings, "all on your own." Mike rolled his eyes at me as if he was talking to a child. "My future wife is going to be here. But, she's coming with her sister. I need you to run interference." He slapped my shoulder and said, " So put your wingman hat on, and I might...just might... name our firstborn after you." 

We stopped in front of a small stage where a local band just started when I noticed a pretty blonde walking towards us. She was short and petite with some nice B cups. She wore a cute little white dress that made her look sweet and innocent.

She was tiny enough so that you didn't have to powerlift like I did to throw her around in bed. I chuckled to myself. This was Mike's type.  

She saw my roommate and quickly walked towards us. I noticed a cute dark-haired girl trailing slowly behind her, absorbed with her phone. The brunette was taller, but she looked a lot younger. When she finally looked up, I could see big brown doe eyes. They were beautiful. 

She gave me one glance before frowning. Great! I had to work hard on charming this one. I get it...She clearly didn't want to be here. I didn't either. I looked at her, frowned, and then looked at Mike. His eyes silently pleaded with me. I groaned, preparing myself to plaster on a fake smile for the night.

We walked towards them and Mike stretched his arms open to the small blonde. He lifted her off the ground with a hug, and smiled wide as he introduced her. "Nic! THIS is Christina!" The pretty blonde looked up at me with a shy smile. 

I reached out to shake her hand. She looked down at my outstretched arm and smacked it away. "I prefer hugs," and leaped into my arms. As I pulled away she grabbed my forearms, "Wow, you're huge." I bit back my normal smart-ass response and just laughed. 

I've heard this before from women and some men when I met them for the first time. At 6'2", 230 pounds I was pretty big. With the physique I developed at the gym, I've been called massive many times before.

I didn't want to read too much into the look she was giving me. I just said, "Yeah thanks, I'm a trainer at a gym in Castle Hill." I turned and grabbed a hold of my roommate's shoulder, pulling him towards us. "I trained Mike up to be the six-pack specimen you see before you," I boasted. Her eyes followed me as I poked at Mike's chest and she blushed a little. He just gave her a goofy smile in return.

"You two do look like the type to eat flavorless chicken and steamed broccoli every day." I whipped my head in the direction of the new speaker. The brunette barely looked up from her phone to see my reaction. Christina chuckled nervously and said, "Nic, this is my little sister Daisy. Daisy this is Nic," She smacked the side of Daisy's arm before she would look up.

Her eyes slowly scanned me from top to bottom. I felt like a live wire fell at my feet.  I stood up straight for her appraisal while I looked her over too. In contrast to her sister in white, Daisy was dressed in all black. Her hair was jet black, past her shoulders, to the middle of her back. She wore an oversized black v-neck with a huge skull on it. You could still tell she had huge tits because they jiggled wildly every time she moved. Her face had dark eye makeup and pink glossy lips on a cute little mouth. I liked all of it.

She had a nice fat ass that she somehow squeezed into some short jean shorts. They were so small, you could mistake them for underwear. They revealed thick thighs that I wouldn't mind getting between. She wasn't toned but her curves seemed soft and squeezable.

I was attracted to her. Time to find out how old she was. "Hey Wednesday Adams, how old are you?" Daisy rolled her eyes. "I'm eighteen," she huffed as if it should've been obvious. "How old are you, forty?" 

My hand shot to my chest in feigned shock. I'm only twelve years older than her. She's childish but thankfully not as young as I thought. Anyway, I wasn't going to let her earlier comment slide."Well, you look like the type to..."

"Why don't we check out the rest of the park?" Mike interjected. His angry eyes caught mine. He knew I was about to hurt this little girl's feelings and ruin the whole night for him. I snapped my mouth shut and watched him as he pulled Christina away from us. 

I looked back at Daisy who pressed her lips together to hide the beginnings of a smile. Her brown eyes locked on mine before her phone pinged with a notification. She just stood there texting, so I just walked off and left her. 

A few seconds later I could hear Daisy running up behind me, trying to catch up with us. I should've had more self-control but I couldn't stop myself from turning back to watch those massive tits sway from side to side. When she caught up with me, I pretty much stayed silent. She looked ahead at her sister and Mike who were engrossed in each other. 

After a few moments of walking side by side, being ignored by me, she finally spoke. "What were you going to say? I look like the type to... to what?" I skimmed over her pretty face, all flushed. My irritation had already subsided. She's just a stupid kid and Mike seemed to be enjoying himself. I didn't see a point in insulting her now. 

I just shrugged before responding with, "Ehh..the moment is gone." She smiled a little before tripping on something alongside me. "Woah!" I called out as I tried to stop her fall. Her soft breasts crashed into the side of my arm as I held her in a twisted bear hug. 

My effort to stop her face plant must have softened her up, if only for a second. She looked up at me, her hand still gripping my forearm. "Thank you Nic! I'm sorry about earlier. I couldn't stop myself." I frowned as I released her to walk. "And...You don't really look forty." I huffed and continued walking. "Apology accepted I guess."

We spent a few more minutes following Mike and Christina from a safe distance as they chatted. We all stopped to eat tacos from a nearby food truck. I got a beer or two and my mood improved. It was then I started up a real conversation with Daisy.

We chatted about her recent graduation and her plans for school. She would look at me with those big eyes  with these long lashes and I had to bite back the urge to touch her, kiss her. She started asking about my job. I started dropping little comments about how pretty she was. She giggled and blushed the whole time.

I bought her some cotton candy because she asked me to. Her indifference from before was replaced with flirtatiousness. I noticed how she touched me more and leaned into me as we walked.  Suddenly we were distracted by a loud cackle. That drew our attention to Mike and Christina walking ahead of us. He must have said something she thought was funny. Christina threw her head back laughing and slapped him on the shoulder. 

"There's no way your friend is that funny," Daisy grumbled. I stopped in the middle of the path we walked. I stared at her for a moment before flatly replying "he isn't" and we both laughed. When we walked up to them, I said. "Why don't we go back to our house? You two can...talk some more. Daisy and I could spend some more time together. I like her a lot." I reached my arm out to pull her into a side hug. 

Everyone raised their brows at that. Daisy looked like a deer in headlights.  Mike gave me a questioning look while Christina eyed her sister for any discomfort. "Daisy, are you okay with that? We can go home if you want." I looked down at Daisy. She looked up at me, and turned to her sister "I'm OK with it."

I kept my arm around her, surprised that she didn't pull out of my hold. Ten minutes later, we were at the house Mike and I rented. Mike quickly dragged Christina away for a 'tour' while Daisy followed me in. She walked around, examining everything, picking up stuff to put them back down again.

I offered her a drink to politely steer her into the kitchen. She followed me and stopped at the kitchen island. She leaned forward, elbows on the counter, with her hands clasped together.  "Can I have a beer?" she asked in this pleading little girl's voice as she bent forward. 

Her tits were now on full display to me. I know she caught me looking a few times earlier tonight. What was she trying to do here? I paused to give her tits the inspection they deserved before I glanced at her face and laughed.

I was under no impression that Daisy actually wanted me. Regardless, I did appreciate the view I got. I was more annoyed that she thought I would be so gullible. I see tits every day at work.

She immediately stopped smiling as my laughter began. I suppose I wounded her little ego.  I tried to soothe her with "Aww baby, don't be upset!" But I couldn't stifle my chuckles. "Your tits are nice," I lowered my eyes and gave her another good look. "Real nice tits," I concluded, nodding my head. Daisy rolled her eyes, stood up straight, and crossed her arms in front of her. 

I just kept smiling. She was cute when trying to be haughty. I didn't mind seeing those huge breasts pushed up more. I caught a little glimpse of some purple lace under her shirt.

"Isn't that what you wanted me to say?" I demanded. Daisy only pursed her lips in defiance. "Did you really think I would give you alcohol if you flashed me a little cleavage?" I snickered.  "You'd have to show me a lot more than that!" I reached out to offer her a glass. "Here, have some juice!"

"I'm not a baby!" She snapped.

"I can see that!" my tone dripping with sarcasm.

"I've had alcohol before. You're not corrupting me or anything," she pouted, ignoring the drink I offered. I let out a frustrated sigh as I tried to keep my focus on her face. "Getting drunk with you would be...a bad idea"

Before she could respond, a loud moan came from Mike's room upstairs. It was followed by the dull thumping of his headboard hitting the wall. I smiled to myself. Mike now had his 'future wife' right where he wanted her. 

The increasingly louder sex sounds made Daisy smirk at me. My cock hardened at her expression. All sorts of thoughts ran through my head. I had this tasty little piece in front of me. Why hold back? I decided to see if she was interested in a little fun.

I quickly walked around the kitchen island, and Daisy twisted around to face me. Her smirk morphed into a beautiful smile as more sounds erupted from upstairs. She backed herself into the island as I leaned in. She pulled away, leaning further back over the counter forcing me to lean over her. Her big eyes darted across my body, waiting for my next move.

"You're not a baby, isn't that what you just said?" My hands grabbed a hold of her waist and pulled her midsection to mine. "Are you hard of hearing, old man?" She quipped. I quickly brought my hand to her chin, roughly sliding my thumb over her lips to swipe her lip gloss off. She surprised me by parting her lips to swallow my finger.

Daisy sucked on the tip of my thumb. I smiled as my cock grew inside my jeans. Her pretty eyes dared me to do more. I leaned in to plant a soft kiss on her lips. "I guess I don't have to worry about corrupting you," I whispered into her mouth. I pressed my body into hers, letting her feel my hard cock. I expected her to push me off, but she just slid her hands under my shirt. I leaned back slightly to see her face. 

She looked ready to be fucked. As I brought my mouth down on hers, I tasted the cotton candy from earlier in the night. Her whole mouth was sweet. I liked it and I dove in deeper. Her sweet tongue slid against my own. 

Her eagerness only excited me. This was a whole different attitude from before. I reached up and grabbed her left breast, hard. Daisy moaned into my mouth. I impatiently pulled up the bottom of her shirt, slipping my hand under to squeeze her breast again. It was so soft and supple in my hand.  My fingers tugged on her budding nipples through her bra.

She let out such a moan, it made me tug harder. Her hands moved to the front of my jeans, tugging at the denim, trying to free me. I backed up a little to slide everything down. Daisy wasted no time dropping to her knees. In the next moment, she was on me. I threw my head back as her tongue slid over my cock slit before sliding her pink tongue up and down my shaft. I almost shuddered in surprise.

Her mouth was wet and warm. I was mesmerized watching those pretty eyes as they stared back up at me. She kissed and sucked and licked me all over. She made long and slow bobbing movements as she eased my cock further and further down. I didn't have some monster cock, but her tiny mouth stretched to take me like an Anaconda inhaling a big meal. She was making these full, sexy slurping sounds, I took a moment to turn my head away to listen for anyone coming from upstairs. I'd hate for them to find us like... "OH GODDAMN!" I cried out. Daisy's hands her hands gripped my as she bobbed her head roughly on my cock, forcing me down her tight throat. 

The light gagging noise almost pushed me over. I feared I was in danger of embarrassing myself by cumming too quickly. Thankfully Daisy pulled away, giving me a moment to recover, leaving a trail of saliva from her lips to my cock head. It was picture perfect. She began nuzzling my balls, rubbing her face against them. I opened my legs wider to allow her to slip further between my legs to lick my perineum. 

"Keep sucking me," I grunted as I reached for her head. She playfully slapped my hand away before pulling her shirt off and unhooking her bra. My head turned to the stairs, fully expecting to be caught. She gripped me, firmly pulling my focus back as she licked the underside of my cock. "Ohhh" I moaned in protest as she pulled my cock from her lips. She held up one of those big heavy tits and  rubbed my cock head over her stiff nipple. 

Her areolas were so big and sexy. I imagined circling them with my tongue. I immediately reached down to squeeze on her breast. My thumb brushed across her nipple over and over. Daisy resumed sucking, cupping my balls in one hand, while roughly jerking me to her mouth with the other. I jerked my hips forward to push myself further in. Saliva fell from her mouth onto her chest. I slapped and pulled at her nipples as she moaned over my cock. 

"I'm fucking cumming!" I hissed as Daisy locked eyes with me. "Let me see it before you swallow it," I blurted breathlessly. She gave me a small nod before I finished. I shot into her mouth four times before I jerked my hips away with the last shot. As I stumbled away, Daisy leaned back on her heels and opened her mouth. I saw a blob of white covering her entire tongue before she threw her head back and swallowed. 

"That was fucking nice!" I murmured before bending to pick up her shirt and bra from the floor. I reached out and pulled her up from the floor. "Now let's go to my room and make you cum." She smiled as I pulled her into my arms and gave her a quick peck on the lips. Her eyes widened in surprise.

As we entered my room, located behind the kitchen on the first floor, Daisy pulled out her phone from the back pocket of her shorts. Before I could protest she said, "I'm texting Christina to tell her you will drop me off and not to worry about me." She put the phone on the nightstand and bent forward and started shimmying out of those tight shorts. I hurriedly got naked. 

Without her clothes on I could see her small waist and the sexy curve of her hips. "You're so beautiful," I whispered, inching closer as I stroked my cock. I needed more time to get ready but I was more than willing to eat some eighteen-year-old pussy. Daisy smiled as she began crawling towards my pillows. 

That's when I saw the shiny black buttplug between those fat cheeks. "Holy shit! Did you have that in this whole time?" I quickly moved to squeeze her ass cheek before she flipped onto her back. In my eagerness, I gripped her knees and spread her legs wide. She revealed a nice, fat, almost hairless pussy. 

"I kinda had other plans for tonight but this is just as good," she explained. I chuckled to myself. Whoever that was for, it's his fucking loss! "This is so sexy," I traced the middle of her pussy lips down to her asshole. My finger circled the rim of the black, jewel-like plug in her ass. I couldn't wait to pull it out. But first things first. 

I spread her lips open and revealed her stiff clit. I leaned in to brush my nose and lips over it. I gave it a long lick and then a suck. Daisy released a loud moan before covering her mouth with a fist. I lifted my head. "You're so wet already. Did sucking my cock get you this wet?" Our eyes met and Daisy responded with, "Less talking and more sucking!" She groaned as I dove back in between her legs.

I ran my tongue slowly over her clit hood. My index and middle finger slipped inside her. I slowly penetrated her, back and forth as my head moved up and down in tandem. In the last few minutes, my cock hardened. I was ready to get inside of her ass but I wanted her to cum first. I was so eager to taste jer juices, I began to move faster. My head shifted from up and down to side to side to alleviate my jaw. I pulled my fingers free from her wet channel and gave her butt plug a gentle pull. 

Daisy arched her back and tried to twist her body to her right side. I  squeezed her ass cheek as it came up off the mattress. I tasted her cum as she rolled back into her back. Her chest heaved and she covered both eyes with the heels of her palms. Her cries were so desperate and sexy. Those thick thighs closed over me like a fleshy bear trap. I pulled myself from between her legs and put my entire weight on her. I wanted to kiss her mouth, letting her taste herself on my lips. 

She wrapped her legs and arms around me with her body still shaking. She sucked on my bottom lip as I squeezed my hand between us to hold onto her breast. I buried my head in her neck as her fingers racked over my scalp. I lifted my head to whisper in her ear, "I want to be inside you," 

She nodded and I eagerly slid down her body. I grabbed both tits in my hands and pushed them together. My head moved back and forth from one nipple to the other, sucking and licking. My hands massaged them, moving them in small circles. It was nice to finally get a hold of them. Daisy giggled and yelped before I finally relented. "Ok let's do this." I pulled out my lube but kept it to the side. Daisy lifted her leg to reach for the plug but I said, "No, leave it in for a bit." I rubbed myself over her pussy lips before pushing myself inside her.

She was so nice and tight, we both groaned as I bottomed out. "This feels so good, Nic," she moaned. I rubbed her clit while pressing down on her abdomen. After a few hard strokes, she came again. Her toes curled. Her fingers dug into my sides as she cried out my name. I buried myself inside to enjoy it. I could have stayed there but I couldn't forget that her ass was prepped and ready for me. I pulled out completely and slathered myself with lube. Daisy rolled herself onto all fours. I held her hips and jerked her towards me. Her thick sexy body giving me the confidence she could handled being manhandled. I massaged her ass before sliding her cheeks apart to gently tug on the plug.