It was the middle of July and I had recently been dumped by my seventeen year old girlfriend. I was twenty at the time and fairly inexperienced. While I really liked my ex, I certainly wasn't in love, and perhaps the biggest frustration and disappointment I was having was that we had just started to get physical with some light play. Specifically, I had been introduced to her beautiful breasts and she had given me four handjobs at that point, and the last time we played she allowed my fingers to roam down inside her panties. While my friends had all lost their virginity and were on to their second or third partners, I was the lone virgin who had only merely had his dick tugged. When the subject came up, they all called me lame, but I knew they were just giving me a hard time. That summer, I was determined to change my course and finally advance my sexual experiences, and fast!
I had pondered the idea of using Tinder or PlentyOfFish, but the idea of putting my photo on something and being 'out there' scared the shit out of me. If anyone I knew found out I was online looking for a hookup? What if my parents and friends found out? I'd be humiliated for life. This steered me in the direction of a phone chat system, and I had found two with free trials for 40mins each. Bingo! I dialed up the first service and to my dismay, the women were mostly thirty to seventy years old and from all over the United States and Canada. Where were the local girls? The girls my age? This sucks! Further to that, I received my first response at thirty minutes into the call with only ten minutes remaining. Soon enough I was out of time. What a disappointment! I called the second service and utilized that free trial, only to discover the same thing. On the call, the service gave me a five minute warning that my time was running out and prompted me to purchase time - fuck that! With four minutes remaining, I hear the sweetest little voice, "Hey, it's Teagan. Just looking to chill with a cool guy my age. I'm eighteen and pretty", she giggled. I hit the keypad to find out what city she was in, and she was local! I scrambled to get out of the automated message that was telling me her city, repeating her profile, etc... madly trying to message the girl. Finally, I got my message off, "Hey, Teagan. It's Sean! I'm free to hangout, and I'm twenty and good looking. We should chill, but please message me back fast because I'm on a free trial and out of time. Please!" I hit send. SHIT! Why didn't I leave my snapchat or text? Dammit! I tried to find her ad again, but she was nowhere to be found, and finally I received another warning that my free trial was over in less than a minute. FUCK!! Just when I thought my time was running out and I was about to prompted to purchase more time, there was a new message chime. Please please please.... "Hey, Sean. You sound nice. I'm not up to much but if you wanna chill I'm just hanging at the Federation Park by the playground, it's close to my house." I attempted to replay the message to ensure I had the right park, but my free trial sadly ended. Dammit! Federation Park? Ok, let's see what's what, I thought. I quickly showered, threw on some shorts and a t-shirt, and made up some excuse with my parents as to why I was borrowing the car, and I drove to Federation Park.
I parked in the lot at Federation Park and looked over the playground area. Just four younger girls on the swings, and no one else to be found. The playground was only a small section of the huge park that had clusters of trees and bushes throughout with large sections of nicely kept grass. I waited in the car a bit, hoping a lone Teagan would make an appearance. Finally, I stepped out of my car and walked past the playground further into the park looking for a young lady that I realized I had no idea what she looked like. I walked past the playground again and the girls on the swings, deciding to walk up and down the street a bit - she said she lived a few houses away. I walked ten houses to the left, and returned to the park before walking ten houses to the right. Albeit the plan was doomed from the start, I was disappointed. Disappointed that there wasn't a lone eighteen year old pretty girl named Teagan sitting on a bench at the park who'd immediately come up to me and ask if I was Sean, and that we'd hit it off and spend the day together followed by some sort of sexual adventure. What was I thinking? My friends are right, I am lame! After spending nearly fifteen minutes or so walking around in circles in front of four giggly younger teens, I decided it was time to give up and shamefully drive back home. I headed for my car, opened the door, and...
"Hey! Are you Sean?", a girl called out just as I sat in my car. I quickly bolted up to look over the roof of my car, scanning the park for Teagan who'd surely save me from a summer of lameness. Nope, no Teagan - just the four girls on the swings. I stared at them awhile as they whispered and giggled. "Teagan's right here!", one giggled as they sat on the swings, swaying casually back and forth. I looked them over - there's no way one of them was Teagan, these girls looked fourteen? Or, had I been catfished and setup on some humiliating prank. "Sean? You are Sean, right?", the smiling brunette called out as she pointed to the petite brunette beside her, "Teagan".
"Stop! Seriously! Just let him go", another smaller brunette whispered loud enough I could hear as she pulled her friend's arm down.
I stood there unsure of what to do. Not only is Teagan not eighteen, she has all her friends around, and this is awkward as fuck! My face turned red, and I slowly started to sink lower towards my car seat.
"Oh, no! Don't go! Come chill with us. For real!", the brunette called out as her friends giggled.
I stood back up and looked at them, dumbfounded. What's the worst that could happen? They could all laugh at me and run away as soon as I got close to them. What's the best thing that could happen? I don't know, they're like fourteen, and this is a terrible idea.
"I think he's shy", the bold brunette said loud enough for me to hear.
Dammit, even a fourteen year old thinks I'm lame as fuck. I'm being shown up by a kid! I closed my door, pride(?) urged me forward as I walked towards the girls, glancing over each shoulder to see if anyone was looking. As I got closer, I could feel my hands getting clammy even though it was hot as hell out. All four sets of eyes watched as I approached.
The bold brunette hopped off her swing and had this wide shit-eating grin on her face. "You are, Sean, right?"
"Ya", I said as I quickly glanced over the girls, afraid to look at them for too long as I quickly glanced back to the brunette.
"I'm Cassie", she smiled at me. Cassie was tall for her age, maybe 5'8, lean, wearing loose fitting little grey shorts that were low on her hips and showing off a very flat little tanned abdomen. She wore a white crop top over a perky small chest, and I didn't have to stare too long to see the outlines of her nipples through the material. Cassie was cute, and apparently the ring leader of the group.
"Hi", I croaked and I held out my hand.
Cassie looked down at it and giggled, "Really? A handshake?" She turned to her friends and motioned for them to get off the swings. She eyed the blonde who stood next to her, "This is, Lia". Lia was about 5'6, average build, cute, but not pretty, but it seemed she filled out her black tanktop fairly well over her denim shorts.
"Hey", I smiled at Lia, and she cracked a smile but seemed to shy to respond.
Cassie leaned and pointed to the redhead beyond the petite brunette, "This is Alex". Alex was pretty plain. She was super skinny, pale complexion, long red hair, and wore a red tanktop over black shorts. The tanktop wasn't hiding anything, because there was nothing really to hide - Alex was completely flat.
"Hey", I smiled.
"Hey", she smiled back.
"And... this is your date", Cassie grinned and hugged the petite brunette. "This is Teagan. Teagan say hi, to Sean", she teased.
Teagan held her face in her hands, and finally after some laughs, "I can't believe you guys are doing this to me". She looked up from her hands, "Hi, Sean". Teagan's face was beat red, and she had beautiful curly brunette hair. The girl was maybe 5'3 and tiny. She wore denim shorts and a spaghetti strap white tankop that covered smaller perky breasts that pointed nearly straight out. The way her tank fit, the faintest of outlines were visible that immediately caught my eye.
"So, you gonna chill with us?", Cassie beamed at me.
"Uh. Sure... if you want me to", I said.
"So, how old are you?", Alex asked.
"I'm twenty. Why, how old are you girls?", I responded.
"We're all eighteen", Cassie blurted as she made wide eyes at her friends.
I was thinking to myself, bullshit... there's no way. Sixteen would even be a stretch.
"Twenty, hey? Hmm...", Cassie looked me up and down.
"Why? Is that okay?", I asked.
"I was hoping you could maybe get us some vodka, but that's okay", she slowly nodded. "But... we should go for a walk? Like maybe in the trees?", she smiled again.
Despite her young age, I was so drawn to Cassie. She was cute as hell, and I was constantly trying my hardest not to stare at her tube top. "If you want to", I said.
"Come on...", Cassie waved everyone along and she walked the group further into the park away from the parking lot, and eventually into a cluster of trees. Her friends whispered a lot, and it made me nervous. "Do you have a girlfriend, Sean?"
"Of course he doesn't. He's on a phone date thing. Duhhh", Lia laughed.
"Na, I broke up with my girlfriend like a month ago", I responded.
"Is it big?", Alex whispered with a giggle.
"What?", I looked to her, unsure of what I thought I heard.
Cassie stopped in a cluster of trees where no one could see the group of them. "This is good, ya?" she smiled.
"Sure. But, what are we gonna do?", I asked.
Lia laughed, "You never answered the question".
"What question?", I said, feeling I was being made fun of and Tegan just looked all around uncomfortable.
"Is it big?", Alex asked while partially covering her face from embarassment.
"Umm... is what big?", I replied.
"She's talking about your dick", Lia giggled and playfully swatted at Alex.
"Uh, are you for real?" I said with a red face.
"Ok, like is it longer than a soda can?", Cassie chuckled.
"What? You girls are crazy!", I nervously laughed.
"Just leave him alone, guys", Teagan piped up.
"Maybe he should show us", Alex stared at me and then looked down to my shorts, "It doesn't look big".
"What? You can't even see anything through my shorts. It's big enough", I defended myself, frustrated that these younger girls were making fun of me.
"Well, then you should take it out and show us", Cassie winked and chewed her lip.
"Crazy. You girls are fucking crazy", I nervously laughed.
"No, for real. Can we see it?", Cassie looked at me with a straight face.
"You wanna see it? Seriously?", I asked. Cassie slowly nodded. Alex and Lia grinned.
"Guys, this is getting out of hand", Teagan slowly shook her face in her hands.
"I'm not just gonna whip it out in front of four girls I just met. Come on now...", I shook my head in disbelief.
"Ok, well what do we have to do to see it?", Cassie raised her eyebrow.
"Well, if we're playing this game, I'm certainly not going first... there's four of you", I figured that would quell their persistence.
"So, if we show you something first you'll take it out and show us?", Cassie smiled.
I gulped. For years, it took forever to get a girlfriend, let alone a girlfriend who'd finally let me remove her bra and feel her tits... and now, just like that, I have four girls wanting to flash me? They're young... too young? Too young... why is life so cruel! My face reddened and my body tingled. I can't do this, I thought. I need to get the fuck out of here! I could tell, Cassie was waiting for her response and there was nothing but this awkward silence.
Unexpectedly, Cassie formed a smug grin and she placed her fingers at the top of her tube top and pulled it down. Two very firm smaller breasts with tiny hard nipples were exposed right in front of me, and just like that. "Fine. Your turn", she said.
I stared at her exposed breasts in disbelief, my gaze dropping down her abdomen that seemed to go on forever. She was stunning, and it seemed if her grey cotton shorts were any lower I'd be seeing the top of her privates. Alex and Lia started to giggle. "Uhh.... umm... but.... uhhh.... what about the rest of you?", I squeaked.
Alex and Lia stopped their giggles, their faces turning straight and pink. "What?" Lia asked, "I didn't agree to that".
"Just show him", Cassie urged.
"I'm not showing him my tits", Lia glared.
"Don't bail on me", Cassie argued, "I took the lead, now don't be a pussy", she glared at Lia.
Alex hesitantly lifted her red tanktop to expose her pale torso and chest that had little signs of any development. Just, two blush pink puffy nipples on a flat chest. I couldn't believe my eyes as I looked Alex over.
"Ok, but how long do I got to do it for", Lia pleaded.
"Until he's done", Cassie giggled.
"Done? What do you mean, done?", I asked as Lia lifted her black tanktop and bra. Two medium sized perfect round breasts spilled out to the sun and Lia rolled her eyes as if it was some absurd chore. The three girls looked to Teagan.
"You guys are awful", she hid her face in her hands again, "I can't believe I'm doing this..." And Teagan lifted her white tanktop to expose the two pointiest perky little breasts I had ever seen. He looked over the girls seeing just about every size and shape, and then it dawned on him - he was next.
"Whip it out", Alex laughed as the girls held their tops to maintain their exposure to him.
I slowly worked on the belt of my shorts, and then the button. I didn't think this was going to end well because I'm a grower, not a shower... and because I was nervous as hell, I was afraid my penis would be soft and shriveled. I unzipped my shorts and all four girls watched intently as I pulled them down slightly along with my boxers to expose my very flaccid little penis, and two smoothly shaved testicles that hung low from the heat. I cringed, waiting for their laughter.
The girls stared curiously.
"It's... small", Alex noted.
"Well, it's not like he has a boner", Lia giggled.
"It gets bigger, right?", Cassie asked.
Teagan just stared at it.
"Ya. This is like totally soft, but it gets bigger. Much bigger. Seriously...", I pleaded my case.
"Well... make it bigger?", Cassie grinned.
"I'm not jerking off in front of four girls. I don't masturbate", I lied.
"Bullshit, all guys tug", Lia laughed.
"Ya, we wanna see you tug it", Alex added.
"Guys, this is super uncomfortable. Can I pull my top down now?", Teagan asked.
"No. He needs to get it hard", Cassie said.
"I need like... stimulation to make it grow", I said.
"Ya. So tug it", Cassie giggled.
"I already said i'm not doing that", I shook my head, "but, feeling your tits would make it grow". I felt shy even asking and it felt like my ears were on fire.
"Fine", Cassie said as if it was nothing.
"What?", Lia blurted.
"They're just tits", Alex rolled her eyes.
"Ya, cuz you got none", Lia snapped back.
"Just let him do it so we can see it better", Cassie laughed.
With my cock hanging out of my shorts, I leaned towards Cassie in disbelief as I was about to touch her perfect body. I gave her breasts a gentle squeeze, admiring how they were way better than my ex-girlfriend's tits. I rolled her nipple between my finger and thumb, and my penis started to shift and grow.
"I think it's working", Cassie said as she stared at my dick.
Alex tentatively stepped closer waiting for my hand. There wasn't much to feel, but I brushed my fingers over her chest and played with her nipples for mere seconds, and then turned my attention to Lia. I took a deep breath, and as I cupped her heavier breasts my cock was sticking straight out to Alex's and Cassie's delight. I gently squeezed Lia's tit and brushed my thumb over it, admiring how she closed her eyes and bit her lip.
"Shit, I didn't think it would grow that much", Alex giggled. Cassie was silent. I looked down to see my cock starting to angle upwards with hardness.
Teagan looked afraid, but she didn't protest as I reached out to run my fingers over her breasts and nipples. I gave them a squeeze and Teagan's eyes closed. Without even looking I could feel my cock throbbing and the faint trickle of the precum that had escaped the tip to run down my shaft.
Alex leaned to Cassie, "Is that his cum?", she giggled. "Did you just blow?" She grinned at me. Cassie's boldness was out the door as she stared at the glistening fluid.
"No. Just, like pre.. cum", I explained.
Alex leaned in closer and held out her finger to scrape it off my tip. I watched as she pulled her finger away, leaving a small strand of fluid connected to the tip of my cock, completely unaware that I was still squeezing Teagan's breast like a stress ball. Alex held her finger up in the sunlight and admired the translucent fluid before she giggled and wiped it on Lia's shoulder.
"Eww! Fuck off!", Lia giggled as she wiped her shoulder. "I don't want his cum on me".
"It's not cum. He said it was his pre.. whatever", Alex laughed. "Well then, what does cum look like?"
I suddenly pulled my hand from Teagan's breast, sensing my hand had overstayed it's welcome. Her face was pink and she opened her eyes wider and looked down to my cock that was oozing precum strands to the grass below.
"We wanna see your cum", Alex giggled.
"Ya. Squirt it", Lia added.
Cassie watched the strands of precum leak from my tip and reach for the grass, glistening in the sun.
Lia nudged Cassie, "You wanna see him squirt it, don't you?"
Timidly for once, Cassie whispered, "Ya. Ok".
"I already said, i'm not jerking off in front of you", I shook my head.
"Aww, please? You like us don't you?", Alex grinned.
"Just this once?", Lia asked.
I tried to think of an excuse, "It's dry. It'll hurt to rub it". I lied, sort of... I mean, if I was horny enough I'd dry rub anywhere if I wouldn't get caught.
"Do you use like lotion? or lube?", Lia asked.
"Ya", I said.
"Got you! You said you didn't masturbate", Alex laughed.
"Well, like not often. Like everyone does", I defended myself.
"But I wanna see it squirt", Lia pouted. "You can play with my boobs if you do it for us", she winked.
"Honestly, I just don't think I could do it with everyone watching", I said with a lump in my throat.
"You should suck it", Alex gave Lia a playful shove.
"Fuck that, I ain't sucking shit", Lia took a step back. "You suck it".
"Guys, I think we should go", Teagan squeaked.
"I'm not sucking it. He's not my date", Alex laughed, and turned her eyes to Teagan.
"Guys..." Teagan said with concern.
"Cass? What do you say?", Lia asked Cassie who continued to stare at my flaring tip that continued to ooze. "Cass?"
"Ya, she should do it", Cassie said coldly.
"Guys, no... ", Teagan giggled nervously.
"Do it, Teagan", Alex urged her.
"Ya, go on... just for a bit", Lia said.
"We've all done it before... time for you to step up", Alex laughed - totally lying, because none of these girls had even seen an exposed cock before in their lives!
I stood there nervously, unsure of what was about to transpire, my cock throbbing and bobbing up and down in front of the girls.
Alex gave Teagan a shove towards me, "It's your turn. Just do it". The shove was hard enough, Teagan stepped into my erection, leaving a wet smear of precum across her thigh.
Teagan stood right in front of me and gulped as she looked up at me.
"Teagan. Teagan. Teagan. Teagan...", Alex and Lia urged her on as Cassie's mouth hang open in shock as Tegan lowered to her knees in front of my throbbing erection.
"I don't know what to do", Teagan covered her face in embarrassment.
"Lick it!", Alex laughed.
Teagan placed her index finger and thumb around the shaft and I couldn't believe my eyes as Teagan reached out with her soft pink tongue to brush the tip of my cock, and cleaning off the precum that had escaped the tip. She pulled her tongue back in her mouth and swallowed. "There".
"No, like full on put your mouth on it and suck it", Lia giggled.
Teagan's eyes flashed up at me for a moment before lowering to the work at hand. Ever so slowly, Teagan closed her eyes and wrapped her lips around the tip of my cock. The warmth and wetness of her mouth was mind blowing as I stared in disbelief.
"Holy fuck", Cassie whispered next to me as she watched.
"Like this?" Teagan looked to Alex with concern as if she wasn't doing it right.
"Ya, you gotta move your mouth on it though", Lia grinned.
Teagan slowly took more of my erection in her mouth, sucking slowly until her cheeks hollowed.
I felt a shot of some drug had flooded my brain, and I was weak in the knees as I experienced the most divine experience in my life as Teagan slowly sucked my cock in front of her friends. It was a high, like I was drunk or shooting heroin. Overcome with lust, and not fully in control of my actions... my hand reached for Cassie's breast and once again I gave it a squeeze as Teagan sucked me.
"Spit on it", Alex giggled.
Teagan pulled her mouth off my glistening erection with saliva and precum trails connecting my head to her lips, and she hawked up some saliva and spit a gob of white saliva on the top third of my cock. The spit hung, and she quickly put her mouth back on it to keep the saliva in play. Subconsciously, my hand had already travelled down Cassie's abdomen... I wasn't even really looking... until my finger brushed her navel. I looked to her, and Cassie looked back at me, stunned. She was so fucking hot... and she wasn't stopping me... I slipped my fingers into her loose fitting grey shorts and they immediately felt the top of the tiniest little panties I had ever felt. Cassie was frozen, her mouth still hanging agape as her eyes lowered to my hand. I closed my eyes as Teagan seemingly worked more and more of my erection into her mouth.
"This is fucking wild", Alex giggled.
"Tell us when you're gonna spray it", Lia laughed.
My fingers pushed further, and I felt the little hood over Cassie's clit and the warmth of soaked little folds of her pussy. Cassie trembled to my touch, long gone was the bold brunette that started this all. I felt the tip of my erection hit something, and then there was a guttural gag from Teagan as I looked down to see most of my erection stuffed into Teagan's throat to the glee of Alex and Lia. It was right at that moment, my finger slipped inside the slick tight hole of Cassie's pussy. I turned for a peek, noticing Cassie's shorts were so low that I could see a little patch of hair and the sexy little lump of her hood as my finger plunged deeper into Cassie's pussy. Cassie let out a gasp. Teagan let out a cough. And then all hell broke loose....
Without warning, an eruption boiled in my balls and a mass so thick with volume rocketed up my shaft and stung my tip as it fired into the back of Teagan's throat. In a panic, I looked down to see Teagan's eyes flash wide open as another slightly painful burst shot up my cock and out the tip, choking poor Teagan as she ripped my spurting erection from her mouth just in time for the third spray to launch a thick rope of bright white sperm across her lip, nostril, her left eye, and forehead.
"Oh, shit!!!", Alex gasped.
Teagan scrunched her eye and coughed up a bubble of sperm as another squirt of semen smacked her forehead as if shot from a sniper's rifle with an audible spatter. The cumshot quickly oozed down either side of her nose. Teagan continued coughing and pointed my erection to the side, causing the next spurt of cum to lob up into the air and hit the side of Alex's foot.
"Ewww!", Alex screamed and laughed. "Quick! Run!", she hollered while giggling as she ran through the trees and yanked her tanktop down.
"Wait, I'm coming!", Lia giggled as she pulled her top down as she ran.
Teagan looked up at me with one eye as her face looked like a canvas of wet white paint that hung from her chin. She continued to cough and keeled over onto all fours, before rising to her feet and stumbling back to the ground.
With my finger still firmly inside Cassie's pussy, we stared at one another for a moment, speechless.
"I should get going", Cassie whimpered.
I slowly withdrew my slick finger from Cassie's panties, and couldn't form any words. I just stared as she slowly pulled her shorts up and adjusted her tanktop. I went to speak, but nothing came out, and yet Cassie didn't leave... she stood there staring at the thick strand of sperm hanging from my cock.
"That was... fun", Cassie shrugged her shoulders as she finally took two steps back. "Tomorrow?", she whispered as she continued to back away. I slowly nodded, and she turned and ran after her friends.
Holy fuck! What just happened!? I looked down at the cum all over my sandals and foot. I felt a fly buzz near my face and as I went to brush it away, I caught the sweet scent of Cassie on my finger. I slipped my finger in my mouth, savoring her slickness that was still present upon it and sucked it clean. I was in heaven. I had my first blowjob. And this summer was off to a great start.