9 comments/ 121640 views/ 33 favorites Angie's First Time By: 5425TVR "Fuck you too, bitch!" I screamed as I slammed the door of my girlfriend's apartment. We had been out; she was drunk and had flirted with several other guys. We left the bar early, fought all the way home and I was tired of the bullshit. She knew I had a short fuse but didn't really care. She felt underappreciated as I shot the shit with my buddies and this was her way to rebel. If the sex wasn't so good, I would have dumped her months ago. As I reached my car, I realized Bill, my roommate, had asked me to spend the night someplace else. He had asked his new girlfriend over and wanted to seal the deal. Not wanting to screw his night up, I decided to drive across town and sleep at my parents' place. As I parked my car, I noticed the lights were still on in the basement. I figured mom forgot to turn them off and I would go down before I went to my room. As I made my way down the stairs, I was surprised. My sister who was a senior in high school had some of her friends over for the night. When I realized this, I started to quickly and quietly retrace my steps. Then, I heard, "Truth or Dare?" My sister asked Shannon, one of the hottest girls I had ever seen. Shannon quickly replied, "Dare." Shannon was the captain of the cheerleaders. She was a blond, 5 feet, 10 inches tall, weighed about 115 pounds and had a stunning 36C-24-36 figure. I can't even remember how many times she caught me staring at her tits and ass. She was fine. My sister grabbed the beer bottle next to her, guzzled the last bit and said, "You cock sucking queen, show us how you can deep throat this." Shannon displaying her sultry sexual charms, took the bottle, seductively teased the head with her tongue and dipped it into the bottle's opening. She slowly licked the long neck of the bottle. Small traces of saliva began to form and run down the neck to her fingers. Seeming satisfied with her efforts to lube it nicely, she tilted her head back and held the bottle at the base with her thumb and fore finger. In one glorious move, she had the bottle down her throat with only her two fingers showing. She gently moved the bottle up and down a few stokes and withdrew it slowly. My sister and her two other friends clapped with their approval. Shannon quickly added, "No one has ever lasted that long. I usually have spunk running down my throat at this point." She followed this up by seductively running her tongue over her lips and then took her finger and slowly wiped the corner of her mouth as if catching the last remains of cum running out the corner of her mouth. Then, as if on cue, she sucked that finger to get the last drop. My sister and her friends cheered. I guessed that my parents were out because the noise would have sent my dad into a wicked frenzy. Shannon quickly asked Heidi, "Truth or Dare?" Heidi was not to be outdone so she chose "Dare" as well. Heidi was a brunette, 5 feet, 9 inches, weighed 122 pounds and had a figure of 34B-26-34. She was the first of my sister's friends to enter puberty. I will never forget the summer day she came over in her bikini top with 'real tits' proudly displayed. Shannon wickedly said, "Anne, get the shaving cream, razor and a scissors. Heidi, you are going to trim that wicked muff of yours." Anne quickly bolted toward the stairs. I turned and hurriedly made the corner before my sister saw me. I sprinted as quietly as possible to my bedroom. My sister ran into the only bathroom of the house only ten feet from my room. I nervously waited for her to burst through my door to bust me for spying on her friends. She must not have noticed because she quickly ran back down the stairs. I turned and walked to my bed. As I walked, I noticed my mom still kept the room the same as the day I left for college. The posters of Madonna, the Go-Go's and Heather Locklear, all in scantily clad outfitters, lined my walls. They never failed to give me a rise and after watching Shannon's performance, I was rock hard. As I stripped my clothes and got into bed, I slowly stroked my cock while I listened to the girls continue their game through the heating vents located on the floor by my bed. I heard the giggles as I assumed Heidi displayed her hairy muff. The snips of the scissors and the surprise of the loud first squirt of shaving cream filled my room. The girls "Oh'ed" and "Ahh'ed" as Heidi's muff slowly transformed from a hairy jungle to a neatly trimmed piece of artwork. Shannon joked with Heidi, "You will attract more boys with a neatly landscaped bush than with a dense overgrown jungle." Everyone, including myself, laughed. Heidi now challenged Angie. Angie was the athlete. She was a brunette, 5 feet, 8 inches and weighed 108 pounds. She was the state champion in five track and field events for her four years of high school. Her toned well-defined chiseled body was the envy of most Olympians because she didn't have to workout much to maintain this ripped body. However, her 32A-22-32 figure was the most boyish of the four young women. The precedent had been set. Angie could not do anything but select "DARE." Heidi, whose devilish mind was churning, knew Angie was still a virgin. Her tom boyish actions and boyish figure had not attracted many suitors. Heidi turned to Angie and said, "Show us your hymen you fucking virgin." There was a pause and Heidi added, "Stop blushing and spread those pussy lips." I heard some mumbling and the girls laughed. Finally after a few moments, I heard clapping and cheering as I can only assume Angie had stretched out her sweet virgin lips and let her girlfriends view her tight virgin ring. When the cheering died down, I heard some rustling. Then, louder than I expected, Angie challenged my sister. Now, my sister, Anne, was the most brazen of all her girlfriends. She led the pack and constantly embarrassed and belittled the girls. She had dirty blond hair, was 6 feet tall, weighed 150 pounds and had a 36C-28-36 figure. As kids, I nicknamed her 'Amazon Anne'. Before Angie could even get her question out, my sister said, "DARE, you little bitch." Angie must have grown a pair because what came out of her mouth floored the girls and me. "Let's stop fucking around; we know your brother is upstairs. I dare you to give him a blow job and bring the proof back here." The girls went wild and my mind raced. There was no way my sister was going to blow me. Quite frankly, there was no way I was going to let her. As I tried to figure a way out of this situation, my door slowly opened and my sister entered. I looked at her and bellowed, "Not in this fucking lifetime!" I heard the girls' chuckle from the basement. She looked at me with those sisterly eyes that read "I can't let that little bitch win." She approached and whispered in my ear, "You do this for me and you'll have all the girls tonight." She could tell I was pondering the thought, but I just couldn't. I whispered back, "I can't." She said, "What if I tell mom and dad you dropped out of college?" How in the hell did she know that? I was failing miserably and hated college life. A friend offered me a good job as a mechanic and I took it last week. But, mom's dream was to have me be the first college graduate in the family. The blackmail worked, "OK, you win, but if you tell mom before I do, I will kill you!" I hissed at the bitch. My sister whipped back the covers. I was naked and my seven inch cock strained and oozed its pre-cum. My sister looked at it almost studying it and gasped, more for the benefit of the girls downstairs, "This is the biggest cock I have ever seen!" I heard mumbled chatter from the girls in the basement. My sister smiled at their reaction and she grabbed my throbbing cock and roughly gave me a hand job. I complained, "Take it easy." This caused a slew of laughter from below. I finally realized I had fallen into my sister's trap. She was planning on embarrassing me as well as her friends tonight. Just then, I had a wicked thought pop into my head. I was going to turn my sister into my sub-bitch tonight while I fucked all her friends. I said, "Oh gawd, I'm getting close." My sister neared hoping to have me cum on her face and take the 'evidence' back to her friends. I whispered for her to open her mouth or I wasn't going to cum. She looked at me with a snotty look and then, did it. I am sure she thought she would close her mouth when I gave any indication I was about to cum. What she didn't expect was me taking her head with both hands and shoving her head on my long meaty pole. She gagged and fought back. I pushed harder. Gagging, coughing and gasping for breath, I held her firm and told her I would keep her there until she passed out or she could give me a proper blow job. She knew I had a temper and knew she cross that thin line that sent me off. She started sucking and I slowly released my grip. She immediately breathed deeply and slowly began to work my cock. I could tell by the look on her face, she tasted the remnants of my girlfriend's pussy and the load I shot deep into her pussy before we went out. She seemed to really enjoy the taste of the combined juices dried onto my cock. As her tongue flicked, she slowly began to hum. I started to get vocal hoping the girls would venture upstairs to watch the show. "Oh yeah! Suck that big cock, sis! All the way. Yes!" I bellowed, exaggerating the affects of my little sister's efforts. I heard more muffled noises from below. I was sure they all wanted to witness this depraved act. I continued my verbal teasing, "Oh baby, you are the best. Suck my cock. Yeah, like that. Oh, yeah." I stopped to listen. Silence followed as I heard the girls whispering as they made their way through the kitchen. I heard one whisper, "Turn it on." I wondered if my sister had the video camera down stairs for her little party. I heard rumors she liked to video 'certain acts' because she would use them to blackmail her friends to do even more dubious things later. As I looked at my door, I saw the big lens of the camcorder aimed in our direction. In a deep voice, I gruffly snapped, "Girls get over here and film this fuck slut properly." The girls were scared shitless and all went into my room with their heads looking down. I told Heidi, who was holding the camcorder, to film Anne's blow job. Now, that Anne knew there was an audience; she tried desperately to make me cum. She deep throated my cock; she sucked the head while pumping my thick monster with her hands, but I refused to cum. The girls were mesmerized by my sister's cock sucking skills and could not believe I hadn't cum yet. Shannon said, "No guy has ever lasted that long with me." I quickly replied, "Suck it then bitch!" My sister looked at me and I motioned her to stand and watch while Shannon moved between my legs. She licked the shaft to lube it up then angled her neck and took me balls deep. She started swallowing and I felt the contractions around the entire girth of my cock. When I didn't blow, she started humming. Still, I held my load deep in my balls. I looked around and questioned, "Is this the best you girls can do?" Heidi handed Anne the camcorder and she pushed Shannon aside. She jerked my cock and I thought she was trying to rip it off. There was nothing sexually gratifying about her twisting death grip. She saw that I wasn't responding to her jacking assault so she tried to blow me. Heidi's blow job skills were just as bad. She used her teeth and had little to no idea what she was doing. Fearing I would lose my hard-on, I couldn't risk any more time with this amateur. I looked at Angie and said, "Ang, your up. Are you ready to suck the beast?" Angie slide between my legs quickly. For being the mouse of the bunch, she knew how to suck. My cock slide down her throat and she tightened it around the entire shaft. It had a pulsing, throbbing sensation with it. It felt wonderful. As the overwhelming pressure built in my balls as she intensified this action, I held Angie's head still and whispered, "It's time," to let her know I was about to blow. She swallowed hard as I shot my first rope. The stream was more than she expected and some overflowed out her mouth and dripped on her small breasts. A glob of cum hung from one of her erected nipples slowly swinging back and forth as she hungrily searched for more cum. The sight caused me to shoot another powerful load down her throat. This time, she swallowed every drop. I could have continued shooting load after load down this virgin's throat; but, I wanted to satisfy all the women. So, I pulled my still raging cock from Angie's sweet lips. She seemed disappointed by my actions. So, I quickly praised, "Angie that was the best blow job of the night! What you have learned as a virgin has you light years ahead of these girls!" Angie smiled brightly and the other girls looked pissed. Suddenly, she noticed the string of cum dangling from her nipple and quickly wiped her finger over it. Feeling empowered, she seductively brought it to her mouth and nursed her finger. When the gooey mix was pooled in her mouth, she pulled the dangling string out and slowly wrapped the ooze around her finger. With a dancing tongue, she flicked the mix to the tip and slowly put her lips around her dainty digit and swallowed my cream. I laughed when she said, "More, please." "There's plenty more for everyone, baby," I piped then quickly added, "Since Anne didn't complete her DARE, what are the consciences?" The other girls laughed as Anne looked pissed and Angie beamed. Knowing my twisted sister, I was sure there was some sort of degrading activity she had built into the game. Angie quickly replied as if reading an instruction manual, "The person that fails to complete a 'Dare' or tell the 'Truth' MUST 'eat out' the challenging girl until she orgasms." "Nice! Lay here next to me while Anne licks that cute little pussy of yours. Shannon, you suck my dick and Heidi, you film everything." Anne and Shannon got on the bed and started working their magic. From the look of it, this was Angie's first time to have her pussy licked. Her face was glazed over; her breathing became erratic and her knees wobbled as my sister flicked, sucked and nibbled her clit. "Angie, is this the first time someone ate your sweet pussy?" I asked amazed at her reactions. "Yes," she meekly panted as my sister stuck her tongue deep into Angie's tight virgin hole. "Oh my gawd! I'm cumming, I'm cumming!" Angie cried. As the waves of her orgasm racked her small frame, I slide my hand across her tight abs and down to her clit. I ground that little nub while my sister continued to stick her tongue deep into her tight hole. Within seconds, Angie came again with such force she bucked my sister off her virgin twat as a long stream of girl cum shot from her drenched hole. My sister thought Angie peed on her. The stream of liquid was intense. It shot across the length of my sister's body and hit Heidi who filmed the whole thing. Another slightly weaker stream fired from her pussy. As Shannon turned to check out all the commotion, the spray hit her in the open mouth and drenched her face. Shannon quickly put her mouth on Angie's squirting pee hole while this spray shot out. I removed my finger from her clit. I was shocked that this little virgin had the mother of all orgasms. Slowly, Angie came down and lay their panting. Drenched from her neck up, Shannon slowly inched her way up to my lips and French kissed me. As her tongue danced in my mouth, she swished Angie's girl cum around my mouth for me to taste. The taste was incredible. The pungent sexual sweetness of a virgin pussy's first hard orgasm had me ready to fuck someone. As the flavorful kiss fueled my raging hormones, I quickly told Shannon to lay with her head to the foot of the bed. I positioned Angie so her virgin pussy was above Shannon's head while she was in the doggie position. Heidi was between Shannon's legs eagerly eating her sweet pussy while Anne filmed the debauchery about to take place. Needless to say, Angie was wet. Her pussy dripped and little beads of girl cum clung to her fair pubic hair. My cock was rock hard but I needed some lubrication so I pushed my throbbing head toward Shannon's sultry mouth and she quickly lubed the entire length of my prick. With gobs of spit dripping from the head, I positioned my blood engorged crown to Angie's virgin pussy. Her lips were so tight. Somehow, I managed to wedge my massive cock head into her tight channel. With this initial triumph, I slowly and steadily pushed my rod toward her inner depths. The resistance, as well as Angie's rapid panting, increased as I neared her hymen. Angie gasped has Shannon lightly caressed her clit and ran her fingers through her sparse bush. After pains taking care and several minutes, I eventually hit Angie's guardian of her womanhood. When Angie grunted at the initial invasion of my fat hard prick, I momentarily backed off my slow and steady assault. The extreme tightness that surrounded my cock was heavenly in itself. I bent down and whispered, "Are you ready sweetie?" She only gave a little nod. Sensing her uncertainty, I soothingly told her to relax as I tweaked a sensitive nipple. Angie jerked at the unexpected act. It was just enough of a distraction for her to begin to relax. So, I slowly moved in and out of her tight pussy avoiding her virginal barrier. Only a third of my cock patiently sawed its way through this virgin's tight pussy. Angie began to relax fully and actually enjoyed the sensual ride. Then, as I pulled back with just the head of my cock between her lips, I thrust forward tearing my way through her barrier. As I felt it rip, I froze. Angie cried out, "Oh dear god!" Through the reflection on the window, I saw a tear form in her eye. Shannon was still between our legs patiently waiting for this special moment. As Angie cried out, I felt Shannon lick and kiss both Angie's sore pussy lips and the exposed part of my throbbing dick as she tried to ease Angie's pain. Shannon kept licking, kissing and teasing. She knew Angie had to work through the initial pain to feel the true sexual awakening that would change her life forever. Shannon was experienced. The pleasure of her tantalizing flicks and prodding soon overcame Angie's intense pain. After a few minutes when her breathing returned to normal, I leaned down to Angie and asked if it was OK to continue. She whispered, "Yes." Slowly, ever slow slowly, I stroked my mighty girth deeper into her pussy. At first, I tried to only go as deep as the last thrust. My goal was to get her in a nice rhythm before I invaded her tight hole's depths. Finally, she worked into a good rhythm rocking back and forth on my hard cock as Shannon caressed her clit. With these sensations increasing her arousal, Angie began to push as I thrust my cock. I could feel her pussy contract ever so slightly around my base. This was the point in Angie's sexual arousal that I longed for her to reach. I began to thrust harder and harder into her unexplored depths. I wanted to touch every part of this dripping pussy before I let her friends have their way with it. After several hard thrusts, Angie took my cock balls deep. When Shannon saw this, she quickly asked us to change positions so Angie could grind her swollen pussy on my fat cock. Angie was excited to try this and I was only too happy to follow this lead. When I was on my back, Shannon quickly cleaned and lubed my cock with her flicking tongue as Angie assumed the cowgirl position. Shannon held my cock at its base to steady my pulsing beast while Heidi, Anne and I watched. Slowly, Angie spread her sweet lips and sank on my meaty shaft until she reached bottom. She let a loud sigh escape her lips as she clenched her ass checks when my rod found her soft spongy spot. As she ground my cock against this treasure spot, she became more vocal. Angie's First Time Heidi suggested she lie on my chest and grind in that position. Angie did this as Heidi surprised her when she inserted a finger up her ass. Heidi sawed first one, then two fingers up Angie's crinkled star while she ground my cock stimulating both her clit and this new sexually charged area in the back of her pussy. The sensations I felt on my cock were incredible. Heidi's fingers were sawing in and out but also wiggling. I could feel them rub through the thin membrane of flesh. Heidi's fingers felt wonderful against the shaft of my cock as Angie ground the bottom depths of her sweet hole on my bulbous head. I was close and prayed I would last until her orgasm. Suddenly, Angie was bouncing, grinding and flailing uncontrollably. Then, another lightening bolt struck and her rain sprayed. Gush upon gush shot from her tight lips. I wanted to taste this mix again and attempted to move my head in line with the streaming flow as she sprang back up into the cowgirl position. Angie's pussy squeezed my cock as it shot the delicious brew. The sensation coupled with the intense show caused me to loose all control. My balls shot their burning contents into this little firecracker's drenched box. After this first massive shot, I realized I wasn't wearing a condom and bucked Angie off my erupting rod as she continued to spray me with her sweet nectar. Shannon and Heidi were so turned on by the sight, they both fought over my cock. Heidi took one rope and Shannon took the next. Each savored the creamy mix. As the girls fought over my pole, I clawed my way to Angie's squirting pussy; only to arrive as the last trickle dribbled over my tongue. As Angie finally came down from her high, she lay panting next to me as Shannon and Heidi now alternated between Angie's and my legs. Shannon started to squeeze my cock as she searched for every last drop; while Heidi used her spear-like tongue to probe for my cum deep in Angie's sweet pussy. When Shannon had my cock hard, she jumped on cowgirl style and fucked me. She humped and ground until she had a nice orgasm while Angie lay next to me stroking my chest. When Shannon's orgasm passed, she traded spots with Heidi. Heidi then cleaned my cock of Shannon's cum. She wanted my hard beast but she wanted it her way. She dragged me to my knees and begged me to fuck her doggie style, her favorite position. As Heidi assumed the position, I leaned over and kissed Angie who seemed lost in a trace as Shannon worked her sloppy hole. When I finished, I quickly lined my cock up to Heidi's trimmed bush. I grabbed my cock and slid it up and down her slit. Shannon and Angie were busy and I needed some lube. When I had enough juice on it, I plunged in balls deep. Heidi inhaled deeply as I sank my fat cock all the way in with one stroke. Heidi was beside herself. She said this was the fullest she had ever felt. She immediately began meeting my thrusts and slapped her ass cheeks against my balls. Some time during all this, Anne gave the camcorder to Shannon and she snuck between Heidi legs. Anne's tongue licked and slurped Heidi's drooling cunt as I hammered her pussy. Anne had her fingers working hard on Heidi's clit. The combination of my intense hammering of her tight snatch and Anne's all out assault on her clit sent Heidi cascading into an orgasmic bliss. Heidi bucked so hard that she sent me flying back to Angie's side. As I watched Heidi continue with her amazing display, Angie took my cock deep down her throat to clean my chiseled rod of Heidi's girl cum. Anne continued her clitoral assault as Heidi finally ground her cunt onto her face. Anne noisily attacked her pussy until Heidi peaked with another mind blowing orgasm. As Heidi slowly recovered, Angie moved to my side and said quietly, "Anne is the only one who hasn't had that meaty dick of yours. Are you going to fix that?" My little minx was a kinky one. I liked that; I liked that a lot. I leant down to my sister who had Shannon cleaning her pussy juiced face and asked loud enough for all to hear, "So Anne, you are the only one who hasn't taken a ride tonight. Ready?" I lay back and told Angie to suck me rock hard while we all waited to see what my sister's reaction would be. To all of our surprise, she lay on the pillow next to me as Angie sucked my cock. She looked at me and said, "Take me in the ass. Angie, get me ready." Angie quickly moved between Anne's legs. Angie grabbed Anne's legs just below the knees and pushed them forward spreading them slightly. She quickly had her ass just at the right height to stick her tongue deep into my sister's ass. After several minutes of tonguing, spitting and fingering her ass, Angie looked at me and said, "She's ready." I got between my sister's legs. My cock was sore from the night's events, but it was harder than ever. I placed the crowned head near my sister's crinkle and pushed slowly. I was amazed at the ease at which my cock slid into her ass. I kept up the slow and steady motion until my entire length was balls deep in her cute little puckered hole. Shannon was on the camcorder and giving the play by play doing her best to describe the event. "Never in the course of anal fucking have I witnessed a colossal cock entering a tight ass so easily," in her best Howard Cosell voice. I quicken my pace. I took my sister's legs, repositioned them above my shoulders and starting hammering away at her asshole. She was grunting and groaning. Her fat tits bounced in her face as she quickly stuck one of her nipples in her mouth and bit hard. The fact that this was my sister, three of her friends were watching and it was my first successful attempt of ass fucking was too much for me. As my balls slapped against her ass, I blew the last of my cum into my sister's dark tunnel. She felt the creamy mix coat her hole as I announced I was cumming. I slammed hard one final time as my ass cheeks clenched together. We were locked in that position for nearly two minutes. My sister tormented me the whole time squeezing her anal muscles around my sensitive prick. When I thought I was finally coming down, she would flex again and prolong my intense pleasure. Unfortunately, my sexual high faded, I rolled off and I lay exhausted next to Anne. Anne quickly told Heidi to lie on the bed. As she did, Anne strattled her face, held her ass cheeks open and pushed my creamy mix into her mouth. As the ooze flowed from my sister's ass, Heidi held her mouth open with her dancing tongue sticking out waiting for the cream to hit her taste buds. When the goo finally stopped, Anne crouched and allowed Heidi's tongue to search her inner depths to pull the last of the nectar from her bowels. Shannon and Angie playfully licked, sucked and stroked my cock as Heidi cleaned Anne's cum filled ass. As the last bit was cleaned off my cock and the girls realized I could no longer perform, they snuggled on either side of me. Heidi and Anne rested near our feet and we all quickly fell asleep. I awoke as the morning light shone directly in my face. I had a strong urge to take my good morning piss. Then, the events from the previous night flooded me as I detangled myself from the mass of girls using me as their personal pillow. When I hit the floor, I turned to shut the blinds and spied the camcorder on the floor. I quickly popped the VHS tape out and slide it into my duffle bag near the door. Not trusting any of the girls, I took the bag into the bathroom with me while I pissed and took a quick shower. As I emerged from the bathroom, I quietly woke my sister to see when our parents were returning. She groggily said, "Around 10AM. They stayed at Aunt Judy's last night to help around the farm while Uncle Tom is sick." I looked at the clock and it was 9:38. I said, "You guys better move then. You only have 20 minutes until they are supposed to return." With that, they all jumped out of bed, gave me a quick kiss and ran for the bathroom. Angie was the last to kiss me good bye. She lingered after the kiss and I told her, "We certainly had a magical night. I hope you will consider going out with me; only this time, just the two of us." She smiled and said, "I'd like that. Call me...SOON." I kissed her more affectionately and left. As I was leaving, mom and dad pulled into the drive. I stalled them for about 20 minutes talking about Uncle Tom and 'college life'. Then, I headed back to my apartment, called my girlfriend and broke up with her. Bill and his girlfriend left for brunch after witnessing the painful break up call. So while I had the apartment to myself, I put the tape in the VCR and watched it from beginning to end. It was a work of art. I shot several loads watching the tape. When it ended, I tried to imagine how I could ever top this sexual conquest. Then, I realized quickly how grateful I was to have the tape to relive the memories. A few hours later, I called Angie and asked her out. She promptly said yes. Now, more than twenty-five years later, we are still together and enjoy an active sex life full of love, respect and the occasional girlfriend or two.