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Strange How the Night Moves

"How I lost my cherry to a future porn star - part 2"

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Author's Notes

"If you haven't read part 1 yet, you should do that first. This story is 100 percent true. I haven't even changed the names because there was no one innocent to protect."

It had been, without a doubt, the hottest night of my life. And then I learned that it was just getting started. 

After giving me an incredible first-ever blow job, Tara whispered in my ear, “The hottest night of your life, and all I got was a mouthful of cum. You still owe me, and you’re gonna pay up!”  

After the store closed at 10, Tara told me to follow her to her apartment. 

“My roommate’s a bartender. She won’t be home until after 2 a.m. And you have work to do.”  

Tara drove to her apartment, which was less than a mile away, with me following in my car. I was shocked to see that it was the same neighborhood where my asshole father had lived. I hadn’t seen him in over two years, since the day I’d turned eighteen, and was no longer bound to court-ordered visits. It wasn’t the nicest neighborhood. Tara’s building and those around it had all seen better days. Peeling paint, unkempt landscaping, and just a feeling of resigned indifference. I found a spot on the street and met Tara at the building entrance.  She led me up the stairs to her small one-bedroom apartment.  

Opening the door, we stepped inside to a sparsely furnished living room area. It featured a couch that looked like it was straight out of a thrift store, a side table with a lamp, an old TV, and a mattress with no bedframe under a window in the corner. There was a small kitchen with an ancient refrigerator and a card table with 3 dilapidated folding chairs as the dining area. A door led to what apparently was a bedroom, but it was closed. The whole place was in desperate need of a coat of paint and the shag carpeting looked pretty threadbare. There were a couple of cheap posters scotch-taped to the wall. Mick Jagger, AC/DC, and Aerosmith. I thought to myself, “So I’m going to have the first fuck of my life in a total shithole….. COOL!” 

As dismal as it was, the kitchen counter featured an amazing variety of liquor, no doubt shoplifted from the store.  There was Johnnie Walker Red, Jack Daniels, Jose Cuervo tequila, and Stolichnaya vodka. 

Tera saw me looking at the collection.  “Hey, I didn’t steal that stuff!”, she said. “Sometimes the sales vendors like to give me little gifts!” I didn’t believe her, but I also didn’t care. I was completely out of my element. Being alone lin an apartment with a girl, even one who had just recently had my cum in her mouth, had brought back my awkward shyness. I softly mumbled, “Okay.” 

“Jeez!”. Tera’s voice softened.  “Relax, Stuart. Why are you always so uptight?” She opened the refrigerator. There was almost no food in it, but there was plenty of beer. She reached to the back and pulled out a bottle of Jägermeister. Opening a cabinet, she grabbed a couple of shot glasses (shoplifted from aisle 13) and poured us each a shot. “Maybe this will help you loosen up.” 

I wasn’t much of a drinker, but I threw it back in one shot, then followed it up with another. Despite it being ice cold, I felt the burning in my throat as it went down. I was still nervous, but I tried to make small talk. “It looks like you had another modeling session”, I said. “I can tell by the way you’re dressed. And that makeup is really sexy.” 

Tara’s face lit up. “Yeah!”, she said. You could hear the excitement in her voice.  “It was another Girl-Girl shoot. I’m not really into girls, but it was still hot. And making so much easy money is even hotter! What I made this morning will cover two months' rent on this dump.” 

The Jägermeister shots were beginning to take effect. I felt more relaxed, and the thought of Tara posing naked with another girl was causing a ruckus in my underwear.  

“So, same as before?”, I asked.  

“No.”, she replied. “This was a different girl. Her name’s Danielle, and she’s gorgeous. Way prettier than me.” 

I felt like I had to protest, but she cut me off.  

“No, it’s true. She’s platinum blonde, and she has the prettiest little tits that sit up all by themselves. I don’t think she’s ever had to wear a bra in her life. Like I said, I’m not into girls, but if I’m gonna get pussy licked by one, I’m glad it was her.” 

The ruckus in my underwear was now fully engorged.  

“Holy shit! Did she really lick you?”, I asked. “Did you lick her?” 

“No, we just simulated it. I’m not gonna go that far.” 

Just then, my smart-ass gene kicked in before my “keep your mouth shut “gene could react. “Maybe you should let her lick you for real. You could use the extra money to buy a bedframe”. 

Tara actually laughed. Then she looked me right in the eyes. “Maybe I should. But I sure need SOMEONE to lick me for real.” 

My brain went into a fog again, and I heard myself saying, “I’d like to volunteer for the job.” 

We both stood up, and I started heading toward the closed bedroom door.  

“No, that's my roommate’s”, Tara said. “I sleep over there.” She pointed to the mattress under the window. “It sucks, but she pays more rent than me, so she gets the bedroom.” 

At this point, I didn’t care if we did it in the middle of Ventura Blvd., I just wanted to see Tara naked. We moved over to the mattress and Tara peeled off her red tube top, then unhooked the half bra she was wearing underneath. When she took it off and her breasts fell free, I was mesmerized. They were round and firm and perfect, and her nipples were surrounded by huge, dark brown areolas.  

I let out a breath and admired them. Then Tara unzipped her go-go boots and tossed them aside before pulling down her miniskirt. All she had on now was a tiny red thong that just managed to cover her pussy.  

As I stood there watching, Tara told me it would be a lot more fun if I took my clothes off too. I practically ripped off my shirt and fumbled out of my shoes before taking off my pants.  My cock was like a tent pole inside my boxers, and I wasted no time in setting it free. Tara lay on the mattress and propped herself up against the wall using a couple of pillows. She bent her knees and sat spread-eagled in front of me, the red thong still in place.  

Again, looking right in my eyes, she said seductively, “Alright, Stuart, pay up.”  

If I’d learned one thing from all of those porn magazines I’d stolen from my dad, it was the various parts of a woman's pussy and where to touch them for the best results. I knelt down on the mattress and positioned my face between Tara’s legs. I started off by licking the inside of her calf, slowly working my way up to her thigh.

Tara had a look of pleasure on her face, and feeling encouraged, I continued working my way up. Just before reaching her thong, I moved to her other calf and started again. This time, my tongue made it all the way to her thong, which I moved to the side. Pausing to take in my first close-up view of a female vulva, I remember how beautiful it looked, but more about how beautiful it smelled.

I gave her the same hot breath treatment she’d used on me earlier in the evening, and I could hear her breathing quicken. Tara was just beginning to get wet. Her scent made my already rock-hard cock throb even harder. I used my fingers to part Tara’s pussy lips and felt her lubrication building. I licked it off my fingers and marveled at the strong taste. Gently, I pushed my tongue between her lips and started licking and sucking. Tara put her head back and let out a soft moan.

As I continued licking, I used my fingers to locate her clitoris. I put a finger into her vagina and used the lubrication to wet her clit. I rolled and pinched the rapidly enlarging head between my fingers and felt her shudder at the sensation.   I continued this for a few minutes, then switched it up. I placed my middle and ring fingers inside her now very wet pussy and started finger fucking her, first slowly, and then gaining speed.

At the same time, I started flicking the end of her clit with the tip of my tongue. I explored inside her with my fingers, searching for her G-spot. Tara’s loud moan told me I’d found it. She let out a guttural “Oh, fuck!”, and started writhing her hips in rhythm with my finger motion.

Suddenly, she grabbed my head with both hands and pulled me deeper into her cunt. Then she let out a huge moan and screamed “Fuck! Fuck! Fuck! Don't stop! Keep doing that!!”

She held onto my head and bucked violently as she gushed onto my face and chin. I held on for dear life as she wrapped her legs around my head and put a death grip on me, moaning with pleasure the whole time. After what felt like forever, she finally relaxed, and I came up for air. I had no frame of reference, but I felt pretty sure I’d just caused my first orgasm. 

“What the FUCK, Stu!” Tara was flushed red and out of breath. Her pussy was pink and swollen and very, very wet. “You’ve never done that before?! Your girlfriend is a fucking IDIOT if she doesn’t want that! That was fucking amazing!”  

For the first time in my life, I realized that I had something women wanted. It made me feel confident and powerful.  

“So, I guess we’re even then?” 

 Tara looked at me and laughed. “No, we’re not fucking even!”, she laughed. “You still owe me big time!"

Tara jumped off the mattress and poured us a couple more Jägermeister shots. We downed them, and she flopped back down.

"Are you ready to make your next payment?” 

I think my rock-hard dick answered her question.  

Tara took off her thong and told me to lie on my back. I flipped over and lay with my feet hanging off the end of the mattress, and Tara climbed up with her knees straddling my head, facing my feet. She lifted her arms over her head and slowly lowered her pussy down on my face.

I started lapping at her clit again, and she ground her pussy back and forth over my face, gyrating like she was riding a mechanical bull. I reached up and took hold of her hips as the mattress shook. Maybe it was good that there was no bedframe, because we probably would have collapsed it. She kept this up for several minutes, grinding and moaning, then leaned forward and started sucking on my cock. It felt fantastic as she plunged my swollen dick head into her mouth, swirling her tongue around it and gently nibbling at the tip. 

“Okay", I thought to myself. "First 69 checked off the list."  As before, Tara then moved her mouth up and down my shaft, but this time, it was much more intense. I continued licking her clit, and I shoved 3 fingers inside her, furiously pounding her pussy. I could tell by her moaning that she was about to cum again, and so was I. A few more seconds, and she pushed herself down hard on my face, while at the same time, she deep-throated me and grabbed and squeezed my balls. She let out a muffled scream as she reached her orgasm at the same time I blasted off in her mouth for the second time of the day.  

Her juices gushed into my mouth and my cum gushed into hers. Somehow, I pumped out an even bigger load this time. Tara took it all in her talented mouth. She lay still on top of me for a bit, my cock still buried in her mouth.  Then she got up and turned around to give me another cum filled kiss. This time, I had a surprise for her. I had held her juices in my mouth, so when we kissed, it all mixed together in a delicious cum cocktail.  I had never seen this particular kink of cum swapping in my dad’s vast porn collection, but I decided I rather liked it.  

Tara lay up against me on the mattress as we both tried to catch our breath.  “You really do have a natural talent for pussy licking,” she said.  

“Thanks. I haven’t had any experience, but I’ve seen plenty of it in magazines.” I told her about stealing my dad’s porn for all those years. “He only lived a couple of blocks from here", I told her.  

“Well, as soon as I start making real money, I will be out of this dump in a heartbeat”, Tara said quietly. “I fucking hate this place.”

I shifted to my side and propped my head up on my elbow. I started gently tracing a finger around her nipples. “You said they paid more money depending on what you would do.  So how does that work?”, I asked. 

“Well, Girl-Girl, no touching pays pretty good, but not great. If you do full contact, it pays a little more. You can get a lot more for Boy-Girl, and the biggest paycheck is for Boy-Boy-Girl with a happy ending. “ 

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I was obviously out of my league here. “Happy ending? What’s that?” 

Tara hesitated a minute before she answered.  

“Happy ending means you fuck two or more guys at once, and they all cum on you.” 

My jaw dropped. “On you?” 

“Yeah." Tara almost whispered. “The modeling agency doesn’t want it in you, they want it on you, so people can see it. On your belly, ass, pussy, tits. But they really want to see it on your face. That’s the biggest payday of all.” 

“Oh yeah, I think I’ve seen that”, I lied. In the early days of porn, facials were very rare. “Would you do something like that?” 

“No fucking way!”, Tara protested.  

Now I was really curious, and I pushed a little farther. “Have you ever been with 2 guys at once in real life?”. 

She told me that she had once gotten drunk and fucked a couple of guys at a party. “It was really hot, but I don’t think I could do it in front of a camera. There’s, like, a bunch of other people in the room at those sessions.  I like showing off my body, and I like when guys fantasize about me, but that’s where I draw the line.” 

I told her she should do what she was comfortable with. “But if you liked it in real life, why not make a little money for it? It would help you get out of here and into someplace more livable.” 

Tara thought about it for a minute.  It felt like she had drifted off to another world.  Then her mood suddenly shifted. “Hey, are you ready to go again? I really need to get fucked, and if you’re as good at that as you are at pussy licking, I definitely want a piece of it.” 

My cock suddenly awoke from its slumber. “Well, let’s find out!” 

Tara told me to lie on my back. She straddled me, again facing my feet, but this time she positioned herself with my cock behind her, slapping up against her ass. I was still somewhat lubricated from before, but Tara slid 3 fingers into her vagina and got them wet with her own juices. Then she reached around and stroked me to get me wetter. By now, I was diamond cutting hard again, and she lowered herself down toward her objective.

Moving ever so slowly, she placed my cock head between her lips and started rubbing it up and down, not putting it in yet. The feeling of my dick sliding on her labia was absolutely incredible to me. I knew that whatever happened next was going to be heavenly. Tara then spread her lips apart and slid just the mushroom head inside her vagina. She moved her hips in a circular motion, letting me feel her vaginal wall wrapped around me. Then, she started moving up and down, taking in a little more of me with each stroke. She kept this up for several minutes until I was finally balls deep into her and I could feel her cervix pressing up against my cock head. My earlier assessment had been correct. This was heaven.  

She started bouncing up and down and letting out a little grunt with each movement. I was thrusting hips to meet her, making it all the more intense. We went on like this for what seemed like forever, and I was really worried that I might pop too soon and ruin everything. Finally, I stopped her and pushed her off me. “Could you turn around, please?” I asked. “I want to look at you while we do this.”  

Tara turned and lowered herself back down, looking wildly right into my eyes. “You want to see me while we’re fucking?”, she asked in the dirtiest possible voice. “You like to watch? You like watching your dick slide in and out of my pussy?” 

Her dirty talk was turning me on even more, if that was possible.  

“Fuck yeah”, I shot back. “Fuck me with that fucking cunt! I know you love fucking! You live for it! Keep it up!” 

Apparently, shy, timid Stuart had left the building. “You love my dick inside you, don’t you?”, I growled.  “Can you feel it? You can’t get enough of it, can you?” 

Tara groaned again. “Fuck me with that big cock! Fuck me harder!” 

She leaned down and fed her gorgeous tits into my mouth. I’d been dreaming of that since the first time she’d set foot in the store. I licked and sucked and bit at her hard nipples as she continued sliding up and down on me. 

Then, she slowed down and stopped. I was confused. “Crap! Did I do something wrong? Is she mad at me?”, I thought. 

“Let’s go doggy style,” she said. 

Feeling relieved, I was all too happy to comply. She got up on her hands and knees and pushed her ass up in the air. I slipped in behind her, but before I started, I leaned down and licked that beautiful ass, trying to force my tongue into the tight little circle. Tara shivered just a little and said, “That feels amazing, but just so you know, I don’t do anal.” 

Honestly, the thought hadn’t crossed my mind, but I filed it away for future reference.   

I gave her ass a few more seconds of attention, then straightened up and brought my hips even with hers. Tara reached back and guided my cock into her. We were both so wet, it slid right in. I took my time and slowly went all the way in and all the way back out. I watched the head of my cock pull out of her, then plunged it back in. I did it several times. I was enjoying the hell out of the view, and I think Tara noticed this.  

“You really do get off watching yourself fuck me, don’t you?” she said.  

“This is something I’m going to want to remember for a long time,” I answered her. “I want to be sure to take it all in.” 

“Yeah, I want to take it all in too,” she said, back to her dirty talk voice. “So, stop fucking around and put it all in!” 

Who was I to argue? I grabbed Tara by the hips and started slamming her as hard and as fast as I could. The slapping sounds of our bodies coming together filled the room, only to be drowned out by our grunting and groaning.

I decided right then and there that doggy was my favorite position. All these years later, that hasn’t changed. It wasn’t long before I started feeling that familiar tightening in my nutsack that told me I was getting close to climax. But I really wanted to make Tara cum again before I went off.

I changed my rhythm so that I would slowly pull out of her, then slam it back in as forcefully as I could. I could tell she liked this. She reached underneath and began massaging her clit and moaning with pleasure. Every time I slammed into her, she rubbed herself harder and harder.

Then I heard the cry starting deep down inside her and making its way out. “Ohhhh, yeahhhhh! Oh, fuuuuck!”. Tara came hard, her body spasming and shaking as the full wave hit her. I had no idea that women could have multiple orgasms, but I was witnessing one right before my eyes. She kept massaging her clit furiously as I continued to pound her from behind. It seemed like she was experiencing wave after wave of orgasms.

Finally, I couldn’t hold back any longer. I threw my head back and slammed my hips forward, burying my cock all the way inside her. When I let loose, it was an absolute torrent of cum, one pump after another, deep inside her beautiful pussy. I wrapped my arms around her stomach and pulled her tight to my hips as I basked in the afterglow of this magic moment. 

We both collapsed onto the mattress, exhausted. Once we were able to breathe again, Tara looked me in the eyes. I could see a wicked smile forming, and she said to me in that crazy dirty talking voice, “Fuck, Stuart, you really made a mess down there.  You better go clean it up.” 

I gave her a confused look and she playfully shoved my head down toward her pussy.  Dutifully, I crawled down and saw my cum lazily dripping out of her and onto the mattress. I obediently lapped it up, sticking my tongue as far inside her as I could, determined to get it all. Tara grabbed me by the hair and moved my head around to all the spots that were soaked with my juices and hers.

After I’d gotten all of it that I could, I moved back up and positioned myself above her face. Then I let all of that cum dribble out of my mouth and into hers. I made sure some of it missed her mouth and coated her lips and chin. It looked absolutely beautiful to me. Then I moved in, taking her face into my hands and shared a passionate kiss, our tongues intertwined with my cum.  

After we lay on the mattress a bit longer, allowing ourselves to cool down, we got up and sat on the couch. Tara grabbed a couple of cans of beer from the fridge, and we sat just sipping and not talking much. Tara actually put the beer can up against her pussy, enjoying the coolness after all the heat we’d generated.  

Finally, she spoke. “So, first time, Stuart.  What did you think?” 

I laughed. “I could definitely get used to this. You were absolutely fucking amazing. I’ll be ready for round two any time you want.” 

Tara spoke quietly. “Look, Stuart. There’s probably not gonna be a round two. I'm sorry to tell you this, but this started out as a pity fuck. I felt bad about embarrassing you, so I figured I’d give you a quick blowjob to be nice.  Then I got horny, so I invited you over.  I didn’t expect much, but then you turned out to be amazing. I haven’t gotten fucked like that in a long time. You were really great. But I’m not looking for a boyfriend right now. I just want to make enough money to get the fuck out of this town. Once I do, I’m gone.” 

I tried to rationalize that in my head. I tried to come up with a reason she shouldn’t go. But I couldn’t. 

“Besides “, Tara said. “You’re gonna take all that amazing talent and use it on your girlfriend. She’s going to go out of her mind.” 

Now I really laughed out loud. “There is a ZERO percent chance of that. If I even tried, she’d probably have God shoot off lightning bolts to strike me dead. After tonight, we are officially through. Even if I can’t keep this up with you, I can’t ever go back to her. You’d be right. My balls really would explode.” 

This time, it was Tara who laughed out loud.  "Okay, but I’m sure you’ll find someone else. Here’s a little secret for you… girls like to fuck just as much as guys. Maybe even more.” 

After another few minutes of comfortable silence, she told me, “You should probably get going. My roommate will be home soon, and I really need to get some sleep. Thank you for a really good time.” 

I got dressed and finished my beer. Then I kissed her again and said, “Thank you for this night I will never forget. Even if it was a pity fuck, it was a great pity fuck. I know you said not again, but I’m hoping you don’t stick to that.  Never say never.” 

As I walked to my car, I realized I wasn’t the same person I’d been that morning. And it felt fucking great. 

Tara kept working at the store for another few months.  Despite all the hints that I dropped, she never took me up on them again. She started missing work days as her modeling career got busier and busier. 

Then one day, she just didn’t show up. Didn’t call in, didn’t pick up her final paycheck. She just disappeared. I even went over to her apartment to check on her, but the manager told me she and her roommate had skipped out. It was like she’d never existed.  

Six months later, I was still working at the wine shop. Since I’d turned 21, I was now legally allowed to sell liquor, and I’d been promoted to cashier. Larry came over to my register and asked me to come back to the office. He opened his desk drawer and pulled out a magazine. It was one of those slick paper hard core porn mags like I used to steal from my father. The front cover had a cute platinum blonde girl with perky little tits that looked like they’d never needed a bra. The name of the magazine was “Pretty Girl #6.”  

“Uhhh… thanks, Larry. Why am I looking at this?” 

Larry said 2 words. “Page 17.” 

I flipped it open to page 17, and there she was. Tara, with her hair and makeup looking sexier than ever. She was wearing a flimsy lavender negligee that had fallen off her shoulders, showcasing her tits. She was on a mattress, just like the one we’d shared. There was one guy laying on it and Tara was sitting on top of him, holding his fully erect cock in her hand. His cum was cascading over her fingers and down onto his balls. There was a second guy, standing above her holding his own cock above her mouth. She was staring blankly into the camera, as his cum dripped down her chin. Tara had gotten her happy ending.  

 

It would be several years before I ran into Tara again.  But it was definitely worth the wait. 

 

END OF PART TWO. 

Published 
Written by Stupalm
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