Do You Remember The First Time

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"OHOHOHHHHH" Cara moaned as she came with a slight shriek. I drank her juices like my depended on it and as her orgasm subsided, I gave her a few licks before she unwrapped her legs from around my head as I kissed her. The mix of her coconut chap-stick+pussy juices overwhelmed me and I'm sure it did her as well.

"You were awesome Tony." Cara panted as I then turned her around and put her head on the pillows and brought her ass towards me. Overcome with lust, I began licking her asshole, which caused Cara to groan and almost shriek in surprise.

"Holy shit Tony!!! You're a dirty boy full of surprises!" Cara moaned and that made me continue to lick her holiest of holes for an extra minute. Not gonna lie, I quite enjoyed licking her ass up and down. I wasn't expecting anal sex tonight but hey why not try something close?

After about a minute or so, I stop and give her a playful smack on her ass, which caused her to giggle. "One more time please." Cara said and I gave her another light smack. "Has a boy ever done that to you before?" I asked. "Nope. Never." Cara whispered. I then grabbed the box of condoms and Cara taught me how to use it. In fact, she was the one who put it on my dick.

Cara then straddled me and I braced for contact as her hot, wet hole was literally inches above my member. "You ready?" She asked me and I replied with "Do it. Please."

Cara then slowly lowered herself on to me, which caused us her to moan and me to wince. The feeling was so different but I eventually got used to it. Cara then slowly started to grind herself on me back and forth. Her messy brown hair was in all over her face and I eventually brushed them to the side so we can look at each other.

"Fuck Tony you feel amazing." She moaned as she reached down to play with her clit with her left hand and grab her breasts with her right as she leaned down to kiss me for a brief moment. The only sounds coming from me were light pants.

After about 3 minutes of steady rocking, Cara then to start making her pace go faster, caused each other to moan. Cara held on to my legs as she rock back and forth on my dick, the sweat building up on her (me too but to a lesser degree).

"My God Tony you're amazing!" Cara shouted as she gyrated her hips for a few seconds more until stopping and whipping her hair back and moaning, which caused me to bring my hands to her breasts and neck, which I felt for a few moments. i then had an idea.

I gently lifted her ass up and made her bounce back down my dick, which further prolonged the pleasure for both of us. Cara got the memo and began bouncing on my cock, the sounds of flesh meeting flesh+moaning filling the motel room.

"Keep going Cara fuck." I moaned and Cara more than obliged. "Shit Tony you're....So fucking big!" Cara moaned as I held on to her hips further bringing her down to my cock. Again getting a read on her body language (mostly breathing) I knew she was ready for orgasm #2) so I began to lightly pinch and rub her clit as she continued riding me.

"GODDAMN TONY RIGHT THERE. RIGHT THERE. " She shouted as I continued to do as she said. Eventually, she came for the 2nd time.

I then threw back down on the bed and put both of her long legs on my shoulders for the Anvil position, all without pulling out from her. "Fuck Tony don't stop baby! Keep going!!" Cara panted as now the sweat was starting build up on me and I complied. 4 Minutes in this position and I stopped as I went into standard missionary position and Cara wrapped her legs around my waist, further letting me into her and continuing my pace.

"Holy fuck Cara you're super tight. You feel so fucking good!" I moaned as I continued. The pleasure was starting to get the better of me and I can feel myself reaching the highest of highs and so did Cara. "In my mouth remember?" She panted as I nodded. 3 More minutes of this and I had it. I was ready to burst. How I managed to last thing long was beyond me.

"Get down babe." I ordered Cara as I removed the condom from my shaft as Cara placed her lips around my member. "Fuck keep going." I urged her and she complied. We never broke eye contact as we were lost in each other and the needy look in her eyes is what pushed over.

"Oh shit here I cum!! FUCK." I shouted and I did. With my dick still inside Cara's mouth, I exploded inside of her with a grunt. My dick was visibly pumping long ropes of cum and not to my surprise, Cara managed to drink up every single last drop even as my dick was deflating. With one last suck, she quite literally POPPED off my dick and showed some of the cum that was still on her tongue to me before swallowing it.

After two minutes of just heavy breathing from us both, I broke the silence the silence. "THAT'S what sex is like? Why did I wait so long?!" I joked as we both laughed and cuddled up next to each other. 'Shit." Cara thought. "Our folks. What will they say?" I reassured her that we'll I will take the rap for our "night out." Cara smiled."

"So...." Cara says looking at my somewhat growing erection. "How about Round 2 babe?" And we did that. The 2nd time was a lot more gentle and sensual. After a couple of more orgasms, we eventually succumb to a blissful slumber.

*Present day*

"Damn Cara was such a great girlfriend. What wrong?" I rhetorically asked in my mind knowing the answer.

End of Chapter 3. _________________________________________________

*When we last left off, Cara and Tony had finally validated their love for each other on, of all days, Tony's birthday. As Junior year came to a close, the lives of Tony, Margot, and Cara began to change. Meanwhile, a mini reunion was in the works as Tony's 27th birthday was fast approaching and several things were going through his head: meeting his first love again while planning on proposing to his current love. What will happen? Read to find out.*

*Present day*

"Hey babe." Margot whispers as she lays on top of me, resting her little head on my chest.

"Hello there." I say in a low tone as I smile and kiss her forehead.

After a long, hard day of doing pretty much nothing but reminiscing while Margot was off doing her thing, we decided to pack it in and fell asleep earlier than we normally would. Such an exciting couple we are I know.

"Um I just remembered there's a mini-shoot today." I told her as I got up off the bed. My job as a TV cinematographer was not as hectic as I was expecting when I entered the industry but it was still fairly daunting. "We're filming the last scene of Westworld." Being a crew member on one of the most anticipated and mysterious TV shows in recent memory was difficult as I had to mum about details but I was able to keep secrets to myself.

"Come on babe you still haven't told me a thing about this show!!" Margot whined. "I'm sworn to secrecy." I said as I closed the door and began to take a shower. Few minutes later, I got dressed and Margot sat behind me, rubbing my chest as her own way of "good luck." "Thanks babe." I thanked as she rested her head on my shoulder and I kissed her cheek.

During the 2 hour shooting session, my mind was focused the entire but there was one thing that somehow....Triggered another series of memories. Of all things, the word "Senior" got me to think about my last year of high school.

*8 Years ago*

"OOOOH SHIT YES!" Cara moaned as I ate her our. It was her 18th birthday and I figured I'd returned the favor for pleasing me on my 18th birthday the only way I knew how: by taking out to a dinner and movie of course!

"Mhmmmh" I moaned against her hot center. From the moment I met Margot and started dating Cara, I grew far more confident not only in myself but around other people, especially girls. Well, sort of. Anyways, ever since I lost my virginity, I became more confident in my sexual prowess and I showcased those talents to Cara at that moment.

"Hmmmm keep going babe!" Cara moaned as her breaths were starting to rapidly increase as my oral assault on her moist mound continued so I decided to increase the pressure but still keep a steady pace. "Ooooooohhhmmmm" Cara moaned in pleasure, close to reaching an orgasm.

"I'M RIGHT THERE OHOHOH!" Cara gasped as she was mere seconds away from reaching her orgasm as I continued at the pace I was going at. Then, Cara came with a loud screech as her juices landed on part of my face as I drank up most of it while others landed on my chin. I then stood up and planted my lips against hers, making sure she tasted her juices.

"Mmmmhm." We both moaned through the kiss. I removed my dress shirt as I began stroking my semi-erect dick to full attention, which Cara then helped me out with as she recovered from her orgasm. She slowly began to jerk my rod gently and began to moan. "Mhmhmm yeeeeah." She moaned in a low voice. She then slapped my dick! Like actually slapped it.

"OW!" I yelped surprised. "What was that for?!"

"Oh nothin.'" Cara teased. "Just wanted to see how It reacted to a slap." She giggled as I roll my eyes. After a few more pumps, she removes her hand away as I slowly drag my fully erect member across the slit of her vagina, teasing her.

"UGH I FUCKIN' HATE WHEN YOU TEASE ME LIKE THAT." Cara gasped, slightly annoyed. Ever since my birthday when me and Cara first had sex and the subsequent morning when we had to tell our parents, our parents understood and urged us to use protection and Cara to get on the pill, which we obliged.

"I dunno. Your pussy seems to say otherwise." I playfully quipped, causing her to moan loader.

After a few seconds of teasing, I slid my member into her hot, tight opening and I instantly groaned. Even with the amount of times we've had, she still had an incredibly tight, vise-like grip around me.

"Ohhhh." Cara groaned as I slowly began to rock back and forth inside of her with slow strokes, gaining low moans from both me and Cara. After a few moments, I began to slowly pick up the face. In doing so, Cara looked up at me with those gorgeous eyes of hers and brought me down for another quick kiss.

"Mhhhm." I moaned as I started to pick up the pace more but as I was about to, Cara flipped me on my back and began to take control as she rode me.

"OH FUUUUUCK." I groaned as Cara began to ride me at a steady pace. My hands instantly reached for her breasts and her neck as I grabbed and massaged each, which let a throaty moan escape from Cara's mouth as the sound of skin-on-skin along with the creaking of the bed filled the room.

"Fuck keep going Cara!: I moaned and she did just that. She mixed it up with a succession of fast rocks and then slowed down to ride me slow and steady, the latter was driving me to an eventual orgasm. As I pinched and played with her nipples, Cara then brought her hand to my throat to lightly squeeze it. It was unexpected but I honestly didn't mind it as I've done it to her maybe twice in our encounters and I always make sure not to hurt her badly and she did the same.

"Oh shiiiit!" Cara moans still holding my neck as she rides me. After a few seconds, I slowly let go of her hands and bring my own to her thighs, rubbing them gently. "Sooo tight hmmmm." I said in a low voice as she began to quicken her pace as she turned her both hands and placed them on my thighs.

"SHITSHITTHERE!!" Cara managed to somehow get out as she now rode me with furious intent, gyrating her hips in the sexiest motion, her long legs giving her a slight advantage.

"FUCK CARA I'M CLOSE." I belted out as she continued her movements.

"In my pussy! In my fucking pussy NOW." Cara shouted, which was enough to push me over. Even with her on the pill, I never came inside of her as I "played it safe." "GONNA CUM! FUCKING CUM WITH ME TONY!"

"OH SHIIIIT." I yelled and came with a grunt. Rope after rope of cum (quite literally) shot up into Cara's sweet pussy, milking me dry for all it was worth.

"Yesyesyesyes!!" Cara gasped as both of our orgasms began to subside as she fell on top of me as I held her in my arms, my dick never exiting her as we lay breathless as we succumb to a deep, blissful sleep.

Senior year hit and life was going....Well alright for the most part. I started doing gigs for local business directing and editing them, mostly fast food commercials. It wasn't the most exciting thing ever, but hey it was a very nice start. Margot started to do more local plays and eventually found her way into local commercials. She was turning into a promising young actress. As for Cara? Well, that's a tough one.

Her headshots had piqued the interests of some pretty well known modelling agencies from the around the world but she sided with one called "Storm Model Management", which is based in her native England. Sadly, this meant she had to miss school but luckily for her, she more than the required credits to graduate so she was planning on graduating earlier than all of us anyways. Still, it didn't stop the 3 of us from still communicating daily.

One day around lunch time, me and Margot did a lot of reflection about these past few years.

"Does it feel like we both just met each other for the first time just yesterday?" Margot asked.

"Hm. You know, it feels a little longer. Just a little. Otherwise, I do think high school has flown by VERY fast. I have you and Cara to thank for that." I said as Margot blushed.

"Awwww thanks Tony. You've really been a really great friend." Margot replied with that huge smile of hers.

"Guarantee you that you and Cara will make it in Hollywood. Hell, you're both a lot closer than me!" I exclaimed.

"Aw c'mon. You're directing."

"Yeah commercials."

"It's called 'paying your dues' Tony!" Margot replied. "You don't just get everything handed to you willy nilly."

"Yeah you're right I guess." I said with a chuckle.

"So how's your nana doing if that's not a rude question?" She asked.

"Oh. Well, it's been 8 months. She was given 7. That lady is really a fighter" I said rather bluntly.

"Oh wow." Margot says surprised, trying not to sound too excited as she knows what the disease is all about.

"Yeah. But....She looks miserable." I said in a low tone. "Her body is becoming more frail, her hair is starting to thin, and she's barely speaking. She just looks like she's ready to go." I said as Margot was just silent. "Do you know what it's like to see someone literally die in front of you every minute of every day? It fucking hurts so much but, in a way, it's helped me prepare for the inevitable."

"I'm....sorry I asked." Margot said in shame.

"No no please don't." I said lifting her head up by the chin. "It's nice to talk to someone about this when the occasion rises. Cara and I would discuss this but...." I turn and look around. "She is not here." In truth, she was doing shoots with a local talent agency.

A week or so later, we went to Cara's house and brought with her some pretty huge news.

"Hey Tony, Margot!" Cara said as me and Margot arrived to her house. We returned it with a big hug as we sat on her couch and Cara proceeded to plant a big kiss on me as she sat my lap. She then told us the big news.

"Guys I just landed a spot on the cover of Teen Vogue!" Cara said in pure delight as we congratulated her.

"Wow Cara that is awesome!" Margot said as she hugged Cara.

"Congratulations babe!' I said as I hugged her as well.

"I start the shoot in January. I'm heading back after graduation." I was confused with what Cara said but little did I know it would spell the end of our relationship.

We started chatting up about our possible plans for the next hour or so before Margot went home. Then, I decided to discuss Cara's career move with her and the future of relationship. I've heard things like this before it's the classic story. Lovers/Friends are inseparable until something happens to one of and they break apart forever.

"So....you're leaving in January." I said matter-of-factly.

"Yeah." Cara said almost in disappointment, which surprised me.

"What's wrong?" I asked.

"Well. I'm excited and nervous but more importantly I'm thinking about you. About us." She said as she held both her hands on my face.

"Really? Because that's exactly what I wanted to talk to you about." I say almost relived.

"Oh? Well then let's talk Tony."

"I'm super happy for you but I'm a little bummed that you're leaving so soon. I thought you'd be here for graduation."

"But I'm graduating in December." Cara replied.

"No I mean in May. With me and Margot and everyone else. I know you have more credits than a lot of the other kids but still...." I told her,

"Tony look.....This is tough. I know that. I'm still getting used to the constant traveling. To be honest, I don't think I can. But I comes with the territory. I never thought any agencies would look at me, let alone sign me to a cover shoot. I HOPE I can be back in May to see everyone." Cara explained.

"Are you kidding me? Look at you." I examined her briefly. "What agency wouldn't want you?" I told her which seemed to brighten her mood.

"Just do you Cara and follow your dreams. You've made it this far." I said as I kissed her forehead as I left her house and went home.

For the next month or so, we carried on as usual. We were approaching the winter break and with each passing day, I was growing more scared for the inevitable day that Cara leaves. "Would she leave forever?" "Would she become successful like I hope she will?" "Will she forget about me, Margot, and everyone else?" These were the things running in my mind.

Two days before the winter break, Cara personally gave me an update on the status of her future and needless to say, it came at the worst time possible.

"Hello?" I answered the phone.

"Uhhhh...Tony. Can I talk to you? In person? It's urgent."

"I'm not sure Cara. They're putting nana in Hospice care. She should be arriving in a while so I have to help out with the necessary arrangements. But...you know what? Sure. Come on over."

"Oh thank you. See you in a bit. Love you." Cara spoke.

"Love you too."

Soon, Cara arrived to my house and....Well it happened.

"Hi Cara. You wanted to see me?" I asked.

"Yeah. Um....There's no easy way to say this." She whispered under her breath.

"What was that?" I said.

"Tony I love you." She said in a raspy voice as I already knew what was coming.

"You're gonna leave and never come back aren't you?" I said rather bluntly as she simply nodded

"I would be happy if you hadn't came to me at this time of ALL TIMES." I said.

"What?? I called you and said I could come over. That it was OK!" Cara said to me, becoming annoyed. "What I wanted to tell you is....I have been signed to a year-long deal with Storm. I probably won't be returning to the United States any time soon."

"I knew it. Fucking knew it." I said as I sprung up off the couch in anger.

"What?? This is MY career, Tony. I thought you'd be happy for me!" She nearly shouted at me.

"Fuck I am! It's just......What about us? This is it right?" I questioned.

"I don't want it to be Tony. This is really hurting me." Cara replied tears in her eyes as I hugged her.

"Shh it's ok." I whispered as I comforted her.

"Would....Would a long distance relationship work? With us?" Cara asked.

"I honestly don't know. You're gonna be so busy and always moving. We'll have hardly any time for proper conversations save for a few messages."

Before me or Cara could answer, my mom came back with my nana from the hospital and we prepared the bed.

"Cara can you help ma with nana on the bed please?" I asked and she did.

As we got the bed and everything set up, all I could do was just stare. I did not want to see my nana like this but I couldn't help but look anyways. Cara then came over to me to hold my arm as we departed the room and went to my room instead. We just held each other in silence for several minutes on my bed, reminiscing about all the times we've had together.