The Jared Chronicles Jared and the Cherry Project Part 5
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This is about the first time I broke a girl’s cherry. My first college girlfriend was a year older than me and I wasn’t a virgin when she took my virginity her name was Deepa and she was a year older than the rest of us as she skipped a year college early on in her life.
She was as tall as me 5.9 had long legs, an incredibly tight ass and small boobs that were impossibly perky. She was the perfect specimen of teen beauty. Even if her tits were bigger, it wouldn’t have made her more attractive because the rest of her was so perfect.
We began dating almost immediately. I was a popular naughty boy and she made friends fast with the group. We went to pubs and parties as the typical things teens do, which included making out and me trying to fuck her. As she stopped each attempt I made, it got more and more frustrating.
Finally, she confessed that she was a virgin and had been afraid to give her cherry to a guy as she and her family moved a lot.Her dad was some corporate exec and got transferred often.
At a party one night, we had some beers and found a private place to ourselves. She may have been a virgin, but told it by herself as long as a guy rubs her clit and gets her off, she could return the favor. She told me she also liked the taste of cum and how it felt when a cock erupted in her mouth. We got a private place where other couples are not allowed and I slid my hand down her unzipped jeans. Her clit sprang to attention under my finger as I rubbed her love button hard. She ground her hips hard against me and threw her head back. Her cunt was steamy-hot and I rubbed even harder.
She grabbed my hand and pressed me into her harder as she came. She panted and groaned and bit my shoulder as she finished. By this time, my cock was ready to rip out of my jeans. I stood up and undid the zipper. She must have been really turned on because she never sucked a cock. Normally, she had one speed with her hand and didn’t use her tongue enough, but that night she was like a porn starlet.
I got really weak in the knees and grabbed the back of her head for balance. She took this as a sign to suck and stroke harder and she responded like a pro. I was making these guttural grunts and sounds while she sucked away on me. I wasn’t sure how long I was going to last.Usually, it took her a while to bring me off.But it quickly became apparent this was going to be much faster.
She looked up at me and said: “You like it like this?” as she got the words out of her mouth, my cock erupted. The first squirt landed right on her chin. She quickly put my cock back in her mouth and sucked me dry. After I was empty, she wiped the cum off her chin and licked it off her hand. I figured we were done for the night and pulled my zipper up.
She then surprised me by what she said. “I want you to be my first. Tonight. I’m ready and can’t wait anymore. My pussy aches and I want to feel sexy. Nobody is at my house.We could go there. I don’t want to spoil my sex mood. Ok?” I almost asked her to repeat what she said, but didn’t want her to change her mind. I nodded, grabbed her hand and we left the party. We drove to her house in a cab and got out of the car. I pulled a couple rubbers out of pocket, but she surprised me again.
“You don’t need those if you don’t want. I’ve been on the pill since I was 14. My periods get all screwed up if I don’t regulate them. Is that ok?”
Fuck yeah, it was!! I had never fucked without a rubber before & after and eagerly looked forward to feeling what pussy actually felt like. We scrambled inside and went right to her bedroom. She got an old towel from her closet to spread under us in case she bled. We stripped each other quickly and I got my first look at her naked.She was perfect. Her bush was naturally scattered and her pussy lips were already swelling up a bit. I had seen her tits before, but the whole package was breathtaking. I guess I was staring too long because she asked if there was something wrong.
“No, Deepa.You are incredible. I just can’t believe I’m the lucky guy who gets to be your first.” I said. She had never seen me naked either and took me in for a minute. I was rock hard again, obviously, and ready to pop her right there, but didn’t want to frighten her. I told her to lay down and spread her legs.
“Are you going to lick my pussy? I hope you want to because I want you too before I get messy down there. I was afraid to ask.” I lowered my face down to her perfect virgin pussy and just stared at it for a second. Her light brown pubes were soft as a feather and framed those lips perfectly.
Her lips were fully engorged and her pussy was wide open for me. I was afraid to finger her too deeply since she still was cherry, so I just used my tongue. As I licked her hard and fast.I didn’t know much about going slow at first back then she ground her pussy into my face. I nibbled and sucked on her clit until she was moaning and trembling. I knew she was close to coming and was curious what would happen if I put a finger in her tight butthole.
I licked my index finger and slid it in slowly. She gasped and rotated her hips and seemed to like it. I was only into the middle knuckle and started making the “Come here” motion with it. That did it , she immediately began to scream and buck her hips and her cunt went into serious spasms. She was having an orgasm that was 10x as hard as any my fingers had ever given her. She wasn’t prepared for the intensity and began to cry as she released. I licked her until she pushed my head away.
“Oh god, that was amazing. You need to stop for a second so I can catch my breath!!”
I held her in my arms until she calmed down a bit. We began to kiss softly and touch lightly. I was still hard as a rock and she grasped my cock with her hand and stroked me a bit. I knew if she kept at that, I was going to lose my load too quickly, so I got the towel and shoved it under her ass. I was ready to deflower this beauty.
“Are you ready?.” I told her. She responded by opening her legs wide for me. I knelt between those perfect thighs and readied myself. She looked at me with total trust in her eyes.
“Promise me you’ll go slow. I love you.” I told her I loved her too and I meant it. I was no virgin and felt something new inside me. Now she was going to feel something new inside her.
We were both shaking a bit as I got my cock close to her pussy. That dripping, virgin pussy. A wet pre-cum oozed out of my cock, which I rubbed onto her wetness. She was grinding her hips and I could feel the heat from her pussy radiate onto my dick. I couldn’t wait anymore and entered her.
She arched her back in surprise and locked eyes with me. She was expecting pain right away but didn’t feel anything but my cock head in her opening. I hadn’t hit her hymen yet but eased myself up against it. She figured out that this was the moment she had been waiting for. I saw her grit her teeth and steel herself for the pain. I could feel the blood pulsing on my cock as I made the final push and tore thru her virginity.
She let out a shout and shut her eyes tight. I slowly went balls-deep into her and she responded by squeezing my cock with her cunt muscles. I withdrew and re-entered her, going slowly to ease her into it. She opened her eyes, which were wet with tears of pain this time. I asked her if she wanted me to stop, but she said no, keep going. I gently fucked that tight little hole and glanced down between her legs. There was quite a bit of blood oozing from her, but the towel was doing its job.
I began to suck and lick her tight little breasts that were tipped with hard little pebbles for nipples. She began whimpering and moaning a bit. I increased the speed of my thrusts but was still going very slowly. I wasn’t sure. But I thought I felt her pussy begin to tremble a bit as I slid in and out of her. I knew I was feeling her pussy grab my cock with every thrust inward.
I didn’t realize it, but she had grabbed my ass by this time and was pushing me into her. Her nails were digging into me and it hurt. I laughed and told her not to be so rough with me and she laughed back. I knew she was getting into it because by this time there was no question that her little cunt was trembling with a future orgasm.
She began to move her hips and arch her back and started to pant hard, her breaths coming short and quick now. Even at that age, I knew what that meant.She was getting close to coming. I kept the same rhythm going and started to kiss and suck her lips again.
She started squeezing me with her thighs and her ass started bucking as her first cock-inside-her orgasm ripped thru her. Her eyes opened wide, but I saw nothing but whites. At that moment, I would have been happy to die immediately after I came. Her eyes rolled back to the front and she locked eyes with me again.
I could tell she was shocked again by her orgasm’s ferocity and intensity. She was covered in a sweat that I wanted to bathe in. She smelled incredible, even with the blood between her legs. I was close to my own orgasm and began to thrust again. Deepa was really charged up after losing her cherry and having an incredibly powerful orgasm. I was going to go nice and slow the rest of the way until I came, but she surprised me again.
“Fuck me hard. Pound me. I’m ready!!” she exclaimed. I gave her a hard kiss and threw her legs over my shoulders. She let out a surprised “Whoop” and readied herself. I slammed into her as hard as I could and could tell she was still a bit tender, but could also tell she wanted me to fuck her hard until I came inside her. She reached under me and started stroking my balls that felt like they were about to burst.
I knew my time was short and told her I was going to come inside her if that was what she wanted. She assured me she did and I cleared my mind and focused on how good her incredibly tight cunt felt. I was absorbed in my own feelings when I felt her start to shake all over again.
As I went into my last few strokes inside her, she grabbed my ass again and screamed, “Oh my god I’m going to fucking cum again!!!!” and let loose with a gush of cum that splashed all over the both of us. It was like someone turned on a fountain or something. I couldn’t hold back anymore and let loose inside her, scalding her insides with my white-hot sperm.
She squeezed me hard with her thighs, cunt, and hands, trying to drain every drop out of me. She succeeded. We both collapsed and didn’t move for what seemed like forever. I know that I was drained. After a bit, I got up and grabbed the bloody towel and cleaned her with it. We staggered to the shower and took a nice hot shower and got back into bed. For the rest of the night, we explored each other.
We were glued to each other for the next two years, fucking like rabbits and doing everything we could think of. She got into anal and loved having me pound her little butthole. She could come just as easy with my dick up her ass as she could with it in her pussy. We ended the relationship when we went away to different colleges.
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Piper and I agreed, then got her parents and Ben to agree, to me going to Piper’s for a few days before Easter, then her coming to stay with Ben and me for a few days after Easter. We were both looking forward to it as I wanted to see what Isaac was going to make us do (Piper’s parents would be at work); and Piper eagerly wanted to see some of the things that I had told her that I got up to. I really hoped that the weather would be just a little warmer so that I could get her ‘out and about’...
We got back home the day before school started again. I’d had so much fun over the school holidays and I wasn’t looking forward to going back. Also, I was so knackered that after checking that I had something to wear for school, I went to bed. The next morning Ben woke me in the best possible way and that sort of set me up ready to face what I was expecting to be a crap day starting year 10. The weather wasn’t too bad as I walked down the lane to the main road to catch the bus to school. I...
Friday night Sue sat in an easy chair in the living room and watched her brother Dave as he, Cindy, and Janet enjoyed a three way. "Fuck me, Dave, fuck me," Cindy shouted as she bounced up and down on Dave's cock. At the same time Janet screamed in pleasure as she sat on Dave's face so he could eat her blonde cunt. Sue watched them and groaned in frustration as she tried to satisfy herself with her hand. Now that she was so close to losing her cherry the young girl felt more frustrated...
Candy Stroker Part 4: Cherry No More! Adam picked me up and asked me how work was. Still sorting out how I felt about Lois and Janelle being bisexual, I guess I seemed kinda out of it. He asked if I was OK, and I said I was tired. He drove me home and we kissed each other good-bye in the driveway. We talked about my 18th birthday that was coming up on Wednesday. I told him my parents had arranged a big family party on Friday night. I got the night off, grandparents, aunts and uncles were...
Candy Stroker Part 4: Cherry No More! Adam picked me up and asked me how work was. Still sorting out how I felt about Lois and Janelle being bisexual, I guess I seemed kinda out of it. He asked if I was OK, and I said I was tired. He drove me home and we kissed each other good-bye in the driveway. We talked about my 18th birthday that was coming up on Wednesday. I told him my parents had arranged a big family party on Friday night. I got the night off, grandparents, aunts and uncles were...
First Time(All characters are make-believe. Continuation to Part 1 of Cherryville)On the other side of Lake Cherryville is where the Girl Scouts are making camp. There are approximately 20 girls ranging from 12-15. The most popular girls are Brandy, Amy, and Stacy. Brandy is the leader. She’s 14 blonde hair and blue eyes. Amy is 14 as well with green eyes and curly red hair. The youngest of the 3 is Stacy. She has grey eyes with brunette hair. The 3 girls always setting trends and all the other Girl...
(Fictional story. None of the characters are real.) It was summer time and the Boy Scouts from Cherryville where packing up to go on a camping trip at the lake for a week. The scouts where from the ages of 12-14. They were all excited about going because they heard the rumors about the Girl Scouts from their town where going as well and setting up camp on the opposite side of the lake. As the boys are loading the vehicles up the camp counselors are discussing the plans for the week and which...
Tad's hands were shaking as he handed a wad of dollar bills to Cherry. "That's nineteen, and, uh, I got the rest right here..." He mumbled as he began to fish around in his right pocket for the last dollar, which was made up of many coins that jingled heavily as he tried to scoop them out. Cherry quickly counted the wad of money, and when she saw the trouble the nervous little boy was going to for his last dollar, she reached out and touched his wriggling wrist. "That's OK," Cherry...
Hello ISS readers.. I’m Cherry. M26. Hyderabad. Tall and handsome. This write up is real which has happened to me 3 years back. It’s gonna be a bit long write up but please do read till the end to know what happened in Vegas and to my Cherry.. Mail your Comments to In 2013 January, I was 23.. By then Had done all sort of naughty things when I was teen, as in, squeezing hot girls boobs in city buses, trains, crowded places.. Especially in Bangalore shopping malls, in scary house, special...
Anastasia's Cherry Gets Popped By Anastasia Messier I didn't have to wait long to find out what was going on in the minds of these devious women. I was pushed to the bed face down and Audrey grabbed my left hand as Melissa grabbed my right. Wrist restraints were quickly put on my wrists and I found out I was in no position to go anywhere. My wrists were strapped one to the footboard and one to the headboard. Renee told me, "Get on your knees...
The next morning I woke up lying on my side with my back to Ben and his cock sliding in and out of my pussy. “I love it when you wake me like that Ben.” I said. “Ben wakes you like that as well does he? Tanya loves it too.” Ryan replied. “Oh sorry Ryan, I forgot that it was you that fucked me last night.” “That’s okay Cherry; Ben’s probably waking Tanya like that as well. If we stay quiet I may get the chance to wake Piper this way as well.” We slowly fucked until I’d cum then instead of...
Chapter 14 The military foursome were going to miss out on their fall semesters, with Scott barely returning in time to start his first semester in late January. The group staying in Winnisimmet were saddened to see the four heading west leave back in June, it was the first time since 8th grade that the group had been separated for any length of time. It was the start of the group becoming their own people, but for the 14 it was still a tough revelation to them. Jaimie and Miles...
This is for all you men and women out there that like some taboo stories.Chapter 1Cathy Jones, walking home from school, felt a secret tingle in her pussy. She had done something at lunch time she shouldn't have done, and now she was busily trying to hide the knowledge of it from herself." Another day, another night of study," she muttered to herself. Lost in her thoughts, she wasn't aware of the heads she turned.She was only sixteen years old, but she was a traffic-stopper. Her youthful hips...