Chubby Young Lover


This a true story of secrecy, sexual exploration, and obsession.


This story took place during my senior year in high school 2011. Trying to be popular in high school was an everyday job. With a rather small class it was hard to impress the very few attractive women in my grade. Playing sports was the main opportunity to attract some attention. What girl doesn’t like a muscular boy who is good at sports? The problem was I wasn’t very muscular and I wasn’t as good at sports as some other boys in my class. I attracted a few girls attention but none that I was interested in.

Life in high school was different for me than it is for most people. Even though I love high school and made some great friends, there was a certain kind of pressure to try and act cool. I would say I acted different in high school than I did at home. For instance most conversations consisted of sex and women. Whether they were women in our class or just hot women we knew or had seen.

In a class with only 85 students I had about four girls that were hot. Only one had a boyfriend and she was the hottest. Most of my friends had lost their virginity by senior year and I felt the pressure to do the same since I was 19 and most of my friends were 18. I often lied about my virginity when people asked me because I didn’t want to be made fun of. I felt somewhat pathetic masturbating at home when I should be with my girlfriend having fun. Problem was I didn’t have a girlfriend.

With the chances of dating one of the few attractive girls in my grade looking slim, I turned to girls in the grade below me. As I went through puberty my sexual attractions changed often. When it came to masturbation material I found new exciting things weekly. My first attraction was younger girls meaning girls in my grade. As I became more nervous about losing my virginity I became interested in older women. I call them Milfs but any way you call them I was attracted to Moms. Something about an experienced older woman with a big set of breasts really turned me on.

My attraction for Milfs still remains but now I was becoming interested in chubby women. Not just older chubby women but women my age who are chubby. In my opinion fat and chubby are two different things. Fat is too big and chubby is slightly overweight but still attractive. In high school most boys tried to avoid those girls and were often overlooked because of their size. As I realized this I found a loophole in the system that I could capitalize on.

One day at lunch I spotted my target. Looking back I wouldn’t call her a target but that’s how I felt at the time. Her name was Rachael. She was an 18 year old junior who was very beautiful. At about 5 foot 5 she was gorgeous. She had very big breasts for her age and had a great ass. Her only flaw was that she was chubby, borderline fat but still attractive in my eyes. As to my knowledge she has never had a boyfriend but it is a very nice girl.

I knew I must pursue Rachael in secrecy because I knew my friends would tear me apart with the jokes. I couldn’t talk to Rachael at school so I would often pursue her after volleyball games. No one in my grade was interested in watching junior varsity volleyball games so I knew it would be safe. After the games I would often talk with her about the game and about school. I was very good at talking to girls and before you knew it we were becoming good friends.

One day after one of her volleyball games we were casually talking and she asked me if I wanted to exchange cell phone numbers. I agreed and our conversations continued long into the evenings. I knew my chances of being discovered by my friends grew so I made up a lie to tell her that we couldn’t talk during school hours. I think I told her coaches didn’t want us to have girlfriends and she fell for it.

As our relationship grew I could tell she was becoming very attracted to me. Our conversations gradually became more sexual. As we explored each other’s sexual experiences I was shocked to find out she has had sex before. I was even more surprised to hear she had sex with a boy in my grade. He was a real loser. A not very intelligent, overweight kid who thought he was a bad ass because he smoked and hung out with the wrong crowd. I was very curious about their sexual encounter and found out he had a small penis. I found that very funny.

We often played truth or dare over the phone. She would often ask how big my penis was but I would try to change the subject to make her anxious and horny. Truth is I had no idea if my dick was big or not. My penis is 6.5 inches erect and I figured it was somewhat big but wasn’t sure since I haven’t seen other boys erections in the showers. I lead her on to believe I’ve received a blowjob but really haven’t. I would proceed to ask her if she would spit or swallow after a blowjob. To my surprise she said swallow. I became very aroused during our conversations and I would often masturbate during them.

Our ambition kartal yeni escort grew and one day I dared her to send my pictures of her naked body. She was hesitant at first but I told her I would send a picture of me naked in return. She gave in and agreed to try sexting. The first picture I received was of her big boobs. They were quite large and sagged slightly. Her nipples were quite big as well. My interest in chubby women grew from that picture. I loved large boobs and hers were amazing. I wanted nothing more than to squeeze them right then and there. I persuaded her to send more and she continued. The next one was a close up of her vagina. I’ve only seen pictures of vaginas on the internet so didn’t know much about them but hers was very attractive. It looked very tight and had a slight pinkish color too it. It appeared she hadn’t shaved for a while but that turned me on even more.

After she sent two pictures of herself she wanted one from me. I became very nervous and tried to find a way out if it. I apologized and said I had to go eat but would do it another time. The next day at school I stared at her the whole time during lunch fantasizing about her body. I felt somewhat awkward when we made eye contact when she quickly looked away.

Later that night I started off by texting her first. We continued with small talk then I asked her if she could send me a picture of her ass. She agreed but only if I would send her a picture right after. I sucked up my fear and said ok. The picture I arrived and instant erection. She was wearing a very sexy pink thong that sank deep into her ass crack. Her large ass was amazing, perfect shape, perfect size. She was bent over slightly so I could see her beautiful mound between her thick, sexy thighs. I often wondered if I fucked her in the ass, if my dick could reach to her ass hole.

I now knew it was my turn to send a picture. She wanted one of a bare skin erection. I didn’t want to send a bare skin picture in case she showed it to other people. In a way I wanted her to show other people but I was still nervous. I was still wearing my compression shorts so I decided I would take a picture while wearing those. Compression shorts are pretty much very tight underwear. Very easy to see the outline of a penis. I got a semi hard on which was basically an erection that could face downward between by legs. The picture turned out great. My penis was easily visible and it still looked big. I sent it and waited for a response.

“HOLY CRAP THAT’S HUGE”, was the reply I received. I laughed and replied “what do you think”?

“That is one big penis, very sexy”

I was very flattered to hear that. Now I knew that my penis was big. A girl with sexual experience said I had a big penis. I now wanted to fuck this girl more than anything in the world.

Immediately after sending the picture I asked her if she wanted to hang out this weekend. My parents were going to football game with their friends and would gone Saturday and Sunday. My original plan was to have a bunch of friends over to drink and watch the game but have Rachael come over sounded a lot better.

“I would love to come over”, she replied and I was thrilled.

We talked about the coming weekend all week. She decided she would just stay overnight and tell her parents she was having a slumber party with the volleyball team. We planned out everything we would do. We decided we should go shopping, then a movie, and have a pizza and chill out on the couch later that night. As the weekend drew closer my nervousness grew. I knew the chance of sexual activity was high was I was also excited.

My parents left for the game Saturday morning and said they would be back Sunday evening. I waved goodbye and then gave Rachael a call. She got dropped off at her friend’s house two blocks away and I went to go pick her up in my truck. She looked very sexy walking down the sidewalk towards my truck. She wore a tight Hollister t-shirt that made her boobs look huge. They bounced slightly and gently as she walked. I had an erection before the date even started. She completed the ensemble with a nice pair of khaki shorts and sandals.

We talked all the way to the mall and proceeded to shop for about two hours. As we walked around the mall we walked by Victoria Secret, this gave me a good idea. When Rachael went to the bathroom, I ran over to Victoria Secret and picked out a very sexy pair of leopard matching bra and panties. I hid them in my other bag so she wouldn’t notice. After shopping we walked over to the movie theatre next door. We saw Bridesmaids which was very funny.

After the movie we drove back to my place and I popped a pizza in the oven and made us a few cocktails. My parents weren’t strict about drinking as long as no one drove afterwards. We ate our pizza and I slipped out of the jeans and put on a comfortable pair of gym shorts. I then proceeded to the couch to lie down.

“May kartal escort I”, she asked as she snuggled up in front of me on the couch. We were now spooning on my couch watching TV. With my head slightly above hers, her ass was directly in front of my crotch. She was trying to get more comfortable and started getting closer to me. She wiggled her ass back and was in direct contact with my penis. My gym shorts had to restrain on my penis so it was snuggled right between her ass. I tried to keep calm and not get an erection because she would defiantly able to feel it but she could probably feel it already.

“Are you comfortable? I’m not squishing you with my huge ass”?

“It’s perfect”, I said in a very smooth way.

Rachael then sat up and pulled me up towards her. She stared into my eyes and moved her lips closer to mine. We passionately made out with each other from what seemed like an hour. Our kissing became very intense. She started sticking her tongue into my mouth I did the same to her. We explored every inch of each other’s tongues. I had now developed a massive erection and my shorts did not hide it very well. We took a brief break from kissing and Rachael looked down and noticed the massive tent in my shorts.

“Oh my, someone’s getting excited.”

“Ha sorry about that, you’re just so gorgeous I can’t believe what’s happening.”

“Well it will only get better”, she said. I could only imagine what the rest of our night would be like.

I asked her if she wanted to go to my bedroom where we could get more comfortable. We walked hand-in-hand to my room and we lay down on my bed. We continued where we left off and started making out some more. My kissing was either getting better or we were getting hornier. She started to slide off my shirt exposing my chest and abs. she rubbed her hand from my neck to my waist and lightly touched the head of my penis. It twitched slightly and I almost came.

“Just relax”, she said.

I proceeded to slide off her shirt over her head exposing her bra and big boobs. I gently kissed her neck and worked my way down to her boobs. I didn’t want to rush things so I just grabbed her bra covered breast and kissed the top of it. I worked my way down her stomach and started to unbutton her shorts. The raised her hips as I slowly slid her shorts down revealing her baby blue thong. Thank god for porn films or I would be completely lost at this point.

To increase her excitement I placed my mouth on her thong directly over her vagina and blew hot air onto her. This drove her wild and she began moaning and wiggling around on the bed. She put her hands on my head and pushed down on it burying my head deeper in between her legs. I could barely breathe at this point and I had to come up for air.

Now it was her turn to undress me. We switched positions and she began untying my shorts string. She jumped off the bed and I lifted my legs so she could slide down shorts off. Next came my boxers, my erection was now pointing straight up and she grabbed my waistband and slowly slid them down revealing the head of my penis first. She was smiling the whole time while biting her lower lip. I was in complete shock. Before I knew it, she threw my boxers on the ground.

She was getting ready to take off her bra and panties when I told her I had a present for her. I got off the bed and went to get the bag from when we went shopping. I brought the Victoria secret bag into my room. I handed her the bag and told her to go change. She went into the bathroom across the hall and soon came back into my room. She walked in the room in the sexy bra and panties I bought her and she leaned up against the door frame in a very sexy pose.

“You look amazing, now get that hot ass over here”, I said.

She ran and jumped on the bed straddling me like I was a horse. It felt like being tackled by a linebacker but I loved it. My penis was now pinned between me and her vagina. I could feel the heat coming off of it. We made out for a few more minutes then she started to take off her bra. She unstrapped it and held her arms across her chest covering her boobs. She lowered her hands and I immediately leaned up and sucked on her nipple. It was so sweet and tender. Her large nipple barely fit in my mouth. I cupped her other breast in my hand and caressed in gently exploring the shape and feel of it.

She the then slid farther down and grabbed my penis in her hand. Her hand was warm and was a great sensation on my erect penis. She gently explored my stiff penis. She then spit on her hand and began rubbing the saliva the length of my cock. She pumped slowly at first and began increasing her pace. She worked her hand in a twisting motion all the way up to the head which was very sensitive. I did my best to not blow my warm, sticky load.

As she worked my length in one hand, she cupped my balls in the other. Working them like she was a nurse giving a physical. She kurtköy escort must have been able to tell when I was going to cum because right before I blew she stopped and told me to switch spots with her. She lie on her back and spread her legs. I slid off her panties and stared at her pussy. She had shaved recently leaving a small patch of hair just above her vagina. I began by wetting my fingers with spit and rubbed my fingers up and down her slit. She moaned softly and gripped the bed sheets.

I then began exploring her crevice with my tongue. This was my first time eating out a girl so I took it slow. I worked her slit like I was licking a sucker. I must have been doing something right because she was moaning louder now. I kept working her with my tongue, trying to go deeper into her. I then tried inserting my index finger while working my tongue so see what kind of reaction I would get. I must have hit the sweet spot because she was screaming now and saying she was cumming. Her hips started bucking and small amount of fluid came out of her vagina. I licked it up and the taste was amazing.

“That was incredible; I’ve never had an orgasm that intense.”

Rachael then moved & sat between my legs, she started stroking my dick with both her hands. She leaned in and licked the tip of my cock with her tongue. Her tongue sent shivers up my spine & I wanted more, a lot more. She then gave my cock a few more slow licks, covering the top with her saliva. Then she opened her mouth and took my cockhead in her mouth & closed her lips around it.

Watching her lips covering my hard cock was sooo hot! She moved her lips down taking half of me in her mouth, and then moved her lips up till just the head was inside. She kept repeating this very slowly covering my cock in her saliva.

I was feeling the warmth of her mouth & the underside of my cock was sliding on her tongue, giving me more pleasure. She increased her pace a little as her hand started caressing my balls again. I was looking down oversized babe, her eyes watching me & her hands working on balls. A few more licks & I came in her hot mouth. She wasn’t joking around about swallowing and kept on sucking my dick and gulped every drop down.

I was soon hard again then she came on top of me straddling me with her legs on each side of me & slowly lowered herself onto me inserting my cock in her hot pussy. My hands were caressing her thighs as she took my entire cock and sat on top of me with her eyes closed & her teeth biting her lower lip. She placed her hands on my chest and bent down to kiss me. She started to move her hips up & then down very slowly letting me feel her pussy wrapped around my dick. I grabbed her plump ass & started moving her up & down on my cock at a steady pace to assist in the pleasure.

“Hhhmmm… Unh! unh! Unh! Unh! Unh!..”

Noise was coming from her lips as well as mine on every thrust as I was enjoying the warmth of her wet pussy and she enjoyed my cock deep inside her. Between our moaning and feeling of her pussy, that really got me going. Now I wanted to really just pound her pussy like in the porn movies so I removed her from my cock.

I totally manhandled her which took all my strength and forced her to her hand and knees. She thoroughly enjoyed this. I positioned my penis behind her hole & pushed my dick inside her warmth. I grabbed onto her thick waist & started moving my cock inside her while pulling her hips towards me at the same time. Her ass cheeks were rippling with every hard thrust & the contact of my body with hers. There also was a loud slapping sound which I’m sure was a combination of my balls hitting her ass and her boobs bouncing like basketballs.

“Unh! Unh! Unh! Unh! Unh!”

The coupled moans persisted.

I was desperately trying to give her a pleasure she would never forget. I picked up the pace one last time, filling her with my cock over and over again. At this point she was screaming very loudly. I had hoped the neighbors couldn’t hear but I didn’t have time to worry about that.

“I’m gonna cum!” She screamed. “Oh fuck you’re making me CUM! Keep fucking me… I’m nearly there…harder, harder, …OH YES! I’M CUM…CUMMING! YESSS!!!”

Almost immediately after her orgasm I was ready to do the same. I couldn’t hold off any longer and warned Rachael I was gonna blow. She was oblivious, basking in the aftermath of the best orgasm she ever received. I drove my cock into her and felt a stream of cum emptying from my balls into her pussy.

“Gimme all of it baby!”

My balls finally emptied and I pulled my soaking wet cock out of her pussy. I collapsed on the bed next to her, completely exhausted. Rachael rolled over alongside me and placed one leg over both of mine. A mixture of my cum and her juices oozed out of her pussy and onto my leg. She wrapped her hands around me and kissed me on the cheek.

“That was incredible.” She said.

We lay in the position for some time, just resting and looking up at the ceiling. It had been about 30 minutes when she began to reposition herself to get more comfortable. She then placed her left hand directly onto my crotch. I was flaccid at this point but the touch of her warm, soft hand made my penis twitch with new life.

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