ASSTR
categories

Chubby Jamie driving me crazy

09/24/2024

I was 20 years old and living in my first apartment for almost a year. I had graduated from high school about 2 years prior and had immediately landed my first position in the business department of a large lumber corporation. There was a company branch site in my hometown, a large metropolis in the South, so I began working from home soon after graduation.

About a year later I moved into my little apartment, on the other side of town from where I grew up. I was very proud of that apartment. What a bachelor pad! Okay, so the apartment itself was kinda small: it had one bedroom, a den, a kitchen, a bedroom, and a closet, all of which were more or less cramped for space. However, the rent wasn’t so high, and there were a lot of extra benefits at the apartment complex.

For example, we got a satellite TV hookup in the main room, and Ethernet was free. In addition, a community pool, exercise room, and bar were available at no entry fee to occupants of the apartments. I liked to keep fit, so the exercise room was a big plus too.

Also, I did enjoy the good drink every once in a while, so I frequented the bar after work hoping to get someone to hand me a glass. (I was underage at the time.) That bar was where, about a year after I moved in, I met sweet, red-haired Jamie.

Jamie had just left high school herself, although in retrospect I don’t believe I asked her whether she had actually graduated or not. She was living in the apartment complex as well and was supporting herself by working as a secretary for a travel agency a couple of blocks away. She was surprisingly alert and seemed intelligent for a girl of her age. I would say that she had more common sense than I did; she seemed to be very worldly and able to take care of her own needs.

Jamie was quite a specimen of youthful beauty at the ripe age of 18. Red hair decorated her head in long straight strands ending in large curls, perfectly crafted. Jamie had very white, creamy skin with no impurities anywhere to be found on face, body, or foot. Only a few post- adolescent blemishes adorned her sexy figure here and there, reminiscent of her years of blossoming. She had a very thin waist and was very slender overall, weighing in at about 105 pounds, I would have guessed.

Jamie loved to wear deep red lipstick to show off her wide, sensuous smile, and it contrasted her pure white face amazingly. She was not unfamiliar with short, tight skirts (mostly black ones), which seemed to be made exclusively for her full curves. Her legs were long and curvy as well, and were always closely shaven. Jamie’s breasts were of a smaller size than the average, but she definitely was not flat.

Finally, her small, cute feet and hands were almost always painted red as well, to accentuate and complete her perfectly rouged appearance. I liked this girl tremendously. We seemed to hit it off almost immediately. Jamie and I liked to go walking around the town, stopping for ice cream or to play a game at a bowling center or laugh at the silly people walking by over a light lunch.

Unlike most teenagers, Jamie was very sure of herself and every action she took: if she was ever hesitant about any decision, it was not at all obvious to me at any time. Her persistent smiles communicated her confidence, and that made her all the more attractive to me. When we started to fool around, I was having a lot of fun. Jamie liked to move slowly, like most girls, but never left me unsatisfied. Jamie wanted to do most of the work herself, but she perpetuated my pleasure and enjoyed studying my intense looks of ecstasy, which she created.

Thus, she loved giving slow handjobs, moving slowly enough so that I hardly progressed at all toward my own orgasm but quickly enough so that the pleasure never ceased. Jamie also liked to be stimulated with the hand, and although she enjoyed mine, most of the time she chose to use her own hand. I gathered that this, too, was because she liked to see me turned on the most, and she knew that me watching her pleasure herself really got me going.

I was always sure to have several condoms on me whenever I was going to meet Jamie, especially once we started fucking regularly. I was not, of course, a virgin, but I didn’t want to catch an STD, and I certainly didn’t want a screaming kid at all, but certainly not at my age.

Anyway, I knew that Jamie was also on the pill. (She popped one of those things daily right in front of me.) It’s not that I was suspicious of Jamie. I knew she had had sexual encounters in the past, but she looked and acted very healthy and I trusted her when she told me that she was clean. It’s not like I could just go up to her and demand that she get tested for every STD out there anyway: that would be awful of me.

However, it was the threat of becoming a father that scared me the most. I just simply never cared for kids, and the prospect of taking care of one for 20+ years financially, emotionally, and energetically never appealed to me at all. So, I opted to use the condoms anyway, even though I knew Jamie was on the pill. Better safe than sorry. Even so, sex with Jamie was always wonderful. She would always bring me up, ever so slowly, toward my release using her hand, and then, when I was getting close, she would slip a condom on me and I’d ride her until I came in her very hard.

It always happened that she came first; her other hand knew exactly what she liked. It always got her very excited when it rubbed all around her clit and labia before I mounted her. Sometimes we would do it doggy- style or with her legs out to the side, but we liked good ol’ missionary the best because it made us feel closer together. I got maximum penetration into her with that position, and for some reason, it always seemed to make Jamie smile even more than before when I came on top of her.

I had only known Jamie for about four months or so when I received word that the local company where I worked was downsizing. I had to move to a different site out of state in order to keep my job. If I was willing to make the move the lumber company would give me a raise in salary.

I thought about it for a long time, but in the end I decided to move away. I thought it was the best decision as far as my career was concerned, and I felt my life should move on away from my hometown for at least a little while. It was certainly a difficult decision to leave my hometown, where I grew up, but it was even harder to leave Jamie, whose company I had come to really enjoy.

When I told Jamie the news that I was leaving, she was very distraught. “Why’re you leaving me?” she asked, her eyes pleading with me.

“It’s not because I don’t want to be with you or that I hate this town,” I explained somewhat fruitlessly. “I have to follow where my career leads me, and right now, if I don’t leave, it would be a stupid career move.”

“When are you going?” she inquired.

“In about month,” I replied. Although I expected her to say more, she didn’t, but she seemed to swell up, and then tears came. All the time, she looked right at me with her gorgeous green eyes. Finally I grabbed her and held her, thinking about what I might do about her.

But both Jamie and I knew she couldn’t come with me out of the blue. Her family was far too proud to allow her to drop her entire life, including her job and apartment just to follow some guy who she’d practically just met. Jamie wasn’t tied down by her family, but she respected them too much to disappoint them.

I thought about marrying her, but I was very hesitant about walking down the aisle with someone I’d met only four months ago. It was just too early in our relationship, and we were too young.

That night I took her to the movies to get our minds off my move. After a few days of emotional instability between us, things were seemingly almost back to normal in our relationship. It was very odd: despite the fact that we only had a short time left together, we were able to laugh, play, and touch each other just as we had before. Those days were wonderful, just like before the news of my move. It was a wonder that we were able to forget about it and just concentrate on each other in the remaining moments, savoring the time we had left to share.

We even had sex a few times in that last month. (We were thwarted much of the time because I was very busy at work packing up and getting ready to leave, in addition to the fact that we were both somewhat depressed.)

About five days before I was to leave, Jamie and I were once again spending the evening together, this time lounging by the pool. Jamie was a knockout in her favorite string bikini, nothing but white flesh exposed everywhere, dressed in red from her cute curls, nails, and tempting lips. She was smiling at me all evening, and it was driving me crazy.

When the sun went down, we got our things and went to my apartment. As we walked to my front door Jamie rubbed up against me and swung her hips in front of me so I could get an excellent view of her round little bottom. I grabbed her flat tummy from behind with both hands and began exploring a little.

She enjoyed that and responded by stopping for a moment and squeezing my hands. Then she turned her head and gave me a beautiful, devilish grin. “Wow,” I thought. “I’m very glad I put those two condoms in my wallet today before I came home.”

We entered my apartment, and Jamie ran to the bathroom to take a quick shower. I could tell that she was very horny, and that was making me hotter and hotter by the second as well. The two of us hadn’t had sex for about a week, and I already had a lot of tension built up.

Jamie emerged from the bathroom wearing her bikini again. (I guess she assumed she wouldn’t be wearing it for much longer.) I kissed her on the lips, then I told her it was my turn in the shower.

“Don’t take too long; please hurry!” Jamie exclaimed as I entered the shower.

I was hard in the shower and was thinking about Jamie’s body the whole time. I couldn’t wait to touch her and make her feel wonderful. When I left the bathroom, I couldn’t find her so I opted to put on some boxers and an undershirt in lieu of walking around naked. Right when I had concluded that she must have left for some reason. Then I heard her calling me from my bedroom. I found her already buried under the covers. “Funny, I was just in here,” I noted to myself.

I noticed her bikini top hanging off of a nearby chair. That was a signal to me that she was naked underneath the covers except for possibly her tiny bikini bottoms. The realization brought a big smile to my face and made my cock jump with anticipation.

I climbed under the covers to join her. My hands roamed all over her body, her tummy, legs, inner thighs, outer thighs, and breasts. I stopped to attack her neck, planting long kisses below and behind her ears. I then rubbed my palm slowly across her shoulder blades, down her arms, and then I grasped both her hands.

Jamie returned my caresses by roaming her hands under my shirt. I kissed her breasts all over, finally sucking her small erect nipples softly, then more vigorously, making her close her eyes in pleasure.

She reached for my hard cock, and rubbed it slowly, “Get these clothes off right now!” she suddenly demanded.

I removed my shirt while she pulled at my boxers, then raised myself and the covers up so I could look at her. She was amazing; her body was a perfect. I could see her entire body from pretty red hair and lips all the way down to cute little arched feet. Only the bikini bottoms impaired the view of her little snatch.

As always, I couldn’t believe that I was about to fuck this girl. It was clear that we were both so hot that we didn’t need any more petting to get us going. We both wanted release.

I quickly hopped out of bed and grabbed my pants. I opened my wallet and searched for one of the condoms, but to my surprise, I couldn’t find any! That was really strange. I knew, I was absolutely sure, that I had put some in my wallet just that day. Still, maybe my mind was playing tricks on me; I had a lot on my mind lately. “Jamie, I don’t seem to have any protection on me. I’m sorry.”

Jamie didn’t seem to be the least surprised or disappointed, and continued to smile at me. “Come here. Come back here,” she insisted. I returned to bed, and Jamie quickly placed my hands on her waist. She seized my thumbs and put them under her bikini strings on each side. Then she curled my fingers around over the top of the same strings, and made a motion for me to pull her bikini bottom down. I hesitated.

Jamie leaned up to me and whispered, “Pull them down. Pull. Don’t you want to pull them down?”

I could tell that Jamie was extremely horny now.

“But I don’t have protection, Jamie. Shouldn’t we stop?” I asked.

“We don’t have to go all the way, I just want to be naked with you,” she replied.

After convincing myself that would be okay, I began to slowly pull Jamie’s bikini bottom down. It was a long journey to slide them down her sexy legs all the way to her beautifully formed feet.

Now totally naked, Jamie reached down and pulled me back up to her. She immediately began fondling my cock and balls as she usually did. I systematically went into contortions. Her light caresses were driving me insane. Then she grabbed my cock between her thumb and fingers and began stroking me as she liked to do.

I was in heaven, but I craved more like weary desert traveler craves water. My orgasm was starting to build, and I pulled Jamie’s hand away. “Jamie, I don’t know. Do you have any protection with you?”

Jamie stared at me for a few moments, keeping her intoxicating smile all the time. Then she then quickly moved her head back and forth to say, “no”.

I was mad with desire, “Well, I guess that’s okay. You’re on the pill, right?”

Jamie then looked into my eyes, and stared at me briefly in silence. Then she responded once again by rapidly shaking her head from side to side to indicate “no” again.

I was in shock. “I thought you were on the pill all this time!” I said.

“Um, I quit using the pill about a week or so ago,” she admitted.

My mind snapped back to reality. Then in a flash I knew what was going on. Jamie had planned this encounter. She stopped taking her birth control about a week ago, knowing that it would quit working by tonight and that she would be unprotected. Further, she must have hidden or destroyed the condoms that I had placed in my wallet today. Now she was making me so incredibly horny that I would want nothing more than to fuck her.

Jamie had already found my hard-on again and was stroking me up and down. For a moment, I let her, lost in the pleasure she was giving to me. But then I snatched her hand away once more. “Jamie, we can’t. It’s not safe. You could get pregnant,” I insisted.

“Oh John, I’m not worried about that. Let’s not worry about that right now. Let’s just have some fun,” Jamie responded. “Don’t you want me?”

I hesitated, but had to concede that I most definitely did want her.

“Look at me, John. Look at my body,” she demanded. Jamie moved the covers down over us to the bottom of the bed so that we were both exposed. Then she began cupping her breasts with one hand, tweaking her nipples and wincing with pleasure. She slowly spread her legs, and with the other hand, she rubbed her clit and hole like she always loved to. “Look at me, John,” she repeated. “Do you like my legs spread like this? Don’t you want to fuck me?”

Indeed I did. The only thing I wanted at that moment was to stick my angry, pulsing cock into that hourglass figure. But I knew that was suicide.

Jamie grabbed my member and began stroking it again. I moaned out in pleasure, and she moaned back at me, rubbing her body against me like a cat in heat. Then, with her eyes locked with mine, she slowly drew my cock closer and closer to her waiting hole. When my tip touched her moistness, I knew this was the last chance to retreat. I hesitated even while Jamie grabbed my behind to draw me into her.

Defeated, I leaned downward to Jamie’s face and kissed her deeply on her shapely lips while I entered her quivering nest. We both groaned in rapture at the initial sensation as I penetrated her. Jamie was so wet that I slid most of the way into her, and only had to push myself in a bit further to make the penetration complete.

I couldn’t help myself, almost at once I began to move slowly in and out of her, and with each stab Jamie dug her nails hard into my back. She cried out as if she were in pain, but there was only pleasure. Intense pleasure!

I moved my hands all over her legs, upturned and in the air, on both sides of my thrusting hips. And I began to pump her a bit faster.

“Oh god, what am I doing? What am I doing?” my mind screamed, but my body did not listen as I continued to drive my rod deep into her like an animal.

I looked down at Jamie, at her perky breasts, her white skin, her visible rib cage, her flat tummy, and her very narrow waist. I knew that in a matter of moments I would ruin that hot little body. Once I came in her, that same tummy would grow out very large and her waist would stretch and her figure would be damaged permanently. I was going to impregnate this girl, and I was powerless to stop it now.

If only I could quit just for a moment, long enough to allow my reason to return so that I could stop. But I knew I couldn’t. The pleasure was too intense, to primal.

“Oh god, god!! Please don’t stop, John. You feel so GOOD!! Whatever you do, don’t stop. Please..” Jamie pleaded with me in ecstasy.

Pound after pound I drilled deep into her, knowing that with each thrust I was coming closer and closer to the demise of my personal freedom as a man. Jamie was trying to entrap me before I left town. If I got her pregnant, then I’d have to be tied to her forever, she knew that.

Perhaps she would make me stay, or would insist that she go with me. She was after my freedom; she wanted my baby. As she drew closer and closer to her orgasm, she began to admit that very fact. “Oh yes, YES! Oh John, it feels so good. SO GOOD! I love you between my legs, on top of me. You won’t get away from me, John. You can’t leave me. You can’t. Doesn’t it feel good? Oh John!! JOHN!!! JOHN!!! JOHN!!! YES!!” she exclaimed as her orgasm overtook her.

I felt her open up very widely and deeply. All of her screams of pleasure and her desire for me to continue pumping her was bringing me closer and closer to my own climax. I started pounding her very hard. I couldn’t help myself.

Then, I felt my orgasm very near. God, my body wanted to cum in her, deep into her unprotected cunt. But no! I had to stop somehow. If only I could hold back.. “AHH AHHHH!!!!” I yelled as I began to cum deep inside Jamie’s prefect body.

She sensed that I was cumming and she grabbed my backside, trying to keep me from abandoning my task. She needn’t have worried, though, because I was far too lost in my orgasm, the pleasure of her body, and the sheer bliss of the moment, for me to stop.

“Knock me up! Knock me up, John! You know you want to! Oh please! Don’t stop cumming in me! Give me a baby!!” she yelled. I came, squirt after squirt, in Jamie’s vagina, my cock head coating her cervix over and over again with my overjoyed sperm.

When I finally finished filling Jamie up with my seed, I collapsed on top of her in utter defeat. She caressed my back and ran her fingers though my hair. I looked up at her, and she was smiling as always, perhaps even a bit more now. “SShhhhhhhhh…” she said. “Don’t worry. It will be all right. I promise. John, you should know that it is close to the most fertile time in my cycle. But don’t worry.. Please don’t worry.”

When Jamie told me about 3 days later that she was pregnant, I had already decided that I would “do the right thing” and propose to her. I postponed my plans to move for about a month so that we could make arrangements for a wedding and get married as soon as possible.

I married her about 3 weeks later, and then we moved out of state to my new location with the lumber company. About 8 months later out daughter Tammy was born. She was quite a handful, always crying, shitting all over the place, and needing to be fed.

Jamie gained a lot of weight during the pregnancy that she never lost. Nearly 40 pounds. She just kept eating and eating. She craved something, so she ate it. Ice cream, doughnuts, cake, steak, you name it. The baby was her excuse to binge. Her stretch marks made from the birth of our baby are quite large and unattractive, and her continued weight gain makes her look like she’s perpetually pregnant.

It’s been 7 months since Tammy was born, and now Jamie wants to have another baby. I don’t want another child, and Jamie and I haven’t even had sex for at least 2 months anyway. I’ve decided to divorce her. I know I’ll be paying alimony and child support for the better part of my life, but I can’t stand to be around that fat woman or the little baby that I never really wanted, even though I have tried desperately to care for her. I’m taking the papers to Jamie tomorrow.