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Jessie sat across the room from me in my history class during my junior year of college.

I’d spotted her on the first day, her shimmering auburn hair catching my eye first with the way she filled out her hot-pink sweater a close second. She was often late, but she always appeared casual and unhurried. She paid attention in class and joked with our professor when she was called on, but as soon as the hour was over, she was the first one out the door.

For the initial weeks of class, I watched her from afar, but one day I decided I needed to get to know her. I got to class early and made sure to sit down at the desk next to her usual seat. But just my luck, she was later than usual. By the time she arrived, someone else had taken her spot, causing her to sit in the back of the room. However, I wasn’t deterred. I took my new seat again the next chance I could. My plan worked, and she sat down next to me.

I’d probably stared at her the entire class, but I’m not sure she even noticed. She’d had a laser-like focus on the lecture. But I was determined to speak to her, so at the end of the hour I made a joke about our professor and she laughed. I asked her if she ever used an instant messaging app I like, and she told me her username.

That afternoon I logged in and sent her a note. We chatted for hours that night. I started talking to her every day, but every time I thought about asking her out, she’d mention some guy she was seeing. She didn’t seem opposed to my flirting, but she never took things further, and by the end of the semester, I’d accepted that nothing was going to happen between us.

Months passed, and I kept chatting with Jessie, but for the longest time, all I had were fantasies. The only action I was getting was in my imagination — until my final semester of college, that is.

A year after we first met, I ended up in another class with Jessie. The first day of the semester, when she walked in and spotted me, her whole face lit up. She was definitely happy to see me — and I was probably twice as happy to see her.

In the weeks that followed, Jessie sat near me, even though there were lots of desks and she could have put plenty of space between us. That made me start to think we had something brewing.

My hunch was right. One day after class, Jessie asked me if I wanted to grab lunch. I agreed, and we had a nice afternoon together. When it was time to head home, she said she’d walk with me to my car. We strolled while talking pleasantly, discussing class and what our plans might be after graduation. She was applying to a master’s program, and I was hoping to go to law school.

Anyway, I was parked in the underground lot on the other end of campus from the dorms where Jessie lived, and because it was late on a Friday afternoon, most of the place was empty. My car was all by itself in a dark corner of the garage; the next nearest vehicle was at least 20 spaces away.

When we reached my ride, I turned to say good-bye to Jessie, but instead of responding, she leaned forward and kissed me. I was so startled it took me a few seconds to start kissing her back, but when I did, I went all out. I wrapped my arms tight around her to hold her in place and then kissed her so thoroughly it started to feel like our lips had actually fused together.

Once we finally broke our embrace, I expected… well, I don’t know what I expected, but it wasn’t what happened next. Instead of an explanation or an excuse, or even a follow-up kiss, what Jessie did was tell me to open the door of the car and get into the passenger’s seat.

She was wearing a dress that day, a rare occurrence, and once I sat down in the car, she climbed in and straddled me. She reached between our bodies, unzipped my fly and pulled out my dick, then lifted up her dress to show me she wasn’t wearing any underwear.

She leaned over and started kissing me again, and as she did, she pulled the lever at the side of the seat to fully recline it until we were horizontal. Meanwhile, as we were kissing passionately, my cock was getting harder by the second. In no time, I was fully erect and ready for action.

Jessie didn’t waste any time. She smiled at me as she guided my stiff dick to her center, then slid down onto me, her slick pussy swallowing me entirely. Stuffed with cock, she moaned happily, then leaned forward and whispered in my ear, “I’ve been wanting to do this for ages.”

I couldn’t form the words to respond. Having her hot little body on top of mine and finally feeling her slick walls wrapped around my shaft had me really worked up. I could do nothing but savor the feeling of finally being inside her.

Jessie, thankfully, was composed enough for both of us, and as I lay stupefied below her, she began to ride me like a born-and-bred cowgirl. Her hips rocked back and forth, and on every fourth or fifth stroke, she rose up and sank back down completely. Her fingers dug into my forearms, and my hands squeezed her slender thighs, holding her tightly as if to reassure myself that she was really there and I wasn’t dreaming.

“From the look on her face, it appeared she was on the verge of a monster orgasm.”

Jessie released my arms and leaned forward, bracing her hands on my chest. The move changed the angle of penetration, and her pussy felt even tighter to me.

I reached up to cup her breasts. Her nipples were rock hard, and I could easily feel them through her dress and bra. I started squeezing her tits and tugging at her nipples, which seemed to make her move her hips more frantically. From the way she started moaning loudly, I knew I’d found her hot button, and nothing could stop me.

We kept going like that for a few minutes, but soon I needed more, so I suggested Jessie lean back and brace herself on the dashboard. She was just the right height to be able to do so without bumping her head, and once she was comfortably positioned, I began to thrust up into her. I pumped my cock in and out of her sweet slit, watching my dick plunge in and out of her.

Jessie started going crazy, moaning loudly and tossing her head. Her hair fell out of her neat ponytail, scattering over her shoulders in a riot of disheveled curls.

I needed to come so badly it practically hurt, but I wasn’t going to be selfish. I wanted Jessie to climax before I did. I reached forward and began to very gently rub her hard little clit. Her body jerked and spasmed at the first touch of my finger, and then she started moaning and squealing as I began rubbing her in earnest, increasing my pace and intensity. From the look on her face, it appeared as if she was on the verge of a monster orgasm.

“Harder!” she cried, and I obliged, adding more pressure until she shuddered and shook.

I felt her pussy clench my cock repeatedly as her climactic spasms wracked her body, and then there was a final moment of release as her juices showered my shaft.

With her orgasm out of the way, it was my turn, and I thrust up hard into her as I shot my load, filling her with my cream seconds later.

As soon as she caught her breath, Jessie straightened her dress, flashed me a smile and walked away.

I didn’t get to talk to her all weekend, but when she showed up for class on Monday, she sat next to me wearing another dress — and a devious little smile.

" />

My Junior Year

Storyline

Jessie sat across the room from me in my history class during my junior year of college.

I’d spotted her on the first day, her shimmering auburn hair catching my eye first with the way she filled out her hot-pink sweater a close second. She was often late, but she always appeared casual and unhurried. She paid attention in class and joked with our professor when she was called on, but as soon as the hour was over, she was the first one out the door.

For the initial weeks of class, I watched her from afar, but one day I decided I needed to get to know her. I got to class early and made sure to sit down at the desk next to her usual seat. But just my luck, she was later than usual. By the time she arrived, someone else had taken her spot, causing her to sit in the back of the room. However, I wasn’t deterred. I took my new seat again the next chance I could. My plan worked, and she sat down next to me.

I’d probably stared at her the entire class, but I’m not sure she even noticed. She’d had a laser-like focus on the lecture. But I was determined to speak to her, so at the end of the hour I made a joke about our professor and she laughed. I asked her if she ever used an instant messaging app I like, and she told me her username.

That afternoon I logged in and sent her a note. We chatted for hours that night. I started talking to her every day, but every time I thought about asking her out, she’d mention some guy she was seeing. She didn’t seem opposed to my flirting, but she never took things further, and by the end of the semester, I’d accepted that nothing was going to happen between us.

Months passed, and I kept chatting with Jessie, but for the longest time, all I had were fantasies. The only action I was getting was in my imagination — until my final semester of college, that is.

A year after we first met, I ended up in another class with Jessie. The first day of the semester, when she walked in and spotted me, her whole face lit up. She was definitely happy to see me — and I was probably twice as happy to see her.

In the weeks that followed, Jessie sat near me, even though there were lots of desks and she could have put plenty of space between us. That made me start to think we had something brewing.

My hunch was right. One day after class, Jessie asked me if I wanted to grab lunch. I agreed, and we had a nice afternoon together. When it was time to head home, she said she’d walk with me to my car. We strolled while talking pleasantly, discussing class and what our plans might be after graduation. She was applying to a master’s program, and I was hoping to go to law school.

Anyway, I was parked in the underground lot on the other end of campus from the dorms where Jessie lived, and because it was late on a Friday afternoon, most of the place was empty. My car was all by itself in a dark corner of the garage; the next nearest vehicle was at least 20 spaces away.

When we reached my ride, I turned to say good-bye to Jessie, but instead of responding, she leaned forward and kissed me. I was so startled it took me a few seconds to start kissing her back, but when I did, I went all out. I wrapped my arms tight around her to hold her in place and then kissed her so thoroughly it started to feel like our lips had actually fused together.

Once we finally broke our embrace, I expected… well, I don’t know what I expected, but it wasn’t what happened next. Instead of an explanation or an excuse, or even a follow-up kiss, what Jessie did was tell me to open the door of the car and get into the passenger’s seat.

She was wearing a dress that day, a rare occurrence, and once I sat down in the car, she climbed in and straddled me. She reached between our bodies, unzipped my fly and pulled out my dick, then lifted up her dress to show me she wasn’t wearing any underwear.

She leaned over and started kissing me again, and as she did, she pulled the lever at the side of the seat to fully recline it until we were horizontal. Meanwhile, as we were kissing passionately, my cock was getting harder by the second. In no time, I was fully erect and ready for action.

Jessie didn’t waste any time. She smiled at me as she guided my stiff dick to her center, then slid down onto me, her slick pussy swallowing me entirely. Stuffed with cock, she moaned happily, then leaned forward and whispered in my ear, “I’ve been wanting to do this for ages.”

I couldn’t form the words to respond. Having her hot little body on top of mine and finally feeling her slick walls wrapped around my shaft had me really worked up. I could do nothing but savor the feeling of finally being inside her.

Jessie, thankfully, was composed enough for both of us, and as I lay stupefied below her, she began to ride me like a born-and-bred cowgirl. Her hips rocked back and forth, and on every fourth or fifth stroke, she rose up and sank back down completely. Her fingers dug into my forearms, and my hands squeezed her slender thighs, holding her tightly as if to reassure myself that she was really there and I wasn’t dreaming.

“From the look on her face, it appeared she was on the verge of a monster orgasm.”

Jessie released my arms and leaned forward, bracing her hands on my chest. The move changed the angle of penetration, and her pussy felt even tighter to me.

I reached up to cup her breasts. Her nipples were rock hard, and I could easily feel them through her dress and bra. I started squeezing her tits and tugging at her nipples, which seemed to make her move her hips more frantically. From the way she started moaning loudly, I knew I’d found her hot button, and nothing could stop me.

We kept going like that for a few minutes, but soon I needed more, so I suggested Jessie lean back and brace herself on the dashboard. She was just the right height to be able to do so without bumping her head, and once she was comfortably positioned, I began to thrust up into her. I pumped my cock in and out of her sweet slit, watching my dick plunge in and out of her.

Jessie started going crazy, moaning loudly and tossing her head. Her hair fell out of her neat ponytail, scattering over her shoulders in a riot of disheveled curls.

I needed to come so badly it practically hurt, but I wasn’t going to be selfish. I wanted Jessie to climax before I did. I reached forward and began to very gently rub her hard little clit. Her body jerked and spasmed at the first touch of my finger, and then she started moaning and squealing as I began rubbing her in earnest, increasing my pace and intensity. From the look on her face, it appeared as if she was on the verge of a monster orgasm.

“Harder!” she cried, and I obliged, adding more pressure until she shuddered and shook.

I felt her pussy clench my cock repeatedly as her climactic spasms wracked her body, and then there was a final moment of release as her juices showered my shaft.

With her orgasm out of the way, it was my turn, and I thrust up hard into her as I shot my load, filling her with my cream seconds later.

As soon as she caught her breath, Jessie straightened her dress, flashed me a smile and walked away.

I didn’t get to talk to her all weekend, but when she showed up for class on Monday, she sat next to me wearing another dress — and a devious little smile.

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