Nice Guys Finish Last

Science class at the end of the day was always a time of near-anarchy for me. The students were loud and annoying, but I and one other girl were quiet- I because I was shy, her because she didn't give a thing for the class (not to mention the teacher was a flat chest and hated to be reminded so). As such, I sat in the far corner of the classroom, and she next to me with a small space between us. We were simply acquaintances, nothing more.

I was your typical nice guy. Freshly 18, I was 6'2 with the normal brown hair nice guys have. I will tell you I was threatening to look at- strong jaw, decent muscles, and my height, as well as a deep, resonating voice I've always had. But I couldn't bring myself to hurt a fly. I figured that, as long as I could intimidate people, they would leave me alone. And my penis? 7.5 inches... Only I was the only one to enjoy it. I must also admit that I was decently hung, at 5 inches, but I preferred not to show it off- I didn't want to make enemies (ridiculous, I know, but I was a careful man).

She was 5 foot-flat. Short rust-colored hair at her shoulders, and she had big, beautiful green eyes. I was a hopeless romantic for her, especially her breasts. I know for a fact she tries to make her boobs look smaller, but twice a ribbon she wrapped her breasts around had broken, and though she tried to hide in the corner of the classroom, I could see them for all their glory. When she walked around, you would guess that they were D's, at most E's. The days the ribbon broke, I saw what must be the most glorious F-cups I had ever seen. I did me best to hide my erection the times it happened- she tried to hide her embarrassment.

The first time such a thing happened there was an intensely awkward moment. I told her as her face flushed, "I won't tell anyone." She looked at me, as if trying to gauge if I was serious. I couldn't look at her- my eyes were focused on the desk. She simply nodded and said, "Thank you." I asked her why she was hiding them after a moment. I found out it's true- having large breasts does give you a lot of unnecessary attention, not from guys staring, but also perverts who tried to touch them, and she was trying to cut it down. I nodded understandingly, as best as I could pretend. We tried to not let something like this get the better of us.

One day, the moment changed. Her ribbon had broken again that day, and I grew a massive erection. My tight jeans weren't helping either, as they rubbed against my head. This erection wouldn't be leaving that day. Her perfume seemed to be stronger, but I wasn't focused on that.

The lesson today was a simple problem for me and a few others in the class, but for this girl (Jennifer. Her name was Jennifer) and all others, it was like Latin. She turned to me when we were supposed to complete an in-class assignment, because I was the only one near her, and asked, "Can you explain this to me?" Her breasts were in a full arc in front of me, her breasts spilling over her tight white top. My erection was still there. I tried to lean over to help her, hoping she could read upside-down. "I can't read upside-down, Michael. Can you just come over here?" I knew I had one shot at her not seeing my erection. Nodding, I swiveled out of my chair away from her, and I tried to stick my dick between my waist and pants waist, to hold it there. I barely got it there- I tried my best to move as little as I could.

The question was a basic heart rate to body mass ratio, unimportant, uninteresting, and irrelevant. What truly caught my attention were both her tits spilling out with what seemed like half a foot from her chest, and the fantastic cleavage with it. And her perfume seemed stronger. I was helping her through the problem when my nose tickled from her scent, and I sneezed five times in a row.

My erection had died down only a little bit, but enough for it to fall from my waist to on top of my leg and then get hard again as I sneezed. I can only imagine her looking at my pants and seeing my cock hard and along my leg. I finally stopped, and I pulled my hips back- though it didn't solve my erection problem, it made me feel better. Her nipples were hard, and they were surprisingly small for such massive melons. She started to stutter a bit, but finally we got through the ordeal. She had her answer, and we both had our view. We left the classroom in silence.

The next day, I feared it would be extremely awkward. Instead, she came in wearing a sweater with a zipper up the front. Her breasts were noticeable, but they were tied down, I could tell. As she sat down, she unzipped her sweater, and revealed her tits. In a swift motion, she had undone her tying ribbon, and her tits pulled at her amazing black tank top. Her straps didn't touch the front of her shoulders, and her breasts, again, spilled out, but not only over the front but the sides as well. I had an erection again, and this time I regretted it. I was wearing briefs this day, and my dick was bent and curled up inside of my pants. I asked me teacher as normally as I could if I could use the restroom. I fled as fast as I could to fix my problem.

I waited in the bathroom until it calmed down. Slowly, I began to go back to class. As I was in the hallway, I saw her. She smiled at me, and began to talk to me. "You didn't really have to piss, did you?" she asked. I remained quiet, my head turning away and my face flushing to show my answer. She then asked, "Was it because you were hard? For me?" I still didn't respond, but began to look around. No students were allowed in the hall ten minutes after class started unless they are on urgent business, and I knew no one would be in the hall, but I still feared someone would hear. She smiled even brighter.

"It's okay," she told me, "I know your dick must have been tangled up. It is pretty big, from what I saw..." She began to walk towards me, her breasts swaying side to side. I was getting hard again, and I made a futile to back up. She pushed me against the wall, and said, "Let me relieve those blue balls of yours... I know you didn't cum by yourself in such short of a time. You look like a guy who likes to make it last." She kneeled down, and slowly unzipped my pants. She reached in, and pulled out my semi-erect cock. I was sad- it blocked my view of her cleavage. The circulation was almost cut off by the small fly of my briefs, and I became truly hard, at my max. She smiled, and stood up. "I like it," she told me. "Please, Mike, don't worry about impressing me- just cum." She started to stroke me slowly, her fist barely half the size of my exposed dick. Then, she got faster and faster. The pleasure was great- I made a face I can't begin to explain. I willed myself with all my might to cum- if I didn't, we would have been there for half an hour. I shot off, only once, three feet from where I stood. She was still rubbing me.

She frowned. "That's it?" she asked, and turned back to me. Her distraction had led her fist to aim my cock at her face. A powerful shot hit her on the nose, exploding onto her eyes and her open mouth of surprise. She let go, but I kept coming. My dick was pointed slightly upwards, and I coated everything- her chest, twice; her stomach; her legs, one for each; her exposed toes from her sandals. I was becoming soft, and when she started to speak again, my dick was red and swollen, but no longer erect.

"Oh my... I wasn't counting on so much... It's all over," she said disconnectedly. She reached into her shirt, finding that my cum had coated her cleavage, and was sliding down her stomach. It was all over her hair, it hung from the corner of her lips, it seeped into her toes. Slowly she began for the girl's room. I looked after her for a while, and once she left, my dick was hanging out and low. As I prepared to put myself away, a freshman girl came out of her class. For what seemed to be five seconds, she stared at my dick, I stared at her. She didn't look anything like a slut- she was one of the girls who forget to grow up, still wearing excessive pink. I quickly put it away (albeit uncomfortably) and ran to my class. Again, Jennifer and I didn't speak to each other for the rest of the day, though I did see white stains over her shirt.

The next day, she kept her ribbon up, her tits contained in her shirt. We didn't speak to the other. As the bell rang to end such an uncomfortable moment, she asked me as I was prepared to leave, "Will you walk me to my car?" I nodded, my nice guy instinct kicking in. It was a hot day; when I got to her car, she offered to give me a ride home. I wholly accepted.

As we drove up to my house, she looked me straight in the eye and said, "Michael, are you a virgin?" Again, my voice caught, and I looked away. She nodded solemnly. "I expected as much. You don't take control, do you?" This time, I responded. "No... I don't," I was ashamed.

She told me to recline my seat. I looked at her curiously, and as she undid my pants, I leaned back. "I'll let you have this one for free," she told me. She lifted up her shirt, revealing a bra that looked big on any woman. She undid her trademark ribbon that was over her boobs but under her pink bra, and it was as if her tits slid forward. At every angle, they were pouring over. I became hard again. Slowly, she started to pump me, and I, in my quiet delight, made my face. Her hand was too small for my dick, too much energy to move her arm all the way up and down. Using both of her hands, she gave me a hand job, only this time I could stare at her amazing melons. After about ten minutes of hard rubbing, I cried hoarsely, "I'm cumming!"

I later learned that, at this moment, in her mind, she was thinking, 'There's no way Michael will cum as much as before.'

She was wrong.

My first shot hit the ceiling, and she began to freak because it was her mom's car. I told her I was sorry, but it was about to happen again. She sighed, and pointed my dick at herself. After six more shots, she was coated in me once more. My cock lay down on my stomach, swollen again. My cum had covered her entire bra, as if it had changed color to a darker pink. I told her thank you. She pushed me out of the car, and sped away. As I got up, to my horror, the freshman girl from yesterday and two of her friends were just two feet from me. The girl pointed at my large floppy and yelled, "I told you!" I pulled up my pants as I ran away, planning on going around the block and then back to my house.

She and I started talking more often. I told her I was sorry I couldn't please her, to which she would respond that she'd been fucked enough that it seemed wrong that I wasn't given a little pleasure. About twice a week for the next three weeks, she would drive me home, take off her shirt and ribbon (but never her bra), and would give me blow jobs, now that she knew the dangers of giving me a hand job. I was surprised at first after, from what I had gathered as her having been in plenty of relationships, she had difficulty deep-throating me. After a week, she had it down pat. As we had done this, she let me see the tag on her bra. Her petite size threw me off- she did not have F cups, but rather a full-fledged 30H, that the thought of, even now, gets my cock in a fit.

The forth week was different. This day, as I got in the car expecting to get a blow job, she drove a different way. I didn't question her- I didn't want to make her mad and ruin this chance. She stopped outside of a house I wasn't familiar to.

It was her house.

She pulled out a medication bottle, and told me to take two. I asked her what it was.

"Promise me you won't get offended?" I shook my head. I wasn't in a place to beg for mercy. "Michael, today, you will lose your virginity." I was in shock, both for the fact that I was getting laid for the first time, and also because I wasn't told that I was until the moment it was to happen. "However, as I have come to know you, that while you do have some endurance, you always go soft after you cum, and most virgins always cum, no matter what, in a matter of seconds." I nodded respectfully.

"So this is Viagra, isn't it?" I asked her.

"It's over-the-counter meds like Viagra, only slightly more expensive, and they help with endurance. I don't want my first lay with him," she nodded towards my crotch, "To be remembered as the time you came so soon... Do you mind?" I almost laughed. Of course I didn't mind! I understood my limits- I wasn't a stud. I told her no, took the pills, and we began for her house.

She sat me at the foot of a large bed, and undid my pants. As she pulled them to the floor, my cock rested on the bed, following the comforter over the side. She took off my shirt, and she began her dance. She moved her hips slowly, rotating them around on her slight frame, and started to pull off her pants. I could feel the blood beginning to go through me, but I wasn't getting hard yet. Her small, slight ass, with just enough padding on it to make it attractive, slowly came out of her tight jeans, her blue thong almost invisible. She danced her pants to the floor.

She turned towards me, and slowly lifted up her shirt. My dick had gained length now, but hadn't gotten hard. She lifted up her shirt to show her matching blue bra, with a blue ribbon visible. She undid her ribbon, and her tits came toppling forward.

She pulled down her thong, which I paid no attention to. It was her breasts I was after. She turned around and undid her bra, and I could see them from behind her, spreading out past her sides. My cock started to rise. She turned around and whispered, "What do you think?"

I was completely hard, and my eyes were on her breasts. Her small nipples were hard, and her eyes were on my dick. I then whispered sheepishly, "Do you have a condom?" Almost like a puppet, she reached into a drawer and pulled out a condom, still staring at my dick. The box said "Small- 4.5-5.5 inches," on the side. I looked at her and asked, "Will these work? Aren't I a little...?" I didn't finish my sentence. She then came really close to me, her breasts on my chest and my dick on her stomach, and whispered, "It's not my time of the month... Just let me know when you're about to cum." I nodded. We kissed, and she pushed me onto the bed.

She slowly lowered herself onto my lap, my cock going in easily, though she felt rather tight. It took her a few tries to take it all. "You're bigger than the others I've had... I forgot I only had the small condoms," she moaned. Eventually, she began to ride me up and down, both of us in pleasure. Sure enough, after what felt like a minute, I had to cum. She quickly got off me and started to rub me with her hands. I coated her body with me, but I was still (to my surprise) hard.

We changed to doggy style, to where I had to work for it. After twenty minutes of ecstasy and coordination for how to fuck and where to go, she came. It was an amazing sensation, feeling her juices around my dick. Her front arms gave, and only her ass was in the air. Ten minutes later, I came, shooting myself all over her back. We continued on like this, cumming at different and longer intervals, until I had cum four times, and her for five.

Finally, after three hours of fantastic fucking, we lay sticky and sweating on a sticky and wet bed, panting. "That was amazing," I gasped, and she nodded as well. I still had an erection, and she took notice. My dick, sore from such a work-out, felt exhausted as she gave me another hand job. I willed myself to cum quickly, my semen covering her hand as I came for my fifth time. We looked at each other and smiled. We kissed one more time.

"Michael... I need to tell you something." She looked at the ceiling, almost embarrassed, and began, "Michael... I lo-" She was cut off by a ruckus at the front door. She started up, a wave of fear on her face. "Oh my God!" she yelled, "My mom!" Without even reacting, I grabbed my pants and shirt, and started out of the back house (my backpack was still in her car). She tried to get up to help me, but her legs gave way, too exhausted from orgasms, and she collapsed on the floor. "Run Michael!" she yelled, and I did, straight out the backdoor. I ran as far as I could, the shouts of an angry mother in the background. I ran until I got to a bus stop, and sat down on the bench. My dick was sore, my legs were sore, everything was sore. I just sat there until dark finally took the suburb, and then called my own mother for a ride home, not even caring to explain my whereabouts for the past four hours.

The next day, we both sat in class. I asked her what happened with her mom. "Don't worry about it," she sighed. Then she said, "Want to come over to my house today?" I smiled.

"Wasn't yesterday enough?"

"It was a good start. Your next lesson is how to cum at the same time..."