My name is Ryan Taylor. I run track for my small suburban high school.
Running for our school's track team often involved bursts of excitement, then long periods of quiet as events took place that we didn't participate in. On long hot days teammates who weren't involved in the next few races found any quiet shady spot to relax and cool down. This was often under the stands. I was a senior who ran mostly shorter races, 400M and relays. With all the practice I was in great shape, strong, but slender. Our small school had enough runners to cover most races with men's and women's events often taking turns. Over the past couple of years the biggest change I've noticed is the girls removing their uniform shirts and cooling down in their sports bras. It was enough to keep a young man energized.
I didn't have a girlfriend at the time. I spent most of my days running and with school work. Not that I didn't check out my teammates. One in particular was a junior distance runner Kelly Rogan. She was about 5-6 strong runner's legs, auburn hair always tied back in a pony tail. On this particular day my early event was over and Kelly still had awhile until her distance events which were usually later in the meet. We happened to be sitting alone. I'd noticed that Kelly didn't ever seem to remove her uni shirt like her teammates. Which was a shame since it seemed she might be pretty well endowed. Sitting there in the hot sun, almost without thinking, I causally asked,
"Hey Kel, how come you don't go shirtless like the other girls?" Immediately I wondered if I'd crossed a line, maybe gotten too personal. I wasn't exactly a ladies man who had a line ready for any occasion. Kelly looked over at me.
"If you must know perv", she said with a hint of a smile, "I'm not as flat chested as most of the runners. I wouldn't want all you guys staring at me."
"Oh, um, sorry." Now I was stumbling over my words. Smooth, Ryan, smooth.
"And anyway", she added, "why don't you guys remove your uni shorts? You're wearing compression shorts underneath. Same thing."
"Yeah but then..."
"Oh so it's different for you."
"Well yeah I guess."
"Boys." She rolled her eyes, but I did notice her checking out my bare chest and tight stomach.
I looked back. She was leaning on the bleachers, letting the sun hit her face, her posture causing her shirt to be pulled taught against her breasts. Her strong athletic legs stretched before her. I couldn't resist.
"How hot would it have to be?"
"Oh I'd have to be pretty hot." She opened one eye and looked at me. "You're persistent."
"You're already pretty hot."
"Ha, you say that to all the girls to get their shirts off?"
"No, they're nice girls, but not my type."
"Well I don't just strip down for anyone. You'd have to earn it."
"Next time we train, I'll race you."
"How long?" I knew I could easily win a shorter race.
"Whew, that's a long way for me. But ok. So what's the bet?"
"You win I run the cool down lap with no t-shirt. I win, you run the lap with just the compression shorts."
I quickly agreed without really thinking about it. Then I heard the coach calling for the 4 x 400 to loosen up. I had to go.
"See you later. Have a good race."
"You too Kelly."
After the meet Kelly and I agreed to practice together over the weekend. Since we had this bet we decided to go for a run on a day separate from our teammates. If she lost Kelly wasn't putting herself on display for the other guys. On Saturday we met at a park with cross country trails the team often used for training. Two laps through the course would be about 3200 meters. I had thought about it and figured maybe I could run out to a big enough lead and coast to a win. It was worth a try. I was wearing just my compression shorts and my loose track shorts. Kelly had her full track uniform. After a short warm-up we got started.
"See you at the end Kelly." As planned I set a fast pace, using my sprint speed to open a big lead. That worked for the first 800m, then I started feeling it a bit and slowed my pace hoping I'd conserved enough for the long distance still ahead. At the halfway point I looked back and saw Kelly well behind me, her steady distance pace allowing her to slowly close the gap. At the 3/4 mark approaching a long uphill I knew I was in trouble. My breath was about gone and my legs felt tighter. A glance back showed Kelly relentlessly closing on me. And she smiled at me. Damn, she knew she had me. On I went up the hill. Before long I could hear Kelly behind me. With the finish in sight she was right on my shoulder.
"Almost there Ryan. You can make it."
I had no breath to answer. I tried for a last kick on the final straightaway. But Kelly had a lot more left and went by me in the last 100. She'd won fair and square. I was gasping for air as I finished. We'd left water bottles at the end of the course and had a quick drink.
"OK, time for a cool down run. That should be easier for you with less clothes." Kelly stood there hands on hips waiting to see if I'd cover my bet. In a moment I'd be down to my skin tight compression shorts and nothing else. Kelly would have a good look at my equipment. A bet's a bet. I put my thumbs into my track shorts and slid them down. I stood holding my shorts and letting Kelly get a good look.
"Damn Ryan. That's kind of impressive." The excitement of the moment had sent some extra blood to my penis causing it to bulge in my shorts. I wasn't huge by any means, but I had a fair sized cock. It looked better in my tight shorts.
"OK Kel, let's get this run over." We started jogging Kelly at first hanging back to get a look at my ass, then catching up and glancing over.
"You know, it's not like I've seen many before. So don't mind me staring."
"Oh I don't mind. I'm just disappointed I didn't win."
"You're such a good sport, how about you win too." With that Kelly lifted her shirt off and I got my first look at her breasts bouncing in her sports bra.
"Wow, thanks. And yeah, you're definitely bigger than the other girls. You look amazing."
That was the last thing I said as my right calf cramped and I went sprawling in the dirt. I scraped my knee and crumbled in the path trying to stretch out my leg.
"Oh shit, Ryan, are you ok?" Kelly tried helping me up. I was now caught between pain and ecstasy as her boobs pressed against me as she helped me to a bench along the path. She helped me stretch my leg and massaged my calf, putting my leg on her shoulder to keep it extended.
"Oh damn. Thanks Kel." I looked down to see Kelly on her knees, my leg on her shoulder and Kelly looking at the bulge in my shorts a short distance in front of her. Kelly ran her hands up and down my leg, squeezing it to massage the muscles. Though the cramp was in my calf I noted that she was working her way well up my thigh. Her hands crept higher. Then with a sigh she let her right hand continue until she slid it the length of my hardening cock.
"I hope you don't mind. You're so sexy in just your tight shorts."
"I don't mind at all, it's making me feel much better." Kelly moved a little closer. She continued tracing the shape of my cock in my shorts. My cock was now fully hard, straining at my shorts. Kelly slid her hand to the base and felt my balls.
"MMM, these shorts are doing a lot of work holding all of this inside."
"I could say the same for your sports bra." I could see her nipples pressing against the material. Leaning forward I cupped her left breast and felt her large nipple under my thumb.
"Another reason I keep my shirt on. My nipples tend to show. Mm, that feels nice." I put my leg down slowly remembering to keep it extended. I then moved to lift Kelly up on to the bench next to me. She got the idea and moved up alongside me on the opposite side of my sore leg. She continued to fondle my balls and stroke my penis through the shorts. I turned to her and went for a kiss, my hand continuing to explore her covered breast. Kelly kissed me back and we continued this way for a bit. Fortunately this trail isn't used all that often, especially on a Saturday morning. I moaned into her mouth, squeezing her breast, pinching her nipple. Sliding my hand down to the bottom of her bra I moved my fingers along the edge and backed off her mouth just enough to look Kelly in the eyes.
"MMm, go ahead, i can put my shirt on quick if I have to."
Using my hand I freed her breasts from their confinement and paused a moment to admire them. Medium sized, firm, large dark nipples and areola standing out on her light skin. I showed my approval by going back to massaging them, caressing, pinching, holding and bouncing. Kelly showed her appreciation by returning her tongue to my mouth and resuming her attentions on my cock. It was now straining against the tight material. There was pre cum soaking through. Kelly looked at me.
"I don't want you getting ideas. I don't normally get naked with guys like this. But I led you on, you went along. So.."
Kelly pulled my shorts over my straining cock which quickly popped in the air when released. Kelly wrapped her hand around it,
"It's the biggest one I've held."
"It's not all that big."
"But it's nice." And she began to stroke me harder. With her earlier efforts this wouldn't take long. I leaned down to suck her nipple into my mouth rolling my tongue over and around, taking it between my teeth. Kelly moaned and sped up her work on my cock.
"Oh Kel, keep going like that. I'm gonna...." Kelly felt my cock swell, felt me tense, aimed my cock straight up and stroked multiple spurts, milking my cum from me.
"Wow, a lot of cum." She looked for somewhere to wipe her hand, then having no choice used her t-shirt. My cock was hopelessly covered in cum, so I just returned it to my shorts. I'd have to take care of this wash myself when I got home. Kelly pulled down her bra and put her shirt back on. She held my face between her hands and looked me in the eyes.
"We're friends, teammates. I'm not what you'd call an easy girl despite this behavior."
"Um, but would you go out with me? Like be my girlfriend? Not just because of this, but I do really like you."
"THAT, was the right response. Yes. And if you're a good boyfriend, then there just could be more of this behavior. Let me help you to your car. Then pick me up for school Monday."
I drove home in wonder. Wondering if she could tell I was a virgin. Wondering if she was. Probably. Wondering at my luck. The hottest girl on the track team liked me. Had actually jacked me off. And let me hold her amazing tits. I was getting hard again just thinking about it. My track shorts were tenting. Kelly had kept watch while I stripped off the compression shorts that were sticky with cum. More likely she kept watch on me. She asked if all the track guys shaved most of their pubic hair. Then made a comment that she assumed it was just the girls. Hmm. But yes it helped with sweat and such. She thought it looked cool. When I got home I quickly took a shower and released another load. Images of Kelly's sweet smile, and full breasts, making it no effort at all.
Monday morning I pulled up in front of her house. I got out to wave to her mother at the door. Kelly gave me a chaste kiss on the cheek and got in. Two blocks later, stopped at a light, she turned my head to her and kissed me full on the mouth.
"That was for Mom back there. This one is for us."
We got to school, holding hands as we walked in. That got some looks and nods. Being in different grades we didn't see each other much during the day. After school I met her outside the gym and we walked together to the track, much closer than teammates would walk. This drew a series of whistles and comments when we joined our teammates. The senior girls "complained" that I was skipping them for a junior and the junior guys "complained" that I was stealing one of theirs. After a couple minutes of this coach broke up the fun and games and we got down to business. This was pretty much the routine for the rest of the week. After practice we'd grab something to eat and find a place to park and make out for a bit. Then Kelly would have to get home.
Saturday I went over to Kelly's house. Met her mother, her parents are divorced, and sat out by the pool. Watching Kelly walk around in a two piece suit caused me to jump in a few times to hide my obvious erection. One time Kelly came up behind me and reach around to confirm.
"I thought so." She kissed the back of my neck and cupped my balls. "I guess you like my swim suit?"
I turned to face her and now my hard cock was pressed against her. Even with the two suits this is the closest it had been to her pussy. She put her arms around my neck and held herself against me.
"Yep, I do like your swim suit. But it's not safe for me to lay out on a chair with you bouncing around in it."
"I could put on something that covers more." As she slid her crotch along my cock.
"Noooo. It's perfect just where it is."
"Well sorry, but my Mom is still around so no more action for the moment." Kelly broke away and floated across the pool. Damn, what a sight. I waited for my cock to calm down then climbed out. After dinner Kelly's Mom said she was running over to her friend's house for a LITTLE while. We could stay out at the pool but not inside together. Once she'd left Kelly sat right next to me.
"We probably have only 20 minutes or so. Bring those lips over here." I leaned in for a kiss and was met by Kelly's tongue. We quickly embraced and kissed deeply releasing some of the built up tension of the day, but creating whole new levels of sexual tension. I caressed her tits and felt her nipples harden, pushing out against her suit. I pulled her top aside and began sucking and licking her breast running my tongue around her long nipple. Feeling the perfect size of her breast, causing her to moan. She took my free hand and placed it on the triangle of her bathing suit bottom. I rubbed my hand over her mound and pressed the material into her slit. Then taking a shot, for the first time I slid my hand into her bathing suit to come in direct contact with her pussy. Kelly's moan turned to a gasp. I took that as encouragement and felt around, finding a small tuft of hair above her slit, then nothing below. Sliding my finger down I separated her lips feeling the moisture from her excitement. I found her clit and rub my finger over it,
"Oh yes, keep doing that. Right there."
I kept up the pressure on and around her clit, bent down to take her nipple between my lips and pressed down on it. Kelly buried her head into my neck repeating,
"more, more, more, ooooh, oooooh"
When I'd finally brought her to the edge she bit down on my shoulder to muffle a scream. I felt her body tense, her hips pressing against my hand. The sudden pain from her teeth cause me to clamped down harder on her nipple and she went off. Not letting go of me until she calmed to the point of panting, "oh oh aaah". Seeing the mark she'd left, Kelly kissed my shoulder, then my face. Then looking at me,
"That was awesome Ryan. Really. But I'm kinda loud and and didn't want the neighbors to come running. Even when I, you know, do myself, I put my face into a pillow. But that was even better. Sorry about your shoulder."
"That's ok, it was worth it to see you like that." I gave her a smile and touched her nipple. "Hope I wasn't too rough."
"No, no, that was great. I can't do all that at once by myself." Then she looked down at the tent in my shorts. "Seems you might need some quick attention." As she reached for my suit we heard her Mom's car in the driveway. "Oh shit, I'm so sorry. I feel bad that you're being left out. Here quick before she comes in, you deserve a little treat you can use later." With that Kelly pulled down her suit to show me her mostly bald pussy. There was just a bit of reddish hair on her mound. It still looked flush from my efforts a few minutes ago. Kelly quickly put her suit together and jumped in the pool to cool down. I joined her and a few minutes later Mrs. Rogan joined us by the pool.
"I'm sure you two have had enough pool time. Ryan better be getting home. It was nice meeting you. Kelly's been talking about you all week."
"Nice meeting you too." She then went inside so we could say our goodbyes.
"I'm really sorry Ryan. Don't think I'm mean, or a tease."
"No problem Kel, I really enjoyed seeing you like that." Then with a few more minutes of kisses I was on my way home for a vigorous masturbation session. I wasn't kidding. Seeing Kelly getting off like that was amazing. And I still had her making it up to me to look forward to.
That didn't take long. After practice Monday, we stopped for pizza with some teammates. Then I drove Kelly home. Along the way she noted that we were a little early and suggested stopping at one of our makeout spots. She smiled as I drove.
"The girls were asking me how you are."
"I said you're a real gentleman."
"What's that mean."
"They know what I mean. Not all over me like a drooling horndog."
"It takes a certain amount of restraint when I see you looking so good."
"Thanks, but yeah. We've known each other awhile, but this is all still new." I knew what she meant. I found a secluded spot and parked. We released the seat belts, then I leaned over to her side. She kissed me, then backed away.
"I owe you. I haven't done this before so don't grade me." She reached down and unsnapped my shorts. She slip down the zipper. I was already breathing heavily. Kelly fished my already hard cock out of my shorts. She felt its length and rubbed her thumb around the head. She looked at me with her hazel eyes and said, "here goes nothing." Then she lowered her head and wrapped her lips around the head of my cock. I leaned my head back. This had to be heaven. Kelly's pony tail rocked back and forth as her head began bobbing up and down on my cock. She gripped the base with her hand, squeezing as her tongue and lips sucked around and over the head. Then she put the first two or three inches into her mouth and sucked on it as she pulled her head up. It popped from her mouth.
"Is that ok?"
"Perfect. Oh god."
Kelly licked the length of my cock, then around the head, she held my balls in her hand rolling them lightly as sucked more of my cock into her mouth. The intense pleasure was building inside me, my balls were tightening, my cock felt fuller, I warned Kelly, "I'm gonna cum."
Amazingly she closed her lips over my cock and just said, "MM HMM." That was all the ok I needed. My whole body tensed, then I could feel my cum rushing forward into her waiting mouth. "Oh fuck." Another spurt. She gagged a bit, swallowed, some ran out onto me. "Fuuuck." Another spurt. Then another. When finally I'd stopped flooding her mouth with cum Kelly swallowed one last time, popped my cock out of her mouth and smiled, with just a bit of my juice on her chin.
"How was that for a beginner?"
"That was damn perfect. Best thing I've ever felt." There's nothing like seeing the girl who makes your world go so happy because she just gave you a blow job. We cleaned up and finished with a few more kisses before rushing to get home in time.
We were happy. The track season kept us busy. School was a necessary evil. But the end of term was approaching. Friends at school started asking if I'd "gotten any". There were many guys jealous that I was with Kelly and most imagined what they'd be doing with her. I kept our activities private. Not really their business and after all we were taking things at a slower pace. Weeks went by and we took what opportunities there were to get to know each other better. Just after my graduation Kelly told me that she would be spending a week at a cabin her Mom owned with her Aunt. She said that I was invited to come along and that she had a cousin who would be there with her boyfriend.
"And one more thing I wanted to talk about with you Ryan. Um, we'll probably be able to find some private time while there and... well I'm thinking it might be time we do it."
"Oh of course. Of course I want to. Sure. Um, you know, this would be my first time, so...anyway, yeah."
Kelly hugged me tight. "Mine too. I never planned to wait or not. Just it had to be the right guy. And you're that guy. I'm sure of it."
"I'm so happy I waited for you to come along, Kel. I guess I should get..."
"Yes, condoms. Bring enough. I hear it's not always so great the first time, so I may want to try it until it's great."