Date Sixteen, First Time—Ginny
"My first time was with one of my hand job buddies. We developed serious hots for each other at the beginning of my first year in college. I gave him hand jobs, and blow jobs. He would rub me off with his fingers and eat my pussy. We got in on pretty good but I would never let him stick it in me, I told him I was afraid I would get pregnant. That was true. I remember the day my older sister, who was only 18 years old at the time, told my mom and dad that she was pregnant. It wasn't a happy day in our house and I didn't want to put anybody through that again.
"By the end of the first semester in college and dozens of hand job dates, I was worried that he would dump me if he didn't get his dick in me soon. I talked to my mom about him and she got me on the pill. I also bought three boxes of condoms in three different styles, 12 condoms in each box. I wasn't taking any chances.
"The first day back at school after the semester break, I rolled a condom over his dick and fucked him until his eyes rolled back in his head."
"What about the hymen breaking and all those other un-virgin details, am I going to hear about them?" Kyle asked.
I told Kyle that my cherry was busted long before that by one of the many rubber dildos I owned, I don't even remember which rubber cock had the honor. All of them had names and I had one for every day of the week, but sometimes I let two or three of them pull a train on me on the same night.
Kyle reminded me that I hadn't told him many details about my deflowering.
"Before getting my first dick I was jerking him off like I had so many times before. My lips were next to his cock head so he couldn't see what I was doing. With my left hand I put the rolled up condom on the tip of his dick and with the next down stroke of my right hand I rolled it down and in place. I moved my head out of the way and asked him to look at what he was wearing. He saw the rolled on condom and said, 'does that mean. . .' I said 'yes' and threw my leg over him and lowered my pussy down on his cock. It went in easy and quick, I was wet and I had already let one of my big dildos fuck me before he arrived. I remember that I knew right away that a real dick was better than any dildo, no matter how realistic the rubber cock might be.
"I rode him hard, I rocked my hips back and forth, and I raised myself up with my legs and dropped back down on top of him over and over. I used my fingers to rub my clit while I rode him and got myself to a climax just before he filled up the condom. I removed the condom and tied the open end in a knot. We used the second condom with me on my knees, and my shoulders pressed down on the bed. We tried every position we could dream up over the next two weeks before we ran out of condoms. Then I bought more condoms."
I looked at Kyle and he had a hot and hungry look on his face. He took off his clothes and lay on his back on the floor with his dick sticking up. "Ride me baby," he said.
I got out of my sweats and dropped down on top of him, burying his dick in my cunt and started shaking my ass and humping him at full speed. I rode him hard and he pumped hard into me with every movement of my hips. I clenched my way through three or four orgasms until I had to stop, but there was no stopping Kyle.
He rolled me over and pulled my hips up, pushed my shoulders down, got behind me, and slammed into me again. At that point he went into some kind of fuck trance. He was holding my hips with his big hands and plowing his big cock into me over and over with everything he had, his hips smacking my ass. By the time he unloaded into me I had already had two or three more orgasms.
The next day I was sore. The muscles on the insides of my legs were hurting, my ass was red and stinging from him slapping it when he had me on my knees, and the inside walls of my pussy hurt. For the next two days, every time I would take a few steps and feel the soreness in my body my cunt would juice up just thinking about the two of us pounding each other so hard. The lingering pains were delicious, almost as welcome as another round of rough sex would have been.
Date Seventeen, 10K Road Race—Kyle
Our city parks and recreation department puts on six big road races every year, they also organize Wednesday night fun runs in a city park. For as long as they have been doing the six races they have been giving awards not just for overall and age group winners, but also for higher weight group winners. It draws more overweight runners into running and fitness. For men there is a category for 200-224 pounds, another for 225-249 pounds and another for 250+ pounds. For women the categories are 160-179, 180-199 and 200+.
My goal has long been to win one of the big races in the 225-249 weight category. I've finished second several times, but a guy named Tony T beats me easily every time. Tony and I are both about the same height, I'm 6'4" and he may be an inch taller than me. We both qualify for the higher weight groups because we are tall and muscular, not because we are overweight.
Several people from the weight group runners have become good friends, we usually go out for a few beers after our Wednesday night fun runs. Unofficially we call ourselves the Lard Ass Running Club. Ellen is a new girl who recently joined the group. I had only seen her run at a couple of the Wednesday night fun runs and those were often more slow jogs.
The Lard Asses were all gathered around the weight-in station as we do before all the big races. When I stepped on the scale, the weight master yelled "225.2."
"Now you can go take a leak and purge," yelled someone in the crowd. We always give a hard time to anyone makes category by a small fraction. Too many times I've come in at 224.5 and been put into the 200 pound category, I deserved a break. Tony T weighed in at 226.5, I really didn't have a weight advantage.
I really did have to piss, when I returned the girls were going on the scale. Ellen weighed in at 160.1. "Make her trim her fingernails and take off her earrings," someone yelled. But for the day at least Ellen was an official Lard Ass, even if she did have the body of a model.
We heavy weights have our own starting chute parallel to the primary starting line. When the gun went off we got a good start. I stayed with the lead cluster which included Tony T, several 201s (those are the serious runners who would not have made their 200 pound weight class if they had removed their Fit Bits), and a hand full of pretenders who would soon fall off the pace. Ellen was the only woman with the lead cluster after a quarter mile when we merged into the main group which was also thinning out.
At the two mile marker I was 20 seconds faster than my intended pace. Tony T was half a block ahead. I wasn't keeping close watch on him, I was enjoying watching Ellen's cute ass a few yards in front of me. Just after the three mile marker, Tony T was on the side of the road with his head down, puking a large recently consumed meal into someone's front yard.
"Did you see that?" asked Ellen when I pulled up beside her. She was looking remarkably fresh, as if she was out for a stroll.
"Looks like Tony T stopped by Denny's for a Grand Slam on his way here," I said, "he needed to make weight." I added when she looked confused.
"That is the guy I came here to beat, let's pick it up, pass a few people and leave him in the dust."
She adjusted to the faster pace with ease and I kept pounding forward. Half way between the 4 and 5 mile markers we turned a corner and Ellen said, "he's coming." Within a couple hundred yards Tony had passed us and was pulling away.
"How bad do you want to beat him?" asked Ellen.
"I want it bad," was all I could get out as I grunted and gasped to keep up the pace as Tony was opening an ever bigger gap between us.
