Twenty Dirty Dates Group Pt. 04

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.

"Stay with me big boy," Ellen said, "let's see what you've got."

Not far past the 5 mile marker we had caught and passed Tony. "Don't let up now," Ellen demanded.

She had finally broken out into a good sweat and looked like she was pushing herself. We rounded another corner and I started to feel like I was running on springs, something was propelling me forward with every step. I was in a speed warp and it was getting easier with every step. We started passing people including some of the 201 guys.

When I glanced back to check on Tony, Ellen yelled at me, "don't look back, stay with me."

I looked up and saw the finish line a couple blocks away. We sprinted the last 200 yards, a virtual all out sprint and we passed more runners on the way. As we approached the finish line a worker directed Ellen into a separate chute and I noticed that they were holding a ribbon across her finish line and a TV station camera guy was filming her.

We both crossed our finish lines in the same time at 37:47. My previous PR had been 39:05. Ellen had won the woman's race, we had passed the underweight female leaders in the final sprint. A Lard Ass had just won the overall woman's race, not just the weight class division, she won the whole race.

I was stumbling and walking wobbly after passing the finish line. A race volunteer propped me up and Ellen ran up and gave me a big hug.

"We kicked his ass," she said.

"You won," I replied almost in shock.

"Proud to be a Lard Ass," she said.

A couple 201 guys joined the group hug and helped me to a chair while Ellen did an interview. We made our way to the parking lot where the Lard Asses were gathering for a few beers. As the runners from our group drifted over to us they were all shocked and proud that one of ours has won the women's race. Even Tony T drifted over to congratulate her and me. Tony admitted that my time was better than his PR. He would not have beat me even if he hadn't stopped to throw up his breakfast. I admitted to him that I would not have run that fast if Ellen had not been pushing me.

"Why was that girl who was built like a Q-tip hugging you after the race?" Ginny asked a few days later when I saw her at work. "I saw you on TV. Have you been fucking her?"

"Would it be ok with you if I did?" I asked.

"As long as you give me the dirty details." We shook hands on it.

Over the next month Ellen showed up for the Wednesday night runs and we always ran together. I was getting faster and losing weight, she was taking it fairly easy to just run along with me.

"Want to have lunch," Ginny messaged me at work.

"Sorry, got plans," I messaged back.

"Gonna fuck the Q-tip over lunch?" she wrote back. I didn't bother answering, I was meeting Ellen for lunch, but the subject of the two of us having sex together had never come up, not that it hadn't crossed my mind.

Over lunch Ellen asked me to go on a real date with her, dinner and a movie. "And maybe some time to get to know each other better afterward," she said without a wink or even the slightest bit of body language to let me know if she was inviting me to a romp in the hay.

Late afternoon on the day of my date with Ellen, Ginny showed up at my apartment.

"I was just in the neighborhood and thought I would drop in," she explained. "I haven't seen you around much lately and I'm going to need more Kyle time soon."

Obviously I was suspicious since she showed up only a couple hours before my date with Ellen.

"What are you doing tonight?" she asked with feigned sincerity.

I explained that I had plans and the conversation went right on with all sorts of other things we had to talk about. She talked a lot about the good times we had and how much she appreciated the two of us being together. She noticed that I had lost weight and she asked if I planned to get skinny and never want to be with a full figured woman again. I assured her that I liked every curve and every pound of her.

I was sitting at my desk chair, turned around so I was facing her. She came up to me and put one leg between mine and sort of sat on my knee while bending over and kissing me long and passionately. When she stood up I could see that there was shiny pussy juice on my bare knee where she had sat. She pushed her hand up the leg of her shorts and pulled out fingers coated with fresh pussy juice which she brought to my lips. As I was licking her fingers she said, "I need to be fucked hard Kyle."

When her shorts fell to the floor, she stepped out of them and took two steps to a chair where she bent over and spread her legs for me. My dick took over my brain and got my pants off in the two steps it took to get to her. Girl juice was running down the inside of her legs when I stepped up and buried my cock totally inside her in one wet thrust.

She wanted it hard, she was getting it hard from zero to full speed in one ass humping, butt smacking, and unintelligible word moaning second. The harder I pounded into her the more she begged for harder, the longer I lasted the louder she asked for more. When I unloaded deep inside her she was in the middle of a pussy clenching orgasm, the kind were the pussy takes on a mind of its own and goes through minutes of involuntary uncontrollable clenching. Finally she turned about and took me into her mouth and cleaned me up.

As we did our best to catch our breath, she sat on a chair front of me, totally naked with her legs spread. As we carried on an almost normal conversation she was probing fingers into her pussy and pulling out strings of cum which she licked off her fingers. I was only wearing an old t-shirt so she could clearly see that my dick was quickly coming back to attention.

"That was amazing," she said, "and I would like some more. Me on top."

With that she took my hand, led me into my bedroom and positioned me on my back on the bed. She put a knee on either side of my head and lowered her pussy down on my face, feeding me her pussy and it's cum contents. Leaning forward she wrapped a hand around my cock as she took it into her mouth. With her other hand she found my ass and started probing. When she was satisfied that she had me throbbing hard she knee walked until she had her still dripping pussy positioned where she wanted, she put her hands on my knees and lowered herself down for full penetration.

Her movement was all about rocking back and forth with my dick fully inside her, no in and out, just rocking and dick tip to cervix rubbing. The longer she went on the faster she rocked her hips. When she leaned over and reached between her legs and mine to stick a finger in my ass, I licked two fingers and pushed them in her willing ass. She may have had one climax that lasted 15-20 minutes or it may have been 100 climaxes, hard to tell. At one point she did a top spin move (not easy for a full figured girl) and turned around facing me with my cock fully inserted the entire time.

I was fully aware that Ginny knew that I had date with Ellen when she arrived. I was fully aware that she was there to fuck me dry before my date. Was Ginny shamelessly refreshing my memory that she was the best piece of ass I ever had or ever would have? Maybe. Was she trying to use me up so I wouldn't be able to get it up for Ellen later? No, she knows I would recover in a couple hours or less. Or was she just plain horny. Whatever the motivation, she got the job done. As I shot my second load of cum up into her pussy my cock immediately went soft.

I mentioned that I was running late and headed for the shower. When I got out she was gone.

She called the next day, she said she got fucked last night and her pussy was sore. I told her that I enjoyed it too and it was incredible how good she was. "You were awesome yourself," she said, "but I was talking about how I got fucked by another man later. But nobody is as good as you, not even close."

After an uncomfortable silence she asked, "how was your date?"

"It was good," I replied.

"Did you fuck her?" she asked.

"Yes."

"How many orgasms did she have?"

"At least three, maybe four or five," I replied honestly.

"Is Q-tip a good cocksucker?" Ginny asked. "How many loads of cum did she get out of you? Did you cum in her cunt or in her mouth?"

"Excellent cocksucker, one load and I squirted it on her ass," I said.

She pressed on, "Was it a hard squirt that went up to her shoulder blades, or a weak dribble of cum that dripped on her ass?"

"More of a dribble than a squirt," I replied.

"Did she suspect that you had been fucked dry before you picked her up?" she said and I didn't answer. "Bring her around sometime and I'll show her what you really like," she said with a kind of smugness and a laugh.

I didn't mention that I lasted over an hour with Ellen and that Ellen told me it was the best sex she has ever had, Ginny didn't ask about that.

Date Eighteen, Milking Bench—Kyle

I had picked Ginny and two girlfriends up at a bar on Friday night. They weren't all that drunk when they got in for the ride home. After we dropped off her friends Ginny said that she would like to spend the night at my place. The sex was good but quick, we both fell asleep and didn't wake up until morning. I woke up with morning wood.

"I'd hate to waste that stiffy," said Ginny as she threw her leg over me and lowered herself down on my cock. It was good wake up sex.

We were driving through some residential streets on our way to get breakfast and we drove by a garage sale. Ginny asked me to stop, she saw something interesting.

What she saw was a massage table. It was narrow, thin and lightly padded, it had a headrest that was like an oversized sized padded donut with a big bite taken out of the side next to the table, we assumed one could use it face down with the donut surrounding you face, or face up with the back of your head on the donut. It was the large hole in the middle of the massage table in the pelvic area.

"WTF," said Ginny. "If you had a man lying face down, his cock would poke through that hole and you could sit on a stool on the side and milk him like a cow."

She bought the massage table, we hauled it to her house and put it in the basement next to her glory hole booth and shackles.

Visualize the positioning and mechanics of a traditional hand job. With a man standing up and the woman kneeling or sitting in front of him, with a man lying down and the woman leaning over his body, with the man sitting in a car with the women (or another man for that matter) reaching over, or any of countless other sittings for a hand job, the person administering the hand job starts at the tip of the cock and strokes down and back up over and over. Call that the thumb up approach. With the milking bench the man has his cock pointed down and the natural method is to start with hand at the base of the cock and jerk down then push back up over and over. Call that the thumb down approach.

Thanks to the clever way that the radius bone interacts with the ulna in forearms, performing a thumb down hand job can be done from almost any position, but according to Ginny, whom I acknowledge being and expert at giving hand jobs, it is tiring and uncomfortable to give a thumb down hand job from most positions.

We dropped off the table and went out for breakfast where we spent most of our time trying to think of a reason, other than giving more comfortable thumb down hand jobs, for the hole in the middle of the massage table.

Personally, I think it is a comfort feature like the donut shaped head rest. A person of either gender cannot lay face down on a massage table without either turning his head to the side, or smashing his nose and chin, and a man cannot lay face down on a lightly padded table without smashing his junk. Later we found out that the previous owner of the table used it as a tattoo bench. When a tattoo is being applied anywhere on the back side of a man it is important that he lay still. It is nearly impossible to lay still for a long period when your balls are being mashed into the table. Cutting a hole in the groin area is a good solution.