Twenty Dirty Dates Group Pt. 01

Date One -The Very First—Ginny

For years I've been fascinated about hand jobs, ever since my older sister had several girls over for a sleep over and they got into a graphic discussion about giving hand jobs. One girl demonstrated the proper way to jack off a boy by holding an unpeeled banana between her legs as she pumped it hard and fast. The same girls later introduced me to female masturbation by demonstrating on themselves. I learned both lessons well.

My name is Virginia, but I'm called Ginny because Virginia sounds like someone who was born 100 years ago. Along with my former fuck buddy, and now loving husband Kyle, we the authors of the Twenty Dirty Dates story series about dates we have had over 4-5 years before we were married. Just to get the physical image established from the start, I haven't seen 150 pounds since freshman year in high school. I'm a size 16 and I'm muscular and fit, my hair is dark brown and long. I'm 5'10" tall, my bra size is 40 D, and my round ass turns a lot of heads. People have suggested to me that I could be a plus size model.

Kyle and I tried living together for a few months after my divorce from a brief marriage to my first husband. We quickly came to realize that there was a real danger that one of us was going to kill the other eventually. We didn't want to mess up the incredible sex we were having because one of us was dead. Kyle was more than a fuck buddy, he was a close friend to talk to about anything, a great dinner date, Mr. Fixit when I need something done around my house or car, my golfing partner and the first baseman and clean-up hitter on our co-ed softball team. He is the sober driver I called when I needed a ride home and no matter how drunk I was I knew I could count on him pulling over to the side of the road and fucking me at least once on the way home. We got together for amazing sex and stories occasionally, and then went our separate ways.

Back to the hand jobs. As my older sister told me when I was in high school, "the best way to keep a boyfriend loyal and happy without letting him stick his dick in your pussy, is to give good hand jobs." For the most part that advice served me well in high school and college. Over the year, with cock-in-cunt action practically guaranteed every time Kyle and I get together, I'm still an expert giver of hand jobs and Kyle is an appreciative recipient.

The first thing that fascinates me about hand jobs is how little effort it takes to get a cock erect. Just some sex talk, a few words about being in the mood and especially a little touching or tonguing and they come to full attention. You wrap your hand around the shaft and you start pumping, a little lube is nice, I keep a bottle of Astroglide in my purse. Thumb-up, thumb-down, nob squeezing, long stroking, two handed stroking, hand-over-hand up, hand-over-hand down, one finger rubbing, even using feet, there are so many ways to give a hand job. Once you get it going they are all appreciated.

Of course the goal is the cum shot. How amazing is that? You rub some skin up and down for a while and this miracle man juice erupts out the nozzle. I could watch it happen over and over. Actually I do watch it a lot.

What are other women thinking when they give a hand job? Wondering when the blast off is going to happen? Watching the man's face to get a clue how close it is? Wondering if he likes it? I know some women think it is creepy to stare, but I watch the cock intensely, I can listen to his moans and hear when he is getting close; I can feel it bulging in my hand. I'll never get tired of seeing the twitch of the cock and launch of the first shot. Obviously what happens to the cock inside your pussy when you are fucking is essentially the same as what is happening in your hand, but you can watch it happen when you are jerking him off.

And what about volume and distance? I jerked off a man once, he was laying on the bed with his head on a pillow, the first shot of cum went over his head and hit the headboard, the second shot hit him in his own face and neck. At the other extreme, some men just dribble out a little cum that runs down their cocks and onto your hand. I'm not an expert on the subject, but I know that how turned on he is, as well as how long it has been since the last time, are factors influencing volume and distance.

My first dirty date with Kyle was a hand job date. We had been working in different departments at United Universal Bank for several months and we both were availing ourselves of every opportunity we had to flirt. One time we ate lunch together and the conversation got a little sexy. On the way back to my desk I stopped in the ladies room, locked myself in a stall, pulled my panties to the side and rubbed myself off while thinking about him and hoping he was jacking off in the men's room. A few days later he asked me out and I had to tell him that I was engaged and was getting married in two months.

"Then we had better go out now, before you are married," he said. How could I turn that down? We met for a drink and after the second drink I could feel my reluctance decreasing and the wetness in my panties increasing. In his car in the parking garage I opened his pants and got his hard cock out for inspection. I've seen bigger and fatter, but not much bigger, he had all anyone needed. I didn't bother getting my Astroglide out, the pre-cum oozing out of his cock was more than sufficient.

My sister's words were in my head when I started stroking. I stroked him slow, and fast, then slow again, I rubbed the slippery pre-cum around and around the knob. I'm right handed and he was sitting in the driver's seat of his car so mostly I did right hand, thumb up cross body stroking. When he was approaching the point of no return I picked up the pace considerably and wrapped my lips around his knob. I have a preference for watching the squirts, but sucking and swallowing is good too, it was too dark in the parking garage to enjoy the view and I didn't want to mess up his suit. I kept pumping and sucking until he was drained, I think it was a lot of cum, I know I had to swallow 3-4 times to get it all down.

After the cock spasms finally stopped and he softened slightly, I raised my head, removed my hand and sat back in my seat. When he came to his senses he leaned over and kissed me. With his right arm around my neck and shoulders and his lips pressed to mine, his left hand found its way up under my skirt, I spread my legs as wide as I could in the car. I was wet through my panties, the girl lube was leaking out of my pussy. I helped him remove my panties and pull the skirt up around my waist. I quickly discovered that his skill at finger fucking a woman was a match for my ability to jerk off men. He also knew just where to put his tongue and how to use it as well.

That was date number one for us. Drinks at a hotel bar down the street from work. Mutual hand jobs in the car in a parking garage. I was weeks away from getting married and I told myself that my marriage would be the end to this little tryst. But at the same time I had hopes for one more shot at Kyle before the wedding. The man demonstrated that he knew how to eat pussy and enjoy a hand job, it would be a shame to miss out on that.

Date Two, Downhill—Kyle

Ginny and I didn't fuck on the first date, but we did give each other hand jobs. We fucked on the second date, more than once. We are making no attempt to keep these dirty dates stories in order from the first to the last, but I do want to start near the beginning so I will write about another very early experience.

My instructions are that I should start with a visual description of myself so that is what I will do, but that will be the last time I will be letting Ginny direct my stories. We will each recount our own memories of the events. My name is Kyle Southwood and I'm a big guy, 6'4" and 225 pounds and well-muscled. I work out regular and spend a lot of time in the weight room. I look like an athlete but I haven't yet found a sport where I excel, I'm a bit uncoordinated at times. People tend to think I'm all about being an athlete, but actually I'm more geek than jock.

Ginny and I went to MBA school at the same university and same time. We believe we were even in the same classroom together a few times, but we never met until after graduation when we both showed up for new employee orientation for our first day of work at United Universal Bank. There were six of us starting that same first day, Ginny and I went to separate departments and we never saw each other at work unless we make arrangements to meet.

It was about a month before her wedding to a guy she had been with for a few years, the weather was nice and she sent me a text asking to get together after work.

"Same bar as last time?" I messaged back.

"No, meet me in the parking lot of the supermarket on 23rd Street."

I drove around the lot and pulled into a vacant spot next to her car. A few minutes later she walked up with a grocery bag. "Get in with me," she said as she stashed the bag in the back seat.

She drove us to a park with a big lake. When she reached into the back seat to get the bag she picked up two empty Starbucks coffee cups from the floor of the car. From the trunk she got a blanket and corkscrew and handed all of it to me to carry.

Ginny had put together a picnic for us; wine, cheese and some fruit. She had a hearty red wine that made no sense with the food she had brought and a sweet desert wine that was even less of a paring, and we were drinking out of used Starbucks paper cups that had been laying around on the floor of her car for a few days. At least she tried. For a late winter day it was very spring like, with a gentle breeze. We enjoyed our picnic in a covered shelter near the parking lot as Ginny explained why we were there.

"In my life I've spent a lot of time with my pants down in the company of a fairly large number of men," she started, "and I've has sex with most of them. I like sex, lots of it, lots of different kinds of sex, with lots of men. Now I'm going to be married and will probably spend the rest of my life with just one man. Before that happens I want to have one last sex romp with a horny man who is dying to get his hands on me."

With that we both fell silent and took a gulp of wine. "Would it be arrogant of me to assume that I might be that man? Or could you be asking me to help you find the right man?"

She took another gulp of wine and poured more into her cup. "Don't try to be cute or charming, I just want to fuck you. I want to ride your big dick until I get tears in my eyes and then do it again."

"I'm in," I said, "thanks for choosing me to be your last pre-marriage sex partner."

"Now you are being arrogant," she replied, "I may have a few more guys lined up for final fucks before I'm marched to the alter."

We put the food in the car, took along the blanket and wine and went for a walk in the woods. We were on a hill side, high above the lake. The leaves were not out on the trees yet, we could easily see out into the lake where a rowing crew was training. With me in a white shirt and Ginny in a red sweater and red skirt I'm sure we were easily visible. We didn't have any trouble seeing or hearing the crew.

"I think the guy in the bow seat looked up at us," she said, "let's give them a show."

We found a spot to spread out our blanket where two trees were growing close together so the view from the lake would be limited. Foreplay doesn't seem necessary when intentions are so blatant. Ginny took off her skirt threw it down. I handed her my pants which she folded up and laid on top of her skirt next to our shoes. I threw my underwear on the pile and she added her panties. With my back against a tree I sat down, she walked up to me with a leg on each side of my body and pressed her pussy into my face. On an occasion like this, pussy eating is foreplay.

With my big hands digging into her sizable ass cheeks she ground her mound into my face. I focused directly on her clit with and an occasional tongue venture through her slit for a taste of the salty sweet girl lube that was oozing my way. When I slipped two fingers into her pussy and applied pressure to her hot spot she began humping my hand. There may have been an orgasm or two in that sequence but she was mute, maybe trying not to disturb the rowers. In the years since then I've learned that silent orgasms seldom have a place in Ginny's sexual profile.

She pulled up her sweater and bra as she lowered herself to her knees, offering her boobs to my face which was coated with her secretions. From nipple to nipple and the chasm between I face wallowed.

"You know, I can reach climax with just nipple stimulation," she said.

"I could do this all day," I offered.

"No, I want some cock. Now!" With that she reached between her legs and wrapped her hand around my cock as she lowered her body and guided me into her wet pussy.

At this point some visualization is needed. We were on a somewhat steep hillside. I was sitting on the ground with my back against a tree. My feet were on the uphill side so they were higher than my butt. Her legs were spread wide around my body and the tree behind me. She was facing downhill with her feet lower than my butt. I think we may have discovered a previously unknown sex aid; hillside fucking. She was wedged between my knees and my chest and was able to take advantage of gravity to get maximum penetration depth. When she started humping her hips to and fro while maintaining deep penetration we were both feeling new sensations.

She got her wish, she was moaning in orgasmic desperation, grinding her hips with all the down pressure she could muster, I was doing my best to push upward but not actually contributing much. Her face was buried against my neck which helped to muffle her moans. When she grabbed my shoulders and pushed her head back so that her back was against my knees I could see the tears of painful pleasure on her cheeks. A few more hip thrusts on her part and I was shooting a major load of cum in a place far up in her cunt where only genuine monster cocks regularly get to visit.

Ginny was lying face down on the blanket with her sweater and bra pushed up to her arm pits, her magnificent ass right in front of me in all of its glory, her legs were spread and a glob of white cum had seeped down slope and was running out of her gaping pussy. I reached for the wine and took a big gulp directly from the bottle, then another.

"Did you bring your lube along babe," I asked.

"Whaaaaaaaaa?" she groaned without moving.

"Did you bring lube? Your ass is looking so inviting the way you are laying there. I'm thinking about lubing up your ass and plunging in," I said as I touched her tight pucker with my finger and making teasing light attempts to slip a finger up her ass.

She clinched her butt cheeks and rolled to the side and said, "give me that wine bottle." After taking a huge gulp she said, "I'm going to drink the rest of this wine and then use the bottle to fuck YOUR asshole."

"No thanks," I replied, "today is all about giving you some last chance pleasures."

By the time we finished the wine we had both backed down from our anal threats.

"You know what I really want?" she asked apparently rhetorically because she continued, "I want the feel of a big strong man on top of me, holding me down and fucking me long and hard. I want you to use me, own me, just pound me until you have had enough."

Laying on top of Ginny, I was concerned about the roots and sticks under the blanket that might give her bruises or as least make her uncomfortable. I was propped up on my elbows to avoid hurting her and we were kissing; passionately, slowly and for several minutes. She gave no sign that she wanted to stop kissing and start fucking so we continued for several minutes. Her arms were around me, pulling herself up into my chest.

"Thank you," she whispered into my ear, "and about that hard pounding. . . now would be a good time to start." She was on her back with her legs spread wide and her knees bent, she was doing her best to meet every thrust. Then she put her legs on my shoulders, allowing me to pound down hard. We moved around a lot and the pussy pumping continued at an increasingly faster pace. I rolled her over and with her face down and lying flat on the blanket I slipped into her dripping pussy from behind and rode her ass hard.

Twenty minutes? Half an hour? I don't know how long the hard ride lasted but we were both exhausted when we finished. Sitting beside each other we watched the rowing team continuing to train out on the lake, wondering if we had been having a harder work out than them.

We got up to get dressed, Ginny reached down to pick up her panties and unexplainably I was hard and wanting nothing in the world except to continue fucking her. Before she could stand up I grabbed her hips and pushed my cock into her again, she looked back over her shoulder in surprise and I continued to pump my cock into her. She took a step downhill and wrapped her arms around the tree that had been my backrest.

She pulled up the blanket to make a makeshift shoulder pad and used the leverage supplied by the tree to push her ass back into my thrusts. We were both turned toward the lake but with her shoulder on the tree she had a better view of the lake than I did. I looked down at her and saw that on her left hand she was holding up three fingers. Moving my head to the side to see what she was seeing I realized that the guys in the crew were all looking our way and applauding. She was signaling that we were at it for the third time and apparently they appreciated our endurance, a good trait for any athlete.

When I finished dribbling the third and significantly lighter load into her well fucked pussy, my cock quickly softened and when I slipped out of her she turned around and took it in her hands. Even her dedicated efforts to lick it clean couldn't get the slightest rise. We got dressed and made our way back the car as it was getting dark. As we were loading up some smiling guys drove by and gave us a big thumbs up, apparently rowing practice was over.

"I've been fucked three times in the same day before," she said, breaking the silence as we drove back to my Jeep. "But that was from three different men, I've been fucked twice by the same man in one day and I had a man get it up for another round just an hour after the first time. You just did me three times in a little over two hours and all three of them were among the most intense I've ever experienced."

"I'd like to claim that I'm a super stud unlike any other you have ever experienced, but this was a first for me as well. You bent over to pick up your panties and suddenly I was ready to go again," I explained. "I don't think I'm the super stud, I think you are just so desirable that I can't help it."

She reached over and took my hand and squeezed it hard. When I glanced her way I saw there were tears in her eyes. I started wondering how long the marriage was going to last and I'm sure it was on her mind even more than on mine.

Date Three, Front Nine Adventure—Ginny

The order of these dirty dates are not chronological other than number one. For my part I just think up a flash back to something we did, check with Kyle to see if he is planning to write about that date. If he doesn't have it covered I start writing.

Writing about hand jobs reminded me of another date that sticks out in my mind.

It was probably three years after our first date. I was divorced and we were no longer living together. On a Sunday morning we took a drive to a resort several miles from the city to play golf, just the two of us. Kyle picked me up early, like 6:00 am; we had more than an hour to drive for an early tee time. I was on the golf team in high school and I hold my own with most men golfers, Kyle is a regular golfer, not a good golfer, we play from the same tees and I beat him every time we play.