My First 26

Mark and I first met in elementary school and we've been pretty much friends for fifty years since then. Over that time we've often had conversations like the following:

Mark: "Man I am so jealous of you."

Me: "Oh boy we go, what now?"

Mark: "Well for starters your rugged good looks, even as we close in on sixty, women still fall all over you."

Me: "Mark, when we were young women fell all over you too, and probably still would if you weren't married."

Mark: "But you're smart too, honor roll all through high school, then a bachelor's degree from Arizona and a Master's from UCLA."

Me: "Mark, I was like twentieth in our high school class and you graduated what third? And your degrees are from Stanford and you even have a doctorate degree."

Mark: "Yeah but, you were born into a wealthy family."

That wasn't quite true. My father was a successful businessman and always had a nice income, but there was never a lot in investments.

Me: "Mark your family was wealthier than mine."

Mark: "But you were a star athlete."

Me: "What are you talking about, you were all league quarterback for two years, I was a wide receiver who got honorable mention my senior year. You were offered scholarships to play baseball, I only started about half our games."

Mark: "You've made love to what like two thousand women."

Me: "The number is 176, and you had plenty of your life and could have had more if you weren't such a devoted husband."

I almost regretted saying that last line, because I was actually jealous of Mark. He and his wife Janet had been happily married for thirty years and Janet was still a knock out. The last thing I wanted to do was encourage Mark to cheat on his wife.

Mark: "Yeah but you have a cock a porn star could be proud of."

Me: "Well there is that."

That sums it up pretty well. I have been fortunate beyond what most men could ever hope for in all the ways Mark described and more. Now the truth of the matter is that there have been many times when those seemingly blessings were turned into a curse. Like when the one woman who might have been a Janet in my life caught me with another woman whose advances I tried to resist, but gave into at the worst possible time. But those are stories for another time. These are the stories of romance and steamy hot sex! I won't tell about all 176, some aren't even all that memorable that I could if I wanted to, just a few of the highlights. And hopefully, there are more to come, 200 sounds like a nice number.

Number One

It was the summer after eighth grade. I sent most of my days at Mark's house swimming in their pool. Mark's sister, Rachel was three years older and she was hot, but her friend Kris was even hotter. Kris was the girl ever guy in the school dreamed about, she had long dark hair, a dark completion and beautiful dark, almost black eyes that just glistened in sunlight. She had a body that I believed destined her to be the centerfold in Playboy in a couple of years. Rachel and Kris would often be at the pool sunbathing and occasionally would get in the water and play Frisbee or something with us.

One day Rachel had a pool party and there were at least 15 girls there. Mark's mom told Rachel they needed to let us be there, but told Mark we needed to leave the girls alone. After lunch the girls decided they were going to go to the mall and walk around and they all went into the house to change. Mark and I snuck in and were watching then peel off their bathing suits when they spotted us. They came after us and even though we were pretty strong for our age they grabbed us and drug us into the house.

One of them decided that we should learn a lesson as to what it's like to be gawked at. The others agreed and they started pulling at our swim trunks. Mark escaped and several of the girls went after him, but I was trapped and soon my trunks were down around my ankles. There I was standing naked in front of about ten senior girls and they just got real quiet. It was like it was the first time they had ever seen an eight inch cock.

"Oh my God, look how big that is." One girl who had been one of the most aggressive said holding her hands over her mouth.

"That's bigger than my dad's" said another, not realizing how that sounded.

"Okay, he's embarrassed enough, let him go." I looked to see who my advocate was and was pleased to see it was Kris. I pulled my suit up and ran home as fast as I could. Mark was locked in his bedroom and wasn't going to come out till his parents came home.

I think the next day or two Mark came to my house and we goofed around there. But soon I was back at his pool. Rachel had been on the phone when everything had happened and hadn't seen me naked. She apologized for her friends, but then added she might want to check things out because the girls couldn't stop talking about my girth. She quickly added that she wasn't being serious.

It was a week later when Kris was back at the pool. She too apologized for her friends and said I wasn't supposed to let it bother me. Since I was going to be going to the high school in a couple of weeks I was worried some of the girls would say something in the hallways and I asked Kris about that. Kris spent about the next forty minutes telling what high school was like and how I should handle things. She asked me about what classes I was signed up and talked about who some of my teachers might be and things like that. Then she asked me what I was doing the next day, I said nothing and she told me to come over to her house in the morning because she wanted to help me with something else.

I went as directed and when I rang the doorbell, Kris answered wearing a men's tee shirt. I wasn't sure if she had panties on, but I could tell she wasn't wearing a bra. Still I was naïve and wondered what this was all about. Kris told me that she was worried about me because I was a good looking guy and when word got around that I had such a huge penis, that the girls would be coming after me in droves and she wanted me to be ready. And then she asked me if I ever had sex with a girl before. I thought about lying and saying I had, but thought better of it and admitting my virginity. Kris said good; because she wanted to be the first and peeled her shirt off. She was wearing panties, but there I was face to face with an absolutely fantastic set of breasts.

She reached her hands behind my neck and brought her lips to mine and started passionately kissing me. Not only had I never had sex, I never really even kissed anyone before, at least not like this. After a minute or so of this, Kris began undoing my pants. I was hard as a rock which made it hard for her to free everything from my pants but she was gentle and continued until I was free, I guess I had taken my shirt off because I was now standing there completely naked and Kris on her hunches in front of me.

Kris took my cock in hand and started rubbing it very gently. Then she kissed it on the head and began stroking. I might have cum pretty quickly, except that I had jerked off a couple of times the night before looking at my dad's Penthouse magazines. I think Kris was surprised at how long I was lasting and stuck her face under my cock and started licking my balls. That felt really good and I wanted to enjoy it as long as I could, but I couldn't hold back and told her I was going to cum. She leaned back and put my cock right up against those beautiful breasts and I let loose. The first couple of streams were so forceful that they splashed onto her face. I think I sent about seven spurts all over her and then a few dribbles. The cum was dripping off her and so she grabbed her shirt and used it to towel off with.

She finished cleaning my cock with her mouth. I thought I was going to die from pleasure. Then she told me I was now ready for my class to begin.

She stood up and slowly removed her panties. Kris had a very hairy bush. She sat on the couch and spread her legs and instructed me to get between them. Then she pulled her pussy apart and began to give me an anatomy lesson. I suspect she was using textbook terms but I wasn't really listening that close. Then she took my hand and showed me where and how she liked to be touched. She then told me to practice what she had just taught me. I spent the next five minutes or so rubbing and fingering her, she was starting to get very wet. Then she told me to use my tongue to do the same things I had just been doing with my fingers. I did as instructed and while I now know I was very clumsy, Kris enjoyed my attempt and had a nice orgasm.

Kris leaned back and took a few breaths and then pushed her pelvis to the front of the couch and told me to do it again. I pushed my face back into her hairy bush and started alternating between licking her clit and thrusting my tongue in her hole. Kris grabbed the back of my head and pulled it tighter against her and told me to go deeper. My tongue was starting to hurt from thrusting it inside her, but then she told me to focus on her clit and insert two fingers in her pussy. I did as instructed and soon Kris's whole body began to tense up, quiver and then seemingly explode as she had a second orgasm.

Kris rested for a moment and then we switched positions and with her between my legs she started massaging my cock. It was already about 95 percent hard and it didn't take long for the final five percent. Kris then began slowly licking it at the base, each lick climbing a little higher till she got to the tip of the head. The next time when she got to the top she pushed her lips down over the head. She repeated this several times, each time starting at the base and licking her way to the top, then taking a little more of me inside her mouth. Finally she took as much of me as she could, maybe a little over half way down my shaft and looked up at me, just holding my cock in her mouth. She then started pushing herself up and climbed on top of me, reaching between her legs to grab my cock and then guide it inside her wet pussy. She pushed her body down until my entire cock was inside her. She grimaced, a kind of half pain, half pleasure look, and just held me inside her for a moment. Then she leaned forward and locked her lips on my and started to raise and lower her hips.

After a minute or so of slow steady pumps up and down, Kris shifted her position slightly, lowering her head on my shoulder and pressing her firm breasts against my chest. I instinctively wrapped my arms around her and pulled her tightly against me. Kris increased her speed and length of her climb up and down my shaft. I had never experienced such great pleasure and couldn't believe this was happening to me. Kris began moaning and then started pushing herself hard against me, pushing my cock as deeply inside her as she could. (Something I later discovered not every woman could do!) She continued for a minute or two and then once again tensed up and then exploded before collapsing in my arms.

Kris rested for a moment before climbing off me. I think she was very surprised that I hadn't cum. She lowered herself in front of me and took about the top third of my cock in her mouth and wrapped both hands around the base and started aggressively working on it. As much as I enjoyed this, I really wanted to cum inside her pussy, so I took intuitive for the first time and pulled her up. She seemed to understand what I wanted and climbed on the couch with her with ass in the air. I stood behind her and stuck my cock between her legs and she guided it into her hole. I started pumping her slowly at first and then speeding up. Trying to maximize the length of my stroke, I slipped out a couple of times before I got my rhythm down. Watching my cock slide in and out added to my excitement and now it was my turn for my body to tense up. Just as I was about to cum, it occurred to me I didn't know if Kris was on birth control, so I pulled out and sprayed a stream up her ass and on her back, Kris grabbed me and inserted my cock back inside and I finished a powerful orgasm.

She asked why I pulled out and I told her, she apologized for not making it clear that she was on birth control. We sat and rested for a few moments and talked about what just occurred and how awesome it was. We then went to her bathroom and took a shower together and then to her bedroom where I got to experience fucking in the missionary position for a long period of time.

Kris apologized, but said if we did any more she wouldn't be able to walk so she finished me off with a blow job. Kris then fell asleep in my arms till about noon, she made me lunch and I headed off to Mark's house to swim. He knew I was going to Kris's house and kept asking me what we did there. I wouldn't give him the details, but I also couldn't wipe the grin off my face.

Kris became my regular tutor that year, seeing me every Tuesday evening when her single mother worked a late shift at their family's restaurant. Kris helped me gets A's in freshman English, but it was her lessons in the bedroom that I've applied over and over again in my life.

It was a great disappointment when she decided to attend an eastern college and over the next several years we'd get together over Christmas break and over the summer. After she graduated she took a teaching job back home and now it was on my breaks from college that we got together. But then she entered into a serious relationship and that halted our encounters, although we still talked from time to time. I was invited to her wedding, but didn't go.

After I graduated from college I started working for my dad as a business consultant. One night several years later after a long day in the office I went to my favorite bar to unwind and Kris was there. Her husband was out of town and we starting talking, after Kris's third glass of wine she told me how I was such a great lover and she really missed having sex with me. I had at that point in time never had sex with a married woman, well not quite true; I had never had sex with a woman I knew was married. I hesitated, but Kris's body looked as awesome as ever and so I offered to take her home. She took me up on the offer and we barely got in the door of her house when she was all over me. It turned into one of the most intense sessions of sex I've even encountered. About three in the morning we were both exhausted and I got ready to leave.

Kris then told me she really needed that, that while everything else in their marriage was great, her husband was losing interest in sex. Kris asked me if we could just get together periodically for sex and I agreed. A few years later her husband admitted to being gay, but wanted to stay married to Kris. She said she would agree if he would consent to her and I having an affair. He agreed and three of us have been good friends ever since. (No we've never done a threesome, not something any of us would be interested in.) So Kris and I have been having sex on and off for forty five years and I still get very excited when I see that she a text message from her.