What are your five (5) most memorable/amazing sexual moments?
For these answers, I’m going to stick to only those moments involving my actual sexual performance. Otherwise, this list would be dominated by moments of my observations of my wife fucking others. These are listed in chronological order:
- The First Time I Fucked My Wife
- Red in the Face
- First Gay Penetration
- Wet Sex and Blow Job Paradise
- Joyful Chaste Weeks
The First Time I Fucked My Wife
For the duration of my now-wife’s remaining three years of high school, I imagined having turned our last moment together before she moved away to Las Vegas into a sexual moment. For all those years, imagining me taking it that next step was always a sure cum. A quick and hard cum every time.
Three years later, she returned to Alaska and stayed at my mom’s house, where I was staying for the summer as well. Skipping past the golden rays of light and cherubs I saw around her when I looked at her standing in the living room for the first time in so many years... Within six hours, Renee, I, and my sister lay in a spoon position, in that order with Renee as the inside spoon. It was an exact replication of that moment that I had been imagining for the last three years.
As a piece of exposition, shortly before the spooning started, my sister had stated that nobody would fuck me. Renee bounced up and down and declared, “I would fuck your brother.” So, I felt I had permission at that point, something I had until that point in my sexual life always sought verbally (“Are you sure you’re okay with this? You want to have sex with me?” ) before learning that many women don’t like to be asked permission first; they want the guy to recognize when it’s alright. Back to the spooning.
As we lay there, my hand rested on her waist, a touch I would later learn was one she loved. Then my hand roamed between her legs, and things got hot from there. My sister left, and Renee and I did what I had so long fantasized about. As my bare dick slid inside her, she looked up at me and said, “Just make sure you pull out.” Another line I affectionately remember her saying is, “Quit teasing me. Fuck me already.” Our first night together exceeded my expectations.
Red in the Face
During the first summer we opened our marriage, I got to shove my face into a red bush. Renee, my wife, was always on the look for playmates for me. She knew I had two main fetishes at the time: Asians and redheads. She never was successful in finding me an Asian lover, but she did find someone who would go down as one of the greatest loves and most fun fucks ever. Kelly is what most would call a strawberry blonde, which I consider a subtype of and one of my preferred reds.
The first night Kelly and I fucked was one on one. I remember her pussy was so hot it felt literally on fire. The next time we fucked, though, I had an FMF moment that will go down in my top five. I’m laying on my back. Renee is riding my dick. Kelly straddles my mouth, grinds away, and cocks her head back to kiss on Renee’s neck. As I look up, I see Kelly’s red patch, glide up past her large, burgundy nipples, up past her freckled shoulders, to see my wife’s face beaming down at me as she peers over Kelly’s headless shoulders. The image is a snapshot I can recall at any moment.
First Gay Penetration
My first adult experience with anal penetration was quick but exhilarating. I should specify that I mean anal penetration by another person in which it actually penetrated me, not failed attempts or toys. Up to that point, I had played with myself for awhile with toys far bigger than the dicks of the two guys I ended up with my first time.
Jeff and John met me through the internet in the early days of the Web. We met at a Chinese restaurant in town. They liked me and invited me back to their place just a few minutes away. It wasn’t long before we were all naked and sucking each other off. One of their fingers, lubed, slides in my asshole for a few strokes. Then a remarkably easy penetration, as Jeff points out as he slips right in. “You’re sure this is your first time?”
Slow plunges to the hilt, as shallow as that was due to his small size. At about the thirty second mark, as I’m sucking his man, his paces quickens and fifteen seconds later, he’s slips out. I reach back and he quakes as I shove him inside. I comment on how wet I am and he says, “Well, I just came.” John gives him an incredulous look, then proceeds to take his turn which lasts about a minute longer than his partner. Although they both came quick, I got what I wanted. Dick and an ass full of jizz.
Wet Sex and Blow Job Paradise
In a cheap hotel room around 2002, I had my first intentional wet sex with someone other than my wife and officially grew to appreciate blow jobs. After a pretty great first time in the woods with my wife, Sumi and her husband, we decided to try a different approach: full swap, different hotels.
After checking in, we took a shower together. I fucked her until she came. We were supposed to be using protection, or at least that was what I thought. Still, I fucked her bare in a very hot shower. When we finished and stepped out of the bathroom, she kissed me deep and said, “It’s been a long time since I’ve had wet sex. I didn’t think I ever would again.”
I thought she meant sex in the shower, which seemed an odd practice to possess such a resistance to. Then I caught her meaning. She thought I came inside her - wet sex. I hadn’t cum, but within fifteen minutes of her telling me that, I was shuddering every last ounce of my sperm inside of her. Once our time together came to an end, I lost count of exactly how many times I nutted inside her.
Interspersed throughout our play were several rounds of dick sucking. At the time, I honestly didn’t enjoy anything past a minute or so. Blow jobs were like massages and made me limp. Not with Sumi. She made me not only appreciate but occasionally crave blow jobs. Although it would be years before I came from a blow job (to date I’ve only cum twice from a bj), she genuinely loved sucking dick. It didn’t matter if I came or not. It wasn’t so much about the load, even if that was a sweet bonus. Her reward came from feeling the dick in her mouth, down her throat. She could even ripple her throat muscles when my cock was buried down it. I still haven’t decided if I should thank or curse her for this appreciation of fellatio.
Joyful Chaste Weeks
In May 2009, I went a stretch of weeks without cumming. I had finally established that romantic relationship I had fantasized about having with Allie. Now, you might wonder how establishing a romantic relationship equals no ejaculations. To tell the truth, I’m still bewildered by the contentment I experienced finger banging Allie, making her squirt buckets, soaking my pillow so I could sleep in her juices. I even forced myself to jerk it out of a sense of obligation http://hecumsto.blogspot.com/2009/05/im-not-dead-just-changed.html . I just recently received a text from her after many years. I’m not sure if I should reach out to her or not. Life would be so much less complicated without her in it, but it would be so much sweeter with her in it.
Bonus: What is one quality you appreciate in a lover?
Degradability. Not that they have some deficiency that makes them degradable. By this, I mean that she gets off on being degraded in one form or another. It can be something as vanilla as being called a slut to be something as extreme as being thrashed about and treated like nothing more than a sad piece of meat. That said though, I only appreciate this quality in lovers who ask or subtly prompt me to degrade them. If I have to present it, I feel sleazy and predatory. Surprisingly enough, a large number of women I’ve been with have pushed me to degrade them to rather extreme levels. The few I’ve confronted about it have said that they feel safe doing it with me because they know I’m actually gentle at heart.