The Anaconda: One Woman’s Experience With A Cock That Was Too Big

Guest post by D.K.

After reading Lady Jane’s post One Woman’s Orgasm, I’ve decided it’s time to share my story. My story isn’t about my orgasm in particular, but the long journey before I ever even reached that point.

I was either 16 or 17 when I really started to explore my sexuality… willingly… with a penis/cock/dick/manhood… whatever you want to call it. There were a handful of times before then, but I don’t really count those. That’s a whole other story I’ll save for another time. I saw my partner’s cock before we ever got in bed with each other, and to be quite honest, it scared the hell out of me. I hadn’t expected it to be so big – big for me anyway. Being the devious girl that I am, I snuck into the shower when he was washing off and boldly opened the shower curtain. Lo and behold this was the day I gave his cock a name – “The Anaconda”. Seriously… I called him the Anaconda for some time. Years later we got married, and the only experience that topped having the Anaconda being thrust into me was when I gave birth to an 8.5lbs baby, and then another one again 21 months later.

Our first time was painful for the both of us. He admittedly likened the experience to “penetrating into a wall,” and politely tried to explain that his head felt like it was “peeling back.” At one point he wanted to stop because it hurt HIM. Okay, I know what you’re probably thinking. You’re either thinking that he wasn’t aiming right or I wasn’t turned on. The truth is I was definitely turned on, but his size made me nervous… and we didn’t really think about lube back then.

The next few attempts probably got us half an inch of penetration. He would swear that I had some crazy regenerative powers, and I secretly wished he were a teensy bit smaller! I know a lot of women would consider his endowment as a positive attribute, but I didn’t feel that way until years later. The first few months were not pleasurable at all. The anticipation of the discomfort hampered my ability to enjoy the experience. He could sense my anxiety and discomfort and I’m certain that it impacted the way we approached lovemaking. He had to be gentle and all I ever wanted was to be swept away with intensity.

After years of this kind of dynamic it really did set a tone in our relationship and marriage. I don’t think I’ve fully considered to what length it set the stage until now. There were numerous times when I wanted him to be more assertive and dominant. He would hesitate A LOT in bed, and that in turn led to a number of other issues (again, for another post). The physical discomfort finally settled into what seemed like paper cuts on my perineal area. Again, this experience was a great precursor to what I would later feel giving birth to my sons – except I had to have an episiotomy to avoid having second-degree tears in my vaginal tissue. I’ll save that for another post, too.

Let’s get back to the Anaconda. So I finally conquered my fear of the Anaconda somewhere after the third year. The paper cut sensation eventually faded away and I learned to relax a bit more. My husband was being more responsive to what I wanted, although he did have to ease into me and avoid certain positions because of how deep he went. I had my physical limitations and he started to figure out the “pussy puzzle” (what he called it) over time. It’s much different today. I’ve been with this man for over half of my life and we have two beautiful sons to show for our successful lovemaking. He still believes there is never a dull moment when he encounters the “pussy puzzle”, but we don’t have the problems we once had. I’m actually looking at him as I type this last section out, so I’ll go ahead and include his words:

“I know this isn’t going to sound right, but it’s just so much easier – you can ‘take it’ and that gives me the confidence in be more assertive and explore with you. I’ll never forget there were a few times that it actually hurt you, and it hurt for a couple of days. That really resonated with me, but I’m glad you communicated with me.”

It has taken us a while to get to this point. We were high school sweethearts in love when this all started. Since then we have grown together and are truly grateful to be able to continue communicating our thoughts and feeling so candidly. It takes time. There is no doubt that we struggled and the experience led to some frustrating moments of misunderstanding. It wasn’t so much the actual size, but more the anxiety surrounding the experience that impacted us at a psychological level. I hope that sharing our story helps to bring a different perspective to your own experiences. At the end of the day, the best you can do is to communicate honestly with your partner!


For guys with big cocks that are worried about hurting their partner when they penetrate them, we recommend watching the video below:

Check out our guide to choosing a lubricant here.

Featured image of woman biting her lip courtesy of adamr on FreeDigitalPhotos