Month: September 2024

Dear Diary,

When I approached the bed, he began to inch toward one side of the bed to give me to room to sit next to him and so I did, but faced toward him and then I reached for his crotch, very gently touching the shaft of his cock and teasing the tip with a finger or two and then in my downstroke, going past his cock shaft and with a more firm grip, I’d cup his balls that had tightened up. There wasn’t any question in my mind that he was ready to cum…and ready to cum a lot…and while I wanted the latter, I wasn’t interested in just a quickie. Thankfully, we had time to play…the whole fucking day actually.

And it was around that time, I remembered to put out the “Do Not Disturb” sign. I quickly got up, moved swiftly to the door and risked opening it in my almost-undressed state to put the sign on the door handle. As my luck would have it, someone was walking down the hall at that time and maybe caught a quick glance, but oh well. Lucky them, right?

I shut the door and then locked it behind me, returning just as fast to Ian as I had left him and continued to give him a gentle hand job if you can call it that asking if it felt good and letting him know that he had a great looking cock. He didn’t speak much other than to let me know that it did and that he liked how I looked as I began to slip my bra and panties completely off. Do you know what that does to a 53-year old’s ego when a young man tells you that you look good? My pussy tingled with delight as I leaned in to kiss him with my tongue and then lifted one leg over his torso to straddle him so that his dick was behind me.

I kissed him hard and continued to do so throughout. Kissing is so fucking important to me, and it really gets me to connect with a lover. I feel it establishes a bond and while sex always seals the deal for me, kissing is a must have for a good love making session, and I wanted Ian’s first time to not be just some fuck, but I wanted him to make love to me as I was wanting to make love to him. I felt I owed that not only to him, but to his parents, and myself of course.

Eventually I broke my lock on his lips, and arched back, stretching myself as I moved myself into a better position. I was still sitting on to of him, but now I felt I could reach behind me to grab his cock. I couldn’t see it, but feeling it, it was still rigid, and the tip was wet with a little pre-cum. I looked down at him and knew the boy was ready for the time of his life with me. I actually asked though, just to be sure and in the cutest way, he told me he was saying something like, “I’ve been ready for this…for you…my entire life.”

“Aww,” I thought. How sweet? Right?

I lifted myself up, with his cock still in my right hand and balancing my squatting self with my left and positioned my cunt right over his cock head and then slowly eased myself down with my pussy lips wrapping around his virgin cock. A little discomfort as I was wet, but hadn’t totally gotten there, but after a little adjusting, he was fully inside of me, and I was resting on top of him.

Ian was a virgin no more and I smiled down at him as he and I both realized that I had just taken his virginity at that point. I was ecstatic about it and I was sure he was too in the moment. I leaned forward and down onto him, being careful to not allow him to pull out on accident but offered held my left tit in my hand as if to feed him with it. He took to it as a baby and began sucking and sucked aggressively as if I was going to miraculously produce milk. I inched up eventually, pulling it out of his mouth and then fed him my right tit in the same manner. Again, I let him suck on both of my nipples for a few moments before I pulled myself up and again fully sat on his cock.

I then lifted my knees up and off the bed and slowly began to fuck him as he grabbed the side of my legs to steady me. I began to speed up the thrusting up and down on his young pole and the intensity of it all increased as well with every thrust down onto his young body. Up and down…up and down…I continued to speed up until I couldn’t fuck any faster. My body was moving almost uncontrollably as I wanted to ensure that Ian’s first was going to be his best too.

My tits, as heavy as they are, were bouncing up and down and Ian would do his best to shift his hands from my legs…to my hips…to my waist…and ultimately to my tits. And then he’d repeat the process in some variation as I bounced up and down on his dick.

I was soaking wet…my pussy for sure, but I was also working up quite the sweat. Fucking is a great exercise! I tried my best to just focus on him with at least some eye contact in the hopes of preparing for him to cum for me, but as fast as I was fucking, it wasn’t terribly easy to do. I did my best though and could sense also in how he’d grip me that he was close. And then boom! I felt a shot right up inside of me. I was close myself to an orgasm, so I continued to fuck at the same pace, not slowing down. I felt another couple of shots and still continued. Knowing that this young man had just shot a good healthy amount of semen inside of me also helped me in working my orgasm.

I did slow down as he clenched my waist harder as his cock was now tender, he wasn’t going to be able to take much more, so I sat directly on him and rocked back and forth…and then pure pleasure! My own satisfaction filled my body…I became a little light-headed both from the orgasm and the workout fuck.

I collapsed almost immediately right on top of him and wrapped my arms around his head in a nice postcoital hug as if to say, “I love you”. He in turn wrapped his arms around me too, even as sweaty as I was. It was nice to just lay there on top of him as his cock was still inside of me. I could feel it softening, but I didn’t want it to. In an effort to keep him hard just a little bit longer, I undid my hug, gave him a deep kiss, and then sat back up straight so that his cock was again fully inside of me and wiggle my body on top of his playfully. His cock was so tender though that he could barely take it. I loved teasing him, but ultimately relented and got off of the kid, swinging my leg over and laying down next to him.

I could feel a good glob of goo fall and had to have hit the bed sheet somewhere. The sheets were pretty wet anyway from my vaginal juices and our sweat from fucking. Ian’s semen just added to the mess and it’s something that I really enjoy…messy sex. I spent a moment trying to catch my breath before I took my finger to test just how messy my cunt was and there was still a good amount of boy cum down there. I absolutely had to and wanted to taste him so grabbed what I could with a couple of fingers and brought it up to my mouth. Yum! Fresh boy meat cum… it’s so fucking delicious. I took a second scoop and then a third, each one with less volume than the last, but still really good. I savored it because, while I knew Ian had masturbated plenty as a teen, this was still virgin cum to me, so it’s special…at least in my head. I suppose I’m weird like that.

He looked over at me, in complete amazement and I could tell that he was thankful and mesmerized by me and what had just happened. We absolutely had a bond secured in the moment which is also special to me. If I never saw him again after that moment, he’d always remember me as I was his first. Thankfully, by the look in his eyes, he wasn’t looking to run away from me, and nor was I from him.

Young love can mean so many things to different people, but to me, it’s the love I feel for someone such as Ian…or Alex, or Nolan, or Danny. I’ve been fortunate to not only experience but develop relationships with four young men over the years as an older, mature woman. It’s one thing to fucking ride a big black teenager in some random parking lot, and by no means do I discount how that happened or how good he felt, because he felt amazing. But I absolutely treasure developing a connection to younger men. Again, I’m likely weird for thinking and feeling that.

Still a lot more to come.

Love you,
Danielle