Well, guys, I couldn’t have told you what I expected when I took Scott’s anal virginity. I didn’t think the day would happen, and I hadn’t planned for it to happen.
So what I did is what I wish a nice boy had told me, before I lost my anal virginity. Which is definitely NOT was happened. That’s ANOTHER story.
So Scott and I dried off and decided to postpone dinner, but got ourselves another drink and smoked some more. We cuddled, and chatted, and sat on the couch and enjoyed each other’s company.
“So, Scott, my love, you need to hear a few things. You know, as you’ve already shown me, how to penetrate an ass. Your awesome size led you to that conclusion as that’s what worked for you getting laid. But you have to get your mind-set into wanting to take your man and give him pleasure. Your pleasure will come from giving me pleasure. Mine is physical, yours is emotional. If you are lucky, I’ll hit your G-spot and it’ll give you physical pleasure. I have been less lucky so far. You know the worst part is the initial sphincter entry, and we both know how to handle that. I’ll take my time, and you can think you are taking a nap, it will be so slow. But then, to me, the discomfort is, with cocks our sizes, bottoming out into your guts. It’s like getting punched in the guts and it hurts. What you need to appreciate is, your man just bottomed out in you and that last inch of cock being massaged by your tight ring is euphoric to him. So for each gut punch you get, you are giving him ultimate pleasure – also you are getting him closer to cumming. Which I always want over as soon as possible.”
“That make sense so far?”
“It does. I intuitively know some of that, but please continue. But why do you want the fuck over fast?”
“Because we are making love already, and he’ll cum and feel awesome and the endorphins will kick in and he’ll love it. Why prolong that mutually desired end result?”
“Huh. Okay. Interesting.”
“So I feel one of the advantages the bottom has, is to make their man feel as awesome, masculine, special, studly, whatever you want to call it, as possible. I call it going porn star, where you can, after red-lining through the pain, ham it up for his enjoyment. Basically lie. Tell me how good it feels, how wonderful, hands and arms and neck everywhere. You are not getting physical satisfaction necessarily, but emotional as my/his emotions are elevated from your words and actions.”
“And remember, each thrust is a gut punch – smaller dicked guys less so, but we are talking about me, so this is going to be a lot of punches in the gut. I love to bottom for you, and I so appreciate your deep and rapid thrusts, but the gentle in-and-outs in between really act as a respite for the me, so I will build those in for our fuck, and then max out the deep thrusts in the shortest amount of time, to help get me off as fast as possible.”
“Following?” And he was rapt attention. “Yeah, continue”
“As you know, there are infinite intercourse positions. The top three being missionary, doggie and standing. There are pros and cons to each. Missionary is the most intimate, as I can look into your eyes and understand where you are in the process. And it is a process. I can kiss you, and you can control my thrusts by grabbing my ass and you also can get access to my balls, in between thrusts. Doggie is great and if you ever bottom for a smaller dicked guy then me, then he can go deeper. Standing is convenient for practicalities sake. You can also consider any of the cowboy positions as you are ‘riding’, but I don’t like the reduced intimacy, and inability to kiss, and I don’t think it’s the best way to lose your virginity. I wanted to have mine taken by the man I loved, not given. It’s semantics, I know, but I wanted him to want it enough to take it, versus me dropping it off like an old newspaper in the driveway.”
“Make sense.?”
“You are too much, Ethan.”
“Then there are a bunch of JV no-no’s, which you’ve already said you’ve experienced across your sexual spectrum. No negatives. No, ‘oh it hurts’ no ‘hurry up’ no ‘you are too big’ or anything else negative. Suck it up, act porn star, and you’ll achieve the end objective as soon as you can.”
“Also, missionary, which is our preferred position, gives the added benefit of putting your cock between our two tight abs. You can lube your dick for fun, and you can let the abs do the work. Or you can give yourself a hand job. But it’s in your best interests to ejaculate fast – but follow my body, if you cum too fast before I’m ready, you are left in the worst case scenario, which is that you are done and I might want 30 min more. And that is the absolute worst, hellish situation. And if you are ever in it, just say done and end the whole fucking thing. So keep your eye on the ‘process’, where am I and where you are. We want to elevate together. And here's a Pro Tip: Talk me through it. 'I'm getting there, I'm getting there' triggers me to get there, too. So use it AT THE RIGHT TIME. Listen and watch the process. Look at my face, eyes and chest. Am I pink yet with exertion? Breathing short? You know the signs, now you need to read them and act accordingly”
“Now, if you time it right, several things happen. First, it will make you feel good, and focus your pleasure on your cock, versus the pain in your ass. Plus, your ejaculations will make your ass contract, bringing me added pleasure. Plus, as guys we are pre-programmed to be cum competitive so that we can impregnate our mutual cavegirl. You cum, it signals to my nuts for me to cum, and wham-o-bam-o, we are done. Got it?
“Geez man, you are too much. Why didn’t we talk about this before? If I knew getting you off would get me off, I’ve have spent a little more time on you, rather than me.”
“Listen, ass wipe, that’s the point of you bottoming. And you are a phenomenal lover. You will also be a more incredibly skilled lover once you’ve gone through the process.” And Scott looked away, with where ever his mind was. It was hard to tell.
“How do you feel about losing your virginity to me? Are you still up for it? You do not have to.” Looking into his eyes, as I pull them back to mine. Where they should be. And we pause.
“Well, I’m high as a kite, and on my many cocktails, but overall I feel very calm and accepting of this. I love you and I really want to experience this with you, I want to live IT with you, I want to learn from you, and I want to give you pleasure.” Fuck. What do you add to that.
“Well, now it’s important for us to not rush anything and to get into the mood. Let’s start with a shower and some foreplay. Your ass will benefit from the best rimming I can do. And would another smoke or drink help?”
So we did just about all of the above. And he was a pro and a stud, let me tell you! Popped his cherry right good, and he said Thank You after. BAM! You want the gory details, I can spell it out, if you want. But I suspect you all can get it from here! Best.
Thanks for reading!
Cheers,
Ethan.