High as cherry pie

To start I want you only in one of my hoodies with your panties on. I’ll have you in my lap as we cuddle together. You get out your phone and start to scroll through tumblr. I notice you start to move and grind on my lap. I move my hands under the hoodie and take control of your hips. Without saying a word I move your hips for you and make you grind on my thigh as I kiss your neck from behind. I tell you to keep scrolling and let me take care of your body. When I say that you let out a main and tense up. I can feel you start to get wet on my thigh. I move my hands up and down on your hip while I make you grind a little harder and faster. Soon enough I move my hands off your hips and you’re grinding all by yourself.

My hands move up your belly to your uncovered tits. I grab both of them and you let out a louder moan this time. I tell you that you’re being such a good girl for me as I massage your tits and tease your nipples. Your nipples are getting rock hard under my touch so I pinch on them more. Your panties are soaked and so are my sweats so I remove both of them. As I remove your panties I make sure to let my hand run over your slick pussy to see how wet you are and you’re absolutely soaked.

Once I get a feel of that slick pussy I go ahead and strip myself down but I make you keep my hoodie on. I tell you to keep scrolling through tumblr and you do as told. I spread your legs open I start to rub your pussy. I spread your lips and explore my way around your folds. I hear you moan more so I keep moving until I reach a sensitive spot. Soon I work my way up to your clit with one hand while the other plays with your tits. You grind against my hand and start to whimper as I have fun with your body. Soon enough your drop the phone and lose yourself in my pleasure. That’s my cue to move on.

I lay you down on the bed and move the hoodie up so I can get a good look at that beautiful pussy. You look so adorable in the hoodie with your legs spread. I start to finger you as I kiss you deeply. I can feel you moaning into my mouth. I have to fingers in you while my thumb gently circles your sensitive clit. I fell you grinding harder so I pick up the pace. I move my mouth away from yours and now you are just filling the room with your cute moans.

I finally bring you to the edge, look into your eyes and tell you to cum for me. Your back arches off the bed and you open your mouth but aren’t able to make a sound. Your juices are dripping onto the bedeviled my fingers are still inside you. Your pussy grips my fingers and doesn’t let them go. I keep moving until you fall back to the bed. I tell you how cute you look as I take my fingers out and give you a kiss on your forehead.

While your body is resting and you’re still trying to catch your breath, I stroke my dick making to cover it in your sweet juices. Once my dick is hard and wet I rub it against the entrance of your pussy to prepare you. Your mind is still lost in the pleasure of the last orgasm so it catches you by surprise when I enter you.

While your body is resting and you’re still trying to catch your breath, I stroke my dick making sure to cover it in your sweet juices. Once my dick is hard and wet I rub it against the entrance of your pussy to prepare you. Your mind is still lost in the pleasure of the last orgasm so it catches you by surprise when I enter you. Your still so wet that I slide in easily but once I’m all the way in your pussy grips me tighter than it ever has before. I can see your eyes start to roll back so I take that as a sign to begin. I move slowly at first and you grind against my dick with every long and deep stroke. I can feel your pussy begging for more.

I pick up the pace and start to thrust harder. Your pussy is making such a naughty sounds as I start to pound it. You were gripping the sheets at first but now your gripping my back. I start to pound that pussy relentlessly. I can feel your pussy getting tighter and your body is shaking. Your moaning and screaming at the top of your lungs as I pound you into the mattress.

Finally I move your arms from my back and pin you down. I look into your eyes and tell you to get ready to take this load. You go quite and I film your pussy with my cum. I shoot so much into you it’s starts to drip out onto the bed. Finally I collapse on you. I roll over and let you rest on top of me. I play with your hair and eventually remove myself from inside you. We both sit there in a mess of our own. I give you lots of kisses as I tell you what a good girl you were.

Thanks to reader @flashdoggy for a topic suggestion.

Milking is the act of taking one’s boycock and stimulating him to completion. As always it is important to have a reason for your actions in mind. Is milking a load from your boy a reward for faithfully following your will in staying chaste? Is this a punishment for a chaste boy who did not do his chores for the 3rd week in a row?

Reasons to Milk

- Chastity: Chastity interacts with milking through the obvious denial and later release. If you really want to know a ton about the interaction between chastity and milking you should be following @chirenon. He’s probably the most prolific poster of male chastity on tumblr (he does occasionally post mmf too, so if you’re squeamish be aware). Regardless, some folks believe that a chaste boy needs to be milked for health reasons, others say that’s bullshit. I cannot definitively find an answer (that seems reliable) either way. 

- Reward: Milking is a reward usually for boys who cannot or do not desire long term chastity. It’s a reward that they wait for however long they’re locked away, and when they have waited for quite some time for orgasm. Outside of chastity, some submissives take it as a sign of submission to give up control of pleasure to their dominant. In this way a dominant 

- Punishment: Chaste men often take great pride in the length of time they’ve managed to stay chaste. If one misbehaves, you can threaten to milk him if he does not shape up. Fair warning though, if your chaste boy takes his chastity very seriously, it would be considered a very serious punishment and if the punishment doesn’t fit the crime you could do damage to your relationship. Alternatively for submissives that are not chaste the punishment side of a milking is when you choose not to stop milking when the orgasm occurs.

Ways to Milk

- Masturbation: A hand with or without lube is standard. If you’re lucky enough to own a stroking toy such as a flesh jack or a gel sleeve those are also fine options. It’s worth knowing what region of the boycock is most sensitive. Sometimes rubbing the head will be all that’s necessary for orgasm. Other times the frenulum (look it up) is the most sensitive spot. The last area that can be worth exploration is the Penile Raphe. It’s the urethral tube that can be seen running along the underside of the penis. Rubbing it in circles, lifting it from the penis and rubbing it between two fingers can be ways of stimulating the raphe.

- Tease and Denial: Better known as edging. Simply put you make a big effort to get your boy as close to orgasm as possible and stop. I do not suggest brinkmanship while edging. I have seen and heard of this mistake a lot. Your objective is to get him close and then back off. Do this over the course of an hour and he’ll be begging you for orgasm. Of course whether he’s earned such a reward or punishment is up to you…