While this is not a recap of any specific experience, it does reflect the approach I’ve taken with several partners in terms of how I’ve introduced them to the pleasure’s of anal play. I hope everyone enjoys it! Let me know in the comments or feel free to send me a PM.
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I gently pull your black panties and t shirt off so you are naked in front of me. I lead you to a padded massage table. I have you first lay on your back and I spread warm coconut oil over your entire front. I massage your body starting with your fingers and hands, working down your arms. I massage the oil into your breasts, rubbing my hands in circles feeling the nipples rub against my palms and then slowly pinching each of your nipples.
I roll your nipples harder between my fingers until they are stiff, little nubs. I then pour more oil on your belly and rub it in circles before dragging my oily, slick hands down each of your legs. I drag my strong hands up and down your thighs all the way to your feet. I massage each of your feet with firm pressure, sliding my fingers between your toes. I grab each foot in both hands in turn and firmly massage the balls and soles of your feet with my thumbs. Not expecting it, you moan as you feel my mouth wrap around each of your big toes as I suck deeply.
At this point, I slide my hands up your inner thighs, all the way up to the V between your legs. I make sure not to touch your rapidly engorging pussy lips yet. I come close, but stop just short. Your hips squirm as you ache to be touched. I run my hands up between your legs and around your belly, never touching the hot, moist center that you ache for.
Your pussy is now aching to be touched, but in our preparation it isn’t time yet. I have you flip over onto your belly and I again pour the oil, starting from the base of your neck and pour a thin line right down the middle of your back and between the crack of your ass. I use my hand to gently spread your cheeks open and pour some warm, slippery oil right on to your beautiful, tight little rosebud. I then let your cheeks close around it. I pour more oil down each of your legs and then start from your feet again. I massage each foot and each toe. I then wrap my lips around each of your toes and suck gently. This sends a thrill through your body.
I continue the massage starting back up at your shoulders and neck. I work out all the tension and continue down the muscles of your back until I get to your ass cheeks. I grab them firmly as I massage them each in turn. I then spread your ass cheeks with one hand and draw my fingers gently down the crack of your ass and then draw slow, soft circles around your asshole. Slow and around and around in the warm, slippery oil. Can you feel that? The gentle stroking of your tight and sensitive asshole?
After softly and gently massaging your tight little hole with my fingers, I lift up your hips so you are on your knees, your ass is pointing in the air and your back is arched. I lean forward, spreading your cheeks and breathing warm breath on your asshole before slowly dragging my tongue from the bottom of your pussy and up to your tight little hole, swirling my tongue around and around. I do this for ages as you feel all the nerve endings in your ass light up with pleasure. At this point, nothing has been inserted. I’ve only been stroking and using my tongue.
This is the important part. Could you be comfortable with this? Could you enjoy the feeling of a persons tongue in your ass without being too self conscious? Could you let yourself go and surrender to the feelings?
With your hips pointed high in the air, I bury my face deeply in your ass. I use my lips to gently kiss your hole and my tongue to swirl around and around. I love and lick every beautiful little crinkled fold. Now, next step. Your pussy and your ass are tightly connected. The more I stimulate your pussy, the more relaxed your ass will become. Your ass is still in the air and my face is buried in your ass. Now is when I reach down with my hand and start to massage your pussy and clit while I continue to lick your ass. Your pussy is so wet now and I spread your juices all over your lips and then rub your swollen clit back and forth quickly.
I hear you start to moan as you now connect the feelings in your clit with the pleasurable feelings in your ass. It starts to blur into one giant sensation.
Now I start with two fingers and slide them slowly but smoothly into your pussy while I still continue to lick your ass. The feeling of my fingers penetrating you causes you to moan even louder. I slide them slowly at first but gradually plunge into you faster and faster. I add a third finger and it makes you feel so full as I simultaneously finger-fuck you and lick your asshole. I curve my fingers downward toward your belly as I thrust to stimulate your g-spot.
With all the pleasure coursing through both the nerve endings of your pussy and ass, we are now at a point where your asshole is starting to relax and we can see if you are ready for penetration.
While I continue to rub your pussy and clit, I take a bottle of water-based lube and start to squeeze some onto your asshole and start to rub it in slowly with my fingers. Because of how relaxed you are and the pleasure you have had, your tight little asshole is more relaxed. You are breathing deeply and you are ready – aching actually – to feel something slide in. I start with one finger, coated in lube and gently press on your hole. Amazingly, your ass opens easily and accepts my finger which slides in. Now you can feel the incredible sensation of one finger in your ass while my other fingers are in your pussy. You will feel incredibly full and stimulated. Can you feel that?
Now you are starting to understand that your ass is designed to give you pleasure. I continue to slide one, well lubricated finger in and out of your ass, twisting it as I go. As I hear you moan in pleasure, I tuck my index and middle finger together, one behind the other, and slide both of them gently into your ass. You feel fuller, but there is no pain.
With me you are on fire now. Your pussy and ass are being stimulated in a way they never have before and now I think you are ready for my cock. Are you? Are you ready for my cock in your ass? I need you to ask me for it. Tell me what you want right now.
You are still on your knees with your back arched and your ass pointed up and exposed. I come up behind you and you first feel my thighs press against yours as my hard cock slaps up against your pussy lips from underneath. You reach down and drag your fingers along my cock from my balls to the tip. I shift back and place the head of my cock at the entrance to your beautiful pussy. Your cunt is so wet that my cock slides in with ease and you let out the most amazing moan as I sink in to you to the hilt.
I then rock back and forth, fucking you rhythmically. I reach down and start to rub your clit with my fingers as I fuck you. You are moaning now but you know what you really need. You then say the words I’ve been waiting to hear: “Fuck my ass. Please, I need to feel you inside me.”
I know now that you are ready. I pull out of your pussy. My cock is glistening with your juices. I squirt another stream of lube onto your asshole and work it in with my fingers. Your sphincter is relaxed and loose now which I test by sliding two fingers easily in, spreading the lube. Are you ready, finally, to have your ass fucked? Tell me again.
I slide my thick cock out of your dripping pussy and I line up the head with your beautiful, tight asshole – the one that I spent so much time hungrily licking and sucking earlier. I press the smooth, bulbous head of my cock against your hole and slowly start to push. I reach down and rub your clit rapidly as I press.
I reach down with my fingers and trace the edge of my cock as it meets the stretched out skin of your ass. The tension feels so good. I press deeper until my entire cock is buried deep in your ass. The silky lube I’ve applied makes my thrusting in your ass effortless and smooth. I reach down and grab a small vibrator, turn it on and press it against your clit as I slide in and out of your ass. This takes you to a new level and you push back against me as I fuck you – never knowing how good it could feel to have your ass fucked. I hold the vibrator hard against your clit and increase my pace. I can hear you are ready to cum for me. My cock is coaxing your orgasm out of you now.
My cock feels so good sliding in and out of your tight, slippery, ass. I can feel the walls gripping me – literally pulling the cum out of me. I can’t last much longer baby. With the vibrator pressed hard against your clit, I thrust once more, deeply and hold my cock still as I hear your orgasm rip through your body. You bury your face in your pillow as your hands grip the sheet tightly into a ball. You scream your pleasure into the pillow as I pump silky ropes of my hot, white cum deep into your ass.
I hold your hips tight as we come down from the high of our orgasms. After awhile, I pull my softening cock out of you now and pull your knees down so your body lays flat on the table. I massage your back slowly to soothe you before pulling a clean, soft sheet up over your body. You lay there in post-orgasmic bliss
Source: reddit.com/r/sexystories/comments/alqhw8/an_erotic_massage_and_intro_to_anal_play