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A letter sent to my cross dressing jerk buddy!
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Hi Lisa,
I'm going to describe how I would jack you off, Little Lisa. You must act out what I describe below.
Of course, there are many ways I could masturbate your little dickie, from a quick, hard aggressive jerk off to get the cum out fast and furious. Those can be fun, but I greatly prefer the other end of the spectrum, a long, slow, languorous masturbation session with plenty of playing and stroking and teasing and building to an orgasm that, by now, is dying to explode.
I think I'd like to give you a hand job while I'm completely dressed and sitting on a dining room chair. Meanwhile, you are ordered to strip, and as you peel off your shirt, you reveal your black lacy brassiere that makes you look so feminine. You wiggle your shoulders side to side as if you had perky little boobs to show off. Next, off come your pants, only to betray your black fishnet stockings, black sexy garter belt, and sheer black panties straining against your stiff little penis. Oh, you are such a little sex pot, all dressed up with nowhere to go, but lots of places to come!
"Put your hands over your head, Lisa" I say with a smile, "and move your hips to show me what a sexy little tart you are, dance for me! Feel the pleasure of dancing around in your lingerie, prancing just like a stripper, showing off your hot body!" "Now move those panties down, not too far, just enough to liberate that aching cock of yours. Now dance some more, so your weewee swings and flops and displays itself! Turn around and swish your ass for me. Show me how sexy you are. Show me your round ass. Ask me if you are allowed to spank yourself, say, "Davey, you're getting me so hot and sexy and I think I need a spanking. Is it alright if I spank myself a little." I'll reply, "Yes, Lisa, show me just how much the little sissy Lisa wants to get jacked off by spanking your bare naked ass Give yourself 20 hard swats on each cheek." As you slap your ass I can hear each swat, spank, spank, spank, spank, spank. Make those ass cheeks good and red!" Spank, spank, spank, spank, spank... "Tell me you need to get jacked off!" spank, spank, spank, spank... Say, 'please jack me off, please play with my peepee, please make me cum. Please, please, please." Spank, spank, spank, spank, spank...
"Okay, Lisa, come close so I can examine your cute little ass." I move my knees apart and you back up towards me until you are standing in between my legs. With my right hand, I ever so gently touch your bottom, caressing your smooth reddened cheeks, one side and then the other, cupping them, soothing them, running my right index finger along the fold of skin at the bottom of each cheek, and then sliding one finger along your ass crack, and you let out a sigh. I say, "You like that, don't you little Lisa?" "Yes, Davey, it feels so good." The same finger now moves from the top of your ass crack to the bottom, slightly deeper between your cheeks, and then upward again, still deeper. Then downward, deep in your ass crack, so deep that on the way down the tip of my finger touches your anus and you tingle with pleasure and anticipation!
Next, my right hand moves further down, touching your excited scrotum and you flinch with delight! "Spread your legs Lisa, Now!" I command. As you obey, my hand cups your balls and just holds them, for over a minute, bouncing them ever so gently, and then giving them a little squeeze that makes you wince. While playing with your balls with my right hand, I reach around your hips with my left hand and touch the tip of my middle finger to the front base of your shaft, touching my right hand, which is still holding your balls. My left middle finger moves slowly, slowly up your shaft, so slowly that it's barely moving, up to the glans of your penis, and when reaching the rim of your glans, slides in a circle around the base of the rim, and then back down the shaft. I do this at least five times, slowly, slowly. You are so very hard by now.
I tell you, "I want to hear noises, sighs, grunts, moans. I want to hear your response to each touch." I take my left thumb and index finger and hold your peter pinched between them at the mid-point of your shaft. With a little squeeze, I pinch and twist your cock and release it, watching as it springs back to straight. Again, pinch and twist and release. I do this ten times, pinch and twist and release, pinch and twist and release....each time at a slightly different part of your shaft, finding the most pleasurable. I run the tip of my middle finger up and down the shaft of your cock, sometimes touching the rim of your cock head, sometimes not. I tell you, "You can move your hips if you like." Your respond with several humps, and I have to scold you, "No, Lisa, just little slow movements, with deep breaths."
Next, I let the tip of my index finger circle around the rim of your glans, some circles slow, some faster, some soft, some with more pressure. You moan and move your hips and breathe audibly. For a moment, I remove my right hand from your balls. I'm reaching for the bottle of baby oil, remove the cap and squirt some onto your cock head. I make a circle with my left thumb and index finger so they are very oily and slippery. "Okay, Lisa, now I'm going to jack you off in earnest. Are you ready? Tell me, 'please jack me off, please masturbate my cock, please jerk me off, I want to come so badly!"
I slide my left thumb and index finger up and down, up and down, first slowly, then a little more quickly. I squirt a large dose of oil onto your cock so it is thickly coated with oil, not just your cock, but your balls as well. I slide me right hand back under your scrotum and spread the oil all over them so I can constantly slide my hand over your slippery scrotum while I take my entire left and grasp your cock, shaft and head. For a good minute or two, I stop and just hold your cock and balls, just feeling the size and heft and rigidity and desire as you try to hump my hands. I say, "That's it Lisa, hump my hands, show me how you want it." Eventually, I start stroking your cock again, so slippery with oil, up and down, slowly, slowly, now spinning my left hand so it moves around the shaft, and then just the head, around the shaft, and around the head, around the shaft, and around the head...
As your breathing gets heavier and your humping becomes more desperate, I command, "Tell me what you want, tell me what you want Lisa." And you shout out loud, "'please jack me off, please jerk my cock, please make me come, I want to come so badly!" And as I jack you off frantically, my oily right thumb moves backwards from your balls, sliding along your perineum, touching your anus, sliding around the pucker of your asshole, and then sliding inside, stretching your sphincter, slipping in to the second knuckle, and then in and out, fucking your ass, and then you release a deep guttural growl of pleasure as your body tenses and releases, contractions and dilations, and a massive explosion, one, two three, four big spurts of thick ropy come arcing into the air and spattering to the floor. And then your body relaxes and you almost fall as you sit down in my lap, my right thumb still up your ass, the palm and fingers still wrapped around your balls, my left hand still wrapped around your cock, moving just enough to release the tapering sensations of pleasure from your now spent penis.
And you say, "Thank you Davey, thank you for jacking me off so good, thank you for making me come, it felt sooo good."
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Posted on : Mar 9, 2019
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