So he says he's new to this. Never really admitted how much he enjoyed anal play until recently. He craves more, the more the explores his ass the more he becomes open to. Says he's curious about men…but in talking with him more I get the jist he is a little confused. I dont care if he bangs a guy or not, but in describing what turns him on…its never a man. Anal play turns him on, that has no bearing on his sexual orientation. In laying out our guidelines he lets me know that his ass holds the key to most of his kinky desires. I ideas and visions play through my mind. I may enjoy this more than I thought. I've never seen him, only talked to him, he's due to be here any minute. I hear a knock at the door.
I open the door, he's standing there not really making eye contact with me. He is really shy, he told me so but I didnt think it was that bad. I beckon for him to enter, he does so hesitantly. "Are you ok? Still want to do this?" I ask gently in a soft voice. I notice the erection in his pants…he must be thinking of what we'd talked about, or he's attracted to me. Either one I dont care, a sign is a sign. He nods, I smile at him. "No need to worry, I remember everything we discussed, I am not in this to hurt or degrade you, only to bring you pleasure, at the moment only your pleasure is on my mind." I reassure him. He looks up at me and gives me the tiniest grin. He's cute, wonder if he knows that…probably not. I walk up to him, he's looking at the floor, I put my finger under his chin lifting his head so that his eyes meet mine. "I'm not that kind, you can look at me, I'd actually prefer it." I pur to him. I realize that he is like a baby deer, skiddish. I dont want to scare him in the slightest, I hear him say, "Ok, I'd just read that most mistresses dont like it when you look at them because…" "Shhhh, I'm not them" I say putting my finger over his soft lips, I wonder what they would feel like wrapped around that same finger. "Suck my finger."…I dont bark the order at him, just assertively yet seductively say it calmly. He complies hesitantly. "When I request something I want you to work hard at not hesitating. Dont stop sucking, you have sexy lips, I like watching them wrapped around my finger. I know it will take trust for you to just do as I say no questions asked, but you can and will trust me. I will not hurt you, I'll say it again that is not my motive. Pleasure is my MO, understand?" He nods with my finger in his mouth sucking away. I remove my finger from his mouth and put it in mine, sucking away his saliva. "Mmmm tasty, ready to get started?" I ask standing there unashamedly with hard nipples that I notice him peeking at, and a dripping cunt, which I'm sure he is oblivious to. He nods at me, I give him a devilish grin and lead him to where our festivities will take place.
We enter the room, I close the door behind us. The lighting is dim, I see him looking around at all the different "furniture" in the room. "Anything in particular interest you, or arouse you?" I question as his eyes move from object to object. He points to a mahogany table with hand cuffs laying on top. Thinking of what we'd discussed I know exactly why, I walk up to his outstretched finger and bit him gently while eyeing him eyeing the table. He turned focusing on me, "I'm not them…you can speak." He nodded again. I glance down at his pants his erection still has not subsided, it was straining against his pants begging to be freed. I thought his pants would burst at the seams soon. I get closer and begin unbuttoning his shirt while examining his face. I peered into his eyes, noticed his arousal and shyness all combined. His eyes had a glow, as if he was slowly coming to life, but the shy self conscious man is never far away, he just hides there in the background hoping to go unnoticed. I gaze at his lips anticipating the moments when they are parted as he pants and moans in pure passionate pleasure. Soon his shirt is unbuttoned and i'm sliding it off of his shoulders, it glides to the floor. I reach down unbuckling his belt, then unbuttoning his jeans, then unzipping his fly. I push his pants down over his hips they pool no the floor at his feet. "Step out of those and sit on top of that table you like so much." I tell him as I go to retrieve my "tools".
I return with 2 strapless strap ons. I place them on the table next to him he looks down at them. "Pick your poison." I say, giving him time to think it over. He picks up the happy valley tango, feeling it examining it, then puts it down. He then picks up the Fun Factory Share, doing the same. "Uhhh I'm new to this, I'm not sure." he murmurs. "How about both…one at a time of course, then you tell me which you prefer after you've tried them both…" I offer. He nods…I think I'm starting to like his shy silence more as this goes on.
So I leave the strap-ons where they lay, and walk up to him sitting on the table with his knees slightly apart. I step between them and touch his chest with both hands, focusing on his nipples. "You can touch me if you'd like. If you'd just like to be touched that is fine as well." I say continuing to explore his skin. I push him back so he is lying on the table, I put his legs up on my shoulders. The table is at the perfect height so that his ass is off the edge of the table with my hips pressed against it. His cock is tenting his boxer briefs reaching up and slightly forward, I caress his man meat with my hand then grasp it in my hand feeling the hot girth. He's hard as steel, I hear his breath catch as I begin to stroke him through his underwear. I let go of his steely rod and grasped the waistband of his underwear and tugged them off his hips. Now he is fully naked before me, his balls laying just between his legs, nice size on those, they look full…as if they need to be drained. I push his legs back towards his chest a bit so that I can get a good view of his asshole. What surprised me was how willingly he held his legs giving me full access to his tender bottom, he must really want this. I look up at him, "Let the games begin." as I kneel down, effectively disappearing from his view. His ass hole was presented to me on the edge of the table, not much hair but not bald either, I like that. Pubic baldness always reminds me of little boys, and since I'm not into pedophilia it always turns me off, however in these circumstances, its not really about me, but this is a plus.
I kiss his left buttock then his right, then I lick slowly from the bottom of his crack to his perineum. When my tongue passed over his asshole he moaned and I felt a tiny quiver. I lick back down passing over his asshole again, same result. I kissed his hole sweetly and felt his hand on my head trying to keep me there, I smiled against his hole. Ok I'll give him what he's paying for. I licked my lips and incidentally his sweet hole at the same time and started giving him a tongue lashing. His ass relaxed letting the tip of my tongue slip inside his warmth. Hearing him moan, feeling his legs tremble, tasting him intimately, feeling his fingers in my hair holding me right where he wants me as he wiggles his ass in my face dancing on my tongue is such a turn on. Usually I dont have to take care of myself until after a client leaves, but this one may be a change of pace for me. I lick his perineum and balls as I slipped a well lubed finger into his ass. I massage his prostate with my finger and balls with my tongue, he is moaning and writing all over the table, his legs on either side of my head now. I lick up the shaft of his cock sucking it into my mouth once I reached the head. I continue working his prostate as I suck him deeply into my mouth. While deep throating him I slip another finger inside him. I'm amazed at how easily my finger entered him, he has a greedy hole that needs to be filled, I love that about him. I continue to stroke his dick with my lips as I stroke his prostate with my fingers. I can feel him getting close to ejaculating. His balls are drawing up close to his body, he's thrusting into my mouth then down onto my fingers. I slide my fingers out of him and stop sucking him, I stand between his legs gauging his reaction. He looks bewildered, like I just took away his favorite toy. "It's not time for that, we dont do instant gratification here. You've had enough of that over your life time, time for something new." I inform him while walking away, I go retrieve some lube, then return.
"This will be cold at first, but it will warm up." I say as I return with some frozen lube "bullets". I can tell he is curious as to what is to happen next. I gently push one of the bullets into his hole, it slides right in, I suck his cock some more while playing with his nipples waiting for the lube to melt inside him. After a couple of minutes I grab the Fun Factory Share, "Watch me." I tell him, I'm standing next to him as he lies on the table, he has an easy view of me. I put one foot on the table so he can get a great view of my dripping pussy, then insert the bulb end of the Share that goes inside me. He hears my wetness as it slides in, I lower my leg back to the floor. "Now that I have a cock, lets get down to business." I say walking back towards the end of the table that has his ass dangling off the end of it. I lube up the business end of the Share, then place it at his opening. "Now just relax. If it hurts tell me. If something feels especially good tell me. Ok?" He nodded
I press gently and the tip slides in effortlessly. I go farther and his ass seems to suck me in, he gasps in pleasure. "Don't you have a greedy ass?" I say giving him a sinister grin. I began moving slowly in and out of him, not touching him at first, just watching. After a few minutes he was panting and writhing on the table. I see him reaching for my hips, he grabs me pulling me into him, I pound him harder. He's really moaning now. He wraps his legs around me, and I grab his hips pulling him into me fast and hard while he flicks his nipples. The sound of our skin smacking together mixed with our moans and heavy breathing is intoxicating. I go between fast and hard, and long slow strokes for a while. Then I decide to change it up a bit. I crawl up on the table with him, the sweat on his back helps him slide back a bit so my knees are on the table. I lay on top of him missionary style and slowly start to work his ass deeply. I feel him trembling beneath me, breathing unevenly, I'm staring into his eyes watching the passion intensify in them. I feel him touch me…this time different then when he was pulling me into him. That was more of a utilitarian touch telling me what he wanted, this touch was more sensual. He put his arms around me and was caressing my back…even grasping my ass from time to time. Then he kisses me. It was unexpected, usually in situations like this I dont kiss, I save that for my personal life. However here I am reciprocating kissing him back, caressing his face and running my fingers through his hair. When I realized what I was doing i broke off the kiss.
I withdraw from his sweet ass get off the table, and walk around to stand on the side of the table where he can see me again. I notice his chest rising and falling at a rapid rate, he has a raging boner it almost looks painful. I slip the Share out of me, my pussy makes a slurping sound I place the glistening toy to the side and pick up the Tango. I slip that in, and look over at him. "We're going to try something else." I say picking up the handcuff thats are still on the table. "Stand up, then turn and face the table." I command him gently. He does it, his ass looks even more amazing from behind, I have to refrain from staring. I kneel down cuffing his left ankle to the left leg of the table. I do the same with the right ankle. Then I get another pair of cuffs and cuff his wrists behind his back. He is standing at the end of the table, legs spread, wrists bound, and a his hard on dangling between his legs. "Bend at the waist." he does it resting his chest on the table. "Are you comfortable?" I ask while gently raking my fingertips up and down his spine. "Yes." was his simple reply, the first time he's said anything in a while. I lube up the Tango and slide into him. He moaned audibly once my "cock" was in as deep as it could go. I stroked the length of the Tango in and out of him several times slowly and gently so he could get used to the new position. Then I increased the speed a bit, his moans became more audible and consistent. I start to really pound his ass grabbing onto the handcuffs on his wrists using them to pull him onto my "cock". He's not resisting at all, as a matter fact he is sticking his ass out more presenting it to me. Oh what a present it is, and its mine for the taking. I decide I want him to ride me.
I slow to a stop and pull out. I uncuff his wrists then ankles. He stands up and looks at me, his face is flush, so is his chest. "Come." I grab his hand an lead him over to an armless chair thats in front of a mirror. "See how sexy you look." I nod over to the mirror for him to look at himself. He stares into the mirror but doesnt say anything. I grab a cock sling and kneel down so I can stretch it over his cock and balls. "Too tight?" i ask looking up at him, he shakes his head, "No." I stand then sit in the chair. I beckon him to come closer, "I want you to sit on my cock, I want to watch you ride me." He steps closer putting one leg on either side of mine, then spreads his ass with his hands and skewers himself on the strap on. I watch him ease down the shaft until it disappears completely inside him. His dick is standing up between us his balls pressed against me. I gaze up at him. He's just sitting there, looking at us in the mirror. I look into the mirror my eyes meeting with his, "Go on, ride me." He starts to move up and down very slowly, I place my hands around his waist not to guide him but just to feel him. I let my hands caress up the sides of his body around to his back, even cupping his ass feeling the strap-on slide into him as he lowered himself onto it. I had my eyes closed just feeling him enjoying him and the sounds he was making. Then I feel him cup my breasts, I open my eyes and he is staring at me, I didnt even realize until then I was moaning too. He tugs at my nipples while he rides me. I look down at his throbbing member between us its oozing precum, I bend down and suck the head of his cock clean on his up stroke. It slips from my lips when he lowers himself back down on me. When he lifts himself again he deliberately holds his cock and aims it into my awaiting mouth, then lowers himself back down on the Tango. He raises up again this time I feel his hand on the back of my head, he doesnt do like before and sit back down instead he does some short thrusts into my mouth, of course the Tango is moving in his ass at the same time. Then suddenly he pounds his ass down onto my cock with a resounding slap. I look up at him wondering if he's in any pain, I see instantly he's not. His glistening cock is bouncing wildy as he bucks up and down making the Tango rub all my sensitive bits. I take some time to watch him in the mirror, then I look into his eyes, "I want you to shoot your cum all over me when you feel the urge, but for now…do what you want, I like watching you." No response from him, he just keeps riding.
I reach down and stroke his cock with my hands, he fills up my hands quite nicely, he moans bucking into my hands stroking both his ass and cock faster. I feel him stiffening more between my fingers I grip him tight, he's so slippery from the coconut oil. He leans back just a bit bracing his hands on my thighs, still grinding his hot ass on my "cock". He looks amazing I can see the Tango going into him, feel his balls brushing against my skin, his cock clamped between my fingers. I look up at his face, his eyes are closed, lips parted, he's panting and moaning. Then he lets out this guttural roar, and thick hot ropes of cum shoot from his cock. I feel his cock straining and pulsating in my hands, I wonder if he'll ever stop cumming. My jaw dropped in utter disbelief, a stream of cum lands in my mouth and drips down my chin, then he shoots again it lands on my breasts dripping down to my stomach. It seemed like every time he lowered himself and the strap-on passed over his prostate more creamy jizz pumped out. Soon his dick stopped throbbing and he was only very slowly and subtly stroking his ass on my "cock". "Keep doing that I'm going to cum." I moaned, he looked at me a bit bewildered but did as I said. Soon I was gripping his ass and lifting my hips pumping into him, then I came hard. I was out of breath and dizzy by the time I realized he was watching me. I take my finger and wipe the cum of my chin and place my finger in my mouth, "Hmm you taste good, you came in my mouth a bit, why didnt you tell me you could shoot like that?" I implored him. "I never have like that before." he said sheepishly with a little grin, he glanced at my breast and his handiwork. "Lick your cum off of me but dont swallow it just taste it in your mouth, see how good you taste." He lets the strap on slip out of his ass as he kneels down to lick my breasts and stomach, once he's done he looks up at me. I beckon him to sit back in my lap he does I whisper to him, "You kissed me before when we were on the table yes?" he nods mouth full of cum. "Lets share your cum thats in your mouth, kiss me again." he does without any hesitation. I taste his cum as it coats my tongue mixing with our saliva, I feel him suck my tongue clean then swallow his load. We kiss a bit longer then break off the kiss.
He stands and begins to put his clothes back on, I remain sitting, cross my legs and watch him. He starts for the door and looks over his shoulder, I wave, he nods, leaves the money on the table by the door before he gently closes the door behinds him.Source: https://www.aneros.com/blogs/shy-guy/