AS we hopped from the tourboat onto the dock I noticed Tony's expression liven and looked around to find what girl was the cause. Found the tight round white-fabric-encased ass. To my surprise not female. Male. One of the crew.
I'd been dating Tony for a month now and was fairly confident he was straight - so far as he knew. 18, horny all the time and just about fucking the ass off me. Fine with me as the
older woman - 29, nearly 30 already!
"I didn't realize you were interested in men."
"I'm not." He blushed and went silent and I let it go - but I hadn't forgotten. Then as we got in the car he said kinda fiercely "Can we go back to your place?"
I knew what he had in mind. Jump on top, missionary position, slam-bam 1min 45secs or 3 to 5 min if I managed to slow things down, thank-you-mam. And he had something to prove now. But I had other ideas brewing.
Back at my place he headed straight for the bathroom and while he was in there I quickly checked my bedside cabinet, opened my special case, got a few things ready and close to hand, closed the drawer, just in time for in a jif he was out with an eager expression reaching his arms around me.
"Just wait a moment" I told him.
"Oh, Jenny...."
"I'll just go get you a beer. You can take your clothes off."
His eyebrows raised and he looked relieved. Puzzled I was being so solicitous as to get him a beer. I got him two and two fresh towels and by time I was back he was down to his underpants. Nice body. Slim but not too slim, good manly chest beginning to get decently hairy. Medium length cock, nicely thick.
Opening the beer I handed it to him and he took a sip, realized he was thirsty after our little trip around the bay and in a minute had downed most of it, on an empty stomach. His arms went around me again, hands everywhere, cock already tenting his white y-fronts.
"Stop it! Wait" I told him fairly fiercely, pushed him hard back so he sat on the bed and before the surprise had worn off dropped to my knees, pulled his cock out and took the head in my mouth. I'm good at that and he pretty soon stopped complaining. Looking upward I saw from his rapt expression I had him going and pretty soon he was moaning and was pretty near shooting when I took my lips away and squeezed the root of his penis firmly to stop it....brushed his thighs and belly lightly, almost as if by accident, with my fingers then cupped his balls lightly.
Looking at his face I saw I'd brought him back from the point of no return and brought different, wider levels of arousal so I took his cock in my mouth again and more carefully this time sucked on it, swiping and swirling with my tongue, slowly, methodically, strongly. Pushing his chest I made him lie back and pulled his underpants right off in one brisk motion, then took his cock in my mouth again....As he started to buck his hips and his breath came hard I reached for my bedside cabinet with my right hand....just made it.....opened the drawer.
He was too preoccupied to notice what I was doing. It surprised him when my finger in the latex glove insinuated itself just into the opening of his anus. I'd used a special lubricant, super slippery stuff called Wet or something like and it went in smoothly. Still for a moment he almost baulked. Sucking real hard, drawing my other hand up and down his shaft I kept him going. He was close to coming and slowly and carefully I pushed the finger further into his ass then felt his hips jerk away then down onto it as he felt something new and good. It did him real quick.With a cry he shot a big load into my mouth, coming, probably harder and better and differently than ever before and I kept twirling and working that finger gently around his virgin ass keeping him in orgasm for a long time - long time for him, anyways.
It took him a few minutes to recover and I lay down beside him, head propped on my hand. I could see the thoughts and worries whirling and when he looked around and caught my eye with sheepish expression I told him kindly "Don't worry, I'm not going to tell anyone you came with my finger up your bottom."
I liked the way he blushed then, it told me all this was new to him.
"It's not right" he mumbled.
"What?"
He repeated it.
"Tony." I lowered my face and kissed his chest, my hand grazing his nipple intentionally.
"Ah!" Involuntarily he jerked. He was really, really sensitive.
"It's normal, don't you know?" I explained: "Lots of people don't realize we all have more nerve endings in the anus than in cock or pussy. It's normal to feel great, if you're touched right."
"But...."
"It's normal" I insisted, kissing him slap on the lips.
Reassured, he shut up and after a few minutes was trying to clamber on top of me to do it the manly way. This time I let him and since it was his second come he was slower and it was good, I enjoyed it and came okay too.
After we awoke from a short doze I opened the second beer, took some, handed it to him. He drank most of it.
"Do you think the sailor boy we saw with the nice ass this afternoon likes it being explored like you?" I asked provocatively, liking the way Tony blushed because now I knew that despite himself and despite whatever he thought about himself he was turned on.
"I'm not gay" he blustered, sitting up and I countered by leaning my head down and biting his nipple gently. He bucked like before and I saw his cock stiffening.
"I know you aren't" I told him matter-of factly. "I've been with enough guys of every different part of the sexual spectrum almost, and I told you it's quite normal."
Oh, I was being very reassuring to him on the surface. Meanwhile my hand took his cock and massaged it and I began sucking his right nipple, the more sensitive of the two. When he was well aroused I said wickedly "Imagine you are him right now. I saw the way he wiggles his ass and I'll bet he likes it. Just relax and imagine you're him."
The idea began to work, along with the beer and carefully I stroked around the rim of his anus, paused to lubricate the glove again, then inserted it. Now it wasn't Tony, it was this other guy with the sexy butt who liked what I was doing and it he got into it more easily. He lay back, panting and moaning. After a minute I felt him pushing down on my finger, let him grind a bit to realize how much he needed and liked it then withdrew it almost entirely making him follow it, then withdrew it altogether.
"Jenny," he moaned, "please." He was hooked.
"Roll over onto your front."
He didn't want to. Time to dominate. "Do it" I told him. "You know you want it like that. Do it." I pushed him over onto his belly and he went. "Open your legs!" They opened abruptly, involuntarily, closed again. I grabbed him by the ankles and opened them. "Open your legs, slut. You know you've got to have it."
I let him lie there a moment with legs open, waiting, anticipating, wanting. He looked over his shoulder, a confused submissive look. I lay my body full length over his and put my arms around his chest, found his nipples and swiped and worked them as I ground my pussy against his butt till I felt myself getting hot.
"How's that feel?" As if I needed ask. Reaching around his front I felt his cock. Rock hard. His butt was pushing back against me, pushing up, searching. "What do you want?" I asked him and when he didn't reply asked again as he pushed up against my mound.
"I don't know" he moaned.
"I know what you, you want to be fucked like this."
"No!" But still he was pushing back, hips raising from the bed and moving in little circles as my pussy pressed his cheeks apart and found his anus.
Without moving from his back I reached out to the drawer and took a slim dildo whose cute curves performed wonders. Quickly lubricated it. And while one hand reached around pinching his nipples, I carefully insinuated it inside him.
As I suspected, he took to it. This dildo was an expensive job of work, near $100 and worth it. He was rubbing his cock into the bed while trying at the same time to arch his hips up to meet me, rotating his butt with actions that came natural to him. He didn't know what all he was doing now. This was new territory, new sensations and desires for him, I'd seen it before and gradually I teased the dildo up out of him making him follow it as I twirled and plunged it, but always withdrew it further till it was right out.
As he looked around over his shoulder at me with panicky hunger I told him "Let's get your butt raised up high like a good girl" and took two pillows and a towel, pushed them under his belly and got his pussy up and open for me. I parted his cheeks, looked at the cute pink cherry waiting to be taken. "Legs open, girl." I made my voice deep like a man. "I'm gonna fuck you. What shall we call you? Tina. How about Tina? Open your legs Tina."
A whimper - the legs opened and I slapped the gorgeous taut round white curves. Lightly at first, then harder. "Tell me what you want" I demanded. "What do you want, Tina?"
My boy-girl yelped and I kept slapping and pinching while he would push his cock into the pillow and then not finding what he now needed, kind of raise his butt, searching for what part of him wanted in there and the other part of him knew nothing about. I slapped, pinched, rubbed and stroked and finally he begged for it.
"I want that in me."
"What? Say what it is you want."
He really didn't want to put it into words and make it real.
"Jenny, please, give it me...."
I had mercy and insinuated that viciously wonderful dildo into him, twirling and dipping. "What is it you really want?" I lay my full weight onto my prey and with my hand on the back of his head pushed his face down into the bed, thrusting and grinding my clit onto the dildo's rounded end. The dildo pushed deep into him and I began fucking him with steady strokes like a man. Pounding, hearing him groan and pant. I was beginning to come and I pushed down hard and came, feeling him jerk and hearing him cry as he came too. I scarcely let his body finish jerking before I rolled him off the pillow. He'd shot a good load into the towel.
"How did that feel?"
"Good." He had a glazed, dazed expression.
"You liked coming like a woman while a man fucked you, didn't you Tina?"
He bit his lip and didn't say anything. Time for some more motherly reassurance. I gave him a hug, pressing my tits against his chest so he'd feel like a man again. "Don't worry about it." I laughed, nicely. "Kinky is fun, kinky is good. It's even normal only not everyone knows it. You're a bigger person when you do."
He lay there with I can imagine what a whirl of conflicting thoughts going through his mind. I'd had a really deep orgasm, deeper than others with him and we both fell asleep.
I woke up a couple of hours later and saw him still asleep. He looked so cute. He'd rolled back partly on the pillows, butt raised invitingly high. I looked into his face. Mouth open slightly. Must be having a dream the way his mouth pursed. What could he be dreaming, Tony-Tina? A natural submissive, unconscious of it till today. Just as I was a natural dominant.
My little sleep had made me really horny and this was always my best time of day for sex anyway so I slid gently off the bed, not to awaken sleeping beauty, and padded softly around the other side to reach my bedside table and took out my pride and joy, a realistic double-sided dong I rarely got the pleasure of using. Black purple color with veins and super mushroom heads, one end twice the thickness and half as long again as the other. I strapped it on, went round the bed again, slid on behind him and very gently began to stroke his butt round and round. Those cheeks so smooth and round and taut great under my hand I was aroused in a moment, stiff and hard. Couldn't resist running my finger down the crack. My groin was so hot and throbbing I just had to move in and rub my prick into the crack a little, kneeding the cheeks with both hands, but very very gently and sensuously. Didn't want him to waken too soon.
He stirred, groaned, his cheeks beginning to press back against my hands. Still he wasn't fully awake as I slid off the bed and went round the other side to look at his face. Mouth open. I just had to... Knealt on the bed and touched the tip of the prick on his lips, inserted it slightly. Still asleep he took it in, sucking like a baby, and I began to slide back and forth gently. Suddenly his eyes opened wide and he tried to move back but I put my hand on the back of his head firmly and held it in.
"Suck" I told him gently but firmly. "You like it. Suck it."
He did. Dazed and uncertain, lightly at first but soon getting into it, a hunger rising that must have layen dormant, maybe been supressed but in the back of his mind. As I moved back to an easier position he raised onto his hands and knees. It just came naturally to him.
"That's right, that's a good girl, Tina" I said taking his head in both hands and sliding it in and out. "Take it in. Breath through your nose. Relax your throat and take it in. Practise so you can take the big ones."
I was coming off and thrusting hard. He gagged but kept trying and I was fucking his mouth and coming, shooting a load. Suddenly I pulled out leaving him gasping, reached out and slapped his ass hard a few times making him yelp.
"What do you say?" I demanded.
"What?" he gasped, not understanding.
"Say thank you, Sir." I kept slapping his cheeks hard, watching them redden delightfully. Though it hurt he was aroused and it was a pleasant pain. I ducked my head and looked. His penis had thickened but hung curved, not up against his belly hard and erect like a man. This was Tina, my woman. Stopping slapping I rubbed cold cream on the hot stinging cheeks, rubbing round and round, caressing, squeezing while on all fours he wriggled and gasped. It was getting so he couldn't stand it any more.
"Oh" he kept gasping. "Oh, Jenny, don't. Oh, please Jenny..."
I slapped him abruptly, hard, a long swinging blow. "Call me Sir. Now. Say Sorry, Sir!"
"I'm sorry Sir." He moaned submissively, loving the strange new emotions and sensations. I stroked his cheeks some more till he began begging again: "Oh, Sir, please, oh, do it."
I wasn't going to make it that easy for him. "What is it you want?"
He still didn't want to articulate it. Until he did he wasn't getting what he needed.
"Say what it is you want?"
Finally he gave in.
"Fuck me, please fuck me, Sir."
"You want prick, don't you? Say it. Say Put your prick in me, Sir."
"Oh....Put your prick in me Sir. Please please put your prick in and fuck me."
Lubricating the veined prick, lubricating his hole with my gloved finger, I pushed it gently in. Paused and let it get used to something bigger than ever entered before. But it was sliding in easily. Tina-Tony was hot and open. In and out, side to side, twirling, finding spots never imagined. Then I was getting to hot to hold it. Fuck being gentle. I pounded in, pushing so hard Tina collapsed forward and I went with her grasping her lovely hips in each hand and thrusting deep. As I came I saw the body beneath me writhing and straighten in orgasm. Tina's first real orgasm, starting in the butt and spreading through the entire body in a warm tingling rush. Though I'd shot my load it felt good as I kept myself pushed hard and tight against the sweet round cheeks, prick buried deep as Tina went on coming and coming in a complete bodyrush.
It was probably five minutes before I slid out and went to wash.
When I came back Tina-Tony was lying curled up, looking vulnerable. Turned to look at me as I slid under the covers.
"That was great." Still slightly shame-faced yet coming to accept it.
"You accept that you like it?"
Tina-Tony nodded.
"I wonder," hesitantly, "what a real one would feel like. I suppose it would hurt too much?"
"Men are such selfish rough brutes" I laughed. "It might hurt a bit, yes. But, really, it needn't hurt in a bad way. You think you'd like to try a man inside you?"
Blushed madly but nodding.
"That can be arranged. I have friends. We'll soon have you on all fours with a real man in either end and two hard bodies standing pricks in hand waiting their turn." He groaned, turned on at the thought and I saw his prick stiffening. I was turning this one into an insatiable bitch. "But first, lots of practise with me. Say Yes Sir." I held either side of his mouth in my hand, forcing his lips into a girlie pout.
"Yes, Sir."
I kissed the lips.
"Now, turn over, raise your butt and open your legs..."
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