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Story 39 - First Time In (mf,teens,anal) by Titmouse
"No, Larry, we can't!" Sharon said, pushing me off her. "I'm just can't do it."
"Jesus Christ!" I said. "This is driving me crazy. Baby, I love you, but I can't keep doing this. My balls are going to explode!"
We were on the sofa in the rec room downstairs at my house, after school. My folks were at work and wouldn't be home for another couple of hours. Sharon put her head on my shoulder, snuggling up to me again.
"I'm sorry, honey," she said. "I know, I know, but..."
"Yeah," I said, "you don't want to get pregnant. You don't want to start having sex, because we'll wind up doing it without protection. You don't want to take a chance. Well, what about me?"
Sharon looked up at me with her brown eyes. She hugged me, pressing her breast against my chest. Her legs were wrapped around one of mine, her crotch against my thigh. I knew she was as excited as I was-- almost as much, anyway.
"I don't know, baby," she said. "I want to do it, you know that, I really do." She moved her hand down to my crotch and stroked my penis through my pants. It swelled against her hand. "Maybe we could do something else?"
"Like what?" I asked.
"I dunno. Maybe..." She hesitated, embarrassed.
"What?"
"What about a..." she moved her mouth up to my ear and whispered softly "...a blowjob?"
I was surprised. I wasn't quite sure what a blowjob was, but I knew it had something to do with her putting her mouth on my prick. It sounded great to me, but I didn't think Sharon was the type to do that sort of thing.
"Are you sure?" I asked.
"I don't know," she admitted, "but I feel like I gotta do something for you, honey. Would you like me to do that?"
"Oh, yeah," I said. "If you wanna do that, yeah, I'd like you to do that."
Sharon moved her hands to my waist and unfastened my belt buckle. Then she began unbuttoning my jeans. She wasn't very good at it and fumbled with the buttons for a long time. I didn't mind. The feel of her hands on my prick was exciting, and it swelled as she worked at the buttons, which didn't make it any easier for her.
"Oooh," Sharon said, "you're getting hard."
"Hell yes, I'm getting hard," I said. "That feels good."
"You like it when I touch you?" she asked.
"You know I do," I said. "A lot."
Sharon finished the last button. Putting her hand on my stomach, she slid her hand down under my undershorts and touched my prick, which was pointing due north. She ran her palm over it and down to my balls, which she cupped lightly.
It wasn't the first time she had touched my naked cock, but it was still new enough to send chills through my body. Sharon grasped my shaft with her hand and tugged on it. She jacked it up and down for a while, and I swelled against her warm, slightly sweaty palm.
"Here," Sharon said, sliding off the couch onto the floor. "Turn around and sit up." I did what she said. She knelt between my knees and began to peel my jeans and undershorts over my butt. "Lift up," she said, and pulled them down to mid-thigh when I did.
This was new. Our mutual groping had been mostly of the eyes-closed, semi-dark variety until this. Although I'd had my finger in her pie a number of times, I'd never actually seen it, nor had she seen me. At least, never like this, straight on, dead center.
"Wow," Sharon said. "That's awesome! Does it always get this big?"
"It does when you touch it," I told her. "It feels like it's getting bigger."
She held it in both hands, pumping up and down on it. It was strange-- backwards from the way I did it and slightly uncomfortable from her unpracticed touch, but thrilling nonetheless. Her hands were damp, but not wet enough to slide over the skin.
"I'm not sure what I'm supposed to do," she said. "Kiss it, I guess." Sharon leaned forward, bringing her mouth close to my prick. I could feel her breath on me. I could see her lips reach out, pucker and kiss the head of my cock. It swelled strongly, responding to her touch.
Sharon extended her tongue and licked at the head experimentally. A moan escaped me, which she took as an indication that she was doing okay. She bent my prick downward, pointing it right at her mouth, and opened her lips. She slipped them around the head and sucked on it gently. I swelled in her mouth and she seemed to like that. She sucked on it some more, turning her head back and forth, pushing her tongue in and out to tease the sensitive, heart-shaped bottom.
"Do you like that?" she asked.
"Jesus Christ, baby" I said, "YES. It's great. Can you get more in your mouth?"
In answer, Sharon pushed her head forward, sliding her lips down over my hot cock. She got about half of it in her mouth, and sucked on that for a while. That felt so good that I couldn't help moving my hips back and forth, gently fucking my prick into her wet, grasping mouth. She got the idea, and began lifting her head and pushing it down again over my cock.
"Ohhh, that really feels good, baby," I told her. "Keep doing that." It was great. It felt better than my hand when I jacked off. Her warm mouth, clinging lips and mobile tongue all worked on me. As her saliva wet my prick, her hand began to slide up and down on it, so that she was jacking me off into her mouth. It was the most wonderful thing I had ever felt.
Sharon pulled her head off my prick, catching her breath, although she kept her hand on me, moving slowly up and down.
"Will this make you cum?" she asked.
"I think so," I told her. "It sure feels like it. It feels real good, baby."
Sharon looked to one side. "I...I don't want you to cum in my mouth," she said. "I'm... It's just that..."
"Oh," I said. "Well, that's great. Now you've got me in even worse shape than I was before, and you tell me that!"
Sharon bent her head back to my cock, pushing it into her mouth again, sucking on it and working it with her tongue. Then she pulled back again.
"Don't be mad at me, honey," she said. "I'm sorry. I want you to cum, I just can't handle the idea of it going in my mouth. I know that's what you're supposed to do, but I'm just not ready. But maybe you can warn me and I can just jack you off at the end."
I think I would have said anything to get her to put her mouth back on my prick. It strained toward her, reaching out toward her mouth. Sharon leaned down and licked it, kissed the head, took me in her mouth again, sucked on it.
She did that on and off for a while, stopping every once in a while to let me cool down a little, then moving back to my cock again. Her confidence increased with a little experience. Where she had been tentative at first, now Sharon pushed her mouth down on my prick strongly, sucked on me vigorously, moved her hand up and down on me quickly. When it was slick with her juice, she let her hand slide up and down on it like an extension of her mouth, keeping her hand at her lips, jacking me off with her hand while her mouth captured me as my prick emerged from her hand, licked me, tongued me, let me slip out again as her hand moved upward, then caught me in her mouth again as her hand slid downward over the shaft.
After a while, I was getting near the edge, my breath coming in little gasps, the feel of her soft hands and warm mouth stirring me, teasing me, coaxing my cum out of me. Sensing it, Sharon moved her mouth off of me, although her hand kept moving up and down, jacking me off, trying to make me cum. But the cool air was a shock after her warm mouth, and she was too inexpert with her hands. Once again, my passion faded slightly.
"It's not working, is it?" Sharon asked.
"It feels great, babe" I told her, "but when you take your mouth away, I start to lose it. Can't you just keep going? It can't be that bad if other girls do it."
She shook her head.
"I'm sorry, honey. I just can't! Not tonight." She paused a moment. "But, maybe.."
"What?"
"Well, there's another way, maybe..."
I couldn't imagine what Sharon was talking about it. We were young and very inexperienced. I knew a lot of names for things, but they were only names. I thought madly but couldn't come up with anything. Except...a friend had once told me what his older brother had done to him. But...
"I'm embarrassed" Sharon said, avoiding my eyes.
"Tell me," I said. "Anything! It's okay, baby. Just tell me. I don't know what you mean."
"Well," she said, "have you ever heard of 'cornholing?'"
That was just what my friend had called it. His brother had stuck his cock up his butt. From what he said, I couldn't tell whether or not he had liked it. But his brother had, apparently.
"I think so, maybe" I said, but I didn't want to say it. What if I was wrong? The thought of it was both strange and sexy. On one hand, surely it was dirty, unsanitary, embarrassing. On the other hand, the thought of pushing my prick into her, anywhere, was thrilling. I tried to picture it, but couldn't. But the thought sent chills through me.
"It's like making love," Sharon said, "but you don't put it in my...pussy. You put it in my...the backdoor."
"In there?" I asked. "Can you do that? Doesn't it hurt?"
"I don't know," Sharon said. "I've never done it. But you know Janice Woodson? She says she did it with her boyfriend, Jimmy. She says it hurt at first, but then it was okay, and then more than okay. She says it's better if you have a lot of lubrication. Then it doesn't hurt so much at first. She says that if you go slow, if your guy is considerate, that you can do it with no problem that way."
"But..but...why?" I stuttered.
"Because you can't get pregnant that way, silly. She says she and Jimmy just had to do something after a while, and that it was either this or make love, and she didn't want to do that either." Sharon noticed that my erection was fading. She bent over and worked on me with her mouth again. Soon, I was fully hard again, not just firm but bending slightly backward in a banana shape. God, I wanted to cum. I wanted to put it in her and fuck her so bad. Anyplace was okay with me. If I couldn't screw her pussy, then I'd be only too happy to screw her ass.
"So," Sharon asked, "what do you think?"
"I guess it'd be okay," I said, "if you want to do it, baby."
"I want to do something," she said. "I want you to cum, honey. I want to be your woman. I'm not too sure about it, but I don't want to do it the regular way and I don't want you to cum in my mouth, so..."
I was ready for anything. "Okay," I said. "Let's do it." Immediately, I realized that I hadn't the slightest idea of how to proceed. "But...how?"
"Janice says they do it just like regular, except that he puts it in the lower hole," Sharon said. "That way, it's just like they were making love, just safer."
She stood up and began unfastening her blouse. When she had released the last button, she reached up between her breasts and found the hooks for her front- closing bra. She opened it and let the side fall loose.
I had seen her tits before, but not like this. Sharon was open, brazen. This was no furtive groping. She wanted me to look at her. I was happy to oblige.
"You like my tits?" she asked, knowing the answer.
"They're gorgeous," I told her. "You know I love to look at them. Can I..." I reached out toward her chest.
"Just a minute," Sharon said. She dropped her hands to her waist, popped the button on her shorts, and slid down the zipper. She turned around, sitting down on the sofa and sliding the shorts over her bottom at the same time. Her bare butt brushed my thigh as she sat down and leaned back slightly, pulling her shorts off her legs.
"There," she said. "Now, let me lie down."
I couldn't believe how open she was. I shifted forward. Sharon fell back, pulling her knees high to clear me, and stretched out behind me on the couch.
"Come on," she said. "Hug me."
I stretched out beside her on the sofa. My thigh slipped between her knees, and Sharon opened her legs to let me slide all the way up. I felt her moist pussy and her wiry pussyhair against the top of my leg. She hunched her cunt against my thigh.
I put one arm around her and slid my other hand up to cup a breast. Sharon was naked except for her socks and the open blouse and bra. I could see and touch her everywhere. My cock was hard as a rock, caught between our bodies, prodding her stomach. She reached down and gripped it with her hand.
We kissed and rubbed against each other. I hadn't realized that she was so hot. I guess sucking my cock had got to her, too. When I moved my hand down to her pussy, it was the wettest I had ever felt, really juicy. I pushed a finger up into her, stroked my finger in and out. I slipped it up to the top where she had showed me her clit was and fingered that little nub. Sharon seemed to like that a lot. She moaned deep in her throat and moved her hips back and forth, fucking herself on my thigh and my finger.
"Jesus, honey," she said, "I'm glad we're finally gonna do something. I get hot, too, you know. I've wanted to do it with you, you know that. Ever since Janice told me, I've been thinking about this. Now I really want you to go ahead and do it."
"How?" I asked, still having no idea how to proceed.
"Well," Sharon said, "first you have to grease me up, and then do you, too." She reached down beside the couch and got her purse. "I've got some cold cream in here that should be okay." She brought out a jar and opened it. A sweet fragrance filled the air. Sharon spread her legs wide, inviting me.
"Go ahead," she said. "Get some on your fingers and grease me up."
I dug my fingers into the jar and scooped up a gob of cold cream. Tentatively, I reached my hand down between her legs. I could feel her pussy, warm and damp. I moved my fingers down further, into the crack of her ass, and smeared the cold cream there. I felt around with my fingers. At first, I couldn't find it. Her butthole was closer to her cunt than I had realized.
When I finally found the right place and touched the tightly clamped muscle, Sharon put her hand on my arm.
"Go slow," she said. "Janice says to go slow, and get it good and greasy. And she says to use your finger to loosen me up and relax my butt muscle."
I went back to the cold cream for more. This time, I put my finger right on the spot. Gently, gingerly, I began to push at the puckered opening, rolling my finger around teasingly, pushing slightly and then relaxing the pressure, spreading the cold cream all over the entrance. Finally, I pushed a little harder and my finger slipped into her asshole. Sharon sucked in her breath and her hand squeezed my arm, but it didn't seem to really hurt, just startle her.
My finger was only about as far as the first joint into her butt. I worked it around like she had said, rotating my wrist and gradually pushing against the tight muscle of her ass. It was very tight at first, but as Sharon relaxed it got a little easier. I pushed my finger in a little more, worked it around some, and then pushed still deeper.
"How does it feel?" I asked her. Sharon closed her eyes and rolled her hips a little.
"It's good," she said. "I didn't think it would be, but it feels good. Not like my pussy, though. But it's real sexy in a strange way. I like it."
Encouraged, I pushed my finger deeper into her butt. It went all the way in, my hand spreading her cheeks to get it in deep. Sharon gave a little moan and wriggled her butt, moving my finger around inside her. I began pushing my finger in and out, and she hunched on and off my finger, fucking it in and out of her asshole.
"Oh, honey, I'm so hot for it," Sharon said. "Come on, put some grease on you and let's do it."
I did what she told me, scooping up more cold cream and (a little embarrassed to be touching myself in front of her) spread it onto my cock. Anticipation was surging through me. I rolled on top of her, keeping my pelvis pulled back so the grease wouldn't get on her stomach. Sharon spread her legs to welcome me.
After a few attempts, it was clear that my prick wasn't going to find its own way. Shifting my weight onto one hand, I reached down between us and tried to guide it in.
"No," said Sharon, "that's the wrong hole! Lower!"
I pulled back then tried again. It seemed right to me, but Sharon pulled away again. My cock seemed to be determined to get into her pussy.
"Here," Sharon said, putting her hands behind her knees and lifting them up and out. "Does that help?"
I could see a little better. This time I got my cock pointed at the right place. I pushed forward and saw it slip down and under her. I tried again, and this time it slipped up and almost dipped into her pussy. Her asshole was rejecting my cock. It didn't want to let me in.
"Damn," Sharon said. "This is driving me crazy. Wait a minute." Pushing her hands against me to hold me up, Sharon began to slide out from under me. "Come on," she said. "Get behind me."
She slipped off the sofa and, turning her face toward it, laid her chest on the cushions. Her butt stuck out invitingly.
"Put it in from behind," Sharon said. "I think it'll be easier this way. Hurry. I'm dying for it."
Kneeling between her legs, I had a clear view of the target. Her rosy, puckered asshole beckoned me. Below it was her glistening pussy, bright blood pink and wet. Holding my prick in one hand, I moved forward until the head touched the tight circle of her hole. I pushed forward and nothing happened. I pressed a little harder and saw the tightly clenched opening spread a little.
Sharon grunted but didn't try to move away. I pushed harder and watched the head of my prick move into her asshole. The sight and feel of it thrilled me incredibly. I had never seen and never experienced anything like it. The broad part of the head pushed into her butt.
There seemed to be a band of muscle about half an inch wide guarding the entrance. I felt my cock clear it with an inaudible pop. Sharon winced and whimpered, and reached back with one hand to press against my thigh.
"Wait," she said. "Oh, God, Larry, wait a second. I've got to get used to it. It's so big."
I was happy to wait, for the moment. From my position behind Sharon, I had a clear view of what was going on, and it was incredibly erotic. My hands were spreading her asscheeks, holding them open so I could get in. The head of my prick was buried in her asshole. I could feel her butt muscle clutching at me, squeezing my dick within her ass. She groaned, and clenched her fists.
"Does it hurt?" I asked.
"A little," Sharon said. "But mostly it just feels big. About twice as big as it looks. I can't believe you can get it in there."
"It looks okay," I said, "like you're swallowing my dick with your butt."
"Let me have a little more," Sharon said. "Push it in slow. I'll tell you when to stop."
I pressed forward slowly. It was fascinating watching my meat push deeper and deeper into her asshole. Her butt muscle clung to my cock tightly, squeezing it steadily. About half way in, Sharon stopped me again.
"Jeez," she said. "It feels like I gotta shit, but good! If feels like I'm completely full down there, like there's no way anything more could get in. I've never felt anything like this."
Neither had I. I rocked back and forth, working my prick in her asshole without going any deeper. I moved back until just the head was still in her, then forward, sinking my cock into her butt again.
"Are you ready for more?" I asked.
"Yeh," she said. "Go slow, though."
I did. Moving very slowly, I gradually pressed into her asshole, going deeper and deeper. Sharon didn't stop me again. She moaned once as I fed it to her, then again as I went deeper still. But she held her butt firm, not trying to avoid me, not pushing back exactly but holding still and presenting a stable target. I saw my cock disappear inside her butt, saw my pubic mound press into the space between her asscheeks, pushing them aside as I worked it all the way in.
Somehow, I knew not to start fucking her right away. Instead, I held my prick deep inside her, pressing forward, pushing it as far as it could reach up into her asshole. Sharon seemed tentative at first, barely able to stand it. Then she began to relax and accept the cock that was filling her back passage. Finally, she begin to push back against me, as if she wanted even more, but there was no more to give her.
Instead, I pulled back, drawing my cock out again until only the head was still captured inside. Then, a little faster this time, I steadily pushed it forward all the way into the depths of her asshole again. Sharon seemed to like that. She moaned and waggled her butt. She rolled her hips, working my prick inside her.
"Is that better?" I asked.
"A lot better," she said. "You can fuck me now. Go ahead. Sink it in me, baby. Feed it to me. Oh, I like it! It feels so good in me, honey."
I started pushing it to her with a little more authority, humping my hips forward and shoving my cock into her back channel all the way to the bottom, then drawing back quickly as far as I could without falling out of her asshole. When I slammed forward again, my hips smacked into the cheeks of her ass with an audible slap.
"Do you like it, baby?" Sharon asked. "Does it feel good to fuck me? Is this what you wanted?"
"God, yes, it feels good," I told her. "I can feel your ass squeezing my dick. Squeeze it for me, baby. Fuck me, now. I'm fucking you. I've got my prick buried all the way in your ass. It feels wonderful."
"I like it to," she said. "I thought I would be doing this just for you, but it's good for me, too. Oh, fuck me, honey! Push it into my ass. Fuck my ass!"
Sharon reached down between her legs and began to massage her clit. She was panting now, and moaning each time I fucked into her ass. She worked her hips around, rolling her pelvis around my cock. She squeezed at it with her ass muscle, dragging on it each time I drew back, then relenting as I slammed my hips forward to bury my cock deep in her butt again.
I was fucking her hard, now, whipping in and out of her asshole as fast and as hard as I could, slapping up against her asscheeks and jerking back only to slam forward again. Sharon was shoving back to meet my cock as hard as I was shoving forward. Her head was back, her teeth bared in a grimace of passion.
"Oh, honey," she said, "I'm gonna cum. I can't believe it! It feels so good back there. Oh, fuck me, baby. Give me your cock. Shove it up my ass, honey. Fuck my ass!"
With a whimper, Sharon began to cum. It quickly built up into the biggest release I'd ever seen her have. She cried out, time after time, never pausing in her movements. She shoved her butt back at me as if she couldn't get my cock deep enough into her. Each time I pulled back, she jerked her hips around, shaking my prick around inside her.
And then I was cumming, too, spurting it out in machine-gun bursts of long held back jism. I grabbed her hips and slammed her back onto my cock time and again while shoving my cock into her asshole as hard and as deep as I could.
"That's it, baby" Sharon cried. "Cum in me, honey. Shoot your cum in my ass. I want it. Give it to me. Fuck me. Fuck!"
Finally, I could do no more. I collapsed over her back, completely wrung out. Both of us were panting, exhausted after our strenuous exercise.
END
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