Brian's physically fit, smart, and sexy 16 year old co-worker on the night shift asks him to help her practice kissing. He gives in to her desires and when it turns out she wants so much more, he graciously takes her oral, vaginal, and anal virginity.
You can find more of my stories at my website: http://brians-kinky-adventures.com
This is broken up into 3 chapters, all of which are right here.
Chapter 1 Brian gives kissing lessons
Several years ago I had a job for a summer where I fed paper into various different kinds of printers at night. I worked with one other person. Her name was Sanya, she was 16, and very charming in her own special way. Normally because of her age she wouldn't have been able to work there, but the owner of the company was friends with her family. She had long brown hair. She was training to be a fireman. That's right, this young lady was going to be a fireman as soon as she became old enough. I wouldn't mind being the guy to show her how to hold a hose while it was ejaculating at high pressure. She had a slender but very healthy, toned body. She always wore tight jeans that did a great job of showing off the nicest looking ass I've ever seen. I think if I was rescued by her, I would probably forget that my house was burning down.
She had an innocent, younger woman type of personality, but it was contrasted by subtle things like those tight jeans that hinted otherwise. Hanging out with the firemen very likely enlightened her to some things. Sometimes I would walk in the room and she would be leaning over the cabinet reading a newspaper in a position that really made her ass look nice. I have a hunch that she was doing that on purpose. Finally one time I said, "Wow, that looks great!"
She looked back at me through her glasses with her underage librarian smile, "What does?" I pretended to be looking just in front of her and vaguely waved my hand at some boxes. "You know, all those boxes that we've already done."
The first time she wore glasses I said to her, "I didn't know you wore glasses Sanya."
"I only wear them sometimes," she replied.
"Well I think you should wear them all the time,” I said. She had a hot, underage librarian look with the glasses. "I really only need them at school," she answered.
"Yeah but you look really good in them."
"Really?" she asked, with a flattered smile.
"Yes, some women look really good with the right pair of glasses, it's that sexy librarian look,” I told her.
She started wearing her glasses often after that. I loved it. Occasionally I reminded her that she looked great in them to make sure she continued wearing them.
The machines tended to run themselves. All there really was to the job was every 10 or 15 minutes loading a new box of paper into a machine. So it got boring. And we got along very well with each other, which, because we had a significant age difference, was both a little awkward but also a little exciting. So it was probably inevitable that the conversation sometimes turned to stuff that wasn't "work safe." Of course no one else was there, so it didn't matter. But it started to feel like a game of dare about what things we talked about. We would sit next to each other and talk and flirt.
One night she asked me about kissing. "Brian, have you ever kissed a girl?"
"Of course," I answered.
"Are you good at it?" She asked.
"I'm very good at it." I told her.
She continued, "I've only done it a little bit. I don't think I know how to do it right. How does a man like to be kissed?"
I thought about it a bit, and finally said, "I'm not sure it's a good idea Sanya, you'll just give a guy the cooties.
"I'm serious Brian."
"Well have you had yourself tested?" I asked.
Finally I said, "Well, I guess there's not a right or wrong way to kiss per se... I'd say just be aware of the mood and do what feels right at the time."
Her face seemed to indicate continued frustration with my answer. "Well, like how much tongue do you think I should use? ...I started dating this guy, and-"
I couldn't keep a straight face, and chuckled.
"What's so funny?" she asked, with a curious smile. Then she continued, apparently slightly offended, "Don't act surprised Brian. You're totally jealous. I was hoping you could give me a few pointers about kissing."
My cock seemed to be growing slightly. "No no, it's not that I'm surprised. Don't worry about it." I tried to get into the specifics a bit with her. "I just like to warm up to it, get cozy with my partner. Hugging and stuff. And then you give them a few pecks on the lips, and then you start sticking your tongue in there, and then before you know it you're making out like, well like highschoolers."
She just looked at me, apparently in thought about what I had just said. Talking about this with her was making my cock gradually grow, and now it was at about 85%.
"I want to practice,"She said.
“That's probably a good idea," I nodded to her. "
“I mean I want to practice with you.," she said.
I thought something like this might happen, but I was still not prepared for it.
"Uh, Sanya..." I put on a fake look of repulsion on my face.. She stood in front of me and leaned over, putting her hands on my chest and slowly moved them up to my neck.
"I just want you to help me practice kissing. Come on it'll be fun, it's not like anyone will know."
The only part of me that was keeping up with Sanya was my dick. "I'm sure you do Sanya. You'd love me to be your guinea pig. Kiss me, molest me, whatever, use me for your experiments and then just throw whatever remains in the trash when you're finished and want to move on. I know how you high school girls think."
I stared into her eyes with a very serious, stern look, and I did my best to make the subtle change into a "you naughty little girl stole a cookie out of the cookie jar, didn't you" look.
She appeared to think for a moment, I guess I slowed her down briefly. Then she nodded with a smile and said quietly, "Yes Brian, that's exactly right." She leaned in closer with a pucker face and planted her lips on top of mine. She gave me several silly pucker face kisses on my mouth, as she pushed herself between my legs, getting closer to me. I grabbed her head without warning and planted my mouth firmly against hers, finally giving in to something I had been itching to do since the first night with her. She opened her mouth tentatively against mine, and I stuck my tongue in licking whatever I could reach. Immediately she grabbed my head, opened her mouth and did the same thing back. It was a passionate tongue wrestling match. My dick was rock hard. This went on for a few minutes, until we stopped. I think she stopped first, so I guess I was the winner of that tongue wrestling match.
We smiled at each other and giggled while we caught our breaths. We moved our hands away from each others' shoulders and down to each others' hands.
Finally she asked, still laughing, "Um, is that how you're supposed to do it?"
I put on a contemplative look, like I was judging fine wine. "Yeah, I thought it was pretty good, if what you're looking for is something aggressive" I laughed and then continued, "Of course there are times when you'll probably want to kiss more tenderly."
I got up to load some paper into a printer that had run out. Then I walked up to her and we shyly put our arms around each other, then we kissed more like lovers, soft and leisurely. I felt her nicely developing chest heaving a bit as it pressed against mine. We spent almost all the rest of our time that night practicing kissing. Our hands slowly wandered all over each other, for the most part just innocent places. After some time I held her close and told her that she was a very nice kisser.
Chapter 2 Does Brian take Viagra?
The next night as soon as we felt certain that no one else was in the building except maybe the janitor, she plopped her sexy ass in my lap and stayed there most of the night. She spent the night cuddling up to me and kissing me. That's mostly how things went the next few nights.
Then one night, at one point she hugged me from behind, sort of by surprise. She stuck her hand over my pants and squeezed my boner between her fingers. "Brian you always have a boner," she declared.
"I don't always have a boner Sanya, just when I'm working with you," I replied.
"Are you taking Viagra?" she asked.
"No," I answered.
"But you always have a boner the entire night!"
"Yes that's true,” I nodded to her in response.
I sat down, and then she straddled my lap and pressed herself against the topic of the conversation. Putting her arms on my shoulder, she murmured seductively, "I'm giving you a boner?"
"You always give me a boner Sanya, sometimes I had a boner just from working with you before we started kissing every night."
She kissed me deep, and tried to press herself against me even more. "Does that mean you want to have sex with me?" she asked.
It was getting a little crowded in my pants. I thought about it a little nervously and finally said, "I don't think I'd mind that."
"You know I've never been with a man," she said.
"What about with a woman?" I asked.
"Not with a woman either. There was one time that I dry humped my friend Megan in our pajamas, and that's it, but we were just playing around. I like you Brian."
She pulled herself up slightly and kissed me deep. One of her hands was firmly around my neck, her other hand was doing something in the tight space between my boner and her pussy. Then I felt her opening my pants.
I didn't bother wearing underwear to this job, so without any trouble her little hand reached in, pulled out my boner, and before I even realized what happened I felt a hot silky vice sliding down my cock, as she lowered herself back down in my lap, with my cock hidden inside her tight virgin pussy.
"Oh God Brian," she looked at me with a look that was something like agonizing and deep pleasure, her hands almost trembling as she lightly clutched my shoulders.
She stared hard at me through her sexy glasses. I watched her breathing deep. She moved up, and then back down, on my boner, then again, and got into a slow rhythm as she tried out her first cock. I grabbed her and gave her a deep kiss. Then I gazed at her wide pretty eyes and said, "that feels really good Sanya."
She suddenly gave me a little kiss and sweet smile, and said "I don't need to be a virgin any more. I found something I like." She put her arms around my neck and rested her head against mine, and continued riding my cock. In only a few strokes it started to feel like cum was going to start spurting out my ears.
"Do you want to get naked?" I eventually asked her. She released my boner from her pussy and stood up in front of me. She pulled off her shirt as I stood up as well. We took off all our clothes but she still had her bra on. I put my hands on her back and released her bra as I kissed her. Her tits were very pretty and suckable. I pulled back just enough to get my hands in front and started gently squeezing her tits.
Her virgin minus 15 minutes, and very fit body, looked really good. "You're beautiful Sanya," I said to her.
"Thanks Brian, you're very handsome and sexy," she replied smiling politely at me.
I continued gently squeezing her tits and pinching her nipples, and kissed her a couple times.
"Why don't you lean against those boxes," I suggested.
She took a couple steps to the boxes.
"Stick that gorgeous little ass out at me," I told her.
She leaned forward against the boxes, and stuck her hot little ass out with her legs spread. I'm not sure I'll ever see a more gorgeous site. I put a condom on as I walked up to her, and nestled the head of my cock between her swollen pussy lips.
I thrust it in gently, then slowly eased most of the way out. I put both hands over her tits and squeezed her tits and played with her young nipples. I continued thrusting in and easing back out. Every few seconds she said "Ooooooh." She sounded very cute and erotic. I could hear her breathing. I could feel her pussy getting wetter with every thrust.
We alternated between several different positions throughout the whole night. We re-stacked some of the boxes so they were just the right height, and she laid down on them and I stood and stroked her swollen pussy. The only thing that looked better than Sanya with clothes on was Sanya all bare, with her legs spread out and my dick going in and out of her puffy virgin pussy. This young woman was perfect, there wasn't one square inch of her body that wasn't beautiful.
Then I laid down on the boxes and she rode me cowgirl. After a little while I told her to lean backwards and thrust her cute little pelvis over me from that angle. I love my dick going in and out of a young virgin pussy at a variety of angles, and I think she did too. Then I told her instead of thrusting or going up and down, to roll her hips. She had to practice it a bit but pretty soon she had a real nice grind going, she looked and felt like a professional call-girl only better.
At that point I really had to taste her pussy. So I told her to move up and do that same thing over my mouth. She thought it was silly. But I had her move up and drop her pussy into my mouth, and pretty soon she was fucking my mouth, just using smaller circles with her hips, while I wiggled my tongue all over, inside her pussy and over her clit and lips. She was so fresh.
She rode my mouth a bit but for most of the night it was just my dick sliding in and out of her pussy like a long distance train chugging away all night. We couldn't get enough. But eventually light started coming in the windows and I knew we had to stop before the early birds showed up.
So I finally let her sweet pussy milk the cum from deep in my balls in gushing jets. We tore our bodies apart and got our clothes on. Some of the boxes had our sweat and goo on them so we stacked them in a place where they wouldn't be noticed until they had time to dry off. Once we were all dressed and everything was in order we wrapped our arms around each other and were in a tonguelock for like 10 minutes straight. But I knew we really were taking a chance even doing that, it wouldn't be a disaster if someone caught us making out but I still preferred that they had no reason to suspect anything at all. So we had to stop and just look normal for that last 20 minutes of our shift, which was very awkward considering the great sex we just had, and Sanya was pretty excited since it was her first time.
Chapter 3 Brian takes Sanya's oral and anal cherries
The next night, shortly after the last person had turned off the lights in the rest of the building, we approached each other with little knowing smiles. I put my hands on her ass and gently pressed her pelvis against my hardening cock while she put her hands behind my shoulder. "So what do you want to do tonight?" I asked her.
"More of what we did last night," she responded. She stuck her hand down my pants and grabbed my almost fully erect boner. "You always come prepared," she said, smiling at me and stroking my cock a bit.
"Why don't you take it out and suck on it?" I suggested.
"Okay but, I don't really know how to, you have to teach me,” she said.
"No problem," I replied.
She got on her knees, unbuckled my pants and pushed them down to my knees. She didn't touch my cock, just asked me shyly, "Okay what do I do?"
"Well, don't be shy. Just do what you'd like to do, and then I'll tell you what feels good to me."
She put her fingers up to the underside of my balls. then she gave the tip of my cock a wet little kiss, I felt her tongue lick the most sensitive spot right under the hole. Then she kissed the tip again, but opened her mouth a bit and put the whole tip of my cock in her mouth, and swirled her tongue around it. "That's perfect Sanya."
"Really?" She asked.
"Yes, that's a great start," I told her.
She did it again but this time wiggled her tongue against the hole. Then she went back to swirling her tongue around the tip. She was putting a little bit more than just the tip in her mouth, and soon she had a couple inches of my dick in her mouth. Suddenly she took her mouth off and said, "You're cock keeps twitching!"
"Yeah it does that when hot young women suck on it. Just keep going," I answered. She put the first couple inches back in and started bobbing on it like an experienced street walker.
I told her, "That feels great Sanya. You're a natural. Don't be afraid to get it nice and wet and sloppy too."
She continued bobbing on it, she had a lot of it in her mouth, as much as she could handle without it hitting her throat. Then she would alternate between doing that and holding it in her mouth and swirling her tongue. All this time she had her hand on my balls. My cock continued twitching.
"Now just lick it, starting with my balls, all the way up to the tip," I told her.
She started doing that, her hot little tongue felt nice against my balls.
"Now suck it just a bit more," I told her.
She sucked it a little more, and then I stopped her and said, "That was a nice blow job Sanya." We kissed a bit and I started removing her clothes. We both got naked and I said to her, "Why don't you lie down on those boxes and I'll lick your pussy."
I ate out her yummy pussy, and made her do lots of delicious moaning and sighing. Her little ass looked great, as it always does from any angle. I dipped my tongue into her little anal pucker. I had to, there was no way for me to resist licking such a hot and cute young ass. Her cute little ass hole tightened up the first couple times from the surprise of being swiped by my wet tongue. She had a nice tangy taste, after tasting it once I had to keep going. She said, "Ooooh, Brian, you're licking my ass!"
"Yes I know," I said. I licked it once more, and told her, "You have a really sexy ass." I slurped in her crack some more. I relentlessly circled her hole. Her hole kept tightening and then opening like she wasn't sure what to think of my tongue going just inside. Eventually I gave her whole crotch a few more good slurps.
"I'd love to put my cock in your ass. Do you want to try it?" I asked her.
"I don't know,” she said. “I mean, it's just kinda weird."
I said to her, "Your ass needs to get fucked Sanya. I could tell just by looking at it the first day I met you. Just go use the bathroom first so that you don't need to use your ass for anything else while I'm trying to use it."
When she came back from the bathroom I guided her to get in the doggy-style position. I had brought some lube and dripped some onto her hole. I smeared it around with my fingers, and wiggled one finger into her tight pucker. "That's just my finger,” I told her. "It will help you get ready for it, especially on your first time." I began slowly finger fucking her ass. My finger doesn't have the same kind of nerves on it as my dick, but I still loved the feel of what might have been the world's sexiest pucker clamped around my finger.
After a few minutes I asked her, "How does that feel?"
"It feels really good!" She replied.
"Your sexy little ass is still squeezing my finger pretty tight, are you starting to get used to it?" I was lying, I could tell she had adjusted to my finger but my dick was a lot thicker, and I wanted her to teach herself to open her pucker more.
She answered me, "It was tight at first but I'm okay Now."
I told her, "I'll put in my thumb then, it's a little thicker, but my dick is still thicker than my thumb."
She said "okay" and I pulled my finger out. Her little gape didn't last more than a second. I lubed up my thumb and eased it in and thumb fucked her ass a bit. She laughed and said "It feels funny but it's kind of fun."
I lubed up my boner and then pulled my thumb out of her ass, and rubbed the tip of my boner against her little hole in small circles. Her little hole had opened up and winked opened and closed a few times. "Let that little asshole stay open for me," I told her. I pressed the tip of my boner a little bit so that just the tip would go in, as I continued moving it in a circular motion. Her little pucker was puckering pretty tight around the tip of my dick. I continued teasing her ass and she opened up a little more.
"Alright Sanya, the tip of my dick is in there and I think you're just about ready. So I'm going to slide it in now."
"Okay" she replied.
I put both hands on her hips and slid my dick in about half way. She squirmed a bit but I kept my dick in there. I lovingly rubbed her back and asked her, "Are you alright?"
"It feels huge!"
I told her, "About half my dick is in, so it's almost the full thickness. I'll just stay still and let you get used to it for a minute."
I was thrilled just to have my dick half way into Sanya's ass. I rubbed her pussy with my fingers and squeezed her tits while we waited for her to catch her breath.
After some time I pulled out of her ass a little, and then slowly pushed it in about two thirds of the way. I had to go slowly anyway since I was also adjusting to the whole experience and could cum in a split second if I wasn't careful. I sure as hell wasn't going to cum just yet, hopefully it was going to be a long night. I lightly ran my fingertips from her shoulders down over her ass and then back up, and started gently squeezing her shoulders and neck. I eased my dick out slowly again, almost all the way out, and then slowly eased it all the way in. She was pretty quiet but I could hear and see her breathing deeply, and tiny little whimpers of intense pleasure as I did this. Her legs spread just a bit as well.
I waited, my dick buried all the way in her hot virgin ass. I gently rubbed my hands all over her shoulders, back, ass, and chest. Then I repeated, slowly out almost all the way, then slowly in all the way. "Brian I'm starting to like this," she said.
I replied, "Sanya your hot little ass feels great on my dick."
I slowly increased the pace. After half an hour I was fucking her at a nice steady rhythm and we were both short of breath and moaning expletives. It's really fun to hear a cute attractive young lady with a toned ass murmuring in her sweet voice, "Oh that feels good. Keep fucking my ass Brian. I love your big hard cock shoved up my ass like that..."
I had to pull my dick out of her ass, because the machines weren't running and we had to reload them. I didn't get up too fast though. I stayed kneeled behind her and rubbed my hands all over her back and shoulders and tits, but I didn't take my eyes off her freshly de-virginized anal pucker gradually winking from a full gape down to almost, but not quite, closed the way it had been before we started. Then I got up and tended to the machines.
She got up too and helped me with the machines. I love watching her bare ass and naked body as she walks around. When we were done with the machines we walked up to each other. I asked her, "So do you like that?"
"Yeah,” she answered. We're going to keep going right?"
I assured her that we would. We wrapped our arms around each other and kissed deeply for a minute. "Well let's stick my cock back in your ass. How about this time you lean over those boxes and stick that those cute buns out at me and I'll shove it up in there.
So we did that and I did fuck her harder this time, my cock disappearing between her cheeks as she struggled to keep standing on her two feet. She was squealing the whole time, they were squeals of agonizing joy and appeals to God and myself to continue what we were doing to her.
I fucked her ass all night, as the man she was giving all of her virginity to, I took it upon myself to make sure that her ass was thoroughly de-virginized and that it would never be the same again. She loved every second of it and I think she understood after that night that her ass was meant to be fucked on a regular basis.
As light started to come in the window, as she was panting and moaning loudly in her own orgasm, my balls unloaded quite generously where they had badly needed to unload all night, deep inside Sanya's ass.
I can't imagine enjoying a job more than that. We spent every night the rest of that summer naked, with my dick reaming her pussy or her ass, or on the floor with her hot naked body lying on top of mine while her tongue plays with my dick deep in her sweet wet mouth, her sexy pussy spread out and trickling juice into my mouth in a steamy 69.
I'm flattered to have taken this hot young woman's sweet vaginal, anal, and oral cherries, and I'm glad we had such a great summer together.