From Co-Worer to Student

This is part three of the first story I have written and felt compelled to put online. It is a work of fiction based heavily on events that I've experienced, a couple female friends, and other things that have shaped me as a person. While many people seem to prefer writing stories that get down to business, so to speak, I wanted this one to feel somewhat more realistic in terms of dealing with personal issues that come into play with a sexual relationship. Thanks for reading! I appreciate any comments, feedback, or advice.

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We decided to leaf through the books while sitting on her bed. While she fetched the books I turned off the TV and picked up our clothes. Once she came back with the books in hand, she led me upstairs and into her bedroom.

The bedroom had a very cozy feel. The walls were off white, as was the covering on the bed. Everything else, the trim, the furniture, and the rest of the bed, were all wood. On a small cabinet in one corner was a small TV. She'd covered the windows with teal colored curtains. Under all but one window was a potted plant. Finally, on each side of the bed was a nightstand with a lamp on it.

Ann set the books on the bed and told me to make myself comfortable while she changed into some different panties. I took off my socks and pants and crawled under the covers with my boxer shorts on. I didn't know if she was expecting me to be naked, but if she was putting on panties again, I assumed that boxers were still acceptable at this point. As I waited I eyed the books. There was no title on the cover, but it was a big book, and the pages looked like they were glossy ones that are usually used for pictures. The book under that one was big as well, but I couldn't see enough to discern what it might contain.

Ann came back wearing a tight light blue sleeveless shirt that showed off her midriff and some panties of the same color that left little to the imagination. The only real significant fabric was the little triangles that covered her rear and her pussy. The waistband rode low on her hips.

"Wow." I said without really thinking about it.

"You like this little getup?" She smirked at me.

"Yeah, you look great." I told her.

"Oh this is nothing, just something to wear to bed." She joined me and picked up one of the books. "Let's see what we can find in here. It's mostly pictures of all sorts of sexual stuff. Some of it gets into different fetishes though. I hope you're not uncomfortable with that."

"Not at all." I smiled.

"Good." She said and opened the book. "Say something if anything jumps out at you as interesting or appealing. I'll do the same."

At first most of the pictures were just men or women, some of whom were naked, that were in a variety of artistic poses and settings. The first picture I commented on was one of a brunette woman who was sitting on a bench with her legs parted. It wasn't the woman I was interested in though, it was what she was wearing. Her outfit, all black in color, was one of those that consisted of a bustier, thong panties, garters, and hose. That was one ensemble I'd always found incredibly sexy on a woman. As I explained this to Ann I noticed a sly look on her face. She smiled as we finished talking about the picture.

There wasn't anything else either of us was particularly turned on by until we were about three quarters of the way through the book. Ann was the one who paused for a moment, licking her lips. The picture showed a woman sitting on a desk in what appeared to be a makeshift classroom set up for this picture. The woman was holding a yardstick and looking at a man who was sitting at a desk in front of her. It was a classic picture of a teacher-student relationship, or as Ann saw it, a role play situation. She explained to me that it was something that she'd often fantasized about when she would masturbate. When I asked which role she usually thought of herself filling, she said she was always the teacher. We decided it might be something fun to try later.

We flipped through the rest of that book without seeing anything either of us commented on, so Ann opened up the other one. It was, as she warned me before turning to the first picture, a more fetish-centered book.

There were some more role play pictures at first. The first image we talked about happened to be another of the teacher-student type. Ann smiled when we looked at it, and we quickly resumed. At about the halfway point Ann stopped me by simply putting her index finger on a page and looking at me. The photo showed a woman who was wearing a strap-on harness and standing behind a man who was bent over a table. The angle of the photo didn't reveal if the woman had a dildo in the harness, but the idea of her sticking the guy in the ass with a toy was easy enough to imagine. As I looked it over my heart started beating faster. One of my little secrets was that I found anal stimulation quite enjoyable. The idea of having a woman involved in it was something I had thought about during many masturbation sessions. However, my fantasy of this wasn't anything to do with bondage. I was only interested in the pleasure involved.

As I had paused to look at the photo, I bit my lip and then returned Ann's gaze. I think we both understood the mutual interest in what we saw in the picture, because we both exclaimed "No way!" at the same time.

"Do you know how long I've wanted to try this with a guy?" She asked me, obviously excited. "Please, tell me you're serious."

"I am." I told her. I grinned and continued. "I didn't think I'd get to say something about it though. I figured you'd think I was a weirdo if I did."

"Oh man, I can't believe this!" She said and kissed me on the cheek. "Some time we really should talk about trying it."

"I think so too." I was just as excited at the prospect as she was.

The rest of the book went by without either of us pointing out anything we wanted to put on our "to try" list. I closed it and set it on the first book.

"I still can't believe you want to try the strap-on." She had a huge smile on her face. "Have you actually tried anal play before?"

"Yep," I answered. "Quite often actually. It can really make orgasms more intense."

"Mmm, you're naughtier than I imagined. I may have to make a special purchase one of these days."

"I think we should do it together if you decide to." I told her. "Shopping for toys together sounds like fun."

"Oh yes, that would be interesting. Maybe we can hop online this weekend and see what's out there." Ann picked up the two books and set them on the nightstand on her side of the bed. "What time do you have to help your buddy tomorrow?"

"We're meeting at 1 o'clock. So I should probably leave here at 12:30."

"Okay. It's just after midnight now. Do you want to sleep now, or are you up for some more play?" She said as she moved under the covers and rolled on her side to face me.

"What do you think?" I laughed. "You're talking to Mr. Night Owl."

"I'm the same way. Come here, I want to cuddle with you for a bit first." She lifted up the blankets and I moved towards her. "Here, face away from me."

I rolled on my side and heard her fidgeting around behind me, then saw her t-shirt flying to the foot of the bed. I thought maybe she would take off those little panties too, but instead she turned off the lamp and snuggled up behind me. I relaxed and let my head sink into the pillow. Meanwhile Ann had put an arm over my stomach and pulled me towards her. Then she scissored her legs around my top leg and pulled it back so our legs were tangled.

"Ahhh," I thought to myself. "This is great." Finally she finished moving and let out a quiet sigh of contentment.

I closed my eyes and concentrated on how her body felt against mine. Her legs, which I hadn't really gotten a good chance to see yet, felt smooth against mine. I could feel one of her small feet against my ankle. Her hips were pressed against my ass, and as we both still had underwear on, I was left to wonder how it might have felt to have her naked sex against my bare skin. Occasionally she ran her hand through the hair on my chest. As for her chest, I could feel every breath she took because her bosom would swell against me, and her breath breezed on my back. Once in a while she would kiss my shoulders, but for the most part she lay still with me.

I dozed off briefly despite not wanting to. The combination of immense comfort from lying next to her, and the exhaustion from the long week, both were enough to lull me to sleep. I'm not sure if Ann was feeling the same way, but one of her kisses woke me.

"Hey, you still awake?" She asked quietly.

"Kinda. I think I drifted off there for a few minutes."

"Do you just want to sleep?"

I turned over to face her. It was dark in the room, but my eyes had adjusted so that I could see her just fine.

"If we do something I'll be fine. Laying here with you is so comfortable it puts me to sleep." I said and reached out for one of her breasts.

"Okay." She smiled. "I just don't want to keep you up so long that you're friend will think you're a zombie tomorrow."

We were both quiet for a few moments. I wasn't sure if she was tired too, not sure what she wanted to do before we slept, or if she wanted me to express what I wanted to do. I knew exactly what I was ready for, so I took this pause to ask her.

"Will you take off your panties?" I asked. "I want to see your pussy."

"Yes." She replied as soon as I had finished. I smiled, feeling glad she wasn't planning on saving this for later.

She pushed the blankets off of us and neatly folded them back to the foot of the bed. After she was done she got down on her knees in front of me where I sat with my back to the headboard. Ann reached out for my hands, and once she held them she pulled me up to her so I was on my knees as well. She wrapped her arms around me and kissed my cheek.

"I'm so wet right now." She said quietly into my ear and flicked her tongue around my earlobe. "I really want you to see the rest of me." She paused for a moment. "Slide them down for me hon." She broke our embrace and instructed me quietly while sliding a hand under the triangle of cloth and covering her pussy with it. I noticed that the fabric had a large darkened spot from where her moisture had been soaked up. She watched closely as I hooked my thumbs around the waistband of her panties. Once the panties were down to her knees, she stood up so I could pull them the rest of the way off.

She was now completely naked, and apart from the hand she was covering herself with, I could see everything. I hadn't thought about it earlier, but her breasts didn't have any tan lines on them, making me smile for a moment as I thought about her in the sun with no top on. Her waist showed faint signs of tan lines though, as if she had actually sunbathed in the nude once in a while.

"Now come here, put your head between my legs. I want you to get a good look." She said after sitting down with her back against the headboard. Her legs were spread wide. "Good, now you get to see the rest of me." Slowly she pulled the hand up over her mound revealing it from the bottom first. My eyes were glued to the spot just below where her fingertips crept upwards.

"There you go." She said after pulling her hand away. "What do you think?"

I licked my lips and spoke. "It's beautiful." And it was, as pussies go.

I'd looked at plenty of pictures of females online, and knew that they all looked different. I guess I had never really formed an opinion on what kind of pussy I found most attractive. As I looked at Ann's I found that it was wonderfully formed. While some pussies are large and hidden behind large outer labia, Ann's was quite the opposite. It was small, and the outer lips were nearly absent. At least that's how it looked while her legs were parted. Instead the outer labia were nearly undetectable mounds than ran parallel to her slit. About half an inch above her clitoral hood she had a small patch of trimmed dark blonde hair. The rest of it was shaved clean. The hood itself was covering the clit completely at the moment. Her inner lips were a much darker shade than the rest of her skin. The very outer edge of each lip was almost brown in color and got redder and then pink going in towards her opening. And as a whole, the lips were parted slightly, and where they met I could see that an abundant amount of her honey had accumulated. Her smell, contrary to what I'd read in various stories, was…well it was Ann's soothing smell of soap and perfume, though there was a hint of a pleasant odor that I assumed was from her arousal.

When I finished admiring the view I looked at her face to find her watching mine intently. We both smiled at the same time.

"Ann, it really is beautiful." I told her and looked down at it again. I'd long hungered to spend time eating a pussy, and was anxious to have my first taste of Ann's.

"Before I let you do anything, as much as I want you to immediately, I'll show you a few things, okay?" She said, drawing a quick nod from me. I again found myself thankful that she was so willing to be an instructor when necessary. She laid a hand between her legs. "These are the labia." She pointed to her dark lips. "Here, under this little bump, is where you'll find my clit, which I'm sure you're well aware of." I nodded again. "Good, now here under where the clit is at, that's my urethra." She'd gently pulled her hood back and I could see a little black hole. "Below that," She continued while parting her lips with her fingers. "Is the vagina. We both know what happens in there." She grinned after making the final comment. "Okay? Any questions my young student?"

"Nope. Well, actually, yes, I do have one. Can I taste you?" I smiled and looked into her eyes.

"There's nothing I want more right now. But before you do that, I want to warn you that if…when you make me cum, I might squirt a little bit." She said and blushed, slightly embarrassed.

I watched her face for a moment, surprised by her being so self-conscious. "Then I have something else new to look forward to." I said and grinned at her, hoping that it would ease any shame she was feeling. I think it worked because she smiled back and bit her lip, looking her confident self again.

Without any further discussion, I stuck out my tongue and ran the tip of it between her lips from the bottom to the top. I wanted to see what she tasted like, and found that the taste was, apart from a very slight sweetness, non-existent. This was the one thing I had often feared would turn me away from enjoying going down on a woman. Discovering that Ann didn't have any unpleasantness between her legs was a relief.

Satisfied that all was well, I tilted my head slightly and pressed my tongue flat against one of her lips, licking the entire length of it, and then did the same with the other one. I found that the lips felt very soft and delicate, much more than I'd anticipated. Ann's wet state told me that she was already aroused, so I decided to stroke her lips a few more times with my tongue, making sure I covered as much of their surface as I could.

My next desire was to explore deeper inside her. Tilting my head even more, to the point that my tongue's breadth was vertical and would be able to access the area beyond the labia, I poked in and wiggled my tongue back and forth while pressing against the walls of her cunt. I wished I could have pushed in even further, but my tongue couldn't reach, so I continued licking as much as I could.

Once I had consumed most of the fluid that had accumulated, I pulled away and looked closely at Ann's hood. My brief stop in stimulation caused her to speak up.

"Scott, you're doing good. Why did you stop?" She asked with a sigh.

"Just looking around before I continue." I told her and kissed her thighs as an attempt to comfort her.

"My clit…use your tongue on my clit." She pleaded. Lucky for her that was a moment a way.

I couldn't see the clit, or at least I didn't think I could. I placed a thumb above the hood and pulled the skin back and got a better look. Now I could see it was quite small, a tiny nub taking refuge under the hood like a small pearl in a clam. I didn't want to just pile on the stimulation, so I stared by simply blowing on it. Ann immediately sighed and cooed at the same time.

"If she's reacting to that," I thought to myself. "She must be getting close to an orgasm already."

I stuck my tongue out and bit down on it so I could use it with more precision. With the tip I pressed softly against her clit, wiggling it a bit to touch as much of her clit with my tongue as I could. When I had done that I brought my thumb down closer to the hood and softly pressed down.

"Oh god yes. Keep that up. You'll make me cum soon." Ann whispered. Each sentence was punctuated by a gasp. "Suck on it. Put it in your mouth."

Not wanting to lose any progress, I licked my lips and brought them around her hood and pressed in with my tongue to touch her clit again. She immediately started to subtly grind her hips upward into my face. Every time she exhaled, which was increasing in frequency, she let out a little high pitched moan. During this whole time her legs had been spread out, her feet almost on the edges of the bed. But as she neared her climax, Ann lifted her legs up and put them over my shoulders, and at the same time put her hands on my head.

I was so excited at knowing she was nearly peaked, so I sucked in with my mouth and rapidly flicked my tongue over her hood. That's when I remembered reading something about giving head to a woman and decided to do it -- I hummed softly.

Her reaction to the gentle sound was instant. Her thighs tightened around my head, locking me into this position until I finished the job. And her hands pulled me forward. This allowed her to fuck my face without worrying about me pulling back. I loved it! I closed my eyes and feverishly worked her clit. It took a few moments, but after pushing under the hood again with my tongue, and humming a little louder, her whole body went rigid. The lock she had on my head was so complete that I struggled to draw breath. I closed my eyes, kept up what I was doing, and waited for her to finish.

"YES!" She yelled without reservation. "Cummmming. Ohhhhhh."

Her hands left the back of my head and reached up for the head board, but her legs squeezed even harder. Meanwhile her back arched up, causing her legs to follow her body up the bed, and pulled me with it. The position was very awkward, but it was a minor price to pay for what I was giving to Ann. Her body started to shake, and that's when I felt her squirt. It wasn't very much fluid, perhaps enough to fill a shot glass quarter full. Most of it leaked out against my lower jaw because I my face was too close to let her actually fire the fluid into the air.

I wasn't sure when to stop what I was doing, but I knew enough that her clit would probably be quite sensitive after having an orgasm. I decided to release my lips from her hoot and just run my tongue around on it, though doing so was not easy with Ann's legs severely limiting my operating space.

"She's just cooling down now," I thought. "She'll loosen up her legs any time now." But she would have nothing of that.

"Oh yesss, I'm gonna cum again. Holy…Scott, keep…my clit. Suck…clit." She patched the words together, gasping between each one, but I knew what she wanted.

I took her back into my mouth and did my best to massage her button with renewed excitement. It took about half a minute before her whole body was sent into a reaction. From her throat came a deep groan that almost sounded like something you might hear from a wild animal. "I'mmmm cummmminnnnng!" Her voice was weak as she shrieked. As soon as outburst ended I let out a quick hum that was a little louder than before. Ann's reaction to this came as another squirt against my face and a sharp cry, bordering on a scream.