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From Co-worker to Student

By: Innocent_Outside



This story is the first 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.

Introduction

Growing up I took to strong morals and could have been considered a goody-two-shoes type of guy. I didn't touch drugs, smoking, or alcohol at all. Nor did I delve into any sexual adventures of any kind. In fact I was never in any serious relationships. While my intent to keep my virginity intact until marriage was something I had no desire to dismiss, I often longed for a relationship. At times I even found myself wanting to simply experience touch, smell, and pleasure of lying naked next to a naked woman even if we weren't doing anything sexual. But I didn't put that at the top of my priorities since my studies, work, and other activities were more important to me.

So at age 25, molded by that desire to stick to my morals, I still found myself as someone who had not yet been in any relationships, and was still a virgin yet not ashamed of that fact at all. Only at that point my desire to experience the physical side of a relationship was much more intense. In fact it was that intensity that ended up getting the best of me.

My job as a programmer at a medium sized company placed me in contact with most of the fellow office staff there in some way. Whether it be the occasional passing and greeting, or working daily on a project, I knew pretty much everyone, and was well liked and appreciated. I enjoyed that position and my work as well, finding that it was both challenging, intellectually stimulating, and a great opportunity in which I could continue to build my knowledge. So I had no desire to do anything that might put my job security in jeopardy.

Despite my great liking of my job and the people who I worked with, I let my strong desire for a physical relationship get the best of me. I'd never have expected to find it taking place with one of my coworkers, something which went against both my morals as well as my desire to avoid any possibility of losing my job.

The woman who finally fulfilled my hunger for physical affection was part of our purchasing department. I'd worked with her on a project in the past, and for the most part before and after that, our interaction consisted of only passing each other in the hall or small talk while we both happened to be getting a beverage in the break area. Normally this type of thing wouldn't even make my think twice about a woman. Yeah, beauty certainly makes a man's mind dwell on a woman, and this woman was a beauty. But a handful of chance greetings throughout the week weren't something I considered to be the first steps towards a sexual relationship.

This lady was different though. She had a playful nature, bordering on flirtatious in a harmless way. Ann was her name. She was around 40 years old, about 5'6" tall, built athletically with what appeared to be ample breasts that she always kept well concealed in her modest clothing. Her hair was very blonde, curly, and about neck length. And her face, while not unattractive in anyway, was one many men might not think of as stunning. Overall she was an attractive woman, but by no means a trophy. The thing that always got me looking at her was her ass. Now there were a number of attractive women that worked there, many of whom were my age, but none of them had as nice a posterior as Ann. While she did dress modestly, her pants always seemed to make her butt look fantastic. The best days were Fridays when she'd wear jeans. Nothing conformed to the shape of her ass like jeans, and whenever I saw her wearing them I made a point of walking behind her just to get a good look.

Now that I've made it clear that I found this lady attractive, I should also explain that I had no intent of ever engaging in a physical relationship with her. None whatsoever. Again, I had every intention of staying a virgin and not putting my job at risk. On top of that, I had no idea if she was married. Meddling with a married woman was something I vowed that I would never do. As it turned out, things would work out much differently that I would have anticipated.

The whole situation that I'm going to lay out in the rest of this story started on a Monday morning when Ann came to me requesting my help on a project that I'd worked on in the past. There were some enhancements and changes that needed to be made to one of my applications, and my programming was needed to make that happen. Ann was the person who'd taken the responsibility of making sure it got done. The big problem was that, due to some upcoming deadlines that her and her coworkers needed to meet, they would need my programming done within one week. It wasn't something I'd preferred to rush through, but when the orders came down from the company president, you didn't think twice about doing whatever was necessary to fulfill them. That Friday, after a week of fast food and long hours, we finished everything we'd set out to do. That's when things started to get interesting.

Part One

"I think that's it." I glanced at her as we sat back after reviewing everything that we'd worked on.

"I think you're right. I'm so happy we finished on time. You have no idea how much this means to me Scott." She was smiling at me. "How about we go grab some real food to celebrate? I'll buy."

"Well if you're buying, then I'm all for it." I was sick of eating fast food all week, and the thought of real food, even if it wasn't homemade, sounded excellent.

"Great. I'm going to drop this stuff off at my desk. How about we meet in the lobby in ten minutes?"

I agreed to her plan and we went about our business. After quickly organizing the paperwork on my desk, shutting down my computer, and stopping in the restroom, I headed for the lobby. She walked in less than a minute later.

"Change of plans. How'd you like some homemade grub instead? I left my credit card at home and I've got no cash on me."

"I don't mind paying." I replied.

"Oh come on, you're not going to pay for anything. I owe you for your hard work this week, and that's that." She informed me as we were walking towards our cars.

"I guess there's no point objecting. I'll follow you to your house."

My mind wandered for most of the drive. I was tired and hungry but in good spirits now that the weekend had arrived. With no big plans ahead, I was going to do nothing but sit around and be lazy.

We arrived at her house in about ten minutes. It was a nice house. Two stories, a grayish-blue color with white shutters, and surrounded by a well kept yard. As a whole it had a very nice feel to it. 

The inside was the same way. There were lots of pictures of various landscapes, which I found out later were photos that Ann had taken, crafty little shelves that supported various knick-knacks, plush furniture, and many other things that offered a comfy feeling. I liked it.

"I'm going to change out of these work clothes and then we'll check out the food situation. Make yourself at home." She said as she put her work stuff down and headed to her bedroom. I took the time to look around a bit.

A few minutes later she returned wearing a dark t-shirt and running shorts. Modest yet comfortable.

We wasted no time heading to the kitchen after that. "Let's see what we can whip up." She rummaged around in a few cupboards and in the fridge. "How about some subs? I've got lots of lunchmeat and everything else we need."

"Good food and no cooking? How can I argue with that?" I smiled as I started to help her get everything out.

"So what have you got planned for the weekend?" She asked as she set a pile of lunchmeat on the counter.

"As little as possible. After this week I'll be doing nothing but laying around being lazy."

"Oh come on. Haven't you got some girl to spend time with, or a party to go to?" She nudged my shoulder; her playful nature in action.

"Not this weekend. Not most weekends actually. My social life has been pretty lame lately."

"I can relate to that. With this place empty most of the time now I tend to stick around here."

We'd both finished assembling our sandwiches and sat down.

"Oh! What do you want to drink? I've got some pop, tea I think, water, and wine." She got up and walked to the fridge.

"Water sounds good."

"Alright. Two waters coming up."

She returned with the drinks and a pitcher full of water, and we started eating. Despite being famished we both took our time on the food. It hit the spot.

"What did you mean about this placing being empty most of the time?" Her comment earlier had me wondering.

"Well the kids are only here every other weekend, except in the winter when they spend every other week with me. So it's just me here most of the time."

"You're divorced?" My surprise was obvious.

"Yep, it's been, oh, nearly three years now. Gosh, I can't believe it's been so long. But anyway, yeah. You seem surprised."

"I am. I just assumed you were married."

"Nope." She smiled at me. "How about you? Divorced too?"

"Oh yes, I'm on my fifth one now." I said sarcastically, followed by a feigned sigh. "I guess I have a knack for it."

"Five is it? You must be on some kind of annual wife rotation then?" She laughed.

"Yes, you're exactly right. I signed up with the local swingers club. But they're running out of women to send my way, so I'll have to find a new club to join." I couldn't hold a straight face anymore.

"I should have known. You always seemed a little different to me."

I just shook my head and chuckled. My glass of water was nearly empty so I reached for the pitcher, only to accidentally knock it over towards Ann. Since it was almost full she ended up soaked.

"Oh crap!" For some reason I couldn't help but laugh as I said it. "I'm sorry Ann." I got up to find a towel or napkins.

"It sure sounds like it funny guy." She didn't seem upset, but she wasn't laughing either. I handed her a towel and she pressed it against her chest and then her stomach. "Good thing that was water. You really drenched me."

"I really am sorry Ann." I was serious this time.

"It's okay." She said as she was wringing out the towel in the sink. "I couldn't let you get away without a little hassle." That's when she nonchalantly pulled off her shirt.

"Oh. Oops." She quickly covered up her chest with the shirt. Her face was turning red, and I had no doubt it was an honest slipup. "I'm so used to being here alone. Well you know about that already. I'm sorry, Scott. I better go change into something dry."

I was glad she did because I wasn't sure what to do while she was standing there. My eyes were trying to look at her bra-covered chest, while my manners were telling me to look away. My eyes won, and I think she saw me looking.

While she was changing I moved the dishes to the sink and started to wash them. Even though she had a dishwashing machine I guess I felt like this would be a good gesture to show her I felt sorry for the spill.

"You don't have to wash those." She said as she came back into the kitchen.

"Oh it's the least I can do after..." I said as I turned around to find her leaning against the counter wearing only a dark blue bra and matching panties. "You forgot to put clothes on."

"No I didn't." She was clearly serious.

I wasn't sure what to say. For a moment I considered what could be going on. Either she was doing this to avoid getting more clothing dirty or she had other motives which I could only assume were sexual in nature.

"I promise I won't spill anything else on you." It was the only thing I could think to say.

She smiled at me. "Want to spend the weekend laying around with me?"

I weighed in my mind the significance of her pun, intended or not. Was she really proposing a weekend of sexual intimacy?

"Yes," she answered the question for me. "I'm asking if you want to sleep with me."

"Okay." It was out of my mouth before I had time to think about it.

She walked over to me and took one of my hands and led me to her bedroom. My head was spinning with worries. What about my abstinence? How would this affect things at work? But my train of thinking quickly changed. Was I really going to have sex with this beautiful woman? What am I going to do when she realizes I don't know what the hell I'm doing?

"Ann," I had to tell her what was on my mind before anything happened. "There's something you should know."

"What? Wait, you're not gay are you?" She said as we sat down on her bed.

"Oh no," I chuckled. "It's nothing like that. I mean, it's complicated for me."

"Well then tell me. The last thing I want to do is hurt you, if that's what you're getting at."

"Okay." I paused, trying to figure out where to start. "Okay, what about work? If we...have sex, isn't that something that could affect things at work?"

"I don't think so. I'm not going to tell anyone, are you?"

"Of course not, but this would change our relationship. It already has." I hope she'd understand.

"Look, my job means a lot to me. And I'm sure yours is just as important to you. If we go ahead and make love," She sat back against the headboard. "I promise you I won't let it change how I, how we do our jobs."

"Alright, it just seems like something that could affect things. That's why I wanted to bring it up."

"I understand. I appreciate you're being thoughtful. Is there anything else?" She had pulled her legs up to her chest and wrapped her arms around them. Out of the corner of my eye I could see her panties were now pulled tight against her pussy, revealing the shape of her lips.

"Yes. I'm a virgin." I blurted it out and stopped without elaborating.

"Really?" She sat up, clearly surprised. "You're really a virgin?"

"Yes, that's why I'm...well I'm really feeling awkward and confused. As much as I'd love to rip my clothes off right now and have fun with you, there's part of me, my morals and spirituality, that's holding me back. I've been waiting for marriage. It's so hard Ann." I sighed with frustration. "And yet at the same time I can't deny that I've had days where I thought about nothing but what I'd love to do with a woman."

Nothing was said for a few moments. Finally Ann broke the silence.

"We don't have to do anything if you don't want to." She was speaking quietly. "As much as I respect what you're dealing with, I still want you Scott." She set her chin on her knees and looked into my eyes. "I'm not going to persist though. This is your decision. Whatever you decide, I'll honor that."

So it was up to me. No pressure at all. I lay back on her bed as my mind started reeling. From the start of our short talk my hormones had been gently prodding me, and in the back of my mind I'd been talking myself into agreeing with her. I mean, what harm is there in enjoying the company of a beautiful woman who just admitted that she wanted me?

Ann sat there silently, watching me. I didn't want to keep her waiting. I wanted to do the right thing though! I knew what it was. I had to tell her no, this was not a good idea. But my brain was insisting that it was!

I opened my mouth to speak. "Okay." Nothing else came out.

From Co-worker to Student Ch. 02



This is part two 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.

-----

"Okay?" She responded a little surprised and unsure what I meant.

"I want to do it." I smiled timidly.

"You've decided? Are you sure? I guess I am asking you to make a big decision." She said. "Maybe you need more time to think about it."

"Ann, I've always fantasized about losing my virginity to an older woman. I just never thought it would actually come true. So, yes, I'm sure."

She put her chin back on her knees and peered at me thoughtfully making me feel rather uncomfortable. 

"I want you to be absolutely sure about this, Scott. I think you need more time. I'd feel terrible if you woke up on Monday morning filled with regret." She spoke slowly, as if she'd thought through every word and didn't want to misspeak. "Why don't you go home and pick up some clothes and anything else you think you might need if we spend time together. Take your time and think about it. If you don't feel right about coming back, it's okay." She smiled as if to assure me she'd understand that decision. "If you come back, I'd be thrilled. Seriously Scott, I once felt the way you do about sex, and I understand where you're at right now. But I think what you'll gain from this would be more than just a weekend of sex. I hope we can become more than just co-workers." She paused again, and shook her head slightly. "I don't mean romantically. Just good friends...with benefits." The smile returned to her face.

Of course I had already been considering what she was offering. My mind raced as she spoke. She was right, I decided. I would head home and figure out what to do. Being able to do so alone, free of the psychological pressure of her nearly naked body, would be a good thing.

We said our goodbyes and I walked to my car. As I started it up I saw her watching me from the front door. I don't remember much about the ten minute drive other than thinking the whole time. I was back at my previous point of making a decision. I knew that the right thing to do was decline her offer. However her comment about what I'd gain had stuck with me. As I considered her meaning, I realized that I could come away not only with her as friend, one unlike I'd had before, but she might approach the situation as something of a teacher. I could ask her to go slow, and show me how to please a woman properly, things I could use when I finally marry. I knew there were plenty of questions that I could ask her on top of that.

I threw some clothes and toiletries into a bag, took a quick shower, and put on some clean clothes. I was ready, and still didn't feel like I was set on what to do. So I flopped on my bed and stared at the ceiling. It was obvious that I couldn't decide one way or the other just by thinking about it. And that's when my longing for the physical sensations of a woman's company took over. I stood up, grabbed my bag, and headed back to Ann's house.

My way back to her house went fast. I made a point to put my decision out of mind. Dwelling on it was just going to distract me from the experience. I cranked up the volume of the CD I was listening to and thought about the next few days. "Oh crap!" I thought as I remembered that I was supposed to help a friend of mine move the next day. I didn't need to do that until after lunch, so it would still give Ann and me some time to be together. I hoped it wouldn't be reason enough for her to change her mind.

I pulled up to her house and saw the garage door opening so I pulled inside. She was standing next to my car as I got out. I wondered if she had been watching for me the whole time.

"I'm so glad you came back." She whispered in my ear as she hugged me. She hadn't put on any clothing while I was gone, opting to stay in only her bra and panties, but did have a blanket draped over her shoulders. As she hugged me tightly, I felt her breasts press against my chest. She smelled so good. Any remaining indecision I had at that point faded away. "Come on, let's go inside."

She grabbed one of my hands and led me into the house, not forgetting to close the garage door on the way inside. As she walked in front of me I notice a spring in her step like that of an excited little girl who was just granted a request that she'd long been denied. I dropped my bag near the kitchen table as she led me through to the living room.

We sat on the couch, facing each other. The television was on low volume and provided some nice background noise at a time when I really didn't want to experience any awkward silences. There was only one light turned on, and it shone softly such that it would have been hard to read a book, but one could still see everything in the room just fine. Ann shed the blanket, and sat at the end of the couch opposite me with her legs pulled up in front of her again and her chin on her knees. I couldn't help but look down at her dark blue panties that were again pulled tight against her pussy lips. That sight alone stirred my hormones.

"I'm so happy Scott." She spoke as we sat down. "I didn't think you'd come back. I want you to know that I'm honored that you're willing to let me be your first partner. It's been a while since I last was intimate with a guy, so if I go too fast, tell me, okay?" I nodded and let her continue speaking. "I want to show you everything. God, that idea excites me so much. I still can't get over the idea that you've never experienced so many things! I'm eager to show you the ropes. I promise I won't disappoint you." A huge smile formed on her beautiful face.

"When I was at home, that was the only thing I decided I wanted us to agree on. I wasn't sure how you'd feel about going slow and letting me understand everything." I must have had a look of relief on my face because she reached out and put a hand on one of mine. "But there's only one problem. I have to help a friend of mine move tomorrow. It's not until after lunch though."

"That's okay." She said, and then thought for a moment before continuing. "Would you want to come back after you're done?"

"Oh. I hadn't thought about that, but yeah, I'd love to." I replied, thrilled by the idea.

"Good," She replied, grinning. "I want you as much as I can have you this weekend. I hope you're a night owl, because I think it's going to be a late one for us."

She stood up on her knees on the couch, and put a hand on the arm of the couch and another on the back of it, so she could lean over me. For a few seconds she was still, studying my face. I caught a glimpse of her modest cleavage out of the corner of my eye, and looked down at it. My mindset of the two of us being professionals threw up a red flag, and I blushed and muttered a quiet apology. As if to accept the apology, Ann leaned over more and put her lips to mine.

The kiss, or "The Kiss" as I remembered it since it was really my first really long passionate one, started slowly. True to her word, Ann took her time, keeping her lips shut as she pressed them against mine. I closed my eyes and sat up straight to meet her. The new sensations sent my head spinning. Her lips felt warm and soft like a down pillow. The perfume she was wearing was very mild and had a slight vanilla smell to it. 

As we kissed her nose pressed against mine causing me to open my eyes. She still had hers closed, so I took the moment to watch her face. Her bangs hung over one side of her forehead because the way she parted her hair, for lack of a better way of describing it, wasn't down the middle of her head. Her eyebrows were thin, and more of a dark blonde compared to that of her hair. They had a nice arch to them and were obviously something she took to grooming carefully. She was wearing just a little bit of eyeliner, but not much other makeup, which I found refreshing. I'd never really noticed it before, but she had lots of faint freckles on her cheeks. And her cheeks were accented by high cheekbones that weren't too angular. Her nose was short and came to kind of a stubby point. I thought it was cute.

I brushed her bangs back and cupped the right side of her face in my hand for a moment before she pulled away. I watched her lips in anticipation of the kiss continuing. They weren't exactly thin, but weren't puffy either. Her top lip had a cupid's bow in the middle, and her bottom lip was a little thicker and always seemed to be pursed as if she was going to speak. Sometimes at work I had noticed that, depending on her mood or what she was doing, her lips would have a slight pout to them.

"That was nice." Ann said softly and gazed into my eyes before getting off of the couch. She motioned for me to move towards the middle cushion. I moved over and she sat on my lap in such a way that her legs were bent all the way, her knees were by my hips, and her crotch was resting above my thighs. She pressed her chest against mine and bit her lip. "You ready to do that again now that we're a little more comfy?" She didn't give me a chance to reply, not that I would have declined. Her arms went around my neck and she put one hand on the back of my head. I wrapped my arms around her and let my hands rest on her lower back.

This time the kiss grew much more passionate. Her head tilted slightly and her mouth opened right away, poking my lips with her tongue. I had no intent of resisting her progress, and gladly welcomed her exploratory gesture by shooting my tongue her way. The taste of a woman's mouth was something I had often wondered about, but eventually assumed that unless she was a smoker or had recently consumed something, that her mouth would probably not taste like anything. I would say that held true with Ann. Aside from the wonderful passion of the kiss, it was the wet warm feel of her tongue and lips that I noticed.

"God, I feel like I'm in high school again." She said as she paused for a breath. "I just wish those guys were as patient a kisser as you seem to be."

She kissed my cheek and then my neck as she scooted her body even closer to me. Her crotch was now pressing against mine. My cock, which I hadn't noticed while we were kissing, was now very hard and pointed upwards. She noticed it and let out a little "Mmm" as if to give her approval of my arousal. Her chest was now pressing hard against me as well. Those soft breasts of hers sandwiched between us. I wrapped my arms around her again and hugged her tightly. This simple feeling of having a woman's weight pressing against me was something I had often longed for on nights when I was feeling lonely. It was just as good as I had hoped.

When she finally pulled away I had leaned my head back and my eyes were closed. I was getting so into how it felt having her laying kisses on my neck and ears that I felt a little disappointed when she stopped.

"Oh Scott, I'm so horny right now." She spoke softly. Her words were a far cry from the professional choice of words I was used to hearing from her at work. "You've made my panties wet now. You promised not to get any more of my clothes dirty, naughty boy." She smirked at me and pressed her nose against mine. I couldn't help but laugh at that comment. "I guess I can let it go this time."

"I hope so. All I was doing was sitting here." I said and laughed again.

"That's not how it feels to me." She said as her eyes darted down for a moment, her way of pointing out my erection. "It's good to know you're enjoying this too." She sat back a bit and laid her hands on my chest. "Can I take off your shirt?"

"Sure." I said.

She took her time undoing the buttons and then pulling it out from being tucked into my pants. I helped her pull it off of my arms. Then she expertly removed my t-shirt by pulling it up over my head. 

"Much better." She stated while examining me. I've always been kind of a skinny guy. Most of my strength is in my legs thanks to running regularly. But my upper body was still in shape, just a bit on the thin side. I also had a fair amount of dirty blonde hair on my chest. She ran her hands from my shoulders down to my elbows, and then over to my pectorals where she stopped and looked into my eyes.

"You feel good Scott." She was about to say something more, but stopped for a moment. "Do you want to see mine now?"

I smiled slightly and just nodded. I'd seen plenty of breasts while browsing the internet, and had copped a feel here and there in the past. But I never had this type of up close and personal encounter with them before.

"Okay, I didn't think you'd say no." Ann laughed. "I hope you like them."

She lifted her arms up and put her hands behind her head making her chest pull upward and her breasts swell a bit. I was actually surprised that they looked smaller than what I was expecting after seeing her figure in her work clothes. And even though she'd been in just the bra this whole time, I didn't take time to really look at her chest closely. Regardless, I was not disappointed at all. I'd never been very interested when seeing pictures of big breasted women before.

"I want you to take off my bra. Just reach around behind me and unhook it." She instructed me. I reached around her back to manipulate the hook mechanism, and in doing so found us face to face again. She kissed me on the lips as I quickly learned how this bra worked. It took a few moments of fiddling with it, but I managed to unhook it. Ann felt that I had been successful, broke the kiss, and lowered her arms so that she could hold the straps.

"Okay, now sit back again." She ordered as she placed her hands on the cups of the navy blue bra. Slowly she pulled the cups downward while watching my face closely. I bit my lip anxiously as her tits were fully exposed. They were, as I theorized earlier, smaller than I was thinking, but nothing for her to be ashamed of. They fit her frame and build very nicely.

"Do you like them?" She asked quizzically.

"Very much," I said. "They're perfect on you. Now you get to see just how inexperienced I am. What size are they?"

"Oh hon, lots of men don't have a clue about bra sizes." She chuckled. "Mine are about a 32B right now, but that changes as my weight changes. Sometimes they'll get up to a 34C, sometimes they get a little smaller. But this is pretty average for me." She cupped them in her hands and looked at them with me. "You really like them? I've always thought they were a little small."

"No, they're perfect. And I'm not just saying that because you're letting me see them. They really look good with how you're built." I hoped she believed that I was being completely honest with her. "Besides, I never thought fake ones looked that good."

"Well if a young man like you approves, that means a lot. I do have to admit that I think they've aged well." She said, and I nodded in agreement. They didn't sag much, and the little sag that was there didn't do anything to make them look bad.

Ann watched me intently as I inspected her now bare chest. Her breasts were very symmetrical. The areolas were between and inch and an inch and a quarter in diameter, and her hard nipples were maybe a touch under a half inch across. The tits as wholes were firm enough that the profile of each looked like a half pear pressed against her chest. The area between her breasts and her upper chest was covered with freckles like those on her face. I smiled at her after observing all of this, and she returned it with a big grin. I think she finally believed my comment about them being just right for her.

"I'm glad you like how they look. But I want to you know if you like how they feel and taste and smell, okay?" She had taken my face in her hands as she said it.

"I'd love to." I admitted.

"First I want to tell you a few things though." She said as she put her hands on my shoulders. "Never forget that to give the entire thing attention. Many guys just play with the nipples, and while the nipples are sensitive as hell, the whole tit feels good when it's touched." Then to demonstrate she put her hands under the breasts and cupped them again and roughly ran her hands over them as she said this. "The nipples are much more sensitive, like I said. A friend of mine once described them as being hotwired to the clit, and I'm inclined to agree with her. If you want to get a woman hot down below," She said as she gave her pussy a firm pat with one hand and then brought her hand back up to the bare breast. "Make sure you start by pleasuring the nipples and the rest of the breasts."

I had given her my full attention as she told me this stuff, and now took a moment to digest all of it. I already felt that her knowledge was well worth knowing. My smile grew as I thought about it.

"Now," She continued. "I want to feel your hands and mouth on them." Her hands went to my shoulders again for a moment and she smiled at me as she anticipated the upcoming pleasure she was going to receive. Then she rose up so she was standing on her knees and her tits were level with my face. She brought her arms around my neck and laid them on my back and gently pulled me towards her.

I didn't want to use my mouth right away, so I had to nudge her away from me. I quickly and carefully took her breasts in my hands. I was surprised at how soft they were.

"Wow, they're so soft." I said quietly. My wonderment was obvious in my voice.

"Yes they are." She said, and sighed as I continued touching her.

First I simply held them in my hands. The only thing that I can think of to compare them to is the softest loaf of bread you might find at the market. Not so soft that they flatten under pressure, but very soft nonetheless. As I finally got over this new discovery, I slowly traced my fingertips along the underside and then around the top of each one simultaneously. After that I took them in my hands so that the undersides pressed against my palms and the nipples were against the middle of my hands. I still couldn't get over how soft they were.

"Don't be afraid to be a little rough with them. Not too much though, they're sensitive. But some nice firm squeezing feels really good." She said as she watched my hands.

Understanding what she meant, I put the webbed part of my hand between my thumb and index finger under each one and pushed up so I could hold each breast completely in my hands. Once I had a comfortable grasp on them, I gave a gentle squeeze, bringing a satisfied sigh from Ann.

"There you go hon. Use your mouth too." She whispered to me.

"I will. I want to take time to enjoy this." I told her. But I was ready to taste these lovely mammaries. I pulled my hands away, licked my lips so that they were softer, and kissed each nipple very gently. No need to get her too excited too quickly. At that moment I wished I had two mouths so that I could give both nipples attention at the same time, but decided that I would do my best to give them both equal time in my mouth.

When I was about to begin exploring with my mouth, I decided that I needed a better angle at which to do it. I put my hands on Ann's hips and pulled her to me so that her crotch was pressing against mine. Then I put my hands behind her lower back and started to lean forward. Ann knew what I was trying to do, and she put her arms around my neck and leaned back. Now I was able to suckle her chest and have her body snuggly pressing against me.

Her nipples were hard, and the way they reached straight up almost seemed like an invitation for a passing mouth to stop and spoil them with pleasure. I started on her left breast. Taking one hand from behind her, I cupped the tit from underneath and pushed it upwards slightly, making it swell more and causing the nipple to protrude even more. While I used my mouth on it, I did my best to continue a gentle massage with my hand. Finally I was ready to let my lips and tongue make contact.




From Co-worker to Student Ch. 02



My first desire was to just flick my tongue over the nipple. I did this for a few moments, getting it wet with a little saliva and drawing another sigh out of Ann. My mouth hungered for more though, so I licked my lips again and formed them into an O-shape and kissed her nipple before softly sucking it in. 

As I discovered with the taste of Ann's mouth, the taste of her skin, specifically her nipple, didn't seem peculiar in any way. Mostly it was the smell of her skin that drew my attention. She smelled clean, like both her soap and that mild vanilla perfume she was wearing. So the taste, if there was one, was more of a product of how she smelled. 

My sucking her nipple drew more of a reaction from Ann that I expected. She had slowly started to grind her crotch against mine. This was, as I thought to myself, a good sign. Her comment about the nipple being hotwired to the clit came to mind. I smiled and continued. As I sucked the nipple I flicked my tongue back and forth over it.

"Oh Scott, that's good." She whispered. "Nibble it a little bit now. Not too hard though."

I released my suction and pondered for a moment how exactly to nibble. Do I use my teeth? Or perhaps use my lips with some pressure from my teeth? I decided to use my lips first. Rather than risking biting with sharp teeth, using my lips as padding seemed like a good start. I softened my lips with my tongue again, and then took the nipple in my mouth again. With it positioned between my lips I gently bit down. Ann's reaction was instant. She inhaled sharply and her back straightened at the same time.

"Yes, that's it. Do it little harder now." She encouraged me.

I applied more pressure and then released it, and then bit again. Now that I had some idea of how firm a nibble she liked, I wanted to try my teeth. I grasped the erect nipple again and slowly applied more pressure until she moaned softly and nodded. To add to her sensation I started licking it through my clenched teeth.

"Oh Scott, that's it. Now do the other one." She continued to coach me. I appreciated the fact that she was being so patient and helpful.

In all my excitement of playing with the one nipple, I'd forgotten about the other one. I quickly moved my mouth over the neglected nub and did the same thing to it as I had to the first one. By the time I had reach the end of that routine Ann had started to grind her hips more aggressively.

I pulled my mouth away from that nipple, planning on going back to the first one, when Ann quickly pushed my head into her chest.

"No, don't stop. You're going to make me cum." She cooed to me.

With renewed vigor I went to work on the nipple again. I sucked as much of her breast into my mouth as I could, then released it and clamped down on the nipple.

"Bite it!" She gasped, and I did. "Harder!" She said loudly.

I didn't want to hurt her, but I did as she asked, and delicately applied more pressure with my teeth while pushing against the tip of the nub with my tongue. As I did this Ann put one of her hands on her other breast and frantically started to squeeze it. 

"Oh god yes! I'm so close Scott! Squeeze the whole thing with your hand while you do that!" She called out hoarsely.

Her excitement was contagious, and I felt like I couldn't satisfy her need fast enough. My hand wrapped around her whole tit and I gave it a firm squeeze while keeping my bite in place.

"Yes! That's it! Don't stop!" She groaned and started to rapidly grind and slam her hips downward. Each time her hips hit mine she moaned, and after half a dozen times her head arched back and she smothered her chest against my face. I tried my best to maintain my stimulation of her nipple through her movements. I must have done enough, because her whole body finally stiffened for a moment and she let out grunt of satisfaction as she hit her climax. I wasn't sure when to stop, so I didn't, and it took her a few moments as she recovered from her peak before she gently pushed me away.

"Damn, that felt good. I can't believe I've gone so long without that." She kissed my forehead. "I'm glad you're a quick learner. We're going to have so much fun together." She said and smiled. 

I wrapped both my arms around her and pulled her to me so that my forehead was against the space between her tits. She put her arms around my head and held me. We remained like that for a minute or two without saying anything.

"Are you okay?" She asked, breaking the silence.

"Oh yes. Just enjoying how you feel when I'm holding you." I replied. She squeezed me as if to thank me for the comment. 

As I held her I realized how all of my longing in the past was well placed. There had been nights where I wondered just how the simple pleasure of the warm embrace of a woman, the feeling of my skin on her warm skin, and the smells, and other sensations, would all feel. Now that it was becoming reality I understood just how wonderful it really was, and was so happy that I'd decided to accept Ann's offer of intimacy.

"Thank you, Ann." I said.

She leaned me back against the back of the couch and she sat back so she could look at my face. "For what?" She asked, clearly unsure what exactly my meaning was.

"For asking me to be with you. I can't count how many nights I spent wondering what this would be like. Things like the simple pleasure of holding a woman, or feeling her skin on mine. I knew I'd eventually find out what it was like, but it always seemed so far away." I said softly as I felt a bit of emotion coming on.

"Ah, I understand. I've missed it too hon. Ever since my divorce I've been virginal. You're not alone in having spent many nights longing." She stated. "I'm glad to hear that you appreciate things like that. A tiny part of me worried that you wouldn't want to spend any time on fun stuff like this."

"Not me. I've wondered about so many things, not just sexual stuff either. It'll be nice to finally experience some of that."

Ann climbed off of me and sat beside me on the couch. "You know, I always assumed you were in a relationship. You're a good guy, Scott. When you told me you were a virgin, I was shocked. How many times have you been in relationships?" She reached out to hold one of my hands as she spoke.

"Well, one I guess. It was kind of different than a normal relationship. Mostly we talked online, so it was more of a spiritual and intellectual thing. There was never any physical contact. I enjoyed it, but it was kind of weird." I recalled the one time I'd met a woman I actually felt I would like to be in a serious relationship with. She wasn't my ideal woman physically, though she was definitely beautiful. But I had fallen in love with her mind and her faith. Unfortunately she had a tendency to run to the bad boy types, leaving me out to dry, which is exactly what happened to end things between us.

"Well somewhere out there is a woman who you'll marry. Hang in there. In the meantime, I think the two of us are going to be able to satisfy more than just our sexual needs. I'll be honest with you, when I'm not at work, things can be terribly boring for me. I wouldn't mind a friend to hang out with once in a while."

"I'd like that Ann." I said to her. My emotions were causing my eyes to water. I'd often struggled with the how things had worked out so far in my love life. Talking about it with Ann, and finding that in a way we were kindred spirits in this regard, made me feel relieved. But at the same time I was sad when I thought back to how often the whole thing felt like a burden.

"Oh Scott, I'm sorry." She whispered when she saw my eyes.

"It's okay." I shook my head and smiled at her. "I'm glad we're talking about this."

"If you're not comfortable with something though, please tell me."

"I will, don't worry." I assured her. "You too, okay?"

"Of course hon." She said as she pulled my hand that she held and pressed it against her body before releasing it.

I wrapped my arm around behind her and pulled her to me. I wanted to kiss her again, so I turned her and laid her down so her shoulders and head were lying across my legs. She smiled up at me as I leaned over to kiss her.

When our lips touched I got this electric feeling through my body, giving me goose bumps. Ann reached up and curled an arm around my neck. I pushed my tongue into her mouth and explored with it. She responded in kind, licking under my upper lip and then sucked it into her mouth. I pulled away from her.

"I really enjoy kissing you." I said with a grin.

"Likewise." She was smiling as well. "Can I ask you something?"

"Sure."

"Before, when you said you've wondered about things, did you mean anything sexual?" She queried as she stood up and sat sideways in my lap. I put an arm around her.

"Yes." I replied, biting my lower lip. I wondered how deep she was going to go with this line of questioning. I'd had some days in the past when I was very horny and ended up looking at some rather unusual things online, some of which definitely piqued my curiosity.

"Like what? I can see you're thinking of something." She said as she observed my expression.

I hesitated for a moment, not really sure how to tell her some of my interests.

"If you don't want to share, that's cool. Maybe I can coax it out of you another way. I have some books that are filled with some interesting pictures." She said and winked. "How about we look at those? I may have been married before, but my husband wasn't the adventurous type. You may just find that we have some unexplored curiosities in common. "

"I can handle that." I told her.

-- More To Come --



From Co-worker to Student Ch. 03



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.

-----

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.




From Co-worker to Student Ch. 03



It took her a bit of time to relax after that. I was barely able to draw a breath through my nose, so I wrapped my arms around her thighs and gave a little pull so she'd know I needed to be released. Thankfully she understood, and I pulled my head away and gasped for air.

Ann simply lay where she was, too tired or too entranced by the fading pleasure to move. I'd caught my breath and sat next to her. I looked her over and found myself thinking that she looked so erotic. Her legs were spread apart again, her arms were extended over her head which caused her breasts to pull up and take a more defined shape, and her face was very flushed, especially her closed eyelids.

"That was…" She whispered weakly. "That felt good." She smiled and opened her eyes.

I leaned over and planted a quick kiss on her mouth. "I'm glad. I really enjoy making you cum."

"Music to my ears, Scott." She sat up and pulled my face to hers and proceeded to lick her juices from my face. "I'm glad to see you didn't suffocate down there. My legs can get a mind of their own sometimes."

"Do you do that twice very often?" I asked. Making her do that had turned me on big time.

"Oh, heavens no. I was just really hot with anticipation. You did a fine job with that sweet mouth of yours too." She smirked and kissed me. "You know…I still haven't seen you naked yet." Her eyes darted to my crotch where my prick was hard and somehow not popping out of the opening in the front of my boxers. Then she looked back up at my face and we smiled at each other. "Can I take those off for you?" She asked and I nodded.

I lay on my back and lifted my hips so she could slide my boxers down. Once they were off she tossed them onto the floor.

"Mmm, finally." She slowly looked at me from head to toe. "Some day Scott, someone woman is going to be so happy she's married to you. But for now, I'm going to have to fill that role." Ann knelt next to me and leaned over me to kiss my forehead. "Can I touch you? I've been letting you give me all sorts of pleasure and haven't returned the favor."

"Yes." I said. "Do whatever you want."

She cooed softly to herself as she planted kisses all over my neck, chest, arms, nipples, stomach, and hips. When she came to my circumcised cock she paused to look at it. I'm not the most well endowed person. At full erection I am a little less than six inches long. After she paused she moved to between my legs.

"Lift your legs in the air for me." She ordered, and I complied by putting them straight up. She sat down so that she faced me, her legs were spread unbent on the bed, and her crotch was near my ass. "Okay, you can put them down." I lowered them so that they bent over hers. She now had a nice seat between my legs and my cock was right in front of her. Plus she could easily watch my face.

"How I've longed for the past few years to feel a man's hardness in my hands." Ann said and licked her lips. Slowly she reached out with one hand and put her thumb and index finger around the base of my prick. I watched her closely. She leaned over and kissed the head, then licked the clear fluid from the tip. 

"Oh, what's this?" Ann said, a little bit surprised. She'd pointed my cock up towards my stomach, meanwhile her eyes were looking down at my balls. "You shave?"

"Mmmhmm." I nodded. I had first shaved my pubic hair in college, and upon finding it very comfortable, hadn't stopped doing it since.

"I've never met a guy who does that." She said a little absentmindedly as her free hand felt my smooth scrotum. "It'll be nice not getting hair in my mouth." She winked at me.

She let go of my cock with her fingers and wrapped her fingers around it so that she was merely touching it without squeezing it. Then she slowly started to stroke me. It was obvious to me that she had no intent of going quickly. I could tell that it wouldn't take much for me to cum, regardless of who was doing the stroking or how fast they were doing it. She pumped me a few times, keeping that slow, patient pace, before removing her hand again.

"How about a little lube to make things nice and slick?" She said. "I just happen to have plenty thanks to you." That said, she put her hand on her wet pussy and got a few of her fingers slick with her own juices. "There we go."

That wet hand grasped my cock again in the same gentle manner, and she continued stroking it. Because she was moving her hand so slow, each stroke took about five seconds. And she'd done this no more than a half dozen times when I felt the sensations of an oncoming orgasm.

"Ann…it won't be long now." I told her. 

She kept doing the same thing and licked her lips. As my breathing started to pick up she leaned over and swirled her tongue around the head of my cock. On her next down stroke she took the whole head into her mouth and gently sucked it while flicking her tongue over the hole. Meanwhile her hand kept doing its thing.

"Ann, I'm really close!" I moaned to her. I'd been watching her this whole time, but the pleasure was so much that I closed my eyes and arched my head back.

After I had said it she sat back up and started stroking a little faster, but didn't squeeze at all.

"Come on baby, cum for me." She urged me on quietly. A moment later the first stream shot out into the air and landed on my stomach. "Oh yes. Keep going; let me see all of it." The gentle strokes continued, summoning another few jets of white fluid out of me, most of which oozed out and flowed over onto Ann's hand. She kept jacking me off until no more remained.

"There we go. Feel good?" She asked while looking me in the eyes. Her hand kept playing with my cock as it lost some of its firmness.

"Very." I told her. "You definitely have a nice touch."

"I like to go slow." She said as she wiped the cum from my stomach with her hand and rubbed into onto my cock before stroking me some more. "Want me to keep doing this?"

"Oh…I don't know if I have any more in me after that." I told her. I'd tried many times while masturbating to bring myself to orgasm twice in a row, and rarely was successful. I usually needed a short break in between to do it. However I was extremely turned on with Ann, so maybe she would be able to do it.

"You'd be surprised what a woman with a couple slow, persistent hands can coax out of you." She stated.

I didn't reply. Instead I shut my eyes and focused on her touch. Her hands, which felt warm when she started, felt hot now. They slid over my skin easily thanks to our combined lube. As she stroked me, she would occasionally stop at the head of my prick. There she'd make the inside of her hand to be shaped like a cone, and she'd gently squeeze and relax it on the head of my cock. This focus on the sensitive head created a lot of sensation, and after she'd done it for a few minutes my cock was hard again.

"There we go." She smiled at her handiwork.

Ann continued her slow, methodical hand job for a while. Neither of us said anything, and the only sounds in the room were my occasional quiet moans, the sound of her hand sliding over my slick cock, and Ann frequently making "mmm" sounds while she played with me. I needed something more if I was going to cum again and I knew what it was.

"Put a finger in my ass." I told her.

"Oh? May I?" She asked, genuinely surprised by my suggestion.

"Yes, please do it. I think it'll push me over the edge."

That was all she needed to hear. Without stopping her stroking, Ann fingered herself to lube up a digit on her other hand, and then spread it around my ass hole. After that she started to massage around the hole, but I stopped her.

"Just push it in Ann. But go slow on the way in. I can take it." I wanted to feel her small finger pushing me open. I'd played with my ass enough to be able to take a lubed finger without any difficulty.

"Okay, if you say so." She said as she positioned her fingertip against my hole and started to apply pressure inward. "This is the first time I've had permission to do this to a guy."

"Really?" I asked, surprised by this. "Well, I'm used to it, so it won't take much for me to be ready to have your…." I involuntarily paused as her finger was all the way in me causing me to moan. "Oh man that feels good."

She slowly pulled her finger back out until just the tip was pushing the hole open, then she pushed back in. It took her a few repetitions before she started to go faster. The hand on my cock sped up as well.

"Oh Ann, use another finger…use two of them." It was my turn to coach her. She deftly added another finger to her probing on her next outstroke. "That's it. God yes. Please, go faster." I said, almost sounding like I was begging.

"Mmm, you're so naughty Scott. You feel so hot inside." She was watching her fingers going in and out of my rear.

All of a sudden I could feel the beginnings of an orgasm. I let out a loud sigh and closed my eyes. 

"Getting close?" Ann asked. "Oh yes, I can feel it. Your hole is pulsing around my fingers. Wow."

I just moaned at her words because they only added to my arousal. My hips had started to move in unison with Ann's hands. After a few moments she just stopped moving them and let me do the work while she watched me squirm. 

"Fuck my hands Scott. That's it hon. Maybe you need a little tighter hole for your cock to fuck?" She said and finally applied some pressure with her hand on my cock which drew a loud grunt from me. "Let me do the work now Scott." She said, and I stopped my thrusting. "Get ready, I'm going to go fast now!" She said in a voice tinged with urgency. And with that her hand on my cock started to pump quickly, a pace that she paralleled with the fingers in my ass.

"Uuuugggghh!" I grunted loudly, pretty much shocked by her sudden change of speed. "Ann, I'm…it comes!"

Moments later I did. There wasn't nearly as much cum this time, but the orgasm was much stronger. I only remember my body tensing up for a few moments and my eyes rolling back. After that I let out a deep sigh and relaxed.

Ann said, "I knew we could do it." She was still stroking me despite all of my fluid having had come out already. "I love being able to give a man so much pleasure with my hands. Tomorrow I'm going to give you some different pleasure though." She winked at me. I knew what she was talking about and eagerly looked forward to it. I hadn't even spent much time thinking about wanting to fuck her proper because I was thoroughly enjoying what we were doing. But now that she mentioned it, I imagined my cock pumping in and out of that little pussy of hers. I definitely wanted to take my time with that.

"It looks like you're pretty much spent Scott." She said as she let go of my soft prick. "I'll have to let you get plenty of rest before I do that again."

"No kidding. I actually feel a little sore now." I told her as I noticed that there was an ache in my cock from her long session of play.

"You'll be fine in the morning. How about we take a quick shower together and then get some sleep?" She asked while using some tissues to clean up the mess I made.

"That sounds perfect. I'm exhausted." I said and rolled off of the bed.

We got in the shower and washed each other quickly. I was a little apprehensive when cleaning Ann's pussy, so she did it for me. It wasn't that I was afraid to or anything like that, I just wasn't sure how deep to go or how hard to scrub it. She assured me we could do it again before the weekend was over, and I happily accepted that suggestion. Once we were finished, and had dried each other off, we got into bed and lay on our backs next to each other.

"Was today good for you Scott?" Ann asked and held my hand.

"Are you kidding?" I said, somewhat surprised that she was even asking the question.

"I'm serious. I told you I wanted to make sure you had time to take everything in and enjoy it." She turned on her side to face me.

"Ann, I wouldn't change anything. I'll probably play it all over and over in my mind for a long time." I said happily as I faced her.

She only smiled in reply, and kissed my forehead. "I feel the same way. I like being with you."

I didn't know what to say, so I put my arm over her waist and pulled her closer to me. Neither of us said anything else that night. After a few moments she turned over and scooted her body against mine. I replaced my arm over her and nuzzled my face against her neck, and Ann pushed one of her legs between mine. I closed my eyes and enjoyed this wonderful position. Not long after that I fell asleep.

-- More To Come --



From Co-worker to Student Ch. 04



I woke up startled for a moment having had forgotten where I was. Once I remembered everything I relaxed, opened my eyes, and smiled. I was also surprised to find Ann not in the bed with me, but I quickly spotted her standing nearby rummaging through a dresser. She had her back to me and was bent over slightly. I took the opportunity to admire her bottom which was in its full naked glory. It was hard to believe that just 24 hours earlier I was probably getting ready for work where I'd be viewing Ann as nothing but a co-worker. Now I was lying naked in her bed after having spent many hours becoming more intimate with her than I had with anyone else.

"Hey you," She said after turning around to glance at me on the bed. "Sleep alright?"

"Kind of. It's a little weird sharing a bed with someone for the first time."

"Feel like getting up? Or do you want to sleep more?" She asked as she slid into a pair of white cotton panties that covered up much more skin than the ones she wore the night before.

"I'm good." I told her and realized, thanks to my stiff prick, that I really needed to use the restroom.

"Okay." She smiled and picked through the drawer again. "Are you hungry at all? We could drum up some pancakes or something."

"Nah, I don't usually eat breakfast." I told her as I rubbed my eyes, trying to wipe out the grogginess I was feeling. "But don't let that stop you if you're hungry. What time is it anyway?"

"Still pretty early, around 7:30," Ann informed me. She was facing me again and putting on a bra that matched her panties.

"It seems later." I slid off of the bed and walked to the bathroom. My cock was pointing straight ahead, leading the way. "Be right back."

Ann followed me towards the bathroom and gave me a little slap on the butt. "You've got a cute ass." She said and slapped it again.

I sat on the toilet without thinking. Standing and pissing with a hard cock isn't a very good idea. Ann sat on the edge of the bathtub and faced me. I felt rather self-conscious about peeing at that moment. As a friend of mine once perfectly described it, I had a shy bladder. I couldn't get myself to go.

"Feeling a little uncomfortable with me sitting here?" Ann said with a quick laugh.

"Yes." I told her and wasn't able to hide the embarrassment on my face.

"Oh come on. It's just a bodily function. You need to relax hon. I hope your spending time with me, being naked and all, will help you get over how shy you can be sometimes." She poked a finger into my knee. "I know you're going to piss, so just go for it. It's not like I'll be offended."

I knew she was right, so after a bit of relaxing I finally let it out. It was one of those very satisfying pisses that guys have when they wake up having to go badly.

"Good boy. Now that that's out of the way, how about we decide what we want to do before you have to go help your friend?"

We decided that the rest of the morning and short time after lunch before I left would be spent doing stuff that wasn't sexual. I think we both knew that the evening and following day could easily be very intense, and the prospect of a little rest before that was appealing. The only exception to our morning of abstaining was when we showered. We cleaned each other and had a couple passionate kisses. After that we did some laundry, went for a walk during which our conversation was light and mostly dwelled on stuff at work. The one thing definite thing we did plan on doing when I got back that evening was cooking dinner together. Finally, prior to lunch, I helped her sort through some old boxes of stuff in her garage that she wanted to eliminate. The time flew by until I had to get going. I wanted badly to call my friend and tell him I couldn't make it, but that just wasn't my way of doing things. So when the time rolled around, I gave Ann a tight hug and quick kiss on the lips, and took off.

The friend I was helping was moving from an apartment just a few doors from my own to a house that he bought about 20 minutes away. Another person, one whom I knew from a few social activities, had come to help as well. Both of them owned trucks which were perfect for moving the big stuff, and I loaded my car with smaller boxes. After six trips, a total of about five hours, mostly because we decided to put most of the big things in place instead of just dropping all in one room, we were finished. The guy who was moving, being a very thankful and generous type, insisted on taking us out for a bite to eat. And despite my urge to decline, I went with anyway but opted for only an appetizer while knowing that Ann and I were planning eating together. That took another hour. So by the time we were completely done, it was around 7 o'clock in the evening.

During the moving time I had managed to put Ann out of mind for the most part. Not because I didn't want to think about her, but because I didn't want my friends to think something was going on with me. I had every intention of keeping my new relationship with Ann to myself, at least for now. Maybe, as time went by, our friendship wouldn't be something to be secretive about. But the physical side wasn't going to be part of my conversation with others.

On my way back I decided to stop at my apartment to brush my teeth and clean up a bit. I also thought that a call to Ann would be a good idea in case she needed anything from the store that would be necessary when we cooked soon. As it turned out she had picked up everything while I was out. There was one last thing that I needed to find out from her. I wasn't positive what would take place over the rest of the weekend, but I knew I needed to find out if we needed condoms. So I asked if should pick some up. She informed me that I didn't need to worry about it. I wasn't sure if she was on the pill or if she'd had a hysterectomy, but I was rather relieved by what she said. I didn't have to pick up anything for the evening, but I wanted to show her my appreciation for my experience with her so far, so I picked up a single red rose on my way to her house.

I arrived back at her place at around quarter to 8. It was later than I was wishing for, but neither of us was worried about the time. We had more than a day left for whatever fun we wanted, and plus many days to come in the future. As we both agreed, there was no need to rush anything. This whole thing was about two lonely people enjoying each others company.

My knock on the door was met by Ann hollering to me to "come on in". I wandered into the kitchen where she was, to my surprise, dressed up rather formally. She'd put on some black pants with vertical pink pinstripes on them and fit her snuggly, doing her shapely ass and long legs much justice. Her shirt, actually it was more like a formal tank top, was pink and had a modest cut in the front that hid all but her upper chest. On her feet were black mules. It was definitely the sexiest clothing I'd ever seen her wear. Her hair was tied back into a short pony tail. Meanwhile her face was still natural looking, with no more than a little makeup around her eyes and what looked like a little blush on the higher part of her cheeks. I literally stood still for a moment and just gawked at her. She looked magnificent.

I, on the other hand, felt very grubby in her presence. I was still wearing my jeans and t-shirt that I had put on to move. Why I didn't think to shower is beyond me. I guess I was just too excited about going back to her house.

"Welcome back. Get your friend all squared away?" Ann asked as she filled up a pot with water. Her words had broken my trance.

"Yep. I'm sorry it took so long. He was nearly begging us to put sort the furniture out a certain way. And then he insisted on taking us out for dinner." I told her and walked closer. I was nonchalantly holding the rose behind my back, and found it more natural to hold it behind the counter once I was leaning against it.

"Still got room for our pasta?" She smiled. "And some special desert after that?" And with that she winked.

"Of course. I only had a little bit to eat." I paused and walked up to her. "Ann, you look incredible. I've never seen you look so amazing...when you're dressed." I flashed a big smile. Then I presented the rose to her. "And this...this is my way of saying thank you."

She'd been putting the pot on the stove when I was talking, and upon seeing the rose she turned to face me. "Oh Scott..." Her voice trailed off as she looked at it, and then into my eyes. "Thank you. I love roses." She smelled it and I watched as she quickly pulled a vase from a cupboard, filled it with water, and put it on the counter with the rose standing within it.

She turned around and moved so she was up against me. Normally she was of the height that her eyes were at about the same level as my mouth. But with the shoes she was wearing her eyes seemed almost at the same level as mine. Her arms went around my neck and she looked into my face for a moment before kissing me quickly on the lips and hugging me. I put my arms around her and held her tight. 

"Scott, I know this weekend is special for you. I can't tell you enough how honored I am that you've let me be your first sex...your first lover. I want you to know that it means so much to me too." She said softly into my ear. I wondered what she meant, but didn't feel like that was the right time to ask, so I simply held her. After a few seconds she pulled back and kissed me on the cheek and then stepped back.

We were both quiet for a minute or two as we savored the sudden intimate mood. Finally Ann broke the silence.

"Chef Scott, my handsome assistant, are you ready to help me?" She asked and pulled two paper chef hats out of a drawer.

"Yes ma'am! What dish are we preparing today?" I jumped into my new role and put my hat on. I loved cooking, especially while doing it with someone else.

"This evening we are going to be going with an elegant spread of spaghetti, meatballs, and a side of gourmet garlic bread. And lastly, for our two guests of non-alcoholic preference, a pitcher of ice cold lemonade to wash it down." Ann said as she put her hat on. "I've already begun with the pasta, and believe now would be the perfect time for you to get going on those meatballs." She pointed to a bag of frozen meatballs that was on the counter.

"Gourmet indeed!" I declared, and we both laughed.

The meal turned out great, and I was glad to have not eaten much at the restaurant. The conversation was light and humorous, never touching on anything personal or relating to what we had done or would do during the weekend. I personally was glad for that because I my anticipation of what was to come was so strong. Maybe Ann felt the same way. Regardless, we had a good time.

Once we were done, our dishes cleaned up, and both of us had used the restroom, the living room seemed like the right place to go, so we ended up there and turned on the television. Ann turned off all but one of the lights, and that one she left on low, much like the dim setting that we were in the night before. As it had been after I'd given Ann the rose, we were both very quiet. It wasn't an uncomfortable silence, but there was definitely a tension in the air. The TV was showing a romantic movie, and as we sat there watching, the scene was one of two lovers in the midst of a passionate kiss. I glanced over at Ann who was sitting on the couch. She was clearly turned on. I could see her bosom rising and falling with each breath, and her mouth was slightly open. My mind started racing, thinking of what I should do. I wasn't sure if she just wanted to sit and relax, or if she wanted me to make a move. I immediately decided that I needed to do something. But being the chicken that I was, I just couldn't bring myself to get up and do it.

I took a few deep breaths and felt my hands get clammy. "I'm not going to wuss out this time." I thought. "I must do this." I looked at her eyes, hoping she would look back. Instead she leaned on her side and rested her head on the arm of the couch. "Is she tired?" I wondered to myself. "No, she's just relaxing. That's got to be it." I looked back at the television. The two lovers had taken their clothing off and it was obvious that they were going to make love. "Damnit Scott, do something!" I screamed in my head. "All I need to do is get up, and kiss her. It's not like she's going to reject me or something. There's no reason to be such a chicken." I was feeling more confident. "Alright, let's do this. If I don't do it now, I'm probably not going to at all." I took a few more deep breaths. There was no way I could let this moment go without acting on it. "Go!" I yelled at myself in my head. So I looked over at Ann and stood up.

I walked over to her slowly and crouched down in front of her. She didn't lift her head off of the couch, so I moved close to her and kissed her on the lips. That first touch of our skin was electric. She let out a quiet "mmm" to herself and cupped my face with one of her hands. I pulled back and brushed her bangs away from her forehead and kissed it, and kissed her cheek and then her neck. She leaned back and pulled me to sit next to her.

My lips went back to hers and she opened her mouth in response. I licked under her upper lip and pushed my tongue into her mouth to find hers waiting. As the intensity of the situation took hold on me, I leaned forward and Ann ended up leaning back against the arm of the couch again.

"I thought about you all day today." She whispered as I planted kisses all over her neck and face. 

I needed to kiss more than just her neck and lips and face. I longed to touch every part of her naked skin. I reached to take pull her shirt up, but she stopped me, leaving me puzzled. She seemed to hot and ready, but I stopped and looked at her quizzically.

"What's wrong?" I asked.

"Nothing." She let out a deep breath. "I have a surprise for you, and I don't want you to spoil it. I just wasn't anticipating you taking the lead like this."

"I'm sorry." I replied and felt a little bit frustrated. But she quickly erased that thought.

"No, it's okay Scott. I'm glad to see you're getting braver. That's a good thing. But I've wanted to do this...to give you this surprise since we flipped through those books yesterday. Here, sit down and close your eyes. I want to do a few things before I show you. It'll take me just a minute, okay?" She stood up and looked at me, anxious for my consent.

"Okay." I nodded, closed my eyes and leaned my head back against the cushion of the couch. 

She had me feeling nervous again. I listened as hard as I could to what she was doing. First I heard the TV turn off, then her walking out of the room and coming back a few moments later. After that I heard a lighter being clicked, followed by something being set down on a table in front of the couch I was sitting on. The lighter, at least that's what I thought it was, clicked again, and another object was placed on the table. Then another click that sounded like a light being turned on or off. Then she walked out of the room again, and returned again moments later. That's when I smelled something. It was the scent of a candle that had just been lit, and the aroma of the candle too, which was a very soothing and subtle flavor of vanilla.

"Please don't open your eyes until I tell you to." She said quietly. "Put your hands between your legs." 

I didn't need to be told twice, so I clasped them together and set them between my legs. Suddenly I felt her weight on the cushion next to my left leg, and then my right leg, and finally her sitting on my lap.

"Don't open them. Put your head up straight for me." She ordered and I complied. "I'm going to put a blindfold on you."

"Why?" I asked, slightly concerned. I trusted her, but this was definitely unexpected.

"Don't worry." She said and wrapped a folded silk cloth around my head to cover my eyes. "Good boy. I'm almost ready. Just relax."

After that she got off of the couch and I heard her doing something that I couldn't figure out. The only thing I knew for sure was that I heard what I assumed was a zipper.

"Okay hon. Hold your hands out in front of you." She said softly. As I held them out she took them into her own and helped me stand up. Then she led me around the table I mentioned earlier. At that point I was pretty sure I was standing in the middle of the living room.

"Now I'm going to use your hands to do something. Don't say anything. Just feel what I put your hands on. Let your fingertips touch and glide along. You'll enjoy this, I promise. Okay?" She said softly and kissed me on the cheek.

"Okay." I responded uncertainly.

First she let go of one of my hands and a moment later held it again. I immediately figured out that she had turned around so that her back was to me because she pulled my arms up under hers and touched my hands on her shoulders. I felt her skin. She felt hot to my touch, likely because my hands were cold and sweaty from being nervous.

"Relax Scott." She whispered and pushed her body back against mine. I exhaled deeply and did my best to do as she asked.

I focused on my hands again. They were still on her shoulders. I moved my fingers a little bit and found a strap of cloth between them. Ann must have noticed I found this because she slowly moved my hands down her chest until they rested just above her breasts. I could feel that the straps were connected to more cloth there. It was some kind of undergarment. I didn't know at the time what kind of cloth it was made of, only that I could feel it was soft and had some sort of pattern on it. But as Ann told me later, this particular part of what she was revealing to me was made of jacquard. 

She let my hands linger there for a few seconds and then took her time moving them down her sides to her hips where she stopped. As my fingers moved along the cloth I could feel the pattern on it. When my fingers stopped I could feel the edge of the garment and her skin. A little more exploration and I found a thin strip of cloth that was separate from whatever was covering her upper body. I figured it had to be part of her panties. 

Again she moved my hands, this time going towards her stomach where my fingers found some sort of rivets or something running vertically. She continued upward until stopping where I could feel the top edge of the jacquard and beneath it her breasts. She was breathing deeply and I could feel it in her chest rising and falling under my touch. I was waiting for her to continue, but instead she flattened her hands against mine, pressing them against her tits.

"Scott, I'm so hot right now." She whispered and eased up on her tits. Her hands then guided me down the middle of her torso along that vertical seam and I found the bottom edge of the patterned garment. Just below that was the top of her panties. I let my fingers roam, touching her soft skin and poking for a moment under her waistband. Ann waited longer than usual that time. I was tempted to let my fingers push down even more so I could caress her pussy, but she didn't let me get that chance.

She pulled my arms straight out in front of her, and in the process pulling me tighter against her back. Back down towards her panties she led me until my hands rested right on the delicate fabric that covered her sex. When she'd said she was hot, she wasn't exaggerating. Through the cloth I could feel not only her heat, but also that the cloth wasn't just damp, it was wet. She relaxed her grip on my hands and gripped them so that she had made my hands into loose fists but had left my index and middle fingers extended.

With each hand she slowly moved my fingers along the bottom edge of her panties going upwards towards her hips. Then she moved back in the opposite direction, ending up with my fingers pressed against her pussy lips. She held one hand away from herself a few inches, and with the other pressed my fingers into her. Under her direction, I massaged her through the panties for a few moments before she pulled that hand away as well.




From Co-worker to Student Ch. 04



"Now I need to sit you down again." She whispered and led me to a chair. "Put your hands on the floor in front of you, and when you feel my feet, I want you to let your fingers explore their way up to my waist. Go slowly."

I placed my palms flat on the floor and felt her toes. I put my hands on her feet and felt that she was wearing hose. Very slowly I moved up, feeling her narrow ankles, then the swell of her calves, her knees, and then her thighs. That's when I stopped. The hose had ended and I felt something different there. It was a wide band of the hose material. 

That's when I realized what she was wearing. I recalled our viewing of the books the day before. I'd pointed out my interest in the picture of a woman wearing a bustier, panties, hose, and garters. I smiled as I put everything together, and slowly felt around her thighs for the garter clips. Sure enough, they were there. Before I went the final distance to her panties again, I my fingertips up and down along her thighs a few times.

Finally, I found the garters again, and traced their route to her waist where Ann's hands met mine. She pulled me up to her and wrapped her arms around my neck. I could feel her breath on my face.

"Did you like that?" She asked.

"Yes." I nodded and smiled. "It was so...erotic. Can I see you now?"

"Not yet. I want you to feel how wet I am." She whispered. I thought I detected a hint of anxiety in the way she said it.

She sat me back down and grasped the index and middle fingers of one of my hands again and brought them to her pussy. First she grazed the tips against her panties, tracing the line of her slit up and down.

"I can feel it on your panties. You're burning up." I couldn't believe how wet she was!

"Yes. I want you to really feel it though." She said and guided my fingers to the side and we pushed the triangle of cloth over.

She was more than hot. She felt like an oven. And she sopping with juices. Everything I felt as my fingers roamed was wet. She seemed in a hurry, and guided my wandering digits to her lips.

"There, feel me Scott. Feel me inside." She said with a deep exhale followed by an audible swallow.

I fingered her labia softly between my fingertips. I knew her body was the same temperature as my own, but everything about her felt like it was on fire. I traced the outline of her pussy starting low and stopping at her hood.

"Please Scott, I need to feel your fingers inside me." She whimpered. Her desire for haste and this obvious display of her need was an immense turn-on for me.

"Okay." I whispered. As much as I liked this first time to touch her pussy with my hand, I didn't want to keep her waiting.

I bent my index finger back so only my middle finger was extended. With the tip of it I found the spot between her lips. In it went, slowly but surely. She was blazing in her hole. The heat felt more intense than what I'd felt moments ago.

"God yes, Scott." She said under her rapid breaths. "I need you to fuck me with that finger."

I reached the point where my finger was all the way in, and started fucking her. After a few strokes she started to move her hips along with my motion. After a few more she held my wrist and my hand turned into nothing more than a toy for her. She sped up the pace considerably.

"Push up Scott. Press against the top of my cunt." She said and gasped as I did it. "Oh god, yes."

Her grip on my wrist tightened as she steadily moved her hips faster. I wanted so badly to see her doing this to herself. I reached up for the blindfold, but she quickly told me to stop. Instead she took my other hand in her free one and held it tightly by the wrist.

"I'm so close Scott. Soooo close." She whispered. Each time she pushed my finger in she moaned and exhaled simultaneously. "Another finger Scott. Please."

I straightened out my index finger for her on her next outstroke, and she quickly plunged both fingers back in.

"Yes! That's it. Ohhhh." She said loudly. Her grip on my wrists tightened and her hips bucked rapidly, slamming against my half-fist. At last I felt her hole tighten around my fingers and she stopped moving my fingers. Instead she jammed her hips against them in quick, short thrusts, each one causing her to let out a louder moan than before. With one last push in, she stiffened and sighed.

"Oh Scott...." She said and let go of my hands. "As good as that felt, I know your cock is the only thing that will really satisfy me completely."

I think I blushed when I heard that. I'm not sure why. Perhaps it was just the raw sexuality of it, or simply hearing her imply the two of us actually fucking for the first time. Regardless, I felt a great wave of lustful heat wash over me.

"Give me a moment to catch my breath, and then I'm going to take off that blindfold." Ann said as she ran her fingers through my hair. I could hear her breathing as she held onto me. "Okay, time to let you see what I've been teasing you with."

She reached behind my head, untied the cloth, and slowly pulled it away. The room was dimly lit, so I opened my eyes without worrying about being overwhelmed by bright lights. A quick glance to the side showed me that the things I heard her put on the table were two candles. They were the only light in the room, but it was enough that I could see Ann well enough.

I sat back and took in the view. Ann was standing a couple feet in front of me, turned slightly to the side. She had a closed-mouth smile on her face, and her eyes had a bit of a dreamy look in them. Her bustier, panties, hose, and garters were all black. She looked amazing. All I could do was shake my head in admiration of her beauty.

"I can't believe you did this for me." I said as I looked into her eyes.

"When I saw how much you liked the picture we saw in that book I knew I had to dress up for you. The blindfold part hit me while we were eating though. I was so...well, you felt how turned on I am. I hope you enjoyed it as much as I did."

"I loved it." I paused and looked her over slowly again. "Ann, you look perfect...amazing." 

"Thank you." She said and kissed me on the cheek.

"How long have you had that stuff?" I wondered out loud.

"Umm, actually I bought it today." She said as she sat sideways in my lap, put her arms around my neck, and leaned sideways so that we were leaning against the back of the chair. I put my arms around her waist.

"You did? Ann, you didn't have to..." I trailed off. I couldn't believe it.

"Shhh. It was worth it." She whispered to me.

We both turned our heads to face one another. I couldn't do anything but smile at her. "I can't believe I'm sitting here with you on my lap." I was thinking out loud again.

"Me too." She answered and closed her eyes. 

We sat there silently with our eyes closed and rested for a couple minutes before Ann spoke quietly. "My husband...ex-husband, he never did this with me."

"Never did what?" I asked with obvious surprise.

"Just sat and cuddled and touched me. He liked digging into the 'good stuff', as he always used to call it." She sighed and wiggled her body tighter against mine. "When you first said that you loved how it felt to simply hold me, my heart skipped a beat. It was like music to my ears."

"Did he ever, like, give you pleasure?"

"Oh yes, he liked doing that. His knew how to put his tongue and fingers to good use. But he didn't think that the little things, like us sitting here, were worth his time." She put her head on my shoulder. "I could sit here all day. I love it."

"Me too." I said and smiled. I let the thought linger for a moment. "Can I ask you something? You don't have to answer if you-"

"Why did we divorce?" She interrupted.

"Yeah."

"I knew you'd ask eventually." She paused. "Mark, that's his name...he's a good guy. Before we married he treated me like a princess. There were some things about him that I had a hard time with, but no one is perfect, right? Anyway, after we married everything was great. We had the kids, everything was wonderful for so long. And then about four years ago I noticed that he was changing. He'd always been a controlling type, and aggressive too. But when he started to change, those parts of his personality became more...more pronounced. I was able to deal with it though, that's just how I am. I can tolerate a lot and let it slide." She stopped to wipe a tear from her face.

"Ann...you don't have to tell me." I said, nearly whispering.

"No, it's okay. I've kept this bottled up for a long time." She stopped again and sighed. "He started to isolate himself from me. At first I didn't know why. I thought maybe it was me, so I started to question everything I did around him. I wanted to please him and was willing to do whatever I could to do that. But he insisted it was not me, it was him. Finally, one day, I finally confronted him and he told me he felt like he wasn't a man anymore. The reason that he was putting up walls between us was because he...he was having impotence problems. The poor guy, I felt so badly for him. But I still loved him, I swear. I knew his mind and knew that he was a good man. I wasn't going to let sex keep me from loving him. But he didn't feel that way. God Scott, he completely changed." She stopped and shook her head. I could tell she was on the verge of crying.

"Ann..." I whispered. I felt totally helpless to do anything. All I could do was hold her tighter and hope it would comfort her.

She took a deep breath and continued. "For a whole year we were like roommates and we bickered all the time. I felt like I was living with a shell of the man I had known for so long. Somehow the kids didn't seem to be aware of most of it. One day Mark came home from his job and told me he was going to move out. I was shocked. Everything was falling apart and I couldn't do anything to fix it. I fell into depression, and like him, was just a shell, a zombie going about my life. I felt that a divorce was nearly certain, and just a few weeks after he moved out, he filed the papers. I begged him not to, but he did it, and wouldn't listen to me when I tried to make up. He's so stubborn. We went through with the divorce and settled on our custody of the kids. That was the hardest part for me. When I walked into the court to decide how much time I could spend with my own children, I felt broken. Mark ended up getting the better end of that deal." Ann paused to sit up, but didn't leave her position on my lap. I wiped a tear from her face and she sighed before continuing. "It took me almost a year before I felt like myself again. A year, Scott." She shook her head.

"I'm sorry Ann. I don't know what to say." I had tears in my eyes. Prior to this I had no idea what she'd been through. My impression of her was one of a person who was always positive, happy, caring, kind, and compassionate. As I thought about her enduring a year of depression and what probably seemed hellish, my heart went out to her.

"You don't have to say anything hon. Being able to talk about it, and having you here holding me, it goes a long way to comfort me." She let out a deep breath that sounded more like one of relief than pain or tension. "After that year, I felt like a new person, and in a way I was. I was single again, had a house to myself, and my job was still secure. I felt very fortunate, and because of that I made a point to never let myself miss savoring the good things that were placed in my life. And whenever I encounter someone who was in need, I make an attempt to help them. My life is so good now Scott. I feel so blessed, even after losing Mark. Everything seems so precious now, so...valuable. I don't mean I didn't realize that before, but after the divorce my eyes were opened." She stopped. I wasn't sure if she was finished.

"I had no idea. Even at work, I mean we only normally saw each other in the hall and stuff, but I could never tell you were struggling." I told her.

"I made a point to hide it. I don't think anyone at work knew. My ability to take on a lot of crap really helped me in that. I wish I'd had someone back then to talk to though. Keeping it all in was terrible for me."

A comfortable silence settled on us after that. Ann put her head back on my shoulder. As I digested what she'd shared with me, I started to cry. I found myself having a new appreciation for her. Not only that, I felt an immense new sense of caring for her. Even thought we'd really only recently starting getting to know each other, I couldn't help but get caught up in the emotion of it all. I'd never endured the kind of hurt and pain that she had, so seeing her to come through it to be the person sitting there with me, I couldn't help but admire her strength. 

"Thank you Scott. Thank you for listening to me, and for holding me, and giving yourself to me this weekend. I hope..." She paused and sat up so she could look me in the eyes. When she saw that I was crying she sighed and got a sad look on her face. "I hope that after you leave tomorrow that it won't be the end."

"Me too." I said.

Ann wiped a tear off my cheek and kissed the spot. "I didn't mean to make you cry. I'm sorry." She wiped my other cheek and kissed it.

"It's okay." I said as I shook my head. "Sometimes it doesn't take much to get me emotional."

"I don't want to get up. Can I just sit here forever?" She said and kissed my cheeks again.

"Sure. But only if we're both naked." I responded and smiled slightly.

"Deal. So, let's do something about this stuff we're wearing then." Ann stood up as she said it. That's when her erotic scheme from earlier came back to me. I think we both forgot about it once the topic of her divorce came up.

"Ann, I'm sorry. We were really...you went out of your way to dress up like that and I went and ruined the moment."

"Don't worry about it. I'm glad we got that out of the way anyway. It was bound to come up eventually. The timing wasn't the best, but it could have been worse." Then she paused and gave me a funny look. "And it doesn't mean we can't carry on with what we were doing."

"I don't know. The mood just seems weird now, you know what I mean?" I asked, unsure if I was the only one feeling that way.

"Yeah." She said and glanced over at a clock. "How about we sleep? It's pretty late. We can get up and start fresh with a whole day ahead of us."

"Sounds good to me."

Ann led me by the hand to her room and gave me a long hug. "Let's undress each other. Then we'll sleep."

I went first, smiling as I looked her over in the sexy lingerie she had on. She stood patiently in front of me, even turning around and bending over slightly to wiggle her ass at me. After unclipping the garters I had Ann sit down so I could remove the hose first. Slowly I coaxed the tight material down her thighs and stopped to kiss each one. Then I inched them off the rest of the way and kissed each of her calves.

With her legs bare, I had her lay up on the bed and straddled her hips so I could unhook the front of her bustier. There were a lot of hooks to open up, and as I worked on them Ann poked fun at me for taking so long. Finally I finished and opened up the bustier, revealing her bare torso. She looked so good, and I was tempted to go back on my agreement of going to sleep so soon. But I decided not to, and helped Ann sit up so she could remove the garment completely.

All that remained were her panties. The triangle of fabric in the front was still dark from her arousal. I put my nose against her the cloth and inhaled deeply. She smelled nice...her own unique mix of aromas. That scent of her soap and perfume and sweat and sex, even years later, was permanently imprinted in my brain. Even the faint smell of vanilla still turns me on whenever I smell it.

I stood Ann up and knelt down in front of her. Hooking my fingers under the elastic band I slowly pulled down the panties. She kicked them aside. Before standing up I planted a soft kiss on her pussy.

Ann was a much hastier than me. She made quick work of my shirt, tossing it on top of her panties. Her hands wandered over my chest for a moment, and then down to the fly of my pants. She pulled them and my boxers down at the same time.

"Much better. I love seeing you naked Scott. And judging from your little friend here, you like me too." Her hand wrapped around the head of my cock. "Come, let's cuddle and sleep." She pulled me by the prick into her bed. After she turned off the light by the bed, we found a cozy position and crashed.



From Co-worker to Student Ch. 05



The sun hadn't come out yet out when I woke up, but I could tell it was getting light. Ann was still nuzzled against me, so I carefully moved away in order to relieve myself in the restroom. When I came back I felt wide awake and restless. It was too early to wake her up, but cuddling with her was very appealing. Or, I thought to myself, I could just stay up and maybe take a little tour of her house. I opted for the latter choice. I found a clean t-shirt and some boxers in my bag and put them on.

So far I'd only seen the kitchen, dining room, living room, and Ann's bedroom and bathroom. The house was bigger than one would expect a single person to live in, so assumed that this was the same house that Ann owned when she was married. Upstairs there were two rooms other than Ann's and after seeing the contents of each it was obvious that the kids stayed in them when they visited. Between those two rooms were a bathroom and a closet. On the ground floor the only other room was set up like a den with a small television, a couple tables, bean bags, an old sofa, and a cabinet full of board games. I figured it must have been a room for the kids to hang out in.

The basement was mostly unfinished. Ann had put many boxes down there, and they were neatly organized and labeled. The part that was finished was a small room containing a desk, a small lamp on a table, a filing cabinet, and a few boxes on the floor. I was about to leave when I saw out of the corner of my eye that there was some correspondence on the desk. 

I respected Ann's privacy, so I didn't read anything, but I felt compelled to see what else was there. I shuffled through a drawer and found two bibles, one of which had dozens of little pieces of paper in it for bookmarks. I smiled knowing I did the same thing with my own bible. I put the bibles back and opened another drawer. Within it were many envelopes of pictures. 

The first few envelopes were full of pictures of various people who I didn't know. One picture caught my eye though. It was of Ann, who looked a little younger, and a young woman who was just as attractive as Ann. She was taller than Ann, had the same type of build, and long straight hair that was red, almost brown in color. Her eyes were brown. It was her smile that was most striking. As I looked at her face I felt myself smile as well. She looked like she could have been my age. I wondered how she and Ann knew each other.

Several more packs of photos later I put them all back and headed up to where Ann was sleeping. It was nearly 8 o'clock, not too early to wake her up, though I wasn't going to do so intentionally. As I made my way back to her I considered trying to fall asleep again, but another idea came to me. Maybe I would wake her with a little surprise, courtesy of my mouth and fingers. The thought excited me.

I smiled as I found her sleeping on her back. She'd kicked the blankets to the bottom of the bed and only a sheet remained over her body. After I took off my shorts and shirt, I slowly pulled back the sheet, carefully putting my weight on the bed between her spread legs. I could barely contain myself, though a small part of me wondered if this was a bad way to wake someone up. I mean, the pleasure would be nice, but what if Ann didn't want to awaken to find she was already working towards an orgasm? I was going to find out.

Her pussy was, to my surprise, already wet. She must have had a good dream, or her body was still feeling turned on from the night before. I littered kisses all over each of her thighs, her belly, and her hips. She stirred for a moment, turning her head aside and shifting her hips a bit before going still. I waited a few seconds before putting my face near her pussy.

Those delicate lips of hers weren't parted like they had been the day before. In the small gap between them I could see her wetness. It was like an invitation for my tongue, so I stuck it out and ran the tip up and down along the darkened edge of each lip. As I did this the lips sort of leaned to one side so I softly pressed my tongue against the bottom of the exposed flesh and took my time licking it a few times. Of course I couldn't let the other side be neglected, so I made sure to lick it as well. And finally I tilted my head sideways and took both labia in my mouth. I didn't suck or squeeze, rather I just held them so I could stick my tongue between them and stroke my tongue back and forth across the inner surfaces. I was greeted by her slick fluids which I gladly consumed.

I must have gotten carried away with having her folds of skin in my mouth because she started to wake up. I thought for sure that after having freed her pussy from my mouth that she'd settle back into sleep, but her eyes gradually open and looked at the ceiling. A few seconds later she saw me and she shook her head and smiled.

"You're so naughty. I thought I was dreaming when I felt something between my legs." She said while rubbing her eyes. "Keep going. I don't mind." She sighed and opened her eyes again. "What a nice way to wake up. I think I'm going to keep you in my closet from now on." She pulled her legs further apart for me, bending them at the knees.

Her hood was looking good by this time, so I let my tongue wander to it. Ann helped me by pulling it back and exposing the clit to me. Her other hand settled on the top of my head, gripping my hair gently.

"That feels so good." Her words were quiet. "That's it, lick my clit. Hmmmm..."

As I was licking her button I eased my index finger into her pussy. "You're so hot inside Ann. And wet too."

"Thanks to that tongue of yours hon." She whispered right as my finger was all the way inside. I pushed up against her g-spot. The reaction was her typical sharp inhale and slight arch of the back. "That's it. Oh god. Slowly fuck me with your finger. And suck my clit, but not too hard."

As I pumped my finger in and out of her I could feel the muscles squeezing it and releasing it. "Are you doing that to my finger?"

"Yeah. Ohhh Scott, I'm going to cum soon."

She seemed to be enjoying this slow type of stimulation so I didn't suck harder or fuck faster. I watched her face as I continued to coax the orgasm out. She had her eyes closed and her mouth open a little bit, occasionally biting on her lip. She looked peaceful. Suddenly she gasped and bucked her hips up causing my tongue to press hard into her clit. That caused an even more violent reaction. Her legs first bent all the way so her heels were touching her ass, and then they shot straight out and she brought them over my shoulders. I knew what that meant, so I took a deep breath. The hand that held my hair pulled me into her now undulating hips. My face was her toy, and she fucked it passionately.

"Ughhh...God I'm cummmmminnnng!" Her voice was shaking. Each time her hips pushed into my face she emitted a little squeal. "Herrrrre it commmmmes!" And with that she moaned loudly and her whole body started to shake. Everything that wasn't shaking was squeezing, including her thighs. I thought she had a vice grip on me the day before, this time was even tighter. I literally couldn't breathe.

She hung there in the thick of her orgasm for what seemed like half a minute. When she finally released me I sucked in a deep breath and laughed. I knew I wanted to wake her up to the gentle tonguing of her pussy. I hadn't expected to get her off this way.

"Good morning." I greeted her finally as I sat next to her.

She struggled to laugh between her deep breaths. "Good morning indeed. How'd you like a permanent job as my personal alarm clock?"

"How's the pay?" I played along.

"Such the smart-aleck." She poked me with her finger as she sat up. "And thank you. That's the first time I've had a wakeup call like that before."

"It was a pleasure." I said and smiled. "Wanna take a shower?"

"Actually, how about a bath?"

"A bath? I haven't had one of those in a looooong time. But why?" I replied.

"I need to shave, and from the look of your face," She reached out and squeezed my cheek. "You need to shave too."

I'd be lying if I said I hadn't thought about shaving a woman before. Ann's suggestion of this bath and shaving was exciting for me. Quite a few years ago I was in touch with a girl who was just a bit younger than me, and we got to talking about shaving her legs. She commented about how when she finally got married that she wanted her husband to shave her legs for her in the bath. That's when the seed of this whole thing was planted.

Ann collected the stuff we needed for shaving while I ran the water. By the time she was back the tub was only half full, so she made sure there was enough soap in the water to get it nice and bubbly. Once it was full it definitely was covered with enough bubbles. I couldn't even see the water.

I helped Ann get in first, not that she needed help. But I think she enjoyed having me hold her arm steady as she stepped over the edge of the tub. I was expecting to sit facing her, but she motioned for me to sit between her legs, and I eagerly complied. 

I can't say how relaxing it felt to not only have the hot water soaking me, but also Ann there with her legs around my waist, her arms wrapped around me, and her head beside mine so our cheeks were pressing against each other. It was blissful.

"I can't wait to make love to you Scott." Ann said and tightened her wraps on me.

"Ann, why me?" I asked her. The question had been on my mind quite a bit since she presented herself to me on Friday evening.

"What?" She asked, clearly confused.

"Why did you decide to ask me to stay here with you this weekend?"

"Oh." She paused. "Well, I guess it was a few things that sort of culminated into making me do it. I mean, it was a long week at work, and after all of those long days and not really doing much else even once I got home, I needed to let off some steam if you know what I mean." She poked my stomach as she made the comment. "But it was much more than that. Don't get me wrong, I was horny, but that was really a small part of it."

"What do you mean?" I asked, hoping she'd explain herself.

"After spending a week working side by side with you I found myself very curious about you. At work you're so...professional. People don't know much about your personal life. Maybe those guys you sit with know about that stuff, but the rest of us don't. Anyway, after spending that time with you, and even after the brief times you helped me in the past, I wanted to get to know you more."

"So you wanted to sleep with me." I thought aloud.

"No...well, that wasn't my original intent. I was apprehensive about asking you out to eat when we finished. When you didn't seem to think twice about it, and about coming here instead of going out, I was relieved and excited. Even then I only wanted to be able to get to know you better. You're a lot like my husband was before we married, but you're also much different than he was, and that's something I find very attractive about you. You're easy going and caring nature...and I guess even your way of keeping your personal life to yourself, it's something that I found myself drawn to this week. I almost found myself perceiving you as playing hard-to-get even though you weren't."

"I see." I replied, though I didn't completely understand. "It sounds like you saw me as a challenge."

"Oh, no Scott, it wasn't like that at all. Please don't feel that way. The only challenge was for me to get enough courage to ask you to stay with me." She kissed the back of my head as she thought a moment about how to continue. "If anything, I saw you as someone I wanted as a friend. The more I was around you and saw your gentle manner, the more I felt attracted to you." She paused again, sighing. "When I...on Friday evening, it wasn't until I was standing in my bedroom after you spilled the water on me that I realized how much I wanted you physically. I felt like a teenager again as I stood there trying to decide what to do. I never expected you to say yes."

We were both quiet for a couple minutes. I was digesting what she'd shared with me. I understood what she did saying, but felt a little awkward as I thought about her wanting to pursue me. It was the first time any woman had confessed such a thing to me. Having it come from a woman like Ann, older and beautiful, made it seem more surreal for me.

"You've filled a hole for me Scott." She chuckled as soon as she said it. "No pun intended. I've wanted for so long to feel appreciated, to be held, to have a friend who didn't judge me because of my divorce. I know it's not been very long, but you've made me feel that."

I sat silently for a bit to think. What she'd said made complete sense. In fact she was filling a hole for me too. The complete lack of physical affection in my life was painful at times, and that didn't even take into account my deep desire to be in a relationship. Ann was probably not the person to start a romantic relationship with, but I felt sure she would be a great friend as well as someone with whom I could engage in the tactile side of things when we both felt the need.

On the other hand I had been in situations that were somewhat similar before. Suddenly spending a lot more time than usual with a person who one finds attractive tends to generate feelings of attraction or, if the circumstances are right, even love. While I wasn't feeling a romantic love for Ann, I'd be lying if I said I didn't have feelings for her. So that whole idea concerned me. How would things be in two weeks or a month after we weren't spending every day in close contact?

"Don't you think that all of this, the feelings and stuff, might just be from the two of us being around each other so much lately?" I asked her.

"Probably. But what's wrong with that? We both obvious have a mutual interest in each other. So why not see where it goes?"

I had to admit she had a point. We were both adults capable of making decisions, and we both had needs we could fill for each other.

"Where do you want it to go?" I posed the question to her. This was really the meat of my curiosity at that point. She'd explained why we were there together, now I wanted to know what else she had in mind.

"I dunno. Let's see what happens, okay? At the very least we'll be more than just two professionals saying 'Hello' in the hallway at work. This may sound selfish of me, but I hope I can have you to myself on many weekends to come. I enjoy your company, and love the way you touch me. What do you think?"

"I think...that I hope for the same thing." I replied.

She kissed my neck and squeezed me tight as a gesture of her approval. "I told you before that I don't want to just be 'fuck buddies'. You're a great guy Scott, and I'm not satisfied with sitting idle and watching as good thing passes me by. Whatever happens happens."

With that discussion done, at least for the time being, we sat quietly for a while. The water had cooled off, so we decided to empty some of it out and freshen it with hot water. Once Ann was satisfied with the temperature and water level, we got back into the tub and sat facing each other.

Ann wanted to shave first, and offered to let me shave her legs, but I decided to wait for another time. I closely watched her do it, and admired how soft and smooth they felt when she was done. She also shaved her pussy, going slowly and telling me her method of doing it so I could shave her sometime later. 

After she was done, and I gave her legs and pussy a good thorough inspection, followed by my approval, it was my turn. My face was covered in stubble, and so was my pubic area and Ann was eager to shave both. First she shaved my face and then followed by closely inspecting her work by slowly kissing it all over. Then I sat on the edge of the tub and she took her time on the rest of me. I walked her through it, though there's not much to shaving a guy other than making sure the hair and skin are softened by cream or hot water or both, and taking time and care while shaving.

Once the shaving was done we washed each other up, while refraining from any fondling or kissing during the process. And then we dried and all that good stuff. We didn't say much after the shaving was done, and by the time we were drying each other, we were both saying nothing at all. I think the anticipation of finally making love was getting to us. I know for me, the bath had relaxed me so much that I was ready to do it slow and gentle with Ann. The other thing that had me excited was how soft and warm Ann felt after bathing. I wanted to wrap myself around her and enjoy it as much as possible!

"So I've been thinking about how we can do this since it is your first time. You probably want to be able to enjoy as much as you can. What do you think of lying on your back and I'll ride you?" She asked as she grabbed a clean towel from the bathroom and we sat on the bed facing each other.

"That sounds good." I said and nodded.

"Okay. I'll go slowly for you. You probably won't last long once you're inside me, so hopefully going slow will hold back your need to cum, at least a little bit"

"Okay." I agreed. "And you're sure we don't need a condom?"

"Yep, your boys are safe with me." She said and we both laughed.

For a few seconds we sat silently and just looked at each others faces. Finally Ann leaned forward, put her hands on my shoulders, and kissed my forehead. She indicated for me to lie down, which I did, and she sat on my stomach. The mood had suddenly become a mix of sexual tension and peacefulness.

"I want you to know that I really am honored that I get to be the first to do this with you Scott." She said as she looked down at me. Her hands ran through the hair on my chest. "It's been a long time for me as you know. I feel like a teenager, I'm so excited."

I only smiled and put my hands on top of her thighs. I was excited too, but my cock was, to my surprise, still soft. Ann, on the other hand, was visibly aroused. Her nipples were hard, and I could see her pussy was already wet.

"Ready?" She said as she moved back so her ass was between my thighs. I nodded to her.

She took my cock in her hand and softly stroked it. Following a few strokes she moved back even more, leaned over, and kissed the head. I could already feel myself starting to get hard, and Ann felt it in her hand too, causing her to smile. She swirled her tongue around the head without taking it into her mouth, and with her free hand she cupped my balls and massaged them. Her expert stimulation had me hard quite quickly.

Now that I was ready, she moved so she was sitting high on my hips again. She leaned over and put her hands flat on the bed on either side of my head. As she looked down she had a big smile on her face.

"I'm going to put you inside me, okay?" She whispered and bit her lip.

"Okay." I whispered back.

She moved slowly positioning her hips above mine and lining my cock up with her pussy. I watched as she pointed me straight up, and then ran the head of my cock along the outside of her hot entrance.

"Okay," She said quietly. "Here we go. Nice and slow and easy. Let me do the work, you enjoy it as much as you can. If you're going to cum, just let it go."

My mouth was slightly ajar as Ann patiently lowered herself onto me. I could barely see her lips as they hugged my cock, almost appearing as though they were beckoning it to enter.

"It's so hot." I thought out loud.

"Yes. God you feel good. You feel so big." She whispered as she approached the last inch.

I may have been a virgin to this, but she felt very tight. I assumed it was because she'd not had sex in so long. But regardless, it felt amazing. Between the tight hole, the abundant juice she was producing, and the intense heat, it felt like putting on a sensational tight glove that just came out of the dryer. But this one was alive and constantly massaging my cock.




From Co-worker to Student Ch. 05



"Oh yes. You're all the way inside. I don't think I could handle much more right now. I'm glad you're not hung like a rhino." She said with a slight giggle. "How do you feel?" She asked as she sat still, my cock completely engulfed inside her.

"Wonderful. It's so tight, and hot, and wet." I replied.

"Good." She leaned over and slid her hands under my shoulders. "Are you feeling like cumming yet?"

"No, I don't think so."

"Okay, I'm going to start fucking you slow then." She put her face against my neck. Then her hips started to swivel forward and backward. "Mmm, this is nice."

I closed my eyes as I set my hands on her lower back. My only hope was that I could somehow last long enough that we could both orgasm, but that was quickly dashed when I felt myself building up.

"Ann...I feel it, I won't last much longer." I whispered. She put her head beside mine so her mouth was next to my ear and her upper body was pressed against mine. Then she started to move her hips faster, and mine joined in the rhythm.

"That's it baby. Cum inside me. I want to feel your body against mine as you do it." She cooed softly into my ear.

"Are you close?" I gasped. My hips were working harder now, and I wrapped my arms around Ann and pulled her tight against me hoping it would give me some leverage to push further into her.

"No hon. It's okay, I want to make you feel good. Don't hold back for me. Close your eyes and feel how tight and hot I am as I'm fucking you." She whispered. Her mouth was literally pressing against my ear. Her dirty talk and her breath on my ear only turned me on more.

"Oh I'm gonna cum." My body started to go rigid. Each time I thrust my hips at hers I moaned quietly.

"That's it Scott. Let it go." She encouraged me, and a moment later I felt the first issue of my load fire into her cunt, followed by a couple more big jets, and then I relaxed.

Ann continued to ride me even as I started to soften, only stopping when she could feel that most of the life had been drained from my cock.

"How was that?" She said as she lifted herself off and sat beside me.

"Amazing. I just wish I lasted longer." I said and watched Ann grab the towel and wipe my cock with it.

"You will next time. We can do it again later once you're at full strength again." She smiled at me. She used the towel to clean herself as my cum leaked out.

"I want to feel you orgasm while I'm inside you." I told her.

"I do too." Ann lay beside me, put her head next to mine, and draped her arm over my chest. "Don't worry about it though. Before long you'll have me squirming when we do that."

I smiled and said, "What's your favorite position?"

"Let's see. Probably the one we just did. I like having control and watching as we make love." She traced her finger nail around one of my nipples as she spoke. "Another one would be if I sat in your lap facing you. Being able to sit up and kiss and have you play with my tits really turns me on. It's more work though."

I was feeling good again, and sat up. "I think it's your turn now." I told Ann.

"Oh? I suppose I could take advantage of that lovely mouth of yours." She winked.

I lay down and gestured herself above my head, but she had a suggestion.

"Want to try something different?" She asked.

I nodded and said, "Sure."

"Okay, lay so that your head is on the edge of the bed, and I'll stand so it's between my legs." She shared her idea with me, and we both got into position.

We had to use a couple pillows under my back and neck before my mouth was at the right level. Ann carefully positioned her pussy over my face and I got down to business. Her sweet little lips were still slick with her juices. They were hanging down and slightly separated, allowing me to graze the tip of my tongue over each one repeatedly. Ann was already getting into it, and she spread her feet apart a little more so that her pussy pressed snuggly against my mouth. I sucked her lips into my mouth and pushed my tongue between them, sticking it as far into her as I could. This drew a long "ahhhh" from her, so I engaged in fucking her with my tongue while maintaining my hold on her lips. No sense in changing what I could tell she was enjoying. Ann reached out and grabbed my hands and placed them on her tits. Eating her was taking most of my concentration, so I simply took her nipples between my middle and index fingers and applied pressure to them.

Ann took only twenty or thirty seconds before I could tell she was going to cum soon. She started to slowly fuck my face while quietly cooing and encouraging me. As her arousal grew her hand reached back and found a place on top of my head and gently pulled it up against her pussy. Her breathing turned to sharp inhales punctuated by quick moans.

We fell into something of a standstill, and for about a minute my mouth, which was now growing tired, worked to please her. I sensed she needed something to push her over the edge, so I took her nipples between my fingertips and squeezed them hard. Ann squealed when I did that and her hips started to grind with much more vigor. "More, I thought to myself." So I pulled her nipples away from her chest, stretching them and squeezing a little harder.

Without warning her grip on my head tightened and she brought her feet together so that she had my head locked. I tilted my head as much as I could so that my chin would rub her clit. Finally, after perhaps ten seconds of this vice-gripped position, I saw her arch back and heard her let loose a loud moan, and then another as she stopped grinding and changed to pushing hard into my face for a couple seconds at a time. As she did this I felt a gush of hot juice against my chin. My mission was accomplished.

She stood there for a few seconds without releasing me. I'd never complain about such a thing, but I could barely breathe, so I gave her a little slap on the butt, and she spread her legs apart so my head could rest on the pillow again. After that she just flopped forward on top of me, lifted her legs up, and rolled off.

"I really love doing that Ann." I told her as I sat up against the head board and pulled her to me so she was leaning back against me.

"Eating me?" She asked.

"Well, of course. But I mean doing it when you've got me in a tight grip like that. I love feeling your body's reaction when you cum."

"Really?" She sounded sincerely surprised. "I've only tried that with one other guy, before I was married, and he didn't like it."

"It's not the most comfortable thing, but I think it's great."

The two of us relaxed for a few minutes before cleaning up and then returning to the bed. We turned on the TV and Ann gave me a long soothing back rub, after which I massaged her ass for long time. I took great pleasure in finally getting the chance to touch every inch of her soft bottom. She must have enjoyed it too as I only stopped because my hands were tired.

Both of us were sore again after that morning of playing, so we ate brunch and took a long nap completely with plenty of kissing and cuddling. When we woke up the clock read almost 3 o'clock. Neither of us had enough energy to mess around anymore, so we showered again, and then cleaned up everything we'd left laying around over the course of the weekend. Once that was done we sat on her couch for some TV. I probably could have headed home, but neither of us was ready for our time together to end.

"So things at work aren't going to change, right?" I asked her as we sat there.

"Yep." She said as she leaned closer to me, and held my hand. "But outside of work..." She let the thought hang for a second and looked at me with a smile.

I answered with a grin. "What are you thinking about?" I knew she was simply smiling about the fact that we could indulge in satisfying each others physical needs whenever we felt like it. But I was curious to learn what her thoughts were about how often this might be.

For a moment she was silent and looked back at the TV. Finally she spoke. "I was thinking about...how I wish I could have you here every night. I miss having a man holding me when I fall asleep."

"As much as I'd love to do that, it's not really practical."

"I know. I'm just fantasizing." She said. "I guess we should figure out how often we want to do this type of thing."

"I agree." I answered with a nod.

"Well...You're welcome to visit whenever you want. Even if we're not, um, making love, I'd love your company. But I know that you've got your own life as well. Maybe we should just take things as they come, and if something works out, it works out."

"That sounds perfect. I just don't want to overdo it, you know? Not that I could ever get sick of this." I chuckled at the thought. "But moderation is probably a good thing."

"Oh, definitely. Let's just see what happens."

So that was our plan. After that conversation ended, the rest of the afternoon and early evening passed slowly as we sat around and enjoyed hanging out. Once 8 o'clock rolled around I decided to go home, though we did entertain the idea of me spending the night with her again.

As we stood by her door preparing to say bye, we stood silently facing each other and smiling. We hugged for a long time before Ann pulled away.

"Are you glad you stayed?" She asked.

"No, it was dreadful." I answered and we both laughed.

"You're such a smart ass." She remarked and held my hands before sighing. She looked into my eyes. "Thank you Scott. I know that you gave me a physical part of you this weekend. But I needed this so much." She said, and I noticed she seemed to be getting emotional. "I meant what I said last night about you filling a hole for me. I've been so lonely and aching for someone for such a long time. I hope we can do that for each other for a while."

I smiled and nodded. "Me too." I thought Ann was going to continue, but she stood quietly for a few moments before I saw a tear run down her face. "What's wrong?"

She sniffled and shook her head, smiling. "Nothing. I'm just glad. I really like you Scott. Not romantically, but really, honestly, as a friend. Being lovers will be something I always look forward to. But I really value your friendship."

"I feel the same way. For some reason I feel like we'll be very close." I said quietly.

"I do too. I just hope that it's not just from all of our emotions from this weekend. Kind of like what you said last night."

"I hope so too." I said, and paused. I held her face in my hands. "Thank you too Ann. I'll never forget this weekend." I hugged her again. "You've taught me and given me so much already. I can't wait to see what else we can share."

We held the embrace for a while. I kissed her forehead and then her lips.

"You better go. We'll see each other every day, so it's not like this is goodbye." She said.

"I know, though in a way it feels like it."

"It does." Ann kissed me once more. "Okay, go get some rest. You're going to need some time to recover from the weekend." She said and grinned. "I'll see you in the morning."

I picked up my bag and walked to my car, waving to her as I got into it. As I started the ignition and drove away, she watched me. I don't remember the drive home, or what I did between getting there and going to bed. Ann was all I thought about. I replayed in my mind the various things we did together, and smiled the whole time. As she promised, she didn't disappoint me, and I wouldn't change a thing about what we did.