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.

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"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.