Roark's End Ch. 01byRoark Calling©
Jenny and I met at a Learning center. I had just moved to Dallas, and was working as a co-op for a big electronics company while finishing up my last few college courses through correspondence. My ex-girlfriend from college had left me in quite a bit of debt, and I wanted to be free from it by the time I graduated. So I looked for, and found, a temporary job tutoring a couple of weeknights, and all day Saturdays.
I was working 6 days a week, and studying Sundays- but that's what I wanted at that time: no women, just focus on graduation, and a permanent position at my firm after that. The temporary job involved a long drive to a suburb, but it gave me time to clear my head, and think. I was able to live anonymously in a new city, and recover from the heartbreak leading up to the breakup with Rachel. I wanted to use this opportunity to concentrate on my future, and start a new life.
Jenny was the director of the center, and reported to the President. She, along with Glenda, the President, interviewed me for the job. She was beautiful, I could see that, but the only thing I cared about was convincing her and Glenda to offer me the job. Rather than paying attention to her looks, I was more impressed with the fact that she was very well spoken, asked me pointed questions about my educational background, and seemed to acknowledge my goals. I was very happy when she called me back in a couple of days to offer me the position, and relieved to find out that I would be able to pay off all my bills according to plan.
The job turned out to be exactly what I had hoped for. I would work all day and run Monday and Wednesday evenings. By the time I got to work Tuesday and Thursday afternoons, I had just enough stamina to focus on the kids and help them with their studies. It was a little better on Saturdays, when I was there from 8 to 5, and I had more energy. I managed to do a pretty good job there, mostly because I enjoyed the tasks, the kids, and the people that I worked with. Within a couple of months, Glenda gave me a raise, and Jenny started to take a liking to me.
We would talk in between attending to different students, and I was drawn to her because she was a terrific boss. She not only rewarded the tutors for a job well done, and also provided feedback and constructive criticism about how to help the students. When I got the first raise, she let me know that she was aware how hard I was working, and that she was very pleased with the job I was doing.
I asked her if there was something I could improve on, and her reply was, "Yes, you could be friendlier."
Still, I did not think much of it at that time. She was around 32, about 10 years older than me, and my boss. Not only that, I wanted to keep my nose as close to the ground as possible. And she was not someone that I would have been really attracted to at first sight. Being a runner, and coming from a tropical background, I always noticed the dark haired, lithe athletic types. Most of my previous dates had looked like skinny cheerleaders. Jenny was different, and more reserved. She did not laugh, she smiled. She had green eyes, curly blond hair up to her shoulders, and was voluptuous. Her 5'6'' frame was always stylishly dressed, and it was easy to notice the gorgeous curves.
It was not too difficult to picture her as the wife of a successful man, with a kid or two at home, and everything in order- except she did not wear a ring. Quite frankly, she made me very self-conscious, and lust was the farthest thing fro my mind when I talked to her.
It was only when we started talking more that I found out that the truth was far from what I had thought. I discovered that she was divorced, and that it had been a long painful process. She did not have any kids, and was also trying to return some sense of normalcy in her life by immersing herself in work.
These facts made me feel me much closer to my boss than before. I realized that we were both living the same life, in different ways. Yes, she was still my boss, but now she was also a friend that I wanted to open up to. As we started going to lunch on Saturdays, I told her about my past, and how I could empathize with her, because I had been burned too. We started forming a bond that grew stronger every week. Pretty soon, my reserved boss would share private jokes by pulling me aside, or confide some work related stuff to me. We also started talking to each other over the phone outside of work, and I could tell she was getting attracted to me. Pretty soon it was a lot more obvious- touching my hair, or commenting on my lean frame, or making fun of my huge pasta meals after running, and offering to cook for me.
It was exciting, but at the same time, a little bit nerve wrecking. After all, I was only 22, with not much experience with older women. The only other time I had been with someone older than me was with Lisa, in Houston, during a summer internship, and even then she was only a couple of years my senior. I also definitely did not want to lose my job, and was worried about what other people at work might start thinking. But I also did not want to give up on Jenny. It was exciting to receive the attention from someone that I respected a lot, and even more exciting because of my self imposed monk hood.
Somehow she started feeling like a forbidden fruit to me. I wanted to hold and comfort her, make her happy, and make love to her. It also did not help that I had not had sex in a long time. I started dreaming about her as I went to bed, and daydreaming about her at my regular job. I would imagine undressing her, and having her naked body next to mine, and then doing to her everything wicked that I could think of.
I would remember how my previous girlfriends had always enjoyed my tongue, and now I wanted to use it on her clit. I would also remember how my ex-girlfriend would marvel at my erection- my normally unassuming penis would become a thick eight-inch monster when it got excited.
Now, I would dream about pounding Jenny with my cock. I wanted to see her face, and the look in her eyes as she came. I had to masturbate every night to relieve my raging hard-on, before I could fall asleep. As my cum shot straight up and fell on my tight stomach, the last thing I could think about before falling asleep was that I wished I came on her soft belly.
Being the straight arrow that I was, I thought for a while about what to do- did I really want to risk embarrassment, not to mention the odd chance of losing my job, or did I want to ignore everything I felt about Jenny? As I was trying to make up my mind, she seemed to sense the tug-of-war in my mind. It turns out I did not need to worry about anything at all. One late Saturday afternoon, there were just the two of us left. I was depressed about having to say bye to her for the weekend, when she came by and asked if we could talk.
I decided right then that I had to get everything out in the open, and said, "I think we need to."
Sensing my mood, she told me that it would be better if we just went to her house and talked. At that point, I wasn't thinking anymore, so I just agreed to follow her. The drive to her house was excruciating. I was at once thrilled and sick- I just had no idea how this was going to turn out. Once we got to her house, I calmly followed her inside. She turned to look at me and brushed up against me, and smiled. Somehow, right then, I knew what would happen next. That touch was like a match striking the bomb. The next moment, we were kissing each other like high school kids, and our hands were all over each other. In between kisses,
I managed to say, "Oh God, Jenny, I have felt like this for a long time."
She just put a finger on my lips and said, "I know, because I've too. And that makes this right."
At that moment, that was all I needed to know. As I was fondling her ass, she was kissing my nipples through my shirt. My hard-on was very pronounced by now. Seeing this, she held it with her hand through my pants, and then turned around to press her back against me. As she led me to her bedroom, my hands were all over her, massaging her stomach, her boobs and all over her clit. I will never forget the way my cock felt against her ass. Once in her bedroom, I started to undress her. After I had unzipped her pants, she knelt down to take them off. Her ass was stuck right up at me, and it was just as I had imagined- firm, but round and full. Still facing her back, I took off the buttons of her sweater, and off it came. She took my hands and cupped her boobs, and started shivering. Her nipples were rock hard through her bra, and I could tell they were big. As I massaged her tits, she just started sighing and moaning, and kept telling me how good it felt.
After a few minutes, she turned around faced me against her bed. While kissing me very deeply, and rubbing her body against mine, she started undressing me. It was then that I finally saw the mirror on the other side of the wall. The visual effect was stunning. I could see this incredibly sexy woman, in black lace panties and bra, in flesh on the front, and through the mirror at her back, undressing me. As she knelt in front to take off my pants and boxers, my cock sprang into the open air, and almost hit her face jumping up. She just smiled, and kissed it at first. Then she licked the top very slowly, and looked at me. I cannot imagine what my face looked like; I just know that my whole world was standing still, and spinning very fast, at the same time. Satisfied, she went back to sucking it very gently.
As much as I was blown away, I did not want to be selfish with her. I had been almost obsessed with pleasing this woman for three months, and I wanted to make sure that I did do just that before satisfying my own needs. As I started to pull her up, she mumbled something about wanting me to come. I just somehow managed to hold her, and then pick her up. I can still remember hoarsely whispering about sucking her, and then taking her bra and panties off. I kissed her stomach and belly button, and then started going down on her.
She started purring again, this time louder than before. My tongue started flickering in and out of her pussy, and I started to slowly rub her clit. I know the result that was coming, but I was not prepared for the way it happened. She started bucking wildly, and shaking. Pretty soon, she had her knees up, and was holding my head with her hands, and coming strong. Her orgasm was at least a few minutes, and it was like nothing I had ever seen before. Needless to say, my ego was sky high by this time. I was ready to penetrate her, and feel all the juices flowing in her.
Sensing my urgency, she asked me to stop for a second while she got some rubbers. It was almost comical, my turning over and lying on my back, with this huge boner pointing up at the ceiling, while I could hear her rummage in the bathroom to find a condom.
As she walked back to the bedroom, we just looked at each other and smiled.
I was feeling so silly that I just said, "I think I have died and gone to heaven."
She started smiling, and said, "You will, once I have you inside me."
She just sat on top of me, with my cock right in front of her, and started rubbing it. It was stretched about as hard as possible, and the veins were about to pop. Smiling coyly, Jenny said, "Would you like to feel a little wet?"
And with that, she leaned forward and started sucking me, this time noisily, with a lot of saliva. Every time her head came up, I could see my cock glisten before disappearing in her mouth again. She took my hands and placed them on her tits. As I slowly rubbed her nipples, she was starting to moan again. Finally, she got up and put the rubber on me, and then lowered her incredibly hot pussy over my cock. It was the most exquisite feeling I have ever experienced. As I slowly entered her, she kept saying how big I was, and how good it felt. Finally, I was all the way in, and she was shuddering again. She had an orgasm right there before I had even moved inside her. As I held her, she was gasping for air.
We lay there for the next few minutes, me all the way inside her. Finally, she looked up and said, "Fuck me, and I want you to come this time."
I sat up a little bit against the pillow, and she started riding me. The feelings of my cock being inside her were earth shattering. I was grabbing her ass, and pumping her. She had her arms resting on my shoulder, and her big tits brushing my mouth. She asked me to lick her nipples, and I was happy to get her excited again. I was starting to realize that this woman had very sensitive breasts, and she received a lot of pleasure from having them played with. In between sucking her tits, I was looking down to see my thick cock going in and out of her pussy. She was tight, and it was a perfect union. As she leaned back a little bit, I could see all the wetness over the condom every time my cock would slide out. Pretty soon, she was riding me hard, and I had one arm grabbing her ass and the other massaging her nipples. I was going over the top. In a very hoarse voice, I told her, "This is it."
She just increased the pace, and started grinding her clit against me, while raking her nails on my back. Pretty soon, we were both coming. My first orgasm was like a flood; I must have kept coming non-stop for a couple of minutes. She just kept holding me tight until I had finally calmed down a little bit, just kissing me very softly as I kept filling up the rubber.
For a while after that, my whole existence was a blur. We were smiling, and crying, and just holding each other tight and kissing. I had never experienced anything as emotional until that point in my life. I was overwhelmed when I was finally able to get up and take the rubber off, as I realized it was more than half full, like a small water balloon.
The rest of the evening was all about lust, and satisfying our desires that we had kept in check for so long. It did not take me very long to get back to half-mast. As I turned and kissed her, my cock started rubbing up against her belly. I immediately started grinning, and told her about my sweaty fantasy of coming on her tummy. She seemed to enjoy listening to me describing my wet dreams, and instinctively reached out and held my hard-on, and started gently running her nail across the head. Needless to say, it did not take very long for me to get really hard again. My head was starting to spin as I was slowly getting lost in her smile, and my hands wandering all over her incredible flesh. This time I put a rubber on myself, and then raised myself up on top of her. As I used my thumb to massage the top of her clit, I slowly inserted a finger in her pussy. It was warm, and wet, and very inviting. I raised her left leg up over my shoulder, and entered her a little bit at a time. While slowly pumping in and out of her, we kept looking deep into each other's eyes. I could not help but look down to see our union. Her flesh formed a perfect round lock around my thick olive member, and it was wet, but snug. As her gasping started to pick up, my cock started twitching deep inside her. Pretty soon she was having another orgasm.
When it finally subsided, she lowered her leg on the bed, and then put her arms around my ears, and said, "I want you to pull out when you are ready, and come on my belly."
That was just about all the encouragement I needed. I started plowing in to her at a furious pace, and she started whimpering like a wild dog in heat. Determined to hang on till she came again, I started to drive her like sprinting the last few hundred yards of a ten-mile run. As soon as I felt a new wave of her wetness around my member, I was pulling out of her and pulling off the rubber. Her gentle coaxing sent me totally over the edge, and this time, I shot a massive load all over her. The first spurts missed her belly completely, and flew all the way to her hair. Some of it landed on her neck, and on the pillow. As the next wave came on, I had recovered a bit and aimed for her stomach. It was warm, and gooey, and landed in thick drops around her belly button. I was still coming, and by now, it was all over her clit. A more erotic sight I had never seen in my life. There was my cum on her chin, her hair, neck and tits, her belly and clit.
As she started rubbing it on her skin with both hands, she smiled to me and said, "Well, you can come on my belly any time you want, as long as you can also give me these pretty pearl necklaces."
I was exhausted, but could not help reminding her that there was another beautiful place I would not mind coming on, and that was her ass.
"Oh yeah?" she said, "Why don't we have some pizza and then let you venture over there?"
We watched TV and cuddled while waiting for the pizza. After dinner, she asked if I wanted to go for a walk. We walked hand in hand to a park near her house, and I was amazed to discover that all my worries about her being older than me were h=gone. It was as if we were equal partners. Her head on my shoulder, my arm around her- this was stuff of novels, and I had barely even experienced these feelings before. We were talking every once in a while, and she told me that I should not worry about work, because nothing would change. We would be just as we had been before, and nobody would know. She also told me that we had both gone through too much to worry about relationships, and that she just wanted us to enjoy each other, and take one day at a time.
I agreed with everything she said, and told her that things might change once I graduated anyway, especially since I might start a permanent job and leave the part time position in her organization. At that point, I was too emotional to think a lot, and was probably looking for any way to justify our desire to be with each other. She was obviously feeling the same way, and it was almost as if we were happy to resolve some things on our minds, but not worry too much, so we could live in the moment.
By the time we were back on her street, walking back towards her house, we were clutching and grabbing at each other again. It was past eleven, and the street was dark and quiet. As we reached my car parked in front of her house, I leaned her against it, knelt down, and kissed her pussy. She shuddered, and lay back against the hood as I continued. I guess she was a little nervous, as she kept looking up startled at the slightest noise, and asking me to stop. She had a very mild orgasm, and then she got up and led me back toward the front door. After unlocking the door, though, she turned around and smiled and said, "It's my turn now, I feel safer here."
And with that, she knelt in front of me and started getting my pants off. When she had gotten my pants and boxers off around my ankles, she started to swallow me whole. I was not fully erect yet, so I watched my whole cock disappear in her mouth, only to feel it starting to grow fast. Soon, her tongue was sliding all over me. She would lick the head, then move sideways and use her teeth to graze this most sensitive part of my body, and then swallow as much as she could, and coat me with saliva. But this was just the beginning. While lavishing all this attention on me, she somehow managed to take off her top, and then pulled out her big soft boobs from her bra cups. Her nipples were hard, and she put some saliva on the tip of her fingers before rubbing it on her cleavage. After giving one last lick along the bottom of my shaft, she proceeded to place my hard cock between her tits, and massage it up and down.
I had never been a 'boob man' before, but I think at that moment, I became one. As my cock went between her tits, the head would appear by her neck, and she would lick it quickly before it disappeared again. She was looking up at me and could tell that I was enjoying the unbelievable sensations, so she started to tease me a little bit. I had pre-cum leaking from the tip of my cock by this time, and she started rubbing it on her nipples. She would hold her tit in one hand, and try to squeeze the tip of her erect nipple to the tip of my cock. By this time, I was holding on to the doorframe for dear life, and she sensed that she would get her pearl necklace soon if she did not stop. At that point, I would have been only too happy to oblige, but all of a sudden, she backed off, and got up.