Jill Jacking Jack

My best buddy (Jim) and I were working on a road construction crew in northern Canada at the time this occurred. The job site was in a remote area so we were put up in a construction camp nearby. We bunked four to a unit and washed outside under a makeshift shower. We work dawn to dusk every day for fourteen days then got a week off, then back at it. Now, I am an avid masturbater as I think most twenty something males are, but on the job, you just didn't or couldn't get it on. As you can imagine, in camp you are either too tired or a lack of privacy keeps your hands off your junk.

Home was a little country town about fourteen hour's drive from camp. We worked hard, made great money and played harder. This kept both of us out of any relationship. Going home was always such a long drive. We usually stayed at Jim's sister's (Jill) apartment in the city one night and completed the trip the next day.

Jill is three years older than us. We all grew up together in the same little town. She wasn't my type at all as far as looks go; small breasts, wide hips, but Jill and I always got along ok. She was a book nerd through school; we were typical boys, so interaction was infrequent. I do remember when we were teenagers that there was a fair amount of sexual innuendo riddled bantering between us, but never thought anything of it at the time. Now Jill was an elementary school teacher and she fit the stereotype perfectly. She could easily be mistaken for a prude when she was in teacher mode. Hair bun'ed up, loose clothing, rimmed glasses... Still I never considered her anything more than my buddy's sister and a friend of sorts.

It was fall and the company planned on one last crew rotation before we would have to button things up for winter. We had just completed our two week stint and were ready to head home when the boss asked us to put in one more week to clean up and shut down as they decided not to bring in another crew. It would be easier to keep us there rather than rotate another crew in for just one week. The pay was good so we readily agreed. After two weeks of pent up urges it was going to be tough that third week. However, work kept you busy and tired. A release would just have to wait. The last day on the job we drove out of camp with the equipment that would need to go to our company shops for storage and servicing. This added several hours to our trip into the city where Jim's sister lived. We finally arrived at Jill's after eleven PM and were dog tired, smelly, and dirty. We just wanted to sleep.

Jill insisted we shower before hitting the hay. She didn't want us two dirty boys sleeping on her clean sheets. Jim got the guest room; I got the hide-a-bed in the living room. The place was small. You entered the second floor apartment into the living room that was only separated from the kitchen by a counter and cabinets. The two bedrooms were separated by a small bathroom. That was it. We were exhausted, so we each took a quick shower and went to bed. The apartment was quite warm so you didn't need many covers. I, in my briefs, crawled under what was basically a sheet and immediately fell asleep.

I awoke the next morning around eleven am. I had that tell tale sign of arousal most men get; morning wood! I cleared my eyes and looked around the room, listened. I was sure I was alone, then made the realization that Jill must be at work. I pulled the sheet back and grabbed my throbbing erection. Oooohhh this would feel sooo good! I needed to cum so bad, it wouldn't take long. I began jerking my meat rhythmically. Just as I was getting into it, I hear a key entering the lock to the apartment. SHIT! Its Jill coming home and she's going to step right into this room from outside. It was Saturday, no school, she was only out shopping. I pulled the sheet over me as quick as I could just as she opened the door and entered.

'Hi' she said enthusiastically. I replied with a softer 'hello' probably showing my frustration. She had some grocery bags in hand she took over to and set on the counter without appearing to have noticed anything unusual.

'Why don't you get your dirty clothes together and I'll put them in the wash for you?' she said as she began putting away the groceries. Then she said, 'Jim took off somewhere already, said he was going to look for a new TV or something'. Jim loved spending the money he made. I was glad he went alone as I hate shopping.

My briefs would do nothing to conceal a boner, but my erection had subsided enough so I could get out of bed, even though my package was still pretty obvious. I went through all my clothes and set aside the dirty ones. Unfortunately the extra week of work had left me with ZERO clean clothes to wear. I told Jill this and she quickly said, 'Well, guess you'll just have to wait in the nude until I get them washed and dried'. There's some of that sexual innuendo. 'Look', she said, 'I only get the laundry room on Saturday mornings so better hurry up or you won't have anything to wear for a week'. I asked her what I was supposed to wear in the mean time.

'Go put on a towel', she said rather sarcastically. I figured she was serious, and it was sure nice that she would wash my clothes for me (as she often did when we stopped in on the way home) so I went to the bathroom and grabbed the largest of her bath towels, which barely made one and a quarter wraps around my waist. Off she went to the main floor laundry with all my clothes while I put the bed away and sat down turning on the TV. The masturbating would again just have to wait, but it was now readily on my mind and my cock would react each time I thought about it. Heaven forbid I get a raging erection in front of Jim's sister in this freaking little towel!

Jill returned from putting in my laundry and went immediately to her bedroom. A couple minutes later I hear her call me to come to her room to see something. Not expecting anything I sauntered to her room and opened the door. There, Jill knelt on the bed facing me, wearing only a pair of lacy, pink panties and a short loose fitting top that I soon realized had nothing beneath it. I'm sure my jaw hit the floor. I'm equally sure my dick went the other way. With a coy smile on her face Jill began to speak,

'I have a confession to make', 'this morning I watched you before you woke up'.

Watched me? My first thought was, watched me do what? I was sure she hadn't seen me pulling myself when she got home or she would have said something. Prior to that I thought I was fast asleep.

'Uhhh, what did I do' was all I could say. My cock was beginning to react to the sight of what I was now subconsciously realizing to be a very sexy woman.

'Well', she said, 'I guess I saw you having a wet dream, and I watched you cum'. She then told me it was really sexy and made her feel pretty horny so she went out shopping to cool down. Then she said she found she couldn't take her mind off it and wanted to see if I was interested in having some fun together. No sex, but we could enjoy the next best thing?

Now my cock was at full attention. That poor towel didn't have a chance. Jill, noticing and giggling told me to lose it and come sit on her bed. My mind went into lust mode. I dropped the towel and all inhibitions regarding this sexual encounter with my buddy's sister. I moved to the bed and sat down. 'Lie back on my pillow and let me start' she proclaimed. 'I think I remember how to do this right' she said questioningly. I wasn't about to argue or question anything. I was in need of some serious relief and way better than self pleasure, I was about to be serviced!

Jill soaked my chest with oil and began slowly and methodically massaging my upper body. She ever so gently caressed my lower abdomen getting closer and closer to my throbbing cock. As the pre-cum pooled she would mix it into the oil. She moved to my inner thighs and lightly caressed around my balls. I was beginning to breathe noticeably harder now. Ohhh this was good. My cock was sooo tight. Jill took her time, slowly getting closer and closer to my cock until finally she began to rub and massage it. She didn't just start jerking it as every other girl I've been with has. She sooo gently caressed it with her thumb and forefinger encircling it. It was as though she knew exactly what I liked. It was beginning to visibly throb and pulse and I knew this was soon to be it. I wanted to hold out for longer, to prolong the sensations, but it was too much. Jill kept the tantalizing caresses up, slowly sliding her lightly gripped hand up and down my cock. The look on her face was happy, enthralled. She was really enjoying this. I looked to see her other hand reach down her panties, she was 'Jilling' Jill while 'Jacking' me.

I looked down at my cock just as I felt the rush of orgasm come over my body. OMG! I had NEVER felt this before! My whole body shook as I came spurt, after spurt, after spurt. I spewed cum like there was no end. Jill let out a little 'oooh, yes, cum for me' as I did. I lay there jolting as she continued to stroke even though I was done. It still felt great. My cock head was so sensitive; I could hardly stand her touching it. But she was so perfectly doing it I just let her continue. Then she abruptly said, 'Your turn to do me, OK'? 'I'll teach you how'.

'What do you mean', I said. With that Jill explained that even though she knew I had been around, she also knew I likely hadn't ever been schooled as to how to stimulate a woman nicely, and, since she was a teacher, who better to do it.

Then she moved with her back toward me, sitting between my legs. She leaned back against me, smearing her back into the cum I had just deposited. She grabbed my hands and placed them in front of her.

'Ok, I like lots of frontal stimulation'. 'My breasts may be small but my nipples are super sensitive'. 'Now, just like the gentleness I used on you, touch me here and here', she said as she placed my fingers directly to her right nipple and clit. Remembering how lightly it seemed that she caressed me I began lightly encircling her nipple and clit with my fingers. She immediately began to moan and breathe heavier. She spoke softly of being sooo horny and would cum sooo quickly. I kept it up, trying to think of doing something differently, but she was responding real well so I decided not to change it up. Jill pressed herself harder into me, squishing my now growing hard on into her butt crack. This made me want to really get her off. I began focussing on her clit with my right hand and moved back and forth from to each nipple with my left. She grabbed and rubbed my legs that straddled her. I could feel her tensing up. I pressed her clit ever so slightly harder and that put her over... She shuddered as I had, and kept shuddering. She clenched her legs together, trapping and pressing my hand harder into her. She grabbed my other hand with hers and pressed her tits together. I could feel my cock staining and hard as a rock as she pushed her ass into it. WOW! Her coming was almost as wonderful for me as my own!

Jill slowly came down from her sexual high. 'Good job' she said. 'Likewise', I returned.

We chatted about this and how it came to be for a while. Needless to say, it lead to a lasting, loving relationship between us that we both feel great about to this day.