Nina

A note to readers: This is a true story which I felt compelled to write to understand and reflect on the circumstances where a lovely lady came into my life. The occasions where this can happen are rare (this was a first for me). There is obviously a sexual element (and I wouldn't be submitting it here if there wasn't) but please do not expect a roller coaster ride of sexual exploits. This was more a story I wrote for myself. However being a previous contributor of stories to this site, I naturally thought I would share it here. Please enjoy it for what it is.

I work in the city, in Sydney. Part of my weekday routine is to sit in a coffee shop and have a nice cappuccino while I do a bit of work on my laptop or scroll the news on my phone. I'm usually a creature of habit in this regard and will usually go to the same place at around the same time.

I had noticed a lady who attended the same coffee shop at much the same time I did. She was there most days. She was middle aged, very slim and quite attractive.

I also noticed that she had a very nice smile. I would often pause what I was doing to watch her order her coffee and greet the staff as that was usually the only time I would hear her talk and see her smile.

Like myself, she also sat by herself.

I had seen her for several months without saying anything but then I started noticing that she was noticing me. A few months ago I had started working out again. Previously I had worked on fitness but this time (for the first time) I went for muscle tone. I had recently started seeing results. Because we were moving into Summer, I had started wearing tee-shirts and that had accentuated my arms and chest. I travelled to work like that and got changed in the office.

The company I worked for owned the building I worked in. Because of that, I had started to occupy a spare, dusty room on the roof of my building. I had to clean it up a bit first but it then had adequate space where I could work out at lunchtime with a few dumbbells and related equipment.

I usually don't like to engage a lot with people in the coffee shop because before you know it you get roped into having to make small talk each time and it's very hard to wind back the position.

However I really liked this lady and I thought to myself, it would be nice to get to know her. What if she changed jobs or routine suddenly, then I'd lose my chance altogether. I didn't want this to be a missed opportunity. Besides, if it didn't work out or things got awkward, I could always go to another of the hundreds of coffee shops in the city.

One day she sat down opposite me and reasonably close. I looked at her, made eye contact and said hello. She responded with a hello of her own and gave me one of her smiles I had only see her give to the staff. Her name was Nina and she worked in an office nearby.

Beyond our initial hello's there were a number of weeks where we made small talk, commented on current events and generally just interacted. We were able to dip in and out of what we were doing personally like we had known each other for a long time. I liked that we could do that.

At one point she made some comments on my physique, which was nice. Not even my wife of 20 years had commented in this regard. I thanked her and admitted I had been working out quite regularly. If I was completely honest with her, I would have said that since our initial hellos, I had actually upped my workout routines. I told her about the room I had on the roof of my building that allowed me to work out during weekdays.

She asked about how she should go about getting in shape. I thought to myself that she already looked pretty good. I wasn't sure whether she was being a bit flirty in this regard or she genuinely wanted to know. I took her question at face value and told her all you needed was a workout mat and maybe some light dumbbells to start -- no need for an expensive gym membership. I threw it out there that I was happy to show her the set up in the room on the roof of my building, if she wanted. I was pleased that she indicated that was a good idea.

I thought afterwards, it was unlikely she would visit my room. It would be great if she did but in this day and age of creeps and so on, I was essentially a stranger to her so I couldn't imagine that she would risk it.

I didn't mention it again but amazingly she prompted me a few days later. Well, I was game if she was and suggested that we could go that morning. We both finished our coffees, grabbed our bags and I led her to my building and, inside, the lift to the 10th floor (the roof). On the way I said to her, "You're very trusting you know." She gave me one of her smiles and light touch on the arm.

I took my key and lead us out onto the roof and then in the room I had been occupying and using for the past two years. It was a bit grim with paint peeling off the walls and next to no natural light (I had hooked up some spotlights to compensate) but it suited me. I never imagined that I would have a visitor to it.

The first thing Nina commented on was the bed that was set up in the corner. I had taken to getting to work super early (even before my workouts) and come lunchtime, I would often have a nap. The bed had been borrowed from some furniture someone was storing on the roof for years. I explained all of this to Nina and I think it made sense to her. She seemed to like the space.

I attempted to show some of my weights and ask her what she was looking for. I got the sense that she actually had limited interest in such matters. "You know, I have trained as a massage therapist," she suddenly came out with. "Never actually took it up however."

This was news to me. What was bigger news was what came next. "If you like, I'm happy to give you a massage... if your tired muscles need it."

If I was a young man, I would have probably declined it and not seen it as the potential opportunity it was. On this day, I said something along the lines of, "that would be great."

She asked me to strip down to my underpants, which I did and I laid down on the bed. I had had massages in the past, so I was reasonably comfortable in that near-naked state. I had also turned down the lighting, mainly so that it wasn't shining into my eyes.

She massaged my shoulders and made some positive comments on my body, all of which were appreciated. It was very hard to make conversation with my face buried in the pillow and I was happy when she asked me to turn over.

By way of further background, Nina is quite the opposite of my wife. My wife has small breasts and a biggish bottom whereas Nina has large breasts and was quite slim and petite. I wasn't necessarily into large breasts but must admit I hadn't really experienced them before. Suddenly, given where I now found myself, I had desires to see those breasts.

Including that first day, the following happened over the course of the next several weeks where we would initially meet for coffee and then go up to the roof of my building which led invariably to a massage. While it might have been nice for all of this to have happened on the same day, life is just not like that and I'm not going to pretend it did:

There were times when Nina would massage my legs and her hands would get up quite high that they were skimming my balls through the fabric. She offered a stomach massage which I hadn't had before. I was a bit reluctant as, while it was reasonably flat, it was far from six pack material. Again, if she was happy to offer, I was happy to receive. Each time she would shimmy the band of my underpants down a bit, exposing some neatly trimmed pubic hair.

She enjoyed sitting on the bed up close to me and massaging the top of my shoulders, my biceps and forearms. I later started to wrap my arm around her waist and she was happy for me to do so.

Other than that first massage, I was always lying on my back. I think we both preferred that as we could talk easily and look at each other.

We talked a lot and got to know each other very well. She knew early on that I was married (20 years) with two boys. I didn't want to hide this fact from her. I learnt that she had been married for 10 years (but was now divorced) and had a daughter of similar age to my boys.

I often joked with her that my wife would kill me if she saw me her and that really I shouldn't be up in this room with her. Nina would sympathise but never indicated that we should back off at any stage because I was married, which I appreciated.

Nina started to playfully grab at my cock through my underwear. It was always quick grabs and nothing that led me to getting hard. However, on one occasion I must have been a bit horny because after a few playful squeezes and other incidental touching I started to get hard. This wasn't lost on her and she mentioned that I looked "quite big."

Nothing further happened on that occasion and I was racking my brains later to think of how I could have progressed the situation. I didn't just want to expose myself to her and ruin it all.

However, the next time when I was semi-hard and she made a comment I threw out the line, "I'm happy for you to have a look... if you like." She took the invitation and used one hand to take down the side of my underpants where my cock was pointing. She grabbed a hold of it and started a gentle stroke. She asked me if I wanted to cum. I was a bit ambivalent given I was a bit nervous and her hand job technique seemed quite crap -- which suggested to me that this wasn't something she routinely did.

Instead, I asked if I could take her top off. After all, I was completely naked at this point and she was fully clothed. She was happy to and then after a minute or two, took off her bra too. I don't remember much of seeing her nice, ample breasts that first time. My head was simply swimming with what was going on.

After a few minutes and as a way (I think) of breaking the tension, she joked about me giving her a massage. I was happy to oblige and we swapped positions on the bed and she laid down on her stomach. She wanted her shoulders massaged. She asked me to sit on her bottom (I thought I was too heavy but it was all ok). Then she instructed me to get in hard around her shoulder blades with my thumbs and fingers. I can't tell you how much she wanted the shoulder massage. She seemed to enjoy what I was doing even though it was probably pretty bad.

Again, nothing further progressed on that day but on each occasion we went further and further. Once her top and bra were off, it was easy to get her trousers off so I could massage her legs. Now we were both naked except for our underpants.

I went to check a message that beeped on my phone only a few metres away and looked back to see her, lying on her back on the bed looking down her panties. I wasn't sure what she was checking out but she saw that I caught her looking so I asked, "Can I have a look too?" She let me and I even slipped my hand down the front a few times. When I tried to take them off her, she didn't want to and said something like 'not wanting people to see me'... Again, that was the end of our session.

The next time, things progressed quickly and when I suggested I take off her panties, she was completely fine with it. Now it was her that was completely naked. I was still wearing my underpants. I dropped a hand between her legs and she wiggled her pussy against my digits. She reached out a hand and squeezed my cock through my underpants. I pulled out my dick for her and she grabbed a hold of it and pulled on it further. She made some very nice noises I hadn't heard come out of her mouth before. I thought I heard her at one stage say, "I want you..." There was again nothing further that happened as we needed to wrap up and go to work. We finished and I think we both thought that sex was definitely on next time.

Each time we met started with a massage. Nina gave my head a nice massage, which then led to an arm massage and then some cuddling. It was all very nice. I got my arm under her and lifted her up and onto the bed. This was my cue to start to massage her. She was on her stomach. I took off her shorts and then her panties. She immediately turned over towards me and spread her legs. That allowed me to touch her bottom and between her legs. She seemed very horny.

I wanted to see her boobs again so I whispered that I wanted to see her fully naked and she was happy with that. I took my underpants off so we were both naked. I got on top of her but my cock was sitting above her pussy. This time I definitely heard her say, "I want you" and before I knew it she had moved my dick down to the entrance of her pussy as she simultaneously pulled it in and pushed onto it.

Compared to my wife who just seemed to go through the motions these days, Nina was very vivacious. She was very much into sex and enjoying it. We carried on missionary position for a while. She then jumped on top of me and I got to play with her big boobs and small arse.

She then asked if I wanted to take her from behind. I was more than happy with that. I licked a finger and reached around to get to her clit. She seemed to like it.

Finally, we laid on the bed together in a spooning position. Even then it wasn't over as she pressed her pussy towards my dick and it entered her for the fourth time. The build-up finally got to me and I had to pull my dick out of her as my cum did a quick spurt, followed by a larger and longer release. I wasn't sure where it all managed to go but I made sure we had tissues on hand.

It was a lovely first fucking session spent together and well worth the lead up and progression. This will no doubt be the start of many more but at this point I thought I'd take the time to write up all that had happened over the course of a few months. There may be another chapter, there may not be...