At the suggestion of a friend, I thought I would share how I started my journey in the lifestyle. It is the opening paragraph of a book we are working on together, so it goes into my background a little more than most stories will, but it gives you an insight into my mindset when I started out......

This will give you an idea how long I have been involved in the lifestyle.  When I first dipped my toe in the water, there were no websites, your adverts were in specialist magazines.  Contact was made by letter, photos were printed (you didn’t have to go to the 1hr photo store to develop them, thankfully you had a printer at home), and contacts seemed to be more genuine and respectful.  I was fortunate, I ran my own business from home, my time was a lot more flexible, so meets were very workable for me.  It was in this time that I made my first contact with the lifestyle, and looking back, it certainly shaped my journey.

So a little about me, I grew up in the country, a very straight upbringing, and I don’t mean in a sexual way.  But you were expected to act in a certain way, and anything else would certainly raise eyebrows.  Sexually, I was late starter, never had girlfriends, and many questioned if I even liked girls.  That was never an issue, but being an introverted extrovert (I love modern tags), it was meeting people and then moving those relationships to a sexual nature was the real problem.  I even lost my virginity in a massage parlour, and I have to say, it was the worst $120 I ever spent, and probably the easiest $120 she ever made…. For the 7 seconds of work that she had to do!  That was probably the moment that I saw the separation of sex and love that has enabled me to explore the life and choices I have made.

The first person I met, was through the “old school” pen and paper method. Back then, my country hillbilly background played a huge part, so it was women that I contacted.  The first person I met, and saw for quite a while, was a married professional woman, who also ran her own business, so her time was a little flexible too. After exchanging paper based messages, we contacted each other by phone.  Yes, there was email, but SMS was more common.  We finally made a time to meet, for me, given my nature, I was nervous as hell, for her, clearly this was nothing new, and that made everything so much easier.  We met for a coffee, at a café in am outer commercial area, so nothing fancy, but given her occupation, it could not have been in the CBD.  I still remember the day vividly, it was a cold and dreary winters day, we were both pretty much rugged up, but she was little, and no amount of clothes could hide that she had a hot little body.  I knew she was a gym goer, but she was absolutely the type of person who would have made my head turn in the street, so she had my attention the minute she walked in the door.  She was older than me, I have always liked older women, the confidence, the experience and the openness that comes with it.  From the moment she sat down, she had me in the palm of her hands, it was now up to me not to stuff it up. 

She knew this was my first time doing this, and I think she sensed my nervousness, so she definitely took the lead.  This absolutely set the tone for my future, strong, confident and sexy women.  We chatted for a while, but I knew that she had an appointment to get to, so it couldn’t go on forever.  As I mentioned, the day was a cold and dreary one, so I offered to drop her off to her car.  She gratefully accepted the ride, little did I know that she had something else in mind.  We walked back to my car, which was very close, and drove to her car, which was parked in a little quiet side street.  We got to her car, and I leant over the give her a kiss before we parted, at which point she leant over with her hands reaching for my zip.  She looked at me with a cheeky grin and told me that everything was ticking her boxes so far, but there was one part that she needed to check before she went back to work.  Her cold hands reached in my pants and found one very hard and hot cock.  Straight away, she smiled and said that was the final part of the test passed.  Her lips left mine and moved towards my now free cock, and I could tell that these were very experienced lips, as this was a blow job like this very inexperienced guy had never experienced before.  I took this as an open invitation to explore her a little more, so I reached over and ran my hands up the inside of her thigh, only to find that she was not wearing any panties.  I suspect that this was always part of her plan, should she like me, just to give a sample of what was to come.  She was already very very wet, and her smooth pussy seemed to welcome the reciprocal attention.  We had absolutely no risk of being seen, the windows were well and truly fogged up with the activities within.  But this was always going to be a short meet, and it was time to clean ourselves up after a very welcome introduction to each other and figure out what the next move was going to be.

It didn’t take long for a message to come thanking me from distracting her from her afternoon of work.  And given her line of work, she really needed her full attention.  I had always considered myself to be average.  Now going back to my upbringing, I grew up in the country, if you were at a urinal, you didn’t look, if you were showering after rugby, you didn’t look, so I always figured that most cocks, except for the ones you saw on porn, were pretty much the same…. it seems not.  Apparently, I’m longer than normal, thicker than normal, but something I had never thought about, harder than normal.  This was something I was about to see more and more through the years, where I was confronted with more and more naked men, and I got to see that more times than… much more times than not, I was the biggest guy in the room.  There is no bigger ego boost for a guy, than to have someone compliment your cock.  You always hope that it is someone you find attractive and not a team mate in the showers at rugby, but a boost is a boost after all.

After the exchanges of messages in the days following that first, mind blowing meet, we decided to follow it up with another meet, with a little more time and discretion to explore each other further.  Timing and location was always going to be the biggest challenge, as both our houses were out of the question, so I suggested I organise a room in the city.  We agreed on the day and then the time than we could meet, so it could fit into a gap in her schedule.  I had absolutely no idea how a meet would go, what did I need, what should I bring, how would it play out.  Well, I found that those things pretty much take care of themselves.  Depending on the time of the day, I figured a drink wasn’t necessary for a lunchtime meet, but for a night time one yes, Condoms and lube are an absolute yes, and make sure there are tissues and towels handy as things can get messy.  Make sure the “do not disturb” sign is out, and not turned to “please make up my room” as that can be a mood killer.  Water is a must, but the most important is to just be relaxed.

Those nerves went into overdrive when there was a knock at the door.  Thankfully this was a time before floors at hotels were locked off.  You could just come up in the lift, an advantage I was to use in this particular hotel with another person many years later.  I opened the door, and before our eyes even met, M just grabbed me and kissed me.  As a nerve killer, it was a top move, and made the potentially awkward first proper meet just that little bit easier.  It was a much warmer day, and she had “gone to the gym” so was in very tight fitting gym clothes which really highlighted her tiny little body.  The room was warm, but the feeling even hotter as our hands quickly went to explore each other’s bodies far better than we had done before.  Even though she was small, she knew how to move my frame around.  I’m not a big guy, 6 foot tall and an athletic build, but she pushed me onto the bed like I was a shop mannequin.  With me completely under her control, she climbed on top of me, undressing me faster than a child unwrapping Christmas presents, and with about as much passion.  Now naked and exposed on the white hotel sheet, M finally got to see all of me for the first time.  I saw that cheeky smile, that I was going to see time and time again in the coming months, as she cast her eyes over me, and that attention quickly turned to my very very hard cock, that was just begging for those lips to devour again.  This time, there was more room, more passion than the first meeting.  It had been a couple of weeks since that first time, and the build up to this just intensified the moment, and the feeling absolutely lived up to the expectation.

M was not going to get everything her own way, I had to see what I had only felt before now.  My hands reached down, and found her figure hugging sports top.  I peeled that up, over her head, and then removed her sports bra exposing the most amazing perky little  breasts.  They barely fell, and were very very firm.  Next I pulled her to her feet and her yoga pants were next to come off, there were less surprises there, except that today, M was actually wearing panties, so one more layer or wrapping before I got to see that smooth little pussy that I has enjoyed only a couple of weeks ago.  So I finally had this sexy woman, naked in front of me.  Somebody’s wife, probably somebody’s mother.  Naked in front of me, and the start of a journey that has yet to reach anywhere close to it’s destination.  This was the woman who set me on a path, and one of the most important teachers I had.  I saw that sexy little look, a look that said, enough of this, you’ve had your look, now I want to enjoy your body.  So she climbed back on the bed, and back to my cock, still standing well and truly to her attention.  If the first experience of her lips has amazing, this was next level.  Hands exploring my body, every part of my body, places I had never had hands explore before.  It took all of my strength not to blow my load there and then, but I really wanted to make sure that I made this moment last.  I have always been a giver in bed, I figure that the more I give, the more I get in return.  So I pulled this tiny little frame up my body and rolled her over, to make my way down her body.  Starting with some very passionate kissing, and kissing that made me completely relearn the way I kissed, kissing from a woman’s perspective, the sensual side of kissing, the art of kissing, kissing that makes the person want more of you, more of you that reflects the way you kiss. 

I made my way down her barely 5 foot frame, enjoying every inch of her soft skin, her nipples very reactive to my touch, her firm breasts appreciating the attention of my tongue.  My tongue now made it’s way towards her pussy, but not directly, there was still more teasing to be done.  Down her thighs, along the inside of her thighs, alongside her gorgeous little pussy, taking care not to actually touch it, but close enough so she could feel my breath, and hope that I would move the millimetres closer to her lips that M so dearly craved.  I felt her hands move to the back of my head, stroking my hair, moving me to where she wanted me to be.  Of every sexual act, oral on a woman is my absolute first love, it’s the ultimate gift that you have, the ability to make a woman come, I think is the ultimate gift.  You do learn that every woman is different, so you can’t be a one trick pony, you have to listen, feel and be aware of the effect you are having, and if you need to make a change.  Today was not a case of that, this was a very responsive pussy, every touch came with response, this was a woman who was sexually free and very comfortable with herself and who she is with.  Not everybody is at that stage, being able to let yourself go and give yourself completely to another, is something which takes years, if ever to reach.  I’ve learnt over the years, the difference between fake and real reactions, and looking back this was all very real.  If the comments on your cock are an ego boost, then the ability to make a woman come again and again, send your ego to another planet.

I thought M was never going to let me up for air, but I sense that she wanted to feel more than my fingers inside her.  She guided me back up to her lips, kissed me softly, and looked over towards the condoms I had placed beside the bed.  She pushed me onto my back and opened the pack like it was second nature, and in one move, slipped it over my cock.  M then straddled me, and guided my cock inside her wet and waiting pussy.  The look on the face of a woman that first time she feels your cock inside her, is just magic.  Talking to people over the years, some cocks just feel good, the shape, the size, where they touch, is all a part that comes into play.  As a guy, we don’t think about that, to us, every pussy feels good, sure, some better than others, but they are all fantastic.  To a woman, there are so many factors that come into play, and I wonder if that comes from what our basic anatomy is designed for, men are there to cum, women are designed to make us cum.  It’s only a relatively recent thing than women are also meant to get enjoyment from sex.  So the shape of a man’s cock has become very important, and it seems that mine was hitting the right spots.  M starting to move her hips, determined to get the most out of me, testing every part of her with me.  I start to feel little parts which seem to be getting a stronger reaction than others, and those parts getting visited again and again.  I can see that look, the eyes almost rolling backwards as she was lost in the pleasure that she was taking.  I say taking, as I was not playing a huge part in this enjoyment, other than providing one part of me, but I more than happy giving that input, as the sight of this sexy woman enjoying herself astride me was something else. 

But good things don’t last forever, and M reached down and started to play with herself, determined that she was going to get maximum return on the time she had that afternoon. The intensity of her movement increased, so did the pleasure she was giving, and that was always going to be a recipe  for an explosion on my part.  I tried to hold on, and I’m sure that was obvious on my face, as she urged me to give it and release my pressure.  I’m not a vocal cummer, but it’s pretty obvious when I’m cumming and she just looked down with a satisfied look on her face that I had enjoyed myself as much as she had.  She looked at the clock, and time seemed to have absolutely flown, and she realized she had to “rush back from the gym” for her next appointment.  There was no mention when we organized the meet, other than the short mid day meet.  But as M was getting dressed, she asked if I was still going to be there after work for the second course.  I hadn’t even thought about it, but I figured that with a little reshuffling, I could make that work.  That was the first of many times we met, be they little outdoor meets during the week, well timed meets at each other’s homes, or the odd hotel meet for a really good workout. 

It was during one of these meets that I discovered that both she and her husband were both swingers.  Now days you would call them ENM, but back then we didn’t have those tags.  This was really early in my journey, and if you remember that I come from a very straight rural background, the suggestion that I join her and her husband in a 3sum, was just not on my radar.  Me and another guy, that sounded gay to me, and not something I had even contemplated.  Although I didn’t realise it at the time, that was the beginning of the end of this relationship.  Looking back, it was the logical extension, and that suggestion wouldn’t even raise an eyebrow with me now, but back then, I really didn’t understand the lifestyle, and I’m sure I’m no different to people dipping their toes into it today.  But I look back at this first person, and I look at what she taught me about the lifestyle, and the grounding in trust and respect that it has.  These are things that stay with me today, so what you will read in the coming stories will be with a view to exactly that.  The trust and respect that people have given me in our meets, will be returned in these stories, but you might actually recognize that it is you in the story.