Confessions of a M.O.D (Mature Online Dater) 4 – Cougartown

The topic of online dating and the “Personal” section of online newspapers/classifieds arose with a few friends over dinner – with opinions being varied and leading to interesting discussion.

Being the inquisitive type, I began doing research of my own and discovered more sites than expected. One site in particular caught my eye which gave me an insight into personal requests from the unusual and different through to the obvious desperate!

I had never intended to respond to these types of ads, however one quite unusual lengthy ad stood out.

It said he was seeking a mature experienced woman to teach him the ways of the world. His articulate wording indicated he was mature, intelligent and creative, with the added bonus of a sense of humour. He described himself as “tall, good looking, in good shape and was professionally employed”. It was unclear if he was wanting a single night crash course, or an ongoing education (I suspected the former).  He wrote that dinner in elegant surroundings would be a positive start, followed by sharing wine and becoming aquainted on the sofa at his (hopefully quality) hotel. He certainly had a way with words!

One tiny detail: He was 27 years old. I doubted his idea of “mature” extended to my vintage, and guessed this was not a serious ad – although as a joke I replied. Well…. his take on the night did sounded very inviting.  I began by asking: “Would there be a queue of women at his hotel door?”….”Would I have to take a number?” ….”Was there somewhere to hang my coat?”.

I gave a fairly accurate description of myself and said I was a “….spontaneous  hands on kind of lady and believed my extensive experience would provide a very positive outcome for both”. I added I was more mature than he may have expected, but this would be compensated by “my levels of enthusiasm, assuming we both felt a strong attraction….”.  Who was I kidding ? I was old enough to be his mother, and some !!!  …  I attempted to sealed the deal by being slightly (?) over the top telling him he would not be disappointed..Rose coloured glasses perhaps?

I did not expect a reply.

A few days later he emailed saying i had been shortlisted for the role as my application was the most interesting and he’d like to discuss the position further. I was amazed, surprised and excited and wore a big smile all day. It did sound risky (even if he was genuine) so I explained I would need to get to know him prior to meeting . We emailed extensively for a day or so and seemed to get on very well indeed. Just prior to exchanging photos, I felt it necessary to remind him I was seriously older than him, to which he replied tactfully: It was my “attitude to life that counted!”

I only hoped I would not disappoint him.

After numerous emails and text messages during the week, we arranged to meet for dinner at an Asian restaurant. I usually arrange a public first meet for initial safety and as a means of declining graciously if necessary. It’s always a case of will each find the other attractive? Will the online chemistry remain in real life ? Certainly from my experience it doesn’t always turn out the way we hope.

All of my usual measures were in place in preparation for the first date:

  • I would catch a cab
  • A very close friend had details of location/s and would text me at 9:00pm, and call at 11:00pm.
  • I realised I would have my period by then, and felt comfortable enough to tell my new Date. He was understanding and said it was not an issue and we’d have dinner and see how we go. Fortunately my calculations were incorrect

I was nervous and excited as I made my way to the restaurant after spending ages getting ready.

Approaching the restaurant, I spotted him at a table.


He was gorgeous!

He had not exaggerated, and was very attractively dressed. I only hoped I would live up to his expectations. I was wearing a new elegant fitted black sleeveless dress, with black lace, black high-heels, and a big smile. I only hoped my suspenders would stay in place for now! ….Ah the things men never have to worry about! I took a deep breath, smiled and walked toward him.  He  glanced up, stood up, winked, and was smiling as he gave me a lovely prolonged kiss.

The conversation flowed well, and we discussed other responses he had received ( I’m always curious about this ) mostly  from women southward of 35 years!  I was thankful he was unaware of my true age. As usual I was too excited to eat, but managed a little and limited myself to three drinks.

I was still surprised he was interested, yet, by now I was certainly aware of the sexual undercurrent. We were at the mirrored body language stage and held hands across the table.  I resisted the urge to place my high heel between his legs, though did so later: his face did not  portray his reaction. I was pleased I had invested in smooth silk stockings when he stroked my leg.

Confessions of a M.O.D online dating tip 2: Its always fun to wear a calm and serious expression regardless of what happens below the table.

Needless to say, anticipation was high.

We discussed life, family, work, goals, etc, and shared a few laughs, felt very relaxed and at ease..though it was fairly evident we both wanted to exit the restaurant soon. He did have a quiet confidence about him,  and I could not help asking why such a mature intelligent attractive  man would require further “tuition” . He explained he had had two relationships of two and three years each and whilst they were lovely girls, both were rather shy, sexually inhibited and neither were, as he put it, too “focused on that side of life”. He said he wanted to experience more, and felt an older woman could accommodate him! I loved his SOH, and he seemed to understand mine.

He went to great lengths to assure me there would be no pressure from him (surprisingly),  that we would sit on the sofa at his hotel, talk, go with the flow,  and added he would be in my capable hands. I told him if he merely wanted to hold me only, which i doubted) that would be fine also. The  last thing he needed was pressure to perform!

I offered to pay half the bill, but he insisted paying.  We held hands as we walked to the hotel and both felt much anticipation. I let go of his hand for propriety sake as we walked into the foyer, and was impressed to see it was indeed a well known 5 star hotel. There were three male uniformed concierge staff available at the front desk, who may have assumed we were Mother and Son, though I suspect his insistence prior of a king sized bed may have conveyed otherwise !  He put his arm around me as we headed to the lifts. Being of a cheeky nature, I couldn’t help squeezing his behind, turning slightly to grin and wink at the staff, who I knew were watching. One winked back, the others smiled !

Grinning at me in the lift he said: “Why does the emergency stop button only work in movies?” .  I wondered if we would continue the movie theme and feel compelled to frantically tear each others clothes off as we entered the room? Similar to the scene in the movie “Fatal Attraction”, where Glenn Close and Michael Douglas did just that sprang to my over active mind. I somehow knew he would show decorum and sensed he was excited yet understandably, a little nervous. I squeezed his hand.

Our room had floor to ceiling windows capturing amazing city views, was beautifully furnished and had an over abundance of lamps. The bathroom was marble and chrome and the oversized bathtub was advantageous. We held each other and kissed, both clearly aroused.

He called room service and ordered Champagne whilst I threw fire sprinkler systems caution to the wind and lit a dozen tea light candles I’d brought, turning five lamps off as I did so.  I placed scented massage oil beside the bed and condoms nearby….

We sat on the couch sharing our drinks, and talked more, though we both knew conversation would end very shortly. Confessing to each other that we were both quite nervous at this point, I excused myself and went to the bathroom to freshen up.

Whilst the air conditioning was a perfect temperature, I suggested he may be hot and would benefit from less clothing.  He obliged and added he had no option other than to follow instructions.

We continued the student/teacher banter giving a lighter note to the night.

I assisted him with his clothing,  which proved a lengthy process. He clearly worked out at a gym often and I must admit Iwas more than impressed with what I saw. I asked if he would lie on the bed as I thought a massage was appropriate at this time after a hard day at the office.  He said it only seemed fair, seeing I was being so helpful, that he assisted me also. I was glad I had spent money on expensive lingerie which he said he appreciated. We continued foreplay and I felt it only fitting to extend this from an educational standpoint!

During a moments break, mental telepathy must have been at play, as my friend rang to check on me… I apologized,  grabbed my mobile , and said pre-arranged : ” I’m fine thanks Mum… yes, works been flat out… yes,….yes… Ok , will call you tomorrow .. Love you too..bye. “

We resumed, continued, explored, laughed and experienced all things positive.  It was exciting, erotic and quite passionate.  Any apprehension we may have had was gone. We kept looking at each other,  thinking this was an amazing experience for both of us. The fact that he was a quick learner certainly helped, though I’m certain there must have been other liaisons besides his two  girlfriends he had only claimed to have!

At one point I stood up, slid my high heels on and purposely walked to the window to admire the view.  I felt compelled to lean forward and position myself against the cool glass, arms out stretched. He immediately stood behind me as close as humanly possible and commented ” I’m really into you!  ” .  I simply replied: ” That was a terrible line! “

Heading back to bed, we drifted to sleep spooning and woke to the sound of the room service door buzzer. We shared breakfast , then I ran a bubble bath whilst he poured the coffee and read the Financial Review newspaper. He continued to smile, so the news couldn’t have been all bad!

We lay in the bath and chatted away, a la Richard Gere / Julia Roberts: Pretty Woman ….then a little later managed to not flood the bathroom floor during turbulent conditions(!). We dozed on the bed, and just made it from the room by 10:00am check out time .

I casually mentioned his Certificate of Graduation would be in the mail. 

Over the next week, we continued with many text messages, emails and calls and he reached the conclusion he needed more tuition. Who was I to dispute his reasoning ??!!  As would be expected, life, work, family, other commitments  prevented us from catching up for a while…

We met on another two occasions for exactly the same scenario, and found these to be just as exciting, these times with a lovely sense of familiarity.  We have also met for dinner and a lunch, and now regard each other as very close friends.

PS… He called at my house to pick me up for dinner one night and for some reason my younger adult child (living with me at the time, unaware of my private life ) did not believe he was “just a friend” The truth be told – they are the same age! If only she knew what her Mother was really like.

Ms M.O.D.

Confessions of a M.O.D (mature online dater) is a continuing saga of ongoings interspersed with some funny and not so positive accounts of one woman’s online dating experiences . Her aim is to provide some insight into the mechanics of the online dating world for mature adults… 

2 thoughts on “Confessions of a M.O.D (Mature Online Dater) 4 – Cougartown

  1. Lisa Reply

    Holy mature mother of god…….you sexy little minx you. Good to know the old girls still have it!

Leave a Reply

Your email address will not be published. Required fields are marked *