It was the same with my male escort work. Often I could feel an emotional connection being established with a client, but they knew it was a financial arrangement and this helped maintain the intimacy on a professional rather than personal level.
I was obviously good at what I did, as my word-of-mouth ‘advertising’ was highly successful.
CHAPTER 46
Highest Bidder Please
Eventually my resolve not to fuck a student was to be broken after my marriage dissolution.
I was approached for a dance by one of my TAFE students one night at the local RSL club. She eventually invited me back to her unit and we enjoyed a very wonderful night of fucking and sucking each other. She admitted she had been keen to fuck me since her very first class. She was an enthusiastic lover but my confidence and skills had been lost in the intervening years during my marriage.
There was an uneasiness between us in classes after that and I became reluctant to repeat the experience with other students afterwards.
During this period I was also put up for auction at a fund raising benefit for the local surf lifesaving club.
This was the late 1980’s and women’s liberation had established itself on the social scene. As a way of establishing their ‘equality’ to men, women felt empowered to run these benefits, which were considered the equivalent to the traditional trashy female beauty contests. I was perplexed how these women made this connection?
I was one of a dozen local ‘celebrities’ who was asked to volunteer myself for this ‘worthy’ cause. At this time I was now also employed part time as the Sports Editor for the leading regional radio station. I also wrote a regular back page feature for the district newspaper and I was a sports identity in the region. As well, I was still employed as a Head Teacher at the TAFE college. In a regional setting I was a ‘celebrity’.
I had performed at a few ‘hens’ nights for my housemates some twenty years earlier but had never been a spectator at a male strip show. I was now experiencing the voracious behaviour of a group of sexually charged, ‘liberated’ women, who were liberally intoxicated. Generous amounts of money were being offered in the auction for a one-night date with each man.
The organisers had purposely kept the more ‘high-profile’ males till the end of the auction to stimulate higher bids. I was ‘offered’ second last. A much better-looking colleague of mine was last. However, little did any of the women in the audience realise that my colleague was gay, in the days when AIDS was rampant and it was unwise for public figures to ‘come out’.
My bidding increased in $10’s until only two women remained in the bidding. Finally, the hammer went down on $210. I couldn’t see the winner very clearly in the crowd. When ‘claimed’ after the auction, my bidder was a reasonably attractive middle-aged woman, probably in her 50’s who worked with NSW Rail in Sydney and was on holidays at the time.
We had a drink at the surf club and she invited me back to her holiday cabin where we ‘consummated’ our date. She had my pants off me as soon as I got through the door. I was amused and intrigued by her vigour and enthusiasm and her stunned reactions when she saw my cock. I suspected at the time her eagerness was more influenced by her alcoholic levels rather than my attractiveness. She went down on her knees as I stood there bottomless in the open doorway to her cabin. I could see car lights moving in the street behind me and could only assume what they could see in the lighted doorway of her cabin.
She was good at this fellatio game and I came in her mouth as she continued to eagerly suck and gulp my juices in her mouth. She then stood up and wiped the mix of saliva and cum from her mouth and planted an open mouth kiss with sloppy tongue on my mouth. I stepped back to catch my breath. Although I’d just managed to orgasm I wasn’t overly ‘turned-on’ enough to reciprocate her enthusiastic sloppy advances.
Trying not to make her feel rejected I suggested we retire to her bedroom where it would be more comfortable. She took my cock in her hand and led me in that direction. As we did I started removing her clothing and bra. Only her skirt remained as we got to the bed and I gently pushed her onto her back on the bed. I slipped off her skirt and found she wasn’t wearing knickers so the next move was obvious.
I hopped up on the bed with my knees astride her body and edged myself toward her head. As my balls moved above her mouth, she pounced. Her hands moved up from her side and she wrapped one hand around my balls and then took them both in her mouth and began sucking. I grabbed my cock which still had my cum and her saliva all over it and started masturbating to get myself erect again.
I’m a ‘sucker’ for having my balls stimulated and I quickly became erect again. I edged myself back down the bed and spread her legs and slid my hot cock gently inside her very, very wet cunt. She was generously loose, vaginally, so my size wasn’t a concern. In fact, I could sense that this could have been the first time for a long while where a cock had amply extended her vaginal cavity and created a sense of ‘fullness’ in her cunt. She moaned and let out a deep breath and then grabbed the cheeks of my bum and pulled me further inside her. I was a little surprised at how many inches of my cock she eagerly ‘consumed’.
I could feel the warmth of her vagina as it opened to receive my stiff shaft. Her body totally oozed and she let out a rush of breath as I tilted my hips to maneuver the hood of my cock to position against her g-spot. I then began my thrusting inside her and exciting her clit with my fingers. She kept yelling “harder, harder,” then screamed “Stop!” and held my bum tight as she grinded her hips backwards and forwards. I could feel my stiff cock rubbing against her g-spot on the roof of her vagina. She finally let out an almighty scream of ‘Oh, my God!’
I thrust my cock just a little deeper inside her and held her tight for a few minutes then started thrusting again. She came multiple times and finally I could feel my juices starting to stir uncontrollably. I came with a rush that made my head spin. I collapsed exhausted onto her with my cock still firmly engorged inside her tight twat.
We smiled at each other and I fell into a brief unconscious stupor.
As I rolled over onto my back she sat up and then went down onto my cock and began sucking vigorously on my limp lump of man-meat.
After we both recovered, shared some pleasantries and a drink, I got dressed ready to head home.
As I left she asked to see me again, but explained that she had to return home the next day. So, she offered me a free First Class Sleeper rail ticket to Sydney at a time convenient to both of us. I saw this as an ideal opportunity to take my kids on holidays with me to see their grandparents, so asked if I could include my three kids in the sleeper cabin, which was agreed.
My ‘bidder’ and I arranged to meet at her home on Sydney’s north shore for another ‘date’. Her daughter, aged in her 30’s, was there when I arrived and I was curious if this was going to be a threesome, which I wouldn’t have minded one bit. However, her daughter left and I could sense there wasn’t any intention for us to leave either. Soon we were fucking each other enthusiastically in her bedroom. She had shaved for this date and I found this very appealing and found myself actively applying liberal doses of cunnilingus to her creamy cunt. In appreciation of her generosity for the rail tickets, I felt obliged to satisfy her needs before mine and she came multiple times before I finally mounted her and fucked every last drop of cum from my balls into her craving cunt.
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