This is a true story however I have had to make some very minor changes to protect the privacy of others.

Last Saturday began in a pretty average way, but then it all started to go crazy. During the afternoon I made a purchase on an internet buy/swap/sell page and all I had to was drive to another suburb and pick it up. Well when I got there the lady invited me in to make sure I was happy with what I bought and she said she was alone in her house. She looked about 55 and I doubt that I was there more than 20 seconds and she starts telling me that she works as a sexual massage therapist. I was surprised that she was so upfront about her business and when she asked me what I did for a living I told her what I did before I retired. As it turned out she knew a lot of people that I knew, and I knew her ex husband. She talked a lot about sex and what she does and doesn't do and I definitely got the impression that she wanted to give me one "on the house". Remarkably I decided not to get involved because she seemed to much like a crazy blabbermouth but we did talk for 30-45 minutes. She reminded me of some crazy people I have met where there moods can flow from one extreme to another, or something minor will cause them to have a complete change of personality. Anyway I negotiated the asking price down by 25%, paid her and left.

I got home about 4.00pm and was feeling like I needed some sexual release so I knocked up a quick advert and put it on a Personals website. My ad started to get some replies from the usual assortment of idiots,no hopers and time wasters. Although, there were a couple of replies that held some promise. Several hours later I found someone that sounded interesting and we agreed to have a NSA meeting and if all seemed satisfactory I would then take him back to my place for a jolly good fucking .He was a mature guy the same age as me. We met about 10.30pm and he had already let me know that he'd only done this a couple of times before. He seemed okay but quite nervous so anyway I invited him back, I drove home and he followed in his car. When we got back to my place he seemed very uncomfortable. I offered him a drink and he swallowed it in one gulp and he just didn't act like he wanted to be there. I led him through to the spare bedroom hoping that he would start to loosen up and then he seemed to have a panic attack or severe anxieties and said things about not being able to do this and what if someone found out about him and some other stupid mumbling, then he quickly walked out got in his car and drove away. What a waste of effort that chickenshit bastard was.

Not to be deterred by the last no hoper I was straight back to my advert and connected with a guy in Spole street West Town. He was a tradesman in the building industry that was here doing insurance repairs and staying at a guest house. He invited me over so just after 11.00pm I pulled a cold 6 pack from the fridge and headed off, the drive there took about 15 minutes. I had a little bit of a hard time finding him but he saw me slowly cruising along the street and waved me down with his torch. He was very easy to get on with and for the first half hour we sat on his balcony drinking beer, talking and pissing over the balustrade. He showed me his hard cock, the length was unspectacularly average but the girth was very thick and so sitting in the darkness we took turns sucking each others penis.We then went into his bedroom and simply indulged ourselves with sucking, caressing, rubbing, nipple play, massage and wanking. By around 2.00am we had done more or less what we wanted, he had cum while I sucked him but I hadn't blown but I was not disappointed by it, and we decided to call it a night. I'd had a good time with him and I was happy.

I was back home before 2.30am and saw that I had left the computer on, I thought I would just re-read some of the replies I got before crashing in bed. While I was doing that a new reply popped up and there was something intangibly different about it, anyway I said hello and we talked for a while. He asked me what I thought about Cross Dressers and I told him that it was my secret fantasy to fuck one that was wearing high heels,stockings, garter belt, basically the whole shebang. He said that he likes to dress up and be called "Totty" and be completely dominated and was I interested. My dick had gotten hard again while chatting thanks to the magic of a Viagra that I preemptively swallowed many hours earlier. This seemed like a dream cum true. He gave me his address, I grabbed a cold bottle of cheap wine from the fridge and was heading back to West Town no more than a few hundred metres from where I had been less than an hour earlier.

From this part of the story on, things might seem a bit confused because I am going to use the terms he and she to describe the same person, this is meant to convey my feelings, mood and emotional involvement with what was going on. I arrived at the house a bit after 3.00am and saw an interior light was on but so were some other houses in the street and I was naturally wary that it could be a prank setup. As I started slowly walking down the drive way I saw 2 or 3 beware of the dog signs but no dogs were barking so I quietly called out her name into the darkened area beyond the carport. "Totty" I called but no answer, another half dozen steps and I called again "Totty" but still nothing. My hard cock was urging me on and overcoming my fear of being eaten alive by the carnivorous guard dog plus I had my bottle of wine as a weapon (I could throw it behind me while running away). For the third time I gently called "Totty" and then she appeared from around the rear of the house and walking towards me. She was absolutely stunningly slutty gorgeous and I couldn't believe what I was seeing just a few feet in front of my eyes. Without consciously saying it I heard myself say WOW and she heard it to and that immediately broke the ice. She welcomed me in a voice like an angel would have and sweet as chocolate and cherries. She led me to the patio out back where there was a table and chairs where the light was better and I could soak up her sex appeal. It was hard to tell but she looked like she would have been in her late thirties. She was only about 5 foot 8 inches tall in purple high heels and black stockings held up with a lacy red suspender belt. The tiniest blue denim micro mini skirt almost but not quite covered her brilliant red string sided panties, however it couldn't quite keep her balls captured. Above this was a perfectly fitting black bustier and to complete the outfit a long wig in a sort of reddish brown colour she was of thin build, almost like a boy and around 60 kgs. She had a Scotch and coke on the go so I started on the wine. He laid down a couple of ground rules, like not taking off his wig or high heels and to keep the mood he had to be treated like a slut and be totally dominated and humiliated. While telling me this she was actively encouraging me to feel her all over and everything was fair game. She told me that I was handsome and that was something I had not heard for a few decades, many times I complemented her on her sexual attractiveness and I meant it. I didn't have to butter her up, it was obvious from the beginning we were going to fuck like rabbits.

He finished his Scotch and I emptied my wine glass onto the garden and so we headed to her bedroom, as I followed Totty to the bedroom I could see this house had been fully renovated I wouldn't even begin to estimate how many hundreds of thousands of dollars it would have cost. Someone spent a truck load of money doing this place up. Anyway she led me onto her king size bed and I strip off as she lays down. I tell her to call me Daddy and I will address her by any dirty ,filthy whore shaming name I fucking well choose to call her, she loves it. Very early on during the foreplay I can feel something in the crotch of her knickers, I thought it was some kind of ring shaped device to hold her cock down between her legs that would make him look more female shaped. Just after arriving I did see and play with his cock, it wasn't particularly thick but his cock while soft was still considerably longer than mine when hard. She was sucking my dick and making sweet noises and promising to be good in the future and when she spoke it was always in a soft feminine way. The object in her panties turned out to be the base of a butt plug that she put in to stretch and prepare her arsehole for my cock. It was a brilliant night of sex for me and she was happy being humiliated and dominated. When ever I felt like it, I would tell her to lay in the middle of the bed and while I straddled her face she was to spread my bum cheeks and lick my arse and try to get her tongue into my arsehole, it was just magnificent. Once in a while if I didn't think she was trying hard enough I would lay her face down and spank her buttocks. When I wanted to suck his cock I would tell Totty that I was licking her clit or if I wanted to give the balls a work out I would say to her that I'm licking and sucking on your labia It was just full on sex. We sucked and wanked, I bit her nipples,she was on fire with passion, I left love bites on her buttocks, we nibbled on each other ears and licked necks,the more that I made her gag on my cock the more she wanted it, we 69'd, Christ knows how many times she "needed" to be spanked and I would only stop when my hand would begin to tingle, we fucked, I buggered her again and again with her butt plug, when we kissed it was like she wanted to suck my tongue right down her throat, I made her massage my prostate, I made up stories of her deceiving me and then verbally abused her and she still wanted more. And then I would spank her again. We carried on like this until around 6.30am when we realised that it was well after sunrise and natural light was entering the bedroom.

The way he stayed in the character of Totty was amazing, even after we finished fucking. He got up to have a piss and while I was laying on the bed I clearly could see him in the ensuite. She put the toilet seat down then lowered her panties with that cute sexy hip wiggle that women have when removing tight clothes then sat down to piss. I was fascinated watching this happening and he was giving me the best performance that he could. Thirty seconds later I watched him count off five sheets of toilet paper and carefully dab the drops from his penis. After flushing it was the same sexy wiggle as the panties came up again. It was a fantastic night of fucking, I had never done anything like this before and I seriously doubt it will ever happen again, the magnitude of this fuck will remain with me and be one of the happiest memories for the rest of my life. Lastly what was odd was that at no time did Totty ever get as much as a glimmer of an erection. Before leaving we again sat outside on the patio looking up to the hillside and listened to the morning bird calls and just talked about life in general. He told me that he'd had a good time but also indicated he only does this once or maybe twice a year and so far never with the same person twice. It really was time to leave now so everything had been said and I shook his hand and walked back out to my car and drove home. My regret is that I didn't kiss her goodbye, he was gorgeous.

Twenty four hours later and its Monday morning and I was still horny and basking in the sexual odyssey of Totty. I sent a friend of mine an email asking if he wanted to screw. He's a shift worker so he can be ready to fuck at different times due to his roster, he's the same man that gave me my first and only prostate orgasm. As luck will have it he was winding down after a night shift and said a nice fuck would put him straight to sleep. I went over and we had a nice relaxing session. He is mainly a bottom so I penetrated him in doggie style, but very quickly I felt the forces of ejaculation approach, I withdrew in time and we had a nice lazy session together. Finally I came in his mouth and he came while I wanked him. It had been a relaxing morning session between two friends with no pressure to perform.

Sometimes I just fucking well amaze myself. What do you think?