Lucky In Lisbon

She asked me to take her top off and wow … that revealed the best boobs I had seen

My wife and I started to plan early retirement. We planned to take trips and live in various parts of the world for a few months here and there. Of course enjoy the grand kids more. Then my world changed. All plans out the window. I was suddenly by myself. The thing I wanted to get away from most, my work, became my rescuer. My children were great. Handled things much better than me.
A couple of years down the track, still working and despite the best efforts of my female friends in the old circle, my interest in sex was confined to the sanctuary of chat rooms. In these rooms I could explore many different fantasies and masturbate. Never thought it would that enjoyable.
Luckily for me, my work sent me to a conference in Lisbon. I think it was a reward or their way of helping me out [they had done plenty for me anyway] because I did not usually go to these things more an executive thing. My boss knew my wife and I had been to Lisbon before and had a wonderful time. Perhaps she thought that would cheer me up a little. She suggested I take some holidays over there and that, as it turned out, was a great idea. I never could thank her enough.
So … the conference was like any conference … presentations, networking, lots of chat and a few nice lunches. Frankly I was glad when it was over so I could just relax and re-acquaint myself with this great city. Sex of course was the last thing on my mind (well with a real person).
The first thing I did was go on one of those urban food walking tours. Then I saw her. This big, beautiful woman. The main reason I looked was I thought she was (now don’t laugh) Nigella Lawson and who doesn’t like Nigella! I looked twice and of course she wasn't. Then I thought … well she wouldn't be part of the walking group anyway most likely a local. Imagine my surprise when she was not only part of the walking group but had this great London accent.
Ordinarily, I would not even think of talking to someone as gorgeous as I thought she was but, being on holidays I had nothing to lose. If I made a goose of myself, I would never see her again. As it turned out she was so easy to talk to. Hi I'm Rusty, I said I bet you are she said! I am Olivia she said. Beautiful name and a comedian too I said. We both laughed. This tour finished with lunch and we made sure we sat together. We chatted incessantly. I thought to myself … well at least I can still have a conversation!
We made plans to catch up later and, as it happened, it was only a 20 minute walk from her hotel to mine. When we departed, she said I'll make you a pole dance before you go home. I just said, rather naively when I think about it now, sure OK but be gentle you know I am nearly 60 and not as supple as I once was. She laughed I laughed and a way we went.
Later I walked to her hotel and nervously waited in the lobby. To my great delight she turned up. We walked down the hill towards Restauradores square. I was that comfortable with her, a mixture of holiday bravado, some alcohol and just being really relaxed in her company, that I placed my hand in hers without even thinking. Luckily for me she just accepted it. I was thinking my luck had changed … finally a woman who is not going to pressure me for sex.
We had a delightful evening, and I walked her back to her hotel. Rather chivalrous of me I thought. Of course we had a drink in the bar and then before I could say goodbye see you tomorrow, she invited me to her room. I was nervous, excited and a little flattered all at the same time. With great anticipation I went with her.
Olivia was the most stunning woman I had seen for a long time. She was taller than me, about 5'10" I'd say, she had a well-rounded full figure that was well proportioned [I am wet just thinking about her]. It was not long before we were kissing and touching. I thought I was going to explode! She asked me to take her top off and wow … that revealed the best boobs I had seen (with a touch of breast feeding sag) and I suckled them like I had not suckled ever! Olivia kept her shorts on but that was OK I had already got more than I ever hoped for.
Olivia undressed me fully. She rubbed her boobs all over me. I don't know to this day how I did not cum. I had not had any human touching [apart from me touching me] for about 3 years. Then she started with the head job. Wow! Squeezing my nuts, swallowing my shaft, just magnificent! I told her I was about to cum, but I think she sensed it before I knew it. She squeezed my cock tight and that seemed to do the trick.
She then said she was going to the bathroom to prepare. Rather feebly I said OK. My head was spinning … finally I am going to get a shot away with a gorgeous woman who just wants me for sex and nothing else. I smiled to myself with satisfaction. Anyway, Olivia reappeared wearing the hotel bathrobe. I thought great more seductive tricks. I was sitting on the edge of the bed as hard as my chubby 6" could be, she stood in front of me and dropped her rob.
There directly in eye line was this big, thick, powerfully erected penis! OMG. I looked at it. I was not horrified or turned off. I just thought how magnificent it was. In what seemed like a long time but probably only seconds I said wow is that for me. Olivia said only if you want it. Then I smiled. Olivia said what's up, I said … you told me you were going to make me a pole dancer … I understand at last! I touched and kissed her magnificent pole.
What do you want to do she said. I said … Could you just lay on me? I want to feel your body on me. She was on top and it was beautiful. I said to her that I was not ready for a full experience just yet. She said OK we have tomorrow. I nearly lost my juice just with those words! Wow she wants me! I said that I would like her to cum on me. I wanted to see that fantastic cock cum on me for me.
Olivia had a little bag with some "helpers" in it. There was a dildo, butt plug, lube and a thing she told me was used for anal cleansing. Olivia took the lube got our erections together, poured some on and began masturbating us. She would have been at least 8" of excitement and dwarfed me a lot.
Now as you would expect my cum was extracted very early, but Olivia kept going and then she shot her cum over me. On my belly and chest. It was a warmth that I needed to feel. She rubbed her cum playfully into my hairs. She made a mixture of our juices with her fingers and palm. She gave me some and she had some. I can't tell you how erotic that moment was! If that was all you had to do to be married at that moment I would have been married!
We laid together kissing, cuddling chatting. Olivia suggested a shower together. She took my hand and led me in. She soaped me first and then I her. I loved her cock and balls. Next thing she starts pissing. I said you want to mark you territory. She said yes. I grabbed her cock and directed her piss on my cock and balls. Another wonderfully erotic experience. I was in another world and hard again.
We finished the shower. Olivia gave me another head job to celebrate my chubby she said. This time she let me cum [what there was of it!]. I masturbated her and licked her shaft. I just couldn't quite do the full head job yet. I was glad to get her to cum again in any case. Olivia did not mind the no head job because, as it turned out, she had plans for me. She told me she was not going to leave Lisbon without fucking me and me fucking her. I said I would like that.
It was time to go, this old guy need to rest. Before I left, Olivia gave me directions on how to use her anal cleanse device [rather obvious once explained]. She said it was best done in private and to get it done for next time which was tomorrow. I can't wait to see her!