Sometimes you never know when things work out. There I was in a bar in Sydney on a Monday after a committee meeting debriefing about the day's events. We had had a few drinks, when I heard a woman with an American accent at the bar order a drink. She was sitting by herself. I guessed she was in her sixties, but certainly well dressed and well-presented overall. I could see that she had a delightfully ample chest. Her gaze seemed to be inviting, so I did the appropriate thing and said hello (g'day to be specific), asked her name and which state of the U.S she was from.
She seemed a little flattered by the attention and responded that her name was Sheri and she was from Nevada. I liked the twinkle in her eye and she had that air of confidence that suggested a woman who had been successful in their career. As we got talking she revealed that she was on holiday, and that she was originally going to be travelling with a friend, but that they had to pull out at the last minute. Rather than waste the fare, she decided to come to Australia by herself.
"No one to have fun with unless I meet some nice locals who will show me the town," she joked, a natural laughter emanating from her.
As we talked it became evident that our sense of humour complemented each other. My colleagues drifted off one by one until there were just the two of us. Rather than just stay at the bar, I suggested we go to a restaurant. I knew a good one around the corner, only a short 10 minute walk away. Sheri agreed and I offered her my arm and we walked together.
As we did so, Sheri voiced that she was too old for me. She said she was in her mid-sixties, and asked how old I was.
"42, and no I am not too young for someone as fun and vivacious as your good and sexy self," I replied.
The meal was excellent as always at the particular establishment I had chosen, and I guided Sheri to some of the tastier morsels on the menu that she was unlikely to have eaten at home. I also introduced her to some of the finer Hunter Valley wines on the wine list. As we chatted she revealed that she had been attracted to me when she first saw me. It was my turn to be flattered. As the evening continued, the talk somehow turned to sex. It's debateable as to which one of us led it there in the first instance. She asked me if I had ever had any encounters with a woman in her sixties and I responded that I had not.
"Your breasts are beautiful, what size are they?" I asked.
"40D," responded Sheri.
I thought I'd go for broke and say something that will either end our evening rather abruptly, or send it an entirely different direction than I suspected Sheri had in mind.
Rather nonchalantly I said, "Your breasts are simply divine, god I'd like to tie them up."
Not unexpectedly Sheri responded with a "Whattttttttttttttttttt did I hear right?"
"Yes, I am into BDSM. Is this something you're potentially interested in?"
Sheri was lost for words, "Ummmmm No.... I mean perhaps yes........... I've never really tried.... Ummmmm.. Ummmm... I don't really know what to say."
I didn't push things, but did explain that I usually met women on line so that a liking of BDSM was already established.
As she got over the shock, Sheri offered that she was fascinated and intrigued by BDSM but she had always been a cowardly lion and had never ventured about seriously considering doing anything like it.
Sheri offered, "What a country, you meet one guy at a bar, and the next thing you are talking about kinky sex and the possibility of being tied up and good knows what else!"
We then spent a good half an hour or so with mostly me talking about what I was and wasn't into. I explained that a partner sets the hard limits and then things that they really want to try and be pushed on. I explained that the key to BDSM play was safe, sane and consensual. By continuing to engage in the conversation, I could tell that there was more than an interest in participating.
In the end I concluded, relax and let your body and mind be led to somewhere that you have never gone before.
"What the hell, I may never get another opportunity and I am very horny now."
"Where shall we go," she asked.
I suggested we go to my place, after we swung past her hotel so she could pick up a change of clothes and whatever else she needed.
Outside the restaurant and in a quiet area of a side street, we did something more conventional. I slowly swung Sheri around and kissed her sensuously and deeply. She responded passionately. We finally broke of our lusty embrace and made our way first to the hotel, then to a taxi, and then towards my place which was about 20 minutes drive from where we were.
When we arrived at my place I took Sheri's arm and escorted her inside. I poured her a glass of wine and told her to make herself comfortable while I got things ready.
I knew Sheri was new at this so I wasn't planning on going through anywhere near a full repertoire of torments. I was planning on taking things slowly and ensuring I gave her a little taste of something different. If she had a good time, maybe she would travel further down the path............
When I invited her into the bedroom, I could see her eyes were full of both trepidation and excitement -- a lovely mix.
"Darling, sit on the end of the bed, and close your eyes, your journey begins."
I started to sensuously massage Sheri's shoulders and neck. Slowly my fingers and thumbs firmly worked their way into soft flesh, my thumbs swirling into the back of her neck. My long fingers worked their way into her shoulders, before I started to caress Sheri's face, particularly her soft cheeks. I ensured my hot breath danced across her neck as I did so. I traced the outlines of her eyebrows ever so lightly. I interspersed my massage of her shoulders and neck with gently caressing her facial features.
My efforts had Sheri purring, so it was time for the next step. I undid the top button of her blouse and then returned to massaging her neck. I then undid the second, getting a clear few from above and behind of the top of Sheri's bountiful tits. I then swished my hands slowly around from her neck to her chest and caressed her, careful at this stage not to touch her breasts.
"Mmmmmm," sighed Sheri languidly as I nuzzled her ear and promised much more.
It was time to remove Sheri's blouse, I undid the remaining buttons and took it off her. She now sat on the end of her bed wearing her bra, skirt and whatever was under her skirt. I would find out what that was in the fullness of time. With my own neck resting on Sheri's right shoulder, I reached around and slid my hands up her side and then cupped her breasts. She moaned as I did so, and I felt her body tense and saw her bite her lip lightly. I repeated the effort, each time I grasped her breasts a bit more firmly, lifted them up just a tad more. For about 15 minutes I teased and caressed her tits through the fabric. Sheri had my undivided focus.
"Aged to perfection," I whispered into her ear.
My own cock was rock hard in its confines as my hands worked over Sheri's tits. I guided Sheri's hand to my crotch and she squeezed instinctively, feeling the hardness there, before I withdrew her hand.
"It's time I had a look at your tits Sheri, I've been dying to see them since we first started talking."
I unclasped the buckle, and slid the bra down, kissing her neck as I did so. Her breasts spilled free of their lacy confines. This time it was my turn to gasp as I gazed down at Sheri's tits.
"So magnificent...... I am going to have fun with these," I said indulgently.
I slid my hands up and cupped them again. My thumbs swum around her nipples wickedly, flicking and squeezing, pushing them in gently. My hands were overflowing with beautiful tit flesh. With each touch of her rock hard nipples, Sheri moaned. The slightest fragrance of wet pussy started to drift liltingly through the room. I spent a good period of time squeezing, kneading and massage Sheri's breasts.
I finally ceased my heavy duty breast massage and came around faced Sheri.
"Open your eyes Sheri," I said.
I looked deeply into her lustful gaze and said, "Sheri, I am going to give me the opportunity to tell me exactly what you want me to do with your tits next. This is not an opportunity I offer to anyone."
Sheri responded, "I need your mouth on my tits and my nipples, I need you to suck my nipples."
"Very well then, I shall suck your nipples into lustful oblivion and beyond, now offer them up to me," I replied.
Wordlessly, I broke our gaze and descended on to her offering. I inhaled first one and then the other nipple deeply. I sucked vigorously and occasionally broke off the sucking to swirl my tongue around the hot and hard flesh.
After such vigorous sucking, I finally asked Sheri to stand up in front of me. Her tits were noticeably red from my busy hands and her nipples exceedingly engorged. Take off your skirt for me Sheri. She did so quickly and stood in front of me in her panties.
"Are your panties wet Sheri?" I asked, and she replied that they were soaked.
"Take them off then."
Sheri stepped out of her panties.
"Beautiful," I offered, before adding, "I bet you didn't expect at the start of the evening, that you would end up naked in front of a man. I also bet you didn't expect what is about to transpire -- a thoroughly spanked ass that will almost certainly end up with my cock in it, a fist in your cunt, and your tits tied and used."
I added after a pause, "and who knows what else."
Sheri grinned expectantly before I asked her turn around, bend over and put her hands flat on the end of the bed. I shifted her legs apart slightly and put my fingers against her cunt.