We met through On-Line Dating and were a mutual source of fun and excitement for a brief period of time and a memory that triggers an erection every time I think of her.
(Bondage, first anal, toys, big boobs / breasts, submission, public nudity, voyeurism)
By Career Councilor: I am a Toronto based, Internet Author, I write stories about erotic encounters for ladies or couples and post them on EroticStories.com Copyright: (c) 2018 by Career Councilor - CareerCouncilor@Outlook.com Redistribution is permitted, if it is done on non-commercial basis and this header is preserved. Comments would be appreciated
We met on-line through a Dating App and her very modest pictures caught my eye. High collar white sweater (very modest but stretched to the limit about ¾ of the way from her waist to her neck) and a conservative black and white patterned dress with some splashes of orange and a black sweater that curved out wide around her upper chest. (By the way, I am a boob man.)
"Some college - 5' 8" - Christian non-smoker, Drink Moderately, Exercise 3-4 times per week, I like travelling, watching sports, dancing and listening to live music. Seeking a serious relationship." (I soon found out that she was a retired teacher with a modest lifestyle living in a harbour front 23rd floor, controlled entry condo with an expansive view and no one could look in her windows except those above the 22nd floor in the next condo, many with telescopes.) Her name was Karen, just over 60 years old and in a part-time relationship with someone that I think she loved but he was not reciprocal and not completely available. They were never intimate. Generally, quiet, seemed a bit timid and I wasn't sure if she would be inhibited or not but often ‘still waters run deep' or the quiet ones sometimes have the most pent up desire.
Initially we chatted by phone and then met for a coffee and I learned: she loves music and performed in six musical theater shows. she took voice lessons for six years and loves to sing. She also loves to dance, eat out, cook, exercise, watch sports and travel.
I think it was our next ‘date' for dinner at a roadhouse that I broached the subject of sex and was totally honest with her that I found her figure stunning for anyone over 40 let alone over 60. I also promised her that we would not have sex together the first night that we slept together, and she found that comforting even if it seemed confusing. I explained that I was not interested in a one-night stand and assured her that I would be happy to do everything else (dreaming about her breasts) except have actual sex until we were more sure about each other.
Over the next few weeks, we got to the point of having great sex in her living room, kitchen, bedroom, (hers and mine) and getting comfortable talking about our past ‘experiences' while I learned more about what could drove her to and over the edge.
A couple of years ago she booked a cruise by herself and met a sexy Italian guy on the plane that was also booked solo on the cruise. Apparently, she actually slept in her own room the first night and then spent the rest of the cruise sleeping in his room experiencing his sex toys and leather cuffs and stuff. (Obviously an optimist that he brought these things with him, solo, on the cruise.) Clearly, he stretched her boundaries (and other parts of her) beyond anything she had even thought of before. She had never been tied up before or even thought of it but seemed to love it. In the following year, she flew to meet him for a couple of wild weekends but other than the exhilaration of stretching her boundaries even more, there was no long-term relationship potential.
She took me out to a very nice restaurant one night and she tried very hard to keep her composure when I slipped my wiggling fingers into her wet anticipation under the tablecloth, but she didn't attempt to stop me. I took her home and tied her to the bed blindfolded and practiced teasing her by starting and stopping a few times to build up her frustration before I let her cum. Yes, I am over 60 now so I do take a little pill that usually results in an erection for 2+ hours so I had lots of time to tease her.
One Sunday afternoon we were on our way to a local English Pub with live music and we stopped at a Sex & Swingers Club on the way, paid our membership and went in to watch basically, just wearing a towel. She was mesmerized by a couple having anal sex in the middle of the floor in the second room and commented that someday, she would like to come back and try that! Anal sex or being watched in the middle of the room? Both she replied. She was approached by a couple of guys as we strolled around and watched other couples which got her thinking excitedly. (I had already shared a couple of my other stories with her including ‘Almost a Threesome'). As we drove to the pub, she confided that she would like to try a threesome, especially if she could somehow arrange for the Italian guy to share her with me. Another evening of fun, intentionally brushing my elbow or arm against her breasts each time I twirled her while we were dancing or pinching her nipples when we were sitting in the corner hidden behind a high table and we though no one was looking. I convinced her to go to the bathroom and take off her bra after we ate, before coffee, desert and more nipple gyrating dancing. When we got into the car in the parking lot, I undid most of the buttons on her top before I put the convertible top down and drove her home with a subtle view of her enormous breasts keeping me excited. I stayed over leaving us both exhausted again.
She mentioned the Italian guy a few more times and while I already had a small selection of toys that we had tried; and while I had been able to make her cum with just my tongue or just my fingers; I knew that I needed to take our games to the next level.
I told her that I was taking her out to dinner on a weekday and that she was to be my ‘Sex Slave' for the evening. She had to agree to do anything that I asked without hesitation or questioning. She responded with a couple of questions about limits and intent before declining the need for a Safe Word. Two days later, I picked her up dressed in a front button thin blouse with a lacy bra that you could easily see thru the blouse as instructed. She was also instructed to wear a short skirt with a (newly purchased) red thong. As she got into the car, it was clear that her nipples were very hard, and her breathing was slightly elevated with anticipation. I instructed her to undo one more button at both the top and bottom of the blouse and we drove away with the wind blowing her short curly hair and me reaching over to check that she followed the underwear prep requirements. The tight thong was already damp as I explored and checked that she had indeed followed all the instructions and was fully shaved.
We just happened to drove by an adult toy store on our way to the restaurant / pool hall, so we stopped in to purchase a medium sized butt plug and some lubricant increasing her anticipation even more as I made her choose which one, take it to the cash and pay for it with a very self-conscious red face as the male casher stared at her protruding nipples and smiled knowingly at me. (In one of our conversations after the sex club, she had admitted that she would like to try anal but hadn't gone there yet even by herself.)
The restaurant is an upscale family roadhouse style with fireplaces near the front windows, a retracting glass roof, 5 or 6 ping-pong tables and about 10 pool tables at the back by the washrooms. During dinner she was completely confused by her ‘Sex Slave' surroundings; a family of 4 with kids about 12-years old at a near by table, a group of business people in suits across from us, a 20-something couple on a awkward first date, two college couples playing pool at the nearest table, eating between turns, two regulars at the next table and 4 guys with beers past that.
I insisted that she not have more than two glasses of wine and I only had one. Just at desert time, the last table at the back of the room opened up so I suggested that we play pool while having desert and a liquor. While she went to the washroom, I set up the table for spots and stripes and mischievously removed the rake from the table giving it to the 4 guys and beers at the next table, promising them it would be more fun if they kept it. I selected a worn slightly warped pool cue for her and an almost new one for me. When she returned, we intentionally stood between the tables as I explained the rules of spots and stripes to her and our special rules just loud enough for the 4 guys to hear while they waited to continue their game.
"Since this is our first game, you will be spots and whenever you sink the #1 ball, you will go directly to one of the men's washrooms, take off your bra and bring it back to me placing it on the shelf beside my drink". Her understanding of the instructions increased her breathing and her face started to turn a lovely shade of red. She started to protest but I reminded her of the rules and of how she trusted some Italian guy that she had just met to tier her up; rebutting any complaint.
Since I am not a great pool player either; the game took a while and as we went along, I had to teach her how to lean across the table to make those more difficult long shots without using a rake since we didn't have one. One of the guys clearly noticed that she was wearing a thong and gave me a thumbs up as he pointed at their second rake. The next time she had to reach for a long shot, I coached her closely, reaching across the table and slid my hand up her exposed thigh finding that the red thong was now much wetter and darker in color. She knew that we were being watched.
Finally, the only ball on the table was the #1 ball after I sunk all of the stripes and the 8-ball to win the game, so she had to try several shots to sink it. She automatically grabbed her purse on the way to the washroom after contemplating her required shot BUT, I told her to leave the purse here so that she could not hide her bra in it causing several new expressions to cross her face anticipating the potential embarrassment. The guys at the next table continued to play distracted pool as they awaited her re-appearance.
She returned slowly with her arms crossed clenching her bra tightly and her large breasts literally resting on her folded arms with her dark nipples sticking out, straining the thin material. Two of the waiters heading past us to the kitchen stopped, the 4-guys stopped, even the waitress coming from the kitchen stopped while I held out my hand for her to give me the bra. She was clearly reluctant but also eager to see what else I had in store for her.
I had already explained that we were going to play 3 games of pool. She literally guessed that for game #2; sinking the #2 ball would be the trigger for her next embarrassment - go to one of the men's bathrooms, remove her bright red thong and return it to me. She played much better and it was a joy to watch he literally lay across the table to reach those really long shots and she started to really get into the game and intentionally tease me with a periodic view and intentionally rubbing her chest against me each time she walked by me to make a shot.
About 3 balls later she sunk the 2 ball and just stood behind the table away from the kitchen door and took the thong off, leaving it laying on the table while taking her next shot. Given their level of on-going interest and distraction, the four 20-something guys at the next table found this 60+ year old lady very appealing which I pointed out to her a couple of times as she exposed herself reaching for a shot and dragging her solid nipples across the table as she started to play to the small audience.
For game #3, she had to undo a button on her blouse or raise her skirt and inch for each ball that she sank before the 3 ball. I also told her that there was another surprise for her in the bag that I bought previously at the adult toy store for her, that I had been carrying around all night for after she sunk the 3 ball. By the time she did sunk the 3, the waist band of her skirt had been folded over twice and her blouse was un-buttoned to just below her breasts, I sent her off to the washroom with very specific instructions for the toy in the bag.
She returned more quickly than I anticipated with the egg-shaped vibrator inserted in her pussy and the pink remote controller hanging out of the waist band of her skirt, almost covered by the bottom of her blouse. I had taped the controller switch so that she could not try it before returning to the table. Each time that she had to reach across the table for a long shot, I turned it on so that I could watch her twitch with distraction as she exposed herself and tried to concentrate.
There were about 4 or 5 balls still on the table when she started to beg me to just take her home a fuck her, please, please just take me home and fuck me she begged as the 4-guys finally left an empty table beside us.
When we got in the car, I extended the controller from her waist band to rest on the center console and insisted that she undo the rest of the buttons sitting with her hands behind her back and the seat belt resting tightly between her massive breasts. At the first red light I turned up the vibrator and put down the convertible top so that the coolish night air would keep her breasts hard and blowing into view as we drove along the busy streets back to her house. A couple of times at red lights I reached my right hand over to check on the vibrator and push it further into its new home, getting her to lick my fingers after I was done. By this time, she didn't seem to care if anyone was watching and smiled with a deep breath as one guy in the crosswalk whistled at us with her top blown open and her bare chest in full view.
Near her condo, we drove down some quiet tree lined older streets and a couple of times at Stop signs, I undid my seatbelt so I could reach across and nibble, bite and pull on her anticipating breasts as I rolled the vibrator switch up and down causing her to pant heavily. When we got to her condo, she had to go to security with only 1 middle button done up to register my visitor's car drawing his undivided attention even as we walked away with him staring at the wet spot on the back of her skirt from when I was fingering her as we drove in the car. Once in the elevator, I undid the middle button and knelt down to suck on her breasts as we rode up 23 floors and I am sure he watched closely.
With the vibrator at about ¾ power, I had to open the apartment door for her and by the time I had the door closed, she was naked and heading to her bedroom begging for me to fuck her playing with the remote on her own. While she was distracted; I grabbed her hands behind her back and velcro-cuffed them and slipped a blindfold over her eyes, starting to steer her to the kitchen with floor to ceiling windows and bright lights. I had grabbed a pillow from her bed and rested her head on the pillow on the dining table instructing her to stand bent at the waist with her breasts hanging down, demanding attention. I moved the vibrator switch up and down a few times as I attached a new spreader bar to her ankles from my kit bag and got out her new purchase from the toy store.
Ripping open the butt plug packaging got her attention, breathing heavily, flipping her head right and left on the pillow to try and anticipate what was about to happen. Instead, I attached four large elastics around the base of each of her breasts stretching them to the limit and then attached a set of tight clamps to each engorged nipple. She was almost frantic, screaming with anticipation, pain and need. When I told her the guy across from us was watching thru his telescope she didn't even notice and just kept demanding that I fuck her hard.
I entered her slowly from behind with 3 or 4 slow strokes, each ending with a very hard push. Her breath started to quicken abruptly so I withdrew and stopped, starting to spank her with a small leather paddle instead and added some weights to the chain between the nipple clamps. I applied some lube to her rosebud which elicited a scream from her as I entered her again with my rock-hard erection in her pussy and my finger in her ass. She started to squirm and pant, so I withdrew and stopped again keeping her focus on my probing finger. I entered her again for a couple of quick deep thrusts as I reached around and grabbed her breasts and pulled on the nipple clamps to amuse myself.
I stood with my penis just touching her pussy and moved my right hand down between her stretched legs to play with her swollen clit eliciting pants and screams as I started to pound her again and she exploded into a combination of shaking and convulsive rearward pushes against my cock. She pounded backward 23 times holding her breath and twitching wildly before going limp and wheezing for breath. I slid all of her upper body onto the table so that she could rest a bit.
Using her cuffed arms as levers and taking little steps, I prodded her across to a near by living room chair, bending her over the low back of the chair as I attached her spread legs to each of the short rear chair legs. She was bent over much further than before and giving me much better access. I sat on a cushion on the floor and reached up with my tongue and fingers entertaining her pussy lips and clit until she came a second time with me reaching behind my head to pull hard on her nipples, screaming louder than before as she exploded briefly letting each deep breath out in an almost staccato rhythm.
As she regained her composure, I started to spank her again with the paddle causing her to wiggle her ass a bit. I added some lube and my finger started exploring again until I replaced my finger with our new medium sized butt plug which slipped in easily at first eliciting a lot of nasty words and then a big sigh as it slid into place and was stuck there.
I inserted a lubed dildo brought from her bedside table into her pussy and turned it on to a low rotating grind as I continued to pay with her new, almost comfortable, butt plug, twisting it and pulling it partially out then letting it slide back in a few times. She alternated between stop, please stop and as I did stop, she changed to don't stop, oh please don't stop and I knew she was getting exhausted.
Standing behind her I removed the dildo and entered her again, slowly at first and then pounding hard but changing my angle of attack each time almost like a butter churn using my hands to either pull on her breasts and nipples or roughly push and pull on her butt plug as I continued to relentlessly pound her from behind. This one was my turn and I told her wasn't going to stop until I exploded in her. (I had masturbated just before I picked her up tonight so when you are a guy over 60, coming a second time takes time, effort, pounding and a cautious amount of lube to get the friction just right.)
I knew she was getting close as she tried to match my rhythm and started to pant again. As her pussy grew tight and gripped my probing penis, she exploded again pumping hard against me for almost 30 more thrusts - a new record. I was almost ready too but needed a little extra friction so I pulled the butt plug out of her ass and inserted myself pushing hard for about 5 strokes before I too exploded which she seemed to enjoy based upon her new sounds and how hard she was pushing back against me. I ripped off the velcro ties around her legs and twisted her body as she collapsed landing on the arm of the chair.
I picked her up and carried her to her bed still wearing the arm-cuffs and nipple clamps. The site of her now dark red breasts straining out from the tight rubber bands got me very hard again immediately. As I crawled across the bed above her to get her another pillow, she took my dangling penis in her mouth sucking so hard that I just froze and never did get reach pillow.
When we woke up a few hours later; her arms tied, breasts stiffened by the elastics, the blindfold had fallen off and her makeup was smeared but she was smiling and panting. I took off the nipple clamps, moved her tied arms from behind her back to above her attached to the head of the bed, re-inserted the butt plug and her penis vibrator on slow. She just smiled and went back to sleep with me biting on her nipples.
We Met Thru On-line Dating; Please Remember to Vote!
NOTE: Your feedback and comments are always appreciated. CareerCouncilor@Outlook.com
|
Note from the webmaster: authors always appreciate feedback about their stories, so by all means write the author a note if you liked the story! The author of this story: Anonymous |