Once again it’s been a long time since I’ve written so over the next few weeks I’m going to try to catch up with some of the things that have happened over the last year and then some.
And, as I’ve said in the past, everything I tell you about is true and the conversations, while they may not be word for word, are, as best as I recall, accurate.
So, with that out of the way I’m going to start way back in April, 2020 when I met Helen at a munch that was not far from the Tampa area and we seemed to hit it off right away.
She is in her mid-60’s and teaches at a college. She plans to retire in a couple of years and is hoping to spend her time offering free tutoring, do some traveling and continuing to pursue her personal interests as a sweet and nasty (old) lady that loves to tie, tease, torture, frustrate, embarrass and humiliate women that want nothing more than to lose their ability to do anything more than what she allows and, depending on what she has in store for them, provide (her) with both sexual relief and amusement while keeping her “toy” in any predicament she wants.
I should note that while she is a bit older than I am (I turned 51 in February) I’ve learned that I can (sort of) tick her off by calling her “old” or “mom”. I love her reaction and, eventually, the consequence of saying it. Of course I could say I don’t mean to tick her off but that would be lying and, unquestionably, I know she is playing the game too.
In addition to rope she loves leather, latex, steel and a few “bondage devices” that she has collected over the past 30+ years which allows her to subject her “toys” to things she enjoys doing to them and, from my personal experience, she may or may not allow her “toy” to get any sexual relief.
And, just another brief note, she does not demand to be called Mistress, Madam etc., and she doesn’t refer to me as her sub, slave, slut or cunt (ugh!) or anything else that may be taken as being derogatory. However, whether I am bound or not she will tease me (verbally) in her own way and when we are out somewhere and I am in no position to do anything but suffer the consequences of my situation.
So, after meeting several times for coffee and dinner where we talked about the things she and I liked, disliked, loved and didn’t love. Some of the things we talked about I’d never experienced but after a lot of discussion I agreed to at least try them. Of course we also agreed on my safe words, limits etc. so I felt relatively comfortable meeting with her for the first time at her house in July.
As instructed I wore comfortable clothes and packed a few nice things to wear later (a couple of skirts and blouses, a dress, garter belt and stockings, a couple of lace panties and bras and my 3” ankle strap heels). Helen said she preferred me to come casual but would love for me to “dress up” later because, as she put it, she had a soft spot for obedient lipstick lesbians (I had to google that to be sure I remembered what that meant).
For a safety precaution I gave my friend Anne (I’ve written about her in the past) Helen’s address and cell number so if she didn’t hear from me by Saturday afternoon (to check in) she could send for the cavalry.
Helen lives a little more than an hour from me and despite some traffic I pulled into her driveway after driving for about 1 ½ hours. As I reached her house I could see that her nearest neighbors were quite a distance away (she told me she had bought an old farm many years ago) and, so, after checking my hair and make-up (I almost decided to back out and go home) I got out, grabbed my bag, walked up to the door and rang the bell.
I don’t think I stood (shaking) more than a few seconds when she opened the door and told me to come in and as soon as I put my bag down she gave me a very warm hug and told me how happy she was that I decided to come.
“Leave your bag here, we’ll take care of it later, come with me to the living room”.
I thought, “that was a short welcome”, but of course I followed her.
The house was really lovely, she has (in my opinion) very good taste, and almost all the rooms have large windows that causes them to feel bright and airy and very welcoming.
“Take your clothes off”.
“Yes my dear, now, you came here to be tied up so unless you’ve suddenly changed your mind, take your clothes off while I go and get some rope and things”.
She turned and walked away and I just stood there (like a deer in headlights?) thinking, well, so much for small talk and relaxing a little from the trip, but I did as told and took my clothes off. I almost left my panties on but I figured she said get undressed so they had to go too.
I don’t think I waited more than 4 or 5 minutes for her to return but I do know that I was blushing (a lot) and my nipples, those awful tattletales, were at attention and when I touched them I felt their “reaction” go straight to my pussy. I knew from touching myself while driving to her place I was (wet) and now, standing naked in the middle of her living room, the only thing I could do was to try not touching myself…too much.
When she came back she was carrying a lot of rope and a tote bag that she put on the coffee table. Looking at me she said, “Your nipples are so big, maybe bigger than you told me, and those tiny breasts won’t get in the way. When we met for dinner and coffee it was hard for me to see just how big they are. We’re going to have so much fun”.
If I was blushing before I was now bright enough to light up, I don’t know, Times Square in New York?
“Come and stand facing me”.
Taking a couple of small steps I stood maybe a foot or so in front of her and for some reason couldn’t stop myself from looking up into her eyes. I know this may sound silly, but they seemed “hungry”(?).
Helen is 5’9” tall in her bare feet, I am all of 5’3” (and sometimes I think I’m being generous with that) so looking up at her made me feel even smaller and, in a way, very vulnerable.
She put her fingers on my nipples and at first gave them a gentle squeeze. I groaned and pushed against them. Smiling (down at me) she squeezed harder and twisted them. I groaned louder and pushed against her more. She pulled them (and me) towards her, and while holding me close gave me a kiss and said, “You smell like you’re ready to explode, we have to do something about that”.
As soon as she let go of me I brilliantly said, “yes please”, and I don’t even remember if I said it very clearly but she certainly understood because the next thing she said was something like, “don’t worry, I have plans for your nips and pussy”.
Moving my arms down to my sides she went to the tote and pulled out a posture collar. Now I have worn posture collars in the past but this one seemed much “taller” than any of the others I had worn.
When she stood behind and put it on it was so tall in front that it forced my chin up and it felt like the sides of the collar were quite high too. As she buckled it and it became tighter she kept asking if I was okay and, despite the fact that it was becoming a bit severe, it wasn’t choking me so I said I was okay. By the time she was finished there was almost no way I could look down without bending at my waist and to look to the sides I could move my head a little but it was easier to just turn a bit. Again she asked if I was okay and I tried to nod “yes” but found it easier to just mumble “yes”. I reached up and put my fingers on its edges but there was no way to make it looser without undoing the buckles.
Reaching around me from behind she used her fingers on my nipples again and I practically danced in place as she played with them. I leaned back against her and with her lips by my ear she whispered, “I’m going to have so much fun with you”.
“Now stand still while I get some rope and make you a little uncomfortable”.
She was smiling so I tried to smile. Uncomfortable? Shouldn’t she have said “more comfortable”?
Taking my hands she crossed them and tied them in front of me. Hmm, not what I was expecting but I knew that I was tied pretty good.
“Now put two fingers in your pussy and when I tell you to take them out they better be soaked”. I said nothing and did as I was told. And it felt really really good.
A slap on my ass, “If you come, I’ll whip you until you can’t sit down, understand”?
“YES”, not much more I could scream at that point.
“Stop, put your fingers in your mouth and keep them there until I tell you to take them out”.
Less than a minute later, “Take them out of your mouth and put them back in your pussy”.
Damn…made me even hornier…
“Open wide”, she said as she brought over my head not a simple cock gag but the kind that has a short cock to go in my mouth and a longer one that sticks out of my mouth and even though it was obvious where this was leading I was flushed and wriggling because of what I was doing to my pussy and when she buckled the damn thing pretty tight there was very little I could say that could be understood. My tongue was held down and with the little movement my head could make all I saw was how the cock in front of me wiggled and jiggled until she told me to stop touching my myself and to “Sit on the floor and bring your ankles up so that you are in a lotus position”.
A little awkward because I really am not all that flexible but I did manage to get my ankles together and used my hands to keep them there.
Kneeling in front of me Helen used some rope to tie my ankles together and then tied my wrists to them. To make sure I had more help staying like that she ran the loose ends of the rope through the ring on the front of my collar, tied a knot, and then finished that off by winding the last of the rope to the back of the collar with a final knot that was impossible for me to reach.
Forced to lean forward with my head/chin held up was not very comfortable. So I figured that’s what she meant by making me “uncomfortable”. But I was wrong.
Using two more pieces of rope she managed to tie my thighs to my arms so that I was fixed in such a way that I had almost no movement. I was literally stuck in that awful bent forward position and with the gag filling my mouth all I could do was groan and drool. It is one of the things that embarrasses and humiliates me the most, drooling like that, and from everything we had talked about she knew it.
Standing up, she pulled my hair forcing me to look at her and asked if I was having fun. I mmmppphhhdddd (NO).
Then, laughing, she said, “I am”, walked past me and sat on one of the chairs.
I felt like so incredibly pathetic, I could rock but that was it, I couldn’t touch my nipples or my pussy, I was stuck and the only thing I could do was make as much noise as I could trying to beg her to touch me while still drooling like a small waterfall. I think a turtle on its back is more able to move than I was able to.
But no matter what I tried there was nothing I could do and it wasn’t very long before I was not only “uncomfortable” but the position was becoming a bit painful.
By the way, if you hadn’t realized from a couple of my previous stories I am becoming (for me) quite the pain slut. No, I don’t want to be cut, pierced or have lasting marks but the pain does things to me that I never thought was possible. And, as I’ve said in the past, I don’t even try to figure out why anymore. I “lovingly” accept it.
Well, enough philosophizing…
I wasn’t paying much attention to Helen, I was all too absorbed in my “situation”, so when she suddenly stood in front me and I saw she was naked (oh my!) my head moved so I could try to see more, my nipples, as hard as they were, felt like they were getting even bigger and my pussy, well, I thought it was drooling too.
“Now let’s have some fun”, she said and when she knelt down next to me she put her hand on my shoulder and pushed me so that I was now on my back and, like all those animal planet shows I’ve seen on TV, I felt even more like the trapped turtle I just described.
I could sort of rock but I wasn’t going anywhere and I certainly wasn’t going to be able to get back up. I was now totally exposed to anything she wanted to do to me and when she put her palm on my pussy I would have begged her, if I was able, to put me out of my misery. I suddenly needed to come (or should I spell it “cum”), anyway, I wanted/needed to come and her hand was the only thing that could do that for me.
“You know”, she said, “you can scream and carry-on all you want, no one, but me, will hear you and, you can bet on one thing, I will make you scream”, and with that said fingers started to enter my pussy. They began to play with me, I rocked and, yes, screamed, I moaned, groaned and wriggled, and those damn fingers just kept playing inside me while her thumb was magically rubbing my clit and then, to add to my frustration, her other hand grabbed my nipple and twisted it!
Just two more seconds I thought, just two more seconds, just…DAMN IT SHE STOPPED…she took her hands away and just sat back and watched me. I was even crying…I screamed and screamed and screamed but she just laughed and when I finally “calmed” down a little she told me that she had plans for my pussy but first things first.
Moving over to my head she spread her legs and as I shook like a leaf I watched her lower her pussy onto (my) cock. Slowly she lowered herself and just as slowly she started to “hump” it and, with my head now held between her thighs, there was nothing I could do but “f_ _k her.
Suddenly she stopped and, leaning forward, put one hand on my breast, pushing it and my nipple very hard, and then moved her other hand to my pussy and I don’t know how she managed it, she put her fingers (3, 4, 5??) inside me and as she played with me she began to “ef” herself harder. It even began to hurt my mouth but all I could do was squeal and try to move with her hand in my puss. I needed to come!
And, when she “came” (she made wonderful noises), I did too. It was one of the best (orgasms) I had had in a long long time and, to my distress, it was only the first of many…
When she finally relaxed and got off my face she didn’t say a word. She very gently stroked my cheek, told me what a good “f_ _ k” I was, and began teasing my nipples again.
I was still, sort of, in another world, and my eyes were closed, but when she tweaked my nipples and put a vibrator on my pussy I was suddenly wide awake!
I hadn’t noticed her reach for it while I was semi-unconscious but she had my immediate attention and even though I was aching (everywhere) I tried to “uselessly” rub myself against it and squeeze my pussy but she would stop and start, she played me like a, what’s the expression, a fiddle?
She sat back, holding my head between her thighs again (but she didn’t put the cock back inside her pussy) and started moving the vibrator up and down my pussy, my clit and then inside me while at the same time twisting and pulling my nipple (my right one!) until I came again. But as soon as I started to catch my breath and relax it began all over again and I know this may sound all “too good to be true” or “made-up” etc. I was trapped in a sort of endless orgasmic tornado (if there is such a thing) and when she finally stopped I was “out of it”. If she had asked me my name I wouldn’t have known it. I was exhausted, spent, and my body felt like jello.
By the time she (lovingly) untied me, and she’s very much into “after care”, all I could do was allow her to hold me before she let me lay down with a pillow from (I guess) the couch and put a throw on me to keep me warm.
I’m not quite sure how long she let me stay like that but when she finally woke me I had a smile on my face that must have been a mile wide.
Helping me to stand, she told me she put my bag in the guest room (second door on the right) and that I should take a shower and get dressed so we could go out to dinner.
Dinner? What time was it?
It was 6 PM and I had arrived at 3 PM, only three hours had gone by? It felt like it had been a full day.
I was still stiff, more so from “coming” so much than being tied up, and the shower felt wonderful. I wanted to touch myself but for the first time in ages I didn’t.
I was happy just being under the hot water…
After the shower I took my time doing my hair and make-up and knew that I wasn’t going to wear the outfit I drove down in. I picked out a nice skirt and blouse, stockings, etc. (after all, she did say she liked lipstick lesbians) and went to the living room because that was where she said she would meet me.
Funny, when I got to the living room everything seemed to be in its place. There were no signs of some pretzel tied woman screaming her lungs out while being fingered and vibrated to ecstasy time and time again until she passed out.
No, everything looked normal and when I sat on the couch to wait for her I couldn’t help myself from tweaking my nipples and wondering where we were going for dinner; I was starving.