Episode With A Web Mistress
Episode With A Web Mistress
Most people assume that I am quite conservative. In public, I do generally portray a conservative outlook. However, behind closed doors, I have a very open mind:| especially when it comes to sex. This is perhaps one of the reasons why I like the Internet so much. I can explore things online that I would not necessarily do in public.
When I first started exploring different fetishes on the Internet, I was excited (and I do mean excited) to find all sorts of stories and pictures. There were a lot of things that I never even considered doing myself, but seeing and reading about them was
One day, I was playing around with Yahoo Messenger and started checking out the chat rooms. I was amazed to see so many people online and with sexually open minds. At first, I was just like any guy; I went into chat rooms just hoping to find a woman to chat with. If I were really lucky, I would find a woman with an open webcam and get to actually see her. Of course, there are many more men online than women, so that didn't happen as often as I liked.
As I looked at the different rooms, I started selecting some of the Fetish rooms. Stuff like Big Beautiful Women, Cuckold Husbands, etc. One that really got my attention was something like "Men obeying Women." I entered the room and hoped to find some hot chatting. And indeed I did, only I was left out because I didn't have a webcam. Of course, the next thing I did was to buy a webcam. As soon as I had it hooked up, I went back into one of the FemDom rooms. (If you hadn't guessed, this is one fetish area I particularly liked and enjoyed). Even with my cam on, it took awhile before I could find a woman to strike up a chat with.
Lucky for me Mistress Silvia was online that day. I credit her for helping me to explore a lot of things that I really enjoyed doing, things that I never had the nerve to try before. On that first day, she played with me for about an hour. She had me strip naked for her and slowly masturbate for her. She “told” me “not” to cum for her because I didn't do anything special in her view. Over our next few chat sessions, I found out what she meant by "special." Mainly she meant wearing women's lingerie and using a dildo on myself. I had never done anything like it before, but I had read about it a lot. Of course, I had to buy the lingerie and dildos, but I am sure glad I did. I didn't think it would be pleasurable at all, but I found that having a woman “tell” me to put on panties and fuck myself with the dildo was extremely pleasurable.
About two weeks ago, she told me that she was going to be visiting my city on a business trip. I immediately told her that we should meet. She said she would agree if I would do a very special show for her. I agreed without hesitation. That night, she played with me online for about an hour and a half. She had me try on several different panties and nighties. She also had me fuck myself with the biggest dildo I had bought. When I felt like I could wait no more, I asked her if I could cum. She said yes, but only as she directed me to. And she also reminded me that if I wanted to meet her in person, that I better do as she said. Again, I agreed without blinking. The she told me what she wanted me to do. She said she wanted to see me cum in my hand and then rub it all over my mouth and chin and to lick my hand clean. As she said it, I became embarrassed. I didn't know if she was serious or what. I wasn't sure what to do at first. Then she said to “do it” again|; my cock immediately got harder. It was amazing. I would never do something like this on my own, but because a woman wanted me to, I was getting excited about it. Within a few seconds I was spurting all over my hand. As the last few drops oozed out, I placed my hand to my face and began smearing and licking. The taste wasn't too bad at first,| but the more I licked, it started tasting more bitter. But at the same time,| I was even more excited about how nasty I was being. Mistress Silvia loved it!| After a few minutes, she said I could stop| and that she would see me soon!
Which brings me to last weekend. We had exchanged relevant info and had decided that I would meet her at her hotel. I arrived at 8pm on Saturday and I was very nervous to say the least. I approached the front desk and asked if they had a key reserved for me. They did, and I headed upstairs to the room. As instructed, I didn't knock, but used the key to enter the suite. As soon as the door opened, I heard low moaning coming from the bedroom area. I slowly went forward hoping to catch a glimpse of my mystery internet lady masturbating. Instead, I was shocked to see
here slowly riding a nice sized cock of an even more mysterious man, a dark skinned man. Just as the thought to leave entered my mind, my Mistress opened here eyes and
looked straight at me.
Mistress Sylvia was a pleasantly plump lady, maybe 5'5", 140 lbs, somewhat wide hips and ample breasts of 38CC, and really an attractive lady of probably her early to mid 50's. She introduced her companion to me as a coworker that she played with while on the road. He struggled to say hello, but was having too much pleasure to really respond. She then had me strip down to my thin panties (which she had instructed me to wear). All though the whole scene was exciting I was also very nervous, especially with her coworker there. He looked Indian or Pakistani, I thought. She could sense I was uncomfortable and told her coworker it was about time for him to go. She told him to go ahead and cum and within seconds he was bucking furiously as he released his cum into her pussy. She rolled off of him and told him to get ready to go, but to suck my cock hard first. I couldn’t believe it. First of all,| I couldn't believe I wasn't already hard, but I guess I was so nervous and all. And second, I hadn't considered any bi-sex being a part of the nights activities.
But being that I was on the receiving end, I couldn't really mind. As he moved my panties aside, I could finally feel my cock start to harden. In one quick gulp he swallowed my cock. Although his mouth felt warm and wet, the same as a woman's, the kinkiness of it was making my cock as hard as a rock. After only a few seconds, he lifted his mouth off my cock and looked at my Mistress. He asked her if it was hard enough for her. She then told me to thank him. I did, and then she said,”Not with words you wimp, with your mouth.” I turned beet red again. I tried to think of an argument, but then I figured, she was demanding and he just had my cock in his mouth, so what the hey! As I sunk to my knees, she told me to clean him up good so he could leave her and I alone. With that as my incentive, I got to work. Because he had just cum, his dark cock was wet, slippery and only semi hard. I gently licked his “cut” cock head which was purplish in color and then took his whole cock in my mouth. I was thinking so much about how unbelievable this all was that I really didn't notice the taste and aroma as different than my own. As I was nearing completing of my job of cleaning his cock, I noticed he was starting to get hard.
Just about when he had a full erection, Mistress told me to stop. She ordered him to leave, and not come back for two hours. He dutifully got dressed and left the room. I just stood their trying to imagine what was to happen next. As soon as the door closed, I found out. The first thing my Mistress did was to have me clean her up as well. She was still laying on the bed naked, legs spread and her crotch wet and seeping her lover’s cum, so I crawled between her legs as directed. I started licking all of the juices left behind from their sex play. This time I did notice the flavors and sexy aroma. It was really strong, but also, very exciting. Their juices were all over her cunt and legs. I licked from her prominent and protruding clit to her ass and all over her thighs. Every time I brushed her clit with my tongue, she let out a moan.
Eventually, I focused more and more of my licking on her excited clit. She grabbed my hair and pulled my face even deeper into her pussy. Mistress seemed to love the way I would capture her clit between my lips, suck it hard and then flutter flick it with my tongue. I was almost to the point of being smothered by her pussy when she began convulsing. Her orgasm was very intense and lasted for well over a minute. As it subsided, she pushed me away and told me to go wash up my glazed face. I happily obliged and headed to the bathroom with a smile on my face and my cock still as hard as a rock. When I came back into the bedroom a few minutes later, I saw that my Mistress was on the internet with her webcam turned on. As I got closer, she told me we were going to have a nice little show for everyone to see.
She started out by having me pose in different positions for the webcam and to change in different lingerie that she had brought with her. The whole time, my cock was as hard as ever and leaking precum. She kept wiping it off with her fingers and having me lick it for her. The I.M.s she was getting from other users on the internet were coming in fast and furious. A lot of them were suggesting different things for us to do and a lot told us of how horny we were making people feel.
In a few minutes, Mistress went to the bathroom while I slowly masturbated for our net audience. When she came back she had on an strap-on dildo. She first had me suck it for our webcam viewers and then she told me to turn around. The feeling was unbelievable as she entered my ass with her strap-on dildo. I could hear the beeps as more I.M.s poured in. Amazing as it was, my erection was having throbbing something terrible . She reached around my waist to slowly started stroking my cock as she also slowly fucked my ass. As she continued, she also sped up her tempo. Before long, my cock was unbelievably hard and she was pumping my ass at a good pace. She finally pulled out and after she had pulled the dildo out of my ass, I asked if I could fuck her.
As soon as she had the strapon dildo off of her, I was ready to plunge my cock into her steaming pussy. However, she had other things in mind. She told me to give her a tongue bath. She wanted me to lick every inch of her body first. I spent probably thirty minutes licking everywhere imaginable, neck, nipples, pussy, ass, toes, armpits, back, belly, etc. I went back to licking her pussy for awhile when she finally gave me permission to fuck her. I moved my cock to her pussy and gently rubbed my cockhead on her clit. She grabbed my hips and pulled me into her. Of course, after the night events, I wasn't able to last long. I tried to hold off by not moving much. Mistress sensed I was holding back and began grinding her hips into me.
Without much warning, my cock exploded into one of the most intense orgasms of my life. Her pussy was overflowing with cum and I wanted to lay there forever.
Of course, she had other plans. She quickly guided my head down to her crotch and had me lick her pussy once again. Once again, I was greeted by the combined flavors of her pussy cream and my cum. This time I noticed that my cum tasted different than her coworker’s load. It didn't take long before Mistress was grinding her pussy into my face and having an orgasm of her own. When her orgasm finally subsided we were both exhausted.
I started getting cleaned up and dressed as Mistress was signing off the internet. Apparently our show was quite a hit. At about that time, there was a knock at the door. Boldly, Mistress went and opened it while completely naked. It turned out to be her coworker. She apologized to him and said she was exhausted and not ready for any more sex. I smiled at that thought thinking at how well I must have pleased her. But then that changed when she told him I would take care of him for her. I was almost already completely dressed and ready to go. I was already coming down from the high of sex and ready to just go home.
Mistress “told” me to do it for her, and promised to make it up to me the next time she was in town. She was kissing me and rubbing on me while her coworker started unbuckling his pants. I then figured, what the heck, I had done a lot of other crazy
things that night. At that moment, his cock appeared “aroused” before the two of us.
Mistress Sylvia helped me get started by guiding his cock past my lips into my mouth. As I sucked on his cock, she massaged his balls and kissed my cheeks. He
was already beginning to moan when she started stroking his cock while I licked that impressive purple cock head. When he started to grunt she pushed the back of my head so my mouth would engulf his cock entirely until I cold feel it brush against the back of my throat. She was also stroking his cock even faster. I was swirling my tongue around his cock one more time before I felt him tense up.
My mouth was then awash with his warm tangy cum. He began bucking his hips and I had trouble swallowing his “load.” As it was leaking out of the corners of my mouth, Mistress was licking it up. He finally pulled back and Mistress began French kissing me and sucking his seed from my mouth. By this time, Mistress and I had swallowed all of his cum, her coworker had zipped back up again. We all stood up and I knew it was time for my exit. Mistress Sylvia thanked us both for a good time and we left together as she headed for bed.
I drove home, tired, but excited about all the events of that night. Now I am just hoping to have another night of fun with Mistress Sylvia. But I am also hoping to meet more people online with similar fetishes.