All rights resereved. Copyright October 28, 2010 by Ardor (firstname.lastname@example.org). The following story is intended for personal use by adults only. No reproduction either digitally or in print is permitted without the expressed written consent of the author. By downloading this story the reader professes to be an adult and that the material is legal in the area in which the reader resides.
The Pegging Party
I couldn't help but feel a little nervous as I sat there in the food court at the mall waiting for Melissa. It was probably a little silly of me to be so nervous after considering some of the things I've done for her on my web cam. I've jerked off for her on cam, I've sucked on dildos for her and eventually even taken each toy in my collection up my ass for her.
Maybe that's exactly why I'm nervous. She's seen every nook and cranny of my naked body in action and all I've seen of her is her face, her fully clothed upper body and some very nice cleavage as she sat there and smiled at me.
God, I can still see the look on her face as I sat there with a vibrator up my ass for a half an hour. I had to sit there and fuck myself, jerk off and all the while try to maintain a normal conversation for a full half an hour. She wouldn't let me come until the alarm on my clock went off. The worst part was that she made me turn the face of the clock down on the table so I couldn't even tell how much time I had to go. God, she was amazing.
We met on Fetlife.com, a social network for kinky people. My profile stated that I was submissive and into receiving anal play. Not to mention at least twenty other kinks and fetishes. She emailed me on the site to say that she was looking for a submissive and asked me to check out her profile. I was to write back if I was interested in talking with her further.
Of course I eagerly went to check out her profile page. How many times does a submissive get contacted by a dominant? Her profile was the standard kind of thing for the site. She spoke about how long she'd been on the scene, a respectable amount of time that showed she probably knew what she was doing, what she was into, a list of pleasantly kinky things but thankfully nothing to far out or dangerous, and what she was looking for, an intelligent submissive male to attend parties and fetish events with. That all sounded pretty damned good.
There was a link to her photos so I clicked it hoping to get a better idea of what she looked like. The picture that showed up near her posts and email was a cartoon of a woman dominating a man so I had no idea of what she looked like.
There was no clear picture of her face. Though disappointed I could understand. Things being what they are on the Internet today a woman has to be careful. Her face was either hidden by her hair or blurred out all together. She had a nice curvy figure without being overweight and long dark hair, which I have always liked on a woman.
None of her pictures were very revealing but one did show some nice cleavage and yet another showed a lovely pair of legs in some very sexy boots. I couldn't help but imagine what it would be like to kneel naked at her feet and beg to kiss those boots.
All of this was very promising but the picture that really caught my eye was one of her and three other women, fully clothed, all wearing strap on dildos. They were standing in a semi circle with their arms around each other's waists like a line of perverted chorus girls. The picture was obviously taken from the perspective of someone kneeling in front of them. Four dildos pointed down at the camera, menacingly, as the women smiled happily into the lens. Their faces were blurred out in this photo too but only from the nose up so you could see their smiles.
These didn't seem like cruel, I have you under my thumb, type of smiles. These seemed like the smiles of women who were genuinely having a good time. They seemed warm, infectious and made me want to do nothing but please them. I don't know what exactly made me feel this way but they seemed like they were genuinely into the same fetish I was into and were having fun playing with it.
In short it spoke straight to the submissive in me and made me weak with desire. My first thought was to run straight to my email and write her back offering to do anything she wanted. I didn't want to come off like some creepy net perv though. So instead of writing back immediately I forced myself to stop and think about my reply.
I'm glad I did because it led to a very nice conversation which eventually led to our web cam chat. She made me register on a free web cam site and then opened a password protected room. Then at a specific time I was to meet her there fully dressed. This was obviously a women who was very well versed in protecting herself on the Internet. Once again I couldn't really blame her and since I wanted what she had to offer I was very willing to cooperate. After all I am a submissive. Isn't following orders what I'm supposed be good at?
What really made this nerve wracking though was that this would be the first time I would see her face. I have to admit that through our emails I had already grown to like her. She was funny, smart, well spoken and kinky as hell. A goldmine for a guy like me so I was determined to be on my best behavior.
I sat there for what seemed like days waiting for her to enter my video chat room. Eventually her name appeared under mine. I quickly opened her video and at last we were face to face.
I was immediately drawn to her. She smiled at me and her voice came through my computer as clear as day. I was done for right there.
"Good evening Keith. It's nice to finally meet you in person so to speak." She said.
"Yes, you too Melissa." I said trying not to look as awkward as I felt.
"Did you do as I asked? Are you completely dressed?" She asked.
"Yes, I am."
"Good boy stand up and let me see."
Since she had made sure I would be wearing clothes I thought it would be a nice touch to get dressed up. I was wearing a nice pair of dress slacks and an expensive dress shirt. I even wore my nice dress shoes knowing that she'd probably not even see them.
I stood up and took a few steps back so that the camera could get as much of me as possible in the frame.
"Oh, very nice. You got all dressed up for me. Do a slow turn for me."
I did as she asked letting her see me from all sides. When I was facing the camera again she said, "Very nice indeed, and so sweet of you to dress up for me, now strip."
I looked at her a little surprised but started to unbutton my shirt. As I undressed she said, "I want you to do exactly as I say, no more no less, do you understand me?"
"Yes Ma'am." I said as I took off my shirt.
"Good boy. You'll find good boys, who do as I say, are well rewarded. Now get to the good stuff. I want to see your cock and ass."
"Yes Ma'am." I said as I kicked off my shoes and undid my belt.
I dropped my pants and then pushed down my underwear. I stepped out of them and just stood there not knowing what else to do.
"Don't just leave those nice clothes on the floor in a pile to get wrinkled. Turn around, bend at the waist and pick them up, but do it slowly."
"Yes Ma'am." I said surprised and excited that she was so eager to see me naked.
Being nervous and not thinking I didn't realize until I had turned around that my pants were now behind me. I spread my legs and bent at the knee so that I could reach between them and get my pants. I didn't I realized the view I was giving her until she said, "I love to see a nice pair of balls swinging in the breeze."
I could feel myself blushing but it was nothing compared to what she asked for next.
"Spread your cheeks. I can see it peeking at me but I want a good look at what you have to offer."
I looked over my shoulder at my computer. On the monitor was the large window that showed the video of her cam. She was looking at me, with a smile on her face, waiting. Next to that was the window that showed the video from my cam. I could clearly see myself bent over and my balls hanging between my legs. If I did what she asked everything would be on display for her.
"Y-you mean you want to see my..."
"Yes, your brown eye, asshole, boy pussy. I want to see it."
Hesitantly I reached back and took ahold of my butt cheeks and pulled them apart.
"There it is. Back up a little. Move closer to the cam."
I looked over my shoulder so I could see the window that showed my camera. Then I backed up until my ass filled that window.
"That's just the way I like to see a man. Naked, bent over and spread for me. That tight little hole is going to get a work out. In fact, if things go well, it's not going to be your asshole anymore. I'm gonna own that thing. I'm gonna pound your ass like bread dough and turn you into an eager little slut for my rubber cock. Would you like that? Would you like to be my well used little slut?"
"Oh, yes Melissa I would." I said in a breathy voice.
"Good boy, now, what have you had up that little hole? It looks so tight and virginal. What's the largest toy you've taken?" She asked.
"May I show you my toys? I have them all lined up for you." I asked looking at her over my shoulder.
"How thoughtful." She said with a laugh. "Yes you may."
I let go of myself, stood up and turned around. When I did she saw that I wasn't hard and asked me why.
"I guess I'm a little nervous." I admitted.
"Aw, honey, you have nothing to worry about, trust me. Your naked, vulnerable body is in good hands. I want to see your full length though. Get it hard for me."
"Y-you mean you want me to?"
"Wrap your fist around your cock and jack off for me. I know a naughty little boy like you has to have plenty of experience wacking off. So no more excuses and get to it.
At thirty years old I was nowhere near a little boy but for some reason the way she talked to me was a huge turn on. I could feel myself start to stiffen before I even reached for my cock. I grabbed ahold of it and started to stroke it for her.
"Don't be so prim and proper. I want to see just how slutty you can be."
I wasn't sure what she wanted at first but then I just decided to make as lewd a spectacle of myself as I could. I pulled the chair up behind me and sat on the edge. I leaned back and spread my legs as wide as I could. Then I started stroking my cock with my right hand as my left hand glided over my balls and went shyly towards my butt hole. As two fingers rubbed up against the opening Melissa asked, "Do you like playing with your asshole when you jerk off?"
"Yeah, I do."
"Good boy," she cooed, "show me what you like but don't come. You're not allowed to come without permission. Is that understood?"
"That's nice. You may also call me Ms. Melissa, if you're very good."
I had closed my eyes and was jerking off for her when she said, "Uh uh, no hiding behind closed eyes. I want you to look straight at me as you jerk off and play with your asshole."
I bit my lip and looked at her image on my monitor.
"That's more like it. I want you to remember who's in charge at all times. Tell me who's in charge."
"You are, you're in charge." I said panting.
"And what are you?" She asked.
"Your naked, little, masturbating, slut?"
"That's exactly what you are and don't you forget it."
"No Ma'am I won't."
"Good boy. You aren't lubed up are you?" She asked leaning in to get a closer look.
"No Ma'am I'm not but sometimes when I jerk off..."
"Hold it right there," she interrupted me, "you are always to be respectful and use only the most polite terms whenever possible. You don't use the words jerk off. You say rub myself. I never want to hear you use the words cunt, tits, asshole or cock. You can say, breasts, bottom hole and dick. If, and when, I allow you the honor you may beg to lick me between my legs but you don't get to say pussy. Is that understood?"
"Yes Ma'am I do." I said as I stroked my hard dick for her.
"Good, and I will use any fucking language I please. So while I can say that I want to watch you jack your cock and finger your asshole what would you say?"
"That I want to rub myself for you and put my finger in my bottom hole?"
"Good boy, but I think we need to get you lubed up and ready for something bigger then a finger don't you?"
"Yes Ma'am." I said breathing heavily.
"Then let go of that greedy little cock of yours and show me your toy collection."
I reluctantly stopped rubbing myself and got up out of the chair. Then I reached for the web cam and pointed it at my line up of toys.
"Very nice. I see you've lined them up in size order. That toy, third from the left, the purple one, is a vibrator, right?"
"Yes Ma'am it is."
"Does it have fresh batteries? Is it clean?" She asked in a doubtful tone.
"Yes Ma'am it has fresh batteries and I washed it after I used it last."
"So you fucked yourself like a cheap slutty little whore, who couldn't get enough, and then you washed your toy clean?"
"Yes Ma'am I did."
"You mean you washed it after you fucked yourself up the ass with it?"
"Yes Ma'am I did."
I wasn't sure how to prove it to her so I brought the toy closer to the camera.
"No silly that doesn't prove a thing. I want you to suck on it."
"Oh." I said suddenly not sure how clean the toy was.
"Not so sure it's clean now are you?" She asked with a self satisfied grin.
"No Ma'am I'm not." I said with a guilty look.
"Let this be a lesson to you. I want every toy kept so clean and sterile that you could eat off it. Now bounce your naked ass into the bathroom and scrub that thing, with lots of soap and hot water, until it shines."
"Be quick, but thorough!" She said as I ran out of the room.
I got the water as hot as I could get it and washed the toy thoroughly. My hard dick never went soft, and got in the way, but somehow I managed. When I was done I ran back into the bedroom and in front of the camera. I looked up at my monitor to see Melissa squeezing her breasts and pinching her nipples through her blouse. Her blouse was unbuttoned at the top revealing more of her cleavage.
As she squeezed her breasts they pressed together and threatened to come out of her blouse. When I saw her I couldn't help but gasp at the beautiful sight.
"Hello," she said with a smile while still squeezing her breasts, "toy all nice and clean?"
"Yes, Ma'am." I said unable to take my eyes off of her.
"Then stop staring at my tits and suck on it like a good little slut.
I bent my head down a little, opened my mouth and slide the vibrator in.
"MMM, oh yeah, that's nice. Now move it in and out a little. Give it a really good blow job."
I looked up at her from under my eyebrows to see her roughly squeezing her breasts. When she saw me looking at her that way her right hand went down between her legs and she said, "Oh fuck yeah, that's, so, God damned, hot."
Then unbelievably, right before my eyes, while I stood there naked, hard and sucking on a vibrator for her she had an orgasm. It was quick but intense and incredible to watch. When it was over she looked at me and said, "Sorry, I couldn't help myself. I just love that look. That sweet, submissive, mouth full of cock, look gets me off every time. You might want to make a note of that."
Since I was still sucking on the vibrator I shook my head yes.
"Good boy, now I think it's time we get that tight little ass ready to be filled. Get that cock out of your mouth, turn around, bend over and lube up for me."
I took the vibrator out of my mouth and placed it on the seat of my chair. Then I reached for the tube of lube that was near my toys. I turned around so that my ass faced the camera and then popped the top on the tube of lube. I looked over my shoulder to see her staring at my ass. The movement must have caught her eye because she looked up at me and said, "Aw, don't be shy baby. You want this don't you?"
I shook my head yes.
"Uh uh," she said shaking her head, "I want to hear you say it, out loud."
"I-I want to fuck myself up the ass for you."
"That's right baby, now, spread 'em and lube up for me."
I spread my legs and bent over the chair. After that I squeezed some of the lube out on my fingertip. I put the tube on the chair seat and pulled open my left ass cheek with my hand. Then I reached back for my butt hole with my lube covered finger.
"Damn, that's fucking hot. Wait a second, don't move."
Despite what she said I looked over my shoulder to see what she was doing. She reached for the keyboard and then I heard a sound like a shutter clicking. Oh my God. She took a screen capture!
I looked at the window that showed my camera's view and saw myself bent over and completely exposed with a finger up my butt. Since I had looked over my shoulder enough of my face was visible that if you knew me you could tell it was me.
"I have some friends, women like me, who'd just love to see that photo. Would you mind if I showed it to them? They're very discrete and I won't give them the photo. I'll just let them see it on my phone."
"Like you?" I asked as I continued to lube up for her.
"Yes, they like to fuck guys up the ass too. In fact I bet they'd all love to take a turn with that tight little ass of yours. What do you think about that?" She asked with a smile.
My mind flashed back to that picture on her profile of her and three of her friends wearing strap ons all pointing at me. This wasn't a fantasy anymore. It suddenly seemed very real.
"Holy shit, are you serious?" I asked looking at her over my shoulder with a finger still up my butt.
"Language mister, don't forget your manners." She scolded me.
"Sorry, you just kinda caught me off guard."
"That's OK baby, don't worry about that right now. Why don't we focus on getting that vibrator up your ass. You do still want to fuck yourself for me don't you? I so want to see your tight little hole all filed up." She said as she started playing with her breasts again.
"Yeah, of course." I said a little shaken.
It was one thing to play a fantasy slut in front of a web cam but did I want this to happen for real?
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