Sweet November Ch. 17

As I maintained my position I scanned the audience and could not help but notice the sly grins on the faces of all the women. Deb announced that they could all open their bags now and they all pulled from their bags a strap-on similar to that which Deb was wearing.

After letting the women admire their new gifts for a while Deb stepped up behind me and rested her right hand on my backside as she turned to address the women once again. "As I am sure most of you have already guessed, these are for your next assignment. As always, you do not have to participate. You can leave at any time with the understanding that none of this will ever be mentioned. However, as always, if you choose not to take on the assignment you will be restricted from participating in any future gatherings. Is that clear?"

Deb scanned the audience for understanding before moving on. "Okay then, onto your assignment. You will have sixty days to complete this one as opposed to the normal thirty as we will be taking the month of December off because we have found it is too difficult to work around all of our schedules during the holidays. Your assignment is to use your new toy on a man and gain proof of that usage. Acceptable forms of proof are pictures, video, or written confessions from the man. The quality of the picture is not necessarily important; it just must be solid proof that YOU are fucking a man up his ass. You can use a camera phone for all I care. Frankly," Deb continued, "You can set up a hidden camera so that he does not even know you took the picture or video. Just...get...proof."

Deb paused for a moment as an evil grin fell on her lips. "However, I do recommend that your man knows exactly what you are doing as it will serve to remind him of his pitiful little self and how he does not deserve you or to serve you."

Many of the women nodded in agreement to her statement and began to cook up ideas of how this could go down. Deb interrupted their chattering to let them know she would hold in highest regard any woman who returned in two months with not only a video, but a written confession as well. After that Deb began to stroke her hard rubber phallus and indicated that she had a few suggestions she would like to demonstrate for those of them in the room who were a little uncomfortable with the idea.

She started off by reminding all the women how badly men wanted and needed to serve them. She went on to say that women were doing men a favor by filling that role. After that, she encouraged the women to approach the men in their lives in a dominating fashion and they would likely comply, as being dominated is a fantasy for most men.

I could not disagree with a word she was saying, but I knew it was all a setup. In addition I knew that if these women did everything Deb said with the savvy and seduction that Deb presented it, they would have no trouble pulling this off.

Deb went on to tell the women that they would have to decide how they wanted to do this. She mentioned that some men might enjoy playing the role of the woman and go as far as dressing up in bra and panties. "You can even help them put on make-up if you so choose," she added.

"Other men may need to be bound and have their ass taken somewhat unwillingly. This may seem cruel," she said, "but this is the only way they can allow you to do what their heart truly desires, but which their 'manliness' will not allow. You will be doing them a favor."

Then Deb stepped confidently around the coffee table where I remained and stopped at the end I was facing. With her left hand grasping my hair she spoke once more, "Now I would like to show you how I prefer to do it."

Turning towards me she pressed the flesh-colored strap-on to my lips before addressing her audience, many of which were formerly seated but were now standing to get a better view. "When preparing to fuck a man's ass it is important to get proper lubrication. You can find this at just about any pharmacy or department store near the condoms, but I prefer to get mine from the man himself."

With that she forced her cock past my lips and into my mouth as she maintained her grip on my hair. "You have to take your time at this point, as I am sure his gag reflex has not been disengaged yet."

Over the next several minutes she continued to address the women, but I have no recollection as to what she said. All I can tell you is that she continued to push her twelve-inch strap-on in and out of my mouth until she had worked most of it in and down my throat. Several times I felt myself gagging, but she would work it back out just in time. By the time she had it two-thirds of the way in, it was well-lubricated and I was hardly gagging at all.

Finally Deb pulled the phallus from my mouth and pushed my head down to the hard table. This had the obvious effect of putting me in total subjection to her, but that would not be enough. As she walked back to the other end of the table she commanded me to put my hands on my ass and open myself up for her.

Of the few times I had been taken up the ass I had never been made to do this before. This may have been as humiliating a thing as I could imagine, as it required me to practically ask her to give it to me and be willing to make it even easier for her. After the way the night had gone, I should not have been surprised.

Almost as quickly as I grabbed my butt cheeks and pulled them apart, I felt the tip of her cock on my anus. Slowly she began to work it in as she addressed her audience further. Methodically she moved her hips and pelvis forward and back in order to gain further penetration. By now they were all standing and had moved closer to us admiring her technique and my complete subjugation.

After several minutes of working her strap-on deeper and deeper into my ass she apparently felt she had laid enough groundwork to take things up a notch. "This is where it gets really fun," she said laughing.

Deb took hold of my wrists in each hand and used my arms as leverage. Then she began to thrust harder and harder into me as she pulled roughly on my arms. I had to flex my arms and pull back just to keep her from pulling them out of socket.

When several minutes had passed she was really going at it and reaming my ass hard. Sweat was rolling down both our faces and while I was moaning in agony she was breathing heavily, out of exhaustion and invigoration. I could only hope her adrenaline gave out soon and she chose to stop.

Deb slowed her pace and addressed the women once again. "Normally I would tell you a good stopping point is just after you reach around and grab his erection and jerk him off. There is something powerful about pointing out to your man how turned on he is by being taken up the ass." She stopped for a minute and let that sink in with her audience.

"However in this case, you will notice our pathetic little slave has lost the ability to get aroused, so I have to determine when he has had enough on my own." This she said as she thrust a few more long hard bursts into my ass and then pulled out.

The women clapped their approval and several made comments amongst themselves about how they could not wait to try theirs out for themselves. Shortly thereafter they began to gather their things and called it a night. I was told to hold that position until all of the women left. This gave them all one last opportunity to slap my bare bottom before walking out the door. I believe every one of them did.

Finally, half an hour after the festivities ended I was alone with the three Ds once again. For a couple minutes they teased that maybe they should each have one more go at me before they sent me on my way. Thankfully they decided that I had done enough and decided to send me back to my hotel room.

Donna handed me a tube sock and commented how I had 'ruined' the thong I had been given earlier, so they weren't about to trust me with any thing else. Then she grabbed my ass one last time for good measure. After covering my most private area as best I could with it I stood there wondering where the rest of my clothes were. To my disappointment they would not be given back.

"You better get going," Diane sneered. "Your ride is waiting."

The three of them laughed as I turned and reached for the doorknob. I looked back one last time to make sure they were actually going to make me run out there like this. Deb winked, Diane smiled, and Donna blew me a mocking kiss.

I quickly opened the door and ran out to the waiting Town Car. Once inside I pulled the door closed. As we pulled away my Asian Princess remarked, "I had a feeling they might do that to you," and then she threw me one of the hotel robes to keep warm with.

"Sorry, that's all I've got. It didn't occur to me until my options were all but gone," she apologized sweetly.

"That's okay," I responded through chattering teeth. "I'll take whatever I can get right now."

"By the way," she followed up, "I put an extra room key in the right pocket." I thanked her and pulled on the robe.

Surprisingly, over the next several minutes as we drove back, we actually had a relatively normal conversation. We did not talk about anything of consequence, but it was kind of nice to have a normal conversation. It seemed like forever since I had one. It actually felt a bit strange. She had been the only constant in my life over the last week and though we rarely spoke I felt like I knew her. It was a bit comforting; odd, but comforting.

As we pulled back in front of the hotel she told me should would pick me up in the morning at eight. She must have read the look on my face as surprise. "Jess wants you back early," she responded shrugging, "I guess she has some things for you to do."

With that I exited the car and headed quickly up to my room. I could only hope as few people as possible would see me running the halls in my robe. Luckily I made it to my room without too much fanfare.

It did not take much thought for me to decide I was ready to climb in bed. I think it may have actually taken less time for me to fall asleep.