I got into my car and started the drive to work. I still couldn’t believe I had seen Terry at the Enema Club, and played with him. My God, he is my boss! If I hadn’t had a little wine, I would have had much better judgment than that. How will I look him in the face today? I was trembling a bit at the very thought. I mean, it had been great fun, but how would I be able to work with him after last night.
I parked in the garage and stepped into the elevator. I walked past the receptionist with the briefest of hello’s and dashed into my office, closing the door behind me. Well, it was a good thing that I had quite a pile of work on my desk. I logged onto the computer and checked my mail. I started making the customary responses to our overseas clients. After I was well into the morning, juggling files and phone calls, I had put the events of last evening out of my consciousness. At least I did until I heard those famous words, “You’ve got Mail!”
I clicked on the only letter in my box, an unfamiliar screename, and found a short note: “This pic is especially for you. Download it and let me know if you like it.” I don’t usually get pics in my business mail. I thought it might be from one of my buddies, a practical joke of some kind. I downloaded the pic, and could hardly contain my surprise when I saw the emerging picture of a female with an enema nozzle in her behind. Oh my god!
I quickly typed a reply: “Who are you?”
The next letter came quickly. “One of your fellow club members.”
I typed back: “I can’t get pics like this! I’m at work!”
Reply: “I know. I saw you come in.”
Oh my god, it must be Terry.
I typed back: “Terry?”
Reply: “Yes, Bess?”
I stopped typing. Oh, no! I was afraid of something like this, although this was not quite what I had expected. I couldn’t think of what to say next. While I was pondering what to do, a knock came on the door. I quickly logged off line and answered the knock. “Yes?”
Terry opened the door, grinning, and walked in. “I thought we’d better talk a bit about last night, or we’ll not be able to work together again.” My stomach was fluttering like crazy. He looked pretty happy, though. Maybe I shouldn’t be so afraid.
I think my smile must have been pretty weak, because he wrinkled his forehead. “Are you okay, Bess?”
“Yes. It’s just that this whole thing is making me a little crazy.”
“Well, didn’t you enjoy yourself last night?”
“Of course, but in the light of morning I thought I had behaved pretty foolishly. I was pretty worried about how things would work after the fact.”
“Honey, things will be just fine. You don’t need to be nervous. I will respect your boundaries. I mean, I had a great time and wouldn’t mind repeating it, but I can also take ‘no’ for an answer. It’s just not my favorite answer.”
“Terry, I don’t know what to say ‘yes’ or ‘no’ about, even. I mean, most of my contacts down there have been casual. If we see one another again, great, and if we don’t, we find someone else to play with. I don’t know how it works when you end up with someone you know well, much less your boss!”
“Bess, do you think you could think of me as just a man for a few minutes? I had a terrific time with you last night, brief though it was. I would love to play with you more often. It was a wonderful ending to what had been a pretty awful day. I walked into work nearly skipping this morning, so excited at the thought of seeing you again. But I guess I need to know if you would ever want to play with me again. Like I said, I can take ‘no’ for an answer.”
“Terry, I had a terrific time with you. It was a lovely end to a perfectly wretched day for me, as well. And thinking of you as just another guy, gosh, I’d love to play with you some more. But, you are my boss. Won’t this be a problem?”
“Okay. I’ve got a solution here. Just humor me and I’m certain I can help us both.” Terry turned and shut the door. I stood puzzled for a few moments, and then returned to my tasks. About fifteen minutes later Terry buzzed me on the intercom. “Bess, we have a lunch meeting with a new client. I’ll meet you in the lobby in half an hour. You needn’t bring anything, since this is a new client and we’re just getting to know each other. I had Gretchen cancel your other appointments this afternoon, however, since this may take the rest of the day.
I cleared my desk of as many tasks as possible and then reordered my desk. I hated coming into a messy desk on Monday. I picked up my briefcase, and walked out towards the elevator, speaking weekend greetings to my coworkers as I left. I walked out of the elevator and waited in the lobby for Terry, noticing for the first time since my interview for this job how beautiful the lobby looked. The warm wood tones were very inviting. Funny how we miss so many things as we whiz in and out of our day.
Terry came out of the next elevator and walked towards me, putting his hand on my shoulder to escort me out the door. “We’re meeting our client at Rudy’s.” Great! I loved Italian food. Terry and I were escorted to a table for three. I sat facing the interior of the restaurant, and Terry sat facing me. He ordered a bottle of Merlot and we made small talk completely unrelated to our encounter. After about a half hour had passed, and Terry had looked at his watch several times, he got up and went to the phone, speaking briefly to the Maitre’D as he walked to the phone. The Maitre’D nodded and walked towards the kitchen. By the time Terry returned to the table, the waiter had delivered plates of antipasto and a silver plate with a domed lid.
“That’s especially for you, Bess.” I lifted the lid and saw a small black box. I looked at Terry and he just grinned. I opened the box. There was a note and a smaller box inside the box. “The client is you, and the time is now. After lunch you may open this box and you will be required to follow the directions inside.” I looked at Terry, but he was already well into his appetizer. I barely ate. I could hardly wait to see what was in the box. Finally, when Terry was full and we had shared an entire bottle of wine, Terry said, “Okay. Open it now.” I did as instructed. Another note and underneath the note, a package of small sized anal beads. I gasped audibly.
“Terry!”
“Read the note, Bess.” I opened it with shaking hands. “You are directed to take this package directly to the Enema Club. You will be given a key and you must go directly to that room. You will wait there for further directions. These beads will be worn by you when the time is right. You will do as directed or you will be fired on the spot.”
I looked at Terry. He was trying to look stern but his eyes were a dead giveaway. Half a bottle of wine in me and I get pretty horny. I tried to look scared, but all I felt was excitement.
I nearly ran to the club. When I walked in, Bob had the key ready and waiting for me. I found the room to be one of the deluxe suites. I had never been in these, but they were huge. Two king beds in each of two huge rooms which were connected by a parlor of sorts. There were two huge bathrooms with showers huge enough for several folks at once and very large sunken tubs. I put my briefcase down and kicked off my heels. I saw a note on the bed. “Go to the screen and type in ‘Terry, I want you!’”
I chuckled and followed his instructions. By the computer, I noticed another note. “Draw a bath in the blue bathroom and get into the tub. Light the candles and use lots of bubbles. Get the wineglasses out and set them by the tub. Don’t get out until you get further directions.”
I didn’t have to get those directions twice! I ran the bath, set out the glasses, slipped off my clothes, lit the candles and slid in. What luxury! I was washing with a nice loofah when I heard Terry walk into the room. He set a bottle of wine down next to the tub and a shaving kit sized bag s well. He took off his suit and hung his clothes in the closet. He slid into the tub next to me. He poured the wine and handed me a glass. “You will drink.” I was a little woozy already, but I tipped the glass to my lips. He knew how to pick them, for sure!
When we had drained the glasses, he took them and set them to the side. He came close to me and started to massage my back. I turned my back towards him and he did a lovely job on my shoulders and arms and started to work his way down my body. I heard him open the zipper of the shaving bag and felt his hands coming back towards me. He lifted me up to the edge of the tub and sat me on the side. He sat down next to me. Then suddenly he pulled me over his lap.
“I am your boss. You must never forget it!” He began to spank me with his hand, not too hard, but against the wet flesh there were sharps pains with each swat.
“Oww!! Why?”
“You need to obey your boss.” He stopped spanking and then thrust his finger deep into my ass. It was wet from the water, but not like it would have been with lubrication. Yowwww!
He pulled it out, and then rammed it in again. I noticed that he seemed to have inserted something. “What is it?”
“These are some suppositories. You must be cleaned out, Bess. Do I have to take care of everything here?” I wasn’t quite certain what the game was yet, but I played along.
“I’m sorry, boss!”
“As you should be. We may need something stronger if these don’t work within the next three minutes.”
We waited together with Terry continuing to thrust his finger in and out, with more and more suppositories…about eight, I had guessed. I was squirming, but I could tell that I wouldn’t be able to use the toilet yet.
“I’m sorry, boss, but these do not seem to be working.”
:”You probably aren’t letting them. But I will teach you to behave.” He pulled out his finger and held me with one hand while he fussed around with his shaving kit some more. Then I felt another invasion, something a bit harder with Vaseline on it. Now another. Then the anal invader. “See how you like this!”
I began to feel a burning sensation. Oh, God, I was on fire!!! “What is it?” I screamed.
“Soapsticks. Are they beginning to work for you?”
“Oh, owwww! Take them out!”
“The only way to do that will be with an enema. Now, slide back into the tub and turn your bottom towards me. Now, bend over.”
He took a bulb syringe and coated the nozzle with Vaseline….I peeked and saw him do it. I heard the air squeezed out and the water sucked back in. He thrust the bulb into my bottom and squeezed very hard. Ooooohhh! I felt burning and cooling at the same time. Squeeze after squeeze. I was getting so full.
“Stop, Terry, please!”
“I’ll stop when I want to stop. You will take three more bulbs.” Oh, God! How could I take it! I gritted my teeth and tried to keep from exploding. Finally, he quit. I didn’t wait for instructions, but ran from the tub and expelled on the toilet….it took so long to get everything out. In fact, Terry walked into the toilet cubicle. “You okay?”
“Yes. Just have a lot to get out.” He shut the door and walked back out. When I emerged, he had the shower running and gently and attentively washed me off. He gave me a big fluffy towel and covered himself with one, as well. He led me into the parlor. When I had dried, he took another towel and laid it on the carpet. “Lie on this. “
I lay on my back and without any ceremony, he entered my vagina. He fucked me as slow as humanly possible. It was almost excruciating, but sweet at the same time. We both came, but gently rather than violently. We snuggled on the towel for a while.
I was almost asleep when Terry got up and went into the bedroom. He returned and took my hand, guiding me into one of the beds, where the covers had been turned down. We lay down and he covered us up. We link our legs and Terry fed us delicious chocolate truffles.
For his final trick, he took the anal beads and made a great production of lubricating them. He slid them into my behind, one at a time and very slowly. When they were all in, he gave them a tremendous yank. I screamed! Then, he put them back in slowly, and slid his now erect penis back into my vagina. He turned me onto my back, threw my legs over his shoulders and fucked me faster and hard. When he was ready to come, he yanked the beads out again and our screams met as one.