A Journey to Control

Chapter 4 - Wednesday

I was still shaking a little when I got the blinds and curtains closed. It was a combination of the nervousness and fear of being seen, along with the excitement and arousal of being exposed so blatantly. I pulled on some jeans and a shirt and sat down on the bed. I was trying to sort out in my mind how I had gone from not having ever done anything more adventurous than reading some risqué stories online, to being naked in a hotel hallway and stroking myself in front of a hotel window in just a matter of a few days. Having worked through lunch, I was starving so I went down to the restaurant in the hotel and ordered a steak and a bottle of wine. The restaurant wasn't packed, but there were several tables occupied. At one table was a group of six women. As I responded to some emails from earlier in the day on my phone, I saw one of them look at me and smile. I smiled back, but panicked a little. Could they have seen me in the hallway? Were these some of the women from the pool? Omigod, how could I have been so stupid to let myself be exposed like that!

I tried to calm myself down, focusing on my phone and email messages until the waitress came back with my food. I dug into the steak (which was delicious) like a starving man. As I ate, I calmed down a lot. Ok, I rationalized, I was just hungry. Everything will be just fine. I had a little more of the wine than I intended, but what the hell, I would sleep well tonight! As I was starting on the piece of chocolate cake I had ordered for dessert, the ladies at the big table got up and started to leave. The one that had smiled at me earlier took a detour to walk by my table on the way out. As she passed, she smiled again and dropped a folded note on the table. I watched her leave before I unfolded the note and read the message. "Nice butt! We're out at the pool every afternoon this week. Stop by again."

Mentally I alternated between hugely embarrassed that she saw me at the pool and recognized me and excited and flattered by the compliment. Would I have time to get by the pool again before I left? Probably not.

I was just finishing up my dessert when my phone pinged. I checked the message and saw that it was from Ms Evelyn! My heart rate immediately spiked and my cock got hard. "Are you available after work tomorrow? I hope so. If so, let me know what time you'll be free." I quickly responded that I would be finished with work around 5 and could be available by 5:30 (No, of course I wasn't eager. Not much!)

I finished up, signed for my bill and headed back to the room. I was mentally re-living the same trip I made just a few hours earlier wearing just the hotel bath towel. I looked both ways down the hall. There must have been 40 rooms along that long hallway. It would have been so easy for someone to have been coming out of their room and have seen me bare-assed naked and sporting a healthy hard-on standing at my door. Just the thought of it gave me a bulge in my jeans. I got back into my room and stripped naked (it seemed like the thing to do, right?). I checked my email again and saw that Ms Evelyn had replied. "I'll be at your hotel at 6:30 sharp. I expect you to be waiting for me in the lobby. ~Ms E"

I was excited by what might be in store for me tomorrow, but by that time the long day and the bottle of wine had me wiped out. So, I got ready for bed and slept deeply until my alarm woke me up the next morning.

Wednesday at work was hectic. The week was almost halfway over and we still had a quite a bit to get done before we left Friday. We were so into our project that it seemed like the first time I looked up it was after 5 pm. I wrapped up my piece of the work in a few minutes and was able to slip out by a little before 5:45. I rushed back to the hotel, showered and brushed my teeth and hastily dressed. It was 6:25! Perfect! Just enough time to get down to the lobby.

I rode the elevator down, excited at the prospects of what the evening might bring. As luck would have it, I was just getting off the elevator when I saw Ms Evelyn walking through the door of the hotel carrying a large shopping bag. I met Her halfway across the lobby. "Hi there!" She said. "So good to see you. I brought a few things for us to try out," She said as She handed me the bag. There was wrapping paper lying on the top, so I couldn't tell what She had brought, but the bag seemed very light to me.

I turned around to head back toward the elevators and She stopped me. "No. I'd prefer to take the stairs." That seemed odd, but since I was only on the 3rd floor I guess it wasn't unreasonable. We walked down the hallway toward the exit sign where the door to the stairwell was and discussed how our day had gone. She said She hoped that She wasn't imposing too much on my work schedule.

I held the door for Her to go into the stairwell. She brushed past me and walked to the stairs, but She stopped suddenly on the second step. I stopped, not yet on the stairs, but admiring the view as She took the first couple of steps. "subbie, I want you to trust me. I will always try and push your buttons, but I will protect you."

"Of course, Ma'am. I know that You will."

She looked at me with a slight smile. "Good. I'm glad to hear you say that. Now, what I want you to do is take off all your clothes and put them in the shopping bag. Make sure you hand me your room key first."

I can only imagine the look that was on my face. "But Ms.Evelyn..."

She smiled at me, "subbie, I will protect You. Now quit wasting time. You know you'll end up doing what I ask."

I looked into Her eyes for several seconds, then took a couple of deep breaths and started unbuttoning my shirt. I neatly folded it and put it in the bag. "I'd probably move a little faster if I were you. I don't know how much use this stairwell gets," She said with a wink. I hurriedly removed the rest of my clothes, looking around before finally sliding my briefs down my legs and stepping out of them. She smiled broadly and picked up the shopping bag, holding out Her other hand for me. I took Her hand in mine and we walked up the stairs together. Her, very calm and controlled, me almost shaking from nervous excitement and fear of getting caught. As we passed the second floor landing, I could hear voices outside in the hallway. When we got to the third floor, She opened the door and looked out in both directions. Apparently not seeing anything, She turned to me and took my cock in Her hand. She stroked it a few times to make sure I was completely erect and then led me by my hard cock out into the 3rd floor hallway. I was hoping we'd make a run for the room, but She would have none of that. She set out at a deliberate pace down the hallway, past the six rooms between the stairwell and my room. When She got to my door, She set Her bag down and pulled my key out of Her pocket. I was frantically looking back and forth down the hallway. But my luck held! Nobody popped there head out of the door to their room. She opened the door and I followed Her into the room. Relief poured over me, my naked escapade on the stairs wasn't going to end up with me getting caught. At least not this time!

Once inside the room, Ms Evelyn told me how proud She was of me and my willingness to be obedient to Her and that I was entitled to a reward. She told me with a smile that She had decided that my reward was that I would be allowed "to empty My balls of all that built up cum, before they turn blue!"

Needless to say, I was very excited and couldn't wait to get started! Ms Evelyn had me lie down on the bed and put a towel underneath me. "Of course, we can't let you release all that cum without a little more teasing, can we!" (I thought that maybe we could, but decided that it probably wouldn't be a good idea to point that out.)

She took out the bottle of lotion - some special blend She had told me. Something that always stays slippery. She started leisurely stroking my cock. For nearly an hour, She alternated between slow strokes, fast strokes and a vigorous massage of my balls. Just when I was sure She was going to take me over the edge, She would back off until I cooled down. Then She started stroking me fast and hard again. I felt like my cock might explode! I know that it had never been harder in my entire life. But again, She stopped just short. My cock was leaking pre-cum all over Her hands.

Then She looked at me, smiled softly and told me to roll over on my stomach. She put a couple of the hotel pillows under my hips to give Her better access to all of me. She used one hand to make sure She kept my cock hard, but with the other hand She began to massage up and down the crack of my ass, spreading the lotion liberally around my puckered hole. She continued to stroke my cock with one hand, but very slowly and gently inserted the tip of Her index finger on the other hand inside me.

I could feel Her finger sliding inside (a first for me!). At first it wasn't really arousing, just a different feeling. Then She started massaging a spot a little deeper inside. It was very sensitive and made me jump when She touched it. "That's your prostate, subbie. Just relax and let me take control." She had stopped stroking my cock now, but still held the head in Her hand. She continued to press down firmly with the finger She had inside my ass. She sawed it back and forth across the prostate. At first, it felt like I really had to pee. Then it started feeling really good. And then...I'm not sure how to describe the feeling.

"Oooh, subbie! Your cock is getting so drippy! You're practically filling my hand." She rubbed my special spot for a couple of minutes more, then showed me Her hand that had been holding my cock. It was practically fully of this thin, clearish liquid. I knew it wasn't urine, but it didn't look like cum either. "Do you notice anything else, subbie? Look down. Your cock isn't hard anymore!"

I checked and She was right. I was almost totally soft! "What happened Ma'am?"

She laughed, "that's called a milking, pet. That's how subbie boys get to cum. All the relief of emptying your balls, but none of the pleasure. At least no pleasure for YOU! I enjoyed it immensely!"

She had me turn over on my back again and cleaned me with a towel. By that time, my cock was shriveled to an embarrassingly small size. Ms Evelyn rummaged around in Her shopping bag and pulled out a box. She took it into the bathroom and I could hear the water running. When She came back, She showed me a very small device consisting of a hollow tube and a ring. I had seen a chastity device before, but never in person. And definitely, never one that was destined for me! Ms Evelyn pushed my soft cock and balls through the ring until it was seated against my body. Then She slid my cock inside the tube, fastened the tube to the ring and locked the little padlock. There was barely enough room in the tube for my cock as it was. And it was about as soft as it could get. There was no way I could get any kind of erection while I was wearing it!

"subbie, it looks so pretty on you! I also bought you a nice pair of pink panties to go with it. I want you to wear them to work tomorrow. And, of course, wear the chastity device too. But that goes without saying, since I have the only keys," She laughed.

With that, She planted a very light kiss on the tip of the chastity tube. "I'm so happy with your new look. Now I really feel like I own your cock. Now don't be staring at the secretaries at work tomorrow. I'd hate for you to try and get hard wearing your new cage!"

"If you can be available tomorrow evening, I'd like to see you again. But if you'd rather just wear the chastity device home, that's between you and your wife and maybe the TSA at the airport! Maybe tomorrow evening we'll go out to a strip club for a bit. OR maybe I'll take you to a male strip club. You'd love to dance for me, wouldn't you?"

I looked up at Her in horror. "No Ma'am. I don't think that would be a good idea. Plus, I think those places mostly draw a gay crowd."

She looked down at my plastic-encased cock. "Well, hmpff, maybe not. But you would look nice on stage! Why don't You plan on meeting me at the Starbucks down the street from the hotel tomorrow night at 6:30? We'll figure out something fun to do!"

I watched as She turned and walked to the door, again admiring the view. I'd like to say that the sight made me hard instantly. But my cock felt like it does immediately after cumming and needed some recovery time. But I swear, I didn't cum! And now, even when I did recover, there was no room for any kind of erection.