The Pleasure Giver Chronicles Ch. 04

Astute readers will notice a striking similarity to an earlier story, The Tired Traveler. That is no coincidence. The stories chart two directions Soma/PG can go in his journey of discovery. I'm torn which way he should proceed, as I'm enjoying exploring both possible tracks. While the stories in this series are designed to be standalone, there is an overall arc as PG moves toward his destiny. So I leave it to you, the reader: which story resonates with you more? Which best suits the Soma you know and (hopefully) love? Let me know in the comments.

I arrived at my room early, as Mr. King's email had instructed. He promised something special today. Knowing his talent for understatement, I shuddered with anticipation, and with a touch of trepidation. On the bed were two pair of beige pantyhose, still in their packaging, what looked like a black corset with many hooks, and a brunette wig. A pair of blue pumps with two inch heels were on the floor. I picked up the note with my instructions and read it. "PG, instead of your normal preparations, shower and shave your face. Call the front desk and ask for Mrs. King when you have finished your shower and before you start shaving."

Puzzled, I took off my clothes and placed them in their usual dresser drawer. As I walked toward the shower, I glanced at the clothes rack and stopped. Hanging there were a blue dress and a matching blue chemise. The dress looked a bit small for me; I supposed that's why the corset was on the bed. My client apparently wanted a crossdresser, but why me? I'm hardly passable and, while I certainly enjoy wearing stockings and sexy lingerie, what I saw was hardly Victoria's Secret. It was almost matronly. I mulled it over while I showered and realized that, as usual, I had no idea what Mr. King had in store for me, and that my best plan was to go with the flow.

I dried off and called the front desk as directed. Mrs. King was brief. "Go ahead and start shaving. I'll be up shortly to help prepare you. Don't start dressing before I get there." With that, she hung up and I returned to the sink and started shaving. Given the time of day, I didn't have much of a shadow, but, given the clothes in my room, I figured she wanted my face to be as smooth as possible. As I was shaving at the sink, I heard the door open and, looking in the mirror, saw Mrs. King enter. She was dressed professionally, as usual, and had a look of business about her. In her hand was a small case, which she set on the dresser.

"Here's the situation," she said, "We have a regular client flying in today. His usual pleasure giver is sick, so we need you to fill in. When he arrives, he wants to be greeted by his wife and given a bit of pampering. He has certain expectations of his wife: she is to be dressed in a feminine but modest style and be waiting for him when he gets in his room. She is to address him only as 'Darling' and will attend to his basic needs when he arrives. He expects her to pamper him before and after his shower. He enjoys a good foot massage, which I know you'll enjoy giving him, and wants oral relief. Following that, she will take her leave of him. The clothes in your room are what he expects her to wear. Since you are larger than his normal "wife," I'll help you with the cincher so your clothes will fit properly. He does not expect you to undress while you are with him. Your speech should be kept to a minimum and should sound female, but not exaggerated. Do you understand?"

"Yes, Ma'am," I answered, adjusting my voice to a soft contralto, trying to approximate Lauren Bacall in timbre. As she had been explaining my duties, my cock had been showing how it felt about this assignment. By the time I finished shaving and turned to her, it was fully erect. She looked at it with a frown.

"It will not do to have that showing...very unladylike," she said, disapprovingly. She opened her case and took out a roll of cotton twine, medical tape and a pair of scissors. "Come over here, so we can take care of that."

I did so, wondering what she had in mind. She reached into the ice bucket (who had filled it? not me), pulled out a handful of ice and squeezed my cock. I sucked my breath in as the cold hit. I felt my nipples growing hard, even as my cock shrank. She held it firmly until it had shrunk to its normal state.

At that point, she tied a slipknot just under my cock head and pulled it between my legs. She moved behind me and pulled until it was nestled in my ass crack and splitting my balls apart. She wrapped the twine around my waist twice and tied it off. My cock wouldn't be visible under clothes and any bit of excitement would cause the twine around my cock to constrict it painfully. She then pushed my testicles up into their original location in the inguinal canals, ignoring my grunts of pain, and taped them in place. During this entire process, Mrs. King was quiet and efficient. As far as I could tell, she was being purely professional, though I suspected she was enjoying my predicament.

"Now, put on the pantyhose."

I sat on the bed, feeling my captive cock being pushed into my ass crack. For a moment, I wondered if it could somehow penetrate my ass, but decided that was silly. I opened one of the packages and unwrapped the pantyhose (queen size, I noted). I rolled the right stocking portion down to the foot and slipped my foot into it, being careful not to put a run in it. I rolled it halfway up my calf, then inserted my left foot in the same manner. I rolled it up to my knees, then stood and managed to pull it up the rest of the way. I smoothed it on my legs and straightened the pantie, which was a control top. So much for sexy...

"As I feared," Mrs. King said, "Your legs are showing too much hair. Put on the second pair."

Sighing, I sat down, carefully, on the bed and put on the second pair of pantyhose. She looked approvingly, as my legs were completely camouflaged by the dual stockings. My crotch was starting to feel warm, and I wondered if I would start sweating there. The stockings were causing my legs to itch slightly, but I knew better than to scratch. I hoped the discomfort would go away soon...

...a hope that was dashed as Mrs. King handed me the black cincher. "Put this around your tummy and snap it up. It may be a bit uncomfortable at first, but your body will adjust."

I wrapped it around my stomach and discovered that it was smaller than I was and that it did not stretch. I looked questioningly at Mrs. King, who looked back impassively with a small grin. I sucked in my gut as much as I could and connected the first hook. I worked from the top down; it started just below my sternum and extended a couple of inches below my navel. The hooks were progressively more difficult to connect and, by the time I had finished, my belly was tightly constricted and my compressed diaphragm only allowed me to take shallow breaths. I was in no danger of passing out, but I was also going to have to move slowly and breathe carefully. I was aware of that part of my body in a way I had never noticed before. I resolved to start exercising more regularly.

Mrs. King then handed me the chemise. I slid that on, surprised at how tight a fit it was. For some reason, I had imagined it would be looser on me, but it, too, clung to me, hiding the snaps on the cincher and covering my upper chest hair. I glanced in the mirror and noticed that, in slimming my waist, the cincher was also pushing up my breasts, giving me a more female appearance. I could see the outline of my erect nipples on the chemise and, at the same time, felt a tightening pain around my cock that indicated the twine was choking down my excitement. Not only that, the sensation of the twine around my waist was more pronounced, being forced in by the cincher. This was going to be an interesting afternoon, for sure: the pleasure/pain had already started.

Mrs. King had me turn around for her; she smoothed down the chemise and straightened the straps. When she was satisfied all was in order, she said, "Now, put on your dress."

I walked to the clothes rack, taking small steps to minimize the stress on my abdomen, and took the dress off the hangar. It was a modest enough blue dress. I pulled it over my head and slid my arms into the sleeves, which ended halfway to my elbows. It had a high collar, with a button top that concealed my cleavage, such as it was. While form fitting, it wasn't tight, and showed my newly slim waist. The dress came almost to my knees. I ran my hands over it to smooth it, enjoying the satiny feel of the cloth...a little too much, as my noosed cock reminded me. Mrs. King zipped up the back and stepped back.

"Almost ready," she announced, as she placed a cap over the top of my head and attached the wig to it with some tape. She brushed it out and fluffed it so that the brunette curls bounced on my shoulders. Opening the case, she pulled out some brushes and boxes and I realized, with a shock, that she was about to put makeup on me. That wasn't something I had anticipated and I gasped slightly...very slightly, as the cincher put an end to that. She swiveled the desk chair until it was facing her. "Sit down," she said. I complied, carefully, eliciting a chuckle from her when I sat the wrong way on my captive cock, and quickly squealed and readjusted my position.

She went to work efficiently. "Don't worry, I'm not going to tart you up, just hide that shadow and make you a bit more wifely." She brushed some sort of powder on my cheeks, which I guessed was a foundation.

"Close your eyes." I did so and felt her applying a pencil to my eyes and a brush to my eyebrows, after taking off my glasses.

"Now, stretch your lips." I knew what was coming and prayed that it would come off easily, knowing I could never in a million years explain the presence of makeup and lipstick on my face at home.

Finally, she handed me my pumps and I slid them on my feet. Taking my arm, she raised me from the chair and turned me to the mirror. I put on my glasses and looked in amazement at the two women I saw looking back; one was definitely not the most attractive woman I had seen, but I was shocked at the transformation she had managed. "One last thing," she said, and wrapped a wide blue ribbon around my throat, concealing my Adam's apple.

"Thank you, Ma'am. This is amazing!" I said, doing my best to make my voice worthy of the work she had done.

"We want you to be an attractive wife. You won't be needing those," she said, removing my glasses and placing them on the table. "Now, your final instructions. Your client's plane was delayed. He'll be arriving here in about an hour. I'll walk you to his room. You'll wait for him there. When you've finished, come to the office, and I'll clean you up. Don't worry about your key card. I'll hang on to it and return with you to clean you up when you're finished. Let's go."

She took my arm, which was good, as I could see very little without my glasses. Everything was a blur, especially when she opened the door and led me out in the sun. I could see the fuzzy outline of a few people walking around. Were they looking at me? I couldn't tell.

"I have to return my makeup case to the office," she said, handing me a key card. "Your client is in room 318. Wait for him there. When he's through with you, come to the office." With that, she went back into my room, leaving me alone on the walkway. I turned toward the stairwell at the end of the building and started walking, thankful for the small heels on my pumps, and taking small, mincing steps, limited by the cincher and the material of the dress.

I walked past a couple of men. As I passed them, I could sense, rather than see, their expressions transform from curiosity to lust. One of them cupped my tush with his hand; I jerked and blushed, then winced as my cock tried to respond. I made it to the stairwell and walked up the two flights, holding on to the rail and stepping carefully in my heels. Behind me, I heard a whistle and found myself smiling. Apparently, I was desirable, perhaps even semi-passable.

I arrived at the third floor breathing as heavily as I could, given the tyranny of the cincher. The climb had unexpectedly worn me out. In addition, I was aware of my cock pulling up slightly when I went up a step. I hoped it wasn't going to be worn raw by the end of this. I passed a maid pushing her cart down the hallway. She gave me a grin. "Nice look, Pleasure Giver." I smiled back weakly and hoped I wouldn't see anyone else. Did she know who I was? Or was I just another motel whore to her?

I arrived at 318 and entered the room. I tossed the key card onto the table and started to close the curtains, when I saw a note taped to the window sill. "To be closed only by the occupant." Stifling some very unladylike language, I sighed and sat on the edge of the chair. I saw a blur on the floor; looking more closely, I saw a pair of high heeled mules. Of course. I took off my pumps and slid my feet into the mules. I curled my legs under me, my toes pointing out, and waited for my client.

I went over the rules for this encounter and tried to ignore the various sensations on my skin that were alternately pleasuring and tormenting me. I could feel the sweat under the cincher and pantyhose. While the various layers of clothing would prevent the dress from staining, I was still unpleasantly warm and, increasingly, sleepy. Between the heat and the restricted breathing, I was soon nodding off...

...until I heard the sound of the door opening. I jerked awake, disoriented for a moment, and then remembered where I was, and why. I slid my legs to the floor and stood as sexily as I could. "Hello, Darling. I'm glad you finally made it home," I said, walking to him to take his suitcase. As I drew nearer, he came into focus. He was slightly taller than I, even in my high heeled mules. His aftershave was subtle, but manly. Never one to wear aftershave or cologne, I was surprised at how pleasant it was on his skin. He was wearing a grey wool suit, which seemed appropriate for such a distinguished face, with well-coiffed grey hair and tired looking brown eyes. He looked at me for a moment, taking me in, then started loosening his tie.

"The flight was delayed, and packed. I'm exhausted. Would you unpack my suitcase while I take a shower?"

"Of course, Darling," I replied, getting into the role. He put his coat on a hanger and, on impulse, I moved behind him and started rubbing the tension from his shoulders. He gave a sigh and leaned back against me. His manly scent filled my nostrils and I felt my cock starting to tighten again. My hands slipped over his shoulders and started unbuttoning his shirt. I could only reach the top three buttons, but that was enough for me to learn that he wasn't wearing a t-shirt, that his chest hair was thick and smooth, and that his nipples were large and sensitive. The pain in my cock was growing, and I knew I wouldn't be able to sit down without serious damage, but none of that mattered at the moment. I was slipping into...subspace? No, something different...something unknown.

He finished unbuttoning his shirt, turned around and surprised me with a quick kiss on my lips. "That felt good, Dear, but let me get my shower so I'm presentable."

"Of course, Darling," I murmured, with an unmistakable, and surprising, touch of disappointment. "Let me hang up your clothes and I'll unpack your suitcase while you shower."

He gave me his shirt and I put it on a hanger while he sat down to take off his shoes. The moment he sat on the bed, he fell back with a moan of relief. I knelt down and took off his shoes, then his socks. After putting them in his shoes and moving them under the desk, I started massaging his feet, using my thumbs on his soles and setting each foot on one of my thighs. He sighed with pleasure as I relieved his tension through his feet. I raised each foot up to give the toes a rub; the odor was noticeable, but surprisingly light, considering he had been on his feet and in a cramped plane all day. I considered giving them a quick kiss, but decided that could wait until after his shower, when he was more alert.

As I started moving my hands up his legs, he stood up and took off his pants. For a moment, I remained on my knees, expecting him to present his cock to my mouth, but he held out the trousers and I realized he wanted me to hang them up. I stood up and took them. He turned on the light and closed the curtain at last. Taking his toiletry bag from the suitcase, he walked to the bathroom. I put his pants on a hanger, feeling vaguely dissatisfied. I tried to determine the reason and realized I had been looking forward to seeing the cock that belonged to such a distinguished gentleman.

I turned to the suitcase and put away his underwear and socks, noting with approval that he wore briefs. I finished unpacking, putting up his hanging clothes and noting that he didn't wear pajamas. He had packed a pair of gym shorts and a t-shirt, along with some sneakers. Before I put them down, I took a quick whiff, catching a scent similar to his feet. My cock was tightening again and I was aware of sweat dripping down the inside of my cincher. Where are these thoughts coming from? Distinguished gentleman? Smelling his sneakers? That isn't me.

My reverie was broken by his voice. "Dear, could you come and dry me off?"

I picked up a towel and walked into the bathroom, my whole body becoming alive. I could feel the pressure of the mules on the top of my feet as I walked; the sensations moved up and intensified the smoothness of the pantyhose on my legs. The silky sleeves of the dress caressed my arm and I felt my cock trying to fill my ass. Even the pressure of the twine was turning to pleasure. I drew close enough to see the drops of water on his back.

I took a breath and started drying him. He hadn't shampooed, so his hair was dry and still in place. I rubbed the back of his neck and shoulders, then wrapped the towel around his left arm and patted him down. I felt the muscles of a man who worked out, but not to excess. Moving down to his hand, I saw the wedding band and wondered what his wife was like. "She's a lucky lady," slipped into my mind unbidden. I shook my head hard and moved to his right arm. My cock was on fire with pain, and I knew I was going to have to get my thoughts under control if I wanted to avoid an embarrassing trip to the ER.

And then, his back! It was covered with a light coating of hair, which was matted down, but not concealing the smooth skin under it. I patted it dry with the towel and couldn't control myself as I placed a kiss between his shoulder blades.

"Mmmmm, Dear, I'm glad you missed me."

Taking that as permission, I knelt lower as I dried his back, kissing my way down his spine as I proceeded to his waist. His legs were spread enough that I could see his balls hanging low. I patted his tush dry and, rather than chafe his crack with the hotel towel, I spread his cheeks and licked the water from its hiding place, making sure that his rosebud was well dried. I was surprised, and pleased, to find no hair around it, in contrast to the hair I could see covering his scrotum. He smelled and tasted soapy clean; I had to linger to trace the wrinkles and ridges of his anal opening. I could feel it twitching from the attention. He moaned in appreciation.

"Dear, what's gotten into you? That felt amazing!"

"I guess I really missed you, Darling."

"I'll have to be gone more often, then."

I wrapped the towel around his legs and rubbed them down quickly, admiring their firmness, but wanting to finish up so he would turn and face me. I was on my knees, with the heels from my mules digging into my tush, adding to the sensations that were fueling my fire. When he turned, I would, at last, be face to face with his crotch.