Spring Break

The man pocketed the bills and list and said, "It won't be a problem. The items will be delivered to your room in an hour."

Karen grinned and slid a twenty-dollar bill across the counter and asked, "Can you make it a half an hour?"

He pocketed that bill, nodded his head and stated, "It won't be a problem. Now please remove this young man from the lobby."

Karen scowled at the man and growled, "I paid full price for my room and if I want my little man to run around naked, then the hotel is going to have to deal with it." She nearly shouted at him when she said, "There are dozens of people all over town naked and I can't understand what your issue is."

I stood there watching her and learned that when Karen got upset, she flexed her muscles and stood up taller than usual. The man behind the counter must've been intimidated, I know I would've been. He didn't say a word.

Karen eventually turned to me, laid her hands on my hips and spun my body around to face everyone in the lobby. Looking back at the man, she asked, "Would you be okay if he were a girl instead of a boy?" She then grabbed my wrists and lifted them above my head once again. "Or maybe you're a closet homosexual who is attracted to this cute little figure." She turned me around like a ballerina so everyone in the lobby got to see all of me. "Or is your problem with this beautiful young man your own petty jealousy? Do you dream about being as cute as he is?"

The man behind the desk began to mumble under his breath while waving at a younger man who was opening the lobby door for arriving guests. The concierge obviously wanted both of us out of his lobby. He passed the list and some of the money to the younger and man sent him to retrieve the items Karen requested. When that younger man darted out the door, Karen smiled at the concierge before she cupped my butt in her hand. She guided me through the crowd and to the elevator. While we waited for the doors to open, we were still the center of attention in that utter silent lobby.

Thankfully the elevator was empty when the doors opened. Karen pushed me inside and pressed me against the back wall. She reached over and punched a button before taking my face in her hands. She told me I was absolutely perfect! She kissed me aggressively while spreading my butt cheeks wide apart with her hands. I looped my arms up and around her neck and kissed her back with an equal passion. Our tongues danced together which only made me hornier.

When the doors opened, Karen had me step into the hallway first. She reached back and slapped my butt hard before telling me we were in room #1215. It didn't hurt, but I'm sure her handprint was on my pale cheeks. I ran down the hallway playfully looking for her room. When I found it, I spun around and saw her walking down the hall at a leisurely pace. She had a smile on her face and her eyes were wandering up and down my body. I tried my best to pose for her, but I have a feeling I looked like a fool.

When she got close enough, she slid her key through the lock. While opening the door with one hand, she reached out and pulled me into her room by my penis. She led me through her room to a small couch with a table. We sat beside each other on the couch and without a word, she pulled my clothes from her bag. After setting them on the table, she laid her hands on my knees, looked into my eyes and finally spoke.

"Aiden, I really enjoyed stripping you on the beach. And walking you into this hotel's lobby was unbelievably arousing. Every single person down there was staring at your cute little body. I'll bet all of those men and women wished they were me right now. Does that turn you on, Sweetie?"

I tried to say something and she immediately shushed me. She wasn't finished talking.

"Sweetheart, I don't know how long you'll be in town..." She hesitated and I figured out she wanted me to tell her how long I planned to stay.

My voice was squeaky when I said, "I'll be here until Sunday, three more days."

She grinned and her eyes wandered over my body before she said, "Honey, I'm here until Monday and I would love to spend every moment we can together."

I squeaked while struggling to maintain eye contact with her, "I'd like that very much too."

She smiled and asked, "Would you now?"

My mind clouded over the possibilities of all the things Karen could do to me. But at that moment, I couldn't think of anything that would top what I'd already been put through. My penis throbbed and my voice cracked when I squeaked, "Yes."

She stood up and without a word, gathered all of my belongings in her hands and crossed the room to the closet. She typed in a code on the room's safe and when it opened, she placed all of my things inside of it. A chill shot through my body when she closed the safe door and hid her hand while typing in a new code. After shutting the closet door, she turned back to face me and grinned, "There, now all your things will be safe and sound for the next three days."

I didn't move. I couldn't move for several moments. The idea of spending this entire vacation with Karen, the beautiful, strong woman I'd just met was like a dream come true. But spending the next 3 days naked was frightening. I already felt so ashamed of what I'd done that evening. There were so many people who took pictures of me. They were most likely already plastered all over the internet. What if my mother saw them? What if my stepfather saw them? He already considered me to be a complete pansy! The idea of everyone I knew seeing those pictures sent a wave of humiliation rushing through my body. And that humiliation made my penis throb hard and a pearly drop of my juice ran down its modest length.

She crossed the room and sat down beside me again, holding my knees in her hand while we faced each other, she said, "Aiden, starting now, if I catch you trying to cover your nudity, I'm going to take you over my knee and spank you. You'll be spending the next three days in your birthday suit. And Sweetheart, we won't be spending all our time in this room."

I whimpered softly while staring into her eyes. Biting my lower lip, I was about to say something, but she cut me off again.

"But while we're in this room, I'll make you cum like never before and you'll also learn what it's like to have your butt played with. You have got such a cute little ass I can't wait to get my hands on it! And you're going to spend a lot of time learning how to properly please a woman with your mouth."

Karen stood up, took my hands and pulled me to my feet. She kissed me gently and whispered, "Sweetheart, this is going to be a weekend neither of us will ever forget."

I would be naked and helpless until such a time that Karen gave me something to wear. She may not do that. She could drop me off at my motel room naked! My roommate would see me naked! As I considered racing out the door, Karen reached out and took my penis in her fingers. She slowly stroked it up and down while whispering in my ear. "Aiden, I'm going to take such good care of you, you'll never want to leave my side."

I whimpered softly and was so terribly close to squirting when we were interrupted by a firm knock on the door. It happened so suddenly, I nearly jumped out of my skin! Karen grinned at my nervous reaction and released my penis from her fingers. She then took hold of my hand and together, we walked toward the door.

Karen stood behind me with her hand on my bare hips. She whispered in my ear, "Answer the door, Aiden. And don't crack it open so you can peek out. Throw it all the way open and greet our visitor properly."

My penis was oozing its excitement and my hand trembled as I reached for the knob. Doing as I'd been told, I opened the door all the way very quickly. Our concierge stood in the hall holding two shopping bags. One of which was rather large, unbranded and made of opaque black plastic. The other was from a familiar drug store chain and was of white plastic.

His eyes quickly darted from my head to my toes and back again. Holding out the two shopping bags, he muttered, "The items you requested."

I reached out into the hall and took the bags from his hand. Before turning away, I smiled brightly at him and squeaked, "Thank you!" I then spun around and stepped aside so Karen could tip our 'helpful' concierge. While I waited, I peeked into the white shopping bag and found a toothbrush, deodorant, a package of several razors, shaving cream, a bottle of hair removal lotion, sexual lubricant and two boxes containing disposable enema bottles.

A soft moan slipped through my lips which attracted the attention of both Karen and the concierge. I blushed and looked away from them both, instead peeking into the black shopping bag. Inside that one, I saw several boxes covered with pornographic images. There was a hot pink butt plug. A strap-on dildo that was easily twice as long and twice as thick as my own penis.

Looking up from the bag, I saw Karen closing the door on our concierge who was grinning at me from the hallway. When the door was shut and locked, Karen guided me back to the living area of her room. After sitting down, she took the bags from me and began to pull out one item after another, placing each on the table in front of us. I sat beside her in silence, watching her work and shivering with both desire and shame while thoughts of what those things could do to me raced through my mind.

After removing the packaging from each item, she handed me the toothbrush, deodorant, razors, shaving cream, hair removal lotion, lubricant, and disposable enemas and sent me to put it all in the bathroom. Before I left her side, I timidly asked, "Karen, um, is all of this for me?"

She looked into my eyes and smiled, "Yes it is, Aiden. Before our fun begins tonight, you're going to have every hair below your eyelashes removed. You're going to have your bottom rinsed out. And you're going to scrub your body from head to toe."

Nibbling on my lower lip, struggling to look into her powerful eyes, I whimpered, "And then?"

She didn't look away from eyes when she reached out and picked up the strap-on. Holding the phallus between us, she said, "Judging by the look on your face, I'm betting this will be a new experience for you." She watched me slowly nod my head to confirm her assumption. "Baby Boy, I'm going to pop your cherry with this."

A soft whimper slipped through my lips. I'd fantasized about being taken with a strap-on a thousand times. But seeing that strap-on dangling from her finger in front of my eyes was tremendously frightening. Very soon, that dildo would be buried deep inside my bottom! I asked with a squeaky voice, "Is it going to hurt?"

She smiled and spoke in a gentle voice, "Sweetheart, I would never hurt you. I promise this will only be a pleasurable experience for both of us." Glancing at my armload of things, she reached up and tapped the disposable enema and said, "Let's start with this."

She then rose up off the couch and followed me to the bathroom. After I'd arranged everything neatly on the counter, Karen picked up the tube of lubricant. "Aiden Honey, I need you to lean against the counter, bend at the hips and spread your legs wide apart." Moving in behind me, she looked at my reflection in the mirror and whispered, "Yes, this is perfect."

While removing the cap from the lube and squirting some out onto her finger, she asked, "Sweetie, will this be your first enema?"

I watched while she coated the long, plastic nozzle with the lube. I whimpered, "Yes." While my hips ground around anxiously. Karen then squirted more lubricant onto her finger. Laying one hand on my naked hip, she whispered, "You are so precious. Baby, I'm going to touch you now."

Every nerve in my body was on high alert. My heart was pounding in my chest as I waited. When it happened, when her slippery finger made contact with my tight knot of a hole, I chirped in an oddly high pitch and my back arched deeply. Her finger slithered and slathered over my highly sensitive little hole. I squealed, "Karen!! Oh My!! It feels so... so..."

While I struggled to find the words I needed to describe the sensations, Karen lined her finger up and slowly pressed it into my body. She watched my reaction in the mirror and after seeing my eyes roll up into my head in pleasure, she whispered, "I knew you were going to enjoy this. Sweetheart, we're just getting started. Just wait until I bury my dildo inside of you."

When my eyes fluttered open, I found Karen was still looking at my face while she slowly fingered my bottom. My hips rolled up high and I moaned softly when she withdrew her finger from my body. After wiping off the digit that had penetrated me, she picked up the enema bottle and bumped the plastic nozzle against my little hole.

While looking at me in the mirror, she said, "Take a deep breath, Aiden."

I did as I'd been told and while I did, she gently sunk the nozzle of the enema deep inside of me. Even after taking that deep breath, I was left gasping for air. The feeling of that hard, plastic nozzle sliding inside of my body was indescribable. I shivered and my hips rolled up high to allow her easier access.

She whispered, "Here it comes." And she then began to slowly and steadily squeeze the plastic bottle. The feeling of the liquid filling my butt wasn't at all negative. I found it to be a very pleasant sensation. While she withdrew the nozzle from my bottom, she whispered, "Aiden, I want you to hold that inside for a little while."

My hips ground around in circles while Karen tossed the empty bottle into the trash. When she returned to stand behind me, she rested her hands on my hips and asked, "How are you doing?"

I whimpered, "Do you really need to ask?" As I uttered those words, I stood up far enough so she could see my rigid and oozing penis. Reaching around my body, she rubbed the pad of her index finger over the slippery pink head of my penis. After she'd coated her fingertip with my juices, she slowly raised that hand and painted my lips with my own excitement. The entire time, she and I stared at each other in the mirror.

She leaned in and licked my earlobe while whispering, "Such a naughty boy." She nipped my earlobe with her teeth before saying, "Sit on the toilet. Call me when you're finished." Without another word, she left the bathroom, closing the door behind her.

I looked at my reflection in the mirror for a few short moments, thinking about all that had happened since I left my motel room earlier that day. Nature called and I tiptoed my way to the toilet and sat down. I was thankful Karen had shut the door on her way out. The noises I made while sitting on that toilet were not the sort of sounds I wanted her to hear. After cleaning myself up with toilet tissues and spritzing the room with the deodorant she'd bought for me, I flushed the toilet. While washing my hands, Karen re-entered the room without even a knock.

Karen didn't mention what had just occurred in that room and I was thankful for that. She sat on the closed lid of the toilet and called me between her spread knees. After filling her palm with hair removal cream, she made quick work of the task at hand. In no time at all, my body was covered with a thick layer of cream that soon had my skin tingling. The tingling became more intense with every second it remained on my body. I found myself dancing around in the bathroom while dealing with the intense sensations.

Karen sat there calmly watching me and said, "Aiden, do you realize I stripped you naked on the beach. I walked you into this hotel's lobby naked. I locked your clothes in my safe. I gave you an enema and now I'm removing all of your body hair. And after all of that, you haven't objected once. You've simply done as I've told you too."

I whimpered while dancing from one foot to the other, "I know! I never stand up for myself. I'm sorry!"

She grinned at me and said, "Oh Sweetheart, you don't understand. Being as obedient as you are isn't a bad thing. Baby, doing as you're told is a good thing. A very, very good thing that I consider a very attractive quality in a boy."

In a squeaky voice, I asked, "Really?"

She smiled and said, "Yes, really. Now hop in the shower and rinse off that cream."

I didn't need to be asked twice. I barely bothered to adjust water temperature before I stepped under the warm water and watched as the cream washed away from my body. With it, my sparse patches of body hair went with it. After all of the lotion had been washed away, I stepped out from under the water. Karen approached the tub, reached out and let her fingertips pass over the places where hair used to be.

With a grin on her face, she said, "The cream did a better job than I expected. I don't think we'll need to use that razor at all. Step back under the water and wash down the soap and shampoo. When you're finished, meet me in the living room."

I took my time and washed my body especially well. Every square inch of my body had been soaped down and rinsed off twice before I turned the water off. The sexy feeling of my soapy hands sliding over my hairless skin was nothing compared to the way the towel felt. When I was dry, I paused to look at my naked, pale and hairless body in the mirror. My penis looked positively tiny without its patch of strawberry blonde pubic hair to hide behind. But that fact made it throb and a drop of its pearly excitement began its slow descent down its smooth, thin shaft.

Stepping out of the bathroom, I tiptoed into the living area and found Karen lubing up the butt plug. I stood there silently watching her until she noticed me. When her eyes met mine, she said, "Aiden Honey, you look absolutely delicious!"

I blushed from head to toe and lowered my chin. In a soft whisper, I said, "Thank you, Karen."

Wagging her finger at me, I crossed the room on my toes. She had me stand between her spread knees, facing away from her. I bent forward and braced myself against the table. Karen once again lubed up my tight little hole. While fingering my behind, she said, "Do you remember when I said popping your cherry would be a pleasurable experience?"

I nodded my head while grinding myself back against her finger. I squeaked, "Yes!"

Pulling her finger out of my body, she next picked up the butt plug. Lining it up with my virginal hole, she let the stiff rubber bump against that knot of nerve endings. "Well, having this inside of you for a while will loosen you up. When I slide my strap-on into your butt, you'll be squealing in pleasure. And not screaming out in pain."

I gasped when she applied pressure to the plug and my wrinkled hole began to stretch out allowing it to enter my body. Karen pressed it in a little bit at a time. She would press a little in and let it slip out. Then press in a little more. When she neared the widest part of the plug, I was moaning and grinding my hips back toward her. She was being so gentle and taking her time. Having her press that plug inside of me was a wonderfully erotic event.

When the widest part of the plug slipped inside of my body, my tight hole pulled the base of the plug snuggly between my cheeks. Karen wasn't finished. She took hold of the base and pulled it out so my hole stretched over the widest part again. She repeated that process over and over until finally letting the plug settle deep inside of me.

Karen rose up from the couch and spun me around so we faced each other. Taking my naked, hairless and extremely horny body in her arms, she kissed me. It was a long, wet, and loud kiss. My arms slithered up around her neck while our tongues danced together and I fought against humping myself against her leg.

When the kiss came to an end, she remained close enough to me that her lips brushed against mine when she asked, "How do you feel, Baby Boy?"