Spring Break

By fantaseeboy.


Shortly after settling into the motel room we’d reserved, the friend I’d come with received a text. He left shortly afterward to join the rest of the lacrosse team that had also come to spend spring break on the beach. I hadn’t expected him to ditch me, so I puttered around the room for a while. I took a shower, shaved my face, even though I really didn’t need to. I added some gel to my short strawberry blonde hair and tried not to part it so severely to one side. But it always wanted to lay that way, which left me looking much younger than my 19 years. I slipped into a clean pair of briefs, baggy cargo shorts, and a t-shirt. Before stepping out the door, I grabbed the keycard to my room, my phone, wallet and stepped into my boat shoes.

The sun was just starting to set as I stepped onto the outdoor walkway or a 3rd-floor room. It was warm and slightly humid, which was a welcome change from the chilly weather at school. The music I heard was coming band’s music beach, only a few blocks away. I worked my way off the motel grounds and toward the beach. There were big crowds of people walking on both sides of the road, and cars packed with college students were slowly cruising down the narrow street. I felt like I was the only person there that wasn’t included in a group.

When I arrived at the beach, I could see a huge crowd of people mobbed in front of a stage. I wasn’t familiar with the music the band was playing, but I joined the crowd and began cheering along with them. Even though I started at the back of the crowd, I soon found myself surrounded by my cheering peers.

After the sun had fully set and the band had played several songs, I began thinking about returning to my room. Standing alone in the dark, surrounded by a crowd is a very discomforting feeling. When I was about to turn and leave, I felt a presence move in close behind me. It was as if whoever had stepped so close to me had done so on purpose. The band’s music was loud, but not so loud that a conversation couldn’t be held without shouting. She leaned in close to my ear, and I smelled her before I heard her. Her musky perfume filled my senses and made me shiver. I’d never smelled anything so sexy. Her low, sultry voice sent a chill up my spine. “This band is excellent.”

Looking back over my shoulder, I was greeted by a woman, not a girl. A woman who was at least 20 years my senior. She stood several inches taller with a very fit build. She wore the flowery print top that left her arms and shoulders exposed, which had more muscle definition than any of my roommate’s friends on the lacrosse team. The white skirt she wore hung to just below her knees and left her muscular calves exposed. Her wavy, dark-brown hair was pulled back into a loose ponytail. She had a beautiful face and wore minimal make-up. I bit my lower lip and nodded my head stupidly in response to her statement. I turned back around and prayed she wouldn’t leave.

The next song the band played must’ve been viral. Everyone in the crowd began pumping their fists in the air to the beat of the music. I joined in and began pumping my skinny arm in the air along with all the other people.

It happened quickly. I felt this woman laid her hands on my hips and then quickly slide them up under my shirt and drag her fingernails from my collarbones to the top of my shorts. My penis became erect in an instant. I’d never had anyone touch me like that before. I had no clue how to respond. I decided to act like it didn’t happen. After a few moments, she did it again. This time letting her fingers trace my collarbones, ribs, gently pinch my nipples, and finally come to rest on my hipbones. She left her hands on my hips while I tried not to do something stupid like spin around and ask her what she was doing. I didn’t want to upset her.

Just before that song ended, she took hold of the bottom of my t-shirt and began to lift it. Higher and higher, it came until I had to decide: confront her or simply raise my arms. I chose the latter. Raising both arms high, she pulled my shirt up over my head and off my arms. I’m not the type of guy who goes without a shirt. I’ve always been rather skinny with fair skin and only wisps of thin, strawberry blonde body hair. But having this strange woman pull my shirt off was a freeing feeling. I suddenly felt alive and electric. And the crazy thing was, no one around us even noticed what had happened! When I turned my head, I couldn’t help but smile as I watched her slip my shirt into the bag she wore over her shoulder.

The next song started, and the crowd came alive once again. Fists began pumping into the air and the crowd tightened around us. The woman behind me rested her hands on my hips, and I felt her warm breath on my neck and ear. She slowly and teasingly slipped the index finger of each hand under the waistband of my shorts. Moving her hands toward each other across the front of my body made goosebumps pop up all over my body. As her hands got closer to each other and the front of my shorts, I unintentionally pushed my hips back against her. I heard her moan as her hands met each other. Her fingers briefly brushed across my underpants right over my super stiff penis. I swear I’d never been so horny before!

Her muscular arms kept my hips pulled back against her body while her fingers slowly undid the button on my shorts. I looked up over my shoulder, and before I could utter a single word, she kissed me. Her tongue shot into my mouth and kissed me with a level of passion I never knew possible. While distracting me with that kiss, her hands quickly lowered the zipper of my shorts and spread them wide open. With that task accomplished, she dragged one hand up along my body until she held my neck. She continued to kiss me while slowly sliding her other hand under the band of my briefs until she cradled my insanely stiff penis in her hand. She didn’t move her hand at all; she simply held my small penis and balls in her large, strong hand.

When our kiss broke, I was left gasping for air surrounded by hundreds, if not thousands, of people. She lowered her hand from my neck pinched first one of my nipples and then the other. That hand soon slid down my body until the thumb had slipped under the waistband of both my shorts and briefs. About that same time, she’d released my penis and positioned that hand similarly on my opposite hip. I knew what she planned to do. I took hold of her wrists to keep them from stripping me naked. I looked back up over my shoulder, shook my head from side to side, and silently begged her to stop what she was about to do.

She smiled down at me, kissed me quickly on the lips, and responded by nodding her head. Even with my hands on her wrists, I wasn’t strong enough to stop her from lowering my shorts and briefs. I know I was blushing like crazy when the stiff prong of my pink penis popped free of my shorts. I struggled to stop her, but I was no match. Finally, when it dawned on me that my penis was out for all to see, I released her wrists and quickly covered myself with both hands. This allowed her the opportunity to lower my shorts far enough that they fell to my ankles.

Leaning in close, she licked my ear seductively and stated loud enough for me to hear over the music and crowd surrounding us, “Step out of your shorts and shoes.”

Knowing people should be gawking at the naked boy standing in the crowd, I looked around. But I didn’t see anyone looking my way. Everyone was staring straight ahead at the band on stage. Feeling like I was about to cry with shame, but more aroused then I’d ever been before in my life, I slowly slipped my foot from my shoe, out of my shorts, and stepped out onto the warm sand of the beach.

Licking my ear again while dragging her fingernails from my collarbones to midway down my bare thighs, she said, “That’s a good boy, now the other.”

Biting my lip hard while cupping my hands over my throbbing penis, I felt so embarrassed! But I did as I’d been told and slipped my other foot free of my clothes. Her hands moved to my sides and slid all the way down my legs. She picked up my shorts, briefs, and shoes from the sand and quickly put them in the bag with my shirt. She rose behind me and laid her hands on my hips, pulling my butt back against her hips. She began to grind herself against me in time to the music. Having her hold me in that manner was somewhat reassuring. I felt safe with her, so near. It’s odd; I didn’t even know her name. But I somehow knew she’d protect me if needed.

After bashfully dancing along with her for half a song while still cupping my hands over my penis, she let her fingers begin to explore my body once again. This time her hands wandered up and down my front while intentionally avoiding my hands and penis. They also explored my back and bottom. With my butt still pressed back against her hips, she could only fondle my cheeks so much. But while she did, she leaned in and moaned into my ear, “If I had a cock, I’d be fucking you right here, right now.”

She emphasized the word ‘cock’ by thrusting her hips against my backside.

I didn’t say, ‘Thank goodness, you don’t have a cock,’ or, ‘Ew! Gross.’ No, my response was, “I’m sorry.”

Shortly after making that silly statement, she laid her hand on my neck and turned my head toward her again. Looking up into her eyes, I felt so helpless and small. Then, her eyes left mine and focused on the necklace I wore. She quickly raised her hands and removed them while stating, “I want my sweet boy to be completely naked.” Once removed, she added my necklace to her bag.

Moments afterward, she let her hands move to my wrists and gently pulled my hands away from my penis. I’d never felt so naked and exposed before. Then, still holding my wrists, she raised our hands above my head. My hips wiggled around my body, shivered with arousal. With my hands above my head and my four-inch stiff penis pointing upward, I began to notice people looking in my direction. I wanted to pull my arms back down and cover myself, but my wrists were held up firmly. All I could do was try to lift a leg to cover myself. It didn’t take long for the people around us to pull out their phones and begin taking pictures and videoing my nudity. As more and more phones appeared, the woman behind me steered my body to face cameras.

First licking, then nibbling on my earlobe, she said, “My sweet boy is going to be famous! So smile for the cameras, Sweetie!”

When more and more people began surging toward us to get pictures, the crowd tightened, and I felt the hands of strangers groping me. I think the woman behind me panicked as much as I did. She quickly spun me around and held me close. I don’t remember if I walked backward or she carried me, but we eventually broke free of the mob of people. Even then, she didn’t slow, she kept moving at a quick pace until we found ourselves in a much less crowded area of the beach. The glow from the nearby hotels dimly lit the area, which allowed us to attract less attention. But there were still small groups of people stopping to stare at the naked boy with the muscular woman. Finally, she released me and held me at arm’s length. Then, in a concerned tone, she asked, “Are you okay? I wasn’t expecting those people to rush us like that.”

Looking into her eyes, I told her I was okay. Then, without another word, she wrapped her arms around my body and gave me a hug right there on the beach. I wasn’t expecting to be hugged, but I threw my arms around her neck and embraced her just as tightly. When the hug ended, I quickly lowered my hands to cover my stiff penis. Then, biting my lip, I whimpered, “May I ask you a question?”

She smiled before saying, “Of course, Sweetie. Ask me anything.”

“May I please have my clothes?”

Her smile warmed, and while shaking her head from side to side, she replied, “I’m sorry Sweetie. You may not have your clothes. I’m not ready for you to cover up your perfect, little body yet.”

Knowing I really didn’t have a choice, I accepted her response and remained standing before her, completely nude. Occasional groups of people were walking around us. I felt their eyes on my body. It was so embarrassing yet terribly arousing at the same time. I’m not sure, but I think I stuttered when I asked, “M-M-May I ask another question?”

Laying her finger under my chin, she forced me to look at her. The smell of her perfume mixing with the ocean air filling my senses again made my penis twitch and throb. Finally, she kissed me gently on the lips and said, “Yes, you may.”

“W-W-What is your name?”

She kissed me again, and her free hand wiggled under my hands so she could drag her fingernail along the underside of my still rigid penis while whispering, “What would you like to call me?”

I whimpered softly from the unexpected contact, and my mind ran wild, trying to find an answer for her. She eventually rescued me by telling me her name was Karen. After I shared my name, Aiden, she spoke in a soft voice, “That is an adorable name for a charming boy.”

We were beginning to attract a rather large audience, and the flashes from camera phones were gathering even more attention. To avoid another mad rush, she took my hand and guided me further away from them toward the nicer, upscale hotels I couldn’t dream of affording. I sort of felt like a child being led along by his mother. At times, I had to run along beside her to keep up with her pace. While running, I couldn’t keep my little erection covered. It was left bouncing around for anyone to see.

We passed small groups of people either sitting or walking along the beach. Every person we passed stopped what they were doing and watched me walk/run along beside Karen. By then, each time I moved to cover my bare penis, she squeezed my hand firmly. Then, when I looked up at her, she shook her head from side to side. I almost asked her for my clothes again.

But just as I was opening my mouth, she began, “The moment I saw you walking toward that concert all alone, I knew you were a very special boy. I could tell by the way you looked, the way you walked and the bashful way you joined the crowd. As soon as I got close to you, I couldn’t keep my hands off you! I knew you had a cute little body under those baggy clothes and I hoped your mother had raised you to be an obedient boy. It’s obvious she did. Or you wouldn’t be walking here with me without a shred of clothing on!”

Our course changed eventually as she led me toward a fancy hotel with more than a dozen floors. As we got closer and closer to the gated grounds of the hotel, I began to panic. It sounds silly, but I was somewhat okay being naked outside with her on the beach. But stepping into the bright lights of a fancy hotel in my birthday suit was a completely different matter. I was scared, silly! My stomach began doing somersaults, and I felt ill!

She felt me pulling on her arm and must’ve seen the fear in my eyes. She had a sympathetic look when she stopped and turned to face me. “Aw, you’re scared, aren’t you? You poor thing. Baby, it’s spring break. There are naked people all over the place. It’s okay. You don’t need to be scared. And once we get to my room, I promise I’ll make everything you’ve been through worthwhile.”

I quickly chirped, “I haven’t seen anyone else naked.”

She kissed my lips gently before saying, “You haven’t been looking closely enough. There are naked girls all over this city.”

I whimpered softly, “B-b-but I’m not a girl.”

That’s when she leaned in and kissed me again. Then, while holding my shoulders in her strong hands and looking down into my eyes, she explained, “Aiden, sweetheart, there are lots of men and women who love to see naked boys. But unfortunately, there aren’t many boys willing to be stripped naked in public. And that makes you extremely special.”

Her logic was confusing enough to make sense. Therefore, I agreed to walk into the hotel with her. She told me not to cover my privates up, or she may have to punish me when we got to her room. The idea of being punished by Karen sent a shiver through my body. I’m not sure if it was a good shiver or a bad shiver. It didn’t really matter. My penis throbbed even harder at the thought.

Using her keycard to open the gate, she led me into the pool area. With the sun having already set, there weren’t many people using the pool, but few couples. And they all stared at my naked body while Karen held my hand and led me toward the brightly lit doors of the hotel. The anxiety of being walked around naked while everyone else was dressed was wildly arousing.

The closer we got to the brightly lit glass doors of the hotel, the faster my heart began beating. I could see dozens of people in the ornately decorated lobby talking in small groups. Of course, they were all fully clothed, which made me feel all the more naked. Out of all of the people I could see through the glass doors, I didn’t see anyone even close to my age. That didn’t really surprise me, the hotel looked extremely upscale, and I doubt many college students could afford such a place.

When Karen reached for the door and pulled it open, I felt her squeeze my hand tightly. Looking up into her eyes, I nearly began crying from the surge of emotions washing over me. Karen held the door open for me and had me step into the lobby first. My legs felt like rubber when I took that first step over the threshold. The brightly lit lobby only emphasized my nudity, and my poor four-inch penis was throbbing out of control. I couldn’t stop myself from lowering my chin and looking at my bare feet. When Karen stepped in behind me and let the door close, I began to notice the lobby becoming very quiet. Blushing like crazy and utterly humiliated, I briefly raised my chin and looked at the crowd.

The reaction to seeing me ran through that lobby like a wave. As soon as someone saw me, they froze, stopped chatting, and looked right at me. Some people pointed. Others simply stood there and stared at me. But one person after another, they all wound up looking right at me. Finally, when the room became completely silent, and every eye in the lobby was staring at me, I thought I was going to vomit. I don’t know how long I stood there with Karen standing right behind me with her holding my hands at my sides firmly, but it felt like hours. Chills of shame and embarrassment overtook my body.

Finally, Karen moved to my side, took my hand in hers, and led me directly to a desk under a sign that read ‘Concierge.’ During that short walk, she squeezed my hand very tightly every time I moved to cover my stiff penis. Finally, the crowd seemed to part, making way for us to pass as we approached a very concerned looking man in a suit standing behind the counter.

As we stood near the concierge counter, Karen looked down at me and said, “Sweetheart, I want you to wait right here. Don’t try wandering off again. I need to talk to this nice man for a second, and then we’ll go up to our room. Do you understand?”

I nodded my head and whimpered, “Y-Y-Yes.”

Karen then released my hand and dug it around in her bag. I stood there beside her, feeling alone and afraid. Everyone in the lobby was still staring, and some of them began talking about me. My emotions were so powerful I felt like I may faint.

When Karen pulled out a pen and small tablet, she quickly scribbled down a list of things. She then withdrew two $100 bills from her wallet and slid the bills and the list across the counter to the man.

The man seemed to ignore the money and list. Instead, he cleared his throat while looking at me with disdain and said in a firm-sounding tone, “Madam, this hotel does not permit nudity anywhere on the property other than in the guest rooms.”

Karen only smiled at him and replied, “I will be taking him directly to my room as soon as we discuss my request. Now, as the concierge, are you able to locate the items on this list for me?” The man’s eyes lowered to the list she’d written out. Before he was able to shake his head and refuse her request, Karen slid a third hundred-dollar bill on top of the first two.

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

Karen grinned, 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 she flexed her muscles and stood up taller than usual when Karen got upset. The man behind the counter must’ve been intimidated; I know I would’ve been. But, 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 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 man and sent him to retrieve Karen’s items. Karen smiled at the concierge when that younger man darted out the door 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 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 and small dick. 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 little penis throbbed, and my voice cracked when I squeaked, “Yes.”

She stood up, 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 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. So many people 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 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 small 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. So 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 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 please a woman with your mouth properly.”

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. Instead, throw it all the way open and greet our visitor properly.”

My small penis was oozing its excitement, and my hand trembled as I reached for the knob. Then, 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. Then, 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. Then, 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. I 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 of 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. Then, she 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 my eyes when she reached out and picked up the strap-on. Then, 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 huge 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.” Then, glancing at my armload of things, she reached up and tapped the disposable enema and said, “Let’s start with this.”

She then rose 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.” Then, 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.” At the same time, 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. But, 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. On the contrary, I found it to be a delightful 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. Then, 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. Then, finally, 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. 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. Of course, being as obedient as you are isn’t a bad thing. But, baby, doing as you’re told is a good thing. A very, very good thing that I consider a beautiful 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. Then, 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. Then, in a 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. Then, 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. Then, finally, 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. Then, 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 my body, my tight hole pulled the plug’s base 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 from the couch and spun me around, so we faced each other. Then, 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 ended, she remained close enough to me that her lips brushed against mine when she asked, “How do you feel, Baby Boy?”

I moaned and leaned in to kiss her. But she pulled away and said, “Use your words, Sweetie. Tell me how you feel.”

My voice cracked multiple times while I tried to put my feelings into words. “I feel really sexy. And I feel really, really horny. And I feel really, really, really happy that you saw me on the beach today.”

She grinned and whispered, “Good boy. Aiden, I’m going to fuck your cute little ass with a strap-on. Sweetheart, I’m going to buttfuck you. How do you feel about that?”

After moaning deeply, I caught my breath and whimpered, “I want it. I want it bad. I never thought a woman like you would ever find me attractive.”

Brushing her lips against mine, she asked, “A woman like me?”

Another moan slipped through my lips before I said, “Yes. A tall, strong, smart, older woman. A beautiful woman.”

She kissed my lips gently and said, “You’re so sweet.” Then, reaching around behind me, she slipped at least one finger between my cheeks and pressed against the base of the plug. Chills shot through my body, and a moan left my lips. “Aiden, what would you like to do now?”

Humiliation burned inside of me when I opened my mouth and said, “I want you to buttfuck me.”

Licking my upper lip with her tongue, she whispered, “Ask me to buttfuck you.”

Moaning into her mouth, I whimpered, “Karen, would you please buttfuck me?” Humiliation burned through my body when I went on to say, “Pretty please?”

After biting my lower lip, she whispered, “Sweetheart, I would be happy to buttfuck you.” She pressed against the base of the buttplug with her fingers, which made me thrust my hips forward. Then, with her lips dragging against mine, she whispered, “Be a good boy and help me put my cock on.”

Whimpering softly, I turned from her embrace and approached the table where her strap-on sat. I stood there for a moment, looking down at the long phallus with its sturdy canvas harness. The idea of that long dildo sliding deep inside my bottom made me rise on my tiptoes as goosebumps formed all over my body.

Reaching down, I picked up the strap-on by its harness. Then, biting my lip, I turned back toward Karen. She stood there regally, watching my every move. “Put it on for me, Sweetie.”

She reached behind her back, and I heard the sound of a zipper. I stood there completely stunned when her white skirt fell around her ankles. She stepped out of her skirt toward me while never looking away from my eyes. She stood there wearing her flowery print top, shiny white satin panties, and white netted beach shoes.

My eyes dropped to her panties when she pointed to that general area. Then, in a sultry whisper, she said, “Look how wet my panties are. You have my pussy gushing with excitement.”

Naked, smooth with an extremely stiff little penis, I whimpered, “I did that?”

She grinned, “Yes, you did, Baby Boy. Doing everything I’ve told you since we met on the beach, without complaint, has made me very horny.” She paused until I looked back into her eyes. “Now, Sweetheart, put my cock on so I can fuck you properly.”

Shivering with excitement and shame, I knelt at her feet and opened the harness for her to step into. When both of her feet were in place, I began to pull the dildo up her legs slowly and over her panties. Without ever touching the dildo itself, I adjusted the harness until it fit snugly around her waist and left the phallus protruding from her pubic mound.

Her chest was heaving, and her face was flushed. Then, looking down at me, kneeling at her feet, she said, “Take it in your hands and give it a kiss, Aiden.”

Everything I’d been through since I’d met Karen had proven to be incredibly arousing. But being told to kiss the dildo that would soon be buried in my bottom took my arousal to a whole new level. The muscles in Karen’s legs flexed when I reached up and took the long dildo in my hands. Glancing up at her, I saw she was smiling down at me and slowly nodding her head. Leaning in more, I puckered my lips and placed a quick kiss on the tip of the phallus.

Karen ran her fingers through my hair and said, “That wasn’t much of a kiss.”

Biting my lip, I looked from her eyes to the dildo. Then, finally, I knew what she wanted me to do. She wanted me to give her a blowjob. It sounds ridiculous, but in my mind, there was a big difference between being butt fucked and giving a blowjob. I believed if I took that dildo in my mouth, I would never be the same again. I would somehow change as a person. But my rigid penis and desperation eventually convinced me it would be okay if I did what I’d been told.

Leaning back in, I placed another kiss on the tip of the dildo. Then, looking up into her eyes, I parted my lips and took the dildo into my mouth. I slid up and down on the shaft a few times before I heard Karen moan. Her fingers were sliding through my hair, pulling me toward her, urging me to take more of it in my mouth. I began bobbing up and down on the dildo, taking as much of it in my mouth as I could without gagging. The musky scent of her arousal caressed my senses, and it was perfectly apparent that Karen was enjoying herself.

After letting me suck on her dildo for a time, she moaned, “Aiden, you are absolutely precious. Sweetheart, are you ready for me to pop your cherry?”

As I slid off her dildo, a string of my saliva was left connecting my lower lip to her dildo. Looking up into her eyes, I whimpered, “Yes, please!”

She offered me her hands, and I took them as I stood up. Then, reaching down, she picked up the lubricant and began guiding me across the room toward the door leading onto the balcony. After sliding the door wide open, she had me step outside first. By this point, I was way beyond caring if we were outdoors or not. I was so horny. I wouldn’t have minded if she guided me into the hotel’s hallway to fuck me!

The balcony was equipped with a small table and a pair of chairs. Beside them, directly outside of the door, there was plenty of room to stand and look over the guardrail. Across the street were three hotels. There were dozens of rooms in those hotels that could have a perfect view of Karen and me being lit from behind by the light from our room.

Karen had me stand at the guardrail, bend at the hips, and look at the street below and the nearby hotels. She suggested I think about all the people who could potentially witness what we were about to do. There were so many windows across the street, many of them had lights on. We were too far up, the twelfth floor, to worry about being seen from the street. But looking through the bars of the guardrail down at all those people milling about on the street was surreal when considering what was about to occur.

She pulled a chair up behind me and, without saying a word, began to pull the plug out from inside of me slowly. I squirmed and rolled my hips up when the widest part of the plug stretched me open. After my muscles pushed the plug out beyond that widest part, Karen applied enough pressure to push it back inside. She did that several times before letting the plug slide all the way out. This left me feeling empty and needing her attention. I turned to watch her set the plug down on the table beside her. Picking up the lubricant, she took her time and slathered the dildo down with ample amounts to ensure the loss of my virginity would be a painless experience. With that completed, she squirted some onto her finger and applied it to my quivering and anxious hole.

Standing behind me, Karen took hold of my hip with one hand. With the other, she aimed the dildo at my trembling hole. Then, after bumping the rounded tip against me, she asked, “Aiden, Sweetie, tell me what you want.”

I didn’t look back at her. Instead, I stared at the buildings across the street. My eyes raced from window to window, balcony to balcony, looking for a sign of anyone looking in our direction. I didn’t see a single soul. The warm breeze blowing over the naked and hairless skin felt magical. Rolling my hips up while arching my back deeply, I moaned, “I-I-I want you to take my virginity. I want you to make love to me. I want to spend the whole weekend with you. I-I-I want…”

Karen pressed forward with her hips, and my wrinkled hole began to stretch over the smooth, rubbery dildo. I arched my back as deeply as I could to provide her with the best angle. When I’d stretched over the widest part of the dildo, I felt Karen take hold of my other hip. She began to slip a little bit in, and then it slips back out. She would then slip a little more in and let that slip out. She worked slowly and methodically. There was no pain at all. I wouldn’t even consider it discomfort. Being impaled on her dildo made me feel like I was the star of a very naughty fairy tale.

The more of the dildo that disappeared inside of my body, the more intense the feelings became. I was being penetrated by a strap-on dildo being worn by a woman straight out of my naughtiest fantasies! Finally, leaning against my back, she moaned into my ear, “That’s about half of it. How do you feel, Sweetie?”

I whimpered while my body shivered with desire. My penis was tough and oozing its excitement. “I feel wonderful!”

While still leaning against my back, she slowly slid the rest of the dildo into my body. When I felt her hips meet my butt cheeks. I squealed at the top of my lungs, “I LOVE YOU, KAREN!!!”

She began to saw the dildo in and out of my body in time to the beating of my heart. Then, after nipping my earlobe with her teeth, she moaned, “Oh baby, I’m falling in love with you too.”

Her thrusts forced me to stand up straighter. She had me pinned between her and that rail. My drooling penis poked out between the bars while she thrust her dildo in and out of my bottom. She wasn’t rough at all. Instead, she was very gentle and aware of my reactions to her lovemaking. At one point, after burying the dildo deep inside of me, she asked, “Are you okay? Do you want me to add more lubricant?”

Arching my back, looking over my shoulder into her eyes, I moaned, “No! Don’t stop! Please! Don’t stop!”

I gripped the railing tightly with both hands. Karen kept a firm hold on my hips while thrusting the dildo in and out of my innocent body. I was covered with a thin layer of perspiration, and I was breathing heavily. I hadn’t even touched my penis, and I felt the orgasm building inside of me like a lit stick of dynamite. Finally, I chirped, “Karen!!”

She never broke her stride and kept thrusting her hips against my bottom at a quick pace. She was also breathing heavily and had a teasing tone to her voice when she asked, “Yes? Is something wrong, Aiden?”

I chirped, “Karen!! I’m going to… It’s going to…”

She growled, “You’re going to cum for me!”

I chirped, “YES!!”

At the same moment I crested in orgasm, Karen moaned, “Let it happen, Baby. Cum for me. It’s okay, I’ve got you.”

My eyes opened wide, and I imagined people standing in every window across the street watching me cum. My toes curled into knots. I gripped the handrail with white knuckles. My eyes popped open wide, and I squealed in a very high pitch. My little balls retracted into my body while my penis flexed hard and a long string of my creamy love shot away from where I stood and fell to the street below.

Karen slowed down the pace of her thrusts but increased the force of them. The sound of her hips slapping against my pale, smooth bottom echoed in the alcove that was the balcony. She licked my neck and bit into the skin. My penis flexed against me, and more of my creamy love erupted out from inside of me, falling to the street. My penis drizzled out several more drips before Karen, and I knew my orgasm had come to an end.

Leaning against me, trapping me between her and the railing, she whispered in my ear, “You are amazing.” She remained standing behind me with the dildo still buried in my bottom, holding me in her arms. She whispered things in my ear like, “You were absolutely perfect, Sweetie.”, and “I may take you home with me when this weekend is over.” I couldn’t stop myself from giggling when she asked, “Do you think your cum landed on anyone down there?”

When she was ready, she slowly slipped the dildo out from inside me and stepped back into the room. So I was left standing on the balcony, hairless, naked, freshly fucked, and head-over-heels in love with a woman who could have been old enough to be my mother.

I stood there on the balcony enjoying the feelings and emotions racing through my body. When I finally turned around, I saw Karen was still wearing her shirt but had removed the strap-on and was stepping out of her panties. While sitting down on the couch and spreading her legs wide, she grinned and said, “Get in here, young man. It’s my turn now!”

Dashing into our room, I dropped to my knees between her spread thighs. My penis was still perfectly stiff. I didn’t soften in the least after I’d squirted off the balcony. But I knew she wanted my mouth on her sex, not my penis in there. Never in a million years would I have ever tried to penetrate her without her telling me to.

Before I even got close to her, her womanly scent caressed my senses once again. I paused to admire her for a short time. I’d never seen a real-life pussy until that moment. Her short, neatly trimmed, dark brown, triangular patch of pubic hair pointed down toward her engorged and peeled open lips. The nub of her clit was peeking out from under its hood, and her juices were dripping down between her cheeks. Karen’s pussy was just as beautiful as she was.

Having seen ample amounts of pornography, I had a pretty good idea of what I needed to do. Leaning in, I started slowly by kissing and licking my way up the inside of her thigh toward her wonderland. As I got close, I could feel the humid warmth of her arousal. Licking along the outside of one lip, I wound up at her clit and placed a gentle kiss right on it.

Karen groaned, “Stop fucking teasing me, Aiden! I need to cum!” She then knotted her fingers in my hair and pulled my face in close against her sex. I began licking, kissing, and sucking on everything near my lips. She ground my face up and down along her pussy. She held me firmly in place with my nose rubbing against her clit and my tongue dipping into her sex. Karen moaned and pushed herself up against my face. I thought I must be doing something right, so I pushed my tongue as far into her as I could while grinding my nose against her stiff nub.

The noises Karen began to make couldn’t be defined as a moan or a groan. It was a more animalistic sound. It was primal. And when the noises she made became louder, I saw the muscles in her abdomen, chest, shoulders, and arms flex hard. Her thighs clamped down against my head, and she never let go of my hair with her hands. Her pussy began to vibrate and quiver beneath my tongue and lips. I was sure she was going to cum.

With renewed vigor, I licked and lapped at her pussy while grinding my nose against her clit. When her orgasm hit, she knotted her hands even tighter in my hair and pulled on it hard. Her thighs felt like they could’ve crushed my skull. And her stiff little clit seemed to throb against my nose. Her mouth was open, and I was sure she was making some sort of noise. But with my head trapped between her thighs, I couldn’t hear a thing.

Karen eventually pushed me away from her quivering pussy. I didn’t realize it at the time, but I was a little aggressive with her clit after she’d just cum so hard. I learned that evening that girls get just as sensitive as boys after they cum.

Sitting back on my feet, my face was glistening with her juices, her flavor filled my mouth, and my stiff, hairless penis was pointing at the ceiling. I watched Karen slowly recover from her orgasm. We stared into each other’s eyes the entire time.

While still sitting between her spread thighs, she whispered, “I meant it when I said I was falling in love with you.”

Biting my lip, I smiled happily and squeaked, “You don’t know how happy that makes me! Because I’ve already fallen in love with you!”

The End.


*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.

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