Spring Break

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." 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. 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 up on my tiptoes as goosebumps formed all over my body.

Reaching down, I picked up the strap-on by its harness. 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. 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 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 slowly pull the dildo up her legs 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. 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. I knew what she wanted me to do. She wanted me to give her a blowjob. It sounds completely silly, but in my mind, there was a big difference between being buttfucked 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 of 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. 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 who could have a perfect view of Karen and I 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 slowly pull the plug out from inside of me. 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. After bumping the rounded tip against me, she asked, "Aiden, Sweetie, tell me what you want."

I didn't look back at her. 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! 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 perfectly hard and oozing its excitement. "I feel wonderful!"

While still leaning against my back, she began to slowly slide 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. 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 being rough at all. 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. 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 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 of me and stepped back into the room. 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 too.

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-live 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 being 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!"