Kissing Booth

My sister’s sorority always put up a kissing booth during the homecoming fair. She asked me to help out by keeping track of the money they raised. She was a junior at the time and I was a freshman, but I’ve always been good with numbers. Math just makes sense to me. And at five dollars a kiss, the math was made even easier.

Throughout the day, the sorority girls would take turns at the booth. None of them were there for very long, maybe an hour at the most. It was a treat to watch the pretty girls come and go all day. My job was to collect the money, keep track of the total, and determine which girl raised the most money.

It was getting late when I heard a mature female voice ask, “Is that little cutie on the menu? I’ll pay double to kiss him!”

As I looked up from my laptop, I saw a full-figured lady staring right at me. She looked to be older than my mother. She had a chubby face with a bright, toothy smile. Her short, golden blond hair was thick well above her shoulders. Her enormous breasts were captured under a loose-fitting sweatshirt with my school’s logo on the front. And she was wagging her finger in my direction.

Two of the sorority girls moved behind me and propelled me toward the counter. They told the woman that I was most definitely on the menu. The woman handed one of the girls a ten-dollar bill and leaned over the counter to get a hold of me. She grasped one of my hands and looped her other behind my neck. She pulled me toward her and soon my lips met hers. She forced her tongue into my mouth and I couldn’t stop myself from moaning softly.

Until that moment I’d never been kissed. I was a nineteen-year-old virgin who had never even held a girl’s hand. I had always been shy and insecure. And I completely lacked the courage necessary to ask a girl out on a date.

And now this older woman was not only kissing me, she was sucking on my tongue, licking my teeth, and nibbling on my lips. I was leaning against the counter and had no idea what I should do with my hands. After a time, I remembered watching the girls loop their arms around the boy’s necks that were kissing them. So I did the same thing, I leaned further over the counter and looped my arms around the woman’s neck.

When she felt my arms around her neck, her eyes opened and our lips popped apart, but she still held me, so I kept my arms around her neck. Looking right into my eyes with her lips brushing against mine, she whispered, “That’s my good boy.” She then glanced down while slapping another ten-dollar bill on the table.

She pulled me back to her and kissed me once again. Our tongues were sliding against each other. I was breathing heavily and my poor penis had never been stiffer. I tried to be sly as I slowly ground myself against the edge of the counter. When that kiss ended, I was left gasping for air and I know I was blushing from head to toe.

She grinned at me while fishing another bill from her pocket. “Come around to this side of the counter, Baby Boy.” And she then slapped a twenty-dollar bill on the counter.

The sorority girls were cheering me on. They helped me to climb over the counter until I sat on its edge with the woman standing between my wide-spread knees. She wrapped her arms around me that time and smushed me against her soft body while sliding her tongue deep into my mouth. My back arched and I moaned into her mouth while she kissed me how I’d always dreamed of kissing a girl someday.

While holding me firmly against her large, soft body, she let one of her hands slip between us. That hand slowly made its way between my spread legs until she gently cupped the bulge of my over-excited penis in the palm of her hand. My eyes popped open but slowly drifted closed while she continued to kiss me and gently fondle my penis. The kiss eventually came to an end and as our lips smacked apart, she asked in a soft voice, “What’s your name, Baby Boy?”

When I failed to answer because I was still trying to catch my breath, one of the sorority girls leaned in close and answered for me. “His name is Sam.”

She smiled, kissed my lips gently, and said, “It’s nice to meet you, Sammy. I’m Donna.”

Donna then looked to the sorority girl who was still lingering nearby. “Excuse me, does Sammy need to stay here?”

The girl looked around for a second and then said, “No, I think we can handle it for the rest of the day.”

Donna looked at me in my horny, inexperienced frenzy and asked, “Sammy, Sweetheart, would you like to come with me?”

I bit my lower lip, leaned in close to her, and asked, “Where are you going to take me?”

She nipped my earlobe with her teeth and asked, “Does it matter?” She then squeezed my desperate erection over my shorts.

Shaking my head from side to side, I slowly slid off the counter until I stood just in front of Donna. She was taller than I thought, a full head taller than me. Reaching out, she took my hand in hers. And before we walked away, she said, “Sammy, don’t you want to say goodbye to your friends?”

Looking back over my shoulder, I saw my sister had recently arrived and was grinning from ear-to-ear, as were the two other girls who were standing nearby. My voice cracked when I spoke. It might have been because Donna had rested her hand on my butt and at least one of her fingers was wiggling its way to parts unknown by anyone! “Bye!”

I spun around while Donna dug her fingers in deeper between my cheeks. I heard my sister call out from behind us, “Bye Sam!! Have fun!!”

Donna guided me through the crowd with her hand on my butt the entire time. As the crowd thinned and we entered the parking lot, she began to squeeze my butt with every step I took. When she backed me against the rear hatch of her SUV, I whimpered softly and asked, “Donna, where are we going?”

She leaned in a kissed me aggressively while slipping her hand back between my legs to fondle my desperate penis. When her tongue left my mouth, she sucked my lower lip into her mouth before releasing it and saying, “I’m taking you home with me. Sammy, I’m going to make you feel so good!!”

For the first time, I mustered all my courage, rose on my tip-toes, and kissed her after slipping my arms around her neck. While we kissed, she wiggled her thick, meaty thigh between my legs and I began grinding myself against her. I was left gasping for air and humping myself against her soft, warm thigh when our kiss came to an end.

Donna leaned forward and teased my earlobe with her lips while she whispered, “Sammy, I’m not the type of woman who usually brings young men home with her. You’ll be my first.”

I arched my back while shamelessly humping myself against her, “Donna, I’ve never, um, you know. I mean, I’ve never been with a girl before.” Turning my head to face her, I whispered, “You were my first real kiss.”

She licked my lips and whispered, “I know. I knew it the moment I saw you. That’s why I paid to kiss you.”

I whimpered softly, “Really?”

She licked my lips and said, “Yes. The moment I saw you, I knew I had to take you home. You looked so innocent and sweet behind your little computer. Sammy, I loved a boy just like you when I was your age. But he slipped away before I could show him what I had to offer. Sweetheart, I’m going to do to you, what I so badly wanted to do to him all those years ago.”

Taking my hands in hers, she guided me a few steps away from her SUV. After tapping on the keyfob, the large rear hatch began to open. While standing out in the open, right there in the parking lot, Donna reached for the bottom of my shirt. She whispered while slowly raising the bottom of my shirt higher and higher, “Sammy, before we get going, I need to undress you.”

Biting my lip while my hips squirmed and ground around shamelessly. I looked around nervously, “Right here? Can’t we wait until we get to your house? Please?”

She kissed me gently once again before saying in a soft voice, “I’m so sorry Sammy. But no, we can’t wait. These clothes need to come off right now.”

My arms rose all on their own while Donna pulled my t-shirt up and off. With her hands on my hips, she guided me toward her car and I soon found myself laying down in the back of her SUV. I couldn’t stop myself from squeezing my very stiff penis with both hands while writhing in anticipation. Donna stared into my eyes while I lay before her with a hunger in her eyes. She took one of my feet in her hands and removed that shoe and sock. She repeated the act with my other foot.

Donna kissed the tip of my big toe and whispered, “Move your hands away from yourself.”

When I hesitated, she whispered, “Sammy, am I going to have to spank you when we get home?”

My back arched and I moaned, “No.” I reluctantly moved my hands well out of the way. Raising my head just a little, I saw two couples standing not far behind Donna. I whimpered softly, “Donna, not here. There are people behind you. Please? Pretty please?”

She leaned in close and kissed my stomach while undoing the button on my shorts. She kissed my stomach again and again while she slowly lowered the zipper. Hooking her fingers under my shorts and underpants near either hip, she looked into my eyes and whispered, “Lift.” Biting my lip, I set my bare feet on the bumper and lifted my hips.

Donna slowly raised my underpants high enough to clear my skinny penis. While sliding both my underpants and shorts down my thighs, she stared at my stiff, little erection with its dusting of light brown hair and said, “Oh Baby Boy, you are adorable!”

Lowering my hips and lifting my feet, Donna then removed the last shred of clothing from my body. After tossing my clothes toward the front of her SUV, Donna laid her warm, soft hands on my knees and spread them wide apart. She stared into my eyes while leaning down slowly. I watched as her lips slowly parted and while still staring at me, she took my entire penis and its little pouch of marbles into her mouth.

My eyes rolled up into my head and my back arched deeply. Donna gently pressed her teeth against the very root of my delicate masculinity. My fingers clawed at the floor of her SUV while her teeth nibbled, her tongue caressed, and her lips kissed my little penis. With my legs spread as wide as they would go, Donna held all of my important bits in her mouth, and her teeth began biting down a little harder. The realization that this woman I’d just met could easily bite off my penis struck me hard and I nearly squirted in her mouth. But she must’ve felt how close I was. She quickly removed her mouth from my body.

I heard the people behind Donna chattering to each other, but I couldn’t understand what anyone was saying. I didn’t dare peek at them again, it sounded like Donna and I had attracted even more of an audience.

While hooking her hands behind my knees, Donna grinned and said, “Baby Boy, this is just a sample of what I’m going to do to you. I’m going to ruin you for every girl your age. You’re going to want to stay with me forever.” And she then did something I never imagined I would experience. She folded my legs back on top of my chest and held them firmly in place. Leaning back down, she poked out her tongue and licked my wrinkled hole! She licked it several times before poking at it with her tongue. She then licked from that special hole up to the tip of my penis. Parting her lips, she took all of my penis and its little pouch back in her mouth once again. This time she bit down on its root even harder than before.

I was squealing in a high-pitch and thrashing about as much as I could, she was holding me in place with enough force to keep me from squirming away. When her mouth slid off of my desperate erection, it was left dripping with her saliva and the impression of her teeth were left circling its root. Reaching down, she gently patted my penis and pouch with her open palm. “Climb into the front seat.”

Sitting up, I immediately learned our audience had grown. At least a dozen people were standing not far behind Donna. They were loosely gathered and I nibbled on my lip while noticing many of them looked rather excited. Most of them had their phones raised and were taking pictures of me in my current predicament. I know I was blushing like crazy. I was naked in a parking lot in front of a large group of strangers! Not only that, they had all seen Donna, a mature, full-figured woman take my whole penis in her mouth and she licked between my cheeks too!!

Rolling onto my hands and knees, I was about to climb over the second row of seats when Donna poked her finger between my cheeks and against my wrinkled hole! I squeaked and giggled before turning around to watch her close the hatch behind me. Completely naked behind lightly tinted windows, I scurried over the rows of seats until my bare bottom was perched on the soft, leather of the passenger’s seat.

While I waited for Donna to join me, I realized I was naked in her car! I had just been stripped naked in a parking lot by a woman I’d met less than an hour before. She had told me she was going to take me home with her. She was going to do to me what she wanted to do to another boy long ago. If the things she’d already done to me were any indication of what she had planned, I couldn’t wait to get going!

She was my very first kiss. Donna seemed like such a kind woman. But she did threaten to spank me. A shiver shot up my spine as I imagined laying across her lap while she spanked my bare bottom. She had also bit down on the base of my penis hard enough to leave teeth marks. Another, even stronger shiver shot up my spine while I imagined Donna closing her mouth on my boyhood. My penis throbbed hard and I struggled not to reach down and touch it.

When Donna opened her door and saw me sitting there so very horny, she smiled and climbed onto the driver’s seat without ever taking her eyes off of me. Leaning over me to grab my seatbelt, she pressed her enormous breast against my face. When she heard me moan softly while inhaling her musky scent, she moved even closer to me so my face settled into her warm, perfumed cleavage. She left me gasping for air and even hornier than I was before when she settled back into the driver’s seat.

She grinned at me sitting naked beside her with my very stiff penis and flushed face. She started her SUV and as she put it in gear, I glanced around and saw the crowd had moved toward the front of her car so they could try and see what we were up to. Donna backed her car out of its space and waited for our group of voyeurs to part so she could drive us home. Donna rolled the front two windows down so they could get one last look at me. The group moved slowly and remained close to the sides of her SUV as we drove past. Phones were raised and I’m sure dozens of pictures and videos of us were shot that day.

I was wiggling, squirming mess of horniness as she left the parking lot and joined the traffic on the main loop around my University. She rested her hand on my naked thigh while we meandered around my school. She glanced away from the road to my naked body quite often. She spoke to me while I tried not to squirm under her warm, soft touch.

“Sammy, I earlier mentioned a boy from my past. I’m amazed at how much you two are alike. It could be the way I remember him, but Sweetie, you are a dead-ringer.” She paused for a short time and I’m sure she was thinking about the boy she used to know. “He was your age when I knew him. He used to come to my dorm room so we could study together. He was such a cutie, I had a hard time keeping my hands off of him!”

Unclicking my seatbelt, I turned my body so I leaned against the door so I would face her. When she stopped at an intersection, her eyes wandered over every exposed inch of my body. I warmed under her gaze and nearly moaned when her eyes met mine.

When we started moving again, she continued with her memory, “It was a different time, it was more than three decades ago. Young ladies were simply not that forward with boys.” She sighed before saying, “But it got to a point that I could no longer resist him. We’d finished studying for the final in our Chemistry course. He had gathered up his books and things and I was walking him to my door.”

She grinned to herself at the memory, “He reached for the doorknob, but I spun him around before he could turn it. I backed him against that door and kissed him. I was his first kiss too.”

Lowering my hands to the insides of my thighs, dangerously close to my throbbing and leaking penis, I nibbled on my lip while listening to her story. My voice sounded squeaky, “Did-did-did you undress him too?”

She glanced away from the road to my extremely horny body, “I would have, but…” She looked a little sad, “I frightened him. He was so small and I wasn’t exactly petite. The poor boy had never been kissed before and I’d nearly attacked him. He slipped out of my grasp and dashed out the door before I could catch him.” She paused while considering what she’d say next, “The last time I saw him was during that Chemistry final. He never returned to school after that semester.”

I continued to squirm in my seat and struggled to keep my hands off of myself. While slowing down to turn onto a residential street, she glanced at me and said, “Sammy, I’ve had thirty years to fantasize about all the things I would have done to that boy if given the chance. I would have treated him like my special little prince! I’ll never have the chance to show him how good I could have made him feel. But now, with you, I have a very similar opportunity that I am not going to let slip away.”

She had been thinking about that encounter for ten more years than I’d been alive! She had been crystal clear when she said, she was going to do to me what she should have done to him so long ago. My entire body quivered and shivered in excitement. She had already stripped me naked in a parking lot, taken my penis in her mouth, and licked my wrinkled hole. Strangers had watched while she took my entire penis and my pouch of marbles in her mouth and bit down hard enough to leave marks around its base. Glancing down, I saw her bite mark had faded away. But the memory of her teeth bearing down on my penis remained.

My voice was soft and a little squeaky when I asked, “Donna, are we almost to your house?”

She glanced at me and smiled, “Yes we are, Sweetheart. We’ll be home very soon.”

She reached over between my legs and with two fingers, bounced my delicate testicles up and down. “Sammy, when I’m through with you, these little balls will be wilted up like raisins. I’m going to drain every last drop of love out of you.” She continued to bounce them up and down while asking, “Baby Boy, I’m going to make you squirt more times than you believe possible. I’m going to take such good care of you.”

Her words left me dripping with desire. I was so caught up in what she was saying that I didn’t realize we’d pulled into her garage until she’d turned the engine off. While the door closed behind us, Donna announced, “We’re home, Sweetheart. Let’s get you inside so I can relieve the pressure in your little jewels.”

Donna got out of her SUV and I watched her every move while she walked around the front of it. She stared at me while I stared at her. When she opened my door, I swiveled my legs out toward her. She took hold of my legs and lifted them so she could kiss both of my big toes. Without a word, she reached in and scooped my naked body into her arms as if I didn’t weigh a thing. I looped my arms around her neck and rested my head against her shoulder. She carried me across the garage and balanced me on her knee while opening the door leading to her kitchen.

She passed through her kitchen and went straight to her dining room. The long rectangular table was surrounded by ten chairs. The only things on the huge table were fabric placemats in front of each chair. She set me down on one of the placemats at one end of the table. After she sat down on the chair between my legs, she wasted no time and pulled me closer to her while I perched on the placemat. She kept a firm grip on my hip bones to keep me from squirming away. Lowering her head, she pursed her lips and as my penis made its way into her mouth, she nibbled on it with her teeth. A few different times during the process, she bit down harder. And when she’d taken my entire penis in her mouth, she bit down and dragged her teeth up its entire length. She nearly had to scrape me off the ceiling. The feeling of her lips, tongue, and teeth on my erection was so intense!

Taking just the squishy pink head of my penis in her mouth, she bit down around its neck. She bit down harder and harder until I tried to push her away while squeaking her name, over and over, “Owie!! Donna! Donna! Donna!!”

When she’d relaxed her jaw and her lips had slipped off my penis, proof of what she’d done remained in the form of teeth marks just under the neck of my skinny penis. I whimpered softly, “You bit me again.”

She licked her lips and bounced my little balls on her fingers. “Yes, I did. And I’m not going to stop anytime soon.” She glanced down at my erection glistening with her saliva. “I have always thought boys like you would enjoy both pain and pleasure. In my opinion, Sweetie-pies like you shouldn’t have one without the other.”

Licking my lower lip, I considered what she just said. For every pleasure, there was an equal pain. The pain of her teeth on my penis was different. It didn’t hurt like getting punched or slapped. It was like a teasing, aching sort of pain. Deep down inside, I found Donna’s idea of pain to be oddly arousing. Never would I have imagined I’d enjoy the feeling of teeth on my delicate penis, but Donna showed me how erotic a little pain could be.

She must’ve known the battle going on inside my head. She sat there patiently, blowing her warm breath on my rigid, virginal penis. She leaned in and planted a gentle kiss on the head of my penis and whispered, “My little prince, do you want me to bite you again?”

My back arched and I whimpered softly, “Yes.”

She kissed my penis again and said, “Yes, what? Ask me, Sammy. Use your words.”

My voice cracked and changed octaves several times while I asked, “Donna, will you please bite my penis again?”

She grinned up at me, “I’ll do even better than that!” She had me lay flat on my back, and after having me rest my legs over her shoulders, she slurped both of my balls into her mouth. I was shivering on the tabletop and unintentionally pushed many of the other placemats onto the floor while I reached for the table’s edges.

Donna moaned softly while sliding her soft, slippery tongue along the underside of my little orbs. She closed her jaw slowly. I felt her teeth close down on the tender flesh of my pouch. Rolling my little balls around on her tongue while biting down on the soft pouch that held them was unlike anything I’d ever felt before. She could have bitten down a little harder and turned me into a eunuch! She didn’t, but she could have. And that fact was not lost on me. My very stiff prong of a penis was standing straight up and drooling its excitement like a faucet. My knuckles were white while I gripped the edges of the table and my legs were looped around Donna’s neck tightly.

“Donna! Donna! Donna!” I chanted her name over and over and over. She started to nip down with her teeth even harder, she was testing the sponginess of my flesh. At the same time, she began to press my balls against the roof of her mouth with her tongue. I whimpered softly. The harder she pressed against them, the sharper those lightning bolts of pain became. The feelings and emotions were so intense, I wasn’t sure if I should scream or moan.

Donna sealed her lips around my pouch and sucked on my little balls. At the same time, she backed her teeth away from my flesh. The vacuum she’d created was a very nice feeling at first. But she began to suck harder and harder while backing away from my body. She was stretching the soft flesh of my pouch and with it, my little balls too. When the first ball slipped from her lips, it popped back against my body and I whined while lightning bolts of intense pain shot throughout my body. The experience was repeated with my other ball popped out of my lips.

My penis had never been so stiff. It was throbbing so hard it ached. My back was arched on the table and my legs still circled Donna’s neck. I was naked in a home I’d never been to before with a lady I’d met a little more than an hour before. Donna was a full-figured woman who was older than my mother. She had stripped me naked in a parking lot and was now showing me how pleasurable pain could be.

Her lips were dragging along the tender flesh of my penis. Her warm, moist breath was tickling that same sensitive skin. In a deep, raspy voice, she asked, “Baby boy, are you ready to cum? Do you want me to make you squirt for the first of many times tonight? Tell me what you want, my special little prince.”

Squirming on the table, I arched my back and moaned, “Please make me cum! Please, Donna! I want to so bad!!”

She wiggled my legs off of her shoulders and had me spread them wide apart. After looping her first finger and thumb around my stiff, throbbing prong, she began to slowly stroke up and down along its petite length. She turned her head to the side, leaned in close, and bit into the place behind my little pouch, but before my wrinkled hole. As her teeth sunk into that tender skin, I lost all control and my orgasm erupted from deep inside of me. My toes curled into knots and my fists clenched the edges of the table with all the strength I had. My head rolled backward and my vision blurred.

A long line of my creamy love spewed from inside of me and shot up into the air. It seemed to linger there before falling onto my goosebump-covered stomach. Donna bit down harder and nipped that tender flesh between her teeth. I squealed both in pain and pleasure as the next surge of my cream shot up only to fall, further adding to the spermy mess on my stomach. As the third explosion built inside of me, Donna quickly moved upward and bit down around the neck of my penis. She bit hard enough to stop my penis from ejaculating anymore.

Raising my head, I looked down at her. She smiled at me with the head of my penis captured between her teeth. She winked at me before biting down even harder. I groaned and rolled my hips down while arching my back deeply. Releasing the pressure with her jaw, she then sucked extremely hard and I felt all of the juices that had been trapped in my petite length, being sucked out into her mouth. She was treating my penis as if it were a straw. She sucked harder and harder. And when she did relax and her lips finally popped off my still rigid penis, I gasped when I saw the usually soft-pink-colored head was a deep-dark purple color due to the hickie she’d given me.

After licking her lips, she smiled at me and said, “Sweetheart, I’ve been dreaming about doing that to a gentle boy for a very long time. By the time I take you back to your dorm, you’re going to be covered in bite marks and completely drained of all your creamy love.” She paused to place a kiss on the bruised head of my penis. “That is if you want me to take you back to your dorm. Baby Boy, I’m hoping you’ll want to stay with me forever. Or at the very least, come and visit me regularly.”

She turned her face toward my spread thigh and maintained eye contact with me while nibbling and nipping at the tender flesh along the inside of my thigh. She worked her way slowly from my knee toward my still throbbing penis. Sucking one of my little balls into her mouth, she pulled it deep into her mouth before letting it pop out free from her lips. She then repeated the process with its twin.

I was gasping for each breath and clawing at the tabletop before she began nibbling and biting her way up my other thigh. She seemed to bite into my flesh harder with each nibble she took. I guessed she was judging just how much pain I could tolerate. And when she figured it out, she consistently began biting into my thigh with the same pressure, enough to make me flinch and gasp, but not enough to make me completely recoil from her.

She pushed my thighs together and back onto my chest before she began biting in zig-zag lines up the backs of my thighs. I whimpered softly as she drew even closer to the underside of my pouch. But that time, she ignored it and went to work on my cheeks. She didn’t nibble and nip at them, Instead, she turned her head, and with her chin between my cheeks, she took big bites across my cheeks. When she’d finished with the first, she turned her head and repeated the process on the other.

Rising from between my legs, she looked at my face nearly hidden between my legs. She smiled and said, “Hold your legs right where they are.”

My hands were sweaty and shaking when I hooked them behind my knees and pulled my legs against my chest. I watched as Donna slipped a finger into her mouth. When it came out, it was covered in saliva. Lowering it away from my point of view, she asked in a soft voice, “Baby Boy, how do you feel about penetration?” She then bumped her finger against my tight, wrinkled hole.

I squeaked, “I don’t know. I’ve never…”

That was when she applied just enough pressure for my little hole to squeeze open and allow the tip of her finger to enter my body. My eyes rolled up into my head, my back arched deeply, and I moaned like never before while still clinging to my legs.

With her other hand, she reached between my legs and pulled my rigid penis upward so it pointed toward the ceiling. She leaned forward and took my penis back in her mouth. She slid up and down along its petite length several times before letting it slip from her lips. Having just orgasmed so recently, my poor penis was sensitive and the contact of her soft, wet mouth was like being shocked with electricity. I squealed and squirmed as she fingered my bottom and teased my still very stiff penis.

Looking around my legs, right into my eyes, she asked again, “My little prince, how do you feel about penetration?” She then pushed more of her finger inside of me.

My back arched and I clung to my legs, pulling them tightly against my chest. A high-pitched moan from deep inside my body slipped through my lips and I felt my penis throb hard.

When even more of her finger slid inside of me, she whispered, “Sweetheart, how do you feel about penetration?”

I whimpered softly, “It feels so good!”

She smiled while fingering my virginal bottom on her dining room table. “Baby Boy, you’re like a dream come true. You and I are going to have so much fun together. I’m going to hurt you so good! I’m going to spank your skinny little behind. I’m going to make you squirt until your little marbles run dry. And I’m going to penetrate you with my strap-on. You’re going to squeal out in pleasure while I pop your cherry.”

My mind was racing. So much had occurred in such a short time. Her promises of what lay ahead were straight out of my deepest, darkest masturbatory fantasies. The fantasies I never would have shared with anyone. The private thoughts that always made me squirt the hardest while playing with myself. Donna was introducing me to new things that were proving to be far kinkier and arousing than I ever would have imagined.

While slowly sliding her finger in and out of my tight little hole, she leaned down and sucked my tingling penis back into her mouth. I lay there on my back, pulling my knees tightly against my chest while Donna drove me wild with both her finger and mouth. Very suddenly, with her free hand, Donna began pinching small amounts of my skin between her finger and thumb. She worked her way up the back of my left thigh, skipped over my hands, and continued pinching up the back of my shin. She was pinching such a small piece of skin, she didn’t have to squeeze hard before I chirped out in pain. Reading me like before, she figured out just how hard to pinch before it was too hard.

Sliding her lips off of my penis, while she pulled her finger out from inside of my body, Donna rose to her feet. In a firm, commanding tone, she glared down at me and said, “Little Prince, stay right where you are. Do not move. Do you understand me?”

I whimpered softly while laying naked on that table with my knees pulled back to my chest, “Yes, I understand, Donna.”

She took several long strides toward what looked like the living room through an archway. I watched her cross that room and then disappear from view. Although I could tell from the sound of her footsteps that she climbed a flight of stairs to the second floor. She walked around up there for a few moments before she began descending the stairs once more.

The entire time she was up there, I held my legs firmly in place and tried my best to remain perfectly still. I did look around the dining room and noticed a large picture window with a lacy half curtain. That gauzy curtain was the only thing hiding me from her backyard. Thankfully, I couldn’t see any houses or even a fence beyond the trees, bushes, and other plant life.

When I heard Donna approaching, I turned my head and waited for her to enter my line of sight. When she did, I saw she was carrying an opaque, black plastic tub. She chuckled, “You can let go of your legs now.”

She didn’t say another word until she stood beside the table. After pulling out the chair to my right, she set the tub down. Donna removed the lid and set it aside before reaching in and pulling out one item after another.

While she unpacked the storage container, she explained, “I’ve picked up different things over the years whenever I thought about the chance I had with that young man I told you about. I’d always hoped I’d get another opportunity to show a gentle boy the wonderful things I have to offer. And now we’ll finally get an opportunity to use these toys.”

The first thing she pulled out was a strap-on harness. It was black leather with metal rings and buckles. There wasn’t anything attached to the harness, it was empty. Next from the box came the dildo. It was a brilliant pink color. It was a cylindrical shaft with a rounded-off end. It looked impossibly long and thick and caused me to nibble on my lip out of concern.

After Donna had attached the dildo to the harness, she set it out neatly on the table beside my hip, she reached back into the box and pulled out a pair of shiny, silver handcuffs. Following that came a scary-looking wooden paddle and a baby-blue buttplug. She grinned while pulling out a plastic bottle. She set it down so I could read the label, it was a water-based lubricant that was spiced with cinnamon.

Still grinning, she said, “I remember reading the reviews about that lubricant. When it arrived, I had to try it. I only made that mistake once. It has a wonderful burning sensation that I’m sure you’re going to love.”

Donna moved back to her seat between my legs. In a calm tone, she said, “Lift your legs back up. Pull them to your chest again.”

After I’d gotten into position, she reached out and picked up the handcuffs. “Let me see your wrists.”

When I held them upward, she locked them together behind my knees. Laying there with my wrists locked together behind my knees, I realized the situation I’d gotten myself into. I was on the verge of freaking out when I felt her gently touch my wrinkled hole and the level of arousal in my body shot through the roof.

“Little Prince, how are you doing?”

I squealed, “I’m okay!”

She pressed against the tight knot of muscles with the pad of her finger, “You’re only, okay?”

I giggled, “No. I’m way better than okay. But I’m sort of freaking out a little. I mean, look at me!”

She slipped her fingers between my thighs and pulled my little prong so it stood straight up once more. She then stood and picked up the cinnamon lubricant. She held the bottle so I could see it while she opened it. Moving it just under my nose, the strong scent of cinnamon made me imagine the red-hot candies I ate as a child.

The fear of having that liquid poured onto my sensitive places forced all other thoughts from my mind. I whimpered softly, “Donna? Is it going to hurt?”

She grinned, “Oh yes! It’s going to tingle and burn. It’s going to feel so good. You’re going to love it, my little Prince.” While she spoke, she turned the bottle over and let a single drop fall onto her fingertip. She then sat back down and after several excruciatingly long moments, I felt her slippery finger touch my wrinkled knot. At first, it felt cool and wet. But after she’d massaged it into my quivering balloon knot, I felt the heat build-up at an alarming rate. In seconds, I squealed out loud and rolled onto my side.

Donna smiled down at me while still gently rubbing her slippery fingertip over that highly sensitive bundle of nerves. The burning sensation grew more and more intense. I felt tears rolling down my cheeks and my breathing came in quick gasps. “Donna! It hurts! It burns! Donna, It hurts bad!!”

She continued to smile down at me writhing on the tabletop and asked in a soft tone, “Little Prince if it hurts so bad, why is your little penis so stiff?”

I gasped and arched my back as much as I could. Tears began rolling down my cheeks. My penis was indeed very stiff. But the burning sensation was so intense, it was obvious my body didn’t know what it was doing. After what seemed like hours, the burning sensation began to fade.

Just when the pain was becoming manageable, Donna whispered, “And that was only a single drop.”

I lay there and watched as she picked up the buttplug and poured way too much lubricant onto it. I was making all sorts of funny noises as I thrashed around on the table. If one drop had burned as badly as it did, I was truly afraid to learn what that plug was going to feel like.

The strangest part of the situation was how calm and caring Donna looked while drenching the plug with that firey lubricant. Glancing up to my eyes, she asked, “Are you ready, Baby Boy?”

I squealed, “No! Please! No! Donna, I can’t!”

But she ignored my pleas. After rolling me onto my back, she lined up the plug and rubbed the rounded tip against my clenched hole. Like before, the burning was a slow build. Donna began to gently press the plug against my reluctant bottom. I couldn’t stop it if I tried. I spread open and felt the intruder enter my body. She worked slowly and diligently but didn’t rush burying that plug inside of me. She was sliding it in and out, each time pressing a little more inside of me when the burning began. By the time I was stretching around the widest part of the plug, the burning of the lubricant became its most intense. When I almost rolled onto my side, Donna took hold of my erection and kept me from moving while letting the buttplug slowly sink inside to its flanged base. That feeling of the plug filling my bottom was unlike anything I’d felt before. Donna had worked so slowly I felt no pain, other than the cinnamon lubricant. But that lubricant was wreaking havoc on my body.

I was sobbing and kicking my shins trying to get away from the burning lubricant, but it was impossible. I had to lay there and deal with the pain of the cinnamon burning the inside walls of my bottom. I cried and plead with Donna to have mercy. She only smiled and gently tapped on the base of the plug which caused erotic shocks to race through my body.

While the burning raged, Donna began to slowly stroke my desperate penis with her first finger and thumb. Her touch slid up and down and felt so wonderful, which was the exact opposite of the feelings in my bottom. It was terribly confusing. My body couldn’t decide which sensation to focus on. One moment the burning was dominating, the next her fingers on my little prong, and the next moment the sensation of that plug buried snuggly inside of my body. I was crying, screaming, moaning, and grunting all at once. I was writhing under her touch, arching my back from the plug filling me up, and begging her to make the burning stop all at the same time.

The burning did eventually fade. As it did, I began to feel exhaustion set it. My breathing and heart rate slowed while the tingling sensation in my bottom remained. Donna released my penis and let me lay there on the table before her in such a lewd position. I felt her warm breath on my still rigid erection and knew she was very close to my body.