Gay Sex

I Transformed into a Toyboy

My first paid encounter as a toyboy.

Spankmasters
May 21, 2024
12 min read
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How I Became a Toyboy
How I Became a Toyboy

I Transformed into a Toyboy

Stepping out of the elevator, I find myself in front of an elderly American woman as she makes her way to her room. I open the door, extending courtesy by stepping aside to let her enter. The suite is grand, featuring a huge window that overlooks the dazzling city of Amsterdam. It's adorned with an impressive view of the city lights. In the center, there's a comfortable seating area with two luxurious chairs and a large TV mounted above a sleek desk. Toward the opposite end, there's a spacious bed with an array of pillows and an impressively large bathroom that boasts a glass wall, stunning white marble, and mirrors on the surface.

As I struggle with the chain lock, due to my cold, shivering hands, the lady walks in, turning down the lights and playing a Miles Davis record. She sits in one of the chairs, currently studying my bare torso.

"What are you waiting for? Undress for me. Give me a sensual, leisurely striptease. Show me your attractive physique. There's no point in rushing to your mother now, young man. So get started, arouse me," she commands.

"Yes, ma'am," I politely respond, feeling uncertain about my next move.

I'm a young 20-year-old who is about to perform a striptease for an older woman. My heart races, and I can't help but notice the pleasure in her eyes as she views me as her prey. My time is running out, but I'm hesitant to leave, and I've already agreed to her request.

Throughout my past relationships, I've always been the one to initiate sex. My female partners, once enamored by me, gladly accepted and even encouraged this behavior. I'd fuck whichever way I pleased, drawing pleasure from their reaction. With the right incentives, I could also get them to perform fellatio or open their legs for a good pounding. My girlfriends loved these moments and appreciated my dominance to a large extent, but I'd never considered playing the submissive part before.

"What's taking so long, boy? Don't you want me?"

"No ma'am."

I take a few steps to the sound of the jazz record, moving my covered body slowly according to its beat. I glide my fingers over my denim-clad groin, feeling an erection starting to form. Looking at her, I see her lips glisten with moisture as she watches my hands work on myself. With each touch, the bulge becomes more apparent between my thighs. I also take my nipples between my fingers, hardening them through my T-shirt, before fondling my chest. Slowly, I advance toward her as the music plays, showing off my defined abs and muscular arms.

She watches from her seat, mesmerized by the spectacle and my naked upper body. I move slowly, palming my butt cheeks, and occasionally turning around to give her a flash of my butt. When I turn back, I pull off my shirt, letting the fabric fall to the floor. I'm naked, except for my socks and still partially flaccid member. Fear and vulnerability course through me, as I display my body in such an explicit manner for the first time.

I take off my shoes, drop my torn jeans, and target her gaze. My ass is now completely exposed, as I fondle myself below my waist, revealing a hardening cock. The ring of inside my briefs barely restricts my growth. Every so often, I slowly spin my body to provide a different view. Feeling more confident now, I near her. She's rapt with attention, fixated on the sight of me.

"Did you enjoy the show? Want more?" she asks.

And so, I counsel her to watch intently as I uncouple my underwear, and turn fully nude, with my swelling erection squarely facing her, as it had never done before. Rarely have I felt so naked, so exposed, or so vulnerable. It all started with an order from an older woman, treating me as her toy. I pray that the change doesn't reach my heart or manipulate my thoughts any further.

Sitting completely naked before a woman at least three decades older, her gaze captivating my body like a possession. I can't escape now—the train has passed. I'm left with her game, playing her toy to secure a bed for the night. My heart beats wildly with anticipation, and I can't help but notice the lustful look on her face as she admires my youthful naked body. Moving forward slightly, I grasp my manhood, my fingers encircling its purple head, as I begin to stroke myself. My erection stands tall, three feet from her face.

~ ~ ~

My journey began when my girlfriend kicked me out of her apartment. We'd quarreled the previous week, even though we had made up. I met her six months ago during the university's orientation week. She was already in her third year, while I was a complete novice in the city, the school, and even in life. I had some intimate experiences, like touching and caressing my girlfriend back home, but that was the extent of my sexual experience. The idea of marrying her was prevalent among the girls in the village, just like in the story. I craved a different lifestyle, full of freedom.

Ostracized, without a place to stay, I spent the following months traveling back and forth between home and the city. For four months, I shared her bed and body, indulging in a student's joyous life of parties and sexual relationships. It was an exciting time, both physically and emotionally, albeit my parents disapproved of my decision. They wanted me to marry the girl next door, start a family, and work in their grocery store. I had dreams, and I wanted a future of my own.

After several failed attempts at finding a place to stay, I found myself in a hotel bar near the train station on a rainy Friday evening. I was in a desperate state, when the last train to my parents' house was in an hour and a half. Desperate to avoid returning home, I began contemplating the futility of my coming back. With a depleted bank account, having spent all my resources on food, drinks, and clothes for my ex-girlfriend, I knew I couldn't afford a room. Fortunately, I had a free train ticket, but I didn't want to use it right now. Surrendering to my parents would mean giving up on my dream.

As I looked in the mirror behind the bar, I saw a beautiful space. Gorgeous atmospheric lighting, gold chandeliers hanging from the ceiling, a red carpet, and velvet curtains. People talking at their tables. Females in nice dresses, men in smart trousers with shirts, and some men wearing ties. I felt misplaced, wearing my worn-out, smelly T-shirt, old jeans with holes, and my plastic shoes. No one knew me here. That was one of the many reasons I chose this place. There was no need for me to meet anybody.

~ ~ ~

The waiter handed me my beer. 'This one's from the girl at the end of the bar, sir,' he said, gesturing towards her. A young, beautiful Asian lady wearing a tight, white shirt and black tie refilled my glass, her hand momentarily grazing mine as she placed it back on the table. She smiled warmly, revealing dimples beneath her eyes. 'Thank her for me,' I replied, unaware that her attention was on me.

'Perhaps she'd appreciate a little conversation, so she doesn't feel alone,' suggested the waiter.

'But I prefer sitting alone,' I said, my eyes fixed on her in the mirror. "She meets my gaze, as if stripping me bare with her penetrating gaze.

'You'll be better off humoring her for a few minutes. She'll order another glass of chardonnay, and I'll top up your glass as well,' the waiter replied fondly.

'Thank you, ma'am,' I said, shaking my head at the waiter's suggestion. I approached her. 'Just five minutes, another beer, and I'll be back to my own space. On the way to the train station, I'd leave for home to nothing.'

At the end of her bar, she thanked me. Her presence had a hypnotic effect on me as I sipped my drink. As the waiter had predicted, she ordered another glass, which was immediately refilled. Without realizing it, I began to speak to the woman. Time slowed as our conversation flowed easily, despite our age difference.

No longer did I wish to go home; I wanted to stay there with her. To keep chatting and repay her kindness. I didn't intend to sleep in my parents' house.

This woman opened up to me like only an American can, sharing the highlights of her life in just a few minutes. She was visiting Europe, drawn to the old masters and architecture. Divorced and traveling alone for the first time, she'd come to Amsterdam as her final destination. Europe had gripped her with its beauty, and her eyes lit up as she recounted all the works of art she'd seen. But the true masterpiece, according to her, was Michelangelo's David. She spoke with a wide grin.

In the meantime, I was sharing my situation with her. I was studying and had just been kicked out by my girlfriend. I was staying with friends temporarily, awaiting their response about whether they could accommodate me for the night. If they couldn't, I'd have to make the journey back to my parents.

Another round of drinks prompted more conversations, covering everything from art to politics to Amsterdam. The first time I looked closely, I estimated her age to be around forty. With her designer wardrobe, gold earrings, and large necklace framing her ample cleavage, she looked rather refined and attractive. But as she moved closer to me, I spotted the subtle signs of aging: the well-nourished skin, the crafted haircut, the professional makeup. Her eyes and wrinkled hands suggested she was closer to the prime of her life than I'd initially thought. Somewhere in her late forties or early fifties, perhaps -- beautifully preserved.

I heard my phone buzz in my pocket. My request for a place to stay in Amsterdam was turning out to be a dead end. Just as I was about to apologize and leave, she made her move.

"Can you help me with my problem, sir?" the waiter inquired as he put my next drink in front of me, catching my attention.

"What do you mean?" I queried, annoyed that my focus had shifted to something other than what I was sharing with this woman.

"If you need a place to stay, I could ask if she'd be willing to share her hotel room with you. It's apparent that she wants to make the most of her holiday. It's about 800 euros and a bed for you," he elaborated.

"No way," I replied.

~ ~ ~

"Come here." she commanded, pointing to a spot near her chair. I cautiously moved toward her, the distance I'd barricaded myself with during our conversations fading with every step. When I got near her chair, she asked me to sit down beside her. My hands were on my backside, offering easy access if she so desired. She seized the opportunity, touching my testicles. I remained still, suppressing my natural response. Her fingers played with my groin, squeezing it and massaging gently. Suddenly, one hand ventured further and held my erection, pulling the foreskin back to expose the head of my penis. I struggled to maintain control, but it was difficult.

"Lick my finger clean, David."

I did as she instructed, licking her finger like a hungry child. She seemed to take great pleasure in watching me. She then led me to her chair and sat down, gesturing for me to do the same.

"Unzip my gown."

When I complied, her outfit was cast off. She spun around, exposing her undergarments to me: her bra and slip. She was generous in the bust department, her large breasts jiggling slightly but still looking firm and robust. She held them in my hands, squeezing them gently. I'd never touched real breasts before, only the tiny cups on young girls. But these were a whole new experience. I couldn't get enough. She asked me to remove her bra, which I did, exposing her breathtaking large, dark nipples. The flesh was soft, soft, and the curves were so enticing. This was in complete contrast to the small, pale nipples myself and my ex-girlfriend. This woman's were real, beautiful, and tempting, and I was inspired by them.

"Lick my nipples, David."

She crooned, as I released my grip on her chest and focused on her nipples. I savoured them one by one. This unequaled sensation meant more to me than those slender, repeated riches I'd tasted before. And when I moved my hand down, touching her wet panties, she moaned like a kitten, encouraging me further. "Go lower, deeper," she coaxed me. I did as I was told. Kneeling before her, I spent what felt like an eternity licking her feet. My tongue traveled over every ridge and bump intently, enticing her with each pass. She seemed to like it. Her legs spread open, and I noticed the smoothness between her thighs, so different from the thicket of hair I'd see in regular porn. Gradually, she eased herself toward the edge of the bed.

I hold her foot in my hand, taking off her high heels and thin socks. I've never used my tongue to pamper a foot before. I suck each toe, putting them in my mouth. Sucking on them. Licking them, as if I were tasting the whipped cream of a chocolate dessert. She watches from above as I'm on my knees, very close to the floor, tasting and worshiping her feet. It's like a dog licking the bottom of her soft, well-groomed feet. My cock head presses against my stomach, between my own legs. She's the first to tell me to worship her by sucking her breasts and feet.

Her legs spread wider. I see a black silk panty with a floral pattern and red thread from below. It's definitely different than the cheap panties my friends wear.

"Lick with your tongue and move slowly upward." She instructs as she opens her legs even more. I resemble a puppy licking every inch of the way up to her secret, hidden place. My hands want to touch her as I slowly move up.

"Keep your hands off, dogs use their tongues."

She takes another sip from her glass of wine when I'm halfway up her thigh. She moves a bit further up on the bed. My tongue touches her silk underwear. She shakes a little when I make the first contact. She moans softly above me. When I look up, she has her eyes closed. Her hands are massaging her breasts. She puts the other hand on the back of my head and pushes my mouth closer and harder on the moist spot in front of me.

I press my tongue against the fabric, so she can feel it. She gets up and settles on the floor with my head in her crotch height. She carefully removes her lace panties. I see a thick bush of dark hair between her legs in front of me. Two red lips in the middle. Not a pristine, groomed pussy, but a coarse bush of hair and a slightly smelly pussy. She moves back to her spot on the bed, my tongue travels, slowly licking upwards from her anus to the holy part. Halfway through, I press my tongue deep into her wet pussy, finally reaching her clit and sucking on it. It's a small nub to play with. She moans and encourages me to lick her clit hard and wet. My fingers find their way inside her wet hole. My girlfriend always liked that.

"Keep your hands away," she says, "I want your cock inside me."

I get up and slide my cock tip into her slit. A first gentle push to open her up, but it's wide and wet like I've never experienced before. After the first push, my big cock enters her tight, warm sheath. Keeping pace and thrusting deeper and harder until I'm as deep as possible. Her hands play with her clit, and my thick cock pleases her deep and tight pussy. I feel her pussy muscles contract around my shaft as she yells that she's coming. I also start to moan, telling her I want to come deep inside her. I pick up the pace, slamming my cock into her as deep, fast, and hard as I can.

"No, stay there, don't come yet." She tells me, screaming like a hog. I don't listen.

"Now release your cum all over my breasts," she demands me.

I climb back on the bed, straddling her belly with my cock in my hand. She pushes her breasts together, creating a space for my cock. I start slamming my cock into it. Moving my hips back and forth. My dick nestling between these fantastic, big, sensual breasts. My hands grip her, her breasts thrusting up and down. I look at her face. Her eyes closed, she enjoys every impact of my hard manhood between her soft womanhood. I get up and stroke myself while she watches. After just five strong pulls, I feel the pressure build up in my balls. I can't control it, the muscles begin to contract and my acrid fluid leaves my piss hole. I didn't come, but I exploded.

A massive discharge of cum leaves my cock head and plasters across her boobs. A second release follows. The third and final eruption lands on her navel. Her entire upper body is covered in my cum.

I lick her clean, desserting the big breasts with their large, dark nipples, the firm belly, the damp pubic hair, her pussy jewels and the moist skin around her anus. She reclines on the pillows, her hands behind her head. I lick her, worshipping like a puppy. Tasting my own cum, her pussy juices, and sweat.

We share a shower, filled with soapy bubbles. I cleaned her vulva using slightly warm water. Next, I gently rub body lotion onto the senior woman's skin. I massage her breasts using the lotion. Afterwards, she cuddles against me on the massive hotel bed's crisp white linens. For a while, she amuses herself with my sex toy, which promptly responds. However, she dozes off in just fifteen minutes after two hours of sexual encounters. Even though I am still somewhat aroused, holding my partially erect penis, I can hear her snoring loudly – much like a pig.

I look at the ceiling, feeling unclean and abused. Although I satisfied her desires, the body wasn't appealing. No petite breasts with delicate, small nipples. No flat tummy leading up to a shaved pussy containing a snug, lightly-scented vagina. There wasn't a nice ass either. It was a body that had borne and cared for children. I loathed myself for engaging in such intimate acts. Perhaps I secretly liked the helplessness. She admired my nudity, giving me tasks without me needing to initiate them. She adored my movements and genitals in her. I ponder over the envelope and its contents she presented in the elevator. My hand grips my penis, and within two minutes, I ejaculate another dose of semen onto the sheets.

I drift off to sleep, consumed by sadness, dreaming of women who crave me. I stand naked on stage, and they bid on my body.

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