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    Orgasms, guaranteed!

    It started when I was between girlfriends and trying to pay for college. My ex told me I was amazing in bed but she didn't feel a deeper connection. I told her that I thought our "connection" went pretty deep. She didn't reply to that text.

    To put it bluntly: I was horny. But it was a generous kind of horny. Thoughts of eating out as many pussies as I could filled my wank sessions. I knew there were girls out there who needed that kind of help. Surely there had to be some kind of mutually beneficial arrangement. Perhaps even a business arrangement. Eventually I learned the term "gigolo," which is sort of like a male prostitute, except he specializes in female pleasure. So I decided to enter the "gig" economy. I ordered a few vibrators and called it a business expense.

    One thing I learned from half a business degree is to have a selling point. After some thought, I landed on my orgasm guarantee. If my client doesn't come in twenty minutes, the session is free. Don't get the wrong impression: I almost always make good on my guarantee. But one of the exceptions was particularly memorable.

    My client was in her late twenties, a grad student in something or other. Tall, with long curly blonde hair that hung over her face. Chest size was respectable but not huge. And, as I'd discover, she had shaved down below just for me.

    A few minutes after arriving, I found myself in her bedroom. Landlord white walls, a mauve bedspread, and a eucalyptus wax melt doing battle with her absent roommate's weed. She muttered something about being stressed out about school and not knowing what to do with her life. I needed to get her mind out of worry mode. "None of that matters for the next few minutes. Get naked, and lay on your back. I'll take care of the rest."

    I don't watch my clients get undressed. I'm there for them, not the other way around. Of course I relieve myself of some clothing as well, but not all of it. I was engrossed in my typical mental preparation and tongue exercises when my client interrupted. Almost insulted, she asked, "are you really going to leave your boxers on?".

    "I'm a professional."

    She stared on hole through my underwear. A moment later, she realized she was naked in front of a stranger for the first time, struck a pose, and said "tada!".

    "Very nice. The bed, if you please." She shimmied onto the full-size and I dimmed the lights. I grabbed the vibrators from my bag, laid my phone out on the nightstand, and joined her on the bed. She was on her back and I was on my knees, between her legs.

    "Are you ready for your guaranteed orgasm?"

    "Fuck yes, but you're going to need to work for it."

    "It's never work when it's pleasure." That line was... mostly true. "Hey Siri, timer, twenty minutes."

    "Twenty minutes, counting down," came the robotic voice, but her thighs were over my ears before it finished.

    One of the hardest parts of this job is pacing. I don't have time to start super slow, but going in full throttle doesn't work either. Instead my go-to is tongue action on the clit, and then seeing how my client responds. In this case, she seemed to relax, but didn't get further than that. After a minute or two, I asked, "how does that feel?"

    "It's nice, but I need to be penetrated."

    "I have fingers and toys."

    

"You also have something else."

    

"I'm a professional," I insisted, and slipped one finger inside her. I began to curl it against the rippled folds of the forward wall. A moment later, I stuck in a second finger. Her head lay back on the pillow, eyes closed, with deep breaths. Good signs. "More," she moaned, slightly out of it.

    With my free hand, I grabbed one of the vibrators, turned it on, and then placed it on her clit. After a moment, I moved it down to get some moisture and brought it back. Then I slowly moved it in circles, never quite leaving the nub, but never letting it get numb either. She exhaled deeply, thrusting her exposed chest towards the ceiling. I thought about giving her boobs attention, but I was out of hands. One held the vibrator, and the other was still inside her. I uncurled those fingers and pointed them straight at her cervix. Then I thrust them in and out quickly. Industry insiders call this move "finger blasting".

    My client continued to have the industry inside her for several minutes. Despite some good moans, she wasn't getting off. "What more could you want?" I said in a sultry voice. But underneath that, I was getting frustrated and worried.

    "Cock..." she breathed, pleading.

    "I told you, I'm a professional." We spent another precious minute in silence as she tried to get closer and my arm got tired.

    "Okay, stop," she said.

    
I removed my fingers, pulled away the toy, turned it off, and set it down. Juices dripped onto the bedspread but that was her problem for later. "What's going to help you?" I said in my customer service voice.

    "Take your boxers off. I want to see it."

    I looked down at myself. The silhouette of my cock poking through was already visible. I sighed, and somewhat awkwardly finished disrobing. I flung the boxers off the bed.

    "I want to touch it," my client said.

    
"I suppose." I moved up the bed so my dick was hanging over her belly where she could reach it. One hand slid the loose skin of the shaft over the head. The other caressed one ball, then the other. It felt nice, but we were on the clock for her pleasure, not mine. Reluctantly, I pulled back and said, "let's get you over the edge."

    "Okay," she murmured, hands falling to her sides.

    I tried every variation of tongue, fingers, and toys on clit and inside her. None of it quite worked. When the timer went off, it was me, not her, who sighed and rolled my eyes. I reached over to turn it off. When I returned to my position, my client was not happy.

    "I would've gotten there if you had stuck it in."

    "I told you this is pro--"

    "It's not professional anymore because I'm not paying you. You're just an amateur now." Her eyes narrowed. "And your results are amateurish."

    The nerve! "I tried everything I could."

    "You didn't fuck me."

    I sighed again, uninterested. My dick twitched, disagreeing. I started to push away from her. "Fine, let me get a con--" The backs on my thighs slammed into her legs, which she had wrapped around me. The momentum bounced and I fell forward. I managed to brace myself on the mattress instead of her body. Her nipples grazed against my chest, and my head hovered inches from hers. We were practically kissing and I could feel the warmth of her breath. A curl draped lazily across her face as her eyes stared unblinkingly into mine. "Put your dick inside me. Bare. Now."

    I suppose the customer is always right. I bucked my hips to get into the right position, and my tip slid through her folds. I inhaled involuntarily and my torso and arms tingled. Usually insertion requires awkward positioning by hand, but she was so wet that I slid down like into a funnel.

    I had enough restraint to hold at just the tip. She closed her eyes, shimmied, rocking her self on my dick. Her textured insides slid and squeezed around me. I clenched my teeth, drawing in breath through my nose like I could smell the pleasure. Then I cleared my head on the exhale, and my gigolo instincts came back to me. I leaned to the side so I could whisper in her ear. My nose dug into her curls and female shampoo scent wafted up my nostrils. "You like that big dick inside you?"

    She moaned assent.

    "You like it bareback? Chasing pleasure despite the risk?" A loader moan, and she squeezed her legs, still wrapped around mine, and pulled me deeper into her. "You want that dick deep insider you, knowing it could explode at any moment?" That was a slight overstatement of my arousal level. I pride myself on my endurance and my restraint. Actually, never mind about restraint.

    "You know, if I came inside you, you could get pregnant." As a professional, I'd pay for Plan B if it came to it, but that was several night's of income. So I was actually a little worried.

    "I could," she said, dreamily, almost playfully. I made the split-second decision to pull the thread.

    "I'd fill you up with my cum, and your belly would grow big and round." I moved my other hand across her flat belly, rubbed in a circle, lingering on the area between her pubes and her belly button. All my weight was on my other forearm but I could manage that for now. "Your breasts would swell, ready to be sucked on." I moved away from her ear and took one nipple into my mouth. I licked across the nub and then gently bit, rolling my teeth across it. Her breath deepened. I switched to the other nipple. I glanced up with it in my mouth, and she opened her eyes. "Fuck, that's hot," she said.

    I let her nipple slip out of my mouth and gave it a quick lick while looking straight at her. The "yes, I know exactly what I'm doing and I want it" look. "Yeah, you like the breeding talk?" I asked playfully.

    "Breeding," she breathed. I sat up and kept thrusting. Her legs still pressed into my thighs. If this would get her off, maybe I could still salvage my paycheck.

    "If you don't let me go," I said with mock concern, "I won't be able to help myself. My hot sticky load won't have anywhere to go except straight into your womb. And you know what it'll do there, inside you."

    "It'll breed me," she said, still savoring the word. A smile grew across those plump red lips.

    "More than likely."

    "Please breed me."

    

"Are you sure that's a good idea?"

    "Yes," she purred. Her calves pressed into mine and pushed me further into her. She was fully relaxed and a smile crept across her face. "You're just my living dildo. My personal sperm bank."

    "I think I'm a bit more than that."

    "Oh?", she challenged.

    "I'm the guy who's going to breed you." I grabbed her hands that had been at her sides and brought them up by her head, and pinned her down by the underside of her wrists. In plank position, I accelerated my thrusts. "You've done it now! You've got a dick inside you that's going to pop at any moment. There's nothing between my cum and your womb. You aren't going to go anywhere until I've pumped my load all the way up that fertile pussy. Welcome to the babytrap, bitch! Population three!"

    She whimpered. Our eyes were still locked. "Make me come and cum inside me. Send your cum deep inside me, fill me, paint my insides white. Breed me. Flood my pussy with your cum until I'm pregnant. Breed me. Cum so hard it's twins! Breed meeeeee--"

    She screamed as orgasm finally took hold of her body. Her back arched and her eyes rolled back. Below, I felt the most amazing squeezing around my dick, and a warm sensation at the base of my shaft. I love it when I get them to squirt.

    I was about to do some squirting of my own. For a moment, I thought about really doing it. Clear skin, luscious hair, smart enough for grad school, this girl had excellent genes. We could get married and I'd fuck her every night until we had a gaggle of kids. But the fantasy passed, and I pulled out.

    It took exactly two strokes of my left hand with the help of her juices. My cum flew out of my cock and onto her belly. I had so much, for a moment it felt like peeing cum. It filled up her innie belly button and ran down her sides into the bedsheets. I arced some up towards her tits but it didn't get that far. I suppose it was fitting that I had actually painted her womb, just on the outside.

    She caught her breath, sat up, and looked down at the mess I had made of her. Both of our fluids were splattered over her abdomen. Squirt dripped off my cock. I ran my hand up from her crotch to push away an errant white bead. "Thanks for not actually doing it," she said sheepishly.

    "Well, I am a professional."

    "I suppose," she said. Not only did she pay me, but she gave me a most enjoyable tip.

     
      Posted on : Oct 22, 2026
     

     
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