Inspired by the amazing feedback I got on another recent post I decided to finally finish an old draft. I hope I’ve managed to keep the tense and perspective straight this time. It does switch from past tense to present tense half way, that is intentional.
Themes include free use, submission, oral, power differences, small cock worship, bondage, infidelity, and blackmail. I hope you enjoy.
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Fifteen years ago I was in a near impossible situation. My entire school career hinged on this final presentation and I was about to fuck it up big time. I asked my classmate James for help, pleaded, begged even, and all he did was shrug and say “you deserve to fail”. I was out of ideas.
“I’ll suck your dick!”
I didn’t even consider what I was offering, but I wasn’t going to let years of school go down the drain. James let out a loud laugh then looked at me like I couldn’t be serious. James was brilliant, but cocky and had a tendency to rub people the wrong way. He had few friends who appreciated his demeanor, and no female friends that I knew about. He was tall and stocky and usually looked unkept, but he was handsome enough if he would just put in an ounce of effort.
I take a step closer – “Anytime you want. Please? I promise. PLEASE?”
He hemmed and hawed. “You aren’t serious” he sounded skeptical and paused a moment. “Anytime?” he then asks curiously. I nodded hesitantly as he stared at me blankly. “Okay… right now then.” – “What!” – “Right now! Prove you will follow through and I’ll help you.” We were alone in an empty classroom, he glanced into the hallway before he pushed the door closed and stood watching the window.
“Prove to me that you’ll hold up your end of the bargain, and I’ll help.”
I slowly and reluctantly crouched and leaned against the door, trying to ignore the possibility that somebody see my head at his waist through the glass. I slowly pulled down his sweatpants and looked up at him, he looked nervous but eager. I lowered his underwear and used my hands to push aside his pubes, took a breath, and leaned in to take his small flaccid cock in my mouth. He got almost instantly hard, the tip of his cock pressed against the back of my mouth as my lipstick rubbed off on the base of his shaft. I closed my eyes and blew him with feigned enthusiasm until he exploded and I swallowed for the first time ever, doing my best not to gag.
I leaned back against the door, processing what just happened. “Will you help me?!” I asked softly looking up at him. He did. And I passed. James took advantage of that offer for months, he even arranged a schedule where we would meet and I begrudgingly kept my word, eventually becoming numb to our daily routine. He had a few spontaneous requested in the evening when he was drunk, which I hated but at least he would usually fall asleep before he would finish. Eventually he got bored and we met less often, and he eventually moved away for a good job offer while I stayed and advanced my career locally. I felt like I had outgrown and moved beyond that part of my life.
Now, 15 years later, I watch in absolute horror as James is introduced in front of my whole team at work as our new product lead. I had not seen him in so long and I wasn’t even sure he would recognize me, let alone remember our arrangement. After I leave the meeting I get an e-mail from his secretary instructing me to meet him in his office at 4:45pm.
“You look well” I say behind a feigned smile as I walk into his office. The chubby and scruffy college kid I knew was now lean, and athletic, and well groomed. He tells me to sit down while he walks past to close his office door, before returning and leaning against his desk. “We both know that certification hanging on your wall is junk. And I’m not sure I can ignore that from a member of my team.” He says coldly while looking me in the eyes.
I feel like I was hit with a ton of bricks. I sit there with my jaw hanging open, staring at him, panicking about how my career is in jeopardy. I ask hesitantly “Are you…. Is this about when we were in school?” He smiles, and calmly replies “Listen… I’m not unreasonable.” He hands me a piece of paper with an address. “Here’s my address, come over tonight at 8, and maybe we can work something out.”
I stammer as my voice cracks “James… It’s been 15 years! I’m… I’m married now!” He reiterates “8 O’clock” as he goes to open his office door and motion for me to leave.
I return to my office and there was a box sitting on my chair behind my desk. I pull out the card, it just said “Wear this – J”. I peak in the box to find a black sheer lingerie set. I mope at my desk for an hour trying to focus on work, but achieve nothing. At 6:00 I called home to say I was going to be late at work. It wasn’t unusual for me to work late, I am our only family income, but I never used work as an excuse for something personal.
By 8 that evening I had changed and taken a cab to the address I was given. It’s a tall downtown tower. The building has a doorman who greets and directs me to his unit on the top floor. I’m wearing the outfit he gave me underneath my work blouse and pencil skirt. It’s tasteful and expensive, but does little to calm my nerves.
“Beth!” He shouts enthusiastically as he opens the door for me. He’s wearing suit pants and a long button shirt with his sleeves rolled up. His apartment is spacious and open with several glass walls overlooking the city. It’s a stark contrast to my little townhouse in the suburbs. I smile nervously and walk inside. He takes my coat and closes the door, then guides me to the kitchen where he pours me a glass of wine. Nervously I begin to ask why I’m here. “James… I… ” but he interrupts me.
“Beth. I want to make you an offer. ” He sits down next to me at the kitchen island. “I’ll forget about everything. Your plagiarized school final. Your sham diploma. Even our ‘arrangement’. ” He puts his hand on my thigh and leans in. “In exchange for one night of complete and utter submission. ” he said with a genuine smile before sitting back up and sipping his drink.
“What does that mean?” I ask taken aback. He stands up suddenly and stares down at me. “It means…. you become my personal **fucktoy** until I say I’m done. It’s either that or you can hand in your resignation tomorrow.” I look away and fiddle with my wedding ring, then I finish the rest of my wine in one big gulp and look up at him. “Fine…. Fine! But after this we’re done. Completely. Forever. Deal?” He smiles. “Absolutely.”
I reach out and go to undo his belt but he stops me. “Not yet.” he says. “First, I want to see you. For all those wonderful blowjobs you gave me, I never once saw what your body looked like.” He lets go of my hands and sits down, then nods his head as if to say “go on”. I get up and stand in front of him like I’m being inspected. “Did you wear it?” he asks calmly, and I nod yes. “Show me.” he commands.
I look down and unzip my skirt before undoing my blouse, I toss my shirt to the side and wiggle my hips as I drop my skirt to the floor and kick it off. I stand awkwardly in his outfit, a tight black two piece set with spaghetti strap top and lace thong bottoms. The set hugs my little body and the sheer fabric barely hide what’s underneath. “Good… I’ve waited 15 years to see this.” He says with a big smile.
He walks over to me and wraps his arms around me as he smells my hair and kisses my neck. His hands drift down and he squeezes my bare ass. I can feel his hard cock press against hip. He lets go and takes a step back and commands “Undo my shirt”. I undo his buttons as I stare at his smooth toned chest. “Pants” he says calmly, as I kneel down and start undoing his belt and fly. “I’m not the overweight scruffy nerd you remember” He says. I drop his pants to his ankles, leaving his underwear which mostly hides his swollen cock. “Keep going” he says. I pull down his underwear, he’s shaved fully smooth and his cock is rock hard. “You shaved” I say with a bit of relief and a crack of a smile. “I told you, I’ve grown up.”. I wrap my hand around his cock and slide my hand down to the base, the tip barely reaches the end of my grip. “Well, not all of you has grown.” I say with a chuckle.
He suddenly reaches down and lifts me up to my feet then forcefully pulls down the front of my lingerie top, exposing my small breasts before he firmly grabs one as he squeezes my ass and slowly pushes me towards the back of the sofa. He spins me around and bends me over the back then pulls my thong down to my knees and kicks my legs apart. I’m draped over the back of the sofa with my knees together and my feet kicked apart. His hand is on the back of my head gripping my hair, and he slaps my ass hard with his other hand. Then again, and again even harder. I gripe about the pleasurable pain, then his hand slides down my backside as his fingers play with my labia before he pushes into me. I moan with sincere pleasure, I don’t remember the last time I’ve been manhandled like this. “Fuck me.. please” I quietly beg him.
He pushes my head further down into the sofa cushion so my legs can’t reach the floor, they are dangling off the back. Then suddenly I feel the head of his cock press against my pussy and he slides into me in one hard thrust as his body pins me against the sofa. My hands grip the sofa cushion and my feet kick as he continues his shallow thrusts, again and again, every time just a little harder until finally he holds me down with all his weight and groans loudly as I feel him cum inside me. He holds me still a moment before letting go and taking a step back, his cum is running down my leg as I get back on my feet.
I expect that might be the end of our night, but no. He pulls my underwear down the rest of the way and I kicks them away and lifts my top off leaving me completely naked. He reaches for his belt and pushes me down on my knees, I start playing with his semi erect cock and he demands I raise my hands. I do and he ties them together with his belt. “Suck me again… for old times sake”. He says as he holds my hands above my head. I lean forward and take him in my mouth then he pushes my head into him until my lips are at the base of his cock. He thrusts into my mouth and groans until he’s hard.
James holds the end of his belt and pulls me back up on my feet and leads me along like a dog on a leash into the next room. His bedroom is massive with a huge bed in the center of the room. He pushes me backwards on the bed and uses a silk tie to tie my ankles together to my wrists. He puts me on my side so my ass is just hanging off the end of the bed and slaps me again, I moan with pleasure as he plunges his cock in my pussy again. “How are you still going!?” I say with genuine surprise. “I’ve been planning this for years.” he says with a grin. This position hits just right and his cock rubs just the right spot, I can’t help but quickly build to orgasm as he thrusts firmly while spanking me. I moan loudly as I cum, my toes stretch out and my hands flail for anything to hold on to but finding nothing. My whole body tenses up and James holds his cock still inside me, enjoying the sensation as I grip him tight during climax.
“Good girl.” He says to me as he slaps my ass while he pulls out. I lie like a ragdoll on the bed, limp and still, as I catch my breath. I feel him reposition behind me and begin to press the tip of his cock against my ass. “What are you doing!?” I ask looking over my shoulder to him. “You once called my dick ‘perfect for anal’, don’t you remember?” – “What I never said that.” – “Yes you did. So I’m going to find out if you are right.” I begin to protest incoherently but James just says “sexdolls don’t talk.” and stuck a few fingers in my pussy as I moaned. He pushed his fingers deep into me as he rubbed my clit with his thumb, I didn’t protest as his cock slowly pushed into my ass. He grabs my hip with both hands and pushes himself into me as far as he could go as he groans loudly. “You were right… I am cut out for this!” he grunts as he takes a few shallow thrusts before he cums again.
James stays still a moment before slowly pulling out, he stumbles back a step before reaching over and untying the tie and belt around my wrists and ankles. I lie on my side on the bed as he tosses me a towel. “You’re done.” he says calmly, and he was right. My legs were weak and felt like they were still tied up. I hold the towel to my pussy and ass as I scamper to the bathroom. I ask if I can have a shower, which he says is fine.
I clean up and begin to put my clothes back on that I left the house with that morning. “You’ll want to keep your ass out of sight for a day or two” James says as he checks out my ass while I change. He points to the slap marks with a clear handprint on my ass. I blush.
After I’m changed I ask again “So, this is it? We’re done? For good?” He looks at me caringly and says “Your secret is safe with me, unless you want to do this again.” he smiles and offers me a drink. I decline, opting instead to go home as his offer to meet again rings in my head.
Source: reddit.com/r/eroticliterature/comments/t6lws1/the_blowjob_arrangement