The Cherry Milkshake [Mf] [age gap] [cutting] [masochism] [vaginal] [oral] [long-ish]

Names are not fleshed out for a reason:

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So, I had this job at this ice cream shop throughout high school and we had a few regular customers I saw in the four years I worked there (from fifteen to nineteen). One was an older guy that often just bought a cherry shake. I’d make the shake when I saw him pull in and then, unlike any other customer, I would run it out to his car, he’d give me the cash for the food and always told me to keep the change. This was a man that paid for a two dollar order with a twenty religiously.

He got into the habit of only coming around when I was on shift and it was something my co-workers picked up on and teased me about because I was shy. In fact, I had a hard time calling out orders for people to come to the window to pick them up because my voice was so quiet that no one could hear me. They noticed he stopped coming around on their shifts because they stopped getting the eighteen dollar tip and I felt bad about it, one was a single mom and really needed the cash, so I stopped running it out to him and gave the order to her to take out while I did other things instead.

That happened a couple of times then he came into the dining room and called me over, ignoring my co-workers working the dining room window, and said, “Can you run my dinner out to me tonight, darlin’?”

I just nodded and, honestly, it unnerved me. This guy is a close friend of the people that owned the restaurant and their son-in-law worked the main cooking section in the back and he was the boss when the owners weren’t there. He saw this exchange go down and saw how uncomfortable it made me and he called me over and said, “You’re not doing that, I’m going to take it out myself.” Thank-fucking God, I felt all of my tension ease with that.

He spent a good ten minutes out there and everyone was watching, it looked like it got a little heated between them and all of a sudden the guy didn’t come around for a while. I thought I was off the hook and I was kind of grateful for it.

But, it didn’t last. The owner of the restaurant switched the son-in-law to days instead of nights with me and the guy started coming back, but sat in the dining room instead of one his car. I was much more comfortable with that, it was well lit and my co-workers could see me the whole time I was out there with him.

Time went on for a while and he started talking to me and joking with me while I cleaned the dining room between rushes of customers. Saying crudely joking things like, “Make sure you reach all the way over to wipe that down,” or “You missed a napkin on the floor there.” (It was on the floor, between two booths across from where he was sitting. It was an awkward spot where I had to kneel down to pick up the trash that had fallen in there as we just had a push broom, not a normal thin broom that would fit between the booths.)

Then he started asking me other things, “What do B and R pay you here?” (Six something an hour)

“I see. How would you like to make twenty dollars an hour? It would just be cleaning my house and cooking me dinner a few times a month while my wife is out of town. You could probably make a hundred bucks in cash or so in one night for just a few hours of work,” he asked.

Did I see the huge red flags? Yes, but did you see how much I was making at the time? A thirteen something an hour pay raise did catch my attention, but the red flags were to glaring and I turned him down. He wouldn’t be deterred.

He asked a few more times, but it was always around co-workers so I looked at them and back to him and said no again. (Fun note: my mom worked at the same place as me and often had the same hours as me, so those co-workers often included my mom.) One night, he noticed that I kept looking to my coworkers then seemed to nod knowingly.

That night, as he was leaving, he grabbed my hips and he pushed me up against the table he’d been sitting at as someone came walking by at the same time, making it seem like he had to, but there was plenty of room for him to walk by without pushing so roughly against my ass to do so, and whispered that his number was in my pocket. Sure enough there was a twenty with his number and first name scrawled on it in my pocket.

Yeah, I may have been a curious idiot and called him. I told my mom I was going to go to a study group on the nights he wanted me to clean for him, instead he picked me up and took me back to his house, which happened to be set back in the woods a good bit with a driveway that was about a mile long. He was really wealthy and owned acres of land in the area, his house was the closest thing we had to a mansion in that city.

I was nervous and honestly expected him to want more than me cleaning his house, but he showed me where the cleaning supplies were and told me what he wanted me to clean then sat back and watched me work or watched tv while I cleaned. After a few more times I got more comfortable and realized this guy might actually not be a complete pervert but this might be an actual cleaning job for a ridiculous amount of money. Cool.

It went that way for about two months, then he started asking me to clean things that were harder and required climbing on a chair, or ladder and such and meant I had to stretch a lot farther to clean the things. (Light fixtures, chandelier, upper cabinets, top of fridge, top of closets, etc.) Sometimes he would put his hands on my waist, under my shirt to hold me steady on an object and I tensed up but he would say, “I just don’t want you to fall and get hurt,” so I let him be a slight perv and help me stay steady, especially on the banister I had to lean over to reach a shelf on the opposite side of the stairs. To clean it with a ladder meant I would have to set up a ladder on the lower set of stairs beneath the shelf. It was just easier to lean over the upper railing to do it.

Of course, the first time he held onto me there I almost fell from getting startled at the suddenness of a body pressed against my ass with his hands on my waist. I may have screamed and dropped my cloth, he may have laughed and apologized then told me not to bother cleaning that shelf more than once a month. Yeah, I could live with that.

I cleaned his house for about six months without issue, then it progressed in a way I hadn’t expected it to.

I normally tucked my shirt in before I started cleaning and the shirt I wore that day didn’t like to stay tucked. He saw scars and some fresh cuts on my hip while I was cleaning when my shirt lifted and he damn near picked me up and threw me on the ground (it was more like pulling me from a sudden standing position down onto the floor on my stomach with my hands pinned to the floor by his knees. He was an old guy, mid-sixties if not early seventies and I was a teenager. It scared the daylights out of me. He lifted up my shirt to look at the cuts on my hip.

His fingertips trailed over them and he was pissed, “Who did that to you?” He asked.

I was scared, trembling, and I didn’t know how to answer. I was shy. No one had ever really paid much attention to me before, no one had ever confronted me on my injuries before. He moved himself down to my lower legs and grabbed my wrists with one hand and pulled me up to my knees then unfastened my jeans with the other. I honestly thought he was going to do more than he did, but he just pulled my jeans down off my hips a little and ran his hand over the scars.

“Who did this to you, L?” He asked me, his voice softened a little as he realized I was fucking frozen in fear.

I was holding my breath and he let go of my wrists and fixed my clothes then turned me around, “I’m not going to hurt you, I just want to know who did,” he said.

I did. I didn’t know how to say that, to admit that. No one knew that about me at the time. I closed my eyes, took a deep breath in then said, “I did,” the words were barely audible.

My gaze didn’t rise from the floor but he let me go and I scrambled away from him, “I’m sorry,” he said.

I glanced up at him, his face was contorted in concern and he ran one hand through his hair, the other rested on his thigh. He sighed and looked at me, “I’m sorry, I didn’t mean to grab you like that.”

My jeans were still unfastened and I had my knees pulled up to my chest with my arms wrapped under my thighs. My heart was racing and I barely heard what he was saying. He came over beside me and I scooted away. His hands reached out towards me and he thought better of it, placing them on his lap instead. “What do you mean, you did?” He asked.

“I cut myself,” I said, “I did this, no one else.”

“Can I see them? You don’t have to…I just…I’m curious,” he said.

I looked at him then stood up, took my shirt off, and slid my pants down and off my legs, easy to do since I cleaned barefoot thanks to his wife’s rule of no shoes in the house. Most girls would have covered their more intimate areas with their arms, I covered my scars. Along my stomach, hips, thighs, ribs, and upper arms. Her reached out to me and grasped my hand, gently pulling it away from my body. The thin white lines criss crossing my body mixed with the red welts of fresh cuts detailed a long history of self-abuse.

“Why would you do something like that to yourself?” He asked.

“Comfort. I work two jobs and go to school. I’m top of my class. All through high school I had to be the best to have a chance and that’s continued into college. It’s suffocating. This…relaxes me and lets me breathe,” I said softly.

“Show me?” He asked as he ran his fingers over the cuts.

“What?”

He leaned back and pulled a folding knife out of his pocket, “Show me,” he said, putting the knife in my hand.

I sat on the coffee table in front of him and pressed the knife into my thigh, cutting a clean slice from my inner thigh out to the top middle of my thigh. It bled freely, the bright red blood flowed over my milky thigh and I closed my eyes, feeling a little woozy. He came over to me and pressed my shirt down on my thigh. I opened my eyes and dropped the knife from my hand.

His hand pressed tighter down on my thigh and I winced, “I-I think I cut too deep,” I said.

He nodded, “Yeah, you did. My knife is like a thin razor, I should have warned you,” he said.

I looked at him and took a deep breath as my shirt tinted red, “I think I need to go to the hospital, V?”

He shook his head, “No, you don’t. Here, just lay down,” he said as he guided me onto my back and put my foot up on his shoulder, elevating my leg to slow the bleeding.

I felt nauseous and lightheaded as he tightened his grip on my thigh, “Hey, hey, L, stay awake,” he said gently.

While I did try, I passed out. I honestly couldn’t tell you if he did anything, but given that when I woke up his hands were coated in my blood and he was stitching my leg closed with some kind of thin blue string and a hooked needle. I felt the needle pierce into my skin and I winced then pulled away slightly.

He looked up at me and smiled slightly, “I’m almost done,” he said with a shaky voice.

I looked up to the ceiling and sighed. I could see my shirt on the floor, it was soaked in blood, V had blood on his hands and face where he’d been wiping sweat from his forehead while he sutured my leg. I could have bled to death and he had acres to hide my body on. He took that risk over trying to explain the half naked girl with a deep slice into her upper leg.

I sat up on my elbows and watched as he put a few more stitches in my thigh, rather painfully. He looked up at me and put the needle down, “Can you let your parents know you won’t be home for a few nights? You shouldn’t move around much until that heals some.”

“Yeah, I can just say I’m staying with friends,” I said. He got me his phone and I made the call.

V left the room and brought back a basin of soapy water and a cloth. He knelt down in front of me and washed the blood from my leg, pushing the edge of my panties aside to clean more blood from my skin. My breath caught and his fingertips lingered on my skin. I lifted my hips slightly, my voice wavered as I said, “You can pull them off if it’s easier?”

His fingertips moved up to the waistband of my panties and carefully pulled them down, stretching them over my leg to keep the fabric from touching the stitched cut. He could have just pulled them down enough to clean the blood from the crease where my thigh connected to my privates, but he pulled them fully off of me then pushed my leg open and began to clean the blood from my skin.

He kept pretending he wasn’t looking at my cunt, but his fingers touched me and his eyes lingered on my bare skin, “Do you have a boyfriend?” He asked me.

“No,” I said.

“Have you had a boyfriend before?”

“No.”

He pushed my leg a little more, giving away that I was somewhat turned on, “Have you had sex before, L?” He asked me.

“Yes,” I said.

V looked up at me, “But no boyfriends?”

“No boyfriends and no choice,” I said, “I’d like to leave it at that.”

He nodded, “Oh.”

His fingertips were resting on my pubic mound and he cleared his throat and started to pull them away but I put my hand on top of his, “It’s okay,” I said.

I bit my lip and he slid his thumb down between my pussy lips and pushed into me slightly. I moaned along with him as I leaned my head back and he leaned his forward. I lay back down on his coffee table and he spread my pussy lips with his, kissing me intimately and dragging his tongue up and over my clit.

It should have occurred to me to mix masturbation with the pain of cutting, but I never had before. Right now my thigh ached but his hands on the backs of my thighs, pulling me towards his face as his thumbs pulled my lips apart, where he found me wanting rather desperately. I moved my hips and he moaned, pressing his lips tighter to me. He started alternating his thumbs, pushing them into me and pulling my pussy open to him. I moaned and he pulled harder at me, licking deeper, his nose pressed to my clit and his tongue dipped into me with need.

I arched my back slightly and V pushed his thumbs into me and rubbed me until I opened up to him more. V let go of my cunt and grabbed my wrists, pulling me up to a sitting position as he stood up in front of me. I helped him get his belt, pants, and underwear. His dick was bigger than I expected and I think he knew that as he rubbed his thumb over my lips and parted them, “You don’t have to do anything, you know?” He asked.

His moans echoed in the room as I rubbed my hand on the lower half of his staff, my lips closed over his thick tip, sucking as I moved my head back and forth on him. I looked up at him, His hair was gray and his stomach was rippled with pudgy rolls of settled fat and loose skin. His pubic hair was mostly gray. It felt coarse as my hands rubbed over him. His eyes were closed and he started to thrust his hips towards my lips, his hand gripped the back of my head and moved me down a little further.

I gagged and he pulled back a little, but I could tell he ached for more. His dick filled my mouth, stretching my lips with his thickness much more than I expected it would. I pushed myself down on him and fought off the tightening gag making my stomach tense and my throat constrict, “Oh, God,” he moaned. I couldn’t help but smile. I was pretty sure everything about this was a sin and he was one of the most vocally godly men in town.

I pulled back and caught my breath as the thick saliva of my mouth coated his dick. He grasped my hair in his hand and tilted my head back with a sharp pull, “Do you like it, L? The pain?” He asked.

I nodded and he pulled my hair a little harder, making me whimper as I winced. I gasped and he rubbed the tip of his dick along my lips, I flicked my tongue at him, licking up the precum that coated his head as he smiled. One of his hands grasped my jaw, the other my hair as he pried my mouth open and started fucking my mouth, banging himself against the back of my throat as I whined and coughed, gagging on his dick and coating it even thicker in saliva, I grabbed his hips and held him back so I could catch my breath and he put his hand on my injured thigh and squeezed, making me cry out in pain as he pushed me back on the coffee table and pushed himself into me.

He held my thigh flush against his hip, ensuring it pulled the cut skin as he pushed deeper. I cried and he leaned over me, “Shhh, L, shhh, it’s okay,” he said.

I nodded and bit my lip, tears streamed from the corner of my eyes and I gasped as he pushed fully into me. He let go of my thigh and my tears subsided as I let my leg fall open, away from him, fresh blood streaked my thigh and his hip. V’s hands moved up my body, grasping my breasts through my bra as he held himself to me.

“I’m going to move again, alright?” He asked.

I nodded and he leaned down and kissed me, his hands moved to my hips as he pulled back and thrust into me hard. I moaned, he kissed me harder and thrust even harder. His hand rubbed my clit and he watched me squirm and arch my back as I carefully kept my leg away from his body. Each thrust into me made my tits bounce.

He might not have been my first, but he was my first willing and non-solo orgasm as he made me gasp and held me as my body contracted in euphoric spasms with the epicenter right around his dick. He groaned and I felt him start to pull out of me, but I locked my legs behind his back and pulled him tighter to me, wincing in pain even as my body continued to contract and tremble.

He ran his hand over my cheek and into my hair, wild red curls haloed around my head as he kissed me and thrust back into me and came inside. My hand reached up to stroke his cheek and hold him to me as he grunted. His dick twitched, releasing a flood of sperm into me.

V didn’t touch me again for the duration of the time I spent at his house healing. He clipped the stitches and pulled them from my skin after a week, then turned me onto my stomach and ran his fingertips along my spine, “Can I cut you?” He asked.

I turned to look at him, “Your wife is due home tomorrow,” I said.

He nodded, “It won’t be deep, I just…”

“Okay,” I said, interrupting him. Whatever he wanted I didn’t really care about.

He smiled and pulled my shirt off then unfastened my bra. His fingertips on my bare skin sent chills through me. He bent me over the kitchen table and made a quick clean slice alongside my spine. I didn’t even feel it until the warmth of my blood started dripping along my skin.

He pulled my panties down and rubbed his hand in the blood on my back then started to finger me, rubbing hard and fast until he brought me to another first and made me squirt on his kitchen floor. He rubbed my blood on his other hand and stroked his cock. My legs were stretched tight as I was on my tiptoes to have my body bent perfectly over his table.

He pushed his dick into me roughly and I cried out, gripping the sides of the table and digging my fingernails into the soft wood underneath the tabletop as he fucked me roughly. His breath was on my neck as his body pressed to mine. His hands clasped to mine over the sides of the table and he kissed my neck as he thrust hard into me, making the table move a good two feet until it hit the wall it was near.

I was insanely turned on by his hands holding mine down on the table, his body rubbing against mine with each thrust, the pain of the table’s edge digging into my upper thighs. He moved his lips over by my ear and whispered, “You wanted this right?”

I nodded and he thrust harder, making me wince as the movement of his body on mine spread the cut on my back as I cried out. His thumbs rubbed my wrists as his fingers tightened on mine, “Such a beautiful girl, pretty little tight and wet body accepting my manhood into her so willingly. I know the blood is only symbolic, but I like the thought of you bleeding by choice for me.”

My body ached with his weight on me and I turned my head to look at him, “I can’t breathe,” I said through a gasp.

He reluctantly pulled up from me and pulled me up into a more standing position, my bra hung loosely from my arms but still covered my tits. He used the table to hold me still while he thrust harder into me. He crossed my arms over my stomach and clasped his hands in mine, pulling me to him using my own arms as he fucked me.

The table edge pressed against my pussy and thighs with each thrust. I moaned and bent my knees slightly and he moaned as he pushed his hips flush to my ass, “You feel so good, L,” he whispered, “so much better than I even imagined.”

My cunt was squeezing his cock with each thrust as he held my legs tightly together. I felt so full and I wanted to tell him to fuck me harder, but he was religious and I didn’t want him to be offended or ruin the fantasy of me being the virginal conquest. His hands left my fingers and moved down between my legs, playing with my clit as I moaned then bit my lip to keep myself from cursing and begging.

I ached and he pulled himself free of me then sat back in the kitchen chair. He pulled my hand and turned me around to face him, pulling me up onto his lap and guiding me back onto him, “Show me you want me, baby,” he said as he pushed my hair behind my ear then pulled me into a kiss.

My hands were on his shoulders and he carefully pulled my bra off of my arms, dropping it to the floor beside us. I looked him in the eyes and began to slowly ride him, rocking my hips over him as I moved up and down. He had one hand on my hip, his thumb rubbing my clit gently as I rode him. His dick pushed on sensitive areas and his thumb teased me as his lips closed over my breasts, one at a time, savoring and licking my nipples.

I thrust myself down onto him and moaned as my legs went weak and trembled as I rubbed myself back and forth against him with his dick fully in me. My head tipped back and his hand supported me on my back as I moaned, “Fuck me, sir,” as my body arched and ached in pleasure of his dick in me.

He groaned and lifted me up onto the edge of the table and thrust hard and repeatedly through my orgasm and quickly brought me to another as I clung to him, “Say it again,” he groaned.

My body trembled and I gasped but I pushed myself back from him with my hands on his shoulders and looked him in the eye, “My pussy aches for your big dick Mr. V., please fuck me hard, sir. Use my tight, wet cunt for your own pleasure and I will get down on my knees and suck your cock clean of us both,” I said in my soft, quiet voice.

He grabbed my ass and pulled me to him, cumming deeply inside of me as I smiled and moaned as he grunted and his balls tightened and twitched.

“Are you on birth control?” He panted as he gathered my hair in his hands and rubbed the back of my head.

I shook my head and bit my lip.

He smiled and kissed me then whispered to me, “Don’t change that and I will take care of you both.”

I kept my promise and cleaned his cock thoroughly with my tongue and lips then he got me dressed and took me home, his cum still leaking from my cunt as I walked into my parents’ house.

That was the last time we were together. I stopped cleaning his house after that and he came to my other job to see what happened but I avoided him and he didn’t take me blowing him off so kindly. He waited out back, in a blind spot, for me to take the dining room trash out and he cornered me in the dark behind the building, grabbed my arm and pinned me to the wall, kissing me hard as I tried to push him away, “Stop, please?” I said.

“Why’d you stop coming over?” He asked, clearly pained.

I looked him in the eye, “I don’t want to have a kid yet,” I whispered.

His hand went under my t-shirt and I squirmed, trying to get out of his grip, “Please, just let me go?”

He shook his head, “You liked it, I know you did,” he said as he thrust me back against the building again, hitting my back on the rough brick.

“They’re going to notice I’m missing,” I said.

He was in tears as he looked me over, “If you say anything about this to anyone…just remember who I am in this town. It won’t go well for you or your family. Remember that,” he spat at me.

I pulled out of his grip and started to run towards the back door, he came after me and grabbed my arm, pulling me tightly to him and putting my hand between his legs as he smiled at me, “You’re a dime a dozen in this town, L. A needy little whore who will ride an old man’s dick for the promise of a little cash.”

He took his hand off of mine and my fingers stayed on his cock, rubbing him slightly as he pulled something from his pocket and slid his hand under my shirt. A wad of cash was pushed into my bra and he pushed me to the ground hard, I cut my hands when I fell. He looked down at me and scoffed as I scrambled to my feet and ran back inside of the building.

My boss saw him grab me and push me down, but none of the rest of it. B and R put me in their office, I was sitting on the floor, crying, and they went outside and after their friend. He wasn’t allowed to be within two hundred feet of the restaurant without the cops being called on him. I didn’t expect them to stand up for me, I expected them to lecture me and tell me not to tell anyone if I wanted to keep my job. B sat in the office with me and her husband, R, went up front and took my place on shift. B asked me twice what happened but I didn’t want to say, so I just said he was mad that I didn’t want the cleaning job he offered me and left it at that. She knew there was more to it, but she just cleaned up my hands and let me tell her what I wanted to then she took me home.

I saw him in passing after that and he always looked like he wanted to come over and talk to me but couldn’t bring himself to do it. Sometimes I wish he had. After him I ended up in an incredibly abusive relationship with no monetary benefit, I had great taste in men. I wish I had indulged in more female relationships. They not only got me off much more thoroughly, but not once did they ever encourage my self destructive tendencies. Guys…they seem to get off on my masochism to an unhealthy degree.

Source: reddit.com/r/Erotica/comments/iob0w2/the_cherry_milkshake_mf_age_gap_cutting_masochism