u/pleasedontfindme69

We laid in the hotel bed together after the shower. I had my head on his chest and he played with my hair. “I didn’t make you cum though” I said, half asleep. “You will,” he answered gently rubbing my back with his rough hand, “I figured you could use a break.” He was right. I was tired, and my body was in total shock. I’d never had anyone make me cum during sex without a significant amount of coaching, and even then, I’d never cum the way I just did.

The events of the night started creeping back into my brain. Tears slipped out of my eyes no matter how hard I tried to suck them back up. He pulled me closer to him with a hand on my back and I buried my face in his chest. Still scratching my back he said gently “it’s okay. You’re okay. I’m here.” I stopped fighting the tears. I’d been in a weird place, not sleeping much, not eating at all, drinking far too much. I felt broken and young. “Can I sleep with you?” I asked through tears. “Of course baby.” He answered and wiped my face. I’m sure I looked like a mess but I didn’t care. He seemed like a nice enough guy and maybe this was exactly what I needed for the night. I turned over and he did the same to spoon me. I fell asleep on his bicep in seconds, with him slowly running a hand up and down my arm.

I don’t know when I woke up but the room was still pitch black. I was groggy and disoriented, but felt immediately comforted by the arms holding me. Still half asleep, I started lazily grinding my hips back into him behind me. I didn’t know he was awake but I felt his hand move from my shoulder slowly down my ribs under the covers to my hip. It pulled me back into him and I grinded into him harder, turning my head to find his lips behind me. With one hand in my hair, the other came up to grab my tit and he started grinding back into me with his cock fully hard. I started to roll over to face him but the hand came up to my neck and he whispered “stay.” He pulled my panties to the side and slowly slid inside of me. We gasped into each others mouths and I felt a wave of pleasure wash over my body. He spread my legs and started slowly circling my clit while pushing in and out of me. I practically whimpered into his mouth feeling my legs quiver. “That’s it baby” he moaned “deep breaths.” I tried, but it felt so good I thought I might accidentally faint. Then, he flexed his arm under my back and repositioned me so that my knees were against my chest my legs folded. I found my whole body wrapped up in his arms under the covers and he entered me from below. In one swift motion, he slid my panties off my feet and stuffed them in my mouth. “It’s a hotel so I don’t care but we can’t have a noise complaint interrupting us” he said quietly.

The second he slid inside I almost came. The angle was unbelievable and I moaned so loudly I’m sure if not for the panties gagging me I would have woken up the whole building. “Do you like that baby?” He asked knowing I couldn’t respond. I just moaned affirmatively and nodded my head. He fucked me harder and continued “you like being taken care of” he said in my ear and I shivered, “you like that I’m too old for you” I was dripping wet all over the sheets, “you like that I know what I’m doing” I was fucking shaking, “you like that I have your whole little body in my arms. All of you at my disposal” that pushed me over the top. My eyes rolled back into my head and my whole body tightened. I felt myself start shaking and once again, tears were rolling down my face. “fuckkkk” i screamed muffled into my gag. I was shaking, crying, and cumming all over him. I felt like I was having an exorcism. He held me together and kissed me over the panties: “that’s it baby” “cum for me” “I’ve got you.” I buried my face in his neck, breathing hard and kissing him. He held me tight and kissed me back hard. My body convulsing and twitching. After a minute, he gathered up my hair into a hand and said “now get on your knees and suck my dick, beautiful”

Desperate to return the favor, I spit out the panties to smile and crawled to the end of the bed. With my ass up in the air, I got to work immediately. I looked up at him with big tear filled eyes and makeup running all over my face, and ran my tongue from his balls to his tip. He leaned his head back and twitched a little. I laughed a little in my head, evidently I shouldn’t worry about being less experienced. I didn’t waste any time teasing him, I spit on my hands and started circling the tip while stroking 2 hands up and down his shaft. I alternated between licking his balls while stroking him and focusing on the tip with 2 hands working around him. Within 5 minutes, he was arching his back into me and I could tell his cock was throbbing.

“If you keep doing that I’ll cum” he moaned and I sped up. “Jesus fuck, Cherry” he tensed and gripped my hair hard. I felt his cock twitch and I took its full length into my throat, feeling his balls throb and empty. His body kept twitching as he moaned my fake name. I smiled, proud of myself, and went into the bathroom to wash my face.

We got back in bed together and I laid back down on his chest. “Can I stay here with you a while” I asked after a few minutes of silence. “You can stay however long you like, but I’ll probably leave before you wake up” he answered. I nodded into him and once again passed out in seconds on his chest. When I woke up the room was bright and warm, I was still naked and my face was pressed into a big fluffy hotel pillow. He was gone and there was no trace of him except for a tray set up by the bed with French toast, fruit, and coffee. On it was a tiny piece of paper that had a phone number.

part 2

A week ago I found out that the man I’d been in love with for 5 years is dating someone new. So being a 21 year old girl in the best shape of my life, I did the only thing I knew how to. I called all of my girlfriends, picked up a couple enormous bottles of wine, and got into the shower to prepare for the night of a lifetime.

I settled on a tiny black dress that hugged my ass and knee high black boots. My long red hair was straightened and I coated my eyes in black eyeliner. Tonight, I was someone else. Anyone else. Tonight, I decided my name would be “Cherry.” We walked into my favorite club and I felt an evil kind of smirk color my face. I was heartbroken and here was a room full of men practically begging to comfort me exactly how I wanted. But patience was key, I didn’t want to go home with the first guy that complimented me. I needed someone to prove I shouldn’t waste another minute crying over my skinny little ex.

Standing on the stage, I found him. The lights were flashing and I was more drinks in than I care to remember. My girlfriend and I were dancing dirty in a glass box above the crowd… grinding, making out, showing off like pretty birds attracting mates. And that’s when I saw him. He was wearing a Cowboy hat and boots with starched jeans and a button up that was left open revealing thick chest hair. He had a mustache that reminded me of tom selleck and was most definately too old for me. Late thirties at best, but you couldn’t have paid me to care in that moment. While making eye contact with him, I grabbed my friend by the hips and bent her over to dance on me, fingers in her waistband. I watched him raise his hand to where I could see it and drag one finger in a “come hither motion.” I smiled to myself, it appeared I’d found my victim for the night

“You’re coming home with me right” was the first thing I said to him after making my way down out of the box, across the stage, and through the crowd. “You’re a bit young for me” he said in a deep gravelly voice with an overpowering southern accent. “Thats exactly what I need tonight” I said wrapping my arms around his neck and pulling him into a kiss. I felt big hands grip my hips assertively. They felt along my waistband and goosebumps raised in my skin. Yeah, I thought to myself, this was EXACTLY what I needed tonight.

After dancing together for an hour and drinking more than I should have, my head knocked into his hotel room door. He pressed me there hands working slowly up my skirt. “I never did ask you your name” he hummed in my ear slowly undoing the hook on the back of my dress. “Cherry” I answered breathily. He slid the zipper down revealing my small perky tits. “A coed named Cherry” he said with a laugh into my stomach. Kissing down my thighs to my boots, “I am most definately too old for this.”
“What do you do for work?” I asked in mild curiosity while he unzipped the boots, leaving me in just thigh high socks and a lace g-string. “I’m a fire fighter” he answered. “Fucking perfect” I said as he picked me up, hands under my ass pressing me against the door.

He carried me to the bed and threw me down onto it, pressing me down to kiss me while I wrapped my legs around him. As soon as he stood up I moved to my knees on the floor and undid belt. I ripped off his jeans and his boxers and enthusiastically got to work. “Hit me,” I said, looking up at him innocently. “No…” he answered hesitantly. “It’s okay, I like it like that” I said still running my hand up and down his thick shaft “be rough with me.” He grabbed my hands and picked me up off the floor putting me back on the edge of the bed. Still standing over me he said “is that how you let these little boys fuck you” I didn’t answer but I was shocked to feel a tear run down my cheek. I wiped it, embarassed, but more followed. He wiped them with his thumb and got on his knees to look me in the eyes. “….you seem so…..broken.” He said after a minute, looking at me almost quizzically.

I didn’t think it was that obvious. But sitting there in my knee socks and panties, in a hotel room with some guy 10+ years older than me, begging him to hit me in the face, I knew he was right. He had both hands on either side of my face wiping away tears and seemed oddly undeterred by my weird emotional response. “I’m not really in the buisness of breaking women” he said softly. “But I have been known, on occasion, to put them back together.” The reaction was comforting. And maybe I didn’t need to have more sex with men who wanted to hurt me. He pushed me onto my back. “I’m going to tell you exactly what to do, so you don’t have to think about anything. I want you to completely turn your brain off and just listen. I’m going to show you what it’s like to get fucked by a man.” It wasn’t what I was used to at all, but the whole thing was turning me on unbelievably bad. He was right, I never knew if I attracted it or if it was just boys my age, but most of the sex I’d had in my life had been rough and degrading. I always said it was what I was into, but I’d never actually experienced anything else.

“Turn over to face away from me and bend over, knees together” he said in a low assertive voice while standing up and taking off his shirt. He was huge, atleast 6’4” and that kind of muscular all firefighters are. “Okay” I answered, voice still shakey from crying. “Yes sir” he corrected me. “Yes sir.” I answered bending over in the big hotel bed. I pressed my face into the comforter, ass in the air, with my arms outstretched gripping the sheets in front of me. His fingers hooked the strings that held my tiny lace panties to my body, and slowly he peeled them down my legs. “So wet already” he mused, firm hands massaging my tight ass. Suddenly I felt his tongue slide up from my clit to my ass and I took a sharp breath. He knew exactly what he was doing, and continued slowly, torturously, licking my needy clit. I was pushing my hips back into him but his hands on my hips held me still. Then he stood up and bent over me, slowly rubbing his shaft against my clit. “Take a deep breath for me baby” he whispered in my ear. I inhaled and realized I had gotten so worked up while he was eating my pussy that I was on the verge of passing out. “I’m going to put it in now, are you gonna take it like a good girl?”
“Yes sir” I moaned into the comforter. “Knees together, arms up” he said. Bending over to grip my wrists and secure them together. I was dripping wet and felt him slowly push his full length deep inside of me. “Holyyyyyy shit” i said, wincing in pain. It slipped in easily because of how wet I was but it had been a while since I’d been stretched out like that. “It’s okay baby” he said in my ear, leaving himself inside of me. “We’ll take our time” he slowly started sliding in and out of me. With every thrust I thought I might have to tap out, it was so deep I felt like my vision was closing in. “Just breathe and don’t think” he said Aparently noticing that I was struggling. I remember thinking he was oddly specific about the position but after a minute, I understood the point. It felt fucking amazing. I started moaning and begging for it harder. “Holy fuck Cherry, you are so tight.” He said shakily into my ear. With one hand on my back he pushed me flat onto the bed and started fucking me hard. I didn’t think it could possibly get deeper but it did and I couldn’t bother to care that everyone in the hotel could probably hear me. I was moaning loudly and screaming his name, feeling myself get closer and closer.

Suddenly he stopped and slid out of me. I tried to catch my breath wiping sweaty hair out of my face. Walking over to the bedside table he called out without looking at me “get on your back.” I did and saw him coming back with a sleep mask. He fitted it over my eyes and secured it tight. I didn’t object. “You need to learn to turn your brain off” god I was so into this. “Let me make you feel good” I heard his deep voice say, but I couldn’t see a thing. I felt so vulnerable. I was completely at his mercy. I felt him kiss my neck, collarbone, and settle on my tits. His tongue circled my nipple while at the same time I felt a hand come to my thighs and part them. A finger entered me and came out to circle my clit while the other hand pinched my nipple and his mouth littered me with kisses and bites. I felt like my skin was on fire. “That feels so fucking good” I moaned, arching my back into him. “Don’t say anything, and don’t perform. I just want you to feel. Take another breath for me baby”

I took his instructions as orders and inhaled deeply. As I exhaled, I blocked out everything except what I was feeling. A low guttural moan grew in my belly. It really did feel so insanely good. His fingers and mouth touched me everywhere all while my clit was growing achy and needy. One finger inside of me became 2, and then 3. I was getting so close, he seemed to know exactly where to touch me. Suddenly the fingers inside of me got faster and hooked upward hard against my g-spot. I moaned desperately and felt myself tightening. “Please don’t stop” I begged. “Cum for me baby” he said and it was all the permission I needed. My body tensed against his fingers and I started shaking. “Oh my god oh my god I’m fucking cumming” I practically screamed. My body started convulsing and I writhed around ghasping for air. I felt another tear fall down my face while I came harder than I’ve ever cum before. “That’s it baby let it out” he encouraged me while holding me as still as he could. I quivered and shook on his fingers worrying I might somehow hurt him with how hard I was cumming. When it was finally over a minute later I breathed a sign of exhaustion and he laughed to himself. He handed me a towel and walked over to the shower to turn it on. Calling to me from the bathroom he said “dont slip on the floor” I didn’t know what he could mean but I slid off the bed and put my feet down into a puddle of water. I had squirted everywhere. I didn’t even know I could do that. I threw my towel down to clean it up and went to meet him in the shower, dazed, confused, and completely in shock over what just happened.

A week ago I found out that the man I’d been in love with for 5 years is dating someone new. So being a 21 year old girl in the best shape of my life, I did the only thing I knew how to. I called all of my girlfriends, picked up a couple enormous bottles of wine, and got into the shower to prepare for the night of a lifetime.

I settled on a tiny black dress that hugged my ass and knee high black boots. My long red hair was straightened and I coated my eyes in black eyeliner. Tonight, I was someone else. Anyone else. Tonight, I decided my name would be “Cherry.” We walked into my favorite club and I felt an evil kind of smirk color my face. I was heartbroken and here was a room full of men practically begging to comfort me exactly how I wanted. But patience was key, I didn’t want to go home with the first guy that complimented me. I needed someone to prove I shouldn’t waste another minute crying over my skinny little ex.

Standing on the stage, I found him. The lights were flashing and I was more drinks in than I care to remember. My girlfriend and I were dancing dirty in a glass box above the crowd… grinding, making out, showing off like pretty birds attracting mates. And that’s when I saw him. He was wearing a Cowboy hat and boots with starched jeans and a button up that was left open revealing thick chest hair. He had a mustache that reminded me of tom selleck and was most definately too old for me. Late thirties at best, but you couldn’t have paid me to care in that moment. While making eye contact with him, I grabbed my friend by the hips and bent her over to dance on me, fingers in her waistband. I watched him raise his hand to where I could see it and drag one finger in a “come hither motion.” I smiled to myself, it appeared I’d found my victim for the night

“You’re coming home with me right” was the first thing I said to him after making my way down out of the box, across the stage, and through the crowd. “You’re a bit young for me little lady” he said in a deep gravelly voice with an overpowering southern accent. “Thats exactly what I need tonight” I said wrapping my arms around his neck and pulling him into a kiss. I felt rough hands grip my hips assertively. They felt along my waistband and goosebumps raised in my skin. Yeah, I thought to myself, this was EXACTLY what I needed tonight.

After dancing together for an hour and drinking more than I should have, my head knocked into his hotel room door. He pressed me there hands working slowly up my shirt. “I never did ask you your name” he hummed in my ear slowly undoing the hook on the back of my dress. “Cherry” I answered breathily. He slid the zipper down revealing my small perky tits. “A coed named Cherry” he said with a laugh into my stomach. Kissing down my thighs to my boots, “I am most definately too old for this.”
“What do you do for work?” I asked in mild curiosity while he unzipped the boots, leaving me in just thigh high socks and a lace g-string. “I’m a fire fighter” he answered. “Fucking perfect” I said as he picked me up, hands under my ass pressing me against the door.

He carried me to the bed and threw me onto it, pressing me down to kiss me while I wrapped my legs around him. As soon as he stood up I moved to my knees on the floor and undid his belt. I ripped off his jeans and boxers and enthusiastically got to work. “Hit me,” I said, looking up at him innocently. “No…” he answered hesitantly. “It’s okay, I like it like that” I said running my hand up and down his thick shaft “be rough with me.” He grabbed my hands and picked me up off the floor putting me back on the edge of the bed. Still standing over me he said “is that how you let these little boys fuck you” I didn’t answer but I was shocked to feel a tear run down my cheek. I wiped it, embarassed, but more followed. He wiped them with his thumb and got on his knees to look me in the eyes. “….you seem so…..broken.” He said after a minute, looking at me almost quizzically.

I didn’t think it was that obvious. But sitting there in my knee socks and panties, in a hotel room with some guy 15+ years older than me, begging him to hit me in the face, I knew he was right. He had both hands on either side of my face wiping away tears and seemed oddly undeterred by my weird emotional response. “I’m not really in the buisness of breaking women” he said softly. “But I have been known, on occasion, to put them back together.” The reaction was comforting. And maybe I didn’t need to have more sex with men who wanted to hurt me. He pushed me onto my back. “I’m going to tell you exactly what to do, so you don’t have to think about anything. I want you to completely turn your brain off and just listen. I’m going to show you what it’s like to get fucked by a man.” It wasn’t what I was used to at all, but the whole thing was turning me on unbelievably bad. He was right, I never knew if I attracted it or if it was just boys my age, but most of the sex I’d had in my life had been rough and degrading. I always said it was what I was into, but I’d never actually experienced anything else.

“Turn over to face away from me and bend over, knees together” he said in a low assertive voice while standing up and taking off his shirt. He was huge, atleast 6’4” and that kind of muscular all firefighters are. His dick fit his stature, it was atleast 8 inches and thick. “Okay” I answered, voice still shakey from crying. “Yes sir” he corrected me. “Yes, sir.” I answered bending over in the big l bed. I pressed my face into the comforter, ass in the air, with my arms outstretched gripping the sheets in front of me. His fingers hooked the strings that held my tiny lace panties to my body, and slowly he peeled them down my legs. “So wet already” he mused, firm hands massaging my tight ass. Suddenly I felt his tongue slide up from my clit to my ass and I took a sharp breath. He knew exactly what he was doing, and continued slowly, torturously, licking my needy clit. I was pushing my hips back into him but his hands on my hips held me still. Then he stood up and bent over me, slowly rubbing his shaft against my clit. “Take a deep breath for me baby” he whispered in my ear. I inhaled and realized I had gotten so worked up while he was eating my pussy that I was on the verge of passing out. “I’m going to put it in now, are you gonna take it like a good girl?”
“Yes sir” I moaned into the comforter. “Knees together, arms up” he said. Bending over to grip my wrists and secure them together. I was dripping wet and felt him slowly push his full length deep inside of me. “Holyyyyyy shit” i said, wincing in pain. It slipped in easily because of how wet I was but it had been a while since I’d been stretched out like that. “It’s okay baby” he said in my ear, leaving himself inside of me. “We’ll take our time” he slowly started sliding in and out of me. With every thrust I thought I might have to tap out, it was so deep I felt my vision closing in. “Just breathe and don’t think” he said apparently noticing that I was struggling. I remember thinking he was oddly specific about the position but after a minute, I understood the point. It felt fucking amazing. I started moaning and begging for it harder. “Holy fuck Cherry, you are so tight.” He said shakily into my ear. With one hand on my back he pushed me flat onto the bed and started fucking me hard. I didn’t think it could possibly get deeper but it did and I couldn’t bother to care that everyone in the hotel could probably hear me. I was moaning loudly and screaming his name, feeling myself get closer and closer.

Suddenly he stopped and slid out of me. I tried to catch my breath wiping sweaty hair out of my face. Walking over to the bedside table he called out without looking at me “get on your back.” I did and saw him coming back with a sleep mask. He fitted it over my eyes and secured it tight. I didn’t object. “You need to learn to turn your brain off” god I was so into this. “Let me make you feel good” I heard his deep voice say, but I couldn’t see a thing. I felt so vulnerable. I was completely at his mercy. I felt him kiss my neck, collarbone, and settle on my tits. His tongue circled my nipple while at the same time I felt a hand come to my thighs and part them. A finger entered me and came out to circle my clit while the other hand pinched my nipple and his mouth littered me with kisses and bites. I felt like my skin was on fire. “That feels so fucking good” I moaned, arching my back into him. “Don’t say anything, and don’t perform. I just want you to feel. Take another breath for me baby” I took his instructions like orders and inhaled deeply. As I exhaled, I blocked out everything except what I was feeling. A low guttural moan grew in my belly. It really did feel so insanely good. His fingers and mouth touched me everywhere all while my clit was growing achy and needy. One finger inside of me became 2, and then 3. I was getting so close, he seemed to know exactly where to touch me.

Suddenly the fingers inside of me got faster and hooked upward hard against my g-spot. I moaned desperately and felt myself tightening. “Please don’t stop” I begged. “Cum for me baby” he said and it was all the permission I needed. My body tensed against his fingers and I started shaking. “Oh my god oh my god I’m fucking cumming” I practically screamed. My body started convulsing and I writhed around ghasping for air. I felt another tear fall down my face while I came harder than I’ve ever cum before. “That’s it baby let it out” he encouraged me while holding me as still as he could. I quivered and shook on his fingers worrying I might somehow hurt him with how hard I was cumming. When it was finally over a minute later I breathed a sign of exhaustion and he laughed to himself. He handed me a towel and walked over to the shower to turn it on. Calling to me from the bathroom he said “dont slip on the floor” I didn’t know what he could mean but I slid off the bed and put my feet down into a puddle of water. I had squirted everywhere. I didn’t even know I could do that. I threw my towel down to clean it up and went to meet him in the shower, dazed, confused, and completely in shock over what just happened.