My night with Cindy
I met Cindy a few years ago. I ran a vintage clothing store, and she stopped
In almost weekly. Sometimes the 18 year-old would just browse, others she’d try on some clothes, usually cute dresses. She would take her time , and buy when she had the money, usually with small bills. One day, after she’d been in the dressing room almost 30 minutes, I felt the need to check up on her, see if she was okay. I went back, and heard some soft moans coming from the stall I’d set her up in. Concerned, definitely curious, I unlocked the door to find Cindy sitting on the bench with her panties around her ankles and 2 fingers massaging her pussy. Surprised, she grabbed everything she could, and ran out of the store and down the street. Unfortunately, she’d forgotten her purse and phone. When Cindy returned a few hours later, she apologized profusely, and promised it would,t happen again. I told her about the time a previous roommate caught me, and told her that it happens. She invited me out for a drink, and that’s where we started.
Flash forward a few years. We’d started seeing each other on a FWB.mentor/ basis. Yesterday, I opened my door to find Cindy standing there in a simple blouse and mini skirt. I let Cindy in, and lead her to my bedroom. I sat down, pull her close, and sit her on my lap, straddling my legs. I push her skirt up around her waist, finding no panties. I gave her ass a firm squeeze with both hands, and pull her cheeks apart to expose her asshole. She pulls her blouse up and over her head, letting it fall to the floor, exposing those sweet, cute tits constrained by a lace bralette that matched her skirt. I let go of her ass, and slid my hands underneath her bralette, slid it up over her head, and dropped it onto her blouse. With my hands re-grabbing her ass, I began to kiss and lick her tits. I avoided her nipples and areola, as I was enamoured with the shape and skin tone of her lovely tits.
I asked her if she was a good girl, as I playfully slapped her ass. “Yes, I am”, she replied quietly.
“Good girls wear panties”, I replied.
“Yes, ma’am” she whispered. She stood up, stepped back, and pulled her skirt down as far as she could, trying to cover up as much as possible.
“So, are you a good girl then?”
“No, ma’am” she replied, even more quiet this time.
“Why didn’t you tell me the truth?”
“I was ashamed.“
“Why were you ashamed?”
“Because I’m a slut.”
As thought about what I was going to do next, she got down on her knees, with her hands on her thighs.
We called that “The Position.”
As we explored our sexuality and her submissiveness together, I had her kneel in front of me when I was thinking about what she needed. I smiled, knowing this was a teaching point. Being a few years older, she came to me seeking guidance. I knew she slept around, and that I encouraged. Sex was something to be enjoyed and experienced, not to be scared of.
“You are allowed to have all the sex you want, however and with whomever you want. If that makes you a slut, so be it. Be who you want to be, and be proud of that” I said to her, and she looked up at me and smiled.
“What you aren’t allowed to do”, I continued, is lie to me. Dishonesty is not allowed. You need to be punished.”
I sat down in a big, comfy chair I keep in my room, and motioned Cindy to come to me. I spread my legs, and Cindy knew exactly what I wanted. She started kissing my inner thighs, one thigh then the other, every inch until she reached my pussy. She stopped and looked up at me, and when I nodded, Cindy dove tongue first into my wetness.
Cindy was good at oral sex. I’d caught Cindy and her female roommate together on many occasions. Today, she was showing me all she knew about pleasing a woman.
My orgasm built up slowly, but steadily. When it did hit, it didn’t seem to end, lapping at me like waves hitting the beach. I could see Cindy slowing down, and she started shifting from one knee to the other in obvious discomfort. I pushed her face away from my dripping twat, stood up, and went to my toy box. I removed a remote vibrating egg, and gave it to Cindy. Instinctively, she slid it into her pussy. I turned it on, then off quickly, just to test it.
I went to my bed, and lied on my stomach. When I spread my legs, exposing my ass, Cindy knew what was expected of her. She positioned herself between my legs, and after kissing my ass cheeks well and good, I told her it was time. She buried her face between my ass cheeks, and delicately began eating my ass, but not with the same enthusiasm as my pussy. After a few moments, Cindy realized that this was not pleasing me, and started making more of an effort.
“2 fingers” I moaned, and Cindy complied almost instantly, sliding them in to my pussy as she rubbed my clit with her thumb. This girl was good at getting me off. I had lost track of time, and orgasms, when Cindy told me that she needed to pee. She smiled when I allowed her to go, but her smile faded when I told her to return with my hairbrush. She was well aware of what was coming next.
I sat up on the edge of my bed when Cindy returned, and she assumed the position, over my knees with her arms crossed behind her back. Using the brush, I spanked her ass to a bright-red colour. Not enough to leave marks, but enough to make sitting uncomfortable. She’d had enough after 10 strikes to each cheek, and I told her to get up. Cindy stood in front of me and started to rub her sore bottom before I stopped her. She was not allowed to enjoy this at all. I sent her into the kitchen to begin dinner while I relaxed on the couch. I would activate her vibrator randomly, when the mood struck me. I’d let her come close to orgasm, then turn it off. The first few times, Cindy would get an expectant look, like I would let her come. After those first few, she’d get an annoyed look and kneel on the floor in a ball, knowing disappointment was near.
Cindy set our dinners on the table, and invited me over. She tried to sit down, but her ass was still too sore. She asked if she could sit on a pillow, but I said no. After thinking about it, she placed plate on her chair and kneeled down to eat. We chatted nicely throughout dinner, not speaking a word about her punishment. After dinner was eaten and the dishes cleared away, we cuddled up on the couch to watch a movie until she fell asleep in my arms. We headed to bed soon after.
I woke around 4am, and decided Cindy had been punished enough. Besides, I wanted her pussy in my face when she arrived the day before, and I’d denied myself long enough. I spread her legs gently, so as not to wake her, and started to kiss and lick her soaking wet pussy. She would stir and moan, but didn’t wake up. I slid 2 fingers into her sloppy wet hole, and rubbed her g-spot as I licked, flicked., and kissed her clit. More soft moans escaped her, and she didn’t wake until she was in the throes of an orgasm. She squirted in my mouth, and I swallowed every drop. (I’m just as big of a slut as Cindy is. Probably more.)
Cindy woke with a big smile on her face, and I rolled her over. I told her to get up on her knees as I took the strap-on from my night table and stepped into it, securing it to my hips. I crawled to her on the bed, on her knees. My big, fake cock was swallowed up by her hungry cunt, and I started to gently rock back and forth into her. As the speed and intensity grew, I grabbed a handful of her hair. I fucked her good and hard, just as she liked. I let go of her hair, and she fell forward. Cindy put her face into a pillow, to muffle the sounds of pleasure that would surely wake the neighbours.
In between the screams of pleasure, she would first ask, then bed me to stop. When I finally did stop, we both collapsed in a tired, sweaty heap. The sheets, the ones that hadn’t been thrown from the bed, were soaked in sweat and cum. I didn’t care, nor did Cindy. We laid there, soaked and sticky, and fell asleep.
We continued to see each other, at first frequently, then not so much, thorough Cindy’s college years. We keep in touch through Facebook, but haven’t actually spoken in ages. She moved away to follow her career dreams, and she’s doing well.
In almost weekly. Sometimes the 18 year-old would just browse, others she’d try on some clothes, usually cute dresses. She would take her time , and buy when she had the money, usually with small bills. One day, after she’d been in the dressing room almost 30 minutes, I felt the need to check up on her, see if she was okay. I went back, and heard some soft moans coming from the stall I’d set her up in. Concerned, definitely curious, I unlocked the door to find Cindy sitting on the bench with her panties around her ankles and 2 fingers massaging her pussy. Surprised, she grabbed everything she could, and ran out of the store and down the street. Unfortunately, she’d forgotten her purse and phone. When Cindy returned a few hours later, she apologized profusely, and promised it would,t happen again. I told her about the time a previous roommate caught me, and told her that it happens. She invited me out for a drink, and that’s where we started.
Flash forward a few years. We’d started seeing each other on a FWB.mentor/ basis. Yesterday, I opened my door to find Cindy standing there in a simple blouse and mini skirt. I let Cindy in, and lead her to my bedroom. I sat down, pull her close, and sit her on my lap, straddling my legs. I push her skirt up around her waist, finding no panties. I gave her ass a firm squeeze with both hands, and pull her cheeks apart to expose her asshole. She pulls her blouse up and over her head, letting it fall to the floor, exposing those sweet, cute tits constrained by a lace bralette that matched her skirt. I let go of her ass, and slid my hands underneath her bralette, slid it up over her head, and dropped it onto her blouse. With my hands re-grabbing her ass, I began to kiss and lick her tits. I avoided her nipples and areola, as I was enamoured with the shape and skin tone of her lovely tits.
I asked her if she was a good girl, as I playfully slapped her ass. “Yes, I am”, she replied quietly.
“Good girls wear panties”, I replied.
“Yes, ma’am” she whispered. She stood up, stepped back, and pulled her skirt down as far as she could, trying to cover up as much as possible.
“So, are you a good girl then?”
“No, ma’am” she replied, even more quiet this time.
“Why didn’t you tell me the truth?”
“I was ashamed.“
“Why were you ashamed?”
“Because I’m a slut.”
As thought about what I was going to do next, she got down on her knees, with her hands on her thighs.
We called that “The Position.”
As we explored our sexuality and her submissiveness together, I had her kneel in front of me when I was thinking about what she needed. I smiled, knowing this was a teaching point. Being a few years older, she came to me seeking guidance. I knew she slept around, and that I encouraged. Sex was something to be enjoyed and experienced, not to be scared of.
“You are allowed to have all the sex you want, however and with whomever you want. If that makes you a slut, so be it. Be who you want to be, and be proud of that” I said to her, and she looked up at me and smiled.
“What you aren’t allowed to do”, I continued, is lie to me. Dishonesty is not allowed. You need to be punished.”
I sat down in a big, comfy chair I keep in my room, and motioned Cindy to come to me. I spread my legs, and Cindy knew exactly what I wanted. She started kissing my inner thighs, one thigh then the other, every inch until she reached my pussy. She stopped and looked up at me, and when I nodded, Cindy dove tongue first into my wetness.
Cindy was good at oral sex. I’d caught Cindy and her female roommate together on many occasions. Today, she was showing me all she knew about pleasing a woman.
My orgasm built up slowly, but steadily. When it did hit, it didn’t seem to end, lapping at me like waves hitting the beach. I could see Cindy slowing down, and she started shifting from one knee to the other in obvious discomfort. I pushed her face away from my dripping twat, stood up, and went to my toy box. I removed a remote vibrating egg, and gave it to Cindy. Instinctively, she slid it into her pussy. I turned it on, then off quickly, just to test it.
I went to my bed, and lied on my stomach. When I spread my legs, exposing my ass, Cindy knew what was expected of her. She positioned herself between my legs, and after kissing my ass cheeks well and good, I told her it was time. She buried her face between my ass cheeks, and delicately began eating my ass, but not with the same enthusiasm as my pussy. After a few moments, Cindy realized that this was not pleasing me, and started making more of an effort.
“2 fingers” I moaned, and Cindy complied almost instantly, sliding them in to my pussy as she rubbed my clit with her thumb. This girl was good at getting me off. I had lost track of time, and orgasms, when Cindy told me that she needed to pee. She smiled when I allowed her to go, but her smile faded when I told her to return with my hairbrush. She was well aware of what was coming next.
I sat up on the edge of my bed when Cindy returned, and she assumed the position, over my knees with her arms crossed behind her back. Using the brush, I spanked her ass to a bright-red colour. Not enough to leave marks, but enough to make sitting uncomfortable. She’d had enough after 10 strikes to each cheek, and I told her to get up. Cindy stood in front of me and started to rub her sore bottom before I stopped her. She was not allowed to enjoy this at all. I sent her into the kitchen to begin dinner while I relaxed on the couch. I would activate her vibrator randomly, when the mood struck me. I’d let her come close to orgasm, then turn it off. The first few times, Cindy would get an expectant look, like I would let her come. After those first few, she’d get an annoyed look and kneel on the floor in a ball, knowing disappointment was near.
Cindy set our dinners on the table, and invited me over. She tried to sit down, but her ass was still too sore. She asked if she could sit on a pillow, but I said no. After thinking about it, she placed plate on her chair and kneeled down to eat. We chatted nicely throughout dinner, not speaking a word about her punishment. After dinner was eaten and the dishes cleared away, we cuddled up on the couch to watch a movie until she fell asleep in my arms. We headed to bed soon after.
I woke around 4am, and decided Cindy had been punished enough. Besides, I wanted her pussy in my face when she arrived the day before, and I’d denied myself long enough. I spread her legs gently, so as not to wake her, and started to kiss and lick her soaking wet pussy. She would stir and moan, but didn’t wake up. I slid 2 fingers into her sloppy wet hole, and rubbed her g-spot as I licked, flicked., and kissed her clit. More soft moans escaped her, and she didn’t wake until she was in the throes of an orgasm. She squirted in my mouth, and I swallowed every drop. (I’m just as big of a slut as Cindy is. Probably more.)
Cindy woke with a big smile on her face, and I rolled her over. I told her to get up on her knees as I took the strap-on from my night table and stepped into it, securing it to my hips. I crawled to her on the bed, on her knees. My big, fake cock was swallowed up by her hungry cunt, and I started to gently rock back and forth into her. As the speed and intensity grew, I grabbed a handful of her hair. I fucked her good and hard, just as she liked. I let go of her hair, and she fell forward. Cindy put her face into a pillow, to muffle the sounds of pleasure that would surely wake the neighbours.
In between the screams of pleasure, she would first ask, then bed me to stop. When I finally did stop, we both collapsed in a tired, sweaty heap. The sheets, the ones that hadn’t been thrown from the bed, were soaked in sweat and cum. I didn’t care, nor did Cindy. We laid there, soaked and sticky, and fell asleep.
We continued to see each other, at first frequently, then not so much, thorough Cindy’s college years. We keep in touch through Facebook, but haven’t actually spoken in ages. She moved away to follow her career dreams, and she’s doing well.
5年前
