Me, A Chaperone?
Sarah and I were laying in bed after a particularly satisfying evening of love making. She surprised me tonight by being the aggressive one for a change. It was nice to let someone else take command. She said that she had something to ask me but didn't know how to go about it. "Baby," I said. "You can ask me anything. You know that." " You're right as usual. Well, my daughter, who you haven't met yet, is going on a trip with her lacrosse team. One of the chaperones backed out and if we don't find someone to replace her the girls won't be able to go. I was wondering if you would like to do it. We're going to the Virgin Islands. The girls have been looking forward to this trip for 3 years." Of course I laughed. Really! Me chaperoning a group of college senior girls. I said that I would love to go but money was tight and I didn't think I could. Oh don't worry about that she told me. The trip was already paid for by the woman who backed out and her money was non-refundable. A free trip? The only question I had is when we were leaving.
We landed on a sultry summer afternoon. The place we were staying at was all inclusive so the first place I headed to was the bar. I had only planned on having one drink and going back to my room, alone, to take a nap. Dierdra, Sarah's daughter, had other plans. She came in just as I was getting up to leave. Please stay and have a drink with me Miss Kate. How could I refuse. We ended up having more than one drink. I was pretty drunk and so was Dierdra. When I drink I also get horny. I was thinking, how can I politely leave and go back to my room and satisfy my itch with my trusty vibrator. I never go on a trip without it. I was making my excuses to Deirdra when she blurted out, " Miss Kate, I have a confession. I was hoping you would be alone so I could get you drunk and seduce you. I think you are a very beautiful woman and I would love to taste your hot pussy." I was a little shocked but who am I to refuse a request like that. Besides getting my pussy licked by a hot 21 year old was much better than a fake dick. I said to her, " Well if it's pussy licking you want, why are we wasting time talking about it. Let's go back to my room and see what we can do for each other.
When we got back to my room, suddenly shyness overtook me. I told Dierdra that if she wanted me she had to do all the work. She got a sly grin on her face and said, " Oh, I don't think that will be a problem." Her whole demeanor change and she looked at me and said sternly, " Take off all your clothes and mine bitch. And hurry." I jumped to obey her. I didn't want Mistress to be angry with me. After we got naked she ordered me onto the bed. She started taking things out of her bag. "I came prepared. I knew you were a submissive little slut so I brought my flogger and my strap-on." My pussy flooded with juice right then an there. I knew that I was in for a special night. Dierdra told me to roll on my stomach and put my arms along the side of my body. "Before we begin slut, what is your safe word?" "Yellow Mistress," I whispered. "Good girl." Now I'm going to flog you. I start gently at first. If you can take it I will get progressively rougher. But I won't hit you harder than you can take. All you have to do is use your safe word and we will make love just like any couple. I was determined not to use my safe word unless absolutely necessary. I had never been flogged but it was something I had always wanted to try. I was unprepared for the first strike. I jumped a little but it was nothing I couldn't handle. When I didn't safe word after 5 minutes of gentle flogging she started to hit harder. My pussy was leaking juices all over. I hadn't been this turned on in along time. After 15 more minutes of alternating lashes and caresses Mistress stopped what she was doing and laid the flogger down. "Wow," she said. " I thought you would safe word long ago. I figured you for a whiny little bitch who couldn't take what I could dish out. I'm impressed baby girl." "Thank you momma," I said. "I only want to make you happy." "Oh you did. But you can do something else to maker momma happy." "What is it momma? Will it be hard for me to do?" I asked. "Oh no little one. It will be very easy," she said as she caressed my cheek. She pulled my hair and told me that I was going to lick and suck her pussy and asshole until she had cum at least 3 times. I was only to happy to obey. I started licking her juicy bare pussy with my tongue. Flicking my her hard clit before moving down to tongue fuck her hole. I wanted to make sure I paid attention to all of her so I started licking back to her puckered little asshole. She tasted so sweet. I worshiped her ass until she stared squirming. That's when I licked my way back to her clit. I licked and nibbled on it until she sprayed my face with her juices. Oooh, she was a squirter just like her mother. I knew how tender she would be after her orgasm so I started my journey downward to her ass again. It was time to pay homage to those round globes. I made tongue into a hard little sword and fucked her ass with it. It wasn't long before I had her ready to cum again. I got a wicked grin on my face but hid it from her. I didn't stop what I was doing. I was going to be a brat and prolong her next orgasm for a while. I knew it might make her angry but I was willing to risk it. Keeping my tongue stiff I move up to her pussy and stuck it in. I fucked her with it for a while until she almost broke her role and begged me to make her cum. I knew I had to give her what she wanted because it would only result in more flogging. So I licked up and nipped her clit. That's all it took. Orgasm #2. By this time my tongue was getting pretty sore so I reached up with my fingers and started stroking her. I'd flick her bean a couple of times before moving down to slide 2 fingers in her dripping pussy. I felt her inner muscles squeezing and trying to suck my fingers in deeper. I slid them out of her scooping some juice and lubricated her asshole and stuck a finger inside. She didn't seen satisfied with one so I slid another in. God she was tight. I liked it. I then used my other hand to rub her clit. In no time she was in the throes of her 3rd orgasm. I let her come down a little before bending down and nipping her clit again. Orgasm #4. She pushed me away and said, "You little, minx. You made me cum 4 times. Good girl." But you did tease me so I will have to punish you. I'm only doing it because I care about you and want you to be a better girl. "Yes momma," I said. "I'm sorry for teasing you. I won't do it again." "Yes you will," she laughed. "It's in your nature. You can't help but be bratty sometimes. Momma knows this and will make sure you don't take it too far." Since you pleased me so much I am going to fuck you with my strap on until you cum and then it's time for night nights. We have a long day tomorrow. "Yes momma," I sighed. "I would like to cum very much." Oh you will. Just not in the way you think baby girl. My eyes lit up. I was excited to see what she had planned. Momma got off the bed and reached in her bag and pulled out a strap on. Another new experience for me. I was beginning to like this trip. She strapped it on and got back on the bed and started kissing me and playing with my tits and pussy. "You enjoyed making momma cum didn't you little one?, momma asked. Oh yes very much. I hope you will let me do it again. She then got on top of me and started fucking me with that wonderful fake cock. In no time I was ready to cum. I knew I couldn't until I had permission but it was hard holding it in. Momma stopped fucking me and pulled her dick out of my pussy. I pouted a little until she brought that cock up to my mouth and told me to clean all my juices off of it. She had plans and wanted to make sure it was clean and spit polished. I was happy to oblige. It wasn't the first time I had tasted my own juice and it certainly wouldn't be the last. After making sure her cock was nice and clean momma made me kneel on all fours like a dog. I was almost positive what was coming next but I didn't want to assume anything. I felt the cold dribble of lube on my asshole and knew I had guessed right. I was going to be fucked in the ass. It wasn't something I had done often but I knew I was in good hands. I trusted momma not to hurt me and knew that all I had to do was safe word and she would stop. She slowly inched her way into my ass stopping every few seconds until I was comfortable before proceeding. Soon I felt momma up against me and knew that that all 6 inches was buried deep in my bowels. After letting me get used to the feel she slowly started moving in and out. Soon I was meeting her thrust for thrust. It felt so good. "Cum for me bitch," momma growled. "Cum while my cock is buried deep in that hot ass." That's all it took to send me over the edge. I came with a scream. I don't think I stopped shaking for 5 minutes. Momma pulled out and lay down on her back and opened her arms. I was content so I crawled in and let her hold me until I started drifting off to sleep. The last thing I remembered until the next morning was momma getting out of bed whispering good girl.
We landed on a sultry summer afternoon. The place we were staying at was all inclusive so the first place I headed to was the bar. I had only planned on having one drink and going back to my room, alone, to take a nap. Dierdra, Sarah's daughter, had other plans. She came in just as I was getting up to leave. Please stay and have a drink with me Miss Kate. How could I refuse. We ended up having more than one drink. I was pretty drunk and so was Dierdra. When I drink I also get horny. I was thinking, how can I politely leave and go back to my room and satisfy my itch with my trusty vibrator. I never go on a trip without it. I was making my excuses to Deirdra when she blurted out, " Miss Kate, I have a confession. I was hoping you would be alone so I could get you drunk and seduce you. I think you are a very beautiful woman and I would love to taste your hot pussy." I was a little shocked but who am I to refuse a request like that. Besides getting my pussy licked by a hot 21 year old was much better than a fake dick. I said to her, " Well if it's pussy licking you want, why are we wasting time talking about it. Let's go back to my room and see what we can do for each other.
When we got back to my room, suddenly shyness overtook me. I told Dierdra that if she wanted me she had to do all the work. She got a sly grin on her face and said, " Oh, I don't think that will be a problem." Her whole demeanor change and she looked at me and said sternly, " Take off all your clothes and mine bitch. And hurry." I jumped to obey her. I didn't want Mistress to be angry with me. After we got naked she ordered me onto the bed. She started taking things out of her bag. "I came prepared. I knew you were a submissive little slut so I brought my flogger and my strap-on." My pussy flooded with juice right then an there. I knew that I was in for a special night. Dierdra told me to roll on my stomach and put my arms along the side of my body. "Before we begin slut, what is your safe word?" "Yellow Mistress," I whispered. "Good girl." Now I'm going to flog you. I start gently at first. If you can take it I will get progressively rougher. But I won't hit you harder than you can take. All you have to do is use your safe word and we will make love just like any couple. I was determined not to use my safe word unless absolutely necessary. I had never been flogged but it was something I had always wanted to try. I was unprepared for the first strike. I jumped a little but it was nothing I couldn't handle. When I didn't safe word after 5 minutes of gentle flogging she started to hit harder. My pussy was leaking juices all over. I hadn't been this turned on in along time. After 15 more minutes of alternating lashes and caresses Mistress stopped what she was doing and laid the flogger down. "Wow," she said. " I thought you would safe word long ago. I figured you for a whiny little bitch who couldn't take what I could dish out. I'm impressed baby girl." "Thank you momma," I said. "I only want to make you happy." "Oh you did. But you can do something else to maker momma happy." "What is it momma? Will it be hard for me to do?" I asked. "Oh no little one. It will be very easy," she said as she caressed my cheek. She pulled my hair and told me that I was going to lick and suck her pussy and asshole until she had cum at least 3 times. I was only to happy to obey. I started licking her juicy bare pussy with my tongue. Flicking my her hard clit before moving down to tongue fuck her hole. I wanted to make sure I paid attention to all of her so I started licking back to her puckered little asshole. She tasted so sweet. I worshiped her ass until she stared squirming. That's when I licked my way back to her clit. I licked and nibbled on it until she sprayed my face with her juices. Oooh, she was a squirter just like her mother. I knew how tender she would be after her orgasm so I started my journey downward to her ass again. It was time to pay homage to those round globes. I made tongue into a hard little sword and fucked her ass with it. It wasn't long before I had her ready to cum again. I got a wicked grin on my face but hid it from her. I didn't stop what I was doing. I was going to be a brat and prolong her next orgasm for a while. I knew it might make her angry but I was willing to risk it. Keeping my tongue stiff I move up to her pussy and stuck it in. I fucked her with it for a while until she almost broke her role and begged me to make her cum. I knew I had to give her what she wanted because it would only result in more flogging. So I licked up and nipped her clit. That's all it took. Orgasm #2. By this time my tongue was getting pretty sore so I reached up with my fingers and started stroking her. I'd flick her bean a couple of times before moving down to slide 2 fingers in her dripping pussy. I felt her inner muscles squeezing and trying to suck my fingers in deeper. I slid them out of her scooping some juice and lubricated her asshole and stuck a finger inside. She didn't seen satisfied with one so I slid another in. God she was tight. I liked it. I then used my other hand to rub her clit. In no time she was in the throes of her 3rd orgasm. I let her come down a little before bending down and nipping her clit again. Orgasm #4. She pushed me away and said, "You little, minx. You made me cum 4 times. Good girl." But you did tease me so I will have to punish you. I'm only doing it because I care about you and want you to be a better girl. "Yes momma," I said. "I'm sorry for teasing you. I won't do it again." "Yes you will," she laughed. "It's in your nature. You can't help but be bratty sometimes. Momma knows this and will make sure you don't take it too far." Since you pleased me so much I am going to fuck you with my strap on until you cum and then it's time for night nights. We have a long day tomorrow. "Yes momma," I sighed. "I would like to cum very much." Oh you will. Just not in the way you think baby girl. My eyes lit up. I was excited to see what she had planned. Momma got off the bed and reached in her bag and pulled out a strap on. Another new experience for me. I was beginning to like this trip. She strapped it on and got back on the bed and started kissing me and playing with my tits and pussy. "You enjoyed making momma cum didn't you little one?, momma asked. Oh yes very much. I hope you will let me do it again. She then got on top of me and started fucking me with that wonderful fake cock. In no time I was ready to cum. I knew I couldn't until I had permission but it was hard holding it in. Momma stopped fucking me and pulled her dick out of my pussy. I pouted a little until she brought that cock up to my mouth and told me to clean all my juices off of it. She had plans and wanted to make sure it was clean and spit polished. I was happy to oblige. It wasn't the first time I had tasted my own juice and it certainly wouldn't be the last. After making sure her cock was nice and clean momma made me kneel on all fours like a dog. I was almost positive what was coming next but I didn't want to assume anything. I felt the cold dribble of lube on my asshole and knew I had guessed right. I was going to be fucked in the ass. It wasn't something I had done often but I knew I was in good hands. I trusted momma not to hurt me and knew that all I had to do was safe word and she would stop. She slowly inched her way into my ass stopping every few seconds until I was comfortable before proceeding. Soon I felt momma up against me and knew that that all 6 inches was buried deep in my bowels. After letting me get used to the feel she slowly started moving in and out. Soon I was meeting her thrust for thrust. It felt so good. "Cum for me bitch," momma growled. "Cum while my cock is buried deep in that hot ass." That's all it took to send me over the edge. I came with a scream. I don't think I stopped shaking for 5 minutes. Momma pulled out and lay down on her back and opened her arms. I was content so I crawled in and let her hold me until I started drifting off to sleep. The last thing I remembered until the next morning was momma getting out of bed whispering good girl.
8 years ago