Hiya! My name is Amanda. You can call me Mandy, everyone else does! I have a lovely story, but I will have to get some background info to ya first. A drunk driver orphaned me about 5 years ago now during a rainy night in October. My parents were the plan ahead sort so by their will I have been well cared for by my aunt and uncle. They had two kids, Sheri and Matt, who, despite living in already cramped spaces, took me in as a sibling rather than treat me as dirt. Matt is the football type, outgoing and popular with the boys and girls alike. He is 21 and attends a state college. Sheri is the total opposite, and somewhat of an enigma. Sheri was 18 and mostly kept to herself away from the house. She did not seem to be interested in anything but her books & her library job she had to help offset her junior college tuition.
I had to attend the same junior college as Sheri. This was part of my parents planning also. You see I have a rather lucrative trust fund my parents had started when I was born. The only thing I could use it for was college expenses and a new car after graduation. Until I graduate with some type of degree direct transfer to a school account can only access the trust. Sheri and Matt had been lucky, too. Matt got a full ride for football, and Sheri’s was all smarts, but part of her was work time required. Sheri always dressed in long dresses nothing revealing at all. At home she was no different; she wore long nightgowns that hid her body. I could tell she was lonely and always saw her looking at a sophomore named Scott. I just never knew why she wouldn’t talk to him.
Well, all this, of course, has since changed. I think I may have created a monster even. It all started while Sheri and I were out for summer break. Her parents always went on a two-month vacation overseas somewhere and Matt had decided to take some of his elective courses over the summer. This left Sheri and me to our own vices. The first night we both had to work late, but I called up Sheri on the way home.
“Hey girl you wanna get a pizza on your way home? I will pick out a movie.”
“That sounds good,” she replied, “just nothing scary or shoot ’em up.”
”Ok, how about a comedy? I think we could both use a good laugh.”
I decided to pick a romantic comedy I had seen that boarded on soft porn to see how Sheri would react. I thought she was still a virgin and likely had not seen a dick other than in a sex Ed or art class.
We arrived home about the same time and changed into sleepwear. For me this meant no clothes, but I put on a long t-shirt that came to my waist. For Sheri, though, she had on a gown that was mid sleeve length and the hem was practically at the floor. I met her in the kitchen, and poured myself a glass of wine. I was comfortable, but my t-shirt rubbed my nipples as I moved around and they were beginning to stand up. I offered Sheri a glass, and when she refused I told her with just us there she needed to loosen up and relax. She gave in and told me to give her a little. When I handed her the glass I noticed her glancing at my chest. We went to the living room and I put the movie into the DVD player. From the moment the credits came on I knew something was wrong. There on the screen was a barely clothed woman holding a vibrator!
“Oh shit,” I exclaimed. Sheri looked up and about choked on her first bite of pizza. “It appears the movie I picked has been switched.” I looked to Sheri and she was just staring at the screen.
“Mandy, what is…I mean I know what that is, but what kind of movie did you get us?”
“I am sorry, Sheri, I did not check the DVD to make sure it was the movie the box said it was. We can find something on pay-per-view instead.” In the dim light I could tell her expression was one of curiosity not horror. So I went out on a limb. “Sheri, have you ever seen porn before?” “NO!” she replied loudly.
“I am sorry, I did not mean that badly. I…. I just have noticed these past years you dress way conservatively. May I ask you something?” By now she had consumed the glass of wine I had given to her.
“Ok,” she said.
“Have you ever been on a date?”
She looked away, but answered, “No, I have never been asked out.” When she looked back there were tears in her eyes. “Mandy, can you help me…with men I mean?”
I got out of the chair and moved to the couch where she was and put my arms around her. “I thought you would never ask! I think we better have a little more wine and loosen up that tongue and mind of yours.” I went back to the kitchen and got the bottle of wine. When I came back I was surprised to see the movie playing. She must have fast-forwarded a little because there was no bullshit-talking going on just a woman taking a huge cock in her mouth. “Did you decide to watch it?”
“It’s ok, I like a good porn every now and then.” With this she visibly relaxed and turned back to the screen. I poured her an ample serving of wine this time and sat back down beside her. “Aren’t you warm in that damn gown?” I paused the movie. “I know you also have a very uncomfortable bra on too. Let’s go up stairs and get you into something that will make you feel better.”
“Uh, Mandy, this is all I have,” she said.
“Not from your room silly. I have a lot more than this t-shirt. We need to make you feel pretty, and then come back down to watch this.”
We went up to my room, and I told her to take off her gown. She looked shocked, but I told her she had nothing I did not have. She tried to refuse, but I walked over and put a finger on her lips. I know you are self-conscience, but I need to know what I have to work with.
I stepped back and said,” Here, this should help.” I slowly took off my shirt and revealed everything I had. Her eyes immediately went south to my mostly shaved pussy, then quickly up to my face. She blushed considerably, and looked away from me. I reached up and took her chin and forced her to look at me. “It is ok to be curious. I know you have not been through the showers with other women. Take a good look, please. By now my nipples were at full erection and pointing at her. I moved my hands down to her waist and slowly began lifting her gown. She made a half-hearted attempt to stop me, but I looked in her eyes and kept steady pressure pulling up. She relaxed her arms and lifted them up as her hem came up and over what I never knew she possessed. There before me in a plain jane bra was a set of 38DDs.
“My goodness! Now there is something I can work with.” Sheri tried to cover herself. “Don’t hide those. They are something to be proud of.”
She looked at my breasts, and said, “Really? They are too big if you ask me.”
“Those are perfect. Mine are two sizes smaller and guys like them, but yours they would fall all over themselves for. What we need to do now is set them free.” I spun her around and popped the clasp on her bra. Her tits flew out like a pellet from a slingshot. She turned around again and saw me nodding in approval. “Ok, I can let the video show you how those can be used. Let’s see you naked like me. Off with those granny drawers.”
She shyly bent over and her face was at eye level with my neatly trimmed ‘landing strip’ bush. She stared a second at it before sliding her own off. When she stood I could tell hers had not seen a razor since the first sprigs of hair grew.
“Now this we have to work on. How can you stand to masturbate with all that?” I asked already knowing the answer.
“I have never tried.”
“Yes, I figured that. What we need to do is get you acquainted with your beautiful body. First though we are going down stairs and finish the movie like we are and kill this bottle of wine. You’re going to need it.” I had mutual masturbation sessions in high school with friends, but I knew she would protest if sober to the idea. I took her hand and said, “Come on girl! We have much too much fun ahead.” I giggled at her expression, and led her down the steps. When we got back in the living room I dimmed the lights, pulled the blinds tight, and locked the doors. I got on one end of the couch and told her to sit at the other. I convinced her to start the movie and got back up. “I need to get some things from my room right quick.” With that I ran up stairs. As I went I thought about what I was doing. I knew I was going to have to seduce this ugly duckling to bring out the natural swan inside. I grabbed some warming massage lotion, a vibrator, and a strap on as a just in case. When I got down stairs Sheri was enthralled in the movie. She didn’t notice the items I had. She had both legs tucked under her, and was leaning on the arm of the couch. I looked in the case and found the scene selection guide and found what I was looking for. The picture was a girl with a vibe in her. I was hoping it would have a scene like this. Sheri had downed almost all of another glass of wine so I refilled it.
“Sheri hon, drink up. I want to position you for an up coming part of the movie.”
“Ohhkay,” she slurred.
Perfect I thought to myself. I got on my knees in front of her, and gently pulled her legs out. I left one foot on the floor and moved one onto the couch thus spreading her pussy open. Her musky scents made me want to dive right into her. I held back not wanting to move too fast. I then got the remote and sat down on the other end of the sofa just like her. When I paused the movie her eyes were instantly drawn to my gaping snatch and me.
“Oh, wow,” she said, “your…umm…is showing.”
“My pussy, Sheri, my pussy.”
“Yesh, your pussy.”
“I have something here for us.”
With that I poured some oil over my lower tummy and handed the bottle to her. She followed my lead and I felt the first drops of warmth flow over my pussy. I turned to the TV and hit the play button. I had queued the movie to the masturbation scene so the girl from the movie was sitting in a big chair with the items I had from upstairs minus the strap on. She started pulling on her nipples then moved down to her pussy. Just as she started to rub herself the movie shit on us.
“Damn, just as it was getting good,” I said. “Well, Sheri, I guess we will have to improvise.”
“What do you mean?”
“That lotion on your tummy is not just for looks babe. Here let me show you. Look at my tummy. See how the lotion has run down me?”
“Yes. I thought it was just for… like… lotion.”
“No, it is for lubrication,” I said as I started rubbing my pussy lips with my fingers getting the lotion warming.
Sheri’s eyes were glued to my pussy as she watched my fingers play about my lips. I closed my eyes and let her just watch. I stayed away from my clit and pulled at my pussy lips. I pulled both sides open to reveal my whole pussy to her. I forgot she was there as I eased two fingers into my hole and began fucking myself with them. I began to moan as my other hand found my clit and I used slow circles around it. Soon I felt the familiar beginnings of a climax hitting me. I rammed my fingers deep inside me as I ejaculated spurting my girl cum all over the seat in front of me. I came around a few seconds later and saw Sheri just staring at me. I looked her in the eyes and sucked my fingers dry and moaned, “Damn that felt good.”
Sheri came out of her stupor and stammered, “What did… how did… oh never mind.” She quickly got up and ran upstairs.
I cleaned myself up and turned off the TV then grabbed my stuff and took it to my room. I went over to Sheri’s door and heard her softly sobbing and knocked on her door. “Sheri, may I come in?”
“No, go away and leave me alone.”
“Please,” I pleaded, “Let me come in to talk to you.”
I heard the door unlock and I gave it a minute then went in. Sheri was in her bed with the sheet pulled up. I walked over and sat next to her on the bed.
“Sheri, what is wrong?”
“I am not like you Mandy. I can’t do what you just did.”
“Sure you can. Everyone does it. Guys and girls all do it. You just need to try. I just wanted to show you how you can feel good.”
I put my hand on her thigh. “Look. Your body is yours and no one else’s. You can please yourself. There is nothing wrong with it. You need release at some point in time or another. I know you enjoyed watching me. I saw it in your eyes when I looked at you and sucked my fingers. There is nothing wrong with liking another girl. You can like both guys and girls. We do need to shave you though. Get some of that hair out of the way and everything will rub you just right, from clothes to sheets like you have on you now.” I stood up. “Just think about it tonight. There is no rush to this.”
I left her room and went back to my own and finished what I started with the vibe this time. I had six more orgasms masturbating thinking of Sheri. I woke early in the morning and went downstairs and started fixing breakfast. Sheri came down about the time I was getting done. I noticed a change in her immediately. Instead of the normal nightgown she wears all she had on was a t-shirt that barely covered her mid thigh. She smiled sheepishly at me and I smiled back.
“Good morning sleepy head.”
“Hey, Mandy. I am sorry I acted the way I did last night. What you did was very beautiful and I guess it just got to me because I am not as pretty as you.”
“Sheri, you are beautiful. I wish I had some of your assets. Let’s eat and if you’re ready we can work to build your confidence. I know of a little boutique that can help, but there is something we must do first if you’re ready and willing.”
“I think I am, but can we take it slow?”
“Yes, dear, I think we can.”
We finished breakfast and cleaned up. Then we went up to my room and I grabbed some trimmers. Then I took Sheri by the hand and said, “Are you ready to come out of your cocoon?”
“Yes, Mandy let’s get started.”
I led her to the bathroom, and spread a towel out on the floor. Then I had Sheri strip. To make her comfortable I did the same. Then I asked, “What do you want left? Nothing, a strip like mine, or some other design?”
“I think I would like a butterfly if you can do it. If not then I want to be bare.”
“I will try. Are you ready?”
She nodded. I told her to sit with her back against the wall and her feet in the tub with her legs spread. I got on my knees in front of her. I turned the trimmers on and told her I was going to touch her with the backside of them to let her get used to the feel before I started cutting so she would not be moving around. Her sweet spot was glistening with moisture and smelled intoxicating. It made it hard to concentrate on what I was doing. I gently put the trimmers against her leg and she jumped slightly at the vibrations. I looked up at her and smiled. Then I moved it nearer her clit and she let out a small gasp. I turned off the trimmers and got some white fingernail polish and painted an outline of a butterfly in her pubic hair. Then I began trimming her bush down. Once I had most of her hair gone I told her I was going to have to shave her lips. Sheri nodded again and I lathered up some cream in my hands and began spreading some on her lips. I let my pinky graze her little clit that had begun to poke out and a small moan escaped her. I then took the razor and held her lips tight to one side and had my hand resting on her slit. I began to shave her lips carefully to avoid cutting her. She kept squirming and I told her to be still.
“I can’t Mandy. Your hand is touching me here.” She pointed at her clit. “I did not know that could feel good.”
“It can feel MUCH better, Sheri. Just try not to move so I don’t cut you.”
I finished up shaving her and when I got done I let my finger run up her slit as I moved my hand. When I got to her clit I rubbed it a little. She started moaning and I looked up and saw her eyes closed. She moved her hips up to try to press her pussy against my finger, but I moved my hand away. I took the sprayer head from the tub and turned on the water and got it warm. Sheri opened her eyes and looked at me. I rinsed off the rest of the cream from her and took a mirror so she could see her mostly bare pussy.
“Wow,” she exclaimed. “I look soooo different now.”
“Yes, now lean back I have something else for you.”
I took the sprayer and turned it on the gentle massage setting. Then I inched the water up her thigh and opened her pussy lips up to reveal her clit. I set the stream on her lips and she began to squirm. I then slowly moved the water to her clit and let the water work its magic on her. She instantly gasped as the water began playing on her clit. I left the water on her clit moving it back and forth. Then I took one finger and massaged her lips outside her hole. Sheri closed her eyes and slid her hips towards my ministrations and me. I took this as a good sign and slowly and gently moved my finger inside her. She began to moan and move her hips up and down on my finger. I did not feel her hymen but I knew she used tampons instead of pads from the stock in the bathroom. I then inserted another finger inside her and moved the water off her clit. I slowly began fucking her sweet hole with my two fingers. Then I bent over and took her clit between my teeth and began flicking it with my tongue while fucking her faster with my fingers. It was not long and she began moaning louder. I knew she would not last very long since she had never masturbated at all. I curled my fingers up to her G spot and began massaging it with my fingertips while still sucking on her clit. Seconds later she came with a loud moan. When she calmed I slid my fingers out of her and moved up to her face and kissed her lightly on the mouth.
“Now,” I whispered, “Do we feel better?”
“Oh, yes. That felt terrific. How can I do that?”
“I will teach you more later.”
“Get a long hot bath. We have some shopping to do. If you want to try something just do what I did on the couch last night to yourself. It won’t take you long to figure some of it out. I can help you with more, but for now let’s just leave it where we are. If it feels good then you’re doing some thing right.” I smiled and left the bathroom and her to do what she would.
I listened from the hall at the door and it was not long before I heard her start moaning again. I smiled to myself and walked to my bedroom to get off again then got dressed to go out with Sheri.
Sheri came down the stairs after an hour in the tub. She had found the clothes I left for her on the bed. She looked at me and said, “I have not worn shorts in a very long time. Thank you for letting me use them.”
The shorts were khaki and fit her snug. “It looks like you found the undies I left in there too. How do they feel?”
“I may cum again soon! They rub me just right, but Mandy what is the pocket in them for?”
“Do you want to know now?”
“I think so, but for sure if it will make me feel good.”
“Oh, it will. You wait right here.”
Before she changed her mind I ran up the stairs, and grabbed the toy that went with the panties. When I got back I told her she had to strip and lay on the sofa. She did so very quickly. I took the panties and slid the remote controlled 2″ vibe into place in them. I then slid them up her legs.
“I need to get you wet for this to work.”
“I already am.” Sheri spread open her pussy for me and sure enough she was dripping. Her hand strayed to her clit, but I grabbed it.
“Oh, no you don’t,” I said. Then I shoved the little dick into her and pulled up her undies.
“Ummm, that is nice.”
“Glad you think so because you will not take it out until I say so. Got it?”
We went out to the car, got in, and she kissed me lightly on the cheek. I looked at her and smiled the started the car. As I did I hit the power button to the vibe and she nearly jumped out of the car. Her gasp of surprise quickly turned to moans as the mini dick did its job. When I turned it back off a second later she began to pout.
“Don’t worry silly, there will be more to come, excuse the pun.”
We drove down town to a small shop that a friend showed me. I told Sheri this was a sex shop so she wouldn’t be too surprised. We walked in and Bob, the owner, was the only one in today.
“Well, hellooooo Mandy and friend. Who is this gorgeous creature you have with you?”
“Oh, Bob stop it, this is my cousin, Sheri.”
“No, Bob, please go on,” Sheri said with a blush.
“Bob, we need help of a special nature. Could I convince you to lock the doors for a while?”
“Sure kiddo, if your gonna pay like you always do.” He walked to the door, turned around the sign, and locked up. “Now what is it an old man like me can help you with?”
“You remember how you helped me when Janice first brought me here?”
“Well, I need similar help with Sheri. She did look like this…” I pulled out a picture I had of her. “Now she looks like she does before you. I need to introduce her to the various ways of self-love before we can proceed to loving others. I have started already, but she needs confidence with men.”
Both of them looked at me. Bob had a knowing look in his eyes, but Sheri had one of confusion.
“Sheri, Bob is a good man, one to be trusted. He helped me out not long after my parents died. You know how I dressed, like a gothic girl. I had no confidence. You remember Janice. She helped me out a lot when mom and dad died. You will have to trust me, but after tonight you will have experienced ALLLLL kinds of love. You said you trusted me. Now you have to prove it. Are you ready or do you want to quit now?”
“I think I am ready. I do trust you, but I don’t know what to do.”
I took her hand and led her to a back room. There was a ‘love’ chair, a big flat panel TV, and all manner of different ‘toys’. As we walked in I turned on her toy with the remote. Her gasp was audible enough for Bob to hear.
“Please strip, Sheri,” I said as I begin to do the same, “Leave the toy on and in you. Then come sit on this chair with your feet in the stirrups.”
Bob went out of the room and brought back some beer in a cooler for us. When he came back in Sheri was moaning. The little vibrator was going at high speed, and I had her hands strapped in the holders on the chair. I was kneading her tits and pulling on her perk nipples. “Bob, be a dear and get one of your self-help DVDs and bring it in here.”
Bob left back out, and I stopped the vibe and Sheri’s loving. She whimpered and whispered for me not to stop now. I smiled at her and patted her on the tummy. I gave Bob the remote for her, and told him to finish her off. I put in the DVD that went with the love chair and started it. When I turned around Sheri was moaning again and Bob was nibbling her tits and rubbing her clit. Sheri screamed as she came, and Bob turned off the vibe. Sheri watched the screen for a bit as it explained the different positions the chair could be used and showed a girl of 18 being fucked on it.
“Are we here to do all of that?”
“Only if you are willing, Sheri. I think you should experience it all as I did.”
“Some of it looks painful.”
“If not done right it can be,” Bob said, “I know how to use and do all of it the best way for you not to feel anything but pleasure.”
“Ok, I trust Mandy so let’s do it.”
Bob reached over and spread the stirrups the entire way apart opening up Sheri for his access. I walked over to Bob and took his shirt off. Then I bent down and took his pants down. When his 10 inches sprang out of his boxers I quickly engulfed it into my mouth. He began to moan as I stroked and sucked him. Sheri watched in fascination as I took all of him in my mouth and down my throat. He popped himself out of my mouth and walked to a table and grabbed a 7-inch vibrator off the table. He turned it on and began rubbing Sheri with it. I took him back in my mouth and kept sucking him while he sent Sheri into another orgasm. When she came down from her high he asked her if she were ready to be fucked for the first time. She nodded and he moved the chair up for easy access to her dripping cunt. I kneeled down between her legs and guided his dick into her waiting pussy. He inched his head into her and waited until she was used to his girth before slowly going all the way into her. Her ass was spread and I began to tongue her little brown hole while rubbing Bob’s balls.
Bob slowly pulled all the way out to the head and this time plunged into her shaking the chair and slapping my chin with his balls. He quickly found his rhythm and slowly fucked Sheri. I reached up and found the vibrator and used her juices that were now steadily flowing to lube it up. I massaged her anus with the tip and slowly pushed it against it. Her little hole opened up around the tip and I eased it inside and turned it on. The head of it rotated and after a minute I turned it on and let it ream her. As her ass became used to the toy I was able to push it in all the way. Sheri’s moans became screams of ecstasy as both the vibe and Bob fucked her. I moved from under her and went to the table and got a massive 14-inch strap-on dildo from the table. I stepped into the straps and tightened it up with the small secondary attachment inside me. I moved over to Bob and told him to move out of the way.
Sheri looked at the fake dick with wonder as I moved into position. Bob went to her head and turned it towards his cock and forced it into her mouth. As she began sucking him off I put the head inside her. She stopped her sucking and whimpered a little but Bob reached down and grabbed her head with one hand and fucked her mouth with the other he pinched a nipple. As he did I pushed the toy on inside and waited until her pussy relaxed. When she got used to it I reached down and rubbed her clit and started fucking her good. Soon she was coming again and Bob pulled out of her mouth and shot a stream of hot cum all over her tits and face. She licked up what she could. I pulled out of her and moved up to her tits and licked them clean then kissed her giving her a taste of his cum that I held in my mouth. Bob moved around and took the toy out of her ass as I took the straps off her hands. She sat up and lovingly kissed us both.
We all showered and fucked some more in the bath. Sheri and I went home and spent the rest of her mom and dad’s vacation sleeping together and enjoying our newfound love.