This is a story of pure fiction. Never do anything with a person under legal age or without their consent.
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Saturday morning
I was having the strangest dream. I drempt that I had been dressed as a little girl and and learned how to please a man. In the twilight of waking up I reached down to play with my morning wood and snapped awake with the realization that I had been with a man, Mr. Williams, and that we had played around. I took a few minutes to think about this as I started to again rub my cock that was in a pair of panties. The
The door opened and Richard walked in "already up I see" he said "and having fun just like I used to when I was your age". Sitting on the edge of the bed Richard reached over and moved my hand away replacing it with his. "I need to know if you are ok with everything we did last night and if it was a one time event or do you want to continue. If you want it to continue I promise it will always be our secret and I will never do anything you don't want".
I sat there with my teen dick being stroked by a man old enough to be my father and I was loving it. Did I want this to continue, for now definately. I hadn't thought much past the "here and now". I knew I had to think about what was said, about how I felt in feminine clothing and if I wanted it to continue. I knew I wouldn't be able to make the decision in the condition I was in right now. Placing one hand over Richards hand to hold it there I scooted toward the middle of the bed bringing him with me. I lay back on the pillow and removed my hand from where I had it on his.
Richard had kept stroking me while he sat on the edge of the bed. Lowering his head he gave me one of the sexiest slow , fuck your mouth kisses. It was a slow kiss with tongues just barely touching and slowly sucking the breath from my body. At this exact moment I knew I would do anything this man wanted me to do for the rest of my life. I also knew that I was going to have one of the most intense orgasms of my young life. I laid my head back on the pillow feeling like all energy had been pulled from my body as The panties were filld with my morning juice.
Richard got up off the bed" you need to get up and take a shower. Wear the panties in there with you and rinse them out, you have soiled them and a good girl needs to clean up." I will be downstairs making breakfast, when you are done with the shower, powder your body with this powder and get dressed using anything you find in the top three drawers of the dresser.
After I had regained my composure from what had just happened I got up and headed in to the private bathroom attached to the bedroom. The large shower was soon filled with steam and I stepped in and just let the water run over my body. I started to examine my body closely for the first time in years. I took the shampoo off the shelf, it smelled of lavender. Lathering up my hair I got to scrubbing my long hair real good. I had a good lather of suds so I took a bunch of it and washed my cock thru the panties. Lowering the panties I took them off and washed them thoroughly, rinsed them under the shower head and hung the on the shower handle. Once I had all the shampoo rinsed out of my hair I took the bar of soap, smelling it it also smelled like flowers. I spent almost 15 minutes in the shower washing very carefull ever inch of my body.
Stepping out of the shower I dried my body with the fluffy towel, I wrapped my hair up in a towel and entered the bedroom to find something to wear. Only the first 3 drawers Richard had said. The first drawer was filled with panties and bra's there were panties from plain to very sexy. Some of the panties were under a bra of matching color. A set at the end caught my attention. A light purple bra and panty outfit. The panties were a full cut almost like what a little girl would wear with ruffles of lace all the way around them in several rows. The bra was a lacy little thing, most likely a training bra as there was very little cup. I slid the panties up my legs and over my round ass and hard cock, they fit loose. Taking the bra in my hands I tried to figure out how to put it on. Unable to hook it in the back I hooked it in the front turned it around and worked my arms in to the straps.
The second drawer had bobby socks, pantyhose, knee highs, thigh highs and some strappy looking things. I selected a pair of black stockings. As I put them on I noticed how they hugged my calf's and stopped just above my knees. They were so smooth and felt wonderful on my skin. I walked over to the full length mirror on the closet door. What I saw was not a boy but a cute little girl looking back at me. My cock was stiff as it had ever been. Going back to the dresser I opened the third drawer. In one end were pajamas. The middle had slips and the other end were pretty nighties. Thinking about the choices Richard had given it it looked like he wanted me dressed for bed for the day. I selected a black flimsy nightie that was like see thru fishnet and went to just below my knees.
I sat down at a makeup table and removed the towel from my hair. I took a brush from the table and brushed out my hair. The more I brushed the fuller it seemed to get. After I had finished with my hair I picked up a bottle of perfume, removed the cap and put a little on my finger. It smelled feminine. As a young boy I splashed some on my neck and put a dab on my crotch.
When I walked in the kitchen Richard has his back to me at the stove finishing up cooking breakfast. Turning he almost dropped the two plates he was carrying. Placing the plates on the table he opened his arms" come to me Sammie. You are beautiful."" Young lady", he said " you need to learn that you only need a drop of perfume to go a long way". He scooped me up in his big hands and held me close to him. His kiss was soft, nibbling at my lip then my tongue. His strong hands held my ass cheeks as he kneaded each one as he opened and closed them.
Putting me down Richard held a chair for me and pushed it in when I sat down. "that is how you treat a lady" he said. Lets eat while it is hot. We are going to need our energy. As we ate Richard said"you look good enough to eat but a garter is supposed to be worn with those stockings. We will teach you what to wear and how to put on perfume as we go".
After we had finished cleaning up from breakfast Richard asked me. "Do you want to go in the living room and watch some videos or go back upstairs to the bedroom". I sat there thinking about what I wanted, watch some videos and then we would wind up in the bedroom or go to the bedroom where I knew we would get right back in to what we had done all last night. My cock made up my mind for me. Just thinking on what I wanted to do it had gotten stiff as a flagpole. The bedroom I said boldly.
Laughing, Richard picked me up and held me close and carried me up to his daughters room, placed me on the bed and went over and closed the door. By the time he had gotten back to the bed I was already breathing hard, I felt like my body was on fire and I had run a competitive race.
Are you ok baby, your face is flushed and you're breathing hard.
Richard, I don't think I have wanted anything more in my life as I have wanted this. I held my hands out and welcomed him in to my open arms. The soft material from the nightie was like electricity on my skin, so soft and gentle yet so exciting and tingling every nerve it came in contact with. WE were laying on the bed with me in Richards arms and must have just kissed and had him rubbing his hands all over my nightie covered ass for close to a half hour.
"Put your head on the pillow sweetheart" Richard said. He picked up the other pillow and with one hand lifted my ass off the bed and placed it under my ass. Gazing down at me He said "I told you that you look good enough to eat and now I'm going to have desert". Standing in front of me Richard removed what clothes he had on. His cock was half hard and had a drop of precum on the tip. He knelt on the bed between my legs and brought his face to mine for another session of french kissing. As he was kissing me one hand was running up and down my leg, working his fingers over to my cock as he got near the top.
Slowly Richard raised the nightie up to just under my chin. Staring down at the little bra I had on he commented"Nice selection. Now in a kneeling position between my legs he reached down and started to play with my nipples thru the bra. He kept this up with one hand while he started to rub my cock in the panties with the other hand. I was hard ad I had ever been and ready to shoot.
Getting off the bed he went to the nightstand and retrieved a small tube he had brought in with him when we came upstairs. "you look so nice in that outfit, it would be a shame to dirty it so quickly". With that said Richard bent down and removed my panties and put them aside. "This will be cold" he said as he applied some lube to my ass crack and lubed up a finger. Sitting beside me he played with my ass crack some before slowly pushing the lubed finger in to my ass. It hurt for just an instant. Seeing me relaxed and laying back on the pillow he started to work the finger in and out of my ass. I closed my eyes and was just laying there enjoying the pleasure that was running wild in my body when Richard pinched one of my nipples real hard. I jumped "that hurt" I said.
I did it because you were about to cum. Notice your clitty has shrunk some Richard responded. Again the ass manipulation and a lesser nipple pinch. Every time I got near orgasm some pain was given to my chest. This went on for quite some time and each time I got close I was at a higher fever of intensity. Sensing that I was again on the verge of orgasm Richard bent down and sucked my whole cocklet in to his mouth. I exploded with every ounce of energy in my body. I lay back on the pillow under my head and felt Richard pulling his finger from my ass. I was asleep within seconds.
When I woke up I was alone in the room there was a yellow and white summer dress hanging on the back of a chair with a note to put it on and come down stairs. I took the nightie off and the black stockings and adjusted my bra and pulled my panties back on. After I had slipped the dress on I went and looked in the mirror and noticed how short the dress was. I remembered seeing Vickie, Richards daughter, in the dress last summer and it was short on her. I used to love her bend over so I could see her panties.
As I came down stairs I could hear Richard talking, I figured he was on the phone and just waked in to the kitchen. I froze in my tracks. sitting with his back to me was a man who looked to be about 45 or 50.
"Come here sweetheart" Richard said, I want you to meet a dear friend of mine. "This is Mr. Butler, Mr Butler this is my neice Samantha"
Mr. Butler said nice to meet you Samantha and stuck out his hand.
I looked at Richard shocked.
Don't be shy Samantha, Be a lady and welcome my friend in a friendly and proper fashion.
I walked over and shook Mr Butler's hand. As I did he placed his other arm around my waist and pulled me closer to his body. "My you are a beautiful young thing" he said as his hand slid down and cupped my ass cheeks.
Looking over at Richard, he didn't appear to notice his friend was feeling me up. I was getting a little scared. Mr. Butler rubbed my ass once more and gave me a little swat and set me free.
Why don't you come over and sit on uncles lap, Richard said. Moving over to Richard he picked me up and sat me on his lap. I could feel his cock getting hard and rubbing between my legs.
Richard and Mr. Butler carried on a conversation the whole time all this was going on. We must have sat there for close to 15 minutes. Finally Mr. Butler said "Keep me informed on how the project is progressing and maybe in a couple of weeks we can get together and see what results you have.
Mr Butler got up from the table shook Richards hand and bent over and gave me a kiss on the cheek as he gave my leg a squeeze.
"Wait Tom" Richard said. Turning to me he said sweetheart be a doll and get me those books over in the corner. Crossing the room I bent over and started picking up the books. The ones next to those as well Richard said. Still bent over I got the other books and then I realized that these men were looking at my panties. I pretended to drop the books and bent pver and wiggled my ass as I picked them up. A little red faced I brought the books to Mr. Butler.
After Mr. Butler had left I turned to Richard and said"I know what you two dirty old men were doing"
What darling were we doing, replied Richard.
"You were looking at my panties when I bent over". What happens if he realizes I'm not a girl. What happens if he tells someone, My life will be ruined I said to Richard.
Taking me in his arms Richard held me close and whispered. "Hush baby, I will never let anyone hurt you and would never expose you to anyone I did not trust. Mr. Butler is a very dear friend and I trust him completely, besides there is no way from looking at you that anyone could tell you are not a girl. Look at yourself, you have a cute round ass, with your bra on you have budding little titties, and your natural long hair just adds to the image. For now, dressed as you are you are my little girl, now give me a kiss."
Taking my hand Richard led me to the couch. Till now I hadn't noticed but on the coffee table was a pizza box and some cokes on the table, I also noticed a box that wasn't on the table last night but didn't give it a second thought.
Mr Butler was nice enough to bring a pizza over when he dropped by. He had called me earlier and asked if there was anything he could get for me as he was on his way over to discuss some things so I asked him to get the pizza Richard said. We sat on the couch snuggling and eating pizza for the rest of the afternoon.
At about 6Pm Richard suggested that I go take the dress off and get my nightie back on and come back down and we will watch some videos. As I was running up the stairs Richard yelled for me to bring down the bottle of lube as well. I took the dress off and laid it over the chair and got the nightie back on. Grabbing the bottle of lube I ran back down stairs.
Richard was on the couch with silk boxers on and nothing else. I cuddled up next to him and he started a video. Like the other day It looked like a young girl giving and older guy a blow job. She had a nightie and panties on. She was bent over the guy on a couch giving the guy a slow blow job and he was playing with her ass thru the panties. Richard was playing with my nipples thru the bra. He was twisting and pulling on them and pulling on the material. I reached my hand in the front of Richards silk shorts and started to play with his cock. It was oozing precum all over my hand.
The guy in the video took the girls panties down. Slowly he started to insert a finger in her pussy. I was getting hot watching the action on the Tv.
"Stand up baby" Richard said. "Take off your panties and lay over my lap"
I did as I was told. As I laid back down over Richards lap I notice the box was gone that had been on the end of the coffee table. Richard adjusted me on his lap so one leg was on the couch and the other just hung down. In this position my ass was pulled open and fully exposed. I felt Richards hand rubbing all over my ass. He was kneading my ass cheeks and telling me how beautiful I was. Every so often he would push a finger in to my boi hole then pull it back out. After a few minutes of this he applied some lube to that finger and started to work it in and out of my ass. I was breathing hard and my cock was caught between Richards legs and he wasn't touching it.
i reached around to rum my cock and 'swat' Richard slapped my ass. You just lay there and enjoy the video and let me worry about pleasing you he said. I glanced at the video and noticed the guy was still fingering the girls pussy but was also working something in to her rear. Richard started to put two fingers in my ass. He worked them in and out for a while. I noticed when he pulled the fingers out but they were back right away the same as he had been doing for the last few minutes, only this time it felt different, it was cold and slid in easily but went much further that his fingers had.
What was that I asked. Richard replied The same as the girl on the video is getting". Looking up I noticed a long black cone shaped item was being pushed in and out of her butt. It tapered at the end and had a couple of tubes or wires coming out of it. Reaching back I could feel the base and the cords coming out. As I was about to ask I felt the most wonderful vibrations coming from the device in my ass. What is it, I asked.
Richard explained. "You have a buttplug up your ass. It has a couple of features. First it has a built in vibrator and the second feature is it is inflatable which means I can make it bigger" having said that I felt the plug expanding my ass almost to where it hurt. He went on to explain " it is just over six inches long and only an inch across when deflated. When I inflate it all the way it is over 2 inches across. Don't worry baby, I won't inflate it all the way, not just yet anyway." Over the next half hour I was driven to almost insanity with the butt plug being turned on and off and inflated and deflated. Each time it was inflated I think it was inflated larger than last time.
Richard shut off the tv, picked me up in his big arms and carried me up to his daughters bedroom, all this with the butt plug still tightly embedded in my ass. I hadn't noticed but he was also carrying the box. Placing me on the bed he again inflated the butt plug, handed me the inflation bulb, and told me to inflate it a couple of pumps every couple of minutes and he would be right back. I turned the vibrator back on as he left and twisted the dial, oh he had only had the vibrator set on 1 and I had it up to 4. Before I could lower it the cum shot out of my cock and all in my panties. I was so out of control I couldn't even touch the control. My ass was filled with this vibrating butt plug going almost full blast and inflated to fill me up.
When Richard walked back in the room I was just laying there shaking and moaning. He reached down and shut off the vibrator and opened the air valve to let the butt plug deflate. He started laughing. "look at you, you're a mess. I see you have soiled your panties. Well bad girls need to be trained properly. Take those off" Richard bent down and pulled the plug from my ass and placed it on a towel on the bedside table.
I got up and removed the panties. I was a mess. I had cum everywhere and the crotch of the panties was soaked.
Richard sat on the edge of the bed and reached out for my hand. He pulled me to him and took the panties from my other hand and placed them on the floor. Pulling me between hims legs he bent down and started to clean me up with his tongue. He licked all the cum from my balls and belly then took my hardening dick in his mouth and proceeded to suck my till I was rock hard again. I was fucking his face as he backed away.
"You realize you were a bad girl" Richard said, "you did not ask permission to cum" Bend over my lap. Bad girls need to be punished when they do wrong. When I bent over my feet weren't touching the floor.
Richard bent down and picked up the soiled panties. Placing the sopping cum soaked crotch in my mouth he said" I don't want to hear any crying and I expect those panties to be clean when I am done. Richard started to spank me, first on one cheek then on the other. He wasn't hitting hard, just hard enough to make it sting. He kept this up for a good 5 minutes.
The whole time I was getting spanked I was sucking my cum from the panties. The hits stung but more they were making me extremely horny. My bare cock kept rubbing between Richards strong legs and the silk boxers. I could feel Richard rubbing my warm ass and he kept up a never ending stream of soft talk telling me how I needed to be a good girl and how I needed to grow so he could make love to me like a big girl. He reached down on the floor, there was that box again, and brought out another butt plug. It was bigger than the first one he had used but quite a bit smaller than the first one when it was inflated. "I want you to put this in your pussie just before you go to sleep at night. This will help you get ready to take a cock up that sweet young ass of yours and you can become a full gurly boi.
Standing Richard took off his shorts and laid in the middle of the bed. "Strip and come up here and make love to Me and make me cum like the little slut that you want to be"
I wasted no time in stripping down and climbing up on the bed. Richard held his arms open and I dove in and gave him one of the most passionate kisses I could muster. Our tongues were flailing in each others mouths. Reaching over I took Richards nipple in my small hand and worked it. Moving from his mouth I followed my hand to his nipple. My hand then moved down to that wonderful man cock and I started to milk it. I had only been sucking on his nipple for a minute or so when I felt his hands pushing down on my shoulders.
The manscent coming off Richards cock was intoxicating to my sences. I was running in overload. My need for a cock in my mouth and the taste for cum was becoming more intense by the minute. I lowered my lips to the tip of his cock when I felt his hands on the back of my head forcing my head down on his waiting cock. I choked as the cock hit the back of my throat and went part way down my throat.
Richard let up on the pressure on my head and started fucking my face. I was sucking as best as I could. Moving my hand I started to play with his balls and could feel them pulling up as he got ready to cum. When he came it was three quick burst that filled my mouth then three or fur more small ones as he held my head still and I was just sucking the tip in my mouth.
I moved back up on Richards body and laid beside him. I was glad I had made my man happy. He lay there, eyes closed and a smile on his face. We rested for a few minutes with me snuggling up under his arm and my head on his chest.
Moving around, Richard got up went to the bathroom and came back in the room bringing his tube of lube he came back to the bed. "Now we're going to work on that sweet young virgin boi pussie of yours. I'm going to make you cum till you beg me to stop".
Lying beside me, he brought his lips to mine for a long tongue fucking kiss. Our tongues were in a battle all their own. I didn't even notice when Richard had lubed up my ass, The first sign was when his finger penetrated me to the hilt with one quick motion. His finger was twisting around in my hole and he was rubbing my prostrate. Our kissing continued as did the invasion of my once virgin hole. Soon enough I felt him inserting a second finger. I felt full as he slowed down his pace and was working them all around, twisting them and pulling almost all the way out before reinserting them and massaging my boi clitty.
I could feel the orgasm building in my young body. I was going to have my first orgasm without anyone touching me. The eruption shot up on my belly cock and balls. I figured now I can rest.
Richard slowed down his motions but never stopped. I again felt my body coming back alive. It seemed like every nerve in me was being assaulted by those two probing fingers. In just a few minutes my cock was again hard and wanting another release. He bent over while still fucking my hole with his fingers and cleaned me up. Licking up all my cum from my stomach then my balls and finally taking my whole dick in his wonderful mouth he cleaned it then continued to suck the life out of me. My second explosion was like an electrical shock. Still that talented tongue and those magical fingers didn't let up. He just slowed down his motions with his mouth and worked those two fingers on my clitty all the more. Unbelievable, my cock came back to life on its own accord. When he swiped his tongue across the head My whole body lifted up off the bed. The explosion of the orgasm was so intense that I passed out.
Hours later I woke up. My nightie was pulled down, I was tucked in and could feel a slight pressure on my ass. I reached back and felt the butt plug firmly in place. With a contented smile on my face I went back to sleep.
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