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Copyright © 2002, Jack Spratt. ALL Rights Reserved
Date of first publication Friday PM, July 12, 2002:
Later in my life I learn my mom always wanted a girl. After I was born mom's doctor advises her that her childbearing abilities are over, she will never have the daughter she always wanted. Subsequently she raises me like the daughter she can never have rather then the boy I am. My dad makes it easy for her. Dad's job requires intensive travel. Sometimes he is away from home for months, allowing mom to do as she pleases with my upbringing. This gives mom ample time to bring me up as young girl. She fusses over me and dresses me in frilly pink things as a baby. All her friends think it is cute and approve. These are not events in my life I actually remember but as a twelve year old I find a box in the attic containing my mom's diaries of how she raised me as a girl with the help of many of her friends.
My childhood friends are all girls my age. My mom only buys me girl oriented clothing and toys. As soon as I am potty trained she has me in cute little girl panties. Since I don't know any differently I accept all the pampering usually given to young girls. At that stage of my life me being treated as a girl is normal. She lets my hair grow long and styles it as a young girl, usually in a ponytail or braids. She enters me in numerous young girls' beauty pageants when I am five and six. I prance around in my short dresses and high heels flipping my skirts so all can see my frilly lace trimmed panties. With the expertly applied makeup I fool everyone. Hell I actually win numerous events and I still have the awards hanging in my room. My small frame works right into her plan for me. Often we do things together, like combing our hair to make it shine, trying new make up and perfume. She buys us matching outfits. Mom shows me her full bra when I get my first training bra and tells me the difference in size between us is because she is older. I often see her in panties and thongs. I never considered the difference between our legs. Mom has a full bush of hair. I just thought her thing is covered with her long black hair. I enjoy her putting makeup and lipstick on me. It makes me feel so attractive.
I have a wardrobe of dresses and skirts. My lingerie drawer is full of girl panties with cartoon designs on them. My lace-trimmed panties are for competitions. Everything is soft and frilly and I love the feel of them against my body.
My first recognition that I am not a girl is when I start school. There is no way she can disguise my male tool. The first time I go to the bathroom with other girls would have been my undoing. My mom finally dresses me as a boy. My problem is I didn't know how to act as a boy. All my movements and actions were totally feminine. Boys avoid me and the girls think I am really different. My school life brings me nothing but heartache, as I am teased constantly.
My name is Alex Bradley. For years my mom called me Alexia. At twelve, I still have a very slight build and look very feminine. All my movements are totally womanly. Fortunately I do very well in school and receive award after award for scholastic achievement. It gives me a sense of accomplishment considering the teasing I endure.
At this age my only friend is Jordon McPhee. Why she befriended me I really don't know. She is thirteen and head of the school's cheerleading team. Our friendship starts when I assist her with her math for a couple of terms. She treats me like a boy even though I don't act like one. Her looks make her the target of all the macho jerks in school. I think she feels safe with me.
I still enjoy wearing my frilly soft clothing. I like girl's silky panties and I have several lacey training bras that I wear when I am at home. My cock is long and thin. I have very little pubic hair and what is there is very fine. Early in life I discover the ability to masturbate. Now this part of my life I really enjoy. The amount of cum I can shoot is excessive by any standard however I wasn't aware of this feat as I have no other boys to compare it with. Perhaps is my long thin cock that gives me the ability to shoot nearly five feet.
Mom buys me a blond wig that allows me to continue to pass a girl. When my dad goes on extended trips mom has me dress as a girl on weekends. We often travel to the next town where I will act out the day as her daughter. I like being a girl and doing girlish things. It feels good to be dressed as a girl as compared to a boy.
Jordon has me over to her home regularly. I continue to help her in numerous subjects and we do projects together. She stands up for me against the bullies in school that tease me continually. She has organized the other girls to help me if the guys start pushing me around. Girls can be vicious when they have a reason.
As the head of the cheerleading squad in our school she has a fantastic body and loves to flaunt it. With that influence over a number of budding cheerleaders many are more then willing to do her favors. One of the favors is to protect me from the bullies. They have made it known that they will not date anyone that hits on me. I have power even as a weakling. It certainly makes my life a bit more livable. Jordon invites me to many gatherings with the girls on her squad. Most don't look at me as a guy but a friend of Jordon's. Secretly I wish I could be one of the girls. I have seen many of them in states of undress that other guys would give their eyeteeth for.
My relationship with Jordon continues to strengthen. We go to school together. When she is ill I make sure she has all her current school assignments and she has does the same for me. She treats me like an equal.
One day, our relationship changes. Jordon invites me to join her at her home. She tells me Mia, one of the cheerleaders, will be there as well. Mia is a beautiful twelve-year old. She has dark chocolate skin with beautiful dark brown eyes. She has been part of Jordon's group of close friends for years. I think they have known each other all through school.
It is Friday night. My mom tells me to be home early as we are going to be mother and daughter tomorrow. She plans on buying me some sexy lingerie at Victoria's Secret. I am looking forward to it.
Mia is already at Jordon's when I arrive. Both girls are in attractive bathrobes. Jordon leads me to her room with Mia bringing up the rear.
"Alex what you see and hear tonight is between us three. I know you like acting like a girl. Mia and I are going to show you how real girls actually act."
I am totally confused. Mia has a smile on her face. What happens next is something that my mom never prepared me for. Jordan locks her door and both she and Mia walk to her queen sized bed. Both girls drop their robes. They are both totally naked.
I have seen the girls in various state of undress before but never totally nude as I am seeing right now. Jordon is blond and has blond hair between her legs. I can see the top of her slit. Mia has big titties with large brown nipples. Between her legs is covered with very thick matt of dark curly brown hair. Her pussy lips are very full and puffy. Both are watching my reaction and laughing.
"Alex is this the first time you have seen girls naked?"
"Yes."
My body is hot with my blush. My long thin cock feels tingly and starts to extend pushing out on my pants. Both girls come close to me, moving slowly. I love the look of their titties and wish I had more. Their nipples are hard and standing out from their lush bodies. I feel things running through my body I have never felt before. My cock is now noticeable. I can feel the heat of my embarrassment running through my body, and then, another shock.
Mia is on her knees in front of Jordon. Her pink tongue trying to get into Jordon's slit. My knees are shaking; I have no idea why. Jordon falls back onto the bed and spreads her legs wide. I can't believe the view. I wish I were Mia who is on Jordon like a cat. Her tongue is licking and I watch her kiss Jordon's cunt many times. Jordon is squirming. Then they switch positions with Jordon between Mia legs. Finally they are done embarrassing me.
"Alex you have seen all of us so it is only fair that we see you: undress."
Jordon voice is very forceful. She has never been that terse with me before.
"Now Alex."
Quickly I undress. My cock is standing out nearly seven inches from my body. Both girls stare at with interest. I want to pump it now.
"Mia, we have a winner. None of the boys I know have anything as long or as thin."
"Larry comes close but Alex gets the prize."
"The way it looks Alex needs to be milked. Do you want to do it or shall I?"
"Maybe we both can do it before he goes home. It will be nice if we can."
Milk me? What are they talking about? Mia moves closer to me and puts her warm hand on my very hard cock. Oh it feels so good. She starts to stroke me. My knees nearly buckle as she brings me close to the brink. Her small hand is easily able to encircle my thin long cock. Jordon is watching every stroke.
"How does he feel Mia?"
"Well, out of all the cocks in our class, no one is close to Alex. Look, his cock hair is as fine as the hair on his head. He feels really cool and the length if it makes it feel like a real pants snake."
The more Mia stokes me the better I feel. My body is telling me that ejaculation is close. Mia grasps me with both hands makes it feel like a caress. Then it happens. Cum shoots straight up in the air and lands on Jordon's breast and tummy. She has a startled look on her face. I watch as she flicks some on her finger and tastes it.
"Mia you should taste him. It is mild compared to the other guys I have sucked."
Mia flicks her tongue to the tip of my cock, licking the last remnants of cum seeping from me.
"Hey you are right. It actually tastes good. Too bad we wasted it."
"Well you can lick it off my nipple."
Jordon has cleaned most of it off her tummy. Mia sucks and then tongues her breast, licking all the rest. I just watch, fascinated.
"I will milk him into a glass. We can share."
I watch the girls' sixty-nine. Their bodies shudder as they bring each other to the brink. It doesn't take long for me to start growing again.
"Jordon, Alex is ready again. Doesn't it look fantastic sticking out from his body? Look at his balls; they don't have any hair on them at all. Alex, lay down on your stomach."
I do as I am told. Soon I feel Mia's finger probing my asshole.
"His asshole is as small as ours. It is tight. Doesn't it look cute?"
Jordon gets a tube of cream and I feel the cold liquid against my asshole. Slowly Mia inserts her finger into me. It feels odd but exciting at the same time. When she starts stroking inside me, my cock seems to gets harder.
"Jordon you milk him I will massage his balls. Ralph says he really cums a lot when I do it for him."
Jordon is studying my long shaft. She seems mystified by its length. From this angle I can see between her legs. Her opening is coated with a film of moisture. Her sexual odor is apparent and very appetizing. How I would love to do to her what Mia did to her. When Mia leans over I can see her as well. Her black lips open, exposing the beautiful pink opening of her vulva. My hips are now pushing toward Jordon as she manipulates me.
"Mia, get a glass from the bathroom, we don't want to loose a drop."
Jordon continues her slow stroking of my shaft and when Mia returns she puts her warm hand on my ball sack. The next explosion is close.
"Alex you had better tell me when you are going to cum. You will be punished if you don't."
"Punished?"
"Yes, from now on you will be my 'Boy Toy' to share. You will be milked every day by some one I designate. There will be a lot of girls chomping at the bit to milk you when it is known how sweet your milk is. The second part of your training will start after you cum into the glass."
What second part of my training? What the hell is going on?
"Jordon, I am going to cum."
Quickly Jordon puts the end of my cock into the glass. The force of my ejaculation causes it to splatter. She doesn't look happy when it soaks her hand.
"We will have to devise something better to get all his milk. We will have to tell whoever milks him next of the problem."
Whoever milks me next? I am lost. Jordon and Mia look at the accumulation it the glass; each putting their finger in tasting.
"Shall we start the second part of his training Mia?"
Mia lies on the bed with her legs spread, her vulva is glistening with moisture. She brings her legs up so I can see her tight asshole as well.
"Alex your job will be to pleasure who ever milks you; for as long as they desire. You saw what I did for Mia. Now it is your job to do her and then me."
Jordon lies beside Mia and spreads her legs waiting. This is all new to me. I never even dreamed of anything like this. Mom and I did things together but nothing like this. Leaning over Mia her scent hits me. If she taste as good as she smells I will look forward to doing her. It isn't long before I realize that this isn't punishment but a privilege. Mia's body tosses and turns as she climaxes. She does taste good. Finally I feel her hand on my hand pushing me away.
"Jordon you are going to like his tongue; he is a natural."
Jordon's taste is different then Mia. Both are good but each is unique. Jordon has her hands on the back of my head pulling me into her pussy. Like Mia she twists and turns as she climaxes. Then she pushes me away.
"He is good Mia. I think we have our 'Boy Toy' at last. Alex will fit in with the girls and has what we have been looking for, a super cock that provides us with sweet cream and soon other things. Can you imagine?"
Both girls giggle.
"Alex you can get dressed now. Remember you are our 'Boy Toy'. Don't tell anyone. We will continue to protect you against the bullies but now you will be paying for it. You are not to masturbate unless you are instructed by one of my girls."
As I dress both of them, still naked, confer about something. Both are sitting with legs crossed exposing the interior of their vulvas. I wonder if mom would like a boy toy.
Jordon speaks
"Alex every day at school some girl will come up to you with this medallion in her hand."
She showed me a distinctive medallion she had firmly in her hand.
"She will milk you in any manner she enjoys and then you will be required to make sure she is totally satisfied before you leave. It will be her choice as to the method. You do not have a choice in this matter do you understand?"
"Why are you doing this to me? I have done everything you have ever wanted."
"Didn't you enjoy it?"
Come to think of it everything I have been exposed too has been fun. I liked sucking both girls' tasty pussies and I can only assume all the other girls will taste as good. Being fingered and milked by a different girl won't be any burden.
"I understand."
I watch them get dressed and both Mia and I leave at the same time. I feel exhausted but happy.
"Alex you have a nice cock and very sweet milk. I am glad you are our 'Boy Toy'. I think you will enjoy all the girls."
She surprises me by leaning over and kissing me on the lips. I can feel my cock react. Her hand is on my crotch, rubbing.
"If I had time I would milk you again. Some one will approach you with the medallion on Monday so be prepared. Have a good weekend and don't play with yourself. Your cream belongs to us."
Mom has me up early to make preparations of our shopping trip. The first thing mom does is shave my legs. After we shower together she helps me dry. For some reason she takes an extra long time drying my cock and bum. She rubs in a lotion on my shaved legs to take away the sting. She coats me with my favorite body splash. We both smell good.
"I have a surprise for you Alexia."
Laid out on the bed is a new short skirt and top in my favorite colors. The skirt is bright red and a matching tube top of red and white strips. Lying on my bra are two inserts. Next to all of the clothing is a restrainer to keep my cock from showing through my skirt.
"You will need them for your new lingerie. You will really turn heads today."
Watching with a new interest as mom dresses I'm wondering if she would like what Mia and Jordon had me do for them. When she leans over in front of me I am mesmerized at the size of her pussy. Her asshole is large compared to the girls. I can feel my cock pushing the restraint. What would it be like to lick my mom's openings?
Mom applies my makeup. What an ego booster. I look sixteen. My new boobs make a world of difference. The black pumps set off my long, shapely, nylon clad legs. Mom gives me a hug.
"Alexia you look good enough to eat."
"So do you mom."
Mom is dress in a similar short skirt. Her ample boobs are pushing out against her blouse. My new inserts have nipples that are evident against my tube top. Our drive to the mall is enlightening. At many stop lights we hear guys whistling at us. Mom smiles and I wave at a number of men.
Walking hand in hand I watch the reaction of the men as we pass. They seem very interested. We both are swaying our tight bums for affect. I can't believe the number of men and boys that do a double take to get a better look at mom and me.
Victoria's Secret is a dream come true. I can't believe all the styles of lingerie available. Mom picks out three bras and matching panties for me. She smiles when she picks up a string thong and throws it in the pile of purchases. She purchases two up lift bras for herself. With her massive boobs she can use them. They wouldn't do me much good. I don't have anything to uplift. What surprised me is she purchases four thongs for herself. With her bush it isn't practical. The last purchase is three pairs of crotch-less panties. She mouths 'for you' at me. The excitement I feel is concentrated on my restrained cock.
We window-shop the balance of the day. We both boldly carry our Victoria Secret bags. Guys look at us and smile, likely wondering what we had purchased and how it would look on our shapely bodies. We stop for dinner at a restaurant before going home.
"Alexia I am going to need your help when we get home. I want to shave my pussy with your assistance. I need to be bare to wear the thongs I bought."
"Mom they look so sexy. I want to try the crotch less panties without my restraint. Do you think they will look good on me?"
"I know they will. Tonight we will start more of your education. It is time you discover exactly what your tool is for."
Is mom going to milk me? Wow! I wonder if Jordon will punish me if mom milks me. She told me not to masturbate. It can't count against me if my mom does it. I can't wait to get home.
"Alexia, go to your room and get undressed. Lay out some of the new clothing for later. Meet me in the bathroom."
It feels good to take of my restraint. My cock is hard sticking straight out from my body. I hope mom likes it that way. In the bathroom mom is just finishing undressing. Her large breasts are sagging just a bit. What I am interested in is between her legs and ass cheeks. She is just like the other girls but much bigger. We shower together. I keep bumping into her breasts and she into my erection. When we dry she sits on the john and gives me a can of lather.
"Alexia the rest is up to you. Lather the hair on my pussy and shave me."
Delicately I do as told. My fingers explore every nook and cranny of my mom's pussy. It is soft and sexy. My cock is extended between my legs. Mom seems to be staring at it. I haven't been milked since Jordon did it yesterday so I have a full load. I hope mom likes it as much as the girls. I am a little apprehensive. Once I get started everything goes well. Finally I rinse off the lather exposing her beautiful vulva. It is so much bigger then Mia's and Jordon's. Mom's outer lips are heavy and puffy. They are soft to touch. Mom's eyes are closed as I explore.
"Mom, do you want to shave your bum as well?"
I can see the hair at the base of her pussy extending up her crack. There is fresh moisture forming on her pussy lips. The scent is fantastic. It is stronger then the girl's but just as potent.
"Alexia; what is a good idea. I don't want any hair showing when I wear my thongs."
She stands and leans against the counter her legs spread. I gently spread her cheeks. Wow what a striking view. The rim of her asshole is wrinkled, not smooth like the girls. The amount of hair is extensive but not as thick as it was on her cunt. Lathering her bum my fingers explore again. There is little resistance as I probe her opening. My finger quickly disappears into the warmth of her body.
"Alexia that feels so good. It has been a long time since someone felt me like that."
"You like it mom?"
"Yes, I have always enjoyed my butt being played with. Your dad doesn't do it anymore."
I shave all the hair, rinse and admire my handy work. Every thing is exposed. Now I hope mom will leave it exposed for me. She moves so she is facing me, my face level with her pussy. Her inner lips have extended beyond her heavy outer lips. They didn't look like that before I shaved her ass. I stare fascinated at the view. Mom is smiling at me when she puts her hands on my head.
"You are a good daughter Alexia. From now on you will be my official shaver. You did a good job. You may kiss me if you like."
Not only do I kiss mom's pussy but I lick as well. She nearly collapses.
"Not now Alexia lets put on our new lingerie. You come to my room. Your education is going to start."
The crotchless panties allow my seven-inch snake to stand out from my body. The panties are a deep red lined with white lace. The new bra with my inserts really sets off everything. Hurrying to mom's room I find her laying on her back in her thong and a lift up bra. She really looks sexy. The crotch of her thong is damp.
"Lay beside me Alexia. What you started in the bathroom is what I really enjoy. Having my pussy kissed and licked it one the best things I can imagine. I will do the same for you. Did you like kissing your mom's pussy?"
"Oh yes mom, can we do it some more?"
"Yes and many other wonderful things. Kiss me again."
Mom arranges her body with her knees up and legs spread. I get in between and pull on her thong. She lifts her bum so I can remove it. It isn't long before my face is covered with mom's ample juice and she is cumming. I manage to spread her ass cheeks and tongue her back opening as well. She rolls over on her tummy allowing me total access to her wrinkled opening. Her body twists and turns as she has one climax after another.
"Alexia you learn fast how to make your mom feel good. Now it is time for me to show you something new."
She has me on my back with my cock pointed to the ceiling. I watch as she tenderly caresses my full length. She seems to be sighing. Her hand slips between my bum cheeks probing my asshole.
"Alexia you are so tight. I remember when I was that tight. You dad took care of that many years ago. We enjoyed anal sex numerous times before we got married. Your dad could cum buckets when he was young."
I feel good as mom continues to reminisce. She is in for a surprise if I cum in her hand. Closing my eyes I think of Mia and Jordon massaging me for my milk. I am shocked when I feel my mom's mouth sucking me. She manages to take my full length down her throat. The feeling is awesome. My education continues. Mom stops.
"Now; the final lesson."
Mom arranges her body on the bed with her legs spread. Her cunt is glistening with moisture. The lips are open showing her pink interior.
"Get on top of me Alexia."
I have a bewildered look on my face but do as I am told. She grabs my cock and guides into her cunt. I can't believe the feeling. I push against her burying all seven inches deep in her being.
"Oh Alexia you feel so good."
The natural tendency kicks in as I start to hump. Mom's cunt seems to be grabbing me and squeezing. The sensation is indescribable. The faster I pump the better I feel. Mom arm's are around me hugging me tight. I can feel her hips slamming to my body. Then it happens. Sting after string of cum shoots deep into mom's body tenses for a climax. I have never felt like this before.
Mom kisses me like Mia did after my milking. Her tongue is playing with my tongue. Mom's nipples are hard and I kiss each one.
"Alexia you did well. From now on we will sleep together when your dad is traveling. I hope you enjoyed this as much as I did."
"I did mom. I want to do it again."
Monday at school it is like nothing has happened. Both girls act normal when we join each other at lunch. A number of the guys are envious of me being able to join two of the best looking girls at school knowing if they approached them their advances would be rejected. They don't give me any hint as to who has the medallion. When three o'clock rolls around I am still in the dark. However while in the hall a very young girl comes up to me showing me the medallion.
"Meet me at the gym at three forty-five."
I watch her continue down the hall. I have seen her in the halls; she is a middle school student; her class uses the pool twice a week. I have never paid any attention to her or her classmates, she has a perky bottom. I am at the appointed place at the appointed time. I watch as she rounds the corner. She has small titties but the rest of her is well proportioned.
"Hi, I am Susan Bradford. Follow me."
Doing as I am told. She tells me that we will be meeting her mom. She will introduce me as a student tutor to help with her math, in which she needs all the help she can get. Being this close to her I can smell her scent. My erection is noticeable. She looks at my pants' bulging and smiles. A car stops in front of us.
"Hi mom, this is Alex. He has been is a student tutor. He is going to help me with my math concepts."
One of the few advantages of looking so effeminate is most women don't look at me as a threat. Mrs. Bradford smiles.
"Alex you have your work cut out for you. Susan has had trouble with math forever. She will need it to get into college. She wants to become a doctor."
"I have been tutoring for nearly a year and have helped other students. I will accept Susan as a challenge."
Once at her house Susan brings me into the kitchen and gathers some drinks and treats.
"Mom we are going to my room. Call us for dinner."
"Susan, I will have to call my mom and tell her where I am."
"You can do it from my room."
Her room is lined with dolls. She has a large bed in the center with a desk and a computer in one corner. She points to the telephone and then locks the door. Mom tells me that it is good that the school recognizes me as a tutor. She is even more impressed when she hears it is a girl I am assisting.
"I hope you pick up some of her attributes. It will help us on the week end."
Susan is standing before me in her lavender blue panties and matching training bra. I have one the same color. She is petite but very sexy looking. I feel my cock stirring.
"Get undressed. I have to milk you. Jordon told me not to fail, we are first cousins. It is an honor Jordon granted me this opportunity to see a guy naked."
As I stand naked before her, her eyes light up as she sees my long thin cock. Gingerly she gropes me. I am going to enjoy meeting new girls every day. She stokes my shaft.
"This is cool. It is so long. Jordon says you really can shoot. It will be my first time. Lots of guys want to take me out but Jordon told me most of them are pigs or jerks. You are the 'Boy Toy' for her friends."
"That is what she told me. You are the first one to show me the medallion. I really don't know what is going to happen."
"I am glad I am the first. I like the feel of you."
My body starts to hump my excited cock into her hands. I am getting close. Susan is eleven but looks older. I certainly would like to try what mom did yesterday with her. My hips are pumping in her hands. She is watching my reaction.
"Jordon says I should have you shoot into a glass. I have never tasted a boy. Actually you are the first one I have ever seen close up."
"Can I see you naked Susan? Jordon and Mia were naked when they milked me."
Reluctantly she removes her panties and bra. She has no breasts to speak of, just hard nipples. What really turns me on is her bare pussy. I hope she wants me to lick her. Her luv lips are partially open with moisture seeping. She has a fine coating of light blond hair surrounding her vulva.
Susan is pumping with the head of my cock pointed into a baby food jar. When I do cum she nearly drops it. My cock pulses, finally going soft.
Lauryn
- 14.04.2020
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