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Becoming Bobbi

Category: Fetish
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I had my “secrets” we all have them. I guess on the one hand we are terrified we will be discovered but on the other, there is that little part of us that wants to be discovered. At least that’s the way it was for me. Meeting Ms. Anders changed all that. Somehow, from that first meeting, she could see all the way through me. She could see that dark secret that I always thought was safely hidden away.

I should start at the beginning and maybe this will all make a little more sense. My names Robert but I have always been called Bobby. I just turned 22 and have been working for an insurance company here in town. I didn’t grow up here but moved after I graduated from high school. I was always a bit small for my age, I’m 5′ 6″ and really pretty slender. Most of the time in school, I got picked on a lot because of my size so I was more than happy to get out of town.

I’ve known I was different when it came to girls for a long time. Looking back it’s pretty easy to see where my “secrets” came from. I have known about my submissive side for a long, long time. I really believe it has always been there. I remember laying in bed when I was 10, 11 or 12, going to sleep and fantasizing about girls in the neighborhood, holding me down and kissing and “playing” with me. It was also around this time that I had my first sexual experiences. They all involved 3 older girls in the neighborhood, the girls were always “in charge”. The first time involved them getting me to strip naked for them. They said they would too but after I had, they refused. I still remember the intensity of my feelings, standing there, naked while they “examined” me. Looking back on it, I know that it is that wonderful combination of sexual excitement, humiliation and fear the never fails to take me into “subspace”, where I willingly submit to whatever She desires. Then there were other times that I was alone with one or the other of them. They would have me undress for them and they would partially undress. They had me masturbate while they watched and often had me lick and kiss their breasts, legs and privates. This continued until I was 15. They were all a couple of years older than I was and started dating guys from school. I still remember the combination of sexual excitement, fear, and shame that I had every time it happen. Even though the fear and shame were there, I kept going back for more and more. They would always begin teasing me and before long I was doing what they wanted. For a while in high school and for a year or two after that, I tried some dating but it just didn’t work out.

First off, I really didn’t find girls my age all that interesting. I always found my self “gawking” at older women. A 30 or 40-year-old woman always seemed so much sexier. In addition they were more assertive and seemed more “no non-sense”, which turned me on too. There were a few times that I tried to approach a woman or two but it never worked. I plan everything out a head of time but I would always get over come with shyness and embarrassment when I tried to talk with them. One of the worst times happened with a woman from my apartment complex. I had seen her around there and she just looked so sexy. She was probably about 35 and I just couldn’t keep my eyes off her.

I happened to run into her at the laundry room one day and tried to strike up a conversation. I was pretty much tongue-tied and did nothing but blush while I tried to ask her about her self. She ended things by telling me I was cute but she just wasn’t interested in “little boys”. After that, my sex life pretty much consisted of cruising the Internet. It was one the Internet that I started to put some names to my “secret” life. I found a couple of sites that were filled with stories and I spent hours reading and then masturbating for relief. I found pretty quickly that stories about dominant women and submissive men were the biggest turn on. In particular, women feminizing their men were the most irresistible. When I would read these stories and fantasize about being with such a woman, I could sometime get that same feeling that I had with the neighbor girls. That feeling of sexual excitement, fear and shame that was always so intoxicating. I also found myself exploring the “adult” bookstores. At first I didn’t buy anything, I just “window shopped” the various thing they had but it didn’t take too long to buy a few “toys”. I also like to wander the malls. In particular, I like to go through the lingerie section of the department stores and imagine what it would feel like to be wearing some of the items. On these little trips, I would always try and look casual. Maybe like I was buying something for a girlfriend. On the inside though, I was always excited and scared someone would “know” my secret. On the one hand I was terrified of being discovered as a submissive sissy and on the other the excitement was too much to resist. I just could not stay away.

It was a beautiful summer day and once again I had decided to do a little window-shopping at Macy’s. It was always a favorite of mine. The lingerie area was a bit more secluded than a lot of the other stores. It gave me more opportunity to look and daydream. I had been wandering through the racks for several minutes and had become engrossed in the bustiers. They were so sexy and as I stood there, it imagined how they would feel and how they would look on me.

“That would look good on you, don’t you think?” I froze, could think and could not speak. I could feel the terror of being caught in the pit of my stomach and feel my face flush with embarrassment. “Cat got your tongue?”

I turned to look. She was 3 or 4 inches taller, slender and blond hair and probably 35 years old.. She was beautiful and her eyes seemed to look through me. I couldn’t hold her gaze, I quickly glanced down. I could feel my face burn with embarrassment. She reached down and took my hand “follow me”.

Without a word, she guided me out of Macy’s, down the mall to the Starbuck’s. “sit here while I get us something.” I started to ask for a coffee but she stopped me mid sentence “I’ll get something that suits you, don’t worry.”

She returned and placed a latte in front of me. Her name was Susan Anders but explained that, considering the differences between us, I should address he as Ms Anders. She went on to ask about what I had planned for the day, where I worked and all sorts of other questions. Through out it all she leaned close and was continually touching my leg or arm. Often sliding her hand up my thigh and across my crotch. Each time she did, my embarrassment and sexual excitement deepened. I was hard and she knew it. All of this was terrifying to me but I didn’t want to stop.

She stood and took my hand again. “You are such a sweet boy, we will spend the rest of the afternoon together. Would you like that?”

There was a part of me that said I should run, that I should escape but I was powerless at that point. “Yes, I would like that Ms Anders” and I followed along.

She lived in a town house not far from the mall. Once there she led me in through the front door and into her living room. She showed me a number of her mementos and then brought us each a glass of ice tea. “Really, the polite thing would be for you to be serving the tea, don’t you think.”

I struggled to say, “Yes Ma’am.”

“You are really rather embarrassed around me, aren’t you boy.”

“Yes, Ma’am”

By this time she was sitting in an over stuffed chair. I was still standing; it just seemed like the right thing to do. I just had the feeling I should wait for her to tell me to take a seat. In a moment or two, she had me pull a footstool and sit in front of here. I felt a bit odd. The stool was kind of low to the ground and I found myself looking up at her.

She continued her questions but they became much more personal. She wanted to know about past relationships, if I had a current girl friend. She then mused about my name and how it’s also a nickname for Barbara.

“Do you spell it with a Y or an I at the end? No matter, if you end it with a Y you should change it to an I. That would suit you much better.”

“You will do that for me won’t you Bobbi.”

Every brain cell I had screamed at me to say NO but when the word came out the were “Yes Ma’am, I will be Bobbi from now on.” Her smile simply overwhelmed me.

“Bobbi, are you enjoying your time with me? I’m finding that you are a type of boy that I have always enjoyed having around. Would you like to spend more time and more days in my company?”

“Oh yes Ms Anders, You are beautiful. I would so love that.”

She leaned toward me place her hand on my thigh and slid it up to my crotch. She looked into my eyes. “You will find that I have a different idea about relationships than those girls you have known in the past. I have had a relationship like this before, it was good for me, it was good for him, and I think it will be good for you. You see, I am a naturally dominant woman, I make the decisions, I call the shots. What this means, Bobbi, is that I take the role in the relationship that you may associate with the traditional male or masculine role of authority in the books or stories of older times”.

“And just so you understand, that means that the male must assume the opposite role, the feminine or submissive traditional role of years past”.

“And I must tell you that it means that I make all the decisions about household duties, money, and the bedroom. All of them.”

“Not only must you accept it, you must embrace it.”

I was a jumble of feeling. It was that same jumble of feeling that I had felt with the three neighbor girls. Fear, sexual excitement, shame and humiliation just like back then I was powerless. I knew that no matter what my mind tried to tell me was the “smart” thing to do, I craved what she had to offer.

She felt me hardened and a devious smile crossed her lips. Her hand tightened around my penis.

“You don’t need to say anything. Your little clit is telling be everything I need to know. Sometime words lie but your body is telling me that you are just the kind of boy I thought you were.”

“Push the stool back and stand up.”

“Now unzip your pans for me and peal them and you underwear down to the floor.”

I had no power to resist but for that matter I didn’t want to. I pulled them down and my penis dangled out. Hard. Excited.

“Kick your pants and underwear aside and kneel in front of me Bobbi and make sure your shirt stays out of the way, I want you uncovered.”

With in moments I was naked from the waist down kneeling in front of her. Her legs were slightly apart, her dress was pulled up a bit and, when I looked straight ahead, I was looking at her pussy.

“Keep your eyes right where they are. I have some more questions.”

I was completely mesmerized by this situation. I was powerless to resist her, nor did I want to. I was captivated by the sexual excitement.

“Now I want to know all about you, everything sexual that has happened to you and all about any older women that just being around has made you hard .. like you are now”.

I talked and she listened. I told her about lying in bed at night and fantasizing about the neighborhood girls holding me down a kissing me, About the three in the neighborhood and the things they had me do, about my attempts and fascination with older women and finally about the internet. Through out all this my penis stay hard and excited. To make matters worse, she periodically flicked it with her foot. I was constantly throbbing but I did not dare touch myself.

“Very good Bobbi, I’m pleased just a couple more things and I’ll let you go today”.

“First, I don’t want you to make a decision today, even if you think the answer is yes. I want you to think about it. If your answer is yes, simply come back on Friday afternoon and don’t make any special plans for the weekend. You won’t need to say anything, you being here will be your confirmation. answer. You being here will be your confirmation. We will not need to discuss it further, you simply will follow my lead in all matters, your submission unspoken”

“Now one last thing Bobbi, I know how sexually excited you are and I know that when you get home one of your first thoughts will be to masturbate but don’t. Your decision will come so much easier if you don’t release the tension. I know it will be hard so I have something to help. Now stand”

After I stood, she left the room for a minute and came back with some ice and some other thing that I was not sure of. She sat back known an applied the ice to my genitals until I was limp again. She took the device and started to fit it to me.

“This is a chastity device and It’s called a CB6000. It will help you keep from masturbation. I’m not going to lack it on but I am going to use a plastic tag. I will know if you remove it.”

“If you come here on Friday, I expect it to be still in place. If you decide not to come, you can remove it any time. Now pull on your pants, it’s time for you to be on your way.”

I left without another word being exchanged and walked back to my car and went back to my apartment. Even though it was late afternoon, I needed a nap. I was an emotional wreck and had a terrible case of blue balls.

I guess I knew all the way along that the answer was yes but that did not make the next few days any easier. I tried to distract myself by reading story after story on the internet. On the one hand, the stories made me want to masturbate more and more but the CB6000 kept that from happening. I wanted relief but didn’t want to disappoint Ms. Anders. Laying in bed at night my only thought to be kneeling before her again.

When I checked my email Friday morning, there was one from Ms. Anders, simple and just a few words.

“If you want to move a head, meet me at the Starbucks rather than my condo. 3pm sharp.”

I was an emotional wreck. I knew that I would be unable to resist meeting her and I knew that she would set the stage for me to beg to be a part of sexual things that had only lived in my fantasies. I knew that in her presence, I would be the worst kind of slut. She would be in control of my sexuality and I would be powerless to say no to any of her requests no matter how shameful, degrading or humiliating they might be.

I had said before I knew I was different. Men are strong and in control of their women. They do what they want and get what they want. I, of course was different. I was powerless the refuse the request of a strong woman. Beyond that, it seemed that when it came to sexual things, all I could fantasize about what being taken by a woman in the most shameful ways.

“I’m so glad you came” she said as she sat down. I felt my face flush and the blood flow to my crotch; I wanted to run but was immobilized. She touched my arm.

“You are such a sweet innocent thing. I will so enjoy bringing out that wanton little slut that I know is hidden inside you. It’s what you want isn’t it Bobbi?”

“Yes Ms Anders” was all I could manage to say.

She smiled and sat back. She was silent for a moment and then she reached into her purse and pulled out a pair of pink lace panties and slid them across the table to me.

“Go into the restroom and put these on. Throw your other ones away; you won’t need any boy’s underwear any more. When you get back we will do a little shopping.”

When I returned, she stood and whispered “that’s a good little sissy, Let’s do some shopping before we go back to my place. She took my hand and we headed in to the lingerie department of Macy’s and started browsing. She sorted through the racks and found several things. “You will be such a sexy little thing when I’m done.”

When she had picked it all out, We took everything to the cashier and waited for the total. As she sorted through the purchases, a puzzled look came over her face and she directed a question to Mistress.

“I’ve been noticing the sizes and I hope they are not to small for you Miss, You are quite tall and these might fit a shorter women a bit better. Are these a gift?”

“Oh no, these are not for me, they are for my boy here. I would think the size is just right for him, or maybe “her” will be more like it when I’m finished.” Ms Anders answered.

The clerk cast a glace my way. “They will look lovely on him.” She then turned to Mistress and said “I’m sure you will enjoy him, I know I would.”

Ms Anders then turned back to me “I think we have embarrassed the sweet little thing but deep down he craves it.” She took my hand and we headed out of the store.

She had picked out a number of things; panties, stockings, garter belt and bustier. I carried the bag and had to scurry a bit to keep up with her. In a short time we were at her car and shortly after, at her condo.

Once inside, she guided me to the living room and took a seat on the couch. “Would you get me an Iced tea? You will find everything in the kitchen.” I of course, quickly completed the task and placed it beside her.

“First of all you need to become comfortable with your place around here. Nothing makes a better statement of that than your clothing. Your first task, when we are at home will be for you to remove all your clothing.” I understood her meaning and immediately began to strip and carefully fold my clothes. Once every thing was removed, I kneeled at he feet and bowed my head.

“Very good, my dear. I see that your chastity device is still in place. I’m pleased.”

She continued on explaining that shortly she would be helping me bathe and also removing all the hair from my body. She went on to explain that she always like her sissy’s hairless. “It’s just one of those things that will help you feel more in tune with your new life. Any one who sees you undressed will instantly know what you are. No man would shave himself at the command of a women.”

“Now boy, I want you to bend over the arm of the couch.” She went to the desk and got a couple of thing from the drawer. As she approached, I could see that it was some lube and a butt plug. “As I told you, I will be the dominant one and you will be the submissive one in all things. It’s time to start preparing your “pussy” for what’s ahead.” She took a few minutes and worked the lube into me. It was a little uncomfortable to start but, in not too long, I wasn’t able to stifle the moans. I felt the plastic of the butt plug as she started to work it in. It started to hurt a bit it stretched me out but, then it was in place. I could not help the moans of pleasure. “My little slut seems to like having his “pussy” filled.”

She had me carry the bags from Macy’s and drop them on the bed as she guided me to the bathroom. Once in the bathroom, she removed the CB6000 and ushered me into the shower. The warm water cascaded over me and she helped to wash my body with a perfumed body wash. I patted myself dry. She handed a bottle of hair remover. She didn’t need to give me instructions. I simply started to apply it to all the parts I could reach. She applied at to the rest.

After the allotted time the water came back on and all the hair remover was washed away. I ran my hands over my body. It was smooth and hairless. I toweled dry and applied the lotion that she handed me. “One more thing before we start getting you dressed. Bend over the sink, we need a little bigger butt plug to stretch you out a little more. I want my slut to be ready for later.”

She worked the new one in and again it was painful at first but she was gentle and it went in with a plop. She reached around and gently stroked my cock. “Always remember, this is now MINE. You will play with it only when I give you permission. I have always found that little boy sluts are always so much more attentive when they are not allowed to cum and I plan on keeping you very attentive and very horny.” She led me into the bedroom; I stood near the dressing table as she readied everything.

First came the bustier followed by the stocking. “Did you notice that I picked white for tonight? Do you know why?”

“No Mistress”

“White is for virgins. Nothing pleases a Mistress more than deflowering a sweet little virgin and turning her in to Mistress’s slut. When you first told me of your sexual experience, I was overjoyed to hear you are a virgin. You have never had sex with a woman and no one has ever taken that tight little ass of your. In terms of intercourse, you will remain a virgin but I will be making you all mine by taking that sweet little ass of your. You will soon be begging for me to fuck you ass.” She finished dressing me and then started with the make-up and finally adjusted a wig on my head.

“When your hair grows out some, we won’t need this, will we?”

She helped me to my feet and guided me to the full-length mirror. I was stunned. I looked like a painted whore. She was standing behind me with a smile on her face. “I rather like the look bobbi, you make a very convincing little slut.”

She reached down and started to stroke my penis, it felt wonderful. “I want you hard and excited.” She continue me and I could feel my self wanting to cum but each time I would start to get close, she would stop and let me cool down. Pre-cum leaked and she coated my lips with it. “I want you to just stay close to cumming; a slut is much more attentive that way.”

“Now my pet, kneel and wait while I change into something more fitting the evening.”

I sank to my knees and lowered my head. I could her moving about the room, opening closing drawers and the closet. “You may look up now but stay on your knees.” I raised my face and eyes and was stunned. She was absolutely beautiful. She took my breath away. She was wearing a black sheath dress that shaped it self to her body. It was slit up the side almost to her hips and showed the tops of her stockings and a bit of flesh above that. It was finished off with black heals. I was simply in awe of her.

I’m sure she sensed my wonder as a smile crossed her face. “Does my pet approve?”

“Oh yes Mistress, you a stunning.”

Mistress led me to the living room and she made herself comfortable on the couch. I almost instinctively knew I belonged on my knees at he feet. I gazed at her beauty. With a smile on her face, she slowly spread her legs and raised the hem of her dress.

“Come, take your place.”

I began to lean closer and she took my head in her hands and guided me to her pussy. “Please me.”

I began to gently lick and probe at her pussy with my lips and tongue. I reveled at the wetness and the scent. I nibbled on her lips and tugged gently. I heard her sigh as she dropped the dress back over my head. I was now in darkness and I simply continued to lick and suck along the length of her slit.

“Take your time, but makes sure you swallow all of my juices, they are to be you new nourishment. I want you to crave them; I want them to be your new addiction.”

Her moans and sighs continued and built to one orgasm after another. At each orgasm, her legs and hands would grip my head and then relax a bit until the next orgasm approached.

I had no sense of time but finally she relaxed her legs and pushed me back slightly. “You have pleased me pet. It is time for you to become mine. Once I have taken you there will be no turning back. Once his Mistress’s “cock” has taken a boy he is hers. Boys remember when he lost his virginity and shapes him for the rest of their lives. They take the woman and make her theirs. They are the aggressor, the dominant want. They make the girl their slut.”

She went on to explain the changes that happen in the psyche of the girl. How she becomes addicted to being the slut. “When a woman takes a boy’s virginity by fucking his ass, he will be forever addicted to her and he will be her slut.”

Mistress reached out and took my cock in her hands and began to stroke it. Time and time again she brought me to the edge of an orgasm but stopped short. She would let me cool down and then bring me back to the edge but never permitted me release. Just as she brought me to the edge again, she said “Do you want me to fuck you Bobbi? Do you want me to take your virginity knowing that, if I do, you will never be satisfied with sex as a man again? Do you want to become my slut, little Bobbi?”

The sane and rational part of me screamed silently in side my brain. It screamed how crazy this all was. How insane it was for any man to be submitting to a woman like this. Here I was, dressed like a fag siting in front of this women thinking about ASKING he to shove something up my ass. I knew what I should be doing is fucking her brains out. I was about to beg a woman to take me in the most shameful and humiliating way that I could imagine. In spite of that sane rational part of my brain, I could not resist. I was addicted to the feelings of shame, humiliation, perversion and sexual excitement that was coursing through my body. Truth be told, I was trapped from the first moment I heard her voice.

“Please Mistress, make me yours, make me your slut.”

She led me back to the bedroom and motioned for me to kneel again. She pulled an 8″ strap-on cock out of a drawer and presented to me. She reached back and released the straps of her dress and let it fall to the floor. I was in awe, the stockings and bustier. Absolutely beautiful. “Put my cock in place, pet. It’s only fitting that you get me ready so I can take your pussy ass for the first time.”

Once in place, she took my head in her hands and guided my mouth to her cock. “Show your respect to cock that is going to take your virginity.” I opened my mouth and she slowly thrust forward. I began to suck and lick it. “make love to it my pet and it will make love to you.”

I reached up and used my hands to steady it as my head bobbed up and down on the shaft. Of course my mind was a jumble of thoughts but my main desire meet her every desire. Mistress brought me tremendous sexual excitement and I desperately wanted them to continue and intensify. The humiliation of the situation aroused me even more.

Her hands eased my mouth off her strap-on; I sat back and looked up at her. She smiled over at me and then reached over to pick up a tube of some sort of lube and a condom. She explained that it was numbing gel and instructed me to apply it to my “boi clit” and then pull the condom on. “Now baby, it’s time for you to loose your cherry. You can play with you little boi clit all you want while I fuck you but it won’t help. That numbing gel will take way all the feeling in it but it won’t remove your desperation for an orgasm.” She signaled me on to my back on the bed and adjusted a pillow under my ass.

There I lay with my legs spread and her between them lubing up her strap-on and looking into my eyes. “I want to watch your eyes and face as I take you and as you become my slut.” She pulled the butt plug from my ass and the I felt the tip her cock at my ass. She leaned in and I felt my self being slowly filled. She pulled back a bit and the it moved in further. “Now baby al the way.” I felt filled and I felt her thighs against me. I moan of pleasure escaped my lips and she began to pump it in and out. Slowly at first and then building speed. “let me hear you slut”.

“Please Mistress fuck me. Make me your little slut.” She kept pumping it in and out and took a hold of my penis and began stroking it. “Would my little slut like to cum? Would you slut.?”

“Yes Mistress, please.” She began to tell me that I would cum but it would not be an orgasm. “Fucking you with the strap-on will milk all the cum out of you by massaging you prostate but you won’t have an orgasm. You’ll fill the condom but you will still be a horny little slut.” She kept pumping faster and faster. I felt closer and closer to an orgasm but couldn’t seem to quite get there. I began to feel an odd sensation in my ass and watched as cum filled the condom. More that I thought was possible. She smiled as it filled the condom and my penis began to go limp.

She shoved the strap-on all the way in and held it there. “You’re are mine aren’t you baby.” I couldn’t speak but mouthed my “yes”. She peeled the condom off my “boi clit” making sure she didn’t let it leak. She brought it to my mouth. “Time for one last lesson. Time for you to l

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