Becoming Bobbi

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osodd_boi
osodd_boi
35 Followers

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 learn to love the taste of cum." I opened my mouth and she began to feed it to me.

osodd_boi
osodd_boi
35 Followers
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27 Comments
AnonymousAnonymous3 months ago

A few grammatical errors but even books for Kindle suffer the same. It still was a very enjoyable and hot read. Please write a follow up story!

AnonymousAnonymousabout 3 years ago
Poor

You don't loose your virginity you lose it.

Bad grammar and bad spelling on a recycled storyline.

RegretsRegretsover 4 years ago
Complete mastery of the subject

At the end, when he was to ingest cum from the condom, surely it would taste of the numbing cream, i thought? Maybe I misunderstood. I wish that he was a bit more aware of what was happening, as he was inducted, in the coffee shop, and in their earlier meetings. He did seem to be over stunned, overawed. I thought that maybe he would not remember very much. He is though a fine subject for improvement. I hope that the chastity device is changed for one with spikes because he seems to have had no difficulty in the few days to their meeting. Of course, there will also be a lock fitted, and the cage is noticeably shorter than the first one. An excellent story. I suppose that the shop assistants working on the girls underwear floor will all have experiences like this one from time to time. How good it would be to hear them told. He is an excellent choice for Miss, and it was good to hear the way she had that conversation with the assistant and the responses from her were perfect. Bobbi is in deep water now, well above her armpits. What will be the outcome?

JoannePareJoannePareover 5 years ago
Wonderful

Hope you keep adding th this wonderful story, i am eager to read more.

Joanne

XO

ramperampeabout 6 years ago
Great story

Thank you for sharing this story.

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