Admissions

Story Info
"He" is taken shopping.
2.2k words
4.18
90.7k
6
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
pinkpony2
pinkpony2
42 Followers

I closed my eyes. I knew what I wanted to say, but was unsure I could get the words out. The silence on the other end of the phone began to become chilling. Finally, incredibly patronizing, "You wanted to make another tape of me dominating the hell out of you, didn't you Steven!"

"Well, I..." my face grew red, my pride pretty much shot, dying to give in to relinquish any sense of self I had left, longing to get what I needed - the chance for full release, to admit all.

"Steven, we've become pretty good friends..."

"I know, that is what makes it more awkward."

"Why? You don't want your friend to fuck you up the ass."

"No, I do. It's just that I...it seems odd, almost a betrayal to you."

"What if I told you, I still wanted to fuck you and use you for the slut I know you would be for me."

"I..." I could not breath, my cock was pushing hard against me denim jeans, straining upward.

"Tell me!" Michelle whispered, "You know you want to. You cannot help yourself, can you?" She paused; as usual, she was right on in continuing, "That is what galls you isn't it? You feel the need to be taken. It makes you feel weak or wrong, but in the end you cannot escape the feelings that I helped grow in you, the desires I let build. You need me to want to use you, don't you."

I was not afraid, even then. I knew she was a good person, but part of me wanted her to be bad, not so much to possess me...well maybe...but more to...to absolve me? I wanted not to care what she thought of me, not to care about what I thought. The reality was that I had thought about giving myself over to someone before her. Even the thought of being used or fucked, even humiliated, by another, had been arousing before Michelle, but discussions with her had made those sentiments conscious, had honed them to the point of need.

I was losing control. I knew that I wanted Michelle to follow one of our scripts, to make me admit all of the intimate desires that I had accumulated. To force me to repeat myself and describe the arousal I felt contemplating her cock, its domination of me, her whimsical governing of me. Her cutting me short when I sought to avoid spelling out specifics and her threatening to involve others by taping our conversation or putting me on the phone with friends of hers. Still, in that case I felt like the user and that kept me away, kept me from pushing the issue. It was something she had to want, not that I could even ask for it -- though it might be freely given.

But, again, I was getting weaker, my will fading as I heard her voice in my head again - giggling awkwardly, recognizing her innate power in the rapport, unsure of her feelings as to my discomfort, then deciding and demanding, "Tell me what you want! I know what it is, but I want to hear you say it."

"How do you know?" I retort trying to draw back, still feeling awkward, feeling as I had foisted an uncomfortable situation on Michelle; Michelle who was a great woman, caring and sweet, hating the fact that she aroused such arousal in me, but somehow (maybe hypocritically enjoying that as well). It had to be her role too; I knew that.

"Isn't obvious," she half sneered half sighed.

"I see what you mean, I am sorry. I am silly," I admitted.

"That's only the half of it," Michelle properly retorted, but I am glad you called, even if only so I could make fun of your basketball team, doormat boy."

"Ouch, that's kind of tough." The Knicks weren't the team they used to be and the Spurs just seemed to get better.

"Truth hurts darling."

"Ok, want a little wager. No that's dumb, I would just be begging to lose. Unless we went two for one?"

"I'll think about it and let you know."

"Fair enough...and Michelle, I am sorry."

"It's cool. Maybe one day I'll be up that way and actually make you do some of that stuff."

"Can't wait."

"Be careful Steven," she laughed again.

Maybe that is what pushed her. I don't know. Possibly, the idea of actually going out on a limb, doing something that was actually out of character, something free, full of expression and craziness. She still recalled their first awkward conversation, knowing that only my heart was beating faster then hers, the stilted words, the suspension of disbelief, the otherworldliness as well as the palpable breathlessness and desire in their tones. Maybe...I don't know...perhaps she won't let me know, that is her prerogative.

The day was crazy. My boss was yelling. Deadlines loomed; my office seemed like one unending stack of paper. I had just finished the last document due on that date, stamped the 14th on it and sealed the envelope. I turned to tomorrow's beast that was virtually tottering on itself, like the turkey in A Christmas Carol that could never have supported its own weight. My cell rang shrilly behind me. It always rang when it was charging even if it was set on mute; I never understood that. The sound was annoying, and I grabbed for the phone to stifle the noise not wanting call undue attention to it.

"Hello." Silence. "Hello."

I was about to hang up, when I heard Michelle state, "I have thought about this quite a bit. There will be five parts."

"What parts..."

"Don't talk! At least, not yet. Today is the first one. Put on your coat and go outside. This is a one time opportunity, as each of the parts will be. Don't make me wait."

"It's 3 pm. Are you serious?"

"Steven!"

I broke, "Yes, Michelle."

"Where are you going?" the office manager demanded as I headed for the door.

"I just have to go out for a little bit."

"Well, when will you be back."

"Shortly." I had not know what else to say. I almost did not get out those words, as Michelle asked if I need her to call back at tell my manager that I was going out to by some panties so a looked the part when I got fucked up the ass.

"You wouldn't." I said believing it.

"Oh really..." she let that hang, "maybe not." "So where is the nearest lingerie store?"

"There is a Victoria's Secret about a mile away."

"Perfect, that will give us some time to talk on the way."

"So what do you want to buy from Victoria's Secret, Steven," she almost sneered as I reached the sidewalk.

"Whatever you tell me to Mistress," trying to grasp what I was actually doing out of work at that time of day, apparently going to by lingerie in public for myself, but jumping into our former play-roles.

"I am not your mistress yet. You will have to demonstrate that. I want to know what you have thought about wearing and what you want to buy for yourself."

"That is really two different questions isn't it?"

"This is not your game. I thought you understood that. This is your warning." The phone went dead.

Now it was my turn to put up or shut up. This was my one opportunity. Even as I told myself that, categorized the situation as an opportunity, I knew I had to play it out, just like I had to dial back the caller id several years before (wow - years). "Michelle?"

"Yes." still frosty.

"I would like to wear a thong with a full front." Still nothing. "Please come to Victoria's Secret and help me pick out the right thing for me to wear. I have thought about a pink or white lace front."

"Better. Now you sound like the slut you are."

"I would be for you."

"You are with or without me, but now I have decided to take advantage of it. What else have you thought of using to dress up, Steven." purposefully saying my name more clearly. There seemed to be a lull in the traffic and I thought that her end of the line was not as clear as it had been before.

"Stockings."

"Really?"

"Yes, Michelle."

"Good, anything else."

"I have thought about getting completely dressed up, with a dress and wig, and I think it would be neat if I had a better build for it, but I am not that dainty."

"So you want to get dressed up, but you don't think you could pass as a real woman."

"Probably, not."

"Maybe, I'll just have you try and give you cocks to suck from guys who don't care. Wait, what am I saying, you did not say that you've thought about sucking a cock, or that you want to have you."

"No Michelle, but..."

"But what?"

"I have."

Exasperated, "You have what?"

"I have thought about sucking your cock."

"Really? Say that again."

"I have thought about sucking your cock and the thought of you making me turns me on."

"Louder slut."

"I have thought about what your cock would feel like and the thought of you making me suck a dick while you looked down at me turns me on."

"I like that, you really could be a slut."

"I am for you."

"I know. Tell me, Steven, what else have you thought about me doing with my cock?"

"Fucking me."

"Well aren't we the brazen one. Fucking you where, Steven?"

"I have thought of you fucking me up the ass with your hard cock, Michelle." Our banter was still almost routine, except I was walking down the middle of the sidewalk heading for a lingerie store during mid-day.

"And does the though of me pushing you on all fours and slide my cock into you get you hard? Knowing it turns me on to take you?"

"Yes."

"Probably hard enough to cum, no?"

"Yes."

"So what would you do for me, for me to allow you to cum. You know that is my decision, don't you?"

"Yes, Michelle."

"Why?"

"Because, you are calling the shots." Silence. "Because my cock is yours..."

"Better, prove it!...I am waiting."

"And do not give me any of that 'Whatever you want crap' I want you to tell me what you would do."

"Aside from dressing up and letting you fuck me."

"You are not letting me, I am indulging your fantasy, you slut, I will enjoy it no doubt, but do not forget who has the cock now. Besides, you want to be fucked. You have already admitted it. Tell me something new!"

"I..."

"Tell me!"

"I would get on my back and have you fuck me so that when I looked up at you I would see the head of my...I mean your...hard cock waiting to shoot on my face." Silence, I could almost hear her foot tapping getting impatient as my heart beat faster still cognizant of the unfamiliar whirring on the line.

"I would beg to have you shoot your load of cum on my face and in my mouth as you fucked me, hopefully you getting off at the same time."

"So you want a hot load of cum sprayed over your face, do you Steven?"

"Yes, I would take a load of cum on my face for you."

"That is not what I asked, is it? You are really pushing me, do you want me to take you shopping or not, slut?"

"Yes, please. I..."

"I am not sure that I want to waste my time. You probably will welch out anyway, won't even go in much less make a purchase or do anything else I tell you to. You are to much of a sissy to even do that much to please me."

I was done. She had me from all sides. If I backed down, I was not gutsy enough to go through with it, did not want to please her and was letting my one chance slip away. "Michelle, I am sorry that I hesitated. You are right, I..."

Her laugh again, I knew this time she was actively enjoying my submission, my discomfort in letting myself go. "I have thought about being cum on and feeling a hot load of cum spray across my face, even going into my mouth, and the thought of that has turned me on, is turning me on right now. The though of you pushing into me, getting turned on by that motion and seeing "your" hard cock above me as you grasp my hips and look down at me telling me to jack-off does turn me on."

"So you want to get fucked, get cum on and swallow cum is that right Steven."

"Yes."

"Yes, what?"

"I want to be your cum slut, Michelle." I hoped this was not being recorded as other conversations had been, even though I was increasingly sure and discomfitted by the thought that it probably was for some later use by Michelle.

"Now Steven, do not tell me anything you do not mean. Is that really what you want. Speak clearly." she admonished.

"Yes, Michelle. It would turn me on for you to dress me up and fuck me with your hard cock. Feeling you get turned on as you make beg to cum on my face and swallow cum for you."

"Better. Now let's go shopping. Don't wimp out; it won't hurt...much." The laugh...

pinkpony2
pinkpony2
42 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
cdCindy1cdCindy1over 6 years ago
please continue

This is a great start. Please continue and tell us what happens next with Michelle your Mistress. One question -- is she a she-male (with a real cock) or is her "cock" a strap-on dildo ? Just wondering.

AnonymousAnonymousover 11 years ago
wow

that was so good it was a real turn on :) <3

AnonymousAnonymousalmost 18 years ago
lmao

No shit! The story is just beginning and then it ends!

AnonymousAnonymousabout 20 years ago
More of the little bitch

Jesus Christ! When does he serve her ass?

Share this Story

Similar Stories

My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Girlyboy About how to turn a boy into a bitch.in Transgender & Crossdressers
Like Mother, Like Sissy A sissy learns he is a princess . . . and a sperm whore.in Transgender & Crossdressers
Pretty Chris-tine Young couple experiment with feminization.in Fetish
Wife Gets Even Wife loses bet but wins the rematch and fems up her husband.in Transgender & Crossdressers
More Stories