Anastasia's Life So Far

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wifestoy
wifestoy
82 Followers

"Anna you little slut, Renee was right you have a sweet pussy baby. And she has really taught you well. You really know how to use that ass. Ooh yes milk my clitty. I have got to cum down your throat, so turn around little miss."

I felt her pull out and was so very disappointed. She however rewarded me quickly shoving her clit in my mouth. I was glad I was fully cleaned out, yet the taste of ass and precum was still so sexy. She shoved her cock right in and I wasn't ready for that and gagged a little.

"Oh sorry Anna I just got so excited and need to cum please suck my cock and fill your belly for me. Ooh your tongue is nice, that's it suck that clit. Mmm swallow that into your throat, sweetness. Oh I can't wait any more I have got to cum."

When I heard this I sucked as hard as I could. I grabbed her balls and that was all it took.

"Ughgh yes Anna that's it. Oh my god I am cumming. Squeeze my balls, yes that's it, suck it, oh yes suck my clit down your throat."

Her first burst almost chocked me. She was right she had been storing up for awhile. She must have cum eight or ten streams of cum. There was no way to swallow it all. I did the best I could but some leaked out and down my chin. I continued to suck and milk her clit for all I could. Her cum was so sweet I wanted to suck down every drop. She pulled her clit out of my mouth and quickly licked the cum from my face. She then gave me another one of her sensuous kisses that was now becoming a favorite of mine. Her lips so soft and full, the kiss so sensuously gentle and hot. She knew how to use just the right amount of tongue to keep you lusting for more. This woman had sexy coming out of every pour of her body.

She must have been extremely horny since she almost knocked me down and went straight for my clit. I knew it would not be long with all the action I had just got.

"Give me that clit of yours Anna I want to taste that sweet load."

She took me right into her throat and I almost lost it right then. Wow could she suck hard and work her tongue. This was incredible.

"Oh, Ughh, I have got to cum." She slipped a finger, then two up my ass. It was all it took I was cumming immediately. She was pressing on my prostate and I was cumming in quarts. I didn't think I would ever stop. I think I actually blacked out. Then next thing I remember was Michelle asking me if I was ok. She was stroking my face and caressing my body.

"Anna have you come back to Earth yet? I guess I don't have to ask you if you are enjoying yourself."

We both started laughing, that was just the understatement of the year.

"Darling you have to get composed so we can continue our quest for orgasms without the cum. I told you we will not finish tonight until I drain your balls of every ounce of cum. And I intend to suck and fuck you dry my sweet."

"Well Miss Michelle if I am not mistaken I believe you said until you are dry we are not done either? So get over here and give me that cock in my mouth. I will suck you till you give me another sweet load."

I took the initiative and pushed her back and started to lick and suck her cock. I slathered her balls and slowly eased my way to her puckered pussy. I could not resist her pussy I had to have it. I slowly licked around the outside rimming her as she moaned. This only egged me on and I stuck my tongue directly into her ass. I started to push my tongue in and out fucking her with my tongue. She was squirming and pushing against my tongue. Wow was this hot! I grabbed her cock head and it was soaked with pre cum. I used it as lubricant to start jacking her off as I continued to ravish her hole. I was alternating with her cock and balls remembering her enjoyment when I squeezed them earlier.

"Oh Anna you are a delight. I, I, oooh god you are fantastic. Fuck my ass with that devilish tongue of yours. Ugh and keep rubbing that clit and balls!"

Her pre cum was just flowing like a faucet. I had to taste her. I quickly moved up and sucked hard on her cock. Taking a lesson from her earlier I eased a couple fingers in there and started giving her a prostate massage while sucking her with all I had.

"Anna please fuck my ass. I want your cum in me when I cum and if you don't stop sucking me off I am going to cum. Slide that meat into me and show me what you got."

I eased my cock to her pussy and my cock was now copiously flowing pre cum. I slathered it all around her puckered bull's eye. Wow was this an intense moment. The beauty of her below me while I was watching my clitty disappear into her tight ass was almost enough to send me over the edge. I rammed into her to the hilt and she gasped.

"Oh, Anna that feels so good. Ream me until you fill me full of your sweet cum."

But I had to stop for just a minute or I would cum right then.

"Anna what are you doing? I want you to give it to me hard!"

"If I don't I'm gonna cum right now."

"I said fuck me now! And you will do it as hard and as fast as your sissy little ass will take you!"

I immediately obeyed and it was only a few strokes and I was cumming just as I thought. I continued to drive my cock home as hard and as fast as my body would let me. Oh the sexy noises that were coming from her pussy filled with my cum and me thrusting away.

It sent me into another orgasm that sent me screaming, and feeling that I would turn inside out. It was one of the top orgasms I can remember in recent history. The intensity of that second orgasm racked my body from head to toe.

I suddenly felt Michelle cumming all over my stomach and chest as well as painting her stomach and breasts. I grabbed her cock and rubber her head in a circular rubbing up and down on the head. I saw some porn stars doing this and it too triggered another orgasm shooting more delicious cum over us again. I starting licking up the cum I could get to and man was it succulent. I had to have more. I pulled out and quickly and replaced my cock with my mouth and started sucking out my own cum. I know I enjoyed Michelle doing this to me so I figured she would as well.

"Why you little minx, you are learning so quickly just how to please and satisfy any woman. Yes my dear that feels wonderful. Just suck and lick outside. You don't need to lick inside. The nerves are so sensitive right now it feels so much better when you just suck and lick the outside while it drains. Yes, my dear that is exactly it. Oh yes Anna you are going to be the absolutely best, I can see this already."

"Michelle what do you say we go get another hot bath and rinse all this off so we can rest a few minutes and get ready for the next round?"

"Anna I am the one who is suppose to be leading you. Look at you taking charge this is just wonderful. I am glad to see that is still there in your personality. Something you may not know is that Renee still wants you to take charge from time to time. Every woman wants their partner to ravish them with some hard-core sex on occasion. This was one thing she wanted to see if it was still existing in your personality or to find out if you were going to be a mere sissy all the rest of your days. Now Renee truly loves her sissy so don't think that is going to disappear, it isn't. Renee does however still enjoy getting hard-core sex from time to time and she hasn't had any from you in awhile. One of my tasks was to see if I needed to recommend this or see if it was still there some other way."

"Well this is good news for me also. I thoroughly enjoy being under Renee's control however there are times I'd like to just throw her down and fuck her hard."

"And she wants you to do that from time to time. Well let's go get that bath and recuperate for the next level, we will not stop our next session until we are both drained."

I got in the tub first and when Michelle got in she straddled me and sat on my lap. She threw her arms around me and laid another one of those wonderful kisses on me. If I didn't love my Renee so much I would be head over heels for this incredible lady. Of course I was rock hard in no time.

"I thought we came in here to recuperate? By the feeling of that clitty sticking in me I'd say you have recouped."

"Well what do you expect when a gorgeous woman lays a heavenly kiss on you? It is inevitable that I am going to get excited. And judging from your nice, sweet, hard clitty I would say you are fully recouped as well."

"Shut up and kiss me Anna, then use that clitty on my ass!"

I remembered what she said about the rough stuff. I started kissing her and put my cock right against her ass. I lifted her up a little and directed my cock head right into her ass. Oh it was so wonderful when she slid right down to the hilt. I knew that having cum a couple of times already I would be lasting much longer. I am going to fuck this woman silly. If not then I am going to have a ball trying. So I grabbed her and laid her on the side of the tub. I started fucking her as hard as I could.

"Ughugh yes Anna fuck my ass! Ughm harder sweetheart, I need you to use my ass. I want you to hurt that thing. OOH yes right there you're hitting that sweet prostate. Agh, yes keep hitting that sweet spot."

She started cumming everywhere; it really surprised me I realized her sweet spot and what set her off. I found the elusive trigger for her orgasm and wouldn't forget it soon. She was cumming ropes and ropes of cum all over our bellies and breasts. She was scooping up the cum and shoving it in her mouth. Then she scooped up more sharing it and giving me a taste. This alternated back and forth till I had to have her tongue in my mouth while we fucked. I continued to hammer away as I felt my orgasm build within me. She was now whimpering and one continuous moans. I was alive with electricity. Then it hit.

"Oh yes Anna please cum I can feel your head growing and swelling, oow yes that's it baby ride me, ride me, UGH yes the hot cum I can feel it filling me full. Keep riding me I am gonna cum again. Yes, Anna, there hit that spot!"

Again she was spewing ropes of cum however I started noticing a decreased volume she was starting to dry out. I was not sure about myself I have not seen my last few loads. I know I was getting sore. My clit was sore, my muscles were sore and by tomorrow I would be very stiff from all this action. I am not complaining however this was going to be a wonderful pain. Every time I felt the soreness I would be reflecting on this wonderful day of bliss.

"Oh Anna you are still cumming too much we must take this to my next plan. First however I want you to eat your cum from my pussy."

I quickly started lapping up my juices coming from her freshly fucked hole. It was so sweet and nasty. I was wondering just how many more levels we could reach. I was soon to find out just how little I knew.

"All right missy, that is good enough for now. March your sweet ass on into the playroom and the real fun is about to begin!"

As we eased into the other room I was frantically wondering just what toys we would be playing with first.

"Lay your ass down on this bench."

She eased me onto the bench, which was designed so you lay down on it from the waist up. She grabbed my ankles and strapped them apart to some restraints attached to the floor. My clit was freely flopping everywhere. She then put a ring around the base of my cock which had a bullet vibrator attached to it. It rested under my balls and the strap only served to keep the vibe in place. She then disappeared to one of the closets and came back with a contraption I had never seen before. It really had me worried. And I guess I was getting very unnerved.

"Anna don't worry this will drain you one way, or the other. I am quite literally going to fuck you silly. This little machine I have is a fuck machine. I will attach a dildo to the shaft and it will do the fucking. It has built in vibrations and I am going to suck down every load you have left. When I get done with you sweetheart you won't even be able to say your name."

"I am a little scared here Michelle."

"Good, that will only make it more intense."

She then came up and whispered, "Remember my sweet I won't do anything that is going to hurt you, but you will be hurting come tomorrow. The way a well fucked pussy needs to feel after some stud or studs fucks you senseless."

"OK Michelle, fuck me silly."

"What, you're not going to beg me to fuck you? All the pleasure I am about to bring you, the least you can do is beg me for this monster cock that is going to split you wide."

"Please Ms Michelle will you please fuck my pretty pussy raw? Please feed that loggerhead up my pussy and make me beg for more. I need to have that man meat inside of me, please feed it to me."

"OK if you insist my little slut."

It was then I noticed the size of that cock attached. WOW it was huge! I am glad I am very well lubed since me ass is going to be a gapping hole tomorrow. The machine slid into place and I heard her turn it on. The familiar sound of a vibrator filled the room and it was then I felt that cock slide into me. The strap she added to the base of my cock with the mini vibe on it was just too much.

I felt Michelle below me and she was wrapping her sexy lips around my ever-hardening clit. Ughgh this cock was truly a monster. The feeling of being so full and getting sucked off by this beautiful woman just never got old. The absolute joy and shear bliss I was experiencing, words could not describe.

This machine had such an incredible rhythm that was consistently popping my prostate with every in and out thrust. I knew I would be blowing soon. Suddenly I felt the machine speed up and the sensations doubled than tripled. The orgasmic feelings were washing over me in wave after wave of subtle orgasms. Building to a point I know would be coming quick.

She then sped the machine up again and this machine was now pounding my ass. I was getting fucked harder than I had ever been fucked and so very quickly too. That was all it took and I started cumming again the intensity was shattering. The machine fucking me to oblivion Michelle deep throating my spurting cock I was sent over the edge again and starting cumming again and again it felt like continuous orgasms. I had experienced multiple orgasms before but none this intense. I was babbling, moaning, screaming, and begging Michelle to use me and abuse my ass. I was thrusting back with every forward thrust of the machine.

Michelle came up to my head and thrust her cock into my mouth. The lust I was consumed with I could have swallowed her whole. I took her deep into my throat immediately and that was all it took she was spurting, but there was very little coming out at all. I just kept sucking her cock like the hungry cock slut I had become. I was sent into another orgasm that racked my body thrashing about and forcing Michelle's cock as far down my throat as I could.

I tossed my head back and her cock popped out of my mouth. I could see it pulsing and nothing was coming out. Did I suck her dry? The orgasms now were pleasant but painful. Each orgasm that came now seemed to be more painful.

Michelle reached down and grabbed my cock and told me, "You're finally dry slut. I am not going to stop fucking you until you have two to three more orgasms."

With that she pulled the machine from behind me, assumed the position and thrust her cock into me. She was nowhere near the size of these dildos so she was fucking a very loose pussy now.

"Oh you little ass slut, you are loose as a goose now."

I could still feel her pounding my prostate and it hit me again. The pain was almost too much, but the pleasure was just as intense. She was fucking me hard but not as hard as I had just been hammered. Michelle's fucking sent me into another multiple orgasm which was just too much to bear. I passed out from the shear pain and pleasure of the evening.

The next thing I remember was Michelle waking me up trying to figure out where I was and why my ass was burning so bad.

"Wake up sleepy head; you were just a babbling mess when you finally passed out. I could not even get you up. You were a quivering mess my sweet. What did you think of last night? How did you like your first time being milked dry? And Ms Ana you were the little slut last night. When I turned that machine on to high I thought you would lose your mind. Shaking orgasms, babbling and crying as well it was truly an awesome sight. I am glad I got to be a part of it. Thank you Ana I love you more for that and hope it won't be our last time."

"Well last night was just unbelievable, a night that I don't know how to top. As for my first milking it was surprisingly pleasurable but also painful. And let me say this I love you too Michelle for taking me into that realm I had never been to before. It will be a moment I will never forget and as you stated I hope the ladies give us an opportunity to continue on our journey into sisterhood."

"Just one question Michelle. When will my ass stop hurting?"

Michelle simply laughed and told me, "in due time, all in due time."

All Email Comments are welcomed good or bad. Criticism can be a great tool also.

Love,

Anastasia

wifestoy
wifestoy
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11 Comments
AnonymousAnonymousabout 1 year ago

The problem is that most crossdressers are just that - crossdressers. They're not gay. And saying that this is autobiographical does nothing for the story. We don't believe anything you say on a porn site.

AnonymousAnonymousalmost 2 years ago

It sucked. I don't like reading like 9 pages of tease just to have it turn around into some gay male thing at the end.

AnonymousAnonymousalmost 10 years ago
Extremely Sensual and Erotic!

Your story was well written and had good story line. I have not experienced what you so ably described.

I want to be a bottom for a loving man or woman wanting to be a man. I want to wear lingerie and be lusted after and strongly desired by men and/or women. I want to sexually please and be pleased. I want to taste and drink cum, both male and female. I want oral and anal sex.

Disregard the hurtful comments, your story was excellent, very descriptive and sensual. You got me hard and horny.

Is there a school that I could win a scholarship to, so I could enroll and learn to be feminine and please a man or a woman?

AnonymousAnonymousalmost 10 years ago

i would find a why out of there and file for a divorce

AnonymousAnonymousover 10 years ago
There Are No Warnings...

Of rape, serious bodily injury, or any of the other things that go wrong for this character. I stopped as soon as the 'wife' said "you're my bitch, do what I say or else bla, bla, and bla" (she's a niiiiice lady), other than to go thru just enough to make me sure about what this was. This is seriously violent fantasy. As far as submissive and dominant go, assuming you are trying to express terms involved within a very complex, and as you indicate, two-way fetish known as S&M or a more modern acronym BDSM. What's written here has nothing to do with those, so just as well it was left out of the tags. The tags need to be changed, even adding the idiotic 'sissy' tag would have helped as warning, but I know thats hard to do. So I felt another note was needed to warn anyone unlucky enough to click on this thinking it has something to do with crossdressing or femdom or even forced fem (since this story has so little to do with any of those) doesn't waste any more time on it - unless they want an extremely cruel and violent story. That's fair at least.

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