Sissies New Years Surprise – Part 1 – free porn video

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“sissy come in here, W/we need to talk.”

“Yes Mistress, coming.”

Sissy enters the room and curtseys, with sissy’s eyes downcast she sees Mistresses finger pointing towards the floor. Sissy hobbles over to Mistress and kneels at Her feet. Today, Mistress has sissy in her black satin maids uniform with pink lace trim and a pink apron. Sissy also has on a matching pink hair bow, pink petticoat, matching pink ruffled panties, black hose with matching garter, a black bra, and black 4’’ locking pumps. This morning at breakfast Mistress had told sissy that today sissy was to clean the house top to bottom leaving nothing unturned. She kept stressing how important it was that the house shined. She had also decided to place ankle cuffs on sissy and tie a 12 ‘’ rope in between, this would make sure sissy took very small steps and of course make cleaning much more difficult, which always amused Her. Finally, She told sissy that tomorrow sissy was going to get her last xmas gift tomorrow.

Its New Years Eve and She had told sissy that T/they would be having a quiet New Years Eve this year, yet now She has sissy scrubbing the house. Having sissy clean is nothing unusual, but it’s usually a room here and there. Something was up and sissy’s head is spinning trying to figure out what She was up too. On Xmas morning She had mentioned to sissy that She had another gift for sissy, but that it would be about a week before it arrived. Then She said, “if you want it that is” with a smirk. Sissy blushed as usual and didn’t say anything. Sissy had honestly forgotten about the gift until this morning, and now here sissy was about to find out. A million thoughts were going through sissy’s head as she was cleaning all morning and she felt very nervous.

Mistress had already spent a ton on all new clothes and uniforms. She loved to dress sissy up in various outfits, so sissy was not surprised on xmas morning when she saw about a million boxes of pretties to open. Sissy was not fulltime; Mistress dressed her when home from work and on weekends. At work sissy had to wear panties, sometimes hose and a cami, and if She really wanted some fun a bra. Sissy’s stomach was turning as she was nervous and knew something was up.

“Now sissy darling, you know how much I love and adore You, yes?”

“Yes Mistress, sissy is very lucky to have You.”

“Good girl” Mistress waited a minute and then took a deep breath. “Okay. Honey this is not easy to say. “ sissy is starting to sweat. “As I said this morning your gift is due to arrive tomorrow and that is also why you’ve been cleaning all morning. I want you to make a great first impression and this will help showcase your talent. Sissy let me ask you a question, do you think something is missing in My life?”



Sissy could barely respond, she tried to speak but nothing came out. Sissy knew exactly where this was going. Sissy had been thinking it all morning that Mistress was going to bring a home a Man. For the last 6 months Mistress had been dildo training sissy and now She was brining in the real thing. Sissy’s practice had mostly been oral, ever night before bed she had to practice for an hour in her new room.

Sissy barely audible spills out, “A Man Mistress.”

“Speak up, I can barely hear You”

“A Man Mistress”

“Excuse me sissy?”

“Sorry Mistress, a Real Man.”

“Good girl. Yes sissy a real man. You see sissy I have sexual needs; yes you are very very talented at servicing me, but I really need to a big cock too. That’s not something you can help me with can you sissy?”

“No Mistress sissy can’t”

“And why is that, sissy?”

She loved torturing sissy about her clitty. “Because sissy does not have a big cock Mistress.”

“What do you have then?”

“sissy has a little clitty, Mistress”

“You do, how little?” She says sarcastically with a smile.

Sissy feels like she is about to cry, here She is about to tell sissy She is bringing home a Real Man and yet She is still has time to make fun of her clitty.

“four inches Mistress”

“Yes four inches, now would you call that a big cock?”

“No Mistress, it’s a small clitty that belongs in panties.”

She chuckles, “Yes that’s true, but is that all? Isn’t there another reason sissy why that little clitty can’t enter Me?”

“Yes Mistress, sissy’s clitty is also in chastity.”

“Bingo! Lift Your skirt and show me”

Sissy obediently pulls her panties down to her knees and lifts her skirt and petticoat.

“Look how cute. It’s so precious. “ She grabs it, “look sissy its barely an inch now, doesn’t even come close to touching the end of the cage.” She lets go and leans back trying to compose Herself. “You see sissy even if it was 4 inches, it can’t really get in Me with the cage on. Of course I could let you out, but it would leak before it even entered me and then it’s definitely not going to get hard. Am I wrong ?”

“No Mistress”

“I didn’t think so. Do you know where this is going sissy?”

“Yes Mistress”

“Please tell me?”

“Your dating a Real Man now and he is coming here tomorrow.”

“Actually no, well your sort of right. Yes a man will be coming here tomorrow, but not for me. I’m not dating anyone…yet. “

Sissy’s heart is pounding, thinking oh my god this is so worse than imagined.

You see sissy this may be hard to understand now, but in time I’m sure you’ll agree. I am going to be thirty next month and need to start settling down and thinking about the future. As hard as this is to do, and as much as I love you I just simply can’t have a sissy here fulltime if I want to try to find a husband and eventually have k**s. I just don’t see a lot of straight men being ok with you living with me, which is unfortunate but reality.”

Sissy is just staring at the floor with tears starting to stream down her made up face. Sissy is trying to listen, but she is in shock.

“I know this is hard sissy, it’s just as hard for me. “ She continues, “For the past month I have been secretly meeting with this man, nothing sexual just discussing you. I met him online and he loves sissy girls like you. I grilled him with questions and I definitely approve of him and think he would be great for you. He has seen pictures of you and thinks you’re very cute and has agreed if and only if you agree to let you live with him and train you to be his sissy boyfriend/girlfriend fulltime. Yes, one of the requirements is he wants a fulltime sissy. He is extremely wealthy and you would not have to worry about working and can concentrate on being the perfect sissy fulltime.”

Mistress paused and looked down at sissy and could see that she was crying. She leaned down and gave sissy a big hug rubbing her back. Because sissy was kneeling and Mistress was sitting on the couch sissy’s face was now much pretty much buried in Mistress’s breasts. When Mistress pulled away from sissy She could see that sissy had gotten her mascara all over her white blouse.



“Sissy!” She yelped, “Look what You did.”, she said k**dingly.

“Sissy look at me….SISSY!”

Sissy looks up with Mascara running all down her face.

“Sorry Mistress.”

“It’s okay baby, you’ll clean it in a bit. Sissy why are you crying, what are you thinking? Talk to me sweetie.”

Sissy looked down again and mumbled, “why a guy?”

“Well let me ask you this. I did think about finding another girl, but eventually she is going to want the same as me. Do you like being a sissy?”

“Yes Mistress”

“Of course you do and you’re very good at it, much better than being a guy. Women are missing out on gurls like you, I think We should all have one, but again not reality and I do very much want a family. So now I could find another hot girl for you to serve, but after a while maybe a month, maybe a year, maybe more She will eventually wants the same thing as Me.” She paused, “ Honey going a year w/out cock is very difficult for a Woman. I’m looking out for your long term future and I think this is the best route. you yourself said you can’t please a Woman with your clitty and I see how talented you are already with pinky and how much you enjoy her.” She was referring to sissy’s dildo, named pinky.

“I know the real thing is much different, but I think you are ready for this and it makes the most sense. You have also said to me in the past, that you would like to be a fulltime girl and with him you can be!”

Sissy still staring at the floor was eating those words, Mistress had teased her into saying she wanted to be a fulltime girl.

Sissy mumbles, “and what if he gets tired of me?”

Mistress exclaimed, “GREAT QUESTION, I was hoping You would ask that… See sissy you are smart. “ She laughed and She knew by asking this sissy would agree to all this. “Well sissy that is the best part, he has agreed to put a significant amount of money in your account that will only be accessible to you if he should get tired of you. It’s enough that you could live happily off of w/out any worries. It’s like a trust fund if you will, although I personally don’t see you getting to use it….if you agree. “ She said with a smile. “I might add you won’t need it if your with him either, you’ll have a very nice allowance. “

After a minute of no one talking Mistress spoke up again. “Who knows sissy, maybe if the damn people in this country can get over themselves and stop being so scared of nothing you two can get married.”

Sissy said nothing, just kept looking at the floor.

“Sissy I’m joking, but you never know. Lighten up, I know this is tough, but I really do think this is best for everyone involved. W/we will still very much be best girlfriends and I’m going to need a maid still, all to which he has agreed.”

“Ok so I know this is a lot to take in right now, so here is what I’m proposing, sleep on it and make a decision tomorrow. If you say no tomorrow then I will call him and tell him you’re not ready, but if I do that at the end of the month you will need to be out of here. Again still best girlfriends, but I need the place to myself. If you agree then at the end of the month you will be fully moved in with him. I’m not just gonna ship you off tomorrow, lots of packing etc to do, plus need to undo Your girly bedroom and make more of an office. “

Mistress grabbed a tissue and wiped sissy’s face and leaned in and gave her a kiss. Sissy was still sniffling.

Mistress clapped her hands, “Now You need to get back to cleaning in case you agree to meet him. Go fix your makeup and please bring me a glass of wine then gets back to work.”

Sissy stood and curtseyed, wiping her eyes. she thought she was going to pass out she was dizzy and took a deep breath to compose herself, she turned and exited the room.

“Sissy!”

Sissy turned.

“Don’t forget my shirt. “ Mistress removed her top exposing her gorgeous breasts and handed the stained shirt over to sissy. “Bring me a new top too…oh and sissy I think it’s going to be a really good new year”, she said with a smile.



Sissy curtseyed and exited the room.



To be continued….

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Previously I told the story of how both my wife and I ended up finding out our daughter was a lesbian and that she was due to get married.For the weeks after the party, we discussed what had happened nearly every night, how we had both fucked our daughter and her lesbian fiancée. Each time we talked about it we ended up having the most amazing sex, with each other. My wife kept saying how she wanted to fuck Sid (our daughter’s girlfriend) again and hopefully if the chance arose, she could fuck...

2 years ago
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Digital Prostate Exam ndash Really ndash Followup Visit

This story is a work of fiction, it NEVER happened. This is chapter two so if you have not read chapter one you should start there (https://xhamster.com/stories/digital-prostate-exam-really-9971785) This series began when I read a story here on XH about a woman going to her gynecologist and ending up in a sexual event. The story has since been deleted so there is no way to send you there. Many men, me included, have no clue what goes on in a woman’s exam but many of us wonder if the doctor may...

4 years ago
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MALA ndash The Village Lady ndash 7

Honey Moon TripRahul got an official trip to abroad, so we also joined him and booked our tickets of the same flight. We did not meet Rahul coz he was in business class with another company guy. All were slept in flight, I saw Alia who talked with the window stranger, and her hand touched his bulge. After sometime, he stood and walked to toilet. Then Alia passed a smile to me and walked behind him to toilet. Then the guy returned and sat and slept. Soon Alia came back and kissed me and shared...

3 years ago
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Ann ndash At The Beach ndash 2 Sun Oil

(This story is the continuation of "Ann – At The Beach – 1. A New Bikini". Please do read that first!)https://xhamster.com/stories/ann-at-the-beach-1-a-new-bikini-9920948My girlfriend Alex, a friend of hers and Alex's younger sister Ann had just arrived at the beach on a gorgeous, sunny day during the summer holidays. Alex asked me to turn over so she could apply sunscreen to my back, and then asked me to return the favor. To my surprise, she'd brought sun oil instead of the typical sunscreen...

2 years ago
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  • 167
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Interlude 3 ndash The FarthestOut Times so far ndash TV

Interlude 3 – The Farthest-Out Times (so far) – TV/CD , mast, fetishesWell, I believe I may have covered most of my fetishes between my previous blog posts and my intro paragraph here on Xhamster, but I may not have covered the extreme maxxximum extent to which I have taken each one. So for a quickie post, left let see if I can remember the “best of the best,” so to speak. I started typing one up for a conversation I was having with another user, and it got me so exxxcited I had to go...

2 years ago
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Julie out on her own ndash First Threesome ndash CDTVTS

Julie out on her own – First Threesome – CD/TV/TS, MFMRemember how Vicky, the blonde busty sexpot, owed me a favor, because she knew I knew she’d blown my best friend Mike at the bowling alley, but was going to keep quiet for her? If not, see the story two entries ago! Anyway, about two weeks later I called her up during the week, when I knew her boyfriend Frank wouldn’t likely be at her place. After a few rings, she picked up the phone.“Goodbody’s Mortuary, you stab ‘em, we slab ‘em, Elvira...

2 years ago
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Julie out on her own ndash Bowling Aftermath ndash CDTVT

Julie out on her own – Bowling Aftermath – CD/TV/TS, MMSo last time I wrote about how my roommate Mike hooked up with flirty Vicky at the bowling alley, how I knew about it, how Mike knew I knew, and how Vicky knew I knew, but how Vicky didn’t know that Mike knew I knew. Confused? Read last entry!Anyway, when Mike and I got home that night, we thought it was hilarious how Vicky’s horny lusts had gotten the better of her, how she’d blown Mike in the bowling alley men’s room while I watched over...

4 years ago
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Vacation Fun ndash Chapter 2 ndash The Next Morning

Vacation Fun – Chapter 2 – The Next MorningWith the curtains closed only a little light shined through the windows, but is was more than enough for Sam’s eyes to take in every curve of Carly’s body. Carly always looks so peaceful when she’s asleeep, and now Sam could freely lay in bed and stare for as long as she wanted or till Carly woke up.Before Carly climbed into bed just a little after midnight she striped down to only her underwear, slowly Sam started tracing patterns on Carly’s bare arm...

3 years ago
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Julie out on her own ndash with Mike and Vicky ndash CDTV

Julie out on her own – with Mike and Vicky – CD/TV/TS, MMSo last time I wrote about and my roommate Mike, how we’d come to terms with my crossdressing, my attraction to him, and his willingness to have a horny busty T-girl go wild on him.Since we both were comfortable with it, as time went on, I began staying dressed more in our apartment. Nothing fancy, but during evenings and practically all weekend, more often than not, if I had no immediate plans to go out, I would wear the following. Pink...

3 years ago
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Julie out on her own ndash more with Mike ndash CDTVTS

Julie out on her own – more with Mike – CD/TV/TS, MMSo last time I wrote about my first sexual experience with my roommate Mike, how I’d “ambushed” him when he came home one night, and I was dressed like one of our sexy busty slutty blonde friends, Vicky. The next morning, I was awake and eating breakfast in our kitchen (not cross-dressed), just in shorts and a t-shirt, ready to do some weekend chores.Mike came in behind me and cleared his throat nervously. He said, “Um, did what happen last...

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