Sissies New Years Surprise – Part 2 – free porn video

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Chapter 2

Sissies Opportunity Blown

Sissy was dead tired. It had been a long and tiring day. Mistress was very picky today at inspection and sissy had to redo some of her work several times. Sissy would admit that some of her work was sloppy, but sissy could not concentrate. Mistress had just told her the biggest news and she still couldn’t wrap her head around it; no wonder her work was messy. As a result sissy had to spend an hour in the corner tonight and was sent right to bed following her chores and Mistresses dinner. Yet as tired as sissy was and as much as her feet ached she was wide awake in bed. It also didn’t help that it was only 8pm. Mistress always loved to humiliate sissy by sending her to bed early.

Sissy had no idea what to do. She knew her options were simple, either move in with this man and be a fulltime gurl or move out and try to live as a male again. She lay in bed with tears coming down her face thinking:

Where would she go?

Could she really try to go and find a new girlfriend at this point and start over?

If she did find a new girlfriend would her clitty be up for the task?

Did she really want to live fulltime as a girl?

Could she really go through with it and live with a man, a Real Man?



As the thoughts were bouncing around in her head she hears the door creek open. In walks Mistress in a stunning black satin gown, with a matching garter and hose. Mistress always came in to check on sissy, but never dressed like this. Sissies clitty was dripping already in her cage while she admired Mistress’s beauty. Mistress walked to the head of the bed and slowly turned around bent over and pulled off Her thong and then placed them in sissies mouth as a gag. Sissy’s clitty wanted to explode in her belt and was in a daze by Her beauty. Sissy suddenly snapped out of her trance and saw Mistress taking pinky out of sissy’s panty drawer. Mistress also took out some straps and She walked to the end of the bed and started crawling towards sissy in a very seductive manner. As She got closer sissy could see that Mistress was wearing a necklace with sissy’s chastity belt key on it. She was a few inches from sissies face and sissy wanted to speak, but quickly realized she had a panty gag in her mouth. Mistress pulled the panty out of her mouth and put her finger up to her luscious lips and shushed sissy. Mistress then leaned in and kissed sissy passionately and with such love, sissy was in heaven.



It had been a long long time since they shared a kiss like this. Finally after what felt like 30 minutes when it was probably only 1 minute Mistress pulled away and put the panty gag back in sissy’s mouth and then slowly removed Her nightie. She took sissy’s hands and placed them on her soft breasts. Sissy slowly and gently started rubbing Mistress’s breasts. “sissy Your gonna fuck me tonight”, Mistress finally said. “Yes Mistress”, sissy barely audible mumbled through her panty gag.



While sissy is still playing with Mistress’s breast, Mistress reaches back and unclasps the necklace. She then pulls the sheets down showing sissy’s femme body in her pink nightie. Mistress sitting up on sissy’s crotch inches her way back and pulls sissies caged clitty out front underneath her pink satin panties. “There she is”, Mistress says and unlocks sissies clitty. She continues, “I hope your ready sissy girl.” Sissies four inches are now at full attention and Mistress places her hand around the shaft and no sooner than She does this sissies clit explodes all over Mistress’s hand and some on her gorgeous breasts.



Sissy was crushed, she knew this was really bad for her case and it was the last thing she wanted to happen. “Oh sissy, how are You gonna to Fuck Me now?”, Mistress says in a sympathetic voice. “Can your clitty get hard again?” She asks but knows that won’t happen. “We will definitely try, but first clean this mess up.” Mistress leans over sissy and once again removes the panties and sissy obediently licks her cummies of Mistresses hand and arm, followed by her breasts and rock hard stomach. “Such a good girl you are sissy. Do you like the taste of cummies?” sissy gulps, knowing how she has to answer and also knowing it has an entirely new meaning now, “Yes Mistress”. “Thats good”, Mistress says with a smile. “I for one was never a fan of cum, I guess I spit as they say”, She said jokingly, and after a pause and a big sigh she continued, “but to each his own, if you like it that is fine by Me.” Mistress places the panty gag back in sissies mouth.



Sissies clitty was now shriveled up and inside her head she was praying that it would get hard again, but nothing was happening. “Come on” she kept saying to herself. On the outside tears are running down her cheeks. Mistress wipes the tears and says “It’s okay hon, everything will be fine, now how about that Fuck?” With that She ties sissies arms to each bed post and same with her legs. “There there, you look so hot tied up like that, I can’t wait to get that clitty in me.” She starts stroking sissy’s clitty. “Come on princess, get up for Mistress, come on princess you can do it.” she kept saying. After about 10 strokes and sissies 4 inches still not erect sissy’s nightmare took place and sissy once again made cummies. It didn’t squirt like last time, but just kind of leaked out on Mistress’s hand. Mistress just made a pity smile and said, “It’s okay honey”. The tears just kept coming down sissies face.
Mistress grabbed pinky and wiped her hands all over the shaft and balls. She then had sissy once again lick Her hand clean and then slid pinky into sissy’s mouth. “You suck on that while I get you ready”. Mistress then placed princess back into her cage and continued, “Princess had two shots sweetie, I’m sorry it didn’t work out for you.” Mistress then untied sissy’s legs and slid Her strapon harness up sissy’s legs. She adjusted the harness so it was nice and snug; it was not comfortable for sissy on top of the cage. She then retied sissy’s legs to the bed posts and then slowly started pulling pinky out of sissy’s mouth. She inspected pinky to make sure all the cummies where gone and then snapped pinky into the harness sissy was now wearing. “Now thats a nice cock, but first things first….”. Mistress maneuvered Her way up and sat on sissies face, sissy knew what she had to do. sissy eagerly went to work and was at work for quite some time only stopping when Mistress would lift up a little to allow sissy to catch her breath. Finally after Her second orgasm Mistress slid Her way down to pinky and easily slid it in her. Mistress started bumping up and down on pinky. Mistress was really riding pinky hard. sissy was wincing with each thrust b/c everytime Mistress came down it would slam the cage into her skin. Mistress on the other hand was in ecstasy screaming with pleasure. “Yes, yes, yes, ummmm god that feels so good. Mmmmm sissy what a nice cock you have.”



Mistress had at least 7 orgasms when She was finally done with pinky. She had maneuvered sissy and her fake cock into various positions and had sissy F Her with pinky for a couple hours. As exciting as it was, sissy was completely humiliated b/c her clitty could not do the job when it mattered most. Deep down sissy knew what her decision would be, but was still having a hard time accepting this.



Mistress finally got up and kissed sissy one more time on the lips before leaving the room. Mistress was satisfied, everything had gone as She had expected. She could see that sissy was upset and wiped her tears away. Sissy tried to speak through her panty gag, but again Mistress shushed her and simply said, “No decision sissy, I want you to sleep on it and tell me your decision at breakfast.” With that She turned and left. “sleep tight honey!”



To be continued….

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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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