
A sissy wanna be, but to shy to do anything The stuff I post is just things I would like to happen.
27 posts
Jcraining - Jenny - Tumblr Blog

Perfect Femininity
🎀Sissy Captions Daily🎀
AMAZING FOR LOOPS (pt. 1 )
This clip is “fire” for playing while watching your hypnos’~
Calling all sissies!!
If you run a sissy blog, please reblog this!! I want to follow each and every one of you little whores~
I am not exactly sure of the source on this, beyond that the creator calls herself Miss Violet, but I just had to share with the class. Throw some headphones on and give a listen.

Friday night Megan and her blonde friend Lindsay were walking home from practice, giggling about some of the hot guys on the team. “Can you imagine kneeling down in front of Bruce? Oh. My. God.” The conversation was making both girls totally frisky.
A limousine pulled up next to them and the two turned and pointed, excited by the rarity of the occurrence. Then the back window rolled down. Naturally they flocked over in curiosity.
“Need a lift, girls?” A man’s voice. Deep and smoky. Two cute little faces broke into a look of utter shock while the chauffeur stepped around the vehicle and opened the door.
Keep reading
A Sissy Surprise “The House Warming
First story ever partialy true and partialy fantasy.Hit me up with your thoughts when your done!
My girlfriend Vicki had been really pushing me to go to her friend Mary’s house warming party on Saturday night. Mary had been quite the bitch lately not like the two of us ever really hit it off. To make things even worse she is aware of my panty wearing secret. Vicki had shared this bit of information with her when she first discovered my little fetish about three months earlier. Since that time every time Mary is around she would drop little comments my way just to remind me she was in on the secret.
Saturday came around and off we went. We got there a little late and there were already several people there and everyone was separated into their own little cliques. We walked in and got a drink and took a tour of Mary’s new place. It was nice but a little cold which I thought also fit her Mary’s personality. A little later Mary walked up to us and asks if we would like our drink refreshed. Sure I said and asked that it not be too watered down. She smiled and told me not to get your panties in bunch that she would take care of me. Nice I thought, doesn’t she ever stop.
The night went on for several more hours and I’d had had a few more drinks and was feeling quite good. I felt warm and tingly all over my body and was very happy and had become quite talkative. Mary found Vicki and I talking in the hallway. She walks right up to us hands me another drink and then whispers something in Vicki’s ear. They both turned and looked at me and laughed and then Vicki walked away towards a larger group of people. Mary walks up closer to me and asked how everything was and how I was feeling. I felt her had brush against my cock and then she dragged he fingernails up my chest and put her had behind my neck pulling me into her. She started pulling herself against my cock which was now hard as a rock and throbbing like crazy. My head was spinning and I felt a warmth flood over my body. The next thing I know we were making out and I had my hands under her short skirt pulling her tight against me. She pulled back and said easy big guy you better slow down a bit. Then she steps back a bit, reaches up and under her skirt, and pulls her panties off and hands them to me. You know what to do with these don’t you, now finish your drink and be a good boy. What the fuck ? Did that just happen? My head was so tingly and my whole body was pulsating like I was having an orgasm and it felt so amazing.
Just then Vicki walks back up to me and asks me how I was feeling. I’m feeling great but a little dizzy I said not knowing if she knew what just happened with Mary. Go in the bathroom and get yourself together she said, splash some water in your face. Doing as she suggested I walked down the hall and into the bathroom pulling the door closed behind me. I quickly tipped my glass back and swallowed the last of my drink and then almost tossing the empty glass onto the counter. I quickly pulled off my shoes and pants and pulled her still warm panties up my legs and over my cock. I instantly felt my legs go weak and I had to lean against the wall and slowly sit down on the floor. I have no idea how long I had been sitting there when all of a sudden in walks Mary. Vicki told me I could find you in here. You’ve been a very bad boy, just look at you laying there on the floor like a stupid little bitch wearing my panties. What are we going to do with you she says and she then calls out for Vicki and together the two of them helped me stand back up and help me out of the bathroom. I see everyone staring at me as we enter the living room. Why wouldn’t they, I am wearing girls panties and no pants and can’t hold myself up to walk. They take me down stairs and lay me out on the bed. Vicki then turns and walks back up the stairs leaving me alone with Mary. Mary then sits me up in the bed and helps me out of my shirt and begins teasing my nipples. The last thing I remember is her biting down hard sending sensations shooting through my body and then everything just went dark.
I came to sometime later only to find myself on my back tied spread eagle in the bed and blindfolded. I felt the silky smooth cool feeling on my legs and I knew I was wearing stockings and heels, or at least I hoped it was because this has always been a fantasy of mine. I could feel someone right next to me and I could hear soft moans and heavy breathing coming from across the room and it was starting to turn me on. Then I felt warm fingers begin to rub lube around and into my tight and very sensitive asshole. I immediately raised my hips and tried to push against the new very inviting sensation. Mary says you’re really enjoying this aren’t you. This feels good in that boy pussy of yours doesn’t it? God yes I answered. I want more I blurted out. She then pushed in another finger and shortly after that squeezing in the third stretching out my tight pussy and it felt amazing. That’s it be a good little girl and enjoy getting what you always wanted.
The next thing I know Vicki climbs onto the bed and kisses me deep and says I hope you like what we have planned for you. From the look of your hard little boy clitty leaking all over your tummy it would seem you are really enjoying yourself. Then she turned around so my head was now between her soft warm thighs. I could smell the scent of her pussy and I knew it was only inches form my face. Just then I feel a soft and warm touch pressing against my cheek and then slide up to my mouth. Without a thought opened up my mouth and sucked the tip of a strange cock into my mouth. I feel the soft cock begin to swell in my mouth as my tongue slides around the tip keeping time with Mary’s fingers as they tease, stretch and fill my new boy-pussy. As I sucked the cock rock hard and it was then pulled out of my mouth and Vicki pushed back. He was going to fuck Vicki right over my face. Vicki pushed back hard and then continued thrusting back keeping pace with the forward thrusting of the strangers cock. Just then I felt an intense burning sensation as my pussy was stretched and penetrated with what I can only imagine is Mary’s whole fucking hand being shoved inside of me. The sensation felt as if the pressure pushed up and out through my swollen little clit as pre-cum oozed out a pooled on my stomach and then began to run down my side. I was almost being fucked unconscious by the fisting Mary was giving me when Vicki moans out loudly “yes, yes harder, fuck me harder, I’m cumming”! I could feel her explode and her juices began to drip down over my face. I honestly believed I was feeling exactly what she was feeling when she pushed back hard, her body shaking and her thighs trembling. The stranger then pushes back against her violently pounding furiously deep inside of her. Finally he pushes in deep and shots his hot load of cum deep inside of her. The thrusting stops and I can hear soft moans and can feel the gasping for air as Vicki collapses over me. The strangers cock just slips out of her pussy and slaps me in the face. I take his cock back into my mouth and as if in desperation I licked and sucked the juices from his still throbbing and swollen cock into my mouth. I suck him deep into my mouth and into my throat stealing whatever cum is left that wasn’t already expelled. I sucked his cock until it had nothing left to offer and went from rock hard to soft and flaccid. The stranger than simply steps back and he is gone.
Mary had slowed down on her thrusts and then without warning makes a big fist and quickly pulls her it out of my aching needy pussy immediately leaving me feeling empty wanting more. Just then Vicky moves and with her pussy directly over my face she squats down over me. I feel her juices and the strangers load filling my mouth. Globs of warm cum mixed with the sweet taste of her swollen used pussy. She is grinding over my face almost suffocating me as I lick and suck every drop and every glob I can get from inside of her sweet swollen cunt. Eventually Vicki slows and then rises up off of my face. I gasp for air and feel so satisfied. Just then I feel something warm, soft and yet hard press up against my now swollen and sore pussy. I know instantly what it is, it is what I have been wanting since the first touchof Mary’s fingers teasing my pussy. It was a cock and it felt different than anything I have ever felt before. I felt the tip push forward and plunge into my pussy stretching me out once again. It push back as his hips push forward against me as his cock sinks deep inside of me.
I feel my legs being untied and the blindfold is now removed and I see a gorgeous, soft very curvy black woman standing between my legs. So here I am living out my fantasy of feeling like a woman and knowing what it feels to be fucked like a woman and I am being fucked by a woman. But it isn’t a woman is it. No it’s a shemale, and aA very beautiful shemale with huge full breasts and who’s big fat cock shoved deep up inside my swollen throbbing fuck hole. I wrapped my legs around her ass pulling her tight against me. She began to pump back and forth and it actually moved my whole body back and forth with her. Her cock is huge and it feels like it could push out my throat as she pushes deep inside of me. This goes on for quite a while and she fucked me silly throwing me around like a little rag doll. She then moves my legs and puts them so my ankles are resting against her shoulders and the back of my legs pressing against her very firm tits. Grabbing my thighs tight she begins to pound me deeper and harder. I grab a handful of sheets squeezing them hard and moan out loudly as she then slammed forward. She stops deep inside of me as I feel the pressure of cum as it shots from her cock unloading deep inside of me. UUUMMMM I moan out loudly as my body suddenly shudders, my head pushed back against the bed and I cum harder than I ever thought possible. I can feel my pussy pulsating like never before. My body convulsed repeatedly and my eyes rolled to the back of my head and my toes straightened out hard. I think I passed out for just a second or at least until she pulled her massive cock from my pussy. Again I felt a void but this time I felt her cum begin to leak from my ass. It felt warm, wet, sloppy, amazing as I feel the cum flow and then drip from my worn out pussy . I was fucked like a little slut and it was everything and more than I could have ever dreamed. Just like the stranger that fucked Vicki the beautiful woman turns and just walked away.
This was amazing I thought as I feel a warm mouth licking the pre-cum from my stomach. It tickled and sent shivers up my spine as the tongue traveled down my side to get every drop that was spent. My clit sprung back to life and was hard as a rock. Mary climbed over me taking my cock inside of her as she pressed down. Vicki then climbed back over my face and began to kiss Mary deeply as they both grind down over me. Mary’s pussy was warm and very wet and Vicki began to get wet once again. All at once the three of us came together. I shot deep into marry as he pussy clinched arouns my cock as if to suck the cum from my cock. Vicki began to shake and her legs gave out and she fell into Mary and I almost knocking Mary off the bed. Mary gets back up and moves to put her pussy over my face. Clean me bitch she said as she squatted over my mouth. Again my mouth is flooded with cum and now the juices from Mary. She tasted like a peach and I couldn’t get enough. Vicki now began to clean my cock with her mouth until it tingled to a point it was uncomfortable. Mary got up and her and Vick moved around to me and the three of us lay cuddled up tight together. Vicki kissed me deep and asked me what I thought. I had no words I just smiled big and stared deep into her beautiful full eyes. I thought so babe she said. Happy anniversary sweetie she said. What I said I had no idea. Why do you think I told your secret to Mary, this night was all her idea. Sorry we had to drug you but I bet you’ll forgive us. With that the three of us fell into a deep much needed sleep.
The next morning we all got up showered and enjoyed a very big breakfast together. I thanked Mary and admitted I misjudged her. She just smiled and said, I know, so do you want to see the pictures everyone took last night? You were a very greedy little slut. Pictures? Everyone? I replied. Yes dear, I invited everyone from the party come down to watch you and record the moment if they wished. I’m sure they won’t mind sharing them with you she laughed!
Send me your thoughts: sy2xdrs@gmail.com
Neighbors Son
My neighbors high school son caught me dressed up the other day. It was late at night & I was dressed up like a sissy slut & I went outside to my car thinking no one was around. He smiled & said hey. You look good. I smiled back and said thanks let’s keep this a secret. Yesterday morning he told me his parents were out of town & he wanted me to come over. I said I don’t think so. Then he said I’ll keep your secret if you do. Just for a little while. I agreed. He told me to dress like I was the other night. I was nervous but got dressed & went over. He opened the door naked and said come in. He was 18 & had a huge cock 9” & super thick. It was kinda dark in the house. He led me by to a bedroom. When I walked in there were 5 other guys all late tend early 20’s. They shoved me onto the bed & pulled up my skirt. I tried to fight them off but they were to strong. The neighbors son pushed his huge cock against my tight hole. He told me they were going to rape me for looking so sexy & dressing like a slut. He shoved his huge cock deep into my boipussy. I screamed. One of the other guys shoved his cock down my throat & started choking me. They all took turns brutally fucking my ass. I think I passed out from pain or being chocked. I wake up feeling like I was getting ripped open. Two of the guys were shoveling both there big cocks into my ass at the same time. Holy shit that hurt. This went on all night. The next morning I woke up covered in cum. I could barely move. There was a note with $40 next to it. Saying thanks for last night whore. Keep your mouth shut & I will too. See you soon.


If I could there wouldn’t be any captions though, because I would be spending all night like that!

Be honest… You’ve gotta do both 😘 PS: If you like, just dm me… I might answer if you tryhard einough ❤😘

The Shower
Hi my name is Shai instagram (shai2a) my hight is 1.80m Am bloond , with a big and nice ass and with some muscles. And a 17cm dick…. And this is my stories.
I play at a basketball league In my team are three guys in the group one17-18 years old And two 16-17 that did this to me.
It was Monday, after a hard and sweaty training session I decide to go to the shower. (The shower room had Two showers with a barrier between them) After a few minutes the three guys walk in to the room butt naked. And I’m nakes of course…. Felt a little uncomfortable … (After all ,I am still a virgin ….). The two younger ones went into the other shower and the older (Simon) came to my shower stall.
I felt discomfort, I headed to leave , but Simon stops me and asks me “What’s the matter?, what ,are you gay ?!” I decide to stay and he starts to soap his beautiful body (abbs, nice chest and a nice little butt) I started to get hard , and he played it as he wasn’t noticing .
All of a sudden he turns to me and ask me to help him soap his back. Me still mesmerism by the view just stared soaping him….
After a few second that felt like a life time in heaven he turns to me and asks me to give him my hands. Im still emphatic from what just transpired so I just gave him my hands. Simon takes something from behind his back, plastic handcuffs and closes them on my hand before I get a chance to react.. just as i was starting to comprehend the situation behind me I see the two younger guys… One of them (Illouz) bends down and puts cuffs on my legs… Itry to run away but fall to the wet floor by a push from behind…Simon…
Simon calles Illouz to help him pick me up, they lift me onto my knees …. And now in front of me there are Three beautiful cocks…. The first Illouz, 18 cm half-hard, beautiful and just the perfect size. The second youngest of the three (Hadar) … 16 cm nice and as hard as a tree lamb !! And third Simon, a magnificent cock (23 cm hard) and still soft ….
Simon is the first to act pushes my face to his cock …. I tried to fight, and not to open my mouth … Simon slaped me across my face and yelled “if not through here …. so from behind!” With no other options I open my mouth and let his cock pushed into my mouth …. It’s huge … barely a quarter came in …. I feel a bit stifled, Simon holds my head and Moves it back and forth ….. I thoght about biting but it was too good …. I enjoyed it ….. Simon continues moving my head back and forth and moaning little moans “Take it !! Take all of it!!” He shouts
The other two are whispering in the background are looking at my virgin ass …. and then my dick, “he’s really enjoying it” one of them says.
Simon begins to settle back on the wall and floor, and I fell on him my face grinding on his dick ….. Illouz lifts my body and Simon pushes his cock back in to my mouth …. (I am now on my knees, two legs together and my but up ….doggy style….) Simon’s dick almost at the peak of its size (something in the 21-22 cm at the moment ….) Illouz goes back and cuts open my leg cuffs … He looks at me to make sure I dont run away, ….. Me, acting like someone who wants it did not move, just continue to please Simon, Illouz spreads my legs ….. He holds both my ass cheeks and separates them, I feel a little sore around the hole …. And then … I loss feeling of my senses … I feel it entered my body….. It hurts so much but yet feels so great! He could barely put it in….. slowly he moves back and fourth , pushing more and more of it every time …. I can see on the edge of my vision Hadar with a stund look on his face …… such an innocent child.
Illouz calls him to come and try me out. Hadar turns to me …. He asks me, “Can I? …. Is that okay?” I dont answer …to busy with Simons beautiful cock. And at this stage of the act I dont even understand the question … Illouz is calling him and he goes … I feel Illouz’s dick going out for the last time …. and without a second od wait I feel the thrill again…. it still hurts, even though all 18cm of Illouz’s dick were just in there. He moves back and forth, I hear his waist meet with my butt cheeks … I lift my head to look at Hadar … And without warning, Simon grabs my face and cums all over it …. so much cum…. My whole face was white …. Simon was Looking dazed and had a huge smile on his face ….he says “great job”, and laughs ….. I turn and see the Hadar pushing repeatedly with an orgasm look on his face …. Illouz approaches me, sitting where Simon sat and pushed my face … That have yet gained its breath back …. To his stunning cock, this time I use my toung …. Illouz enters a loss of senses, laughs, slaps me on the cheek and pushes My head up and down as much as possible …. I feel Hadar beginning to slow down and beginning to startled …. …. And then …. I feel his sperm rushing into me filling me! And I cum with him …. Illouz continues for some time,but finally cums up in my mouth … it tasted a bit salty but amazing….. They left me on the wet floor ….. full of sperm…..there love juices…
The END
Rape Fantasy: The New Football Team Special Assistant Part 2
The sound of the running shower was what I heard first. Then the sensation of the water hitting my naked body. When I opened my eyes, I was met with the murky and fuzzy empty showers of the boy’s locker room. The area was covered in mist of the hot water that was hitting my bear skin.
When I moved my head around, I could see no one around. I tried to move my body, using my arms to lift myself up. That’s when the pain, shot through my body. The soreness of my hips, and the burning of my inner crotch. The pain escaped through my mouth in a grunt and moan; as I moved out of the wet shower room.
I walked around the locker room in a daze. Then sat down one of the bench’s. As the memories of what happened to me started to return.
- Hours Earlier –
My mouth was on fire, the lack of air was making that even more of a struggle to make it moist. Each time this guy’s big cock pushed forward and back, it barely left my mouth each time he pulled back. His bell-end would rest on your tongue for just a split second, before pushing back into your throat. You gagged and chocked just like before; when you mouth and cunt were raped for the first time.
The rest of the team joined you in the shower room, you opened your eyes to and gazed through the mist of hot shower water. These boys stocking and enjoying the site of you naked body, and your mouth being violated once again. The boy fucking your face finally let you go, pulling his cock from your mouth; letting out a satisfied grunt as his cock plopped out from my maw.
But my rest bit only lasted a few seconds. They boy still had a hold of my hair, and pulled me towards two other boys their cocks standing a full attention in my face.
“Well bitch? Do your job and lick those cocks!” Said the boy gripping my hair. My face was pulled towards their crotch’s. My lips pressed his cock, a soft grunt escaped him.
I felt the tight grip on my hair leave, and then my lips being parted once again. Once again, my mouth was stiffed with another man hot and thick rode. The feeling of his head grinding against my throat, and making it dry. I could hear the moans and heavy breathing of this boy from below me.
Then I felt my world shift. My head was pulled away from his cock, giving a moment to catch my breath; only for my mouth to occupied again by another cock.
“Ahh~ Fuck yeah! The coach go us a good one!” I heard this boy say, thrusting his cock into my throat at a rather slow pace. “I fuck I just want to fuck her.” He said, slowly pull his hip back, and then forward again.
The slow fucking felt completely different from the rapid and hard pace of the last two boys that ravaged my mouth and throat. I felt his cock throb against my tongue, each time he thrusted into my throat. I could feel my throat getting more and more wet, as his head pushed into my throat. When he held my head still, and left his cock in my throat. I start to choke and gag, and started to panic.
I could feel my head getting light again. My mind was starting to go white, as my body started to beg for air. The choking and gagging, echoed through the showers. I used my one of arms and started to tap onto his leg and thighs; desperately trying to get him to let me go.
I was meet with the sensation of something hot and stick suddenly being pumped into my stomach. My eyes rolled back into my head, as he continued his unwarned orgasm.
When he let me go, body slumped down onto the wet floor, my mouth oozing out a stream of white liquid; a stream of tears once again started down my face. I was breathing again, but I knew that this would last long.
The boys started to shift me around again. This time, one of them was on his back, with my body sprawled on top of him. I could feel something hot pressing against my pussy, looking down, I could see that this boy was more than happy to be in this position, I felt his hands against my hips, then my ass. His strong hands massaged and kneed my ass, he even gave me a few slaps.
“Come on yeah little slut smile a little.” He said reaching up and putting his hands on my face. “I know you’re going to love this.” His hands, slide against my hair gently, then he pulled into a passionate kiss, his one hands cupping my face and keeping me from pulling my head away. While his other and positioned his big black cock, into my pussy.
I could only moan into the kiss, the sound coming out a muffled and slurred; as his tongue invaded my mouth. His hips moved up and down, his big cock pushing into my cunt with a ravaging pace. I could feel it stretching and pushing deep into my pussy, the feeling of hit hot rode, pushing deep into wasn’t like before, this time it was much more passionate, as he was trying to get my pussy use to the feeling of hit big cock.
With each thrust my pussy started to get more and more even though we were in the showers and soaking wet; my mind thought that it was purely coming from my cunt.
“Ahh~ See, I told you would start to love this.” He said, putting his hands on my ass again, and give me a few soft smacks. “Hey, I think you ready for more.”
With that he reached up and grabbed me by the head, forcing me to turn and see what was coming. My eyes widened with fear, as I watched another boy walk up behind me. His big cock moving over towards my ass. I mouth opened to try and tell him to stop, but all that that came out was moans and panting.
“Don’t worry,” The boy said, pushing his bell-end into my ass. “Just relax, and just take it!” I felt my body shiver. The thickness of his cock, and the heat of the boy’s head, pushing deep into my ass; made my scream out.
The sounds only seemed to make the boys in the showers more aroused. They didn’t have any shame to stroke their cocks in front of the girl that was having both her holes violated at the same time. My body was being ravaged like before: only know I could yell out, but I could only moan and pant.
I could feel each of the cock grinding and churning against each other, the sensation of their big and thick cocks even between my ass and pussy. It shouldn’t feel good, it should have felt bad having my body being violated again. Yet, I was starting to feel something.
“Only shit! Grahh~ Little bitch is moving her hips now!” I head the boy below me say, “Starting to feel good now huh?” He asked putting his hand around my neck.
I couldn’t say anything, I didn’t want to say anything. My body was moving on its own now. My mind was a slurry at this point; any words at this point, were just an incoherent mess. Suddenly you let out a loud howl, as you ass was struck hard.
*Smack* “Come one bitch! Say you want more!” *Smack* “We all want to know you love this bitch!” *Smack*
I felt my ass burn from the hard spanning from the boy fucking my ass, my ass most likely was turned red from this hard assault.
“She ain’t sayin nothing! Ahh~ Let just finish her off!” The boy below me said.
I felt the hand around my neck tighten, my moans and voice sounding horse and shallow. My mind slowly started to waver again, my eye starting to roll back into my head.
They continued to thrust hard and fast without a care from my wellbeing again. The sound of skin smacking against each other filled the shower room. The boys around us that were stocking their cocks, loved what they were seeing. Watching me falling to their big cock raping my holes at the same time, my raspy voice leaving my mouth.
“You ready bitch! We cumin now!” I heard one of them say.
They thrusted hard. Each cock pushing right to the base, their hips smacking into me. I couldn’t even let out a moan, as my tongue flopped out of my mouth; and my back arched. My orgasm was silent, even as they pumped me full of their hot and sticky cum. I could feel their cock throbbing each time they pumped me full of seed.
When they finally let, me go, I finally felt my pussy and ass being pelted with the water from the showers. No doubt agape and oozing with cum as I shiver and quiver from the afterglow of my raping. I felt something grab onto my wet hair and pull my head up. My eyes barely focused on the figure in front of me, only really looking at the fuzzy image of an enlarged cock.
“You work for us now bitch,” He started with a cheer echoing through the showers. “Congrats on being the new special assistant for the team.”
I couldn’t say anything, only nodding my head in agreement; with a smile forming on my face now.
To Be Continued.
Brainwasher loop audio mp3 to play while scrolling tumblr








わちを

Conservative mom trying to deal with her 18 year old rebellious son.

[My Twitter]
[My Streams]




Here’s a little something y'all might enjoy 😉



❤️ Find more of my captions at kimmie-cumslut.tumblr ❤️
💖 Check out my Patreon! 💖

🌺Follow and Reblog. Spread the SISSY Life 🌺


YOU SAID YOU WANTED TO GO OUT
GET DRUNK AND GET FUCKED
YOU DID IT ALL, SISSY

CAUGHT DRESSING UP…
PUSHED TO YOUR KNEES
HIS HAND ON THE BACK OF YOUR HEAD
YOU HAVE NO CHOICE
STRANGE THAT THIS “ACCIDENT” HAPPENED THREE TIMES TONIGHT…