In this fourth book in the “Tricked Sissy” series, Chloe is about to start college and she thinks she’ll be leaving her sissyhood behind, finally able to have straight sex again! But Sarah has a surprise in store for her – a surprise that will lead to some very fun sexual encounters for Chloe!
This 28,000+ word erotic story contains very explicit adult material, including oral sex, masturbation, anal play, gay sex, CNC, BDSM, voyeurism, exhibitionism, chastity, sex with machines, being tied up, and more. This story contains ONLY ADULT CHARACTERS and is strictly for ADULTS ONLY!
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Chapter 1 – Car Ride
It would be odd going back to be called Connor instead of Chloe, but I don’t think I would leave “Chloe” entirely behind; after all, I had grown my dark hair out quite a bit (it was now just past my shoulders) and had done enough squats to make my butt “really juicy” as Sarah put it. I also didn’t get much of a tan during summer so I was still rather pasty, plus I had taken to shaving frequently the little hair I had on my body so that it was always nice and smooth ‒ I liked it that way!
I was still wearing women’s clothes until the end of summer and it felt a bit of a shame to go back from the nice, smooth, light fabric to my usual “dark shirts and jeans”. But one thing I definitely wouldn’t miss is the cock cage! Over the last several weeks I barely got the chance to touch my own clit!
Ah shit, that’s another word I’d have to get used to again: saying “cock” instead of “clit” when talking about my penis!
Anyway, Sarah promised me she’d give me the key to my cage as I moved to my dorm on campus. I’d finally be able to jerk off normally! Although I do have to admit that using the several dildos, vibrators, buttplugs, and even real dicks really made my orgasms feel stronger ‒ but I was going to leave that behind me (no pun intended).
I had insisted Sarah give back my clothes she had stolen to be replaced with the girly clothes she had bought. I wanted to give back the feminine clothes, but she said she’d just put them in a duffle bag and keep them “for when I changed back” ‒ hah! Like that was ever going to happen! But she kept true to her word and helped me pack on the week of my move. She had even offered to drive me and my stuff to campus!
Sarah had spent the weekend before the move at my place. We had some final fun with me as her sissy slave and I ended up cumming a few more times still with my cage on; it would be nice to be able to finally touch my cli…my cock again, but that would have to wait until she dropped me off on Monday.
Monday arrived and I woke up, ready to get going!
Sarah and I had come to an agreement on what I was to wear on my first day. She ‒ of course ‒ wanted me to go full girly, but I wouldn’t budge on going as a man. Eventually we set on a pair of dark blue exercise shorts that extended down halfway my thighs and a fairly tight black sports shirt. Despite the outfit really bringing out my curves, I thought it was still manly enough ‒ plus that choice of clothing was better than her “mini skirt and crop top” suggestion for my first day.
One thing I did have to give in to was my underwear: she wouldn’t budge on a pair of satin black tanga panties. But that’s fine ‒ not like anyone would know anyway. Plus, women’s panties still felt way more comfortable to the point I was considering to keep wearing them. I wasn’t going to tell Sarah though as I didn’t need her to get any ideas; I’m just thankful she didn’t insist I wear a fake bra as the shirt was way too tight to hide any fake boobs.
“My cage is very obvious in these shorts! Look at the bulge!” I complained as I dressed up in front of her. “Can I please take it off now, Mistress?”
“We agreed that you would wear the cage until it was unlocked. We also agreed I would give you a key once I dropped you off. Plus, you’re the one who chose the shorts you were going to use! I’m not going to unpack all your clothes just because you’re self-conscious! No one is even going to notice!”
I huffed, knowing it was pointless to argue with her. Yes, I had chosen which shorts, but the choices she allowed me to have were either these ones, daisy dukes shorts, or a pink ruffled skirt. So not really a choice! But fuck it, she was right on the main point: no one would be looking at my crotch anyway!
Sarah decided to go full sex-bomb with her outfit to drive me to the campus: a satin black corset top with red flower stitches that held up her 30 C tits and pressed them up together, resulting in some lovely exposed cleavage and showed off her sun kissed shoulders, a red faux leather pencil skirt that glued to her shape, and black laced gladiator sandals. She made it a point to show me that she wasn’t going to wear panties or a bra as she dressed up in front of me. Her green eyes shone through her blonde curly hair. If my cock wasn’t in a cage (and if I hadn’t been sexually exhausted from the weekend), I’d surely be hard as a rock right now. The necklace with the key to my cage disappeared between her breasts.
“Seeing as you’re still my property until I drop you off at the campus, Chloe…” Sarah began as she wiggled into her skirt, “I want you to wear something extra for me in the car.”
It didn’t really sound like a question or request, rather an order. I had sat down on the bed to put on my sneakers, and fearing I’d have to change into another outfit, I froze in place.
“You’ll wear the remote controlled butt plug while we’re driving. Then once we’re there, you can take it out and keep it with you. Think of it as a souvenir.”
I considered arguing with her, but she had conditioned me so well over these past weeks that the thought didn’t really materialise in my brain.
I simply got up, went to my bedside drawer, slid it open, and pulled out the bottle of lube and the black, thick, silicone plug that could be remotely controlled by Sarah’s phone. I had used it a few times since she gave it to me, and, I’ll admit, it was quite pleasurable as it was designed specifically for those that had a prostate.
I pulled my shorts and panties down to my ankles and lay over the bed, making sure to really put my ass out. As I had done many times before, I opened the bottle of lube, squirted a generous amount over the plug and spread it around with my own fingers, then proceeded to insert the lubed up fingers into my own little hole.
Once everything was nice and slippery, I pressed the “on” button from the plug and began inserting it gently past my ring. As the shaft passed the halfway mark, the vacuum pressure kicked in and my butt swallowed the rest of the plug until the flared base did its job by preventing the whole thing from entering me. As this happened, I let out a moan of pleasure. I was going to miss this!
Sarah simply smiled at me and gave an approving nod.
I pulled my panties and shorts back up and stood up, feeling the plug rub against my p-spot. She didn’t pull out her phone to connect to it just yet, but I knew she probably would do so while we were driving.
Once we were all dressed, I grabbed my suitcase with all my bedding stuff and my backpack with my laptop and study materials. Sarah kindly offered to carry the duffle bag with my clothes to her car.
I hopped in the passenger side and waited for Sarah to shut the car boot. As she sat on the driver’s seat her skirt immediately rode up her legs until it barely covered her shaved pussy. Although I’ve seen it many times this summer I couldn’t help but stare at it, remembering its sweet taste. She must’ve known that would happen, and also must’ve known I was going to gawk at it. So to help me “behave”, while I was busy staring she unlocked her phone and used the app that controlled my butt plug.
The sudden vibration inside caught me off guard and I let out a small yelp and turned my attention to her. She simply smiled, satisfied to be getting me off one final time. I could tell she had set the plug in the random vibration mode, as it continued to vibrate at varying speeds while she began driving and not looking at her phone anymore.
My little cock cage had suddenly become tighter. Even though I’ve used it pretty much everyday since she put it on me, my dicklet would still get as hard as it could given the constraints. I initially kept my hands by my side, but once we hit the highway Sarah stretched an arm to my lap and began fondling my balls and cage over my shorts. I couldn’t help but wiggle in my seat as the vibrations kept me aroused, and although I was sexually spent for the day, I felt the need to cum.
Sadly the butt plug had a sensor in it that could tell when I was getting too aroused and it would either slow down or stop completely, then ramp up again once my hornyness subsided. This just resulted in me edging constantly without giving me that sweet release, leaving me very frustrated.
I knew Sarah could override that function on her phone, so to convince her to let me orgasm I thought I’d give her some pleasure under the hope that she would return the favour;
I brought my hand to my mouth, licking my fingers to get them well lubricated, then proceeded to put them down between her legs over her exposed pussy. She let go of my balls and kept both hands on the wheel – after all, we both wanted to get to my campus alive and in one piece!
My fingers began gently rubbing her outer labia, spreading them gently to reach the inner. I took my time and kept an eye on her to make sure she wasn’t getting too distracted. As she spread her legs, her skirt rode up a bit more, which gave me further access to her sweet pussy.
I went from rubbing her inner labia to gently applying pressure to her clit, moving my fingers in a gentle circular motion. Her breathing increased, but her eyes were still on the road, and as my focus was on her and not my own pleasure, my plug detected that and began vibrating again, much to my delight.
I put my other hand under my shirt and began playing with my nipples. Playing with her pussy with one hand, touching my own tits with the other, and the butt plug vibrating against my p-spot, made me feel like I was touching my own pussy and gaining pleasure from it. I often wondered what it would feel like to have a cunt instead of my sad, little dicklet; and this felt like it was the closest I could get to that feeling.
Sarah was getting close and she probably knew that the only way to get pushed over that final hump was to dedicate 100% of her focus on what we were doing.
Pulling onto the hard shoulder of the motorway, she turned on her hazard lights and put the car into park. She could finally close her eyes and just let the feelings roll over her as I jilled her into an orgasm. As she reached it, her legs clamped shut onto my hand and she moaned loudly, still holding onto the wheel.
As soon as she opened her legs slightly, I removed my hand from her and grabbed my own balls. She quickly unlocked her phone and turned the vibrations on my plug to the highest setting. I yelped. I could feel the pressure building up to an intolerable level and I was ready to burst at any moment. My head snapped back and I held my breath, ready for the sweet release.
Then, nothing.
Sarah had turned off the butt plug and I started squirming violently in my seat, trying to get that last bit of pleasure. She strongly slapped my hand holding my balls, causing me a considerable amount of pain which had the effect of also killing my hornyness.
“Don’t you dare cum, you dumb sissy!” Sarah ordered. “If you do, you’ll just stain those nice shorts! We can’t have you arriving at your uni with cum stains, can we?”
I looked at her with pleading eyes, but she turned her gaze to the road again. Turning off the hazard lights, putting the car into drive, and checking to merge, she sped the car up, leaving my orgasm behind. I was angry and aroused and not only did she know it, she also revelled in it.
She didn’t turn on the plug for the rest of the ride ‒ which thankfully wasn’t very long.
Once we arrived at the campus she drove me to my dorm and parked. Sarah got out of the car and walked to the boot where she began offloading my bags onto the sidewalk while I checked on my phone the directions to my room. She helped me carry the duffle bag with my clothes as I took the backpack and suitcase.
There was a queue outside the building where students were lining up to pick up the keys to their dorms. Sarah’s outfit had turned several guys’ heads as we walked towards it, and even a few of the girls gawked. One guy even gave me a thumbs up, probably thinking she was my girlfriend. I just smiled back at him.
Sarah offered to stand in the queue as I gave a quick walk around the building to check it out. She was being unusually helpful, but then again maybe she was just feeling bad about how she treated me in the car.
Once registered, she waved me to follow her into the building. We went to the second floor which was marked as the males only wing ‒ which was a bit of a relief. I found my dorm, knocked and waited for an answer that never came. I used my keycard to unlock the door and entered to find the standard living dorms for any student: to the right of the door, a wooden wardrobe big enough for two people went extended to the adjacent wall. On the wall opposite the door, a big window with two desks and two chairs with space in between them to stand in front of the window, and on either side of the desks two bedside tables followed by two beds on opposite ends of the room. The bed directly in front of the door was empty, while the other one was made with navy blue sheets ‒ probably the bed my roommate had picked out for himself already. The bathrooms were communal, so there wasn’t a lavatory in my room. My roommate seemed to have already settled in before I arrived, but there was no sign of him.
Sarah dropped the bags on my bed as I checked my phone to see the next activity. It was an introduction class for newcomers and it was starting shortly, so there was no time to unpack or even take out the plug.
“Well, I’ll let you get to your class, babe.” Sarah said as she gave me a hug, pressing her boobs and her hips into me. “I’ll make sure to visit often as it isn’t much of a drive, so you behave Chloe, ok?”
I didn’t even notice her using my sissy name at first, but having her pussy essentially rubbing against my pelvis reminded me of one final thing:
“Thanks Mistress. But…what about… uh…” I stammered and looked down to my crotch.
“Ah, yes. The key I promised.”
She grabbed the keys to her car she had put down on my desk and fished one of the keys from it. I looked puzzled, wondering why she was giving me this key and not the one hidden inside her cleavage.
“It’s a copy”, she answered before I could ask. “I’m keeping this one” she said, pointing to the necklace between her boobs, “as a memento, a sentimental reminder of this last summer.”
She put the copy in my hand and I was about to drop my pants to finally remove the cage, but as my hands grabbed my shorts, Sarah interrupted me:
“You can do that later! Your intro class is starting now and you can’t miss it. Go!”
Sarah grabbed my hand and followed me out my room and outside the building, always walking with a sway in her hips. In the car park, she gave me one last hug and wished me well, telling me to text her later.
Sarah noticed the stares we were getting (some people must’ve thought I was a girl) and decided to pull me in to give me a long tongue kiss, which caught me off guard. I could feel blood rushing to my clit…no! Penis! But before long, she broke off and began walking to her car, turning to wave at me before getting in.
I remembered what I was doing, so I rushed to the main building, pocketing the key for my cage. I found my way to the auditorium and had to squeeze past a few people to get to an empty chair. Due to the narrow rows many of the taller men had to stand up so I could scoot by, my back turned to them. At first, it just felt like I had to rub past them because of the lack of space, but the more men I passed by the more I noticed most were intentionally standing there to feel my butt press against their crotch. I was certain a few even kept their hands by their side and felt me up as I passed by! They must’ve known I was a guy and not a girl, right?
The introductory class was initially pretty boring, just covering some do’s and don’ts around campus such as only men allowed in the men wings of the dorms and vice-versa, curfew times, acceptable dress code, how the university was very diverse and open minded, yadda yadda. I was kinda losing focus on the speakers in the big hall.
Suddenly I felt a bolt of electricity shoot up my insides, making me jolt and nearly jump out of my seat while at the same time catching the attention of some of the people around me. First I thought it was an electric shock, but quickly realised it was my butt plug activating. That bitch knew I’d be in a class!
Thankfully the vibrations were low enough no one could actually hear it, but I could definitely feel it rubbing against my prostate. It was initially low key enough that it didn’t bother me much, but every so often the vibrations would increase massively for a second and that would make me suddenly grab the side arms of my chair. This went on for a few minutes, until the vibration strength stabilised at a medium speed ‒ which was intense enough without being audible.
I could feel my cage getting tight again and even some precum leaking from my clit, and began worrying that the liquid would be visible on the front side of my shorts. And although I desperately tried to focus on the centre stage, my breathing was getting heavier and my lust was getting unbearable. If this kept on for too long I was certain I would cum right there ‒ and because of all the edging Sarah put me through on the drive here, it was surely going to be a considerable amount of cum that would certainly drip down my shorts. I couldn’t let that happen, not on my first day!
I decided to go to the bathroom so I could remove the plug and my cage, but for that I would have to scoot by everyone again; the problem was that if my butt rubbed against someone’s crotch, they’d probably feel the vibrations coming from my ass. But that was a risk I knew I had to take, plus chances were that I wouldn’t even see these people again anyway!
Thankfully this time most guys just remained seated and simply moved their legs to the side as I passed by, which meant they didn’t have to feel me up earlier. Horny bastards!
As I was about to pass the last guy before the aisle, Sarah turned up the vibrations in my plug again. The shock made me lose balance and I fell butt first onto the guys’ lap, which pushed the butt plug further into me and momentarily turned my legs into jelly as the wave of pleasure doubled. He instinctively grabbed my hips to steady me, which made it slightly harder for me to get up again as I wiggled myself to get back on my feet.
The man finally let go and I managed to stand up again and move into the aisle. I turned to him to mouth “Sorry” and saw a smirk across his face; he knew!
The vibration speed lowered again which enabled me to walk as straight as possible towards the door of the auditorium. I looked for the signs to the bathroom which was thankfully empty, but I still headed towards the stall on the far side and locked the door.
I pulled my shorts and panties down and was about to reach around to remove the plug, but remembered it was fairly bulky and it wouldn’t fit in my pockets. It would have to remain in me until I got back to my dorm, no way around that.
But then I realised that, if I were to jerk off now and cum, the refractory period would keep me flaccid until the end of the intro class. And thankfully, I would be able to finally do it as I had the keys to my cage in my pocket! Ideally I wanted my first masturbation session since being locked up to be a special occasion, but now was not the time for celebration.
I fished for the keys in my pocket and inserted the key into the small pink padlock of my same coloured pink cage. “Finally free!” I thought to myself as I tried to turn the key.
The key did not turn.
A bit odd, sure, but just like with USB devices, there’s always three different ways to insert it!
I took the key out, inserted it again and tried turning it. Nothing.
Then I tried turning it the other way. Still nothing.
I took out the key and tried again.
It then dawned on me: this key was not the right one for this lock.
I was going to kill Sarah!
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Love and kisses,
Chloe