This is a fictional story I started writing for Literotica, and I thought I would share it here. It's in multiple parts so I'll add them as I can.
Enjoy!
******
My wife Tiffany had been hinting for a while about my birthday surprise. She wasn’t great at keeping secrets, and I normally figured out her surprises in advance only to have to act surprised, but this time she was being super cagey. She asked if I would be able to leave work at noon that coming Friday so I figured we were going out of town for the long weekend (Monday was a holiday) – probably to a quaint B&B for a romantic weekend, or maybe even to the city to check out one of the swingers clubs we’d found online.
Ever since I had come out to Tiffany about my desire to crossdress and revealed “Chrissy” to her, our already-good sex life had morphed into another level of hedonistic pleasure. After some time for her to process it, she was supportive of my crossdressing and being a sissy. What started as us fantasizing about what we would do with another man who could dominate and cuckold me while satisfying her desires quickly became a reality. We joined a swingers dating website and began playing with a few couples. I found a couple of men to play dress up for. She found a man to be her “boyfriend.” He wasn’t interested in seeing me dressed up, so she would fuck his brains out and then come home to me. Some of our hottest lovemaking was when she came home full of his cum - which I would obediently slurp from her dripping pussy - before we fucked like horny teenagers. We had talked about checking out the swingers clubs in the city but had never found the time to make it work. I was hopeful that this was her plan, so I cheerfully took Friday afternoon off from work.
“You got tomorrow afternoon off, right?” Tiffany asked me Thursday morning on my way out the door to work.
“Yeah. Why? What do you have planned?” I asked her.
“None of your business. That’s why it’s called a surprise,” she shot back as she ran her hand over my ass and then rubbed me through the front of my slacks. “You still park in the garage at work, right?”
“Yes. Why?!?”
She pulled closer and whispered in my ear “Don’t. Worry. About it.” She then moaned lightly in my ear and I could feel my cock begin to stir under her touch. Clearly, I would be getting absolutely nothing done at work for the next day and a half, and she giggled knowing she had gotten in my head.
I probed for more details Thursday night, but this woman who wasn’t always great at keeping the surprise was suddenly throwing out confusing details and disinformation liked a trained CIA operative. However, I knew if she was working this hard to keep her secret, that it wasn’t just a romantic getaway at a B&B and had to be the swingers clubs we had so often fantasized about. I spent Friday morning fantasizing and daydreaming about all the naughty things we could get into, what it would be like to see my wife in a writhing, naked ball of humanity and enjoying every minute of it. The time finally came and I’m pretty sure my feet didn’t hit the ground between my office and the exit to the parking garage next door.
I crossed the parking garage towards my car and saw an attractive woman in business attire step out of a black Lincoln Navigator. She looked authoritative but sexy – hair pulled up in a bun, dressed in a black pencil skirt and a white blouse, black nylons and black heels. Her outfit accentuated her curves well without being over-the-top slutty and her glasses added to her air of authority and intelligence.
“Chris.” I thought I heard her call out. I’m not Chris, I thought to myself, but Chris is probably a lucky guy. I continued walking and wondered if maybe I’d see this hot woman – or someone like her - at the swingers club in a few short hours.
“Chrissy.” I heard her call out this time. I might have misunderstood her the first time. Hearing my sissy name called out loud made my heart jump a little but I knew absolutely no one outside of my wife and our few partners knew my secret so I was positive she wasn’t talking to me. I kept walking past her and nodded in an awkward why-are-you-looking-at-me-and-yelling-a-random-woman’s-name way.
“Chrissy!” she yelled and I looked at her over my shoulder. “Yeah, I’m talking to you, sissy.”
My head was swimming and my whole body froze as I heard the s-word. I slowly turned to face her.
“Um, my name’s Greg. I’m not sure who you’re looking for,” I tried to reason as the gears in my brain ground to a halt.
“No,” she said as she walked over to me, “your name is Chrissy, and even with your boy clothes on I can see you’re a little sissy bitch. Now get in the car. You’re wasting my time.”
I stood there looking back and forth between her and the black Navigator, not knowing what to do next. After what seemed like forever the sound of my text alert made me jump and I quickly grabbed my phone to check the message.
You should probably do what she tells you to, CHRISSY. It was from Tiffany. So this – whatever this was – was the surprise. And it appeared they had timed this very well.
I swallowed hard and cycled through all of the possible scenarios in my head.
“Shouldn’t I just follow you? If I leave my car here people will wonder why my car is still here,” I told her, still under the impression I had any say in the matter.
“It’s taken care of. Give me your keys and get in the fucking car. NOW.”
I handed over my keys and started toward the SUV. She followed close behind me and I saw her signal to the SUV out of the corner of my eye. A large muscle-bound man with a large tattoo on his forearm hopped out of the front passenger seat and she threw my keys to him. When I got closer, I could see the tattoo was a 1940s-style pin-up girl – a cute brunette winking back at me as she fell out of her underwear. He opened the rear door and ushered me inside, my new female “friend” climbing in behind me. I watched as the large man closed the door and then walked towards my car, got in, and drove off. I hoped my car insurance would cover him in case he got in an accident, but I was pretty sure I didn’t have random-stranger-involved-in-kidnapping-the-insured coverage. I sat in the middle in the back seat, another very large man seated to my left.
“Go,” the woman commanded the driver and the Navigator pulled out of the parking spot. Then she turned her attention to me. “Look at me.”
I turned towards her and folded my hands in my lap, feeling slightly claustrophobic between her and Cap’n Muscles to my left.
WHACK! When I had turned to her she hauled off and slapped me across the face. I was not expecting that at all, and my head reeled for a moment as I’m pretty sure I saw cartoon stars or birds.
“Don’t ever waste my time or keep me waiting again. Do you understand?” I nodded slightly and even though it didn’t really hurt, my eyes watered a little at the shock of it all. “My name is Sydney. You may call me Mistress Sydney, Mistress, or Ma’am. I understand you have a birthday coming up and this is your present. You will do what you are told to do, and you’re gonna fucking like it, right?”
I nodded again, looking deep into her eyes and seeing that it would be best if I did what I was told.
“I have talked extensively with your wife about what kind of things you like and what your limits are. You will not be given a choice about what happens to you, and there will be no safe words. I own every inch of you until Monday evening. You will be my little sissy bitch to play with as I see fit. If you are ok with that we’ll begin. If not you can get out and go home.”
“But my car is…” I started to sputter when WHACK! She slapped me across the face again.
“Yes or no, sissy?” I couldn’t tell if she was enjoying this or not, but she was certainly serious.
My eyes welled up a little more and I looked at the floor in case I would get another slap for starting to well up. The muscled man sitting next to me grabbed me roughly by the chin and forced me to look her in the eyes. “She’s talking to you,” he grunted.
“Yes,” was all I could muster.
“Yes what, whore?”
“Yes, Mistress Sydney.”
“Yes, Mistress Sydney, what, slut?” She teased.
“Yes, Mistress Sydney. I will be your little sissy bitch.”
“Beg me. Beg me to be my little sissy bitch and maybe I’ll allow it.”
My cheeks grew even redder as I was being humiliated by this dominant woman in front of both the driver and Cap’n Muscles. There was no salvaging any masculinity now and it was probably best to accept I had no control over my situation. My shoulders slumped and the man to my left let go of my chin.
“Please, Mistress Sydney, please, ma’am, please I want to be your little sissy bitch. Please?” My voice went up on the last “please” and I cringed at just how effeminate I sounded.
Sydney chuckled under her breath. “Of course you do. I knew you were going to be a compliant little sissy whore.” She turned towards the front of the SUV. “Did you get all of that, Tiffany?”
That’s when I heard my wife’s familiar giggle come over the speakers of the SUV. “Oh, yeah. Loud and clear. Happy birthday, and have fun, sweetie! Oh and hey – Sydney – try not to be too rough on my little sissy bitch. You break her you buy her!”
My wife, my new friend Sydney, the driver, and Cap’n Muscles all shared a good laugh and the driver ended the phone call. Holy fuck. Tiffany had heard everything. She had seen me dress up, and she had seen me suck cock, even watched while I got fucked once, but she had never heard me beg for it like that before. She wasn’t great at dominating me because she was never sure exactly how far to push me and it was something she wasn’t comfortable with. I respected that but she knew it was also something I enjoyed. If she couldn’t be the one to do it, at least she apparently liked it when someone else did.
“Well then, now that that’s out of the way, shall we begin?” Sydney purred at me, clearly relishing her role and relaxing into it. She reached into the seat back in front of her and produced a pink fuzzy collar with a little bell attached and a pink leash. Even though I was not resisting, the man to my left held my head with two hands as Sydney slipped the collar around my neck and fastened it. She attached the leash with an ominous CLINK and gave the leash a good tug – pulling me towards her – to make sure it was secure. The man to my left turned my head towards Sydney and she quickly applied bright red lipstick. I caught a glimpse of myself in the rearview mirror, still in my work clothes, with a hot pink fuzzy collar around my neck and bright red lipstick on my lips. I looked – in a word – ridiculous.
I only had a moment to contemplate how silly I looked when Sydney handed the leash to the man on my left and instructed “Be a dear and suck Roger’s cock, will you?” Before I could even begin to process that the man on my left, aka Cap’n Muscles, was named Roger, my neck was yanked down and I found myself staring at the head of his cock. (When had he pulled his cock out? Had his cock been out on display this whole time?)
I started timidly, licking slow circles around the head of his cock. He was only half hard so I was able to wrap my lips around him and get all of him into my mouth. He could tell I was having trouble with access so he unbuttoned his slacks and pulled them down with his boxers. I could feel him getting harder in my mouth and I could feel my own erection growing. Sydney reached into my lap and grabbed my erection, sighing when she did.
“Ah. Is sissy enjoying the cock in her mouth? Makes your clitty hard, doesn’t it?”
“Mmmhmm” was all I could mumble around Roger’s growing cock. As he grew harder I was having trouble fitting him in my mouth. He wasn’t massive but I was at a bad angle. I think Sydney must have sensed that and pushed me towards the floor. I complied and slid down onto the floor while Roger readjusted to give me a better angle. He grabbed the back of my head and pulled me off of his cock.
“Lick my balls, sissy. Put my balls in your slutty mouth.”
I did as I was told and began to tongue his ballsack. He was mostly shaved but I could feel the rough hairs on his scrotum scrape across my tongue. He jerked his cock and slapped it against my forehead.
“Look at me when you lick my nuts, whore. Look at me and let me know how bad you want my load.”
I was becoming lost in the moment and blurted out, “Yes sir. I want your load, please, please cum for me.”
My desperation elicited a chuckle from Roger and the driver. Roger pulled up on the leash and drove his cock back into my mouth, making me gag. He slipped my leash under his foot and used his foot to put tension on the leash, using it to make me bob up and down on his dick. The little bell on my collar was making an embarrassing jangling sound and I thought I heard the driver humming something, although I couldn’t place the tune.
“Jingle bells, jingle bells, jingle all the way, oh what fun it is to ride with a sissy that’s fucking gay!” the driver sang out and both he and Roger erupted in laughter.
“Dude,” Roger called out, “don’t make me laugh when I’m tryin’ to nut in this little bitch’s mouth. You’re fucking with my rhythm.”
Roger abandoned the leash altogether and grabbed the back of my head, pumping in and out of my mouth, occasionally bottoming out and pinching my nose closed until I struggled for air and my arms flailed helplessly. His grunts intensified and I could tell his orgasm was building. My eyes were watering from all of the gagging, and I realized I was moaning involuntarily.
“Ok, sissy,” Sydney spoke up, “he’s going to cum on your face and you’re going to let him. You’re gonna let him paint your face like the whore that you are. IF you understand me, moan like a little bitch.”
I moaned louder and shook my head up and down as best as I could. Roger tensed and held my head in place as he began to shoot his load. The first few blasts went down my throat but Roger quickly pulled out of my mouth and sprayed the rest of his seed on my face. I closed my eyes and stuck out my tongue getting splashed over my left eye and all over my tongue, chin, and cheeks. When he was done Roger rubbed his cock all over my face, smearing his cum everywhere and getting some into my mouth. For good measure he slapped his dick across my still-red cheek and then slipped it back in my mouth.
“Go ahead, sissy, clean off his cock,” Sydney told me as if she had just told me to unload the dishwasher. I licked the last bits of cum from Roger’s cock, licking up and down the full length of his softening cock and even giving his balls a little bit of attention.
“Wow,” said Roger, “when they go back to lick your balls again that’s when you KNOW they’re a complete whore.”
Roger and the driver laughed again but Sydney was all business.
“Thank Roger, sissy,” Sydney instructed me.
“Thank you, Roger,” I meekly blurted out, avoiding eye contact.
“No, really thank him, and look him in the eyes. Thank him for honoring you with his orgasm. He could have blown his load on a face much prettier and sexier than yours. Thank him for sharing his cum with you.”
My cheeks flushed red but I had a feeling hesitating was only going to make things worse. I turned to him and could feel even more masculinity oozing away as he looked down at me. “Thank you, Roger, for giving me your cum. It was an honor to pleasure you, sir. I hope I satisfied you.”
Roger burst out laughing again, and I got even redder, finally breaking eye contact when I thought that I might actually cry for real, and not just from being slapped or gagged.
“Now sissy, come sit next to me again.” Sydney patted the seat next to her and I did as I was told. “Look at yourself in the rearview mirror.”
I couldn’t quite bring myself to do it, so Sydney lifted my chin with her finger, holding it there so I could see myself in the rearview mirror. “You see that mess? Smeared lipstick, cum dripping from your chin and drying in your hair. Eyes welled up with tears. Take a long, hard look, sissy. That’s you. That’s the real you that you hide under boy clothes. That’s the real you that’s destined to be a fucktoy for real men. That’s the real you that’s just dying to get out. Well don’t worry, sweetie, Chrissy is going to get to come out this weekend. Just you wait.”
“Yes, Mistress Sydney.”
With that she ran her finger up through a glob of Roger’s jizz on my chin and slid her finger into my mouth. I sucked her finger into my mouth, eager to taste more of Roger’s seed. Eager to accept. Eager to slip further into Chrissy’s world. Eager to submit to this woman I had just met.
