The Rendezvous Pt1 (Sissy Story by CassidyCaine)

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The Rendezvous Pt1 (Sissy Story by CassidyCaine)
Nick looked at the email he d received from his wife at lunch again as he got ready to leave work. It had been a month since he d confessed to her his love of dressing up in women s clothing after he d kept it hidden since they first met. But, Nikki was insistent so he had tried to share that part of him. She had worried he was gay or didn t want her anymore but he d assured her that wasn t the case. Yet after all that worry, she had emailed him to tell him that tonight she wanted to play with his fantasy and role play a little to see if she could get into it. She had rented a motel room and would have her naughty maid outfit he d gotten for her and he would be the bad crossdressing guest who catches her stealing things.

It wasn t really one of his fantasies, he wanted her to be the dominant one, but it was an acceptance he d not expected. The note had said to get completely dressed up and meet her in room 207 so as soon as work was done he was out the door. Traffic was too heavy with all the nervous energy in his system with so much to do to get ready. It would be the first time he went out in public and the first time his wife had seen him dressed up which only ramped up his anxiety.

Traffic finally lightened as he got into the suburban streets near his house, finally pulling into the driveway of their little two story home that was a clone copy of the rest in the development. He drove into the garage and shut the door behind him so he could secretly slip out fully dressed later. Quickly running into the house, he made a straight line for the upstairs bedroom. Opening the closet, he pulled out the plastic bins that held his secret treasures of feminine wear he d been collecting over the years. Agonizing over the limited choices, Nick set out what he thought would be good for tonight as he stripped off his men s clothing.

His slight form gave him an advantage in the looks department but he had to put in a lot of work to get things right. In the shower, he lathered himself good in his wife s flowery products and rinsed off before applying the shaving cream. Thankfully, he wasn t a hairy man but he carefully shaved his legs, underarm and face so he was baby smooth. Next came the moisturizers before moving on to the make-up, a process he d been perfecting for years when he could. He liked to go with a more earthy tone consisting of a lot of beige and reds with just a little green in the eyeshadow. Then he pinned his hair back and slipped on a blonde bob wig, amazed at how much different he looked in the mirror.

He could already feel Nikki coming out as he walked back to the bedroom. First he slipped on a pair of lavender panties and a matching bra with breast forms built into them, carefully tucking his privates back as he d not been able to pick up a gaff. Next, he clipped on a garter belt and rolled a pair of black nylons up his legs, attaching them to the belt. Then, he pulled on a silky white blouse and tucked it into a black skirt that fell to his knees before he slid on a matching jacket. The last touch was the calf high leather boots with chunky four inch heels he d picked up on a discount rack.

Double checking himself in the mirror, he took a deep breath as he considered the next part of things. Grabbing his only purse, he put in a touch up make-up kit in it along with some other odds and ends he thought he might need. Carefully negotiating the steps, he went downstairs and slipped into the car to sit a moment as he gathered up courage.

The car started up and butterflies exploded in his belly as the garage door opened. Backing out, he quickly drove out of the housing complex as fast as he could while avoiding looking at anyone on the sidewalks. He had to keep reminding himself to keep the speed under the limit as he rode to the motel, not wanting to keep his wife waiting but not wanting to get pulled over and have to explain his dress. He was thankful the place wasn t far and he was pulling into the motel parking lot before his anxiety overflowed his senses.

Looking over the numbers on the rooms, he pulled into a spot near the stairs to the second floor and killed the engine. He glanced around the place now lit only with fluorescent lights as the sun had set, giving him some shadows so he didn t feel like he stuck out. Once he was sure the way was clear, he got out of his car and headed upstairs to 207.

Pausing at the door, he realized he d have to knock and hoped it wouldn t spoil the fantasy for her. Nick knocked lightly and peered down the balcony with a surge of paranoia. The door opened and his worst fears were realized as a man stood there smirking at him making him look over at the room number quickly. I m sorry, wrong room, he stammered. His mind told him to run but his legs were frozen in place with fear.

Get in here Nikki, the man growled. As he did, he reached out and wrapped his fingers around Nick s upper arm, yanking him into the room. The door slammed shut behind him before a flash blinded him followed by an electronic click. When his vision cleared, the man stood between him and the door. He wore black dress slacks and a well fitted dress shirt with messy black hair. His tanned skin added to the sharp, angular features of his face so his raised cheek bones looked dangerous.

Confusion played over Nick s face as he remembered he had called him by the feminine name only one other person knew about. Who… who are you?

I m hurt, Nikki. You don t remember me. A bright smile was on his face as his eyes roved over the female dressed man. I m Wyatt, I work with your wife.

Jack s eyes widened even as the confusion remained, not understanding why he was here. Did my wife send you?

In a manner of speaking, yes. Please sit down on the bed and I ll explain. He looked pleasantly at Nick for a moment while he waited for him to sit down but his face grew darker as the man just stood there. Sit down!

As if on autopilot, Nick sat down on the bed when he spoke with such authority.

Good, Wyatt said, walking to stand in front of him. You re wife confided in me your proclivity afraid you were gay. I told her I d take you out for a manly night to butch you up and get you over this silliness. I m afraid she s a bit submissive herself and just doesn t get this but I do. He reached a hand out and placed a finger under his chin to lift Nick s gaze to his. You re a little sissy who craves daddies cock but you can t admit it.

No, Nick exclaimed. His cheeks turned a bright crimson as he shook his head. It s not like that, I m not gay. Now get out of my way, I m going home.

The slap across his face shocked him and he let out a girlish cry as tears brimmed in his eyes. Did I say you were gay? You re a sissy hitch and a good sissy always craves cock. Now, you are going to wise up and do as I say or I m going to send your dressed up pick to your wife telling her you came to me begging to suck my cock after I picked you up.

But, she wouldn t…

Please, she already doubts your sexuality. And she expected me to be picking you up at your house. Sadly, you wife is poor about writing her password down so I just logged on into her computer and sent you that email before deleting it.

He stared up at the man in shock realizing he d been set up and couldn t figure a way out. He knew his wife would believe it after how she had freaked out about his confession. What do you want?

To give you what your sissy heart has always desired. He stepped close to Nick and grabbed his arms pulling them behind his back. Trying to cooperate, he heard the jingling of the metal cuffs too late they were clicking shut around his wrists so all he could do was struggle against the steel. Be good about things and you ll find this night to be very pleasant. Fight against your nature and you ll regret it.

I don t know what… His words were cut off as Wyatt suddenly flipped him around with surprising strength and speed so he was face down on the bed. Nick felt the dress he was wearing being pulled up over his ass to bunch you around his waist. A yelp escaped him when a large hand swatted first his right ass cheek hard and then his left cheek leaving burning imprints on his panty clad rear end. Tears welled up in his eyes at the rough treatment even as he denied feeling any thrill at the spankings.

This is a night for Nikki. And Nikki doesn t sound like that, does she.

Nick turned his head so he could see his tormentor and stare at him in stunned amazement. He d not told his wife about the specifics of dressing up like Nikki, about the feminine demeanor he put on, including speaking in a softer, higher pitched voice. No, he said, in a soft, sultry voice.

Good, Wyatt said. His hands slowly pulled me up and around so I was setting at the edge of the bed with him leering over me. Reaching down, he slowly unzipped his trousers and reached into them to fish out a large cock with a bright red head, the tip glistening as it hung half erect in the air.

Nick started at the man s erection for a moment, realizing it was the first other cock he d seen this close. Watching porn didn t really count compared to seeing a hot, excited dick in the flesh. It was interesting to note how different Wyatt s was compared to his own, where his was smooth and average, his was thick and veiny with a shaft that seemed to get bigger as it moved from the base up to the large helmet, or perhaps it was because of the curve it looked that way. It was when he heard the slight snicker that he realized he d been staring at the man, looking up into Wyatt s eyes.

It s ok, I know you ve waited for this moment for a long time, take it in. Then open those pretty lips for me.

I m… I m not going to…

He didn t slap me with his hand like Nick expected, cringing waiting for it, but instead cupped his chin and pulled his gaze back to him. Nikki has been wanting this for a long time. Now, remember what I said about doing good and what happens if you don t.

Taking a deep breath, Nick steeled himself knowing he had to do this for his marriage or say goodbye to the last few years of his life. He let his glossy red lips part until his jaw hurt and pressed his tongue against the bottom of his mouth as he gazed at the monstrosity before him. He watched the man grip his cock by the shaft, an inch or two down from the head, and shuffle forward so his bulbous head rested on Nick s tongue.

The first thing he tasted was the sharp, sweet taste of the precum coating the head and leaking out. It wasn t as disgusting as he had thought, it was actually a bit nicer than his wife s juices. Realizing he was expected to perform, he swirled his tongue around the head, tasting more of the juices, and feeling the rough texture of the helmet. A small moan brought his gaze up to Wyatt and he felt a fleeting moment of accomplishment at having provoked such a response but quickly berated himself for such thinking. He was being forced to do this.

Rubbing the flat of his tongue up against the glans of the cut cock, he sealed his lips around the rim of its head so they pressed tight along the shaft. Sucking gently, he moved his head down the shaft an inch or two before pulling back up. He could hear Wyatt breathing harder as he sucked harder on his cock, feeling his saliva coating the cock in his mouth. Nick kept pushing a little farther down the shaft as his tongue pressed up along the underside, his cheeks hallowing out as his head bobbed back and forth faster. He tried to remember what he liked in a blowjob though he had to remember before his wife as she didn t care to do such a thing.

Soon, his sucking brought the head of the man s cock near the back of his throat, leaving several inches he couldn t do anything to with his hands behind his back. He kept sucking up and down as the shaft grew wetter. Just as he started to slide back down, he felt a hand on the back of his head and Wyatt thrust forward until his cock head was wedged in the back of Nick s throat, cutting off hair. He held him there as his lips opened and closed around the shaft, trying to get air and failing.

Finally, the man pulled back letting Nick suck in a lung full of air, tendrils of saliva clinging from his painted lips to the cock. Tilt your head back a little and stick your tongue out, keeping it down, act like you are going to yawn. I know you want the whole thing in you, Nikki. To be a great cock sucker. You can do it. You want to do it.

He didn t give me a chance to reply as he slid his cock back into Nick s gasping lips though didn t shove too deep. He tried to do as he said as his cock got towards the back of my throat, tilting his head back and sliding his tongue out like a ramp for the man s shaft, moving like he was going to yawn. His jaw was aching as he felt Wyatt press deeper into him then he had, the gag reflex taking hold. He held him there until it subsided and then pulled back out to leave the head in his mouth. After a breath, he pushed back in deeper again and held himself there.

Wyatt continued to do this again and again as Nick desperately tried to breathe and please him at the same time. He slurped at the cock coated in spit from the deepthroat attempts, just wanting the man to cum and get over it. After a few times, he suddenly felt the brush of fabric against his nose and realized he was sliding deep into my throat and he wasn t gagging. Through all of this, he could feel my own erection raging in his panties, shifting on the bed so the man wouldn t see it. It was embarrassing to think deep down, he, or Nikki, was getting excited by this.

You re a natural cock sucker, Wyatt said, driving himself deep into his throat. His hands suddenly left Nick, letting him pull back enough to look up at the man with teary eyes, seeing he expected him to continue. Taking a deep breath, Nick drove him lips down the length of the man and pressed on until he felt the head passing down his throat. He continued with the deep throating without any more prompting as he felt some satisfaction in accomplishing something many women wouldn t do. Over the slurping of the cock, he could hear the man moaning with each stroke, his scent filling the crossdresser s senses.

As he worked his lips up and down the man s cock, he could hear him growing more excited, feel the urgency as his hips rocked the shaft into him. Soon, he heard the man cry out as he was deep in his throat, feeling the cock pulse and grow larger. Nick started to pull back but the first shot went straight down his throat, making him choke. He moved to pull his head back but hands held him so cum spurted across his tongue and he was forced to swallow. The first taste of the warm semen was strange, not exactly repulsive with its creamy, salty-sweet texture but wrong in every way. The cock kept spurting into his mouth as he sealed his lips around the head so it didn t dribble down onto his blouse, lathering his head over the top as the blast grew lesser.

After a few moments, the man seemed to have stopped so Nick swallowed what was left in his mouth before lapping his tongue over the head. Once he was sure it was clean and wouldn t drip, he pulled his head back, letting the erection drop from his lips. It felt like the semen was still coating every inch of his mouth and throat as he sat there on the bed. He felt completely humiliated having to suck on another man s cock just because he liked dressing up in female clothing, being used like a whore.

You did good, Wyatt said, provoking a dirty look from Nick. Oh, what, is the little sissy sad because he got all worked up sucking cock like a good slut and doesn t get relief.

I didn t get…

Before he could finish his sentence, Wyatt shoved him back onto the bed, pinning his handcuffed arms behind his back. He wiggled helplessly as the man pulled his disheveled skirt up and yanked down his panties to reveal the hard-on there, sticking straight up in the air. You liked being a little cocksucking sissy, Nikki. Look, your body even knows this is what it wants. So stop pretending.

Nick just lay there fighting back the tears and not understanding why he could like this, why this turned him on. He had pleased a man and he d liked it. Nikki had gotten to shine. But, he wasn t gay. He loved his wife. This couldn t be happening.

Wyatt suddenly moved away from him and towards the bathroom area in the back, plucking something off the sink counter. Nick saw the red light then before the rest of it coming into view. It was a video camera and he could only assume it had recorded him sucking cock and swallowing a load while getting hard because of it. Edited right, it would probably look completely willing.

That s right, Wyatt started, putting the camera into a backpack. Your ass is mine. So you had better be a good girl, Nikki, and make Daddy happy.

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