Watching Pt. 02

Watching Part 2

After our adventure with Leo, Hailey and I didn't talk about it - well, not directly, she patted my bum and called me "cutie" once in a while. I also noticed that she left the sissy engagement ring that Leo had given me in the key dish by the front door where we would see it everyday.

One morning she was in the bathroom getting ready when I was overcome by her new slim beauty. At thirty-three she had never looked hotter in all the time I'd known her. Running my hands down her waist I told her how sexy she was. Naturally, we ended up having a hot n' heavy quickie. She rarely denied me, and often challenged me.

Afterwards she squeezed my love handles, "You know...we're not a match anymore. You should go on the same diet that worked for me."

She was right. While she was now perfect, I needed to lose some weight. I took her advice and after a month of eating only beef, butter, bacon, and eggs, I had lost ten pounds each week.

With my own new trimmed up body she suggested we go on a weekend trip to celebrate. She assured me she would plan it all. I only needed to hop in the car after returning home from work on Friday. I asked what the plan was and guessed we'd go somewhere warm with a beach to show off our new svelte bodies. I couldn't have been more wrong. Her only answer to my question was to smile wryly and say, "It'll be...a date. A real date, or should I say a pretend date. I guess I don't know which it'll be."

She was deliciously ambiguous and the anticipation coursed through my veins.

Friday, with a kiss, she asked me to load a suitcase in the car and at the last minute she ran back into the house to grab my engagement ring. When I asked about it she was coy, saying, "You never know when you might want to put it on. It's been so long since I've seen you wear it."

We drove to a little town in upstate New York. For such a small town it seemed quite cosmopolitan: being decorated in pride flags and a banner - "Welcome Faaaaabulous Crossplayers". Hailey was rubbing my cock while I was driving and I didn't stop to think much about our surroundings. She kept saying how hot she felt knowing her fantasy was coming true.

We got up early the next morning whereupon I discovered that she had packed me only girly undergarments and one change of my regular clothes. It was a first for me to wear frilly stuff under my clothes - but why not? We rushed out the door and to a salon, though I didn't think she needed any help getting prettier. Her hair and nails were perfect. The whole time she kept saying "I can barely wait to see you tonight." I was looking forward to our date too.

There were rows of women sitting under hair dryers or getting mani-pedis; tall, short, thin, fat, old and young. When she announced loudly at reception that, "He's here for a full femme make-over. Make him as passable as you can." My face burned in surprise and shame - to be outed so publicly. But Hailey merely pointed out the obvious fact I had missed: Red-faced and wanting to crawl under a rock, I followed her pointing finger only to see that all the other patrons were guys and they were ALL getting made up: the festival the town had announced in its welcoming banner was revealed to be a cross-dressing event with hundreds of sissy guys descending on the town this weekend to explore public outings.

My heart leaped and I was both thrilled and terrified. I came close to bolting for our hotel, but when my dear wife reminded me how we do things for each other because we love each other, I consented.

Hailey lounged nearby watching me getting dolled up. Hours later when they were finally done with me I totally looked like a middle aged woman. Even pretty for a woman my age. In fact, compared to the other guys in there I was slimmer and sexier.

Looking myself up and down in a mirror I saw the truth of it as Hailey gushed, "Darling, you totally look the part. No one could know." She squeezed my boobs and bum, "These look so real. And you've got a fantastic ass!" I stared, amazed at my own femininity. With the professional make-up, even my chin looked like a woman's. Hailey kissed my cheek, "I've never been prouder of you."

By now we'd been there half a day. Hailey took me by the hand, like girlfriends do, "Come on. Let's go get lunch and see who we can fool. I bet all the men will be checking out your ass. It's so much smaller than most of the lard butts walking around."

As we walked I judged everyone we passed. Was that woman in the spring jacket really a guy or did she just have thick ankles? A frumpy woman crossed the street in front of us and I whispered to Hailey, "She's a guy. Right?"

My secret wife returned my whisper, "Nope. And you're better looking." She pointed to a girl standing a head taller than the nearest real woman, "But she's totally a man." He was ghastly, but clearly enjoying strutting down the street oblivious to the looks people gave him.

Suddenly she stopped, "Look at the reflection in the window. That guy behind us is totally checking you out. It's making me hot to think how he wants to plunge his cock up your pussy. Little does he know..."

We crossed through a park in the town square when suddenly and impulsively she plopped us down on a park bench next to a gazebo. "Jackie..." she spoke loud enough for the guy on the next bench to hear her clearly, "...don't you ever want to do something naughty? Something my husband and your boyfriend can never know about?" Afraid to speak and give myself away I tugged at my skirt nervously, sitting as quietly as could be. She continued, "Here in this town where no one knows us, we could sow our wild oats one last time before you get married..." She fingered the diamond on my finger. "Let's give the first guy who propositions us a story to brag about forever." My eyes went wide as I noticed the man look up from his paper. Her eyes bore into mine and she kept speaking brazenly, "That's right, a blowjob! I bet this gazebo is private enough." I appraised the massive structure, nodding dumbly. She leaned close, "Do it for me, Jack. If you love me. Please. I wanna feel like he only wants you. Like I'm nothing to him and you're all that matters."

The next thing I knew he was standing right before us, "Excuse me ladies." That's right: he called us ladies. My heart just about thumped out of my chest. At first I assumed that everyone knew about the festival. But why would they? It was a busy bustling place with a population of a few thousand. "Are you two from out of town? He asked. "I could give you a tour."

Hailey lifted my hand, letting him take it, "You're so kind." She smiled at him mischievously. "We have a one o'clock reservation. What can we see in fifteen minutes?" She flirted, stroking his arm, "We're all yours." Then stopped herself, "She's all yours."

The unsuspecting predator was really our prey, and I forced myself into our new exciting ruse, wondering if I could follow through. My stomach was uneasy and I had a horrible case of cottonmouth as we headed toward the main part of the structure.

He patted my bum as I walked up the steps before him, "You're a foxy slut. I sure am lucky." Then as we moved to a secluded corner of the gazebo I felt so absolutely female. Somehow that word 'slut' was far more feminizing than being called a lady. As he said it I heard Hailey groan under her breath and I knew it turned her on.

Standing behind a podium she pushed on my shoulders and I stumbled forward, falling to my knees right before the expectant stranger who wasted no time in pulling out his hard ruddy dick and hanging balls. Wow! He was hard for me. I guess I really was foxy.

Hailey merely stood aside waiting while the man announced, "OK, girl, do your stuff. To Hailey he said, "You! Don't be worthless. Rub the spoo out of my balls for your friend. I'm gonna give your pretty friend all my cum and you can just wish it was you getting it." Did he really just call me 'the pretty friend'? Could he possibly think I was prettier than Hailey?

I knelt there not sure how to get started when he reached out to grab my head. Hailey virtually swatted his hands away, "Watch the hair! And we just did our makeup."

He tsked disparagingly, "You women and your hair. But, you're in a rush, aren't you?"

I took my cue and lifted his dick, pointing it at my face. With a shrug I plunged into my task while Hailey caressed the spooge from his balls. In between my painted lips it felt bigger than it looked. And being in control this time, I could feel every ridge and vein at my leisure. The flared crown, the slit on the tip, and the widening shaft, were all aspects of a cock I had failed to experience last time. Whereas this time I could run my tongue over every crevice and shape, exploring the soft textures.

It was strange to see my wife's hand on another man's equipment. Not that he knew she was my wife. Shy at first, she threw herself into it, massaging his nuts and coaxing his juice to seep out for me. And boy did it seep out. This guy had a steady stream of sweet precum constantly leaking onto whatever part of my mouth it happened to be nearest.

The slickness of his juice helped a lot because I was so nervous I couldn't quite produce saliva. In fact, I think most of the 'lube' I used to reduce the friction of cockskin on lipskin was precum.

I tried to go as deeply as possible but needed to gather juice to ease the way. After his cock was slippery from head to base I tried again. I got like four inches in me on my second go, but each attempt after that went deeper. Soon enough I was bouncing my forehead off his jelly belly. His round stomach got in my way, frustrating me that I had to tilt my head to suck as far down the shaft as I wanted.

When my lips finally touched his short pubes I felt pride. Then I bobbed repeatedly, proving over and over that I could do it.

The helmet was just touching the entrance to my throat which got me thinking about taking it further. Could I?

My new femmy fingers with a fancy polished called 'metallic cabernet', were lightly resting on his thighs to steady myself. I slipped both hands around to the back of his legs, feeling the smooth wool of his suit pants as I did. Then with firm pressure I pulled, driving the blunt end forward until it lodged slightly at the back. Steeling myself for what might be uncomfortable, I pushed my throat onto his cock and it worked. With a pop, it crept in maybe an inch, until his pubic bone against my lips would allow me to go no more.

It didn't hurt and I didn't gag. I was thinking how amazing I was. I bet he was thinking I was amazing too. I was also thinking about what I could do with a bigger cock. And lastly, as I was holding myself impaled there for a long moment, I was thinking how I couldn't breath and how I was glad he wasn't using his hands.

I pulled off, gasping for breath, with a generous dollop of pre-cum in my throat. Hailey was cheering me on, "Wow, Jackie, I had no idea you could do that."

I coughed slightly, "Neither did I." I had completely forgotten about my male voice, but since it came out as a choked off croak he didn't seem to notice.

He threw one arm around Hailey's shoulder and mauled her tits with the other. I was ready to stand up to beat the shit out of him for groping my wife, but she put him in his place with a well-timed painful squeeze of his nuts.

Re-focusing on the blowjob, his hips started thrusting erratically. I felt like I was done deepthroating him, but he had other ideas. It battered my esophagus, but fortunately it rarely thrust forward at the same time I bobbed down. Though it still made my eyes water.

My unnamed feeder brought his hand down to stroke his cock, accidentally beating my lips a few times in the process. With only the thick head in my mouth I felt his knees shake and knew he was close.

Hailey became frantic, yelling, "Not on her dress! And not the hair either. Or the face." It never occurred to me to worry about any place other than my mouth. And I wasn't completely sold on the notion of tasting and ingesting his cum.

His leaking increased in volume dramatically, making me wonder if I'd missed his orgasm. But when the real deal started there was no mistaking it. He swore like a truck driver, wanking fast into my mouth which I opened wide to receive his cum, even though I had definitely decided by now that I didn't want it. I only did it for Hailey.

She worked his nuts passionately, doing her best to bring him off fast. And when the first shot jetted out, hitting my chin, she used his balls like a lever to push his cock into my mouth, while rabidly yelling, yet again, "Not on the dress!"

Well, none got on my dress. And a whole bunch went in my mouth. I would've preferred the reverse. Leo's cum had been fine, and this guy's precum had been sweet, but his actual cum was thick and sticky and vile.

I bent forward, spitting the viscous slime on the floor, yet still at least half remained in my mouth, stuck to all the corners in stretchy strings of bleachy goo.

When he was done filling my mouth, he laughed while leering at Hailey, "You two should kiss now. It's the only way you married whores can get any fresh seed anyway."

I didn't want to expose her to his nasty white crap, but she tilted my face up and kissed me before I could stop her. We shared his messy cum, her passing it back to me, then sucking it from my mouth. She couldn't get enough, as if she wanted it to be gross, and that broke down my barriers.

Excited by her love of the degrading experience, I offered, "Let's smear it all over our faces while we kiss." But she reminded me that it would ruin our makeup.

Lost in her own excitement, Hailey continued frigging her cunt furiously, finally cumming with a series of high pitched grunts. Meanwhile my cock was bound and trapped deep between my legs, leaving me helpless to get any relief.

After it was all done, and he was gone, I felt used and dirty, which I guess is a more typical female response. But hiding my negative feelings for the sake of Hailey's fantasy, I simply smiled falsely saying, "Now that was a surprise!"

"That's nothing." She winked, "I've got something special planned for you, Sweetie. You're gonna be the center of attention and I'll just stay on the sidelines. But first, you've got racoon eyes, and we need to fix your makeup. If I had known we could just fix my makeup I would have wanted him to shoot it on my face instead of my mouth.

Acting playful and flirty, even as I felt more foreboding feelings, I replied to her earlier statement, "Really? And just what do you have planned. It couldn't be any wilder than what we just did."

"Wilder? I suppose not. But it'll definitely be more intensely intimate - and...real?"

She had me hooked, I craved seeing her so worked up, "OK, spill it."

"I'll tell you over lunch."

Thirty minutes later, sitting across the cafe table from me with a strong drink she let me know, "You're going on a date. A real date, or a pretend date, it depends, but it's with a real man. He's gonna take you out for a romantic dinner and dancing and treat you like a real woman." Suddenly there was a sparkle in her eye and her voice got all keyed up, "You're gonna be my hot wife while I watch everything!"

Sitting at that public table I felt kinda tingly inside, but scared too. "How? Who? Am I just gonna pick-up some guy? A random you-know-what in a gazebo is one thing but surely I'm not good enough looking for an actual date."

"Don't sell yourself short. You're better looking than half the real women in this town." I looked at the people near us to see if they overheard her declaring that I wasn't a real woman, but she just went on talking just as loudly and casually as she wanted, "Besides..." She fiddled with my ring, "You're engaged. Who do you think you'll be dating?"

"What? Leo's here? Where?"

"He gets in tonight. Plenty of time for us to get you a new outfit and primped for your first sissy date."

Back at our B & B I had butterflies and couldn't stop looking in the mirror, first with only doubt, and then with faltering growing confidence.

Finally, I thought I was ready, but Hailey insisted on more plucking. Next she ushered me into the bathroom for an enema. "Why?" I asked with pleading eyes.

But she silenced me, "You wouldn't deny your fiance his due? Would you?"

I stammered under my breath, "I guess not."

My dearest wife had me practice walking, and sitting, and talking without sounding too much like a man. It was a crash course but she said I'd do fine.

At the appointed time there was a knock on the door. I was filled with trepidation and I worried I was gonna toss my cookies. She motioned for me to go answer the door and at the last minute added, "Honey. One more little thing. Could you really enjoy yourself? Give in to pleasure so I can see you really enjoying your man and the cock I could never give you."

I nodded, thinking I would do my best, but not at all sure I could actually follow through with how inhibited I was feeling now that the moment was here.

She patted my bum, propelling me toward the door, "And one more thing. I want to feel like he's a better lover than me. I mean, he's got an actual cock and all I have is this little clit. When you're doing it with him, will you tell me how much better his cock is?"

As the door cracked open Leo charged in all manly and in control. He glanced at Hailey briefly then turned all his attention to me, "My, my, what have we here? You look ravishing!" He grabbed me dominantly, pulling my body against his. With one hand cupping my ass and his face buried in my neck he whispered, "And a ravishing is what you deserve."

I felt sure he was going to drag me over to the bed right then to have his way with me, instead he took a little high-waisted jacket from Hailey, and draping it over my shoulders led me out into the night.

The restaurant was dimly lit and crowded. I looked around nervously wondering which of the couples might include a guy like me: a 'sissy' as Hailey had labeled me. And to tell you the truth, dressed as I was, and knowing what fate had in store for me, I felt the part.

I thought two of the 'ladies' in the place might have penises constrained back between their legs. Searching for an Adam's Apple I confirmed that at least one did. She was way hotter than me. For a second, I wanted to be the guy on a date with the glamorous beauty. To be the guy who would get to bed her. I wondered if he knew she had a dick. But then I heard Leo's charming voice, "Let me top off that glass for you. Any girl as pretty as you deserves to be treated like a princess." I lost all thoughts of any other couples.

We had a delightful meal and Leo was a perfect gentleman. My mind even drifted to thoughts of what kind of husband he would be. Would he dote on me? Bring me flowers? If he did I would need to show my gratitude.

Would he be a good protector? Would he bring home a big paycheck like I did for Hailey?

Hailey! I scanned the room quickly and found her alone at an out of the way table by the kitchen watching us. She smiled gleefully at me, sipping her wine.

After dinner Leo brought me to a small bar. The place was packed but he took me by the hand and led me through the crowd to a table that was amazingly available just in time.

We drank and laughed too much, all in sight of Hailey, who found a spot at the bar where she fended off the advances of desperate men so she could watch Leo make his moves on me.

On the dance floor his hands groped my body lasciviously while I ground my derriere back into his hard package. I completely forgot about Hailey until I saw her coupled with some guy right next to us. Leo pantomimed an obscene gesture, indicating what he had planned for me, and she winked at him in manifest approval. Her dance partner only had eyes for her, but I knew she would leave him high and dry.