Watching Pt. 02

Later, back at our hotel lobby, I was tipsy, and Hailey was wasted. Leo had drunk more than me but didn't seem fazed. On the way to our room, down at the end of the hall, I noticed a girl kneeling in front of her date delivering what appeared to be a fantastic public blowjob. I suspected she was a sissy like me. 'like me', what an odd thought to have.

Leo carried me across the threshold with Hailey trailing behind. Then unceremoniously dumping my body on the bed, he said gruffly, "Be right back."

Meanwhile Hailey was the epitome of lighthearted mirth. She lit candles and sprinkled rose petals on the bed, while my man drained his main vein oblivious to the rude sounds coming out of the open bathroom door. The loud stream just reminded me of how strong and masculine he was.

When it was my turn to freshen up, Hailey helped me redo my makeup, we giggled like teen girls at prom. I had to pee too, but like Hailey I had to do it sitting down with the way my member was strapped back between my legs.

When we finally emerged, Leo was reclining naked in the bed, his hands behind his head like a man who was in total control. The sheet covered him from the waist down giving me a yearning to see his meat once again, if only to admire it.

He looked at Hailey dismissively, then pointed to a chair with his eyes. To me he said, "Come here lover. It's been too long."

I felt conflicted. My wife is my lover and she was right there. Sure, I had sex with him once, and he coerced me into being his pretend fiance. But to be his lover implied a level of intimacy I wasn't comfortable with. I looked to Hailey - she had said this weekend was going to be an intimate weekend. Was this what she meant? Had she known I would feel this way?

Her eyes were glazed over and she was way past the point where she teased herself with the vibrator - it was already drilling into her cunt with its second appendage tapping her clit. She was watching me, but she wasn't responding to my unspoken question. I followed her gaze and saw that she was studying the lecherous way Leo appraised me.

He grabbed my wrist, and when he jerked I flew forward landing on the bed next to him. Leo ran his hands over my body possessively, feeling me all over. He spent a lot of time on my breasts appreciating their jiggly realisticness. He kneaded my ass, and secreting his hand down the back of my panties found my cockhead, which he teased with one finger. It wasn't the only thing he teased back there.

As he explored, he gradually removed items of my clothing until I was left only in my corset, garter, panties, and stockings. Hailey had put me in a white lacy bridal set which I posed to show off. Now when he caressed me his hands touched bare flesh as often as lingerie covered flesh. The steady hum of Hailey's vibrator continued the whole time.

He rolled me onto my tummy and straddling my legs peeled down my panties slowly. I now understood why Hailey had put them on over my garter. I thought surely I was about to lose my virginity.

He had this bottle of lube with a pointy applicator tip which he inserted into my nervous asshole before giving it a generous squeeze. The gel was cold and gooey as it made its way up my rectum, preparing me for my first cock.

Leo lay on top of me, gently rubbing his cock between my buns, getting everything slick from the leaking lube. He grabbed both my wrists holding them tight. I wasn't planning on fighting him, but if I did, he had me pinned.

I heard Hailey's vibrator switch to a higher speed as she asked, "Is it in him? Is he your bitch yet?" Leo just kept frotting my bum, ignoring her.

After a while of tenuous anticipation, he flipped me over onto my back again. Leo played with my cock and balls for a bit, telling me how much he liked them. I hoped he would blow me. Not just because it feels good but also to delay what they had planned for me.

And if he blew me, maybe they would forgo the fucking so he could stuff my mouth like last time. It would even be hot if he straddled my chest, kneeling on my immobilized arms, since restraining me is apparently a thing he likes. Apparently, I get off on it too.

But I didn't get to taste his cock. Without warning Leo suddenly grabbed both my ankles, hoisting them up onto his shoulders. My nylon clad legs were pushed back against my realistic boobs, exposing my helpless hole to his menacing beam.

I held my breath as my "fiance" lined up to break my imaginary hymen. I wondered if it would hurt when he broke my cherry. Then at the last moment he unexpectedly said, "Hailey, put me in."

The vibrator clicked off, then she approached tentatively. Her hand hesitated as she reached for Leo's glistening dick. Then down below my line of sight I heard her gasp as she made contact. Leo's steel eyes bore into mine: his intent to fuck me never wavering.

I felt the blunt end touch my bung, knowing it was my wife who was pressing it there. As more and more pressure built up I looked away from Leo to gauge her feelings. She looked scared but captivated, now using her fingers to try to force the head to go where it didn't quite fit. A tiny bead of perspiration trickled down her temple from the intense emotional effort in which she was engaged.

I was compelled to drive the situation forward, "Do it Hailey! Fuck my sissy pussy with his cock." Then I added, "His cock which is so much better at fucking than any of your miniscule equipment."

That moment felt like the right time to really give her what she wanted, "Hailey, he's got such a wonderful cock. So big, not like that little thing you've got. In fact, you could never fuck me like Leo's about to. You should just put a real man's cock in me, then watch how a real man treats his woman."

She looked instantly hurt. Then she smiled, captured by her lust to watch me being taken.

The big head popped in and it was my turn to gasp. My whole body tensed and froze from the excruciatingly painful intrusion. Leo took control, "Give it a minute. It'll be alright." To Hailey he said, "Don't let go. I want you to be responsible for this. You are the force behind everything aren't you?"

Her face changed as she realized he was right. If she had thought we were a couple exploring some mutual kinks she now fully saw that it was her compulsions behind it all.

Leo put some weight behind the shaft that was entering my last innocent refuge as Hailey guided it home. The pain was gone now, replaced by a burning stretch as my sphincter was deformed and expanded from the tumescent invader.

Deeper it went, filling me with a bloated sensation, until finally he crushed her tiny hand between my ass and his body, forcing her to let go. Her assignment finished, she returned to her chair, again merely a watcher.

Leo took a few slow gentle strokes, but increased his speed gradually and continually until he was pounding my sissy hole hard. It was uncomfortable for a while, but gave way to the thrill of being abused for my wife.

His organ hit my prostate, causing precum to ooze from my dick, but it didn't feel like it would give me an orgasm and it didn't feel intrinsically special.

I had surrendered to them and it felt good to be a receptacle for their indecent desires. In my mind's buildup I was going to be hard as a rock at this moment, but in reality my penis flopped back and forth impotently with each of Leo's vicious jabs.

I took the moment to push Hailey's buttons, lying I said, "Oh baby, it feels amazing how his big cock is plowing into me. It's hitting all the places you never could."

I may have been playing a role, concerned about what Hailey was feeling. But Leo played no such games.

I had little choice but to study his face during the assault and what I saw there was a pure self-centered concern for his own hedonistic pleasure. He attacked my ass with a fervent lustful passion, grinding and building to his orgasm and leaving Hailey and I to be observers of the wicked event.

When he came, he drove as far as he could, holding himself deep within me, throbbing and shooting pulses of goo into my being. Then with a heavy grunt he was done.

Leo pulled out, leaving me empty both physically and spiritually. We were nothing to him. He'd had his fun and I was a mere recepticle. And while I felt a sick satisfaction in being a cum-dump, the relationship lacked meaning.

When he withdrew I felt his spooge leak out of my gaped and sore hole, soiling the sheets with a filthy mixture of lube and cum and you-know-what.

I breathed a sigh of relief. My anal ordeal was done and I'd survived.

Leo removed my legs from his shoulders but kept holding me by my ankles so my gooey hole was still visible to them. He turned maliciously to Hailey, "Clean the sissy's pussy."

Her jaw dropped. "Come on, wifey. You've been sitting there doing little more than humming yourself. Get over here and soothe your femmy hubbies hole."

She reached for her underwear, approaching my displayed sexual opening as if to wipe me clean. "Not like that." He barked. Do it the right way. With your mouth."

I was sure she would refuse as I beheld a look of disgust she wasn't quite able to hide, even as she lowered her face to my backside I waited for some objection. Instead she stared at it and said, "I guess my fantasy was to be a cuckette and this will definitely do the trick."

When her tongue touched my asshole I forgot all about her aversion and twisted admission. The sensation of a hot wet tongue on my battered fanny was out of this world.

I couldn't help but moan. Hailey couldn't help but make tiny mewling sounds of revulsion. And Leo laughed, pushing her face deeper into my sloppy pussy, "You brought this on yourself, Hailey. Clean the sissy's anal creampie real good. Make her feel good for all she's done for you."

My forgotten and flaccid cock returned to life, grazing her forehead as it stood up straight and hard. Leo placed her hand on my dick, moving it up and down until she took over wanking me. He told her, "When it stops gushing cum you can lick her trannystick until she's had her reward." She ate me with a passion I didn't understand as she lay on her fingers, grinding her tiny clit hard on them in an attempt at yet another orgasm.

In time she moved to my ballsack, thanking it for all the time it had spent tucked back uncomfortably between my legs. Next she moved to my shaft licking up and down with a shame-fueled appetite I'd never witnessed before.

Lastly, she attacked my cockhead, devouring it and jabbing the opening to her throat. When I was close to cumming she rolled us over so I was on top, pleading, "Fuck my throat like he did to yours that first time."

I had wanted to fuck her throat like that, but was afraid to hurt her. At this moment I didn't care and apparently neither did she. I treated her mouth like a cunt, thrusting and jamming my cock down her gullet. Obscene choking noises filled the room while I face fucked my darling's prone body for the first time.

Leo was behind me, watching my slick brown winker clench as I pistoned, "Go on Jackie, call her a bitch. She wants you to. Do it!"

I couldn't hold out long at all and was glad she never tapped out. I came in a rush of jiz that she never tasted. Grunting and succumbing to his urging I voiced his nasty suggestion, "Bitch. Bitch. Take it all."

When Leo left and we were alone I felt ashamed at the things I had done. She must've too as she couldn't look me in the eye.

I spooned her and she spooned me back, falling asleep, cradling each other all night.

On the drive home we held hands the whole way, never letting go. We had experienced and shared her fantasy and if this is what it took to be closer to her I'd keep being her sissy. I'd keep letting Leo, or even other guys blow their loads in my mouth or sodomize my ass. Because I love her.

Eventually, as f reading my mind,she broke the silence, "Do you love me?" I squeezed her hand in reply.

"No, do you really love me? Enough to do anything?"

I feared the worst. Would she want me to dress like a woman all the time? Would she want me to get my dick cut off? "Yes, I love you more than anything."

She went on, explaining herself, "I thought that's what I wanted. To watch you with another man while I was discarded as a useless dickless cuckolded wife. But when it really happened, mostly I felt left out. I was hardly part of the action... I'd even lost control to Leo."

She watched my eyes. "Go on..." I told her.

"Well, I heard this word. It's 'femdom'. Have you heard of it?"

Author's note:

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