Watching

Then quite unexpectedly Leo pressed his cockhead at the juncture of my lips, forcing the tip to enter me. I felt it brush against the front of my teeth, knowing I was mere moments away from fully sucking cock. Any thought I had of not doing it dissipated with my chances of escaping.

From above me Leo said, "You're looking very sexy with your lips on me." Then turning to Hailey he asked her, "Don't you think she looks hot?"

I could hear the lust in her tone, "Never sexier. Your position reminds me of a flick we saw where this guy made love to a girl's hot lips while pinning her arms to the bed."

I remembered the movie too because after we watched it Hailey let me pin her down with her arms above her head just like in the video, except that we did missionary. Did she remember refusing me oral, saying it was 'degrading' that way?

Leo responded casually, again like I wasn't a part of the discussion, "Sure, give me a sec."

He grabbed my wrists with improvised violence and pushed down on them with his weight, holding them outstretched far above my head. I don't know if he was speaking to me next, or Hailey, but he asked, "Ready, baby?"

He didn't wait for an answer and in the new position his dick was angled better to plunge in - just not deeply.

Staring at his abdomen and shaft I saw like four inches plow into me. Hailey would've watched the same four inches enter me too. It filled my suddenly less manly mouth, flattening my tongue. He made it seem so easy, I was impressed with his prowess.

Holding still for some time in this sexual push-up stance I could feel his heartbeat through his manhood. Hailey, who orgasms easily with her vibe, had her first of the night, mewling slightly.

Leo noticed, and consulting with Hailey, said, "You like? I can keep doing this for a while."

And he did. I lay there helpless as he repeatedly pushed and pulled his wetted penile shaft in and out of my mouth. It wasn't bad. He didn't jam it down my throat. It didn't hurt. I was able to keep my teeth out of the way. If he came now and we were finished, I could be satisfied that I was open minded and had had the experience even as it stripped some of my machismo away.

I felt his dick twitch a couple times then he held completely still, edging himself in my mouth. Wide eyed, I grasped the sheets again waiting for the flood that never came.

Hailey asked disappointedly, "Oh, did you cum already?"

To which he replied, "Don't you worry yourself. I can go for a long time.

She squealed in delight as my heart sank. Then she said, "Leo, buddy, I think your lover's ready for something new, there's no excitement down there. She was right of course, my dick had shriveled up.

Leo's look pierced my eyes, "I think something new is exactly what we need."

I too was thinking that I could be ready for something new, especially if it sped the night along. A simple swap would be great.

Letting go of my wrists he sat back on my chest with his balls on my chin and his dick still partly in my mouth, bent down as it were. He just held it in there, plugging me up.

Then he turned to Hailey again, "I'm not exactly gay you know. What I really like is to make love to crossdressers. Virgins are best. Married virgins are better. And straight married crossdressers are the best of all. Are you and Jackie game?"

She sounded both thrilled and frustrated, "Of course we are. But none of my stuff will fit her."

Leo directed Hailey to find his keys, telling her that all we needed was in his trunk. She jumped up faster than a cat after a mouse, rushing out to get the box.

Meanwhile with a slow gently rocking motion Leo see-sawed the head of his dick in and out of my mouth, making it difficult for me to raise any objections, not that I knew what I would say besides a feeble, 'I don't want to.' Clearly my wanting or not wanting something was irrelevant.

When she returned Hailey dumped the contents of the box in the chair she had so recently occupied and started rummaging through the feminine stuff.

I couldn't really turn my head to see but soon enough I felt her rolling stockings up my legs. When she tugged the tops of the thigh-highs in place she patted my flaccid penis, "Buddy," she said to Leo, "your lover needs a change of pace again."

Happy to oblige, he lifted up, removing his dickhead from my mouth, only settle down again, stuffing his wrinkly balls in there.

I saw Hailey peering at my humiliation over his shoulder, "Huh, I didn't know that was a thing. How creative. We should probably have you over more often to show us new stuff." The thought filled me with dread.

She found a lacy thong in the pile which she proceeded to put on me. As she was lifting my legs, Leo responded to her thought on creativity, "That's nothing. Watch this!" Saying so he gyrated his crotch on my face, making sure his balls really moved around in my mouth, but which also caused his cock to spin in a circle, batting my face with it every time it went around.

Back at the pile in a flash, Hailey was talking to herself, "We don't really need a garter...but we'll use this padded bra, and of course, a wig." From the sound of her voice I knew she was looking my way, "Do you want vivacious red hair or innocent blonde?"

With my mouth still stuffed with cum laden balls, Leo tapped his cock on my nose, "Come on Jackie, it's rude not to answer a sister."

Having surrendered long ago I did my best, mumbling, "I'll take the blonde one."

There was no way my words were intelligible and Hailey answered me, "Ok, if you want the red one, then you can have it. I love that you're feeling so adventurous."

I'd lost the will to resist or even take part in directing my fate. The two of them sat me up on the edge of the bed again while Leo finished dressing me and Hailey applied makeup. I pretended to like it.

Satisfied with their work they sat on the bed in my place and had me walk around, pose, and play with my soft penis in a useless attempt to get it hard.

Finally, exasperated, Hailey said, "It worked before when you watched Leo bounce for you. Stand here in front of our buddy."

She got off the bed and came around behind me. Leo commenced bouncing his cock again, then reaching around me Hailey fondled my dick and balls.

Her hands were comforting, warm, and soft. The female touch really helped.

Guiding me to my knees she said, "Get a closer look. A nice cock like Leo's always looks better from up close."

The touch of her hands and the feel of her body against my back did the trick and my dick rose to attention again. She shrieked joyously, "Oh goodie. You just needed to be closer to such a magnificent tool."

After all the parading around I'd lost any shame I had: they had touched my previously untouched anus, put his cock and balls in my mouth, beat me with it, and dressed me up like a girl. I had nothing more to lose.

I glanced at Hailey as she whispered in my ear, "Leo deep-throated you. It's only fair...". When I looked back, he was holding his cock, pointing it straight at me.

He said, "This is my favorite part. I'm going to break you now. Though I have to say, I've never done it when the wife was present before." I had thought I was already broken. Was he planning to fuck my throat? Would he be violent?

He took my head in his hands, so I braced myself for him to force my mouth down on his cock. But his hands were surprisingly gentle.

Lifting my chin slightly he spoke softly, "Jackie, baby, look me in the eyes." I looked up from his menacing cock, right into what I discovered were baby blue eyes.

Next he leaned forward and kissed my forehead, "You're the prettyest sissy I've ever made. You've got beautiful sexy lips and an ass to die for." When he complimented my butt he reached around and gave my cheek a delightful squeeze. The resulting closeness also put my face right in the crook of his neck. His skin was warm and smooth and I could smell his pleasant cologne.

Then he reached around with his other hand to grasp my other cheek. Caressing them appreciatively he kept talking, "You've got me more turned on than I've been in a long time.

His hands roamed pleasantly all over my body, but when they were between Hailey's breasts and my back I remembered how I had wanted this night to go. I'd wanted him to handle her boobs, to make love to her while I watched. But now it was she who was watching him make love to me. Moreover, she was feeling up my traitorous erection as he did it. She squeezed my cock in anticipation, saying, "Honey, you feel so impassioned tonight. It must be the fiery red hair."

With her hands still stroking my stiff erection, she was generating no small amount of carnality in me. All the while, I could feel their four arms surrounding me, rubbing against each other.

Neither of them seemed interested in the other, and both of them were giving me their undivided attention.

Hailey kissed my neck lovingly, "Let go baby." Then she laid her head on my shoulder.

With my head also on Leo's shoulder I started to relax a little. I didn't think about it but impulsively I placed a tender kiss on the side of his neck.

He groaned gratefully, moving his hands to join Hailey's on my overstimulated privates. "That's right girly. Show me how much you like this."

"Yea," added Hailey, "Show us how much you like it."

Leo kissed one side of my neck while Hailey kissed the other side. He said, "Touch me girl. Put your hands on me." They had been calling me a girl for a little while now but it still took me a second to realize he was talking to me and not her.

I lifted my hands of my own volition, placing them on the side of his ribcage. His skin wasn't soft like Hailey's. And I felt some of his wiry chest hair with my thumbs.

"That's right baby. You're doing great. Keep going."

I moved my hands up and down his sides feeling his muscles there. In return his hands stroked my wig then held my head to his body affectionately.

My lips were pressed into the skin near his collarbone while my hands kept stroking his body: his hips, his strong thighs, and finally I reached down to manipulate his sex organs.

His cock was powerfully majestic and his testicles were no doubt full of his manly seed. The heat was so strong it shocked me.

"That's so good, baby. You've done it. You've crossed the line." I wasn't sure how I had only now crossed the line since all I did was handle his package, while earlier it had actually been in my mouth.

Taking hold of my waist he then pulled me away from Hailey's exhilarating touch, and up on top of him as he laid back on the bed. My made-up face lingered above his burning eyes, my bra encased chest rubbed on his burly one, and our engorged organs mashed into each other's. Hailey said, "You two look just like a regular couple with the pretty little girl on top of the handsome brute."

We continued grinding, our hard shafts scissored together, leaving little trails of mixed liquids. Our balls jostled together too, both wanting to spill their primordial contents. And our legs were entwined like I had done with Hailey so many times before, like I had wanted her to do with Leo.

The difference was that she was watching my entwined legs instead of me seeing hers. I would have been so turned on to see her like that and now I wanted to turn her on instead. Nevertheless, the stockings felt so sexy and feminine that I didn't mind a man's legs rubbing on mine.

I put my lips on one strong pectoral muscle feeling its solid bulge. Then I kissed around his masculine chest, the hairs tickling my chin. Kissing my way down, with my long red hair trailing on his tanned skin, I noticed his nipples, so unlike hers, on my way to where I needed to go. Leo made contented sounds then taking my arms stopped my progress, "Do you feel sexy, baby?"

I think my mascara'd eyes must have shone, "Yes! Yes I do."

"Do you want to please your man like only a woman can?"

I couldn't stop smiling, "Yes! I do. I really do."

From over in her chair again, Hailey called out, "Then do it already! Take that big cock in your pouty red lips and show us just how much of a slutty whore you can be." I winked at her before continuing.

Flipping my hair out of the way so Hailey would have a clear line of sight, I hovered above his valiant cock and virile balls trying to decide where to begin to bring him the most pleasure.

She wasn't touching my dick anymore. No one was. But I knew her eyes were on me. My cock, swaying below me, still throbbed hard for her to see, proving to my love that my passions were ablaze. I stuck out my tongue giving the provocative head a single swipe, for Hailey as much as for him.

"Wait," cried Leo, "Are you my girl? Mine? Am I the only man who's cock you'll suck and the only man you'll let ravage you?"

"Yes! Yes! I'm your woman. Yours! Do to me what you will." I sat up to put my hair in a ponytail. In the chair, the vibrator's hum clicked up a notch.

He spoke to my wife again, "Hailey, will you hand me that little box?"

I looked to see that with her free hand she picked up something tiny from his pile of things and tossed it to him. He opened the box to show me a sparkling engagement ring. For all I knew it was costume jewelry, and I didn't think it would be a binding arrangement, but I melted inside.

"Jackie, will you do me the honor of being my sissy?" Hailey gasped, as the vibrator clicked off, then she waited silently, watching to see what I would do.

I was overwhelmed. "Yes. Anything." I answered him. "I'll be your sissy."

He placed the diamond on my finger. "Then I've broken your masculine will. For me you will no longer be a man but you will submit voluntarily to my desires according to your female nature."

Leo took hold of my face in both his hands directing my mouth to his thick crown. I opened wide and he pulled me down as far as he could on the first attempt.

I heard the vibrator start again. This time the buzz wasn't proof of her absence but evidence that she was fully enthralled with watching our sordid activities.

Never letting go, he rocked my head up and down, pumping his cock up into me at the same time. More and more of it made its way into my subservient mouth until finally his cockhead touched the entrance to my throat.

Leo twisted my head a little to get a better angle, then with flexing biceps he pulled hard forcing the rest of his cock down my gullet. Somewhere off to the side I could hear Hailey having a long rolling orgasm.

My stretched throat was only a bit smaller than his girth, so while it was tight he managed to get it down alright.

My eyes watered horribly, dripping black make-up stained tears onto his stomach. I fought the urge to pull back, bracing my hands against the mattress to stay where he wanted me.

He would fuck his shaft all the way down then pull me off while I gasped to catch my breath. Then do it again.

I thought back to when I first saw Leo sitting at the table with Hailey and how I wanted to voyeuristically watch her lustfully sink to her knees with her back to the wall, then take his overexcited cock into her irresistible mouth. I wanted to sit with my back to the wall for Leo to use. I also wanted to have Hailey sit for me, but now I added a new dimension to my vision where I went all the way down her throat. Something we'd never done.

After ten or fifteen repetitions I was breathing hard when he asked, "Are you ready for a face-fucking?"

Hailey and I had certainly never done that. I haven't wanted to hurt her before and she was just never quite that sacrificial. Not that I haven't dreamed of doing more with her. But just how would a guy ask his beloved to do something that could be painful?

I looked up at his lecherous gaze. "Ok. Give me a second." If she wanted to see two guys do stuff, then I was going to show her lots of stuff. And just like I had felt a little smug satisfaction when Leo had deepthroated me as she never would, I was gonna prove that it wasn't that hard.

Staring down at the reddened beast I kissed the tip of his precum dripping cock and said, "I'm ready."

Instead of pulling my head down he rolled us over so I was on my back and he was on top. It was the same push-up position as before but now he was facing my feet and wasn't going to just play around in my mouth. This was going to be serious.

And boy was it! He started right away, fucking deeply into my throat in long forceful fucks. In and out, never giving me time to breath.

It didn't last long. Six pumps or so and he buried the whole shaft to the hilt. I felt it spasming and twitching. I felt his balls contract. And I knew his cum was filling my belly.

It was disappointing not to taste it, but maybe next time.

Leo rolled off exhausted. I clapped my hands to my throat trying to massage the pain away but also, with a heaving chest, sucking in much needed air.

I looked over at Hailey, still in her tight sequined red dress which was hiked up above her waist. Her feet were bare, drooping over both arms of the chair, and her distended pussy lips looked well taken care of.

Mostly she looked exhausted too, after cumming so many times. I've seen her cum twice in a night, three times rarely. But from what I heard I think she did it six or more times.

I reflected on our previous talks we had while watching porn. She must have a few secret fantasies and she must have really liked seeing me with Leo to spur her on to such depths.

Leo got dressed, collecting all his belongings including everything I was wearing except the ring, "He tweaked my still taut erection while removing my thong, then turning to Hailey he paraphrased her, "Buddy, I think your lover's ready for something new, there's some pent up excitement down there."

And he was gone.

Laying naked on the bed and feeling like myself again, I looked to Hailey sprawled over the chair with her head laid back, "I take it you had a good time?" I asked her.

"Oh honey, your idea to have a threesome was pretty good."

"You know," I said, "technically it wasn't a threesome. And really my idea was for me to watch him with you."

"Well it turned out to be hot nevertheless. Just like that story.

"Well it did end up being great, but I've been left high and dry over here."

Seeming to ignore me she offered her opinion, "Wow! I'm surprised you let him do all that to you. It even looked kinda brutal. Do normal people do it like that?"

I wanted her to submit to me as well so I told her, "It was fun and a blast to submit and make him happy. But I did it mostly because I love you. Right? You said if we love each other we do anything.

She mulled it over, "That we did." Then, "whaddya think the ring thing was about?"

I laughed, "Meh, just drama. But it felt neat and really set a mood."

With a burst of energy and wordiness she lifted her head, "You think we'll hear from him again? Would you do it again? And what should we do about that?" She said it pointing to my hard-on. "My pussy's a little raw from an hour riding the vibrator. Would my honey like a little blowjob?"

"Well actually, when he was abusing my face I liked being such a sub, and liked being so giving. So yes, I would do it again, for you. But during it all, I couldn't stop thinking about you." I hesitated briefly, "Can, can I do it to you?"

She stammered surprised that I'd asked, and I'm pretty sure she wanted to say 'no' but was no doubt also feeling trapped by the night's events. Her head shook side to side almost imperceptibly, but in contrast the faltering word she uttered was, "Y-yess."

Then probably fearing the worst she asked, "Under you on the bed like that?"

I smiled slyly with another idea, "I was thinking more along the lines of you sitting on the floor with your back to the wall." She nodded her understanding, forcing a smile.