She-Male Babysitter

"We won't hurt Michelle. She is in a safe place, with safe people. Go ahead and take Arlo's jacket off. One step at a time."

Michelle gave a little nod, more as if getting up her resolve than replying to Jessi. I nodded back, just to add my reassurance to the mix. That seemed to work, because Michelle's nervous smile turned into a grin bright enough to outshine the lightning, and she immediately reached up and slid my jacket of my shoulders, letting it fall behind me.

Her hands rested briefly on my shoulders, but then slid along my chest to where the open neck was closed conservatively by a button above my nipple height. Michelle paused again, and glanced at Jessi. Although my wife's face was turned in our direction, her eyes were dreamy and unfocused. A quick glance down her body explained why. Jessi's right hand was cupping her swollen tit, teasing the nipple so hard that the droplet of milk dangled dangerously. Her left hand was just travelling down her belly and stroking her labia as we watched.

"May I?"

Jessi just nodded.

Without another word, her fingers fumbled with my top button. Finally, it sprang loose. Her palm rested on my sternum. I felt the warmth run down my torso straight to my groin.

I took Michelle's hand gently, guiding it to the next button, and the next. After she undid those, she seemed to have gained confidence again, tugging my shirt out of the waistband of my pants, and peeling it off me, dropping it on top of the jacket.

Michelle seemed to be regaining her confidence. Without a glance at Jessi, our babysitter quickly undid my belt and opened the button on my pants. The weight of my manhood was all that was then required to force the zipper open. The pants puddled around my ankles.

"That is just so beautiful," Michelle spoke.

"Touch it dear," Jessi replied.

A line was definitely about to be crossed.

As Michelle wrapped her hand around my girth, my wife grabbed my hand and guided it to the babysitter's cock. Together, our hands held that throbbing meat. A shiver ran through my body. Michelle stroked my shaft. Jessi and I copied her movement.

"You better take off his wet underwear."

Michelle pouted dramatically, but released her grip on my cock and did as instructed. I stepped free of then, and kicked them into a corner. Michelle gigged girlishly, covering her mouth with her free hand.

"He looks so silly standing there in just shoes and socks."

"Shall we pause and take them off?"

"Let's."

The two women dropped to their knees in front of me. With remarkable synchronization, they untied my laces and lifted my feet free. It took only a second more to slip my socks off.

It shocked me when Michelle, after a quick glance at my wife as if to seek permission, kissed the top of each of my feet, and proceeded to slowly lick all around., starting on the top, then the soles, then up to the ankles, finally focusing in on suckling my toes. In hindsight, her fascination with Jessi's stockings could have been a clue, but this unusual fetish brought me unexpected pleasure. Warmth flooded through my body. My cock started to leak precum.

Jessi raised up on her haunches and quickly licked up the droplet dangling from my dick. She turned her head, lifted Michelle's mouth off my toes, and pressed her lips to Michelle's mouth. My wife, faithful to me all these years, was snowballing our she-male babysitter at my feet. My head spun, my balls roiled. My cock twitched.

The kiss ended. Jessi pulled her lips away, but held her face close to Michelle. With fingers guiding the young babysitter's chin, my wife urged Michelle to taste my seed direct from the source.

That moment as Michelle's lips touched my tip was punctuated by another flash of lightning, and faint distant thunder. The storm outside was passing, while the passion inside was growing stormily.

Unlike Jessi, Michelle did not settle for just a taste. She planted her lips around my swollen throbbing purple helmet. Then she reached up and fondled my aching balls, before sliding that hand up my shaft. Slowly, she drew the fist back to my root, lowering her lips as she worked, until my full length was buried deeply in her throat.

Michelle might profess virginity since her transition, but she clearly knew how to give a great blowjob and was not shy to deliver.

Jessi had been the first woman to give me head, and I had never cheated, no matter what she feared about my attraction to the students. Michelle's blowjob was the first I was receiving from anybody but Jessi. It was made even more special by my knowing that Jessi not only approved, but was participating. As Michelle's tongue curled around my hardness, my wife lifted the babysitter's fuzzy pink sweater, revealing a lacy underwire bra that matched Michelle's panties. Hard young nipples pressed against the filmy fabric as we saw that our she-male sitter had indeed received implant surgery, and possessed very realistic firm breasts, a perfect shape and size for her body.

My wife grinned. She glanced up at me, more to share our excitement than to ask permission, because we were clearly past that point. Then she eased Michelle's left boob free from the lace. My first sighting of the engorged bubble gum nipple made my cock throb enough that a tiny spurt of seed shot into Michelle's mouth. I watched her throat moving as she swallowed, which also gave me a perfect view of Jessi lowering her lips to take Michelle's nubbin into her mouth. At the same time, my wife took Michelle's cock in hand and stroked it. Without stopping her oral attention to my cock, Michelle fondled Jessi's right tit, cupping it in her palm, kneading it, then thumbing the nipple. The milk flowed. Michelle glanced up at me, and then pulled her mouth off my cock just long enough to bring her wet fingers to her mouth and suck them clean. When she resumed the blowjob, the extra creaminess gave special lubrication to her efforts.

Jessi let out a familiar sigh of pleasure as she removed her mouth from Michelle's tit just long enough to pop the other side free and plant her lips on that one.

"Do we want me to fill Michelle's mouth now, because I'm very close to exploding?"

Both women popped their mouths free and gazed up at me before looking each other in the eyes. This triggered a fit of simultaneous giggles. Michelle seemed to be taking Jessi back to her youth.

Michelle idly stroked my cock slowly, maintaining my hair trigger readiness, but maintaining the grip of the root with fingers of her other hand, not letting it blow just yet.

"Are you happy just to have sucked it? Do you want to watch it fuck me?" Jessi suddenly got a wicked grin on her face. "Or... do you want Arlo to fuck you?"

That last dramatically timed question led to Jessi's grin spreading even wider.

"How many times can he come and still get hard?"

"We've never shared another woman together, let alone a special woman like you, so I can't really say for sure. I do know that with just me, he gets going for round two really quickly. I bet we can get at least three rounds out of him today, unless he blows too full a load on round one or two."

"Then I want to swallow the first load, if that's okay with you. I've never done that before and would love to know what it feels like."

"Not every woman loves it like I do, but you should find out for yourself. The only thing is- I insist that you don't swallow it all. Save some to share with me."

Michelle grinned and nodded.

By this point, I knew better than to ask if I got a vote. Besides which, the way my cock was throbbing told the tale. I had never been this excited in my life.

Michelle again raised her head and swallowed my cock whole, stopping with her lips meeting her fingers where they gripped my root. Her nails raked my balls and my taint.

"If I need to trigger an orgasm from Arlo, I stick a finger up his ass to stimulate his prostate, so be careful- if you do that, you will get great gobs of goo in your gullet, but he might empty out too much to still be ready for another round right away."

"I don't need that right now," I spoke for the first time in what seemed like forever, "My seed feels determined to seep up my shaft, and explode into Michelle's mouth. It will happen soon even if she tries to hold it back."

Michelle pulled her mouth back, holding just the bulb in her lips.

"You like the babysitter sucking your cock, don't you? I bet you want to fuck her naughty little ass too."

Jessi chuckled. It was more of an evil laugh.

"I ought to make you suck her cock- though since she is female, maybe you'd rationalize that it is just a giant clit? But if it's just a clit, how will it be able to fuck me? Do you want to watch Michelle fuck me? Because I need to be fucked."

Jessi paused and looked directly at Michelle. "That is if it is okay with you, baby. I don't want to ask you to do something that you think is nasty because Mikey used to do it."

My wife reached over and stroked Michelle's erection.

"You don't need to answer right now, you have your mouth full. Just know that I want to make sure that you are pleased in all the ways you prefer."

Michelle was so excited that she accidentally bit the flap of flesh joining my helmet to my shaft. She again took my full length into her throat, saliva leaking out of her lips, lubricating as she went.

This time, when her lips met her fingers, she released her grip. The surge of seed slammed against the back of her throat. It seemed like she might vacuum me clean, and swallow every sperm out of my sack.

Jessi must have being reading my mind.

"Save some in your mouth to share with me, and leave some inside Arlo for round two."

Michelle raised her head, removing my cock from her mouth. A string of semen ran from her lower lip to my tip until she pushed a flow of gism out of her mouth, allowing it to run down her chin.

Jessi allowed some to dribble onto Michelle's cleavage before she bent over and hungrily licked Michelle's chin clean, working up toward those glistening lips. Upon reaching Michelle's mouth, my wife kissed our she-male babysitter deeply. The movement in their cheeks indicated that they were fiercely twisting their tongues around, sharing the seed Michelle had saved for that purpose.

The intensity of the situation ensured that my cock stayed erect. In the momentary silence, I listened for any sound of children awakened by the storm, but all was quiet as Jessi pulled away from Michelle's lips and kissed down the babysitter's neck, nibbling softly. As Jessi dabbed her tongue out to capture the stray droplets of semen scattered across Michelle's chest, the young she-male bent forward to lick the last drop of semen that was dangling from my slit.

I hoped that Michelle might continue, licking me clean, but suddenly, she was too busy moaning, grabbing fistfuls of Jessi's hair as my wife chewed on Michelle's tender nipples. Her cries grew louder.

"Ohhhh... ohmigawd... this is what a female orgasm is like."

I watched as a single spurt of semen shot out of Michelle's clit, as Jessi had suggested we call it. It landed on my wife's thigh. Both women were still absorbed with each other, having returned to sharing a deep kiss, perhaps Jessi's way of stifling the sound of Michelle's joy before the kids heard.

The goo glistening on Jessi's flesh held my gaze. Without conscious decision, I dropped to my knees, bent over, and licked it clean. Having previously tasted my own semen, the saltiness was not surprising, but there was a floral sweetness that was unexpected, and pleasant. Another line had been crossed. I was glad I had. This unexpected adventure was thrilling me in ways I could never have imagined. I did not want it to end.

Jessi reached down and grabbed my hair, pulling my head up to meet the two women. We all touched tongues, then Jessi and I tried kissing Michelle together, both our tongues battling for space in her cheeks. We ended up collapsing on the floor laughing.

"Oh, look. Arlo is still stiff." Michelle pointed at my erection.

"So are you, darling," Jessi answered.

"If Arlo fucks you, may I eat your cream pie? That's always been a dream of mine."

Jessi took hold of Michelle's hand and gently led it back to my cock. With Jessi's help, Michelle began just slowly stroking me, keeping my hardness full. Jessi then took hold of my hand and led it to Michelle's sex. Whether we called it a cock or a clit, it felt strange and familiar all at once.

"Of course you may, darling, if that's what you desire. Do you also want to fuck me? Because if it's okay with Arlo, I would really like that."

Michelle nodded shyly, chewing her bottom lip, and muttered "yes".

"And Arlo needs to play with you a bit more, I think, if both of you agree."

Another tiny nod of Michelle's chin. I wanted to respond, but felt frozen in time and space.

"Arlo, do you mind if Michelle fucks me?"

I was hardly in a position to complain, having had a great blowjob courtesy of the she-male babysitter, and being promised even more fun. My head moved side to side as I muttered, "not at all, I think it would be exciting to see."

"Would you lick that cream pie out of Jessi like I want to eat the one you deposit?"

My mind was reeling at the prospect of crossing lines that I had always assumed were firm. Boundary walls were tumbling, and my wife was not just along for the ride, she was driving the train.

"That would only be fair of him." She giggled. "Besides which, I do love being eaten especially after being filled to the brim. Arlo is very good at that- for a guy."

Both women laughed lustily at the suggestion that women naturally had a home field advantage at cunnilingus.

I noticed that there had not yet been a suggestion that I perform oral sex on Michelle. I found that I was unable to tell whether I was pleased or disappointed by that omission. Her organ looked delicious, in a way that I had never considered before. I was more than a little jealous of the likelihood that my wife was about to feel that fill her mouth.

"Where should we start then?" Jessi asked. The question was clearly directed to Michelle.

"Haven't we already started?"

Both ladies laughed loudly. I winced a bit, afraid of them waking the kids, but I guess if the urchins slept through the thunder, they were down for the count.

"I want to lick your clit," Jessi blurted out. Michelle's organ throbbed at the prospect. My tongue flicked across my lips.

Michelle glanced at my face. Noting my expression, she suggested, "How about you and Arlo do it together? I think that idea excites me the most."

"If you come now, will you still be able to fill me up with your cream? Because if you just want to fuck me, you're ready now- we don't really need to fluff you."

"Not sure." Michelle was a bit short of breath, excited already anticipating how this unexpected threesome might turn out. "But if I need time to recover, that could be when Arlo fills you up, and I eat that cream pie first."

No one bothered to ask me if I was willing to taste Michelle. I was just a pawn in some bigger chess game going on around me. Being desired was enough for me. Shivers ran through my shoulders. My cock stiffened to previously unimaginable size, especially for round two. If I needed to rationalize what I was about to do, I could claim I needed or wanted the recovery time, but that would be a lie- I could have watched Jessi suck Michelle and recovered just fine. Deep down, I wanted this, perhaps as much as she did.

Jessi sealed the deal by giving first me, and then Michelle, scorching kisses. I know mine shook me to my toes. Watching the ladies kiss made my body quiver.

Breaking off the smooch with Michelle, Jessi gave me one more glance, then shifted her position, one stocking clad leg tucked under her, the other reaching out behind, all the better to lower her head toward our sexy she-male babysitter's hardness. I could not resist the urge to reach over and stroke that leg, loving the silkiness of the stocking. Michelle watched what I was doing, her grin growing wider.

Neither of us was watching at the moment my wife tasted the first cock she had touched since we had become young lovers so long ago. Michelle's moan got my attention.

Jessi had Michelle's member gripped firmly in her tiny hand, which made it look huge. My wife deep throated Michelle effortlessly.

"Be careful, I'm already right on the edge. If we want Arlo to get in a few licks, you need to make sure I don't spurt my whole orgasm into your mouth."

"Even with the hormones, I hope you come buckets," Jessi giggled as she pulled her lips up to where she was just warming Michelle's member with her breath.

"Your turn," Michelle smiled at me, a smile that could melt hearts, and tumble walls. If I had any remaining doubt, that removed it.

"Try twirling your tongue around the tip," Jessi suggested.

After trying that, I smiled, having enjoyed my first taste of penis, even though, being a she-male member, I could still rationalize that I was not sucking a man, therefore this was not gay, nor bi. Maybe just a bit gender fluid. The term 'hetero-flexible' pooped into my brain from somewhere.

"Kiss it then lick it down each side," Jessi instructed. She in turn bent lower and sucked Michelle's balls. When my tongue reached Michelle's root, it touched my wife's tongue. I felt a spark connect us. My body shook harder, my cock throbbed harder.

I licked up the underside, not waiting for Jessi's direction, since her mouth was full, but knowing that I would enjoy just that if it was me receiving the blowjob. Michelle quivered in response. I eased her bulb into my mouth, pausing to adjust to the sensation.

Michelle was so excited that she thrust her hips off the floor, forcing me to take most of her into my mouth. She wisely stopped short of forcing her way into my throat.

It took me a bit to adjust to this totally new sensation. Once again, it was like time had paused, or given way to eternity, and did not start again until Jessi's tongue slid off of Michelle and licked my scrotum. That sent a shiver up my spine, but also drew my brain back into reality.

Michelle took my hand in hers and guided it to her tit. I kneaded the unfamiliar flesh, amazed at how it felt both like my wife's boob and yet so different.

"I think you like the taste of my ladyboy clit."

"He can't seem to get enough of it, but its my turn."

Jessi elbowed me out of the way, causing Michelle's wet organ to drop from my mouth, just a thin string of drool attaching us.

I shifted my head into position to suck on Michelle's left nipple as out of the corner of my eye I watched my darling wife bob her head up and down, taking more of Michelle in her mouth with each stroke, stopping occasionally to lick the swollen flesh. Jessi's cunt was rubbing against my leg. My hand trailed along her body until my fingers reached her clit, which I started flicking with my thumb.

Jessi was now taking all of Michelle into her throat, and then pulling back. She stabbed her tongue into the slit, which made her and Michelle moan in unison.

"She tastes like a dream, Arlo, you need to try some."

I let Michelle's nipple plop free and turned my face to meet my wife's lips. Her tongue stabbed past my teeth, sharing just a hint of the tiny taste she had sucked out of Michelle. I had never tasted semen except my own, but Jessi and I had never been shy about that, so I had learned how diet affected how I tasted. Add the dimension of it being someone different, and the female hormones, and Jessi was right - it was different, and delicious. I resolved at that moment to taste more.

My wife resumed sucking our babysitter. She looked so sexy, and just slutty enough. Somehow, seeing Jessi with a she-male was less threatening, and more thrilling, than if it had been another guy.