She-Male Babysitter

[Note to Readers: This is not a story with quick short sex scenes, so if that is your goal, it might not suit you. There are detailed sex scenes, or one long detailed sex scene, take your pick. The use of the infirmary apartment setting is an homage to John Irving's The World According to Garp, which otherwise shares nothing with this story. My thanks to Carnevil9 for a proofread. All errors or omissions remain mine]

"A shemale babysitter - what... the... fuckity... fucking... fuck... fuck?"

"If you didn't so obviously drool over the PYT female sitters that the service sends, I wouldn't have specified a guy this time. I know this service only sends college students over eighteen, but I won't stand for you blatantly flirting with them. Every time you drive them back to the dorm, I worry that they might offer to go further than just flirting. How was I to know they'd send a shemale instead? I thought Michelle was a cute little coed, but it was too late to ask for a substitute."

"Since we live on campus, I almost never drive them to their dorm. Usually I just walk them, unless it is raining. Since you are breastfeeding, it only makes sense that I be the one to do it."

"But you know how hormonal the breastfeeding makes me, and that means I'm jealous even without good reason. Plus, the college code of conduct means that you could lose your job if you did harass a student."

"It isn't harassment if they make the first move."

Which I knew was untrue- the power imbalance would still get me in trouble. Fucking students just wasn't worth it when I had a wonderful wanton wife.

"Oh great, that really allays my fears. You DO know that just having sex - including touching- with a student- is forbidden, I trust."

"Nice to hear that you trust me somewhat."

By this point, we were halfway across campus, headed toward the President's annual bash honouring the faculty members retiring that year. Since my wife was the head nurse at the campus clinic, they had provided us with an apartment attached to the infirmary, where students stayed overnight if deemed unsafe for their dorm, but not sick enough for hospital. Tonight, another nurse was on call, but babysitting was not included. Fortunately, the college also had a matching service that paired students looking for work with faculty looking for help, in our cases, sitters for our three kids ranging from six months to six years.

"There's enough risk with you and the students you teach. Just because they are engineering students, don't think that I don't realize they can be just as hot as some little Arts chickies. In fact, with their schedules, class is about the only place for them to meet guys, and some are bound to like dirty old men."

"So do I need to worry about you and Mikey?"

"You mean Michelle- get with the program."

"Avoiding the question. Don't think I haven't learned to spot that in a few years of teaching."

"Well, I thought it was very reassuring of Michelle to explain her transition when I told her I had asked for a male sitter."

"You'd think the service would update their index."

"You heard Michelle explain that they won't or can't until she gets her official gender change registration. For now, she's technically just a cross-dressing male as far as they are concerned."

"I think I was still in shock that they didn't warn us. Do you think someone at the service did it on purpose because they resented you asking for a male babysitter?"

"Maybe they thought I trying to get lucky, and were jealous."

"Maybe they still figure you'll try to get lucky."

"Maybe they'd still be jealous."

"Avoiding the question again."

"Oh, that was a question?"

We had been so wrapped up in our repartee that neither of us had noticed the sky darkening until that moment, when our conversation was interrupted by a brilliant lightning flash followed instantly by rolling thunder.

"Maybe that's your answer- the Gods are angry." she suggested.

"Angry Gods or not, those were close enough together that the storm must be right over top of us. We better find shelter."

"Trees aren't safe, and all the buildings on this part of campus will be closed since it is Saturday."

"We're closer to home than to the President's residence. Best if we dash towards home. With any luck we won't get wet."

No such luck. By the time we got home, we were both totally soaked. Jessi's tits were still swollen from breastfeeding, even though she had pumped shortly before Michelle had arrived, and the wetness made her sheer blouse transparent, displaying the lacy underwire bra she had selected for a combination of sexy and support.

"Shhhh, don't slam the door," Michelle whispered as soon as we entered. "I just got the kids to sleep. I'll go grab some towels. You two stay put, don't track water too far."

Michelle pirouetted and practically danced out of the foyer. I noticed that Jessi's gaze focussed on Michelle's ass, which twitched very femininely. If I didn't know that Michelle was still biologically Mikey, I would have thought it was a very attractive female student we were seeing. As I watched my wife watch the shemale sitter, I noticed that Jessi's headlights had come on. I was sure her nipples had not been trying to push out through that expensive bra a moment earlier.

"Dry Jessi first," I instructed Michelle upon her return.

She handed me one of our fluffiest oversized bath sheets, and proceeded to wrap one that looked even bigger and plusher around Jessi. Michelle kept hold of the top edge and started to rub the fabric to dry my wife. She steered the back of the towel up the back of Jessi's head, massaging her hair. That created a gap in the front, through which I could see that Jessi's nipples got more excited with each moment. As quickly as the evidence of my wife's arousal appeared, it vanished behind the towel.

As I tried to glance casually at my wife's tits, my gaze shifted downward. I saw that Michelle had grown quite a tent that was lifting the hem of her short skirt. Jessi seemed not to have noticed.

Just as Michelle's hands moved down alongside Jessi's boobs, there was a huge flash of lightning, accompanied by the loudest thunder clap that I had ever heard. Jessi leapt in surprise, tumbling against Michelle. That pushed Michelle's skirt up against her firm belly, revealing the biggest and fattest cock I had ever seen, fully erect, popping out of dainty pink silk panties with lacy flowered borders. The tip bounced off Jessi's hip before Michelle's hands dropped the towel and grabbed my wife's shoulders to steady her.

They both blushed adorably and laughed nervously. Michelle quickly moved her hands off Jessi's body, not touching her tits, as she had come so close to doing. The towel fell in a puddle at Jessi's feet, leaving her obvious arousal undisguised.

My cock was throbbing in my pants. Without looking down, I knew that it would be apparent if either woman cared to look, but their eyes appeared to be fixed on each other. I tried to convince myself that my excitement was strictly caused by my wife's sensuality. Before I succeeded there was another burst of lightning and thunder, close enough that the windows rattled.

"The babes seem not to mind the storm at all," I said after a moment silently catching my breath. Jessi and Michelle swivelled their heads in unison, staring at me, probably shocked that I would comment upon something so mundane when the air was charged with more electricity than the storm outside contained.

What I was really thinking was 'Thank God they didn't wake up and interrupt this, whatever it is.'

I had no clue whether my wife or our new shemale babysitter were thinking similar thoughts. Jessi's nipples certainly were not shrinking, and her tits were heaving as she caught her breath. One button had popped loose on her blouse, revealing a lot of creamy valley between her breasts, and an enticing amount of the lacy off-white bra.

Michelle's eyes were fixed on that space, which allowed me to glance down and confirm that her cock was continuing to throb without my wife noticing my curiosity. If anything, it seemed even more monstrous than before. The head was an angry purple, with its single eye winking at me. Inside my pants, my organ pulsed, as if it was trying to say hello to the visitor. I moved my towel in front of my groin to hide it.

"We better get out you both out of these wet clothes before you catch cold," Michelle finally spoke, after what was either seconds or hours- time had lost all meaning. "Stay here. I'll go up to your room and find something for you to change into so you aren't trailing water through the whole house."

This time when she left the foyer, both Jessi and I were unabashedly staring at Michelle's ass. If I had not been told she was a male, and confirmed it by seeing her endowment, I would have thought it was a particularly fine example of a female dancer's tight young butt. As she climbed the stairs, her glutes rippled magnificently, the edges of the pretty pink panties peeking out of the short skirt.

Jessi and I turned towards each other simultaneously.

"Do you think she got that hard just drying me off, or was she jerking off before we got home?"

"I don't know, but you looked so sexy all wet that even if she was totally flaccid, that boner was a natural reaction."

Jessi blushed, a pink rose blooming on each cheek. The colour covered her neck and ran down all the way into her cleavage, disappearing beyond the bra. I could smell the scent of her excitement. This surprised me a little. Like me, Jessi had always been faithful. She had resented the jokes about nursing students being loose, and as a campus nurse, had always maintained a professional distance from her student patients. Maybe it was just all the electricity in the air.

"Geez, you call that natural? That's supernatural. And here I figured a lady boy would have a teeny shrivelled thingie..." Jessi mused.

"Well, she did get to touch you before we saw it. She also got a real eyeful."

"So did we. This is not at all what I expected when I asked for a male babysitter, and even less so once Michelle explained her situation."

"No, I suppose you expected to just give her a blow job as you walked her home, like the ones you fantasize about me getting from the real women."

"Honey, Michelle is a real woman. She just comes with something extra. And not just a little extra."

Her blush went from pink to scarlet, so I held off on accusing her of avoiding the question, figuring I had my answer. Before I had a moment to figure out where to take this conversation, she spoke again.

"I notice that you aren't exactly turned off by the goings on." She was looking down at my crotch, where my erection still had not subsided. "I suppose that you got that just from looking at me?"

"Things are very confusing. All the thunder, all the lightning."

"Your cock does not seem confused."

"Michelle seems to be taking a while."

"Maybe she is enjoying playing with my panties. Or is trying on my bras."

"That doesn't bother you?"

"She enjoys being a girl, honey. Say- do you think her tits are real?"

"Real? How could they be real?"

"I mean does she have implants, or is she wearing falsies? Or were you too busy checking out her ass and cock to notice her rack? But then I guess you never have been a tit guy."

"Tit guy? Nothing wrong with your tits sweetie."

"Why thank you. But I notice how you stare at the sitters' legs, how your eyes caress their backsides, but when they bend down right in front of you wearing a low-cut blouse, you look away. Or is that just to avoid popping a stiffie in front of their faces? Because that is what they are probably hoping to see, you know."

"Is that what Michelle wants?"

"Honey, Michelle wants men to react to her as a woman. If you see her monster cock and still get hard, that still validates her."

"Then why did your tits turn her on so much?"

"She might be a woman, yet part of her is still very much male."

"As I said, this is very confusing. Besides which, I didn't get a decent look at her tits, with the sweater she's wearing."

"Oh, isn't that darling? Such a lovely pale pink, very feminine. But it isn't bulky or baggy, it fit her curves perfectly, if only you bothered to look."

I remained silent- what could I say, that I was too busy was looking at Michelle's cock, and then her sweet ass, to notice her tits? Jessi was correct that although like all guys I loved looking at and playing with nice tits, my personal focus was always on legs, feet and rear ends. As I contemplated how much Michelle's attributes had turned me on, my cock twitched afresh.

Jessi pressed her palm against my bulge.

"It's okay to be confused darling. It is also okay to be turned on. In case you haven't noticed, I am."

I was disappointed when she moved her hand, but then she grabbed my wrist and guided my fingers to her hem, pulling the bottom of her cocktail dress upward until my fingernails grazed her soaked panties. That caused my aching cock to throb harder. If I didn't get relief soon, I would soil my pants with semen. I prayed that Michelle would leave soon, so that I could fuck my wife.

Jessi shocked me by unzipping my pants and snaking her hand into my fly, stroking my bare cock directly. Suddenly, the lightning and thunder rattled the windows again, startling Jessi. She jerked away, but did not release my member. As a result, it flopped clear out of my fly, stick out straight hard and proud. Any moment now, Michelle would arrive with fresh clothing. My erection would be exposed, and I would not have time to hide it.

"Be right there," Michelle's voice carried from upstairs. "It took me this long to check everywhere for sweats. What kind of parents don't own sweats? Anyway, now I need to figure out what else to bring you. I'd bring you jammies, but all of Nurse Webster's seem to be built for sex, not modesty. And I can't find any at all for Professor Webster."

I wondered how to explain that I slept nude as Jessi spoke. "There are robes hanging in the master bathroom."

"Great. I'll bring them right down. Don't worry, I'll turn my back while you change."

Jessi gave my rod one more stroke then removed her hand. I started to try to fold the hardness back into my pants, figuring that was why she had stopped teasing me.

When Michelle reached the last stair, I enjoyed the mixture of shock and lust on her face. Jessi had started a quick strip tease, her fingers lingering on the last button that held her dress together. My cock had not quite fit back into my pants, my fingers still struggling with my turgid flesh. It must have looked like I was jerking off.

Jessi undid that final button. With a shrug of her shoulders, the dress puddled on the floor. Her arms went expertly up behind her back and grasped the bra clasp.

"Do you want me to just drop this? Or would you rather watch my husband help me?" Jessi giggled, much more girlishly than a thirty-something nursing Mom ought to. "Maybe you want to take it off of me yourself, Michelle?"

Michelle's cock had shrank while she had fetched our robes- I had to wonder if she had relieved herself while fondling Jessi's dainties as well and that had something to do with it. Now, it sprung upward and outward, once again lifting her skirt.

"P...P...Professor Webster can do it, please."

"Oh, honey, call him Arlo."

Stepping behind Jessi I unfastened the clasp one-handed, which is how she had preferred from back when we were dating. I caught both sides of the back strap in my fingers, and held it in place for the moment. Jessi cupped the front, her boobs heavy in her hands. Michelle's tongue wet her lower lip and her cock nodded in anticipation.

"Are you both ready for this?" I asked.

"Yes please, Arlo..." Michelle begged.

"I feel like there should be cheesy music and a stripper pole," Jessi said, then without warning just dropped her hands to her sides. The front of the bra sagged so quickly that I almost had no choice but to let go. The breast pumping was long enough ago that just a touch made droplets of milk appear on each tip.

Michelle's eyes bulged like a cartoon character. Her hard on surged stronger. She seemed to take the step forward without conscious intention.

"Oh, my undies are wet too, I better get them off."

Jessi shimmied her hips as her thumbs found the waist of her panties, nudging them so that they joined the rest of the clothing on the floor. Jessi still was wearing silk stockings, garter belts and low heels. I wondered why she had worn the panties outside the garters. That is not something she typically did. I also could not recall her wearing stockings since the baby was born.

Her pelvis thrust toward Michelle, and rotated, catching my attention as our she-male babysitter took another step closer.

Another round of lightning and thunder sent a fresh shiver through each of our bodies, causing the naked bits to shimmy further, but did not interrupt the events.

Jessi danced to silent music, and kicked her heels off, catching them in her hands. She seemed lost as to what to do about them, so I reached across and took them, gently, placing them on the side table intended for keys and mittens.

"My stockings seem to be the only things that aren't wet, but perhaps you could check to make sure, Michelle?"

Michelle dropped the robes and fell to her knees in front of my wife.

"I love stockings," Michelle purred, reaching her hands up towards the tops of Jessi's last bit of clothing. "I need to get some."

"You certainly have the legs for it, doesn't she Arlo?"

I was too focussed on admiring how delicate Michelle's fingers were, and the perfect manicure, finished with glossy pink nails the exact shade of her panties. All I could do was nod.

"The tops seem dry, but the lower legs would have been below your dress, so are more likely to be wet, I should check all the way along, if that's okay with you, Nurse Webster."

I noticed that Jessi had not corrected Michelle about calling her Nurse Webster, but I had been demoted from Professor Webster to Arlo.

"Maybe Arlo needs to get out of his wet clothing too, before he loses his voice completely. Michelle, honey, do you mind waiting to check the rest of my legs until he does that?"

"M..m...may I help him?"

"He looks like he could use a woman's touch."

It seemed that I did not get a say in the matter.

For the first time since we had unexpectedly returned home, our brand new she-male babysitter focused her attention on me. Michelle's eyes swept over me from foot to the top of my head without pause, but then dropped again to gaze at the obvious bulge in my trousers. Her tongue wet her lower lip. She glanced nervously over at my wife, who gave a simple nod of her head in reply.

Michelle closed the gap between us, standing close enough that her breath warmed my exposed chest, but then paused again. I imagined that her nipples were perky under the loose fitting sweater. I wondered what sort of bra she was wearing, and recalled Jessi's question about whether they were implants or falsies. It appeared that we soon might find out. I discovered that I did not care. Thoughts of suckling them made my cock throb harder.

The storm was still active, once again rattling the windows. Michelle jumped nervously. This brought her erection so close to me that it almost brushed against my pants, within which of course another hard on raged.

"It's all going to be fine as long as the kids don't wake up," Jessi reassured Michelle, though she might have needed the reassurance herself. "Are you a virgin my dear?"

"Michelle is," the babysitter responded. "Mikey's naughty cock liked to do lots of nasty things."