This takes place back on a Monday in July of 2021. My kids, who live with their mother primarily, had just come to stay with me for a month while their mom and her boyfriend traveled out of the country. It was great having them around more, but a bit of an adjustment to my lifestyle. The night before this story takes place, McKenna, the girl I had been seeing fairly regularly, did her first overnight while I had the kids, albeit somewhat unplanned. The four of us were doing a pizza and Luca movie night and both she and my kids fell asleep, resulting in me carrying her off to bed just as I had done with the kids moments earlier.
McKenna awoke early in the morning and woke me up for a quickie before sneaking out before the kids got up. She had plans to drive to San Diego with friends from her old job and would be back in a couple days.
The kids and I had a great day, going to a jump park, getting shave ice, and taking a trip to the library as well. We had plans for another dinner and a movie (this time just the three of us), but those plans were derailed when I got a call from our scheduler at work. ‘Hi Jan, what’s up?’
‘Hi Jack, do you remember **********?’ He was/is a high profile, public eye figure. I don’t want to give too much away here, but his wife had needed surgery and worked with me a couple years before.
‘Of course, sure, what’s up?’
‘He just called and is flying in this afternoon and wants to schedule surgery tonight. He is insisting on you doing it though.’
‘I’m not scheduled and know nothing about his case.’
‘I know, but he’s insistent. Says it has to be tonight and has to be you. They are sending over the consult he got in London.’
‘Jan, I have my kids tonight.’
‘I know Jack, but you know him… What can I do to help with the kids?’
‘Ok, give me a bit to figure something out.’
It was not ideal, but a cash payor, especially a VIP, was hard to say no to, and my practice really relied on those, even if I personally could take it or leave it. I turned my attention to figuring out a babysitter solution. My first thought was Sophia, a college student who had sat for my kids twice earlier in the year. I wasn’t totally sure about this one though, as we hadn’t really talked since a hookup back in February. Worth a shot I thought, so I sent her a text.
Me: <Hey Sophia, it’s Jack. Long time I guess – any chance you could watch my kids tonight?>
After what seemed like an ungodly amount of time, but in all likelihood was only like 5 minutes she replied back with <Oh hey yea a long time. I moved back home for summer maybe for good not sure. Sorry otherwise would totally do it>
Me: <No worries Sophia> So, back to the drawing board. I asked my kids, ‘Hey guys, when you have babysitters, do you know who your mom uses?’ I wasn’t sure I was entirely going to get accurate info from a couple of kindergarteners but figured I would try. As a last resort, I could try getting ahold of their mom, but since she was in Europe, the time difference wasn’t working in my favor.
My daughter told me their favorite is Skylar, which was great news to me, as that was a babysitter for whom I actually had contact info. She was our go-to babysitter when we were married, but like several of our friends and certain dining venues, my ex-wife Vanessa “got” Skylar in the divorce. Now that said, the last time I had had any contact with her was probably in late 2019, and few and far between were the times where I had ever coordinated with her, as Vanessa primarily handled it. It was lucky I even had her number, owing to a summer where she was effectively our nanny when we went on a family vacation.
*Not to break up the story, but I’m going to introduce a last name here. To be clear, this is close to, but not my actual last name, and for purposes of the story and others to come, I think it is better than just leaving a blank like I have in past stories.*
I sent my opening text, hoping that I could connect with her before having to resort to begging my friends for the use of their babysitters/nannies/au pairs, what have you. <Hi Skylar, it’s Jack Miller. Any chance you could watch the kiddos tonight?> My kids were trying to get my attention, as they wanted me to build with Lego, so we went back to that. After about 20 minutes my phone notified me of a new text. Sure enough, Skylar had responded.
<OMG! Dr Miller I haven’t seen u in 4ever. Id luv to watch them. What time do u need me?>
Me: <How early could you start? I was thinking like 5 or so? Should just be a few hours I think?>
Skylar: <Shoot, I am working a double today and Im not in the neighborhood anymore so probably like 7?>
Me: <That’ll work, not a worry> I gave her my new address, called the office back to lock in the procedure timing, and got back to an epic Lego build.
We were just wrapping up dinner when I saw a Jeep Wrangler pull up in front of my house. I hadn’t seen Skylar in probably 20 months, and as she made her way up to my door, I was a little taken aback if I’m being honest. Vanessa and I had started hiring Skylar a little over five years ago, when Vanessa felt comfortable having a neighbor watch them, and when our neighbor Colleen mentioned her *very responsible* 13-year-old daughter was available to babysit, Vanessa took her up on it.
Skylar was in fact very responsible, and the kids took to her immediately. She became our go-to babysitter for years, and at times, also served as a “mother’s helper” and even nannied for us on vacations.
So now to see her walking up to my door in cutoff jeans and a Dutch Bros t-shirt, I was surprised to see how much she had changed in the nearly two years since I had seen her last. Still petite at probably 5’2” she was no longer the awkward, skinny teenager with braces. I opened the door as she was about to knock, ‘Oh my gosh, Dr. Miller, how are you?!’ she exclaimed. I had held out my hand to shake hers and she leaned in and gave me a hug. She smelled like shampoo and bore a striking resemblance to Sarah Hyland.
‘I’m great Skylar, and you know you can call me Jack. What about you, how are you doing?’
‘I’m good. Just graduated and saving up for my first year of college. I’m headed to Emory this fall.’
‘Oh wow, how did you pick Emory?’
‘After my parents got divorced last year, my dad moved to Atlanta, and I visited him and toured it.’
‘Oh, I hadn’t heard they got divorced.’
‘Yeah, they split up. Mom waited until after I graduated to sell the house, so we live like 40 minutes away now. Kind of a pain but since I’m leaving soon anyway, and only really work, it’s fine.’
I gave her the nickel tour of my place, and when the kids heard her voice, they ecstatically took over. I told her I was headed out and made my way to the surgery center. The procedure was going pretty well, but when we hit a minor complication, I realized there was no way we’d be done in the couple hour timeline I had told Skylar. I took a momentary break and texted her.
<Hey Skylar – looks like it is going to take a bit longer. So sorry, but can you stay a couple more hours?>
<No problem Dr M! Kids are asleep I just need to let my mom know. She doesn’t like me driving late especially when I get up early like today - but I should be ok>
<Oh no! Early morning for you today?>
<Yah I started a little before 5 this morning. Ill just take a nap on your couch Ill be fine>
<I can get you an uber home tonight and get you one tomorrow to get your car.>
<U dont have to do that. Ive done late nights for Vanessa before too but I usually just stay the night in their guest bedroom. Its ok tho Ill just have a coffee l8r after my nap lol>
<Sorry I don’t have a guest bedroom! You are free to sleep on my couch tho. Sorry if that’s weird to even suggest. I hate that I put you in this position.>
<Oh don’t be Dr M! Its ok. I may do that, Ill just see how I feel l8r>
I went back to the procedure, and as expected it took a couple more hours. Once I wrapped up post-op work, and checked on the patient, it was a little after midnight when I got back home. I quietly made my way in to the living room where the TV was still on and Skylar was asleep on the couch. Letting her sleep, I put a couple things away in the kitchen, making just enough noise to rouse her.
‘Oh hi Dr. Miller, everything go ok?’
‘Yeah, totally did. I feel really bad about keeping you so late. Do you think you’ll be okay to drive?’
‘I told my mom I was going to stay the night, she was fine with that, liked it better.’
‘Ok, cool. Let me get you a pillow and blanket. Again, so sorry about this. I’m glad your mom was okay with you staying. Maybe a little surprised. Did you tell her I offered to get you an uber?’
‘Umm, well, I didn’t exactly tell her everything. I just said I was babysitting the kids, I didn’t say I was babysitting here!’ she said with a laugh.
‘Oh! Well, I guess what she doesn’t know… right?’
‘Exactly!’
I went to the hall closet and grabbed a spare pillow and a fleece blanket. ‘Did everything go well with the kids?’
‘Oh totally, they are angels. So much fun.’
‘Great, well, I’m going to go clean up but I’ll check and see if you need anything else before I head to bed. Thank you so much Skylar, I really appreciate it’
I retreated to my bedroom suite, and after getting out of my scrubs, started my shower and got in. I was probably two minutes into my shower when I caught movement out of the corner of my eye. Before my brain could even process what was happening, the shower door opened and a totally nude Skylar joined me in the shower. Her light olive-complected skin had light tan lines, and her small B-cup breasts were topped with light brown areolae and nipples. While she had some darker hair on her arms, it at least appeared she had removed it entirely from her legs and pubic region.
‘Skylar! What are you…’ my question was interrupted by Skylar bringing a finger to my lips as she closed the distance between us. As she pushed against me, she leaned up to kiss me while a hand reached down and grabbed my cock. She grasped it firmly as she kissed me. I could feel myself start to stir as she did, but broke the kiss nonetheless. ‘Skylar, I don’t think this is a good idea.’
‘Why Dr. Miller? I’m 18 and you’re not married anymore.’
‘It’s just, I’ve known you since you were a...’
‘Shhh, it’s ok. I want this,’ she said, before kissing me again. Her hand hadn’t left my cock the entire time we talked, and it was rapidly hardening in her grip as she stroked it. As the water fell on my back, Skylar broke the kiss and knelt in front of me, looking up at me as she moved her mouth to the head of my probably three-quarter erection. As she continued to stroke the shaft with her hand, she massaged the head with her tongue, never breaking eye contact with me.
Skylar continued to suck me for probably 3 minutes, although her mouth could really only fit the head and an inch or so of the shaft in it, but her hand helped the cause immensely. She broke contact briefly to free her mouth, looking up at me and saying, ‘I think we’re wasting water, do you want to turn the shower off?’
I reached back and turned off the shower as Skylar stood up. We stepped out and grabbed two towels, drying ourselves off. ‘Are you sure about this?’ I asked her.
‘Oh my god yes’ she replied, ‘you have no idea.’
I hung up my towel, and went to reach for hers when she said, ‘um, you may want to grab that towel, and any others you have. I, umm, get, like really wet, and it can get messy. I like… umm, you know what squirting is, right?’
‘Yeah, ok.’
‘I know, it’s weird. My mom always says I need to use my towels for more than one shower. She said no one goes through as many towels as I do. I would be so embarrassed if she knew why.’
‘Not weird, it’s hot’ I told her, as I grabbed a couple more towels. I pulled back the comforter and put a few towels on the bed. ‘Do you want to lay down?’ I asked her.
‘No, you lay down, I want to go back to what we were doing.’
I laid down and Skylar moved to the side of me, grabbing my cock and putting her mouth on it again. She again struggled to take much more than she did in the shower, and the angle wasn’t working all that better. She kept working it though, moving her body more towards the top of the bed as she positioned the slight upward curve of my cock into her mouth.
Her knee was now right against my body, and I took the opportunity to reach over and lift it up, pulling her atop my torso. As she straddled me, her smooth, hairless slit appeared over me. Her labia were tiny, and it was apparent she was freshly shaved, save for a couple stray bits of stubble she had missed. She was also incredibly wet already, her labia glistening in the dim light.
I brought my tongue to her pussy, causing Skylar to moan quietly against my cock. The wetness coating the entirety of her pussy was sweet and slightly salty, and I thoroughly enjoyed exploring her with my tongue. The stimulation was apparently too much for Skylar to continue concentrating, as I felt her pull up off my cock, whimpering slightly as I continued licking her.
I teased her momentarily, moving my tongue to the outer labia, eliciting a whimper of protest. I licked upwards towards her taint before flicking my tongue across her ass a couple times. ‘Whoa, that was my butt Dr. Miller, wrong hole.’
I pulled away, ‘I know what it was Skylar. And seriously, can you call me Jack?’
‘Umm, I’ll try but you are always going to be Dr. Miller to me, I can’t believe you just licked my butt though. That was crazy.’
I moved my mouth back to her pussy, focusing now on her tiny clit. Skylar moaned quietly, but as I focused on that spot, her breathing and the quiet moaning became faster in pace. She said, ‘Umm… Dr. Miller, umm, I mean… um, Jack, you should stop, I’m gonna, mmmm, okay, you should stop, I don’t want to cum on you like this…’
I pulled away just enough to say, ‘it’s okay, I want you to’ before moving my mouth back to her clit. As I resumed, it took only like 30 seconds for Skylar to lightly cry out while simultaneously, a not insignificant amount of fluid emanated from her pussy, flooding my mouth and across my face.
Skylar was shaking as she came, and when it stopped, she rose up to say, ‘Oh my god, that is so embarrassing. I’ve never cum like that in that position with a guy. I’m so so sorry.’ She turned around and was now kneeling on the bed next to me, as I used a corner of the towel to dry my face off.
‘Don’t be, that was so hot.’
‘I want to make you cum.’
‘Great! Do you want to go back to what you were doing before I took over?’
‘Um, so I overhead Ms. Mil… uh, Vanessa, talking once about you guys having more kids, and she said you had, you know…’
‘Wow, you heard her talking about that?’
‘You’d be surprised at all the things nannies and babysitters hear. That’s why I sort of knew you were, like, bigger. Although not this big. Fucking wow. But yeah. So, anyway, I want to fuck you.’
‘OK, let me grab a condom.’ I said as I started to get up.
‘No, don’t! I mean, um, my ex and I always used them and I, uh, I always wanted to know what it would feel like without one, but like, you know…’ she trailed off.
I contemplated this for a moment, but the little head quickly won out, ‘Yeah, ok, sure’ I replied, ‘How do you want to, uh, start?’
Skylar had the biggest smile on her face, ‘Can you lay back down?’ I did so, and she immediately straddled me, hovering above me on her knees and grasping my cock with one hand. Her naked body looked small above me, and she had a look of determination on her face as she lowered herself down.
As the head of my cock made contact with her labia, she appeared to realize it was not going to be an easy task, and brought a hand up to her mouth to get spit before moving it back down and rubbing it on her lips and attempting again. Again, though, my cock was met with resistance. She moved it every which way down there, towards the front, then back, attempting to find a way to allow the intruder to enter her.
She eventually settled on force, and pushed down while holding me firm against her. I could feel the slightest give, but even then, it was at best the first half an inch of the head of my cock nestling between her labia and perhaps pushing into her vagina. After five minutes of attempting it, she paused and said, ‘I don’t think it’s gonna work like this.’
‘Yeah, you’re just really tight.’
‘Well, I mean, I think it’s you, not me’ she said, sort of teasing. ‘Can we try another position? I really want this.’ She moved off of me, and as I sat up, she took a position on the side of the bed on her hands and knees. She was in more of a traditional doggystyle position, her back parallel to the bed, not the sluttier, chest-against-the-bed, arched-back version I had gotten used to over the past month with McKenna.
I moved to the bedside table to get lube. Skylar watched me, her tongue sort of out and moving slightly along her top lip. Returning to my place behind her, I took in the sight in front of me. Skylar’s thighs, her ass, and especially her pussy had a sheen of wetness on them from squirting. What was most noticeable, however, was just how absolutely tiny her pussy was. The width, as well as the distance from her clit to her perineum - she was just small. As I brought my lubricated index finger down to her, I noted I could completely obscure any view of her labia with just one finger.
She was dripping wet, but I still applied the lube, given our difficulties just now in penetration. As the cool lube touched her, Skylar giggled briefly before letting out a short, breathy moan. My finger slid, barely, between her labia and as it slid briefly into her vagina, I felt the walls grip it tightly. *This is going to be a challenge* I thought to myself.
I removed the finger and placed both hands on the cheeks of her ass on either side of her pussy, pulling apart lightly to get better visual. As her labia parted, I saw the dime-sized opening of her vagina. Realizing just how much of a challenge this would be, I grabbed the lube again, coating my cock before placing it against her slick opening. The head of my cock, glossy with precum, Skylar’s saliva, and now lube, dwarfed the pussy it was about to enter.
Holding her ass with one hand and my cock with the other, I began to push in, the resistance of her tight opening pushing back against me until the lubrication did its job and I felt the head of my cock slide in. Skylar was breathing out rapidly, in a Lamaze-like manner. I paused, the head now fully inside her. ‘Are you okay, do you want me to stop?’
‘No, umm, oh my god, I just… um, go slow, ok?’
With steady pressure, I resumed the initial penetration. Skylar’s rapid breathing had me worried she would end up hyperventilating, but she slowed her pace while still exhaling deeply. When I was about halfway in, I pulled back, leaving just the head in before resuming my forward motion. Skylar immediately gasped and moaned. 'Is that okay?’ I asked her.
‘Oh my god, Dr. Miller, it’s good, I just…mmm, oh god, you’re so big, it’s like stretching me.’ And looking down, it really was. Her ass looked so petite in front of me, and I as held her cheeks in both hands, I could see my cock just absolutely stretching the lips of her pussy as I moved in and out.
The lube at least was helping the situation, combining with the wetness in Skylar’s pussy and I was able to get a good pace going. It went on like that for seven or eight minutes, Skylar whimpering, with intermittent interruptions of ‘Oh Dr Miller, oh god’. Skylar began to moan more, the whimpers now replaced with a more guttural sound and some sharp ‘Oh’ expressions coming as well. I could feel her pussy starting to clench around me before she let out a loud moan. I apparently timed an outstroke to coincide with that moment, and as the head of my cock reached the last outer inch or so of her pussy, her clenching forced it entirely out of her as another stream of liquid was released. This lasted probably only five seconds, but seemed like forever as it splashed against me, the bed, and the floor of my bedroom, with Skylar screaming/moaning all the while.
When she came down from it, she turned, eyes wide, ‘Oh my god, Dr Miller, I’ve never cum like that with a guy inside me.’ She looked down at my cock, ‘You’re still hard!’
‘Well, yeah, I haven’t cum yet.’ I replied.
‘Oh wow, I um, the longest my boyfriend, well, ex, lasted was like 3 minutes. I just assumed…’ She moved slightly up, now kneeling on the bed, light drips of liquid still coming from her pussy, her inner thighs soaked. ‘Lay down on the bed? I wanna try that other position again.’
I laid down, and Skylar straddled me. She grabbed the tube of lube on the bed, and squirted out a little to her hand before applying it to her labia and vagina. She grabbed my cock, still slick with her wetness twitching with my heartbeat, the head hovering above my pubic bone. Her small hand looked even tinier gripped around it, and as she brought it up into position, I again marveled at how it looked next to her similarly small pussy.
Skylar started to push down onto me, as the head wedged between her lips. I had been watching it enter her, but my eyes shifted up to her face. Skylar was starting directly at me, mouth agape as I entered her again. Slowly, but without hesitation, Skylar continued to slide down my shaft. As she did, her mouth widened, silently, while her eyes mirrored that, opening wider the further down she slid.
As she reached the base of my cock, she paused. Now breathing deeply, I watched as her small B-cups breasts rose and fell. She began to lift up, moving only an inch before coming back down, her pussy lips splayed around my shaft tightly. She repeated the motion, slowly, just an inch up before coming back down. Skylar spoke, breaking the silence in the room that had previously made her breathing and the light squelch of where we were connected the loudest thing in the room. ‘Dr. Miller, I bet you didn’t think you’d be doing this when you called me, did you?’
‘I can’t say I did Skylar. I’m sure you didn’t think it either.’
‘I mean, I’ve been *thinking* about it for a while’ she replied, starting to pick up her pace, both in terms of speed and the depth of movement. ‘Oh goddddddd!’ she moaned, ‘This is so good, so much better than I imagined.’ She continued moaning as she rode harder. This continued for several more minutes. I grabbed her hips, more to steady her, as her pace was quickening and as tight as she was, I was a little worried that a miss on a downstroke could be painful for us both.
Skylar’s pale skin had a sheen of sweat. Her doe-eyes were still wide, as she moaned with a smile on her face, framed with the light-brown curls of her hair. I could feel the impending orgasm began to build. ‘Skylar, I’m gonna cum soon.’ I warned.
‘Mmmm’ she moaned, ‘Do it in me, I want to feel it.’ My balls tightening, I could feel the shaft and head expanding slightly as my body prepared to cum. Before I could get there though, Skylar moaned again, loudly, while I felt her pussy squeeze as she experienced another orgasm.
She was fully locked down on me, pussy pressed against my pubic bone and balls, so there was no ejecting me from her like last time. The warm fluid of her orgasm spread out over my abs, flowing down onto the towels I was lying upon.
Her pussy continued to squeeze me as she came, and the pulsing against my shaft and head pushed me over the edge. I felt my own pulsing as I came, and apparently, Skylar could feel something as well, her eyes again widening as I emptied my load inside her, her mouth breaking out into a smile. ‘I am *definitely* going on birth control when I get to college. I love the way that felt.’ Keeping my cock buried within her, she bent down towards my face and kissed me. ‘I’m so happy you were my first like that though.’ She kissed me again as my cock began to soften inside her.
She eventually pulled off of me, a more than insignificant amount of cum flowing out of her, before laying down next to me. I got up and began to collect the half dozen or so towels we had laid out on the bed. I threw them in the hamper and peed. Coming back into the bedroom, I saw Skylar still on the bed, touching herself. She noticed me walk in, saying, ‘There’s so much of it in me! And it feels different down there, this is the first time my, umm, you know, feels like, open after.’
‘It won’t stay like that, just temporary.’ I said, attempting to reassure her.
‘I hope not, I’m a little sore too, actually.’
‘Yeah, that’s temporary too. You should go pee though before you go to sleep.’
‘Yeah, I was about to get up. Umm, is it okay if I sleep in here with you?’
I didn’t think that needed asking, I certainly wasn’t going to have her go back out and sleep on the couch. ‘Oh, yeah, of course.’
‘Oh, can you get me a water or something? I feel, like, totally dehydrated right now.’ That wasn’t terribly surprising, given it appeared there was at least a good quart or two of fluid in the various towels I had collected from the bed.
I went to the kitchen and grabbed two waters, returning to the bedroom to find Skylar under the sheets. As I got into the bed, I handed her one of the waters. She took a sip before leaning over and kissing me. ‘Good night Dr Miller’ she said upon our lips parting, ‘and um, thank you for tonight.’
‘Good night Skylar’
I made sure to set an alarm that was early enough that the kids wouldn’t hopefully be up before us, and then drifted off to sleep.
I awoke early the next morning with the alarm, feeling a bare ass pushed against me, or more accurately, my extremely hard morning wood. Briefly forgetting the events of the night before, I tried to figure out whose pert ass was against me. It was too slim and petite to be McKenna (as her athletic ass is unmistakable in bed).
Bringing my arm around, I felt the slim nude body in my bed, as I heard Skylar say, ‘Good morning Dr Miller!’ My hand was venturing down her belly and as I reached her pussy, she parted her legs slightly. She was warm and *very* wet. As my middle finger parted her labia, Skylar turned her head up towards me and let out a sigh. My rigid cock was still pressed against the cleft between her ass cheeks. Shifting my hips down, my cock sprung forward, brushing against her labia.
Looking back at me over her shoulder, her doe-eyes fluttering she whispered, ‘You’re so hard…’ before biting her lip, and then continuing, ‘but I’m sooo sore. Like, you know the phrase re-arranged my guts? That’s how it feels today, like everything is umm, throbbing and sore inside.’ I had heard it before, but usually it was in the form of a text message, rather than while their ass is pressed up against me.
‘It’s okay, I totally understand.’
‘But, um, Dr Miller, I don’t wanna leave you like this.’
‘It’s O…’ she interrupted me by flipping over and pulling me in for a kiss while reaching down and wrapping her petite hand around my cock. As she broke the kiss, she moved down my body, kissing my neck, chest, and abdomen before finally reaching my cock.
She pulled the sheet off of us, her curls a little wild with bedhead, reminiscent of how she looked when we used to hire her. She was holding my cock with one hand, staring at it before looking up at me. ‘I don’t even understand how this fit in me. I tried three fingers once and I couldn’t get them in, and look at three of my fingers next to it!’ She started to stroke the shaft while still staring at it. ‘No wonder I’m so sore.’
She moved her mouth up to the head, licking it before opening wide to take it in her mouth. She grabbed the lower part of the shaft with her other hand and did a twisting motion with her other hand twisting in the opposite direction. She pulled her mouth off momentarily, ‘Let me know if this is ok. I’ve wanted to try this but my ex-boyfriend’s wasn’t big enough.’
‘If you make it a little wetter you can grip it tighter.’ I felt bad critiquing her technique, but since she asked…
She spit on it a few times before looking up at me. ‘Like that?’
‘The wetter the better’ I responded, ‘just like you.’
She smiled before working to get a large amount of saliva in her mouth and spitting it out onto the head. It dripped down and she used her hands to get it along the shaft. Wrapping her lips around the head again, she gripped the shaft tighter and began rotating again. The lubrication on her hands made it feel considerably more pleasurable. Not the wettest though, there was still a risk of Indian burn.
She continued sucking and rotating, moving her lips along the top of the shaft and the head, and flicking her tongue against it. Every 15 or so seconds, she’d add even more suction and swallow. ‘If you let that drip out instead of swallowing it’ll feel even better.’ I suggested.
She pulled off for a moment, ‘I don’t want to drool on you.’
‘Oh you should absolutely drool on it. And not that I want to gag you, but if you do gag, the saliva gets thicker and slicker.’
‘I’ll try’ she replied before putting her mouth back on me. She pushed down a little more, her teeth lightly scraping against the head. A “gawk” quickly came from her throat. I heard her try to swallow before she instead, opened her lips, saliva running out.
‘Just like that.’ She repeated the motion, “Gawk”-drool, “Gawk” – drool, “Gawk” – holding it there for a moment, followed by lots of drool. She sniffed before breathing through her nose. Her hands were now coated in spit, and she began to rotate her hands faster. ‘Mm, that feels so good Skylar.’ I said to encourage her.
She apparently appreciated the complement and began to go even harder. Her hair was now obscuring the view, but that didn’t detract from the feeling of her hands and mouth in their coordinated effort, nor the sounds they were making in the silence of the early morning. She continued like that on me for probably 7 more minutes. She’d gotten comfortable with the drool, and there was now a pool of her spit on my crotch. A few times she’d bring me back into her throat and with another “gawk” came the thicker saliva to join. She pulled off of me for a moment, pulling her hair out of the way with one spit covered hand. Looking up at me with her brown doe-eyes she asked, ‘Am I doing good Dr Miller? Tell me if you need me to do something different. I know it’s taking a while.’
‘So good Skylar. Don’t stop.’ She smiled up at me before taking me into her mouth again. Two more minutes of it.
‘You last so long. I’ve never done this for this long.’
‘It’s ok, you can stop if you want.’
‘No, I don’t want to stop. I want you to cum. Do you know how long I’ve wanted to do this?’ *She told me, but it need not be repeated here.*
Back into her mouth, she sped up even further, the noise of it getting even louder. Perhaps because it was her added to the physical sensation and I realized I was about to climax. ‘Skylar I’m gonna cum.’. Undeterred, she maintained her pace until I unloaded in her mouth with a groan. I heard her sputter for a moment before the tell-tale sound of swallowing. She had had to switch from letting herself drool on my dick to swallow, and some cum didn’t make the transition, drizzling out and down her hands. She continued sucking and stroking and I was about to tell her to stop when she pulled her mouth off and stopped the rotation.
‘You cum so much.’ She said while licking her lips and looking at the cum mixed with saliva on her hands still gripped around me. She released me, strings of saliva connecting her fingers to my cock. Her mouth and chin were similarly coated and she used the back of her hand to try to wipe it away but ended up getting just as much on her mouth. ‘I’ve never done this and have it be this messy. Look there’s like a glob of it on my thumb,’ holding it up for me to see before she licked it. ‘Was that good for you?’
‘It was great. Thank you’
‘Oh my god Dr Miller, you don’t need to thank me. If anything I should be thanking you for like teaching me.’
‘It was like one tip.’
She was getting out of bed and stretched her slim frame before looking at the clock. ‘Oh my god is it 6:40?’
‘Yeah?’
‘Oh I have work in 20 minutes!’ she scrambled around to get her clothes, pulling on a tiny bralette and throwing her Dutch Bros shirt back on. She grabbed her underwear, pulling it to her nose. ‘Ew. Don’t judge me, but I don’t want to wear these two days in a row’ grabbing her jeans shorts and pulling them on. She stuffed the thong in her pocket.
‘Probably a good idea.’
She walked into the bathroom and looked at herself in the mirror. ‘Oh wow, this is gonna be hard to hide.’ With the light on, she could really see how red the skin was around her mouth, in addition to the saliva and cum glaze. She washed her face of the spit, but the redness she’d just have to deal with.
I joined her in the bathroom, my naked frame dwarfing her. ‘Thanks again for last night.’
‘Dr Miller, ermm, Jack, I mean, I told you I have been thinking about that forever.’
‘I meant taking care of my kids.’
She laughed. ‘I sorta *took care of the kids* in more ways than one.’ She said, putting it in air quotes.
‘Oh that’s bad. Ok, you need to get to work. Don’t forget the cash on the counter for the babysitting.’ I walked her to the door, still nude.
She put her arms around me, pulling me down to kiss me on the cheek. ‘Bye Dr Miller, I had fun.’
‘Bye Skylar. Drive safe and if I don’t see you, good luck at Emory.’