Babysitter Lauren

The stories that follow are true tales of my sexual journey. They are based upon true events and relationships. Some have been embellished a bit just for entertainment purposes, and of course the dialogue is not likely to be 100% accurate in every instance since these events happened over a period of more than ten years, and there was alcohol involved in some of them, but for the most part everything is true and accurate.

My name is Phil. As background, I grew up in Virginia and have lived in southern Virginia my whole life. I had one serious high school girlfriend, and then in college I pretty much played the field. I am 6'5", about 240 pounds, former college athlete at a D-1 school in Virginia. I've kept in shape with almost daily exercise -- running, weight lifting etc.

These tales begin while I was still married. I met my wife Caitlin in graduate school, where I was studying forensic accounting. Unlike the other women I had dated and been with previous to meeting her, she was serious and ambitious, and at that stage of my life, I figured it was time to settle down with someone like her, have a real relationship, raise a family etc.

We had a good and active sex life, and she knew from the start that I had a high sex drive. We didn't do anything crazy, but we covered all the basics and the quality was usually pretty good. Some things were a no go for her, but that was fine with me. I had had plenty of crazy sex in college so I didn't feel like I would be missing out on anything.

But as our family grew and life became busy, we fell victim to the same old story. Caitlin wanted sex less and less frequently, and accused me of being horny all the time. If I reminded her that she knew this and always liked that about me, she would scold me for not growing up. So, we ended up splitting up.

I have come to enjoy rough sex as the dominant party, sometimes combined with a dose of humiliation, with the right partner. Everything from spanking and hair pulling, to name calling, spitting, and golden showers. I don't do it with everyone, and over the years have been a pretty good judge of who would like it and who might not.

As you all read my stories, it may seem that I've been very lucky when it comes to sex, but luck comes from confidence. Women are attracted to confident, alpha male types. But believe me, I've struck out way more than I've scored.

I write these stories now during my second marriage, with the encouragement and assistance of my second wife, Wendy, who is a fine editor as well. Some of the stories are not super exciting, but you take the bad with the good, and I decided if I'm going to tell my story, I need to tell it in full.

Lauren

When I was still married to my first wife, Caitlin, we employed a series of smokin' hot babysitters. Our friends would always make comments to me (in private of course) about how I must be in charge of hiring the "help", but in reality, it was Caitlin that always interviewed and selected the babysitters. Believe me, I never complained.

We were in our mid-thirty's when we started having kids. We only had two, so when our youngest was born, I was about 36. Caitlin decided to go back to work when the little one was about one, and this changed my life forever in many ways.

First of all, going back to work, and working a lot of hours in a new job she loved, made her very tired at night, and with two little kids, there was less time for us to be intimate. We became impatient with each other - me wanting our usual frequent sex, and her wanting me to leave her alone. You all know the drill.

After a year of juggling the after-daycare routine without help, we decided to look for help with the kids after daycare/preschool, so we could both work full days. I hated it, because being somewhat of a traditionalist, I would have preferred that we raise our kids without daycare or extensive help, but Caitlin wanted to work, and the extra money was nice.

Insert Lauren. A graduate of the local Christian college, Lauren was about 26 (I was 38 at the time) and sure didn't fit the mold of the usual graduates from that school. Long, tanned legs, a tattoo on her calf, long blond hair. Kind of a Barbi doll, standing I'd guess around 5'10." Super nice, to be sure, but a naughty side just beneath the surface that I immediately picked up on.

Lauren started with us in the early fall. She'd get the kids from pre-school by 3:30, get them cleaned up, play with them, start dinner etc., until we got home. She would be at the house most days until about 5:30 or 6:00. Sometimes I might get home early, occasionally an hour early, which gave me and Lauren a chance to talk while the kids were watching TV or coloring or doing whatever kids do at that age. They were always close by, still pretty young, but we had some privacy to talk. We flirted slightly, as I found out more about her.

Her father and mother married young and were still happily married. She lived at home, worked as a waitress in the evenings, sometimes at lunch, and worked for us in the afternoon. Nothing unusual or out of line with her upbringing or family life, just a nice, normal young lady trying to find her way.

We got along well. Sometimes she was still at the house with me when Caitlin got home, and Caitlin would always have a snide comment about me in front of Lauren, and it did not go unnoticed.

One day Lauren commented to me "It seems like Caitlin is not happy about something."

I replied, "She's not happy about anything."

Lauren laughed and said something like, "Well that can't make for a happy marriage."

I took a chance and said, "Yeah, and not for a happy sex life either."

She chuckled and blushed a bit and said, "Sorry to hear that."

At the Christian college Lauren graduated from, everyone there believed that you should wait for marriage to have intercourse. That explained why so many of them got married right after graduation.

Over the first month she worked for us, as our conversations became more and more personal, I learned that she had a high school boyfriend with whom she had had sex, but her boyfriend at college wouldn't have sex with her until they were married.

As she approached graduation, she found out that her boyfriend had been fucking his high school girlfriend, which, she said, explained why he never really pressured her into sex.

I asked, "Didn't you guys do anything?"

She paused for a second, and said, "Well, let me put it this way, I'm really good at giving blowjobs."

Now it was me who blushed.

Fast forward about two weeks - that comment had been on my mind (and in my pants) since she made it, and I was anxious to see where I might be able to take it. Sex with Caitlin had dwindled to pity sex every couple weeks, without very little oral to speak of, so it was starting to become a mini- obsession. I love oral, giving and receiving, so I was living in a fantasy over Lauren's mouth since that comment.

One day Lauren was supposed to take the kids to a friend's birthday party at Chucky Cheese or someplace like that, and meet Caitlin there, but I secretly arranged for a neighboring parent to take the kids instead of Lauren taking them.

I got home early and began my usual chat with Lauren, who then said, "Well, I guess we better get going."

I said, "Oh, I guess I forgot to tell you, Mrs. Smith is taking the kids to the party since she's going too."

Just about that time, the bell rang, and the kids said their goodbyes and off they went, with me telling them their mom would meet them there.

I knew I would be alone for the next two or three hours, so I invited Lauren to stay and have a glass of wine. She accepted, and now the ball was in my court.

Lauren wasn't exactly shy, and like I said I could tell she had a bit of a naughty steak (which she confirmed with the blowjob comment), but taking it to the next level would be delicate.

After a few minutes of friendly chit chat, I asked her, "So, I'm curious, with your last boyfriend, you said you took care of him, but did he ever take care of you?"

She looked confused for a second, then blushed with understanding.

Looking away, she admitted, "Not really, no. Occasionally, but honestly, he didn't seem to like that, and it showed. He wasn't good at it."

I said, "Well that's too bad, stuff like that should work both ways."

She paused, then asked, "Does it work both ways with Caitlin?"

I said, "It used to, early on. The but last few years it has worked mostly one way, me giving to her, with an occasional pity blowjob, but even that has really stopped. In fact, you couldn't even call it a blow job anymore, she doesn't do it to completion, if you know what I mean."

She looked at me wide-eyed, like it never dawned on her that oral sex could be used only as foreplay.

She stammered and said, "You mean, she never, in her mouth, like, swallowed it?"

Now I was getting bold, loving where this might be going.

I replied, "Never once. In fact, the one time she took me 'all the way' (I used air quotes) early in our marriage, she made me tell her when I was going to come, and then she just let it shoot all over the place. She was kind of grossed out by the whole thing and hasn't done it since. She hates the, you know, 'end product.'" (air quotes again).

After a brief silence she said "That's too bad. I find the whole thing hot, and I love it, especially the 'end product.'"

Now it was time to be even bolder. My first boss once told me, if you want someone's business, sometimes you just have to ask for it instead of beating around the bush.

"You gotta take your shot!" he would say.

So, I took my shot.

I looked at her and said, "Would you do it to me?"

Even though she knew what I meant, she played the game, asking, "Do what?"

She was going to make me say it.

"Give me a blow job, and swallow my cum, right here, right now," I said.

We were sitting across from each other in a little sitting room off of the kitchen. Lauren put her glass down, took three steps over to me, and dropped to her knees in front of me.

She whispered to herself, "It's been so long" and reached for my belt.

I had kicked off my shoes, I was in my dress slacks, which she easily unzipped and slid down over my feet. She rubbed her hand over the bulge in my underwear, and said, "Oh my."

Time to brag a bit.

Early in our sexual relationship, Caitlin had measured my dick at slightly over eight and a half inches long and seven inches around.

In college, I had earned the nickname "Q." Apparently, word got around that my dick was the "size of a cucumber" and my cock head and balls were "as big as cue balls." Hence the play on words: "Q." An exaggeration of course, but you get the picture.

When Lauren pulled my underwear down and saw my cock stand up as hard as it's ever been, the look in her eyes was pure hunger and disbelief. She had told me that in addition to her college and high school boyfriends, she'd jerked off one other guy in high school a couple times, so she'd only ever seen three dicks before.

She looked at my dick hungrily and said, "I've never seen anything so big!"

I enjoyed a swell of pride. It had been many years since anyone made a fuss over my dick, so I soaked it up with joy. This was soon forgotten, however, as Lauren leaned forward and slowly ran her tongue over the head of my cock. She looked me in the eyes as she ran her pursed lips up and down the front of my shaft, and returned to the head to lick away the precum.

I grabbed my shaft and started to stroke myself a little, which fascinated her, probably a first for her to watch a guy stroke himself.

I said, "Lick my balls," and she eagerly dropped her mouth to my sack and swirled her tongue around my balls, sucking each one gently into her mouth as best she could. After a minute of this, I grabbed her by the hair (gently at first) and moved her mouth back to my cock and worked the head between her lips. Then I pushed her head down slowly onto my cock, and let her take over from there.

Pure heaven!

She took me about half way down and used her hand to perfection in sync with her mouth and tongue. Up and down, alternating between eye contact and looking at my cock, and I could feel myself reaching the boiling point.

I decided not to tell her when I was going to come, but instead just let it happen. I grabbed her head and held her still, firm but light enough that she could pull away if she wanted to, but she didn't. She kept her head still and took my cum.

My cumshots are not for the faint of heart. Typically, my loads consist of about five or six hard shots, then three or four smaller shots, then dribble for a couple seconds. Probably a good quarter of a cup or more, and bigger in the morning for some reason, or if I've been holding it for a while.

I could see Lauren's cheeks fill up with cum and hear her throat working to swallow it all. She eagerly took it all, and it must have been a monster load since it had been a while.

She kept her mouth on my cock until she was sure I was done, then she sat back on her haunches and said, "Holy Shit! That was awesome! I wasn't expecting so much. It just kept coming and coming, no pun intended."

I could barely speak; it was the best blowjob I had gotten in at least ten years.

I stammered something stupid like, "You're telling me," And pulled my clothes back on.

She sat back down, finished her wine, looked at her phone and said, "I better get going, working an evening shift tonight."

She grabbed her purse, leaned over and gave me a quick peck while I sat there with my mouth hanging open, opened the door and said, "See you tomorrow."

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Over the next few days, I thought about how this could be a more regular thing. She lived with her parents, so meeting at her place was out, and my time alone with her always involved two kids in the house.

Our TV Room had a sliding pocket door which separated it from the dining room, sitting area and finally the kitchen, where Lauren and I did most of our talking. Over the following weekend, I installed several nanny-cams in the house. One was pointed right at the sliding door. I had connected a closed-circuit link to the computer on the desk in the kitchen.

The following week when I came home a bit early, Lauren had just come inside with the kids, and they had settled into the living room to watch whatever the latest Disney movie was. Lauren and I sat in the kitchen talking. It had been about a week since our encounter, and I was anxious for more. At first, like the last few days, we went about our business like nothing had happened.

Finally, I said to her, "I really enjoyed last week."

She paused and said, "I did too," then turned to put some dishes in the sink. I walked up behind her, moved her pony tail to the side, and lightly kissed the back of her neck.

She froze at first, but instantly melted. To this point we hadn't even kissed. How many times in your life do you get an A+ blowjob without having first kissed the girl? She turned her head toward me and I kissed her, gently at first, but then harder.

She froze and said, "We can't, the kids."

I walked toward the living room, poked my head in and saw the kids under blankets watching the movie.

I said, "Hey kids, I'm gonna close the door, the sound is loud and Lauren and I are talking."

They grunted something like "OK," and I closed the door.

I walked back to the kitchen and opened the computer and up popped a live feed of a camera pointing right at the sliding door.

Lauren gave me a mischievous smile and said, "Wow, you've really thought about this huh?"

I walked to her, kissed her deeply and rubbed her firm tits through her blouse.

She rubbed the bulge in my pants and said, "Well I've been thinking about THIS" and dropped to her knees in front of me.

There I was, back against my kitchen counter, alternating between watching the babysitter suck my cock, and the image on the computer. If the door opened, I figured I'd have about seven seconds to get my cock out of Lauren's mouth and get my pants up. I just hoped I'd never have to find out if that was enough time.

This position gave me a much different angle than sitting on a chair. I could look straight down at her and look into her eyes while she pleasured me. She cupped my balls, nibbled the head of my cock a little, but then knowing we might be short on time, really got after it. Deeper than before, she swallowed about three quarters of my cock and stroked me with her hand.

Before long, I erupted, holding her head still and pumping my cum into her mouth. This time she pulled back a little so that the cum pooled in her mouth rather than going right down her throat, not an easy task with the volume of my typical loads. Again, she held that position until I was done throbbing. She let my cock fall from her mouth, opened up to show me my load, then swallowed it all down.

She stood up, kissed me on the lips (I could taste my own cum a little) and said, "Your cum tastes good, Caitlin doesn't know what she's missing."

With a quick goodbye to the kids, she was gone.

This pattern repeated itself once or twice a week over the next two months or so. Lauren willingly sucked my cock, swallowed my cum, cleaned up the dishes, and went on her way.

I was starting to feel guilty - not over my wife, but because I wanted to pleasure Lauren in return. I wanted to taste her so bad, I'm sure her pussy was pure gold. I thought about how I could pull that off, but it seemed to me it's riskier to eat pussy in a kitchen than to give a blowjob, just in terms of the positions you need. I'd gladly lay her on the kitchen table, spread her legs, and tongue her pussy until she came, but I'm not sure seven seconds would be enough to pull ourselves together if the door opened.

I wasn't worried about Caitlin. She always parked in the garage, and hearing the garage door open would be plenty of warning. But I couldn't risk being busted with my face between the legs of the babysitter by the kids.

One time I did whisper to Lauren something like, "I'm desperate to return the favor."

Her response, "Maybe someday," was all I needed to hear to keep hope alive.

During this period, Caitlin and I did have our standard duty sex every two or three weeks.

One time she said, "You haven't asked for oral in a while, how come?"

I replied, "Well even though I love it, I know you'd rather not do it anymore, so I've kind of given up on it."

Yeah, it was a cheap shot and designed to make her feel guilty about how little she cared about my wants and needs, but I didn't care. I was getting regular blowjobs, and there was no risk that pissing off Caitlin would result in any less sex.

Caitlin surprised me by going down on me that night, although as usual she faced away from me and I couldn't see her face. Caitlin gives pretty good head. We'd been together for a long time, so over the years, especially in the beginning, she had perfected giving me oral and understanding how to pleasure me. I've never had a complaint about the quality, when she was into it. Enthusiasm is the key to a good blowjob.

She was doing her thing and it was feeling pretty darn good, different from Lauren but really pleasurable all the same.

One time I had asked Lauren, "Is it OK that I don't tell you when I'm going to come?"

She said, "You don't have to, I can tell. Your dick gets just a little bit harder and the head swells up a little about five seconds before you come, so I'm always prepared."

Armed with this information, I decided not to tell Caitlin that I was going to come. She was probably expecting that the oral would be foreplay, as it almost always was, and I'd eventually stop her and fuck her in one position or another. But once she felt me harden and swell, she'd get the message, and the next move was hers.