Lilly's First Handjob

This is my first story submission for Literotica. I trust you will enjoy it and would love to hear your feedback.

A special thanks to volunteer editor Phone101 for her work on this.

** All characters in this story are 18 older **

*****

The knock on the door came as a surprise at first, but then I remembered that we had organized for Lilly from across the street to come and look after the kids while my wife and I went out for a work function dinner and drinks.

As Angela, my wife, was still in the en-suite blow-drying her hair, I jumped up off the couch expecting to open the door to who I thought would be the awkward, shy young girl whose family had lived directly across from us for as long as I could recall. Instead, when I casually opened the front door, I received quite a surprise.

Replacing my mental image of a short, scruffy brown-haired girl with braces was the now very grown up Lilly. While still shorter than my 5 ft 9, she was clearly taller than I recalled. However, it wasn't her height that caught my attention. It was a warm afternoon so she was dressed for comfort with cute blue shorts made from a very thin fabric, revealing the outline of darker underwear. She also had on a very bright yellow top, which highlighted the perfect set of very ample breasts that defied gravity and hugged her cotton tee tightly.

I had only a second to make this observation when I was met with yet another surprise. No sooner had I fully opened the front door when Lilly beamed at me with a big smile and stepped inside with an enthusiastic hug. "Hi Mr. Andrews," she said, still beaming. At that point, Lilly perhaps realized that pressing herself against me so enthusiastically may have been just a bit too friendly. She she took half a step back and reset herself, her eyes darting to the ground.

I took this opportunity to quickly look her over head to toe. Her hair was quite long and neat and was tied back in a ponytail that hung forward over her shoulder. Under her well-developed breasts that surprised me, I noticed that her frame was otherwise quite thin but filled out in all the right places. She was, dare I say, a perfect 10...and lucky for me was now 18 years old.

Before I could say a word Angela appeared from the bedroom en-suite , still wrapped in a towel, and greeted Lilly with a smile. "'Come on in Lilly, you're just in time. We're heading off in 5 minutes. Just make yourself at home". Lilly did just that, regaining her earlier excitement, skipping forward into the house to see the kids. I paused a moment before closing the front door to watch her skipping along, with those wonderful breasts bouncing as she went.

For a teenager, it was an easy gig for easy money. Basically Lilly just had to hang out with the kids for an hour, tuck them into bed, and then watch TV until we got home. After Angela gave Lilly her instructions for the evening, we headed out for dinner and drinks.

It was a work related function so the next few hours went quite slowly and I found myself reflecting on that friendly hug that Lilly had given me when I opened the door for her earlier that evening. Her young, full and firm breasts felt wonderful for that brief moment when she said hello and pressed against me, but I imagined that they would feel even better in my hands. Of course that could never happen. I'm sure that by now Lilly would have a boyfriend and would not be seeking out the attention of someone old enough to be her father, but at least it was a thought that I could carry with me when I fucked my wife after we got home.

Actually, by that time, it was looking like sex was off the cards for the night as Angela had just had a few too many drinks of wine and could barely stand after our night out. When we got though the front door, I helped her straight into bed and said I would check the kids, sort out paying Lilly for her time, and make sure she got home safely too.

As expected, I found Lilly plonked down on the couch watching TV with the kids having gone to bed upstairs hours ago. Once again I was met with that lovely beaming smile from earlier. "Oh hey Mr. Andrews, how was your night?" she said, jumping up from the couch. But she was just a bit too chirpy, I thought, and I detected that she was slurring her words a little. As if she saw me processing the situation, once again her eyes went to the floor and the smile receded. "So, where's Mrs. Andrews?" she said as if trying to divert my attention from my current thoughts.

"She had a pretty big night and went straight to bed, and it looks like perhaps you've been doing the same," I said, as I fished a vodka-mixed cocktail bottle out from behind one of the cushions on the couch and held it up to her face. Immediately the smile from Lilly's face fell. "I thought it would be ok to have a few drinks after I put the kids to bed." But she couldn't have been more wrong.

I was furious. "We're not paying to you to sit on our couch getting drunk Lilly. If you think I'm mad, just wait until I tell Angela!"

At this point, not only had the smile gone from her pretty face, but tears began to fall down her cheeks and Lilly slumped back down on the couch. "'Oh please don't tell Mrs Andrews, I couldn't bear it if she was angry with me and told my parents."

At that moment my wave of anger had passed and I felt sorry for Lilly. It also helped that she was so damn cute. "Listen" I said, "perhaps we can just let it slide this time but it can't happen again."

Once again, a beaming smile returned to Lilly's face, and she leapt up and launched forward, pressing herself against me with a firm hug. Still slightly slurring her words, and still wrapped around me, she sighed "oh thank you, Mr. Andrews. I promise I'll make it up to you."

I had to take advantage of this moment. Lilly's body simply felt too good against mine.

"Ok then, how about right now," I remarked with a bit of a chuckle, but hoping it wouldn't be taken as a joke. Understandably, Lilly seemed confused. "'What do you mean?" she asked, sounding uncertain.

"Well quite frankly I'm disappointed with what you've done, but I'm even more disappointed that my wife is too drunk to fuck me tonight, so I think you can help me out."

Hearing this, Lilly took a step back and then sat back down on the couch again, still looking confused. She hesitated with her words. "I, um, I don't know what to say. I know I messed up and don't want to get in trouble, but I've never done anything like this." To me, that sounded like she was willing to participate in whatever I had planned.

"It's ok Lilly," I said firmly. "'Just do what I say and everything will be just fine." I was surprised to see that Lilly smiled again at that point so I pushed on with the plan I was making up as I went along. "You can start by taking off your t-shirt and bra. You've pushed your tits against me too many times tonight to not let me see them." Amazingly, Lilly complied and I was rewarded with a spectacular view of her breasts as she stood up and followed my instructions.

I was now standing just a meter away, directly in front of her, and I whispered, "Lilly you are so beautiful. Come and give me another hug." As she stepped in and wrapped her arms around me, her bare breasts pushed against me.

My face moved down to kiss her on the neck as I brought my right hand up to cup one of her perfect tits. At that moment, she sharply breathed in. "Oh Mr. Andrews," she sighed, "I uh, I don't know."

I cut her off. "Don't worry, Lilly, you're just making it up to me, we'll be done soon."

With my face in the softness of her neck and with one hand on her breast, my cock was straining against my pants so much that it hurt. Continuing to hold her close I moved my other hand that had been resting on Lilly's back down to the zipper on my pants and with one swift movement I released my swollen cock from its confines. I then reached up and pushed Lilly's right arm down until I had her hand in mine and then moved it to my hard cock that was already leaking with pre-cum.

"Wha...what do you want me to do," she said nervously. "Like I said, I've never done anything like this."

I was somewhat surprised. "Don't you do this with your boyfriend?"

"N-no, I've never had a serious boyfriend...so umm."

"You've never had sex then?" I questioned, as I moved her hand to wrap around my cock.

"No, not at all," Lilly said quietly, as i felt the warmth of her hand squeeze slightly on my now throbbing cock.

"Well, don't worry about that right now, tonight you're just going to help me out a little. Let's sit down on the couch, and I'll show you what I need you to do." As I said this, I lifted her so she could look into my eyes and then directed her to sit next to me. With her topless and with my hard cock poking out of my pants, it was quite a sight.

As we moved into sitting position I made sure that her small, warm hand never let go of my cock which was now quite slippery. "Just move your hand slowly up and down sweetie, and give it a bit more of a squeeze when you're at the top," I said, as i moved her hand though the motion. It felt simply wonderful as she continued to do this for a few minutes while I proceeded to cup and play with her perfect young tits. All she could do the whole time was stare at her hand moving up and down my shaft, occasionally licking her lips and breathing deeply.

I felt myself getting closer to blowing my load. "Ok Lilly, spit on your hand, then start moving it up and down faster and hold my cock tighter. We're almost done." For someone who had never done this before, Lilly certainly had magic hands and 15 seconds later I shot a load of cum so high into the air it ended up in her hair.

I chuckled, "don't worry, that will wash right out. You'd better get dressed sweetie."

As Lilly put her bra and shirt back on, I leaned forward and pushed some 50 dollar bills into the back pocket of her shorts, taking the opportunity to squeeze one of her firm ass cheeks. As I did this, I wondered how it might be to be able to explore this part of Lilly further. "Ok, you're all set sweetie. Good job...I mean good hand job anyway," I laughed.

Even Lilly managed to crack a smile at this as she headed towards the front door, again giving me a great view of her ass in those tiny shorts. Just as she was about to walk out, I remarked, "I think we might need you again next week Lilly," and winked at her.

Lilly winked back. "Sure," she said with a smile, and closed the door.