Babysitter Tom

The date was a total bust. Fred wasn't a bad guy, but we didn't connect at all. He was fairly attractive, but came from the corporate finance world; and as a single mum, I was the last thing he needed in his life. I was more than relieved to jump into a taxi and head home by 9pm.

Let me tell you a bit about myself to start with, before I go any further -

I'm 32, brunette, and of mixed race. My mum is from India, and my father is English. I'm fairly petite at 5ft 5inches tall, and my skin tone is a light olive brown. My daughter Cassie is four years old, and she means the world to me. Since her father left three years ago I have been completely focussed on Cassie. I run a small internet business from home, which allows me to easily shuffle work and family life.

Tonight was the first time I had been out on a date in about two years. I don't really have a lot of time to date at the moment, but every so often I accept an offer for a night out. Shame it didn't work out with Fred. Better to know sooner rather than later I guess, although I was kind of hoping to get laid. It's been a while.

When I stepped out of the taxi I could see the lights on in my living room. I looked through the window and watched Tom for a moment before I headed towards the door. Tom lived with his parents around the corner from me. He had just finished school, and was eagerly waiting to start university in a couple of months. I had known him since his family moved to the area a few years ago, and he had always been my go to guy when I needed a babysitter. He had a real connection with Cassie, and I knew with him, she would be in safe hands; he really loved her like a brother.

Tom came to greet me at the door when he heard me turn the key. He had a gleaming smile on his face, as he held the door open for me. Such a gentleman.

"Cassie is fast asleep, Mrs Lewis. She was good as gold!"

"Good good. You know I'm never worried when she's with you." After taking off my coat I checked on Cassie and she was in a deep sleep. I closed her door, than headed back down. I noticed the house was looking in great shape and I looked to Tom.

"Sorry Mrs. Lewis. I just had some time to spare after Cassie fell asleep. Don't have any work to do over the summer, and nothing was good on telly earlier!"

"You're a real star Tom. You can call me Elaine you know!" I couldn't believe he had vacuumed! The one job I hated the most.

"I know Mrs. Lewis!" he said through a big cheesy grin. "How was your date?"

"He was okay I guess. Don't think I'll be seeing him again though."

"Oh no! Sorry to hear that!"

"It's okay! So what's your plan for the rest of Saturday night? Time for you young things to head out?"

Tom started laughing. "Not tonight. I'm just going to relax at home." As Tom stood up and turned off the TV I watched him. His figure was incredible. His arms had just the right amount of muscle, and his chest abs could be seen through his t-shirt. He was perfectly groomed as always and had a smile that melted my heart.

I felt my pulse start to race as I told Tom I was going to open a bottle of wine, and asked him if he wanted a glass.

"Sure Mrs. Lewis. Like I said I've got nowhere to go tonight!" I told myself he was eager because of the free alcohol although other thoughts began to scratch at the back of my head.

I fetched a bottle of Shiraz from the kitchen, and Tom grabbed the glasses from the cupboard. We sat down on the small two seater sofa and we spend the next half hour talking about everything under the sun. He told me about his university course; and his friends and family.

As Tom topped up my glass of wine he changed topics. "So do you think you'll be in need of my Cassie sitting services again before I head to Uni?"

"Not sure yet!" I smiled. "Have to see if I'm given another reason to go out again!"

"I'm sure you'll find somebody soon." Tom said as he looked at me and smiled.

I couldn't take my eyes off Tom. There was something about him that was alluring me in a way I couldn't explain. There was something new about him - something different. He was no longer the kid who used to walk past my house every morning. He was changing into a real charming young man. I reached out and grabbed his hand. "I will. Don't worry about it. I wish there more guys out there like you! You girlfriend is so lucky to have a guy like you!"

Toms hand didn't pull back. In fact, quite the opposite. His fingers closed around my hand and he looked me right in the eye. "I don't have a girlfriend Mrs. Lewis. I've been waiting for the right person."

I felt an overwhelming urge to lean forward and kiss him! What was going through my mind? This was my neighbour's 18 year old kid. He was over ten years younger than me. It took a lot of self-control to hold myself back, and an even longer time to decide how to respond. I was going to ask Tom to tell me about his last girlfriend, to try and take the focus off the two of us, but my words came out all wrong. "When were you last with a woman Tom?"

I didn't actually hear the words come out of my mouth, but Tom's jaw dropped and he began to stutter. "Erm. Erm. What do you mean? I mean...I mean it's been a while. I mean.. I've never really.."

"Oh my gosh. Tom. I'm sorry. That's not what I meant. I mean I was asking when you last had a girlfriend." I could feel myself blushing, and I was stuttering myself! I felt like a school girl with her first crush! I noticed that Tom had pulled his hand back. I looked up at Tom, I was feeling flustered; his eyes were focussed and trained on mine. No his eyes were seeing into my soul. Piercing right through me.

He tried to speak but I could tell his mouth was to dry. His mouth just hung there. Open. Right in front of me.

No words came to my mind either at that moment in time, but I managed to reach out towards his hand slowly. His hand came and met mine half way and before I knew it our fingers were interlocked. I looked up from my hand and met his gaze, no longer as a friend but something much more.

I could hear Tom's heart beating loudly as I leaned forward towards him slowly. I took the wine glass out of his other hand and placed it on the table a few inches away. All the time, slowly leaning closer into him.

"Mrs. Lewis." Tom said quietly as I placed my hand on his face.

"Yes Tom?" I asked passionately. Tom looked away quickly. I knew there was something he wanted to say, but he just didn't have the courage. "Tell me Tom. You can ask me anything." I whispered.

His eyes flickered between my eyes and lips. He was trembling slightly and I soon realised it was fear of rejection, not the situation holding him back.

"Do you want me to teach you about being with a woman Tom?" I wasn't sure if it was the two glasses of wine at dinner, plus the one just now; or the fact that I was incredibly lonely and horny, but I couldn't believe what I was suggesting. I felt butterflies in my stomach; my heart was pounding in my chest loudly.

Tom's eyes lit up a moment later and he leaned in towards me. He let me pull forward the last inch as he closed his eyes and I planted a soft delicate kiss on his lips. It wasn't until a few hours later that I would discover that it was actually his first kiss.

The kiss was short, sweet and passionate; it left us both desperately wanting more. We both pulled away and just looked at each other, silently asking each other if we were sure if this where we wanted things to lead.

My mind was screaming at me to stop. This was my neighbour's kid, ten years younger than me! His parents were friends of mine. My heart and body was telling me something very different. They were urging me to lean in, tear his clothes of and let him fill me up with his passion.

I could tell by his huge smile that he wanted this as much as I did, and I leaned forward once more into another kiss. We were both a little more forward and aggressive this time, letting not only our lips meet but my arms wrapped themselves around his neck tightly.

The kiss was remarkable. I felt breathless and winded, and his skin was so soft and smooth.

I pulled away after a few moments and stood up, I felt a little dizzy. I alluringly walked towards the living room's door and closed it. The last thing I wanted was Cassie to walk in. As I walked back to Tom, at a snail's pace, making him wait and linger in the moment I noticed his jogging bottoms. Being a soft material the bulge was incredibly noticeable and I was transfixed.

Tom noticed what I was looking at, and his first reaction was to cover it up. Before he got a chance to I was stood right in front of him. I clasped both his hands in mine and wrapped them around my waist. He tried to stand up, but I pushed him down and I leaned forward and kissed him once more. I felt like a mistress, taking care of a king. I was filled with years of lust that was primed to explode, and I could tell so was he.

"Mrs. Lewis." He moaned as I began to kiss his neck. His shoulders. His biceps. His forearms.

I let me tongue run all the way to the tip of his fingers. "Promise me Tom."

"Anything." He moaned.

"This will stay between us. Only us. Nobody can find out. Not your friends; not your family. I can't have this coming back to Cassie."

"Okay." He moaned as I grabbed his hand from around my waist and moved it to my breast. I could see I would have to help guide Tom.

I moaned out as he began to squeeze. Noticing my response he quickly moved his other hand to my other breast and began to massage them both in unison and squeeze. The feeling was incredible. No man had touched me for far too long, no man had made me feel so wanted in far too long.

I wrapped my hands around Tom's neck once again and kissed him passionately. This time I leaned in and was tempted to sit myself on his lap. I held myself back and instead I dropped to my knees in front of Tom. My hands moved down slowly while I tickled his tongue with mine and I pulled his t-shirt over his head slowly.

His chest was incredible. It was chiselled like a painting, and not a single hair stood on it. It was perfectly smooth and unblemished, like a master piece of art. I ran my hands over his chest and I began to kiss his chest. I was surprised to see how hard his nipples had become; and I instantly became aware of how hard mine were. I could feel them pressing against by black lace bra, and my full length red dress.

I licked his nipples and he moaned as his hands fell to his side. After several long moments, I felt his hands brush my hair behind my ears, and his hands reached for my breasts again. This time it was easy for him to locate my nipples through my dress and bra and he squeezed hard and tight, and gently twisted.

I completely lost control. I knew it would happen sooner or later, but it was sooner than I had anticipated, and I wasn't mentally ready at all. But that's what made it amazing. I felt as if one million caterpillars had erupted into butterflies in the pit of my stomach and between my legs. I was burning, my whole body on fire. I couldn't control the orgasmic contractions, and my eyes were lost in Tom's. My jaw hung open and Tom sat there smiling with joy.

It took me a few moments to recover, but when I did I kissed Tom hard and whispered a big thank you in his ears as I stood him up from the sofa. I wrapped my hands around his waist and began to pull down his jogging bottoms. I left them wrapped around his feet as I looked at his black boxers. I wanted to saver this moment before I pushed things further, but I knew there was no going back. I leaned forwards and gripped his underwear with my teeth and pulled them down gently, letting my fingers tickle his legs as they descended.

As his boxers slipped over his penis, it recoiled, and slapped across my face.

It was all I could have dreamed of. It was a penis out of a pornographic movie. It was perfectly shaved, circumcised, and the size was immense. As it stood tall against his stomach it went past his belly button by at least two inches. It was magnificent. In terms of actual size I couldn't say for sure, but it was definitely the longest and widest I had ever laid eyes upon. I looked up at Tom who once again stood there smiling, nervous and almost dumfounded. I stretched my hands upwards and pushed Tom back onto the Sofa as I leaned in for a closer inspection.

I used my hands to gently tickle behind his knees as I took my first lick. It was slow and long. His penis bounced forwards a couple of inches as he felt the warmth of my tongue. His moan was deep and full of relief, and the drops of pre cum that surfaced told me to move on quickly. He wouldn't last long.

Down on my knees I could feel my pussy juices were now dripping over my ankles; fortunately all hidden by my long dress. I placed my two hands against Tom's chest and pushed back hard. He wasn't going anywhere.

I looked into Tom's eyes as I ran my tongue up the outside of his thick long penis very slowly. I stopped an inch from the top and then once again licked up the left hand side, then the right. I could feel Tom's heart beating heavily.

I closed my eyes as I ran my tongue around the tip of his cock. He moaned and shuddered as I did so, and I couldn't help myself from wrapping my lips around the tip of his girth tightly. I closed my eyes and pushed back hard on his chest as I slowly let my mouth engulf Tom's girth.

I focussed on the top three inches, moving my lips up and down, swirling my tongue over his delicate skin. His breathing became heavier as I slipped my mouth further down his cock. His cock hit the back of my mouth and I was struggling to let my mouth open wide enough! I could feel the edge of my lips straining around the monumental girth, and when I opened my eyes I almost gagged, realising there was still another three and half inches to go!

God his cock was huge.

I pulled back for a moment and Tom opened his eyes. "That was amazing Mrs..." before he could finish his sentence I forcefully wrapped my lips around his cock and pushed down as hard and as fast as I could. His long thick penis was stretching my mouth in every direction and I couldn't remember the last time I felt something so sensational and satisfying. The girth was putting so much pressure on my lips that they felt on the verge of tearing. As I pushed down I could feel his cock pushing deep into my throat. I could feel the base of his cock against my lips. Somehow I had managed to swallow his whole girth.

"Oh my god..." He started moaning as I sucked deep and hard. I was a little shocked to feel Tom's hands on the back of my head, keeping me in my place.

I loved it.

I sucked harder and deeper, as he moaned louder and louder. A part of me prayed that Cassie couldn't hear, but another part of me didn't care. It was mummy's time to play, and God this was a good game.

I suddenly gagged on Tom's cock and pulled away quickly. Tom's moaning and breathing was heavy and I knew he wouldn't last much long. Tom was young and I was sure he would be bounce back quickly, so I pulled my hands away from his chest and began to massage his balls as I began to focus on the top few inches of his cock again. I sucked as tightly as I could, almost squeezing the life out of it. I knew soon my reward would come, and I would saver every last drop.

Tom's moaning became deeper and louder over the next few minutes until he started begging me not to stop. "Please...don't stop Mrs. Lewis. Please. That feels amazing...oh my god." I stopped letting my lips do the hard work and let my tongue take over. I swirled it around the tip of his penis delicately and massaged his balls with my right hand, while I used my left hand's nails to gently scratch at his legs and chest.

"Oh my God. I'm going to...I'm going to cum Mrs. Lewis...Don't stop." Tom's voice became almost high pitched as engulfed his cock in between my lips once more and gently bit down around his girth.

The sensation I felt, as his cock began to pulsate wildly in my mouth was incredible. His whole body was jerking; the tip of his cock was wrestling with my throat. I was on the verge of Cumming again he hadn't even laid a finger on my bare flesh as yet! A moment later he let out a loud moan as his penis erupted.

And man was it an eruption. It seemed to last for minutes. I could feel the heat and pressure firing against the back of my throat. I did everything in my power to stop myself from gagging this time, and managed to pull back just enough, so only his tip was tightly nestled between my lips. I suddenly became aware of his hands over my head again, and I heard myself breathing as heavily as he was, but through my nose.

My mouth was full, completely full. My eyes were bright and wide, and looked at Tom who looked as if he was about to pass out, but with a huge smile across his face. I looked him dead in the eye as I slowly raised myself to his eye level. He looked at me breathlessly, and I opened my mouth slightly to show him how full it was; as I did a small portion of his cum dribbled down my chin. I quickly closed my lips and swallowed everything. The feeling of his thick cum flowing down my throat left my body tingling. It was a little salty, but tasted amazing. I wanted more. I had a huge grin on my face and so did Tom.

Tom grabbed my waist and pulled me close. My body slumped on top of his and I could feel his cock against my dress. His penis was still jumping, and I leaned in closer to feel the revel in the sensation. He wrapped his arms around my neck and kissed me. I was a little shocked, but what really took my breath away was what he did next. He licked his own cum off my chin then kissed me deeply. The feeling of our tongues swirling together over his cum was something new and exciting. Something I had never experienced before. This was a boy, no a man, who was completely comfortable with his own sexuality.

A couple of minutes later I pulled away to catch my breath. "Mrs. Lewis that was amazing. I don't know how to ever thank you."

I just looked at Tom and smiled for a moment. Before I could decide on what to respond Tom kissed me once more. He slowly stood up with my arms tightly wrapped around his neck. My legs wrapped themselves around his waist. I was not ready to let go yet.

Tom walked me slowly across the room and sat me on the corner of my dining table. I pulled him close and watched him eagerly as his hands wrapped around me and began to pull at my dress. I inched myself off the table, and a moment later my dress was slipping over my shoulders, and then onto the floor.

"Wow." Was all he could say with words. His penis was growing hard again which told me all I needed to know. I tried to kiss him once more but he pushed me back, and lay me down over the table. My legs dangled over the edge, as Tom stepped in closer to me. His ever growing penis rubbed at my black lace underwear, and he leaned down on top of me. I could feel his warm minty breath on my face as he began to kiss my neck. His hands pulled my arms out, high above my head, as his kissed me all over. His fingers slowly tickled me, as he worked his hands towards my bra.

I struggled to keep myself from pulling him straight into me, and I almost lost control again when his strong teeth lovingly bit into my nipples through my bra. I had to cover my mouth from screaming out in ecstasy. His touch was strong and forceful yet delicate at the same time. Every time I tried to reach for my bra to open it he pushed my hands back into their rightful place above my head. I secretly hoped he would tie my hands up.

Tom kissed me again, this time leaving me feeling winded, then began pulling at the middle section of my bra with his teeth. He forcefully pushed my bra out the way with his mouth and a moment later my bra was around my neck. I smiled at him, impressed, and lifted my head giving him easy access to remove it completely.