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The World's Hottest Sitter Ch. 01

By: Reminiscing



Thanks to all who voted for my previous tale "My first time with Tammy." I have decided to commit my pre marital life to prose as some kind of reprieve from the constrictions that marriage makes so much of us feel. So what you read here is accurate to the best of my recollection, and is not aggrandized in any way. After the first story I received numerous messages asking whether that was my first time having sex. The answer is no. This is the first time I had sex...

And of course everyone in this story is over 18.

**********

I am the oldest of four children. We were quite the raucous bunch. Later in their parenting years my parents decided that they needed to spend time together without us. We loved that. Honestly. I was involved in sport with some aspirations of a career. My father supported this as he had played representative football and had then married the town beauty queen. When they went away for weekends a friend from church would stay over to mind us all. I was obviously old enough to do this, however I had to leave for training and should have been studying also.

The best thing about this friend from church was that she was hot. Smoking hot. Tina was 28, worked with horses at a racetrack and was definitely fit. Average height brunette with very pretty features covered in tanned skin. Never did I flirt with her. I could never get a word in edge ways due to all the men at church flirting their arses off with her. When I found out she would be staying at our house for three nights I had my first wet dream I was that excited. 

The first night she stayed I was at the gym until fairly late. When I got home Tina was bathing the younger kids and had already made dinner. Our parents were already gone. I told her I would have a shower and felt really awkward now that she was actually at our house. I'm sure she smiled at me the whole time. That is what I remember the most. Her perfect teeth. And her cheekbones. 

After I showered I walked to my bedroom with a towel around me. Tina bumped into me in the hall way as she left the kids room having just put them to bed. She was so much older than me I felt but so tiny when I stood over her. I could feel my cock filling with blood as she smiled up at me with her delicate features. I remember her telling me she would shower too and then tried to get past me. My fit body was still only capable of supplying blood to one place at a time and it got awkward as she tried to side step me.

Once back in my room I lay on the bed thinking about Tina in the shower. Could I peek? Try the I forgot something line? After only a couple of minutes the door was pushed open. It was Tina. Damn those country girls and their water saving two-minute showers. She was smiling at me, so I smiled back. She settled on the bed next to me, a towel wrapped around her. It barely covered her and boy did I notice. Her legs were fantastic, tanned, taught, shiny and smooth. All in two minutes? I still wonder how she did that.

Our conversation was verbose. Filled with nervous tension from me, and smug smiles from Tina as she realized how nervous I was with a girl on my bed. She asked me to detail my experiences with girls. I told her that I once had a girl friend and had kissed her numerous times even stripping her to her waist. We had fooled around in each other's pants but never gotten further. Tina asked me if I had ever had my dick sucked. I told her that I hadn't but would love it. She laughed, and told me that we would see. She kissed my navel and hovered over my legs. Her towel fell open, showing me her sexy little body. I actually looked at her stomach muscles and compared them to mine, just to make sure I was fitter! The vanity of youth.

When she pulled my towel open my cock sprang up. I didn't notice it getting hard. When her hand encircled me I went to heaven. I still love the feel of a feminine hand on my hard on, but then who doesn't. She sucked the head into her mouth with great force. I thought it was almost painful, but decided to defer to her greater experience. Tina sucked my balls, stroked me hard and had me ready to come in five minutes. I'm sure she wasn't trying too hard. 

"Do you want to come?" Tina asked me smiling cheekily. I nodded.

" Are you going to come in my mouth?"

"Not unless you want me to..."

"Since this is your first one, I think you should come as hard as you can. Make it good. Impress me"

Tina went back to a rhythmic sucking and stroking technique that I knew would get me there in no time. As soon as I felt the first wave of ejaculate pump up my cock I tried to come harder, make the pulses more powerful. Tina looked up at me for a few seconds. When I didn't stop coming she looked back down, her face contorting as she swallowed my load. The feeling was unbelievable. No orgasm is as good as having you come sucked out of your cock. As soon as I had finished Tina sat up, licking her lips. I pashed her. Kissing her intensely for a minute or so. She laughed again, asking me if I enjoyed it. I told her she was an angle of pleasure.

Then she patted my thigh, stood up and fixed her towel before walking out the door. My head spun with the complexities of this situation. My dad would probably be proud but my mum and her church cronies would lynch me. The next few days would be different to anything I had known before. Of that I was sure.

To be continued.....

The World's Hottest Sitter Ch. 02



This is a continuation of The Worlds Hottest sitter, please read it first. All my stories are as accurate as I can recall them. I will not embellish in any way, so I am sorry if some moments are awkward but that's the way life and love is! This story is my first time, which obviously occurred after I turned 18.

*

I lay in bed in a post orgasm glow considering the events that had just transpired. This amazingly hot woman had just given me my first blow job. As inexperienced as I was I knew it was good. Even today I doubt I've had better. I slept well after that and woke up early. I left the house for a big day of hanging out with friends, as teenagers do. I was apprehensive about going back to my house. I had never been in this situation before and didn't know how to handle it. I settled on smiling and nodding as a tactic. 

When I came home that night my smile was met with a cheeky smile back. I couldn't stop looking at her legs. Tanned and long in proportion to her small body. Little green shorts that were probably sprayed on, a white Singlet that hugged her tightly with a sports bra underneath. Her sly looks at me were probably meant to seduce me but instead made me nervous! I was young and inexperienced. 

When the young kids were in bed I crept into Tina's room. She smiled at me from under the covers as she read a book.

"Hello, are you looking for a replay of last night sexy?"

I could only grin.

"Well I think tonight is my night. What do you think?"

I smiled "What did you have in mind?"

I sidled over to her, lying on top of the covers. She pulled me to her passionately tongue kissing me. I groped her breasts until she pushed me away. Tina pulled her shirt off, the sports bra following it a moment later. I lowered my head down and began to lick them all over before nibbling gently around her nipples. Tina's hips began to thrust as I teased closer to her nipples. I loved being able to tease a lady I considered to be experienced and older. Well she was 28!

"Ok, now it's my turn." 

With that statement she kicked off the covers and pulled her white panties off. She spread her legs and pulled me toward her pussy. I knew what she wanted. I dived at her pussy, leading with my tongue! I lapped at it, I explored her folds, I sucked on her clit, I tongue fucked her little hole. The joy I felt at having a hot wet pussy at my disposal was incredible. I slid my fingers into her and gently fucked her as I licked her clit, trying hard to build a rhythm. I am not sure I was doing as good a job as I thought because Tina was able to quite coherently tell me to fuck her. Now!

I had planned for this to happen so I brought a condom with me. I knelt between her legs as I unwrapped it and tried to put it on. I had been taught that girls would want me to war one, but Tina was stroking my cock and raising her hips off the ground as if she wanted me to slip it in unprotected. Surely I was wrong.

I slid forward and lined up her pussy. Tina looked at me with the most lustful expression I had ever received. I sunk straight in to my balls. No having to work it in, or painful stretching. She loved every inch. I had to ask if I was big enough. Isn't that what happens? Women have to "handle" it? Tina laughed as soon as I asked.

"Its fine darling. It's the same as ones I've had before, but bigger than others. Its how you are going to use it that I care about."

That did it for me. I wanted to use it the best! Unfortunately I was a teenage virgin, and thrusting into a very hot, very wet vagina that belonged to the most beautiful woman I had ever seen did not conspire to make this a sex session of epic proportions. Tina grabbed my arse and pulled me toward her, putting her feet on the back of my knees so that she could thrust her pussy up at me.

"Squeeze my boobs," She gasped.

I did so. My balls tightened. 

"Squeeze my nipples"

My balls pulled up tight. I realized how full they were, ready to burst.

"Fuck! You are a hot fuck baby"

They spasmed. My cock turned to stone. My arse had a seizure, thrusting like crazy. As my testicles tried to jump out my cock I realized I was coming. Never had I come like this. 

"Oh baby, are you coming already?"

I could not reply. My face was numb. On and on it went. My self ministrations had never resulted in this kind of intensity before. What was going on?

As soon as I opened my eyes Tina laughed.

"Enjoy yourself? I thought this was about me tonight?"

"Sorry. I didn't even feel that coming. It just sorted of came over me. Fuck that was intense!"

Tina giggled, "I'm sure. What am I meant to do?"

I had pulled out and was removing the soaking wet filled condom from my cock. I stayed kneeling between her thighs as I tied a knot in it. Tina's hand found my cock and began to stroke it. I didn't realize I was still hard until she commented on it. 

"Could you do it again? It's still hard"

I was instantly nervous. 

"I only have one condom."

Tina laughed at me. 

"Don't you want to feel my pussy? I want to feel your cock. Not with plastic over it."

I expressed my reservations. Tina thought it was funny. She didn't criticize me, just giggled as if I was silly. A very serious matter to a young man. Then she rolled over onto her knees, looking back at me. Her aroused, shiny pussy was just beside her pretty face from my perspective. I could make an exception.

I moved between her calves. She arched her back. Her pussy opened. My cock throbbed. I slid it unprotected into her pussy. It was hot. It was wet. I pushed in deep and stayed still once I had reached as deep as I could. Tina moaned and squeezed. I moaned back at the feeling.

"I guess you like that? Fuck you are deep. That's intense."

I began to stroke. All the while noting how much of her juice leaked out around my cock. My pubic hair was soaked. My breathing shortened. 

"Pull my hair. Not to hard though. Grab all of it"

Was she serious? Why would you want your hair pulled? I did as she asked and started to ride her like a pony. My balls tightened again. This time I was scared though. What happens if I come in her? Best not too I thought.

"Are you going to come? Your breathing is really short?"

"I am tyring not too. You feel so good. Where do you want me to come?"

"Well, lets put that off until I have come okay? Just think about something else for a minute. Roll on your back and I will do all the work for a while"

I did as she told me.

It was so sexy as she held my dick and lowered her pussy onto me. All my life girls had played coy, like I was a sleaze bag when I smiled at them. Here was this woman enthusiastically humping me. I was in heaven. 

"I need to come, okay. Just hold off until I have had an orgasm and then it's your turn."

"What if I can't though? Can we just do it again in a little while?"

Tina had begun to grind down on me. I looked up at her titties, her rippling abs, and her pussy sliding across my pubis. 

"No, don't come in me. I'm not on the pill. You have to pull out okay? Just enjoy it."

I was really terrified then. I had just come and had no control over it. Why was I doing this? I decided to man up and try to fuck her properly.

Tina was in a world of her own on top of me. She rode back and forth-in ever-increasing sex frenzy. Closer and closer she came to coming. I realized I was in a race. Could I hold off for a longer period than it took for her to come? As she picked up the tempo again I realized that might not happen. As her breathing drew close together my balls tightened.

"I am about to come! Please stop!"

"Just a minute! Hold off! I'm going to come!"

My balls tightened further. I was terrified that I might come. I held off for another minute of two when suddenly Tina began to come. She rode me in a fury, grinding hard.

"Oh fuck I am going to come! Please get off me!"

Tina's only response was to keep coming. Maybe she started coming again. I thought about that as my balls erupted, my hips bucked again. Tina did not stop, grinding faster and faster on my ejaculating cock. My head smashed back onto the pillow involuntarily. 

Tina stopped thrusting eventually, collapsing onto my chest. 

"Fuck, I am sorry! I couldn't help it. You just felt so good. What do we do now?"

I was terrified of what just happened. I did realize as it happened though that this orgasm was bigger and more intense than my first one. Tina laughed as she caught her breath.

"I'm on the pill. I just wanted you to last a bit longer. Don't worry about it."

She lied to me! Oh well. I started to move again. I wanted to know what all the hype about sloppy seconds was about. And after all, I could come in her all I wanted...