tagMatureFucking My Babysitter, 25 Years On

Fucking My Babysitter, 25 Years On

byjjames1976©

This is a true story that happened less than a month ago. I have been going over and over it in my head since it happened but without anyone I can really talk about it with I felt the urge to write it down and submit it here, I hope you enjoy....

I grew up in Melbourne, Australia, but now live and work in Sydney.

Having not being able to get back home for christmas due to work, I arranged to come home and see my parents for a weekend right after New Years, arriving Friday and flying out again on Monday.

My parents however were leaving town for a couple of weeks Sunday night to celebrate their 39th wedding anniversary and then go and visit their grand children. I decided to stay the extra night anyway so I could maybe catch up with some old high school friends or just take it easy, any excuse to take Monday off work.

The weekend flew by quickly and uneventfully, but it was nice to just be hanging out with my parents and relaxing in the old home I grew up in. Before we knew it it was Sunday night and after a rushed early dinner I helped load their luggage in to the car so I could drive them to the airport.

While on our way out there my mother got a call on her mobile. I wasnt really paying attention to the conversation until I heard her say:

"Um, yeah I guess thats fine, the only thing is James will be there tonight, if you dont mind that I'm sure he wont either." My mother said.

Oh great I thought, which of my parents friends have I just been signed up to entertain tonight.

"Remember Rebecca?" My mother asked after hanging up the phone. "She used to babysit you when you were little."

"Yeah I Do." I replied.

In fact I remembered her well even though I hadnt seen her for probably more than 15 years. When I was about 11 or 12 she used to babysit me after school until Mom or Dad got home from work. She was the daughter of their friends and roughly 10 years older than me, and back when I was 12 I was totally infatuated with her.

As far as I could remember she was the first girl I ever really had 'those' thoughts about and I remembered how I used to think she was the coolest and most beautiful girl in the world. She had the most beautiful face that was almost always sporting big round sunglasses and a cheeky grin, with long light brown hair almost to her waist, and a nice slim athletic figure. But my strongest memory of all was of her amazing and very large breasts. To this day I still remember the extraordinary time that I came home from school to find her sunbathing in the backyard facedown with her bikini top untied. I sat outside near her pretending to play my state of the art "catch the parachutes" handheld video game when really I was just staring at the side of her boobs.

I saw her whole breasts briefly soon after as she sat up a bit to put her bikini top back on. I must have thought about that moment thousands of times over my early teenage years.

"Well." My mother continued. "She is back in town until the end of January, and since her parents place is going to be crowded with all the other kids, we are letting her house sit at our place while we are away. She was going to be coming Tuesday, but now it looks like she will be coming late tonight. I hope that's ok with you, I've made up the spare room for her, show her where the extra bedding is if she needs it."

"Yeah thats all fine." I replied.

I was acting casual but I did feel a little wave of excitement and nervousness run through me, as well as several other thoughts, I'm 35 so she must be about 45 now I thought. I wondered what she would looks like now, and I wondered what her breasts would be like now.

I got home and showered and then got comfortable on the couch and watched some tv while drinking a gin and tonic (the only alcohol I could find in the house). That helped ease a few of my nerves about being reunited with the woman I used to fantasize about as a teenager.

I think I must have drifted off for a bit because before I knew it was 11 o'clock and there was still no sign of Rebecca. Just when I was considering going to bed I heard a key turn and the front door open. I jumped up and turned to meet her.

"Oh sorry, I didn't know if you'd still be up and whether to ring the bell or not, so I just used the key your mum left for me. So, Hi James! Wow look at you all grown up, you're looking good, I hardly recognised you." She said cracking that same cheeky grin I remembered from over 20 years ago.

"Hi!" I said enthusiastically greeting her with a hug. "You're looking good too."

"Oh I dont know about that she said." She said with a laugh.

I laughed too "Yip, tell me about it." I said awkwardly not really knowing why I said that. She was older looking than I had expected but still looked great for 45, the long brown hair was gone and was now shoulder length and blonde, I liked it, it looked very youthful and cool. And she also no longer had her slim figure but was by no means fat and still very attractive. She was also not as tall as I had thought, she was 5 foot 5 at most, I am 6 foot but for some strange reason I was kind of expecting her to be bigger than me still.

She was wearing all black, a skirt that went down below her knees, a tight long-sleeve top with a thin see through a short-sleeved blouse over top. I couldn't be shore with just a quick glance but it seemed her breasts had gotten even bigger than I remembered.

"Your room's down here." I said grabbing her suitcase and pointing down the hall. She walked ahead of me down towards the spare room giving me a good chance to check out the rest of her figure. I noticed she still had quite a slim waist but quite a sexy big round bum that looked great in her tight black skirt. All in all she was still very hot, an older more curvy version of the 22 year old beauty I remembered.

After showing her to her room I returned to the lounge and made myself another gin and tonic,

"What ya drinking?" Rebecca said as she rejoined me in the lounge.

"My parents Gin and tonic." I said with a smile. "Would you like one?"

"Um Actually I brought a bottle of wine with me." She replied "I think I might have a glass of that."

So, we sat and drank gin and wine and talked for quite a while, reminiscing about old times, me telling her about living in Sydney, her telling me about Queensland where she had lived for the last 10 years. It was good fun.

"Wow, look at the time." she said eventually. "I think I'm going to jump in the shower and then hit the hay."

"Yep true, I should get to bed too, back to sydney tomorrow for me." I said yawning and stretching out my arms.

"Well it was great to catch up." She said standing up and momentarily loosing her balance.

"Whoops! I guess 3/4 of a bottle of wine will do that to ya, time for a lie down." she said giggling.

I stood up too and she hugged me goodnight. Feeling her breasts press against my chest was a nice little thrill to end the night I thought.

"Night James, It was fun catching up with you finally." She said as she headed off to her room.

As I was cleaning up the kitchen I could hear the shower running and couldn't help but imagining her in there drunk and naked with water and soap running all over her hot curvy body and how amazing it would be to be in there with her.

I was still in the kitchen when I heard her leave the bathroom and go in to her room and close the door. I thought that was going to be the end of our little reunion. Oh well, I thought, I guess I should get some sleep too. I was in the process of turning off the lights when Rebecca popped her head out of her room. Although she was trying to hide it I could see she was still wrapped in just a towel with another one wrapped round her head.

"Um James, this bed is really soft, and I have all kinds of problems with my back."

I wonder if that's her huge breasts fault I thought to myself.

"Well." She continued. "I see there is actaully two mattresses on here, do you think your mother would mind if I took the soft matress off and just slept on the bottom one."

"Yeah of course, that's fine." I said. "I'll help you move it off"

"Ok Great, just give me 1 second to get dressed first." She said as she closed the door behind her.

"Ok come in." She yelled out moments later.

I went in to find her sliding the sheets and blankets carefully off the top matress. she still had a towel wrapped around her waist covering her lower half, and she had put on a black t-shirt on over top.

I saw what she meant when we moved the matress, it was incredibly soft, as it buckled in half as we lifted it off the bed pulling her forward on to the bed letting out a rather loud "Fuck!" as she fell.

"You ok?" I asked.

"Owww that hurt, tweaked my damn back, I'll be ok." She said putting her hand to her back.

"Are you sure Rebecca? I'm sure my parents have some pain killers around or something that would help."

"It's ok thanks James I have some with me, lets just get this matress out the way so I can lie down."

We moved the matress out in to one of the other bedrooms and re-made up her bed again, Rebecca laid down carefully and said:

"Ah thats much better, thanks so much James, you're a life saver."

"No problem, are you shore there's nothing I can do for you and your your poor back?"

Although I wanted to I stopped myself from offering a massage but to my surprise, and delight, she cracked that cheeky smile and replied:

"Well, if you could give me a teeny wheeny back rub while I blow dry my hair that would be devine."

"Sure no problem." I said trying to act casual again but feeling another wave of excitement flow through my body.

"You're the best!" she said plugging her hair dryer and perching herself on the edge of the bed. I went and sat behind her and asked her where it hurt.

"Everywhere!" She laughed. "But just below my shoulders its really bad." And with that she turned on her rather loud hair dryer, leaned her head forward and started drying her hair.

I put my hands on her shoulders and started massaging them through her t-shirt, as she started slowly straightened her back, correcting her posture. I then started running my thumbs in circles slowly over her upper back.

The loud hair dryer stopping any real chance of small-talk which was fine by me. Although as I worked my way down she arched her back and I heard her faintly groan in appreciation. Then she turned off the hair dryer and placed it down on the bed.

"Oh god that feels amazing james, please dont stop yet." She said as she turned and lay down flat accross the bed sideways. "Just a few more minutes, pretty please!"

I moved to the middle of the bed, kneeling beside her and continued working my way slowly down her back.

Rebecca's t-shirt had ridden up a little exposing a small strip of her lower back just above the towel. I gathered up some courage and casually grabbed each side of her t-shirt and pulled it up to just below her breasts exposing her whole lower back. I continued massaging her lower back with Rebecca now getting more vocal with each stroke, softly moaning as I rubbed my hands slowly up and down her back. Each time I moved my hands higher up her back I pushed my hands further up under her t-shirt, pushing it higher and higher up until the sides of her breasts were partially exposed.

Rebecca had a nice tanned back but I could now see the side of one of her breats and it was completely white. I now ran my hands up each side of her back running my fingers very close to the sides of her breasts, she let out a long moan and I felt my cock starting to grow.

Getting more confident by the second I grabbed the t-shirt again and asked:

"Can we take this right off?" As I started sliding it over her head not waiting for an answer.

"Ok." She said a little hesitently as she raised her arms allowing me to slide it off completely, then resting her head on her hands again.

The sight of this hot older woman lying topless on the bed combined with her moaning sensually every time I ran my hands over her naked body had me so turned on my cock was growing harder by the second.

I decided to move positions so I was straddling her thighs with her legs together, still wrapped in the towel. I ran my hands in broad strokes all the way up her back to her shoulders, leaning over her pressing my now hard cock against her ass.

"Oh God." She said softly.

I then ran my hands back down the sides of her back, running my hands slowly over the sides of her breasts each time.

This continued for a while longer, slowly pressing my cock against her ass while running my hands over her entire back while she moaned more and more. At one stage I slid my hans right under her breasts and start squeezing and massaging them, running my hands over fingers back and forth over her nipples. Neither of us said anything apart from the occasional moan. Next I slid down her body and told her I was going to work on her legs.

I moved down so I was straddling her lower legs just below the towel. and started massaging one of her calf muscles, then working my way slowly up her leg pushing my hsnds up under the towel. Getting halfway up her thigh then moving to the other leg and working up that leg, getting higher up her thigh this time, massaging higher and higher up her inner thigh. Then back to the other leg, my hand getting so high up her inner thigh this time my hand brushed against her underwear.

.

"Oh you are wearing underwear, we wont need this towel then." I said to which she laughed and replied:

"oh wont we?"

I Unwrapped the towel and pulled it out from her. I then stood up and removed my shirt and shorts so I was just in my boxes. I straddled her thighs again staring down and her big sexy ass in her plain blue underwear that covered her whole ass. I put my hands on her upper thighs and worked my way up to massaging the bottom of her hot ass and rubbed my thumbs up and down the sides of her pussy through her underwear. She was getting wet through her panties as I slid my hands under the material and grabbed and massaged her cheeks, this time running my thumbs under her panties and up and down the wet lips of her pussy. She kept moaning and breathing faster as I continued massaging her ass and pussy.

I then slowly slid off her panties and took off my boxes making us both completely nude.

"We shouldn't be doing this." She said as I climbed back on top of her so my hard cock slid between her ass cheeks and pressed against her pussy, I leaned over pressing my chest against her back, sliding my hands under her and grabbing her breasts and started kissing her neck.

"Do you want to stop?" I whispered in her ear as I squeezed her amazing breasts.

"Mmmmmm no." She groaned "Fuck me."

I sat back up spreading her legs apart, and moved so I was kneeling between them, grabbing my hard cock by the shaft and rubbing the head of it up and down her dripping pussy.

"Mmmmmm God, fuck me James!"

After teasing her pussy a little longer I slid my cock inside her. My cock is pretty big and thick and she let out a loud "Uggh, my God" as I slowly pushed it deeper inside her pussy. I Grabbed her ass in my hands spreading it apart as I started sliding my cock in and out of her.

Both us were moaning as I leant over on top of her again, reaching under her and grabbing her breasts, squeezing her hard nipples pressing my body against hers, sucking on her neck and shoulders as I pushed my cock deeper inside her pussy.

"Mmmmmm harder James." She moaned.

I sat up again I pulled her back up on to her knees and start fucking her doggy style.

"Oh god, harder, harder." She cried

I started pounding her faster and harder from behind, her breasts were slapping together, my balls were slapping against her pussy.

She was moaning loud and shouting: "Mmmmm dont stop! Don't stop! I'm going to cum!"

While still fucking her pussy I took my middle finger and sucked on it getting it nice and wet before sliding the tip in to her hot ass. She moaned hard and I felt her pussy squeeze my cock tighter.

I pushed my finger deeper up her ass while still pounding her pussy from behind while she screamed:

"I'm cumming I'm cumming!"

I felt her pussy tighten and squirt cum all over my cock as she fell forward flat on the bed with me collapsing on top of her.

"Oh fuck, oh fuck that was amazing, did you cum yet?" She asked me.

"Not yet, turn over I want to cum on your breasts." I replied.

She rolled over and I straddled her waist, she took my cock in her hands and starting jacking me off. It felt amazing watching her lying on her back with her huge tits shaking inches from my cock while she stroked my cock faster and faster. It wasn't long before I came hard all over her breasts and stomach.

We both passed out shortly after and we only had a quick conversation in the morning as she was leaving to go see her family. She gave me a kiss and with a wink said:

"Well thanks for the fun night, if you are ever in Queensland we should catch up again."

We exchanged phone numbers and she was gone and hadn't returned by the time I left for the airport.

I have been feeling weird about that night ever since, but I cant stop thinking about it and am already thinking about making my way up to Queensland for a visit. So maybe there will be a chapter 2 to this story sometime in the future.

Hope you enjoyed it anyway, felt good to write it out and kind of 'tell someone' as I have not told anyone in my real life about what happened.

Report Story

byjjames1976© 3 comments/ 94530 views/ 12 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartmondotoken, ahbhu and 10 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (3 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (3)

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel