I do a bit of traveling locally and I usually stop in the same places for gas and lunch and whatever. I guess I am what is referred to as a regular. Anyways, there is this little diner I stop at about once a week. I usually sit in the same booth and have the same waitress. Becky is in her late 20’s, mom of a 8 year old. She had her kid just out of high school and married the guy who knocked her up. She is tall, about 5’10” and she is all legs. Nice tight ass from working on her feet all day, and B cup tits. I would not describe her as curvy, she is more of a twig. She is nice to look at with a fairly decent crooked tooth smile, and she has a pleasant personality.
Lately Becky has been a bit flirtatious. She started dropping sexual comments this summer and I chalked it up to her hustling for a bigger tip. I don’t fall for that kind of thing so I just have been kind of letting it go. About 3 weeks ago she really changed gears. She moved on to straight up propositioning me. I blew it off for the first two weeks but last week I called her out on it. I told her it wasn’t nice to tease an old guy. (I am 48) She followed up that is wasn’t a tease. She told me that the bit of grey in my hair made her wet as hell. She said I could have my way with her anytime I wanted. This woke my cock up and immediately let the little head take over the thinking for me. I laughed and told her I was a kinky old perv and she should be careful what she asked for.
She looked me dead in the eye with her hazel eyes and said “challenge accepted”. I told her that I really enjoyed eating at this little diner but I don’t think I could look her in the eye after I had seen her O face. She laughed and said I would have to hit her from the back then. I told her I had a better idea. She told me that she got off work at 2 and her kid got home from school at 3. Her hubby worked 2-10 at the local Foundry and if I wanted to meet her at her place at 2:15 we could get a quick fuck in before 3 o’clock. I told her to text me her address and I would meet her at 2:15. She brought me over a Red Bull on ice with my bill and told me I may want to slam it to kick my old ass into high gear.
I left the diner and saw an appointment. I cancelled my 2:00 and headed to the grocery store. I bought a gallon of ice cream and a black magic marker. I asked the clerk for a paper bag and I headed over to Becky’s house. It was a cute middle class ranch home about a mile out of town. I pulled my truck in the driveway behind her SUV and went to the side door. She was waiting for me in grey sweatpants and a white t-shirt. It was obvious that she was naked underneath. Her nipples poked into the winter air as she opened the door. She asked what was in the bag. I showed her the ice cream and had her put it in the freezer. I told her I bought the ice cream just to get the paper bag. She looked at me with a confused and innocent face. I wrote “slut” on the bag with the marker and told her to put the bag over her head.
She looked a bit confused until I told her I didn’t want to look at her face, but I wanted those beautiful long legs wrapped around me while I fucked her. She instantly responded with a serious “Yes Sir” and I knew this next 40 minutes was going to be intense. She put the bag on and asked what I wanted. I told her to stand there and not to move until I told her otherwise. I pulled her grey sweatpants down with one pull and lightly brushed her thighs and ass with my fingertips as I walked around her. Her skin immediately showed goosebumps and her nipples stiffened up and I grazed her stiff nipples. I told her to raise her arms above her head. She obediently obliged me and stood there with her sweat pants around her ankles, her shaved pussy exposed and her t-shirt lifted slightly above the slight stretch marks that marred her otherwise incredible figure. I lifted her shirt to expose her breasts. They were no longer full and had a bit of a deflated look to them. I am sure she was self conscious of them. I could see a tear making it’s way down her neck from under the bag. I caught it with my index finger and asked if she was alright. Her response was “never better Sir” in a quivering voice. I reminded her that I was a kinky old fucker and I would stop if she wanted. Becky responded with “Feel my cunt sir and tell me what you think.” I slowly traced my finger over her tiny belly and gently probed her labia with my middle finger. She quivered ever so slightly as I felt what could possibly be the wettest and warmest pussy I have ever experienced. I told her that she was as moist as a piece of homemade cake and she giggled just a bit.
I pulled her arms through the t-shirt and left it hanging around her neck. I twisted it to choke her just a little bit and walked her across the house to her and her husbands bedroom. The comforter was pulled back already in anticipation of our mid afternoon hook-up. I bent her over the side of the bed while holding the t-shirt around her neck. I told her to keep those long legs straight as I stepped back to look at her dripping wet pussy peeking at me between her spread legs. I love this view more than anything and I savored it for a few moments. I looked over at the clock on the dresser and it said 2:30. I didn’t want her kid walking in on this, so I decided to pick up the pace a bit. I could lie and claim to be some sort of stud with porn star endurance, but that is not the case. I figured with a few position changes I may last 15 minutes with this long legged lolita. I took off my shoes, pants and dress shirt and stood behind her. I thought she may be close to orgasm from her wetness and I thought I should take care of that first so as not to totally disappoint her if I prematurely ejaculated. I put my left hand on the small of her back and traced my right hand up her inner thighs until I cupped my palm against her labia and used my index finger to find her erect clit. I told her not to move as I probed her cunt to get my finger wet with her surprisingly slippery wetness and then I slid forward to her clit. I gently rubbed as she shook and bucked. I enjoyed watching her legs quiver as I eased her through her first orgasm.
I then firmly slapped her on her ass and told her to roll over because time was a wastin’. I pulled my boxers down and put her knees over my shoulders as I wasted no time plunging my 6″ of erect disappointment into her exposed and open vagina. I used my thumb to massage her clit as I raw dogged this waitress on her bed. Her wetness was nothing short of amazing. She wasn’t a squirter, at least not for me, but oh my. I pumped for a few minutes and she pushed back and did her best to show me how well she fucked. I slid her long legs off of my shoulders and they found their way around my waist as I got as deep as I could into this young mother. I probably should have worn a condom, but I am the king of pull outs and I wasn’t too concerned, until she locked me in with those legs. I decided to slow her down by playing with her tits a bit. I know she wasn’t too proud of the way they laid there deflated while she fucked me missionary. Her pace slowed considerably and I was once again in charge. The bag on her head was starting to work it’s way up from our carnal wrestling match so I reached up with both hands and pulled it back down over face. The look of this skinny mom with “SLUT” written on the paper bag covering her face was a little too much for my perv mind and I had to abort the mission now, before I impregnated this fertile fox.
I did my best Randy Macho Man Savage and broke free from the death grip Becky Wonderlegs had around my waist. I sat on her chest and pinned her down while I jacked myself off into the paper bag encasing her head. I looked at the clock, 2:52. I had about 4 minutes to find my clothes and get the hell out of there. I jumped off of Becky and the bed and grabbed my pants. Becky sat up and pulled the bag off of her head. Her face and hair were covered in my 3 day build up of baby batter. She looked at me with a deadly serious stare and said “What the fuck?”. Then she cracked a smile with her crooked white teeth and said, “We are for sure doing this again.”
I may have to find a new lunch stop.
Source: reddit.com/r/gonewildstories/comments/eq92eh/fantasy_happened_unexpectedly_mf
This was just depressing