Family surprise, part 1. Sometimes a person can surprise you, this is the story of the time an entire family surprised me. I suppose a bit of background is in order. My name is Mathew Webb, I'm 37 and a retired stockbroker.
Being retired my seem odd at 37, but the truth is that I made a lot of money in the .net bubble, cashed in my shares, and have been living handsomely on my investments since then. Life is good. Being so focused on my career I pushed people away, never forming a close relationship, and when I retired I was determined to make up for it.
It was 3 years of painful discovery, going from relationship to relationship with young women, always looking for the 20 year old bleached blond bimbo, always disappointed when they showed more interest in my money and material things than in me. That all changed when I met Laura. Laura was 35 and a single mom. Standing just five feet tall, brown hair, and not fat but definitely on the plump side, she was everything I never looked for.
We met at a local restaurant, I had stopped in for a quick bite and she was my waitress. She was just going to take my order, but with her warm green eyes, her friendly smile and - if I'm honest - her generous breasts, I stretched out the conversation.
The restaurant was quiet and she seemed happy to talk to a new face. We started off talking about the restaurant, but then I slowly moved it on to her, finding out her name, that she was a single mom, and that she was just working here so she could save up and move her family back to her parents in California.
I finished my meal and she brought me the bill. When she bent forward to put the bill on the table I couldn't help but stare down her top, her breasts pushing against her waitress uniform, my dick standing to attention.
God how I would have loved to put my dick between her breasts and fuck them till they were covered in my cum. I paid the bill, thanked her and was about to leave the restaurant when I thought fuck it, here was a women who knew nothing about me, seemed like a nice person, and who I would like to get to know better. Short story even shorter I asked her out, she said yes, and we've been going out for the last 2 months. I still hadn't met her family, but we'd spent a lot of fun evenings out together.
I'd kept hidden from her how much I was worth, even going so far as to buy a small car to take her out in, rent an apartment in town to take her home to, and let her pay for the odd thing.
I had to know that she liked me for me, and she did. We were on our way to her place after spending the evening at a comedy club and I decided the time was right to let her know the truth about me. She looked so good tonight, just in dark blue jeans and a loose red blouse.
I couldn't help glancing at her breasts as they bounced up and down in time to the car. "Take a picture", she said smiling, "It lasts longer". I blushed, I had been caught.
Laura reached out her small hand and put it flat between my legs, gently resting it on my dick. It began to get hard and I could see Laura feeling it grow. "I like you, let me do this" she said, then she undid her seat-belt, leaned over and pulled down my zip.
This may seem hard to believe but I was so determined Laura like me for me that I had held out on close physical contact. Tonight I couldn't hold back any more. As we sped along highway 15 I tried to look dead ahead, hoping no one could see what we were doing. Her hand felt inside my pants and her fingers grasped around my dick.
"Wow!" she said with a sly grin, "Somebody's been keeping a big secret from me" I blushed again, but God it felt good. I'd always thought my dick was pretty average, a shade under 8 inches, definitely not as thick as my wrist.
But hey, I guy likes a compliment. One thing I knew, I could come cum. A lot. Women often got a surprise when I came and I got a kick out of that.
Holding my dick in her warm fingers Laura pulled it out my pants. It stood up straight and hard and she slowly licked the top, circling her tongue over the head. She bent it back a bit and ran her tongue up and down the bottom.
Without taking her head away from my lap I heard her say: "I've waited so long for your cock, I wanted to do this from our first date." She kept licking before she admitted, almost guiltly, "At work today I fucked myself with carrot and pretended it was you." She licked some more, then chuckled, "I should have picked a bigger carrot" She then went back to licking my dick, her spit running down the shaft, then she opened her mouth and put it round the head, sucking softly as she kept licking the top.
She slowly moved her head down my dick, taking more and more in, trying hard to get down to the bottom but stopping with a couple of inches to go. She pulled out for a breath then dived back on, moving up and down faster now. I slipped my hand under her chest, cupping one of her breasts.
She moaned but kept on sucking. I could feel her hard nipple, and I took it between my thumb and forefinger, squeezing it through the fabric. I pulled it softly and she moaned some more. God her tits felt so good. She hadn't been sucking long but it had been so long since I had last had a women suck my dick that I knew I wouldn't last.
I told her so. "I'm gonna cum!" I shouted it, almost as a warning, I hadn't told her about how much I could cum and I wasn't sure how she would handle it, would she want to even keep her mouth over my dick when I came?
"Cum" her response was muffled, her mouth full of cock, and I did, I took my hand off her tit and put it on the back of her head, softly pushing down as I felt myself erupt. Spurt after spurt filled her mouth, so much that I felt her gag and some cum come running out of her mouth down my dick.
I felt like I would never stop cumming, but Laura kept her mouth over my dick long after the last spurt, her tongue lapping gently. She pulled her mouth up my dick, keeping her lips tightly closed and keeping as much cum as possible in her mouth. Eventually she reached the top of my dick and took her head off, sitting back up in her seat. She turned towards me so I could see her face, the cum dribbling over her full lips, down the side of her chin. She made an exaggerated swallowing motion and opened her mouth to show me it was empty.
I pointed to cum on her chin. She took her finger and scooped it into her mouth. Then she looked down at my dick and saw some cum still on it, she bent down and licked it up, running her tongue all around until it was clean. She tucked my dick back into my pants and pulled up the zip. Then she sat up in her seat and put her seat-belt back on.
I didn't know what to say, her mouth had worked so well, but I had done nothing for her. Yet.
We arrived at her house and I was wondering if she would invite me in, and maybe she would have, but at that time another car drew up. What the hell! I thought, don't tell me she's married. "That's my daughters," she said, "looks like there home early" Two girls stepped out the car.
Like their moms they were short, with brown hair, although unlike their mom they were skinny. I couldn't help but notice that both girls had nice breasts, not as big as their moms but a real handful. God what was I thinking, they were young enough to be my daughters.
Despite this I felt my dick begin to stir again.
I later learned that the older one was Trisha, she was 15, and the younger one was Kathy, 14. "I had a fantastic evening" Laura said, planting a soft kiss on my cheek, "see you tomorrow?" Without waiting for an answer she got out the car, smiled at me and walked over to the girls. Putting her arms around both she walked them in to the house.
All in all a great evening, and I hadn't even told her the truth about me yet. To be continued. Please let me know your thoughts, what you liked, what you didn't.
The story for part 2 already exists, since this is my life, but I really want part 2 to be fun to read.