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My Night with the Waitress, Part 1 of the Night

"This was written for a a special peron to me! I hope she likes reading it completed."

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I had been on the road all day and was tired. It was about 10pm at night, and snowing. I had been fighting the snow for hours as it came down in sheets. I came upon on this little diner with plenty of room to park my tractor and trailer. I hadn’t seen anyplace else in hours so I turned into the lot. I could tell it hadn’t been plowed since the snow started. I had to cut a path through the snow just to park.

I got settled and looked over at the diner and only saw one car parked out front, but the open sign was on. It had been hours since I had been out of the truck so I figured I’d at least get a cup of coffee and some eggs, if I could. I got out of the truck and stepped down into well over 12 inches or more of snow. I hadn’t realized the depth of it on the road. I trudged on over to the diner’s door and had to pull it open against the snow that had piled up. I didn’t see anybody as I walked in and gave a low shout to see if anybody was here.

This little gal of about 5’4” tall came from the back. I was struck by her delicate looks. She had shoulder length light red hair, a small figure with nice breasts, that looked full, and a cute little freckled face. If I had to guess her age, I would say she was barely out of her teens.

“Can I help you sir?” she asked.

It took me a moment to answer because I was so awestruck by her. “I was hoping to get a cup of coffee and some eggs maybe?” I finally replied.

“I’m sorry sir, but the diner is closed,” she told me.

I just looked at her a little dejected. She must have felt sorry for me, because she decided to make a pot anyhow. I asked her what she was still doing here if the diner was closed and she told me her car wouldn’t start. She said she didn’t have anybody that could come to get her tonight with the weather the way it was. So she decided to just spend the night in the manager’s office, but must have forgotten to turn the open sign off before going back there.

“Oh, where are my manners? I’m Wendy,” she said to me.

“I’m Sam, Wendy,” I said to her.

She fixed me a cup out of the new pot and pulled herself one. We sat chatting and I discovered the cook had taken off without making sure she was ready to leave. Typical jerk of a kid, is what I thought. I discovered she had a 3-month old baby at home, with her mom babysitting. I also found out the father had high tailed it out on her the moment she found out she was pregnant. I felt sorry for her having such a tough time of it. We continued to chat for about an hour, when I noticed it was getting cold in the diner. I asked her what was up with the heat and she told me it was on a timer. She said there was a blanket in the manager’s office she was going to cover up with to keep warm.

I sat there for a few minutes thinking about her being in here in the cold and I’m out in my nice warm truck. I just couldn’t do it.

“Wendy, I’m not trying to be forward here or anything. I have two beds in my truck and I keep it warm all night. If you’d like, you can take my extra bed. Then in the morning I can see if I can get your car started or somebody will be here at the diner again,” I told her.

“I don’t know. You seem like a nice guy, but I just met you,” she replied. She was also thinking to herself that he is a good looking guy and seemed pretty decent.

“Well the offer is there. I don’t want to see you freeze in here tonight.”

We sat and chatted for a while longer as we finished the coffee. I was getting ready to go back out to the truck when she spoke up.

“I think I’ll take you up on your offer of your extra bed. It’s gotten way colder in here already,” she said.

I replied that was good. I didn’t want her to freeze or get sick. I told her to lock up or whatever she needed to do, Then I would walk out with her.

She went in the back and turned off the lights in the place. Just a faint glow from the security and emergency exit signs glowed when she came back up to the front. She had pulled on a jacket while back there. We headed for the door and out to my truck. As we walked towards the truck Wendy said it was a pretty color even under all the snow.

I reached up and opened the passenger door for her. I showed her where to grab to climb up in the cab. She reached up and grabbed the handholds, but couldn’t quite pull herself up into the cab. I reached out without even thinking, and put my hand on her ass, running my hand along her crotch and giving her a small goose in the process. My intention was just to give her a slight boost, but my hand slid on her pants. She jumped a little and turned around to look at me. I apologized for touching her that way. She just looked at me, then smiled and got on into the cab. I hoped there was no harm, no foul. I went around and climbed in the driver’s side.

“You made it look so easy getting up here. You didn’t even need somebody to feel you up, did you?” Wendy said to me with a smile.

I just kind of turned a shade of red at her comment. “I’m so sorry that happened,” I said to her.

“Oh, it felt kind of nice. It’s been a while since I had a man’s touch,” she replied.

“Still I’m sorry for that,” I said. “You can swivel the seat using the lever by your knee. Then just stand up and come on back here into the sleeper area. I’ll get you all settled in for the night.”

She swiveled the seat and stood up. I motioned for her to come on back. Being a custom sleeper I had more like a small efficiency apartment instead of a normal sleeper. I pointed to my table indicating she should sit down. I turned and was getting ready to lower the extra bunk from the wall when she said I wouldn’t need it. Surprised I turned back to her and she was just removing her jacket. I just looked at her for a moment.

“I would like to repay your kindness of offering to keep me warm,” she said.

She stepped up to me and kissed me hard on the mouth, sliding her tongue between my lips to dance with my own. To say I was shocked would’ve been an understatement, but I think I recovered reasonably well. I reached around her and pulled her tight to me as I returned the kiss with the same passion. We held the kiss for what seemed a long time before we both came up for air.

Wendy stepped back from me and started to pull her shirt over her head when she stopped suddenly. I figured she was having second thoughts about this. Then she swore a little bit and I just looked at her wondering what I had done. I guess she saw the questioning look on my face.

“Sam, I’m sorry! I wasn’t swearing at you or about you. I told you I have a baby at home. I’ve been breastfeeding her since birth. I have to use a breast pump before coming to work so mom has milk for her. I’m usually home by now to feed her. I noticed as I was taking my shirt off for you that I’m leaking breast milk. I do that when I don’t use the pump or get to feed the baby.”

Wendy stood there telling me as she was topless. I could see a thin milky layer on her nipples as I was looking at her beautiful full breasts.

“Here let me get you a towel or something,” I said.

She saw I was a little transfixed on her nipples with the milk leaking from them. Wendy looked at me and said “Haven’t you ever seen a woman when she has been breastfeeding?”

“No,” I replied a little unsteadily.

Standing there in her jeans without a top on, she beckoned me to her.

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“Come here a little closer to see. See how the milk runs from my nipple. When my baby nurses she pulls it right through my nipple,” Wendy said.

As she was explaining this to me, she was gently squeezing one of her nipples and I could see the milky fluid pool on it. I was just staring transfixed at the sight of what she was doing.

“Would you like to taste my milk?” she asked, taking her finger and running it through the small pool of milk that had gathered.

She lifted her finger to me offering it to me to suck on. I leaned forward and took it in my mouth, gently sucking it. The milk tasted sweet on my tongue, not what I would have thought.

“Wendy, that was a taste I had never experienced before. Thank you so much for sharing that with me,” I told her.

Wendy smiled and said, “So you liked it? Come here -- I will give you a better taste.”

She reached out and pulled my head towards her breast. I leaned forward and took her nipple in my mouth, gently sucking it. I tasted her milk, but I didn’t feel any more coming from her. She told me to suck much harder than I was. The baby has to draw it from her as it will only leak small amounts. I did as I was told, and sucked much harder. As I did this she let out a very excited moan of pleasure. I started to taste her milk now. It seemed the harder I sucked the more milk I got from her breast, but also the more she moaned in pleasure.

I was loving the taste and texture of her nipple as it was flowing her milk in my mouth. She took her hands and pulled me from her nipple to my disappointment. My disappointment was short lived as she guided my head to her other breast. I quickly took this nipple in my mouth and started sucking her for all I was worth. My reward was a steady stream of milk coming from her breast into my mouth. As I was doing this she continued to moan more loudly.

I realized as I was sucking her nipples she had unbuttoned her jeans. She had slid one of her hands down the front of her pants and was slowly massaging herself. I decided she might need some help so I took a hand and cupped the crotch of her jeans over the top of her hand. I pressed into her hard, pushing her fingers tighter to her mound. This elicited another longer moan from her.

“OH GOD! This feels so good. You’re sucking me so hard compared to my baby girl. I get so aroused when I nurse her and now I can feel my pussy just flooding my panties,” Wendy moaned out to me.

I withdrew from her nipples and took her head in my hands. I leaned into her for a long passionate kiss. Our tongues danced their dance, as I helped her continue to massage her pussy. I turned her around towards the bed and gave her a slight push. She flopped back on the bed with her legs hanging over the side of it. I reached down and grabbed her feet pulling them to me. I untied her work shoes and pulled them off. I then grabbed her socks and gave them a quick yank. I just tossed everything behind me not really caring where it landed.

I held her feet for a moment kissing her toes and the tops of her feet. She giggled and squirmed a little on the bed. I reached up to right above her knees and grabbed a handful of her pants. I could see they had already worked down her hips some, so I just gave them a quick tug pulling them down her legs where I slid them the rest of the way off of her. This left me looking at the sexiest and wettest pair of light pink panties I had ever seen. I could see her pussy lips through the wet material of her panties. I just stood there staring until she spoke up.

“Hey are you going to just stare or you going to get in here with me?” she said, smiling at me with the sexiest smile.

I didn’t need to be asked twice. I stood before her and stripped my shirt off. She whistled a little at me so I gave her a little pose. She giggled and waved me on. I unbuckled my belt and turned my back to her as I slid my pants down. I slid my underwear down with my pants so I was standing bare assed towards her. I heard her moan a bit, so I turned to look. I saw she had a hand in her panties, fingering herself and the other hand pinching a nipple. I stood awestruck as a large squirt of milk arched from her nipple and landed on her taut, smooth belly. I instantly became harder than I already was seeing this. I finished stripping and slid onto the bed beside her.

“Oh my breasts are so full of milk. I need you to help me relieve some of my discomfort,” Wendy said with a pleading smile. She reached out and pulled my head towards her breasts whispering for me to suck her until I was full.

I obediently did as I was told. Taking one of her nipples in my mouth and sucking greedily on it. She moaned loudly as I sucked. Suddenly I felt her hand reach for my hard cock. She wrapped her hand around my cock and started to stroke me lightly. I adjusted to make her reach easier. She continued to stroke my cock as I was sucking her nipples. I would alternate between them, always keeping the pressure on her nipples to get all the milk she had to give.

She was moaning and squirming as I sucked her nipples and she stroked my cock. She pushed my head away from her nipple, and then she pinched her own nipple hard.

“Open your mouth wide for me baby,” she said to me.

I did as she said and was rewarded with a long squirt of milk from her nipple right into my mouth. I was in heaven right then with this young lady. She continued to stroke my cock as I sucked and played with her breasts. I reached down with a hand to find her mound. I slid my hand over her tender button and she jumped. I could feel how excited she was. I slid my hand on down to feel her swollen lips. She moaned as I ran a finger between them. She continued to stroke my cock as I was stroking her pussy along the lips. I started to lift my head from her breasts and she said, "No" as she pushed my head back onto her breasts with her hand. Who was I to argue with this young lady? I was loving the taste of her milk and she was reeling in pleasure from it.

I felt myself getting harder in her hand. I was getting close to cumming, as I laid there sucking this beautiful girl’s milk-giving breasts as she stroked me. The closer I got, it felt as though she could feel this. She started stroking me faster, pulling my hard cock for all she was worth.

“Oh Wendy I’m going to come if you don’t stop,” I told her around the nipple I had in my mouth.

“I know you are,” she replied to me. With that she redoubled her efforts on my cock. I couldn’t stand it much longer and forgot all about stroking her pussy. I took both hands and cupped her breasts sucking each greedily as she was bring me closer to climax.

She bent down and kissed the top of my head just as I started cumming. I shot my cum all over her tummy and even splashed some close to her breasts. I reached down with my tongue and licked it off her skin and returned to her nipple, sucking gently in the post climax moment. I finally stopped sucking her nipples and pulled back a bit to see the mess I had made. I had never seen myself cum so much. It was pooling on her tummy and trailed all the way across her. I had clearly made a mess.

I looked up at this young lady and I could see the absolute delight she had in her eyes.

“Wendy, that was so intense. I have never experienced the sensation of a woman’s milk before. Then to have you make me cum as I was nursing from your nipples was so amazing,” I stammered to her.

“Oh Sam, you don’t know how good it felt. I really did need to relieve some of the pressure, but now I’m so...

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