My Second Time Being Milked

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A man enjoys being milked by girlfriend who adds another girl.
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NTsarina
NTsarina
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Author's note:

This is the second part of the "My first experience being milked" story. Since I spent a lot of pages setting up the story and introducing Hans and Annie in the first part, I decided to jump into the action from the start in the second part. I tried to find an editor, but no one responded.

*****

I looked down at the blonde head bobbing up and down and wondered how I could have been so lucky. My balls contracted and I let out a low moan as I filled Annie's mouth with my cum.

"Thanks honey. I really needed that," I said.

She licked my cockhead a few times and then wiped some cum off her chin with a finger and smiled at me. "You are welcome. I know things have been hard since we came back, but I am glad things are looking better."

She lay down next to me on the bed and snuggled in close. Her face was facing the window and her ass pushed against my cock. She was naked, Annie always slept naked. I cupped one of her breasts and slowly massaged it. She was warm and smooth, and so different than my ex wife. One of the reasons was that Annie was much younger, only twenty four, while my ex wife was close to fifty. I was forty five, but feeling like twenty five. Annie had that effect on me.

"You know that the big day is almost here," she said.

Christ, I thought, her birthday. I had tried not to think about it. Not that I don't love her, but she only wants one gift and that gift is something I don't like.

"Yeah, I know," I said.

"Are you nervous?"

"Not really, it won't be the first time."

She giggled, "No, it will be your third."

I let go of her boob and kissed her cheek, "What about a nice little cute puppy instead?"

She found my cock behind her and gave it a squeeze. "No, I want to milk you properly, and you promised you would let me."

I sighed and laid back again, letting her have her way with my cock, which grew hard again. Her ass felt very inviting so I adjusted my position and slid inside her wet pussy.

"Oh, that feels good, honey," she purred, and pressed herself harder against me.

I figured it was a good way to escape the inescapable, and grabbed her boob again while I fucked her from behind.

After showering together we sat down for breakfast. It was a sunny day in late October. We had been back in the states for about four and a half months. When we got home from the flight there was a letter waiting for me from my wife's lawyer where he said that she was going to sue for full custody of our son. The following months had been grueling, but now it was finally over. She had lost and I had the right to see him every other weekend. Then the bitch moved five hundred miles away, so it could only be ones every month. I didn't have the energy to go to court again, so I talked with my son and decided to do the best we could with the shitty situation. He is a mature fifteen year old, and one hell of a student.

During this time Annie had been a great support, not only emotionally but she had helped me with my construction business so I could work with my lawyer. She didn't know one thing about cement, wood, screws or nuts (pun intended), but she was a good administrator. My guys were a bit flirty with her in the beginning, but she handled that by telling them she was out of their league and she only had eyes for me. They sulked for a few days, but when they noticed she got more jobs for us, and therefore more income for them, they took her in as part of the gang. Annie was a great negotiator; she could talk a man into redoing his entire kitchen when he had just asked us for a cupboard.

I live in a University town somewhere in the middle of America. I wasn't born here, but moved to this town with my ex wife. She had been a professor at the University up until she moved away. It's a big place, I think there are some twenty thousand students and they leave their mark on our town. There are bars and burger joints on every street corner. In the summer you can walk down the street and enjoy watching coeds in tight t shirts not wearing any bras, and with long firm legs. I love it here.

"I'm going to that flea market today," said Annie, after we finished breakfast.

"Oh, OK. I thought you were coming with me to the office."

"No, you can handle it."

I put on a puppy face, and said. "But I will miss you."

She gave me a kiss on the cheek. "That's good, because it will be so much more fun when we see each other later."

We left at the same time, her on a bicycle and I in my truck. She would bicycle anywhere; I guess that's her Swedish part. Luckily, our town is flat like a pancake so it's easy to get around on a bike.

I met up with some customers in the morning and in the afternoon I spend time with my foreman going over new projects. It was hard to concentrate. Every hour that past brought me closer to the milking.

Annie loves to milk me. I have only done it twice and that was in Sweden when I first met her. I didn't know at the time that she had a fetish for it. It's not that it scares me. It's more that I don't like the feeling of having her finger up my butt. The sensation when she rubs my prostate is fantastic, but still it's not my thing. I love normal fucking, licking pussy and having my cock sucked. Maybe I am old school, but that's just the way I am.

When I drove up to the house I had rented I saw Annie standing outside talking to a man with a pick up.

"Hi honey, Tim here, was nice enough to drive me home with what I bought."

"No problem, have a nice day."

Tim got into his pick up and backed out. On the other side of the pick up stood Annie's bike and what looked like a table.

"Why did you buy a table, don't we have enough?" I said.

"It's not any kind of table, it's a portable massage table, and I bought it for us."

I put my arm around her shoulder and pulled her close. "That's why I love you. You always think about me, and now you can give me one of those Swedish massages every night."

She laughed, and said. "Not so fast. That table needs a bit of work, but when it's ready it will be my milking table."

I stepped away from her. "You're what?"

"Come here," she took my hand and pulled me along with her. When we stood beside it, she continued. "I will make a hole where your cock will hang down. I can sit on the floor under and just open my mouth and let your nectars drop down into my mouth."

"And who will make the hole, not me."

She picked up a bag next to her bike and opened it. "Roger was nice enough to show how to use this," she was holding an electric saw in her hand.

"Oh, I see. Well, while you play Bob the builder, I will be having a drink. See you later."

While I mixed a Gin Tonic in the kitchen I watched Annie working. Roger had been a good teacher. She was done by the time I had had my first sip. She folded the table and brought it with her.

"Make me one of those," she said when she walked into the kitchen. She had left the table in the hallway.

"How did it go?"

She drank some from her glass. "I'm very pleased; I think it will work great. You will find out tomorrow evening."

The following day was Annie's birthday. I had bought her a necklace and some clothes. I woke her up with breakfast in bed and sang happy birthday to her. Then we fucked and I left to work. She wanted to do some more work on her table she said.

After I finished work I went by a supermarket and bought some wine for the evening together with two steaks and a pre made salad. I had some potatoes at home; I would throw in the oven and make us baked potatoes. While I drove home, I thought about the table she was building and how much it meant to her to milk me. I thought it was an obsession, almost like an addiction. I had asked her where she got the need to do it from but she couldn't give me a straight answer. In the end she had put it down to control. She liked being in control of my orgasm, and she loved to suck the pre cum directly from my cock.

"I'm home," I called out when I closed the door behind me.

"I'm in the living room."

I dropped the bags in the kitchen and went to look for her. I found her standing by the massage table in the living room and when I walked up to her and put my hand around her waist she kissed my cheek.

"What do you think?" she said.

The table looked like any other of its kind. Except there was an oval hole in it. "I guess that's where I will put my cock and balls?"

"Yes, dear and I will be underneath sucking you."

I looked at the thing and I realized it was impossible to do what she wanted. "You know you can't reach my ass from under there?"

"Of course I can. I will stick my hand through the hole behind your balls."

"It's too small."

She stepped closer and looked at her handy work. She stuck her hand through the hole and shook her head. "Fuck! You are right."

"Sorry honey, I knew you worked hard to make this." Inside I was smiling.

"Don't worry, I have a plan B."

I took her around the shoulder and led her to the kitchen. "And what would that be?"

While helping me with dinner, she said. "Do you remember that vibrator you bought me?"

"Uh-hu."

"Well, I thought that we could use that."

I looked at her from where I was standing by the stove. She was at the kitchen table uncorking one of the wine bottled.

"How would your vibrator help us out? You still won't be able to reach around."

With a loud plop the cork came out and she grinned at me. "You will use it."

"What?"

"Yeah, it's perfect. I will help you insert it, but once it's inside, all you have to do is to slide it in and out."

An image flashed before my eyes of me fucking myself with her eight inch dildo. "I don't think so."

She stood and poured two glasses and took one over to me. "Oh, honey, it's my birthday, and you want to make me happy, don't you?"

Her hand that wasn't holding her glass rubbed my cock through my pants, and he came awake.

"Of course, babe. Anything for you."

"Thank you," she said and kissed me on the cheek.

All through dinner I kept thinking about what was to happen. Annie noted my lack of attention to what she talked about. "Hans, are you OK? Are you freaking out because I asked you to use the vibrator on yourself?"

I took a sip of my wine, and said. "Yes, I am. You know I don't like it."

She took my hand in hers. "Honey, you like to jerk off, don't you? This is almost the same thing, just that, well, you stick a fake cock up your ass." She said the last words with a crooked smile.

"Very funny. I'll do it, but only because I know how important it is to you."

"I love you."

While Annie went to look for her vibrator I got undressed and lay down on the table. It was narrow and I didn't have much room to move. I could only spread my legs a few inches to either side before they dropped off. My cock and balls fitted perfectly in the hole she had made, so that was a relief at least.

"Here we go," she said when she came back.

In her hand she held the vibrator and in the other a tube of lube. She was already naked and her firm boobs hardly moved as she walked towards me. Her pussy was shaved apart from a thin line above her clit.

"Be gentle," I said.

She kissed my ass cheeks and then began to rub lube around my anus and inside it with her finger. The feeling wasn't bad, it tickled a little and I must admit that my cock grew in size. I heard the low buzz when she turned on the vibrator and when the tip touched my anus it tickled even more. She moved around the area, pressing down gently and after a few minutes I moaned. Yes, I know, I say I don't like it, but at the same time the feeling is very intense.

"I think you are ready," she said.

"If you say so, darling."

She put the tip of the vibrator right on my anus and began to press down. I did what she had taught me and breathed slowly. When it slid in I gasped and almost bit into the bed. There was a sharp pain as the cockhead opened me and then it diminished as my anus adjusted around the shaft which was thinner.

"God, you look sexy," she moaned.

"I don't feel very sexy."

"Oh, shut up, I know you like it, you just play hard to get."

Like I said before, the feeling isn't half bad, but you feel like a complete idiot with a dildo sticking out of your ass.

"Hold here, and if you want, you can move it back and forth a little," she said, and placed my right hand on the toy.

It was an odd position and I wasn't very comfortable. I soon forgot all about it because Annie's lips closed around my own cock and her hand played with my balls. I couldn't see what she was doing, but whatever it was, it felt fantastic. She actually sucked on my glans, while using her hand to pull down from the base towards the head. I say actually, because during a normal blowjob the girl will slide her lips up and down the shaft. Annie kept her lips around my cockhead and sucked.

The vibrator was doing wonders to my prostate and after a few minutes I got that feeling of taking a piss, but I wasn't. It was a tickling feeling inside my cock and I knew the pre cum had begun to flow. I heard how Annie took my cock out of her mouth, and then she said. "Mm, you taste fantastic, keep going for a little while longer and then you can take it out."

I did what she asked and I could hear how she swallowed under the bed. I counted to three hundred and then pulled the vibrator out of my ass. As soon as I did, a whole other type of pleasure had come over me. Annie knew what I had done and instead of just sucking, she began to move her lips up and down my shaft while massaging my balls. My orgasm grew and when I came it was an eruption of cum.

"Wow, considering it wasn't a perfect set up, I say it worked pretty well," said Annie when her head showed up next to mine. She had cum on her cheek and a drop in her hair, and was wearing a big smile.

"Happy birthday, baby," I said.

She hugged me and then pulled me off the bed onto the floor. My cock was still semi erect and she used her hands to make me hard again. Then she straddled me and slid my cock inside her warm and wet pussy.

"Mm, you feel good," I moaned.

"You make me feel good, big boy."

She rode me until she heard from my breathing that I was close to coming and then she switched and I slid into her ass. She gasped once, twice and then she buried her face in my neck and moaned. "Fuck my ass, Hans; I love how you fuck my ass."

When I came for the second time that night I kissed her on the mouth and cheeks, and said. "You are the horniest woman I have ever met."

She kissed me back and pushed herself up, using her hands against my chest. "I have an idea. I hope you like it."

I became suspicious. "What is it?"

"Well, the table works fine, but the problem is that once you get horny enough, you don't want to or can't move the vibrator correctly so the flow of milk stops."

"Oh, I'm sorry. It's kind of hard to concentrate when you have a rubber cock up your ass and a beautiful woman sucking your cock."

"No need to be sarcastic, darling. We will simply find someone to help out."

"Like who, Roger?"

She laughed and hit my shoulder with her clenched fist. "No, stupid, I thought about another girl. Someone young, and eager to try new things. I could check out Craig's list and other similar sites for a woman who is looking for a couple to play with."

"Yeah? And what happens if she turns out to be a psycho and kills us?"

She got up and took my cock in her hand. "This thing needs more attention, and it's obvious that just you and I can't do it. We need help. Think about it. Wouldn't it be nice to fuck a sweet eighteen or nineteen year old pussy?" she gave me a wink.

Don't get me wrong, I love young women, but I already had one. I loved Annie and I didn't feel the need to bring someone else into the relationship.

"Not really, you are young enough for me."

She kissed my forehead. "You are so sweet, but you are a terrible liar. Give me a week or so, and I'll find us the perfect plaything."

Then she lowered her head and wrapped her lips around my cock. The girl loved her milk.

During the following days I spent a lot of time thinking about Annie's plan to bring someone else into our sex life. I guess I was happy about it being a woman and not a guy. Before I met her, Annie was part of a free spirit group in Sweden, which her boyfriend at the time had started. She had been with men and women during that time, both individually and in orgies. I on the other hand had no such experience. My ex wife and I had had a regular sex life as married people have, once or twice a month and always the missionary position. When I was single and in college I almost had a three-sum with two girls, but I was too drunk and passed out before I even got my pants off.

I spent some time on the internet and found out that milking was popular in the fem-dom niche. I watched a couple of videos with women in black leather leading around men with masks that they bound to beds or wooden crosses and then milked. It did not look like something I would enjoy and I prayed that Annie wouldn't find one of those to take home.

Two weeks after Annie's birthday, she called me at work one afternoon. "Hi, honey. What time do you get off today?" she said.

"Around five. Why?"

"We have a date; meet me at David's pizza house."

"What are we celebrating?"

"Nothing, we are going to meet Ashley."

"Oh, and who is she?"

"She is interested in learning how to milk a man."

"But.."

"See you later."

After she hung up I sat and stared at the phone. Ashley, how old would she be? Did she like to dress in leather and whip her man before stuffing a twelve inch dong up his ass? The thought made me shiver. I hoped Annie knew me well enough not to bring someone like that into our relationship.

I arrived at David's just after six and when I walked in I saw Annie in a corner booth. There was someone else sitting on the opposite side of the table, but I couldn't see her face since she had her back to the entrance.

Annie stood when I approached, and said. "Hans, this is Ashley."

I looked down and the face that looked back at me and smiled was not what I had expected. She was young, a lot younger than Annie, and she looked like someone's secretary. Big glasses, conservative hair cut, plaid skirt, sensible shoes and a white and blue pullover. Her eyes were dark brown and when she had smiled, she had straight white teeth.

"Nice to meet you, Mr. Kallberg."

Her hand was warm and dry in mine, and small. "Nice to meet you too, Ashley. Don't call me Mr. Kallberg, Hans will do."

"Sure, Hans."

"We already ordered the food, but if you want a drink, that is our waitress," said Annie and pointed at a blonde standing by the bar.

I got her attention and signaled I wanted the same as Annie, a beer in a frosted glass. I wanted something stronger to keep my nerves in place, but I didn't want to seem like an alcoholic in front of Ashley.

"How did you meet?" I said, breaking the silence, after I had sat down next to Annie.

"On Craig's list," said Annie.

"I put an ad in a few weeks ago, about being with an older couple and Annie answered it. We exchanged a few e-mails and found out that I was looking for the same thing as you," said Ashley.

I looked around us and the closest people were a few tables away. I leaned in across the table towards Ashley, and asked. "What did Annie tell you?"

I thought I saw her blush for a second. Then she drank some of her wine, and said in almost a whisper. "She needs help milking you."

"Oh, and what else?"

"Not much, just that she had made a table and afterwards realized it was impossible to do what she wanted."

"Have you done anything similar before?"

She giggled. "No, nothing like it, but it sounds cool."

"Cool, eh? Annie, are you sure this is such a good idea?"

NTsarina
NTsarina
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